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7 Late-In-Life Virgins Tell the Story of Their First Time

7 Late-In-Life Virgins Tell the Story of Their First Time: Apatow Productions

Apatow Productions

I lost my virginity at 17. I was a senior in high school. I’m not bragging. At the time, it actually seemed late because my best friend had lost his years earlier. Little did I know that I was one of the lucky ones. Check out these stories from people who didn’t lose their virginity until very, very late. Really puts my shame for not having lost it earlier into perspective.

1. Alcohol definitely helps

I was/am 34. Just lost it last fall to a good friend/neighbor. We had been friends for years but never went out anywhere together. I’ve spent most of my adult life avoiding dating due to horrible social anxiety but am very comfortable around her. One day she suggested we go out to breakfast and I agreed. Several Bloody Mary’s later led to us drinking together at my place which led to me making a move. That led to the bedroom.

2. Quite the turn of events

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

3. Not the best experience

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.

4. Talk about sealing the deal

I was 34, never been in a relationship, and was just finally tired of it. I put up a personal ad online and had a few guys message me. I didn’t put on the ad that I was a virgin, it was just like any other ad there. Got a few responses, but one guy seemed slightly better than the rest. We agreed to meet, had a beer, went back to his place, and got that show on the road. I left about 15 minutes after it was over, glad it was over and done with. 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. 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 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.

5. That’s quite the secret

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. Fuck 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.

6. Could be worse…could’ve been 30 seconds

I lost mine at 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.

7. A truly happy ending

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. 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 blowjob. 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 fucked 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.


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