[This is my first submission to Literotica. Much thanks to my volunteer editor amerks29hockey for her help in this. All remaining errors are mine. This story is 90% true. The names have been changed to protect the guilty.]
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My real first time intercourse is nothing to write about--quick and unsatisfying for both of us, and my girlfriend cut me off as of the next day. Can't really blame her.
My most erotic early encounter was this one with my third lover:
At the end of my sophomore year in college, my brother, two years older, was set to be married at the college chapel. I obtained permission from the college to stay in the dorms five days after they were officially closed. Just about everyone else had left even days before that, as they finished their final exams for the term.
Jane, the girlfriend of one of my roommates, broke up with him before exams started, but they were still on fairly good terms. She was planning to tour Europe that summer but needed a place to stay between the times the dorms closed and her flight left. Matt told Jane that she could stay in his room (we had a two bedroom suite with a living room between the bedrooms containing bunk beds), since the room would be open with my extension. In addition to the convenient place to stay, she liked the idea of having a guy in the suite for security, with the campus emptying of students rapidly.
I had coveted Matt's girlfriend Jane ever since they got together last fall. Matt and I were amateur photographers and he had taken some terrific photos of Jane. She had an allure that really came across on film. Tall and athletic looking, with legs longer than her torso, she was 5'9" with long straight dark brown hair that stretched down her back to her waist. Her breasts appeared smallish, but a B cup suited her body type well. She was probably twenty pounds over what a model's body would be, but that made her more desirable for being closer to normal. Her little button of a nose sometimes seemed to turn up as she often lifted her chin to reveal an elegant swan neck. She had an impish grin, with sparkling eyes, though, which told you she was not snobby in the least. On more than once occasion in the dorm darkroom when Matt and I were developing our pictures, I told him how lucky he was to be with her. He knew.
I had broken up with a girlfriend myself a couple of months earlier. Kelly was smart, sassy and pretty with a great rack on a nice 5' 4" body, topped with wavy red hair down to her shoulders. Kelly attended another college about an hour's drive away. After several months of dating and trying to overcome her Boston Catholic schoolgirl notions about sex, the most I had accomplished sexually was to uncover and suck her lovely globes and slip a finger into her wet slit. I finally gave up and told her it was time for us to move on.
So, at least theoretically, Jane and I were both available to each other, romantically speaking. When Matt finished his exams and was packed to go home for the summer, I helped carry his luggage to the airport shuttle bus two blocks from the dorm. Jame walked with us. Just before he boarded he embraced Jane and gave her a deep farewell kiss. My gut fluttered in envy. Jane blushed a little as she turned away to walk back to the dorm with me. We walked in silence all the way.
The dining halls had closed, so for several days we pooled resources to make dinner on a hot plate in the living room and eat together. On those dinners Jane and I had together alone, we started to get to know each other as something other than girlfriend-of-roommate and roommate-of boyfriend. Despite my long-standing attraction to her, I did not start out thinking I had any chance with her. While not exactly taboo, trying to seduce my friend and roommate's girlfriend, even an ex-girlfriend by a week or two, would be considered bad form. Plus, I didn't think I was up to the challenge anyway. Although I was not a virgin, I was not experienced. She was a year older and being a hot girl at an Ivy League school where the ratio of women to men was 4 to 1, she was pretty far above my status.
The night before she was to fly to Europe, I attended my brother's bachelor dinner party at his off-campus apartment. It was a tame affair, no strippers or any other girls. A group of about 10 of us listened to music, talked about the Vietnam War, played the word game Balderdash, listened to The Allman Brothers music, drank beer and smoked weed. Not long after we ate, perhaps emboldened by the alcohol and marijuana, I began to talk myself into making a move on Jane. Around 11 I had worked up enough courage to try. I stopped in my brother's bathroom to slug and gargle a glassful of mouthwash before walking back to my dorm room.
The coolness of the nighttime air and the exercise of the 15 minutes it took to walk the distance back to my room helped clear my head. Sober but nervous, I slipped the key into the lock of the door. I entered the dark and quiet living room and closed the door behind me. The room was lit only by moonlight through windows on the far side. I hesitated. Should I turn right to Jane's room or left to my room and my own bed? I noticed Jane had left her bedroom door open, so I turned to the right and stood in her doorway. She had closed the curtains to the bedroom window, so only a small sliver of moonlight entered. My eyes still had not adjusted, so I couldn't see anything, but I knew the room. It opened as a rectangle to the left from the entry door. Three feet straight ahead of me was the closet. Immediately to the left on the near wall was the only desk. Further down to the left were two tall metal dressers. The bunk bed was on the far side, across from the desk and just to the left of the closet -- just six feet away from me.
"Are you still awake?" I whispered.
"Yes," she replied. "I'm glad you came in. I was afraid I wouldn't get to say goodbye before I left in the morning."
