Monopoly'd

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.

'Your turn.'

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.'

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