My First Anal!

Story Info
He gets 'talked' into anal sex.
1k words
4.32
134.9k
31
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
MrJimJim
MrJimJim
127 Followers

Once I had finished giving my first blowjob, I knew it wouldn't be my last. In fact, I stopped counting!

One of the guys I sucked on often was nice. Latin, firm, long slender cock just perfect for being naughty with.

We had been together enough times we were comfortable in each others homes. We would fool around at his house or outside in the rain. I would always swallow his cum. We were that comfortable.

One night after wine coolers we decided to videotape ourselves. I told him it was OK as long as I could see his cock go all the way down my throat.

"Deepthroat?" Anthony asked.

"Deepthroat." I replied confidently.

"Are you really ready for that, Jim?" He asked. "Do you want your cock in my throat or not?" I answered sternly.

With the camcorder whirring, I suddenly found myself getting the back of my throat and below impaled at a slow pace. As time went on, it got faster and faster, until eventually I knew what he wanted to do.

He groaned and lurched his hips forward, then jerked back quickly. I felt 1 spurt across my tongue and I was as hard as a rock. The next 5 or 6 strong spurts lept from his cock he had popped out of my mouth and went streaming across my face. That made me send my own spurts shooting down my legs and soaking my pantyhose. When I was done, I licked it up like a greedy dog.

After we both were soft we collapsed on the couch next to us, satisfied. Getting a facial had always made me cum so hard.

Before he left to get more wine coolers, he leaned over and whispered "I want to do that to your ass. I'll bet my cum will feel twice as good inside you."

That caught me off guard. I had never considered myself gay, just very easy and open-minded with my mouth. I was somewhat reeling, the words making me stiff again. Before I knew it I was jacking off and cumming again!

He got back with the coolers as I was slurping up my load. "I see you like the idea" Anthony said wryly. "No" I replied bashfully, and hurried to bed.

Over the next 6 weeks Anthony would drop little hints to me. "I bought some lube today" or "I wish I could fuck a tight honey" were among his favorites.

But I was scared and confused. I didn't know what to think. Someone tell me what to do!

A week later Anthony got a promotion, and we were all celebrating. We all drank way too much and eventually we all fell asleep. I'll never forget when I awoke...

I was laying face down, half in and half out of sleep. I felt Anthony kiss my back and shoulders, which only meant one thing... Anthony was horny. From the feel of his hard member that touched me some, I would've said VERY horny! He'd never been that solid before, I always had to suck start him.

I felt a pair of hands on my shoulder, but something wasn't right. They were backwards!

I tried to turn over to get a better look, but those strong hands held me firm.

Next I felt warm oil being poured all over my body. Along my shoulders, down my back, down the crack of my ass, and along each leg.

Then panic. I felt Anthony's cock pressing against my virgin rosebud!

"STOP!" I yelled. But it was too late.

I felt the head of his cock press against my hole harder. I tried to hold tight, but the more I tried, the harder he pushed. I couldn't even make a noise.

I felt the head of his hard slender cock force itself into me, and there was a flash of heat around my hole.

I almost blacked out. It hurt! I managed to whimper "It hurts. Oh it hurts". My only reply was "Shhhh" in my ear.

Without warning he heaved his slender latin hips forward, and my hole engulfed his entire rod in one swift shove! My cock twitched to life and got firm, then rigid, then hard. What?! That can't be from this!

He slid his cock almost all the way out, so very slowly, stopping just before the head peeked out. It made my cock quiver, and I was getting used to this stiff intruder.

The hands let go of my shoulders, and I turned to see a look of sheer ecstasy on Anthony's face.

"Fuck me" I managed to get out clumsily. His eyes opened and centered on me quickly, as I pulled him from his ecstasy for a moment.

"Fuck me!" I got out louder, and his look of surprise turned to something naughty and devilish.

He pushed back into me, then out again. Slow at first then building up to a full-out ramming.

I was moaning as this stud ravaged me like he had never fucked before. And I heard it.

His tell.

He was about to cum...

So many thought raced in my mind. Is he going to cum inside me like he said? Is he going to cum all over my pantyhosed ass? Would he pull me up and shoot streams of thick cum across my face.

He came. The feeling of his spunk flowing out of his cock into me was more incredible than anything I can describe! He came long, and he came hard. I could feel his cum spurting into me, then cooling. It was amazing!

After two or three spurts, I became light-headed. The room started to spin. And...

I felt myself unleash a load of cum harder than I have ever cum before. EVER!

The room went dark. The air got cooler.

When I woke, Anthony was just out of the shower, and calling cabs for guys who started waking up.

He came over to me and said "You sure changed your mind in a hurry. Did you like getting fucked and spunked?"

"I don't remember" I said as his face showed his puzzlement. "You will have to refresh my memory after everyone leaves" I said with a smile.

To this day, I cum instantly when someone cums inside me!

MrJimJim
MrJimJim
127 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
8 Comments
Riki1942Riki1942over 5 years ago
Pantyhose Anal

My Buddy and I usually wear latex catsuits when he fucks me but, sometimes we wear pantyhose, and he always cums inside me bareback. If I haven't already shot my load, knowing he is filling my insides with his sperm when he cums almost always sends me over the edge like that. We do it a LOT but, if I could, I would always have some of his cream inside me. I get hard for hours after we have sex every time I think about what I have inside me. I usually slip a butt plug in when he pulls out just to make sure it stays in there what it's supposed to be.

AnonymousAnonymousabout 6 years ago
Sounds like you got a winner

Hot story....very nice. I am sure, by now, you have enjoyed 'face to face'. How did that go? Which do you prefer?

AnonymousAnonymousabout 7 years ago
Me Also

I love a 5 and 1/2 inch or 6 inch fat cock up my ass, and I also cum as soon as I feel hot cum shooting into me. What a GREAT feeling

AnonymousAnonymousover 9 years ago
Fantastic!!!

I was 45 when I got fucked for the first time. I knew I could take it, since I had taken more than half of a 10 inch doubleheaded dildo. When it was over I felt like such a little bitch! This guy had me moaning and groaning like a whore in heat. I lost all control and came all over my own face and chest. It was so fantastic!!!

AnonymousAnonymousalmost 13 years ago
Not into panties... butt

I Do Love a hot cock in my ass. My first cock that fucked my ass was a nice 6" cock so I now knew how my girlfriend felt when I was fuckin her ass.

I went 20 years before getting fucked again but wanted a bigger cock this time. I met a guy online with an 8" uncut cock that said he was a top but also wanted me to give him a blow job. Having never sucked an uncut cock before I was very willing and fell in love with uncut cocks, so much more to play with!

I sucked his cock for quite some time before he wanted to fuck me and it hurt like hell but I really wanted to be fucked again as I was no longer getting any at home due to an accident and injuries my wife had suffered. The guy took his time and eventually got it all in then fucked the hell out of my abused ass. Before he came he pulled is cock out of my ass and turned me around and jammed his cock back down my throat. Made me feel very dirty as I cleand his cock and felt him cumming on my tounge and feeling his cock in my throat again. Haven't done that again but sure would like too it was great!

Show More
Share this Story

Similar Stories

Boyfriend Gets It in the End She convinces boyfriend to try out his hung friend.in Gay Male
First Time with Neighbor Daddy 18-year-old boy is taken by older neighbor.in Gay Male
Bicurious Fantasy Becomes a Reality My fantasy of being submissive to another man is fulfilled.in Gay Male
Straight Turnout Strait guy is turned out by an experienced man.in Gay Male
Becoming His Girl An older man teaches a boy to forget his girlfriend.in Gay Male
More Stories