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 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. 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 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.
Within seconds, I felt an orgasm the likes I had never felt before building.
Not stopping, Penny had reached her other hand between my legs and had started to apply long, back-hand strokes to my straining erection. It was all I could take.
I exploded, groaning loudly as I came like never before. Cum spilled forth, splashing a little as it hit the table. Exhausted and breathing heavily, I turned my head to look at Penny. Her face openly beamed with an expression of immense pleasure and satisfaction.
‘I think I found what I was looking for,’ she said, sounding very please with herself.
‘Well, I can’t have all the fun,’ Penny said, as she picked up two towels, holding one out, as I gathered my composure.
‘I guess we should continue,’ she giggled.
Penny quickly mopped up while I dressed, leaving my pants behind. Bending to sit back down, my rear end felt very loose.
‘I feel like…such a little slut,’ I said, hanging my head.
Looking back up, I added, ‘And my ass feels like you could park a car in it.’
Penny covered her mouth, as she burst into laughter.
‘Awww, poor baby,’ she managed to say sarcastically between coughs.
‘Well, I thought it was the sexiest thing I have seen in ages,’ and with that, the last of our inhibitions were gone.
Pointing a finger at Penny I jokingly threatened, ‘I just can’t wait until the shoe is on the other foot.’
Penny just winked and said, ‘Well, just remember what awaits YOU the next time you wind up there.’
Stuck in jail, I watched as Penny played on; the sexual tension climbing with each roll.
On her third roll, I moved my piece into the “visitors” area. Turning my attention to the dice, I realized where Penny had landed; “Chance”. She picked up a card from the deck. This time it was the ace of spades. Checking the notepad Penny looked up.
‘No way,’ Penny said in disbelief.
‘What?’ I said. ‘Tell me!’
Penny turned the notepad around. In bold letters were the words “You have been busted for smuggling. Go directly to jail.”
‘Oh. Yeah. Ah, Miss. Kindly assume the position,’ I said calmly as I stood up.
Penny dutifully placed her hands on the wall and spread her feet wide apart. Using both hands, I started frisking her, quickly working my way round to her breasts.
Penny’s breasts felt amazing. As my hands passed over her erect nipples, Penny pushed back into my hard-on.
‘Trying to bribe an officer?’ I asked, my shaft sinking in further between her undie covered cheeks, as I continued “frisking”.
‘No I wasn’t officer,’ Penny said sounding so very innocent.
Removing my hands from her breasts, I stepped back. From behind, I reached down between her legs and I gently cupped Penny’s pussy making her jump a little.
The excitement had left her undies soaked. Her wetness seeped between my fingers.
‘Of course you weren’t,’ I said mockingly.
Giving Penny a little squeeze I asked accusingly, ‘What are YOU hiding?’
‘Nothing sir,’ Penny replied, whispering hoarsely.
Leaning in, my mouth touching her ear, I whispered, ‘I don’t believe you.’
Through her undies, I could feel Penny tense; her body beginning to tremble with anticipation.
‘Please remove all of your clothes and climb onto table,’ I said calmly.
Fighting a smile, Penny walked to the living room, picking up a cushion from the sofa, before arriving at the table.
‘I want to co-operate in any way I can officer,’ she said, replying in a submissive voice, as she quickly discarded her t-shirt and undies.
Penny hopped up on the table, but instead of kneeling, she laid down on her back; legs straight, arms by her sides, cushion beneath her head.
As I came to stand by Penny’s toes I gave her a questioning look.
‘I just assumed you would search me from top to bottom,’ she replied, with a sly grin.
Penny then gracefully drew her feet into her, splaying her legs wide, exposing herself fully.
I stared openly in awe at the sight that lay before me.
Seeing my pleasure, Penny opened her thighs even wider causing her lips to part, revealing her glistening inner lining. I could hear my heart pounding loudly as I took in the whole scene.
Penny cleared her throat loudly, spurring me back into action.
Tickling her toes, I asked, ‘So, where did you hide it?’
Penny, giggling, answered, ‘Search me.’
I began stroking her leg, slowly moving up her inner thigh. Reaching the top, I slid my hand beneath her cheeks and slowly drew a finger all the way up to her stomach. Placing my hand over her mound, I gently slid a finger in her pussy. Penny moaned softly as I began to fingering her.
Adding a second finger, Penny began moving her hips down to meet my strokes. In no time, the only resistance I could feel was Penny’s controlled clenches, as my fingers drove in and out.
Tapping Penny’s thigh, she looked at me questioningly.
‘Everything okay?’ I asked.
In response to my suggestion, Penny reached down and forced a third finger into her opening. She groaned with pleasure as my finger bottomed out deep within her. I stroked upward, trying to stimulate the elusive nerve endings of her g-spot.
Penny was rocking up and down on the table with each stroke. Her lips looked to be bursting at the seams, stretching to cope, but I felt little resistance.
Now writhing, Penny was close. Her whole body was involuntarily thrusting harder and harder, her back arching. Her breaths were becoming shorter and shorter.
All of a sudden she burst out, ‘Oh shit, I’m cumming! Don’t stop! Don’t stop!’
With that I felt her muscles contract sharply. Grabbing my hand, Penny forced my fingers obscenely deep inside her. She moaned loudly as I felt them stretch her insides. Penny slammed her legs together, trapping my hand in the process, as she rode out the last waves of pleasure that were sweeping over her.
Spreading her legs again, now relaxed, Penny smiled.
‘What was that were you saying again?’ she asked.
‘Oh, I was just saying that I think we can say I have searched you thoroughly,’ I said.
‘Well, I think you have exhausted one avenue of investigation…for now,’ Penny said, as she rose up on her hands. Then flipping over she finished, ‘But…I don’t think you have explored this one.’
A little amazed, I picked up the tube again. While I was preparing, Penny slid the cushion beneath her hips, as she waited patiently.
‘Perhaps, I might assist in a small way?’ Penny asked a moment later reaching back and pulling her cheeks apart.
‘Just to prove I am more than willing to help,’ she added.
Looking deep into Penny’s eyes, I became a little nervous. I had never done this to anyone before. Yes, I had pleasured myself in the past, extensively, but I had never had the opportunity to play around with someone else.
Sensing my apprehension, Penny smiled softly.
‘Hey, I have been looking forward to this ever since I had you up against the wall,’ she said in a reassuring tone.
‘Just take it nice and slow, and we’ll see how we go,’ she finished.
Hearing Penny’s words, I became instantly brighter. My excitement now growing, I slowly ran my finger between Penny’s cheeks, coating her opening as she had done mine. I gently began circling but Penny raised herself a little off the cushion indicating I should enter. Applying a little pressure, my finger sank in easily. I started slowly pumping Penny, the whole while Penny tilted her hips back in time.
Softly moaning, Penny whispered, ‘You can add another.’
Withdrawing, I applied more lube while Penny again held her cheeks wide. I felt my excitement climb as my eyes stared at Penny’s now slightly gaping opening.
Feeling the tips of my fingers at her anus again, Penny held her breath in anticipation. With a little push, the two fingers entered. Feeling little resistance, I still thought it best to pause just inside.
‘Keep going. I love the feeling of being stretched,’ Penny chimed.
I continued pushing in deeper, stopping only when I could go no further. Penny moaned, panting a little, but I could see she was wearing a satisfied smile. Pausing for a moment, I slowly withdrew. No sooner had my finger popped out, than I pushed it back in, stretching her open again.
As I continued, Penny moaned louder with each stroke. It was amazing how effortlessly my fingers slipped in and out. Not sure how far this adventure would be going I touched Penny’s hand.
‘So, do you think I will find anything if I continue my search?’ I asked, in the vein of our game.
Penny’s smile spread even further. She wriggled her toes and replied, ‘I don’t think you have really begun to get to the bottom of this.’
She then pulled herself up onto her elbows and knees and, sounding like there was no other option, said, ‘I guess you will just keep on searching until we find something.’
Taking the hint, I leveled three fingers at Penny’s entrance. Feeling my touch Penny nodded indicating she was ready. For the first time, my fingers met resistance as they pried her open once again.
Penny inhaled sharply as an involuntary spasm forced her to clench tightly. I stopped. She was breathing hard for the first time, the strain showing. Gradually, her breathing slowed and her face relaxed.
‘Okay?’ I asked.
‘I’m okay,’ she said taking in slow, deep breaths. ‘You can keep going.’
I resumed, my fingers gradually disappearing inside Penny. It took roughly a minute before my fingers could go no further. I rested, my fingers buried deep with her. Slowly I reversed, backing all the way out before placing my tips back at the opening and pushing back in.
To help herself relax, Penny had begun playing with herself, her fingers dancing between her lips.
A few minutes passed and Penny had began pushing back, driving my fingers deeper. Her speed increased, as her fingers moved faster between her legs.
‘I’m so close. I’m close,’ was all she kept repeating then it happened.
Penny’s whole body tensed. I felt contraction after contraction around my fingers as Penny, finally taking a breath, let out a series of yelps. It was intense to watch. Penny’s was obviously rocked to the core, collapsing on the table not moving. I withdrew my fingers as Penny shuddered a little.
‘Oh my god,’ she repeated over and over, her eyes shut tightly. She was in her own world.
Calming, Penny opened her eyes, ‘That was fantastic!’
‘It was so intense. I almost past out!’ she said in disbelief.
‘That was definitely the most intense thing I’ve ever witnessed,’ I said truthfully.
Penny climbed off the table and shook herself a little. She collected her clothes, gradually got dressed before sitting back down.
We were quiet for what seemed like an eternity. Penny just beamed at me. She looked tired yet so content.
‘I don’t think you’ll survive another examination,’ I said testing the waters, hoping that games night wasn’t officially coming to an end.
‘Oh, I think I could surprise you,’ she sneered back. ‘I have a feeling you’re not the only repeat offender.’
With that, Penny tossed the dice at me.
Now it was my turn to roam the board, Penny sitting on the sidelines. First roll, I landed on one of Penny’s properties, however being in jail, I didn’t have to pay. My second roll landed me five spaces shy of jail-time.
‘Come on number five,’ Penny said, watching the board anxiously.
I rolled and breezed past, landing again on one of Penny’s hotels. She swore, knowing that some cash might come in handy.
Penny now picked up the dice and rolled. Her piece came to rest safely on her own space to which Penny exaggerated a motion of relief.
I rolled doubles and move to “GO”. Rolling again and wouldn’t you know it, I was back on “Chance”. I picked up a card and held it in front of my face.
‘Let me see Penny,’ complained, notepad at the ready. ‘I want to see what’s in the cards.’
I dropped the card on the board. It was a joker.
‘That wasn’t meant to be in the deck, but I guess it could be…um…a role reversal card. You know? You can use it to trade places if, say, you find yourself in jail,’ Penny suggested, pausing before adding, `If you really wanted?’
‘Guess I’ll have to decide next time,’ I said, raising my eyebrow.
‘Won’t that be interesting?’ Penny replied, as I watched her eyes flash wild.
Penny rolled and this time, she landed on “Community Chest”. She quickly picked up a card and held it aloft. Nine of diamonds. Searching the notepad, Penny became very excited.
‘You are a hypnotist. Using your skill, hypnotize the player to your left by counting to ten. When you reach ten, the player will close their eyes. You may then ask the player to either answer any three questions, or perform any act you wish. The player must comply. Finish by counting to three and snapping your fingers.’
Penny was doing her victory dance again as she finished reading.
‘Oh, I am going to have fun with this,’ Penny rubbed her hands together.
Sitting on the coffee table, she began counting. Upon reaching ten, I closed my eyes wondering what I was in for.
‘I have some questions that I want answered truthfully,’ Penny said.
I nodded that I understood.
‘Do you think I’m attractive?’ she asked playfully.
‘Hell yes! I have always thought you were stunning,’ I answered sincerely, adding, ‘Especially you butt.’
‘Why have you never asked me out?’ she asked evenly.
‘We go out all the time,’ I replied.
Penny pinched my nipple in response.
‘You know what I mean?’ she said, sounding impatient.
‘I’ve wanted to. For a long time,’ I said honestly. ‘But to tell you the truth, I really just didn’t think you would say yes.’
There was a long pause. I felt Penny’s hair fall around my face as her lips touched mine. We shared the softest of kisses; our lips parted slightly, our tongues barely touching.
‘Silly boy. I have wanted you since we met,’ she professed, adding in that sexy voice. ‘And now you are mine to play with! That is, if you still want to play?’
‘Even if we weren’t playing, I would still be yours to play with,’ I replied, very content.
‘But I don’t think the games over yet. In fact, it seems to be getting more and more interesting. Oh, and that’s three,’ I said, looking in Penny’s eyes now.
Penny replied in a sultry voice, ‘I guess it’s your turn.’