Living in Boston I had an almost relationship with someone I worked with, Jennifer. I didn’t make a move because the company would term one or both of us if something happened. This led to me being an idiot and never making a move. Someone else ended up dating her. Now I was in a situation where I had to hear her talking about this guy and it drove me up a wall. My own fault but the situation led to me being quite jealous.
While I was having these issues at work there was a girl, Tanya, that was constantly flirting with me the entire time that I was in the city, I met her through a mutual contract job that I also had. Tanya was cute and fun to hang out with but not someone I would actually get into a real relationship with. A lot of times my friends think I am too timid in these situations and that I just don’t go after women. I don’t have issues getting along with women, I have issues because a lot of women want to have a full on relationship with me and it’s led to some hectic situations to say the least.
About a week after Jenn started with her new BF I was hanging out with Tanya, her roommates, and some of their friends. There was a new guy there who she had met from her other job. We’ll say his name is Josh. Now physically I’m a big guy with a thin athletic frame, I’m 6’4 white and begrudgingly I look like Michael C. Hall.
Tanya is about 5”2 and Josh was actually shorter than she was. Like I said previous issue from work, some jealousy going and now I’m looking at this girl who I know wants me and I know she could end up going back with this guy instead. That option would lead to me going home alone and horny….and really drunk.
At that moment I decided I was taking Tanya for the evening, Josh was just going to watch it happen.
We were at some club and everyone was dancing. Tanya went to get drinks and I went with her. We were chatting at the bar and I started just absent-mindedly rubbing her back. Tanya responded very positively and soon we were dancing pretty roughly on the floor and later on ended up in the corner making out. When it started getting late Tanya told me we were all going back to her place.
I love teasing women in public, sneaking a kiss, doing things that would embarrass them if we got caught. I’m very much polite and nice. The kind of man that no one thinks would do something like that and I am extremely respectful until I get the green light. Once I know a woman wants me to touch, wants me to explore her body, then we’re going to be having some fun. Tanya and I had been making out all the way back from the train, and I full on discretely not so discretely groping her every chance I got. Spontaneous stuff to tease for the right amount of time. Thirty minutes to get back to their place by public transport and I was riling this poor girl up the whole time.
Josh actually got a little desperate and tried to make plays for Tanya when we were all there standing in the kitchen. At this point I already knew what was going to be happening as soon as Tanya showed me her room, I sat in the kitchen and tried not to laugh.
Tanya finally showed me her room she basically slammed the door behind her and was on top of me. Everyone knew what we were doing, at this point Tanya did not give a damn about discretion.
Now I was fully exploring her body with my hands. I love when women are wearing clothes but they’ve finally given me full access to touch them, strip them. Usually I take a bit more time undressing a girl but Tanya was already ready to go.
“Oh I’ve wanted you so bad,” she said in my ear after we were both fully naked and entangled on her bed. After we had stripped our clothes I got on top of her on the bed. Tanya was the smallest girl I had been with at this point but her chest was great and her ass was amazing for a girl her size. At this point I was deeply fingering and holding her down with my other arm. She squirmed beneath me and moaned in my ear. That did it and I got the condom on and started fucking her.
My ear is one of my big triggers, girls breathing heavily close to my ear, whispering into it. Drives me up a wall which I why I love missionary position. The other thing that she did that I liked was that she was able to wrap her legs around me, not something that everyone can do. This woman was a huge turn on for me in bed.
I fucked her like that for a while and then she got on top for a bit. Watching a woman face me as she bounces on my dick is great
This isn’t some brag or whatever but condoms kill my sensitivity and even if they didn’t most girls just end up collapsing and saying they are too tired when they’ve been with, many times before I actually finish. It’s not a brag because let me tell you something, the shitstorm of insecurity that can happen when a girl doesn’t make you come and you try to tell her it’s okay, not something you want to deal with.
Tanya eventually got tired after we had switched to doggy for a bit but with her small frame there was something I was able to try with her. I held Tanya down and started fucking her prone. She was trying to be quiet but she really started moaning. The whole feeling of the experience was physically and mentally great. I was now just on top of this girl able to just fuck her as fast as I wanted, when I finally felt myself about to come I actually wrapped both my arms around her entire body and pinning her arms to her sides. Finally I came and rolled off of her.
“Holy shit,” was all she said at first and then immediately we were making out again. I guess it’s the erogenous thing but making out with someone gets me hard again almost right away.
Tanya couldn’t believe it when her hand went across my dick. “You told me you came.” She said sounding a little annoyed
“I did,” I replied. “I’m just already hard again.”
“Fucking seriously?” she said
I think we initially started a little before 1am and it was getting closer to 3am. It was late and usually I’d be fine just saying to leave it but Tanya wasn’t okay with that.
“Do we have another condom?” she asked me
“I don’t,” I said.
“If you don’t have anything I have an IUD.”
My dumbass drunk self did not know what an IUD was. In fact the first thing that came to mind was IED and I was really fucking confused. What I did know was that I was clean and I told her so.
“Then just fuck me again without the condom because that was already good.” Tanya replied.
This time I started a lot slower, it was actually the first time I fucked a girl bare. When I could finally feel it starting to hit me I wrapped her up again. My arms were actually fully crossed behind her back as I had her arms and body pinned. I picked up speed and she was wrapping her legs around my back.
I came inside her but still I held her tight for a few moments.
“Are you going to let me go?” she asked.
“Do you want me to?” I answered.
“Honestly I love the feeling of you holding me down like this when you’re fucking me.”
We made out a little more and then I moved over next to her and we finally went to sleep.
When we woke up we started fucking again. A bit more sober but we already knew I had came insider her once so all bets were off at this point. The hottest part of the morning was one time after I came insider we were spooning and I got hard again and she just slipped my dick right back inside her and we slowly fucked again. The following morning I think I came three or four times inside her.
Josh had left before we even left her room. I know the entire house heard us in the morning. I felt a little bad because I had literally just made someone feel the same way I did and in a much more direct way. He never hung out with us again if I was around and after Tanya and I called it quits they did end up dating.
This is my first time submitting a story, or writing something like this. This really is a true encounter I had. I left some shit out but as good as the sex was my stupidity should be plain to see as well. If you liked it let me know. Anything you felt detracted or anything also let me know. Definitely weird writing about an event like this but that’s why we have throwaways.
Source: reddit.com/r/gonewildstories/comments/a6ihhd/how_i_m_learned_that_i_love_sex_with_smaller
I haven’t even finished reading your story yet but… did you say *begrudgingly* look like Michael C Hall?
??? don’t begrudge it, honey!
Laughed in the middle reading your story. That confusion in the middle was funny.
I personnally find it easy to fake it when using a condom. You just tell her you came and dispose of the evidence (the condom)
As a very small woman 5’2″ and 110 pounds I like the feeling of being engulfed so to speak.
I’m 5’10” and I envy petite girls; they can be fucked against a wall or pinned with no problem. And when I first read IUD, I thought of an IED too haha xD
Bruh there’s a reason no one ever figured out Dexter was a serial killer, pretty people get away with murder (get it?) so don’t sell yourself short xD
I loved this story and was thinking about it all day… one of the hottest I’ve read here. Just wanted you to know – cheers!