My New Lifestyle Pt. 01

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Tom discovers his new passion for shemale cock and more!
10.6k words
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Part 1 of the 2 part series

Updated 06/10/2023
Created 09/05/2021
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My New Lifestyle - Part 1

Kneeling on the floor I gaze up at her smooth ebony skin across her taut stomach and upward to her perfect breasts with their dark nipples standing erect and firm. Peering between her breasts my eyes connect with hers as she smiles back at me. Her lips are full and thick and colored bright red, which sets off her glowing white teeth. Her long, dark curly hair frames her beautiful brown face as she speaks to me, still with that beguiling smile.

I couldn't really hear what she said due to the combination of the loud music coming from outside the dimly lit room we're in and the fact that my head is firmly held between her thighs with my face buried in her crotch. I can almost read her lips and I'm pretty sure she said, "Do I taste good to you tonight, sweetie?" I try to nod my head as I stare back at her with a hungry look in my eyes, trying to convey just how happy I am to be back once again between her legs and tasting the flavor of her brown skin.

This is the fifth time I have been here with Shauna, in this back room of the strip joint behind the stage, the room where performers take their special guests. You know, the ones that are willing to pay that little bit extra for some special treatment. Well, more than a little bit extra actually, but Shauna is definitely worth it! This would be obvious to anyone who witnessed this moment as she thrust and gyrated her hips into my face while my mouth hungrily worked to experience and taste every savory moment.

I looked up once again to those beautiful brown eyes as her long fingernails traced their way up the back of my neck and into my hair, causing a tingle to run up my spine and sending an electric shock through my penis as it strained within my pants. Her hands then gently but firmly grasped my head as she thrust her hips forward even harder, and I saw her lips move once again. I couldn't understand everything she said but watching her lips I had no doubt about the last four words she uttered before breaking back into that devilish smile, "SUCK...MY...BLACK...COCK!"

Oh, did I forget to mention that Shauna is a black transexual? Well, she is, and she is the most perfect t-girl that I have ever experienced. I don't want to make it sound like I'm an expert on shemales, not at all, but over the past six months they have become an obsession with me.

I should clarify, though. While T-girls in general fascinate me with their supple feminine shapes, rounded hips and breasts, and their smooth skin all contrasting with the jarring reality of a cock and balls dangling there between their legs. It is a confounding sight that, at first, I had difficulty in comprehending. Yet, it didn't take long for me to realize how intriguing and arousing they had become to me. But I have also learned what excites me most of all are black T-girls with their large black cocks and hairless balls! I don't know why they appeal to me so much more than white t-girls, but the sight of those perfect black she-cocks beckons to me, calling me to touch them, caress and stroke them, and of course to taste them.

My obsession started just six months ago when I was in Las Vegas on a business trip. I had gone out on the town with some coworkers and after quite a number of drinks and visiting a few of the strip clubs I was ready for more naked women and more booze. My coworkers, though, were partied out and ready for bed. It was 2:00 a.m. and I wanted more so I stumbled off on my own until I found another promising establishment with several gorgeous girls out front coaxing the people on the street to come in for the show.

Although I was pretty loaded, I do distinctly remember that I was struck at how these girls were noticeably taller and more full-figured than the girls from the other clubs, but they also exuded more raw sexuality as they preened and cooed over me on the sidewalk. I was quickly hooked and followed one of them inside where she led me to a front row seat. Her name was Candy and she even stayed with me at the table, teasing me, taunting me, complimenting my looks, and just generally buttering me up. After a few minutes she even climbed onto my lap just as the first performer came out on the stage. I remember that my dick felt like it was about to burst feeling Candy's tight ass rubbing against it.

I was in heaven, intoxicated and with an attractive girl on my lap fawning over me, when I noticed the sultry performer onstage. She was tall and black with long straight black hair. Her costume didn't cover much, but it didn't stick around for long anyway. Soon she was down to just her shiny gold G-string and high heels. Her tits weren't large, but they were perfectly round with large nipples. Her body was tight, and her legs were long and muscular. I had always found black women attractive, but not necessarily more or less so than any other race, but there was something about this black dancer that enthralled me.

Candy noticed how I was staring at the black girl on stage. She smiled and said, "Daphne's great, isn't she? She's so pretty and such a great dancer. She's been teaching me and hopefully I'll get to go on the main stage soon!" I just nodded and then Candy said, "Hey, Sweetie, do you want to meet Daphne? I can get you a private dance in the back room for only $200. I'd love to take you back there myself and give you a private show because you're so cute, but I'm on sidewalk duty tonight to bring in customers. You understand."

I nodded that I did understand, and Candy took that as a sign that I wanted the private dance with Daphne. Candy smiled at me and then made a quick signal to Daphne onstage to let her know that I wanted a private dance and then Candy took me by the hand toward the back room. I started to hesitate but then, in my drunken state, I decided "What the fuck! I'm here for some fun!" I followed Candy and we left the main room just as Daphne was starting to pull her G-string off. I only caught a glimpse of her tight ass before ducking through the doorway.

Candy led me to a private, dimly lit room with a red velvet sofa and a strong smell of perfume. She said, "Give me the $200 and wait here for Daphne. She'll come in as soon as she's done onstage." I took out the money and tentatively passed it over to Candy. She seemed to catch my reticence, so she assured me by saying, "Don't worry, honey. Candy will be right in." Then she leaned down and gave me a small kiss on the cheek and huskily whispered, "I promise you won't be disappointed!" As she whispered, she lightly glided her hand up my thigh and brushed over my penis and gave my erection a gentle squeeze. She then quietly squealed and said, "My oh my, you are certainly ready for her, aren't you? I wish I could stay and show you a good time too, but I have to go. Bye, bye Sweetie!"

As Candy twirled and left, I could hear the applause from the main room, and I tried to will myself to sober up enough to be ready for Daphne. It took a minute but soon Daphne entered the room and loomed over me. She was even more impressive standing over me and what little light there was reflected from her skin, shiny with sweat from her stage performance. She was as tall as me even without her heels, so with the five-inch heels she was wearing she towered above me, but her pretty face softened her intimidating size.

I stumbled to say something, but the only word I got out was "Money."

Daphne said, "No problem, honey. Candy gave me your $200. That will get you a five-minute private dance. Another five minutes is only $100 more, but you can decide that after the first five minutes, OK?" I nodded and Daphne smiled and started to dance for me.

Her body was perfect, and she slowly twirled and turned so that I could see it all, although she was now back in her full outfit from the stage. As she stripped again, but this time only for me, I admired her firm, muscular torso and legs. Her ass was tight and smooth. When she took off her top, she straddled my lap and shimmied her tits right in my face. I started to lean my head forward to give them a little kiss. Daphne quickly, but gently, pushed my head back and said, "Sorry, baby, but touching costs extra!"

She stood back up and began to slowly swing and gyrate her hips as she pulled down on the waistband of her G-string, but then she stopped and said, "Gee, I'm sorry Sweetie, but the 5 minutes is up. Do you want another 5 minutes? I promise you'll get to see everything I got!" I didn't even hesitate, and I fumbled for another $100 and handed it over. Daphne took the money and smiled and then resumed her position standing in front of me, swaying her hips and tantalizingly pulling down on her G-string.

She bent slowly over as she slid the panties over her ass and slid them down her legs and then gingerly stepped out of them before rising slowly back up. I scanned slowly down from her pretty face, over her round tits, across her strong abdomen and down her long legs. She had her legs pressed together as she ran her hands across her body and then downward, down toward her crotch. She shifted her stance slightly as she parted her legs a little and then gently reached between her thighs and pulled out a cock and balls!

I think my mouth was already open, but it must have opened even wider. I didn't move, but just stared forward in shock. I don't think Daphne even realized how surprised I was to see that she had a cock. I'm sure her regular customers aren't surprised by this. She continued to dance for me, sensually moving her body to the music playing in the other room and occasionally giving a short stroke or caress to her cock and balls to accentuate them for me.

Maybe it was my intoxication or maybe it was just the shock of the moment, but I didn't react the way I would have expected to react when the beautiful woman you are aroused to see dancing naked turns out to have a cock. And now that it was free and being occasionally stimulated by her hands, I could easily see that hers was much more impressive than my own. I absentmindedly reached down to feel my own penis and was both surprised and embarrassed to realize it was still very erect and it jumped at my touch.

Daphne noticed me touching myself and she smiled and said, "That's OK, baby! Get into the moment. Just don't take it out of your pants cause that's against the rules." Embarrassed, I quickly pulled my hand away from my penis just as Daphne stopped dancing and stood before me with her hands on her hips and her cock hanging down, partially erect and quite long. She was just a little breathless from the dancing and in her sexy low voice she said, "Time's up again, baby. I'm sorry. I can give you another five minutes for $100 if you want."

My mind was still trying to grasp the situation in front of me: a pretty black girl with an impressive cock standing naked in front of me and an erection in my pants as hard as a rock just screaming for some attention. Then Daphne stepped closer, and I saw her cock sway side to side before she leaned forward with her eyes looking directly into mine and in a soft voice said, "But for $200 you can touch me wherever you want! What do you say?" She winked at me and grinned the sexiest grin.

Looking back now I would have sworn the next words didn't come from my mouth, but I clearly heard my own voice say, "Yes, please!" I had no choice then but to hand over the $200 and then my heart began pounding so hard I could hear it in my ears. Daphne set the money to the side and started dancing for me again and it seemed as if she was actually dancing to the rhythm of my heartbeat! She moved closer to me so that I was near enough to touch her, and she slowly swayed and turned so I could see everything close-up. Her tits and ass were terrific, but my eyes always returned to her cock.

Two minutes had already gone by, and I hadn't touched her yet. She must have thought I was either nuts or drunk. She leaned down again and said, "Don't you want to feel my body, baby?" As she spoke, she ran her hand across the bulge in my pants and then added, "I think you do!" She then took my hands and gently guided them to her breasts, and I clumsily caressed and squeezed them. Shen then stood up and turned around and I ventured on my own to stroke her ass, which was firm and smooth.

Daphne turned back around so that her cock was now directly in front of my face and said, "Sweetie, you're almost out of time and I have to go back onstage soon. This is your last chance, baby!" Her pleading words echoed in my head and my fears almost won out when I had that same thought from earlier that night, "What the fuck! I'm here for some fun!"

I slowly reached out with both hands and gently grasped Daphne's cock. She gave me an obligatory moan as if I had given her great pleasure, but I knew that wasn't true. Instead, I was focused on three sensations that burst simultaneously into my mind: how large and heavy her cock felt in my hand even though it wasn't fully erect yet; how my own arousal level had just jumped up another notch; and the surprisingly strong urge I suddenly had to wrap my lips around the wide tip of her cock and suck on it!

My heart was racing but the moment was over. Daphne stepped back, pulling herself free from my grasp. She swept up the money and her clothes before turning back to me, leaning down and quickly saying, "I like you, honey! You should come back tomorrow night and I'll give you an even better dance." She surprised me with a quick kiss on my lips and then ran out the door with a parting, "See you tomorrow!"

I stumbled out into the night air and made my way back to the hotel. I don't even remember how I found my way back or how long it took. I vaguely remember a fitful night of sleep and then the ringing of my wake-up call for the next day of work meetings. When I ran into my coworkers that morning, they all commented on how awful I looked and they all guessed that I must have had a great night out, making up their own stories of my possible conquests. None of them guessed anywhere close to the truth and I just smiled weakly and agreed with their imagined tales.

When my coworkers suggested a repeat for that evening I begged off and told them I wasn't up for another night like that. I was being both honest and untruthful at the same time and I wasn't even sure which was which just yet. I knew I didn't want another night carousing the strip clubs with the guys, but I wasn't sure I should go back to the shemale strip club even though every time I thought about it, I could feel my excitement level rise. At first, I vowed to myself that I would never do that again, but I knew I was kidding myself. I wanted to go back, and as the day wore on, I realized I had to go back!

After my work meetings ended, I returned to my room and slept hard. I had to, but I set my alarm for 12:00 a.m. I quietly left the hotel and nearly ran into my drunken friends as they stumbled back from their second night out. Flagging down a cab I told the cabbie the name of the club. He gave me a disgusted look and shook his head but took me just the same. The girls were still outside coaxing customers, but I didn't see Candy amongst them. I entered and took a table off to the side and waited about an hour before Daphne finally appeared onstage.

My heart raced the moment I first saw her, and my penis immediately swelled. No matter what I told myself about these feelings, my body couldn't lie. I had to confront this! About halfway through her set, when she was down to just her G-string (a red one this time) Daphne noticed me in the crowd and smiled. My breath stopped for a moment as I nodded and gestured to the back, and I was so relieved when she nodded back indicating we could meet after her set. But this time I stayed to watch the entire performance. Who knows, if I had seen her in all her glory up there on-stage last night I probably wouldn't have gone to the back. Strange how thigs work out!

All my doubts from earlier in the day vanished as I watched her dance, and when she finally stripped off her G-string and I saw her perfect cock again as it moved and swayed as she preened around the stage, I was aching to do better than I had the night before. I even grew a little jealous as I watched other guys, and even a couple of women, put money in Daphne's garter belt, but I knew that I was just being silly. My heart raced even faster when I realized her act was ending and I almost fell over my table as I rushed toward the back room.

I had to wait outside the room this time for Daphne to let me in and soon she arrived, now dressed again but so damn sexy! She took me into the room, and I immediately pulled out a wad of cash; I don't even know how much was there, but it was much more than I had given her the night before. Daphne looked at the money and gave me a knowing smile and said, "Hold on, honey! Let's take this a step at a time. I'm not in a rush tonight because that was my last show. Now, why don't you tell me your name."

I paused, wondering if I should reveal my real name, but then I just blurted it out anyway, "Tom!"

Daphne giggled and said, "You're sweet, Tommy! Now just sit back and let's figure out what you really want." I sat back and took a big breath and tried to calm down. Daphne could see that I needed some guidance, so she said, "Since I like you so much, Tommy, I'm going to give you my special deal. Last night you gave me $500 for 15 minutes with just a few minutes of contact, do you remember?"

Boy did I remember! I nodded and she continued, "Tonight for that same $500 you can have me for a full half hour." My heart raced and my mouth went dry because I wanted to speak up and say that I wanted more than just watching her dance for a half hour. I started to speak, but then she said, "You can touch me too, Tommy, but only if you ask first and I give you permission. Agreed?"

I quickly nodded yes and thrust $500 towards her. She giggled again, took the money and then pushed me back on the velvet sofa and immediately began to dance for me. I watched her and tried to relax but kept hoping she would undress quickly. She did, but still slowly enough to drive me wild with anticipation. She knew what she was doing to me!

Before long she had exposed her round breasts and was down to just her G-string and her high heels. Daphne suddenly stepped forward and climbed onto my lap and straddled me so that her breasts were in my face. She giggled as she leaned in and brushed her tits back and forth across my face, tracing her nipples around my mouth. I started to open my lips to take one in, but Daphne pulled back and said, "You didn't get my permission yet, Tommy!'

I immediately blushed but saw that she was prompting me so I said, "May I lick your nipple, please?" She smiled and nodded and offered her left breast to me as I opened my lips and gently kissed and licked her nipple. Soon I was sucking on both her tits, and she even grabbed my hands and moved them to her ass, so I squeezed her ass as I sucked her tits. I was in heaven but still wanting more. After several minutes of this lap dance Daphne pushed herself off me and then looked down at my pants. She cooed at my noticeable bulge and said, "It looks like 'Little Tommy' wants to come out to play too! It's too bad we can't do that for him, but I can show you mine if you like! Are you ready for that, Tommy?"

I hungrily said yes and was then startled when Daphne with one quick motion stepped up onto the sofa in her high heels and straddled me again, but this time my face was staring straight at her crotch! She laughed again and said, "I'll bet you like this view, don't you?" I nodded again as I scanned up her body taking in the sights and smells of her skin so close to me.

Daphne said, "These new panties are so tight. I need your help, Tommy. Please take them off me, won't you? But do it slowly." It's good she added that last part because in my excitement I probably would have ripped her panties down so fast I would have knocked her off the sofa. I restrained myself and grasped the waistline with my fingertips and then pulled them down sloooowly; first one side, then the other, inching them down over her ass and down her thighs until she had to move her legs to pull them off completely.

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