Black Cross Dresser Chronicles

Story Info
Black cross-dresser bangs hot Black couple.
2k words
3.54
15.8k
5
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
Samuelx
Samuelx
2,101 Followers

What's up people? My government name is Omar Woodson but you may call Madame Orillia. The Black Canadian cross-dressing diva extraordinaire of metropolitan Toronto, Ontario. One of a few outspoken Black cross-dressers in town, and definitely one of the most wickedly fun and entertaining. Lots of Black men like to wear wigs, skirts, nylon panty hoses, bras and panties behind closed doors, but I am one of a few who can actually admit it.

As Madame Orillia, I like to have fun with both sexes and all races, but I got a special fondness for people of African descent. My people. That's why, when a shy young Somali guy named Ahmed Suleiman approached me and told me that he found me attractive, I was flattered and told him that we ought to get together sometimes. I love Black men and Somali guys, with their Afro-Arabian good looks and exoticness, well, they totally light my damn fire.

Ahmed Suleiman is a criminal justice student at the University of Toronto, and he's a newcomer to the vast, lovely province of Ontario by way of Alberta. Apparently, there's a lot of Somalis in the Edmonton region of Alberta, where Ahmed was born and raised. The Somali brother had never been to a city as huge as Toronto and was fascinated by life in the GTA. As a Toronto native, I gave Ahmed a proper welcome in the best way possible.

Ahmed and I got together at my apartment, and we definitely had a lot of fun together. I was dolled up to the nines with a long black wig, bright pink skirt, and bright red high-heeled shoes. I'm five-foot-ten, and kind of chubby, which totally works for me in my Madame Orillia persona. I'm that rare black cross-dressing diva with a natural booty, and the fellas can't get enough of me. I know Ahmed was delighted to get his hands on my thick black booty.

We got down and dirty, Ahmed and I. For real. I laid the tall, lean and athletic Somali stud on my king-sized bed, and sucked his long and thick dick while fingering his butt hole. Then I rolled a condom on Ahmed's dick and climbed on top of him. Ahmed gripped my hips and slammed his thick dick into my well-lubricated asshole. While fucking me, Ahmed cussed in the guttural Somali language and for some reason, it really turned me on.

Ahmed fucked me real good, and I cried out his name as the Somali dude relentlessly pounded his dick into my asshole. Nothing beats Black on black sexing, folks. As a Black cross-dresser, getting fucked in the ass by a masculine, well-endowed Black stud from East Africa was a dream come true for me. I love the brothers and I cannot lie, folks. Unfortunately, Black communities around the world have a negative view of gays and that's a damn shame. Lots of brothers who are gay or bisexual would love to have fun with a sexy Black cross-dresser like myself but the constraints of culture, religion and internalized homophobia keep them away. Such a shame, for real.

Ahmed and I had a lot of fun that first time, and the Somali stud surprised me by taking me out to grab a bite at a Caribbean restaurant the next time we saw each other. Much to my surprise, Ahmed seemed comfortable being seen in public with me and that surprised me because he's a Somali and the Islamic culture he hails from sees people like me as unclean. When I asked him about that, Ahmed told me that he considered himself bisexual and didn't give a damn what his fellow Somalis thought of him. Wow, I wasn't expecting that!

Ahmed and I embarked on a relationship, one that surprised me because, well, it made me really happy. Ahmed is bisexual and likes to fuck a tight pussy every now and then, and I decided that I would be okay with that. The mistake a lot of queers who get involved with bisexual men make is that they attempt to "gay" them up. Me? I found it hot that Ahmed's long and thick, magnificently dark dick fucked everything that moved.

I'm close friends with this six-foot-tall, busty and big-bottomed Jamaican chick named Aisha Thompson. We hooked up once, back when I was confused about my sexuality. Aisha fell in love with my alter ego Omar Woodson and couldn't stomach the fact that I am truly Madame Orillia, and that Omar is just a disguise I wear in the vanilla world.

We all have to make compromises in order to get by in this world. I work as an account manager at the downtown branch of the CIBC. Believe me when I tell you that as diverse as the Toronto business world is, it's not ready for openly queer Black male professionals in drag. So, I wear a suit and tie at work, look and act masculine, and make my money. Ahmed has seen me in my Omar Woodson disguise and thinks I'm cute, but he's only comfortable fucking me when I'm Madame Orillia. Works for me, as far as I'm concerned.

Anyhow, long before I admitted to myself that I'm a Black cross-dressing sissy, long before my Madame Orillia persona was born, I dated Aisha Thompson. We went out and had sex plenty of times and Aisha and I fell for each other but in the end, things didn't work out. Even today, on occasion, I get hard over a female but six days out of seven, I think of a hard black dick up my ass when I'm in fantasy land. See? Aisha and I could never work out.

Still, knowing that Aisha Thompson was still thirsty for me, I decided to use that to my advantage and get her in bed with Ahmed and I. The way I see it, I'm just managing my affairs. I'd rather Ahmed stick that bisexual dick of his into a pussy of my choice, one that I can control, instead of letting him run around the GTA. I approached Aisha with the idea of a threesome and the tall Jamaican cutie was all for it. Ahmed took some convincing, but he was down for it too.

The three of us met at my place, discussed the details over some red wine, then we got down and dirty. As the sweet and sexy yet lovely Madame Orillia, I led Ahmed and Aisha to my bedroom, and we had ourselves some fun. The two of us got naked, while I kept my drag gear on, and I feasted my eyes oh Ahmed's tall, muscular body and Aisha's big tits, curvy body and big round ass. Damn the Jamaican chick's got a booty on her!

I sucked Ahmed's thick dick while Aisha watched, fingering her hairy pussy. Just as I remembered, Aisha didn't like to shave down below. I remember going down on her, licking her pussy, and getting hair on my tongue. Good times. Once I got Ahmed nice and hard, the Somali stud put me on all fours, rolled a condom on his thick dick, smeared lube on my asshole and shoved his magic stick into my bumper.

I welcomed the feel of Ahmed's thick dick in my butt hole and the Somali stud pumped his dick into my derriere. Aisha watched us for a while, then joined in on the fun. The sexy Jamaican gal spread her thick, shapely thighs wide open, exposing an obvious target. Grinning, I buried my face between Aisha's legs and began licking her pussy with gusto. I teased her clit with my tongue while fingering her cunt and soon I had Aisha squealing and moaning in pleasure. I hadn't gone down on a female in a while but some things you never forget how to do.

The three of us continued with our fun, and now it was Aisha's turn to get fucked. The busty, curvaceous Jamaican gal grabbed my dick and sucked it while massaging my balls. At the same time, Ahmed got behind Aisha, smacked her big butt and then eased his dick into her cunt from behind. Hard and fast Ahmed began pumping his dick into Aisha's cunt. Aisha as I remember is a lusty screamer and her lack of screams ( as Ahmed slammed his dick up her cunt ) puzzled me until I realized her lusty mouth was filled with my hard dick.

Aisha Thompson sucked my dick until I came, and the first time in ages, I came all over a woman's face. Trust me, as a Black cross-dressing sissy, I don't do this sort of thing too often. Ahmed finished pumping his dick into Aisha's cunt and pulled out of her pussy. I smiled at Ahmed as he pulled the condom off his long and thick Somali dick and rubbed his dick on Aisha's thick Jamaican booty, before shooting his load all over her butt. Nice, I thought.

Aisha was still horny, and Ahmed and I needed a moment to recover since we both just came. Yes, I'm a Black sissy but biologically I am still MALE and I got the same sexual limitations as other men. This frustrated Aisha, so she took out her frustrations on Ahmed and I. Seriously, the bossy Jamaican bitch put us on all fours, side by side, and proceeded to lick our asses. I smiled as I felt Aisha's tongue in my asshole. Man, I actually missed the Jamaican chick's kinky games!

Aisha licked and fingered our asses, Ahmed and I, but the highlight of the evening came when the Jamaican diva donned a strap-on dildo and fucked Ahmed with it while making the Somali stud suck my dick. As a Black cross-dressing sissy, I tend to be quite submissive to the males that I deal with sexually. I was quite surprised that Ahmed went along with Aisha's plans and let her fuck his ass with the strap-on dildo. Surprised me, but also turned me on, to tell you the truth!

The three of us continued with our fun, and soon Ahmed and I turned the tables on Aisha, with her permission, and fucked her. The Somali stud and I sandwiched the kinky Jamaican diva between us, and filled her holes. Aisha rode Ahmed, who smacked her big butt and thrust his big dick into her cunt. I got a shot at Aisha's ass. Gently I spread her plump ass cheeks, lubricated her and then pressed my hard dick against her asshole. With a swift thrust, I penetrated Aisha's asshole.

Aisha's shrill scream echoed throughout my apartment as I entered her asshole. Grinning, I smacked her big butt while burying my dick deep inside her butt hole. At the same time, Ahmed sucked on Aisha's tits as he buried his dick inside her wet, hairy pussy. What an unusual tag team we made, seriously. A bisexual Muslim brother from Somalia and a Black cross-dressing sissy fucking the living hell out of a busty, big-bottomed and wonderfully freaky Jamaican chick, cramming our dicks in her pussy and asshole. Hot damn. This was definitely one for the ages. Ahmed and I fucked Aisha until she begged for mercy. How cool was that?

Much later, Aisha Thompson, Ahmed Suleiman and I hit the showers, and then we hung around my place, drinking and chatting. What can I say? A good time was had by all, ladies and gentlemen. Ahmed and I put Aisha into a cab and sent her on her merry way, then, hand in hand, we went to bed. A lot of my fellow Black sissies are stunned that I got myself a sexy, masculine and openly bisexual man as my significant other. The secret of my success? I let Ahmed be himself. The Somali stud is attracted to both guys and girls, hence why we have regular threesomes with Aisha now, but Ahmed assured me that he loves only me. That's good enough for me, folks.

Samuelx
Samuelx
2,101 Followers
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
AnonymousAnonymousabout 9 years ago
As usual

Worst fucking author on this site.

Share this Story

Similar Stories

TS Sexy-Tary Georgia's Boss has fun with her slutty Tgirl PA.in Transgender & Crossdressers
His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
A Black Cock Slut Dana gets a black daddy.in Transgender & Crossdressers
Party Slut Never fall asleep at parties!in Transgender & Crossdressers
A Shemale Vacation Ch. 01 Amsterdam whore with something more.in Transgender & Crossdressers
More Stories