Gin

Bree removed her undies, twirled them on a finger and discarded them on the table. It was our first game of strip gin rummy.

I watched Bree do a little spin as I scooped up my winnings; a sexy, little, black lace thong. I was surprised, but delighted, to see that she had decided to try something new. Gone was Bree's wispy blonde, but always neatly manicured, triangle of hair. In its place...nothing. Nothing, but smooth, clean, hairless skin.

Noticing the focus of my attention, Bree took a seductive step closer.

"So is that it?" she asked.

"Not if you don't want it to be," I replied, flashing a playful grin.

"Tell you what. If you win the next hand, I'll strip," I proposed, leaning back a little.

"But if I win, you do a small favor of my bidding. Agreed?" I finished, giving Bree a devious smile.

We'd had a fun evening with our usual circle, but it was discretely obvious early on, that we were both in the mood for a little fun of our own. A decision by the group to move on to another bar had been the opportunity we seized on to make a polite excuse, and head back to Bree's place.

`Am I right in assuming this favor would be sexual in nature?" Bree inquired, shuffling the cards.

"Perhaps," I replied, trying to sound nonchalant.

We had fallen into bed on numerous occasions over the years, so Bree wasn't too concerned where the game was heading.

Sitting back down, she dealt the cards signaling her consent.

Losing in such short measure was a little obvious on my part. Especially when I threw out two kings that Bree had been patiently waiting for. However, Bree didn't seem to mind me tanking the game.

As I removed my boxers, flag flying at full mast, Bree looked up at me. Her eyes were sparkling.

"Well, what shall we play for now?" she asked, sounding far too innocent.

As she took a sip of wine, I picked up the cards.

"How about we play anything goes gin-rummy?" I suggested.

"And by "anything goes" you mean," she began, giving a playful yet intrigued look.

"Well, anything and everything is fair compensation,' I offered, casually.

I could see a knowing twinkle in her eye, as she contemplated the suggestion.

"Anything?" You mean?" she asked, raising an eyebrow.

"If you win, you may ask of me anything your heart desires. And vice-versa," I replied, matter of fact, matching her grin.

"Sounds interesting," Bree said, looking very pleased with the concept.

"But I think we should make a few ground rules," I cautioned, as I reached for the deck.

We quickly agreed that the loser would try their best to fulfill any request, but that the winner would allow the "Uncle" clause for whatever reason. The request would last five minutes, or until the winner was satisfied.

"Which ever comes first, right?" Bree added, causing an excited moment of silence, and an exchange of excited glances.

"Agreed?" I said, cards poised at the ready.

`Agreed," Bree chirped, promptly filling our glasses again.

"Let's play."

The "anythings" were very garden variety to begin with. I went down on Bree. She returned the favor.

A winning hand later, I asked Bree to climb up on the table, and play with herself, while I sat between her legs, taking in the sexiest thing I'd ever seen.

The following hand, it was my turn on the table. Having performed my usual set routine, I sat up on an elbow and looked over at Bree.

"Now that we're both warmed up, shall we set the bar a little higher?" I asked, climbing down from center stage.

"I was just thinking the same thing," she answered, as she dealt again.

As we looked at our cards, both of us could sense the tension building.

My imagination was running wild with possibilities. We hadn't really been adventurous in bed, but I thought we had both had been on our best behavior.

On various occasions, we had both ventured a finger here, or a mouth there, by accident. Secretly, I had always hoped that they weren't just accidents. There were so many things I wanted to try. I just didn't want to freak Bree out.

Ten minutes passed, both of us sitting on the edge of our seats.

"Yes! Gin!" she exclaimed, slamming her cards down.

"I was waiting for that card forever," Bree beamed.

"Well, what would you like me to do for you now?" I asked, humbly.

"Well, I would like you...to...," she said, slowly.

"Yes?" I said, matching Bree's cheeky grin.

"Tickle my ass with your tongue," Bree finished, her face blushing a little.

I couldn't stop from grinning.

"Okay," I agreed, after playfully pretending to think about it.

"Are you sure?" she said, with a giddy smile.

"If that's what you would like, I'll try my best," I replied, honestly.

For a moment, neither of us moved. All we did was smile at each other.

It was Bree who finally took my hand and lead me to her bedroom. Without a word, she took a pillow and placed it in the middle of the bed. Slinking her way across the covers, Bree came to rest with her hips over the pillow. The slight elevation of Bree's hips by the pillow, gave her butt an irresistible quality.

I gave Bree's feet a tickle before parting them a little, revealing her perfectly smooth pussy. Bree looked back over her shoulder, as I placed a knee, either side of her calves.

Walking my hands out, I hovered over the small of Bree's back, before giving it a light kiss. Bree buried her face in a pillow, and let out a little squeal. Her skin prickled with goose-bumps as I laid a trail of kisses down her back and on to her cheeks.

Bree raised her hips higher, searching for my next kiss. Feeling I'd teased her enough, I put my lips to her cheeks and slipped my tongue just in to the crease. The moment my tongue touched her skin, Bree froze.

I buried my tongue deeper until my nose started to press in to her crack. Wriggling it around sent Bree in to a fit of giggles. As she turned to look at me, I grabbed Bree firmly, and gently pried her buttcheeks apart.

Looking deep in to Bree's eyes, I slowly leaned in, and traced my tongue round her unsuspecting opening. Bree closed her eyes, as a little moan escaped her lips.

Dragging my tongue over her taught ring sent Bree's face back in to the pillow, muffling her screams. For the next few minutes, I swirled, flicked and lapped at Bree's ass.

The third time Bree raised her hips, I got the message. Before I could stop to consider what I was about to do, I did it. I plunged my tongue in her ass as far as I could. Bree gave a loud moan, and pushed back in to my face.

With the fingers of one hand now frigging her clit and my tongue thrusting in and out, Bree was on the verge. Within seconds, she was climaxing, her ring pulsing around my tongue, and body trembling.

"Oh fuck!" she exclaimed, rolling on to her back.

"That was better than I ever imagined!" Bree exhaled, as she performed a cute little shimmy.

"I'm glad you liked it," I said, pleased.

"Oh, I liked it. I REALLY liked it," she declared, as she leapt up and gave me huge kiss.

"Come on," Bree said, dragging me up off the bed.

"Let's play some cards," she said, more than a little enthusiastically.

Returning the dining table, Bree gathered the cards, and shuffled up.

It seemed like the game was over before it started. Just three rounds, Bree was laying down a winning hand.

`So, what would like to do this now?" I asked, my body already tingling with anticipation.

Bree didn't answer right away. Instead, she stood up, walked over and stood behind me.

"So, would I be right in thinking that you'd like to try to slip something in my bigger backdoor?" she asked, demurely.

I smiled, but didn't answer.

"Well, let me ask you this. Ever had anything up there?" Bree asked, coyly, patting my butt lightly.

"No. Not as yet," I replied, in an intrigued tone.

"Well, that's no good now is it?" she said, disapprovingly.

"I think it is time we RECTIFY the situation," Bree surmised.

Taking my hand, she concluded, "Let's head to my bedroom and get you nice and comfy."

A few minutes later, I was laying face down on Bree's bed, with a pillow under my hips, raising my ass skyward. Bree sat at my side, a tube of lube in one hand, and the dildo in the other.

Smiling deviously, Bree put down the dildo, popped the top on the lube, and began coating her fingers.

Suddenly, the length of Bree's fingernails was somewhat of a concern, but I quickly discovered that Bree's nails were trimmed very short. I thought it strange I hadn't noticed before, but then again, why would I normally care.

"Nervous?" she asked.

Smiling a little apprehensively, I nodded.

"Yeah, me too but don't worry. I'll be gentle," Bree said, reassuringly.

"But something tells me you are going to do just fine. Now, are you ready?" she asked.

Not really waiting for my response, Bree parted my cheeks and began smoothing the lube over and around my opening. She circled a finger slowly, and then rested the tip at my entrance. My muscles instinctively clench at Bree's touch.

"Just relax," was all I heard, before Bree's finger slipped in.

There wasn't any real pain, just a weird discomfort and a slight burning sensation as her finger crept gradually deeper. As I began to think to myself what the big deal is, I felt a sharp twinge.

"Whoa! What was that?" I gasped.

"I think I just passed your second ring. Don't worry. It'll feel better in just a sec," Bree cooed, stroking my back.

"Just try to relax, after all...there's a lot more to come," she said, mischievously.

I looked back to see Bree with the biggest grin across her face, as she waved the dildo at me.

"Ah ha. Well, be gentle. It's my first time," I said, trying to sound sweet and innocent.

"But not your last," I heard Bree mutter, half under her breath, as her finger resumed its course.

In no time, any discomfort had been replaced by very pleasant sensations, as Bree now steadily fingered my opening.

"Ready for another?" Bree asked, over my shoulder, as I felt her wiggle her finger.

"Yeah, it actually feels pretty good," I replied, a little surprised at the honesty of my response.

A moment later, Bree had applied more lube and was busy sliding two fingers slowly between my cheeks. As before, there was a little discomfort, but it was quickly forgotten as the pleasurable tingles continued to grow.

I was getting into this, and so was Bree. I involuntarily arched my back, as she stepped up the pace and depth.

I didn't realize it, but I was groaning a little with each thrust. I must have inadvertently been spurring Bree on, as she didn't warn me when she added the third finger.

In actuality, I barely noticed the slight stretching sensation, as the spike in the intensely, insane tingles took all my attention.

"All right, I think you're ready," Bree said, as she reached for the dildo.

As she stood up, Bree patted my butt and said, "Roll over. I want you on your back for this."

I flipped over, revealing a raging hard-on, as I stuffed a pillow behind my head. Bree parted my legs, allowing her to kneel between them. Looking down, she tapped my knee indicating she wanted more porn star, less rock star.

Complying with her wish, I felt very exposed, but Bree didn't give me time to think. While I had been getting comfortable, she had been lubing the dildo. She now had the tip nestled against my opening.

"I've dreamed about this," Bree said, and with that, she gently pushed the dildo in.

It felt bigger, much bigger than her fingers. Uncomfortable? A little. Painful? A few more twinges, but nothing unbearable.

As the toy slowly continued, I could feel my opening give way, stretching to accommodate. I had closed my eyes instinctively, but I now had them open, wanting to see Bree's reaction.

She was entranced; staring openly between my legs. A moment later, Bree glanced up and met my eyes.

"You okay?" she asked, a little concern tainting her voice.

"Yeah," I half grunted.

"It feels really big," I added, trying to get more comfortable.

"It looks really big," Bree said, trying not to laugh.

"I am so turned on right now. This is the sexiest thing I have ever done," she breathed, heavily.

A few moments later, which felt like forever, the dildo stopped moving. Bree paused briefly.

I could feel my body relax, as she slowly reversed until I felt the tip pop out. Then it returned, driving gently back in.

My labored breaths were matched by Bree's, as she delved deeper and deeper. With her free hand, she grasped my shaft and began stroking it in time with the thrusts.

Unconsciously I had started rocking my hips, as I felt my orgasm building. Bree increased her pace, now fucking me with long, deep strokes. Then, it happened.

The intensity seemed to shoot through the roof all at once, making me cum harder than I could remember. I groaned loudly as my orgasm exploded over my chest, a few large drops hitting my face and the pillow.

"Holy shit!" Bree gasped, as she released her grip.

After few moments, she slipped the dildo out and stood up. Walking to her dresser, Bree picked up a towel, handed it to me and gave me a kiss.

"That was awesome," she said, smiling kindly.

"Was it good for you?" Bree asked.

"I think that would be a yes," I answered.

"I haven't had an orgasm like that since...I can't remember. It was so intense."

"I thought you might like it," Bree said.

"I know I did," she chirped, looking very pleased with herself, as she skipped across the room.

"Your turn to deal," she called out, as she headed back to the dining room.

Standing up, a little shakily, I followed.

I dealt the cards once again and found myself starting with less than a great hand.

Out of shear desperation, I had taken a few chances and now sat one card from victory. Bree had looked smug but now seemed frustrated.

Picking up a card, Bree cursed and placed it on the pile.

"Come on. I'm so close," she said, impatiently.

"So am I," I thought, taking a look at what she had discarded.

It was all I needed. Looking Bree straight in the eyes, I just smiled, waiting for her to respond. Then she twigged and began smiling herself. She raised her eyebrows questioningly and mouthed the word "gin". I nodded in reply.

"Well, well. What would you like to do today young man?" Bree said, in a seductive voice.

"You...as you did me," I said.

"I thought you might say that. At least, I hoped you would," she said, agreeably.

"Shall we retire to the bedroom?" she asked, very theatrically.

"After you," I said, in my most gentlemanly manner.

I watched Bree walk down the hall, my gaze following the sway of her rear. She looked back, her face aglow with excitement. As I reached the door, Bree dove on the bed, twisting midair and landing on her back.

Picking up the lube, she threw it in my direction and then flipped over, as I came to kneel at the end of the bed.

I was smiling, barely able to contain my own excitement. My eyes transfixed, as she tucked the pillow under her hips. That little elevation made her so obviously vulnerable.

"So," Bree started, looking back over her shoulder, biting her lower lip.

"Unlike you, I have been...experimenting a little," she said, slowly.

Raising an eyebrow, I grinned, "Oh really?"

"It has only been recently. And by myself, but I think it is safe to say, after our last trip here, you and I share another mutual interest," Bree grinned wickedly, as she finished speaking.

As she rested her head down on the pillow, she cautioned back, "Slow and steady wins the race."

"I'll let you know what I need...until we get going," Bree added, smiling ear to ear.

Slow and steady I thought to myself, as I gently parted her cheeks once again.

Bree relaxed as my fingertip began to coat her ass with the cold lube. Satisfied that Bree's backdoor was ready, I gently slipped my finger in.

Bree moaned as my finger came to rest. I didn't want to move as I felt her muscles clench, then relax, around my finger.

Then slowly, I began sliding in and out, each stroke trying to push a little deeper just to see how Bree would react. In answer, Bree just rolled her hips forward each time, helping drive my finger to new depths. Remembering to add more lube, I paused to withdraw.

"You can add another finger," Bree whispered dreamily.

Adding a second, I re-entered slowly but still found little resistance.

Wanting to experiment, I began trying stretch Bree further. I watched as an opening would appear then vanish, as she adjusted to perfectly encircling my fingers once again.

Over and over, in every direction, my efforts had the desired effect. Her entrance yawned wider and wider, and took longer and longer to fade. It was incredible.

Bree was still lightly thrusting her hips however her rhythm now prolonged each stroke. She was moaning more frequently and her breathing was much deeper. Bree's hips were hovering over the pillow, her knees splayed wide, causing her cheeks to part with every thrust. I could see her fingers dancing between her thighs sending her ever higher.

Remembering how Bree had slipped me her third digit, I decided to add a twist. With the timing of a magician, I turned two into three, not missing a beat. Bree looked back, her eyes wide, and her mouth agape. Her face was a mix of emotions. Then, just as her reaction began to subside, I slipped my thumb in between her lips and sunk it in as deep as I could go.

At that moment, Bree moaned like I had never heard her before.

Her body rose off the sheets and, balancing on all fours, thrust wantonly against my hand. It was all I could take. Removing my hand, I stood up beside the bed. Turning Bree over so she lay at the edge of the bed, I pushed her knees out and back, spreading her obscenely wide.

Our actions were teetering on desperate, as I moved between her thighs, and pulled her hips closer. Bree reached down to help guided my tip.

Making contact, I didn't hesitate. With one firm, gentle thrust, I disappeared inside Bree.

Bree's head shot back, her neck straining, as she gripped the sheets. I could feel her contractions around my shaft, as she gradually gave way to my advance. She was holding her breath, her body rigid. I thought to stop, but while I could see her struggling, Bree never gave any indication that I should. As I came to rest, my hips against the back of her thighs, Bree took a long breath.

A few moments later Bree had regained her composure. She was now beaming, a broad smile across her face. She giggled as I felt her squeeze my shaft a few times.

"You're bigger than I remembered," she said, chagrined.

"I think EVERYTHING feels bigger when it comes to that part of the anatomy," I countered.

"I can attest to that personally, thanks to you," I added, wearing a knowing grin.

Buried deep in Bree, I was thankful for having cum a few times earlier.

The sensation was unbelievable. Combined with the taboo of the situation, I would ordinarily have careened over the edge.

Bree gave me a coy smile and playfully wiggled her hips. Taking her gesture as an invitation, I slowly withdrew, paused at Bree's entrance, and then plunged back in.

Her eyes were locked on mine, as I gently drove in and out, both of us uttering moans of pleasure.

Bree's hands were absently tracing her body, but soon came to rest. One was cupping her breast while the other focused between her thighs.

Bree was biting her lip which added fuel to my fire. Without regard, I began driving deeper and deeper into Bree. In response, Bree was stroking herself in earnest, groaning as our bodies slapped together. Her face contorted as my push turned to a shove, my thrusts now plunging deep inside.

"I'm so close," Bree pleaded.

"Faster. Faster," she begged.

I answered by abandoning any restraint, pounding Bree hard and fast. Bree too now seemed completely unbridled as she thrust her hips and fingered herself viciously.