(Thank you all for your patience. I finally have a chance to sit down and write this second part. Just a reminder I was 25 when this occurred)
On the morning of the night we planned for him to take my virginity, I woke up feeling super nervous but also super excited. I masturbated twice that morning thinking about it. That night he took me out to a very nice restaurant. The entire dinner my stomach was in knots but my pussy was getting very wet. We went back to my place and began making out. I took my heels off, he took his shoes and socks off, and our bare feet were soon touching as our tongues danced. I took his shirt off and started sucking his nipples, then he pulled my dress down and kissed and licked my breasts and nipples, making me super wet. He suggested we take a shower together, which sounded lovely to me.
We went to the bathroom where we finished undressing each other. In the shower we washed each other and then pressed our naked bodies together as we made out. It felt so fucking good! He began rubbing my clit and sucking my nipples and in no time at all he made me cum hard. He said he thought I may have squirted a little but under the water he couldn’t stay for sure. Then I knelt down and took his cock into my mouth and blew him until he came in my mouth. We kissed gently as we dried each other off and then walked hand in hand into my bedroom.
He layed down on top of me and pressed his naked body into mine as he kissed me deeply. I loved feeling his bare chest on my bare breasts, his bare feet touching my bare feet, and of course his cock on my pelvis as he slowly became hard again. He started kissing down my neck to my boobs and sucked both my nipples for a long time. Then he kissed down my stomach, down my leg to my feet. He kissed and licked my feet and sucked all 10 toes one at a time. He was driving me insane. Then he kissed back up to my pussy and ate me out until I came even harder than in the shower.
Then we made out some more and he asked if I was ready to lose my virginity. Before I could doubt myself I said yes. He asked if I was sure and I said yes. It was at that moment he realized he’d left the condoms in his pants, which were still in my bathroom. As he left to go get them I lay there naked on my bed, wondering what sex was going to be like. And for a second I started to doubt my decision. I considered backing out, and I hoped he’d understand. But when he came back in and I took in his naked body again, and saw his fully erect cock bouncing as he approached the bed, I knew I wanted to do it. He climbed on top of me and kissed me. As I watched him put the condom on he asked one more time if I was sure I wanted this. I said yes.
So he very gently began putting his cock inside me and yeah the stories are true, it did hurt. The only thing that had ever been inside me were my fingers. Hell just one month prior NOTHING had been inside me besides tampons. So yeah there was pain but it wasn’t nearly as bad as I was expecting. He got himself in, asked if I was okay. When I told him yes, he began kissing me and very slowly moving in and out. As he fucked me we kissed for awhile, he sucked my nipples, then go back to kissing me. Eventually the pain faded and it started to feel pretty good. Not orgasmic good (not yet anyway) but I very warm feeling. He eventually picked up his speed and we fucked for awhile longer before he suddenly stopped thrusting. I asked what was wrong, he said he was starting to get close to cumming and wanted me to cum first. Now at this point I was feeling pretty good, way better than I was expecting, but at this point I knew when an orgasm was approaching, and I just wasn’t feeling that. I’d also read most women don’t cum their first time. I told him it was okay, he’d already made me cum twice with his fingers and his tongue, and to just go ahead and cum. So he started thrusting again while our tounges danced and before too long moaned into my mouth as his cum filled the condom. We made out for a little bit longer before he started to pull out.
As he got off of me and took the condom off, I was suddenly extremely overwhelmed. I started crying. He immediately asked what he’d done wrong. I promised him he hadn’t done anything wrong, I was just overcome with emotions. He held me and cuddled me until I fell asleep in his arms. I woke up the next morning, still naked, with a text from him that he had to run home before work, how much he cared about me, that he hoped I was okay, and to call him later. As the memories, both physical and mental started coming back, I started playing with my tits and rubbing my clit. I was sore but not unpleasantly so. I ended up masturbating to two orgasms remembering the events of the night before. And in that moment I realized I had zero regrets.
(I’m so sorry to do this but I am gonna have to make this three parts. The final part is gonna be a little streamlined because I’ll be catching up to the present but I’ll still have some sexy details to make it worth your while)
Source: reddit.com/r/gonewildstories/comments/u9jmyd/fm_overcoming_my_repressive_upbringing_part_ii