I love this site. I have wanted to contribute for a while because I have so many stories, but finally mustered the courage. Writing them is quite a turn-on!
Natalie and I dated in our sophomore year of college. She was a classically beautiful brunette with short curly hair, a broad smile, a skinny body and huge tits and she was definitely looking for 'safe' ways to experiment sexually.
After only a couple of dates, I remember she started asking me about masturbation, how often I did it, what turned me on, etc, always very curiously, always smiling when she asked. Then, as now, I masturbated at least once a day, often more, just to release the pressure because my dick was always hard.
Part of the problem was the fact that I shared a room with a roommate and neither of us were willing to admit we did it, so I would sneak back to my dorm between classes to get myself off. Sometimes I made myself cum in the bathroom of the economics building, an older campus building that had a small bathroom with a locking door, always fantasizing about the girls in my afternoon class, just a few feet outside the thin door. I was definitely ready for a girl like Natalie.
But Natalie mostly flirted and asked pointed questions, never revealed much about herself, and more importantly, even after we'd kiss for hours and she'd get me hard as a rock, she'd never finish me off. Then she invited me to spend the night with her while her roommate was home in Connecticut.
She climbed into bed wearing a tight half t-shirt that barely covered her enormous full breasts and a pair of high cut panties that showed off her toned, soccer legs all the way up and most of her small but shapely ass. I was in boxers and my erection was obvious and I was leaking precome so bad that she must have felt it when she was grinding against me, but after kissing me for a while, she told me it was time to 'get some sleep' and even though I tried to fondle her tits and to guide her hand to my throbbing cock, she demurely pushed me away.
It took me at least an hour to fall asleep with her cuddled in my arms, but she dropped right off. I don't know what I started dreaming about but my body took over and, while I was sleeping, I must have wriggled out of my boxers.
To my embarrassment, I awoke with my hand around my thick, hard cock, stroking myself. I am only six and a half inches long, but my meat is so thick that I can barely get my hand around it, and my balls are enormous, which I think is why I need to cum so often. As soon as I realized what I was doing, I jumped awake, startled. In the half-light I could see she was grinning at me.
'I'm so sorry!' I protested, 'I didn't realize what I was doing.'
'It's OK,' she said. 'I could see you were turned on when we went to sleep. Do you need to come?' I needed to come so bad, and I told her so. 'Then go ahead and finish yourself,' she told me. 'I want to watch.' She pulled down the sheet and there I was, my cock bolt upright, tight with desire and drooling precome in my fist. I took off my shirt so she could see my abs (I am a very lean, six foot one inch, 160 pounds) and I looked down at myself and then at her sculpted legs and I started going at it.
It felt so good to finally be stroking in front of Natalie. She had been turning me on for so long and I wanted to give her a show. I slowed down my stroking and used the flat of my palm to push my cockhead out away from my body so she could see my length and fullness and, when I let go, my dick slapped against my stomach and my huge balls bounced.
Somehow this broke down Natalie's reserves and she groaned slightly and reached her right hand into her panties. I could see the shape of her index finger moving in circles beneath the thin fabric, and I felt my balls tighten. 'I'm going to come,' I told her. 'Do I make you want to come?' she asked me. 'Yeah,' I groaned. 'Then come!' she replied, her own breathing tightening in her chest.
I sped up my stroking, my finger and thumb in a vice grip around my cockhead and jerked myself faster and faster until I felt the first tickle of jism rising up my shaft. Right at the peak of my stroke, I tightened my whole hand around my meat and pumped, tightening the grip on my shaft.
I shot almost a continuous stream out over her covers and then three or four heavy spurts all over my chest and neck. Natalie cried out, 'Oh my god, I'm cumming!' and started bucking furiously next to me and as I glimpsed over she had pulled her panties down so she could fan out her hand in a broad arc-like motion all over her clit and pussy. It was so beautiful, the sound of her cunt slapping wetly and the sight of her tits bouncing, and I felt myself spurting more as my cock jerked uncontrollably in my hand.
Two more spurts shot out, one hitting Natalie on the forearm, one landing square on the bottom of her stomach. She started to come again, writhing as she did, moaning louder now (loud enough that I worried somebody on her hall would hear her) and when she came again or still, she lifted her whole ass off the bed and moaned, part roar, part whine.
It was the beginning of a beautiful relationship and Natalie's curiosity quickly grew. I will tell the story next time of how she convinced me to do some more experimenting with masturbation, but right now, I have to empty my balls because typing this has got me so horny I can't sit still.