Beginning of a Beautiful Friendship

[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."

I could tell from the direction of her voice she was in the top bunk and her head was at the far end from where stood. I stepped over to her so my face could be near hers. The bed was just high enough that we were face to face while I stood on the floor. My eyes were starting to adjust, though all I could see of her was a silhouette. I could tell she was lying on her side facing me. I reached up to stroke her hair.

"I've really enjoyed getting to know you this week," I said. "I'm glad we had this time together."

"Me, too." She put her hand to the back of my head. We pulled each other together and kissed softly and unhurriedly.

Slowly, ever worried she would put a stop to my advances; I moved my right hand from her hair across her shoulder, down her rib cage to her hips. As I went I pushed aside the sheet covering her and surveyed what she had on as my hand made its slow journey: a cotton tee shirt and bikini panties. This was long before thongs came onto the scene and what she had on was about the smallest thing women wore back then. She didn't break off the kiss and our tongues played with each other. I took this as encouragement and slid my hand under her shirt, reaching up for the hardening nipple on her chest. I traced my forefinger around it trying to visualize it through my touch. I could feel her breathing rate increase.

I was convinced I could have her. Without breaking off our kisses I used my feet to push off my shoes and socks. While my right hand squeezed her breasts and explored her flat tummy, her rounded ass, the mound and then the hemline of her panties, my left hand unbuckled my belt and unbuttoned my jeans. My belt was two inches wide and had a large metal cowboy-style buckle. Once I had the waist of my jeans and boxers past my hips the heavy buckle carried them to the floor with a clunk. Her head snapped back a

little with a gasp. The heel of my right hand was touching the bare skin above her panties; my palm cupped her mound and my fingers pushed against her swollen labia. She wasn't backing away from me there. She had flexed her upper knee to give me access between her legs and despite her gasp of surprise, recognizing what it meant for my belt buckle to hit the floor; she pressed her pelvis into my hand.

It was time. I stepped onto the lower bunk, grasped the side of the upper and swung my body up over hers. She turned on her back as I came up and I lay on top of her. Her arms wrapped around my chest and her legs opened as I placed my knees between hers. Propped up on my elbows, I cradled her head in my hands. We kissed again, deeper and with more hunger. My hard erection was pressed against her, dividing the lips of her pussy through the cotton fabric.

"Wait!" she cried. "You're on my hair." I straightened up on my knees. She lifted her shoulders enough to pull that gorgeous waist-length hair up from behind her to fall over the top of the bed out of the way. I took the opportunity to hook my fingers behind the waistband of her bikini bottom and she lifted her hips to help me slide it down and then lifted her legs above my head so I could pull it past her ankles and feet. After tossing her panties on the floor I sat back on my heels. I peeled my own t-shirt off. Her legs wrapped around my hips and I was able to caress the entire front of her body, from the inside of her thighs to her perfect tits. On the way I grazed my thumbs over the mound of her cunt, through the dark hairs growing there and flattened my hands across her fluttering stomach. I circled her breasts with my fingers, at first avoiding the yearning hard nipples at the center, but then pinching them gently between forefingers and thumbs. I returned my thumbs back to the lips between her hips and stroked slowly and softly. She was moist there but as I stroked I dipped between her opening petals and found more slick fluid to spread upwards and over the nubbin of her clit. Just like the shampoo instructions, rinse and repeat.

While I was working her she had one hand cradling my aching balls and the other lightly grasping my shaft, her own thumb spreading the slickness of the drops at the end of my prick all around the swollen knob. When I knew she was ready I slipped my knees backward and leaned over her, supporting my weight on my hands placed on either side of her shoulders. She kept her hand on my cock, making sure my aim was true. I slid my throbbing cock through her open and sopping wet lips and into her canal in one long, slow stroke. I eased myself down onto my elbows at her side and grasped her shoulders. I pulled her body as hard as I could to bury my cock as deep as I could into her. We kissed again, open mouthed and devouring each other. Her feet were hooked around the backside of my knees and her hands clenched my ass. She wanted me as deep into her as much as I did. I then started rotating my hips, stirring the pot of her sex and pulling out and pushing back in just an inch or two at a time.

Only a few minutes passed in this ecstasy before I felt her whole body begin to tense up leading to her climax. She broke off our kiss and her head arched back, mouth open in a silent scream. Then it hit her, the jerking spasms from head to toe. Her hands left my ass and her arms hugged my back as she cried out.

"Ahhh, ahhh , aahhh, aaaaahhhhhh!"

I didn't know if it was the sight of her coming or the clenching of the walls of her pussy that sent me over the edge. So much cum spurted forth I thought my balls were dissolving. I imagined my whole body might be sucked up through my cock, turning me inside out into her womb. I don't know if I made a sound more than a squeal and lights were exploding in my head. At long last I collapsed on her as we both tried to catch our breath.

After a minute or so, I shifted the weight of my upper body a bit to the side, setting my head on my cocked arm. My cock deflated some but it was still inside her. As I smiled at her, my cock would twitch, producing a clenching twitch of her own. Sometimes her puss would clench and I would twitch in response. Eventually I went limp entirely and slid out, followed by the ooze of our mingled juices. I lifted off of her and stretched alongside her. She laid her head on my upper arm and we cradled each other, soft caresses exchanged in the exhaustion of our bliss.

I awoke on my back with the morning light pushing through the curtains, hearing the sparrows chirp. Jane's head lay sideways on my chest, her arm around my waist and her top leg hooked over mine. Her lower shoulder and arm nestled at my armpit and I could reach with that hand to her lower back. I could feel the firm muscles below her skin. I could feel the curved dimples in the low of her back just above the mounds of her delightful ass. I loved watching her sleep and I loved seeing her stir gradually to consciousness as I caressed her back and ass. She smiled without opening her eyes. I could tell she was awake, so my caresses became more purposeful.

With the hand draped across her back I found the crease between her cheeks and slid a finger along its length. She clenched the muscles of her butt to get away but that forced her still damp snatch against my thigh. My cock was already awake and stiffening when her fingers began their own exploration. Without lifting she shifted her head just enough to see what her fingers were feeling. With fingertips or nails she felt its entire length, touching each swelling vein, the sharp ridge of frenulum below the Cyclops eye—the rounder ridge defining the difference between the penis shaft and cock head. She pulled the testicles up away from my crotch, not hard, just enough to see how much skin comprised the sac.

When a drop of clear fluid appeared through the eye she shifted her head downward, pursing her lips to engulf the tip and suck out what fluid she could.

"Mmmm. Tastes great," she said.

"Less filling," I replied, mocking the Miller Lite commercial.

She giggled. "Oh I wouldn't say that. I found it quite filling last night."

She then slipped the lips of her mouth over me again, not taking me deep but just an inch or two beyond the head. My balls began to rise, which she could notice from hand massaging them as she sucked.

"I think we have time for another round before I have to go, "she said, rising to her knees and straddling my hips.

"I certainly hope so," I agreed. I grabbed her hips enough to pull her forward and up just enough for my straining cock to align with her gash. Pushing her back and down, the head found its mark. Still holding her hips I pushed down just enough for my cock to pierce the top inch of her. I pulled her up, the tip of my cock pulling out the lubrication to her outer lips. Three more times of this movement, each dipping slightly more than the last, gave enough slime to slide deep inside her.

This time we were more leisurely pleasuring each other. The urgency of the night before was gone. We were taking our time. She sat upright, rocking her hips back and forth so the top of my cock sometimes would rub the nickel sized flesh of her g-spot and sometimes crushed her clit.

"You know you surprised me last night. When you came in and started kissing me I just thought it was going to be a lovely goodnight kiss and grope. I was a little shocked when I heard your belt buckle hit the floor."

"Was I too bold?"

She leaned over me, the nipples of her breasts grazing mine as she continued to rock against the erection lodged inside her.

"Umm. No. Ummmm. Just right. Ummmmm, ummm, ummmmmm. Oh my god..."

Once again the spasms of her body and her quim pulled my own orgasm gushing into her. This time we could look each other in the eyes as we came.

After catching her breath, she got up, showered and headed out the door to catch her fight. I had her itinerary and she planned to check in at the American Express offices in the major cities of her tour so I could send her letters... This was an age before the Internet or cell phones. I even sent her a box of chocolates at one stop for her birthday.

We were lovers all of the next year. It took us two or three months to get up the courage to tell Matt, but once we did we were open about our relationship. It was a wonderful year. After she graduated we went our separate ways. We've each married others and raised kids and have kept in touch from time to time. Each of us have had a life's experience since we were lovers. For me, however, nothing has matched the sheer eroticism of that first night with Jane.