Long time reader, first time contributor. This is a true story.
When I was in college, I met a girl who was a little bit younger than me. We really hit it off well from the start. Let's call her Katrina. She had a great sense of humor, was very shy at first, and had a bit of a tomboy flare. We started a relationship a few months after meeting each other.
Katrina was 5' 2', had shoulder-length, straight black hair, medium-sized body, size C something boobs, a nice butt, blue eyes, and glasses. I was 6' 1', with dark brown hair, athletic build, and a 7' cock. All of my pubic hair was shaved except for the triangle, which was neatly trimmed.
After several months of dating, and her being protective of her virginity, it left us thinking of ways to take our relationship to the next level. She lived with her parents, and we would often cuddle on her couch while a movie was on. We started to advance a bit, but hadn't escalated more than kissing and touching each other a little over our clothes. After a few of these sessions, she allowed my hands to wander up her shirt, but never under the bra. She didn't let me explore the southern hemisphere either; she would always casually move my hand away if I got too close to her pussy. Once, while she was on her back and we were making out, I guided her hand to the material over my hard cock. She instinctively started to stroke it, but we had to quit our session from advancing too far, because she always had family close by.
We didn't have a private place to go for our play sessions. One evening, on one of our dates, I suggested that we drive somewhere private and fool around in the backseat of my car. She said we could give it a try as long as we were back by the 1am deadline that her parents imposed on her. We drove around for about an hour. Our first failed effort was behind a supermarket that had closed for the day. We started fooling around only to have the night stock crew members, going back and forth to the dumpsters, interrupt the moment. We drove around some more and found a secluded part of a local park that had minimal lights. The inside of the car was illuminated just enough for us to be able to see and fuck around. I cracked the window, and we moved to the backseat.
The car started to get a bit cool since it was mid-winter, but things quickly heated up. She first laid on top of me, and we began thrusting our tongues into each other's mouths. During our make-out session, I ran my hands all over her butt while she felt up my chest. I curled the fingers on my right hand and slowly grazed over the length of her butt crack several times. My left hand snuck down the back of her pants a couple of inches, and I teased the topmost part of her crack and cheeks. Then, we switched spots, and she laid down across the backseat while I positioned myself on top of her. To my surprise, she unzipped her sweater to reveal that she was only wearing a sexy peach-colored bra underneath. I wasted no time and went to work on her tits by sucking and nibbling on the fabric. She laughed and said that it would be much more enjoyable if I took her bra off. We sat up, and she did the hard part of unfastening the clasp, while I took off my sweatshirt. I was so horny that I could have just ripped off her bra and motor-boated those beautiful tits, but instead, I quickly thought of a more-romantic approach. Still sitting up, we kissed passionately for several minutes, and I nonchalantly removed her bra while looking into her eyes. I laid her down, moving from her mouth to her neck, and finally to her breasts.
Her boobs were kind of perky, the areolas were perfectly quarter-sized, and her nipples were hard and protruded out a few centimeters. I licked and sucked on the left one while playing with the other with my hand. Her skin was so soft with a faint salty taste. She moaned and ran her fingers through my hair. Feeling bold, I dropped my hand from her right nipple to the crotch of her jeans. She didn't shoo my hand away as in previous sessions, so I started to earnestly rub her pussy through the denim with my fingers. After a few minutes, I tried to slip a hand under the front of her jeans, but she moved my hand back to over-top. Somewhat frustrated, I moved my full attention down to her pussy and started to massage her jeans with both hands where her wet hole would be. She squeezed her boobs together and sighed deeply a few times with approval. I moved myself up slightly, implying that I was in desperate need of some touching. She didn't wait a second and grabbed hold of my hard cock through my khaki pants.
She had previously told me that she had never done anything before with a guy. Her stroking through the pants wasn't giving me a lot of pleasure, but because of me being so horny while working on her for so long, any added sensation meant that I could bust my load pretty quickly. I stopped her hand for a moment and told her that I was going to cum. She asked me if that wasn't the goal of our session, and I replied, yes, but I didn't want to cum in my pants. Looking at the clock, it was almost 12:30am, and I knew we'd have to be quick to get her home on time, or else I'd have to answer to her parents.
I leaned into the front seat, opened the glove box, and grabbed a handful of napkins. Offering the stash to her, she conservatively took one napkin and placed it on her stomach. Having not beaten off for a couple of weeks in preparation for this moment, I knew that one napkin would be useless, but the devil on my shoulder told me to go with it. I hesitated and then placed the dozen or so remaining napkins on the back dash behind the seats. I leaned up over her and unzipped my pants. Being a little stubborn, I wasn't going to let her have access to my balls, since she didn't give me skin access to her virgin slit. Her hand reached in and tried to extract the seven inch monster from its cave, but she was having trouble with the material from my boxers being so tight against my cock. I reached in my fly and pulled it free. My cock was swollen and pulsated in rhythm to my fast heartbeat. It was ready for attention.
She lightly grabbed my cock backhand style with her right hand and began to stroke very short strokes on only the near-base of the shaft. This wasn't really doing much for me other than realize that she had been truthful about her never pleasuring a guy before. In the essence of time, I took her hand and repositioned it over my cock head and upper shaft and tightened her grip. She then began pumping her hand a little quicker, while I massaged her tits once again. I moaned a bit for dramatic effect as I could feel the pressure mounting. It wasn't long before my hot, milky load erupted in several powerful spurts. I didn't actually see the cum shoot out of my cock, but I did see my orgasm's aftermath. There was cum in her hair, on her sweater, tits, stomach, and cheek. The lone napkin had turned into a soggy mess.
She was obviously taken by surprise. She was giggling and reaching for the extra napkins while saying that she didn't know it was going to spray like that. I squeezed the last bit of cum out of my cock and wiped up with one of the napkins. After we got ourselves situated, cleaned-up, and dressed, I drove her home, arriving just a few minutes past 1am.
Our relationship stopped a couple of months later due to some bad decisions on her part. Although some negative thoughts come to mind when I think of her now, there is a sense of accomplishment knowing that the first cock to unload on her was mine. Every now and then, this gem of a memory pops into mind when I need to beat off.