Cross-Dresser Fucked by Hot Sissy

Story Info
Anal and oral fun between to hot sissy cross-dressing sluts.
1.1k words
4.26
126.6k
40
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

Today I was feeling particularly horny and decided it was time to get some action again...! I jumped online and setup an online account with adult friend finder!

With my online account setup under my assumed identity I tentatively chose some revealing photos to upload... It didn't take more than a couple of hours before my pictures were up for all to see and a flood of contacts started to flow thru to my inbox, "hopefully one of these can help fill my 'other' box, I thought to myself".

After chatting with a few of the contacts, a girl named Louise, asked if I was keen to catch-up... I said that I was keen but apprehensive at meeting sight unseen... She suggested we have a video chat first to ease the tension, and I agreed immediately...

After connecting with Louise, we quickly loosened up and began to show each other our assets! As we quickly gathered steam, I began to imagine Louise sliding her cock inside my mouth and then fucking my boi hole hard and fast...!

As I was picturing this in mind, Louise sent me a message stating that she "liked what she saw, and she wanted me to be a good girl and cum over a suck her cock, and spread my legs for a good hard pounding...!"

By this time I was frantically rubbing my hard panty clad cock, and I was in quite a state, so without thinking I replied, "I can't wait to drop to my knees and feel your smooth un-cut cock grow hard in my mouth, and then spread my legs and feel it pound my tight boi hole...!

Within minutes Louise, sent me her address details...! I quickly changed my soiled black satin panties, for a pair of black lace, open back, ruffles panties! I then pulled a matching bra over my size D breast forms! Next came a black garter and a pair of thigh high stockings with red bows at the top. I then chose a tight black calvin klein singlet and put it on too! I then put on a pair of tight women's black guess jeans, and a pair of red 6" pumps. I quickly pulled my long brown wig on, threw on a splash of makeup and I was ready to go!

I jumped in the car and headed off to Louise's place... Upon arrival I was greeted by a stunning Louise dressed in black high heeled shoes, thigh high stockings, a short black and white zebra mini skirt and white satin blouse...

Louise quickly ushered me inside and guided me to the couch... A quick scan of the area revealed a large plasma screen playing porn which showed to lesbian hotties fucking each other with a purple strapon!

With the porn playing it was a short time before we were both excited and Louise put her arms around me and drew me into her warm embrace...

We started to passionately kiss as we began to explore each others feminized bodies. I felt a warm surge flush through my entire body as I tentatively grazed my long nails across the thin lace barrier covering her gorgeous smooth uncut cock...

I was glowing as Louise began to loosen my jeans and started playing with my own stiffened pole through my panties...

I was so hot now, that i wanted to taste Louise's cock, so I pushed her back against the couch and lowered myself to my knees, positioning myself between her spread legs, I gently reached inside her lace panties and started stroking her smooth cock.

As she was starting to harden, I gently lowered my mouth and began giving her light licks, and swirls with my tongue! This brought about an immediate response as Louise grabbed my head and started fucking my mouth with slow deep thrusts!

As Louise continued fucking my mouth her cock grew more and more until eventually, the tight firm head popped out it's skin inside my mouth.

It felt very strange as her knob hit the back of my throat... I was enjoying this immensely and then it happened, Louise's body tightened around me suddenly and shook several times as she squirted a wave of cum down my throat... I was surprised, and although some juice did leak out I managed to swallow most of it....

Louise was glowing and she guided me to lay on my back on the couch, and spread my legs! I complied with her request and she reached into my panties taking my hardened cock in her hand and quickly started sucking on it...

She sucked on my cock and she also spread my tight boi hole and stabbed at it repeatedly with her slippery tongue... It felt fantastic and I was writhing in ecstasy as her fingers worked on my cock whilst her tongue explored my now loosened slippery hole.

After receiving some of the best oral attention I've ever had I asked Louise to stop teasing me and start fucking me with her gorgeous cock...

Louise acted on this request immediately and positioned her hard cock between my slippery cheeks and slowly started pumping back fourth. Her slick cock slipped easily back and fourth between my cheeks, and across my warm hole for some time before I reached down between my legs taking her cock and placing it inside the warm entrance of my hole...

This was heaven, as I gently rocked back and fourth, her cock slowing sank deeper and deeper into me, until finally she was buried in me! Louise grabbed my spread legs and supported them as she gently fucked me with a steady rhythm... After fucking me like this for about ten minutes she asked me if I would like to try doggy style and I was happy to oblige! I got of the couch and assumed the appropriate position for my next pounding!!!

Louise moved behind me and in one powerful thrust she buried her cock to the hilt inside me... As she fucked me my own hard cock slapped from side to side between my legs.

From here, she started to frantically pound her cock into me, until eventually she screamed I'm going to cum...! To this I shouted, "fill me up baby, I want your seed deep inside me!"

With this, Louise shuddered, her body tightened and then she began to fill my slippery wet hole with her juicy warm sperm. Seconds later my own stiff cock started erupting warm sticky cum down my legs as Louise emptied her last drops into me...

At this point I was spent and we both decided to call it a night and with that I threw my clothes back on, gave Louise a quick kiss, thanked her for the evening and headed out the door...

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
17 Comments
AnonymousAnonymous2 months ago

Crossdresser all my life, sissy since, oh, IDK, 2015 maybe. Closeted gay, anyway, for 40 years, I've had one play partner who dressed and was into the sissy stuff, too. Wish I could get rid of all my hair (I can only shave my chest from neck to thighs, my ass, too. I'd love to get with 6 or so neglected guys my age (62) or older (or younger!) for hot CD group sex! Imagine all those horny slots, shaved smooth, all sorts of girly underwear, toys, lube (and some good herb!), writhing around on a king size bed, sharing holes and cum, rubbing, teasing, licking, stroking, mmmm.......makes my mouth water just thinking of all the naughty things to do! Who needs girls when other cd's are around! horny4cum69@proton.me

AnonymousAnonymous2 months ago

I thought it was great--no pussy-footing around, just getting right into sucking cock, fucking and eating cum. Very well written, hope he/she will write more!

AnonymousAnonymous12 months ago

Hot,hot loved it it made me cum.

AnonymousAnonymousabout 1 year ago

Good story. I meet up with my sissy friend who i came out to with my jeans and shirt on under this i had a bra thong and micro skirt and hold up stockings on. After a short time i pulled my shirt top to one side showing him my bra strap. He was shocked never ever thought i was a sissy. We went back to his house a i striped off to show him that i was a sissy and he was the only one to know. We kissed and sucked each orther, untill i asked him to fuck me. He put lube on mt virgin pussy and took my cheery. Some pain at first then i pushed back on his cock and could not belive how great it was pure bliss, afer a shot time i felt him cum deep into my pussy, and i became his sissy cum slut. I should have do this years ago.

AnonymousAnonymousover 1 year ago

buy condoms

Show More
Share this Story

Similar Stories

Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
Tricked Into Pegging And Sucking! Husband learns to love pegging and cum.in Transgender & Crossdressers
Like Mother, Like Sissy A sissy learns he is a princess . . . and a sperm whore.in Transgender & Crossdressers
Our Sissy Slave My girlfriend and her friend force me to submit.in Transgender & Crossdressers
Her Bulge The woman at the gym has a bulge in her spandex.in Transgender & Crossdressers
More Stories