My disclaimer:
This TG story is completely true. I live and work full time as Christina and have for almost 24 years. But I had not had an encounter like this until 2002. Up until then I had dated very little and most of my intimate encounters had been with women or other TG's
Classification of this story is TG
My name is Christina Marie Rosales
E-mail luvlaceandsatino1@gmail.com
This is my first story submission. I can be reached for any clarification on the story through my e-mail
My Journey to Sissification with Frederick
I have always been a crossdresser and it was more of a way of life to me and not a sex fetish. It felt so natural and over the years I had become very comfortable with it. It was not a secret at work for I often wore feminine clothing such as girls jeans, blouses, and girls sandals. A few times I have worn business dresses, and always very conservative. I also always felt very comfortable with all the women at work and they treated me as if I were one of them. I would wear very light makeup, and always kept my hair very long.
Although up to this story, I had never really dated men, even though I was very attracted to them. I always felt awkward, and when it came to kissing, I wanted to so much but they would be so rough with me. And they would want to feel me up and I wanted to stop them and take it slowly. I would say no, and then they would never ask me out again. I wanted my sexual experience to be deep and personal, and not something like a one night stand.
So this story begins with my regular trip to the grocery story on Thursday after work. Is a Safeway in my neighborhood that I go to every week. I was wearing a long tan skirt, a lacy top, 3” brown pumps. So I wasn’t like making a fashion statement or trying to attract anyone. I would always bring my own bags and push a basket and carry my list. This day, I notice a tall Black Man who was gorgeous in one of the rows, and when we passed he remarked “hello beautiful”. I smiled and said “thank you” and passed on. I felt this little excitement and sort of stumbled in my heels and he reached out and grabbed to so I wouldn’t fall. When I looked into his eyes I could feel his power and it was overwhelming. I muttered something and he said “Do you need help?” I said no and moved on. But I could feel his eyes on me as I reached the end of the row and turned.
I finished my shopping and paid for the groceries and headed towards my car. When I got there and opened my purse to find my keys, he came up behind me and asked “Shall I help you with your groceries?” This time I submitted and said yes. I opened the trunk and he placed all the bags into my car. I watched his strong muscles and the way he moved, and my eyes fell to his crotch, and he caught me looking. “See something you like”? he said. I again smiled and looked down, and he reached out to my face and gently moved my head so I looked into his eyes and he said “You need a man like me, don’t you?” I was so weak in my knees and I just looked into his eyes and muttered “Yes, I do”. He then said he had seen me before several times and he had hoped to meet me that day. He said “I know you are a TG, and I want you to be a sissy for me, and I want you to come to my home this evening and let me show you how”. I couldn’t say no even though I was scared and excited at the same time. He then said “Give me your number, and I’ll call you and tell you want to wear when you come to my home” So I gave him my number, and he kissed me on the cheek, patted my behind and said “Tonight you will learn to be a proper sissy”.
I rushed home, unloaded and put away the groceries and jumped into the shower and cleaned myself all out. I didn’t need to shave my legs or anything for that matter as I am naturally hairless all over. But I did a touchup in my pubic region. I pulled out some panties and bra when he called me. I answered and he said “I want you to dress like a sissy, a short dress, ruffles, poofy slip, garters, white stockings, gloves, highest heels you have and curl your hair. Now write down my address and I expect to see you here in 2 hours” I said yes, and he replied “Say Yes Master”. And I said Yes Master, and he said “Good” and hung up. I had a sissy maid dress that I had only worn once and it was packed away in a box. I panicked because I need to iron it and find all the things that go with it. And I had to turn on the curling iron, dig out my highest heels and luckily I had one pair of white stockings as I don’t often wear them. Nothing really matched as the garter belt was pink, the sissy maid dress was black and white, and the highest heels were red. I looked at everything and sighed and said “Here goes”. I got completely ready and made my face, curled my hair and set it with spray, grabbed my purse and cell phone, took one more look at the mirror by the door and thought “You look like a sissy whore” and out the door I went. I carefully walked to my car in the driveway almost falling 3 times. Once in I set the gps and headed off to his home. I got to his house but not in the two hours, from his call it was 3 minutes past the time. I hurried to the door, rang the doorbell, and he appeared. He said “You’re late” and I said I got here as fast as I could. He took me by the hand, led me in and closed the door. He said “Get on your knees” and I obeyed, and me brushed his crotch against my face and said “You will learn to be on time and to obey me, and to obey my dick.” He took my hand and raise me back to my feet and told me to walk across the room and make sure to sway my hips. I did this and he told me to spin around so he could see all of me, which I did. Then he said “Come here and I did. When approached him, he told me to get on my knees again, and when I did he said “Always look up to my eyes first, say Master, and then look down” And I complied. He chuckled and said, stand up, sissy, its time to begin your training. I did and he took me tome one of his bedrooms.
In the bedroom was a table with many items. The first item he picked up was a pink chastity device which he put on me. He said that I could no longer pleasure myself and this would help me learn to pleasure him completely. The next item he picked up was a buttplug that was huge. He told me to turn around and bend over which I did, and he lubricated it, pulled my panties down, and placed it inside me. He then pulled my panties back up. But the bulge of the chastity device could be clearly seen. He took the next item which were a set of furry handcuffs and he put my hands behind my back and handcuffed me. Then he took a collar with a leash on it and placed it around my neck. The last item he took was hobbles that tied my ankles together so I could only take tiny steps. He then took the leash and led me all around the house with it, slowly as first so I can learn to walk this way. All the time he kept talking to me explain what each item was for and how it would help develop me to becoming a true sissy.
He then took me outside to the backyard, and he had a nice patio area with a sofa, and Jacuzzi and a pool. He took the leash off and told me to walk around freely and get used to being outside like this. I loved the feeling of the breeze under my very short dress and the way the chastity device wiggled as I walked. He told me to come to him, and I did and he said “From now on, when I call you, you come and fall to your knees look up and say “Master” and then look down” So I did this and he touched my head and said “You are my good sissy, and soon you will fall in love with me” He had me bring him refreshments, and clean up the kitchen and a few other things. Each moment though I was becoming more and more comfortable this way. As the evening was getting late, he told me that he had to work and he knew I had to work, and that it was time for me to go home soon. He called me and I went to him, and as I was on my knees before him with my head bowed, he told me “Pull my dick out and kiss it” I did this, and he moaned, and said “Kiss it again” I did this and he asked me to take his dick into my mouth. By now my mouth was watering with desire to do this. I did, and I started to suck and he said “No, just let my dick lay there in your mouth. I want you to get used to my dick being in your mouth.” So I kneeled there with his dick in my mouth for about a minute, and then he said “Suck it, gently” so I did, carefully and gently. His dick started to grow and get larger, and soon I could barely wrap my lips around it. He then grabbed by head and forced his dick all the way down my throat and I worked hard to keep from gagging. He held it there in my throat for about 10 seconds, and then pulled it back and said “Make me cum in your mouth” So, I started giving him the best blow job I could possibly give for the next 10 minutes. My mouth hurt because of his size and my jaw felt like it was dislocated. Just before he came, he said “You are my sissy and I love my sissy. And because I love my sissy, I am going to let you taste and swallow my semen” with that he exploded into my mouth. I had to swallow 3 times to get it all down. I had semen dripping down my chin, and onto my dress. When he finished he pulled me up, and said “I want to see you tomorrow night, same time, and wear the same thing” I said “Yes Master”. He said he had wanted a sissy for his own for a long time and then he confessed that he had been stalking me for 3 months, he knew where I lived, where my parents lived, where I worked, and where I banked. I was a little scared but he said that he wanted to know who I was and that he was watching me to make sure that I would be a real sissy and become even more of a sissy for him, and that he wanted me to come out more at work, wear sexier dresses, and make him want me every night. He would be the Master/boyfriend and I would be the sissy/girlfriend. He then gave me a queen of spades sticker and said “Place this sticker on your ankle, and wear a short dress and sandals tomorrow so everyone can see that you belong to me. He then took off the collar, handcuffs and hobbles, and placed a necklace on me that said “I Love BBC” and told me to wear it from now on. He also said I could take off the chastity device so I could continue to “pass” at work, but that I must wear the buttplug everyday for a week, so I would be open enough to take his dick inside me. He then kissed me on the forehead and told me not to wipe off his semen from my face until the morning. That I should learn to love to wear his semen proudly.
All the way home all I could do is think of him, and how I would please him the next night and the next night, and how in a week I would feel his dick inside me. It was so big it scared me, but I knew I had to feel him.
The next day i proudly wore a mini sundress to work, with sandals and my painted toes, with the queen of spades clearly seen, and my new necklace. All the girls stared and then smiled. Some even winked at me. One of the girls came over to my work station and whispered in my ear “Now you’re a real girl, Christina, there is no going back” she giggled and told me congrats.
I had to excuse myself and go to the ladies room because I was leaking in my panties thinking about him! I had to place a pad to soak up the leaking, I was so horny for him!!
And that’s how I became Master Fredericks Personal Sissy