People Tell What It’s Like Losing Their Virginity at a Late Age

Wendy Stokesby:

Love & Sex

Do you remember how old you were when you lost your virginity? I went to an all-girl private school and remember being one of the only girls at my high school who either never had sex or wasn’t on birth control. I used to look forward to my friends’ stories of doing it for the first time—that ism until my first encounter at 17. I remember it like it was yesterday.

Though I wasn’t as young as my friends were when they lost their virginity, I still gave it up at an early age, IMO. But there are some people who didn’t wait until they were in their early-late 30s, even 40s to do the deed. A Redditor asked the question, “Those who lost their virginity very very late (30’s, 40’s etc), how did it happen?”

Both men and women chimed in to give their personal accounts on what it was like popping the cherry (or blueberry):

1. 27-year-old here who only lost it 6 months ago. There are some things that apparently made me “really good” in bed which I thought was kind of “de facto” for sex – like paying attention to her whole body, not just gunning for PIV, selflessly stimulating her, rubbing g-spot, etc, so it’s feasible.

Then there are other things which I was pretty laughably bad at (like going down on her, for instance) initially.

Then again, she knew from the offset I was a virgin and was really f*cking understanding about the whole thing, which helped a lot. Went through some things in a pretty clinical manner. (TheTjalian)


2. I was 30 and had never had a boyfriend or been on any dates. I came from a pretty religious background that I had long since left behind but I still had some hangups about sex and how it was this huge momentous thing. I’d built it up so much in my mind it was ridiculous. Add to that I’m pretty socially awkward, shy, and very cautious. Well 30 comes around and I’ve had enough. F*ck it, I just want to get it over with so I sign up for OkCupid with the intent of just going on some dates and having fun. First guy I chat with is kind, sweet, and funny so we meet up for drinks. By the third date I’m ready to lose it, but I didn’t tell him he was my first. It was a little painful but I faked my way through it, and there was a tiny bit of blood which I blamed on maybe starting my period early. I figured I’d never see him again so I tried to not feel bad about the stain on his sheets.

Well he was even kinder and sweeter and funnier than I had anticipated. A fourth date became a month became a year… Etc. four years later leads us to today. We’re celebrating our first year of marriage in a month and we just bought our first house. He’s my absolute best friend but he still doesn’t know he was my first. (Harmenia)


3. I was 33, a lesbian who only dated a few girls, also late in life. I’d been seeing a girl long-distance and she came to visit for a few days. That first night we fumbled but I had no experience and she was used to someone else being “in charge.” She told me she didn’t want to hurt me, that I was like “a 12 year-old.” I turned towards the wall and cried. The next night she touched me and I eventually got off. I’m counting that as sex. That was a few years ago and we’re married now…maybe done that a handful of times. I guess that counts. (Time_Ocean)


4. I am 34 now and was 30 when I lost my virginity. I suffer from social anxiety and depression, which means that it will take a very long time to actually get comfortable around people. Between that and the fact that none of the people I fell in love with were interested in me, it just never happened (one night stands or hiring a prostitute or stuff like that were out of the question, as it would trigger major anxiety attacks).

I had developed feelings for a friend and, as it turned out later, he also for me. Since it was a long distance relationship, we would talk a lot on the phone/online and really got to know each other well. He knew of my anxieties and never pressured me into taking it to the next step – he would wait until I was ready for it.

He came over for a lengthy visit when it finally happened. The first two nights we would still sleep in separate rooms, then in the same bed, and after a week… it just happened. A little over a year later we got married, and still are. ([deleted])


5. I was 36 when it happened for me. I hired a prostitute. She was a big woman who I found on craigslist and we discussed how it was my first time before we met up. She took good care of me and helped me through some issues I was having with getting an erection. After about an hour I had finally achieved vaginal intercourse. I paid her for her services and haven’t ever been laid since. (L-Chron-Hubbard)

6. I lost mine at 39. Yes, 39.

I had my first naked-with-a-girl experience at 23, but when she told me she wasn’t in love with me, I physically locked up. Took me months before I could even masturbate again.

Eventually I got together again with the same girl, but during foreplay she played with my penis and I came immediately. That was the last day in college and the end of that story.

Second time, I was 34. I actually penetrated but it immediately went limp. That was an amazing confidence builder.

The third time was with my current wife. We had gone out on a few dates. We had watched a movie together at her place, kissed the first time that night. She asked if I wanted to sleep over in the literal sense of the word. I didn’t sleep at all, fully erect the whole night. We did the deed in the morning. I came in 1 minute.

Things were already better the second time and now we have a totally normal and very satisfying sex life. I’m a happy man. (lost_it_at_39)


7. It was about 2 months before my 36th birthday. After living most of my life as a morbidly obese, depressed, alcoholic foreveralone, a sequence of events occurred that made me decide to change.

In 2012, a woman asked me out on a date (the first time this had ever happened) and at first I said yes, but later I backed out, blaming it on social anxiety. The woman was spectacularly unattractive, but really I was just too embarrassed at my lack of experience to go through with it.

A short time later a family member died in a horrible car accident. He was well-liked in his community, and hundreds of people showed up for the funeral. I sat there at the service and imagined how if it was my funeral, how few people there would be, and how little they would have to say about me.

That was the catalyst, and over the next few months I started to feel a little better. I realized I was no longer depressed, and I had a desire to change. I joined subreddits, and although I never participated, reading the posts made me slowly realize that change was possible.

In early 2013, I read a book with a diet plan that I thought I could stick to, so I tried it and ended up having great results. I quit drinking, and over that year I lost about 90 lbs (130 in total today) and my confidence grew, somewhat.

At the end of 2013, I decided that I really needed to meet women, but I was too embarrassed. Browsing reddit one day I read a post on how to hire a prostitute online, and decided to do it. At the time I thought it was the only way to gain the experience I needed to meet real women.

I didn’t tell the girl about my past, just the fact that I had lost a bunch of weight and was shy. It was awkward, but even though it wasn’t ideal, afterward I felt as if a huge weight had been lifted off my shoulders. My whole life I had agonized over the fact that I would always be alone and a virgin, and suddenly things were different.

I got a little crazy after that, and ended up hiring about a dozen different girls over the next few months. I ended up really hitting it off with one, and we started seeing each other, and have been together about a year. She’s quit the business and we’re pretty happy now.

It’s not a story I’d share with anyone I know, and I’m not exactly proud of it, but i’m not exactly ashamed either. Sometimes you gotta do what you gotta do. Luckily in this case it worked out, and if nothing else, I’m much better off than I was before. Also, sex is really, really nice. (Badger_Dick)


8. About a year ago, at 35. I lost it to an Asian “masseuse”. It lasted all of 30 seconds. It wasn’t particularly enjoyable, but at least I won’t die not having experienced sex.

Background: After 35 years of waiting for the right person, and then finally, finally finding that person, only to find out that she doesn’t feel the same way about me… well, I basically decided to stop saving myself for anyone. I’ll never have the love I want, and I won’t be able to “give myself” to her, so I decided to just throw my virginity away by visiting one of these Asian massage parlours that one hears so much about. I’m not proud of it, nor do I regret it. After waiting so long to give it to someone special, it suddenly became useless to me. (throwaway49576)


9. I’ve always had an inferiority complex with women so I turned to men for sex. I had my first gay sex at age 36. However I was still interested in women. One of the few friends I have that knows I’m bi, decided to help me with women by taking me to a special masseuse that would cost $120. My friend is Vietnamese and knows I have a thing for Asians (male or female), so he took me Vietnamese massage parlor.

It was a regular home in residential neighborhood of Southern California. We came to the door and an old woman spoke to my friend in Vietnamese. He then told me I was all set and I was let in while my friend went back to the car to wait. As I came in, I saw a hall with red lights over each of 6 bedroom doors. Out of the last came a girl, maybe 24, who had a great body, but not a very attractive face. She took me into her room and after a mild back massage asked me to turn over. I did and it was only a few minutes of rubbing my chest that she worked her way down and asked if I wanted a blow job. I said “okay” and she went for it. I rubbed her clit through her panties while she sucked me. She then paused and asked if I wanted a condom. I was confused but said “yes.” She put it on me and then, after quickly dropping her panties, climbed on the table, got under me and put me inside her. I f*cked her, noting that her vagina was much softer than anal sex I had with men. Afterward, she gave me a towel to clean up and I left. My friend waited outside, anxious to hear my verdict. I described what happened and he said, “You were supposed to get your choice of women. You didn’t get your choice?” I said “No,” and he said “That’s f*cked.”

So that’s how I lost my virginity at age 49. I’m 51 now and haven’t been with a woman since. I’m considering finding a foreign woman online that wants to marry an American so I can have a family. That’s probably a bad idea though. (omnichronos)


10. 38, she was 36. I was in relationships before, but I didn’t want to go that extra step, which in my mind would signify serious commitment. Until I found her. We knew each other for a few years, but started dating only last spring. Over time we got increasingly more intimate until one day we decided to go all the way. “You do realize that I’m committing myself for the long run, don’t you?” I asked her before we started. She nodded. We moved together last month, and if everything goes fine, I will propose her in a few more.

I know this is going beyond the scope of the question, but a few things I’d like to highlight. I don’t know how common they are for us late-comers (sorry for the pun), but here it goes:

  • For our first sex I bought a condom that was way too small. I guess I thought my penis was on the small side, from watching all the porn videos in my youth, but we never finished the first time because the condom kept slipping off.
  • I struggled to finish. At first, love making was a chore – we ended up both bruised and with sore muscles and joints. Thrusting it in for 30 minutes can be quite tiresome and not much fun. My girlfriend has to finish me with her hand.
  • We also had issues with proper condom wear and on more than one occasion the condom broke. I then learned I had to deflate the bubble on the top and pull my foreskin back when putting the thing on. One time I finished inside my girlfriend, which caused the only crisis in our relationship. No arguing or anything like that, more an “oh shit” moment.
  • Speaking of condoms: Neither of us had any experience with intercourse without it, so we figured if I kept up with wearing one all the time, we won’t be “inconvenienced” by knowing of anything better.
  • Over the course of our experimentations we tried various positions from porn videos, and I gained serious appreciation of the physical fitness and acrobatic skill of the actors. Anything other than missionary or cowgirl is far beyond our abilities. And we are physically fit and fairly active.
  • Until this day, after more than half a year of regular love making, I’m unable to finish as quickly as my girlfriend. She’s frustrated because she thinks she isn’t good enough, but I’m glad, because I don’t think I’d be able to continue after I’m done. (Bruncvik)

Original by Ashlee Miller

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