Craigslist Success!

Story Info
A day of firsts!
1.3k words
4.01
42.3k
7
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

For weeks before it had finally happened I had spent time in the shower secretly rubbing my chub titties and fantasizing about being molested by another man. I had never touched another cock other than my own and the idea of being treated like a girl had always made me so aroused. When masturbating I had never experienced harder orgasms than while I had my finger in my fat ass or while I sucked my thumb like it was a rock hard cock.

I was trolling craigslist one day while my family was out. There were only a few people in the world who knew of my desires and none of them were in my life at the time, so it was my secret to keep and I had kept it well. With recent news of an upcoming event that would keep my family out of the house for hours, I had decided to post and see what I might be able to set up.

The ad was simple and to the point. Roughly an hour later I had received a few responses. Nothing special at first; A guy who wanted to, but couldn't be free when I needed; Another who was a completely impatient jerk who got mean with me, then there was Shaun.

Shaun seemed like a real straightforward person. He was a very friendly black guy who was honest enough to let me know that he was in a wheelchair. He wasn't confined to the chair, however, he just needed one to get around. I was intrigued, so we set up a meet at my house. I had never felt so comfortable about someone online and figured if he was some kind of psycho I could probably defend myself against a guy in a wheelchair. The morning came and I had helped my family on their way. After a quick shower, I sent Shaun my address and he came over.

I was so nervous as I watched him pull into the driveway. "Oh my god, oh my god." I murmured. "This is it. I'm finally doing this..." I shut the door behind him and he moved from his chair to the couch. I sat next to him as we chatted a bit and I lit a joint I had rolled before he arrived. I passed it to him and he took a huge hit of smoke that billowed out from his lips.

"So, let's see what you got.." he said to me as I hit the joint.

"What do you want to see?"

"Shit, let's see everything." He answered. I sat forward and pulled off my shirt. Then stood up and took off my pants and underwear and sat back down beside him. He watched me for a second as I smiled at him, then, he leaned forward and took off his clothes using the wall for support. As he sat back down on the couch, I was shaking now more than ever as his large cock sat comfortably against his balls.

"Can I touch it?" I asked, stupidly, as if he would have said no.

"Yeah..."

I grabbed his soft cock. It was warm and big in my hand. At least 7 inches and slowly getting harder as I stroked him. "Let's see your head game..." he whispered. I lowered myself so that his cock was only inches from my mouth. I put my tongue against the bottom of his cock and licked all the way to the tip. He let out a moan of pleasure as I took his manhood into my mouth and started working my tongue around his head.

His cock felt so big in my mouth and as it grew, I found myself moaning and sucking harder and faster as my head bobbed like a buoy on his shaft.

As I sucked him passionately, I felt his hand touching the back of my head and rubbing my hair. Without warning he grabbed the back of my head and forced me down onto his cock. I began to gag as it was being pressed into the back of my throat. Oddly enough, I had only became more aroused as I came back up for air and tried to let him throat fuck me over and over again.

"Mmm, yeah. Bend over the couch and let me see that ass.." He said to me. I pulled myself from his crotch and bent over the couch. He was sitting back in his wheelchair so that my ass was face-level to him. I could hear him stroking his hard cock behind me as he looked at my eager-ass in the air. Without warning I felt him grab my ass cheeks and spread them apart. Then he darted his tongue into my ass and I remember seeing colors. It felt so good to feel his tongue licking up and down my asshole and I moaned in delight each time I felt his tongue enter me.

It wasn't too long that we had decided to take the party to the bedroom.I climbed onto the bed and put myself into the doggy-style position as he leaned against the dresser for support. He lubricated his cock with some lotion and then he rubbed my asshole with a generous amount. Then I felt his hands on my back as he positioned himself against me. His cock poked at my hole then I felt the pressure as he began to enter me. I began to moan as it worked its way into me and then suddenly popped into my ass. I could feel his whole length in my ass as he shoved hard to make sure it was all in. His hips were pressing hard into my ass cheeks as he held them spread open. He began moving his hips up and down and I could feel every inch of him rubbing me from the inside as he did.

I moaned and whimpered as he began to thrust his cock in and out of me, only stopping at times to force himself all the way in and hold it there as I quivered and cried out in ecstasy. He had been so rough with my ass that I remember we started doggy-style and we had wound up with me face down on the bed as he fucked my ass hard.

"Ungh... Yeah, who ass is this?" He asked me as he held his cock in me.

"Your ass..." I whimpered as he trusted me twice, hard.

"Yeah, that's my ass..." He said as he began to violently hump my asshole.

"Yeah... Yeah... Oh yeah... fuck it..." I whimpered between thrusts. He pulled himself out of me and sat me back up in doggy position and fucked me some more. This time he was stroking my cock as he fucked me. I couldn't hold it any longer once he started to jerk on me and I remember cumming all over his hand. After cumming I had relaxed a little more and he continued to fuck away at me. After a few more short moments of pounding my now devirginized asshole, he rolled over onto the bed beside me. "C'mon... get this dick.. Suck it."

I hesitated at first thinking his cock was just in my ass and now it's going back in my mouth. "Fuck it..." I thought and bent back down onto his crotch and sucked his cock until he was filling my mouth with cum. I really didn't even know he had shot a load into my mouth until I realized he was moaning with pleasure and his cock started to get soft. It had shot all over the inside of my cheek and I realized it when I sat up and felt it swirl around my tongue. I'm not sure why, but, I remember chuckling as I leaned over and spit it into a towel. He must have thought it was pretty funny too as I remember him chuckling when he heard me spit.

Soon, we were both dressed and after some friendly chat, he was leaving. We still chat secretly via email and we are planning another get together soon for more fun.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
AnonymousAnonymousabout 8 years ago

Older chub wanted. I couldn't believe it, no one wanted older, but there it was. I answered, 61,like to meet see what develops. That will be it. The reply came 5 hours later, and we agreed to meet at a café, in his town, 25klms away. I dressed, casual but neat, arrived late, I recognized him straight away. Tall, slim, mid 50s, short greying beard. Nervously chatted but soon at ease, after a second coffee, would you like to come back to my place. I did. The nerves came back, an older place but neat, like a drink, mm, bourbon if you have, nice, calmed me a bit. Look, im going to shower, bed rooms through there,feel free to join me or leave if you want, I hope you stay. He left, I heard the water, I went into the bedroom, it was dimly lit. I undressed down to my sheer underwear, laying on the bed. I heard him come in, glad you stayed, he walked over, standing with his cock over my face, I leaned up, stroking it, it grew, I took it in my mouth, mm, fresh, manly, hardening. He reached for my cock through my underwear, lets remove these. I did, nice, his fingers stroking my semi hard cock, then his legs straddling my head, his cock back in my mouth, his mouth around mine, he straightened up, leaned over and grabbed something, then my cock was back in his mouth as a warm slippery hand stroked my balls, slippery fingers teasing my hole, I felt my cock go harder than it had for a long time, his mouth moving up and down, one finger slipping inside me. I'm going to cum, the finger pressed inside harder, my cum shooting into his mouth, so much, it had been a long time. He slowly emptied me, then straightened up again, that was good, you had quite a load, yes, I cant believe it, its been a long time, you were great. Roll over, if you want, I did, easing me back on my knees, stop me if you don't like as I felt his breath on my hole, then his tongue, I jerked forward but then stayed still. Whats not to like as he rimmed me, I looked back, he was stroking his cock which looked hard and long. He stopped, I felt his slippery fingers enter me, one then two, moving around then leaving me. You o.k with this as I felt his hard cock against my chubby bottom, I pushed back, do it. I felt him position his cock then a sharp push as his cock entered me, the first in such a long time that I had almost forgotten the initial pain. He didn't wait too long as he eased into me, further with each push until he was soon fucking me, his hands gripping my shoulders as his cock revived feelings in me that I had not had for such a long time. You have a great ass, I like them big as he fucked me. I couldn't reach my cock, I didn't need to,it was hard and leaking cum,spasming as he literally rode my ass over me until I felt him spam and my insides were filled with warmth as he stayed deep in me. Eventually, he shrank and pulled out, no cuddling, you can shower in there if you like. I did, feeling my stretched hole, my still alive cock. When I got out and dressed, he had a coffee waiting for me. He said, Rob you have a great ass, the type I like to fuck. I hope you want to come back, just contact me when you want another fuck. I am not in it for a relationship, just good old fashioned fucking. I was back there 2 days later again on my hands and knees while Len used my willing hole.

AnonymousAnonymousover 9 years ago
LOVE IT!!!!

I would give ANYTHING to have my asshole reamed just like that right now!!!!

AnonymousAnonymousover 9 years ago
hot

would love a big cock to fill me up

63lsmith63lsmithover 9 years ago
OK

A 3 star read.

Share this Story

Similar Stories

Straight Guy: Big Dick Syndrome Seeing colleague's big dick in hotel room makes him curious.in Gay Male
My First Real Gang Bang A person finds his true orientation in a special gang bang.in Gay Male
First Time with Neighbor Daddy 18-year-old boy is taken by older neighbor.in Gay Male
How I Became A Gay Cock Slut Young married man is seduced at a resort.in Gay Male
Becoming an Anal Sex Whore Learing to love anal sex, from toys to the real thing.in Gay Male
More Stories