Where it happened: college
Langauge: English
Sex: Male
Rating: 6
Category: Straight
My first time was with a girlfriend (Katie) in college during our freshman year. We had dated for a while but had never done more than kissing, groping, and fingering. On Halloween night we were in her room alone (her roommate was out of town). Katie lived on the 12th floor in the Williams Village apartments, which are 15-20 story dorms just off campus at CU-Boulder. The large window in her room looked out over Highway 36, and Katie liked to sit on her roommate’s bed (beside the window) and watch the cars on the highway at night. We had been doing some heavy kissing and groping, both in nothing but our underwear, earlier in the evening, and Katie was pretty turned on. After taking a bit of a break from making out, she position herself on the bed by the window, but rather than sitting, as she normally did, she was on her hands and knees staring at the highway below.
As she watched the cars, I came from behind and began dry humping her, “doggie style.” She clearly liked this and after awhile wanted to take off her panties. However, afraid someone would see us at the window, she moved to her bed. We both took off our underwear, and as before, she positioned herself on the bed on her hands and knees. From behind, I slowly began rubbing my cock on her labia and clit but not in her vagina. She was remarkably wet and really turned on by this time. I continued to stroke her labia with my cock until we both became so wet and her vagina was so gaping that my cock slipped right in. She inhaled sharply and moaned slightly as I slid my cock in and out of her pussy.
This went on for only a minute, when she pulled forward and told me to lie face-up on the bed. I quietly complied, and she positioned herself over me on her hands and knees. She slowly slid her vagina down over my cock and began working away on it. Although a virgin, her vagina was, in a word, roomy. I had fingered her many times before this, and over that time she was able to take additional fingers until it was common that I inserted all of my fingers.
Stretched out on the bed, I fondled her breasts but lay absolutely still as she slowly, rhythmically pumped away. Neither of us were using condoms, nor was she using birth control, so I held off cumming, not wanting to get her pregnant. But she kept pumping and pumping and pumping until I couldn’t hold it anymore. By now my head was spinning and the explosion from my dick was accompanied by fireworks in my head.
Katie kept pumping away until she came, quietly. She collapsed onto my chest and soon began softly crying. She was not distraught, but clearly these were not tears of joy. I waited awhile and asked what was wrong. She paused before answering, “I had hoped to wait until I married for my first time.” Now she felt as though she had betrayed that hope. Instantly, what had been a seminal experience in my young life turned sour and guilt-ridden.
Katie climbed off me and went to the restroom. I cleaned up using the sink in her room and waited until she returned. I apologized awkwardly and then left to go back to my dorm on campus. We continued to date for the remainder of the year and into our sophomore year. We also continued to kiss and grope a bit and even tried a little oral sex, but never had vaginal sex again. As a couple, the first time was the last time.
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