My First Time

by Prettyboy

11 Aug 2023 2884 readers Score 8.7 (54 votes) PDF Mobi ePub Txt


My name is Sheldon. I am 35 and married. I  am 5-11, 175 lbs with brown hair and eyes. I love my wife, Chrissy,  and for years our sex was good. Now I am having a harder time getting an erection. I notice boys more and have started watching gay porn.  I get hard seeing guys suck and fuck each other.  I have started playing with my hole with my fingers. It feels good sticking one or two up my ass.  I just went  to a sex shop and bought a dildo that is 6”.  I put some lube on it and slowly slid it inside my hole. Oh fuck it feels good there. I move it in and out now. Am on my back with feet in the air sticking it deep in my ass. Am really hard now as I fuck myself.   It does not long for me to cum.  I enjoy fucking myself now and watching lots of gay porn. I have always been into fashion. I like wearing leather jeans, leather jackets, and  wearing pink.  I also like a tight fit in my clothes, particularly my jeans and the feel of tight denim around my ass.  I am also turned on by gorgeous boots and cool sneaks so I wear cowboy boots with high heels or high top sneaks when I do myself. 

I want sex with a guy now. I dream of cock, sucking one and feeling one up my ass. I love looking at boys’ asses and sometimes get hard looking at young man’s tight ass.   It is evening and I am sitting on a bench in a park where gay men hang out.  After a while a guy around my age sits down with me. He is a gorgeous guy around 6ft with black hair. He is a runner and is wearing a blue tank top, blue shorts and white Nikes with blue swoosh. I am wearing a pink tee, tightwhite denim shorts and Superstars with black stripes.

“I’m Hank. I haven’t seen you here before”

“I’m Sheldon nice to meet you”

We chat for a while and Hank suggests we go to a pub nearby and have a beer. We hit it off chatting at the pub. We both like baseball and talk about the local team.  After a while Hank puts his hand on my crotch. I don’t mind, in fact this is what I want now. He rubs my crotch and it starts to get hard. 

Hank invites me to his place. When we get there we embrace and we kiss. I am nervous and excited. I tell Hank that I am married but want so much to have sex with a man. 

“It’s Ok, Sheldon. I have had sex with first timers. Let’s go to my bedroom”

We take off our clothes except for our sneaks.  We are holding each others cocks now which are rock hard.  Hank goes down on mine. He licks my balls, then my 6” shaft and finally starts to suck my dick.  Oh fuck this is so good. This is what want so much. I am excited and climax in Hank’s mouth. 

“Why don’t  you suck mine, now Sheldon”

I can’t wait and take his cock in my mouth and greedily suck it. 

“Slow down man. Enjoy licking my shaft and playing with it, bro”

I lick his gorgeous cock and then start to suck it again.

“That’s it bro, enjoy my cock. Nothing better than enjoying another queer’s dick”

After a few minutes, he pulls his dick away.

“I want to fuck you now. I know you are going to love feeling my cock deep in your ass. BTW I love your tight ass. It looks good in your tight white denim shorts. I am going to make love to your ass and hole before I fuck you”

“Oh Yeah, do me. I want to be fucked so much. I am pretty sure I am a bottom.”

I am on my back now with Hank licking and kissing my ass. He starts to play with my hole with his finger which have lube on them now. Next he licking my hole. Oh fuck this feels so good.

“Oh do my hole, that feel so fuckin good”

“I will fuck you with my tongue for a while so your pussy is warm and wet and ready for my cock. A boy’s  pussy is tighter than a women’s, bro and feels so good around my cock. I love fucking boys and men so much.”

Hank lubes his cock and starts to slowly enter me. Because I have used my dildo a lot, it doesn’t hurt.

“Oh yeah, Hank. That feels so good. Fuck me now, Fuck me good.

“Your pussy feels so good, bro. I am going enjoy fucking your boi cunt”

Hank  takes me with me lying on my back with my feet in the air. He is holding my Superstars as he pounds my ass.  

“I like your Adidas, man”

He is  licking them now.  I am in heaven being fucked and seeing my Superstars in air being licked.  Oh fuck, I am cumming OHHHHHHHHHH

“Good bro, you are real bottom bitch for sure. Can’t hold back any more. OHHHHHHFUCK

Hank goes down on my hole and licks his cum there. 

“Oh fuck that was so good. For sure I want to bottom”

We agree to meet again so I can suck his cock and feel his dick deep in my pussy. I feel so good knowing I am a queer bottom boy who loves cock. Fuck yeah!