My first sexual experience with a woman happened during my third year away at college. I was raised Catholic, went to an all-boys Catholic high school, lacked confidence, was painfully shy around girls, and had no idea how a boy was "supposed" to act around girls, let alone approach them for intimacy. I was afraid of being rejected, I guess. And besides In those days just about everything "intimate" was a mortal sin.
Fall quarter of my junior year, I was invited by some of my ROTC mates to a party off-campus. It was a set up blind date; a chum's girlfriend had a friend who was just as shy as I was and wanted to meet a "nice" boy, i.e. virgin who wouldn't try to rape her on the first date. There was beer at the party, soft lights and slow music. We were dancing a slow dance. She moved closer and closer as we swayed back and forth to the music. I was getting hard. Pretty soon we were so close that one of her legs was between mine against my crotch, and one of mine was between hers. My arousal was really prominent and she pressed into me with the same curiosity as I showed to her.
After the party we agreed to meet again and had some fun dates. Eventually, this led to French kissing make-out sessions in my car. She was the first girl I ever got to put my hand on, and then inside, her panties. Hot and wet....one of life's great mysteries revealed. She was the first girl to ever put her hand inside my pants, and then underpants. On subsequent parking forays in the deep woods, she put my hand on her and showed me how she liked to be rubbed. I took my pants and shorts down exposing my boner, and she stroked it in what I realized was a very knowledgable way.
I had a single room in my dorm, and we had study date nights, Wednesdays, I think, when guys could have girls in their rooms until a certain hour. Our study dates always ended up with us at least partially undressed on my bed making out. One fateful night, we found ourselves totally naked and very excited. A friend who knew about my inexperience had given me a rubber I kept in my wallet just in case something should happen. I sat on the edge of the bed, put in on, and turned around to her. She invited me on top and helped me in. After awhile she said, "You know that new birth control pill? I taking part in a study about here at school. I can't get pregnant. You don't have to wear that." So I rolled if off my erection, tossed it on the floor, and she once again invited me in. Only this time the sensation was spectacularly exciting as I slid into her. I was spellbound, moving up, down and around as she held my bottom and moved me around inside her. I had a climax like I've never had since. We laid together a long time after that, until the last minute when study date time was over and she had to leave.
We dated for several months after that. I'd heard talk that she was well known around the fraternities as experienced. But it didn't matter to me, only that I had a lot more to learn and she could be a good teacher. She liked to suck me and jack me off. She was a nursing student and on more than one occasion showed up with examining gloves and K-Y. She was my first real sex, and also the first to show me how good she could make feel, and how hard I could cum, with her finger in my rectum working on my prostate.
Eventually, we broke up. There wasn't much else to the relationship besides mutual horniness and sexual frenzy. We both knew when it was time to move on. Beware of set-up first dates with nice girls looking for nice boys.