So I’m a sophomore in high school and the strangest thing happened, Mandy, a junior who was the sister of the girl I had a huge crush on, inexplicably asked me out on a date.
I was a prude, you could say, a product of my parents’ conservative mindset, and kind of repressed about sex, goofy about it, almost, but Mandy was a really cute girl, a soccer player, not the skinniest girl on the team but she had an adult sexuality about her, she looked like someone who was about 22 when she was 17.
She gave me a hand job in her bedroom about a month after we started dating, I came after less than a minute. My first blow job came after a Spanish study group at the town library. We went for a walk that took us behind the high school. In the back field, in almost total darkness, she started kissing me, and she pulled my pants down, and I pulled her shirt up over her head. The ground was very dry, and next thing I knew she was kneeling completely naked and sucking my dick. I laid down before I fell down and I’ll never forget how it felt to run my hands over her naked body, squeezing her breasts, caressing the creases of her hips as she kissed up to my mouth and back down again, ran her warm lips over me again and again. She was covered in goose bumps from head to toe, but she felt so good. I came; she took it in her mouth, but spit, which I learned she always did – as reputations went in school, this was better than being labeled a “swallower.”
Then she climbed on top of me and started rubbing her slit against me, it felt so incredible, although stupid in light of the fact that I was still dribbling come. She asked if I had a condom, and I didn’t, so that was how far we got. And something unclicked that night, too. Our relationship kind of peaked. She blew me a few more times, and I rubbed her to orgasm once, but pretty soon she dumped me, for someone who was a bit more aggressive. Man, that hurt. I sulked for at least a year.
Somehow I got all the way to sophomore year of college, still a virgin. I promised myself that at my summer job in a bank, I would open up, be one of the gang, get a girlfriend, have sex. I had worked in the bank summers during high school but this was an internship, in the offices instead of as a teller. They sent a letter with the names of all the interns. Three guys and four girls. I figured at least one of the girls had to be hot.
So, it turns out that 3 of them were. What a summer. This guy Chuck and I became good friends fast, and that helped, because having someone there I was friends with helped me loosen up and be myself, and as it turned out I started charming the girls. One of them, Andi, was easily the cutest, she was about 5 foot 4, blond, 105, she ran 2 miles a day and she just had this great personality. Kelly was a lacrosse player, she had a great body and great piercing blue eyes, but she was so into herself and being a lacrosse player. And Michelle, she was cute, as tall as Kelly, thin but not as athletic, but she had this sexuality to her that was kind of under the surface. She was buttoned up, the smartest of the three, very shy.
Andi had a boyfriend, who didn’t treat her all that well, but you could always tell when they had been together, she was a lot sassier. All 5 of us (including Chuck) hung out, increasingly often as the summer went on, and Andi and I went on a few “dates,” though I didn’t think of them like that because of her boyfriend. The day after the internship ended, we all went to Vegas for a weekend – Chuck went to school out there and we crashed at his place. There was a lot of drinking, some vomiting, and Kelly made out with some guy and then fucked him in our room with the rest of us “sleeping”. I was sharing a bed with Andi at that point, and I was so turned on, it was everything I could do not to touch her, and looking back, I really should have.
So anyway, the weekend was over, and I drove the four of us back (Chuck stayed at school) and incredibly I had spent the summer with 3 hot chicks and still not gotten anywhere. We dropped Michelle off in San Bernadino at a friend’s, and Kelly off in Encino, and Andi asked me to drop her off at her apartment at USC, where she stayed all summer and was going to be a sophomore. (I went to UCSB.) I let her out and she stood there and was like, “You don’t have to leave right away.”
So I went in with her and I was so tired after two days in Vegas partying the whole time, I just plopped on her couch and we watched TV. She sat on the floor making a decoration of some sort for her room. We chatted about nothing much.
She listened to her voicemail messages on speakerphone, and there were two new ones. She went into the kitchen to get some water, and the messages ended before she got back. She yelled something and started running back to the living room, but not before the first saved message started – it was me, some random msg I had left during the summer. She shut it off, but I had heard some of it. She was so red. But it was exactly what I needed to know – she liked me too. She had saved the voicemails I had left all summer.
I told her to come over to me. She straddled me on the couch, and we kissed, it was such a dynamic moment, and I was so hard so fast. I rubbed her bare skin under her shirt, her bare legs below her shorts, and she knelt lower until our hips were together beneath our clothes. We kissed for a few minutes, our shirts came off, her bra, she had small round tits that she offered to my mouth, one after the other, I sucked on the nipples. I unbuttoned her shorts and felt lower and lower. When she reached for my pants front and undid them and slid her fingers under the waistband of my boxers, I shivered with lust. I lifted her off the couch, she wrapped her legs around my waist, and we kissed all the way to her bed, which was actually her roommate’s, but she didn’t care at this point.
I laid her on the bed and slid her shorts and panties off; she sat up and pushed my pants and boxers down. Her face was right at my crotch, and she did the natural thing, she took me into her mouth, once, twice, and so on, until we both knew it was time. She laid back, I knelt between her legs, and after I missed twice, she guided me into her, I slid in like I knew what I was doing. I trusted her enough to know she’d have said something if she wasn’t on the pill, and so I hoped her boyfriend was pretty faithful. (He wasn’t, but it turned out all right.)
I came in under a minute, but I didn’t even feel embarrassed, because we really had worked up some passion that summer, and both kept it pretty close to the vest. I let her know when I was ready again, and it wasn’t long, and we fucked again, and I lasted a good while longer this time. I’ve never really been able to come twice quickly. I’m sorry to say I never made her come that night by sex, but I did stroke her to orgasm and then we went over to her bed and fell deep asleep. I woke up the next morning and she was showering. It didn’t feel right to do anything more that morning, but we went out to breakfast and I felt so weird knowing that I was sitting there with my friend who I’d just fucked. We talked about liking each other all summer, but that talk kind of petered out and we started chatting about random stuff. I left that afternoon and I visited her a few times during the fall. The sex got better each time. She got a belly ring, which was sexy.
The funny twist in the story is that Andi and I are still friends, but it’s Michelle who ended up being the girl I fell in love with – the next summer, when Andi and I had a brief falling out because she had gotten together with some new guy from school, I got to know Michelle, and her quiet charm got into my heart in a way I’d never felt before. It didn’t hurt that Michelle could make me come by blow job in five minutes flat. We got married five years later. Michelle has no idea about Andi and me, although sometimes I think she suspects. It’s always a twinkle in our eyes, and sometimes I think Andi and I will have another fling, but we both are in committed marriages and it will have to be a pretty convenient opportunity for that to happen.
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Road Trip
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