Where it happened: His 'house'
Langauge: English
Sex: Female
Rating: 5
Category: Straight
So, almost 2 years ago, I was dating this wonderful guy, who I was with for over half a year. Now, before this guy, I was with another in a 2-year long-term relationship, but I was young and stupid then. I never regretted letting Josh into my life, though.
Josh was 18 at the time, and I was 15 (I am now one week away from being 17, and he is now 20). I hated this age difference, but my mother approved of the relationship and we’re still friends to this day! Not together, but I talk to him almost daily and he’s sort of like a brother… Who you’re still strongly attracted to! Haha.
Anyway, it was during late July that this happened. I decided I wanted to go to his house/ his friend’s house (he lived there for family reasons…) and we sat around for a bit. We played some video games and talked and stuff (We’re both talkers). My mom didn’t let me over to that house, but I was with my dad that weekend, so, yeah. But, anyway, his roommate was there. He was a sweetheart, though, and he just… ignored us! In a good way! Well, when the time came. He’s kind of a man-whore… after Josh, I dated him. Oh well, that’s a story for another day. He was really nice, at least! lol
So, Josh’s roommate had a few friends online, and they were joking around that Josh needed to lose his virginity. I was a little embarrassed, but nevertheless, I agreed, and we mutually agreed to lose it to each other. Things got very romantic very quickly. We were on his roommate’s futon/destroyed couch (it was caved in) and we started stripping each other. This was not the first time with us getting ‘familiar’ with each other, but it was still odd that his roommate didn’t mind that we were going to do it literally behind his back!
The heat was turning up, and we were being so gentle. I didn’t go down on him, or him to me, this was an ever-so-slightly pure circumstance. Thankfully, he was loaded with condoms, since we were both awaiting the day this would happen.
So, it finally came to the point where his penis was at the mouth of my vagina. I had an odd feeling he wouldn’t go in, but I was/am an avid masturbater and I was slightly stretched. Also, he wasn’t amazingly gifted (He was skinny and hot. A huge penis was pushing it!) but I didn’t want anything so large it would make me cry.
At the point where he pushed in, I felt a pop, and I thought it wasn’t so bad. He was holding me, telling me he loved me, etc. It was very nice. But, when he started to thrust, I felt sore, and this didn’t go away.
Note: his roommate is STILL SITTING IN FRONT OF US playing video games!
At a few minutes in, his roommate’s mom knocked on the door! We both bolted to opposite sides of the couch and covered up with blankets. Our experience ended there, since I was too sore to keep going. But, stupid me, I thought it would be nice to have a threesome, in a way. One thing led to another, and his roommate eventually ate me out, with my boyfriend watching. I was still highly hormone-induced, and very stupid, and I have felt guilty ever since.
In the end, he broke up with me that night, but we got back together, in a way. We had sex twice more in the following 2 months before he was off to college and got a girlfriend. The last time was phenomenal and very loving. Also, we were alone for once (as roughly the same thing that happened during our first time happened our second time).
I may not be together with this wonderful man anymore, but he is probably one of my best friends. He is single now, but I have found someone else who will not lie to me and speak his mind if I’m allowed to do certain things (Like, sleep with your roommate?). I have been with him for over a year now. And, fun fact: he happens to be that roommate’s step-brother! Our friend group is very tightly knit….
Anyway, that was my story, and it was, in all, one of the best moments of my life that left me with a positive outlook on sex and the likes. 🙂
Processing your request, Please wait....
