Where it happened: Ann Arbor, Michigan
Langauge: English
Sex: Male
Rating: 7
Category: Straight
I dated Karen briefly when we were freshmen at the University of Michigan early in 1969. She wasn’t my idea of my ideal girlfriend. Except that she was a successful student at a prestigious university, she reminded me of the Rolling Stones’ song “Factory Girl” on their album “Beggars’ Banquet” (just released then). We had no classes or interests in common and we did not even talk much, as you will see. Karen did tell me that she was a virgin and that she took birth control pills to regulate her periods. I remembered that!
That fall as sophomores we dated again. I had just turned 19 and was a few months younger than her. We both lived off campus in apartments. While necking in her bedroom one of us, I forget who, removed her shirt and I massaged her nipples through her bra. Karen pulled off her bra and exposed nice breasts. It was the first time I saw a partially naked girl. She was down to her panties. She said I could stay the night rather than walk home in the frosty cold of the October night.
“Should I remove my trousers?” I asked her. (I was wearing the rage in rags: bell-bottoms!) Normally I didn’t sleep in my clothes. “No,” said Karen. I spent the night with her in her bed anyway. Maybe she was in her period.
The next Saturday we dated again. I knew sex was imminent. This time Karen was ready. Since I had respected all her requests that far, she trusted me to deflower her acceptably. I think her motives were curiosity, interest in me, and competition with her roommate, who had just acquired a boyfriend. My motive was curiosity but my feeling for Karen was that it would be kinder to leave her intact for someone who liked her more than I really did. But curiosity won.
After seeing a movie (VCR’s didn’t exist) we returned to her apartment. I chatted with her roommate until Karen led me by hand to her bedroom. We sat on her bed and I massaged her nipples and unsnapped her bra. She quickly removed it, exposing her breasts, and then unbuttoned my shirt, which I removed. She pushed off her skirt and this time she pulled her panties off, too. She was naked for me! Boldly, she undid my belt and unfastened my trousers.
We lay on her bed and maneuvered into missionary position. My underpants were still on. I wondered whether she just wanted to neck more. I didn’t have to ask: She slipped her hands down my buttocks and pushed my underpants down, bringing my erect penis out. Her hands held me there while I kicked them off. For the first time in my life my penis touched a woman’s vulva, and for the first time in her life a penis touched her! Karen tugged on my hips to tell me to penetrate into her.
I thrust forward. My penis felt her warm flesh and cold air simultaneously. “Am I in you?” I asked her. “Go on,” she murmured ambiguously, imagining I knew what I was doing. I didn’t know, but it felt pleasant if strange to thrust so I did until I came and ejaculated. But in fact my penis had slipped beneath her vulva and only her thighs had stimulated me. I left a cold puddle of semen on her sheets. I was mortified. My mind is thankfully blank from then until I fell asleep! My next memory is of Karen nudging me awake in the dark.
“Let’s try again,” she offered. (No kidding.)
I groggily mumbled something to the effect, “Go back to sleep.” I had no desire and Karen had no foreplay skills. Had she caressed my penis to erection we might have screwed successfully. Advancing my sexual career was not a big personal goal for me and having Karen as a girlfriend was not a goal at all. I declined to date her again after that night. She was unhappy that I left her frustrated when she had been so close to sexual experience and embarrassed her in front of her boyfriend-equipped roommate. But I was firm. For a while!
(Continued in 1969: Part 2, Make Love, Not War)
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