Join the best erotica focused adult social network now
Login

Losing My Anal Virginity

"How I lost my Anal Virginity after trying for many years!!"

73
10 Comments 10
4.7k Views 4.7k
1.8k words 1.8k words

This is my story of losing my anal virginity after trying for twenty plus years. I have been with many men and t-girls over the years. Many have had me in the position to fuck me put for some reason or another they just couldn't push their cocks in. This is the story of the first guy that was able to!

After many attempts through craigslist (before it did away with the personals section) and doublelist, I tried an ad on menforsexnow.com. Had the ad on there for awhile also with no luck. Now I'm not the most fit guy or the greatest looking. At the time, I was in my mid- to late-forties; I weighed over 210 (with some what of a belly), and I have a six and a half inch that is just your typical average cock, with a good mushroom head.

I'm going through the ads and message a few. There is one that greatly interests me but he talks about how he has a swimmers body and he is fit. I decide not to message him, as I'm thinking there is no way he would be interested.

After a few more hookups with more blow jobs and no one able to get hard enough to fuck my ass, I go back to that guy's ad with the swimmers body. I message him thinking this is never going to happen, but can't hurt trying. I lay out my stats and tell him that I'm looking to lose my anal virginity.

He (let's call him R) responds back after a few days and is interested. After a couple more messages back and forth, we set up a time. Now I'm a GM for a local retailer in town, and I live over thirty minutes away. So the only time I have is during my lunch break because I'm also married to a lady and need to get home after work. R sends me his stats: 36, gwm, 6ft, 165, 9.5" with a nice thickness. Now I'm like, how is that going to fit in my ass? Hopefully this isn't another try and can't get in.

So the day finally comes and I'm meeting him at his interior design store, which isn't open on Mondays or Tuesdays. His staff isn't there, only him.

So I arrive and knock on the back door as I'm nervous as hell. R opens the door and he gladly let's me in. I take a few steps in and he closes the door behind us. We make some small talk as we head further inside his store. We make it to an area that he has set up for us. We are out in the showroom but it is completely surrounded with decoration and sample books on shelves that it's completely blocked from anyone's possible view.

R asks if I'm ready, and of course I am!! I'm thinking that this is going to be the time! R has me sit on the love seat and gets down on his knees in front of me. R unbuckles my pants and pulls them off. Then down go my boxers, leaving my rock-hard cock out for anyone to see. R reaches for my cock and slowly touches it. Running his fingers up and down my shaft. Running his fingers on the underside of the head of my cock. He tells me to take my shirt off before he takes me in his mouth.

I'm now completely naked in front of this guy who is between my legs, swallowing my cock. My cock is pulsating with every movement he makes with it in his mouth. Stroking and sucking me and I'm moaning with this intense pleasure that I have not felt before. Even after all these others have sucked my cock. R reaches up and runs his hand up my chest to my nipple and tugs and pinches them. He's bringing me close to exploding. Sensing that I was gettIng close, R releases me from his mouth and stands up. Time for him to get undressed.

R starts taking off his shirt, his chest is hairless and very well looking. Definitely the swimmers body. R continues to get undressed while I just sit there and watch. Pants come off and he has on briefs that accentuate his cock. His cock is hard and the outline of it in his briefs makes his cock look huge. I reach over and run my hands down his chest to his briefs. I grab the band and start slowly working them down in anticipation of his cock popping out. The anticipation was well worth it as his 9.5-inch cock is now in full view, and it's a masterpiece!

He is shaved and his cock is beautiful. I'm sitting on the edge of the loveseat with my hands wrapped around his cock. I lean in and lick the tip. Swirling my tongue around the head of the biggest cock I've ever touched. Leaning in more as I start to slowly take his cock in my mouth. I take more and more in as I start sucking on his cock. I start bobbing my head on his cock, trying to get more in each time. Getting a little more than half in my mouth now. Working to get more. Releasing his cock from my mouth as I start licking the underside. Feeling the hardness in his cock, I have no doubt that this will soon be buried deep in me.

BriaCooper
Online Now!
Lush Cams
BriaCooper

Grabbing his cock and taking it back in my mouth as I start jerking mine. Grabbing his cock and sliding my hand down it as I take it in my mouth. Continuing to bob up and down with my mouth as I stroke his cock. R is moaning with delight as I take in as much as I can.

I release his cock as we move over to the padded blanket he has set up on the floor and get into sucking each other. My cock is just pulsating as R strokes and sucks me also. R starts thrusting more with his cock, trying to get as much in my mouth as possible. I release my grip on his cock and let him have his way with my mouth. His cock is pistoning now in my mouth as his clean-shaven balls are hitting my face. I start to gag a little as he enters my throat. I push back a little to get some air. R asks me if I'm ready to take his cock. I've been ready for years and I know this time is the time.

I move to my hands and knees. R grabs the lube as he knows I will need it. Before he puts any on me he bends down and starts by spreading my ass cheeks. Looking at my entrance and moves in closer to start licking it. R is really working his tongue in my hole. I'm moaning with pleasure while stroking my own cock slowly.

He rims me for a good few minutes. He moves away and then I feel the cold liquid being rubbed into my opening. He's using a lot and pushing some into my ass with his fingers. I hear him stroking his cock with the lube. R grabs onto one of my hips and moves me back some. I feel is cock up against my ass cheeks. The anticipation is feeling overwhelming as I'm about to have R's cock in me. R asks if I'm ready. I've been ready for years and can't wait any longer.

I feel the head of R's cock pushing at the opening. My entrance starts to slowly open as his cock starts pushing in. Scared to death, but ready to accept this cock. He gets the head of his cock in me. The lube is doing it's job. I feel the stretching of my opening. There is a little pain involved as he gets a little deeper. The thickness of his cock keeps stretching me further open. He pulls back some and pushes more back in slowly. R is taking his time getting himself all in me. I have him stop for a moment as a shooting pain goes through me. The pain subsides as he resumes pushing in. R asks if I'm OK and I'm feeling great that I have someone fucking me. R starts to fuck me now. His cock feels great deep in my ass. Feeling his cock starting to slide in and back, in my ass. He's starting to pump a little faster now. I'm moaning with this pleasure of a cock deep in my ass. Telling him how great this feels. R starts to pick up the pace as I'm stroking my cock and know that I'm going to explode any moment.

The sensation of finally no longer being an anal virgin, the pumping action that R is unleashing on my ass....I explode and start cumming. Pulsating rope after rope of cum. R has stopped as he let's me finish my orgasm. I'm now lying face down on the blanket...spent.

R now moves his cock back to my ass, slowly re-enters. He pushes in again and starts pumping. He has a good rhythm going. I'm loving the feel and tell him to go faster. Pump my ass harder and faster. He says he is ready to cum. He wants to cum on my back and ass. R keeps driving hard and fast into me, then suddenly he pulls out and is on his knees, stroking his cock.

I feel the first glob hit my upper back, then another and another. Cum keeps splashing on my back and now my ass. Seems like he can't stop. He's letting out moans and moans as he covers my back and ass. R has finished and grabs a nearby towel to wipe off his cock. He runs the towel down my back and ass, cleaning up his cum-soaked fuck toy. I feel him press his fingers between my cheeks and run it over my hole. Did he just push some of his cum between my cheeks? Guess I'll find out later.

I turn over and see that he is still somewhat hard. I get back to my knees in front of him and take his cock back into my mouth. I start to taste his cum as a little more leaks from the tip. I run my tongue over the opening and get more to come out as I stroke him.

That's the first time that I have tasted another man's cum and it will not be the last I taste his... or swallow one of his loads. He will also be the first to breed my ass. This relationship builds into a weekly and sometimes more than once a week get-together.

More stories to come about R and my get-togethers.

Published 
Written by MikeA
Loved the story?
Show your appreciation by tipping the author!

Get Free access to these great features

  • Create your own custom Profile
  • Share your erotic stories with the community
  • Curate your own reading list and follow authors
  • Enter exclusive competitions
  • Chat with like minded people
  • Tip your favourite authors

Comments