It was long time ago, so this story is to the best of my recollection.
I was at a military technical school in Illinois. I had made quite a few friends at school and there was this one girl in particular, Carol, which I hung around with. We got along great. I was engaged to a girl back home but Carol and I were just friends and fellow students.
One day we took a drive in my newly purchased, used car up to Chicago. We saw the sights and the Sears Tower and had real nice day. We started back home and got stuck in the middle of rush hour traffic. It was beastly and we got lost. Soon it was well after dark. It was really late by the time we ended up near an airport and found a motel advertising cheap rates. She suggested we not try to drive back in the dark since we were lost and that we stay here and start out fresh in the morning. I was for it so we stopped to get a room. We didn’t have much money left because we had only planned on a day trip. She got down in the floor of the car and I was going to get us a single room. They wanted the money up front and I didn’t have enough on me. I told the attendant that the rest of my money was in the car and got the rest of the money from Carol.
We were finally in the room and began to get settled for the night. I saw the 1 bed in the room (luckily it was a full size bed). We were just friends and had not even so much as kissed up to this point but I thought, “OK, one bed, two people. I’m not prude. I can do this.”
Things kept getting better. She undressed down to her underwear without even a thought and said she was going to take a shower. I sat on the bed and flipped through the channels while she washed. I was still dressed when she came out of the shower wrapped only in a towel. She tossed her bra and panties on her pile of clothes. She sat on the bed for a few minutes and brushed her hair. Then she took the towel off and I got a glimpse of her naked body as she climbed under the covers.
I took my turn in the shower and thought long about what I should wear when I left the bathroom. Apparently she had no hang-ups about nudity. Since we had never done anything that could be called romantic in the past, plus the fact that I had a fiancée back home made it was a hard question. I decided to play along put play it safe. When I exited the bathroom I had my underwear on but I carried my clothes.
She was siting up in the bed watching the TV. The bedspread was draped loosely around her and her tits were exposed. I tried my best to play it cool and tossed my clothes in the chair and climbed into bed with her. She immediately huddled up close to me saying it was cold. I put my arms around her.
Now my brain was finally getting the message that she wanted more than just a night’s sleep before we went home.
You can probably figure that I did a lot of thinking. My fiancée and I hadn’t progressed beyond me feeling her tits. Although I had seen her naked, I hadn’t even fingered her but I respected her decision about that and never pressed the issue.
Now here was a woman. Naked, in my bed, sending me very clear signals that she wanted it. Not having seen my fiancée for a couple of months while I was at school made me lonely and horny. What to do…what to do.
I reached for the remote and turned off the TV. Then I laid down under the blankets and she came with me. I rolled over a bit so I was looking down at her. Just to be safe and that I wasn’t misreading her signals, I said, “Good night,” and kissed her. She put her hands around the back of my head and kissed back. She kept her hands around my neck and we kissed again. I wasn’t misreading her signals. We kissed long and hard. My hands almost immediately moved to her tits. They were smaller than my fiancé’s but they were as firm as a citrus fruit. I kept kissing her and feeling those firm tits for quite a while. Then I dared to venture down with my kisses. I got to her neck with my kisses and she wrapped her legs around my right leg and pulled my thigh up tight to her crotch. When I got down to her tits I ventured to touch her bush. The hair was stiff and curly. I rubbed her there for a bit, then moved down between my leg and her crotch. I clumsily parted her pussy lips but found her wet vagina quickly. I inserted my finger and, being new at this, began to slide it in and out. She pulled my underwear off and gently wrapped her hand around my cock and stroked it slowly. After a while she moved my finger to where it would do more good. Her clit. We kept at that for about 10-15 more minutes then she shifted us. She moved under me and guided my cock to her vagina. At last I was there. I pushed and didn’t have the right angle. It took a few tries and she raised her hips up to meet me before it slid in.
As I pushed into a woman for the first time, I marveled at how it felt. The tightness, the wetness, how the folds of her vagina felt against my cock. I went straight to thrusting in and out of her pussy and, of course, I came in less than a dozen strokes. I pumped my cum into her and she smiled at me. I didn’t really know what to do after cumming so quickly, but she didn’t seem to mind.
What I did know was that I was still hard as a rock. So I put it to good use. I kept stroking in her pussy. She lay there under me and I wondered what it felt like for her. I tried some variations on the angle to make it better for her but, while she enjoyed it, I couldn’t tell how much. She never gave me any sign when or if she came.
I stroked her for 45 minutes before I came again. By this time I was tired and covered in sweat. After releasing my load in her I stopped and held her close. I ventured to ask how many times she came. That’s when she told me that she had trouble having orgasms and the only way for her to get one was with the help of a vibrator. I thought, “Oh well. At least I tried.” We lay there for awhile to recover from our love-making and fell asleep.
The next morning, we made love once more. This time she got on top of me and straddled me while I watched my cock disappear up into her. She rocked back and forth on my rod for a few minutes. At least this time I had the wit to try and help her along too even though she said she needed a vibrator to orgasm. I reached up and thumbed her clit while she rocked on my cock. Realizing that this would soon end, I concentrated on the feeling of sliding in and out of a woman. Again, the silkiness of her vagina moving against my cock was wonderful.
Then she started to rise and fall on it. I kept my thumb in place as best I could. I lasted longer with her this time but it still wasn’t very long before I came and spurted into her pussy for the time. She continued to ride me for a while before she stopped and got off me. After lying there a few more minutes we dressed and, in the light of day, left for the base. All in all it was a good trip.
We never made love again. Even though I felt guilty for cheating on my fiancée, in reality, Carol and I were just good friends who decided to be intimate with each other. Neither of us had any intention of raising it to any higher level, such as boyfriend / girlfriend. Especially since we would be stationed half way across the country from each other.
After we finished school we each went our separate ways. I went home on leave only to find out my fiancée had another boyfriend. Carol and I kept in touch for a number of years, even after we both eventually married others, but it was mostly at the holidays. Even though there was never anything serious between us, she will always have a special place in my heart as my first.
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