Strip Poker & The Ultimate Release

It had been a couple months since my last weak relationship ended. Outwardly, it seemed to have all the right ingredients, yet I never felt comfortable with her. Adding to my frustration was being sick of the city I was in. Recently, I even inquired about a transfer with my employer. With Christmas approaching, I didn't feel much like celebrating. I needed a change.

Wanting to get myself out of a rut, I returned to an online dating site I swore I'd never use again. Oh, lucky me, I still had some unused credits. Skeptically, I edited both my profile and what I was looking for.

What was I looking for? I really didn't know. If love came along, I'd embrace it. If naughty fun came along, I'd embrace that too. I decided to be much more open this time, having learned that the perfect recipe isn't always perfect. So here I am, a 34-year-old guy in the city, looking to get out there...

As I browsed through profile after profile, I found I had a bias against the fancy type of city girl. I wanted something more than superficial. A profile soon caught my eye. Rebecca was 27 and lived outside of the city, and her profile and photos gave off a good, natural vibe. She looked down-to-earth, confident, and adventurous; she had some wild travel pictures. Her main photo was obviously cropped from a climbing photo; the mountains in the background, hooded REI jacket, no makeup, and windblown red cheeks gave it away. I messaged her:

"Could a mountain girl get along with a water guy?

She responded, "There is a lot of water in the mountains, you know."

And just like that, we were messaging back and forth. I made it a point to avoid lengthy chatting and suggested we get a drink the next night. That would be a Monday, but she had plans; we then immediately agreed to meet on Tuesday.

I'd drive out to her area, and we'd meet at a neighborhood pub. I didn't know the spot, but she told me she'd be outside on the bench. I followed her directions to the place, parked, looked up, and there she was, about 50 feet away. She stood up when she saw me. It was winter and she was bundled up in a North Face, but I immediately noticed how good her snug-fitting jeans looked--I could tell she had the legs of a skier. We exchanged our awkward first hellos and had a light hug. I sensed some mutual relief that we both came as advertised.

I opened the large wooden door for her, and we walked into the cozy lodge-like establishment richly decorated for Christmas. We removed our jackets at the table, and I had the opportunity to get a good look at her. She stood about 5'8" with long, dark brown hair in a simple ponytail. Her form-fitting cream-colored cable knit sweater was both outdoorsy and sexy. I could tell she had an athletic body and breasts larger than what could be detected in the photos. She wore little makeup, but in person, she was prettier than her action-shot-laden profile led me to believe.

The conversation came easy as we exchanged stories of our adventures, travels, and yes - skiing. I learned she lived in the area her whole life and was working in a medical clinic as she studied for a master's degree. Time flew by as we enjoyed a couple of beers and shared some appetizers. I liked her. Don't blow this, Paul, I thought to myself. We both had to work early, so we decided it was time to call it a night. Outside, we had a much better hug and went our separate ways.

On the drive home, I debated with myself if I should have kissed her. On one hand, we had a great time, and I wanted to show my interest. On the other hand, it probably wasn't the best spot at the front door, and I didn't want to come on too strong, too soon.

I messaged her on Wednesday night to tell her how much I enjoyed meeting her. She agreed and then, a short while later, said the dreaded words, "You're a really nice guy."

Ugg, this never goes anywhere good. She was about to move away from me, so I called her.

As she answered, I said, "You can't nice-guy me already!"

"Nice isn't bad!" she said as she laughed. "You're very polite and a gentleman."

"But?" I said.

"I don't know. What??" She responded.

"It was a first date; of course, I was a gentleman. I always am. But I'm not always nice."

"You're not nice? I've known a few of those types."

"Of course I'm nice, but not the lame nice guy."

"Well, now I'm confused," she chuckled.

"So, if you're not looking for a nice guy, what are you looking for?" I questioned.

"I don't know, maybe just some excitement or something interesting; I'm bored. Maybe the holidays just have me down and skeptical. But a gentleman is still good."

I could tell that she found the back-and-forth amusing and probably liked me challenging her assumptions. But now what? I thought I just needed to throw something crazy out there.

I bluntly asked, "Ever play strip poker?"

"Haha, no, never! She responded. "I don't even know how to play poker. Why?"

"Let me teach you," I assured her.

"What part, poker or stripping?"

"Poker. I'm going to assume you know how to take off your clothes. Unless you're too nice for that sort of thing."

"Ha! OK, Saturday?"

What? She really agreed to it? I was just trying to spice up the conversation; I didn't think she'd actually go for it. We set it up. Saturday, 7:30 at my place.

I heard from her on Thursday, and I dreaded that she would back out as I read the message. Good news! She was just asking for poker rules! I sent her some sites to learn a basic five-card draw. But she still warned me to coach her before we played and warned me that she would be bundled up in layers.

By the time Saturday afternoon rolled around, I had my place looking good and had made a long-overdue repair to the gas fireplace. I even dug out my small fake Christmas tree and made an effort to be festive and cozy. I made sure to have some of the Winter Ale she ordered at the pub available, as well as some wine. The cards and chips were checked and stored in the desk drawer.

I had warned her about parking, and about 10 minutes early, she rang from the lobby. I buzzed her up and opened the door. Before I could say anything, she triumphantly declared she found parking right in front - a Christmas miracle!

It was cold outside, and she was bundled up as warned. I offered to take her coat and wool beanie.

"No way! I need the layers!" She joked as she handed them to me.

The black leggings she was wearing confirmed that she had great strong legs. She wore a bulky, rustic sweater that hid more than what I saw her last time.

We walked in, and she accepted my offer of an IPA, which I poured into a nice glass. We exchanged a hearty "cheers," and both seemed oddly comfortable considering what we had planned.

I then showed her around. My apartment was on the 20th floor, and she loved the nighttime view of the city and asked to go outside on the balcony. We leaned against the railing, standing close together. She looked toward the adjacent building, squealed, and pointed.

"What's going on over there?"

"Umm, wow. I think it's what it looks like."

We saw a man sitting on a sofa close to an apartment window with a woman on her knees before him, giving him a blowjob.

Rebecca strained to see. "No way, everyone can see! Do you get to see stuff like that all the time living here?"

"Not really; I've never seen something so obvious," I explained as we shivered and stepped back inside.

"Binoculars!" Rebecca exclaimed as she grabbed them off the shelf by the sliding glass door and spun around to go outside again.

"Yep, that's what's happening! They're showing off on purpose!" she said as she handed me the binoculars for a turn spying on them.

We laughed off the neighbor's blowjob, but it stuck in my mind, and I assume hers too. Going back inside, I turned the fireplace on, and Rebecca checked out my photos and books, making comments and asking plenty of questions. We were laughing, talking, and really getting along. I almost thought about skipping strip poker and doing something else, but would that seem too nice? I decided to be casual, continue to enjoy her company, and proceed. About 45 minutes after her arrival, I suggested we play some practice hands of cards.

We sat at the table, and I dealt some basic five cards. Rebecca understood some basics but still didn't know what a good hand was or exactly how to bet. I let her win a few, and she seemed to be getting the hang of it.

"Can we sit on the floor by the fire? I'm still so cold."

"Good idea; I'll get us some fresh drinks and move the coffee table out of the way."

And there we sat, with a view of the city, a warm fire, and Rebecca looking nervously cute in the light of the fire. Then she abruptly stood up and marched off.

"I'm getting my hat and jacket. They count, even if I'm not wearing them, ok?"

"Deal, but I'm wearing four pairs of underwear," I joked. "You can leave the jacket there; I'll spot you two pieces of clothing."

We settled back in and went over the rules. five-card draw, with betting before and after one draw of as many cards as you like. We each get 10 chips to play with. If you need more chips, you buy them from the other player. One chip for one article of clothing. You cannot buy your clothes back. Ante is one chip with no limit on betting.

"Here we go," I announced as I dealt the first hand.

Rebecca raised me one chip, and I threw it in on my pair of threes. We both drew three cards. She raised me another chip, and we revealed our cards. Rebecca won with three kings. Pleased to win the first hand, we both proceeded cautiously as we got the feel for the game.

It was back and forth the first few hands, but Rebecca was getting the good cards. I advised her to bet more with a strong hand, but she still tended to be conservative.

She was down to seven chips and dealing when I finally got great cards--pairs of queens and tens. I raised three, and she matched. I drew one card, a queen, making a full house. She drew three cards. Wanting to clear out her remaining chips, I bet three, and she matched it. Flipping the cards, she had aces and fours, losing to my full house. Now things were happening!

"I guess I need more chips," she calmly stated with a sigh.

I gave her two chips for her coat and beanie from our earlier agreement, and she proceeded to take off her socks and sweater in exchange for three more. Pulling the heavy sweater over her head, she briefly revealed her very toned and sexy tummy. She was left wearing a white ribbed tank top, highlighting her perky tits, thin waist and hinting at a white bra underneath.

An hour into the game, and ready for the next hand, she had five chips and was still wearing her leggings and tank top. In a much stronger position, I had 15 chips and all my clothes. At this point, I could just bet so much that she'd have to fold or remove more clothes. I decided to not hurry and not to be too be aggressive unless I got unbeatable cards.

As it turns out I didn't have to worry about that strategy as Rebecca was getting better cards and now understood how to bet. With a few hands, the tables turned, and she now had most of the chips. Then it was my turn to deal. She smiled as she looked at her cards, and I groaned, gazing down at mine. Was she starting to bluff me? She raised two, and I went with it. She took two cards, and I took four. I ended up with a decent hand of pairs of kings and jacks. She bet another two, and I was forced to use my last chips to call it.

We flipped our cards, and she squealed in delight as she revealed four sevens! I smiled and hung my head in defeat. So much for my advantage. I needed at least five chips to play, so I had to buy them from her. I stood up and removed my socks, sweater, belt, and button-down shirt. She protested the belt and the fact that I was wearing an undershirt but relented and handed me four chips. I told her how happy I was to be rid of my sweater; it was getting too hot next to the fire.

While the thought of being naked in front of Rebecca turned me on, I wanted to see her bare body even more. I was good with either scenario but decided that if I could win the next hand and get even on chips, I'd then play very aggressively.

She now had 15 chips and was wearing her top and bottoms. I had just five chips with jeans and a T-shirt. As she dealt the next hand, I got up to get us fresh drinks.

My next hand was nothing, but I raised two anyway; she folded, bringing me to a much safer eight chips. Now it's time to be aggressive.

She dealt me three aces. I bet three, and she matched. We both took two cards, and I then bet my last four chips, which she matched. If I didn't win, I would have to be naked to play the next hand. She revealed three kings, thinking she had won, as I proudly displayed three aces.

"No way! That was mine!" She shouted with a smile and a slap to her forehead.

I now had 16 chips to her four as I asked, "What comes off first, tank or pants?" Don't worry about that; I'm winning next!"

We ended up splitting the next two hands, with her netting only one chip. It was my turn to deal again my deal. I had nothing in my hand, and Rebecca bet one. After the draw, I had pairs of threes and nines. Again, she bet, and I matched it. Showing our cards, I narrowly beat her two sixes and eights.

Going into the next round, she appeared nervous, but so was I. Knowing the stakes, there was an unspoken sexual tension. She only had two chips left, enough for the ante and a single-chip bet. If she wanted to stay in against me, betting two or more, she'd have to show me her bra or panties. We'd been at this for a while, and we were both committed. I was going to raise the two chips, no matter what.

She dealt the cards between us onto the carpet. Again, I had nothing, but I still raised two chips.

"Guess it's getting serious now," she conceded as she stood up.

She leaned over and started to peel down her tight yoga pants, revealing the most beautiful athletic legs with strong thighs; they looked even better than I had imagined. I was pleasantly surprised by her choice of panties, lacy white, with satin tightly pressed against her pussy. I could see her dark pubic hair through the lace right above.

She noticed me staring and cupped her hand over her pussy, and with a giggle, she said, "Maybe not the best choice."

"No, no, I like them," I comforted.

"I'm sure you do!"

She sat down in front of me, legs crossed, no longer bothering to cover her mound. I tried not to stare between her exquisite thighs.

We continued, both knowing that she was still out of chips. Having a weak hand after the draw, I raised her one, forcing her tank top off to match my bet. Remaining seated, she quickly whipped it up over her head, tossing it on the couch. Her white bra gently held what looked to be perfect handful breasts; it matched her panties and was just as sexy. Despite the warmth of the room, I could see the slight outline of her nipples pressing the fabric and part of her areolas through the lacy edges. Her waist was slender and strong, with the flattest tummy and a cute belly button. She simply had a stunning natural body.

"Everything else I have is utilitarian, so you get to see my fancy undies," she laughed as we showed our cards.

"Whew! I needed that one!" Rebecca exhaled as she collected her meager three chips.

She soon found herself out of chips again when she wanted to raise after the draw of the next hand.

"I have a proposal," she offered, knowing she would otherwise have to remove her bra. "I'll show you my ass if I can skip putting in the two chips."

After pretending to deeply consider the offer, I accepted, and she flipped onto her stomach, affording me a view of her sculpted ass covered with traditional bikini-style.

"No, no no," I protested, "bare ass!"

"As long as I've got these on, I'm keeping them on!" she countered. "I'll just bend over."

Before I had a chance to respond, she sprung up, faced away from me, and slowly bent down and touched her toes, wiggling her butt as she widened her legs. I was mesmerized by the view, especially the patch of tight white fabric barely concealing her pussy. I could also see the top of her ass crack through the sheer material.

Hardly able to focus on the game, tension was increasing. She won that hand, bringing her chip total back to a more comfortable seven. I ached to see her nude and would bet accordingly.

Having laid out the cards again, I bet three, and she matched. We both drew more cards, and I had a flush. She had three chips left. I bet four. She threw her three in the pot, reached behind her back to unclip her bra, and flung it behind her in one motion. Her breasts were impossibly firm, not laying flat but protruding from her body. Pencil eraser nipples atop broad areolas are pinkish with clearly defined edges and minimal bumps.

I was staring as she startled me with, "Not sure where I go from here."

"I'll donate three chips to you if you get us some drinks and put on a new CD." I offered.

She smiled and got up. I'd never seen such a perfect body, and my jeans now conceal an uncomfortable erection. I took her all in as she walked into the kitchen and returned with two beers, she bent down seductively to hand me one. I continued to watch her as she stood browsing my music, wearing only her sexy little white panties. She put on "A Christmas Gift for You from Phil Spector."

A Christmas gift, indeed.

Soon, in the same position of needing chips again, I had a proposal for her to avoid trading her last garment for a chip.

"I get to feel your tits, and you don't have to put in any more chips this round."

I'm not sure if she even answered, but I remained sitting on the floor as she rose to her knees and moved over to present both of her perfectly firm breasts to my face. I grasped the back of her thigh and I alternated cupping one breast and kissing the other, with her nipples getting harder. I'm not sure how long that went on before she sat down again.

We were still in the middle of the hand and got back to it. I won again. She was out of chips and options.

"Sorry, but I'm just not a nice guy." I told her with a smile, "Hand them over."

She agreed, "Well, I guess you won!"

Rebecca slowly pulled down her panties over her incomparable thighs, revealing her pussy. She stepped out of the dainty fabric and handed them to me. I wanted to put them to my face, but instead lay them on top of my hard earned chips. A wide patch of medium trimmed dark hair contrasted with a shaved area below. Her inner labia peeking out was visibly wet and swollen. She grabbed a small blanket from the couch and threw it on the floor before sitting on it. She sat on her butt with her arms wrapped around her legs and her knees at her chin. Her juicy mound in shaded view.

Still in playful negotiations, she said, "I'd let you touch it if you were naked too."

"Touch what?" I joked.

I quickly undressed, my cock springing from my boxer shorts. I stood above her with my full erection sticking up at a 45-degree angle, with a significant amount of pre-cum oozing out. Hot from the warmth of the fire, my clean shaven balls hung low. I enjoyed Rebecca' eyes fixed on my penis. Finally, I got down, kissed her, and caressed her face. We both stretched out on the blanket, our hands exploring each other. I had butterflies and was entranced by her scent and soft skin.

I pushed the cards and chips out of the way, positioned her on her back, and kissed her neck and down to her tummy. It smelled so good, I could have stayed there all night. I slowly moved down, avoiding her pussy. I kissed all over her thighs again and again before finally licking her deliciously swollen labia. I spread her with my fingers and firmly sucked her clit, her juices were flowing as I inserted a finger, promptly finding her g-spot. She said it was too intense on her clit and she couldn't take it. I backed off and licked it gently as I fingered her. Soon she was bucking and moaning in orgasm.