Straight Female / 22
My First ThreeSome
This happened when I was 15 and I was secretly meeting with a person who was coaching our female football team, he was called Brian and was about 27ish years old. I was part of the team and got close to Brian and he was divorced living alone. After training sessions, I would walk sneakily back to his as his home was really close by and go for naughty fun and then go home without anyone knowing. The sex was fun and being with someone older made me feel grown up and I thought it was pretty cool.
One week he asked me if I wanted to go to his on a Friday evening for a small party. I was confused at the time as he always said he wanted to keep things secret, but I kinda wanted to agree since I liked him so much. We talked about it and I would go to his on the Friday at like 8ish and it would just be him and one of his friends there to watch a film, his friend was called Dean.
I tried to look as good as I could with one of my best T-shirts and jeans, and put I on makeup for him using my best stuff. I got there insanely nervous, I can remember my stomach was super weak and my arms even felt funny when I got to his house and was shaking a little. When Brian let me in I was breathing weirdly but trying to hide it and act calm.
They had been drinking and was joking around with me and then Brian started kissing me, I was trying to be cool and let him kiss me since I was trying to impress him but it was kind of uncomfortable with his friend there since I was so young and never experienced this and we was supposed to be keeping our relationship secret because of my age. Brian would kiss me and laugh with me, he would tell me it was ok and I should relax so I would try.
It started with Brian making jokes about me kissing Dean which in time turned into a sort of a dare for me to. I did end up kissing Dean in the kitchen and then that turned into me kissing them both on the sofa, and somehow that turned into them both fondling me and then fingering me.
When that moved to the next stage I can remember them both getting me undressed for them and giving them both oral sex on the sofa. Brian then laid behind me on the sofa and fucked me while I sucked Dean as he sat by my head. From there I remember laying on the sofa with my legs dangling off while they took turns fucking me and it was a weird feeling having one after the other, especially as I was young and didn’t really understand what I was doing or what this situation was about. Brian then put me on his living room floor and did me doggy and Dean was in front of me doing my first spit roast.
While I was in that position and sucking Dean I then lost my anal cherry and Brian put it in my butt slowly. I really didn’t like it and asked what he was doing and he told me to try it and relax and so he kept going. He would push it in a bit, pull out, use more lube and try again. They would both tell me how good and pretty I was and since I was like this with two guys I didn’t want to say stop. Brian had anal sex with me in that position for a what seemed ages and then he stopped and told Dean to do the same. While Dean did that, Brian watched and was asking me questions close to my head while Dean did it and I can remember agreeing with his questions and moaning really loudly which he told me I was good and doing the right thing.
I’ve been asked this a few times by people who know this story. Yes, they tried to DP me but it hurt like hell. It happened with Dean sitting on the sofa and he told me to get on top of him so I did. We was having sex that way and then Brian tried to go in my butt, but everytime they both got in me it was like a fire down below and I couldn’t handle it. They both tried maybe three or four times and for a short time they did manage it and at one point they picked up the pace and both fucked me, using me at the same time, but I told them to stop. That was my limit.
When they both stopped, Brian bent me over the back of the sofa and had me doggy. They both took turns and used my pussy and butt, the anal part was always a lot to try and deal with but they would both tell me I was very good at it and that my butt felt really good. Brian cum first in my pussy and Dean fucked me in my butt after Brian did that and finished over and in my butt.
After that I went home and felt really sore below, mostly from them trying the DP and also my rear was hurting from the anal sex I had with them. I stopped going to football and stopped seeing Brian after that.
One week he asked me if I wanted to go to his on a Friday evening for a small party. I was confused at the time as he always said he wanted to keep things secret, but I kinda wanted to agree since I liked him so much. We talked about it and I would go to his on the Friday at like 8ish and it would just be him and one of his friends there to watch a film, his friend was called Dean.
I tried to look as good as I could with one of my best T-shirts and jeans, and put I on makeup for him using my best stuff. I got there insanely nervous, I can remember my stomach was super weak and my arms even felt funny when I got to his house and was shaking a little. When Brian let me in I was breathing weirdly but trying to hide it and act calm.
They had been drinking and was joking around with me and then Brian started kissing me, I was trying to be cool and let him kiss me since I was trying to impress him but it was kind of uncomfortable with his friend there since I was so young and never experienced this and we was supposed to be keeping our relationship secret because of my age. Brian would kiss me and laugh with me, he would tell me it was ok and I should relax so I would try.
It started with Brian making jokes about me kissing Dean which in time turned into a sort of a dare for me to. I did end up kissing Dean in the kitchen and then that turned into me kissing them both on the sofa, and somehow that turned into them both fondling me and then fingering me.
When that moved to the next stage I can remember them both getting me undressed for them and giving them both oral sex on the sofa. Brian then laid behind me on the sofa and fucked me while I sucked Dean as he sat by my head. From there I remember laying on the sofa with my legs dangling off while they took turns fucking me and it was a weird feeling having one after the other, especially as I was young and didn’t really understand what I was doing or what this situation was about. Brian then put me on his living room floor and did me doggy and Dean was in front of me doing my first spit roast.
While I was in that position and sucking Dean I then lost my anal cherry and Brian put it in my butt slowly. I really didn’t like it and asked what he was doing and he told me to try it and relax and so he kept going. He would push it in a bit, pull out, use more lube and try again. They would both tell me how good and pretty I was and since I was like this with two guys I didn’t want to say stop. Brian had anal sex with me in that position for a what seemed ages and then he stopped and told Dean to do the same. While Dean did that, Brian watched and was asking me questions close to my head while Dean did it and I can remember agreeing with his questions and moaning really loudly which he told me I was good and doing the right thing.
I’ve been asked this a few times by people who know this story. Yes, they tried to DP me but it hurt like hell. It happened with Dean sitting on the sofa and he told me to get on top of him so I did. We was having sex that way and then Brian tried to go in my butt, but everytime they both got in me it was like a fire down below and I couldn’t handle it. They both tried maybe three or four times and for a short time they did manage it and at one point they picked up the pace and both fucked me, using me at the same time, but I told them to stop. That was my limit.
When they both stopped, Brian bent me over the back of the sofa and had me doggy. They both took turns and used my pussy and butt, the anal part was always a lot to try and deal with but they would both tell me I was very good at it and that my butt felt really good. Brian cum first in my pussy and Dean fucked me in my butt after Brian did that and finished over and in my butt.
After that I went home and felt really sore below, mostly from them trying the DP and also my rear was hurting from the anal sex I had with them. I stopped going to football and stopped seeing Brian after that.
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# 77058 - by
Madison22 / February 22, 2025
