Night Walker

Story Info
A john fulfills his anal fantasy.
1.8k words
3.25
65.7k
1
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

I have on my new red stripper shoes. I must say my feet look damned good in them. They make my legs look so much longer. Now I am the height as the average man.

A green Caprice Classic with some nice rims drive by. I hold out my arms like what's up but the driver doesn't even slow down. He probably doesn't have any money.

Some old lady in a Cadillac. I don't know what the hell she's doing on this side of town. She probably lost. Forgot to take her Alzheimer's medication or some shit like that. I'll probably see her on the street next to me in a minute.

It's quiet tonight. Everybody probably out celebrating Independence Day. I wish I could get down to the corner at those fireworks. I bet I could find some people looking to party.

Nice. A Yukon Denali. My favorite SUV. The driver rolls a few feet past me. I walk over and pull my skirt down over my ass. I lean in his window with my tits hangin' over the window.

"Hey baby. What's up? You lookin' to party?"

"Yes. How much are you charging?"

"First I'd like to know if you are a cop?"

"No I'm not a cop. How much?"

"Why don't you give me a ride and we can work some shit out?" I want to seeing how nice the interior of his Denali is. There is a car seat in the back. Probably some lame man cheating on his wife. Poor bitch. I'll probably be getting at least $75 out of this dude. He couldda bought some baby clothes or some shit.

"Get in."

"So what are you into Daddy? I can give you anything you want but you have to provide the room or I know a place if you think we can handle this in the car."

"I have a hotel room not too far. What I am looking for is a blow job and you fucking me in the ass with a strap on."

"I can take care of that baby." These guys are a dime a dozen. They are gay but marry women to satisfy everybody else or they just like it in the ass but their wives are too stuck up to give it to them. That's why I believe I am in the service industry. I gotta do this bitch's dirty work.

"You don't have much to say baby." He manages a smile. It is probably his first time. He looks like he is going to change his mind any second. All I know is he's gonna pay me for my time and he better take me back to my corner. He didn't even ask for a peak at my goodies and he didn't even ask my price. I am going to see if I can get more than I usually do from this fool.

It was one of the nicer hotels. It's not like those one-hour motels I am used to. It's some swanky shit. Nice big lobby with those floors you can see your reflection on. Damn I look good. Some lady with white curly hair and some fur wrapped all around her neck can't seem to take her eyes of me. I want to know what she's staring so hard at. She looks retarded wearing some fur thing around her neck and its eighty degrees outside. Fuckin' rich people.

We go straight to the elevator and up to the third floor. His room is pretty nice. Nothing special. I see a laptop on the table. Maybe he is some kind of business man. Seems like an all around normal guy except for the taking it in the ass thing. Whatever floats his boat. I just want to get paid.

"So you want to just get down to it or do you want to talk and shit?"

"We can get started."

"Ok, first you need to pay me. It will be one-eighty an hour. If it is less than an hour, you still pay me one-eighty. I need the money upfront. He has an envelope that seemed to be stuffed with twenties. I knew I should have asked for more.

"Ok, now the rules. Don't fucking kiss me. I hate that shit. You get anal and a blow job so don't ask to fuck me unless you plan on paying more. Got it?"

"Yes."

I sit him on the bed and stand in front of him. I pull down my denim skirt so it drops to the floor. I pull down my tube top so it stopped at my waist. I move closer to him and straddle his lap. He takes my tits in his hands and rubs them. I'm so used to this that it doesn't even turn me on. I can already see he is feeling good

I stand up and ask him for his strap on. He pulls out some ugly purple thing. Probably eight inches. What a freak. He fixes all the buckles and shit. I look down and see this thing stickin' out. I'm glad I don't have one of these things for real.

He remains seated on the bed. I reach down and pull his shirt over his head. Then I take off his pants. Now I'm really starting to feel bad for this man's wife. She probably has something on the side too 'casue there's no way she was getting satisfaction from his cock. At least I'm not going to have to worry about choking tonight.

I do my usual technique. My goal is that I can get a guy to cum before we get to the sex. Usually in twenty minutes or less. Then I can get paid the price to fuck for a simple blow job. You would think I would get in trouble for this but they are usually so ashamed for shootin' so fast that they don't make a big deal about it.

Since this guy's dick is so small, I am sure to use a lot of throat. I use my index, middle finger, and thumb to make a ring around his cock. I wrap my full lips around the head of his cock and rub my tongue over the hole. I quickly move the ring up and down the length of his cock for a few strokes.

I run my tongue down the length of the underside of his cock. I love that ridge. I stop in the area between his balls and ass hole and probe the area with my tongue. I roll his balls around on my tongue while I continue to stroke. His body keeps jerking. I know I am doing my job.

I slide my mouth down the length of his cock with my tongue grazing the ridge. I can fit his entire cock in my mouth. I feel the head of his cock in the back of my throat. I push my head down as far as possible so that he can really feel my throat. I turn my head left and right rubbing my throat on his dick head. I feel his hand on the back of my head pushing me harder.

Fortunately I have learned to do this and breathe. I take one hand and gently push his balls up to my mouth. I stick out my tongue and lick his balls while the head of his cock is probing my throat. I feel him thrusting his hips as he begins to fuck my mouth with quick jabs.

Finally, he lets me off his cock. I think I got him pretty worked up so while I'm fucking him, if I stroke him right, he should cum pretty fast.

"Get on your knees."

"Well actually I wanted to get on top of you."

"Shit. Less work for me." I lay on the bed and he crawled towards me. This is something new but there is a first time for everything, even when you have been in the business as long as I have. He straddles me and I hold the cock so that it is pointed straight at his ass.

He works himself down on my cock with no lube. He stops when the cock was completely inside. I took the moment to gently hold his cock.

He starts easing up and down on the cock. I match his rhythm stroking his cock. I hold him very lightly. As he started speeding up I added a second hand to his cock. I rotate my hands around his cock and moved them back and forth on the top and bottom half of his cock. He starts moaning. I knew I can get this guy to cum pretty soon.

I let him enjoy the sensation for a while. I tightened my hands around his cock. I feel his body jerk and his rhythm is interrupted. He is quickly back on track and I removed one hand in exchange for long fast jerks of his cock. I spit on my hand and rubbed it on the head of his cock. It is slippery. I put my thumb on the "V" on the underside of his head and continue to move my fingers along his cock.

I think he is close. I take my hand off of his cock and judge his reaction. He is surprised. I let him ride wondering if I am going to put my hand back on his cock. I make a ring with my fingers and start stroking him quickly. I cup his balls in my other hand. I feel them draw up a little and I know he is about to cum.

I stroke the top half of his cock, knowing in a few seconds I am probably going to get covered in a huge load. He comes completely off the cock and leans over me. I stroke him as fast as I can. He spurts cum all over my stomach. I lengthened my strokes milking out every drop of cum. My stomach is covered with the biggest load I have ever seen.

He rolls over on the bed. I give him a few seconds to recover. He probably just lived out one of his fantasies.

"Can you get me a towel or something." He goes to the bathroom and gets me a towel. I am happy to get this mess off of me. I check the clock and see that it all took only thirty minutes. Job well done.

He watches me get dressed. "You know you need to take me back right?"

"Oh yeah. Sure." I wasn't really asking him but I let him enjoy his moment. I guess I have time for a couple more johns tonight.

He stops at my corner. I open the door. "Wait. Is there a number or something where I can reach you. I come to town about once a month or so. I thought maybe we could do this again."

"You know my corner babe." He drives away. Poor guy. Another Caprice Classic and this one stops.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
amasterfoundamasterfoundover 17 years ago
Good story

I liked this story. You did a good job detailing what was going on. It would have been better if you had included more about their feelings. Try to get the reader to feel and see what is going on.

This story will be mentioned in the Authors hangout review thread on the forum.

Share this Story

Similar Stories

Coming out to a Friend How I told my friend I am a cross dressers.in Transgender & Crossdressers
Straight--With a Twist Two hot wives swing their hubbys in a new direction.in Group Sex
Mistress Watching Mistress watches Rory intently, as she is used by a stranger.in Transgender & Crossdressers
A Pegging Request My wife agrees to use a strap-on on me.in Fetish
Falling for my Wife My future wife's confession made her more desirable.in Loving Wives
More Stories