Two First Times

Losing my virginity was the biggest anticlimax ever. I was 19, a freshman in college, and I just itching to get laid. It may sound stupid now, but I hadn't dated much in high school, and I was really afraid that I would die a virgin. I was shy, and I didn't have a very good self-image. Also, I had discovered the joys of penetration early, and I had built up penis-in-vagina sex in my mind as the ultimate sexual pleasure. I was dating this guy who we'll just call Mr. X. He was a couple years ahead of me, but seemed so much older. I knew he wasn't all that, but that was alright. He was smart, fairly cute, and had the hots for me.

We had been fooling around for a while already. I liked sucking his dick, and it was fun making out with him. He hadn't actually made me come yet, but that was ok. I was pretty good at doing myself.

I should have known it was a bad idea when he didn't want to use a condom. He promised that he wouldn't come inside me, but I was having none of that. He argued, sulked, and complained, but I was firm. I should have walked out then and there.

Well, it didn't hurt; I'll say that much for it. It wasn't much fun either. I had been fucking myself with improvised toys for years (some quite a bit larger than his penis too), and I don't even remember losing my hymen. What is was was uncomfortable, selfish, mechanical, and over mercifully quickly.

He never spoke to me again after that night. I hadn't told him I was a virgin (I was embarrassed), and I don't think he knew he was my first. He stopped calling and avoided me outright. I saw him around, but I never spoke to him again. I don't know what his deal was. I was a wreck. Not that I cared that much about him in particular; I just thought there must be something horribly wrong with me to make him act like that. I thought I must be terribly unattractive.

At thanksgiving break, I stayed at school, while my roommate and almost everybody else in the dorms went home to see family. It was too far for me to travel and I couldn't afford it. I was feeling really low. I was exhausted from midterms, and still an emotional wreck from being used and dumped by Mr. X.

Kathleen lived in the dorm across the hall from me. She was beautiful. I mean, like super-model beautiful. Tall (not as tall as me, but tall), long red hair, flashing blue eyes, curly eyelashes, tight butt, big (but not too big) breasts, amazingly fit; I don't think there was an ounce of excess fat on her, and she had beautiful shoulders. I love a girl with a nice back, and hers was amazing: toned and muscular. She was a dancer, and I had wanted her from the moment I saw her. Needless to say, we barely even spoke to each other. She had a boyfriend, a couple years older, disgustingly good-looking, and probably wealthy. I was a tech theatre major at the time, and I was always wearing grubby clothes and working in the theatre.

It turned out that Kathleen was one of the only other students on my floor who had stayed at school for the holiday. She had a roommate, Nancy, who scared me. Nancy was another dancer, beautiful too, but severe and aloof. But Nancy had gone home for the holiday.

I had certainly thought about lesbian sex before. Actually, it was one of my favorite fantasies as an adolescent; up there with fucking the brains out of that boy on the track team (among others), and having anal sex (preferably with a skinny, smart punk-rock poet). But I had never actually had a crush on a girl until Kathleen.

Saturday morning we had breakfast in the dining hall, all 12 or so of us 'orphans'. I worked up my nerve and asked Kathleen if she would like to hang out and play cards or listen to music or something. She said sure, later on. I swear that was the longest conversation we had ever had up to then. My heart was pounding, and my head was full of lustful thoughts.

Understand that, although I had a healthy fantasy life, and had been masturbating to thoughts of Kathleen for months now, I didn't really know much about the mechanics of girl sex. When I was in high school, I had assumed that lesbians had to use strapons to have sex. (Not that there's anything wrong with strapons!). Research and reading had since informed me that oral sex was a big part of it. Problem was I had no idea what one was supposed to actually DO once you had your face in the pussy of the one you desired. I guessed that I would make it up as I went along. If I even got the opportunity... God I wanted her! It was a long afternoon.

I remember that I spent the day in an agonizing mix of anticipation, trepidation, lust and frustration. I didn't want to go out in case Kathleen knocked and missed me. I tried to read. I tried to watch tv. I went down for lunch. I masturbated. I took a shower. Waiting was driving me crazy. She probably wouldn't come by after all; she was a popular girl, she had a boyfriend, we had never even spoken or hung out before.

Kathleen knocked on my door about six. She looked beautiful. Her hair was done up in a bun. I noticed that she had a dusting of freckles on her highly defined cheekbones. Her blue eyes flashed. I felt giddy, almost sick with lust and nerves.

We hung out in her room and talked and played cards. I honestly don't remember what we talked about. All I could think about, more than anything in the world, was that I wanted to kiss her. And I wanted her to kiss me back.

She mentioned that her shoulders were stiff; she had been working out that afternoon. Heart pounding, I offered her a massage. She accepted. I sat behind her on the floor and started to rub her shoulders. Touching her, my hands on her skin, well, I was getting really physically turned on at that point. It was incredible.

Kathleen groaned, told me that my hands felt great. I couldn't stop myself. I leaned forward and kissed her softly on the cheek. I was totally prepared for her to freak out, to throw me out of her room. Instead, she turned her head and kissed me on the lips.

I can't describe the sensation of that first kiss. It was heaven. Not an orgasm, but better in a way. I didn't ever want it to stop.

She pulled back. "Is this ok?" she asked. In answer, I kissed her again, harder, hungry for her.

We kissed for a long time. We spent over an hour, just kissing. We didn't talk, we didn't undress or grope, just kissed each other's mouth, face, neck. We pressed our lips together and breathed each others air.

We found ourselves on her bed, with me lying on top of her. She said something like "Please Andrea I need you to touch me" and brought my hand to the ample swell of her breast. That was enough for me. I unbuttoned her shirt and with her help unsnapped her bra (I never understood before why guys found it so difficult!), lowered my lips to her erect nipple, and tasted her delicious breast flesh for the first time. I was in heaven!

Well it didn't take us long to get naked. I was incredibly turned on. It was the first time I had ever been that wet before; by the time she pulled off my jeans, I had soaked all the way through them. She looking incredibly beautiful naked, all muscular and slim and feminine and sexy. Her breasts were large and round; her pussy was nearly shaved, with just a neatly trimmed patch of reddish hair covering the mons. In comparison, I felt like a naked giraffe. To my lasting joy and astonishment, she didn't seem to think so at all. In fact she seemed almost as turned on by my body as I was hers.

She was a little more experienced; I gathered that she had fooled around with girls before. She taught me how to eat her pussy, how to lick her clit. I loved it!! I had, of course, sucked guys off before, and I really enjoyed doing that, but this was amazing! I loved the taste, the smell, the sensation. I loved having her wetness on my face, making her squirm and shake and come. I flicked her clit with my tongue and fingered her pussy. I wanted to probe her puckered little asshole too, to stick my tongue up there, but I didn't. I didn't want her to think I was a pervert.

She went down on me next. It was great. It was like I had always hoped that sex would be like. It wasn't the first time I had had orgasms with another before, but it was the first time I really surrendered to it.

We spent the entire night together. It turned out that she too had a vibrator, and we took turns fucking each other. It was such a turn-on to see the red toy slipping between her lips, filling her pussy as she diddled her clit. I loved it when she fucked me with her toy. I've always liked having something inside me when I get off, and having her drive it into me set me off again and again. I wanted to be utterly hers. I really wanted her to stick the buzzing rod up my asshole, to spank my clit silly while she fucked me in the ass. I was, alas, too shy to ask for it.

We slept in her bed, cuddled together, sticky and naked and tired. We had sex again in the morning, lazy sensual and slow. Then we went down to the cafeteria and had breakfast together. We had skipped dinner the night before and had worked up quite an appetite!

We had a lot of sex over that thanksgiving holiday. It was amazing, life-changing sex for me. The problem was, I wanted her to be my girlfriend, and she already had a boyfriend. I was convinced that I was in love with her, and she just wanted to fool around. At one point she half suggested that we do a threesome (and I could totally kick myself!), and I laughed it off. We got together a few more times after school started again, but it wasn't the same. It felt like we were sneaking around, and I felt like I was competing with this guy. I was jealous. And the truth was, aside from the sex, we didn't have all that much in common. We couldn't find much to talk about. Truth be told, I don't think she was that bright. So we drifted apart. We became less than friends, but more than acquaintances. She got engaged. I got busy with school. We totally lost contact. I hope she has a good life.