Taking Virginity

[ErosWired]

Note: This question is not an opportunity to glorify the abuse of underage persons, so if that’s what you were planning to do, kindly move along, thank you.

Note also: This question asks about the experiences and views of men who have taken someone’s virginity, not the views of those who have had their virginity taken - which would be, at some point, every one of us. I am, however, posting a related question asking for these views.

Have you ever (legitimately, not in fantasy or roleplay) been somene’s very first experience of sex? One usually hears this referred to as “taking their virginity”, but taking implies coercion or nonconsent, or at least dominance or aggression, and that obviously isn’t always the case. If you have, how do you feel about having done it?

It’s an irreversible act, a bell that cannot be unrung, and is generally life-altering at some level. For some, it is s rite of passage and a goal they‘ve yearned for; for others, it’s an untimely introduction to a world of trauma that they aren’t prepared to cope with and don’t want to live in. The direction it goes may have much to do with the way it’s handled by the one providing the service.

I have no doubt that there are some here who wouldn’t give such considerations a second thought; men for whom finding an anal virgin is like finding a hundred-dollar bill on the sidewalk - they’re going to fucking grab it. I have no doubt there are men on here (I trust a minority) who see a sexual virgin as a problem to be solved - See? That was quick. I have no doubt that there are a handful of men who see sexual virgins as the choicest of prey. If you are any of these, I’m not going to judge you if you say so here, but I would be interested to know that you exist, and why you feel the way you do.

For the rest of you, how do you feel about the experience, in hindsight, for better or worse? Would you do it again, or avoid it?

Edited April 9, 2023 by ErosWired

[NWUSHorny]

I've been sought out and invited to take the anal virginity of several guys. The 1st time was with a 22 year old when I was 20, when I had only fucked 2 other guys and before I lost my own anal virginity, so I was really out of my league. The most recent was with a 19 year old when I was 50, which felt somewhat uncomfortable with that due to the age difference.

Since I'm somewhat larger than average (I know I sought out someone smaller to loose mine to) I always take my time eating him out and preparing him by very gently finger massaging his hole (I hate being fingered, so I am very careful not to over do the penetrative part of fingering) then encourage him to either back up on my dick doggy style or letting him sit on it (I've found doggy style works better) at his own pace. While I don't generally do relationships, quite a few of the guys whose virginity I took became at least occasional fuckbuds, so I like to think I did something right. Several of them quickly evolved into major sluts, that I have fucked repeatedly while cruising or at sex clubs.

Edited April 9, 2023 by NWUSHorny

[hntnhole]

On 4/9/2023 at 10:17 AM, ErosWired said:

For the rest of you, how do you feel about the experience, in hindsight, for better or worse? Would you do it again, or avoid it?

First, thanks for the incisive response.

This is the principal reason I tend to avoid "bringing out" a new guy.  It's happened a few times, and unbeknownst to me at the time.  I would much rather avoid being "the first", in favor of allowing the bottom to come to terms with his Lusts, and then help him expand and deepen his cravings once he's comfortable in his own skin.  I have no problem helping a newbie figure things out - after all, I went through the whole mess at one time - but without the actual sexual act taking place. 

To me, it's well worth it to wait to be the 100th, rather than the 1st.

[ErosWired]

18 hours ago, NWUSHorny said:

The most recent was with a 19 year old when I was 50, which felt somewhat uncomfortable with that due to the age difference.

What made you uncomfortable about the age difference? I’m curious because I had a sort of similar experience a couple of years ago with a young man of 21 (me at 53) who wanted me to help him learn to Top. It wasn’t a case of virginity, but there was still a sense of him being very new and extremely vulnerable. I was glad he came to me and not someone else, because I knew I was going to treat it a sensitively as humanly possible. Yet normally I would avoid such a situation.

[NWUSHorny]

@ErosWired I'm sure it is mostly cultural conditioning, but I feel like an age difference of more than 5 years with a 19 year old is somehow wrong. Weirdly if he had been a 30 year old it wouldn't have bothered me. With a 19 year old I just feel like he would have been better off experimenting with one of his peers rather than someone who had been fucking more than a decade before he was born. We probably need a psychologist to figure out why I think it is ok with someone well into adulthood but still young enough to be my son.

 

 

 

[ellentonboy]

I happened to place an ad when Craigslist was still offering personal ads.  I had great success with that site, and met guys who became repeats and were not from my regular sources like adam4adam, or barebackrt.  I received a notice that a guy was interested and when I communicated with him he told me he was 18.  Young guys are not my thing, but he said he was really hoping I would give him a chance when I met him and that he had documentation of his age.  

When he arrived he was at least 6 foot 5 and was a senior at a Catholic High school in Pinellas county where I live.   He had his Florida Driver's license and said he was looking for oral and he seemed determined to get it.   So I agreed, he was really handsome and polite.   I explained to him that I was old enough to be his father and he just laughed.  He  told me the girls he dated would not blow him, and he said he was so horny and wanted to experience having sex with a guy.  He gave me his phone number, actually put it in my phone for me, and told me to stay in touch.  He came over in the middle of the school day and had to get back to class.  I wanted to die when he made that remark.  

He stayed in my mind unlike alot of guys I have met, he was great looking, a great body and very nice to deal with.  He texted me again, and asked if I would consider letting him fuck me.  I said yes, I didn't talk about condoms, but when he arrived he was well prepared with his Magnum Condom and I didn't say no.   The experience was nice, he was very nice about everything and I have to say I had a good time.

A few weeks went by, and I received a follow up text.  This time he had requests.  He knew where I lived, he literally could walk through the front door and neighbors could not see what was going on in the living room.   He wanted a situation where I was on all fours, and blowing someone.  I asked a guy I played with in my apartment complex if he would participate, this guy was I believe 29 at the time and he agreed.   Again, this was going to be in the middle of the school day.  The 18 year old came over, we were on the couch in the living room, I heard the friend I was blowing say "hey, how you doing" to the kid and I felt him stick his dick in me.  NO CONDOM.  Now we have never had a conversation about that,  and since our first anal encounter, I assumed he would be wearing a Magnum.  This time, he wasn't.  After he shot his load, he asked to use the bathroom to wash his hands or whatever, I said yes and my regular buddy was looking at me with a funny expression.  He said, "he does know your poz correct?"  He came back into the living room, said goodbye to my friend still naked on the couch, and hugged me goodbye.    I felt so guilty, I didn't know to text him and tell him or just leave it be.

This time period, I believe it was 2017, was when Craigslist pulled the plug on their personal ads.  I got a new phone, and to be honest I really could not track him down.  I am sure he has fucked plenty of guys since me.  However, to this day I feel guilty not communicating better, I assumed he would wear a condom but he didn't.  

I do feel guilty, and today, I always make it clear as to my status.  Had he been in his 40s I wouldn't feel as bad, I could justify it in my mind that someone in my age range would know better.   But someone who was a senior in high school?  I still feel bad.

[PigBoyDallas]

Without giving the ages of the guys involved, yes, I have taken the virginity of a number of guys. Truthfully I can't remember how many. With a lot of them it was a lot of time spent having to explain that their concept of it being "perfect" as they imagined was never going to happen. Many were desperate and just wanted it to be done with. Others wanted this elaborate seduction and romance and felt they'd never get it. But I'm patient and a good listener and offer to be very gentle and sensitive. Some never can agree to the final act but love kissing, making out, stroking, sucking, and more. I remember one guy recently where we got to penetration but he just couldn't bring himself to let me cum inside him. He's been messaging me since then wanting to meet up again but still can't agree to me cumming inside him. I know eventually he will. I'm patient. I know I will be his first. I've already let him penetrate me and cum inside me and was his first. He loves that I will gladly let him cum inside me whenever he wants.

I'd taken the cherry of another guy in recent days where I was his first as well. He'd fucked other guys but had never taken it in the ass and was kind of the attitude that he wanted it over and done with. I wound up spending the night with him and over the course of several hours pumped three loads in him as well as taking several of his loads. He admitted to liking getting fucked but admitted he thought it would be a bigger deal or hotter, saying that the way guys talked about it, it would be way more exciting or hotter. I was kind of offended, but he admitted he preferred topping and enjoyed that more, which made sense.

[LetsPOZBreed]

I've taken only one guy's.  I was a few years older than him and had some experience under my belt.  But I also remembered my first time and that I had to be gentle.  He was definitely nervous, of course, as was I.  He made me promise to "go easy" on him when we got to fucking, and I gladly obliged...didn't get to the point of finishing inside him, though.  I did get to play with him a few more times afterwards...once after I'd moved away, I hooked up with him when I went back for a visit.  He'd clearly gotten more experienced and was quite the good bottom boy by then.  Think if I'd stuck around my hometown for longer in life, we'd have gotten together more - I don't regret it, and I think we both got enjoyment out of the experience.

[FelchingPisser]

I know some men prize taking virginity, but that is not me.  I have.  It was either the first or second time I fucked.  It was a school mate who knew what he wanted.  He was surprised that I had more to put up his ass than any of the inanimate household objects he'd been using as dildos.  It was not a roaring success.  I was as much of a novice as he was.

Once I knew what I was doing, I used to be besieged by guys on Adam4Adam, begging me to break their cherry.  I refused.  I always told them to find me again once they'd taken 10 regular sized cocks.   I love experience.  I want men who have skills--and really know that they want size.

Now, I have taken many men's virginity for fist.  I am a great teacher for that--with medium collapsible hands and the patience and know-how of how to get into most men--and enough experience to know it won't always happen the first few times.

[ErosWired]

3 hours ago, PigBoyDallas said:

I remember one guy recently where we got to penetration but he just couldn't bring himself to let me cum inside him.

This sounds as though you don’t consider a person’s virginity lost until he’s taken a load. I think most would consider the simple act of being penetrated by another man the defining act, although there is definitely a point-of-no-return aspect the first time a male is bred by another male.

[ErosWired]

I find myself wondering how a Top knows for certain that the hole he’s using is virginal (we have no hymen, and even if we did that’s not a guarantee). One sees any number of profiles online that advertise ‘virgin ass’ that are plainly not. Indeed, the skepticism of claims of virginity is such that the man who took mine did not believe me when I told him.

[NWUSHorny]

We mostly have to take a bottoms word for it. I had watched in frustration my most recent one ride a sizeable dildo like a pogo stick, a week before I took his virginity, so I was definitely unable to tell based on the feel of his fuckhole. In fact he is typically tighter when I fuck him now, almost 4 years after he lost his virginity. He also hasn't let me bareback him yet, although he has barebacked and bred me at least once. It is possible he is just a good actor, but for whatever reason I believe him.

Edited April 10, 2023 by NWUSHorny

[Bokkierob]

I've taken the virginity of a few men - from 19 to 38 and I've enjoyed them all. It's never the best fuck - I like if ruff and deep but it's still fukkin horny to be a young man's first top. I've always tried to make it a memorable (horny) experience for them. One horny session was with a 22yo boy who had been sucking my cock for a while. He had a beaut beefy ass and he always reacted well to me fingering his hole. One day we'd started to fool around and I was teasing his hole and he asked me to fuck him. I wanted his ass so he didn't need to ask twice. I fingered his hole with 1 then 2 then 3 fingers to get him loosened up a bit then i ate his hole and got him wet. I put him on his back and opened his legs. The second I pressed my cockhead on his hole his whole body trembled. He closed his eyes and gently moaned. I pushed a bit harder but slowly until half my shaft was inside him. I let him rest his asshole for a few minutes before I want balls deep in him. I gotta say he felt real good on my cock. Again I let his asshole rest until he opened up wide enough to take my shaft. I gently fucked him for about 10 minutes. He was moaning loud now and was clearly enjoying it. I told him I was gunna cum and he just said "fuck yeah" After I shot my load I stayed in him while I jerked him off.

[hntnhole]

On 4/10/2023 at 11:17 AM, ErosWired said:

I was glad he came to me and not someone else, because I knew I was going to treat it a sensitively as humanly possible.

So am I.  I can hardly imagine a more caring man to bare his (sexual) soul to.  

[Guest]

32 minutes ago, hntnhole said:

So am I.  I can hardly imagine a more caring man to bare his (sexual) soul to.  

From limited time on this site ErosWired has impressed me with his conduct and advice, and nature.

On the flip side, I would love the opportunity to teach someone. My first time included oral and anal and no coaching on how to take a dick.  I still have flashbacks! 🙂