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I had had a triad of failed attempts with my first girlfriend. The first time, she kissed me with tongue and started to stroke my cock, I was so taken a back it took me a while to recover composure. Then she took my hand and inserted it in her blouse on her tit. That got me going. Then she asked if I wanted to join the club.
I took that as an invite to fuck her. We were on the sofa in my mom’s house when everyone else had gone to bed. There was a garden chalet so we went out there and removed a few more clothes and started the heavy kissing and petting. I then pulled down her panties and freed my cock and tried to insert it. She was a bit shocked and said what about protection. No protection available for 40 miles. In the 80s you needed a mainstream chemist to buy condoms. So that was the end of that.
She was a little older than me and had a car and a few days later, she drove me down to her house, 100 miles South. Her parents were out so she grabbed me and pulled me to her parents’ bedroom, lost her clothes, ripped mine off and pulled me onto the bed. Again, we had no condoms but she, by that time had decided that she needed to get fucked badly. We were both virgins and her comment about joining the club was meant as a reference to that.
So there we are, naked on her parents’ bed, with them potentially returning at any time, trying to have sex for the first time. She was tight as hell and my cock got sore when my foreskin was folded back. We had never heard of KY, she was as dry as hell and closed like a clamp and I was reeling in pain as my foreskin got pushed back against dry pussy lips. It was a comedy of errors. After about 15 mins of struggling, pain and frustration, we decided to abort before her parents walked in. Whew!
The next attempt was a few weeks later. My mom had a flat in town and I had a key. It was usually rented but at that time it was vacant. So I called my GF and we went over to fuck. I had bought some condoms and we lay down in front of the electric fire – winter in the UK – and peeled off enough clothes to get action but without freezing. We put some cushions on the floor underneath us. I fingered her and loosened things up a bit. She got a bit wet. She asked me not to put on the condom to start with as she wanted to feel my skin. I had spent the best part of 3 weeks stretching my foreskin so it rolled over the head nicely. So we were both prepared. I got my cock lined up and gave a small thrust to enter her. My balls must be made of reinforced concrete as they had managed to hold in enough pressure to blow Mount Vesuvius. As my cock started to enter her and the foreskin rolled back, I exploded. I pulled out and she freaked, ran to the bathroom and started washing while screaming about getting pregnant.
All in all it was a highly memorable experience. 2 non events followed by a fiasco! We never did manage to do the final deed. I don’t count 1/3” of penetration as popping her cherry! So I remained a virgin for another year while she went off and found another hunk who had “experience”.
Its always one of my regrets. I adored that girl and wish to fuck I had “had” her!
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