Sissy training

Hello, this is my transformation story. It all happened 2 years ago. I was just a normal 22-year-old boy. I had a normal life, a normal job, and good friends, and everything was going great. I should have been happy, but I was not, something was missing. I trained a couple of times a week, but my body always seem a little skinny and girlish, and I could get a girlfriend. Come to think of it I didn’t want one, I just wanted to watch movies and play games all day. The days were coming and going and I mostly did what I want, but I kept being border with my life. Due to my boredom, I started to chat with strangers online. I loved to visit, chat rooms, live camera shows, and so on. I met a lot of people that way, and It was nice entertainment for a while, plus I loved to hear about people’s sexual experiences and stories. This started to turn me on, and not only a regular story the kinkier the better. I got really into, trannies and sissy stories, I found the idea of being fucked like that fascinating, and given the way I locked it was perfect for me. Moving forward I found an ad for “sissy training” and an email nothing else. I decided what the heck let’s check this out, thinking that this is most probably a fake, so I wrote a quick email saying hello and that I’m interested in the ad and that’s all, and I went to bed. The next morning, when I checked my email, I saw a reply with a skype name, so I just added them. I figured I needed a girl’s name so I just typed, “Hello I’m Viki”. In an hour or some, I got a reply, “good you already got your slut name picked, you ready for your life to change”. I was surprised by that reply and a little excited, I still thought this is not real, but some scam. Still, I replied with “Yes”, and since I wanted to know more, I asked for more information to prove this is not a scam and so on. And the reply was, that this is not a scam as there is no money involved here, and if I’m willing to join the program, we can make a call and everything will be explained. I thought about it for a while, what program, I was ready to forget It, but my curiosity was big and I figured a conversation won’t hurt, so we agreed on a time and made the call.

Before the call, the person on the other end asked if I mind turning on the camera so we can see each other, and I didn’t want to reveal who I am at first so I said no problem, but still made the call with my camera off. When she picked up, the first thing I saw on the other end was this beautiful woman, with large breasts, red hair, and lipstick, wearing a red nightgown, and smoking a cigarette. She told me she couldn’t see me, I was still not sure if I wanted her to see me, but she was so hot I could resist.

• “Great I can see you now, my name is Dahlia” – she said with a smile.
• “Hello. I’m ….”
• “You are Viki right?” - she interrupted me.
• “Yes.”
• “Love to finally see you, how are you.”
• “Good.”
• “Great, I guess you have a lot of questions, about the short ad with no information, and what is all this about right?”
• “Um, Yes, not sure what we are even talking about, but I was curious.”
• “Curiosity is good; it will help a lot. Look let me give you a quick explanation, of who I am and what I do and if you agree to my term we can talk more and I will try to answer all of your questions without spoiling the fun.”
• “Sure.”
• “Great, ok let me start with that, I wasn’t born Dahlia, this is the name I chose, and that’s why I said it’s good you also have chosen a name that is the first step. I’m a trans woman, 10 years ago I discovered who I am and I loved every second of my life since then. I’m also a very successful businesswoman, I have my brand of lingerie and sex toys. So let’s say I’m doing good in life. Since my transformation, and yes the breasts are fake, I decided I want to help young people discover who they are. But also I like to do it in my unique way for a special few, and I hope that is you. As I said I don’t see any money, I’m just there to help and have fun, if you are willing to go true to my program I promise you, you will not regret it. But I need to know you are in before going any further, I want you to be committed and finish the whole program no matter what.”
• “I’m sorry but I’m still now understanding what this is all about.”
• “Oh, sorry, the program I’m offering is sissy transformation, what that means is I’m helping you discover your true secret identity. My program will teach you all about how to become an obedient little slut, and it is all free and private. After completing the course, you can keep living the way you want and have fun in secret, you can embrace your new self the way I did, or just go back to your old life, and just have some unforgettable memories. Also after we start, if you feel like this is not for you, you can quit, but I’m only giving you one chance, if not I expect you to do what I say. Sound interesting?”
• “Yes, very interesting, I’m not sure what to ask even”
• “Awesome, let me give you some more details first.” – she replied with a smile. “But before that, I’m letting you know I have done this a couple of times, and I like to keep it private, you don’t tell anyone, and you don’t say anything, this is a special opportunity I give only a few people, and I don’t know why yea, but I chose you. I normally post this ad for a day once a month, and I get tons of replies, with a lot of questions, but I like how simple your email was, I had a feeling you can say. So you willing to keep this a secret, the conversation and everything that happens after, and are you willing to let me transform your life? I will let you think it over.”

My mind was going like crazy, what will this be, what will happen, will I like it, I know what sissies do in movies, and I read stories but is this for me, I have never even touched another man’s cock. But then again, ones in a lifetime experience, and she said it was all a secret and I can quit if I want. I don’t want to waste this opportunity. Although scared, I was so bored with everything that there was no way, I would say no to this.

• “Miss Dahlia, I’m in, I agree to keep all of this secret.”
• “Fantastic, and relax sweetie you don’t need to call me Miss, yet.”
• “But I wanted to tell you, I’m not experienced in all of this, I just like to read stories. I have never even touched another man’s dick, and I have had sex just a couple of times, with girls.”
• “O that’s fine sweetie, even better my first virgin, I’m so excited. What made you contact me then?”
• “Honestly I was bored, but also I loved to read stories about, sissies and to watch gay and trans porn, I like it, and it seems like something I want to try but never dared to do so. Even now I’m still a little scared.”
• “Don’t be Viki, I can feel we will have a lot of fun you and I. So let me explain how this will go now. All expenses are going to be paid by me, I will book you a flight and you can come to me. We will set you in a nice hotel. Then your transformation will begin. I don’t want to spoil anything yet, but we are going to be together and have tons of fun. I want you to take a 2 weeks’ vacation from work or whatever, tell everyone else you are on a business trip and that’s all, as soon as possible. You good with all that?”
• “Hell, yes.”
• “Perfect, now without spoiling anything, you better get prepared for all of the stories you read to get real, get your dick ready, get your ass ready, and you need to do everything I tell you to. You ready?”
• “Can’t wait.”
• “Also, here is something for you to think about on your way over.” – she lifted her nightgown, and under it, this beautiful thick cock appeared. I couldn’t tell how big it was, but I knew I wanted to feel it inside of me, and she was right I could not stop thinking about it.

That was most of my initial conversation with Dahlia, she booked me a flight, told me where to go, and be ready for pretty much anything. I knew what was about to happen, I was going to get fucked and rapped, and I was going to have to suck dick and serve as a slut. And surprisingly to me, I was so excited, my dick was pulsating, and my ass was itching and ready. This will be my new life. So in 2 weeks, I had taken time off work, and I was on my wait to meet Dahlia and get this adventure underway.

Day 1

My plane landed early in the morning, and I took a cab to the hotel I was told to go to. When I arrived I called Dahlia, and she told me to wait for her. I was in front of the hotel waiting, then suddenly I could see her waving at me, I started walking toward her, but I didn’t expect her to jump on my arms or the wet kiss that followed. You couldn’t tell Dahlia was a trans woman just by looking at her, so for people walking by I had the most beautiful woman in my arm kissing me in the middle of the street. She said it was great to finally meet in person, she grabs my arm and leads me inside the hotel. Dahlia told me she books us an adjacent roomс, just in case we need them, but we will mostly stay the in the same one. While we waited at the reception for the key cards, she took my arm and placed it on her ass, and whispered in my ear that I can squeeze, grab or touch her as much as I want. Her ass was so amazing and I was so excited, I got hard there in the middle of the lobby. We took the elevator up to the 18th floor, and while ridding she grabbed me by my package and pinned me to the wall of the elevator, and we started to make out, this time I didn’t think of it and I just grabbed her ass and started to stick my tongue into her mouth.

We got to the room, and it wasn’t just a normal hotel, the room was a big apartment, with a big soft bed, a great view, and an amazing bathroom, I was stunned.

• “Do you like it?” – she asked.
• “Wow, this is too amazing, it’s too much.”
• “Nothing’s too much for my whore, now sit down and let’s talk.”

She started to explain to me what is the plan for now. To start I was supposed to address her as Mistress Dahlia, and I’m to obey her every command. If not there will be punishments. The first few days she said she will go easy on me, but I better learn fast. She asked if I needed some time to rest after the flight, but I said I was ready to begin, which made her smile. She told me the first thing she wants to do is see me naked, so she told me to strip. Well, I was told to listen to her every command so I did just that. And there I was, fully naked with a soft dick, which I covered with my arm, I normally didn’t shave my body, so I had hair on my legs, chest, arm ass everywhere, I just shaved my pubes a little, cuz I liked it like that. She told me that there is a lot of work to do, also told me not to hide my cock anymore like that, she wants to see me. Then she picked up the phone and called someone, then told me to get dressed. We left the room and went down to the hotel spa, and then she introduced me to 2 girls and told me they will take care of me. We went into a room, and they told me to strip and lie down, and that my mid hurt a bit. Then started to vax and shave all my body here, they also shaved my ball and dick and told me to lie on all fours, bottoms up, and shaved my ass. When we were done I was clean like a baby. All I had left was the short hair on top of my head. I went back to my room where Dahlia was waiting for me. We sat down and drank some coffee and talk for a while, while I was getting used to my new shaved body. Then she told me my training will begin this afternoon if I’m ready. Then she left for a bit. I was walking around the room, watching the view and imagining what will happen next. When Mistress Dahlia, came bag she was carrying a large bag, which she put on the table.

• “So Viki, let me show you what I got for you” – she opened the bad, and it was filled with all kinds of dildos, vibrators, plug cock rights, and so on. - “To be a proper sissy we will need to teach you how to handle a cock, how to suck it, how to play with it, and how to ride it. Your job will be to make your master happy and fulfill his every desire. But before we get to that, we will see what you got. First thing first goes take a shower, and clean yourself, also use this, and yell if you need help.”

She handed me an anal douche, which I had never used before. I went into the bathroom and took a shower cleaning my body, especially my dick, I left my ass for last, I soaped up nice, but since I had never used an anal douche, I called her for help. She walked into the bathroom and told me to fill the tank with water and bend over. Then she stuck the hose up my ass and filled it with water, then told me to push it all out. It came mostly clean but we did it a couple of times just in case. She told me I need to do it every day; we don’t want any accidents.

All ready and clean we on the couch and started to talk, me with only a tower, and Dahlia still wearing a cute sun dress. She took one of the dildos we had and handed it to me and told me to show her what I got. I didn’t know what to so I just stuck it in my mouth and started to suck it. She laughed at me and took the dildo away.

• “No no no, you are rushing into it, let me show you how it’s done. You have to play with it first, slowly with your fingers run then up and down, maybe grabbed it softly, then you can start to kiss the head, lick it up and down, play with the balls, lick the balls, lick the head, and then start to take it in slowly like it took big to take it all the way the first time. Also, enjoy it, enjoy the taste, the feeling of how it’s getting harder in your mouth.”

While explaining to me, she was also licking and sucking that dildo slowly. It was so hot watching her do it that I got hard in a second. She then left the dildo on the table and removed her dress, I could see her white bra on a tiny flower and panties, hiding that big thing between her legs. She then pushed me back on the sofa and started to kiss my chest slowly doing down on me. My almost 6-inch dick was rock hard already when she got to it. She took it in her hand and started to kiss it, licked my balls, and while playing with them she started to slowly take my head in, kissing and licking my dick all over. Then he took into her mount and started to blow me. The best blowjob I have ever had. She was playing with her tongue, she was lightly biting my balls, and masturbating me. I enjoy it so much, even too much. It didn’t take long for me to start shaking. The moment she felt it she took it all the way in and I started to cum inside her mouth. She took every last drop in, and then kissed me, with a cum filled mount, which she transferred into my mouth.

• “Don’t waste it drink it all, you need to get used to the taste, and your sperm is pretty nice actually.”
• “Dahlia, that was amazing.”

She slapped me right across the face.

• “I told you, Mistress Dahlia. But I’m glad you enjoy it, you will learn to do the same. Also, you came way too fast we have a lot of work to do. Today you are forgiven, but you will learn to ask permission before you cum, got it?”
• “Yes Mistress Dahlia.”
• “Good, I will leave you all the toys to practice and will be back tonight. You don’t deserve to see me naked yet.”

She left for a few hours, and I took the time to practice a bit with the dildo, and also to eat and rest as I knew that this is just the start.

Dahlia came back in a couple of hours, wearing the same cloth. It was already around 10 at night, and she told me if I was ready for round 2 to come to the bathroom. I went in only wearing a boxer and I saw her sitting on the bed, dress already on the floor. I sat next to her and we started to make out. As I was playing with her boobs, she took her bra and I could finally see them, just perfect. I started to lick her nipple and pushed her back on the bed while licking her whole body. When I got to her panties, she told me to take them off with my teeth, which I did and this nice cock was right in front of my face. I didn’t use my hand just started to lick it up and down, I wanted to taste that thing so badly for the past few weeks. She was getting hard and I could tell that her thick cock was bigger than mine. I tried to do everything she taught me earlier, taking my time enjoying the taste. She started to caress my head and push it down, while I was trying to fit that 7,7-5-inch cock inside my mouth. She grabbed my chin and pulled me for a kiss. Told me I’m a fast learner but today it is not about that. Then he forced me on my back, took my boxer off, and started to suck me off again. I loved every second of it, but then she grabbed my balls and pulled them down, told me to not enjoy it too much, and to remember not to come too soon. Dahlia climbed the bed and sat on my face and told me to eat her ass, and so I did. I was licking the ring and sticking my tongue inside. She was on all fours ass up and I was still eating it when she begged me to stop teasing her.

• “Stop teasing me and fuck me already, I want to feel that cock inside of me.”

I spit on my dick and her ass one last time, and I started to slowly penetrate her. It was going in so easily, not her first time. She pushed herself back on me and we started to move together. Her ass was so soft; I could feel my dick even harder than ever before inside of her. You could hear my wall slapping her ass, and I could see in the mirror her still hard cock, slapping her tight under us. I was getting too excited again when she stood up and pushed me down on the bed. “Remember do not cum without my permission.” Then she mounted me and started to jump up and down on top of me. Her boobs were bouncing, and she was playing with her nipples, while I was holding her ass and fucking it as hard as possible. She had her eyes closed and biting her lips. I don’t know if it was fake or not, but I didn’t care it was amazing. Her dick was slapping me on my belly, still semi-hard. I took initiative and turned her on her back, dick still inside of her, and started to fuck her missionary. I grabbed her cock with one hand and started to masturbate, while she was sucking the fingers of the other. I fucked her like that for as long as I could, but It was time for me to cum:

• “Mistress can I cum, please let me cum inside of you.”
• “No, keep fucking me, yes keep going.”
• “Mistress please I beg you, let me cum.”
• “Keep going a little longer, yes keep fucking me, yes harder, yes.”

I was holding on for dear life, having no idea how I could keep fucking her, then she told me,” you can cum on top of me”, in that same moment I just pulled my dick out, and I started to cum the hardest I have ever finished, there was sperm on her dick arm, chest, and stomach. I collapsed next to her, while she was still masturbating, then she came all over herself as well.

• “Well what are you waiting for, clean me up.”

I started to lick the mixed sperm off her body. I swallowed some, shared some with her, and finally, we fell asleep in each other arms.

Day 2

In the morning we woke up next to each other, took a shower together, which was nice, and went down to the hotel lobby for breakfast.

• “How that you saw what it takes to make a guy come, we need to teach you to do it. Today we will start, you better be ready. Also on a side note I liked the way you fucked me last night, it was very enjoyable, we will be doing that again soon.”

This made me so happy, on the one hand, I got to fuck such an amazing tranny, on the other, the fun was just about to begin. We went back to the room and Dahlia told me to wait for her to come back. In a few minutes she shoved up again with another bag, this one had woman’s cloth. She told me today that we are not only going to learn how to satisfy a man but also how to dress for them. I spent the whole morning trying different panties, thongs, panties, long socks, heels, and bras (not that I had any breasts), but they were push-up bras. She got me some skirts, tank tops, and dresses. I look kind of hot in them.

While I was trying these cute little light blue thongs sticking up my ass, with garter, and these high white heels, she told me to kneel in front of her. She pulled her panties aside and told me to suck them, which I did. I was taking my time, playing with her cock, slapping my cheek with it. When he told me to lay on my stomach. Then she pulled my tongue aside licked her finger and stuck it right inside of me. There was no pain and I enjoy it. She was licking my asshole and playing with her finger. Then she lubed me up, picked a small vibrator, and asked me if I was ready. All I did was nod, and I could feel its head trying to go inside. With her soft touch and a lot of lube, the dildo got inside me without too much difficulty. There was a little pain, but it was fine considering this was my first dildo. She holds it inside for a couple of minutes, then started to fuck me with it. After she noticed it goes in with no resistance at all, she grabbed a little ticket and did the same thing. This one I could feel, filling me inside, and I started to moan under her touch.

• “You like that don’t you, slut, we are going to make a good sissy out of you after all.”

She kept picking up the past, and I kept moaning. I locked down and I could see my dick getting hard and leaking pre-cum. Dahlia then took a but plug lubed it up and stuck it inside of me. She told me to wear it all day, so I can be ready for her. The idea of taking her cock inside of me got me so hard that I could explode. With a plug inside my ass, she told me to go dressed, in normal cloth, and that we are going shopping. Well mostly she was shopping I was just carrying the bags, but still with a plug up my ass the whole day.

In the evening we got home, and she told me to take it out and wash my ass. I could see in the mirror that my hole is bigger now. We had some room service.

• “You better leave room for dessert.” – she told me while moving towards the bedroom.

She was complexly naked on the bed, waiting to be served. I was already naked, since she didn’t let me get dressed after the shower, so I just sat on the bed next to her and started to kiss her body all over. I already knew what to do, so I was playing with her cock for at least half an hour. She was enjoying the time we had together, then she pulled me on top of her, her cock still inside my mouth. Nothing could stop me from sucking her, and after she sucked my cock for a bit, I could feel a finger inside my asshole, then 2, then 3. She took me to the edge of the bed, I was on my back, legs up, and she was lubing my ass and her cock.

• “This might hurt for a bit, but remember you are a dick-craving slut, and you need it inside of you.” – she said and started to push it in.

I screamed at the initial sharp pain, trying to stay relaxed so she can penetrate me fully. I even felt a tear down my cheek, but I still wanted her inside of me. She slowly and steadily penetrated me fully, and with cock in the ass she leaned on the top of me, and we started to make out for a while. Distracting me from the pain, she holds her dick in me for a while. Then all of the sudden I started to feel movement. We were still making out, but she started to slowly fuck me. Taking it a little out and back in. She took her dick out and kneeled to lick my ass, before penetrating me again. She kept fucking me like that, I don’t know for how long, but the pain was fading away, and all I could feel was that dick, penetrating me, filling my ass, hitting my prostate. I could feel every inch of it going in and out of me, she was playing with my cock, but I didn’t care I just wanted that dick to never stop fucking me.

She put me on all four, before penetrating me once again, this time it wasn’t slow, she was full-speed rapping that ass. I could hear her thighs slapping against my ass. I could even keep my pose, so I was forced down on the bad, ass up, and she had her foot on my face pushing it down, and fucking me hard as she could. Maybe not ideal the first time, but I loved every second of it. The domination the pain, that cock. When she got tired, she told me to ride her. And so while she rested, I was riding on top of her. Going cowgirl and reverse cowgirl. I could feel my dick leaking pre-cum and I would touch it, but I feared could come without permission this time. After a while she grabbed my ass once again, I was still on top of her, facing her, and she started to fuck me faster and harder again. I was lying on top of her and my dick was between her rock-hard belly and mine. I felt the friction and I was going to cum. The moment she screamed, I felt her filling my ass, and also my dick started to cum at the same time all over us. She was filling my ass so much; I could feel the sperm licking from it. We lay there covered in cum breathing heavily. She told me good job on not coming too soon, and it ok that I came with no permission, but I can keep asking her if I want to just for fun.

An hour passed, with us, just hugging and not talking, then she asked me how it was, and how I’m feeling. I kissed her on her red lips and told her it was amazing. “Good cuz they’re a lot more from where that came”. Then she got up and returned with a different plug, a bigger one. She put it inside my cum filled sore ass and told me that I will sleep with it tonight. She also put one inside hers, so I don’t feel left out, and she fell asleep in my arm.