My New Lifestyle Pt. 02

My New Lifestyle - Part 2

It's been a month since that amazing night I had with Shauna and her 19-year-old boyfriend, Andre. After that I had made a standing weekly appointment with Shauna and said I would gladly pay the extra to have Andre join us too. Luckily for me, he did join us the very next week and I spent a considerable sum on just one glorious hour with them both. Perhaps it was just the novelty of this newfound experience, or maybe I was testing my resolve to see if my previous week's arousal for that young black man and his impressive cock was simply a momentary infatuation or, in fact, something much deeper. Either way, most of my attention during that hour was spent on Andre.

Don't get me wrong, I wasn't turning away from my absolute passion for Shauna and her feminine body, with her nicely rounded tits and ass, or her shemale cock. Not at all! I gave her some close attention that night too, and she rewarded me as usual with a large helping of her delicious cum. It mingled well with the taste of the large helping of Andre's cum that he was kind enough to share with me. But I left that night hoping for yet another night with them both together. Over the following few nights, I even dreamed more than once of languishing my attention on Andre's big, black cock. I realized this was obviously no momentary infatuation.

I was disappointed at our next appointment with Shauna because Andre wasn't there. Shauna said not to worry, that he was briefly out of town, but she more than made up for his absence and I was quickly reminded of why Shauna was still the best She-cock I'd experienced yet.

On the very next appointment I was let down again and Shauna didn't elaborate on why Andre wasn't able to join us. She seemed secretive. I stopped asking because I sensed that she didn't want to talk about it. I think to make up for my disappointment she suggested a different two-on-one scenario by bringing in another T-girl performer, Cheryl. I agreed.

Cheryl was an excellent dancer with a fine body and firm breasts. I had seen her perform several times onstage. She was very good, and her cock was sizable enough, but she didn't come close to Shauna in her sensuality or sex appeal. Cheryl is white and it reinforced my suspicion that non-black shemales (or I guess I should say 'non-black cocks' really) just don't hold as much appeal for me. I left there that night thinking I might never be able to recreate those magical two nights with Shauna and Andre together, but I still held out some hope that next weekend would be better.

For some reason, that next week was tough for me and I kept daydreaming about my next visit to see Shauna and, hopefully, Andre. I couldn't wait for Saturday to roll around again. When it did finally arrive, I went downtown in high spirits, hopeful for a great night but also prepared to just have a good time with Shauna alone. I was resigning myself to believing that the short fling with Andre and his delicious black cock was just a fluke. I was mentally preparing myself for another disappointment.

The evening started even worse than I imagined because, firstly, I couldn't get my usual table near the front, so I watched from the side and farther back. I kept looking around for Shauna because she was usually around somewhere, and I thought maybe she had another customer in the back. I felt a little jealousy at that, but I knew I was being silly. I hoped she should soon be onstage and that would be my cue to get ready for our private party! My mouth watered at the thought.

An hour passed and still there was no Shauna in sight, so I flagged down my waitress to specifically ask about Shauna. She left to speak to the manager and when she came back, she was very apologetic. She told me that Shauna wasn't performing tonight, and then she handed me a note. I was crestfallen as I took the note. Unfolding it I read the following message:

Dear Tommy, I'm so sorry I won't be able to see you tonight, but I promise to make it up to you very, very soon. But don't be too upset because there's someone I want you to meet. Her name is Annie, and she'll be dancing onstage tonight. I've been working closely with her, and I think you'll love her. If you like what you see, you can reach out to her for some fun. I promise I won't be jealous, baby, cause I know I'm still the best you'll ever have!!! Love you! Shauna.

The waitress said, "I'm sorry Shauna won't be here tonight, sugar. Tell you what, the manager said to stick around and have a drink on the house. What'll you have?"

I figured why not; I'm not doing anything else tonight. So, I ordered a bourbon and watched the show. I was finishing my drink and thought about slipping away quietly when I heard the DJ announce the next performer, "Ladies and Gentlemen! The TG Club is proud to introduce a new performer to our stage. We're excited to present her to you, and we know she will excite you too! Please welcome to the stage, Little Miss Orphan Annie!" I perked up to see this new dancer. She must be the 'Annie' that Shauna was recommending to me. Perhaps tonight wouldn't be a total loss.

There was a bright flash of lights, and the music was cranked up a notch with a driving beat and onto the stage skipped a young black woman in a schoolgirl outfit. My interest immediately peeked to see she was black, and I was impressed by her brash entry and initial appearance.

Although, I must say that she didn't really look like any schoolgirl I saw when I was a teenager! Yeah, she had on the obligatory red plaid schoolgirl skirt, but it was short, short, short! It barely covered her ass. And at the front of her skirt, I could see even from my crappy seat location brief glimpses of her panties straining to hold back a sizable bulge. Those in the front row must have had quite a view up and under her skirt. From where I sat, she looked to be well endowed!

Those people also had a good view of the white fishnet stockings stretched tight across her long shapely legs and the five-inch shiny red high heels she wore. Although she certainly didn't need those shoes for the added height because I could see that she was probably over six feet tall even without the heels. She towered on that stage dwarfing any of the prior dancers.

She also had on a starched, pure white shirt, and it was tied up to reveal the brown skin of her midriff. The shirt was also unbuttoned at the top and open in the front enough to show off a bright aqua-colored bra underneath. The bra shone with flashes of sequins and that's when I noticed that the bra matched the glimpses of her panties that I could see beneath her skirt as she danced around the stage.

Another thing that stood out about Annie was her physique. She looked quite muscular, and her bare arms and midriff had muscles that were well defined. And then there was her hair! It was an unnatural color for a black girl, or any girl really. It was bleach blond, shiny and long and styled into two very long curly pigtails tied up with red ribbon bows. Her pigtails were whipping around and around as she twirled and moved. Although it was obviously a wig, it played well with the bold, campy schoolgirl outfit of a stripper, whether she be female or shemale.

What was odd about this visual snapshot for me was how much Little Miss Orphan Annie differed from every other performer I had ever seen at this club. Shauna is a good example. Shauna and the other performers are more obviously feminine and sultrier in their appearance. They all have good bodies to be sure, and some are very fit with hard flat abs and good definition, but they all are still very 'womanly' with nice round breasts and asses, despite the cocks between their legs.

But even that was another difference. The other girls don't emphasize their cocks immediately and usually even hide them away until their big reveal later in their stage act. In contrast, Annie was flaunting the bulge of her large cock from the very start as it strained at the lacy aqua-colored panties! Compared to the others Annie was all hard angles with more masculine features simply wrapped in feminine clothing and hair.

As I watched, Annie took off her shirt and I could see that her apparently large breasts were just a stiff padded bra. She was flat-chested, without cleavage and with no feminine breasts at all; just what appeared to me as well-defined pectoral muscles. And now that her shirt was gone, I could also see that the muscles on her shoulders and biceps were nicely sculpted.

Annie wasn't really a shemale or T-girl at all, but rather a transvestite or crossdresser in drag, although a very good one. I was a little confused to why Shauna was so insistent that I see Annie dance, although I will admit that Annie was an excellent performer onstage and carried off her brash outfit and character very well. She certainly exuded raw sexuality in her movements and appearance.

I'll even admit that Annie's performance was getting to me. The titillation of her revealing short skirt and the straining panties beneath, as well as her smooth dark skin shining with sweat as she exerted herself so enthusiastically on stage. The growth of the hard-on in my pants was a dead giveaway to the effect Annie was starting to have on me. Perhaps Shauna knows me better than I know myself!

For the first time I focused on Annie's face, which played along with the theme of her outfit with bold, brash make-up. Her lips were thick and full and painted ruby red. There was a heavy amount of rouge accentuating her already high, chiseled cheek bones. But most striking was the vivid light blue of her eye shadow and the heavy, dark eyeliner she used to make her eyes look enormous. From a distance it made her look quite attractive, in a burlesque way.

But there was something else there in her face. Something gnawing in my mind just below the surface. It wasn't until she looked up into the crowd, in my direction, possibly even looking right at me... I suddenly stood up and I felt sweat trickle down my forehead and into my eyes. I wiped it away and then took several steps forward, closer to the stage. Could it be? No!

I kept moving forward and walked right up to the stage like the guys wanting to give money to the dancer. I stared at Annie for 30 seconds while she danced further away down the stage, and then she turned toward me. I continued to stare as she strode closer and closer, suddenly looming above me. Her short skirt bounced upward and from this vantage I could see everything. I couldn't take my eyes off that big beautiful black cock bursting through those sparkling aqua-colored panties.

I kept gazing as she stood directly above me and spun for the audience. I noticed that one of her balls had slipped out from the leg opening of her panties and the tip of her long cock was just escaping above the waist band. That was it! That was the black cock that I had languished over! There was no doubt in my mind!

Just then Annie squatted down with her legs spread wide so that her cock was just below my eye level. I watched it come closer and then I had to tear my eyes away to look up into her face. I was right! Annie's full red lips parted into a big smile and her eyes twinkled. She looked stunning and my heart fluttered as I spoke just loud enough for her to hear over the music, "Hi Andre!"

She gave a sly smile and closed her eyes for just a moment and then opened them wide while replying, "My name is Annie, sugar!" She stood back up and gave another smile and a twirl to the audience and then she turned her back to me and in one swift motion she parted her legs and bent over from her hips until she was nearly doubled over! She was now looking back at me through her own legs with her hands on her ankles! I was impressed with her flexibility and so was the crowd.

The crowd roared as her pigtails flopped down onto the floor, but I was focused looking upward, right up her skirt at her tight ass, at that one black ball trying to escape, and to that large, heavy black cock stretching out those poor but valiant panties. I reached into my pocket and pulled out a $100 bill and looped it into the top of her stockings as I ran my other hand slowly up the back of her strong and quivering thigh muscle and toward her ass.

My own cock was straining now, but it jumped again when Annie's upside-down face parted those full red lips and asked, "Meet me in the back in fifteen minutes?" My throat was dry, so I could only manage a nod, looking like a fool. Just before standing up, she added, "For a thousand you can have me for an hour!"

Then she stood up and twirled back to face me and the audience and reaching up under her skirt she began to pull down on the front of her panties to unleash her cock, but then she stopped. The audience roared, so she did it again, and then stopped again as the audience cheered for her to let it out. I was still standing next to the stage, looking up at her just a couple of feet away with the roar of the crowd around me.

Suddenly Annie grabbed her panties with both hands and violently tore them off her body! Her big cock immediately sprung free and straight out, and the audience just went wild! She looked down at me and gave me a wink and then, looking out and smiling to the audience, she bent her legs and lowered herself slightly while reaching out to put a strong hand on top of my head.

Annie lowered herself until her cock was level with my face and then she mimicked to the audience as if she was pushing her cock into my mouth, mimicking the action by opening her red lips in a perfect "O". She then nodded to the audience and acted out her facial expressions to convey that I was giving her a good suck! I didn't know what to do, so I just stood there.

I'm private by nature and I almost wanted to run and hide from this scene, but I was also aroused and excited about discovering who Annie really is and what I was about to do with her in the back room. I wasn't really sucking her cock now; it was just part of her act. But it was exciting to have her pretend to fuck my mouth with her stiff black cock was just inches away from my face. I could have easily moved forward and really taken it into my mouth but that was against the club rules. I wasn't about to get banned from this place and ruin a good thing! So, I just stood still and played along.

After a few seconds of this she stopped and acted like she was extracting her long cock from my mouth with a flourish and then she quickly squatted down so we were once again face to face. Annie brought her face right up to mine. With a large hand she reached out and gently cradled my chin, bringing her lips almost to mine she said, "You're a good sport, Tommy! Thanks for playing along!" Then she pulled my face closer and pressed her lips into mine for a kiss, still playing to the audience, before she quickly stood up and danced away.

This time I didn't even hear the crowd until I turned around to see them cheering and whooping at what they thought Annie had done to me. I must have turned beet red from embarrassment and I quickly scurried back to my table, relieved to have some anonymity in the dark. By the time I sat down Annie was giving her final bows and then she skipped off the stage just like a schoolgirl.

My heart was racing, and it wasn't slowing because of the anxiety and anticipation of what was to come. I glanced at my watch and realized I now only had ten minutes until I had to go to the back room with Annie, so I quickly went toward the bathroom to straighten myself up. As I headed for the door an inebriated older male customer at a nearby table must have recognized me from what had just happened, and he started cheering me loudly.

He grabbed my arm and cried out so that everyone could hear, "Hey, you're the lucky bastard from up front, aren't you? Man, you're a lucky bastard! How did she taste, Fella? I'll bet she tasted good, didn't she? HAHAHAHA!"

I tried to pull myself away from him, but his grip was surprisingly strong, and he was in very high spirits. A woman sitting next to him looked annoyed at him, or at me, or maybe at everything. The guy kept yelling, "And did you see the size of her cock? Man, that thing is huge! My wife here told me she wants to suck a big black cock like that instead of my shriveled dick! But I showed her, boy, I told her that I'd rather suck that colored girl's big ol' dick myself than have to eat out her dried old pussy any day! HAHAHAHA! She didn't think that was so funny, did you honey? HAHAHAH!" He nudged his wife hard with his elbow and she gave another scowl as he said for anyone to hear, "Man, that was a big dick!"

I gave his wife a sympathetic look just as I managed to squirm away from his grasp and make a break for the restroom. I doubt it would have helped her mood, but I could have confirmed to the woman that Andre's (or I should say Annie's) big cock was a pleasure to suck and she should only be so lucky!

When I got to the bathroom, in the mirror I saw why I was so instantly recognizable; I had a bright red smear of lipstick across my mouth. Quite a few other guys were giving me looks as I cleaned myself up, either nodding their heads in admiration or shaking their heads in disapproval, I guess. I left the bathroom and headed for the backstage rooms. The bouncer guarding that entry must have been told about me because he directed to me the farthest room in back.

I only had to wait about five minutes when I heard the door open and in strutted Annie. Alone in this room and standing on the same level with her I saw just how tall she actually was in those heels. She stood a good eight inches over me, but her face was smiling and attractive as she looked down at me and quietly said hello.

I marveled again at how good her make-up and wardrobe were that they completely transformed the attractive young black male Andre, who is strong, lean, and handsome, into this electric feminine presence of the transvestite performer "Little Orphan Annie!" She was even speaking in a higher voice while in character as she thanked me again for being such a good sport and then with a twirl she said, "So, do you like what you see?"

She was currently wearing a long silky robe, but I could see through the gap that she had made a partial wardrobe change. She still had the same blonde wig, fishnet stockings and red high heels, but she had changed her clothing. I said, "You look fantastic, Annie! I was stunned to realize it was you. I can't wait to see more!" I suddenly remembered the money and I quickly dug out the $1,000 from my pocket and handed it over.

Anni smiled as she accepted the money and then she gently pushed me back to the sofa to sit and said, "Then let's get started baby! You just tell if you want something special from me. I'm here to show you a good time, Tommy!"

I gladly sat back to watch as Annie started to slowly dance and move for just me alone. Since she wasn't performing for a large crowd, her movements were more subtle, still sexy but more sensual than her stage dance. I only had to wait about thirty seconds before I saw what she was wearing under her robe as she discarded it and moved in to dance close in front of me. My mouth must have been hanging open because she gave a girlish giggle as she watched my reaction.

I was stunned at what I saw. Annie was wearing just a simple, sheer, and very bright pink babydoll negligee with pink fur trim around the base and matching pink panties! She had also added a white garter belt and straps to go with her white fishnet stockings. That was it, nothing else!

The negligee was so transparent that I could clearly see her dark, flat stomach and her ab muscles below. I could also see her natural flat chest and dark nipples. She was no longer wearing the padded bra to even pretend that she had breasts. I was actually glad about that.