Down On Your Luck

Story Info
He gets lucky, or does he?
1.6k words
4.29
86.6k
14
0
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

What can I say, I'm an ordinary guy down on my luck a little when it comes to the fairer sex, in fact its been about four months since I was last with a woman. There's no obvious reason for it, I'm 6 foot plus, well built and fairly good looking in a rugged way, just since my fiancée left me I just hadn't had the interest, instead its been work, work, work.

Others at work knew since my break up that I'd been a little down ad they continuously invited me out for drinks on a Friday after work, after weeks of saying no I thought, well its got to be better than cold pizza and warm beer at home.

We all left work, still in our suits and headed for a pub on the outskirts of town. Spirits were high and within an hour the table was already starting to fill with empty pint glasses and packets of crisps. A few left after the first hour leave just me and another guy from the office, and a few more drinks went down before he suggests a stroll in the fresh air into town to a more lively pub, after what I'd drank I was up for it.

He was right the pub was more lively and I was loosening up slightly. We picked a spot bar the bar and leant against it most of the night, talking about work, sports, news and of course women, the drinks slowed a bit to a sensible pace and so far as they'd promised the night was perfect it was lacking one thing, a lady.

There was no point getting down about it because ladies were still looking at me on the odd occasion, one such woman was sat with another woman, she had long black hair, a slim figure, beautiful green eyes and what must of been by the look of them firm 36c breasts. Best of all she was looking at me and staring at me when she smile at her friends story. Then she stood to go the bathroom, it was then I noticed she was about 6ft in heel and had the most sexy arse I'd ever seen, or seen in a long time.

Another hour passed when my friend shocked me and said he wanted to go home now as he had an early start, I was shocked, I wanted to stay and look at this beauty a little more.

"Then stay" he said, next thing I knew he'd grabbed his jacket and left.

Well, I'm not a lover of standing in a pub alone drinking, but I ordered another beer and decided once done I'd head home for a weekend of doing nothing. Stood alone I'd lost sight of the beauty, knowing my luck she'd gone to another pub when I wasn't looking, then I felt a hand run up the back of my thigh and touch my ass. Startled I jumped turning to see who was finally touching me.

"Friends left you?"

It was the girl from the table looking more stunning up close.

"So, are you off to a club?" she asked politely. "umm..no I doubt it I'm not one for clubs" I stuttered, hey I'm out of practice with women. "You?" "No, my friends are going but I think I fancy an early night" she replied then ordered another drink.

"so" by now I'm looking for things to say. "you live around here?" "oohhhh" she chuckled. "Offering to walk me home".

Within half an hour she'd relaxed me and we were walking the quiet streets back to her flat, it was on my way so I didn't mind, and she was good company, the walk was a few miles. We talked about a lot of things including football which was great I'd never met a woman who knew so much.

We stood at the door to her flat and she leaned forward and gave me a very soft kiss on the lips.

"Nightcap?" she said with a smile.

Within no time we were fighting our way through the doorway pulling at each others clothes. After a lot of kissing on the soft she had me down to my boxer shorts and she was kneeling between my legs kissing me wearing her hold up stockings, thong and bra. My erect cock had slipped through the fly of my boxers and was smearing precum over her cleavage. Roughly she pulled my legs so I was sat right on the edge of the sofa and she pulled my boxers off revealing my cut eight inch cock. Without a word she pressed her tongue in the space between my ass and balls and worked up, her tongue pushing my balls apart and working up my cock, stopping at the tip to tease me, by now I was ready for anything.

Her tongue still working she looked up "hmm are you open to games" she asked briefly before devouring my cock right to the base. While my cock was deep in her mouth I felt her tongue working its way around my shaft like a snake.

"Oh god yes" I stuttered.

While still licking and kissing she pulled a holdall from the back of the sofa, by now my cock and balls were soaked, and I could feel her spit running down to my asshole. Using her one hand she jerked the base of my cock, but tight, so tight I wouldn't cum while she handed my up a blindfold. Eagerly I took in and my world plunged into darkness while my cock was on fire with delight.

"Good boy" she whispered.

Her finger worked around my ass, pressing lightly mixing the spit in, then the tip went in making me groan and within no time she has two fingers working my little ass while she sucked my cock. She had slipped a cock harness on my, my balls were separated and my cock wildly throbbing with the veins popping out from the chrome ring at the base of my cock. I wasn't going to complain as her mouth was giving me too much pleasure, then she stopped and from what I could guess she was standing, my point was soon proved as she grabbed me and made me stand. She kissed me deeply pressing her tits into me letting me know she'd removed her bra. Without a word she grabbed my painful cock and led me through the house, only till I was pushed backwards did I realise were must have been in the bedroom.

In a flash I felt my hands cuffed to the headboard and then my legs tied, before I could moaning I felt myself in a venerable scary position, my ankles were also tied to the headboard, which brought my legs up and back exposing my cock and ass to her.

"Hey what the hell" I questioned before feeling something round and rubbed being forced in my mouth, a bloody ball gag, I was helpless.

"I'm sorry" she said a little out of breath, but you might like it too much.

What I couldn't see was that when naked to go with her firm breasts was a throbbing angry looking 8 inch cock just like my own. The head was purple and glistening with her own precum. You think if I'd know I'd of walked her home!!

I felt more lub being spread on my ass but all I could do was moan into the gag, it was useless she'd made me her prisoner. Her breathing was ragged, she was excited. But my ass soon got the bad news as she removed the blindfold and let me see her erect hard cock. MY eyes widened as she smiled and pressed it against my anus. Now my ex hand fingered me there before, all men like it, but not something so long, wide and real!!!

Inch by inch she entered me never slowing, tears ran down my face from the burning pain. All the time the cock harness had my hard cock bouncing on my stomach, although if the harness wasn't there I'd still be hard. Soon she was working in and out slowly but building pace and the pain was giving way for pleasure, she was fit and could control herself, not once did she touch my cock but after ten minuets I felt my cock betraying me and the heat of an orgasm building through the harness, seconds later I came harder than ever before in my life, I coated my chest and face in my own sticky hot cum, longs thick strands of cum covered my from my nose to my cock, she smiled, knowing her job was done. Next was completely new to me, I felt her cock explode filling me deep inside with a very hot liquid, she was cuming in me. And she was cumming a lot. Soon after that I passed out.

*****

Hours later I woke with the sun coming up and braking through her bedroom curtains. I wasn't cuffed, I was free, my ass a little sore but still wet. My own cock stirring into its morning good status. She, who's name I still didn't know was lay with her back to me fast asleep. I was getting out of here, but my cock was raging, it needed to cum again, quietly I reach below the blankets for a quick rub only to hear her waking voice.

"Me first slave not you"

On the word slave something strange clicked in my mind, I cuddled up to her back and began stroking her dominating cock.

Please rate this story
The author would appreciate your feedback.
Share this Story

Similar Stories

Finding My Dream Wo(man) Never knew I wanted a tranny till I found one.in Transgender & Crossdressers
How I Met My Shemale Shy man dates a shemale.in Transgender & Crossdressers
She's Hung A transgender love story.in Transgender & Crossdressers
Amanda and Me Ch. 01 A shy IT guy meets someone.in Transgender & Crossdressers
His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
More Stories