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****Warning, this story contains man/boy love, diaper usage, piss play, and love. If this is not the sort of story that you are interested in, or not allowed to read, then please leave now. Should you wish to read this, then I hope that you enjoy it. As always, I write for myself, and share with those that might enjoy such stories, so I do not require your feedback to continue posting, however, with that said, I do appreciate the comments that you are kind enough to share with me, as well as any constructive criticism, flames shall be soundly ignored of course. Should you wish to do so, contact me at erich5748 ail. Also, remember that Nifty is our friend, and needs our donations to help them operate, do what can to keep this service free, as I do what I can as well. Well, here you go, I hope that you enjoy.****
I just got home from school, and my parents are both home, which I do not know why, and before I could ask, said that we need to talk. Oh shit, I hope they did not find out my secret. I am Skye, I am ten and a half years old, I live in a run down and smelly old apartment, in a run down and smelly old apartment building, in an even more run down and smelly old city. The walls are paper thin, the carpet is thinner, the hot water is about as hot as my piss is, with probably less pressure, and the cold water smells worse than the halls do. I go to an elementary school that has more bullies than most schools have students in total, and while I am not yet on their radar, I know that with what I like, that should they ever find that out, I will be totaled. Now my parents say that we need to talk, and I am starting to sweat.
My little brother Reilly is not here at the time, he is probably back at the hospital for more testing, or he likely has to stay again. He is really sick, the doctors say that the chances are not very high that he can survive for too long, he is only six years old, and cute as can be, but he is so sick all the time, I truly feel bad for him. The doctors told my parents about an operation that might just be able to save him, but there is only one doctor in the world who is willing to do it, and has had a success rate of ninety percent, but he is clear across the world, and the operation will cost in excess of one hundred thousand dollars. Between both my parents I doubt they make that much total in four or five years. Then there are the costs of getting him and at least one of my parents there for the two to three weeks that he will likely need to spend in the hospital. We do not have any sort of extra insurance that can help, and they already said they would not have anyway.
I had told my parents that I will do anything I can to help out, I offered to go get a job, quit school and do whatever I can to save him, I really do love Reilly, and I meant it. It is not like I have a lot of options to me anyway, even if I stay in school. I live in one of the poorest places in the entire country, and sadly, all us kids know that the chances of us escaping this hell hole just are not really there.
So, I gulped, and went and sat down on the chair, facing my parents, I hope that nothing shows on my face, I will try and play it off for as long as possible if I can.
“What”s wrong, is it Reilly?” I asked.
We all know that there could come a day when his little body just gives up, and I have dreaded that day too.
“In a way, yes, but, we”ve, well, we sorta found a way that you might be able to help him. You said you”d be willing to do anything to help him, right?” My dad said, and the way both he and my mom are blushing, it is making me wonder what the hell is going on.
“I”d do anything to help him out.” I said once again.
“We”ve found someone who”ll pay for the operation and everything, as long as you agree to be his personal assistant for minimum of one year, but possibly until you”re old enough to go to college as well. He says that if during the year, you both find that you”re compatible, that he”ll ensure that you go to the university of your choice for whatever you want as well. This not only helps Reilly, but possibly gets you outta this trench as well. You”re so fucking brilliant, but you”re being buried down here in the gutters. The odds of you escaping just aren”t there, but, we”ve found a way, that is, if you agree.” Dad said, as fast as he possibly could.
“What kinda personal assistant?” I asked warily.
“He promises that he”ll never hurt you, but, well, we know your secret, and we”re okay with it. He”ll likely be able to help you discover yourself.”
“Oh. That kinda assistant.”
“Only if you agree though. He said he”d explain everything to you if you agree.”
“I promised Reilly that I”d do anything to help him, and yeah, I kinda am gay, thanks for understanding, so, if that”s what he wants, then that”s what I”ll do.”
“Are you sure. Reilly wouldn”t want you to sell your soul to save him, that”s so much to ask, but, as his parents, we”d do almost anything to save him, but, asking that of you is too much for us, we hadta ask you ourselves, make sure you”d be willing, we can”t sell your soul like that, but, we do know what you want and need, and he can give it to you, and then so much more too if you work well together.” My mom said this time.
“Way down here in the gutters of the world, our souls are already sold anyway, I might not enjoy it, but I will do it, willingly. Neither you nor Reilly are selling my soul to save him, I”ll happily do it.” I said.
“He”s gonna pick you up this Monday. We”re to call him and tell him that you agree, and then he”s gonna get everything arranged. Now, we hadta tell him your other secret as well, we promised that we”d never tell anyone, but, he kinda sorta hadta know that.”
“Oh, I guess he woulda found out anyway, and he doesn”t have a problem with the fact that I”ll wet the bed for life, and that I haveta wear diapers every night?”
Yes, my shame that I carry. There is something wrong inside my head that sends the wrong message to my bladder when I sleep, so, I pee almost constantly, so, as such, I wear thick cloth diapers and plastic pants to bed every night. Reilly is still a bed wetter as well, but they have not yet found the same flaw in him, so hopefully he will quit, his brain flaw is elsewhere, hence his issues.
“No, he says that he”ll ensure that you”re as comfortable as can be in that regard as well.”
“Oh. Okay. And where does he live, I can”t imagine that anyone who has that kinda money lives anywhere near here, so how will I get to school?”
“You”re right. He probably has a few different houses, but the one that you”ll be living in is in the country, and he”s gonna home school you. We haveta give him all your records and sign a whole bunch of papers and whatnot. We really hope this works, and not just to save Reilly, though we don”t wanna lose him, but to allow you the opportunity to escape this place, and he can give you that chance.” My dad said, though he does have tears in his eyes.
“Will I be allowed to come and visit do you think?”
“Absolutely. He says he won”t take you away from us completely, but because you”ll live a fair ways away, it won”t be weekly or anything like that. Probably once a month or so he figures.”
“Oh good. I wanna be the one to tell Reilly. He”ll be crushed to know I”m going away, and no one should haveta tell him but me.”
“Agreed. He”d definitely never agree to you leaving just to save him.”
I feel suddenly more free. My parents know the truth of who I am, and they are okay with it. I am going to go away and save my brother and possibly even save myself at the same time. I should feel sick, I should feel dirty, doing what I will do, but, you know what, I do not.
No, instead I feel better. Clearly this new man is not only gay, but very rich as well. Maybe I will never love him, but if he is willing to use me to get what he wants and needs, then I too will be more than willing to use him to get what I want and need.
That evening, Reilly got home from the hospital, he is especially pale, and we went and sat on my bed, and I told him everything. I did not tell him that I will essentially be a whore, I just told him that I will be a rich mans assistant. At six, and very sheltered because he has spent most of his time in the hospital, I doubt he understands just how much assisting I will be doing. I would have known at six, but I do not believe that he does, at least yet. He will likely figure it out soon.
We cried a lot together, we cuddled up, and he admitted to me how scared he has always been, but that it was always my hugs that made him feel strong, but now he will not have that. I promised that I will still hug him as often as I can. I offered to get Reilly diapered and ready for bed, and he allowed me to, and so I made it a very nice diapering, and then he asked to repay the favor, and I allowed him to. I do not normally, because I have needed to take care of risen problems a lot lately during my diapering, so I have not allowed him to that often, but I do not have that problem tonight, and Reilly made it a very nice diapering for me as well. In fact, I have solely been the one to get Reilly into and out of his diapers since he was about three and a half, and I was five or six the last time I allowed my parents to diaper me up, even though I have true and proper pin on cloth diapers. I had to learn how to fold and pin them correctly and everything. Reilly still prefers me to diaper him, and has had zero desire for me to show him how to do so, even though I have offered. He asked me if I would now.
I did not bother going to school for the rest of the week, I stayed home with Reilly, so that my parents could both work, and we talked a lot. I did teach Reilly how to diaper himself from now on, so that he knows, but the funny thing is, he asked at about two o”clock that afternoon, and did not take it off until I changed him for bed, and boy was he soggy. I did not mind, and mom and dad said nothing about it either, but I have to admit, I have done the same thing, and enjoyed it clearly as much as Reilly did. I am scheduled to be picked up at about nine or so on Monday morning, and Reilly burst into tears on Sunday night before bed and begged me not to go.
It was heart wrenching, but I promised him that I am doing it for him, to help him to get better, and to maybe, just maybe get myself out of the hell hole we are in, and that I would do anything for him to help him to get better. I made him promise to get better for me, because I do not really want to have to do this for nothing, and he promised that he would do his best. We slept together, because Reilly really wanted to be close to me, one last time, both our thick cloth diapers pressed together all night as we slept, we were so curled up together. It was by far the nicest sleep I have ever had, even my dick behaved itself, a rather large nuisance lately, well, not large, but you know what I mean.
I have everything packed up, it is just eight thirty, I am scheduled to be picked up at nine, and Reilly has barely let me go all morning. We stripped and cleaned each other up from our nearly saturated cloth diapers, I washed and dried them, and then packed mine with the rest of my clothes and whatnot, not that I have a lot, we are rather poor after all, and now I am nervously waiting.
At almost ten minutes to nine, we heard the knock at the door, and instantly Reilly started crying. He knows that it is time.
When my dad answered the door, a very handsome man entered, he is dressed sharply, way too nice to be in this neighborhood, that is for damned sure. But as I looked at him, I have this nagging feeling that we have met before. Introductions were made, his name is Sterling, I would say that he is low thirties, just over two meters tall, and about eighty kilograms, and it all looks like it might be solid muscle too. He has very nicely cut light brown hair, bright blue eyes, really nice lips and nose, and I just went really fucking hard.
I have been looking for just such a man for a while. My parents might have known I was gay, but what I hope that they do not know is how much I was searching for a man to fuck and fill me full, and Sterling is definitely going to be that man. I just hope that he will be nice and not demand too much. I am still very much a virgin, though not by desire. I would have happily gave it up almost two years ago already had the right boy, teen, or man come along.
Once all the pleasantries were over with, Dad gave Sterling all the paperwork that he needed, and he checked it all over to ensure that it was all in order, and he was happy that it was, and then he said that it was time to go. Reilly would not let go and was bawling his eyes out.
I picked my baby brother up, cradled him to me, hugged him tight, and whispered into his ear. “I”m doing this for you Baby. You know I”d never leave you for any reason, but I”m doing this so that I don”t haveta lose you. You”re too precious to me, I promised you that I”d do anything to get the money to let you have the surgery to save your life. If that means going and doing this with a hundred men, that”s what I”ll do, and I”ll happily do it for you.”
“He”s gonna fuck you, isn”t he?” He whispered into my ear.
“Yes, that”s the deal, I”ll be his live in service boy, maybe I”ll enjoy it, I”m gay, I already know that, but even if I weren”t, and I hated every second of it, I”d still happily do it for you.”
“Absolutely Baby. You mean the world to me.”
“Once I”m better, do you think maybe I can come live with you as well, I wanna feel a peepee in my bum too. I”ve dreamed about it for a while now.”
“Oh yeah. Sometimes on the computer at the hospital I look at naughty movies, and I really like those ones. Does that mean I”m gay too.”
“Oh, that”s hot, and it just might. Tell you what, you do your best to get better, and once you are, if Sterling is nice, and I know he”d treat you how you deserve to be treated, then I”ll ask him, okay, but only as long as I”m the one that gets to take your virginity, would you like that?”
“Oh yeah. Can I tell you a secret?”
“Last night, as we were sleeping, and you had your diapered peepee pressed into my diapered bum, I dreamed that you pulled both our soggy baby diapers down and you slipped your peepee inside my bum hole and fucked me and filled me fulla pee.”
“Wow, glad I”m not the only one that dreamed of that. Tell you what, you go get better Baby, and the first time we”re able to, we”ll make that dream come true.”
“Okay, I”m totally gonna go get better then. I love you Skye.” He said, and then kissed me, right on the lips, thankfully he did not slip me the tongue.
“Love you too Baby, now, let me go, so that you can go get better, okay.”
“Okay.” He said, and then wiped a few last tears from his eyes as I set him down.
I went and hugged my parents goodbye, and they both asked me one final time if I was sure, and I said that I am, that I would happily do anything to save Reilly.
Finally we are on our way, and it was a silent walk down twelve flights of stairs, since the elevator probably died when my parents were kids, and down to the street. When we arrived, I found a limo there waiting for us. Wow, sure as hell have never seen one of them down in the slums. Gee, I wonder how many people will put two and two together and come up with I just got sold. Probably every person there over the age of five. Oh well, it is the truth, and clearly Sterling does not care, and really, I do not either.
Sterling opened the door for me and I climbed in, and then he climbed in behind me. I just have one backpack full of things, and half of that is in diapers. The interior of the limo was like nothing that I have ever seen before, and I have seen the interior of them on TV a few times. Where there was supposed to be a window to the driver, instead there is a large screen TV, and on a shelf beside it are a few different games systems and a blue ray player. The drawers underneath it have a lots of games and movies.
“Wow.” I said as I looked at it all.
“Yeah, I”m in here a lot when I”m traveling, and I enjoy that, so I had this made for my tastes.”
“Have we met before, I feel like we have.”
“I wondered if you”d remember. It was almost a year ago, I was the one that came to your school and tested you.”
“That”s right. You weren”t as dressed up, you were testing me for an advanced program.”
“Exactly. You”re incredibly bright. Your talents are being wasted in this dump. You”re the one that found me first though, babyskye3215.”
“Oh, so clearly you know my tastes. So, who are you then, I don”t email or chat with anyone by the name of Sterling?”
“No, I don”t use my real name, and everything I do is routed through a few places first. I”m gbdl21648, clearly I do it like that to protect me. I started hatching this plan a little more than a year ago now, you told me more than enough to know what I hadta offer. Now, in a way, yes, I paid your parents to have sex with you, but I truly detest that sort of thing. I never want you to feel as if you”re nothing but a whore to me. I started falling in love with you before we even met, and I hope that eventually that love will be returned. If all it ever is to you is getting the money to help your brother get better, then so be it, I will let you go, it won”t be entirely willingly I admit, I”ve searched long and hard for a boy just like you. You know as well as I do how much of a boy lover I am, and how much of a diaper lover I am, and we both want so many the same things.”
“Truthfully, even though I never actually met you, at least I didn”t think so, I”d already started to fall in love with you as well. You always talked so nicely to me. So many of the others just wanted me to take pictures of myself and send them, they wanted rude and nasty, and while I wouldn”t complain about that every so often, it”s not what I wanted and needed. You and I are alike in that way, that”s why I liked you so much, and why I still chatted with you. I don”t know if we”ll truly fall in love with each other, in which case I”ll put in my years service, but maybe we will, and I”ll stay on. You”re a boylover though, what happens after I turn fourteen and am no longer really a boy any more?”
“I”m fully gay as well, I believe I”ve told you that, I do enjoy being with older teens and even young men too, so that won”t be a problem. No, you won”t likely haveta worry “til you”re at least twenty, possibly twenty five. You”re an insanely pretty little gay baby boy diaper lover, and I think that you”re gonna grow to be even nicer looking still.”
“And are we really gonna getta wear real diapers, proper thick thirsty tape on baby diapers, so gloriously thick it”ll take me an entire day to fully fill them?”
“Oh hell yeah. Already have lotsa thick thirsty baby diapers for you.”
“Oh man. What are the odds that you have some already here?”
“Do you honestly believe that a gay baby boy diaper lover such as me wouldn”t?”
“Oh, I guess not. Why haven”t you offered to diaper me yet?”
“It”s not my place to do so, you haveta ask.”
“Oh, please diaper me up like I deserve.” I ask, and am already stripping naked in order to get what I have so desperately wanted and needed for years already.
If I could have, I would never have potty trained, and I would have happily wore my diapers all day every day. I have worn my cloth diapers a few times, but it is hard to hide such a thing, and I honestly had no idea how my parents would have reacted to that, so I never really did it that often, only when they were not home to witness it did I risk it. Even though I really should have though, I doubt that I have ever went pee before bed, why bother, not only was I going to be wearing a nice thick thirsty diaper, but I have known I was a diaper lover for a very long time, and I loved peepeeing my baby diaper as soon as I had it on. I would sometimes hold it for an hour or even two before getting ready for bed. I never wear pajamas to bed, but I always wear them, and get ready for bed at least an hour before bed time, so even though my parents knew that I was diapered, because how could I hide such thick diapers, but I doubt that they ever truly knew. Sure, I am sure that they may have suspected certain things, but knew, probably not. Reilly did know, because I know he did the same thing, and we admitted it to each other more than a year ago.
As soon as I am naked, I even took my shoes and socks off, I laid down on the couch in the back.
“My my, Baby sure is excited.” Sterling sighed as he petted my little diaper monster.
“Oh yeah. I think you have at least a little bit of a clue just how often I”ve dreamed of this. I believe I told you what I feel is the perfect diaper change, several times, and if you”d be willing to, I”d like just such a diaper change right now?”
“Sucking and fingering included?”
“How many fingers?”
“As I”ve told you before, I can slip four of my own fingers inside myself, so try for three of yours.”
“And how many baby boygasms would you like me to give you?”
“I believe I”ve also given you that answer before.”
“You sure have, so ensure you”re soft enough to tape up.” He grinned brightly.
From a drawer under the couch, Sterling pulled out a gloriously thick disposable baby diaper, as well as a large bottle of the original and best baby lotion, and a jar of the same diaper rash cream I keep at home for myself and Reilly. Sterling slipped the diaper under my baby bum, and then squirted way more lotion than was needed into one hand, and as he sucked my little gay baby bone in, he started tickling my little gay baby bum hole to gain entrance.
I have played for a couple years already, dreamed about the day I would finally get sucked and fucked, but, already, not even having Sterling inside me, it is feeling better than I have ever dreamed. Then he slipped his first finger inside me, and I came, hard. Never before have I had one of my little gay baby boygasms nearly wipe me out, but this one damn near did, and it took me way longer to come down from it than it took Sterling to cause it in the first place.
“Wow, that feels fucking amazing.” I whisper.
Sterling mumbled something around my hot little baby cocklett, but did not detach, and continued to suck and finger fuck me. Almost half way to my second baby boygasm, Sterling must have felt that I was ready, so slipped a second finger deep inside me.
I admit, I moaned extra deep with that. Truth be told, I have not used just my fingers, since they were not always enough to scratch my really deep itches, but Sterling”s fingers are way longer than mine are, and with just his fingers, he is very nicely scratching my really deep itch. And then I came again.
This time I took even longer to come down, and I am feeling better than any one person should, I swear it, certainly a far cry better than I have ever felt in my entire life.
Once more, Sterling never even stopped, and only a few seconds after coming down, Sterling started slipping his third finger inside me. It is a bit of a stretch, his three fingers are certainly bigger around than my four, but he is going slow enough for me to accommodate him easily enough, and even though there are little twinges of pain, the incredible feelings keep overriding them.
This time I took a little longer to cum, but this time it took even longer to come down, and amazingly enough, I am still hard, and Sterling is still sucking and fingering me masterfully.
Sterling does not have all of his three fingers in me yet, and after every few seconds he goes just a tiny bit deeper, opening me up just a tiny bit more, and it is starting to get a little tight and uncomfortable, yet, still, the amazing feelings are still overriding the discomfort. I have known that I was gay for a long time, I have stretched myself well for almost as long, and I am so close to fisting myself it is not even funny, I am talking I would have likely tried it within the next week or two had Sterling not come along. Hell, I still might, preferably while he watches.
Then I felt Sterling fill me as full as three of his fingers could possibly fill me with, his fist is pressed against my gay baby bum, I am officially more full right now than I have ever been before, and while there is still some pain, I feel better than I have ever dreamed was possible, and then I exploded in my most amazing orgasm to date.
I woke up, I have no idea how much later, and I am still full, but I am diapered wondrously thick now, and I already feel wet. It took almost a couple minutes for the fog to clear, and when it did, I looked around to find Sterling, sitting in the chair, watching me, now in only his diaper, which appears to have been freshly changed.
“Took you long enough. You were asleep for damn near half an hour.” He grinned brightly to me.
“Fuck, that was amazing.”
“Glad you enjoyed Baby. I didn”t go too far or too fast for your shockingly little gay baby bum did I?”
“Oh, no, definitely not. That was perfect. I”m pretty sure that the laws of nature state that no one should be able to feel as good as you made me feel.”
“Good, I”m glad.”
“I still feel full, did you slip something inside me?”
“Yep, a nice little butt plug.”
“Nice, as you probably recall, I”ve dreamed of that since, well, as long as I can remember actually.”
“Yep, hence the reason you”re so thickly diapered and plugged.”
“I was asleep for almost half an hour you said?”
“Yeah, about twenty five minutes I guess.”
“I shouldn”t be this wet yet then, did you help me along you nasty gay baby boy.” I ask, though I am probably grinning every bit as brightly as he is.
“Oh yeah. I was so fucking hard, I knew what you wanted, and so, I helped you wet your baby diaper. Four loads of cum, and one massive load of piss. I was nearly bursting by the time you passed out, and that was one of your biggest fantasies, so I gave it to you as well. I wouldn”t normally do anything to someone without asking their permission first, but you did ask for the baby diapering of your dreams, and that was absolutely part of it, so I felt that it”d be what you wanted anyway.”
“Fuck yeah, and it”s more glorious than I dreamed it”d be. Now I can”t wait to give you as nice a diapering.”
“Then this evening we have a date. Now, we needta talk.”
“Okay.” I said, sitting up so that we could talk.
“So, first and foremost, you are my personal assistant, which means you will be working at times. I do still run some of my businesses, and so, in that regard, you will actually be working with me and learning. Then there”s learning. That”s your biggest single job. When you”re not working for me, you”re doing school work. Six hours a day, six days a week is what you dedicate to your school work. I imagine that with as bright as you really are, that this”ll be no issue whatsoever, and as such, I fully expect you to be well above your peers in just a few months, possibly a full grade higher than them by the time four months passes, and two grades or more before the year passes. Within that six hours per day, at least one hour shall be dedicated solely to university courses, once more, the tests I had you take say that what I”ve chosen for you shouldn”t be any problem at all.”
“May I ask a question?”
“Of course Baby.”
“What courses have you chosen for me?”
“One of the tests that I had you do was an aptitude test that tests you in all sorts of ways to see what sort of things you might be interested in. I doubt you fully remember all the tests we did that day, it was an entire days worth. What I found was that you”d do incredibly well in business management, in line with what I myself do. I own and run a few fairly large businesses, though I no longer do much of the day to day work, and I only go into the offices maybe once a month now. So, the courses that I”ve chosen for you will help you in that, and then what you learn as you help me will help even more.
“So, for the most part, that is your learning, though an extra hour per day is dedicated to physical fitness as well. I swim or do water aerobics every morning for an hour, and so too shall you. Now, sex, you are not in any way my sex slave, and while I absolutely desire to make love to you, and you me, I will never make you do that. What I”m looking for is a willing partner. I hope my mark was not missed in you, I strongly feel that the two of us are very much compatible and as such, I truly hope that I”m not just gaining an employee, but a full partner as well, business and personal. I”ve had few partners over the years, far too few if you ask me, none like you though.
“No, not one of them was young, most were really late teens or early twenties, twinks you”d call them. Sadly, most of them just were not smart enough for me. I find it very hard to spend much time around stupid or dense people, I find them very draining. The day we spent together doing those tests, not only were you incredibly bright, but also witty, and not once did you shrink from doing another test, in fact, you loved the challenge, and when you found a tough question, you just said, ooh, a tough one, and then promptly figured it out, especially math. In fact, you”re even better than I in math, and there”s none I”ve ever met before that I can say that about.”
“Really.” I said, in shock.
“Absolutely. I told you then that you”re incredibly bright, I urged the school to bump you up a grade, and or challenge you more, they refused, they couldn”t care less about you, sadly. So, I knew I hadta figure out some way to get you away from there. I hadta figure out some way to get you out, you were gonna be buried, and you and I were so much alike. It was me that found the doctor who claimed to have such high success rates at helping Reilly, and no, I had no clue what it”d cost. Truthfully, I hoped it wasn”t gonna be so much money, that”s a huge cloud hanging over your head, I wanted a willing partner, not someone who felt obligated. In the end, though, it is what it is, and with all luck on our side, it”ll work out for the best. Again, though, I hope that my helping your brother, paying so much money, is not making you feel that you”re nothing but a whore to me, that”s the sorta thing that”d just disgust me. I paid for sex once, it was horrible, and since then I”ve never so much as fathomed paying for sex again, and such is the reason that sex is not part of your duties for me, I don”t want for it to be a duty. I do truly wish to make love to you at least once, but if after that, we never do, then so be it. I want it to be your choice.
“As for other duties, pretty much just helping to cook and clean for the both of us. I have no other staff, given my desires, I really don”t want others too close to me too much. My driver lives a short way from my house, well, almost an hour away, and though he”s signed a non disclosure waiver, I still never allow him to truly see what I like. I just hate driving, I”d really rather pay someone else to do that, and it allows me to do work during the long car rides I often have to take, since I live so far from town. I do have access to a helicopter as well, it”s for my business, so sometimes if I haveta go further away, that”s what I”ll take instead.”
“Oh, okay. I don”t know how I”ll feel about sex yet, but as you well know, I do truly want it as well. I don”t honestly feel that your paying to help Reilly as being a dark cloud over my head. In a way, you”re gonna help me every bit as much, and maybe, just maybe we”ll get to really love each other as well. You”ve told me a lot about you, I already feel I truly know you, our likes and dislikes are very similar, so, maybe this”ll work out for both of us. And, just so you know, tonight is the night I want my virginity taken. Since I learned what you were wanting, I knew that the first night hadta be the first time too, so that I knew. I haveta know if we could truly be together, or if it”ll just be a job for me. Maybe if it is a job, I”ll learn to enjoy it, but maybe not. I hope that what I think I feel is more than that though.”
“If you”re certain, then I”ll do my utmost to ensure that it”s the single most amazing experience of your entire life then.” Sterling smiled warmly.
“Thanks. So, how much longer do we have “til we get to your house then?”
“Our house now, but still almost two hours.”
“Oh, really, we really do live a long way away then, huh.”
“Yes. We have pretty close to ten thousand acres out in the middle of nowhere, up in a really nice mountain valley. We have our own private lake, there”s something like twenty creeks leading to it from all the mountains surrounding us, and then one large creek or small river leading out of it. Back when I had the place designed and built, I had them damn the lake, which made it rise something like fifteen meters, and that”s what we use as power. We live on the hill above the lake, though we”re on a natural ledge, and as such, we have some pretty spectacular views. You”ll get to see all sorts of wildlife, but that also brings up the only real problem about living there. Under no circumstances are you to ever go outside at night, and even during the day I strongly suggest you not go without me and my gun. I never go out without some sort of weapon. During the day, you haveta worry about cougars and bears, and at night, the wolves would have a nice little snack of you, and they will take you. I would”ve tried having dogs and cats, but they”d never last a week. And they”re brave fuckers, I”ll often look out one of my patio windows and see one or more of them sitting there, watching me. They”re beautiful, don”t get me wrong, but don”t agree to be a guest at a dinner party, I assure you, it won”t end well.”
“Fuck, never even seen a real animal, other than pigeons and rats and whatnot. The rest sounds amazing though, but totally not going outside without you then.”
“Wise choice.” Sterling laughed.
“So, what do we have to do that”s fun then?”
“Lots. We have a really nice pool, games room, theatre, gym, and library too.”
“Oh, um, I can”t swim. Never even seen a pool in real life.”
“Really. That”s actually pretty sad, to tell you the truth, but not really surprising either. I”ll teach you though, it”s easy, and at your age I”m sure you”ll learn real fast.”
“Yeah, I know, but I lived in the middle of the slums of one of the dirtiest cities in the world. We had zero money for shit like that, and the only pool anywhere close was closed down before I was even born.”
“You may think it was the dirtiest, but trust me, your home sweet home was considered paradise to some. I”ve personally witnessed far more horrible places than what you grew up in. It was disgusting seeing how some people live. No, you had it bad, there”s no doubting that, but, you truly should be thankful that you did have all that you had, for there are those who had far less. Your apartment building, for instance, was actually one of the nicer ones I”ve seen. I know, it wouldn”t win any awards, probably ever, but there was one in Mexico where I went to scope out business dealings that was so atrocious I nearly lost my lunch, from the previous three days. There was mold and bugs and rodents galore. The smell was so horrible you can”t possibly imagine. They had upwards of twenty people living in the same amount of space that you and your family lived in, but there were no beds. There was also no running water, no toilets, they collected rain water for everything, and all their bathroom needs were collected in pails and left to rot until it was full, then it was just dumped in the gutter. There were others that were worse than yours, but that was the worst that I personally saw.”
“Really?” I asked in disgust.
“Absolutely. Once I get you up to speed on things, and you become my actual business personal assistant, you”ll get to see things that you never imagined. Hopefully most of them good, but there will be bad as well.”
“Oh, you won”t make me watch as you torture and kill a rival business owner or maybe a corporate spy, will you.”
“No, oh god no, I”d never do that.” He said in disgust. Then he grinned, “Nah, I pay others to do the dirty work for me. Just kidding. I”d never do anything like that. No, I pass those on to the police to handle.”
“Oh good. Living where I do, death is just a fact of life, even I”ve seen someone die, it”s not nice, but we all know that our turn is coming. The simple fact is, forty is considered seriously old, and if you make it to sixty, you must be nearly immortal.”
“Yeah. I know. Believe it or not, you and I didn”t grow up all that much different.”
“Really, you were a slum kid too?”
“Yep, gutter born and raised.”
“How”d you escape then?”
“In a way, kinda the same way as you, only I searched out the men who”d pay me. I started selling my little pussy when I was seven, the first man to fuck me hurt me, bad, but he paid me a hundred dollars, and so I enjoyed every fucking second of it. No, I was a whore, plain and simple, and I had hundreds of men, sometimes several times, usually every night of the week was a different man. I also knew that to escape meant that I hadta do spectacularly in school, and so, I did my absolute best, but, in a slum school, your best really doesn”t mean much to those in universities and whatnot. I was fourteen when I graduated, and at first, the man who ran the university that I was going to go to said that I didn”t qualify, blah blah blah, just because I was gutter trash. So, I let him fuck me with wild abandon, in fact, I got half tuition the entire time I went because I let him fuck me like he could never fuck his wife. He wanted dirty, raunchy, nasty, he wanted to tell me what a dirty pig I was, all that, and I let him. I graduated two years early, ten years worth of university crammed into only eight years, and how I paid, I sold my soul to any man who”d pay. I hated every fucking second of it too, but they never knew it, I made every last one of them feel like they fucked me like they were a god. I was a primo whore, I charged a lot, and they got a lot because of it.”
“I damn near started selling my ass a year ago, but my dad begged me not to go and earn money any way necessary. I told him I was gonna go get a job, do what was needed to get money, I think he knew, I didn”t then, but I agreed. He made me promise to just stay in school and do the best I could there, and to let him worry about the money.”
“Yeah, I know, you told me.”
“Oh, forgot I told you that.”
“So, when did you get started wearing diapers then, I don”t remember if you ever actually told me?”
“No, I never did. I was and am a full time bed wetter and frequent pants wetter. I actually have something wrong in my bladder, but though I tried going to the doctor when I was a kid to figure it out, he just pretty much brushed me off and told me I was wasting his time. He said if I wet the bed, then wear diapers, so, I did. Like you, I had thick cloth diapers, I went and bought some with the proceeds of my first fuck in fact, and that night I had by far the best sleep ever. Not only was I incredibly drained from being fucked so wildly, and he used me for nearly three hours, but, I also got my very first diaper that night, and didn”t wake up soaking wet and freezing cold, and slept for nearly sixteen hours. Of course, I leaked, which was probably why I did wake up, but it was way better than I”d ever experienced, and so, I wore diapers every night from then on, and I loved it.
“I was your age, so ten, when I started wearing just two cloth diapers and my rubber pants during the day to contain my frequent accidents. At first it was because I had to, but, then, you know, it wasn”t all that long before I never even tried to go pee in a toilet, and I was loving them. The men who paid to fuck me, wow, I brought out the kinky in them, wearing diapers like I was. Boy did they love the fact that they were fucking a baby boy. It wasn”t until I was out of university and got my first real job that I found disposable diapers, and I haven”t worn a cloth since. I loved my cloth diapers, but, I love these way more.
“And by the way, even when I started working, I”d still sell my ass to any who wanted it. I also happily allowed myself to be fucked all the way to the top. Within two years, so, when I was twenty four, I was running the entire place, became CEO, and then I made my boldest move ever, I did a hostile takeover, took full control of the company, and made it grow even more. That same year, I took over three other companies that were failing, just managing them, but within a few years, they were mine as well. I was twenty eight when I had our home built for me, and I stepped back from the day to day operations. I no longer desired to be fucked for other peoples pleasure, and the first time I had sex, and actually got to fuck my first ass, when I was twenty eight, it was horrible. I was using him like I”d been used, and I cried and I cried and I cried. That”s when I knew.”
“Wow. That”s both horrible and amazing.”
“What”d you learn?”
“That I needed to find a lover. I never had loving parents, at least you have that, and from the time I was seven, I was used and abused. Sure, I asked for it, begged for it in fact, I thought it”s what I needed, it filled a hole in me, I needed to find and feel intimacy, but, that”s not what I found. I kept telling myself, maybe the next one. Yeah, well, the next one never arrived. Then I paid a young whore to be what I”d always been, he was maybe fifteen, I never asked, he never said, we really didn”t talk, and so, I fucked him, I fucked him hard, I filled him full, I used him and I abused him, and it hurt me more than I hope you can imagine. We”d agreed on a hundred dollars, but, when he tried his best to console me, that it was alright, that it”s what he wanted, I told him what I”d been and done, that he and I were the same, and that I”d just done to him exactly what I”d hated about my entire fucking life. I cried the entire time. He tried to tell me that he enjoyed it, but I laughed and said I said the same thing so many times it wasn”t even funny, but that I know the truth. I gave him every penny of cash I had, probably close to three thousand dollars, and told him to go and quit this life, go do something good for himself. He contacted me a few years later, merter escort and told me that with the money I gave him, he put a down payment on school, and that he was going to college, that he had quit that life, and he thanked me profusely.”
“Oh, that”s nice.”
“Yeah, he”s never contacted me since, I hope he”s still doing okay. That”s the reason why I wanted to rescue you so much, as well the reason I can”t just fuck you. I”ve never made love, nor never been made love to, I started falling in love with you a long time ago, and I do truly hope that we can make love to each other. I hope I”m not too badly damaged for that.”
“I don”t think that you are. I do truly hope that we can make love, and that maybe you”ll be healed, because clearly you”re not.”
“No, you”re very right about that.”
For the entire rest of the long drive to what will be new home, at least for a short while at any rate, we talked and talked and talked. We have talked so much in the past that we do already really know each other anyway, but we are saying even more than we could ever say in an email. It was really nice, actually. No one knows me as well as Sterling already did, nor I he, he says, now we both know each other even more. Just getting to sit there in just our diapers, talking was so nice.
When we were getting close, Sterling said we have fifteen minutes until we arrive, we got dressed, so that the driver would not see how we are currently attired. My pitiful clothes barely covered the gloriously thick diaper, but they will do all that they need to do, since the driver will really not even see us anyway, Sterling says. He will pull us right up to the door, and he was told that he never has to open doors for Sterling, and that as soon as we are out, that he is welcome to head home until he is needed again. Sterling says this is his standing order to his driver. I admitted that he must have a super easy job then, once or twice a month take Sterling somewhere, never have to get in or out, and he said that he probably does love his job, but that it can sometimes be days at a time that they are away for as well, but that his driver always gets a really nice hotel room as well.
As soon as the house and the valley came into view, I admit, I think my jaw may have hit the floor. Holy shit, it is truly stunning. It appears to just be one level, and huge. There is a large glass dome right in the centre of the house, and if I had to guess, I would say that the entire place is nearly as large as our entire apartment complex was. There are more doors and windows than I can possibly count, and the gardens that I can already see are huge and spectacular.
“Wow, would you look at that, it”s, beautiful.” I said in awe.
“Thanks. As soon as we”re free to do so, we”ll strip back down to our soggy baby diapers, and then I”ll take you on the tour.”
As Sterling had said, the driver simply pulled up to the door, there is a large cover so that he could drive us right up to the door and even in the worst weather, we would never get wet, and we got out ourselves, we each grabbed one of my bags, and as soon as we were out and the door closed, the driver pulled away. We headed inside, Sterling did not even have to unlock the door. Man, I cannot imagine leaving any door unlocked.
The front entrance of the house is actually at the back of the house. Sterling says it is the dark side of the house, because he kept this side closer to the hill and the trees to get the better view and far more space on the other side. There were no real gardens to speak of at the back of the house because of this, but I had seen that driving up, that all the gardens were on the other side.
As we walked in, I was greeted with the most amazing house I have ever imagined. It is large and open, the ceiling probably every bit of two stories high, at least by what I am used to. We entered right near the centre, and just ahead is where the large glass dome is. I can see straight through to the other side of the house, and there is a large wall of glass there, looking straight out into the yard. There are hundreds of plants under the glass dome, many are decorative, but many I can also tell are fruit or vegetable plants as well, since I can clearly see tomatoes, cucumbers, and many others there.
To our right as we enter is a large closet for storing shoes and coats, and then past that and to our right still, is the kitchen. I have seen pictures of restaurant kitchens, and most of them are nowhere near as large, but it is the most stunning kitchen I have ever seen as well. To our left is a large living room, and there is a massive fireplace, so large in fact, I am certain I could go and stand up inside it rather easily. The dining room is to our right as well, but hidden more in behind the closet wall, but I get to see it as we leave the entry way, and it too is beautiful.
Past the living room is a hallway, and that is where we head. Sterling tells me that this is the bedroom wing, and when I asked, he tells me that there are six bedrooms, every one of them large, bright, and with a massive washroom all to itself. The largest, of course, is Sterling”s, and likely mine as well, though he tells me that I will actually have my own bedroom, should I choose to use it. We just go right to Sterling”s though.
Wow, what a bedroom. The entire outside wall is glass, though Sterling also says that they are actually doors that can open up completely and bring the outdoors in, when needed or wanted, but that it can be dangerous, for the reasons he already told me about. The bed is massive, there is a fireplace almost as large as the one in the living room, there is a really nice seating area by the fireplace, and I bet it is wonderful for curling up and reading. Then he leads me to the bathroom.
Holy fuck, his bathroom is every bit as big as our entire apartment was. We did not have a huge apartment or anything, two bedrooms, a bathroom, kitchen, and living room, but, that amount of space as a bathroom, holy fuck. The tub is huge, my whole class at school could have probably fit in it, same with the shower, and I actually lost count of how many shower heads there were, I got up to thirteen in my quick count, inside a small room is the toilet and what I am told is a bidet, and then inside another closet is the washer and dryer. The counter top is actually a huge slab of wood, and the sinks are carved right into it. There are a lot of wood and natural stone details all throughout the house, very organic feeling, but they truly shine in here.
“My god, I”ve never imagined a bedroom and bathroom so amazing in my life.”
“Thanks. It took me a long time to design all this, and even the architect who took all my ideas down thought I was crazy, but I think it turned out very well.”
“Very well isn”t quite the right choice of words if you ask me.”
“Yeah, but it”s the only ones that come close.” Sterling laughed.
“So, how many people come and clean all this for you?”
“Once a month, a team of four ladies comes in and cleans everything for me, except my bedroom and bathroom, those are off limits to everyone, this is my private space, only seen by me, and now you.”
“Yes, in fact, other than workers, you”re my first guest here. I know, technically, you”re an employee, but I”m still holding out for more.”
“Because, this is my private sanctuary, it”s never felt right to bring people here. Now, other than looking, we are here for a reason, so, mind terribly if I strip you down to your sexy soggy baby diaper?”
“No, as long as I get to strip you down as well.”
“Okay.” He said happily, and then came and stripped me until I am in only my diaper again.
“Fuck you”re stunning in just your diaper.”
“Thanks, so are you, now let me strip you as well.” I said, and then proceeded to do so.
“Ah, much better. I truly hate wearing clothes, I”d much rather just wear my baby diapers all day, every day, and never haveta get dressed.”
“Yeah, as you know, I dreamed of that for so long, and now I get to. Thanks to you.”
“You”re welcome. Now, let”s go tour the rest of the house.”
Sterling showed me the other bedrooms, and they are all very nice, and large, just not quite so nice and large as his own. We checked out the kitchen, living room, and dining room more as we passed through each one, and they are nice. On the other side of the kitchen is a large butlers pantry, a large wine room, and then what would technically be a butlers bedroom. Sterling said that he included it, only because should he ever sell, a house such as this demanded such an inclusion. The entrance to the massive four car garage is at this end of the house, and we even peeked in, but there is absolutely nothing in there. Sterling says he really does not like driving, so he does not even own a personal car.
There is a set of stairs leading down from the mudroom, and when we arrived downstairs, I nearly forgot to breathe. I have seen pictures of games houses that are designed to hold a hundred people or more at a time that are not as large or as well set up as Sterling”s basement is.
“Oh yeah. This is amazing.”
“Believe it or not, but the upstairs is only as large as it is because of all that I wanted down here.” He said proudly.
We entered into the games portion, but not only are there dozens, if not hundreds of different arcade and table games, but it is interspersed throughout the most amazing mini golf course you could possibly imagine. To our left as we came down the stairs is another door, that must lead directly underneath the garage, and Sterling confirmed that, as he led me through that door.
Through that door, we found the pool. One wall is glass and looks outside though, but that should not be possible. When I asked, Sterling said that there had been a natural cliff there that he had decided to take advantage of, by doing just this. The fact that the garage is above us, and so, the entire massive space is concrete enshrouded, was done on purpose, so that the moisture could not hurt any wood. All the walls are tiled in beautiful marble, the ceiling was stuccoed and then painted to look like a cloudy blue sky, there are five doors other than the entrance, two bathrooms, a sauna, a steam room, and then the pool utility room. The pool is huge, and there is a really nice hot tub right next to the glass wall. The ceilings down here are incredibly high, I am guessing four meters, but Sterling says closer to four and a half.
From there, we headed to the other side of the massive basement. There is a hall, and only two doors. One on the wall as we walk down the hall, and then the other at the end. The first door we passed, we entered, and found the theatre. There are only twenty seats, but is large and luxurious. It reminds me of theatres that I saw in old movies, places that used to be held in much higher regard than they are now. The screen is massive, and I was assured the sound system is second to none.
From there we headed down the hall to the last door, and when opened, the door hid a shockingly large gym. It is nearly as large as the gym my old school had in it. There are several doors in here, they all lead to various storage rooms, each holding different things. There is workout equipment around the exterior of the large room, there are basketball nets up, various nets for other sports strewn about, mats for doing floor stuff, pretty near everything.
“Wow, why”d you do this?”
“To keep in shape. I actually enjoy working out, and like I said, at least one hour per day is dedicated to either here or the pool, strictly for exercise. But also for fun. Sadly I”ve never truly used this gym for much fun, because of course I”ve never had anyone to play with, so we”ll be able to play a lot down here now.”
“Wow. No wonder upstairs is so large then. Why not just put all this in other buildings though?”
“It probably woulda been cheaper to do so, but that”s not what I wanted. I wanted it all in one, and really, like I need to give a damn about the money, I could”ve built twenty of these houses then, I could build more now.”
“Fair enough. Not used to having money. Hell, not used to having any of this at all, so it”s gonna take some getting used to, that”s for sure.”
“Know how you feel. You know, until I built this house, I stayed living in cheap, shitty apartments, I had nothing, I wanted nothing. I grew up with nothing, and even though I had more than enough money to buy the entire apartment buildings I lived in, for there were four, I still never truly spent it. About the only thing I splurged on was getting a car and a driver. Until I bought this place though, it wasn”t even a limo. I bought the limo strictly because I needed a more comfortable ride for the long commutes, and it really does suit my tastes much better. Even still though, I have a hard time truly spending money. This house cost more than you could possibly imagine, and I had near daily mental fights and or breakdowns because of it, and only the day I moved in did they finally stop.”
“Yikes.” I giggled, but I think I know what that would be like. I grew up with no money either, so spending money is hard to do.
“Yeah. I”m probably the only multi billionaire that has a hard time spending my money. Granted, my businesses spend money like it”s going outta style, but then, we”re also making shit loads more because of it. It”s funny, I have zero problem spending company money, but, it”s like they say, you have to spend money to make money. Granted, I am super anal about them spending unnecessarily as well. All funds have to be authorized by me first, and that”s my biggest daily chore, going through all the daily financials.”
“That”s good though, having someone keep a tight leash on them prevents them from spending stupidly, because otherwise I”m sure they would.”
“Oh yeah, that they would. Every last business I took over had massive problems with that, and was the reason they were failing. I even caught one guy, a super high up guy, buying shit for his office that was nowhere near needed, and he was using company money to do it. I told him flat out that every penny he spent on his custom bar, desk, fancy bathroom, and assorted other shit, he had to pay back, plus interest. That was when I was younger and didn”t keep near as much watch over them. I told him flat out that it was because of that exact sort of behavior that his company had been failing in the first place, because they were spending way more money on stupid shit, than they would ever be able to earn.
“I ended up firing him, because he refused to not only pay it back, but listen to me. He thought I”d never be able to run the company without him, he thought he made the company. So, I grabbed one of the janitors, taught him what he needed to know, and gave him the asshole”s job instead, and told him so. I also black listed him, and he”s now poor and working a dead end job. No one blatantly tells me that I”m too fucking stupid to run a company and that if I so much as look at him wrong, he”ll make certain all my businesses go bankrupt within a year. Every year or two, I call him and ask him how he”s doing, and how it”s going, taking me down, because I”m too stupid to run a company. I did that not all that long ago, and he finally broke down, sobbed, begged me to remove the black listing, to hire him back, anything. So, I gave him a job as a janitor. He can work his way back up, the hard way this time, and maybe learn that there”s a price for success.”
“Nice. Now that”s a lesson that I”m certain will stick with not only him, but everyone else as well.”
“Exactly. Even when I catch my employees doing that which they know they”re not supposed to do, I almost never actually fire them, I figure out some sort of punishment. If they stole money, they have to pay back every penny, plus interest, but they also get a demotion to the position beneath them, and the one who was beneath them gets promoted into his or her place. No one”s allowed to harass said person for that though, because work place bullying gets special treatment. No, they then have to work their way back up to the position they lost due to their stupidity. As for work place bullying, they get docked one hundred dollars for every word of harassment that they give. I have cameras nearly everywhere, or listening devices where cameras would not be permitted. Every employee knows this, they had to sign documents saying that they understand this, yet at least once per year, I still get one or two doing it anyway.”
“How”d they not slam you for breach of privacy?” I asked curiously.
“I own the buildings, I can do whatever I want within reason to protect the entire population. The computers are always on the lookout for certain key words. They then flag me to a particular video or audio clip, and I watch and or listen to see what transpired. Oh, they fought it, and I had almost thirty people quit because of it, but, honestly, they were the people who I knew I was going to have the largest problems with anyway, so no big loss.”
“Nice. I like that you do things differently, and work to make everyone safe and happy.”
“Of course. My employees are amongst the happiest, I have amongst the highest employee retention, I don”t have part time employees, every employee from the lowest to the highest gets paid a fair and competitive wage, as well they all get profit sharing, so a good annual bonus when we do well. I never lay anyone off, I try my best to never fire anyone, I make sure and listen to their needs and wants, and do what I can to make my businesses the best places to be. My employees may not be the highest paid, but they get the best bonuses and benefits, again from the lowest to the highest, they all get fully paid medical and dental, stock options, retirement funds, they get the works. Even the janitors retire in comfort.”
“That”s good. So, what do you run then?”
“I have a legal firm with five offices, an accounting firm with four offices, an investing company with twelve offices all over the world, and a bank that has seventy branches now.”
“Wow, so, how many employees do you have then?”
“About eighteen hundred now I guess.”
“Yeah. So, anyway, what do you think of your new home?”
“It”s truly amazing. Like I said, it”s gonna take some time getting used to I think, but that”s something that I”m not against.” I said, and Sterling laughed.
“Good. Now, we needta go make lunch, I”m getting hungry, and you could use some good food. At least you”re not malnourished, you had caring parents who did all they could for you, but you”re still a little too skinny to be healthy. Granted, I don”t think you need to really add weight, just fill in more and add muscle, which we absolutely will do for you.”
“Okay. We always had food, just never so much as we all wanted. Dad says I”m probably starting puberty, which is the reason why I just can”t seem to get enough food, but there”s not really more to be had. I”ve grown a fair bit this past year, and it was already tough keeping me in clothes, but thankfully there”s a good thrift store near our house, and they always have lotsa clothes for cheap there for me. They”re just not always the nicest, but at least I was no richer nor poorer than anyone else around me, so I never got made fun of “cause my clothes were too small or mismatched.”
“Trust me, for all that, you are truly blessed, because, like you heard, I didn”t have even that much, and I”ve seen that even I was blessed, because there were those who had even less than I.”
“Which is truly sad.”
Sterling led us to the kitchen, and he had me help to make lunch, and we talked and laughed the entire time. When we sat down to eat, it was an amazing meal, and I finally feel full, and said so. We also had lots to drink, so that we can pee our diapers lots and lots, which is nice. I always have to be careful to not drink too much during the day, because if I have too much, then I have to go pee too often. I do not have a problem wetting my pants, my last daytime accident was when I was six, but I do have to go to the bathroom quite frequently the more I drink, I can hold for maybe an hour, but two if I only drink just enough to keep the thirst away. It is quite maddening, to tell the truth, and so, I have wanted to wear diapers just so that I could get enough to drink and not have to find a bathroom so often.
Trust me, in school, having a bladder the size of mine is a bad thing. There are ten bathrooms throughout the school, but six of them were closed up permanently due to damage, and they were never repaired. Thankfully the idiots of the school realized they could not vandalize any more bathrooms or we would all be forced to piss and shit our pants, because we doubted they would fix them even if we had none at all. So, with having so few bathrooms to service the nearly ten thousand kids we had, getting to use them was always a challenge. I know, it was not ten thousand, but trust me, when you are about to piss yourself, it sure as hell feels that way. It got to the point that boys would happily share two to a toilet or urinal when needed. Hell, I even once saw one boy taking a dump, while all the other toilets were already two deep, and another boy said he had no choice, and told the boy shitting to open bahçeşehir escort his legs, and he peed right between them as he was shitting. There were no doors on any of the stalls any more, so it was easily witnessed, and there was no shame in it. You do what you gotta do when you gotta pee. It was not even uncommon to see boys whip it out in the school yard and just piss wherever, because the bathrooms were always so crowded anyway. I cannot tell you how often I dreamed of wearing diapers to school. Hell, I bet half the kids there probably would have for that reason, not to mention the serious lack of cleanliness of the bathrooms, they were usually disgusting beyond compare.
Sterling said that he understood this well himself, because he had grown up in very much the same situation, and his school had not been any better. It is really nice that I have someone like Sterling now who does truly understand where I have come from, and look where he is now, so maybe, just maybe, I too can escape.
“Can we go for a walk outside and check it all out now, your gardens are beautiful, and I”ve never actually gotten to see a real garden before?” I asked once we were all cleaned up.
“Certainly, and we don”t haveta wear any clothes either, just slip on our shoes.”
“Okay.” I said happily.
We went and put our shoes on, and then Sterling led me outside. We had to have toured the entire yard for nearly two hours. I got to see so many amazing flowering plants, as well as more fruits and vegetables, I stopped and smelled almost every flower I could, I sat on a bench and just looked at one garden for at least ten minutes, I got to see so many beautiful birds and small animals, and even a few insects that I have never seen before. We don”t get hummingbirds, robins, bluejays, ladybugs, butterflies, squirrels, chipmunks, and rabbits in the city.
Normally all I see are pigeons, crows, rats, cockroaches, flies, and fleas. City wildlife, the ugliest of them all.
We even sat on a swinging bench overlooking the valley beneath us and the lake for easily ten or fifteen minutes, and I got to see some deer who were wandering through peacefully, they are truly beautiful animals. It is, by far, the most at peace and relaxed that I have ever felt in my life. Sterling tells me that he loves to come out here first thing in the morning in nothing but his super soggy night diaper, with a hot mug of tea, and just enjoy the beauty around him, and so, I of course tell him that that is exactly what I want tomorrow morning as well.
I am now getting really wet, not only did Sterling peepee my baby diaper well for me, but I have also wet it a fair bit myself now, and I am starting to get full. However, there is one thing far more full than my diaper, and that is my horniness tank, it is about to burst.
“Sterling, I know we said we”d wait “til tonight, but I need you now. I need you to take me to your bedroom and make hot gay baby diaper love to me. I needta finally feel what it feels like.”
“Are you sure Baby, as in absolutely, positively certain.”
“We don”t haveta do it so soon, if you need to hold off and learn to love me first, and stretch further, then I”ll happily wait. I”m still a little bigger round than the plug in your bum is, I”ll still hurt you I think. I don”t wanna hurt you.”
“I know, and I even know that it might hurt some, and I”m okay with that. I needta be sure about what I feel for you, and I want it sooner rather than later.”
“If you”re absolutely certain then Baby.” Sterling said, standing from the swinging bench we are still sitting on, and putting out his hand for me to take.
I clasped Sterling”s bigger hand in my little one, and we walked hand in hand to his bedroom, but maybe ours from now on. I know, that really, in a way I am still just an employee, but that is truly not what either of us want. I have wanted and needed what we are about to do for a shockingly long time, considering I am only ten. I would have happily allowed almost anyone to fuck me all the way back as young as Reilly, maybe even younger.
When we arrived, Sterling picked me up and laid me on the bed, then proceeded to remove my shoes, since we had both just put our shoes on our bare feet. He kicked his off as well before climbing onto the bed to join me.
Sterling then pressed his face into my soggy diaper, feeling not only the soggy mass, but my hot hard little gay baby erection buried inside. I am not huge by any stretch of the imagination, or asshole, maybe nine or nine and a half centimeters long, and probably only three or so around, I have tiny little balls still, and of course I am still hairless. I still have my foreskin, and it rarely ever retracts fully to expose my dick head. However, the amount of pain that I am in right now, I feel as if I just might be a little bigger than I normally am, and it feels like my foreskin might have fully retracted. It is super tight.
For easily two minutes Sterling mashes his face, and I can hear him breathing in, sniffing deeply of my scent. My god, I have never experienced anything so amazing in my life. And I am about to cum.
At least I do not have any actual cum to waste, so as soon as I can no longer hold off, I let go, and explode in another massive orgasm.
As soon as I come down, Sterling pulls down the front of my soggy baby diaper, inhales my entire package, and starts really making me feel like a god. Until this very morning, I had never been sucked, and it was fantastic then, it is more so now. Sterling then reaches inside the back of my diaper, grasps hold of the butt plug still lodged firmly inside me, and starts pulling it out, and as soon as he meets resistance, he lets it slip back inside me. He only has to do this four times before I let it go. Instead of pulling it out completely, though, Sterling then slips it right back inside me, and then proceeds to pretty much butt plug fuck me, well, I am totally not against that.
And then I came.
Sterling did not stop though, he just kept right on going, and I know the reason why. He says that he is still larger than the plug, and I believe him, and I also believe that he needs to loosen and relax me even more. I have still not seen him naked, and I am perfectly okay with that. I lasted maybe five more minutes like that, before I came again, and as soon as I do, Sterling slips the plug back in fully, but then removes his hand, and starts poking the hole in the back of my diaper like he knows I want. We had talked about this in great detail. We both want to make full diaper love, through both our soggy baby diapers, be filled as full as we can fill each other, and allow our already soggy diapers to catch what we cannot keep hold of.
As soon as Sterling has my diaper prepared, he prepares his own, but I still cannot see him, and then he lifts me up and moves me, lays me on my side, and then crawls in behind me. He whispers into my ear tenderly, “Are you ready, are you certain?”
“Yes.” Is all I whisper back to him.
Sterling then reaches back inside my diaper, pulls out my plug, and I give it up very willingly, and almost as soon as it is out of the way, Sterling slips his erection inside my diaper, and presses it to my hole. We are laying on our left sides, his left arm is underneath me, holding me softly, tenderly, lovingly, his right is guiding his dick where it belongs.
The intense heat from his dick seers my hole as it kisses it deeply, and with just a tiny nudge, his head slips inside me. As soon as he has the head of his dick inside me, Sterling releases his hold, and wraps his right arm around me now, and holds me even more tenderly, he is hugging me as he enters me.
Already I can feel the tears coming down, I am not in pain, well, really, it does hurt, a little, but, it feels far more loving already.
As soon as Sterling feels that I have relaxed enough, because the pressure on his dick head must have been intense if it feels this tight to me, he starts slipping even more inside. I tried not to hiss as the pain increased, and the tears came down more, this time as much in pain as in love, and Sterling just kissed my ear and whispered once again, asking if I am sure that I want to continue. I whisper back yes, but to just take it nice and slow, which he replies that he will go as slow as I need.
Sterling does not stop kissing my ear and my neck, and the feel of that almost makes the pain disappear, never before have I felt anything so loving. My parents love me, I know that, they have hugged and kissed me every day of my life, but, until this moment, I do not think I truly understood love.
No, love is willingly giving yourself up to the pain, while your man goes as slow as he possibly can, holding you, kissing you, whispering to you how special you are. I can feel Sterling”s tears dripping onto me every bit as mine are dripping down. Likely this is almost as painful to him as it is to me, I am that tight still, but, it is more than just the pain. We are giving to each other something that neither of us has ever experienced. I am not really sure how to explain how I feel. Of course there is pain, it is quite intense, yet there is so much more than just the pain. It feels like we are fully connecting, and though we both know that Sterling is hurting me, instead of driving us apart, it is binding us together far more than anything could.
At almost five minutes in, Sterling is still not even fully inside me, I cannot feel our diapers pressed together yet, but I know that he is getting close. Every thirty or so seconds, Sterling will slip just a tiny bit more inside me, and each and every time, I hiss or moan deeply, sometimes both. I am no longer even hard inside my soggy diaper, yet my horniness is still shockingly high.
The last two minutes of insertion felt the longest though, and caused the most amount of pain. Not only is Sterling considerably larger around than anything I have experienced before, but he is also far longer too. Finally though, Sterling slips all the way inside, and our diapers are pressed together the way I have dreamed of for a very long time. The tears are still rolling down, from both of us, Sterling is holding me even tighter, and I even have my arms wrapped around his, holding him to me. At times the amount I gripped his forearms, I am sure that had to hurt as well, yet he never made a sound, other than his soft tender whisperings into my ear.
“You did it Baby, you took me all in. How does it feel?” He whispered.
“Very full, very good, very painful.”
“Yeah, I know how you feel Baby. I went as slow as I possibly could to allow you to take me far more gently than I was for my first time.”
“I know. It hurts, but it also feels amazing, and I love you for allowing me to work into it slowly, instead of just slamming it all in.”
“I could never do that to a virgin, hell, I couldn”t even do that to a seasoned slut.”
“Thanks.” I whispered as softly as we still are.
“May I start now Baby?”
And so, Sterling starts pulling out, but after at most a centimeter, he slips right back inside, and pauses. He pauses for maybe ten seconds, and then does it again. He does this for about a minute, and every time he does, I make a deep groaning sound from within, it still hurts, but my god, it hurts so good.
Then he starts pulling out about two centimeters, and then slipping back in and pausing, only this time he pauses for just a couple seconds longer, before doing it all over again.
For another couple minutes, Sterling keeps up this pace, still holding me tight, whispering to me how amazing it feels, well, it is starting to feel even more amazing to me. I am finally starting to loosen up, to relax to the very much desired intruder. My groans of discomfort are slowly morphing into moans of pleasure.
I am now finally starting to get hard once again, I can feel that I am getting nearly as big and hard as I had been when we started, and I am starting to truly feel good. The tears are still pouring down, do not get me wrong, now they are no longer tears of pain. Sure, there is still some discomfort there, I am not exactly big, and Sterling is certainly nowhere near small, yet, I not only took him, but I want to take him over and over again.
Almost two minutes later again, and Sterling is now pulling almost half way out, before slipping back in, and pausing as he gets as far inside me as he can, only now he is also grinding his hips a little, doing things with his dick inside me that I had no idea were even possible. I am now getting shockingly close to cumming, and neither one of us has touched my diapered dick, but that too is what we both wanted, we wanted very much to try making love and letting the other cum from just anal stimulation. Neither of us were even certain it was possible, but we both wanted to try. Well, one more minute later, and we not only found out it is possible, but amazing as well.
Deep in the back of my mind, as I was cumming, I heard Sterling groan, and say fuck me, and then I felt him explode in me as well. It took almost two minutes for me to come down, and when I did, the tears started coming down even more. I feel Sterling filling me up so much, his cum is making me amazingly sloppy, and I am now fully relaxed, like I never imagined that I could be before.
Sterling is now going full in and full out, pulling his dick fully out of my wanting little gay baby bum, before slipping all back in, yet he is going every bit as slow as he has been all along.
“Oh my god Baby, that was amazing.” I whisper as soon as I am down fully.
“Oh yeah, you gripped and pulsed on my dick so hard I thought you were gonna rip it off, but it was so amazingly intense, that it caused me to cum harder than I”ve ever cum before. You should be able to taste it, in fact, it felt so much.”
“Nope, not yet, but soon I will taste your cream. Do you haveta go peepee Baby, “cause you know I want it deep inside me too.”
“Oh yeah, I knew how much you wanted to feel it, so I”ve been holding it back so that you could truly enjoy it.”
“Then fill me up please Baby.”
Sterling pushed all the way back inside me, paused, concentrated to pee, and then proceeded to fill me up fully. I have no idea how or why I would have dreamed of this so much, but I always have, for about as long as I can remember in fact, and finally feeling it, a whole new round of tears escape. Tears of immense joy and pleasure are pouring out of me. I am not even sure how I can have more tears to offer up, but I do, and so too it seems does Sterling, because I can still feel him crying.
As soon as he finished peeing inside me, Sterling started making sloppy cum and piss love to my gay baby diapered bum, and pleasure the likes of which should not exist exploded throughout me. Knowing who and what you are, and finally getting to feel who and what you are, are so very different. I had known I was a gay baby boy diaper lover before, had known that I needed to be fucked and filled full of cum and piss, and then be piss fucked until my fucker could not fuck any more. Feeling it, however, is so much more everything than I ever dreamed was possible.
For almost five minutes more, Sterling made gay baby diaper cum and piss love to me, and this time it was he that came first, but almost as soon as I felt him explode, so too did I. It was absolutely amazing.
Still Sterling did not stop. In our emails to each other, Sterling once admitted that he could almost always go for three cums in a row, but, on occasion, he could force a fourth out as well. Fuck, I sure hope that he does so now.
Almost ten minutes later, and still Sterling is holding me, whispering to me, making the most tender love to me, we came again. Sadly, though, that was it. Sterling started going soft inside me before we even came down. We stopped all movement, other than his kissing my ear and neck still, and just stayed with him as deep inside me as he could be, I am holding onto him for dear life, he is holding onto me for dear life. Almost five minutes later, Sterling shrank down enough, and I expelled him. We both sighed in deep love.
As soon as Sterling slipped out of me, I rolled over, Sterling only letting go of me just enough to allow me to turn around and face him. As soon as I was, we hugged each other again, and I kissed my man as deeply and tenderly as I possibly could. I have no idea what I am doing, but it does not feel that Sterling does either, and it seems that together we are learning the arts of kissing.
For damn near ten minutes we laid there, kissing each other, it was so much better than I dreamed it could be. We both have tears pouring down once again. Finally I broke the kiss.
“We both need ruined soggy baby bum changes, and I”d love for you to slip a bigger plug inside my gay baby bum please.”
“Okay Baby, and would you finally liketa try being triple diapered?”
“Oh yeah.” I moaned.
“Good, then we”ll each get triple diapered Baby, and you can slip my plug inside me as well.”
“Goody.” I said happily.
Sterling let me go and slipped out of bed to grab all the supplies that we are wanting and needing, and already I miss being held by him. He was back only a minute or two later with a large load of supplies, and I moved myself into position for a very good soggy baby bum change.
Sterling pulled the tapes on my diaper, pulled it down, and then cleaned me up with a baby wipe. As he did so, he happily proclaimed that I am not bleeding, so I did not tear, though he does inform me that I am very well bruised, but that he has really good bruise cream to help me with that. He puts a lot of bruise cream on me, then more onto the plug, so he will use that as both lube and medication, and then asks if I am sure, because it will likely hurt, probably a lot, and I nod happily.
Slowly and as gently as he can, Sterling slips the entire thing inside me, and as the widest part opens me up, I hiss, and then it slips all in, and I sigh. He then proceeded to take one diaper, poked hundreds of holes in it, put that onto me, and then prepared my other even bigger and thicker diaper by putting a gloriously thick diaper doubler into it, and then proceeded to put that onto me as well. As soon as it was all taped up, he had me get up onto my knees, and then he proceeded to tape it on real well with some good sturdy packing tape.
“Mmmm, now that”s nice.” I sigh once he is done.
“Oh yeah, and you look especially hot like this as well.” Sterling sighed.
“Thanks, now it”s your turn, lay down Baby.”
Sterling took my previous position, and I have to admit, seeing him laying there with his soft dick poked out the front of his sexy soggy baby diaper like it is, is really fucking hot. I pulled the tapes, pulled his diaper down, and exposed all that he has to me for the first time, and it is spectacular. Since he is soft, I cannot tell how big he truly is yet, but his balls are huge, and hairless, though so is his pubis. I gently clean him up with some wipes, then lotion and cream him really well, making sure to lotion and cream his baby bum hole well enough to slip his plug inside him, and as soon as I am sure that he is ready for it, I slip it inside him, and he sighs deeply as it slips in. It is not a huge plug, but still probably close to twice the size as mine is over all, but he assures me that his largest might frighten me, but that he enjoys it on occasion, yet he cannot wear it for long. This one, he claims, he can wear all day easily.
I prepared Sterling”s inner diaper by poking hundreds of holes in it, and then taping it onto him, and then prepare his outer diaper with a nice big doubler, and tape that onto him as well. Finally I get him to kneel, and I proceed to ensure that his diaper will not easily come off with the packing tape.
“Ah, much better, thanks so much Baby.” He says happily as soon as I have him properly diapered.
“And thank you. That was, without a doubt, by far, the most amazing thing that I”ve ever experienced in my life. Being made love to so slowly and tenderly, then getting diapered so wonderfully, I really do think I love you, and I hope that that”s exactly what I”m feeling, because I never want it to end.” I said, though, once more, I am failing at finding the words to truly describe how I feel at this moment.
“I”m glad that”s how you feel Baby, because that”s exactly how I feel as well. I can”t wait “til tomorrow morning when I get to feel you make gay baby diaper love to me as well now.”
“Do you think we”ll be able to, I”m still kinda tiny.”
“I think we”ll manage just fine, but I don”t think you”re tiny, I think you”re right where you should be for your age. However, with that being said, there”s an old rumour that says that if you get your dick sucked, a lot, that it”ll make it grow more. It”s not a medically proven fact, or anything, but hey, if you”re willing to try it, I”d be more than willing to try as well.” He grinned brightly to me.
“Ooh, a medical experiment, I think I could get behind that one. We thinking, one, two, three, or ten times a day that we”ll haveta do it?”
“At least twice, but more couldn”t possibly hurt either.”
“Mmmm, now that sounds nice. We should use you as a control sample though, if it works for me, then it might work for you too, so we”ll haveta test out that theory.”
“I like how you think.” Sterling smiled even brighter still.
“Mmmm, goody. I think I”m gonna really like living here.”
“And I”m definitely gonna love having you living here too. It gets kinda lonely around here all by myself sometimes.”
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