Where it happened: Chicago
Langauge: English
Sex: Male
Rating: 9
Category: Straight
Maria was her name. She was a girl of the neighborhood near the schoolyard where I hung out with the other guys of the gang. It was in Chicago. I was between 7th and 8th grade. The summer of ’69. Maria was of Haitian and Puerto Rican disent. I was a gangly, little Pisan in a very culturally diverse neighborhood. Maria was older by 5 to 6 years. I think she was going to be a senior in high school. Maria was exactly pretty. She had teeth that were crooked and hair that was absolutely unruly. But, what she lacked in good looks she made up for with her body and personality and SEXUALITY.
By then, I was past puberty and understood what my “manhood” was for…I just hadn’t had a chance to use it other than masterbating whenever I could.
It started when I started chatting to Maria on occasion as me and my friends walked by her stoop. Sometimes she would ask for a cigarette. Yeah, I know I started everything young. One night during the summer, I was near dusk and I was walking past her house and she was sitting there all alone and I stopped and chatted with her. As we talked she walked around the side of the house between hers and the tenement building next door. Suddenly, she asked if I have ever ‘Frenched kissed?’ To be honest, I didn’t even know what Frenching meant. I told her “no.”. She asked if she could show me. I considered it for just a minute then said, “okay.”
She lead me in through the darkened gangway between the two buidings into a corner where we could not be seen by others passing by on the sidewalk in front of the houses. She took my hand in her face, turned it toward her and planted a soft, gentle kiss on my lips.
Now, let me tell you more about Maria. Despite her physical faults,she also had many attributes. First, there was the fire in her eyes, a passion that sparkled when she became excited and she was as tall I was at the time, maybe 5’9″ with long, shapely legs, slightly bowed that made her walk look sexier some how. She was long, lean with medium sized breast that were very firm and ‘V’ shaped waist that flared out to small, smooth rounded hips and a lovely, small, round firm ass that looked great under a dress. And, Maria only wore dresses. Maria’s skin was like creamy and smooth and the most delicious shade of brown – not too dark, not too light and her skin was flawless.
As Maria first kissed me, I just took it in. It wasn’t the first time I kissed a girl but this was more than just a one-time lip kiss sort-of thing. After a minute, I began to relax and sensing this, Maria began probing her tongue into my mouth. My God, what is she doing! I found Frenching, especially the way she did it to be very sensual, very exciting. Soon we we holding each other, pressing our bodies together and before long I too was seeing what it was like to stick my tongue in to her mouth.
We continued to kiss and we did so, we became more comfortable, more familiar with each other. We were the perfect height for each other. Niether having to bend down or reach up..our mouths were there, eye to eye, toe to toe. As Maria pressed into me, I could feel her tits against my chest, her belly against mine and I was absolutely loving this new sensation of really getting intimate with a female for the first time. Before, I knew it, I had a raging erection in my pants.
Maria would make the most wonderful purring, love noises as we grew bolder. She would press her groin and belly against my rigid member and I would grind back against her while caressing her ass over her dress.
We seemed to kiss a long time, maybe thirty minutes and by the time we stopped, I had run my hands over her ass, thighs, her waist and although I tried her tits, she stopped me. “I better get inside before my Mom starts looking for me.” We parted for that evening but that night was just the start of my education concerning woman and sex.
Things progressed rapidly from there and lasted all throughout the summer and somewhat into the new school year in the Fall. The next time we “Frenched,” Maria remarked what a fast learner I was and as my cock grew to stone once again after kissing and petting each other for what seemed like forever she asked me the next remarkable question, “Have you ever had a handjob?” I thought I knew what she was talking about. I said, “you mean like jacking-off?” She said, “Yes, but I will do it for you…you have a nice hard cock here, let me see you jizz.” WOW! Yeah, she started rubbing my hard penis through my pants and you could tell this excited her by the noises, and faces she made and her eyes and hands. Her hands were also manicured nicely with long thin fingers like her body that fit nicely into mine. She told me to relax, then stopped her kissing and unzipped my pants, reached into my shorts and literally had to pull it out it was so hard and high up in my shorts. Then she said, “Let’s undo these pants and let your balls out.” Oh my God did that feel good and she made me feel better telling me how warm and hard and good my cock felt in her hand.
She would stand to one side, sliding her thigh up and down my leg, whispering in my ear, asking if her hands felt good on my big hard cock. She would occasionally rub my balls with one hand while continuing to stroke me.
To be honest, I didn’t last very long. It felt SO GOOD to feel HER hands on my cock verses my own. And, while doing so, she would let me feel her ass and even rub up her firm tits encased in her tight dress and bra. As my orgasm neared and my cock swelled harder, she would say things like, “oh yea, let me see your shoot it out, jizz all over baby!” And, she always liked to see it come out of my tip.
Now back then, my jizz load was tremendous with thick, scalding strings of while sperm that hung like ropes from the end of my cock until it was jerked off and more came spewing out. Maria was truly excited seeing my cum in the dim light of alleyway as I ejaculated what seemed like a never ending load of cum all over her hand, forearm, the ground…everywhere. She loved to see me breathing hard, eyes exploding in my head as wave of wave of pleasure overtook me while her pretty little hand stroked me ectasy. To say we both enjoyed it was an understatement and I was hooked from then on.
It didn’t happen every night that summer but probably at least once or twice a week, I would meet Maria at dusk and we would sneak down some alley nearby and find a quiet, secluded place under a porch or in a corner somewhere where we would kiss and pet and eventually she would pull out my cock and jerk me to my hearts content.
I couldn’t keep this secret forever and I was soon telling my friends about Maria the whore who loved my cock and loved jacking me off. My friends hung around more which meant hanging around Maria more and before too long she would not only kiss just me but sometimes one or two others of my friends as she would tell us to get our cocks out for her to stroke. By the time she was done with the 3rd, we oftentimes would ask her too jack us off again for a second time. She fucking loved it. We loved watching her do it to us but she never would suck us or let us finger her pussy or see her tits or fuck her although we did talk about it and think about it often.
One night, my friend Mitch and I were playing ball at the schoolyard across from her house. It was around 7:00pm and she came by with her little sister and started flirting with us, then getting more aggressive, demanding our attention away from playing ball and onto her.
At that particular time, we weren’t interested especially with her little sister at her side and told her to go home. Boy, was she mad. As we were resting about an hour later, she came storming up to us, yelling to us in Spanish then English telling me that if I was a man, I would fuck her and fuck her NOW!
I thought for a moment that she had turned looney or something but Maria was just horny and wanted cock and she wanted mine now. The three of us found a secluded, darkened spot about a block away, off the alley in an alcove leading to a basement of building.
The kissing, the petting, it was all there again, only this time more passionate. I asked her to jack me off and she did it only after I promised her that I would fuck her later. I agreed but, I was scared. I didn’t know what to expect. I had never seen or felt a real pussy with my fingers, much less my cock.
She jacked me off, as always beautifully as Mitch stood by watching and waiting his turn, stroking his cock slowly. Mitch was somewhat bigger than me in size and Maria seemed to really enjoy his longer, thicker penis. When she had finished bringing him off she turned to me and asked if I was ready to fuck her. This was all happening faster than I could have imagined and too slow things down a little, I asked her to show us her tits. She didn’t want to but I told her I wouldn’t fuck her unless I could see and touch her tits first.
Reluctanly, she pulled down the top of her dress and pulled up her bra to expose her tits. We asked her to step into the light a little bit so we could really see them good. Man, she had a perfect set of tits, a perfect handful of firm, soft tittie flesh capped with dark, brown, small but hard nipples that I gently touched with my fingers. I rubbed those tits until she said, “that’s enough, now fuck me.”
She lead me to the wall and stood against it pulling her dress up. Guess what? No panties! All I saw was a small patch of dark, curly hair as she grabbed me cock and rubbed it up and down her wet slit, raised her leg, grabbed my ass and pushed me forward to penetrate her. Soon, I was stroking into her pussy and beginning to enjoy and inquire about the new sensations on my cock. It felt wet, very wet and I wondered if she was bleeding or something. She was breathing hard, rolling her head back and hanging onto to me for what seemed like her dear life.
Stupidly, I pulled myself out of her and stood briefly into the light to check my dick. Nothing! Nothing but wetness. No blood. So this must be what pussy is like! Yeah. I continued fucking her until I was about to explode but didn’t want to cum in her knowing I could get her pregnant as we weren’t using condoms. As we were catching our breath, Mitch moved in and told Maria it was his turn and asked her to lie down on the cold cement floor which she did willingly. She pulled up her dress and I could see with a thin stream of light shining on them both like a spotlight as Mitch slowly entered her and then begin fucking the living daylights out of her with his big cock.
She was trying not to scream out her pleasure and I knelt next to her rubbing her tits again as her eyes pierced mine with lust as Mitch was fucking her good and hard. I stroked myself and then pulled up her bra again to see those beautiful tits. Maria was loving our cock, my hands and was shaking visibly, her head moving side to side as her breathing became more erratic and I placed one of her hands on my cock again.
You could tell all of us were going to cum. The pace was frantic as Maria jacked me cock over her tits and Mitch fucked her and she was moaning in ectasy and us guys were grunting, trying to make it last. I popped first, I think spraying my jizz all across Maria’s tits and belly, neck…man, I made a mess. Mitch stopped moving, grimacing as he shot his own volley of cum inside Maria. Maria looked panic stricken, yet wildly excited, moaning loudly, breathing very fast and heavy and then she passed out.
Scared the holy shit right out of us guys. We thought for a moment that we had killed her. But, she just plain passed out with the force of her orgasm and Mitch’s cock and balls were absolutely soaked with a combination of their juices. Finally, after about 3 minutes of talking, and fanning Maria, she came to. She said that she passed out it felt so good and she never had so much fun!
We walked her home and for whatever reason, I never fucked Maria again after that but she was my first experience and I thank her to this day for all the joy and pleasure we shared during that hot summer of 1969.
She gave me enough to know that sex is great but not so much that I knew it all. To this day, I love it when my wife jacks me off and we mutually masterbate each other. It almost as good as fucking sometimes and even better as I sometimes recall my first time with a wild, older, girl named Maria.
Processing your request, Please wait....
