I'd been chatting with Elle online for over a year. We met in a chat room that I don't remember, When that got too busy, we went to an instant messenger service. Later, when we were bored one night, we moved our "relationship" to a game room to play some checkers. Elle was usually the loser, but she enjoyed playing anyway.
We hit it off right away, and our conversations ran from movies and music to sex (likes, dislikes, and some cybering). After the first month or so, she admitted that she was (unhappily) married with kids. Now, being single (never married), I had no intentions of getting seriously involved with a married woman – especially one with kids – even if we were the same age. But I was in the military and in a female-deficient situation, so I happy to while away the hours talking to the fairer sex.
We had exchanged pictures, and I saw that she had short (above her shoulders) blonde hair, blue eyes and a big chest (38D and entirely natural). Then one day, playing checkers and getting bored, Elle hit on the idea of betting on the game. The wager was a topless photograph. In a stunning reversal of fortune, Elle won. I paid up with a shirtless photograph of me flexing – not that I have a huge amount to flex, but back then I was pretty cut. Elle claimed she liked it.
Elle lost the next three games. She deferred payment because her husband was home and she couldn't take the pictures. The next day, I had a picture of Elle in a black lacy bra that I could see her pink nipples and areolae through, one of her in a handbra, and one with her showing her bare tits.
Later, we played a few more games, and I won all but one. I owed her a picture of me in my boxers. As a special treat, I made sure that my dick was swollen to the point that it was clearly visible beneath the thin cloth. I sent the picture before going to bed.
I left the specifics of Elle's four pictures up to her, but told her that if I had to show my underwear, so did she. The next day after work, I logged onto email to find that Elle had come through while her husband was at work. There was a picture of her sitting on a chair, wearing faded jeans and a white bra. The next one showed her with her jeans were undone and pulled open to show a triangle of white cotton panties. In the third picture, the jeans had been removed and her legs were spread. The last picture was a close-up of her panties. I could make out the outline of her pussy lips through the thin white fabric.
It was a few more days before Elle and I got to play checkers again, but when we did, I won. Repeatedly. For my pictures, I requested more panty pictures, in different panties, pulled tight to show the lips, etc. I got my wish – sheer pink panties that showed she had only a thin landing strip for pubic hair (and more than just a hint of the pussy behind it) and cotton panties pulled tight against her fat lips.
And so we passed the months. I never could get her to show her pussy, but I got all sorts of pictures in various costumes and panties and poses. In return, she got a few from me in various states of undress, often while I was hard (or nearly so). She claimed that I was significantly larger than her husband.
Also, our chats got more sexual. I found that although she still had sex with her husband, it was unsatisfying (short dick, too quick, etc.). At my prompting (I don't know what possessed me!) she agreed to try anal sex with him, but he didn't use any lubrication so it hurt and she made him stop. I promised that if I ever got the chance, I'd use lubrication. I also found out that she'd had her tubes tied after her second child was born.
Finally, I was scheduled to move. Elle was the first to bring up the possibility of meeting (we had joked about it before, but it hadn't been possible at the time). We decided on a schedule that would let me spend a week in her town while her kids were attending vacation bible school, ironically leaving her free to pursue adultery. We even agreed that she'd provide the lube, since I didn't know what kind she wanted.
It took months for the last couple weeks to pass.
Finally, I arrived at the hotel we had agreed upon. It was on the other side of town so she was unlikely to know anyone near it, and she had arranged with her husband for a "night off" and this hotel would accept the voucher for a free night at a local casino. I arrived late, so I rented a room for the week and settled in to wait.
The next morning, at the time she said she'd be driving the kids to VBS, I tried to call the cellphone number I'd been given, but I didn't get an answer. Not wanting to leave a message in case her husband could get to it, I opted to call every ten minutes or so. I got a reply on the third call. I told her I was at the hotel, and she said she'd worried when I didn't call the night before. I explained the situation of arriving late and not knowing her husband's schedule, and that mollified her. She said she'd be at the hotel in about ten minutes. I gave her the room number and we hung up.
It actually took her closer to thirty minutes, but there was a knock on the door around 9:30. I opened it to see Elle in person for the first time. She was shorter than I'd realized (5'1") and curvy – definitely not fat, which was how she saw herself in spite of my protests. And she wore a pair of denim jeans and a sleeveless blouse with mother-of-pearl snap covers.
I invited her in and we hugged. I loved the way her big breasts squished against my chest. After the usual preliminaries (How was your trip? Any problems finding the hotel? Etc.), Elle sat down on the edge of the bed to look at the television I hadn't turned off when she knocked. I sat at the head of the bed and patted between my legs. Elle grinned and scooted backward across the bed and lean against my chest and I wrapped one arm around her waist and draped the other over her shoulder.
A few minutes later, I got brave enough to place my hand over her breast. Elle didn't react, so I rubbed it gently. She grabbed my hand and held it still and tight against her breast. After a minute, she put her hand back in her lap. When I squeezed softly and rubbed the fabric covering her soft tit, Elle didn't react so I continued.
During a commercial, I tickled her and we took to wrestling across the bed. I managed to undo the top few snaps on her blouse. When the commercial was over, we went back to sitting and when I grabbed her breast, I slipped my hand under her shirt and got a handful of lacy bra. It wasn't until I went looking for a nipple to pinch that Elle realized where my hand was. Again, she put her hand on mine and held it still, but that didn't stop my fingers from lightly pinching and rolling her nipple, making it hard. Eventually, Elle stopped trying to stop me and unsnapped her shirt the rest of the way, exposing a white lacy bra, to let me put both hands on her tits.
When I tried to slip a hand down the top of the bra cup to hold her bare breast, Elle playfully fought me. We wrestled again and I managed to strip her shirt completely off. When we stopped wrestling to rest again, I undid her bra strap. I assumed she'd noticed, because I wasn't exactly subtle about it. But when I slid my hand into the loosened bra and cupped her bare breast, Elle was flabbergasted.
"How, when did you do that," she exclaimed.
"Just now," I admitted. "When we were sitting down."
"I never felt it," she said shrugging her useless bra off. I cupped both of her breasts and proceeded to roll and play with her nipples until they were both hard. Elle squirmed and twisted as she watched television, but never tried to pull away.
Eventually, I eased up on her and rested one hand on her belly. It was a little soft, but that's not unexpected in a thirty-ish mom-of-two, and I rubbed softly in circles from her bellybutton to the top of her shorts. I slipped my fingers under the waistsband and she allowed them to stay. She didn't even say anything when I undid the button on her jeans to make more room for my hand. It wasn't until I unzipped her shorts that she noticed.
"Damn! How do you do that? If I'm not careful, I'm going to look up and see you on top of me!" I just grinned and pushed my hand deep in her shorts to cup her panty-clad crotch. She tugged her shorts down to loosen them and make them more comfortable. When I started rubbing, though, Elle pulled away and ran to the bathroom.
"Made me have to pee," she said when she returned. Her shorts were still undone and flapped open exposing a triangle of white cotton. Instead of snuggling back against me, though, Elle lay across the foot of the king-sized bed and watched television. I scooted down close to her and started rubbing her back. Shortly, my hand was rubbing under her shorts to cup and squeeze her panty-clad ass cheeks. Karen never looked away from the television.
After a few minutes, I got braver and slid a hand under her panties to rub her bare ass. Elle didn't object. She still didn't object when I slid my fingers between her legs to gently brush against her pussy. In fact, she spread her legs to make it easier.
Elle's pussy was already wet, a fact I ascertained when I slid a finger up and down her slit. Getting no objection, I started rubbing her juice all around her pussy. Then, I slid a finger into her pussy and fingered her. She was soft and wet and warm inside. It wasn't but another minute before a second finger was plunging into Elle's willing hole.
"Don't start something you can't finish," was the only admonition I got. Elle was panting and moving her hips in time with my plunging fingers. I made the mistake of looking at the clock – quarter to eleven. She would have to leave in fifteen minutes to go pick her kids up. I glanced at my suitcase where the condoms were packed and decided to just finger her and rub her clit. Besides, I thought, she's coming back tonight for the whole night. All too soon, Elle had to get dressed to go get her kids. I showed her to the door and patted her ass and went back to watch television until this evening.
To this day, I wish I'd just pulled her clothes off and fucked her bareback. Ten years later, I still jerk off thinking about doing just that (as well as all the things that came after).
That evening, about five, Elle called me. She was downstairs in a second-floor room and I could come over any time I wanted. Going to another room was a surprise to me, but it made sense when she explained that she had to actually use the voucher she had, or her husband would know something wasn't right. I quickly stuffed my toiletries in my suitcase and used the stairs to go to her room.
I knocked softly, and she let me in with her finger to her lips. She was on the phone talking to "him" to let her know that she had arrived and that she was going to enjoy the evening alone, etc. Five minutes of this crap and me not able to say a word. I satisfied myself checking her out. She was wearing shorts (summer in the south – what else would she wear?) and a t-shirt. I could see the outline of her bra under her shirt. Finally, she hung up and turned to me.
"Sorry you had to hear that, sweetheart. But if I didn't call him, he'd have called me later and it might have been more inconvenient."
"No," I told her. "You gotta do what you gotta do." I wrapped my arms around her and pulled her close. "Just like I gotta do you." I grinned lecherously at her.
"Give me a minute," she said, running to the bathroom. I heard her peeing.
