Tiffany's Halloween Costume

Tiffany's Halloween Costume Conversion by Kandi

This story contains adult material. Please read no further if you are below the legal age. Please also contribute to Nifty to keep it free!

Here I was, down on my knees, sucking this John's cock for $80.00 while he was parked in the fancy hotel casino's parking garage on an upper level, my long blonde hair pulled to one side, so he could watch me suck his delicious cock, hoping that the little pillow I kept in my purse would keep my knees from rubbing on something sharp and laddering my back seamed stockings. They were the only pair I had for tonight, and felt that they really made me look sexy, even if the rest of my clothes were a bit slutty, but when you are a tranny whore, sometimes slutty is what brings in the bucks! My very short, black, pleated skirt was just past my bottom, so it still showed the garter straps by about an inch, the tall 5-inch pumps made my legs go on for days, the red top was fitted and unbuttoned just enough to show some cleavage of my large "DD" breasts, barely contained by the black lace bra. His cock was big for a white guy at about 7-inches and surprisingly tasted decent instead of the truckers, or gamblers who usually reeked from sitting in a chair all day! As much as I liked being fucked in my bussy, sucking a real man's cock just did it for me...something naughty about being trans and trapping them just turned me on like nothing else did these days. When he finally spurted into my mouth, I made sure to seal my lips about his cockhead so I could savor that muchly needed cream that seemed to rule my life now that I worked for Tyrone!

I guess I should tell you how I got this way. You see I was not always a trans call girl named Tiffany. I used to be a smallish sized guy named James, who stood around 5'6", weighed in at 130 lbs. had medium length dirty blonde hair, blue eyes, and just a smattering of freckles across my nose and cheeks, working as an Accounts Receivable guy in a fairly big company. I was dating a girl named Lisa, who was Milano, so was darkly complected, long curly hair, deep brown eyes, maybe 5'5" and about 125 with a body that was slender, but curved in all the right places who worked as an anesthesiologist at the hospital!

About a year ago this time, about the start of October, the Hospital that Lisa worked at, announced their annual company party for Halloween. They would do the normal "costume draw from a hat" because it always made for a fun challenge when someone got a gender specific costume draw that was not their standard gender, like two years ago, some guy got Zatanna ( the lady spellcaster from DC comics who dresses, well, somewhat risqué), but he did such a nice job of coming as 'a cross-dressed Zatanna', that he took the first place prize of 10 grand! However, as good as his was, the best was last year when some big-busted woman pulled Captain America, and she showed up as Captain Carter from the old Marvel "What If?" strips with a muscle shirt under the costume and a nice plastic shield that they repainted...She took first place unquestionably! These parties were always amazing, employees were always allowed to bring a 'plus one' if they were married, dating or living together like we were. These parties were replete with a ton of expensive, very good foods, an open bar, dancing, several contests that awarded expensive prizes and of course the top costume contest that offered up a $10,000 prize so that made the cosplayers very competitive. This year as the costume hat (that looked like a sorting hat from Harry Potter, except upside down) was passed about with the usual costumes of Scary Nightmare, Werewolf, Caveman and Rockstar already taken, Lisa finally drew her costume and immediately upon sharing got catcalls from all the nurses around as her card was simply labeled "Hooker"!

That night, once home, Lisa tells me of the costume and I at first laugh thinking I will see her dressed really slutty, so it will be fun watching her dodge the offers from everyone all night while I am thinking about setting up a rendezvous in the coat check to fuck her silly as I am already hard and dripping thinking about her being my slutty whore for the night and how I will get to fuck her in all the wild fantasies I have had since a teen! That is when she springs the idea on me of how we will mix this up with,

"James, honey, I think we should mix this up, you be the Hooker, I will be your Pimp and I bet if we do it right, we will win the prize! We can shave your body, dress you up sexy as I know you are already thinking about how I will look, so you can be the arm candy, while I dress over the top as the pimp! We take the 'couple prize' for sure. You know I will make it worth your while with anything kinky you want after, even anal! Maybe even spring for that big 55-inch Wall TV you want?"

"No way am I dressing up like a chick, let alone a whore...err hooker, and having everyone at the party make fun of me. I would never pass anyways so that idea is right out!" I put my foot down.

Lisa snuggled up to me, kissing me on the neck while stroking my penis, whispering seductively,

"But Pookie, you know I will be the one protecting you, fucking you in the coat room or bathroom like I KNOW you were just fantasizing about. You know I will make it worth your while, and I am sure you can look good enough that no-one will even know it is you, we can even give you a completely different name like Jenny, or Amber, or oh, how about Tiffany, that way I can eat you for breakfast?" she teased.

"You can't guarantee any of that and . . . Groan, that feels so good baby!" I said through clenched teeth as she unzipped my pants to pull out my now hard 5-inch penis!

Lisa dropped to her knees and started to suck on my penis. Her skills were amazing, bobbing up and down, licking, stroking, actioning my head with her tongue, playing with my balls, prolonging the inevitable. She would look up at me with my penis buried in her mouth, batting her eyes, smiling then slip off of it, and whisper,

"Pretty please baby, for me?"

I shook my head, gesturing for her to suck my penis once again, which she slowly began once again, bringing me to the edge and stopping several times until my balls were blue as a plum and I was begging her to finish me off!

"Dress as the hooker to my pimp, baby, and you can get your reward unless you want me to stop?" she wheedled.

"Not gonna dress as a girl, so fucking suck my dick!" I stated matter of factly.

Lisa just grinned up at me, my penis inches from her mouth, dripping saliva or precome from my dickhead to her lower lips, wiped it up with her fingers, slipping them sexily into her mouth, to suck the precome, saliva mix off them while watching me tremble in need. She started to stand, and I whined out,

"You would do anything, and I get the TV and NO-ONE would be able to know it was me? How can you guarantee that? Please let me come and I will do it!" I capitulated so easily I felt!

Lisa grinned, clapped her hands, dropped back onto her knees, stuffing my penis into her mouth once again, pumping my shaft until I released with a groan, grabbing her head to insure it was not another tease, as my orgasm lasted for 5 or 6 spurts which she greedily swallowed, licking my cock clean, standing up, kissing me and then saying,

"God, baby, you taste so good! When I finish the makeover, you will be a total babe, not the handsome hunk you are now! I love you and will get you the TV after the party! We will have to start your makeover about a week or two prior to the party which is the Saturday prior to Halloween so next week, we start your training to be my little bimbo hooker! This will be so exciting!"

Lisa rewarded me once again, later that night, in bed, by letting me do her anal which was not her favorite position, but one I really thought was super erotic!

That next night, Lisa is online ordering clothes, lingerie, heels, a wig, Nair, and jewelry for me, a crazy pimp outfit, a chest binder, hat and walking stick for her!

About a week later we start to get the packages in the mail. Lisa immediately pulls me into the bathroom to cover me in Nair from nose to toes (except a little landing strip over my junk) and then washes it all off after about 10 minutes. My skin is absolutely smooth, silky feeling, devoid of any hair and so different looking that I am amazed! She powders me after putting on some scented lotion, then comes the panties and I stop her, asking,

"Wait, the party is not for two weeks, why are we doing this now? What if someone sees me like this?"

"Silly goose. You must practice dressing, walking, make-up, mannerisms, your voice, and how to flirt as a girl so you can pull this off. We will dress you each night and practice so you can be convincing the night of the party!" she responded.

"OK. I get I might need practice, but doesn't that mean you do too? I mean you need to learn to walk, be aware of your swinging dick, talk deeper and all that too, right?" I asked timidly.

"You're right, so after we work on you, we can work on me! Then we can interact as our characters together after I get changed! Thats's a great idea honey!"

So I put on the purple satin and black lace backed thong panties, learning how to tape and tuck, then came the big breasted breastplate in "DD" cups, which when finally on, made me shudder in how much I now looked like a woman! Flat in the front of the panty, big hooters bouncing in the air and only the 'masculine' face gave it away. Next was struggling with the matching black and purple bra, which I finally fastened in front and rotated, slipped my arms through the strap, then hefted the 'girls' better into the cups. I marveled for about 2 minutes on how real they looked, bouncing when I moved, then came the black lace under bust corset with garters that Lisa used to reduce my waist to about 22 inches. Then Lisa slipped the corset straps under the panties and at my questioning look said,

"So you can pee later silly, without taking off the garter." Her grin implied other things as well.

Next came the black, back seamed, reinforced heel, stockings with lace tops that I attached to the garters. The feel of the taut strap against my front and around the curve of my bottom, had my penis twitching, so that I got a little flushed and Lisa noted it with a grin and said,

"Yep, I know just how you feel honey. Dressing sexy is quite the thrill and I knew you would like it!"

Like it, I felt so damn sexy and was only partially dressed. I couldn't imagine how erotic it would be when fully dressed! Next came a short, fitted, black leather, micro-miniskirt that barely covered my ass, which Lisa left unzipped until she slipped a dark shiny, purple, sleeveless, blouse on that buttoned up backwards with the buttons on the wrong side...which she then left unbuttoned to expose a ton of my now heaving cleavage! Lisa then gave me some inch long square tipped press on nails, a 18 - 20 inch long blonde wig, a black choker with an amethyst stone pendant, some black 5-inch Dor-Say heels with the sexist little ankle straps, then sat me down and said she was going to teach me how to do make-up!

Lisa started by plucking my eyebrows to get a thinner more femininely androgenous look, then putting on a light foundation, blending, some light pinkish blush, then did my eyes with extra-long eyeliner wings, dark purple and smokey eyeshadow, dark burgundy lipstick, then tons of mascara so my lashes just popped! Looking in the mirror, I could not see any trace of the old James! I knew I was a slim and not very muscular guy from all those years jogging, but never in all my wanderings did I ever think I would make a pretty girl! I was actually kind of hot I thought, and then thought 'if I saw me in a club, I would be hitting on me!' Then came the walking, sitting, talking, and mannerisms, and I immediately changed that thought into 'If I saw me, I would wonder what the hell was wrong with that chick!?' It was two hours of walking from one side of the room, smoothing my short assed skirt under me as I sat in a chair, learning to keep my legs closed, asking for a glass of wine in as feminine a voice as I could, then standing, walking with one foot crossed over the other in short little mincing steps to the other side of the room, perching on a bar stool, asking for a drink, winking at Lisa, playing with my hair or biting a lower lip till she was satisfied that I looked almost normal. Then it was an hour of make-up and by then I was exhausted, and we still did not get to her costume!

The next day, we ate a quick dinner after work, then redid the whole process, me dressing, doing my make-up and then finally changing Lisa into her pimp costume. When it came time to stuff her shorts, I held up a pair of my tubed, athletic socks and she just grinned, shook her head no, then revealed a double ended dildoe that inserted into her, leaving about an 8-inch, realistic cock exposed! Shaking my head, I just helped her stuff it into her tightie whities. She moaned a little as I helped her adjust it in the underwear, as it rubbed against her clitoris, then again when she had the tight slacks on that showcased her 'bulge'. Wrapping her chest, putting on the button shirt with plenty of fake bling 'necklaces', the hat and jacket, Lisa was truly able to look like a pimp, straight away. We had her practice her voice, which she deepened easily. I had to admit that Lisa was able to transform much easier than I had, as my practice began anew. It was not easy being a woman I finally admitted at the end of the night. Things got a little weird when she gave me a nighty to wear to bed saying I needed to keep thinking like a woman while she kept thinking like a man so kept the dildoe on. Needless to say, waking up in the morning being spooned by her and having that phallus rubbing between my cheeks was a bit exciting and disconcerting all at the same time!

We spent the next two weeks 'practice dressing' each night until the Friday before the party, when Lisa brought out a simple little red cocktail dress, a set of black pantyhose, a black panty and bra set, the wig, jewelry, etc and told me to get dressed as we had a dinner date! I panicked about going out like that in public, but she said not to worry as it would be less stressful than the first time being at the party. She wore a simple little halter dress, heels and left her hair down with big earrings and drove us to a little Italian place where we had salad, light pasta, a couple glasses of wine and were flirted with by both the waiter, the busboy and actually got checked out by several guys, and after settling down, I became comfortable as a woman out in public so that by the end of the night, Lisa said,

"See honey, I told you, you make a cute girl and the fact that guys are hitting on you is proof! Now should we head home so I can reward you for being such a cute, sexy thing tonight?"

"Mmm, yes please! I am so horny for you after waiting these two weeks, I almost can't wait!"

The drive home had us caressing each other's leg, but Lisa never touched my crotch, while I had been fingering hers almost from the get-go. Once home, I started to strip, but Lisa stopped me to keep me dressed enfemme as she wanted to see what it was like with a woman. She knelt before me, undid my panties, untaped my tucked penis, before taking me into her mouth. As I mentioned, Lisa is an amazingly gifted cocksucker, so I was shooting my load in moments. She stood, licked her lips, kissed me and pushed me down whispering 'my turn' so I dropped her thong, that was almost translucent with her juices, and dove into her gloriously wet snatch, bringing her to a quick orgasm as well. We retired to bed with both of us in little babydoll nighties, falling asleep quickly after once again making slow love to each other.

The next morning when we awoke, I could feel her spooning me, cupping one of my huge breasts, while she snored softly onto the back of my neck. I felt my crotch twitch, pushed my bottom against her as she sometimes did to me when we were reversed and felt her respond by pressing more firmly against me. When I felt her kissing the back of my neck, I knew she was awake so spun about to start kissing her back, playing with her breasts under her little nightgown, and grinned as she moaned, then she did the same to me! It was so sexy and erotic, that I started to fondle her more, kissing her neck, biting it, caressing her body, kissing my way down to her sex until I was between her legs, lapping away, tonguing her quivering clitoris. I could hear her moaning about being such a sexy bitch, that she loved my tongue on her, when I thrust a finger inside her, using my long nail to lightly tickle her inner clitoris, she arched her back, moaned, grasped the back of my head, groaning out 'right there baby, yeah just like ...that...oh yeah...coming girlfriend!' and with that she shuddered, bucked, and arched her back squirting her orgasm across my face! I kept at it until she slowed down then she arched her back again, crying out that she was coming again, and once again, squirted her come on my face before coming down and pushing my face away from her now oversensitive clit.

When she threw me onto my back and started sucking, I expected the usual BJ, but when she stuffed a finger inside me, I moaned in sudden excitement. Her finger played with my prostrate, while her hand cupped my balls. Her mouth was balls deep on my shaft when I followed her lead, cried out, arching my back and shooting deeply into her mouth. Lisa licked me clean until I also pushed her off my now overly sensitive cock. Looking up at me with a smile, she just winked languidly before saying,

"I always wanted to be blown by a girl and that was fabulous baby! You are just so sexy as a girl; we may need to keep you this way!"

We started coffee and breakfast still in our nighties, teasing and kissing on each other, it was so romantic it made my heart flutter in happiness! Then it was off to the bathroom, where we once again redid the Nair on my whole body to insure, I was silky smooth all over. Then it was putting on a pair of Lisa's panties in white, with a matching white t-shirt bra, some super tight jeans, a white button shirt with a lace, camisole undershirt to help 'hide' the bra, light day make-up, the wig, some simple open toed, flat sandals, then filled up a medium sized purse with my ID, keys, a tampon, rubber, some basic make-up and we were off to the salon for makeovers!

Once there, they sat us next to each other to start the pedicures then had another lady come forward to do our nails. Lisa asked that her acrylics, be removed and then just polished after being made neat, while my press-on nails were removed and replaced with inch long acrylics that were painted in a light purple, pearlescent polish and lacquer that was also later used on my toenails. Once the mani-pedi was complete, they moved us to the hairdresser section and worked on shortening Lisa's hair and lengthening mine with extensions! I never felt so pampered at a barber! This was an exquisitely romantic experience and now it made sense to me on why women made such a big deal of it! Bonus was that we came out of the shop looking fabulous! We window shopped at the mall for a short time after that and I really started to notice guys checking us out, or what I thought was guys checking Lisa out, until she snickered and made me realize that one guy almost walked into a kiosk checking me out! We ate a small lunch at the mall food court so I could get a little more used to the longer nails and eating around these huge melons attached to my chest, since they would be there till late at night, so Lisa felt I needed to get used to them for longer than a couple hours!

Once back home, we started on getting me ready since it would take at least and hour for us to get into costume and the hotel where the party was being held was also about an hour away. This meant once again, slipping on the black and purple panties, bra, corset, tape tucking my penis, slipping on the back seamed stockings, doing my make up really big and heavy so it looked exaggerated like so many prostitutes did, then adding the little leather miniskirt, and purple satin top, and all the jewelry and such she had gotten...I looked damn sexy and really did not think anyone would recognize Tiffany as being James unless they got under my skirt! The ONLY person I expected to do that was now dressing in tightie-whities, black dress socks, that polyester light blue suit, slicking down her hair, binding her chest and not to forget, that double headed dildoe which made me question why she felt she needed that, but she just smiled when asked! She made a slight, androgenous looking man, but she looked like a guy none the less, and I obviously looked like I was a prostitute! Lisa looked at me and complimented me with,

"Tiffany, honey, on this Halloween party night, you make a beautiful woman and my little slut hooker in that purple satin top, black leather miniskirt, and matching black and purple lingerie. With those tall heels and blonde extensions, the makeover at the salon this morning, no-one will recognizable you as a man! We will win for sure! Let's get going so we can make an entrance...I'll drive since I am the man tonight!"

Lisa opens the door for me, and I sit down ass first in the seat, smoothing my very short skirt under me as I had been taught, then slip my legs into the car while looking up at my pimp with a smile, before giving a quick 'up-skirt' to tease. We were about 15 minutes from home when Lisa's cell starts ringing. When she picks it up, all I can hear is her side of the call.

"This is Lisa...No, I have tonight off as scheduled...what happened to Johnny?.... OK, but can't Jamie take it as she is the back up?...But...damn it, we are headed to the party...OK, let me get him home and be there in 30-40...Dude! I can't just leave him...emergency? Who...Oh, OK. Let me check...Honey?"

"I get it, some emergency at the hospital and only you can fix it, just leave me at the upcoming bus stop and I can catch a taxi or bus home. It's cool baby, work needs you and I can cope!" I replied in the hope that she would really understand and maybe just take me home, as dressed like I was, I was suddenly nervous!

Lisa dropped me two blocks later at a bus stop with $20 bucks cash to insure I could take the bus or have cash for a taxi or UBER.

Pulling my phone out of my bag, I looked up taxi services, then made a call to get one to pick me up and bring me home.

While I waited for the cab, I paced back and forth, impatiently waiting, worried about how I might look when several cars passed by, honking or I would see guys waving at me, thinking I was some tramp, party girl, I am sure. I felt crazy to admit that I kind of enjoyed the attention even if they thought I was some whore for their amusement. About 15 minutes later the taxi driver showed up, spun his window down, checked me up and down and introduced himself as 'Rodrigo'. As I climbed into the back of the cab, I saw the driver eyeing my legs as my skirt lifted. He couldn't keep his eyes off of me. Truth be told, I was dressed provocatively, so should have expected this from guys, especially after what had been happening while I waited. The driver just kept looking back in the mirror at me, like he was `crushing' on me. He was staring -- he didn't even try to pretend he wasn't looking. I reached down to pull my skirt back down in a vain attempt to cover my garters. It had hiked way up when I bent over to get into the car -- way past the tops of my stockings. This made me happy that he thought I was attractive for some reason that left me a little bewildered. He started talking small talk after I gave him my address,

"What was I doing dressed so hot? What was a very pretty girl like me doing out all alone? Why was I out without a guy. Was I headed to some party and that was the address I gave him? Where was I from? Was I a student at the local college? Could we get together, did I date black men? Etc.?"

I turned on the overhead dome light in the back of the cab and went to my purse and retrieved my compact and lip stick. I knew I didn't really need a touch up, but I thought I would give him a show. I grabbed my makeup mirror, pretending that I didn't notice him staring at me. I then popped open the compact and examined my lips. I pretended to have some trouble steadying my hand to apply my lip stick, so I slid my knee up so my skirt hiked up again exposing my lace top stockings. He was getting quite the show now. I could see him craning his neck to see in the rear-view mirror. As seductively as I could manage, I applied the color to my lips -- pursing my lips, rubbing my lips together, etc. His mind wasn't on his driving now. I noticed he had some trouble staying in the lane of the road more than once.

With that I slid back into the back seat, shut off the light and straightened my skirt. I felt so powerful right then and there. I am not sure why, but I also was very aroused too, so decided to have some fun with him too. Slipping my finger between my lips, I sucked on it pensively, then let it slip out so that just a nail was 'hanging' on my lower lip like I was deep in thought for about 20 seconds, then dropped it back to my lap. I was enjoying things very much now...I could tell he really wanted to fuck me and I was loving the feminine power of it, wondering why I was enjoying this newfound power so immensely. I turned, slid back into the seat, then I looked straight at him in the mirror and said,

"Did you enjoy the show?"

He looked at me and sheepishly replied,

"Yes, very much."

"See anything you like???"

He just smiled and blushed like he had been caught in the act, which he had been. Rodrigo tried to get a phone number and asked if I would like to go out sometime. I just grinned at him and let him know I was already seeing someone. Was that him calling me a cock-tease under his breathe? The taxi meter seemed to go up much quicker than I remembered from my last taxi ride. By the time we were close to my and Lisa's apartment, the meter already read $30 and I only had about $34 after realizing that I had only had $14 before Lisa gave me the $20 earlier!

I rifled through my bag, panicking just a little, to see if I had more, it was full of all of the things that I had put in it for tonight's party -- make-up, condoms, tampons, keys, ID, etc...Nothing else of use like spare lost cash though. Now the meter was up to, $34 dollars already. That was all I had. I figured 'Okay, I could give him some money that I had at home'. A little while later, he finally got me home -- we were at $35 now. I went in and ripped the place apart -- nothing. I could have sworn I had some cash floating around. I always threw whatever I had in my pockets in a tray on my dresser. I searched frantically in the house. Nothing, no cash anywhere!

I had nothing ready and kind of panicked even more until I decided to just deal with it as best I could.

I walked back to the curb where the taxi sat waiting. I noticed my car in the driveway. I went to the car and looked everywhere -- nothing. Now the meter was reading $39. I explained to the driver and asked if I could give him a check. He pointed to a sign that read `NO CHECKS, NO ...' He paused for a moment and said,

"Perhaps you could pay me some other way. What else do you do other than a show?" and smirked at me.

I wanted so badly to get inside the house, get out of this costume and go to bed. At this point, I thought, what is it gonna take, a blow job? I was strangely excited about it and deciding that blowing him dressed as I was, a hooker no less, was a decision that came very easy somehow. I didn't hesitate or think twice about it, and I told him,

"Let me in and maybe something will cum up."

He opened the front door for me eagerly and I climbed into the front seat. He immediately unzipped his pants. I reached across and massaged his already growing member through his shorts. He started groping my breasts and tried to kiss me. Later I would recall thinking to myself that it was strange, I really didn't want to kiss him, but I didn't think anything about blowing him and swallowing his cum. He pushed my head down in his lap, his hands were everywhere. He went from my breasts to my waist, to my ass, to my legs - he started to reach up the inside of my thighs and I pushed his hands away, then he opened his pants and I saw that big black cock, I couldn't believe it. He was huge, way bigger than me, like he was a porn star with a cock that big! It looked to be about nine inches long and almost as thick as a beer bottle. I remember thinking to myself, I CAN'T DO THAT! WILL IT BE GAY? Initially, I just had trouble getting it in my mouth. I just sucked the head. He started pushing and I did manage to get it about halfway down as the shaft got slicker from my spittle. He held my head and moved me to his needs fucking my mouth slowly, then faster all the time getting deeper. I was making a sound like some porn star with all the slurping and sucking noises. Then he started to blow, and blow did he ever. I had the head of his dick in my mouth when I felt the shaft jerk and spasm as he started to cum. With one jet, he filled my mouth! My mouth didn't accommodate all his first jet, as I felt some go shooting past my lips. I needed to swallow harder. I reacted as quickly as I could, but it wasn't fast enough. I felt it splash inside my mouth with such force as it hit the back of my throat! More leaked free past my lips. I kept bobbing and swallowing. Again! And again! He came with a lot of cum very quickly and I couldn't keep it all in. Then he just buried his cock down my throat. I could feel his jets of cum hitting the back of my throat. I almost gagged but relaxed my throat and just tried to swallow. As I swallowed, I realized I was using my throat muscles to stroke his cock! I suddenly felt that I was becoming an accomplished little blow job artist, almost as skilled as Lisa with only my first ever blowjob. I looked up to see him looking down at me and felt as though he was feeding me his cum. He pulled out as I caught my breath. Then he started to subside, so I dutifully sucked him dry and polished him clean.

"Damn girl, you got some skills and a girl like you should maybe not be working the streets in this neighborhood as I think it is owned by some big-time pimp, so you be careful now you hear, and your meter is considered paid in full!"

As I walked back up to the house, I realized that I was putting extra swish in my steps in hopes that he was checking me out...then wondered why I was doing that as I got to the door and looked to see if he had been watching my ass. He WAS! He was also on the phone, I assumed getting his next fare, when he waved goodbye with a smile and drove off, lighting up his 'available' sign.

Once inside, I realized how excited I was, my penis...and now I would never call it a cock as I was only about half as big as Rodrigo had been...was hard and my panties were full of wetness! SHIT! I had CUM from blowing that guy and my penis was still hard thinking about my first ever blowjob! I strutted, yes strutted across the room to the couch and dropped my panties below my penis to scoop up some of the mess to help clean up, then looked at it, puddling in my hand, slimy feeling, smelling of sex, and slowly brought it to my lips to lap it off my fingers! What was I doing, why is it tasting so good, Is there something wrong with me? My penis twitched in need, and I used my other hand to start to stroke myself slowly while licking the cum off of my hand, then scooping up more from between my wide-spread legs. I felt so naughty and slutty...and even sexy for some reason! All I could think about was how Rodrigo's cock had tasted. His big black cock! I could see it in my mind's eye as I bobbed up and down on it, his cock twitching in my hands and mouth, his cum spewing into my throat...and as I thought about that, I tensed, let out a long drawn out cry that was almost a groan of passion and came hard with ropes of cum spraying up before landing on my hands and thankfully not on my outfit as I knew I would have a very hard time explaining that one! Then I once again did the unthinkable and lifted my hand to my mouth to devour my own jism! Wanking myself slowly and gently to release every drop, before licking it off my fingers, as I relaxed and slipped my penis back down to somewhat tuck it.

Just in time, I thought, as there was a knock at the door! There was no time to change, or hide, as the lights were on and it might be Lisa returning home for something, so I just went to the door and opened it. Infront of me, was a tall black man, well-muscled, dressed in a nice suit. He eyed me up and down with a grin of appreciation before saying,

"Hi. I am Tyrone and was on my way to a party when my car broke down. Can I use your phone please to call a wrecker?"

"Sure, I guess it can't hurt, my cell is right there by the couch, help yourself!"

Thanks. You're very attractive, dressed up for something nice I see? I hope I am not keeping you from something?" he asked.

"Naw, it's all good, and thanks by the way. My other half got called into the hospital on our way to a party, so I just got home and was about to go change, when you knocked."

He picked up my phone, dialed a number and said,

"Yeah, hi! I need the crew...Over at...umm what's the address here please" he asked towards me.

Once I gave it, the one-sided conversation restarted.

"OK...an hour? Alright, I'll be waiting." Then he hung up and turned to me as he handed me my phone.

"My names Tyrone and I am a 'commodities broker' here in town, you must be?" he asked.

"Oh. My name is...Tiffany. You must have an exciting job. One that pays well based on the car and your clothes look expensive, so what does it entail?" I asked to be polite.

"Well, I create 'commodities' for other businesses, clients, travelers or casinos so they can reward or service their customers. Think of it as setting up marketing with a 'sexy sells' mindset. I bet a good-looking girl like you would enjoy the work. Lots of opportunity in marketing. What do you do now?"

"Oh, I am just an accountant, and have no mind for marketing, but it sounds fascinating." I responded.

He was looking at me with an appraising eye that made me a bit uncomfortable, but also gave me a little flutter that he thought I was attractive, and it had me once again thinking about Rodrigo the taxi driver. I must have stared at his crotch a bit to long to see if he was hung like the taxi driver, or that myth about black men, when I heard him say,

"Baby, a pretty girl like you, if you want it, you just have to ask!"

Looking back up at his face, I stuttered something about not being like that, that I was just thinking, thinking I best have him wait in his car, when he stepped close, grabbed both my arms, got really close to me, his face inches from mine, sniffed before saying,

"Girl, I can smell the cock on your breathe and Rodrigo is one of my eyes, so I know what kind of girl you are. Sluts pandering their pussy in my town, either get beat for being bad, join my stable, or get iced, so what's it gonna be babe!?"

"What do you mean...I am not that kind of girl, I am not even a girl, let me go you ass or I am calling the cops!"

He shook me, then dropped my one arm and slapped me, hard, right across the face! I was seeing stars. What is it about a guy who thinks slapping a girl is the right way to calm them down, and why does it have to be right on the upper cheek, so it seems to radiate across the whole face like that!?

"OK, OK. I will do whatever you want, just don't hurt me! I don't have any money, but you can take the stereo system!" I wailed.

"Oh, you got something I want baby, you just may need to become part of my stable then! White girl as fine as you able to suck cock like Rodrigo says, you may be a high-ticket item I am guessing! Now get on your knees and show Daddy Tyrone what you gave to my boy Rodrigo! and no teeth or I will just cut your throat bitch!"

Dropping to my knees, I gently pulled down his shorts, exposing his now fully erect cock. I began to kiss and lick the side of his shaft. I took it into my mouth and ever so slowly and gently started to suck it. I felt it respond to the touch of my mouth. I removed it and slowly stroked his cock up and down with my hand, pushing my spit down the length, as I looked up at him with a lusty look saying,

"Mmmm. Even better than Rodrigo." knowing suddenly that my life depended on his ego being stroked as much as his cock! His cock was even bigger that Rodrigos! It must have been 11-12 inches in length and even a little fatter around than Rodrigos!

With that I took the head of his dick into my mouth gently sucking and working it with my tongue, looking up at him the entire time. I worked it deeper and deeper into my mouth, groaned a muffled,

"Mmmmm"

I twisted and rotated my head as I licked and sucked the head. Then I slowly bobbed up and down, first sliding my tongue down this side, then next on the other, slow then fast and back to slow again. I paused when I finally was able and deep throat him and started to do that same swallowing technique I had learned on Rodrigo, I held it there as long as I could then popped off to catch my breath while still slowly wanking him or playing with his heavy black balls, then slowly pulled back sucking gently. I stopped with the head again in my mouth, licking the underside of his frenum, and worked it as he moaned,

"Oh my. Yeah. That real good baby."

I removed him from my mouth, looking up at him as I lick the underside of the head.

"Oh, yes. I can't believe how good your cock tastes!" I said as I stroked him and took him back into my mouth.

I worked him deep throating, bobbing, stroking, slurping, working the head like a tootsie pop -- all the tools I had practiced earlier. When I sensed he was ready to blow. I pulled back, my mouth open, tongue just tickling the head, while my hands gently massaged his sac. I was teasing him, wanting it to last!? I went back to work after a minute of teasing. It took a long time until he erupted. My mouth was sore, I could tell my lips were puffy from his pelvis pounding against them. All night long I had dreamed of cocks exploding in my mouth like I was some porn star cocksucker. I knew I was dressed as a girl, but did it make me gay since I was honestly enjoying this? Dressed as a high-cost hooker, I reasoned I was a girl, so this was not gay, it was normal! That was what I was justifying in my head when he erupted. I expected a lot of cum, but he just kept cumming and cumming. I pulled away with my mouth open like a greedy baby bird, his cock inches from my open mouth, extended tongue as he spurted across my face and into my mouth. He kept coming in what felt like forever, and I am sure that it wasn't, but it seemed like it must have been thirty or so blasts before he stopped. My, did he unload a lot of cum! It tasted different from Rodrigo...it went down smoother, almost sweeter, I guess. I WAS enjoying it! I had come just as he had! No, that can't be. Just get that thought out of your head I told myself. I just kept sucking him until he was drained and cleaned before he forced me off him, still hard. He could see the little bulge in my skirt I am sure as he looked at me, then grinned before saying,

"Shit you are a hell of a cocksucker, now get over here and spread those long sexy legs, facing the wall sissy, as Daddy Tyrone is gonna bang that sweet ass of yours marking you as all mine!"

"Oh, god no, not in my ass, it will never fit, it's huge!" I begged.

"It's gonna fit sissy, and I think you gonna like it and beg for more!"

I could feel the hardness of his cock pressing relentlessly against my rosebud through my panties as I moaned suddenly in lust for him to fuck me! He spreads my legs, pushing aside my panties and rubs his large cockhead around in my spunk and then pushes it into my ass pussy as I moan, as he slowly pushes his big black cock in, slowly filling me as my hands splayed out onto the wall so I could press back in support against the invasion of my nether region.

"Look how big it is and Oh My God it's too big, I don't know if I can take it, Ohhh.....God....Ummmm, I love it! Fuck me with that big black cock of yours and make me your little sissy slut. Oh god I am gonna come already!"

It hurt somewhat so that when he stopped at just a few inches inserted with my gasping request to wait, I could now feel his hand on my lower back petting me to soothe me from my agitated state. When I finally groaned just a few moments later, the invasion continued until I felt his hips press up to my ass cheeks. Tyrone once again stopped, except for small subtle movements as he swiveled his hips before starting the withdrawal making me groan once again. The sensation was amazing as I felt it slip out. This must be what it was like as a girl, I thought, as he suddenly started to push back inside. After pushing it in and out a few times he starts to pick up speed and force. He keeps pumping his cock into me and I can hear that slapping, squishy, sex sound that is so stimulating and suddenly I can feel myself pushing back against his invading cock and moaning, I could hear myself making vocality's like some porn star; groaning, moans, little yelping cries of pleasure, begging for him to fuck me, to spank me....and then he did! With a loud smack, I felt him swat my ass, then again, every few strokes as he pushed in and out making me yelp in excitement. In a short time, he was pumping in and out of me as my ass pussy loosened so that the pain transformed into a feeling of sexual arousal. I seemed to feel myself pressing back against him as he thrust forward and tightening my sphincter as he pulled out. When he grabbed both my hips and started to just pound me, it happened. I shuddered in a whole-body orgasm, squirting up onto the wall in front of me. My legs went weak with only his cock inside me and the wall I was leaning against keeping me upright as I let out a long, drawn-out cry of orgasmic bliss. I never imagined that it could be like this, some hot, living thing inside me making me feel so good so that when he forced his cock into my boi-pussy, striking against my prostate, I started to have uncontrollable shaking orgasms, over and over again, begging him to never stop fucking me, to make me his little sissy bitch! I could not believe that just a short time ago, I was questioning my `hetero-ness', and now listening to myself beg to be fucked like some slut in need of a fix, I knew I would always crave this feeling!

Tyrone was not done however, as he had not come yet! His big black cock pushed into me relentlessly, my ass now loosened enough that he was sliding in and out easier than he did initially so that I was again starting to build to orgasm. When he pulls his big black cock out of me, I feel empty for just a moment until he slams it back inside of me, balls deep making me shudder and cry out. He does this about half a dozen times, complementing me on having such a fine pussy built for fucking big black cocks like his. Then he pulls out one final time, spinning me about, taking me in his arms so that my legs wrap about his hips, my arms go over his shoulders clasping behind his neck, he then carries me to the couch and when he sets me down I take off my top, skirt and panties so I am just in my Bra, corset, stockings and heels. Then he lifts my legs up over his shoulders, spreading them apart so he can fuck me with no impediment. His big black cock is making me quiver in sexual throes of pure lust until after what must be 20 to 30 minutes but felt like much shorter in my delirious sexual frenzy, I felt his cock grow and get hot just before it starts to shoot streams of his treasured cum into my hungry ass pussy while both of us cried out in orgasmic exultation!

He stayed inside me for a short time and as he pulled out, I dropped to the floor and took him into my mouth to clean him and taste his musky maleness one more time. I can feel his cock leaking residual drops and I swallow as fast as I can, sucking hard to insure that every precious drop of his seed is consumed by my hunger for more. As I pull back and wank his shaft, I realize I LOVE the taste and want even more of it! So much so that I can feel my small man leaking while I shove him back inside my mouth. I keep sucking on his cock cleaning away all the come from it worshiping his cock like it is my god! As he finally becomes to sensitive for my wanton ministrations, he pushes me off his cock and says, "Gurl, you are so sexy like that! You look so natural with a black man's cock in your mouth and sissy pussy. I bet you want it all the time, now, don't you?"

I responded with his cockhead inches from my mouth, panting in still active lust, and looking up at him from my kneeling position,

"MmmHmm!" and gently sucked and licked and cleaned his black cock until he pushed me off it once again.

He settles next to me, with me curling up next to him, almost purring in contentment, my long nailed fingers tracing through his dark chest hair as Lisa sometimes used to do to me and I look at him as he says to me,

"This may hurt, but I think you will thank me later girl. You are just too good a fuck to pass up."

I start to ask what he is talking about, when I feel a prick on my neck, I startle and see he is holding a small syringe and things drift away into darkness like I am falling asleep after a hard day's work.

I woke up slowly, groggily, and that should have been a clue as I normally wake up fairly quickly, but I also noted that I was secured to the bed I was in and that there were monitors and tubes attached to me. I must have made a sound as I was scared a hell, imaging something terrible had happened, before recalling the party that never happened and what DID happen! Suddenly there was a lovely redhead standing over me, she had her long hair tied back, black rimmed glasses, and the most kissable lips I had ever seen!

"Relax Tiffany, there is nothing wrong, we just took the opportunity to adjust some things as you were kind of out of it when brought in by Tyrone. Your breasts, face, throat, ass, and belly have been fixed from all the trauma you experienced. Your face is now so much more feminine with the reconstruction, and lovely pouty lips just like mine! We also shaved the Adams apple, tightened the vocal cords, gave you real "DD" breasts, laser hair removal, did a little lipo on the tummy to bring it down to 22, then added that fat to your bottom so you have a little more cushion for pushin! Oh, yeah, I almost forgot, we stuffed a time release Progesterone implant into both arms so you should be swimming in female hormones by now, along with androgen blockers, you will look even more fabulous than when you came in! Welcome to womanhood Tiffany!"

I made some scream of negation but what I really heard was something like "Mrg-grgl, mft!" as my pouty lips, dry mouth and sore throat conspired against me. The nurse(?) just smiled, patted my shoulder, offered me a sip of water through a straw, then exited as I drifted back into a deep sleep.

I wake back up again in what I think must be the day as the room lighting from outside is different and the pain is almost gone. The same nurse greets me with water and says that the bandages have been removed and I seem to have recovered quite nicely and look so pretty! Pretty I think, why would I look pretty? Then I recall the talk about the facial feminization, the trachea shave, the laser hair removal, the implants! Holy shit I was made to look like a girl and how long have I been in here I wonder?

A few moments of panic before a doctor(?) comes in with "Smith" on his nametag and I giggle thinking he even looks like the old "Lost in Space" guy. He tells me that I should be able to be released as soon as Tyrone comes to get me later this afternoon, that all the procedures have been quite successful and well done if he does say so himself! The virtual stimulus they performed each night while under sedation for recovery should have taken hold as well so I can expect to be performing in no time for Tyrone to help pay back the procedure costs I wanted.

When I tell him I never asked for these procedures, he smiles, sighs and then shows me a signed contract by my old name of James...and it sure looks like my signature! He comments that the missing person report filed by Lisa was closed upon this being fed to the police along with the request that Lisa be told I was no longer wanting to be in contact with her so she was awarded the house so she could move on with her life. My restraints were removed, and I was given some tight, black and black lace thong panty that my now very tiny penis was easily tucked into, an "E" cup bra that I was told might be my new size after the hormones really kicked in, a light purple top, some black wedge sandals.

About an hour later, Tyrone came in wearing slacks, a button shirt and I looked at him and then right at his crotch, recalling how big his cock was and then how it felt, then suddenly I was staring at it, licking my lips, wondering if he would fuck me with it again! He grinned and let out a light chuckle before saying softly,

"Looks like the programing took Doc! She is looking at my crotch with obvious hunger!"

"Hmm, seems to be. I would say this bitch is gonna make you a ton of money sir. May even be my best work yet!" Dr. Smith crowed.

"What the hell are you talking about!? What have you done to me and when can I get out of here and reclaim my life!?" I demanded.

"I will allow that talk to me this time as you are new to all the changes you wanted, that I paid for in advance and you will now be my employee until that cost is repaid with a modest interest of course!" Tyrone stated pointedly, like it was non-negotiable.

I blustered about suing, was shot down by the signed contract, complained about not being able to prove how I was as Tiffany when I was given my purse from that night that now had ID as Tiffany and then told that I had been in this room for a little over a month as the operations were performed, the changes I requested completed and the subliminal training done each night so yes, I was no longer James. I was now Tiffany in a very legal sense, Lisa was no longer looking for me as the missing person report was closed when the police were given a copy of the contract, and I was starting my new life tomorrow as part of Tyrones stable of prostitutes that worked the neighborhood near where Rodrigo the taxi driver picked me up. So, I would be near the hotels and the casino turning tricks for 50 a BJ, or 100 a fuck. I owed a mere 50k so doing the math in head, I just had to do a mere 1000 blowjobs to pay back the bill and a few more to cover interest and when I said that aloud, Tyrone smirked that I only got 10% put towards my bill as the rest went to my clothes, room and board, utilities, checkups, etc. so that meant a bit over 5k in blowjobs, so I knew I was stuck this way for some time! He also mentioned I would get a 5% cut for personal expenditure, like smokes, or food and drink while working the streets. He then showed me the hotel I had a room in to take my customers to if they did not want services performed in their car.

Tyrone took me to my new lodging and explained that I would start working tomorrow night. The clothes in the room should all fit me, I had regular monthly checkups scheduled, and I would be expected to put in my payments along with a log on what was performed each night to the lady watching the hotel office.

I can't help myself, but I look at his crotch and can just see an outline of his massive love muscle and lick my lips and take a drink of water and say,

"That's what has me worried Tyrone. I can't seem to stop thinking about men and their cocks! I dreamed all night last night of being banged by big black cocks, sucking on cocks, dressing slutty so I can attract more cock! I get you want me to be your whore and make money, but this was supposed to be a joke costume for a party and now look at me, I really am a whore! I mean, now, I look like a hot babe, and all I can think about is swallowing your seed and having you fuck me silly, what is happening to me?"

All I could see was his package and how large it was and when he asked, "Well, what do you think you need to do about it Tiffany?"

All I could say was "Umm I need to talk...to get you to change..."

"Yes?" he queried.

"I can't take it. . .you've changed me...I dream about . . . I want to...oh damn it, you bastard! I need your big black cock in my mouth now!" and so, saying, I strode over to him unbuttoning my blouse to showcase my large breasts and then opened his trousers so I could pull out his large black cock and moaned "oh god it looks so good and big like I knew it would! I want it in my mouth!" and that's when I popped the head into my mouth and moaned again around it and started to bob up and down on it licking the eye and underside while pumping his length with my hands and spitting on it to get it wet so more would fit into my mouth!

He just moaned in response and said, "Yeah that's it baby, suck my big black cock you sexy sissy bitch!"

I forced more and more of his massive meat down my throat and pulling back to lick his shaft more and finally as I forced that last bit down my throat I could feel his short tight pubes against my nose and knew I had several inches of big black cock in my mouth and throat and it tasted so good I knew I would do this every day if he let me! I pulled back up and took a breath while circling his head and bobbing on that helmet a few times before forcing him back down my throat and swallowing a few times. Back up, jack him, lick the head, tickle his balls then back down the length. I kept this up for several minutes while he held the back of my head and kept my hair away until he stiffened in my mouth and pulsed a load straight into my belly! I pulled off his big black cock and opened my mouth with my tongue extended as his next few spasms of ejaculate filled my open waiting mouth. I then looked up at him stuck his head in my mouth sucking and swallowing down my reward. I felt a surge of wetness in my panties that told me I had come as well. I continued to lick him clean and then kissed the head and softly put his shrinking cock back into his pants and as I stood up whispered,

"Oh My God your cock tastes so good! I want it inside me you big black cocked stud!"

With all that said, Tyrone reached down to take me by the hand, pulling me close, pulled my jeans and panties down, wrapped his arms around me and started to nuzzle my neck as I straddled him, feeling his cock start to throb underneath me. I could feel his manhood twitch and grow harder, firmer as I wrapped my arms about his shoulders, letting out a little moan, turning my head to suck on his tongue while grinding into his manhood. Feeling my chest pressed against his, my nipples hardening just like his manhood was, the thrill of that trouser snake pressed into my belly made me horny all over again even though I knew I had just had an orgasm just a few minutes ago! I could not understand it, but my body was reacting to his advance and kiss just like some horny teen would and I could not help myself from reaching between us and stroking his cock. It. Was. Huge! I had always been proud of my manhood before this, but this was just way bigger than I could have ever imagined except maybe in porn!

He grinned at me and said,

"Good Girl! I knew you liked sucking cock with that sexy mouth of yours. And you are so naturally good at it baby!" making me feel good and happy.

After several minutes of him teasing me, I knew that meant he was about to fuck me with that big cock and I eagerly waggled my ass in presentation, grasping it and rubbing it under my little he-clit and spouge from earlier so it got lubed up as I begged,

"Fuck me with that big giant cock of yours Tyrone! Shove it into my bussy and breed me! I want to feel like a woman! Fuck me!"

Tyrone did not hesitate and slid his cock into my boi-pussy in one swift plunge about halfway making me cry out about 'how big it' was and 'that I could not take it' but he pulled out to just the head and then stuffed it into me again a little farther, making me feel stuffed like a Christmas goose, balls deep to overflowing. To prevent my yelp of pleasure, I bit down onto shoulder so it came out as a low moan as he grabbed my hips and started to piston in and out for several minutes until I started to squeal, cry out about how good it was, making noise like some whorish porn star...I was a verbal fuck and it was so exciting as I had never been that way before, but I had a steady litany of cries, moans, comments and noises as he pounded my wet ass-pussy. Our juices were dripping down my thighs when I could take it no longer and yelled out that I was coming again as my orgasm hit me like an explosion in my belly as I forced his cock out of my pussy, squirting up onto his chest from my limp little clittie! I had never come like that as a man.....it was the most intense orgasm of my life and his cock twitched at my ass-pussy, seeking entrance back inside me.

Tyrone pushed it into me as I gasped in shock. He let me get used to it again for a few moments like a master ass-man, then continued to push into my back door until I felt his hips strike up against my ass cheeks. His hand suddenly spanked my right ass cheek, several times making me squeal and jump, as he started to drive into me hard and fast. He spanked me a few more times telling me to 'take his cock' while I moaned about loving it. Then he grabbed my hair and pulled it back so that my back arched as he pushed into me fucking me fast and hard like a pistoning sex machine. I groaned as I thrust myself back onto his cock, pushing with the strength I had in my arms to gain as much of his cock into me as I could get when I felt his shaft grown hot, thicken and start to pulse his seed into me. It triggered another orgasm on my part as I felt his seed painting my insides! I was crying out in pleasure and kissing on him like some devoted little fuck puppet calling him 'Daddy' telling him how much I loved his cock and how 'it owned me!'

The next day, Friday, my first as an actual prostitute working for Tyrone.

In the apartment, I dressed carefully. First the bikini panties, and I thought it would be best not to tuck so there would be no doubt about my being trans, then the garter belt and hose. I finished with a short skirt, in black, and a bright red tank top. It was stretched so tight that my nipples stuck out, and it barely covered them. The high heels made my ass and chest more pronounced, and my short steps made my hips swing sexily. I put the makeup on heavily, with very red lips, and dark smoky eyes. Then I put on some huge hoop earrings. I went to the mirror to check my appearance. What a tramp! What had I gotten myself into? As it became dark, I left for downtown. As I got to the bus stop by the casino, I could spot the other hookers working the streets. They frequented a large part of one section of the downtown area, so I was not too worried about being in another's' area as I walked provocatively toward a main street and struck a pose under a streetlight in typical cliche repose. My heels and tight skirt caused my hips to sway, and I worked to exaggerate that motion. My hair swung over my shoulders as I turned to look into the windows of passing cars to attract the Johns. This was near the main hotels where the business trade and casino was, so the sex business would be here too.

Within 5 minutes, the first man approached. His suit was mussed, and his tie was loose around his neck. "Hello, want to party?" I asked.

He paused for a minute, and then said, "How about a drink."

"Sure", I replied.

We walked into the nearest bar and sat at a table. He could not take his eyes off of my huge breasts in the tight clothes. He ordered drinks, and we quickly got down to business. We set a price, which he paid in advance, and then left immediately for his hotel room. This was great I thought. Easy, and fast.

In the room, I gave him a blow job, and then brought him to arousal again. He entered my bussy, and we moved our hips together as he became more and more aroused. Finally, he came, and so did I. We lay for a while, then I got up to leave.

"Thanks!" he said as he gave me a nice tip.

Over the next 6 hours, I met with and fucked or blew more men. Each time, I had a wonderful orgasm myself. I quickly found men who wanted my services, and I made a lot of money. Each time, I felt more pleasure that the last. I loved it! I was able to do two tricks an hour for most of the night. Many of them wanted only a blow job, which I could do very quickly. Even then, I was loving every minute.

The night was great. I made a fortune, and I began to get a reputation on the street as a good lay with a preference for black men. I wanted their sperm in my mouth. I needed the climax from having them cum inside me. I loved the feel of their huge black pricks entering my body and moving in and out. I loved to tease the white guys and then bring them to the edge, holding them there before giving release.

Saturday was much of the same, and when I turned in at the end of each night, seeing the madam/hotel managers eyes pop open at the amount I brought in made me giggle to myself quietly as I knew I had been pushing myself to get the tricks.

Sunday was a little slower so I only made about $800 that night, but while wandering back out to the street from the casino/hotel where my last John had taken me, I had to do a double take on the couple coming towards me. It was Lisa, arm in arm with my old best friend! I smiled when he checked me out, but neither him nor Lisa even recognized me as being James, so I knew I had changed drastically enough that neither of them saw me as more than some pretty girl at best or just some trampy slut at worst.

Over the next two weekends, I again was top earner for Tyrone and each weekend that I was, he took me to a nice dinner, where I got to wear a nice evening or cocktail dress and be his date. The best part was the oh my god sexual marathon he provided. I was addicted to his cock, and he knew it!

One Monday night, when it was slow, he came to the streetlamp I normally parked at, signaled to me I was 'off the clock' and led me back to the casino/hotel and up to a room. The room was nice, if still a small hotel 'single' but it had a small fridge, desk, and all the usual hotel stuff.

Once inside, he pulled his tube snake out and waved it at me while I dropped to my knees and started to suck on his head and shaft getting it lubed up again. He impatiently pushed it down my throat and started to face fuck me while holding the back of my head. He was rough, and it was turning me on to have his big black cock push past my gag reflex and feel his throbbing cock slide down my throat until I could feel my nose against his pubes and looked up wide eyed into his, with slobber dripping down onto my chest, in amazement that I had taken his entire length so easily now where I had struggled before to even take half of it. When I pulled back up, I licked his head, cupped his balls and started to massage them and let my fingernail scrape against his bung hole. This must have been a trigger as he forced his massive length back down my throat, balls deep, and started to pulse his load down into my gullet with a long groan of release. I pulled up off his cock and then gently started to suckle and lick his love muscle clean until he pushed me off it and said,

"Damn bitch! You're a natural born cock sucking Ho with some serious skills! Your customer base is about to explode! I have decided to move you into this room, so you can work at the casino. The Johns here are a bit more discerning so dress not so much streetwalker like you been, and more high class call girl in a nice expensive skirt and top or fancy dress. The security knows who you are and will be cool as long as you are not fucking someone in public...or well, obviously fucking them in public in front of everyone else, so be discrete if that's what they want!"

As he stopped telling me this, I cried out in joy then dropped back to his cock to celebrate. I sucked hard on his head and tickled his balls with my nails to get him hard and when I knew he was ready, I stood up dropping my soaked panties, straddled him and fed his man meat into my boi-pussy and sank down onto it about halfway and moaning out how big it was and how full I felt! How much I loved the feel his big black cock inside me. His cock twitched at my words, so I knew he liked it too, and his hands dropped from caressing my chest to grabbing my hips as he started to feed his length into me, going deeper and deeper with each thrust until I felt his balls slapping against my ass cheeks. Wrapping my arms about his strong neck, I started a steady bounce and grind that had me spurting my load onto his belly in short order. His hands kept me in place, and he started to pound his massive cock into my hole as if he was in a frenzy to come...we both cried out and moaned in sexual frenzy until I felt his rod spasm and paint my insides in an orgasm that triggered my own once again.

I was making mewling and happy noises as he picked me up and carried me to bed where I fell asleep with him behind me and an arm curled over my side cupping one of my breasts. In the morning, he was gone, but a note on the bed said: Congrats Tiff, you earned a nice upgrade and I am sure you will keep me happy by bringing in the big bucks!

After about a month of working the casino, I had gotten into a rhythm with the staff, the maids, security and even the front desk and concierge. They all liked me, and I liked some of them well enough to take them into the back and blow them. The one I like to blow the most was this sexy little dark-skinned girl with a wonderful figure and skin like smooth chocolate that tasted just divinely sweet. My tongue and her pussy became fast friends, and she even recommended me to some of the guests as a diversion during the slower weekdays!

It was comical to me that after this time, the white guys typically had a smaller penis than the black guys, but came way faster too, so I could turn more tricks with white guys, but black men were so much more satisfying due to their much greater size and stamina. I guess that old wife's tale about the size of black men was based in some truth after all!? One night, my little desk lover, Knecole, came to me to say that there was a convention showing up that night from some porn industry and that she had talked to Tyrone about it, and wanted me to be the entertainment. I only needed to take care of about 100 horny dudes who were paying $100 bucks each to have me suck their cocks and blow their loads on my face in a huge Bukkake party if I was interested?

"Shit yeah I am interested! Thats a crap ton of cash and all that cum all over me, fuck that will be so hot! Oh, you should come as my chaperone to make sure everyone pays and help me clean up after, then if you want, I can clean you up as I bet watching all those guys come all over me will make you so horny you will need my face to get off on! Yum, I can't wait!" I responded.

"Damn. Tiff honey, sometimes I think you really are doing this cause you really are just a slutty tramp and not because of all the money you making!" she replied in exacerbation.

"Honey, the sooner I get Tyrone paid, the sooner you and I can be together!" I whispered.

"Yeah, but what about Tyrones BBC? You gonna give that up just for me baby girl...I am thinking not as I hear you sometimes screaming in happiness when he fucks you...you know you just another hole for him right, girlfriend?" she taunted.

"Yeah, I know, but yeah his cock is so...overwhelmingly good, I find it hard to resist. But maybe when it is just you and I, I can resist...especially if you use that nice big horse cock strap on me!?"

"You're horrible! Now get along and go get ready for that party...it's tonight at 7pm you little slut!"

back in my room, I had just enough time to shower, put on my make-up, deciding to wear just a cute little black leather and white satin lace bra, panty and garter set with tan nylons that had a back seam, black 5-inch stiletto heels and my long trench coat to walk through the hotel casino up to where I would meet Knecole who would escort me into the their ballroom where the presentation for the party was being held.

once we got started, I dropped my trench coat so that Knecole could grab it and move it out of the way.

I smiled and began to dance for the guys while drinks were served. I strutted around the big main table where most were gathered. While the bra and panty set were mostly opaque, I knew they could see everything. Once drinks were served and the waiters were gone, Knecole started talking again,

"Let me tell you about her day so far. Tiffany has a shitty job so she called in sick for work. She is so hot for cock she is a working girl on the side. She plans on trying to take all of you on to see if she is as good as she thinks she is, and she is doing it just for the fun of it aren't you honey?" she asked.

I felt my bussy tingle, stopped dancing and blushed hotly.

"Yeah" I finally answered.

"Good girl. Don't be shy." Knecole cooed, then went on further with,

"I'm sorry baby. I don't want to embarrass you. I was just letting them know what they're getting."

Then as she stopped the music, she pointed at me again and asked,

"What do you think Gentlemen can she take you all on?"

They all clapped and told her how happy they were with me. I smiled and preened for them. I was so hot thinking about sucking all their cocks, my bussy was soaking wet from being tucked and leaking.

Knecole smiled, pulled out the nearby empty chair, pulled up the tablecloth and said to me,

"I want you to suck all of their cocks really good. If you do a good job, I'll make sure you get fucked by at least the ten guys cocks you like the most. Would you like that?" she smiled.

I wanted it so bad; I was tingling all over.

"Yeah!" I answered eagerly.

"Better get busy then girlfriend." she said pointing under the table.

Everybody chuckled while I scurried under the table. I quickly made myself at home and was greedily sucking cock under the table. Knecole collected my things and had the waiters serve dinner. I sucked cock after cock while the waiters and waitresses bustled about. When the waiters left, I crawled back out from under the table and started sucking cock again.

While I worked on giving everybody blowjobs, they had finished dinner and were sitting around talking. While they talked about what a treat Knecole had provided, I got so hot I had to start fingering myself. Tyrone and Knecole knew I was just what these horny adult video guys were looking for. They all agreed that I was perfect and how grateful they all were.

I was so turned on listening, I was fingering myself hard while sucking cock furiously. When they stated to cum, that warm wonderful feeling of orgasm washed over me, and my orgasm busted loose. I squealed and moaned while I swallowed as fast as I could but as per the deal, I let some splash across my face. When I regained my senses, his cock was already soft in my mouth. I smiled and crawled in front of the next in line.

I sucked cock, had guys gather around me so I was jacking some off, while sucking on another. I was in cocksucking heaven! There were cocks of all shapes and sizes, big ones, short ones, skinny, fat, straight, curved, even one guy who was uncut! Guy after guy either started to come in my mouth but always sprayed across my face or couldn't hold on and was about to come from jacking their meat, so stepped up to come across my face while I was busy drinking down some other cock. I was on my knees, then on my back over a table, then in a chair with a couple guys deciding that they could not wait and pulled my panties down to fuck my ass-pussy! They would stop just before coming, so they could move to my face and spray their load on my face, in my hair, my ears or one guy even spurted up my nose, so I ended up snorting his jism!

It took several hours for all the guys to come on me, but when I looked down at the other end, I saw that Knecole already had gathered up my things so we could leave after I freshened up my face.

"Good Girl." Knecole cooed after I came out of the bathroom having cleaned up all the come and removed my make up.

I looked around, all the staff were gone and noticed most of them were mulling around the room. I walked around and talked to them. They all told me how good I was and how much they hoped Tyrone and Knecole would bring me by again. I told them how much fun it was and hoped they would too. It made me so hot, I could feel cream pie start to leak down my leg.

I had a big smile as everyone watched me put on my topcoat. There were ten envelopes stacked where Knecole was sitting. she picked them up, thanked everyone and hoped they enjoyed dinner and the show. They all agreed they thought I was great. I smiled and told them all thanks.

Knecole tapped me on the shoulder and gave me one of the envelopes saying,

"Put this in your purse." she told me.

"What's this?" I asked confused.

"That's yours. You did good. It's your tip for tonight." she said as she stuck the others in her pocket.

When I opened it there was stack of crisp $100 bills with $1,000 clearly printed on the band.

I felt my pussy twitch, smiled and stuffed the envelope into my coat pocket. She gave all the waitresses, waiters and bus people cash. Then she tipped the Concierge again. I followed close behind her blushing the whole time. When we got to my room, Knecole reached inside my coat to play with a nipple and talk about how hot it was to watch me be a bukkake queen and get fucked by all those guys who could not wait. She opened the door to my room, escorted me inside then pulled my coat off, tossing it to the floor, pushed me onto my bed, used her cell to send a text, then sat on my face! Five minutes later as Knecole was coming for the first time, I heard the door open, and shortly after that I heard Knecole say,

"She did real good Tyrone. You may need to fuck this slut really good as all that cock has her going real bad!"

That is when I felt his cock push into me balls deep with little resistance as my ass-pussy had been pre-lubed from all the loads left inside me earlier. I could feel his cock filling me and hitting all those right places that the others had missed. I came almost immediately, Knecole came several times and Tyrone once after about 45 minutes of pounding that big black cock into me like a mad man!

It took about a year as Tyrones top earner for me to repay him the 'loan' of my transition, and by that time, Knecole and I were seen as a lesbian couple using a huge black cock strap on for penetrative sex. I kept working for Tyrone as After being a successful prostitute for a year and a half, the money and fulfillment was far more satisfactory than that of a mid-line accountant.