Originally posted in FetLife, part of my quarantine boredom fight.
This one is another time trip, back to the early 90’s. I had been living in the City for several years and had kind of put the kink side of my personality on hold. I had gotten into a relationship with someone I met through friends, and while our sex life was great, I wouldn’t describe it as vanilla, it wasn’t full bore kink either. Still, when she left New York (and me) to take a job in Europe I was not sure what to do next, go the whole marry a “nice” girl, 2.1 kids, house in the burbs, or embrace my other kinkier side. This little adventure helped me make that decision. There is a lot before we get to the sex, that’s how it happened, sorry if you want only “the details””
I really didn’t want to go. I mean I REALLY didn’t want to go. But my friend Paul was one of the few people who I was really close to. We had both started at our jobs around the same time and managed to advance together without being rivals, rare in an industry that can be pretty cutthroat. It helped that after a night of drinking way too much alcohol, we had exchanged enough stories to figure out that we were both a bit on the kinky side. Neither of us told the other everything, but I heard enough from him to know he liked his women wild, and very strong. He knew enough about me to know I had used personals to hook up and that I had some handcuffs, paddles etc. Oh, and I knew Paul liked big women. And he wanted me to go with him to a party for “Big Beautiful Women.” He showed me a card with the ad and location.
Nothing wrong with a curvy woman, I love curves myself, but what I pictured in my head was a bunch of guys lining the walls drooling over women but too nervous to talk to them. It just didn’t appeal to me. Paul was a good friend and had recently done me a couple of favors, so I decided to take one for the team and go along with him, with one caveat. If they have nametags, I’m out. I kept picturing everyone sitting around like a bad high school dance.
We got to the venue around 11, we could tell things were just starting to get moving. The party space was actually nice, it was down near the foot of the Brooklyn Bridge on the Manhattan side. This was before most of the financial district went residential, so the streets were deserted. The place itself was actually hopping. There were at least sixty to seventy women there, all races and all varieties of “Big and Beautiful”. Roughly the same number of men. Some of the women were what you might just call very curvy, some were very, very large. I have to admit, I was totally wrong about the vibe in the place. It wasn’t full of sad people. The women were obviously enjoying themselves, some dancing, some drinking, some talking. And the men were interacting with them too. Obviously, like any gathering there were some wallflowers, but this scene wasn’t bringing me down at all.
Paul and I grabbed a couple of drinks and walked around, checking things out. Paul stopped to talk to the woman who organized the event. She introduced Paul to her friend and they went off to dance. I headed to the bar to get another drink, and literally bumped into her almost spilling her drink
“I’m really sorry, that was totally my fault”, I told her, I could see she was a bit annoyed, and it was my fault, I wasn’t paying attention. When she saw I was legitimately apologizing, not just doing the club “excuse me” makes it OK to shove you thing, she smiled and said “Diane.” I returned her smile and gave her my name. The bartender came over and I ordered a club soda, Diane gave me a quizzical look and I said, “I’m driving” she nodded her head, understanding.
As Diane and I walked away from the bar to somewhere a little less crowded I subtly checked her out. I’m sure she did the same to me when I was ordering. She was short, maybe 5’2. Curvy if you were trying to be nice, overweight if you weren’t. We did the normal, getting to know you exchange that people do at these kind of events. Where do you live? What do you do? This is a great place, the DJ sucks (or the music is great) pick one. After hearing all about her roommate problems and her listening to me complain about airports we had exhausted all our small talk. She took the initiative.
“So you like big women?” she said with a half smile.
“Actually, I like all kinds of women”
I could see she was half annoyed, half disbelieving. “No, look I know what that sounds like, but it’s true. I have dated a lot of different types of women, I don’t have a type.”
Still a bit miffed “C’mon”.
“No,” I answered “Really, I came here because a friend asked me, not because I need someone to look a certain way.”
“So you’re only here because of your friend?”
“That’s why I came, I stayed because you seem like someone interesting.” I think she could tell it was true- I was enjoying talking to her, especially her being willing to push back a bit. Yes I am dominant, but nobody likes doormats. (At least I don’t).
After that, more small talk, she got me out on the dance floor to do the white man shuffle. I could tell she was enjoying herself, and I was too. We exchanged numbers, I could tell that was all that was on the menu that night. Paul had disappeared with a Domincan hotttie so I drove home alone.
I called her. The next day. I had no idea where this was going, but at worst I was going to have a decent dinner and at best, well who knows where “best” would land. We both worked downtown, and went to dinner at some nondescript place down there. Dinner was quick, more small talk then we went to a bar close by. We sat down at a table and Diane got right to it.
“All types of women, what does that mean?”
“Well, I had a steady girlfriend for a while, we ended it back in November, but I have some history, and that involves some women who are all fairly different.” I could tell she wasn’t judging me (yet) she was just curious, so I continued, “I’ve mostly been with women my age, but I’ve been with some who are older. Some were thin, some weren’t. Some were white, some weren’t”
“Exactly how many-“ I cut her off, “Not going there. It’s not some obscene number” and in truth it wasn’t a huge number. The sex was mostly kinky, but not with a huge number of partners at least not by New York standards.
She took a minute to absorb that, “Older?” I nodded. “How much older?”
“Less than 50, more than 45”. Now she was interested, and a bit turned on. I was late twenties, she was maybe one or two years out of college so the gap was significant.
“How did you . . .” she trailed off. So I told her. Not all the details, if you want those, read The Townhouse, but I told her I had answered a personal ad, from a married woman. At first I think she was going to react negatively, but when I told her the husband knew, she was silent, she processed that.
“So she was, you guys did some weird.” I cut in sharply, “No. We were together. We had sex, we had fun, maybe we did things you haven’t done, maybe you have,” I held my palm up, “just don’t . . .”
“I’m sorry” and she did seem to mean that, “it’s just that the husband knowing kind of took me off guard”.
“No problem. I know it’s out of the ordinary, maybe that’s a better way to phrase it.”
“Do you still see her, them?”
“No, it kind of ended on its own, fun for a while though.”
We sat for a little bit, nursing our drinks. “You really came there with your friend?”
“Yes, that was him who waved to me on his way out, remember?”
“Yeah, so uh. . . ” she hesitated
“I liked talking to you, I liked the way you carried yourself,” looking her directly in the eyes, “I like how you look.” I said it deadpan, she took it in and knew I was telling the truth.
“Thanks” she said softly. Then after a few seconds, I could feel her knees and leg under the table gently rubbing against mine. She was looking down at the table, a little nervous. I reached under the table, and feeling her knee then up her thigh. She looked at me and smiled.
“You live in the East Village, right?” She nodded. I knew from our previous talk her roommate had moved out a couple of weeks before. I just smiled and we both got up and went outside to grab a cab.
She sat next to me in the back of the cab, on the short ride up I continued to grab her thigh, but never went all the way up between her legs. She lived in a railroad walk up, over on Avenue B. The cab turned his light off and sped away as soon as I paid him. Then we were inside and up to her apartment.
We sat down on the futon in the main room, she leaned over and started to kiss me. This went on for a while as we both roamed over each other’s bodies. After a couple of minutes, she broke off and stood up, “I’ll be right back,” then went off into her room and closed the door. A short while later the door opened. She had changed into a black teddy, and was standing there smiling. I got up, came over and as she lay down on the bed I got undressed. I took out some condoms and laid them on the nightstand then got into bed with her.
While the teddy looked great Diane seemed a little reluctant to take it off. At first I thought she wasn’t up for full on sex, but soon the top was down and I was enjoying her dark, dark brown nipple. The bottom had a Velcro fastener so I had easy access to her pussy.
We had great sex. She came, I came, after a short beak, we did it again. By itself, it would have been a great night. But afterwards. . . . it got that much more interesting.
“So tell me about that couple”
“Diane, I wouldn’t talk about you to someone else,”
“No, I don’t mean their personal stuff, their names, but what you did, how you were together.”
I looked at her, “You mean what we did when we had sex?” She nodded. “Maybe what was different than what we just did?” She nodded again. “You know, I just had a great time, I think you did too” I gestured to the sheets on the floor and the condoms sitting on a paper towel.
I think I embarrassed her, which I immediately regretted, she rolled onto her side facing away from me. I got to my elbow and pulled her back over. “I’m sorry, talk to me, tell me.”
She hesitated, then it all came out in a rush. “I’m sick of being the good one. I’m everyone’s good friend, all the guys talk to me about their problems, my girlfriends all talk to me about theirs. I’m the same age as they are and it’s like I’m their mothers. Nobody thinks I’m . . .” she trailed off. “I’m not a virgin, I mean obviously, but. . .” I just waited.
“I want to be more. . . Especially when, with a guy, I want different, I want more.”
I looked over at her, and I knew exactly what she meant. I knew why she was at that club, I knew why she wanted me to go home with her. In a lot of ways we were similar, I was just a little further along the road.
“More.” I raised up, looked at her until she met my gaze, then said “We can do more.”