Taking A Young Man’s Anal Virginity

by GreyBear

What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Germany
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Single
Religious affiliation: Atheist
What’s your sexual orientation? Gay/lesbian
How many sexual partners have you had in your life (including oral sex)? I really don’t know, quite a lot
How many hookup stories have you here posted before? 0

Taking A Young Man’s Anal Virginity

How long ago did this hookup happen? 3 days ago

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? The beautiful young man (no names here) is 19 years old and very inexperienced. He has just embraced his queer sexuality. He is short and slim, has cute brown eyes, a slightly dark toned skin, curly dark brown hair.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I went to a gay sauna in need of sexual relief. I do this quite often as I am single and casual hook ups are my cup of tea.

I mostly get to do it with men around my age or maybe 10 years younger, but occasionally I am lucky that young men are willing to have sex with me. I am a top, and men who are into bears and daddies are usually the ones that are attracted to me. I do my best to stay in shape so that I am still able to pick up guys despite my age.

I was in the shower room when I saw this stunning young man come out of one of the saunas. I looked at him and I noticed that his gaze was on me as he took a shower. I moved next to him as we were showering. I kept on looking at him and was about to make a move when he stepped out, dried himself with a towel, gave me another look and went into the dark room. I rushed after him, still wet.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I found him in the dark room and made contact with him touching his shoulder. This way he’d be able to demonstrate that he’s not interested simply by moving away. Quite the opposite happened. His hand wandered over my hairy chest and soon I could feel his lips on my nipples. We embraced, our stiff penises touching each other. He went down and started sucking me. I leaned back and enjoyed the incredible luck I had that night. To test the waters on how far I can take it with this obviously submissive toy boy, I started fucking his mouth, but only gently to not offend. He let it happen and seemed to like it.

I realised I would cum soon if I would let him go on further. I whispered that I don’t want to cum yet but would love to have time with him in one of the private rooms. He stopped, kissed my balls and stood up again. I took him by the hand and went to one of those little closet rooms where couples can be by themselves. The boy had obviously not seen those before and was amazed. He told me this was his first time visiting a sauna. I replied that he quite expertly knows how to pick up.

Inside, we embraced and I found out that my little friend is quite into kissing as well. We french kissed. He sat on my lap, we mutually fondled our penises. He furiously licked over my chest, he really seemed to love doing that. I courteously kissed his penis, but in this setting where I am the older top and he is the submissive young kitten, it is clear who will suck whom. So he continued sucking which obviously is his fetish.

I asked him whether I could fuck him. The boy replied he had not been fucked yet but would love to have the experience with me. I told him to turn around.

I kissed his firm little arse, rimmed him, stuck my finger up his anus to lube him in, put the condom on, lubed it and rubbed my stiff member against his arse, then pressed it against his rosetta and pushed it in as gently as I possibly could. The boy cried out in pain, but I knew what had to be done and pushed further, trying not to hurt him too much. The spring chicken accepted what is good for him and gently moaned as I pumped into him doggy style. Occassionally I would stroke his penis during this procedure I have a lot of experience in.

I was enjoying myself but I wanted to prolong the situation and also get more intimate with the boy. I pulled out and asked him to lie on the bench. He did and I went on top of him. I applied more lube while I sucked the cute little penis a little bit to reward the boy for the pain he had endured.

Then I pressed myself in again into the tight, inexperienced arsehole and fucked on. This time he could fondle my nipples and lick my chest. we also kissed again. I pumped on as he moaned. I instructed him how to postion his legs to ease the pain of his first anal experience. I got a bit rough on him when heat struck me and i worked towards the most satisfying orgasm.

I pulled out and stripped of the penis. the boy was obviously disappointed when he realised I had cum. He asked to lick off the sperm which was still on my penis. He wanked himself as he was doing that, contiuned to lick my balls until he shot off his sperm.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We went to the bar and I invited my young lover to a drink. We had an intimate chat. The boy told me that he was still very inexperienced. I had only been his third man. He had only done mutual wanking and blowjobs with two other boys so far. The boy told me that he was very happy with the experience we just had and the way he lost his anal virginity.

He admitted to being confused about his attraction to me, an older man. I explained to him that it was quite normal and common for young men to be attracted to old men. There is nothing wrong with that, it is just natural. I had fucked several young men, maybe not as young as he was, in the recent years. I told him how proud I was of my conquest with him. That seemed to both calm and flatter him.

I asked him whether he wanted to become my boy toy. He said he’d think about it but for tonight, his experience had been intense enough and he’d rather withdraw for now. I gave him my telephone number and he left.

The boy has just texted me and told me that he wants to drink all of my sperm as it shoots out of my fat penis. I guess that is a good sign that I will see him again, lol.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), It was easy / convenient

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? A friend of mine congratulated me to this hook up.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Having fucked such a young man. He is just 19. I liked how submissive he is. I could do with him as I pleased. It is so fortunate that nature has intended that young men feel desire to please old men.

What was the WORST thing about this hookup? nothing, all perfect.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

You have a hookup story to share? Submit it here!