Where it happened: Her Dad's New Cadillac
Langauge: English
Sex: Male
Rating: 8
Category: Straight
I refer to story 27124 which I sent in the other day. I need to add something about what happened here. This girl was my best friends sister. At the time she was 22, seven years older than I was, and she was undoubtedly the most gorgeous looking woman I have ever fucked in all my life. Though I never got to see her naked the story which I tell is both bizarre and almost hard to believe, and I wonder if such has ever happened to anyone else.
I had been with my best friend at his house all day, and by the time I was supposed to be going home it had started raining quite hard. Mary-Ellen, my friends older sister, had said that she was going down to the store to pick up some milk, and told her brother and myself that she could drop me off if I wanted.
Well, this is the way it went. We got into the car and started driving the half mile to my house. She asked if I had a girlfriend. I told her that I didn’t, not right now.
“You ever made love to a girl?” she asked.
“You mean… sex?”
She nodded. I admitted that I hadn’t.
She smiled, and then suggested I was kind of cute, that I had a butt a lot girls would dream for. I appreciated the comment, and told her I thought she was cute as well.
“What do you mean by cute?” she asked.
I told her that I’d seen her in a bikini, that she looked real sexy.
She asked me to explain.
“I guess you kind of look good, in a bikini.”
“What kind of good?”
“You know,” I told her.
“I don’t,” she said. “Tell me?”
I wasn’t sure what to say. She was older and more mature than I was, and it seemed that she was playing with the words which I was saying, wanting me to say something I might regret.
“You’ve got nice tits,” I suggested, looking away from her and kind of embarrassed that I’d said it.
By now we were stopped outside my house but it didn’t seem like she was in any hurry for me to get out.
“So you like my ‘tits’?” she asked, kind of laughing.
I nodded.
“I guess most guys like ‘tits’,” she suggested, “the same way that girls like seeing guys butts – especially naked ones.”
I agreed, and then it was that I felt her hand on leg, just gently massaging it as we talked. My penis started to react, and started getting hard. She was teasing me, her hand slipping up and down my thigh as though she knew. We kept talking, and she was turned toward me, her short skirt pushed somewhere up her thigh as her knee now touched against me. Her hand roamed further, closer to my crotch, her fingers almost touching the stiffness underneath, and then I dared to touch her, the naked flesh of her knee right there in front of me.
Suddenly I felt it, her fingers beginning to touch against the hardness of my youthful cock, just brushing against it as though it was she hadn’t realized it was there.
I wondered? Did she know? Did she realized what it was? She just kept talking, about all sorts of things, as though her mind was not on what she was doing with her hand.
My hand slipped up, touching the softness of her inner thigh a little bit above the knee; and then it was that her hand appeared to discover the lump inside my pants, and her attention seem diverted to the part of me she handled, the part which she now held.
“Nice,” she commented softly. And then it was her hand slipped up and found the fly, slowly undoing it, pulling it down.
My hand slipped up and found the panties, and I started playing with the mound of it, too scared to go inside the panties, just squeezing on the lips of it and feeling the hair of the thing as she started now to reach inside my Jockey briefs and found the naked penis.
She played with it a moment then she stopped, then pulling away my hand she straightened out her clothes and suggested we take a ride, to ‘see who’s down at the lake front this time of night?’
The moment we were down there, she took her panties off and slipped them down her legs and onto the floor and then resumed the position she was in when we had pulled away from my house, and her hand was right back in there as now she began to remove the naked penis from my pants. In a moment my hand was right up her thigh, this time without the panties in the way as my hand beheld the biggest lips and the hairiest pussy I had ever felt before. She was wet, and as I touched her there it seemed that she was anxious to have my finger go inside.
She leaned across and kissed my cock, the head just in her mouth, and then she leaned the seat right back and then got up and straddled me, and was holding on the penis, seeking for the entrance as she guided it toward the part, then pushed to me as now I slipped it in.
I was sucking on her breasts, the only part of nakedness I actually ever saw of her; and as she fucked my anxious penis I could feel that sexy roughness of the skin, the parts of her inside which seemed to lock around my penis each time the stroke came out. We fucked it seemed forever before it seemed I’d cum, and then it was it seemed she really got excited and she moaned and fucked and cried aloud, then gasped like she might die!
I felt it spew from out of me, filling her inside, and then when it was over she just sat there for a while, my penis still within. She kissed me and she squeezed my butt and told me I was cute, and said that though she really liked me I should never tell a soul; and if in fact I ever did she’d tell them that I’d lied and she’d make me feel a fool. She squeezed the penis in her, and fucked it one more time, and then it was over she started up her fathers car and drove me home.
The ending of the story is really not too good, because that very next morning I went and told a friend at school. By the end of the day my best friend, whose sister it was, had heard the story too. He was mad that I had said such a thing, and knew it wasn’t true, but then it was he told his sister, the one that I had fucked!
Well, that was it, probably one of the most embarrassing times of my life! Her dad phoned my dad, and her mother phoned my mother, and my ‘best’ friend from that day never spoke to me again! About a week later this girls boyfriend cuts me off when I’m riding my bike home from school, and gets out of his car and punches me so hard in the gut for ‘making up stories’ that I think I’m going to die!
People now were calling me a pervert, and I could hardly stand being around people, knowing they were all talking about me, and not a soul believed me!
A lot of years have passed since then, and a lot of lessons learned, but no doubt the biggest lesson learned was that women who want the secret kept get really wound up mad when you go blabbing you had sex with them when they don’t want folks to know!
A few years later I had a job as a civilian working with the Navy in San Diego where I did repairs and handyman jobs on the married quarters housing. In a period of just eighteen months I had the pleasure of having sex with thirty-two ladies (ages 18 to 42), all of whom were married, and whose husbands were away at sea.
The process was the same with each, and they would invite me in for lemonade or coffee. Then it was that they would ask me if I had a girlfriend. When I would respond that I didn’t, the subject always seemed somehow to turn to that of sex, and then how long that it had been since they had done it. When it seemed like the right time to ask I would suggest I gave the best massage in all of San Diego, and then it was with just a little coaxing that they’d end up with just their underwear on and lying face down on the bed.
I’d give them the best massage I am sure that there was, and then when I knew that they were ready I’d turn them over, and without saying a word I would slip their panties off, and fuck them as they lay there on the bed. It worked every time, and I got myself a reputation, even such that I began to get referrals! I kept things really simple though and never fucked the same woman twice, not wanting to get involved in their lives as they waited for their husbands to return; but if it was I’d ever told a soul that I had fucked any one of them I would have been done for and my career as a handyman would have been finished! I am sure too there might have been more than a ‘punch in the belly’ when their husbands got home from sea!
I thank Mary-Ellen, the most beautiful woman I have fucked, for that lesson that I learned!
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