I officially lost my virginity at 21. It was New Years Eve/Day, in 2003/2004. My best friend (girl) wanted me to meet her good friend/ex-boyfriend for a while. She had "become" a lesbian and moved on to girls, but had a very brief thing with this guy, in high school. Well the guy had only been with girls and let her know he had gay/bi feelings.
Long story short, my friend and I were at a NYE house party, gettin drunk, doin drugs, partying all night, etc. Unbeknownst to me, she invited her guy friend over for us to meet (she was actually trying to hook us both up!). Well we met, hit it off, hung out the rest of the night, and a few of us went back to his house (where his parents and sister were sleeping). They had a big, fancy house and he basically had the 2nd floor to himself, so we went to his room and continued our pot-smoking & drinking and just chilled for a while more. Eventually the girls went home, but he asked me to stay with him, so I did. We ended up making out and started fooling around and then we both just started REALLY going for it.
He was SO horny and eager, he just wouldn't stop humping both my holes. The first load happened when he had my back against his headboard...fucking my throat. He gave NO warning and just started pumping his load down the back of my throat. I had to swallow or choke, so he just drained his balls down my throat.
We rested a tiny bit, all while still making out and fooling around and his dick finally made its way to my ass, for the first time. His dick was about 8-9 inches and medium/thick. We finally managed to get it inside me and he just humped for all he was worth and pumped his 2nd load in me (officially making me no longer a virgin AND getting my first load up my ass).
Again, we had been partying, fooling around, and fucking all night, so we rested and took little catnaps and lounged around. I remember us still messing around when the sun finally came up. Eventually, we had to start saying our goodbyes to one another, but he asked me to take a shower with him first. Again, the bathroom/shower was big and nice, so we started fooling around and making out yet again, under the hot water. My hole was tender, but still slicked up and loose from all the previous fucking, so he had me pinned against the shower wall and got his big dick deep in my ass again. He was still SO horny and didn't go slow or take his time. He literally humped my ass like a jackrabbit, with fast strokes. After a while of this pace, he unloaded his 2nd load up my ass, again with no warning...he just started nutting in me, while he continued to fast-hump. Of course, I held all the cum in me, when he pulled out.
We finished rinsing off and I finally left his house around noon or so, devirginized and having taken 1 load down my throat and 2 loads up my ass.
The story actually didn't quite end there...
I went home, rested, etc. and he asked me to come back again that night. I can't recall all those details, but I did go back, we played more, and he ended up filling my ass with another load and sucking my dick and swallowing my load (his first dick/load).
So all in all, I ended up getting fucked several times and taking 4 or 5 of his loads over that course of time (I think I might have swallowed 1 more, but not 100% sure). He was only in town for the holidays and he went back to art school afterwards, but we repeated the same ritual for a few years after that. For about 3 or 4 years straight, we always met back up at subsequent New Years parties...we flirted, partied, and went back to his parent's house where he bred me and filled me up with more cum and we'd part ways until the our next NYE hookup!
And that was how it all went down for me!