How I lost my virginity

To describe my first time in a few words, “It was very painful, very bloody.” I was 16 and living in Ft. Meyers, FL. My boyfriend “Kenny” was 18. We had been dating for a while and losing my virginity to him was basically driven by momentum. At the time, it felt like it was just the next step in our relationship.
As a teen, I had matured pretty quickly. I’m tall, and by the time I was 16 I had reached my full height (5’ 10”). I was thin and small chested and had been having my period for several years. At the time I lost my virginity, I had been using tampons for several years. The reason I mention this is that when I first tried using tampons, I realized I was fairly small or tight “down there.” Even now, as a sexually-active adult, I generally use “teen tampons” just for comfort.
Kenny’s parents owned a boat. One night we were out on a date and ended up at his parent’s boat. Their boat had what is known as a “cuddy cabin” which is basically a bed built into the hull below deck. It’s a v-shaped bed built into the front of the boat. We were on the bed and making out. I had a sense that “tonight was the night.” One thing led to another and we got into some heavy petting. I knew I was in trouble when Kenny started to finger me (the first time I had been fingered) and it hurt a lot. His finger wasn’t much bigger than the tampon applicators I had been using for years, but even the tampons were uncomfortable for me to use. Kenny managed to work his finger into me and the pain lessened a bit, but not much. He had opened his pants and I reached down for his penis was as shocked by what I found! Although I had nothing to compare it to at the time, Kenny’s penis was really big! Looking back now with a lot more experience, I know it was unusually big. So, it wasn’t just the perspective of a nervous virgin. It seemed like he was getting even bigger in my hand! I took my shorts and panties off and he had taken off his shorts and underwear. I noticed him take a condom out of the pocket of his shorts and was relieved. I certainly didn’t want to get pregnant. At the time, again not knowing any better, what I didn’t realize was that he had an unlubricated condom – probably not the best choice to use with a virgin. I wouldn’t even want a guy to use an unlubricated condom with me now!
So, I was a nervous young virgin with a fairly narrow / tight vagina (more on that later) about to have sex for the first time with a guy who had an unusually large penis covered in a dry condom – not the best idea. Again, what did I know? Kenny got on top of me and I opened my legs for him. I was excited and wet. He reached down and positioned himself, then slowly pushed into me. The pain was immediate and intense. He kept slowly working his way into me until he was fully inside of me. The pain really didn’t let up hardly at all. And, as he pushed into me, I felt my vaginal muscles being stretched a lot. He continued pushing in and out for several minutes until I knew he came. I could tell because I felt “something different” happening in me and by the way he was breathing and moving. I was glad it was over. He pulled out and the pain stopped. I was somewhat in shock. As he got off of me, I could see some blood on the condom in addition to what looked like a lot of sperm inside of it. While I was grateful not to have all that sperm inside of me, I was concerned about the blood.
As I started to get up, I felt something wet between my legs and reached down to find blood. It wasn’t the color blood that would come out of me during my period, it was a bright red color. There was also a pretty big blood stain on the foam pad I had been laying on. I remember thinking to myself at that moment, “I guess this is why they call it getting your cherry popped.” Kenny really popped mine. He sort of panicked, worried about the blood stain not coming out of the foam pad. We were eventually able to clean that up. I went into the small bathroom in the boat and cleaned myself up as best I could. I made a make-shift maxi pad out of toilet paper and put it in my panties. By the time I got home, the toilet paper was pretty bloody but my vagina had stopped bleeding.
Being older and wiser now, and having been to gynecologists, I have learned that I had a very complete and thick hymen as a virgin. This accounted for the sharp pain and bleeding. And I discovered that I suffer from a condition called “vaginismus” – or unusual tightness in the vagina. This accounted for my struggles with tampons prior to losing my virginity and the huge stretch I felt when Kenny entered me. So, needless to say, my first time was not a wonderful and romantic experience. Years later, in my late twenties, I tried anal sex for the first time. It was definitely uncomfortable and a little painful, but losing my vaginal virginity was much more painful for me. Women I’ve talked to about “both of their first times” have generally told me the opposite – their first anal sex was more uncomfortable for them than their first “regular sex.” – Julie S.


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  • Kenny is a lucky guy, you had to have been super tight that first time. The first time I had intercourse it was also her first time, I was really stupid and hard as a rock, I did a few little pushes against her outer lips then just plunged right in like three or so times. She screamed out and pushed me off, she rolled over on her side with her hands between her legs curled up. I thought that was how you had sex with a girl, she was not permanently hurt of course but I know it did not feel good for her and told her sorry, I got her a towel and we laid in bed for a bit while she recovered. She wanted to try it again a few hours later but told me to take it slow and easy, I did exactly what she wanted to do telling her to guide me and tell me what to do. We had a great time for quite a while that day, she was still sore the next day but could not wait to do it again.

  • Years after losing my virginity, I met the man who is now my husband. At some point during our relationship, we "traded" stories of how we each lost our virginity. So, my now husband, has heard the story I shared on this site. What I didn't share on this site, but my husband found out over time, is that my first boyfriend Kenny is also the first boy I gave oral sex to. Early in our marriage, my husband attended my high school reunion with me and had a chance to meet Kenny. I think it was a little awkward for him meeting Kenny having heard the stories of how I lost my virginities to him. - Julie S.

  • Have you at least given your husband your anal virginity Julie or did another man take that from you?

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