Where it happened: School
Langauge: English
Sex: Male
Rating: 5
Category: Straight
My first time.
Throughout high school I didn’t date much. I went to an all boys school, Lane Technical, and was very busy in academics and music, and just didn’t think about the complications of having a girlfriend. None were dropping into my lap anyway. Although attractive (as I look back on myself) I didn’t see myself as desirable to the opposite sex and nobody in my family ever talked to me about the real stuff. No brothers, no sisters, and no friends at school who had more experience with girls, so as Handel would say, “I walked in blindness.”
When I got to college, at our first freshman orientation, I met C and was immediately attracted. She was shy, modest, spoke very articulately, and was from the Chicago area like myself. She was a Fine Arts student. I began calling her and we would meet. She was very shy and so was I. I think we wrote letters back and forth but I didn’t as much as hold her hand for the first couple of months. It was heady enough having someone who appreciated me for my best qualities, and she obviously was flattered to have my attention. When we went home for the Winter Break, we took the Greyhound together. She gave me a gift, the Brahms Fourth Symphony, the CSO conducted by Carlo Maria Giulini. A beautiful gesture. On our bus trip, we quietly held hands, and that was exquisite for me. Something in my upbringing taught me that if you really liked and respected a girl, you didn’t get physical with her. That was what you did with those “bad girls.” Of course, I probably wanked a thousand times to the thoughts of being with those bad girls, but when it came to real relationships in my life, I felt very held back. My belief was that women don’t like sex. They suffer to put out what they have to to keep their men. I thought the male anatomy was strange and ugly (compared to women’s, as exemplified by their breasts and skin. I’d never really seen a pussy, so that was a mystery to me.)
When we returned to school after the break, things became more developed. We sent notes to each other in our student mailboxes. One day she came to my dorm and we visited in a lounge downstairs. Nobody else was there and we were sitting on a couch, I on the arm and she leaning with her back on my chest and laying the length of the couch. From that angle I was reaching my arms around her and feeling the marvelous softness of her breasts. She didn’t seem to object. This was incredibly exciting for me, but she offered nothing more and I certainly wasn’t going to ask for more. But it registered with her. We began seeing each other on a Friday or Saturday night, where she would come to my dorm room (My roommate, bless his soul, would vacate the place for us) and we would neck and fondle all evening on my bed. We were kissing by this time. She said she was hot and I said take off your sweater, and she was shy to do so. I didn’t know she was bare underneath otherwise I wouldn’t have been so bold. Then she did. And so for the first time I got to see, touch, and kiss a real woman’s breasts, skin to skin. It was incredible. We both had our pants on, but bare on top. I guess we both felt mutually inhibited from stripping further at the moment. I was grateful for the bounty I already had. I didn’t have the term “blue balls” in my vocabulary but they got to have been mighty swollen and unrelieved, and I probably thought of those breasts a lot in the privacy of my own bed and bathroom as I took care of myself.
C didn’t say much about what was going on in her mind, although it was very stimulating for her too. We were good friends and shared a lot of conversation and laughs all the while. What else could sustain us for all those hours laying around. Then in one of her letters she to me said she definitely wanted to ‘go to bed’ with me but it wasn’t the right time. I didn’t know what that really meant but I happily accepted the fact that it was on her agenda. Frankly, I didn’t know the mechanics of it. She came over one day in response to a romantic note I sent and we grappled with each other on the bed. I put my hand down the back of her pants and she immediately withdrew it, which confirmed my fear that she wasn’t interested. We got into a semi-69 position and I was nuzzling her pussy, and she immediately pulled away. I felt something hard there. (I believe now it was a panty shield, and she was having her period.) But this withdrawal I took as another confirming sign that I was overstepping a sexual boundary. So I didn’t know really what this declaration “I want to go to bed with you.” meant and when it would materialize.
Then in April or so, we had tickets to see the Ressurection Symphony No. 2 of Mahler at the St. Louis Symphony. [We had a series subscription together, and a lot of our dates had been to go to the symphony.] When I came to pick her up, she was in a white dress that was all puffy and gossamery. It looked like a wedding gown to my eyes. It had a synthetic feel to it. Perhaps it was a nightgown. We kissed in greeting. This was a night where her roommate was gone for the weekend and we would have the room to ourselves. She said she didn’t feel like going to the symphony. I said, “What do you want to do?” She said, “This.” and kissed me more and I was feeling her through that gown. She said the equivalent of “Get your toothbrush and get back here ’cause this is the night!” I went back to my dorm room, and was a little bewildered by what I was getting into. I didn’t have condoms, and I didn’t forsee that on the agenda anyway, that would be too much, but I didn’t know for sure. I must have dallied because she telephoned me to say, “Where are you?!”.
I came back there and we put the two beds together. We got into bed. She was in pajama bottoms and so was I (the same kind of configuration like on our necking nights at my room) but we both knew some ceiling was removed. I didn’t know how high the ceiling was. In all honesty and sincerity I said, “Could you give me an anatomy lesson?”, and she said “No.” I really could have used one. Perhaps she was being shy and coy and really wanted me to to take over and find out for myself somehow. I said something like, “What can I do [how far can I go?]” and she said, “Anything.” But I didn’t grasp that “anything” really meant ANYTHING. I didn’t sense she did something to protect herself from pregnancy and I knew I didn’t have anything. I did take her pajama bottoms off and for the first time in my life licked and tasted her pussy, which was cool. I could go on and on about that alone. I didn’t know what to expect. Now, one minor disappointment was that I imagined her pubic hair would be soft as a ktten’s fur, and it wasn’t … it was hairy-feeling. I liked the smell … and I spent quite a while indiscriminately licking. Finally she said, “That’s enough of that.” and put her pjs back on. And that was all I had the courage to do. There was no move from either of us to mutually touch each other to orgasm, or other sexual play stopping short of intercourse. I had gone father than I ever had in my life and it was good enough.
We didn’t have anymore amorous nights to explore it further until beginning of sophomore year. She got an apartment with a friend and came back to St. Louis a week early to help set it up. I came early to help out and looked forward to hot nights together.
But they never materialized fully. She confined our budding sex life to the nighttime sleeping hours. Neither she nor I had gotten courage to talk about contraception and learn about each other’s bodies. On one night where we earnestly tried to fuck, I tried to get it in but didn’t know that it was okay to use my hand to guide my dick or she could use her hand to get it where it should go. I had this mistaken notion that the love canal was perpendicular to the abdomen, so I was trying to go at almost a right angle to the direction it needed to go. Probably not enough lubrication either. No help from previous experience. Perhaps she was shy at heart because she knew we didn’t have protection. I was assuming she had quietly taken care of it, but didn’t ask, … and I don’t know what she was thinking about it, but she was too shy to ask either. Pehaps that was for the best. But it was a frustrating night.
Within a month or two, she left school and went back to live in Chicago, because of some psychological issues not important to get into here. It was a hard breakup for me and I was lonely for awhile.
Because I didn’t have success with intercourse, it left me wondering for a long time if I was physically okay. I mean, I could easily get an erection and ejaculate when I masturbated, but why was I ineffective when I was with a real woman. I didn’t have enough perspective to blame it on anything else but something about me. That was a burden I carried for another year or two. It made me unconfident with girls. I was rather like a young kitten who has the ability to catch a bird but doesn’t know what to do with it once he has it. Well, I hardly would get to that point of decision because I didn’t go after love and romance with the same patience and creativity as I had with C.
How I broke out of the vicious cycle is for another story.
I still think that my extremely slow coming to know sexual experience with C was valuable and a good way to start, because I really did develop the friendship and other aspects of relationship before getting physical and it was a good foundation. I think these things can happen quicker. I mean, two months before holding hands, is really extreme. But it was right for her and right for me, and when things did boil harder, we were both ready for the next step.
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