Think about your first time..

Think about your first time having sex and have far you've come since that first experience (assuming you've gained more experience since then)... If given the opportunity for a "do over" with the experience you have now, would you do your first experience over again (with the same person) or no, it was what it was and you're not interested in changing that experience?

(Bonus: Share stories of your first time below).

Yes, I would love to re-do my first time using the experience I've gained over time. 8
No, I was what it was and I am ok with that 6
Don't Care... had sex! 1
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Comments ( 9 )
  • esquire_nj

    I was 17 my first time having intercourse. I have gotten head many time prior, but never made all the way to full on sex. On Oct 14th (yeh I remember the day lol) at 2am (yeh I remember the time) my girlfriend and I were getting back to my house after having a fun night with other friends going to haunted houses and what not. Both our parents were cool with each other and we assumed they already thought we were having sex, even though it just mainly oral and mutual masturbation type stuff. So it was nothing that we would spend the night with each other. Once we got in I took a shower and then she did. However, while she was showering I fell asleep on the bed still in my towel. At some point during the night I guess my towel came off because I woke up and noticed I was spooning her naked. She had on one of my t-shirts and her panties on. However she was sleep and resting so peacefully lol.

    My bedroom was in the basement. I kinda had a little apartment down there. I had a bedroom, living room, full bathroom, mini kitchen area and a room for my weights. Everything but a stove lol. So when the lights were off it was total darkness. You wouldn't even know what time of day it was without looking at a clock. At some point, I was in my head thinking about how good this felt being pressed up naked against my girl. My penis was dumb hard and seemingly perfectly sandwiched between her butt cheeks. At around 5am I was woken up to my girl sitting on top of me and sucking on my neck and kissing on my chest. I had (and still have) a nice athletic body (I played football, basketball and ran track... oh and I was also a straight A student too). She has kissed on my chest and abs before but this time I was totally naked so my penis was hard and throbbing. She could obviously feel it because when I put my had down her panties, she was DRIPPING wet. That was the wettest I've ever felt her. Keep in mind, it is still PITCH BLACK.

    Long story short, the moment got to us and one thing after another, my girl put my penis in her. She slowly slid all the way down on it. The feeling was great on my end, but I could tell she was experiencing some pain, because of how tight gripping me. However she was on top and was in control of it all. Once she got all the way down on it, we kinda just laid there for a minute or two... in shock that we were having sex. I was also in shock because I realized I had no condom on and didn't have any even if I wanted to stop and put one on. I told her this and asked if she wanted to stop because there was no condom and she said with pleasure "absolutely not."

    So then we started kissing and even though she was on top and I was laying on the bed, I started thrusting in her slowly. I distinctly remember the feeling of my penis "opening her up" the deeper I went. I always felt like I had a nice size penis for my age and that "opening" sensation was an ego boost too. I was so in love with how good that felt. I was also amazed that I did not nut in 30 secs lol. What seemed like 20mins was only about 8 lol and I told my girl that I was getting ready to nut and that she needed to get off of me. Little did I realize that she was in a state of shock because she froze up and never moved, but was still "riding" me a little. I kept warning her ..."hey lol you REALLY gotta get up." No luck. My very first time having sex, I nutted what felt like GALLONS of cum into my girl. My penis had never throbbed so hard in my life. I thought I was dying lol. I wrapped my arms around her so tight while I was cumming and as I was cumming, she orgasmed too. I felt her vagina pulsating on my still erect penis.

    As soon as the cumming sensations stopped she immediately starting crying and I thought she was sad that she just lost her virginity. I asked her if she was going to be ok and so said something like, "im not crying because I am sad, I am crying because that was so beautiful and Im happy that we just experienced that together" ...I immediately smiled (even though she could barely see it) and started kissing her.

    We washed up a bit, I put on boxers and then we went to sleep spooning. Later that morning, we had sex 2 more times in different positions (missionary then doggy). Still no condom but we didn't care at that point. Thankfully we didn't have a pregnancy scare and no STDs and what not.

    That was almost 10 years ago. We are good friends but not in a relationship with each other. In fact she is probably about to get engaged to one of my best friends and thats great! Would I change that experience ...never! We had an experience that felt like something straight out of the movies and I wouldn't change that for anything.

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    • Wow. Very nice story.
      Thank you for sharing.

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  • IrishPotato

    If it was up to me, I'd wipe out all of my experience if only I could have my only time with my current girlfriend.

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  • nikkiclaire

    This thread just seems creepy to me. 🤤

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    • donteatstuffoffthesidewalk

      dear penthouse letters this sorta thang never happens to me but the other day....

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  • lordofopinions

    My first time was on my parents couch. They were out and I knew they would be gone a while so we started necking. One thing led to another and I was banging her. I came so much some leaked out and got on the couch cushion. I cleaned it best I could then flipped it over hoping they never noticed. As far as I know they didn't.

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  • justfkinwork9000

    No retake. I fucked the hell out of her for 45 minutes before I came on her big titties. Top 5 best memories.

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  • McBean

    The second girl I had sex with was pretty cool. I married her.

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  • Ummitsstillme

    She had a reputation. I was 16. I was terrible but she didnt tell me.

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