Boy #44, first time with an Instagram star

I often see hot guys at the gym, but even in my late 30s, despite all the sex that I’m having, I’m still shy when it comes to pick someone up.

I met this young guy, the kind of twink still at the university, about to graduate, with the body of a student, naturally slim, toned but not muscular, the skin smooth with just some last sign of youth, but also with the slightly aggressive look of someone who is about to test his expectations and to show what and if he is worth.

Was he looking at me? Was he attracted by me? Was he flirting or was he only flaunting his beauty?

Once we were next to each other in the steam room of the gym and he spent most of the time stretching his body towards me and rubbing gently and discreetly his balls, until we remained alone and we immediately kissed. I touched his cock, it was hard, he put his hand between my legs, toward my ass and I didn’t stop him, behaving like a bottom.

We went out of the locker room at the same time, we looked casually at each other outside of the gym and we departed. I checked immediately on grindr, scruff, hornet, no hint of him. Then I tried on Instagram through the tag of the gym and there was he, smiling, training, hugely popular on Instagram, like 800 likes for a selfie, almost one thousand for a selfie with a piece of body.

He was from abroad, South American, phd student, into design, fashion, art.

I sent him a private message on Instagram and we soon started teasing each other with sex requests. He appeared to be really into me, he was top and wanted to fuck me. I wrote that I could be bottom for him, I was not at all interested in positions, I just wanted his body, I wanted his attraction for me, I wanted the narcissism that I got from his desire and youth.

Anyway, meeting this guy was almost impossible: first the graduation, then his parents visiting him for ever, then the first job, then the flu, then the weekends out visiting more cities, the nights out, the friends, life in general.

I discovered I could be dumped by him again and again and never give up. Did I want him so bad because he was so young? Because he was not so easily available? Because he was so popular on Instagram? He made me think about the book “Super sad true love story”, where people has a sort of fuckability index that anybody can detect as soon as they enter into a place. Well, my university guy seemed to be hugely popular and highly fuckable.

I told him that he could ask me anything and I would do it.

He had a fetish with underwear. He asked me to give him my briefs after gym, so I could wear them while jerking off and think of me, feeling my smell, imagining to fuck me. Then he asked if I had jockstraps (I never did) because the very idea of me wearing them drove him crazy.

One Saturday I went to a sexy shop and bought one pair, even I felt completely awkward with them, not sexy at all, but from the changing room I sent him a pic (with filters, because I really believe jockstraps don’t suit me, and come on, he is a also a small star on Instagram).

We met twice, over 16 months of courting from my side.

The first time we both had no more than 15 minutes free. He came to my place right after a university lesson, late afternoon. He used the toilet, I heard him pissing after hours of studying. We had some seconds of embarrassment, after all we had said digitally, then we started kissing with urgency and passion, I unbuttoned his jeans, slid his boxers down and went down on him. I gave him a long blowjob without stopping, sucking, and kissing and licking his balls until he came into my mouth. I spat his cum in the sink, while he dressed up.

He liked it so much that he texted me every single day for a while day.

The second time we had the whole evening. He came to me again and I waited for him wearing a t-shirt and the jockstraps.

I wanna say it clear and soon: wearing jockstraps really loosed my inhibitions, made me willing to do anything under his command.

We started kissing again, same position, same passion, he spanked me hard a couple of times. We went to my bedroom and he asked me to lay over him, spreading my leg. I could feel his boner pressing on my buttocks and I wanted it inside of me so badly. I turned around and told him to lick my ass and make me wet. I could probably have come in that position, with the jockstraps on, my ass on his face, watching his hard cock. We had to stop before I lose my resistance.

I told him to fuck me the way he wanted. He made me laying on my back and put my legs on his shoulders, which is not the position I like most as a bottom (the few time I’m bottom, I mean). He wore the condom with some difficulty, which is something that often happens when I’m having sex with under 26 guys: is it out of experience or bareback is getting so popular among the young?

He penetrated me only after I helped him: this made that moment even more exciting, this lack of easiness, this desire mixed with embarrassment, this doing sex in a way that I desire more with my mind than with my body.

He pushed very hard, without complete control, he went outside a couple of times and I helped him back again and again. It was a bit painful to me, I really wanted him to come as quick as could. When I started masturbating – he wanted to see my cum on my body – he pressed badly my ball with his body and I had to ask him to move differently. I kissed him and he spat in my mouth. It tasted good and I told him to do it again.

Finally he came, I didn’t. I stayed under him watched his body still moving slowly inside mine, his beautiful smooth chest, his dark nipples, his mouth panting, his eyes half closed watching me with a sort of gratitude. He asked me if I wanted to come, I told him just to lay on me and stay as long as he wanted. I felt the smell of hairs, bodies, lube, condom, ejaculation, hot air in the room.

He took a shower. I waited naked for him in the other room.

He dressed up and was about to go. Then he started kissing me. I’m not good at good-byes after casual sex, this is something I can never learn, but he surprised me. He stayed on the threshold smiling, kissing me gently on the lips, with his tongue, smiling again, holding me. I didn’t want to go.

Weeks, months later I kept wondering if I wanted to have sex with him again. I decided that I didn’t, that my narcissism and my sense of beauty have already been satisfied.

Sometimes I still see his selfies on Instagram with more than one thousand likes and I smile about his fuckabality score and obviously about mine. Pity that I cannot share it, it made me more popular just in my mind.

I still have the jockstraps in my drawer, I never wore them again since then.


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