How I Became a Chastity Sissy for Black Men

By Bi Guy

Published on Sep 25, 2024

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After leaving home for a three months business trip, I arrived at my hotel and began to settle in. The hotel was on a busy street with several shops, bars and restaurants, so there would be plenty around for me to do without having to drive anywhere.

I immediately logged into Grindr and updated my status, "SubBttmHotel." I have always been attracted to larger, athletic masculine men. Since I have a very small build myself (5'5", 140#, 27" waist) and can still fit into XL boys clothing, I naturally feel submissive around these men. I found myself especially attracted to the confidence and swagger of black men.

Once I had unpacked, I figured It would get myself prepared for some fun by cleaning out my ass and showering off the airplane stink. I also like to keep well groomed, and since the people I would be working with would not see me in shorts or short sleeves, completely shaved smooth from my ears down. The feeling of having a completely shaved body caused me to become semi-hard and turned on. I slipped on my bikini underwear, shortest shorts, t-shirt and flip flops and settled into the chair to explore Grindr.

While showering, I received several of the usual "sup" and "hi" messages, but one message stood out. His status said, "10inBlkDom" and his message was simple "Hey white bitch" with a photo of his smooth, sculpted body sporting an enormous erection. I clicked on his profile which stated he was looking for a white boy to own and preferred small, hairless guys that are open to poppers, chastity, cross-dressing and bareback. It also stated that limits would be respected and challenged, but he demanded complete submission.

While I never tried chastity and cross-dressing, I wasn't opposed to it. He had my immediate, undivided attention and I let him know that. During our half-hour chat, he learned where I was staying and for how long, my limits and curiosities, and that I had not cum in two weeks so our conversation had me completely turned on. He also wanted to know my drink of choice (Whiskey Coke) and favorite shot (Fireball).

During our final chat topic, he learned that I was cleaned out, shaved smooth and freshly showered. His last message to me was, "OK bitch. Remove your underwear so you are only wearing a t-shirt, shorts and flip flops. Leave everything else in your room but your room key and ID...you won't need anything else. Join me in your hotel bar. I am already there and I am the only black guy in here. You have ten minutes. -Sir"

My heart started pounding and hands were shaking. This was it. The moment of truth. I couldn't believe he was already here. I took a minute to gather myself and replied with, "Yes Sir." I removed my underwear and put my shorts back on, placed all my valuables in the safe, slid my room key and drivers license into my front pocket and stood by the door. It was only 6pm on Saturday and I was free until Monday morning. I had only been in town for three hours and I am already on my way to meet a huge Black Master in a very vulnerable situation.

The elevator ride was the longest ever. The doors opened and I walked across the hall into the bar. The were several people in the bar, but there he was, the only black man in the place sitting alone at a high top table. He was even bigger than I imagined. He looked like he could play for the NFL, and dressed in an expensive looking suit with combat boots. My first thought was if this guy got me alone, he would have complete control and there would be nothing I could do but submit. I was both terrified and more aroused than ever before in my life.

I walked to the table and extended my hand to shake his saying "Hello Sir, I'm David." He shook my hand (his was twice the size of mine), and said, "Hello bitch, have a seat" as he motioned to the obviously gay server. When the server arrived, he ordered for both of us. "I will have a Jack and Coke, and she will have the same...and four shots of Fireball." The server gave me a smirk and a wink. I could feel my face burn red with embarrassment.

As we were waiting for our drinks, he explained to me how the next three months would go. I would remain locked in chastity and only wear panties (no boy underwear). I was to keep my body completely shaved and be available for him to use during non-working hours. I was to obey him completely and would be spanked severely for infractions. My limits would be respected, but he would strongly encourage me to drop or stretch them.

When the drinks arrived, he took one, handed me one, and pushed all the shots in front of me. "Drink up bitch. This should help you relax a bit. Take your time, but finish them by the time I finish mine. When you are ready, you will hand me your room key and ID. This will signify that you agree to be owned until midnight tonight. At midnight, you will have a choice to be released or continue to be owned for the remainder of your trip."

I had not eaten all day so the two shots I downed were already kicking in and I found my self being more relaxed. He also had a very assertive but non-threatening way about him which made me feel like I was not going to be hurt, but would definitely have no choice but to comply. I a weird way, I felt safe. I swallowed the last shot an worked on the last few sips of my drink. By now my head was spinning and I was feeling very submissive. I reached into my pocket and grabbed the two cards, and without hesitation, placed them on the table in front of him.

He put the cards in his pocket and stood up. I stood up as well. He was easily a foot taller than me. "Let's go for a walk," he said. With that, we walked out the front door and down the street. After about two blocks, we stepped into an adult toys store, and were greeted by the owner. "Hello Master Dan. Who do we have here?" My new owner said, "This is Britney. She needs a cage and some panties." I again felt myself turning beet red, but this time was different. The booze in my system made me feel more naughty this time. The clerk came around the corner and put his hands on my shoulders, "It's ok sweetie, there's no judgement here. I know what he wants. Go back in the change room and take your shorts off. I'll be there in a sec."

I made my way back to the changing room and removed my shorts while I came to terms with the fact that I was now "Britney." The clerk soon came in holding a pink chastity cage, hand lotion, a towel and some tiny pink satin panties. He had me apply a generous portion of lotion to my cock and balls and the instructed me on how to install the cage. Once completed, my 7" cock was reduced to a 1" nub. The feeling was amazing! "He likes his gurls to have the smallest possible clitty, and whatever you do, don't call it anything else around him, and your ass is a pussy, got it?" I nodded my head, and with the he returned to the counter.

I stepped into my new pink satin panties and admired myself in the mirror. They were just big enough to fit, and with my new cage on, it looked like I had nothing in front. I could feel my clitty stiffen up at the sight of the gurl in the mirror. I slid on my shorts and made my way back to Master Dan. He was just finishing his purchase and I noticed him putting a couple small bottles of poppers and lube into his pocket. He turned to me and asked how I was feeling. "A little tipsy, and with my clitty locked and panties on, I am feeling very submissive." "Good bitch. Let's continue," he replied, and out the door he went. I followed obediently.

We continued down the street for another two blocks until we came to a storefront that had no signage, just all blacked out glass. He opened the door and ushered me in. We were in sort of a foyer with a second blacked out glass door. He showed the bouncer my ID and he waived us in. He opened the second door into a long dark hallway. Halfway down the hall was the admission and coat check counter with a third blacked out glass door. I could hear music coming from door at the end. There was a sign that stated "The County Health Department Requires Shoes and Underpants Must Be Worn At All Times ."

He looked at me and told me to remove my shorts and shirt and give them to the person behind the counter. I looked a bit dumbfounded for a few seconds when I realized I would be in public in nothing but panties and flip flops. I was immediately snapped to reality when he yelled me, "Now Bitch!" I quickly removed my clothes and handed them over. The attendant placed my clothes in a bag and hung it on a hook, then proceeded to write a 22/23 on my chest with a sharpie.

While I was getting prepared as ordered, he put a few things in a small black fanny pack. He then handed over his coat and removed the rest of his clothing so that he was wearing nothing but a black leather jock and black combat boots. I was in awe of the the sight before me. He was massive, and the jock could barely contain what was inside it. I suddenly felt very small but safe at the same time. Once everything was set, the clerk wrote a 22 on his chest, then looked at me and said, "23, your clothes will not be returned unless you are escorted or released by 22. If you understand and agree, indicate so by stating a verbal yes." As if in a trance, "yes" automatically came out of my mouth. With that, he circled the 23 on my chest. "Welcome and enjoy!" We continued down the hall and through the door.

Once through the door, I was relieved to find the almost everyone was only wearing underwear and shoes, including several skinny, hairless "bois" wearing panties. The place was dimly lit and the music playing was just loud enough to mask any conversations happening. There was no DJ yet since it was so early, but they had the dance floor lights on and there were a couple of bois in panties dancing that seemed to be enjoying some sort of chemical induced euphoria.

I followed my Master to the bar where he ordered two more drinks and a couple more shots of Fireball for me. I pounded the two shots and within a couple minutes began to feel the effect. With the drinks I had before, these two pushed me to the point where I started to feel horny and uninhibited. I suddenly realized I was in a room full of people in nothing but flip flops, panties and a chastity cage, and it was beginning to bring out the gurl in me, dancing in place and presenting my ass to everyone. I was getting a lot of looks from the other men which was really turning me on.

Master Dan noticed and said, "I knew you were a sissy faggot. You just needed help finding your true self. Just wait til I fuck you through your second hole. You really gonna know what it's like to be a gurl. " I had only heard about the "second hold" but never experienced it. I couldn't wait!

We made our way to a corner high-top table. It was in a secluded corner away from the main area. "Take off your panties and flip flops and put them in the corner," he ordered. I did as I was told as he began to inspect me, squeezing my ass and pinching my nipples. He told me to suck on his finger and get it nice and wet as he shoved his finger in my mouth, but It obviously wasn't eager enough. He slapped me across the face and grabbed me by the throat. "Suck it like it's a dick!" I sucked like my life depended on it.

Once it was nice and wet, he pulled it out of my mouth and started to work it into my ass. "Push that pussy out and let me in." He reached into his fanny pack and handed me a bottle of poppers. "Take four deep hits of this." I sniffed long and deep and soon felt the familiar effect, and like magic, hid finger slid all the way in. I let out a bit of a gasp. His finger was almost as big as most dicks I have taken before. I noticed we were building an audience, but the poppers made me enjoy the attention.

With one finger in my ass, he reached into his pocked and pulled out a butt plug with his other hand and shoved it in my mouth. I knew what was coming next so went to town getting it wet. "Four more hits," he said as he pulled the finger out of my pussy, pulled the plug out of my mouth and pushed it into my pussy. By now my head was spinning and with the plug in my pussy and the cage on my clitty, I was now in full slut mode, ready for anything. "Good bitch. Put your panties back on."

While we were enjoying our drinks, several of his friends stopped by the table to say hi. Each time, he introduced me as Britney, the faggot auditioning to be his new bitch. They talked about me as if I wasn't there, each giving me a smirk as if they knew something I didn't. By now I had lost count of the drinks, but I knew I was feeling well. the combination of the plug, panties and cage had me acting like a cat in heat and my clitty was dripping like crazy.

The place was pretty full by now so we were surrounded by guys in their underwear, including three of his friends hanging out at the table. One of them asked, "how well does she suck dick?" "I don't know. Let's find out," he said, turning to me. "Four hits of poppers, bitch." I took four hits of poppers and instinctively dropped to my knees. Normally I would be apprehensive about sucking a dick in public, but the booze and poppers removed all inhibitions. I slid his jock down and his thick, veiny cock popped out and hit me in the face. I took him in my mouth and sucked him the same way I sucked his finger earlier.

He continued his conversation as I sucked him off. I could hear an occasional cat call and comment. I loved the attention and my clitty was oozing and straining against my cage. "If this bitch's pussy is half as good as her suck hole, she is going to be a lot of fun," he said to his friends. They all laughed and one asked, "Why don't you find out right now? "Good idea," he said. "Bitch, take off those panties and stand up." I stood up and placed the panties on the table.

"Put your hands on the table and do not take them off." He positioned himself behind me and began pulling the plug out of my pussy. Once it popped out, he shoved it in my mouth, which forced me to breath through my nose. The taste of my ass juices turned me on even more. He pulled some lube out of his bag and greased up his cock and my hole, then pulled my hips back and positioned him self at my entrance. With one hand on my hip, he held the open bottle of poppers under my nose. Since I had to breath through my nose, I was soon seeing stars. The combination of the poppers and the position I was standing caused my pussy to automatically push out and open. I was ready and he knew it.

He began a constant push inside me until he hit bottom and held it there, moving from side to side. I had never felt so full of dick and the intense pressure on my prostate caused me to shake a bit. He started fucking me slowly, only pulling back an inch or two and then hitting bottom again and again. He let me know that he was only half way in, but I could barely keep my balance since my knees were so week.

After about five minutes of this, the moment he was waiting for arrived. He could feel I was wide open and breathing heavy. He held the bottle up to my nose which forced me to inhale several big huffs. This time when he hit bottom, he began to push into me harder, when suddenly "pop!" Something inside me popped and all ten inches slid the rest of the way into me. I let out a loud "Ooooooh!" and nearly passed out. He held me tight so I wouldn't fall as everyone around us noticed and started to watch the show. he whispered in my ear, "That's your second hole opening up."

Once I regained my composure, he let go. I can only explain was happened next was that I bloomed like a flower. I was completely wide open like never before. He began to fuck all ten inches into me, slow but steady. Each thrust forced a bit of cum to ooze out the hole in the end of my chastity cage. I was moaning like a banshee and shaking uncontrollably as I had several anal orgasms. He wrapped his arms around me to hold me up and basically used my like a human fuck doll. I felt him swell up as he let out a ROAR and buried his cock all the inside me. I could feel him shoot a burning, massive load into, at the same time something shot out of me as I screamed. It was either piss, cum or both...I can't be sure.

He let go of me, causing me to drop to the floor, shanking and whimpering, as his load ran out of me, down my leg and on to the floor. The audience around us erupted in a round of applause and then quickly went about their business. Once he caught his breath, he pulled up his jock, slammed the rest of his drink and squatted near me. "Do you want to continue for the next three months or do you want to be released, bitch?" "I - - want - - to - - continue - - sir," I replied. "Then ask me properly, bitch."

I knelt in front of him with my head down, "Please may I be your bitch, Sir?" He thought about it for a bit and responded. "Yes you may. Tomorrow, I will bring you an entire sissy outfit. When I message you, you will have one hour to clean your pussy and get dressed. You are to act like a sissy bitch whenever you are dressed. If you disappoint me at any time, you will be spanked, bare ass until you are bright red. See you tomorrow, bitch." He stood and walked out the front door, leaving me a naked, kneeling on the floor.

I gathered myself, put my panties back on and made my way to the clothing counter. When I reached the counter, the clerk said, "22 has released you," and he handed me a bag containing my clothes, ID and room key. I quickly dressed and walked back to my room as his cum continued to run out my pussy and down my leg. During the walk, I began to run the evening through my head, realizing that while I had several orgasms, I had not actually cum, and was horny as ever. Unfortunately, the chastity cage would prevent me from masturbating and seeking relief.

The next night he messaged me on Grindr, and the night went just as he described. After about a week, he was able to push all the way into me with one stroke, and bred me dressed as a gurl every other night for the next three months, only releasing me once a week to clean. After two weeks, I was constantly aroused and dripping, and thought only of him fucking me as any sort of relief, and I craved it.

On my last night, he removed my cage once his cock was buried inside me, and started stroking my rock hard clitty as he fucked me, holding off so that we would cum at the same time. I have never cum so hard and so much before or since. I think I actually passed out. Once he was done, he walked out the door and blocked me. I never heard from him again.

To this day, I am only interested in dominant black men, and I must be locked in chastity when meeting someone, and if they let me dress as a sissy, it's even better!

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