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Times in my life. Lisa pt 2
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Times in my Life - Lisa
15/01/2026
Back again with another of my adventures.
My stories are all true and happened pretty much as I write. I don’t get into bra size or penis length. To be honest don’t think I ever looked or asked.

So onto the story of the day.

This happened during my time as a pizza maker a job I held through high school and into my early working years. This happened early 80’s as I was a young man newly into the working world but still naive in the way of the world. I had been having “lessons “ from an older woman that i worked with ( times in my life. Jane ). She had been quite the teacher and I think that my sexual progress was amazing. But she was married and not always available.

As we worked in this restaurant there was always flirting and a lot of sexual talk. One young waitress Lisa was a co worker. Who I often chatted with and was always giving it back to me.

Lisa was a good looking young woman about 5’5” and had an amazing pear shaped body. Small tits on top of a very flat stomach and wide hips. The thing about her that always fascinated me was the gap between her legs. I swear to this day I have yet to see a woman with such a gap. She had very short blond hair and her face was hidden behind a huge pair of glasses.

A plain girl but intriguing non the less.
One Saturday night as we worked out shift and the flirting and banter went back and forth she asked me what my plans were for the next day. I told her that my entire family was going away for the day and that I would probably spend the day naked in bed.

She laughed and said that I should go running with her in the morning. lol. Fat chance of that I said. She then dared me to run with her and not be so lazy. She then said that she would be at my door by 9 and to be ready to run. I told her that she had no idea where I lived and good luck with that. But she was insisting that she knew. So I made her a bet. If she was there by 9 I would run with her. But if she was late that she would have to join me in bed naked. She laughed and said no way. So I dared her back.

As the night progressed, the talk kept going and and we both called each other chicken. Finally she wore down and very sure of herself she made the bet.

Now the fun part of all this is that my older brother and his family lived next door to us and many people thought I lived there. So it could get interesting
The morning came and my family left the house and there I was alone and and decided to get up and dressed in case she did show up. I was expecting a phone call with an excuse to cancel.

About 10 to 9 I look out and sure as can be there she is knocking on my brother door. lol. I had her! As I looked out the window I could see her in her running shoes and a loose t shirt atop of some nice shirt Adidas shorts. Loved the 80’s !! I waited and watched as she started to become frustrated as nobody was answering the door. Finally as I made sure it was after 9. I opened the window and waved to her. The look on her face. I told her to come on over !

She came to my house and I had to prove to her that is where I lived. And then said a bet is a bet. Time for you to pay up ! She said no way. Hahaha. Joke was on me. So I said no problem I was got g back to bed and she could join me or not.

I went up to my room and got naked and climbed back to bed. A few minutes later she came up. She said I can’t believe I am doing this ! She asked me what I was wearing and I told her I was naked under the sheets. She asked me to prove it and I quickly lowered and the realized the sheets and she was in shock. I said want to join me. She sat on the bed and told me that while she has had sex she has never been naked in the light with a guy. I said first time for everything. She wanted to close the curtains and darker the rock.

She said she was very shy about her body as she did not like the way she looked. I told her that she probably had an amazing body and that she had nothing to be ashamed of. After a few min she gave in and stood and pulled her shirt over her head. She had a nice white bra on. Nothing sexy and having small tits everything was covered.

The shorts came next. Leaving her in a dark pair of bikini panties. She wanted to join me under the covers like that. But I insisted that the bet was naked. So with a scowl on her face. First she lowered her panties revealing a nice blond bush covering her pussy and then with even more fear she reached behind and undid her bra. She said that she did not have much in the boob dept and she was very shy about them Once I saw them they were beautiful. Nice small mounds topped by bright pink areolas and pencil eraser thick nipples.

Her face was bright red behind her glasses. I took a few minutes to admire her body it was incredible. I pushed the cover ls down and she saw my hard cock standing straight up. Jump in I said and she washed to time.

I pulled her to me and we started to kiss Deep. Long kisses. Her tongue was in my mouth in an instant. God this girl could kiss!! I pulled up for air and asked her how far she wanted to take this. She said a bet is a bet and she was willing to pay. As long as I had a condom. I told her that I did. And then went back work on her body. I kissed her mouth and then neck. And worked my way down to her fits.

Holding her by the waist. I placed my mouth on one of them and sucked the whole thing in my mouth. They were very firm and her nipples rock hard. She was moaning as I feasted on one and then the other. Which one was not in my mouth my hand mauled. Rolling her nipples between my thumb and finger. She was moaning and thrashing. Telling me how good it felt.

Now was time to put my lessons from Jane to good use. I kissed my way down her flat belly. Licking her belly button Lower I went. She asked me what I was doing. I told her I was going to eat her pussy. She said she had never had that done and was I sure I wasted no more time as buried my face in her blond bush. Using my tongue to open her pussy up. The gap between her legs was amazing. Her pussy was laid bare to me. Even though shaving was not a thing back then.

Her blond pubes were neat and sparse. I used my fingers to her up better and expose her tiny clit. I slid a finger inside her. She was so tight that it barely went in. My tongue was working her clit with small licks. Followed by deep sucks and the occasional light bite. I worked my finger slowly in and out of her. She was on fire. Her pussy getting wetter and wetter
She was moaning and just rambling.

I was feasting. Her pussy so fresh. This was the first young pussy I had tasted. And the difference between hers and Jane was amazing. I kept going and she started to buck her hips into my face. I took my finger out of her tight pussy and grabbed her ass with both hand and really attacked that pussy I did not take much longer and she let out a scream as a grew came all over my face. She came and came. She almost smothered me she was pushing into me so hard.

I kissed my way back up her body. And gave each tit a nice long slow suck until I met her lips again. The kiss she gave me made the others before seem weak. She was a wild woman.

She asked me where the condom was she wanted me inside her. I reached into the nightstand and grabbed one and got up on my knees to roll
It on. I looked down and was amazed. At the sight. Her face was flush. Her tits red from my sucking and her pussy all damp and matted. I asked her to take her glasses off as I really wanted to see her face. When she did she revealed the most beautiful blue eyes. I told her she was beautiful.

I grabbed my cock and put it to her pussy and asked her if she really wanted it. Please she said. Give it to me. I put the head to her opening and slowly pushed in. She was as tight as a vise. I was only her third she said. But they had only been real brief. I went back and forth with my cock. Each time pushing a bit more in. Finally I had I all the way in. Now I am not the biggest guy. But this girl was TIGHT. I held it there and just slowly moved my hips and we started to kiss again. And then her hips started to move. She wanted it. Give it to me she kept saying.

So I started to fuck her. Long slow strokes. Almost all the way out and then slowly back in. I was in heaven. After a few minutes of this I started pull it out slow and then slamming it back in. She loved it. There were no more holding back I wanted this pussy. I started to fuck get hard. Our moans and groans filled the room. No way I was going to last long. But we had the day. So I pounded her. She responded by pushing her hips up to meet my stokes.

I felt my balls tighten grabbed her ass and pushed as deep as I could and I could feel the cum erupt. I filled the condom with what seemed like a gallon of cum. I fell on top of her. She wrapped her legs around me and we kissed and kissed. As she felt my cock soften we pulled apart. And she asked if I had more condoms. And if we were going to run in between. To be continued ...
Poster: JD


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