I 37[M] hooked up and got punched in the face by a 28[F] during sex.

This is story #5. I hope you have enjoyed the others as much as I do writing these out. I have a photographic memory and getting these in writing has made me smile.

We will call her “Abby” for story purposes. Abby was a solid 10/10. She always got a lot of attention everywhere she went. She was blonde 5’4” 120lbs with a set of DDs and a very cute pussy. She was always given free drinks at any bar I saw her at and even the ladies were hitting on her. Abby and I had mutual friends but I never hit on her or told her I thought she was gorgeous. This may have led to us getting more involved.

I wouldn’t have dated Abby as it would have been a nightmare having to fend off the constant dick fest she was subjected to in her DMs but I would never pass up a chance to have sex.

I 37[M] had a one night stand with a 32[F] therapist and it went south after. Then a week later she meets my best friend by pure chance.

This is story #4 from me. Amazing sex but she was a bit unhinged.

I was on a dating site for a bit after a big break up and had some success meeting new people. A few caught my eye and I casted out a wide net. I got a message from a beautiful woman who had massive tits. She was asking general questions and wanted to go out on a date.

We will call her “Kate”. Kate had just recently lost a lot of weight and was getting back out in the dating world. We discussed our lives and seemed to have a decent connection. I invited her out to dinner and if things went well I would invite her back to my place for a drink.

We met at a nice sushi restaurant and Kate looked fantastic. She was about 5’7” and had the biggest tits I’ve seen in person. They were massive and I don’t know where the hell she could have found a bra. It was difficult to focus on anything else. She lost about 60lbs and luckily those tits remained.

I 37[M](19 at the time) got physically stuck inside my girlfriend 38[F](20 at the time).

This is story #3 from me. This is by far the funniest/scariest time I’ve had sex.

My girlfriend and I were rabbits. We fucked every chance we got. She was my third serious girlfriend and at that age we could not get enough. This event however caused her to not want to have sex for a few days before she broke.

We will call her “Sarah” for story purposes. Sarah was a stunner and stopped me in my tracks the first time I saw her. She was 5’ 95-100lbs with a nice set of Bs and a cute little ass. I am 6’3 and at the time I was fairly fit. We hit it off and started dating. The second date we had sex and she loved to be on top. She would get the angle just right and cum so hard. She was on birth control but didn’t want me to cum inside her at first. It took a few months but I finally got her to love taking my load deep inside her tight little pussy.

I [M]37 had an interesting evening of public encounters with [37] F.

This is story #2 and happened about 15 years ago. Still remember it like it was yesterday as this story is bat shit crazy. Now I know we are on the internet but I have to say this is all 100% true.

I was a lead singer of a local band at the time and we played the same dive bar every Sunday night. We ran an open mic night and we would get the usual Sunday crowd to have a good time. We got paid $200 to play and drink all the alcohol we could manage on top of that. Not a bad gig for some younger guys. This night an old friend from High school showed up with some of her friends. We will call her “Jenny” for story purposes. We had sex a few times our senior year but never really dated. She always said that I fucked her so good she couldn’t stay away too long.

My band played our set and I could see her staring at me the whole time. My guitar player knew our history and just gave me the look after the set knowing what might happen. I got everything set for the open mic and told the guys I was going to pop outside really quick.

I 37[M] had an old school caveman encounter with coworker [34] F.

I’m going to be posting a few of my previous encounters to hopefully give people something fun to read. This will be #1.

First off I am not the greatest with monogamy and haven’t been the best human being but these sexual encounters hold some fond memories.

I worked for a shitty outlet store and hired a few friends that I’ve worked with before to make things a little better. I ended up hiring my cute assistant manager from one of my old jobs as we always flirted and talked a lot about sex when we were alone. We never made moves on each other because we were both married. Also this was a few years ago so we were younger than ages listed.

Now we will call her “Carrie” for the story sake. Carrie had just separated from her then husband and was becoming increasingly flirty. She would come in wearing short dresses and really loose tops. She had small tits and never wore a bra. She is short and skinny as hell so it worked for her. Carrie is about 5’1 and 100-110lbs. I on the other hand am not small. I am 6’3” and about 240 at the time. I would also joke with her that because I’m a bigger guy it didn’t translate where it counted. She would just laugh and say yeah sure.