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A Short Story
By MrStanley, USA

Fancy a quick one? Enjoy this short story from the pen of MrStanley.

Upholding the great tradition of erotic fiction with the added twist of the latest AI-generated artwork. But are they really fiction? You decide! 

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Story 4 - Alessia Meets Thai Ladyboy
Recounting Alessia’s meeting with Tip, the slim Thai Ladyboy!

In this scorching episode, Alessia takes a vacation in Thailand and goes to the city of Pattaya. She's there to meet some of the pretty Ladyboy Transsexuals that populate that resort city. Many Americans and Europeans come here for sex vacations

Alessia Travestita in red dress in Pattaya, Thailand

Alessia arrives in the hot, humid city and takes a cab to her upscale hotel near Walking Street.

(Encounter now related from Alessia point of view, present tense)

The long flight made me feel dirty, so I shower and clean myself up. I decide to stay in my room and use some of the services provided. I put on a sexy red translucent dress over my lean muscled body. For my appealing feet I don a revealing pair of golden thong sandals. I decide to sample the “massage” service offered by the hotel.  I call room service and give them my credit card information for the masseuse services. The charge is 3500 Baht per hour (100 US Dollars).

In only a few minutes there is a knock on my door. I unbolt the door and see a very pretty petite Thai “Lady.”  

“Are you, my masseuse?”

“Yes, Mam, my name Tip. You are English?”

“Yes. My name is Alessia. I’m from a small English city near Manchester,” I say as I shake her hand.

Tip is very thin. I estimate she is about 95 - 100 pounds and around 5 foot 3 or so. She has fairly large hands and feet. Her skin is olive coloured while her hair is jet black. She is dressed in a very light low-cut yellow dress with red platform high-heeled shoes on her pretty red painted toes.

Thai Ladyboy in Alessia Travestita fiction

“What kind of massage do you want?” She asks as she looks me over.

“I want your entire package.” I say as I look at her bulging semi-erect penis outlined in her sheer dress. I don’t think she understood my pun.

“Do you want one-hour service or two?” She asks.

“Does the two-hour service include sex with the massage?” I ask.

 “Yes. If you like. My specialties are deep tissue massage, prostate fuck, cock suck, ass fuck and hand job.” She answers in her Asian accented pidgin English.

“You assume I have a cock?” I ask her with a smirk.

“I see you big dick poking against dress when we shake hands. You pretty tranny lady. I am ladyboy. My dick very fat and long. Fuck, suck long time. I make you beaucoup happy.” Tip says in her deep Asian accent. 

Near the back of the room is a padded massage table that is about three feet high.  Tip holds my hand as we walk toward the table.

Alessia Travestita Massage Table

“You very pretty Tranny lady. You tall very strong. I love your muscles. I skinny no muscles.” She comments as she helps me out of my clothes.

 I slip out of my sandals as she hands me a small towel to conceal my genitals. Tip gently positions me on my stomach. My back and rear are totally exposed for her massage therapy.

“I give you regular massage first. Then we do what you like. How long you want regular massage, pretty lady?”

“How about 30 minutes then we can do some fun stuff.” I reply.

Alessia Travestita massage

Tip is tiny, but very strong and wiry for a petite ladyboy. Her hands feel amazing as she rapidly works over my shoulders, back, arms, thighs and calves. The last five minutes of our regular massage she pops the joints in my fingers and toes.

After that, she informs me it is time for our intimate massage.

“OK. Alessia, you want me naked like you?”

“Of course I do.”

She slips off her dress and has on a very sheer black G-string. It is apparent that Tip has a large penis. She slides her thong to the side to reveal a huge thick member.

Thai ladyboy by Clovis Luik in Alessia Travestita fiction

“You like big cock?” She asks as my eyes take in her very impressive organ.

“Yes, I do.” I say as I scrutinize her thick long semi-erect penis. She is easily more than six inches already.

“What you like me do?” She asks. 

I rollover on my back. My massive mammoth erection is at its 8 inch extent. Tip smiles as she admires my cock.

She coats her hand with a big bottle of lube. Tip strokes my thick erect penis with one hand while she tenderly scratches my shaft with the sharp fingernails of her other hand. The sensation is extremely gratifying. 

“You big cock like mine!” She remarks.

“Can you massage my prostate now?” I ask.

“Yes. I get you wet now.” Tip positions me on my knees on all fours on top of the table and holds my legs apart.

I feel her stiff moist tongue on my loose wrinkled anus. She slides two lubed fingers deeply in my ass hole and massages my prostate very vigorously. Tip adds another two fingers and uses her hand to open up my rectum. She includes her thumb and then thrusts her entire hand wrist deep inside my clenching anus. Tip fucks my ass with her fist until my hard penis drips huge gobs of semen as my prostate reacts to her milking. I grunt and pant in pleasure.

Alessia Travestita gets fisted

“You want my big cock in ass?” She asks.

“Yes of course.” I say as I observe her reflection on the mirror hanging on the wall alongside of the massage area.

I gaze at her extremely petite form as she moves on all fours behind me. I see her erect penis now. She is certainly as well hung as I am. Her big hard cock is dark brown with a pointed glans. Tip’s big penis is curved and contains huge angry prominent veins along its vast length. She puts her hands on my hips and spreads my ass cheeks wider for her pleasure.

“I love your ass hole! It open for me. I fuck your ass now. You want me use condom?” She asks in her heavy Asian accent.

“No, Tip I want you to fuck me bareback in the ass.”

My cavernous rectum gapes open from the recent fisting. I feel her glans slip into my loose wet anus. I clench down with my sphincter on her length as she slowly sodomizes me.   

“Feel very good Alessia!” She squeals with delight.

Tip pounds her immense erection into my clenching anus with extreme vigor, violence and velocity. Her gigantic testicles slap at my impaled stretched ass hole with each downstroke of her gargantuan cock. Her massive semen filled orbs hang low in their sack. My sphincter struggles in its attempt to strangle her huge hard steely penis.

“That feels amazing Tip! Fuck me hard, I am about to cum!”

Alessia Travestita fucked by Thai ladyboy

She pounds me for a few more strokes and abruptly jumps off the table.

“I suck you now. You big cum in my mouth.” Tip yells.

Tip the Thai ladyboy suck Alessia Travestia

Gently, I rollover on my back and watch as this gorgeous lady boy leans over me and inhales my pulsing profuse penis deep into her throat. Tip is an accomplished deep throat artist and repeatedly swallows my extensive length balls deep. Her pretty head is a blur as she bobs on my convulsing cock.

“I am cumming, Tip!” I grunt in gratification.

Tip’s greedy eyes gaze at me as she deep throats my enormous length enthusiastically down to my testicles. I grip her head and hold it down as I shake with a full body orgasm.

My lengthy erection erupts in her mouth as her eyes bulge as the force of the hot bolts of my cum fill her throat. She closes her eyes and concentrates on swallowing the massive loads of thick hot salty semen. Tip spits out my semi-erect cock after consuming all of my ejaculate.

Tip enjoys Alessia Travestita's hot cum

“I love pretty Tranny Lady very much. Me like your big dick. You cum very much.” She says as she smiles at me.

“Thank you, Tip. I enjoyed the fisting, ass fucking and cock sucking. I want to reward you now.”

“You pay more money?” Tip asks.

“Yes, of course. You earned it. I am satisfied now. I want to pleasure you.”

I stand up and kneel before her. Tip stands upright and glares at me as I squat down in front of her. It amazes me that a Ladyboy so small has a big healthy 8.5- inch cock.

“I want to suck this amazing dick!” I say.

“You suck Tip’s big cock! Make me happy! I give you my beaucoup big dick.” She says in her Asian pidgin English.

I clutch Tip’s colossal dark brown veined penis with my hands and worship its thickness and length. I suck the tip of her pointed glans avidly into my mouth. My lips envelope her massive girth of her shaft as I swallow her span into my throat. Her giant testicles dangle low in their sack and bump my chin as I deep throat her length on each downward plunge. My slick slippery slimy throat hurries  her impending orgasm. I attack every inch of Tip’s profuse prominent penis with speed swiftness and urgency.

 

“You like my big cock! Feel very good! I cum soon.” She says as she grits her teeth in pleasure.

I renew my oral assault upon her rigid stiff erection. Tip smiles at me as she holds my head by my long blonde hair. My thin lips stretch around her girth at the base of her veiny thick cock. Her entire dick is buried deeply in the back of my silky wet throat. This sends her over the edge.

“I cum! I cum! You swallow deep!” She yells in orgasm.

A huge volume of hot salty semen blasts the back of my throat. I hold her length in my throat and mouth and swallow her vast load. Several more jets of lesser semen discharge into my throat.  

 

“You very sexy lady! We spend night together. Fuck and suck each other all night.” She says as I lick the last drops of semen from her semi-erect cock.

Alessia Travestita takes a load from thai ladyboy

“How much more will that cost me?” I ask as I still hold her impressive penis in my hand.

“10,000 Baht. Very good price.” She remarks.

“I will give you 200 British Pounds Sterling. In cash.” I respond.

“Very good. We take shower. Go dinner then fuck suck all night.”  She answers.

 

To Be Continued>>>>>>>>>>>

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Alessia Travestita's friend Amelia
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