A Young Man's Sexual Odyssey Pt. 02

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The Vibrating Tranny Hooker.
4.1k words
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Part 2 of the 3 part series

Updated 06/08/2023
Created 09/29/2016
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erectus123
erectus123
462 Followers

Note-All characters are mature adults who participate in consensual sex, there is no sexual violence and all scenes conform to Literotica guidelines.

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A Young Man's Sexual Odyssey - a 3 part series

Part One -The Faithless Fiance and The Spider Gals

Part Two -The VibratingTranny Hooker

Part Three -The Korean Love Fandangle

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Note - this is the second part of a three part story - you might read Part One first so you know what is going on, but in brief this is what happened; a newly graduated Petroleum Engineer discovers his Fiance blowing the family's Mexican gardener, in response, the young graduate heads to Las Vegas where three Spider Women dismantle his body and spirit.

Each part of the series deals with different aspects of sexuality so be prepared for diversity.

Thanks for checking out my stories, the sexual aspects are based on my true life experiences so you should feel the ring of truth. Best regards, Erectus 123

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Part Two- The Vibrating Tranny Hooker

I rested up the entire day at the Las Vegas Hotel. I used the pool and sauna and had a nice breakfast at the small downstairs Casino restaurant. Flapjacks and eggs, bacon and a slice of ham, then wandered around a bit, I was totally destroyed by the events of the previous night. As I was having trouble keeping my eyelids from closing, I went back up to my room, closed the drapes, turned on the TV's music channel and fell asleep early in the evening.

I was so worn out from the Spider girls that I awoke the next day way past noon. I felt hungry so I went down to the Casino and again got a nice breakfast even though it was past lunchtime, rye toast and two sunnyside eggs with sausage and a fruit cup on the side. With all the activity I wasn't worried about cholesterol. The casino wasn't crowded, it being a weekday, there were only a few players. The dealer was a Latina women, half naked in the revealing casino outfits yet wearing a striped red bow tie above her well exposed cleavage. I gambled for about forty minutes and soon I was down $150, which was my limit.

I was about to leave when my eyes focused on a young woman sitting two seats over in a tight fitting dress. She had been there a while but I was concentrating on my cards. She was a tall big breasted curly haired very attractive black girl. She seemed to be winning as much as I was losing. Since my chip stack was pretty much gone, I moved over two seats so I was next to her and started a conversation. She introduced herself as "Traycee" and she kept smiling at me with the most beautiful white teeth that were set off by her darker skin, and the tightness of her dress left little to imagine. She just kept playing as we talked. She seemed to have no trouble doing two things at once. She wore a sleeveless spaghetti strapped raspberry colored gown, probably one that our beloved late Prince would have approved. Her feet, well formed but large, were bare but enclosed in and what must have been six inch heels with multiple little straps. She wore a big blingy ring you could not miss with a large purple stone on her third finger that captured your eye as she waved her hand to punctate her conversation and shout directions to the dealer whom she must have assumed was deaf. Her curly hair was wildly cut and long enough to touch her bare shoulders. When ever she leaned forward to sneak a peek at her hole card, her two very full globular breasts rolled forward looking like two ripe honeydew melons waiting to be hand picked. As I looked at her I got a firm erection, I had thought my dick had died and gone to heaven, but it hadn't, my mojo was back!

I guess she could do three things at once as she must have noticed my excited state as she sort of pointed at my chubbed up cock with her pinkie finger and said,

"We better get that big boy to work."

She gathered up her chips, took off her high heels to better navigate out of the casino barefoot and took me by the hand. I suggested we head up to my room, as we approached the hall exit that led to the elevators, she pigeon holed me by my shirt collar grabbing it tightly with her long painted nails and whispered, you know I'm a tranny don't you?"

"Nope, that's news to me, but I'm game."

She kissed me hard on the lips and thrust her tongue in my mouth, she tasted like some tropical fruit. Then her voice dropped a full octave,

"We gonna have some fun!"

It turned out she was a tranny hooker taking a day off, a sort of bus man's or bus woman's holiday I think is the expression. She lived in Vegas and escorted to earn her living. We got up to my room, ordered some drinks from room service and spent the next few hours laughing and enjoying each other's company while the TV's porno movies played on.

She had a bunch of stories that kept me laughing. According to her, most of her clients we straight, not gay, and were more interested in being fucked than in fucking her. This certainly surprised me as she was a super fem as far as I was concerned and I was very much looking forward to fucking her.

She had a few joints in her tiny purse that we smoked together even though it was a non-smoking room. We laughed at everything. There was even a porno with a little person, with no disrespect, a female blond haired midget, who took on three big guys in every way sexually imaginable; we thought it was hysterical, then I realized what happened to me Saturday night wasn't so different. Once the weed buzz started to wear off I started to reach for her breasts and what she called her pussy. With her help I unzipped her tight dress and we lifted it off over her head. Then she denuded me as well. I couldn't take my eyes off of her or keep my hands from touching her.

She was quite novel, a fascination for me, my first transsexual. Her cock was flaccid but enormous, she took my hand and pressed my fingers against it, the flesh was refreshingly cool to the touch, but I wasn't into cocks or her well defined balls which hung softly behind her cock. Instead, I reached for her breasts, her most feminine asset, her tits were perfect in every way. They were firm and very large, she kept telling me to squeeze her tits harder. I did as she asked but became fearful if I continued squeezing they might explode. She paused me for a moment and asked me, "Have you ever gotten a New Orleans Fuck?"

"What's that?"

"Oh, I'll show you. Come closer, I want to suck your cock. I suppose it was at that moment that she'd surreptitiously mouthed a condom onto me."

She sucked my dick like a vacuum cleaner nozzle, I was afraid I'd blow my load at that point but she moved into an all fours position on the bed and motioned me towards her, guiding my erection, that she hand lubed, into her honey spot, that felt just like a cunt, but smoother. I thrust for a while,

"Fuck me harder" she said.

As I thrust harder and harder her ass took off, she vibrated her bottom like a washing machine that was totally out of balance dancing across the floor. Believe me, I've never been to New Orleans but that night I was transported. Of course I had no trouble fitting inside her warm ass, she was wide enough to take several cocks. But then she tightened her ass down and I felt as if she was squeezing me tight, milking me. She continued vibrating and I lost control after about ninety seconds and dumped my condomed load right inside her warmth. After the sex party of the previous day I wasn't surprised when I had concluded fucking her and she held up the condom saying,

"Hey big boy, how come so little cum."

"I'm sorry, I apologized, I've done a lot of fucking this week. My balls are running on empty."

After her delightful vibrating routine, she asked me quite delicately asked if she could fuck me,

"I really want to put my cock in your tight ass."

When I looked down, her cock was hanging there like a whole filet of beef, it was so large it scared me. She had no pubic hair so her cock looked like a naked cactus, a small tree trunk, a danger sign if I ever saw one. I guess the flirting and her hopeful promise of taking my cherry, as she called it, led to her increased arousal and excitement as was evidenced by the firming up feeling I was now getting as she pressed her huge meaty member against my thigh.

Getting fucked was something I was unprepared for, so I had no choice but to ask her to spare me her penetration. After my humiliation of the last few days I was not equipped to be skewered by her horse cock, through magnificent, it was more than I had the courage to confront. I promised on my next Vegas trip my "cherry" belonged to her.

Not too happy for the moment, she insisted I suck her cock. I was seated on the sofa chair and she walked up to me, put one knee on the side and stuffed her semi-hard cock into my mouth. But my mouth could hardly open wide enough, while her cock became firmly erect. She grabbed me by the back of the head and kept shoving her cock's head deeper into my mouth until my face began to turn blue, I just could not breathe, her cock was so large it cut off all breathing passages. I tried to suck air on the sides but it was hopeless. That moment, just before I thought I might pass out, the image of my ex-fiance Loren managing to mouth Juan's enormity flashed through my head and made me realize how unprepared I was for cock sucking. Maybe she could give some lessons, but that wasn't a rodeo I expected to compete in.

Thankfully she finally withdrew, pulled me over to the bed and graciously resigned herself to leaving my ass hole empty, after repeating her request several times. Nevertheless she rolled me over sideways as I tried to catch my breath and she placed her enormous cock between my legs, squirted some lube on me and started pumping, when I could feel her big balls slapping my ass and her big cock rasping my dick's underside I had my regrets about not being prepared for an anal onslaught, but my regrets were quickly inundated by a shower of hot semen she shot between my legs, drowning my cock and balls with a ropy thick cum shot. She held onto me tightly as if I was a lifesaver. Eventually she fell asleep and I pried myself loose and tiptoed to the bathroom to shower off her thick cum, not so easy to remove as it had begun to dry and was crusted all over my thighs, cock and balls-nature's glue! But I was glad she got some relief and if I'd have been suck-cessful at the attempted blowjob, she would have certainly drowned me with her cum.

She was obviously staying the night, and I really enjoyed her company. When she woke up I ordered two steaks, wine, fries and more from room service. We ate together, she loved to eat, she even finished my fries and drank what ever wine was left in the bottle. We watched two movies until our eyes closed on their own. She spent the night curled up against me like a big puppy dog and the humility I wore like a vest from the Spider party girls evaporated and I began to feel a manly confidence again. Any aversion I might have had to 3rd sex activities was gone and I was amazed that even with her enormous cock and balls she was more feminine than many woman I'd laid with in the past.

When I left early in the morning to catch my flight back to Dallas, she was twilight sleeping. She opened her eyes long enough to say,

"Goodbye, call me when you are in Vegas, I still want that cherry."

"You got it!"

Then she fell back asleep. I left $300 on the bed table and a thank you note. Although she hadn't asked for money I knew she was a working girl and didn't want to be a freeloader. Believe me, I have no doubts that black lives matter, but also black pussy and her cock that she referred to as "her clit", well, that matters too.

On the way out the door, I met the cleaning woman in the hall. I tipped her $25, asking her to clean up and spray the room down so I didn't get listed or billed for smoking up the place. She was a nice Mexican lady who said she'd take care of it all, once Traycee had woken up and vacated the room.

When I went down to the lobby I began to feel a little guilty. Traycee had given me such pleasure, but did I return the favor in kind? I thought not. I don't know if it was a feeling of remorse or my curiosity about the "cherry picking" she seemed so desirious of.

Making up my mind, I went into the hotel store and bought three plastic bottles of water. I took the elevator back up to the room. She was still sleeping but the money and note were no longer on the bed table. She opened her eyes as I closed the door.

"You wanted my cherry?"

"Oh yes, I do"

"Well I'm giving it to you. Just give me a little time to prepare myself."

I didn't intend to return to Texas the same man, something had to change to make this the turning point. The old life with Lauren was dead and this was how I was going to bury it-with Traycee's cock deep in my ass. No, I wasn't going gay, but I need an abutment and this was going to be it.

I used each of the water bottles as if they were enemas, gently pushing the sliding nipple cap into my ass and squeezing the plastic bottle until all the water was inside me. Then I expelled it into the toilet evacuating to the best of my ability. By the time I got through the last half bottle I was clean.

I showered off and toweled down and came back into the room. Traycee was up and alert. She'd pulled out a black plastic container of what she said was the best lube, a silicon based product that she guaranteed was the finest.

She instructed me to position myself with my ass at the end of the bed. Without telling me what she was doing, I felt her place my hands through loops and then she did the same with my feet. She tightened these restraints and secured them to the bed so I was spread eagled while still on my knees.

I was surprised, "Is this necessary? I can take it like a man."

"You think you can, but Baby this is your first time and believe me this is going to hurt going in, with luck you'll be smiling by the time I pull out, but I've got to keep you in one place. I can't fuck a moving target. Then she slipped a sleep mask over my eyes and I was alone in the darkness.

"What is this for?"

"So you can concentrate and never forget this sacred moment."

"Don't be scared, If the ropes are too tight I'm going to loosen them. Try to relax. It takes ten minutes or more for the sphincter to loosen up so just relax as I try to open you."

With that she started massaging my butt and then rubbing my ass and it felt very nice. Then little by little I could feel her inserting her finger into my ass hole.

"Oh baby you sure are tight."

I don't know how long she took but it was a while, little by little she got one then two and then three fingers into me when she got three fingers and her thumb she thought that was enough.

"Just take it easy with me," I begged, I knew I was totally in her control. "Please be gentle," I moaned, as if my life depended on it.

"Oh I will. Just relax baby, I've got you lubed real good. We gonna have some fun right now."

I could feel she had positioned herself behind me. She rubbed her big cock's head against my anus and she adjusted her trajectory carefully, she began to gently insert her dick. As she entered me I could feel a crushing pain that was illuminated by a blue white blinding light, more pain than I had ever anticipated. I cried out, and she put her arms around me as if to comfort me, or so I thought, but no, it was to leverage her piston into my deepest depths and with a flick of her hips, not at all gently, she jammed her horse cock right inside me, at least 4 or five inches and I screamed. But to no avail, once more she bucked into me and I lost my breath as she went balls deep of what must have been 12 inches of hard flesh, I must have passed out momentarily and when I came to I could feel her hot breath on my neck and her rapid breathing as she claimed dominion over me. She continued humping me, her big balls slapping my ass as she pounded and then woosh, as she moved in and out of me most of the pain was gone and a feeling of sexual stimulation came over me. My dick was erect and I could feel that cum was leaking out of it. She reached around as if she knew and grabbed my dick and jerked it rapidly and to my surprise I came. Then as if in harmony, I could feel her big cock contract as she let out a low bass cry and her cock started to spit out enough semen to fill my ass with hot cum. As she kept humping, my eyes filled with tears and I rocked forward in pleasure, pleased as she kept cumming and she fell over me so as not to lose her foothold on my soul, and in this manner she covered me as I finally collapsed under her onslaught, falling forward on my belly, still feeling her penis going through its final contractions.

It was at that moment that I heard a key in the lock and the Mexican lady opened the door, crying out,

"Oh Dio Mio!"

What a sight she must have seen, there I was, tied ass up, masked, on my knees, bleeding and leaking cum-oh my God I could never come back to this hotel. And Traycee, looking up, her huge cock wet with semen and lube responding to the maid as if what we were doing was perfectly normal,

"Not yet hon, we're not finished yet, Thank you. Muchas gracias,"

And then Traycee returned to her finishing act even before I heard the door slam and then the rapid pitter pat of running feet down the long hall.

Traycee kept ploughing me and I began to hope she would never stop, finally her massive cock finally began to soften. When she withdrew her horse cock from my battered rectum and untied me and took off the sleep mask that covered my eyes, I sensed from her facial expression she was not at ease. I looked down and saw that drops of red blood were dripping out of my ass turning my cock and balls red, puddling on the sheet.

"What's happened," I exclaimed.

"What happened? Baby what happened was I fucked you, your cherry is mine forever, I own you now."

"Will I be ok?"

"Sure, in a few days you will stop feeling as if my cock is still inside you, then you will heal up and in a week or ten days you'll be fine, ready to go again."

"But you didn't wear a condom?"

"Don't worry honey, if you don't got nothing I will be just fine."

"But..."

"Don't you worry, I was tested two days ago and I'm clean as a baby's butt."

"Thank God. Thank you Traycee, Thank you for taking care of me. I'm glad you got my cherry. But I don't think I will ever repeat this again. It was just too painful at the start."

"With time you may change your mind, as you practice taking it in the ass, it gets easier, it's no big deal to learn to fit my cock inside you and you will learn to like it better every time I fuck you. It's a sensation unlike any other, once you have experienced it you have to repeat the experience."

"I get that, when you were full inside me I never wanted you to leave. I'm sure whatever you say is correct, but I don't expect to return to this too soon."

"You treated me like a lady, and I appreciate that, but once you been fucked by Traycee you sure as hell are gonna be coming back for more."

I wasn't quite sure if that would be the case as I showered off, stuffed some wadded up toilet paper in my leaking ass to cover the bleeding, got dressed and kissed her goodbye and left the room. The Mexican lady was cleaning the room nearby so I tiptoed past hoping not to be seen.

"Goodbye Sir," she shouted after me, "Come back soon!"

Maybe my squeaking suitcase gave me away.

Then I caught a taxi parked outside the hotel.

"Take me to McCarran airport, please"

The cab was driven by a hung over Scotsman with a full ginger beard wearing a red plaid kilt. Las Vegas is a bit of a freak show. Seeing how I was duck walking, he added,

"It looks laddie, like you got ass fucked to beat the band, how many guys was it?"

erectus123
erectus123
462 Followers
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