The first time I ever had sex I was ten years old. The girl was 12. I hated the idea and it took weeks of her negotiating before she convinced me to put my dick in her pussy. This was in the 1960's and in those days boys were not as worldly nor knowledgeable as today. I had no idea where babies came from other than it was something to do with the female body. I didn't have an older brother to explain it to me and both my parents were repressed. But they had no problem hiring a beautiful 12 year old girl to baby sit their 10 year old son and his 3 year old brother. She went on at great length about how "pretty" I was and how much she loved my long "pretty" hair and "pretty eyes" and "pretty lips" and on and on. I was still at that point in my life where girls were ICKY!
But then one day she finally convinced me by giving me an impromptu massage that ended up being her groping my ass and as it turns out I rather like having a beautiful older woman grope my ass.
Clothes were removed, genitals were tickled and before I realized it my blood covered little prick was all the way in her warm, wet soft pleasantly tight pussy and we were playing with each other's nipples, her's considerably larger than mine and I realized she smelled kind of nice and her face was not hard to look at.
Turns out that girls are not as icky as I had previously surmised. Alice was especially not icky. In fact Alice was quite lovely and despite her annoying habit of referring to me as pretty, I find I liked her a lot. We never dated. Socially we couldn't be seen together. I was a fourth grader and she was a seven grader but she explained that we could fuck and "practice making babies." And it was Alice who told me all about sex and how to make babies and where they come from and all the ins and outs, pun not withstanding.
She was my first. She was not my best. But she was no where near the worst. She was, however, the yardstick I compared all other lovers to. We fucked repeatedly until I was 14 and she 16. Turns out she lost interest in me when she met a guy who had the nickname Mr. Ed.
My best fuck ever was a little girl named Jen. Jen was a little girl in size not age, at least not in age compared to me. I met Jen when I was 28 and she was 16. 16 was legal at that time in that state. Jen was about four feet tall and slender and flat chested and looked like she was around seven. She liked to dress up like a small child and pretend she was three and call me Daddy. I could take or leave the little girl routine but she was heavily into age play and I went along because of the promise of a good fuck. Jen was very pretty but she was never going to have big tits and she would never reach a normal height. Basically I dated her despite her size not due to it but she was pretty enough to make fucking her appealing. What made her the best fuck ever was the fact that my average size (since all men exaggerate you should read this as slightly below average) dick when in her pussy made me feel like I had a cock the size of my arm. The first time we fucked she complained about how huge my cock was. That only served to make my cock harder and throb more. She insisted I take her virginity and that I absolutely must complete the task no matter how much she begged me to stop. So in this particular case no meant yes and I did the "R" word. I shoved it in, held her tight and fucked her. Fucking her was like I would imagine fucking a three year old would feel like. She was absolutely the tightest I have ever fucked ever. When I was done cumming inside her I stayed hard. I rested keeping it inside her then after a while fucked her again but this time slower and she came a few times while I did that before I came a second time. This time I went soft after but stayed inside her soft until I couldn't stand it and had to piss.
She sucked me hard again and I fucked her again. This went on for hours and I fucked her more times in that first day than I ever fucked anyone else before or since in the same time period. I dated her for a couple of years before she decided she preferred girls.
The worst fuck ever was when I got drunk, a rare event for me, and when I said drunk I meant falling down three sheets to the wind plastered drunk. When I took her home she was a teenage supermodel. When I woke up she looked like that woman who played "Mama" in "Throw Mama from the train." You know the one, she looks kind of like an uglier version of Walter Matthou in drag. She was around 400 pounds, she was about thirty years older than me, was harrier than an ape, grey buzz cut, and stunk like a septic tank filled with burning rotting corpses. She was also looser than a fifty five gallon drum with a big rubber bag in it. I could only stand to glance down at her for a second and swore I saw maggots crawling around between her legs. I sobered up in record time, threw on my clothes and half dressed fled the place only realizing an hour later we had done in in my bed.
Hours later I found she had left. I burned the sheets and mattress and fumigated the apartment, changed my phone number and a few weeks later moved when I found she mailed a note to me.
The strangest fuck I ever had was when I went out on a date with twins. They were very attractive. They wanted to fuck first date and didn't mind sharing. We got to where we were in a three way make out with my two hands groping their tits and their four hands groping me every where and we were almost naked when I noticed something wasn't quite right. I'm not gay. I have no interest in dating guys. But somehow, having both of their cocks in my mouth at the same time while one sucked my dick and the other sucked my balls didn't seem so bad if I just thought of them as really big clits. Besides, if you added up their ages I would still be older than they were and somehow it feels less weird when the other person is a lot younger. That was the only time I ever explored my inner bi. It felt ok mostly because I was able to just think of them as girls. After all, they were really pretty
I was 14yo and I had been masturbating since I was 12yo. A family moved down the street, two boys and their sister. Her name was Cindy, and she came to my house one day. My folks had gone somewhere for the day so I had the house to my self. Anyway after some talking about nothing much, Cindy says I want to do something I saw my mom do to her dad the other night. I said ok, not ever thinking what she was about to do.
She just pulled my pants down and started to play with my cock. She didn't put it in her mouth, she just rubbed it. Being only 14yo I was steel hard in about 45 seconds! She just kept rubbing until I felt that "sensation" of impending release.
Sure enough within a few minutes I began to cum and watched as Cindy just kept rubbing my hard cock until I was spent. She just laughed and seemed so proud of herself that she could what her mom did to her dad.
I don't remember how many times Cindy would come over and make me cum, but to this very day after all these years I remember it all like it was yesterday.
I was 13 and knew a very nice girl she was the same age, One day right out of the blue she put her hand down the front of my jeans grabbed my cock which wasn't that big back then and said have you put that in a girl before? I was stunned and horny all at the same time, I said no I hadn't she smiled lifted her skirt and showed me her panties and told me now was my chance, We were soon both naked and she showed me what to do inserting my cock into herself for me, It was all over quite quickly but I was hooked and wanted more and I got it too for a year we did it as often as we could she seemed always eager and ready at anytime, Sadly she moved away with her parents leaving behind a very grateful but horny boy.
I stared masturbating at 12 years old. At 14 my best buddy and I started jerking-off together looking at girly magazines. Then one day I gave him a blow job and liked it. He started blowing me to. Then at 17 a girl that was 16 that I worked with asked me out. One night of heavy making out and rubbing against each other she asked me if I ever did it. I said no she started laughing I was so embarrass. We got naked in the back seat and I put my cock in her. I was going around in circles she said no hump. I was so embarrassed I couldn't cum. So I pulled out faked it in a napkin.
Worst. She cried and I got blood all over my cock. But I married her anyway and we joke about that now.
She invited me over for a swim while her parents were out for the night. We were all over each other in that pool, then went inside and had Crown Royal. We were so grown up! We went for it after that and ill never forget how awkward it was. I didn't even finish I felt so bad. But we learned and it got better over time. We've been together now for 14 years, since we were both 18.
