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Mentor

Age when it happend: 18
Where it happened: friend's bedroom
Langauge: English
Sex: Male
Rating: 6
Category: Straight

Alright, well here it is for all the world to see! I was basically a loser with the ladies while in high school as the Aerosmith song goes. I openly admit that then I was quite socially inept and had few friends and even fewer female admirers. I was convinced, as I graduated in 1988, that the loss of my virginity was a loooooong way off. It also didn’t help that I went to an extremely conservative high school in an extremely conservative town where it seemed the girls all had their legs cauterized shut at age 14. BUt I did have some luck or I wouldn’t be writing this after all.

I went to the downtown movie theatre one night just to see a movie by myself. At the candy counter I couldn’t help but notice the nice breasts and smile on one of the girls working that night. I started to talk to her and her co worker and found out her name was Sheila. I didn’t get that she was flirting with me so I just went back to the movie, popcorn in hand. I came out to use the washroom about a half an hour later and Shelia was cleaning up all by her lonesome, her co worker was then gone. I invited her to come sit by me and watch the rest of the movie of she so wanted to when she was done with work. I had no idea she was going to actually find where I was sitting in the not-very-crowded theatre and do some very heavy making out with me. She was a little on the plump side (the way I like ’em ever since) so her breasts where quite firm and up to the task of being squeezed a lot that night. I had my hand far up her shirt in no time and was digging my hand into her crotch through her pants to the point where I thought I just may have been bringing her to orgasm. We must ahve made out hard and heavy for at least 45 minutes when the movie finally ended. I had made out with other girls before and even done the heavy petting thing but this girl just didn not care about subtlety at all. She didn’t care who saw us at the theatre that night. But I don’t think anyone did. We went to her van and made out a little more after that, too, but she refused my attempt to get her in the back and go farther. I had a hard on that could have cut diamonds by then. Alas, I was used to the familiar “N” word. I must have gotten up at least 8 shirts by then in my life just to hear that word. Little did I know that Shelia had other things in mind.

Two weeks later I got a call from her (we had definitely traded numbers) and she wanted to get together. My friend Art was having what amounted to a week-long beer bash at his place while his parents where out of town. His high school jock buddies would com eover by day and hang out in his cool, dark basement watching cheap oriental martial arts movies by day before the usual party unleashed as soon as somebody’s brother’s friend or whoever managed to get a keg over there. Then the rest of the recntly graduated would show up and drink themselves into pre-collegiate oblivion. I liked Art, he was a real friend. And his jock buddies, the crowd that I avoided throughout my career as a professional high school loner, weren’t so bad either. It’s just that I probably wanted less to do with them and their scene than they wanted to do with mine. I suggested to Shelia that we get together and hang at Art’s before she had to go to work. She set it up so her Mom would drop her off at the theatre under the pretense that she was going to work early. Where she really went was my car waiting to pick her up behind the theatre. We drove straight to Art’s pad and went to the basement where the usual assortment of jocks, no doubt virgins themselves, where thoroughly amazed that yes, I had actually made some kind of contact with a girl. She was looking good, too. Cleavage in full effect, baby! I sat there with her fir a few minutes, she making no secret of her lust towards me as she played with my hair. I asked her if she wanted to go upstairs to get a glass of milk. She said yes so up we went.

We didn’t even get to the kitchen. We immediately grabbed each other in a lustful clawing in the hallway, all lips together and hands run through hair like we didn’t give a fuck. We went into my friend’s bedroom where we continued to kiss and I stood her in front of me as I lifted her shirt up over her massively firm breasts. I sucked her deliciously huge nipples as she groaned with pleasure. I was getting the feeling that yes, this girl was indeed loose enough morally to say yes to me. I thought that maybe losing my virginity was supposed to be something I’d do with someone I loved or some shit like that. Yes, I did contemplate waiting. But I also thought that considering how things had been going, this was going to be the last chance for quite somw time and I’d better take it. “Wanna do it?” I asked her. “Of course.” was the reply. I couldn’t believe that this had finally happened. I didn’t get the “N” word.

I went to my friend’s drawer where I knew he kept the rubbers and got one out. By now it was getting pretty damn hot in that room, not just from our arousal but from the fact that the air conditioning wasn’t on, the door to the room was closed and the shades that where drawn over the window didn’t do a very good job at keeping the sun out. It was going to turn into a hot box in there that a guy the age I am now could never withstand. But I was a little younger then and sufficiently motivated. She lay down on the bed for me and I pulled her pants down. Her shirt was already uip. So far it had never occured to me to take all my clothing off with a girl but this seemed like the time. I asked her if she minded us getting fully unclothed. She said she wanted to leave her pants and shirt on, I have no idea why. BUt I wasn’t going to argue. I removed only my shirt and then put that rubber on. The heat was really getting to me by now and it was going to get worse as we started to fuck in a moment. I got on top of her and some cold words flashed through my mind right then. To this day I half regret even thinking them but I’m sure I wasn’t alone in that thought at this moment. The thought was “Jeff, you could do better but you might just have to wait a long time to do this again.” It was almost like a voice from another dimension the way it came to me. Then I started kissing her again and we did the usual fumbling around as I tried to get my penis into her vagina. I wanted to put it in without assistance but after trying to press it in to places on her genitalia where there are no openings, she finally grasped it and helped me slide it in. It was a much smoother entry than I thought. BUt I didn’t quite get that accomplished rush that comes from sex acts nbowadays. Maybe it was nervousness or the nearly unbearable heat.

I pumped my cock into her for some 45 mintes as we wrestled around and kissed and tried to ignore the awkwardness of having our clothes on. We where drenched in sweat. And after a while I had to admit I was finding it difficult to come due to the heat. My body was concentrating more on sweating and doing what it could to keep cool than the act of orgasm. But I knew I was never going to forgive myself if I didn’t orgasm here. I’dve been scarred for life. I stopped for a minute and looked at her. She did look quite beautiful lying there. WE may not have been much of anything to each other but I have to amdit that she meant something somewhere to me since this was my first. She had been kind and generous with her body to me and I was grateful for that. I’d call her after we had done this but she seemed to lack any real interest, dropping a ton of hints that she had a steady boyfriend but I seriously didn’t care. By then we had both had what we wanted. I didn’t dislike or disrespect her for that. Even if she said she had no idea I was a virgin. She didn’t believe me when I told her afterwards.

She sensed I was having a hard time coming. “What can I do?” she pleaded. I never thought a girl would be so dedicated to pleasing me. With that we began to thrust like never before, she bucking her hips to meet my cock going in and out of her. I was going to come or pass out trying. I finally dud get that feeling, however distant, that an orgasm was on it’s way. Sooner than I thought, mypenis tensed again and again in her, spewing come into that rubber like there was no tomorrow. I even wondered if it was going to break but of course it didn’t. I pulled out of her after some afterplay and cuddling. The condom, I was surprised to find out, only had the tip filled with semen. It ahd done it’s job well. The orgasm itself was okay, I had had much better from masturbating, but this was my first time with a girl and the unbelievable heat of the room, I’m sure, contributed to my somewhat lackluster climax. We straightened up a little and went downstairs.

I collapsed onto the couch, panting like a dog from what was probably borderline heat exhaustion. It took me a full 15 mintes to stop it. Shelia looked graceful and composed as she walked model-stead over to me and sat down with her arm around me. The jocks parked at the basement bar gave me a lingering look of disbelief. But they all knew what had transpired. It was one of the sweetest moments of my life as those guys, who thought I had been an outcast and would never lay anyone, where forced to acknowledge by way of hard evidence that I had indeed done it. They found the used rubber in the garbage afterwards and by that night I was being congratulated by every male at the party. I accepted this even though I felt no bragging or elaboration was necessary. After I caught my breath I took Shelia to the theatre since it was just about her worktime.

Months later I did meet and fall in love with another girl, the first time with her was spectacular. I don’t know if I can apply any Godly reasoning to such a subject as to why certain things happen during sex, but it was a mindblowing experience when, for the first time with this girl I really loved, (or any girl for that matter) I got to lay on top of her with all of our clothing off. That almost made leaving the clothing on with Shelia worthwhile.

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