True story: How one beceomes sissy. Written by Stephanie

I guess my story is like a lot of other transgenders. I have known since I was very little that something about me was different. I learned at an early age though that voiceing how I felt was met with much resistance and sometimes even disdain. So I hid my true self for so long. I learned to be a boy, even though it always felt wrong. But after several failed marriages and a life changing event, I finally admitted to myself who I truly am. I am Stephanie. That is where this story begins.
After splitting from my last wife and moving into a place of my own, my feminine side, my true side, started to take over. The new found freedom allowed me the time to express who I truly am and have always wanted to be. I started by searching the internet for a site that was designed to help me in my journey to become more feminine. I found places with hypno MP3’s and such, but then one day I stumbled upon the perfect site. It is called Anna Malice Sissy Self Hypnosis. It had everything I was looking for! Stories, hypno gifs, videos of all sorts, it is a sissy’s paradise! It didn’t take long after finding Anna’s site that I started to move full steam into my transition from wimpy male to a sexy and slutty female.
I started buying all sorts of womens clothing. I am blessed in that I am tall and slender, so it made it rather easy for me to find clothing. Panties and bras came first, then jeans, blouses, shoes, dresses, makeup, wigs, breast forms and lingerie. I went a bit crazy buying things at first. The first time I applied makeup, I must admit I looked like Frankensteins bride, LOL! But thanks to youtube, I watched several videos on how to apply makeup and soon got at least adequate at appling it. My ultimate goal was to be passable in public. I didn’t want to look like a man wearing womens clothing and makeup. I wanted to be a woman.
My first foray into going out as Stephanie was a successful one. I went with a friend that I had made on Yahoo to the Halloween parade in Chicago’s Boystown. I had a professional makeup artist do my makeup that night. When he turned me around to the mirror and I saw myself for the first time, I was stunned and so happy! I was actually seeing ME in the mirror for the first time in my life! I won’t go into all the details about that night, but suffice to say that I passed as female and I had the time of my life!
After that night and getting pretty good at applying my own makeup, I started to surf transgender dating sites and places on the internet where men who were looking for transgender women congregated. It didn’t take long before I found “THE MAN” for me. He was a bit older than me, sweet yet dominant, willing to help me with my transition and best of all…he is Black! I have always had a thing for Black Men, I don’t know what it is. The skin contrast, the way they are alpha males. We talked online and got to know one another really well. We discussed my boundaries, what we wanted out of a relationship both sexually and emotionally, about my transition and just everything. It wasn’t long until we set up our first meeting. Now comes the good part!
We decided to meet for a 3 day, 2 night date in Indianapolis. He is from Dayton, Ohio and I live west of Indy, so it was a convenient place for us both. He booked a nice hotel for us. Very nice room with a king sized bed for our playground. He arrived before me and got checked into the room. He then went out to do some shopping. I arrived shortly after him. He had left me a key at the front desk. My instructions were to go up to the room, get myself all femmed and sexy for him and text him when I was ready. Since I wanted everything to be perfect, it took me almost two hours to get completely ready. My makeup, hair, clothes were all ready and so was I. We were going out to eat at a casual restaurant, so my clothing was casual as well. I wore a skin tight pair of teal colored jeans, a white cami top and high heels. Of course under it all was a very sexy pair of panties, bra and thigh high stockings. I texted him that I was ready. He immediately texted me back and told me that he was in the lobby of the hotel and for me to come down to meet him there.
I waited about 5 minutes, checked my hair and makeup one last time, then opened the door and walked out into the hallway towards the elevator. As I made my way to it, I passed a married couple. I noticed as I passed by, the husband checking me out. He turned and checked out my ass as i walked by, which promptly got him smacked by his wife! Even after the smack, he still watched me walk to the elevator. So I made sure to add just a little extra shake to my hips and ass. As I got in the elevator, I turned and winked at him as the doors closed!
When the elevator reached the ground floor, the doors opened and I saw my Man sitting on a couch in the lobby, reading a newspaper. I took a deep breath and confidently walked in his direction. As I strode towards him, he looked over the top of his paper and saw me. A huge smile spread across his face as he folded the paper and stood to greet me. He held his hands out to me, I took them and he pulled me into an embrace. First a hug, then a long deep, lingering kiss. It started softly, just our lips meeting, but soon our mouths opened to one another and our tongues found the other and the kiss deepened. I felt his hands slide down my back to my ass. I could feel his manhood stiffening in his pants as the kiss got more intense and as he squeezed my ass. When we finally broke the kiss, I noticed several people in the lobby staring at us. I just smiled, took him by the hand and we walked outside into the evening air.
The restaurant where we were dining was close to the hotel so we decided to walk. We walked hand in hand down the street, making small talk about Indy, the weather and other things. We arrived at the restaurant and was quickly seated. We talked about all sorts of things through an incredible dinner. It was easy to tell we were hitting it off very well and there was an intense sexual passion hanging in the air around us. We decided to forgo desert in order to get back to our room, as our passion was bound to get us in a bit of trouble in the restaurant. We couldn’t keep our hands off one another all through dinner!
Upon arriving back at the room, he opened the door and let me in. As he closed the door, his demeanor changed, as I knew it would. We were now in a bedroom and I was his sissy. He was now in control of me totally. He grabbed me and kissed me hard, shoving his tongue deep into my mouth. I greedily sucked on it, tasting him. He broke the kiss and pushed me away. “Get out of those clothes, now bitch!”, he commanded. I took a step back from him so he would have a good view as I undressed for him. I first took off my cami top, to show him the sexy bra underneath. His eyes were shining with lust and excitement as I shed each piece of clothing. As I took my jeans off and let them hit the floor, he saw my sexy panties and the thigh highs for the first time. He walked over to me, grabbed me and turned me to the wall and said, “Stick that ass out you sissy bitch.” I leaned forward and planted my hands on the wall, arched my back and stuck out my ass. “Such a fine sissy ass you have there gurl”, he told me as his hand came down hard on my left butt cheek with a loud SMACK! I felt the warm stinging sensation as a bright red handprint became visable on my ass. The first smack was quickly followed by another loud smack on my other ass cheek. “Oh, fuck yeah! You like that, don’t you sissy?”, he asked me. I breathlessly replied that I did, which brought about another two quick but firm smacks on my ass. My ass was stinging and bright red, but it felt so good!
He moved behind me and grabbed my wrists, pulling my hands from their position. He pushed his body against mine, pinning me to the wall. He kissed me on the neck and whispered in my ear for me to turn and get down on my knees. He released his grip on me, I turned and immediately dropped to my knees before him. There was an obvious bulge in his pants. I reached up to undo his pants but he smacked my hands away. “Uh-uh, not yet bitch. You just stay there on your knees with your hands behind your back until I tell you otherwise.”, he ordered. I quickly complied and put my hands behind my back, interlocking my fingers. He looked down upon me as he started to unbutton his shirt. “Look at you”, he said, “Fucking little white sissy bitch whore on your knees in front of a Black Man!” I just looked up and him and smiled, not knowing exactly what to say, I just knew his words were true and made me so horny for him! He finished unbuttoning his shirt, pulled it off and threw it on a nearby chair. For his age, he was in very good shape. His chest was muscular and well defined. His stomach didn’t show a bit of fat, it was tight and smooth. HIs chest was slightly hairy and very sexy. He watched with a bemused look on his face as my eyes drank in his features. I’m sure he could see the fire starting to burn in my eyes. My need and desire for him was growing by the second.
“Now you little sissy bitch, now you can undo my pants…but slowly.”, he instructed. I reached up and carefully opened his belt, the button on his pants, then I slowly slid the zipper down. His Big Black Cock sprang from the confines of his pants and smacked me in the face. Before it stopped moving I caught it with my mouth and started to gently suck the head. His precum had already started to flow and it tasted so good on my tongue. “Oh hell yeah, now that’s what I’m talking about”, he said, “You caught that Black Cock with your sissy mouth before it even stopped moving! What a cock hungry slut you are!” I moaned my agreement as I started to suck more of his impressive cock into my mouth. He was cut, almost 9″ in length and very thick. I had to open my mouth so wide to allow him access. He placed his hands on the back of my head and started to fuck my mouth, forcing more of his cock in with each forward thrust. He reached the back of my throat on about the fifth stroke and caused me to gag a bit. He didn’t care. With his next thrust he went even deeper, forching his thick, hard cock into my throat. He had a very firm grip on my head and I couldn’t move away as he shoved the entire length of his cock down my throat and held it there. “Fuck yeah slut, take ALL of that Black Cock! I fucking love it!”, he exclaimed. I did my best not to gag anymore and to open my throat to his assault on my tonsils. Tears started to run down my face as my eyes watered. But neither of us cared. He was fucking my sissy throat and I was in heaven. A MAN was finally using me as I wanted and needed to be used!
He finally withdrew his cock from my throat and rubbed it all over my face, covering my face with his precum and my saliva. He smacked my face with it a couple of times then told me to get on the bed. I crawled over to the bed, I knew better than to stand. I was to be submissive and on my knees for him, never on my feet unless he told me so. I climbed up onto the bed as he instructed. “All the way up to the head of the bed, bitch”, he ordered, “face down ass up like the fucking white trash whore you are!” I obediently moved to the head of the bed and lowered my face and raised my ass. I felt two more sharp smacks on my ass, bringing the bright red color back to my cheeks. He reached up and literally ripped my panties off of me, completely destroying them. Two more spanks on my upturned ass followed. He then grabbed my ass cheeks and thrust his tongue into my already moist sissy pussy. I moaned loudly and pushed my ass back against his face as his tongue probed my sensitive boi pussy. He licked me for a few more minutes, bringing my lust to a fever pitch. As he withdrew his tongue, he spanked my upturned ass again…two smacks on each cheek. My little sissy ass was on fire!
I heard him spit on his cock, then I felt his hands on my hips. He rubbed his throbbing cock across my sissy pussy a few times and then I felt the head start to enter me. I instintively pushed back against him and let out a low moan as his cock penetrated my sissy pussy for the first time. He stopped and pulled back just a bit, then his grip on my hips tightened as he slowly pushed the entire length of his Black Cock inside my eager pussy. He held it there, deep inside me. “Yeah, you like that don’t you sissy? You like that Big raw Black Cock deep in your fucking sissy pussy, don’t you?”, he hissed. I answered with a breathless “yes” and pushed my ass back against him. My pussy was so full and so stretched, it hurt just a bit. But the pain very quickly turned to pleasure and he began to fuck me in earnest. His hands still having a firm grip on my hips, he fucked me hard and deep, with long strokes. Slamming his cock into me with each thrust. I opened the bottle of poppers that I had in my hand, took two deep hits and my lust overflowed! He started pounding so hard…I could feel his heavy balls hitting mine with each powerful thrust. Soon I felt him start to stiffen and his cock got even bigger inside me. I could tell his first orgasm was approaching and that triggered mine. As I started to squirt my sissy juice onto the bed, my ass pussy started milking his cock. It was too much for him and with one final incredibly deep thrust, he emptied his balls deep inside me. I felt the hot cum rush from the head of his cock. I felt the heat of his seed as it spread through me. This triggered my second orgasm and I bucked wildly against him. My sissy clitty squirted more sissy juice onto the bed as he pumped jet after jet of hot Man cum deep inside my sissy pussy. We both finally collapsed forward onto the bed, his body pinning me down with his cock still inside me.
As our breathing started to become normal again, he rolled off of me and lay on his back. I rolled to my side and could see his cock glistening with his cum and my pussy juice. I slid down and took his cock into my mouth. I knew that he expected me to clean his cock and I wasted no time. The co-mingled taste of his cum and my pussy on his cock was intoxicating! I felt his hand snake down my back, then a finger easily slid inside my fell fucked pussy. He left it there for a couple of seconds, then pulled it out. It was covered in his cum. He brought his finger up to my face and I opened my mouth and sucked his sweet nectar from his finger. I had left a butt plug on the night stand before our dinner and he told me to raise my ass so he could insert it. I was to keep his cum inside of me, to not expel a single drop of it. His cum was to be joined with my body through osmosis. His seed would spread to every cell in my body, his DNA infusing itself with mine and taking over, creating the need for more of his seed on a daily basis. He inserted the plug, then told me to suck his cock hard again. His second load was to go down my throat so that I would be seeded from both ends for the maximum effect of his DNA taking over mine. I sucked his cock for all I was worth. First making him hard again, then after a time feeling him stiffen and his cock explode his next load of cum deep into my throat. I swallowed it greedily, taking every drop. I now belonged to him, he owned me and that is how I wanted it!
We had the most amazing stay at the hotel. He took me two more times the first night. The second night two other BBC’s took me as well as he watched then joined in. He had placed an ad on Craigslist, unbeknownst to me. But I didn’t care. I was his to do with as he wanted. They all fucked me bareback the entire night, pumping load after load of hot semen into my willing body. My transformation into a BBC cumslut was complete and my devotion to him was unwavering.
Since that first weekend together, I have moved in with him. We found a nice place in Indy. My transition to female is going very well. I have started hormones, I have a fantastic new set of 38D breasts that he bought for me and my closet runneth over with sexy clothes, lingerie and high heel shoes. I am in sissy heaven. I am owned, as I should be…as I always dreamed and wanted to be….my life now has meaning and is complete! I had become the sissy I always wanted to be!

Authors note: If you like this story and want to read more of our adventures, please let me know in the comments section. Of course constructive criticism is also appreciatied. Thank you for reading my story!

Stephanie <3