Cougar Pegging Party Ch. 02

Temmuz 20, 2022 0 Yazar: admin

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Authors Note:

*This story is a sequel to the story “Cougar Pegging Party.” It uses characters and ideas set up in the previous story, but should be enjoyable on its own as well. Thank you for reading.*

It was a beautiful summer morning at about 10 am when I heard my phone chime with a text sound that I only had set as a notification for alerts coming from a few specific and notable contacts. I immediately perked up, responding like a Pavlovian dog who’s bell had just been rung to let them know it was time for dinner. At this point, a couple of months had past since the debauchery-filled night where I had fallen victim to the five commanding women who had tied me up and systematically dominated my virgin ass with a variety of sex toys, so I guess I should fill you in on how things developed following the event.

Although I was essentially tricked, overpowered, and had my body forcefully violated in a variety of filthy ways, I can’t deny that the night I went to help Denise out with her sales party had awoken something in me and that I wouldn’t change a thing about how it had gone if I had the chance. My intense introduction to femdom and pegging was extremely arousing to me and to my delight, none of the women had any intention of letting up after turning me into their play thing that night. You might think that juggling the sexual demands of 5 women would be next to impossible, but they made sure that everyone was getting to make use of my body evenly and regularly, and thanks to Denise being able to supply next to any imaginable toy or piece if equipment, all of them were getting to basically try out anything they were interested in on me.

I had already had a huge variety if different instruments used on me and was starting to learn each woman’s kinks/fetishes and how to best please them individually or in different combinations. There was a lot of variety between them (with me even sometimes getting to fuck some of them in a more traditional manner from time to time), but all were fairly interested in femdom domination on a fairly regular basis.

To make sure that I was available and ready to go at any of their beckoned calls, Wendy had put together a shared calendar where they could all block out times that I would be of service to them to avoid conflicts. It would also send me reminders as to not miss a scheduled appointment and gave the ladies an option to leave me detailed instructions for any preparations they might want me to take into account, such as wearing special outfits or making sure my asshole was ready for toys of different sizes. I was available for them at pretty much any time as well because of it being summer break from school as well as all five of the moms pooling money together to give me an allowance each month, meaning I could dedicate all my time to my new job and not have to worry about another source of income. Wendy had even helped me organize my school schedule to take a gap year following summer break so I could really be dedicated. For an entire 12 months, I would be on call to fulfill the sexual desires of 5 separate, stunning milfs at a moments notice, and I was very excited for what might be coming.

My phone went off, reminding me that I had a pre-scheduled service visit that was going to occur that evening. Even so, I didn’t really need the notification to remind me that morning, as I had already been following the given directions for preparation for some time. A couple weeks ago, I was looking at my calendar to get my plans ready for the week and saw that Denise (the mother of my childhood best friend and the woman who was supplying all the other moms with all the sex toys they were using on me) had reserved me for the evening ahead of time and left limited, but also very specific, instructions for the event. All that I knew was that I was going to have dinner with her and her husband, Josh, before he had to leave for my friend’s soccer game and that neither me or any of the other women were to use my asshole in any way for a week leading up to that night excluding a single small butt plug.

I was looking forward to getting to see my friend’s dad, as despite seeing Denise very frequently following my initiation as her and her friends play thing a few months back, I had not seen him in a while. We had always gotten along well and he was very personable and fun to joke around with. I was also confident that he didn’t know the things his wife and the others did with me, as it was important to all of them that it stayed as our little secret. At that point, the only people that knew were me, the 5 women who had shared me that first night, and my step mother who had apparently initiated the whole event. The other note, however, spurred my curiosity. Up until then, it was rare that I would go more than a day or two without at least one of the ladies ravaging my backside in one way or another. It probably should have been obvious to me, but I continued on without realizing that someone big was coming.

To kaçak iddaa be completely honest, following the instructions for that week proved surprisingly more difficult than I would have thought it to be. Since my awakening, I had come to really enjoy being on the receiving end of anal play. I didn’t need to do it much with how busy I was with others, but on the couple of occasions where I found myself masturbating on my own, I had been using larger toys I was given by Denise and the others to feel my hole stretched and probed. Not being able to experience that feeling for an entire week had my mind almost exclusively focused on it at all hours. Whether I was, shopping, relaxing at home, or out doing something else, something or someone fucking my ass was always in my thoughts. I had to actively make an effort for my fingers not to wander southward when jerking off, and I even found it a little difficult to maintain an erection without my prostate being more stimulated. The small toy that was allowed helped a bit, but it was barely and inch diameter and it had trouble even staying in for the first day until my sphincter had a bit of a break and start to return to its original state.

That evening, I pulled up to Denise’s house once again and noticed a text from her that had come in while I was driving over.

“After you come in, check the top right drawer in the bathroom.” – Denise

As I walked up to the door, I could feel my ass start to twitch around the small plug, which had a much tighter fit now, with anticipation. I guess the week long stretch of not being used was getting to me, and I had to remind myself that I had to make it through dinner at the very least before anything too spicy would happen. After knocking on the door and waiting a few moments, I was greeted by the sight of Josh opening the door. Josh is about 6 feet tall with a little bit of an average, stocky dad-like build. He has black hair that is usually combed neatly to the side and almost always has a big grin on his face when talking to other people, always ready to crack a joke.

“Hey, Joey!” He said, “come on in, dinner is almost ready!”

He stuck his hand out to shake my hand while kind of pulling me through the doorway past him.

“Thanks, long time no see! I’ve been looking forward to this!” I said as I stepped inside.

As I looked around, Denise was standing in the kitchen over the counter while putting the finishing touches on one of the side dishes that we would be having for dinner, only a foot or so away from the stool that I had been tied to and fucked on not all that long ago. She smiled at me knowingly and gave the rest of my body a quick glance that would not be noticeable unless specifically watching for it.

“Hey Joseph! It’s good to see you! Ready to eat?” she asked, pretending as if we didn’t see each other frequently when everyone else was away from the house.

“Absolutely! I just need to run to the restroom real quick if that’s alright.” I said while giving Denise a subtle wink.

“Sure thing, you know the way. Don’t get lost on the way there!” Josh joked as he clapped me on the back.

I made my way down their hallway to the bathroom and locked the door behind me. Once inside, I squared up to the sink and my hand made its way to the top right drawer as I had been instructed. I slowly pulled it open, which revealed a wooden box with a paper note taped to the top of it. I opened the envelope and pulled the note from inside.

“Put this in and wear the panties under your jeans to dinner. ~D” it read in a fine cursive script I recognize as Denise’s hand writing.

I set down the note and picked up the wooden box, which was about the size of a small notebook and looked to have once been a jewelry box or something similar, and set it on the counter top. My hands trembled from my nerves and anticipation as they reached for the lid, my mind racing for what could be inside. As the lid was slowly lifted open, I got a good picture of two items in the bottom of the box, a tiny pink thong with frilly lace and an interesting looking sex toy that I wasn’t familiar with. The toy was a dark purple and looked to be some type of dildo with a flared base. The shaft was a mostly consistent diameter with the exception of the tip which widened into a teardrop shape and a section in the center that appeared to have accordion-like ridges to add texture to its length. It was fairly hefty and about 5 inches long and maybe 1 1/2 to 2 inches in girth. Not wanting to keep anyone waiting, I grabbed a bottle of lube from the same drawer that held the box, and pulled my pants and boxers off to get prepped.

I slathered the toy with lube and pulled the small plug out of my hole, leaving it quivering to be generously filled once again. As I began to press the tip of the dildo up to my sphincter, it became clear that the mandatory week-long break my ass had been given had resulted in more of an impact than I had realized. My body was not allowing kaçak bahis the toy to easily slip inside me, so even the lube and firm pressure were not gifting me with the sweet penetration I was craving. In response, I lifted one of my legs onto the bathroom sink and used my free hand to pull one of my cheeks aside, offering as direct of access as possible to the toy to my insides. With another firm push, I felt the toy’s bulbous head start to open up my backside and once it had cleared my rim, the rest of the toy slid into place to stretch the depths of my bowels. I then grabbed the thong and pulled it up onto my hips. It was surprisingly comfortable in the front despite not being designed to hold my manhood, while the g-string gripped between my cheeks, helping to hold the toy firmly in place. I would have been worried for the toys weight pulling itself out if it weren’t for the firm grip of my tightened ass and the pressure from the thong, but their teamwork was holding the base of the dildo firmly against my body. I felt my cock began to stiffen thanks to the stretching of my asshole finally returning, but I quickly reminded myself that Denise and Josh were waiting and pulled my pants back on. I quickly glanced in the mirror to see that my jeans hid the dildo and thong quite well before pulling the door open and making my way back to my hosts.

As I walked into the kitchen, Denise was starting to bring the food to the table, along with our plates, and Josh had already taken a seat with his back to the kitchen. I walked around the table and sat in the chair across from him, leaving the seat next to him for Denise once she was ready to sit down.

“I haven’t seen you in a while Josh,” I said as Denise put down the last bit of food and returned to the kitchen one last time for her drink, “how have things been?”

“Pretty good!” He responded, “the soccer team is killing it so far this year! We have been trying this new thing where…”

As he started an in-depth description of the team’s new strategy, Denise made her way back to us with her drink. She didn’t go right to her seat though. As she approached she pulled something from her pocket and held it up while right behind Josh’s chair, staying out of his view. A lust-filled smirk spread across her face as she showed off the item in her hand, a small purple remote with several buttons on it, and pressed one of the buttons while staring deep into my eyes. My eyes widened and I jumped, knocking my leg against the table, as a sudden pulse of vibration emanated from the toy, which was pressed firmly against my prostate in my sitting position.

“Whoah! Are you alright?” Josh asked concerned as Denise sat down in the chair next to him, sliding the remote under her leg to hid it.

“Oh yeah,” I said quickly “Just had a sudden leg cramp, sorry about that. Tell me more about the new plays.”

Josh continued on with his very in-depth description, but I was no longer processing anything he was saying. I felt my heart race as I realized what had happened. The toy Denise had left for me was some type of remote vibrators, meaning this dinner was going to be a lot more interesting than I had anticipated. As if having a dildo up my ass and wearing a thong wasn’t enough to hide at the dinner table, I was also going to have to control any outbursts caused by Denise’s control of the vibrations. As Josh rambled on and I collected my thoughts, Denise’s hand slipped under the table and I felt the rumble start up again deep inside me. This time it was a much lighter buzz, but after a minute it started to slowly increase in intensity. As it started to ramp up, Josh shifted the conversation and brought his attention back to me.

“Anyway, that’s going to keep our boy busy for the next few months. Do you have any specific plans for this summer?” He asked.

I wasn’t sure if I would be able to answer in a normal voice while my prostate was being stimulated by one of my mistresses, but I couldn’t just stay quite either. I took a short pause to gather my focus and responded.

” I actually decided to take a year off.” I said, “I got a new job recently and wanted to focus on that for a bit to make some money.”

My words came out surprisingly evenly and it seemed that Josh hadn’t caught on to anything being out of the ordinary.

“Oh! That’s great!” Josh responded, “Never a bad idea to start saving up. You better give it your all though. Even small jobs can look good with a solid letter of reference!”

“That’s true!” Denise piped up in response to that.

“I actually know his new bosses. They can be pretty intense, your going to have a Full Load this year.” She said slyly, licking her lips in satisfaction while watching me squirm.

“Well, don’t let them ride your ass too hard!” Josh laughed without realizing the true irony of his words.

At this point, the toys vibration had built up a fair amount and Denise noticed me shift a bit in my seat.

“Oh come now,” responded Denise, “Riding an illegal bahis employee can really help them reach their full potential.”

As she said this, Denise looked at me again smiling knowingly and gave a wink with here eye opposite the side of John. As she wink, another button was pressed and the whole situation stepped up to another level. I flinched as Denise and Josh laughed and I felt the toy move in a new way, separate from the building vibrations. The tip began shifting forward, moving deeper into a couple inches before moving back to its initial resting place. Apparently, it had multiple modes and was also capable of thrusting back and forth within me, the head now vibrating and massaging the lump situated deep in my ass. This almost brought me to climax right then, but I somehow controlled my urges, probably thanks to practice the last few months had offered being used by all the women. My thong grew noticeably tighter as my cock continued to stiffen, with its tip staring to poke out of the top and leak precum onto the fabric of my pants. John continued to drone on as I barely attempted to control my urge to let out passionate moans and send cum oozing into my clothes.

“Don’t you think?” John asked while looking at me, following up a question that I had completely missed in my distracted state.

“”Mmm hmmm” was all I managed to get out while the toy continued to drill into me, it’s vibration and rate of thrusting continuously growing as time continued on.

With the continued increase in intensity of the toys movements and stimulation, I wasn’t going to be able to last much longer before I gave myself up. Things were also only made worse with Denise staring at me with a suggestive stare, continuing to make subtle innuendos that threatened to give away my shame and suggestive gestures while continuing to adjust and ramp up the buttons on the remote hidden beneath the table. I’m sure that, like me, she was soaking wet as well, scheming up the many new and dirty escapades that I would be subjected to later in the night.

She continued to boost the speed and ferocity of the plugs pounding until I thought I couldn’t contain myself any longer. A loud and passionate moan began to build in my rump and travel into my gut towards my lips to escape, when against all odds, Josh finally looked down at his phone and noticed its clock.

“Oh, shoot! I’ve got to get going!” he said, “Sorry to run so quick, I’m going to be late for the practice. It’s been great catching up Joe!”

As he made this realization, Denise back up the on the controls just enough to to allow me a quick response.

“Yeah.” I managed quietly while giving a quick nod.

Josh didn’t seem to take any notice to my strained voice and was out the door quickly after standing up. Denise immediately pounced as soon as the door shut.

“Pull your pants off and get those legs up!” She commanded firmly.

I immediately obeyed, as the loyal servant I had become. Yanking my jeans off quickly by the ankles and slipped my posture down in the chair, allowing me to grab my ankles and present her with easy access to my bottom and the toy. My erect penis was sticking out of the waistband of my thong by about and inch, which was now also pushing even firmer onto the base of the mechanical stopper in this new position. She moved to me quickly, keeping one hand dedicated to the remotes buttons while the other reached forward towards my backside. She adjusted the toy to its maximum settings and used her free hand to begin quickly pressing on its base as well. This brought me over the top.

“Aaaaaaaah!” I moaned loudly as my cock erupted without any physical contact, launching my seed towards myself as I held my feet up in the air.

Having my legs up put me in a perfect position for the torrent of sperm to be delivered directly onto my face, with a large amount of it smearing itself across my tongue thanks to my mouth being wide open from my passionate exclamation. I had barely made it through, with my face being painted just as Josh’s car had barely made it out of the driveway.

“I’m impressed.” Denise said very casually as she reached up and shoveled the remaining sperm from my face directly into my mouth, “I didn’t think you were going to be able to hold it in!”

She smiled as I wrapped my lips around her finger, sucking them clean and swallowing the mess that I had made.

“Well then, we better get moving. We need to get you prepped for the rest of the nights activities.”

She quickly got me up and giddily lead me into her bedroom where there was an attached bath.

She quickly ordered me to get undressed and started to search for something in her closet. I obediently pulled off my shirt and dropped my pants. I kept the toy inserted in my ass, which was continued to pulse and thrust into my depths at a much more mellow rate now, and kept the thong helping to hold it in place on. As I neatly folded up the garments I had removed, Denise turned around to address me again, holding an outfit that she had pulled from the back of her closet.

“I put this together for you special for tonight.” She purred, “I just know you going to look stunning.”

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