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It was only ten when games night had begun to wind down. Everyone else had pled early start so by the time all the goodbyes were said Penny and I were the only two that remained.
I had known Penny for five years and had had a crush on her for at least three. In the last year we had become very close friends, most of our secrets out in the open, so the two of us hanging out wasn’t anything new.
Penny asked if I wanted another drink to which I replied an enthusiastic “Yes”. While Penny poured our drinks, I put some music on.
‘You up for another game?’ Penny asked, head in the fridge.
‘What the hell,’ I shrugged.
‘Any ideas?’ I asked.
‘How about a quick game of monopoly?’ Penny suggested, handing me a drink.
‘Sure, but you know there’s no such thing as a quick game of monopoly?’ I replied.
Pausing for a moment I added, ‘Isn’t this going to be kinda lame with just the two of us?’
‘Well, we can make it a little more interesting. We don’t have to play by ALL the rules.’ Penny said, ‘In fact, we could add a few of our own. Be back in a sec.’
And with that, Penny headed down the hall to her room and returned with the game.
‘Now, to make things a little pacier, I think we should start with three grand. Also, no restrictions on buying first time round and passing go pays five hundred for the first three rounds. Agreed?’ Penny peered up from counting out the money.
‘Sure,’ I confirmed.
Looking at the board I spotted the jail space.
‘What’s it cost to get out of jail?’ I asked.
‘A thousand,’ Penny said. ‘Oh, and “parking” is just parking. No money, okay?’
‘A grand huh?’ I pondered.
Penny just gave a casual shrug so I shrugged, collected my cash and sat down at the coffee table. We rolled to see who would kick off. Penny won in a landslide. Her first move landed her on “Chance”.
‘By the way, any monetary punishments are multiplied ten times,’ Penny said, as she turned over the card. ‘That applies for utilities and stations as well.’
Holding up the card, Penny read aloud, ‘Pay property tax of fifty dollars.’
‘Oh, she’s off to a good start,’ I quipped, rubbing my hands together.
Penny just paid the five hundred into the bank and said, ‘We’ve only just begun.’
‘Oh, one more thing,’ Penny said as she took a sip of her drink.
‘If you can’t pay the bank for any reason, the bank may seize a property for resale; no mortgaging to get out of debt. If the player wishes to keep the property, they may offer the banker an alternative payment as long as the banker agrees. I’ll be banker when you roll and you when I roll. OK?’
A little confused, I just nodded in agreement as I picked up the dice.
Ten minutes later, most of the properties had been snapped up, the extra cash making for real-estate boom. Each of us owned a set of properties with a few houses, along with a scattering of stations and a utility each.
For the next five minutes, Penny and I bantered and bartered, which earned me a set of railroads and Penny, a row of orange properties and both utilities. The haggling continued until I landed on the last property for sale.
‘What can I offer to stop you buying that property?’ Penny asked, intently.
She needed it to complete her last set and both of us were down to around a thousand dollars.
‘Well, it’s worth three hundred so I’ll leave it in play for six.’
‘Bit steep just to leave it,’ Penny countered, ‘I’ll give you two.’
‘Five,’ I said, without hesitation.
Penny was silent for a moment.
‘Tell you what, if you buy that property and give it to me…’ I began to protest, but Penny held up a hand. ‘Hear me out. I will, in return, flash my breasts for thirty seconds.’
I thought I had misheard, but Penny just looked at me waiting for an answer. In disbelief, I counted out the necessary three hundred, paid the bank and began handing the property to Penny.
‘Hold on,’ I paused and smiled wickedly. ‘I think I need a show of good faith.’
Penny, looking a little irritated, thought for a moment. Reaching behind her back, and under her t-shirt, she unhooked her bra. Wriggling beneath her t-shirt, Penny finished holding her bra out.
‘Will this suffice?’ she asked.
Grinning at each other we made our exchange. Smiling, Penny laid the card down completing her final set. Looking me in the eyes, she then stood up and, with a little hesitation, lifted her t-shirt. I had always admired Penny’s curves, but seeing them in the flesh was just incredible.
After what seemed like an eternity Penny lowered her t-shirt and asked, ‘Satisfied?’
As Penny sat back down, we could see each other’s excitement level climbing. Penny had a plan but I could only imagine what she had in mind this evening.
‘Very’ was all I said, contented.
It wasn’t long before Penny’s tactic had paid off. I was strapped for cash while Penny kept hounding me to sell her this or that. I had a mere fifty dollars in small change thanks to my previous turn. But when I thought I couldn’t be in a more kaçak iddaa desperate state, I hit a new low.
Go directly to jail. Do not pass go. Do not collect two hundred. Penny was bouncing in her seat as she moved my piece into the slammer.
Leaning forward, her elbows on the table, Penny began to speak, a little excitement in her voice.
‘So, I thought it would be fun to play some of the characters like “The Warden” or “The Prisoner”. Don’t you?’ Penny queried, as she set the piece down.
‘Sounds…interesting,’ I replied tentatively. ‘How would it work?’
‘I just figured we’d take on the roles as they happened,’ Penny replied.
I nodded in agreement.
‘Like right now, you’re in jail…’ she paused.
I tilted my head not quite following.
‘Which would make you “the prisoner”,’ Penny continued.
As the penny dropped, a sly grin spread across my face.
`So that would make you…’ I trailed off.
‘The Warden,’ she finished.
Penny, wearing a very wicked grin growled, ‘Prisoners need to be searched for weapons so…up against the wall!’
I laughed, ‘You serious?’
Penny, still wearing that huge grin, stood me up and faced me to the kitchen wall.
‘Spread ’em!’ Penny playfully commanded.
As I placed my hands on the wall, and parted my legs, I felt Penny’s hands. She was frisking me!
She started with my arms, then my neck and back, my chest and stomach, as she worked her way down.
As she patted down my pockets, Penny said, ‘Are you hiding anything?’
As I turned to look at her, she reached round and firmly grabbed my crotch.
‘Ah. No ma’am!’ I answered with a start.
I was now trying to hide my growing excitement at the turn of events.
‘I think you are,’ Penny said, in a playfully accusatory tone.
As I pretended to plead my innocence, Penny cried aloud, ‘Strip search!’
I turned to look at her again, but she just looked back expectantly.
‘Come on! Get those clothes off mister!’ she said, almost laughing as she spoke.
A minute later, I was standing in my undies facing the wall. Standing very close, Penny again reached round and grabbed hold of what was now a not so subtle hard-on.
‘So what’s this then?’ Penny questioned, in a suspicious tone.
I opened my mouth to answer, but stopped as her hand slid inside my waistband and began stroking my shaft. Penny continued on till she sensed I was on the verge.
It was at that moment she asked casually, ‘Are you hiding something from me?’
‘No ma’am,’ I replied in a whimper.
After a pause, Penny raised an eyebrow, stepped back and said, ‘I’ll believe you…this time. Put your clothes back on and let’s continue.’
Regaining my composure, a thought crossed my mind.
‘Penny, what would have happened if you didn’t believe me?’ I asked, as I handed her the dice.
Penny smiled and said in a sarcastic voice, ‘Well, I would have had to really search you, wouldn’t I?’
Taking a sip of her drink she added, ‘But don’t worry. I’d have been gentle.’
As we continued, Penny and I became acutely aware of each other whenever one of us was in the vicinity of the infamous corner. Penny had a narrow miss, but instead landed on my only set, giving me a much needed boost of cash. My roll landed me on “Community Chest”, but as I reached for a card, Penny touched my hand.
‘I have another idea,’ Penny said, in a very suggestive voice.
‘Ok,’ I replied, enthusiastically.
‘What do you have in mind?’
‘I always thought it would be fun to make up the “Chance” and “Community Chest” cards so… I have written down a few things.’
Penny paused for a moment to reach down into a backpack close by. From the backpack, Penny produced a small spiral bound notepad.
‘Fifty-two things in fact. One on each page.’
She sat forward a little more as she continued.
‘Now, each page corresponds to a card in a regular card deck. If we switch the two piles for a regular deck of cards, whenever we land on either “Chance” or “Community Chest” we could pick a up a card and look up the corresponding page in here.’ Penny finished, pointing to the notepad.
‘What do you think?’ she said, shifting in her chair excitedly, her eyes bright.
Without hesitation, I reaching out and picked up the two piles from the board.
‘I’m guessing you have a deck?’ I asked, as I packed away the no longer required elements.
Penny grinned and pulled a deck of cards from the bag. As she shuffled, I became very curious as to the contents of the notepad.
‘Can I see this list?’ I asked, with the saccharine of a girl scout selling cookies.
‘No. I’ll do the looking up, but I will show you what’s written,’ she answered with finality.
Nodding, a sly grin on my face, I pick up the top one.
‘Three of clubs,’ I said holding up the card.
Penny opened the note pad and hunted for a moment.
Clearing her throat she said, ‘You are a lone shark. The player to your left owes you two grand and you have come to collect. kaçak bahis If the player has insufficient funds, they may offer you an item of clothing to make up the difference. No clothes to offer. YOU may make THEM an offer that might interest you. Any offer will be considered.’
As Penny finished counting she inhaled sharply.
‘I have fifteen hundred,’ she said looking back up at me with a twinkle in her eye.
Holding out my hand, Penny handed over the money.
‘And the balance?’ I asked.
Penny stood up, walked over and stopped a few foot from my side. Facing me, she slowly loosened her pants and then let them fall to the floor. Penny was wearing a plain pair of white undies. Stepping out of her pants, she picked them up, handed them over and returned to where she was sitting.
The next few rolls were unbearable. Both Penny and I couldn’t sit still. We taunted each other, as we moved our pieces round the board. Neither of us paid any attention to the money, our focus was on the dice.
It was Penny’s turn, and as the dice came to a stop, we both sat in silence. Penny moved her piece around the corner, placing it on “Chance”. I couldn’t believe how nervous I was as Penny leaned forward and picked up a card from the deck.
It was the ten of hearts. Flicking through her notepad again, Penny found the page and began recited what was written.
‘You have decided to pursue a career in exotic dancing,’ she read. ‘Offer your skills to the player to your right for the price of five hundred dollars. If they accept, take the cash, strip to your birthday suit and get to work. Your performance will last for one song of your choice.’ She showed me the page as she finished.
I couldn’t stop smiling as Penny stood, eyes trained on mine.
‘Would you like a dance?’ Penny asked, in a sexy voice, as she began moving closer.
‘Sure,’ I said, feeling more than a little dirty, but in a good way.
Clearing my throat I asked, ‘How much?’
‘Only five BIG ones.’ Penny said, now straddling my left thigh, her knee pressing into my groin.
Picking up a five hundred dollar bill, I gingerly slipped it in her waist band and said, ‘Please, dance for me.’
Penny rose and walked to her computer. A moment later, an appropriately sexy song was pumping out the stereo’s speakers.
Penny was fantastic. Her moves were both graceful yet enticing, as she slowly shed her t-shirt. As she wiggled out of her undies my heart was pounding. Penny was completely hairless. Noticing where my attention was, Penny smiled a sexy little smile and danced over to my chair.
Facing away, Penny lay on my lap resting her head on my shoulder and draping her arm around my neck. As she ground herself into my groin, I felt her clasp my hand and lift it to her stomach.
I was in heaven. Penny ran my hand across her midsection and down her thigh, avoiding contact above or below. As the music finished, Penny stood back up, turned round and gave me a kiss on the cheek.
I was breathing hard and my mind was racing. Penny had just given me a lap dance. Only fifteen minutes earlier she had had her hands where I had only dreamt. What was next?
‘Hey!’ Penny said, snapping me out of my trance. She was dressed and sitting ready.
‘Your turn,’ she said, sounding a little impatient.
We played on. The tension was incredible. Both of us narrowly avoided what seemed to me to be multiplying hot spots. But then I became a repeat offender, landing again on the infamous “Go to jail.”
‘Wooohooo!’ Penny whooped, while doing a little victory dance.
I groaned, playing the victim, as I got up. This time Penny grabbed my arm and led me to the wall. She placed my hands in position and kicked my legs further apart.
‘I’m only going to ask you once,’ Penny said, forgoing the pat down.
‘What?’ I replied, innocently.
‘Where is it?’ she repeated, looking at me with a wicked grin.
‘You know I WILL find it?’ her question sounding more like statement.
‘I don’t know what you’re talking about,’ I said, trying to sound casual, even though my heart was trying to explode out of my chest.
‘I guess that’s it then,’ Penny said, speaking in her low, sexy voice.
Turning my head, I looked at Penny. Both of us were breathing hard, our skin glistening. Penny walked to the kitchen sink and began washing her hands.
‘You’re leaving me no choice but to conduct a full body search,’ she said, matter of fact, as she walked to the kitchen sink and began washing her hands. After drying them, she returned to my side.
‘Do you see that over there?’ nodding in the direction of the table.
I hadn’t notice, but Penny had placed something on the dining table. I immediately went rock hard as my gaze fixed on that something; a tube of lube. I looked back to see Penny’s smile growing a little nervous as my expression registered just what she was suggesting.
In the past, Penny and I had talked about, among other things, sex. One drunken evening, Penny had managed, through shear persistence, to get me to confess I had a illegal bahis thing for anal sex. I had explained that I didn’t have much experience, but it was what I fantasized about most.
I recalled at that moment Penny’s reaction to my admission was a raised eyebrows, and a knowing smile.
‘I guess you have a job to do,’ I said, a huge grin letting Penny know I was up for whatever she had in mind. Penny visibly relaxed, relieved at my response.
Her nervousness completely gone, Penny picked up the tube and held it up.
‘This is your last chance. Where is it?’ she threatened, grinning wildly.
Knowing Penny was making sure I wanted to go through with this I replied, ‘Search me officer.’
‘I would ask that you remove your clothes,’ she said.
A moment later I stood facing the wall wearing only my undies. Penny pulled at my waistband.
‘I meant all your clothes, as in you…naked,’ she said, in stern voice.
Penny was transfixed, staring at my hard-on, as I removed my undies and tossed them aside. Flicking open the tube, she squeezed a large dollop of lube onto her finger.
‘Now, if you relax things will go much more smoothly for you,’ Penny said, in a soothing tone, as she disappeared from view.
A moment later, I felt her hand caressing my cheeks. As Penny gently gripped my left cheek, she slowly pulled them apart, leaving me feeling very exposed.
Satisfied both of us were ready, she cooed again, ‘Just relax.’
Delicately, Penny ran her finger from deep between my legs, passing all the way up between my spread cheeks, returning to rest the tip of her finger over my opening. She began circling her finger, gently stretching my opening in all directions.
Penny must have been kneeling as I could feel her breathing. A minute later, I felt a little pressure as her finger tried to enter. As my ring gave way, I closed my eyes and let out a quiet sigh.
Gently, but firmly, Penny began working her finger deeper inside my rectum. Periodically, she would pause to apply another generous amount of lube to her finger, and then resume her pace.
‘How does that feel?’ Penny asked a little concern in her voice.
‘It feels…good,’ I said honestly. ‘Really good.’
Hearing my answer, Penny removed her finger again. There was long pause. Thinking that my time might be served, I began opening my eyes when I felt Penny return.
A moment later, my ring again surrendered to her advances, but something was different. An instant later I knew Penny had added another finger. My resulting moan gave Penny the license she needed, as she drove her fingers in as far in as she could.
It didn’t take Penny long before she had established a rhythm of slow, very deep strokes. Opening my eyes, I became aware that Penny had moved into view. She was kneeling with her legs parted slightly. Needing only one hand to continue her “interrogation”, Penny now had her other beneath her undies; her fingers moving in unison with each thrust I felt.
‘Still okay?’ Penny asked sounding more curious than concerned.
‘Mmm hmm,’ I answered, suddenly feeling a little embarrassed at how much I was displaying my enjoyment.
‘Shall I continue my search?’ Penny asked, that nervous little smile returning, but her eyes were burning.
Breathing heavily, I smiled from ear to ear. I knew what she was asking.
‘I think you might have to widen your search and probe a little deeper,’ I replied, looking Penny straight in the eyes.
‘Well, you had better climb up on this examination table,’ Penny said.
I climbed up on to the dining table and knelt on all fours. Not satisfied, Penny moved my knees further and further apart until I was completely exposed.
‘That’s much better,’ Penny said, in a reassuring voice, as she reapplied lube to her fingers.
‘Remember, just relax.’ she reminded.
As before, I felt Penny spreading my cheeks and the cool sensation of her lubed fingers as they re-entered. Penny drove in and out for about a minute before she withdrew completely and gave my cheek a tender squeeze; a warning.
Penny slowly began pushing three fingers in a little. This time, I felt a twinge of pain; my ring straining to stretch wider. Penny paused, watching me intently.
The pain subsiding, I gave a brief nod.
Penny responded by applying more pressure, moving a little deeper, then pausing to let me adjust. She continued this pattern until I felt her knuckles rested against my cheeks.
Looking back, I saw Penny was staring, a smile plastered to her face.
‘This is amazing. I’ve never, ever done anything like this to anyone before,’ she said, slowly withdrawing her fingers and then sinking them back in.
Over and over, Penny drove in and out, her fingers soon moving, once again, unhindered. Feeling this, she began to stretch me even further, pushing out in all directions as well as rotating her fingers back and forth.
‘How does that feel?’ Penny asked.
‘Really….fucking good,’ was I could stammer, as Penny drove back in.
Penny began to increase her pace. As she did, she also applied a little more pressure downward.
Suddenly, what had been a pleasurable tingle grew dramatically in intensity; Penny’s adjustment having its desired effect.
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