Sissy Taylor's Secret Past

Hi, my name's Tyler and this is my story.

For as long as I can remember, I always felt different from everyone else. I never really found my place as a man in the world but was never sure why. I spent so much time lusting over different girls, but never pursuing them, always just rubbing my dick to the thought of them. I watched endless amounts of porn, and for some reason I always preferred interracial. Watching a video with a white guy always turned me off for some reason, I always wanted to see a big black cock and a curvy white girl. I also always had a preference for humiliation and gangbangs.

Even the way I played with myself wasn't masculine. Instead of pulling out my cock and jerking it like any real man would, I would always rub it through my underwear or shorts. I always told myself it was for privacy in case I got interrupted, but the truth is it just felt more natural.

I think part of my issue is my looks, but also my personality. Although a fairly tall man (5'10), I also had a curvy body that would've fit better on a woman. I've always had thick thighs, a big butt, and slim waist, giving me the classic hourglass shape. Plus I have really long eyelashes and have always been called pretty (not handsome, always pretty). On top of that I've never been what you'd call an "Alpha male". I'm naturally awkward and submissive, deferring to others, both men and women alike.

I've dated women throughout my life, and I definitely have a type. Strong, independent, white girls with a booty. They always took charge in the relationship and I always was along for the ride. We would have sex, but I'd be lying if I thought any of my partners were satisfied by me. Between being only 5 inches rock hard, not being dominant, and cumming way too fast, it's not a recipe for success. My relationships usually ended the same way, they would get bored of me, and leave me/cheat with someone else (usually big, strong, black guys that dwarfed me in comparison).

My life changed when I started dating Eliza. She was the most beautiful girl I'd ever seen. The classic girl next door, 5'4, with curves for days. We had gone to high school together, but she never paid me any mind. She could've had her pick of anyone, from the basketball team, to the future doctors, to the sorority girls lusting after her. One day in the city a few years after college she was in front of me at a coffee shop. I didn't think she even noticed me but when it was my turn to order the barista told me it was already taken care of and handed me a drink. I was lost but she simply pointed to the table in the corner where Eliza sat waiting.

I walked over to her sheepishly and said, "hi".

She giggled and said, "omg you're so adorable, have a seat".

I did as instructed and she asked, "don't you like the drink I bought you?"

I blushed and took a sip.

It was some sort of super sweet, creamy warm tea. The kind of thing any basic white girl would've ordered. It wasn't something any self respecting man would be caught ordering.

"Thanks, it's um really good," I told her.

"Hehe you're welcome, I thought it seemed fitting for a boy like you," she replied with a smile.

A boy like me? I wondered to myself what she meant by that.

"Anyway, I saw you in line and I decided, you're going to be my new boyfriend, k?" she continued.

"Umm... ummm... what?" I stammered.

"You silly boy, I don't like repeating myself but I'll make an exception this time. You're going to be my new boyfriend," she said firmly but with a smile.

I was too stunned to speak, so I simply nodded my head. From then on my life was a blur. My whole life revolved around her.

The dynamic of our relationship was obvious to anyone paying attention. She was the outgoing, assertive, gorgeous woman, and I was the quiet, submissive, guy who wasn't particularly impressive in any way, just happy to be included. I'm sure people would laugh at the guy following behind this incredible woman like a pathetic puppy, instead of striding forward side by side as equals.

There is one thing Eliza doesn't know about me though, my biggest secret and greatest shame. I used to get bullied a lot in school, all the way through college. In particular there was one worse than any other, Derrick. He was the captain of the basketball team, he was 6'5 full of muscles, and based on the rumors he proved the stereotype of black men's BBC correct. For some reason he always went out of his way to target me. It was relentless and I didn't know how to handle it.

Looking back, I should've gone to therapy, but I ended up with a different coping mechanism. I started to crave it. It became a kink of mine, craving to be humiliated sexually, to be submissive and feminine for a superior black man. It consumed me. My porn habits became more extreme, and I spent so much time in my room on the computer thinking about it.

Finally I couldn't take it any more and caved. I went on Reddit and found a BNWO sissy personals subreddit and made a post. I put some information about me, including my location, my pathetic desires, my feminine boy measurements, and where I felt like I belonged, on my knees, dressed up like a slut, for a superior black man to use and laugh at.

It only took a day for a response, but that day felt like an eternity. It came from an account named BigDaddyD10.

It simply said, "good to see another white boy has learned to accept their true place in the world, what's your address and when can you meet bitch?".

I was stunned by the power in the words, but even more stunned by the small bulge which formed in my pants.

"Hello sir, thank you for responding to my post. I am glad you were pleased by it and I hope I can keep pleasing you going forward. Here is my address and I would love to meet as soon as possible, to begin taking my place as your slave," I replied desperately.

Looking back I can't believe how quickly I volunteered that information. What if someone found out about my secret? What if this was a mistake?

After five minutes of torture I got back a short message.

"Good girl, tomorrow 10 pm, be on your knees, naked, with the door unlocked when I get there. Don't you dare think about cumming tonight either. From now on you only cum when I say you can," he replied with strength and power.

I wanted to rub myself soooo bad the rest of the night, it was torture. The next day wasn't any easier, wondering who this stranger was and what he had in store for me. I can't tell if I was more horny, nervous, or excited.

Finally as 10 o'clock came, I unlocked my door, stripped off my clothes and waited patiently on my knees in the hall. Finally I heard someone approach. My mind began to race, what if its not him? What if someone else finds me like this?

Before I could move, the door swung open and I heard a voice, "knock knock, where's my bitch at?"

I gulped and my stomach turned... it was Derrick! He was huge, muscles bulging. He towered over me when I'm on my feet, so with me on my knees it was truly a pathetic sight.

He saw me and just started to laugh, "well look at what we have here. I always knew I was right about you. You really are a pathetic little bitch!"

He grabbed his crotch and said, "I bet you've wondered if the rumors were true. Time for you to find out".

He unzipped his pants and out flopped the biggest, thickest dick I had ever seen. It wasn't even fully hard and still it was easily double the size of my tiny pick cock. I couldn't take my eyes off it.

I heard a click and saw a flash.

I quickly snapped out of it when I heard a voice.

He said, "There's going to be some rules now that I'm in charge, and just in case you think about disobeying me, this picture will go all over campus".

I started to panic but figured I'd better play along. I nodded my assent.

"Good girl. Rule one, from now on you aren't a man anymore. With how tiny that thing is, I don't think you ever were. With that said, when you're in my presence you will no longer have a mans name, you will now be my sissy, Taylor. You will also stop pretending with mens clothes, it will only be women's panties, bras, lingerie, or other outfits I require. This includes a wig, until you grow your hair, eventually makeup, and some nice fake tits to make you a proper bimbo. You will also need to be hairless at all times," He stated plainly but I knew he meant it.

I was in shock but this was all turning me on so much I couldn't help myself. I spoke and was surprised by the high pitched voice that I heard.

"Yes Daddy, I could never compare to a man like you. I'll be the best slut ever for you," I said desperately.

He smiled and I was happy to see I was pleasing him already.

He then continued, "That's what I like to hear. Rule two is that you will never be on your feet in my presence. You belong on your knees or bent over at all times like the slut you are.

You will also need to buy a dildo, I want to attach it to a chair for you to sit on. It will be your sissy seat".

"Mmm yes sir, I'll get all of that right away," I replied.

"Good girl, now crawl over here and beg me for your reward," he said.

I crawled, and for some reason I felt my bubble butt swaying as I went.

He reached down and spanked me to watch it jiggle.

"Mmm you've got a nicer ass then most of the girls on this campus. You'd make an awful lot of sluts jealous," he said with lust in his eyes.

"Thank you daddy, I'm glad you like it," I said with pride.

The sad thing is I really meant it.

He saw my gaze still hadn't left the massive specimen hanging in front of my face and said, "I've seen that look a million times, if you want something you know what to do".

I replied instantly, "Please sir, please can I suck your magnificent cock so I can become your black owned white slut. I need it so bad, I just want you to use me".

He laughed and said, "Damn you really are a desperate bitch. Lets see how much you can take".

I timidly started to kiss it. Then slowly taking it into my mouth, bobbing up and down, in and out, over and over. It was so big I could only fit about half in my mouth but I kept trying. He seemed to enjoy seeing how cock hungry I really was.

*Flash* another picture of my shame, on my knees covered in spit, with a massive cock in my mouth. He then grabbed my head and started pumping, in and out aggressively fucking my mouth. I was just a hole for him to use. Eventually he reached a climax, pulled it out and blew the biggest load ever all over my face, I was covered. *Flash* One final picture to seal my fate.

He laughed again and said, "That seals it, now you're my property. You're officially a black owned white sissy slut."

I stayed there on my knees, exhausted but proud.

He then said, "I'll be back tomorrow at the same time. You better have everything I told you about and be ready to serve".

"Yes master," I replied.

I spent the whole next day getting ready. I went shopping for everything. Thongs, bras, and lingerie from Victoria's Secret. A massive black dildo that almost matched my masters cock. I got some makeup at Sephora, and a tutorial too, which was so humiliating. Finally I found a store that sold fake breasts. The woman was so helpful, helping me pick out a chest plate of massive 38 E sized boobs. They also sold wigs so I got a long blonde one, to help finish the bimbo look. When I got home I showered and shaved every inch of my body. It was incredible how soft and delicate my soft white skin felt.

The next thing was to set up my "sissy seat". I pulled out the massive black cock and stuck it to a chair in my kitchen. It was hard not to lust after it but I couldn't get distracted. I then pulled my new fake tits over my head and it felt so good. After I pulled up my matching pink thong and bombshell bra I couldn't help but check myself out in the mirror. Damn I look hot!

I put on my blonde wig and did my makeup the way the girl taught me. By the time I was done I didn't even recognize myself, I looked like such a sexy slut!

The rest of my time I tried to keep from touching myself and waited patiently for my master. Finally 10 o'clock had arrived and I heard a car door shut.

I wasn't sure what position to be in so I quickly got on my hands and knees facing away from the door, arching my back and presenting my juicy white ass for anyone who walked in to see. I was face down ass up as they say. I couldn't believe how slutty this felt, every breath feeling my gigantic breasts swaying, shaking my ass slowly and seductively in preparation.

Finally the door opened and I gulped. I didn't see who came in, and they were silent. The only noise came from the heavy footsteps advancing towards me. Then came the click and *flash*, followed by a smack on my ass.

He aggressively told me, "Mmm mmm mmm, all the guys are gonna want a piece of you once they see this. Now let me get a look at my little white slut".

I lifted my head and showed off my new tits to my new master.

He continued with amazement, "Wow look at you girl! I always knew you'd look better as a sexy white bitch. You've done so good for me, I just have one addition."

He reached down and placed something around my neck. I felt it click into place and knew it was some sort of collar.

"Why don't you crawl over to the mirror have a look?" He suggested.

I did just that, slowly swinging my hips, feeling my tits bounce as I moved. Then I saw it, it was a sparkly pink collar with the words "black owned sissy slut" written in glitter.

His bluntness continued as he said, "Tonight we're gonna make you a real slut, you already look the part. I'm gonna bend you over and breed you like the bitch you are."

I didn't know what to say. Did I really want this? A part of me inside yelled "I'm a man," but on my hands and knees, dressed like the biggest slut in the world, with a red handprint on my ass, it was hard to believe that were true.

I just whimpered, "yes daddy, breed me and make me your slut".

He smirked instead and said, "you're gonna have to earn it first, I could use some entertainment."

He tossed a pillow onto the floor and continued, "show me how desperate you are for this dick, hump that pillow like a good whore, and don't be afraid to put on a show".

I couldn't believe what I'd been reduced to. I spread my legs and climbed onto the pillow and began moving my hips back and forth. Slow at first but eventually getting more and more into it. I could feel my tits bouncing while I bounced up and down, then riding back and forth. I can't imagine how desperate I looked, begging to be used like a pathetic whore.

I said with rising desperation, "Please daddy, fuck me like your good girl, I need it so bad. I need to be used, pleaseeeee."

He pondered for a moment and said, "Hmmm I guess you've been a good girl, you've earned a not so little reward."

He motioned for me to crawl to him so I did. He whipped out his glorious black cock and told me to start sucking. I was so desperate I dove right in and went crazy. I could tell I was doing a good job because it wasn't long before he grabbed my head.

"Bend over bitch," he said.

I did as I was told without a second thought. Presenting my big juicy butt, begging to be pounded for the first time.

I felt something cold pressing against my hole.

Sensing my nervousness he reassured me, "Relax, it's just the lube, you'll be thankful for it in a minute."

He then teased me for a few minutes before I felt something massive inside me. I thought I might split in half at first, it was so freaking big. Thankfully he took his time, allowing me to adjust. Eventually I did and he started sliding in and out, slowly getting deeper inside then back out. The tempo started to pick up and before I knew it I was fully getting fucked. I mean fucked like a bitch in heat, getting spanked on my fat ass and pulled by my hair.

"Mmmm goddamn girl, I love to watch the way that butt bounces on this dick," he started to shout.

He kept pounding and I lost track of time. It felt soooo good. I wanted to cum so bad but knew I wasn't allowed.

The pounding continued and eventually he said, "get ready bitch, you're about to be bred, then there's really no going back".

He pumped a few more times and then I heard a grunt and felt an explosion inside of me. One final smack of my ass and it was over. I had just gotten bent over and fucked, dressed up like a total whore, and now had my bully's cum dripping out of my butt.

Just like that, my life changed. From then on I was expected to be ready and waiting whenever my master wanted me. He would show up at all hours, expecting me to service him. Sometimes he'd make me wait on my knees for hours. Sometimes he'd make me fuck myself in my sissy seat. I never knew what he had in store. He even invited his friends over sometimes to show off his pathetic sissy. Sometimes they'd host parties and I'd serve as their sissy maid. Sometimes they'd make me twerk for them like a stripper. Sometimes they'd circle around me and I'd go around getting all of my holes used.

Unfortunately like all things, it eventually came to an end. Derrick had to move away and we lost touch. As wild as it was, I was looking forward to putting it behind me. I tried to go back to being my old self. Being a normal guy who dated women. Then out of nowhere I walked into that coffee shop and met Eliza.

Everything was great, or at least as great as it could be for our type of relationship. That is until one day she came home and said she had made a new friend today at the gym. Apparently he was a new trainer and had just moved to town. He gave her an incredible workout and she wanted us to all hangout. I could never say no to her so I agreed. He was going to come over for dinner on Friday and I couldn't remember the last time I'd seen her so excited. She got all dolled up and wore quite a sexy dress that showed off every inch of her incredible curves. She looked like a total knockout and for a second I had a flashback to when I looked just like that.

We got ready and I was in the kitchen preparing dinner when I heard a knock at the door.

"He's here!" Eliza squealed.

I heard the door open and I heard her invite him in to the living room. I kept cooking and she popped in for a second to pour some wine for the two of them.

"You finish up in here then come join us. He can't wait to meet you!" She said as she ran out of the room.

I did just that and made my way to the living room. I heard giggling as I walked down the hall, I think she might've been tipsy from the wine.

I walked in and what I saw shocked me. My beautiful girlfriend was sitting on the couch with her legs sideways, laying across the lap of none other than Derrick! My jaw hit the floor and I froze. He turned to look at me and just smirked. Finally his voice snapped me out of my daze.

"Omg what are the odds? If that isn't my old pal Taylor," he said with a huge grin.

"You two know each other? And his name's Tyler," Eliza said.

"Oops, my mistake," Derrick said with a smirk.

Sheepishly I replied, "yeah we knew each other a bit at school".

"Omg I had no idea! This night just keeps getting better!" said Eliza.

"Your boy here is being shy, we knew each other quite well," he told her.

I don't think Eliza saw it but I swear he winked at me when he said it.

The night continued and I brought out dinner. When I returned Derrick was holding the remote control.

"Derrick says he has a movie he wants to show us. Apparently he was an actor and it's something him and his friends made. Isn't that so cool?!" Eliza said with genuine excitement.

I could tell she was entranced by him like so many others had been.

He patted the couch next to him and told me to sit down. I did just that.

He pressed play and my jaw dropped. It was a video of the greatest hits from our time together. It started with that very first time he fucked me, then progressed to all of the different times he'd used me. All the parties when I was a maid, to the gangbangs with his friends, even a hidden camera showing me sitting on my sissy seat. It ended with me humping the pillow that very first time. I had no idea how much of a desperate whore I had really looked like. Then the final shots were him blowing his load all over my face, showing me covered in cum and smeared makeup, and finally a zoomed in shot of the collar reading "black owned sissy slut".

I was too shocked to speak, too stunned to move. I just sat there frozen.

Derrick had the biggest grin on his face as be turned to Eliza.

"What do you think of your "man"? She puts on quite a show doesn't she?" he asked her.

I don't know what I expected but it certainly wasn't what I got.

"Omg I always knew he was pathetic, and he definitely can't fuck for shit, but I can't say I expected this. I must say though, I'm kind of jealous of how much of a slut "she" was. I never said this, but I used to be a size queen. It was black cocks only for this girl," she said proudly.

Derrick chimed in and said, "oh you just caught a glimpse, Tay Tay here is the biggest slut I've ever met in my life. She'd do anything just for some black cock, right Taylor?"

Resigned to my fate I simply replied, "yes master".

I thought my life was over, and in a way it was, but not the way I expected. Instead of leaving me and exposing me, Eliza decided we were BOTH going to return to being black owned sluts. From that day forward Derrick was both of our masters. My previous rules returned with some new ones added.

His tone shifted to a more serious one, "Now that you're both my bitches, I don't want you getting any ideas. That pussy is black owned only, and you are to be pussy free. Your only sexual gratification will be from getting fucked like a girl. And just so you don't get any ideas, you're going to wear this from now on."

He held up a tiny pink cage. He wanted to lock me up in chastity! My brain was struggling to protest but instead Eliza interjected, "omg it's so cute! Your tiny little clitty is going to look sooo adorable in pink. Besides it's not like you'll need it anyway!"

I was immediately defeated and gave up hope. Derrick pulled out two identical collars, this time mine said "black owned sissy bitch", and Eliza's read "black owned slut". Unfortunately for me, truer words were never spoken. As we would soon find out.