First Time

I was 18 and very much a virgin when my brother lost his driver's license. Terry was 5 years older than me and since I didn't have a job, I became his chauffeur. I would take him and his girl friend out and they would drink and dance while I drank soft drinks or coffee and watched. At the end of the evening Terry would tell me to find a dark alley or someplace to park so he and his girl Jenny could make out. They didn't make me leave, so I would watch in the mirror and end up with a raging hard-on by the time they were done. The up side was that I learned a lot and got free shows. This probably started my liking for voyeurism that continues to this day.

Then one night my brother passed out before we could find a place to stop. I didn't realize this until I had pulled down an access road along a set of railroad tracks. When I stopped Jenny said, "This is a nice private place, but he is out."

Before I could say anything she got out and hopped into the front seat alongside me. Jenny looked across the bench seat at me and said, "What do you think when we get, ahhh, busy back there?" nodding at the back seat.

Looking her in the eye I figured the hell with it, I would tell her the truth and said, "Honestly, Jenny, it makes me horny as hell. I always go home with a hard-on after watching you two have sex."

Jenny leaned over and put the palm of her hand on my cheek, "that has to be rough to deal with every time we go out." Her hand felt like flame on my cheek, I nuzzled into it, enjoying her touch. "What do you do about that?"

I smiled at her and said, "I jack-off of course."

Jenny laughed and said, "Of course you do. What else would you do?" Then she gave me a knowing smile and asked, "If I gave you something to look at can I watch you jack-off? I have never seen that."

I was dumbfounded to say the least, but answered, "Take your blouse off, play with your pussy, and ok, it's a deal."

Jenny didn't say anything but started undressing. Jenny was 22 at the time and very trim. Later, I found her measurements were 32-22-36 and she was a C cup. Jenny had a flat belly and her titties stood out, passing the pencil test easily. As she undressed I reached over and flipped her long brunette hair back over her shoulder, telling her, "I don't want to hide this view." She laughed.

Jenny leaned back against her door and crooked one knee up onto the seat. She took one nipple in between her finger and thumb and started rolling it and tugging on it. I didn't realize a nipple could stretch that far before watching her. She reached between her thighs with the other hand and sloooowwwllly drew her middle finger up the edges of her outer lips, barely splitting them. She had her hair trimmed very short, almost gone short, which was unusual in those days.

I pulled my already hard cock out of my pants and began stroking it. Her eyes locked onto it. I am no porn star, having an average 6 inches of cock, but it is rather thick. I maintained a slow steady pace, hoping to prolong it so I got to see her have an orgasm.

Jenny pushed her finger between her lips and found her clit. I watched her pull its hood back and she began rubbing directly on it. Then she let go of her nipple and inserted two fingers into herself. She began pumping in and out of her pretty pussy while playing faster on her clit. I could hear her breathing deepen and quicken. Her hips began pumping into her hand and I noticed her eyes were still glued to my cock. Then she started moaning deep in her throat.

Jenny's moans got louder and she moved faster. I could see that she was extra wet. Her juices ran out of her and down the crack of her ass, her fingers glistened in the moon light. I pointed my cock at her and pumped a little faster. "Do you want me to shoot it at you Jenny?"

"God, yes, let me see it cum."

I moved my hand a little faster and squeezed a little harder for a few minutes and then, there it was. "Jenny, I'm cumming." I gasped. My first rope of cum landed on her tits and made a little splatting sound I came so hard. The next two or three landed on her thighs and lower legs. The rest kind of oozed out, covering my hand and the head of my cock.

Seeing this Jenny lost control and came also. She convulsed and almost screamed as she came. Jenny panted and her body jerked like she was having a seizure. After a couple of minutes she noticed my cum on her. "What's this?" she cooed at me. She smeared it around on her skin and then tasted her fingers. "Not bad," she smiled at me.

Jenny then leaned over and took me into her mouth after licking my hand, she wanted all of it. "You taste good, I like it, not bitter like your brother's." She bobbed her head on me for several minutes. Being 18, I got hard again in her mouth. Soon I grabbed the back of her head and pumped up into her mouth in time with her head bobs. My first blowjob and I was loving it.

I was breathing hard when she suddenly stopped. Jenny pushed me back into the seat and straddled me. She reached down in between us and grabbed my cock. She lined it up with her opening and slowly sat down on me. My cock entered her and I was no longer a virgin.

Jenny slowly moved up and down on me, making me groan in pleasure. My hands sought her tits and began massaging them roughly. This was a totally new experience for me. She was hot, wet, tight, and slick all at the same time. It felt like my cock was in a velvet glove. Jenny had enough muscle control to make it feel like she was milking my cock as she moved. I was so entranced with the feeling she was producing in me that I became very vocal, grunting "Oh, fuck you are tight on me. Your cunt is so good on my cock. Fuck me Jenny, fuck me." Suddenly I was cumming, my hips thrust up into Jenny as I delivered my load deep inside her swollen cunt. She cried out in a wordless semi-scream and I felt her pussy spasming on my cock, milking me dry. Jenny collapsed on my chest, gasping for air, as I tried t catch my breath. She gasped, "Oh fuck, that was good. I have never cum like that with Terry."

The result of my first fuck was many more sessions with Jenny. I would drive for Terry's date with her, and the usual make-out session afterwards, then after taking Terry home I would go back to Jenny and give her a second dose for the evening. Terry never did find out.