Cadogan Street Carpark

Story Info
A story of cross-dressing lust.
1.5k words
4.13
53.8k
8

Part 1 of the 2 part series

Updated 09/22/2022
Created 03/20/2010
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

My name is Peter and I am 49 and married but a secret sissy cocksucker. I have a very dirty secret. The feel of women's lingerie against my skin makes my 6 cut cock harder than steel. And it's more than just the cross-dressing. I am bi sexual and I would love to submit to dominant older or younger men.

I remember as a child my older sister Janette had the best and softest bras and panties I had ever worn. The first time had been out of sheer curiosity, I wanted to know what girl's underwear felt like compared to my plain white Y fronts. So when everyone left the house when I was 15 and a horny teen anyway I made my way to the clothes hamper and grabbed a pair of my sister's underwear and then ran back to my room. My finger clasping her dirty things were trembling but locking my door I stripped down naked. At the time I was just starting to fill out so I still had a bit of a slim girlish build to my body. Janette wasn't that much bigger than me other than in the tit department and I had often spied on her with my cock in hand and feeling it shoot hard as I watched my own sister dressing and undressing.

When I looked at myself for the first time in the mirror my cock was like a bolt and rock hard. I knew at once that this was the thing for me. I pranced around in Janette's things for awhile and then collapsed onto my bed, my cock throbbing and leaking cum. The underwear were already dirty so it's not like I felt bad for wanking myself off to the strongest orgasm of my young life. Then it became a nightly ritual. After everyone was asleep I would sneak downstairs, grab the bra and panties she'd worn that day and then put them on. I was always careful to not make any noise or get caught.

But marriage and a career followed and precluded me from my secret desires for many years until I finally came back to them, once morning when my wife left for work and I was in the house alone. I stripped and slid her fishnet hold ups on followed by pink lace panties and a bustier. Within seconds my cock was like a rock again and I wanked happily as I looked at hot porn. This became my new ritual and it wasn't until I finally got up the courage to meet that my dreams all came true.

I soon made contact with a few dominate males some older some slightly younger that loved the idea of me servicing them while dressed up like a sissy as they looked at porn. The one that really caught my eye and made me hard was you as we talked about kissing and caressing and touching and wanking and sucking.

After several long conversations and sending him several pictures of me dressed up we agreed to meet.

And this is why I am now sitting in my car with an overcoat on and nothing underneath but a black lingerie set that I had bought specifically for you to see me in. It is a black halter top teddy with matching holdups and panties. Very tight and very very sexy.

My fingers drummed the steering wheel nervously. Jonathan would be my first encounter I would be having in a few years. But, being dressed so sexily I felt like a virgin, it was thrilling but also scary at the same time. We had decided the covered parking of Cadogan Street would be the best place to meet up and we could drive somewhere more discreet. The second fourth level was perfect and I sat in the next to last spot near the wall. I knew we would have great coverage from prying eyes. The flash of headlights caught my attention as a sleek black Vauxhall pulled up alongside me. The windows were darkly tinted and the headlights flashed twice. It was him. After he turned his engine off I waited a minute before making my way over. My heart felt like it was going to burst from my chest as I opened the door and slid inside.

"Take off your coat, slut!" You order in your smooth English accent. I nod and slip the coat off as you run your hand down my bare shoulder. My cock is semi hard against my panties and already starting to leak.

I keep my eyes downward as you recline your seat back and unzip your grey trousers. You have no underwear on and your cock springs into view instantly. It looked bigger in person than it did on the computer. A full thick 7 inch cut cock pulsating and throbbing for my mouth. It is straight and topped with a thick mushroom head. Precum is already gathering at the tip.

Licking my lips I ask. "May I suck your cock sir?"

"Show me first!"

"What?" I query then remember. "Oh, oh yes sorry!" I reach into my coat pocket and remove photos of my 2 daughters, aged 19 and 21 in their sexiest dressed poses along with naked and half naked pictures of my wife, along with pairs of dirty panties from all three females in my life.

You place the pictures on the dashboard and sniff the panties and I watch as your cock seems to grow even bigger and harder.

"Yes, slut!" You grin. "Suck it all you want." You close your eyes and relaxe as I bend over and run my tongue along your hot shaft. My taste buds explode at the first taste of cock in so long. I moan softly and waste no time and taking you into my mouth. Slowly my mouth begins to glide up and down your cock, sucking and swallowing. You moan every so often and even pat my hair, but soon the dom begins to come out in you as you push my head down, making me take all of it into my hot wet mouth.

"Good slut, take Daddy's cock!" You purr and begin to thrust up as you push my head down, my nose touching his pubic hair and your cock almost choking me. But the scent of you is so manly and thick. My cock aches and the urge to stroke grows, but I know I aren't allowed to cum until you have. As you thick head fills my throat I swallow, making you groan out and thrust more.

My right hand slides down to cradle your thick balls, my fingers caressing and rolling them around in the silky flesh. Your balls draw up to your body, the skin growing taunt around them. I know you are close now. I can taste more precum with each upward stroke. I feel your hand slide to the back of my neck and with only a little pressure you push me down as your cock suddenly explodes. Gagging a little I pull up when able to. It tastes salty and sweet at the same time and thick as well, clinging to the back of my throat but I don't care. I am here to please you as you ogle my wife and daughters.

There's a huge cum stain on my panties now and I need to cum, badly.

"May I cum now, please sir?"

You grin and nod. Slowly, watching the expression on your face, I pull the black panties down and pull at my cock. Licking your cum from my lips I stroke very slowly before my cock and balls explode. I make sure to tilt my cock against myself to keep cum from hitting you or your car. Moaning I fall back against the door. Thick white blobs of cum decorate my stomach panties and the top of my black teddy.

After the world stops spinning I reach into my coat pocket and pulled out a cloth handkerchief and clean us both up before tucking your cock into your pants. As I slide on my coat and prepare to exit the car you speak. "That was good. We should do it again soon."

"Yes we should. You know where to find me." I have a smile on my face as I slip from the car and return to my own.

You drive away first and soon I start my engine and drive home. I pick up my cell phone and dial my wife's number.

"Hello?"

"Hi hun, it's me. Listen how about we go out to Soho tonight? It's been awhile since we've gone out to a nice dinner."

I could almost hear her smile through the line. "Oh that sounds wonderful. Let me call Kathy and I will be home in about an hour."

I smile, more than enough time to shower and hide my outfit. "That's fine. See you at home!"

She hangs up and I head home. My mind is on sucking Chris again instead of dinner with my wife. Maybe next time we'll go a bit further. Who knows? All I know for sure is that it will happen again and I looked forward to it greatly.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
7 Comments
AnonymousAnonymous3 months ago

I to have had such an adventure. I placed an advert as a sissy cocksucker and got many replies. The one I met was a guy in his sixties with a very thick 8 inch cock who could keep a good hard erection even after cumming. We met at his house and I was dressed in a short black dress, stockings suspenders, a thong black bra with false tits a wig and well made up with my cosmetics. When he saw me he had me on my knees and was a real Dom making me lick his balls and throat his cock before having me lie on my back before penetrating me hard and humming deep inside me. He had me suck him again and wanted to give me a facial which I love and even though he had only fucked me he produced a big load which covered my cheeks, nose and forehead it covered me like a mask . That was 5 years ago and we meet once a month for wild sex in lots of positions and I also meet other men. If you would like to meet and fuck me let me know I just love cum.

cdCindy1cdCindy1about 6 years ago
just like me

I loved your story. I am just like you - a married sissy who dresses in sexy women's clothes while sucking big cock (only some men like CDs, others just want me naked). I also let the men I meet fuck me because it makes me feel like such a woman, with a cock in my man-pussy. My wife doesn't know as I'm still in the closet with my secret gay CD life. I would love to hear from you about if and when you will tell your wife.

AnonymousAnonymousover 12 years ago
* ANOTHER CD

your story fit me to a tee. As as crossdresser there's nothing in the world that can match sex with a guy while crossdressed. I've got everything from very large fake tits, full make up, wigs and all the clothing that I can find to make me look and feel like a whore that's giving my "pussy" to a man. feeling and seeing his hard cock knowing that soon I'll be sucking it and then be getting fucked. I love to be dominated and abused. The more dirty names they call me the better it is. I love going fully dressed into ABS locations and spending hours with cocks in my body and seeing others waiting for their turn. I've been fucked 25 times in one session and would have took more had they been available. While the thought of actually being a woman has entered my mind I don't think the thrill would be the same. It's a great life.

PicturePainterPicturePainteralmost 14 years agoAuthor
Thanks

Thank you for your comments and what a turn on the story and your comments are. mmmmmm. part 2 to follow very soon. if you want to email please do on picturepainter123@yahoo.co.uk

AnonymousAnonymousalmost 14 years ago
I too am a married sissy cock-sucker

I loved your story. I am just like you - a married sissy who dresses in sexy women's clothes while sucking big cock. I also let the men I meet fuck me because it makes me feel like such a woman, with a cock in my man-pussy. Please tell us what happens next !!!!

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

How I Became A Gay Cock Slut Young married man is seduced at a resort.in Gay Male
Backseat Introduction Girlfriend's dad and boyfriend share the back seat.in Gay Male
Becoming a Sucker Pt. 01: Trucker Has Me A married man goes to a rest stop and is forced to suck.in Gay Male
Accidental Cocksucker A straight man is drawn into the world of black submission.in Gay Male
Cocksucker Straight married man submits to a young stranger at airport.in Gay Male
More Stories