Where it happened: Backseat of the Car
I basically I had been wanting to do stuff since as far back as I was aware of the oppostie gender in a sexual manner. All my friends had done stuff. I knew a handful of people who had gone all the way and everybody else has apparantly made it to third base with ease. 18 years and 9 months on, and I had done nothing. Seen a boob here, made out with a girl (literally only one) and had a million ‘false starts’ where it seemed like an opportune time or situation but nothing ever came of it.
Finally one weekend my parents give me the house and, naturally, I have a party! Nothing happened at the party, as I was too busy hosting, BUT I met a girl there. A couple of girls. We agree to chill some other time. Low and behold, the very next week they call me and we drive around, hang out. I start talking to them online and one of them basically ‘agrees’ to fuck me. So two weeks later I pick them up from school on a Friday at 3 PM, and we drive around all day. We go to a football game, drive around some more, one of them leaves, we drive some more, and eventually they want alcohol so after much debate about cops and how we shall get it and getting lost everytime we try and get it, I literally hand them off to a guy who knows where to get some alcohol, and I go home. I even picked my dad up along the way.
I’m at home, eating and reading a magazine, thinking my night might be over with nothing to show for it, when they swing by about twenty minutes later with some alcohol and we go up the street and they drink. They drink and drink and both of them get drunk and get weird and very physical with each other, and they complain and they get horny and she expresses interest in another guy and then she wants to be left alone. all over the map. Eventually I go back to my place, park just outside my house and while my friend is away getting some sleeping materials, she and I and her friend chill and talk. Eventually the guys get back and girl number two goes outside to talk with my buddies, entrusting me to look after my very inebriated love interest.
Finally, I realize I have been left alone in the car with the girl I wanted all along. So she and I sit and talk for a while. She has done stuff. Lots of stuff. I have done nothing. She is swooning around like she is drunk, but talking like she is sober. So I ask if she wants to do anything with me and she says I can feel her boobs and maybe eat her out. So we drive around the block (through some side streets so that there is no way some nosey friend could follow us and ruin the moment) and I park, selecting a spot as carefully as possible without having gone too far from the other guys.
I get in the back seat and we discuss what I can do. She takes off her pants and I feel her pussy. It’s quite wet, and she is rubbing herself. She says she doesn’t particularly want to do anything but doesn’t care so she lets me eat her out. I get pussy juice all over my face. She is very wet and warm. So I eat her out even though I have no idea what I am doing. She seems to like it, because she is rubbing her clit and her breast. I stay down there for about five minutes. The backseat of my car is cramped and I am on the ground, with my head stuck between her thighs like I am being squeezed in a vice. Eventually she starts gushing liquid and my mouth and part of my face is soaking wet, so I get up. She has no idea if she orgasmed or not and I have no idea if I was any good. Then she says: anything else?
I ask about a blow job. I take out my dick and She looks at it, flicks it with her fingers and says she’ll only lick it. As she is going down, her phone rings. It is our pesky friends around the corner, inquiring as to how things are going. She talks to them incoherently for about two seconds and then shuts off the phone. When she goes back down, she goes all the way and really starts to suck it, stroking it, making slurping noises. It felt good but to this day the most memorable part was that it was actually happening, more than the specific feeling of it. She is down there for only about a minute. Then she comes up and says can we go now? I sheepishly ask for some more BJ action and she immediatley goes back down on me, this time eper and harder and for a good three minutes or longer. Probably not too long to the experienced, but to a guy who has done nothing before, it was a hefty sample of things to come.
She finishes the blow job and gets up again and we talk. I ask about sex, she says some other time I point out we’d already done basically everything else so we might as well get the sex over with. So she agrees, takes her pants off again and leans against the door. I put a condom on and move in. Because A) I had never done it before and B) we were in a rediculously cramped space, I just barely, and very awkwardly, made it into her pussy. I went to it for a minute or two, not really sure how it was going. I looked down and saw I was inside of her and I could feel the warmth of her body on my cock, but besides that I just didn’t know how to describe the feeling. Then I thought that maybe if we did it doggystyle I could maneuver better. So I pulled out, she turned around and I tried to go back in, but I aimed too high and went into her ass. I kept fucking her and she didn’t complain, but when I stopped a few mintues later she mentioned in a surprised but non-too-angry manner that I had just fucked her in the ass. So I pull way back and clear her body. The condom slips off as if it knows we are done, and I throw it out into the bushes. Then it takes me about ten minutes to find where I had left my keys. I drive her home (which takes a rediculously long half-hour or so) and then go home and go to bed. Then next day I tell my close friends what happened, and then wrod spreads like wild fire. Eventually a guy who is mostly harmless but does stupid shit to piss me off, tells the girl, without ever having talked to me about it, that I told him the condom fell off while I was still fucking her. So she flips her shit and before I know it all hell has broken lose, with everybody calling everybody else and me being the evil center figure. We get it straightened out and then I stopped talking to her. I thanked her for being so nice and to this day I hold her in my heart in a very special, unique way.
It was a big deal at school because I was a late bloomer and thought to be a goner for sure, and yet, as people talked to me, I realized I was in a fairly exclusive club of non-virgins at school, a club much smaller then I had known it to be. Over all, I was happy with my first time. To this day it is still sinking in, that I did what I wanted to do for so many years and how my fantasy became my reality.