Living in a high rise among regular rooming houses and homes gave me the chance to use my binoculars. I had found a woman on the second floor of an apartment building across the parking lot from my building, and in full view from my room on the 5th floor, who liked to do her exercises in the nude. And she never bothered to close her curtains. Either she didn't know she could be seen or she didn't care. Today I had stripped down and I was naked with a boner and ready for her. She did not fail me.
She started her usual jumping jacks and her tits were bouncing up and down and my hand was stroking up and down my cock. I did not cum fast. I was ready for the second act. She would always turn away from the window when she did her toe touching with her legs spread wide and her ass hole winking at me. I loved the look of pussy from behind too. I kept stroking.
After that she would move on to sitting on the floor with her legs spread wide again. This time she would face the window and you could get a great view of the cunt as the lips spread while she was bending her back and touching your toes at the end of her luscious legs. About this time, after she had exercised for 15 minutes, I would start to shoot my spunk out in the tissues I had ready. God, it felt good.
This was always when I started wishing I could actually fuck some girl's pussy. I was 25 years old and still a virgin.
It was complicated and yet quite simple. I was shy. And when I did get to take a girl out, which was not often, I would try to make a move and if she said no, which they always did, I backed off. I never pressed for anything from a girl. Maybe they wanted me too. I don't know. All I knew is that I had been jerking off for years and had never felt a real pussy.
We had a local coffee house that I always went to on Fridays and Saturdays. You know, the old style coffee house where they played music or read poetry to a small crowd. I even would get up and read poetry myself on occasion. It was lousy poetry, but then most of it read there was not the greatest.
One Saturday I was scheduled to read some poems with another person. A girl named Debora. I had seen her there often. We all knew she was Jewish. That was a little different simply because the coffee house was run by a Presbyterian church. But actually we got all kinds there. The church never interfered. They were just trying to keep college kids off the streets I suppose. Everyone there was of college age or older. I was older because I had taken 4 years off to serve in the Navy.
Debora was tiny. Only about 5 feet tall, with long wavy black hair that glistened as if it was oiled. She usually wore counter-culture clothing that fit her style. Her hair was often tied up with a scarf and her blouses and skirts were made in India. She wore sandals and smelled of patchouli. I liked her. But we had never really talked. I was usually busy serving coffee and tea. I did that on a regular basis just to get to meet people.
This night Debora and I were reading together. And we enjoyed the smatterings of applause we got from the small crowd. It put us both in a good mood. So good that I dared to ask her to come back to my place and talk. I thought we might actually get to be friends. She grinned as she said yes.
We walked back to my apartment. It was only 2 blocks away. Debora took my hand. I was sweating and I am sure she felt it, but her hand was so soft and I was getting hard already. We took the elevator up to the 5th floor and on the way she drew my head down to her lovely face and kissed me. If I had not been already straining my pants I would be now!
I opened my apartment with my key, closed the door after Debora entered and she grabbed my hand again and dragged me over to the sofa. We fell together onto the cushions and she was making out with me before I even had a chance to think. But I sure as hell had no objections. She was lying on her back. I was on top of her kissing and just feeling a woman's body under me. Her breasts were so fucking soft and the nipples were pressing into my chest. Her hands were running through my hair and I did the same to hers. We were really making out. I loved it.
My cock was hard and laid straight up my jeans. I started humping her pussy when her legs spread apart. I had never dry humped before, but I was loving it. It was the closest to fucking I had ever gotten. I could feel the warmth of her cunt as I fucked her with our clothes still on. She was humping me right back. It only took about five minutes for me to shoot a wad of spunk into my underwear. She had orgasmed too. She had screamed it out when it happened.
"Wow, James, that was something else. Lots of fun. I've never done that before. Let's do it the real way next time, okay sweetie?"
She grinned at me as she gathered up her stuff and got ready to leave. Oh shit, I thought to myself. This is the last I will see of her!
"So what time do you want me to come by tomorrow? I can cook us something if you want."
"Oh, well, you can just drop by about 6 or so. I'll have stuff to cook. I'll see you then. Want me to walk you home?"
"Nope, I have to stop off somewhere. Later lover."
She kissed me goodbye and skipped out of my apartment and I locked up for the night.
Heaven! God I felt good. I was never so fucking happy in my life. A girl liked me. And she fucked! Damn!
I didn't sleep that night. Maybe a little. But not much, I know that. I got up and went to classes but all my thoughts were about Debora and what we would do that night. I stopped at the local alternative coop grocery and got some stuff I thought she might like. Me, I didn't care about the meal. I wanted the dessert.
At 6:30 Debora arrived to flit around the room and check out my kitchen. I would find that she was always late, but this time I thought I had been stood up. Hearing the doorbell was like hearing a full orchestra playing just for me. She did some magic in the kitchen and a great meal appeared on the table. We dined with some Janis Ian and Leonard Cohen playing in the background. We drank some cheap wine and had a ball.
I helped clean up. Well actually I did all the clean up. Debora was sort of dancing around my apartment checking out my books and paintings. She stopped at one point and said something about my books.
"I judge a man by how many different publications of Shakespeare he has. You have 3 different ones, so you pass lover."
That was just dumb luck on my part. I gathered books like some people gathered flowers. I picked them up and kept them all until they fell apart.
"Are you ready to really fuck me now, lover? No more faking it my man. Let's do this. I want to use the bed this time."
This was it. I was going to lose my cherry. We giggled our way into the bedroom, throwing off clothes as we went, and were naked when we fell on the bed and my leg went between her two legs and I felt the hot pussy wetness on my thigh. Her hand went to my cock and started stroking it. It could not get harder but I didn't want to cum to fast. I went for the gold and actually touched pussy for the first time. Hers was nice and hairy with wet droplets on the short and curlys. I rubbed it and found the clit. I had read all about sex. I may not have done it but I had sure as hell studied it.
I knew the clit was sensitive so I was gentle. I just rubbed it with my thumb until she started moaning and humping up against my thigh. Her grip on my prick tightened and I almost groaned with the pain, but I liked it too. Then she was moving my dick towards her pussy. She wanted to be fucked. I wanted to fuck. We were going to do this. Hell!
Spreading her legs apart, she made it clear what she wanted. I grabbed my cock and guided it to the opening that was pulsating for me. Her labia were swollen and pink. They were dewy with moisture. I softly pushed my cock into its first cunt. I never will forget that feeling. Jesus, it was the best thing in the fucking world! I pushed harder and she grabbed my ass cheeks and pulled me deeper into her pussy. She knew what she needed.
Her legs wrapped around my waist and she started bumping nasties with me. I was fucking her but she was fucking back just as hard. Her legs were pulling me in. I was trying to fuck her as hard and as fast as I could. Then she took a hand and offered one of her luscious tits to me. She wanted me to suck it. Fuck yeah!
I sucked it as hard as I could and stretched the nipple out and let it spring back. Then I gave it a nibble and she squealed with lust. All the while I was thrusting my prick deeper and deeper into that juicy cunt. I fucked her so hard her head was banging against the headboard of the bed. I couldn't take much more of this. I could feel juices oozing out of her pussy and lubricating my hard cock. I felt the walls of her cunt almost sucking up my cock and taking it in farther and farther.
With a cry of triumph I shouted out, "I'm cumming."
She humped me faster and faster and took all the strings of jism I shot into her pussy and wanted more and more. And she was kissing me with all her tongue rammed down my throat. Her hard tits were pressed against me and I rose up and just rammed as hard as I could and she fucking screamed with passion.
I will never forget that. She was my first pussy. She would not be my last. But for the time being we were inseparable.
Debora was not only my first fuck. Oh no. She was ready and willing to teach me everything she knew. I don't know if she ever really knew she was my first. It didn't matter. More lessons were ahead.
In the following weeks Debora was my rock. I loved her of course. The next weekend she came over and we had dinner again. But this time she wanted something else. I was to learn that my Debora was a real cum slut. She loved cum. Hers, mine, almost anyone's. She even loved eating pussy. So she told me later. This time it was my turn.
She slowly undressed me. She talked as she disrobed me and told me how much she loved my body and what she was going to do to it and what I was going to feel. I was living the dream. She tossed off her own clothes and knelt before me. She gazed up with her green eyes into mine and wiped her hand on her pussy. Then she took that hand and massaged the juice into the head of my prick and slowly took the head of my dick into her hot mouth.
Her hand cradled my balls a moment and then she squeezed them and made me cry out with pain. I wanted more. She jerked them down as she sucked my whole cock into her mouth. Then her tongue was making swirls about my dick from the base to the tip, but never letting it fall out. Then she started jacking my cock with her hand using her spit as a lubricant. She took the head between her teeth as she jerked me off.
She let go of my prick with her mouth and spoke to me.
"I need to know when you're going to shoot. Okay Jimmy babe? Let momma know. I want it in my mouth and on my face and on my tits. Okay, lover? You do that for momma."
No fucking problem. She went back to sucking me off and jerking me at the same time. I started fucking her face while I held wads of her hair in my hands. And then I had to give it up. I had to shoot.
"Fuck, Debbie, fuck here it comes, baby."
I started shooting as she quickly moved her face in the line of fire. I filled her wide open mouth and moved on to her face, soaking it well, and then hosing down those luscious tits with the nipples like fucking rubies. I came and came. I had saved lots of cum over the years, or so it seemed. Then I leaned down and kissed her cummy face and just loved her.
That was a good night. We slept together all cummy and gooey. It was fun. I was getting to know sex and loving every second of it. Debora was my adorable one.
The next weekend, after a long week of finals we were able to get together and have our usual vegan meal. Debora was a great cook, but animals were never on the menu. But cock and pussy were, after the regular meal.
Tonight we made that happen. Debora was showing me how to really eat pussy. While she sucked my cock in anticipation of another cum shower. I was on the bottom and she was grinding that cunt into my willing face. I bit her clit as she liked me to do and she squirted on my mouth. I sucked it all up. Her mouth was fucking my prick, moving up and down with her lips tight as fast as she could. I was making her cum and cum. I had one good cum in me and I was trying hard to save it to hose her down again.
At last I had eaten the pussy so much that the swollen lips were too tender for me to touch anymore. She had given me all she had, and now I would give her mine.
"Debbie, babe, its coming. Its going to shoot."
She took her mouth off and grabbed and squeezed my cock. Then, when I was about to burst, she released it and I sprayed her face with my spunk. Her mouth sucked up what it wanted and she guided it all over her face again. She was a great cum slut. I shot all I had and then she sucked every bit of cum out of me that she could get. She smacked her lips and then made out with me for another 10 minutes as we pressed our bodies together with my arms around her and her tickling my nipples.
Then she had to go.
School was over. I got a note from her in my mailbox the last day of school. She was leaving. She had finished her courses. She would get her diploma in the mail. In a day she would be on a kibbutz in Israel. It had been too hard to tell me in person.
I never saw her again.
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<a href="https://www.lushstories.com/stories/first-time/twentyfive-year-old-virgin-part-one.aspx">Twenty-five Year Old Virgin (part one)</a>