Playing the Game

"It's been a long time," she said uncertainly, as she rubbed her hands nervously along her thighs. "I mean, the divorce was five years ago, and we separated a year before that."

"It doesn't matter to me. The only question is, are you going to let it matter to you?" I kept my voice low, and held my gaze steady. I wanted to make sure that this was something she wanted, and not something she was doing under pressure. We were sitting on the floor, in front of the fireplace, on a soft, worn rug.

I had begun thinking about the game several hours ago, shortly after we got in the car. It was spring, and Rachel and I were driving to her cabin to open it up for the season. She had bought it a decade or more ago with her now ex-husband as a vacation getaway. Since the divorce, she had been maintaining it, but it was tough on her. The real estate crash meant that she couldn't sell it for what she paid for it, so she had no choice but to maintain it as best she could. We both lived near Troy, New York, so it was an almost 7 hour drive to the small town on the coast of Maine that provided the mailing address for her cabin.

The cabin itself was small affair, built as a three-season refuge for middle-class factory workers and civil servants who wanted to escape the city for a while to hunt, fish and relax in midst of beautiful rolling hills, small lakes, and the ocean shore. The cabin was furnished and had a living room, small kitchen, a couple of bedrooms and a bathroom. The rooms and the furniture were all rudimentary, but serviceable for a week or two at a time. The centerpiece of the house was the sliding glass door that opened on a small patio with an expansive view of the boat dock and lake beyond. A field-stone fireplace flanked the glass, providing warmth and light on colder evenings.

Usually, Rachel went up to the cabin for a weekend in May to get it ready for the summer. Scheduling that weekend was a problem, since she had to juggle her son's sports and school schedule, her job, and her other obligations back in Troy. Opening the cabin was a two-person job, involving cleaning the place after a long winter of disuse, getting the water and utilities restored, and stocking the cabinets for the summer. Rachel's son, Brian, usually went with her to the cabin, but sometimes his schedule didn't allow a weekend away. On those occasions, Rachel would go with a friend or relative for the long trip. This time, I volunteered.

I'd been watching Rachel for a couple of years now. My wife and I moved into the house down the street several years back, and we met Rachel and her family through neighborhood events and church and school meetings. We were all very friendly, and spent a fair amount of time with each other, sitting on the porch and sharing stories and drinks. We had all been to the cabin several times and enjoyed spending time with Rachel and Brian. One evening a couple of weeks ago, Rachel had mentioned that she needed to go open the cabin, and my wife and I volunteered. When it came time to leave, Brenda had to complete a project at work and couldn't go, so Rachel and I decided to go alone.

Rachel was not a classic beauty, but then again, neither was I. She was of average height, slightly heavy, with full, mature breasts and graying hair. Her eyes sparkled when she laughed, giving her face an attractiveness that wasn't apparent on first glance. I enjoyed spending time with her, and we had engaged in some spirited conversations. I had never really spent much time alone with Rachel before, so we had never had any really intimate conversations. I knew she wasn't adverse to discussing sex and other intimate topics, but we had just never had that kind of conversation. While I didn't intend to try to seduce Rachel, I certainly wouldn't avoid an opportunity to get her to loosen up and be a little freer. Since my fetishes involve voyeurism as well as reading and listening to stories of sexual adventures, I thought I might try to get her to talk about her sexual history.

We left early on Friday, in order to get to the cabin that evening. We would stay in a hotel on Friday, since the water wouldn't be on until Saturday. We would spend Saturday working on the cabin, and stay there Saturday night before returning on Sunday. I had only that long to get the stories I longed to hear.

My plan was simple. I would direct our conversations to dating, relationships, and families. Since we both had teenage children, it was natural to talk about our expectations for their sexual relationships in the context of our own histories. If that didn't get me what I needed, I knew that we would spend Saturday night with some adult beverages, so I could also use that to my advantage.

The drive was uneventful, and I learned a little about her personal history and about her divorce. We had known that the divorce was not Rachel's fault, but we hadn't known that she had walked in on her husband and his lover not once, but twice. Of course, he promised to mend his ways, but after the second time, she told him to get out. We chatted casually as we puttered about the cabin, getting things organized for the day of work ahead on Saturday. After we broke for dinner, we headed back to the hotel to relax and swim in the hotel pool. Since we were trying to economize, we were sharing a room at the little hotel. Rachel took her small bag into the bathroom to change, and came out dressed in her swimsuit and covered with one of the hotel robes. She was surprised that I was already changed. I said, " Well, you know how guys are. It doesn't take us long." To be honest, I wouldn't have been upset if she had walked in on me naked, and she seemed smiled a bit, implying that the prospect didn't disturb her all that much.

We went down to the pool area and spent about half an hour in the pool and hot tub, splashing around and just generally relaxing. We went back to the room to change, and this time I waited until she had finished in the bathroom before I went in and changed. We had a couple drinks in the small lounge attached to the hotel, and then went back to the room. We were both tired after the drive, and the rest of Friday evening passed uneventfully.

Saturday was more promising. We got back to the cabin and set about getting it ready for the summer. After all the moving, cleaning, cutting, trimming and repairing, we went to the store for supplies and food for dinner. We also decided that the evening's libations were to be margaritas, so we got plenty of tequila, mixers and ice.

After dinner, we started a fire and settled in. We both enjoyed board games, so we inventoried the cabin's supply. Scrabble looked promising, and as the evening wore on and the tequila flowed, the words we spelled became more adult. When I finally went out on "quim" (on a triple word score, no less!) we laughed ourselves silly.

I decided it was time to move on to the next part of my plan. "Any thought on what to play next?" I asked innocently.

"Oh, I don't know. Most of these require more people, so we don't have a lot of choice." She looked around and her eyes lit up. "What about Trivial Pursuit?"

"Great! I love that game." We got it out and set it up, reviewing the rules and categories. "Hey, I've got an idea. Want to make this a little more interesting?" I smiled in what I hoped was a disarming way.

"Maybe. What did you have in mind?"

"What about 'Adult Pursuit?'"

"'Adult Pursuit?' Is that a drinking game?" she said, looking puzzled but interested.

"No, not really. It helps to be doing some drinking, but the game doesn't involve drinking. Basically, it's more like strip poker and truth-or-dare. Every time you land on a wedge space or in the center, you get a question like normal. If you get the question wrong, you have to take off a piece of clothing. If you lose all of your clothing, but the game hasn't ended, the next time you miss a wedge question, you have to do what your opponent tells you to do. Also, if you are the question asker, and you have lost your clothes, if the opponent misses a question, you can retrieve one of their pieces of clothing (not any of your own) and use the discard the next time you miss a question. The only exception is that you can't put the piece of clothing on in a way it is normally worn. For example, if you take my shirt, you can't wear it like a shirt. You can put it on your head, or lay it across your lap, but it can't be a shirt." As I made the explanation, I could see that she was interested yet apprehensive.

"Uh...," she said hesitatingly, "I'm not sure."

"I forgot one of the most important rules. When you have run out of clothes, you have to do what I tell you (or vice-versa). But, those requests cannot be for any sexual physical contact between the players or to do something that would bring embarrassment to the players. You can't make someone run outside naked, take pictures of themselves or the other player, call or text someone, or do anything else that might be harmful."

"Well, that part makes sense. What did you mean by sexual physical contact?" There was still some interest in her eye, and she took a nervous sip of her margarita.

"I can't make you touch me in a sexual manner. I could say, 'massage my temples,' or 'massage my shoulders,' but I can't ask you to touch my butt or my dick, or kiss me. If I do, you can refuse and I forfeit the right to have you do something that turn. Of course, you don't have to refuse, but you have that option."

"I noticed you didn't say anything about personal contact..." she noted slyly.

"Very observant. One part of the game is that I can tell you to touch yourself and you have to do it or forfeit your next opportunity to tell me to do something. The only exception is that I can't tell you to do something that is physically painful for you." I waited expectantly for her response.

She still hesitated. "Jimmy, I haven't had a date since my divorce. Men haven't found me all that interesting, and I really didn't want to date with Brian still at home."

"Well, I suspect you already know that I find you interesting, or I wouldn't have suggested the game. Brian isn't here, so we don't have to worry about that. Brenda isn't here, and since the rules prevent physical contact, we aren't doing anything terribly wrong." I said it gently, simply, and breathlessly. I was surprised about how stimulated I was about playing this game with Rachel.

She still hesitated. "It's been a long time," she said uncertainly, as she rubbed her hands nervously along her thighs. "I mean, the divorce was five years ago, and we separated a year before that."

"It doesn't matter to me. The only question is, are you going to let it matter to you?" I let her response and my comment that hang in the air. I knew that at that point, anything else I said would be too opportunistic. I waited, fiddling with game board and dice. Finally, I looked up at her and smiled slowly. She looked at me, nodded and smiled, and said simply, "Ok. Let's play."

The game started slowly, with both of us skirting around the wedge spaces and missing some easy questions. I thought that Rachel might need some extra encouragement, so I decided that I needed to be the first to take something off. On my next turn, I managed to land on the green wedge and missed the question. Turns out I didn't have to fake a wrong answer, since I have no clue what it was supposed to be. I slipped off my shoes and passed the dice to Rachel.

We went back and forth like this a couple times until we were both at the point where a shirt or pants were going to go next. Once again, I decided I needed to be first and on my next wedge, missed a brown question. Looking embarrassed and a bit chagrined, I undid my jeans, slipped them off and tossed them aside. My dick was semi-stiff and was clearly visible through my shorts. I looked up at Rachel and smiled nervously as she surreptitiously eyed me with a slightly hungry look in her eyes.

Soon enough, her turn came. She missed a question and realized that she needed to take something off. I watched her as her hands twitched a bit, as if she couldn't decide whether to take off her top or her jeans. Finally, she rose up on her knees, unsnapped her jeans, and slid them down her legs. She sat back, lifted her legs and slipped them rest of the way off. She set them aside, smiled nervously, and passed me the dice.

I watched her little show, but tried not to stare. She had shapely legs, and I enjoyed the slow revelation as she slid the jeans down. She was wearing cream-colored, lacy boy-shorts style panties, which were modest yet flirty. I caught a glimpse of shadow of pubic hair, and I thought I saw a small wet spot forming. I hoped she was as interested in the slow show we were giving each other as I was.

The game went on. I quickly lost my shirt, leaving me with just my shorts, which were now fully stretched forward by my boner. I caught Rachel several times looking at my boner and the wet spot that was forming from my pre-cum. A short time later, Rachel missed another wedge question and lost her shirt.

She sighed and looked at me, working up the courage to pull off her top. She took a sip of her drink, set the glass down, and quickly, like someone pulling off a bandage, whipped her shirt up and off. She dropped it on the pile of clothes and sat back, watching me watch her. Her bra was a matching cream-colored lace, showing a little wear, but still cute. Her mature tits bulged out of the cups slightly, and her nipples were dark, hard, and poking out at the fabric of her bra. I could tell by the way her breathing quickened that she was nervous but excited.

We took a short break so that we could hit the bathroom and refill the drinks. I watched her as she headed for the kitchen and the bathroom beyond. Her ass filled the panties nicely and wiggled deliciously as she walked. While she was finishing up in the bathroom and getting the drinks, I stoked the fire and added some more wood, and headed to the toilet. When I got back, Rachel had filled the glasses and settled back down in front of the fire. She said, "I see you built up the fire. Thanks. I was getting a little chilly."

"No problem. I was glad to see we had plenty of wood." My banter was innocent, but I was waiting to see if she would make a dick joke out of the softball I had just served up. She didn't disappoint.

"Oh, it looks to me like there's plenty of wood here." She smiled mischievously at her own double entendre as she glanced down to my dick. It had returned to its fully upright and locked position, and it looked like she remained just as excited, if still with a hint of trepidation.

We resumed the game, playing with a little more excitement. I lost my shirt, and Rachel began to hope that I would be the first to bare it all. I thought she was right, and decided to make it happen. I figured if I was naked, she wouldn't have a reason to quit the game early. My chance came soon, and I missed a question in the middle. Since we had agreed that the middle would count as a penalty-eligible space, I knew the time had come. I stood up, took a deep breath, and eased the waistband over my stiffy. As it cleared my shorts, it popped up and bobbed in front of me, the head moist with pre-cum.

Rachel eyed my nakedness and unconsciously licked her lips, her eyes fixed on my throbbing erection. I had no misconceptions about my size. I knew I was middling, at best, and I was nothing to write home about looks-wise. But I was clean, healthy, and able, and Rachel, at some level, knew that what she was seeing was sex, simple and uncomplicated. She didn't have to do anything about it, and in fact, probably wouldn't, but the fantasy of sex was there, twitching in front of her. She swallowed and pick up the dice as I sat back down, my erection jutting up from my lap.

Rachel got several questions in a row correct, then hit a wedge space. Try as she might, she couldn't come up with an answer, and it was her turn to expose something. Slowly, she reached around her back and fiddled with the clasp of her bra. It parted, and she slid the straps slowly down her arms, letting the cups peel away from her C-cup tits. They were everything I hoped for -- full, slightly pendulous, with large aureolae and stiff, dime-sized nipples. They swayed gently as she dropped the bra on the pile of clothes and sat back down. I could tell she wanted to cover her boobs with her arms, but we had agreed earlier that no covering-up was permitted. She kept her arms down at her sides through main strength of will, but I could tell she had to think about it.

Soon after, she hit another wedge space and once again, it was her time to suffer the penalty. This time, she showed less reserve, standing quickly, hooking her thumbs in her panties and whisking them down her legs. Her bush was full and lush, shot through with streaks of gray. I could see her pussy lips peeking out between her legs, coral-colored and moist with her excitement. She sat back down, steeling herself for the next stage of the game.

Now the game got interesting. Since we were both naked, the penalty for missing a question was having to perform an act at the behest of the other player. Here I thought I should take the lead and made every effort to ensure that she missed the next wedge question. My efforts were rewarded, and she missed a yellow question. I cleared my throat, took a sip of my drink and said, "I would like for you to play with your boobs while you tell me about the first time you let a boy take your top off and suck on your tits."

She stared at me and blanched, just a bit. She opened her mouth, and then closed it again, holding back on an objection. After taking a breath, and a gulp of her drink, she put her drink down and began to stroke the underside of her ample tits and spoke. "I was probably 17 or so, and had been dating Jesse for maybe 6 months. We had made out, of course, and he had felt me up, but I hadn't let him take my shirt off yet. Well, we had a day off school, and my parents were at work. I had just started to take my clothes off to shower when the doorbell rang. I threw on a robe over my jammy bottoms and naked chest and answered the door."

"It was Jesse. He said he was on his way to the library to do some research and wanted to know if I wanted to come along. When he noticed I was still wearing my jammy pants, he started stammering and I could see that his dick was getting hard. I told him I hadn't taken my shower yet. He said he would wait, so I invited him in." As she was relaying this story, she began to rub her boobs, lightly as first, and then with more intensity as she became involved with the memory. She was rubbing vigorously, pulling and pinching her hardened nipples.

"I explained to him that I was just changing to shower, and he winked and asked if I wanted him to wash my back. I said no, thanks. He held out his arms for a hug and kiss, and I certainly didn't mind obliging him. His arms went around me and he kissed me, long and deeply. As we kissed, his hands caressed my back, and discovered that there was no bra under my robe. He suggested that we sit on the couch. Slightly breathless from the kiss, I agreed."

"As we sat down, my robe parted a bit and he could see the tops of my breasts. We resumed our kissing, and it wasn't long before his hand found its way inside my robe, and he fondled and squeezed my boobs with great enthusiasm, if not much style." As she got to this part, her breathing quickened and her face reddened. She also started stammering again, but continued with the story. "It wasn't much longer before the robe was open and off my shoulders, and my naked chest was open to his hungry gaze. He quickly bent and took a nipple in his mouth and began to suck and nip on it."

"It was amazing! I had never gotten such a rush from touching my tits before, and the