Short Tales 04: Tranny on a Train

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

After about the 4th or 5th shot down my throat, Bogdan released his grip, and I was able to let some of his length back out of my throat. He shot twice more into my greedily sucking mouth. It tasted like bliss!

I loved it so much I nearly came, hands-free, myself!

I swallowed every drop, then wrapped my lips around his cock so that I could tongue his head's eye for more.

Holding my head gently, Tata forced me away from his cock.

Every Trans prostitute in the world will tell you that this is the dangerous point. Your 'John' has shot his load, gotten rid of his sexual frustrations, and will often freak out now.

"I'm not a fucking faggot!" They'll snarl at you and then try to beat you to prove to themselves how manly they are!

Bogdan merely leant forward and kissed my cum stained lips before guiding me up onto my back on the bed.

He didn't slowly stimulate my erogenous zones as he lowered himself down this time. He flicked a tongue across my nipples, briefly tongued my belly button, and then took my rock-hard cock in his hand before going down on me.

Bogdan could easily swallow all five and 3/4 inches of me. He was a genuinely gifted cock sucker! Bobbing his head slowly up and down, he alternated between sucking fervently and softly. Between swirling his tongue around my glans and lapping at the eye, and bobbing the whole length slowly and about half of it quickly, I soon reached the point of no return.

"I'm going to cum, Tata," I informed him.

Sucking all of me into his mouth, Bogdan flattened his tongue along my shaft and sucked firmly but gently.

With an almost womanly squeal, I came, copiously, into Tata's warm, sucking mouth! I was truly in heaven! Load after load, I squirted into Bogdan as he moaned and swallowed it all.

As I came down off my cum high, Bogdan wrapped his strong arms around me and cuddled my back to his chest.

Stroking my hair, he said, "That was unfuckingbelievable fucking! I cannot believe you could swallow it all, draga (dear one). Nobody has ever taken me all the way!"

Leaning back, I kissed his chin, "I wanted to please you, Tata," I told him. "I want to be the best girl I can be for you!"

Unbelievably, Bogdan was hardening against my ass! I had managed to swallow all of him. Was I going to be able to take all of him in my ass, my 'boy pussy'?

I didn't know, but I was surely keen to find out!

Turning to face him, I wrapped my arms around Tata's neck and kissed him, "Make a woman of me, Tata, please?" I pleaded.

Bogdan lifted himself slightly, so I could lift my knees and, still lying on my side, wrap my calves around the back of his knees. His dick was now throbbing against my taint.

Wriggling my butt, I kissed Tata again. Tata moaned and began to kiss me passionately, thrusting his hips to meet my wriggles.

Bogdan rolled onto his hands and knees with me still clinging to him. With a deep manly roar, he pushed me off him onto the bed and forcefully shoved my knees up and apart.

I expected Bogdan to try and dry fuck me as he was so turned on, but he was too much of a gentleman to do that! Instead, he went down on my ass.

Holding my knees back and apart so that my hips were lifted slightly off the bed, Tata began to tongue my rosebud. Forcing more and more of his invading tongue into my ring, Bogdan added more and more saliva to my already dripping boy pussy.

Slipping his index finger back inside me, Tata gently spread my rosebud and forced his wetness deeper into me.

Satisfied I was ready, Bogdan offered his magnificent cock to my lips once more.

"Make me as wet as you can, mališa. I do not wish to hurt you!"

I eagerly complied! Sucking him all the way down to his abdomen, I lashed his penis with my tongue and made the head and shaft as wet as I could.

Letting him slide out of my mouth, I lay back down and lifted my knees up and apart, as a woman would do, to accept her lover into her secretive parts.

Tata slipped between my young thighs, kissed me on the lips, and looked lovingly into my eyes.

"I will be slow, so your pussy has a chance to get used to me, yes?"

He was huge, so, a little fearfully, I nodded. I needn't have worried, though. Tata had prepared me to take him so well that he slid home without me even experiencing that usual twitch as a cock passed through my knot.

Holding me tightly to him and kissing me, Bogdan gave my boy-pussy a chance to adjust to his width and girth. He began to slowly rock his hips back and forth, making his cock move deliciously inside me.

Unbidden, my legs wrapped around Tata's hips. I started to, unconsciously, move with him. Holding still as he withdrew, then pushing up at him as he pushed into me.

Faster and faster, Bogdan fucked me withdrawing more and more of his massive dick as he did. Then, just as I thought it couldn't get any better, the head of his big cock rubbed across my prostate.

With a surprised grunt, I twitched and bucked my hips up at him.

"That's it, devojčica! Right there," Bogdan crowed and stroked into me again.

I thrashed and bucked like a wild thing on the end of Tata's superb cock. I was moaning like a right dirty slut!

"Fuck me, Tata! Oh, fuck this boy-girl well. Fuck my ass, take my boy pussy. I am all yours! Have me, own me!" These were just the things I remember moaning to him.

With a deep growl, Bogdan came in my ass. Feeling his cum squirt across my prostate sent me into ecstasy, and I began to cum too. Just from being fucked in the ass!

Bogdan must have spurted in me at least six times. Every time he squirted across my prostate, I would squirt too. My juices spread between Tata's body and mine.

Bogdan finally slowed to a stop. My boy clitty was still twitching and trying to cum as he withdrew his softening cock from my ass.

Tata went down on me and licked and tongued all of my juices from my pelvic area. Kissing my soft cock, Tata said, "We will now sleep. You are exhausted, and I do not need much sleep, so I will be gone when you wake up. Look for my note, yes?"

Bogdan cuddled me to his chest again before insisting I roll on my side so we could spoon as we slept.

Gently kissing the nape of my neck and almost absentmindedly playing with my nipples, Bogdan drifted off to sleep. I followed him down almost immediately. He was right. It had been a long time since I could afford to let my guard down and let myself drift entirely away.

The life of someone living on the streets is to sleep with one eye open, so to speak.

In the morning, as he had said, Bogdan was gone. I looked for his note and found it in an envelope on the dining table.

I opened the envelope and took the note out. It read, "Moja draga mala (my darling little one), I need to spend my day at the office. When you step outside, you will find my driver waiting for you. He will take you shopping for clothes.

Choose some outfits but make sure you select an evening dress because I am taking you to an important, for me and my company, dinner tonight and I need you to look veoma lepa (very pretty). You will need shoes, lingerie, etc., too, no?

Money is an object not, yes? The driver, Ivan, will pay for everything!

Be a good girl, and I will see you tonight at my home, yes?"

The End.

Epilogue: Now.

The above happened about a year ago. Tata still treats me as if I was his little princess. He sent me for some male to female cosmetic surgery hence the 34C boobs and the fact I am hairless all over my body except for my head.

He paid for makeup lessons and deportment lessons and sent me to a 'finishing school' so that I could make small talk with all people.

I accompany him as his 'niece' to his company events and act as the hostess at his dinner parties and office dos.

I wanted to get 'bottom' surgery to complete my transition to female, but Tata says he likes sucking on my cock too much! Sometimes, when Tata is really horny, I fuck him with my boy clitty, too!

We still ride the Cleveland train from time to time, so if you see an older distinguished gentleman with 'salt and pepper' hair, that is more salt than pepper now with a small pencil moustache, holding the hand of a stunningly pretty black-haired woman who is probably little more than a third his age riding in your carriage say hello. Tata might even ask you to come home with us!

The End.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
AnonymousAnonymousalmost 2 years ago

That was a very good story. I'm good to see her get off the streets and Tata really appreciates her for who she is. You know love is blind and by the way you wrote the story he really loves you. Thank you again for the opportunity to read your story.

CharletteCharlettealmost 2 years ago

Oh such a wonderful story !

I so enjoy a man who treats a gurl with respect rather than as trash he thinks so little of.

The entro to the story was sad for me as i have known gurls who were kicked out of their home in their teen years for trying to be the person they felt most natural and comfortable with, rather than faking being a happy male to appease mostly a disapointed father.

Abruptly ending the story with quick explanations detracted from what could have been a warm, fuzzy, wonderful prelude to a continuation of another several chapters of life with Michelle and Dan.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Snowed In Snowed in, with his best friend's cousin.in Transgender & Crossdressers
Futa House A boy unwittingly discovers a gold mine of girlcock.in Transgender & Crossdressers
Loving Yvonne A new neighbor changes a young man's life.in Transgender & Crossdressers
Ms. Jackson Ch. 01 Boy is torn between his longtime girlfriend and her sexy mom.in Mature
My Adorably Hung Summer Roommate Darren meets Danielle, a petite redhead w/ something extra.in Transgender & Crossdressers
More Stories