Five Nights at a Conference Pt. 01

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.

She was enthusiastic as one stripper on stage started coming around, shaking her tits at us.

"Oh my god, John," she said to me. "Can I get her to rub those things on you?!"

"Uh, sure," I said, "just give her some cash." That quickly started a habit of her paying every stripper around to gyrate wildly on me. She was liberal with her cash—she had written a surprising bestseller on analyzing images, and had money to burn—so I got a lot of tits in the face, certainly more than I would have paid for myself. It was stripper heaven. My cock was rock hard.

"You like it, right?" she said. Then she wanted to try it herself too, and had the strippers start rubbing their tits in her face. She got into it, and was licking their tits, going farther than most guys get to in the same situation.

Then out came a real hottie, the girl in the school girl costume we had seen earlier, although hers was a little different; she sported a button up shirt and a red skirt. Her tits were compact and curvy, and her legs were long. Her overall body was very toned. Her face was very sexy, with brown hair. Ashley was immediately attracted, and sat up straight.

"This girl!" she said. "This is the girl we need to give you a lap dance!"

The girl did her number on stage, and Lauren was staring. She put her hand on my crotch, and started rubbing me from the outside. She looked at me.

"You like that?" I just looked back with smoldering eyes. When the girl finished, and made her way around the stage, now only wearing white panties, Lauren paid her a 20 for a lapdance for me. The girl, Ashley, was happy to do so, and started giving me a very hot grinding dance, all the while looking at Lauren, sometimes seeming to eye-fuck her, and even fondling Lauren's sizable tits.

When Ashley was done, Lauren said she might want to see her back again, and Ashley said sure thing. I had a giant hard-on, and was only a hairsbreadth from coming from Ashley's constant ass-grinding, not to mention what she was doing with Lauren. Lauren's nipples were now rock hard and protruding even farther than before. We turned back to the show, and she slipped her hand inside my pants this time, slowly jerking me off under the stage.

Her hands moved slowly up and down my shaft as we watched the other strippers onstage. I didn't look at her, feeling like if I did, it would break the spell.

"Oh my god," she said, murmuring. "Oh my god. I love this cock!" Her hand felt small around my shaft, and I could tell that she was impressed by its size. "What is it?" she said, "Tell me how big it is. It feels like..."-and here she seemed to be doing some complex math calculations- "...eight inches!? Is that right?"

I looked at her and smiled. "Give the girl a kewpie doll," I said.

Her eyes opened.

"Seriously? Oh my god," she repeated. "And it's so fucking thick!" Her voice lowered. "I need this cock in my mouth," she said, her red lips looking sultry. "And other places." Like I said, I had been on the verge of coming five minutes ago; I don't know how I held back at this point.

Just then Ashley the stripper walked up, once again fully clothed.

"I see you're having fun," she said. "Care to come into the back rooms for some more fun than you can have out here?" Lauren's eyes were pure lust as she looked at her hand in my pants, and then roved up and down Ashley's toned, hot body.

"Yes, definitely."

As we walked back, Lauren gave my dick another squeeze through my pants.

"It's my time of the month," she said, "so I can't fuck you like I'd like to. But I can make sure we both have some fun."

Ashley gave Lauren the same treatment, not wanting her to be left out, and ran her hand in front of Lauren's crotch. Lauren's eyes opened wide, and Ashley got a big, sexy smile.

"Mmm, yeah, I can tell you're ready to rock as well, honey. I'm looking forward to you two. I'd like to get a little of that."

"Thank you," Lauren said, her face turning surprisingly red given what she'd already done tonight, "but just him tonight."

In the back rooms, Ashley explained the rules to Lauren, who promptly laid down the pile of cash needed to get the maximum experience. Ashley then took charge. She had us both sit in a single chair, with me behind Lauren, watching Ashley strip down again. She told me to fondle Lauren's tits through her clothes. I happily complied, thrilled to finally get my hands on the tits that I had fantasized about years ago—with a sharp upshot in fantasies over the past hour. They were heavy and soft, and I kneaded them relentlessly, feeling their thick hard nipples with excitement, the thin t-shirt fabric and bra doing nothing to hide their amazing texture and buoyancy.

When Ashley stripped down to her skirt, Lauren stopped her.

"It's much sexier to keep it on, isn't it?" she said. "You still get the signifier of the uniform, but get to see the tits." A literary analyst to the end.

Lauren then leaned forward and started fondling those very tits of Ashley's herself, clearly enthralled. She moved one of my hands from her own tits to Ashley's, then placed her hand on mine so we could both feel Ashley up. Then Lauren bent her mouth down and started sucking on one of Ashley's nipples, feasting on her supple tit flesh.

"God, this is some sexy depraved shit," she said. "I love it."

The stripper seemed to be enjoying it as well, and smiled lasciviously.

"OK lady. Now it's his turn. I want you to sit in the chair there," She said, pointing to another one nearby. Lauren sat. "Now, open your mouth like a little bird waiting to be fed. Because I think this fellow is probably about ready to blow."

She had me stand up, and turned me towards her. Then she stood at my side, unbuckled my pants, pushed them down around my knees, and then pulled down my boxer briefs. She held my now massively-protruding cock, and started jerking me off. I felt Ashley's great tits pressed against my back, and was looking at Lauren's rack so tantalizingly near-visible through her tight white shirt, and her sexy mouth, her tongue swirling around her lips. I was indeed ready to blow.

"You do want it in the face, right Lauren?" Ashley said in a purring voice. "That's where I'd want it. I think you've been waiting for it, haven't you? Tell me where you want him to shoot his load."

"Oh god, yes you're right. I want him to come in my face. John, I want your cum all over my fucking married face, I want you to mark me like your whore, I want to drink that shit like a fucking dirty slut!"

The stripper's hands were skilled at their job, and after that scene of Lauren begging, my cock exploded in a gush of cum, blasting several sticky shots straight into Lauren's waiting mouth, saturating it so only the tongue stood out of a sea of viscous white. She closed her mouth to swallow, clearly delighting in her meal, but I wasn't done shooting, and shot five more across her cheeks and chin and nose before she opened her mouth again to get some more shots, at which point I finally starting to slow my blasts. Her face was criss-crossed with multiple slimy streaks of white that were staying in place like frosting on a donut.

The stripper slopped some dripping cum off my cock with her fingers, then offered her fingers to Lauren to clean off. She did so, sexily sucking each finger. Then the stripper repaid the compliment, and holding Lauren's cum-swaddled face, she licked her clean, slowly running her tongue over her face. Then they kissed, and swapped my cum back and forth several times in long gooey strings before Lauren ended up with all the cum, and swallowed it.

"Wow," Ashley said. "Your man sure can shoot. I've jerked off a lot of guys, and most can't shoot even a quarter of what he did just then. I wish I could be a fly on the wall for what the two of you do later on." She grinned and winked at Lauren.

"My man, yes," Lauren said with a smile. "Mine for the next few days anyway."