The day after my old boss, Charlie, was finally transferred back to the Midwest, I skipped out on poker night, and Mike, Larry, and I went out to a bar in one of those chain restaurants to drink to his departure. We don't have anything in common except work, so after complaining about the job (and wishing Charlie a speedy funeral), we ran out of conversation. I noticed that a group of people -- four guys and a woman -- had congregated at one corner of the bar and were playing some sort of trivia game: questions would come on-screen, and they would punch in their answers, and either cheer or moan (I found out they were playing against teams at other bars). They seemed to be having a lot of fun, and the woman seemed to be one of the leaders of the team -- she answered mostly the arts & literature questions, and she traded quips with all of the others (and some of 'em were fairly racy, although it seemed that her teammates didn't always pick up on those). Mike said he had to get back to his wife, and Larry left at the same time, but I stayed and followed the trivia game (hell, it wasn't like I had anything else to do). One of the guys looked like a jerk, but he knew his sports history; the others had their specialties, but really the five of 'em just seemed to be having fun together. Mostly, though, I was intrigued by the woman. She was smart -- no doubt -- and funny, with a cute face, and better-dressed than the situation called for. She was also big. Not disgustingly fat, but way bigger than would be considered attractive by anyone I knew. Still, she sounded like fun, and I wished I could find a way to get to know more about her, without being too creepy.
I didn't feel like I could impose on the game, so I came back to the place the next night (you've probably got an O'Horgan's near you -- it's that chain restaurant that's so all-fired Irish that the Korean hostess, the Latino busboy, and the African waiter all wear shamrocks). There was no game that night. The bar girl told me they had 'em two or three times per week, but that one crowd only came on Tuesdays, and they weren't a formal team; whoever sat in could play. I decided to blow off poker again and drop by the following Tuesday.
As soon as the game started, I knew I was out of my league. I felt like a high-school dropout on Jeopardy. I was only able to answer one question; one of those physics facts that I remembered from high school and that was hanging around my head unattached to anything else. Worse, it was early in the session, and I immediately got dubbed the "science guy", so I looked worse and worse as the evening wore on when I couldn't get anything else right. Luckily, these folks were really only in it for the fun (or maybe I didn't look so bad because they got so few other questions right), and I was able to hold my own in the wisecracking and silliness. And I got introduced to Kathy, who (I hoped) was grateful for my attentions.
After the game was over (jeez, did we suck!), two of the other guys left early, and I hung out with the other two guys and Kathy. Little by little, Ray and Paul were saying less and less, and Kathy and I were talking more and more. Finally, we were alone at the bar, and I admitted that I had no memory for trivia, but she sounded like fun when I had overheard the game the previous week, and I had come because I wanted to meet her. And would she allow me to take her out on Friday?
Why the hell did I say that? Kathy was way heavier than anyone I'd ever dated (not that there had been a huge number, and not that they had been fashion dolls, but this was out of line even for me). I wasn't a "chubby chaser". I had visions of those freaks: fifty-year-old guys living in their mother's basements cruising for free internet porn in their underwear in the dark. Still, it was said, and she was delighted. I couldn't break it now. Maybe I could get away with just coffee and get her home. I got her number and directions to her house ("It's upstairs, and you can park in the back next to my car"), and agreed to get her on Friday.
It was a great first date. She came to the door dressed in a black pinstripe suit with a lace top under her jacket that showed off her cleavage. She was dressed way better than I was, but she said not to worry, she usually dressed up a little. She was nicely made up (just enough, not troweled-on or anything), and her hair was newly done and colored. We went out for coffee, and stayed for dinner, and almost closed the place after they moved us to the bar so they could turn over the table. I heard about her family ("They're all screaming nutcakes, but we really like one another. You're much more likely to see us on 'Comedy Central' than on 'Cops'."); I heard about the trivia team ("Do you believe those guys? To them, I'm just one of the boys. I'm not sure they even know I have boobs. I mean, I know what size bras I gotta buy to cover these girls; you'd think they'd be impossible to miss!"); I heard about her job ("The bank is SUCH a bore. I wear lingerie under my suits just so I can feel rebellious during the day."). I asked about the suit she was wearing, and she said, "Look, I know what I look like. I know who I am. And while I like myself the way I am, I know that I can't wear stuff that younger and thinner girls can; I'd look silly in it, or worse. I mean, can you imagine me in low-riders and a midriff top? I'd just look like a careless pig. So I tend to overdress a little bit most of the time, so I can get to feel at least a bit attractive and in control." I talked about my life, such as it was, and what I did for work and for fun. It turned out we'd read a lot of the same stuff; we liked the same movies; neither of us could make heads or tails out of modern music. We made jokes about everybody, we flirted all over the place, and we were just a bit sickening to anybody near us, I'm sure, but we had a lot of fun.
So I drove her home, parked in the back, and walked her to her door. We kissed, kind of long and slow. Then she pulled out her key, and said, "Look, I like you, and I had a great time, but I've gotta end it here for tonight. I hope you'll call again, 'cause I'd really like to see you."
I was always prepared for this, and pulled out my best Shakespeare: "What, wilt thou leave me so unsatisfied?"
She laughed (she obviously recognized the quote), and said, "Look, you're just not gonna climb my balcony tonight, OK, Romeo?" She stood there a few seconds, and put her key in the lock. And then she stopped. She looked at me again and said, "Wait. That last was, like, kind of a test. The last guy that I told I didn't want him to come up gave me a black eye and a fat lip. So this time I had one hand on the key, and the other on the pepper spray. But you didn't get all pushy or scary... and I'd really like you to come up. I would. I'm sorry I wasn't completely up-front with you, but, uh, don't you want to come up and use the toilet, or something? I can promise the most inconvenient bathroom in three counties."
I didn't even think about it. "Yes, I want to come up. Who could resist such an invitation? The most inconvenient bathroom in three counties? And you're not even going to charge me admission?" We went up, into her apartment. She showed me the bathroom (she was right about inconvenient; it was under the roof angle, and to use the toilet required a certain amount of contortion). I noticed there was only one open toothbrush, but there was a Spiderman toothbrush still in the box.
When I came out, she had opened her suit jacket, showing that the top was lace all the way down, and her bra showed underneath. She reached up and kissed me, pushing her ample boobs into me. I held her and kissed her there, but she said, "Y'know, there's a perfectly good couch across the room,", and led me to it.
We kissed for (how long? I don't know), when she pulled away. She said, "I want to slip into something else. I'm not sure it's more comfortable, but I'm fairly sure it's more likely to get me what I want," and she left me alone on the couch. While I was alone, I looked around. Bookshelf, check. Good stuff; similar books together; lots of topics, not too much girly frippery. Pictures of (probably) family and friends on the walls and shelves, no "Hello Kitty" or similar junk. Clean (unlike my place). Simple but comfortable furniture.
While I was taking inventory, she came back in a red gown, slit on both sides, and a short jacket with short sleeves. She sat down next to me on the couch, and we started kissing again. It seemed like the purpose of the jacket was to come off, because it slipped off quickly and she made no effort to replace it. The gown was cut low in the back, with spaghetti straps. When she moved, it barely constricted her large, lovely breasts. I ran my hands down the exposed part of her back, gently stroking and tickling her. She hunched her shoulders together, and I could see down her cleavage. I asked, "What would happen if I pushed aside those straps?"
She said, "This," and pushed the straps off her shoulders and lowered the top of her gown, which fell to her waist where she sat. Her large breasts were exposed, with large, dark areolas and nipples that were already somewhat stiff. I held one of her breasts. I'd never been with a woman whose breasts were so big, and the weight was surprising -- and a turn-on in itself. I reached down to adjust my cock, and she said, "I could do that", and began to stroke my cock through my clothes.
"Hmm," she said. "I want to do two things here, and I don't know which I want to do first, or how to bring 'em up. I want to say both, 'You've obviously got way too many clothes on,' and 'You know, there's a perfectly good bed in the other room where we could spread out some more.' Is it too much to ask both at once?"
"Nope, not too much," I said. "In fact, I consider you the picture of good manners. Lead on, and I'll take care of some of the clothes myself," and I peeled out of my sweater, t-shirt, shoes and socks, and chinos, leaving my shorts on.
"Nice view," she said from the bed. "Bring it over so I can get a better look." She was stretched out, and one of the slits of the gown had opened so I could see an expanse of leg; she had beautiful, unblemished skin. She had not replaced the top of her gown, and her exposed breasts caught my eye. I lay down next to her, and started kissing her nipple, and sucking on it. Her nipple got firmer in my mouth, and she sighed. She started stroking my back, and put one leg over mine so we could grind ourselves together; I was hard, and she was warm. Even her warmth was a turn-on. I noticed her perfume, and then I noticed her own aroma between her breasts. I kissed between her breasts so I could keep my nose there. I felt the weight of her large breast on my cheek. My cock was throbbing in my shorts.
"In case it's not clear enough, I am hugely turned on," I said.
"It's clear. I've got an idea what I can do about it," she said.
She turned me on my back, and took the waistband of my shorts in her hands. I hoisted my butt up so she could remove them, and I lay naked on her bed. She hung her breasts over my mouth, where I sucked on each in turn, then she used her nipples to stroke across my chest, my stomach, my cock, down my thighs and legs, and then back up to my cock. She held herself so that my cock was in her cleavage. She was so warm and soft.
"Do you want to press the girls around him? And what can we call him, by the way? 'Penis' is so clinical."
