1. Winnie Losing our Virginity


    Date: 5/9/2024, Categories: True Story Author: Steweird 

    ... supremely hard and I wanted to get back on top of her as soon as Winnie was done her tears.

Finally, she quit crying but instead of saying “Okay, let’s start fucking again.” like I naïvely hoped she might, she whispered like a little lost girl “Can you take me home now....please?”

She could plainly see my penis was still fully erect. How could she possibly not see it, sticking up between us like that inches from her breasts, my knob almost brushing her nipple? She had to have known I still wanted to finish our little back-seat romp.

Disappointed as I was, I kissed her on the forehead and gently said “Okay, get dressed” even though my pecker was urging me to callously go back at it on top of her like the insensitive son-of-a-bitch I was. I just did not have the heart to force her to put out.

Deep down inside I knew it was me and my stupidity that had blown my chance for a lay that night. The rational part of me understood that Winnie needed to go home but it was still hard to stop having so much fun in mid-fuck.

I drove all the way to her place with my hard-on painfully crammed inside my zipped-up jeans. I hugged her ‘Goodnight’ then went home ...
    ... and jerked off a couple times in frustration.

(Comment below. Tell me about a lover that mistreated you...or that you mistreated?)

EPILOGUE

We eventually broke up when Winnie finally grew up and realized we had nothing in common and that I just wanted to screw her. I started dating a nice girl, Réjeanne, who had tits as big as Marian’s and Winnie’s combined so I finally got to play with some real hooters! Winnie went on to date other guys.

Winnie and I kept in touch, though. When she was between boyfriends and feeling horny she would phone me up to see what I was up to. I guess it shows you what kind of boyfriend I was that I didn’t even think about Réjeanne; I just went over there for a hump with my old flame and left Réjeanne wondering where I was that night.

Winnie used to tell me about other guys she had met. By then she was fucking all the boys on their first date with her; after all those years of putting up with her stubborn virginity and all my hard work to pop her balloon these guys were getting it from her without even having to take her out for a second date; she just went back to their place and let them lay her! Can you believe that?
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