Straight Male / 45
High School Crush At Reunion
I had always had a crush on Robyn since middle school, but she wasn't interested.
Robyn was absolutely beautiful. Tall & brunette with sparkling blue eyes.
Even in high school, she not only wasn't interested, but she would do her best to embarrass me by telling her friends what a loser I was.
I finally gave up. After high school, we obviously didn't keep in touch.
Twenty years later, I decided to attend our high school reunion. As fate would have it, there was Robyn. Still beautiful, but obviously older like everyone. I wasn't going to say anything to her due to the way she treated me back in high school.
After a while, she came up to me. Within a few minutes, I learned she was married & had 5 children. She was living in another state, but really wanted to reconnect with some old friends. Her husband stayed home to watch the kids. She was mainly a stay at home mom, but she was a choir director & volunteered at her church.
I told her I was single, never married, & no kids. I lived locally. I founded and sold a couple companies & was between things at the moment.
Over dinner, she ignored everyone else at our table quite rudely, but just focused on talking to me.
Then she asked me more about my companies. I told her they were tech companies, but the details would probably bore her. Then she asked what I knew she really wanted to know. How much money did I make from selling them?
I told her it was kind of embarrassing to talk about. She persisted in knowing. So, I told her. The first one for 7-figures & the second one for 8-figures. She was astonished. She had to think for a moment: You means millions & over ten million? Yes. That's right. She said I must be joking. I said I don't like fo brag. I don't flaunt my wealth.
She asked if we could have a drink. We had several. She was blowing off all her old friends she came to the reunion to see.
After a couple of drinks, Robyn revealed she felt totally overwhelmed as a wife & mother. Her husband & her were fighting all the time. Taking care of the kids was absolutely exhausting. Then, she revealed something extremely personal: Her sex life was in a shambles.
I told her that I was sorry she was so unhappy. I told her there was a time back in school when I wanted nothing more than to be with her, but after the way she treated me, that time had passed.
She said she totally understood. She said it had been a mistake to dump all her problems on me.
I told her no. I appreciated her honesty.
I offered her a ride to her hotel & she accepted.
Robyn asked if I wanted to come up to her room. I accepted without hesitation.
As soon as we got to her room, I took her into me arms & kissed her passionately. I pushed her against the wall. She was wearing a hot pink dress that fell to her mid thigh. I reached around her back & unzipped it. It fell to the floor. She was wearing a matching silk & lace bra & bikini cut panties.
I picked her up and carried her to the bed. She didn't say a word. She took off her C cup bra. I slid off her panties. I took off my clothes. I had condoms just in case of a situation like this, but then I decided I wanted to cum in this high school dick tease.
I began to fuck her as she immediately moaned. I talked dirty to her & she loved it. I fucked harder. I got her into position for doggie style as I thrust savagely, mercilessly. She screamed. I felt more & more like I was hate fucking her for all the times she had rejected me in high school.
Finally, I fucked her in the missionary position & looked deep in her eyes as I exploded deep inside her like a volcano exploding. She exclaimed, "Oh God! I'm not on the pill." I assured her things would be alright, but she was freaking out. I calmed her down. Honestly, her emotional pain & discomfort, that I inflicted on purpose, turned me on.
It was arguably the most satisfying sex I ever had.
Afterwards, she said she would like to keep in touch. I told her we could.
And we did. About once every month or two, I would fly to her city & we would meet in a hotel for the kind of sex her husband was unwilling or incapable of giving her.
She talked about leaving him for me, but I firmly told her I didn't want to be a stepdad. She understood, even if she was disappointed.
I finally had my high school crush Robyn, on my terms.
Robyn was absolutely beautiful. Tall & brunette with sparkling blue eyes.
Even in high school, she not only wasn't interested, but she would do her best to embarrass me by telling her friends what a loser I was.
I finally gave up. After high school, we obviously didn't keep in touch.
Twenty years later, I decided to attend our high school reunion. As fate would have it, there was Robyn. Still beautiful, but obviously older like everyone. I wasn't going to say anything to her due to the way she treated me back in high school.
After a while, she came up to me. Within a few minutes, I learned she was married & had 5 children. She was living in another state, but really wanted to reconnect with some old friends. Her husband stayed home to watch the kids. She was mainly a stay at home mom, but she was a choir director & volunteered at her church.
I told her I was single, never married, & no kids. I lived locally. I founded and sold a couple companies & was between things at the moment.
Over dinner, she ignored everyone else at our table quite rudely, but just focused on talking to me.
Then she asked me more about my companies. I told her they were tech companies, but the details would probably bore her. Then she asked what I knew she really wanted to know. How much money did I make from selling them?
I told her it was kind of embarrassing to talk about. She persisted in knowing. So, I told her. The first one for 7-figures & the second one for 8-figures. She was astonished. She had to think for a moment: You means millions & over ten million? Yes. That's right. She said I must be joking. I said I don't like fo brag. I don't flaunt my wealth.
She asked if we could have a drink. We had several. She was blowing off all her old friends she came to the reunion to see.
After a couple of drinks, Robyn revealed she felt totally overwhelmed as a wife & mother. Her husband & her were fighting all the time. Taking care of the kids was absolutely exhausting. Then, she revealed something extremely personal: Her sex life was in a shambles.
I told her that I was sorry she was so unhappy. I told her there was a time back in school when I wanted nothing more than to be with her, but after the way she treated me, that time had passed.
She said she totally understood. She said it had been a mistake to dump all her problems on me.
I told her no. I appreciated her honesty.
I offered her a ride to her hotel & she accepted.
Robyn asked if I wanted to come up to her room. I accepted without hesitation.
As soon as we got to her room, I took her into me arms & kissed her passionately. I pushed her against the wall. She was wearing a hot pink dress that fell to her mid thigh. I reached around her back & unzipped it. It fell to the floor. She was wearing a matching silk & lace bra & bikini cut panties.
I picked her up and carried her to the bed. She didn't say a word. She took off her C cup bra. I slid off her panties. I took off my clothes. I had condoms just in case of a situation like this, but then I decided I wanted to cum in this high school dick tease.
I began to fuck her as she immediately moaned. I talked dirty to her & she loved it. I fucked harder. I got her into position for doggie style as I thrust savagely, mercilessly. She screamed. I felt more & more like I was hate fucking her for all the times she had rejected me in high school.
Finally, I fucked her in the missionary position & looked deep in her eyes as I exploded deep inside her like a volcano exploding. She exclaimed, "Oh God! I'm not on the pill." I assured her things would be alright, but she was freaking out. I calmed her down. Honestly, her emotional pain & discomfort, that I inflicted on purpose, turned me on.
It was arguably the most satisfying sex I ever had.
Afterwards, she said she would like to keep in touch. I told her we could.
And we did. About once every month or two, I would fly to her city & we would meet in a hotel for the kind of sex her husband was unwilling or incapable of giving her.
She talked about leaving him for me, but I firmly told her I didn't want to be a stepdad. She understood, even if she was disappointed.
I finally had my high school crush Robyn, on my terms.
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