I was sitting at a literature conference, eating a late snack before the final panel of the day.
It had been an interesting but tiring day, and I was figuring out my plans for the night. I was alone, and didn't know anybody else at this particular conference, as it was on a theme I had only recently gotten interested in; I was there to get up to speed on the subject.
I had been horny for most of the afternoon. After a few hours of listening to talks, your mind wanders, and can't help but start imagining what kinds of tits were under all the professional blazers and dress shirts of the panelists. Most of them were probably not so amazing, but some of them had to be worth seeing. Plus, sometimes you just want to see some tits you haven't ever seen before. My wife is hot, and I love her tits, but new tits keep your ardor alive. A visit to a local strip club in the conference's city would be just the ticket. At home, strip clubs were a no-go: not only was my wife not a fan, but I was a professor, and there was always a chance that I'd run into a student there. That would not work at all! But here, hundreds of miles away, I was free to check out some T&A on my free time. Get some lap dances, go back to the room and jerk off—sounded like a plan.
Then a woman walked up to the small cocktail table where I was standing and eating, and asked if she could share the table. It was crowded, and there were no free tables, so it was a natural request.
I was surprised at my luck. After a few minutes, I found that not only was she pretty attractive for an academic, she was spritely and fun to talk to. I figured I had no shot at her though. I'm married, but a cute chick like this, outside the 500-mile limit? I didn't feel too guilty about fantasizing, anyway.
But she had a kind of academic demeanor that seemed to keep her from realizing her hotness. She was a bit introverted, although she was actually pretty funny. But she didn't flash her hotness to the extent that a more outgoing woman would.
She was medium height, wearing a suit jacket that seemed to be covering up a nicely-sized rack, although I couldn't really tell under the blazer, and a knee-length skirt that made me wonder about checking out her ass later on when she turned around. Her legs had meat on them—they weren't fat at all, they just weren't the scrawny model look you see in a lot of younger ladies these days. Her face was cute-not sultry, not beautiful, but round, with brown wide eyes and pursed lips, and shoulder-length dirty blonde hair. Nobody that you'd immediately be bowled over when you saw them walking by, but when them come up and talk, you check them out. Kind of a home-spun Midwestern cute kind of look. She had a nice smile and humorous, questioning eyes that didn't quite take you entirely seriously.
But after about 5 minutes of talking, we both suddenly realized that we knew each other-we had gone to grad school together, quite a few years ago by now. And we had both had kind of a crush on each other that had never been realized due to having boyfriends/girlfriends at the time. Lauren was her name.
I was happy to see Lauren was still looking good. I was annoyed that the blazer was keeping me from fully scoping her tits. I had loved looking at them back in the day, and I wanted to know what they were like now, so much later. Back then she was already well-endowed, with nice D cups-round, heavy, the kind of things that stretched already semi-threadbare grad-school t-shirts to the limits of their material. My favorite thing, in addition to her round ass and her too-sweet-to-give-blowjobs-but-you-bet-they'd-be-great-if-she-did lips. Definitely fodder for some masturbatory material in years past.
We ended up talking for a while, and moved down to the hotel bar, where we got kind of sloshed, and were having a good time.
My cock was honestly getting a little harder just thinking about the days I used to fantasize about her long ago. I noticed she was wearing a wedding ring, and she saw mine, so we talked about our spouses, who we were both happy with. But we continued to talk along the edge of flirtation.
"So what have you been doing here with your free time so far?" she said. "Jerking off in your hotel room all the time?" I think she meant it as a joke, but I decided to up the ante.
"Yeah," I said, "I'm taking care of things, sure."
"Taking care of things? How often do you need to do it? God, guys are crazy."
"As often as I feel like it. I'm away from home, not much to do. Couple times a day, depending on my levels of boredom. And the stimulation I've run into during the day."
She sat there, absorbing it. This conversation had suddenly gotten real.
"Hey, I can always use some help. I don't know what kind of expertise you've got in this area."
"Yeah, I'll take a rain check," she said sardonically. Or at least her voice was sarcastic. Her eyes were not so sure. They were open, questioning—questioning herself for even broaching this topic in the first place, perhaps.
I looked at her with a smile. It would pay to stay confident here. "Yeah, you got it."
By this point in the early evening, she had taken off her jacket, underneath which she wore a sleek, but not quite body-hugging, long-sleeve light blue shirt. Her tits were still in amazing shape—she was stacked for sure! Having kids had pushed her tits from a D cup into at least a double-D, and at least from what I could see with her shirt unfortunately on, they looked great. They were big, they were round, you couldn't in any way not notice that they were amazing. Again, these were not a perky teen's tits, they were a woman's tits, but they looked fucking great.
She decided to switch the topic (or maybe not), and asked what I was doing that night. I sat there for a second and thought about how to answer. Fuck it, I thought, take the risk. Let's keep pushing the limit.
"I was thinking about going to a strip club," I said. "Mary's not a fan, but I'm getting a little lonely here, and figured if I was going to get my rocks off I might as well see some boobs in real life first."
She was an edgy girl, as shown by her earlier probing question, and I waited and watched to see how she would react.
"Really!" she said. She seemed to be thinking. "You know, I've never been to a strip club. What are they really like? I've only seen them on TV." Another pause. "Can I come? Bring me! I want you to bring me to a strip club! We'll see boobs, you'll jerk off to them, I'll have an adventure, it'll be fantastic."
Well, you know what they say about not looking a gift horse in the mouth. She said she had to go back up to her room to get ready, and I should meet her in a couple hours.
At 10, I knocked on the door to her hotel room. She opened it, and my eyes popped a bit. No longer wearing conservative academic dress, she was looking extremely good. She was wearing a semi-transparent white t-shirt that clung tightly to her torso-and especially her tits, which were clearly stretching the material to an extra degree of semi-transparency, reminding me of the old days, and showing me the contour of her lovely mammaries to a degree I could have only dreamed of earlier that day. I could see her white bra underneath. Her nipples, just slightly smaller than thimbles, were making obvious tents out of the material, even through what obviously had to be a heavy bra to hold up those breasts. The neckline was a V neck, and scooped down fairly low to show some of her considerable cleavage. Her tits, packed against each other as they were, made one hell of a decolletage, but were still round and bouncy as she stepped out the door. Yep, double Ds if not larger.
And below? I mean, shit. She was wearing a purple tartan pleated skirt that went only halfway down her thighs. I mean, fuck. And below that, she was wearing long white socks that went up past her knees. A Catholic school girls' skirt and thigh-highs? Fuckity fuck-fuck! She wore some more makeup now, too, including bright red lipstick that showed off the shape of her full lips. She smiled.
"You like?" she said. "I figured I needed to look good to go someplace like this. I didn't have everything I needed, so I went shopping. I saw there was one of those slutty teen stores in the mall nearby, so lucky for us! I don't how how those young bitches get away with wearing this shit every day, but it feels right for me for this occasion!"
My eyes were kind of popping. "Yeah, uh, it looks good. No doubt about that! You're going to out-hot the strippers!"
She smiled mischievously and wrapped her coat around her, unfortunately covering up her amazing body.
It couldn't hide her attitude though. Her whole homespun, semi-reticent-mousy thing was gone. Now she was one burning hot MILF.
We did a couple shots down at the bar at her insistence, then a few minutes later we were stumbling out of the hotel and walking through the cold winter weather towards the strip club. It was a fairly high class one, with an equally fairly high cover. They informed us that it was fantasy night, and all the strippers would be dressed in fantasy costumes instead of standard bikinis. It was hot inside, full of the not-so-high class smell of beer and sweat. There was one main stage, lined with stools, and a number of tables around. Up on stage was a goddamn hot woman, wearing her own Catholic school girls' uniform, or at least part of it. Clearly Lauren had had the right idea in her own dress tonight. The stripper was tall and lithe, and wearing only the skirt, socks, and heels of her costume, with her shapely c-cup tits swinging around with the music. Walking around the tables were two other strippers, fully clothed in their costumes, one dressed as a French maid, the other as a cheerleader. The maid had pretty sizeable F- or G-cup tits, and the cheerleader's rack was probably between the other two girls at a D.
Lauren looked wide-eyed at the whole scene.
"I can't believe I'm actually doing this," she said. "This is perfect! Although I am annoyed that one chick stole my costume!" She walked quickly up to a table near the stage and ordered a round of drinks for us.
We sat at the edge of the stage, and I gave her a stack of ones, and explained how it worked. She was all eyes. A number of ladies went by over the first half hour, some hot, some not. Some had ridiculously fake tits, some were naturally sexy. Lauren commented on all their positive and negative qualities, and handed out the bills. The girls were interested to see her, and flirted with her.
