From Boy Toy to Baby Girl

I was in college and I had been hooking up with this woman for a while. A tall brunette over twenty years older than me. We matched on Tinder. I did not tell her how relatively inexperienced I was with women, so our hookups had so far consisted of her telling me what she wanted me to do. And when she didn't tell me directly, her hands would guide me to where she wanted me to be. I was eager to please. I touched and licked and fucked her however she desired. I should have realized that revealing this eagerness might leave me vulnerable to other kinds of demands.

We had developed somewhat of a routine by now. Her job kept her busy, so when she wanted me to come over, she would simply text me 'tonight?' I would always say I was free. There were no plans I wouldn't cancel for this woman, though I wasn't sure if she knew that yet. After I said yes, she would message me a time. The time was when an Uber would pick me up outside of my dorm to take me to her place. When we were done with our activities, she would order me an Uber back.

Until one night our routine was disrupted. She said 'tonight?', I said yes, she sent me a time, per usual, but then she added "Bring a travel bag. You are staying over tonight."

Yes ma'am, I thought.

When I got there, she seemed different. Was she nervous? Excited? It was hard to tell. She had made it very clear to me so far that I was simply a boy toy. Little more than a transaction of pleasures between us. So I still had trouble reading her emotions.

Eventually after some idle chit-chat over a bottle of wine, we made our way to her living room and sat together on the couch. We usually fucked in the living room, so I had never actually seen much of her impressively large house. She put her hand on my leg. I thought this was the cue to start our normal activities, but she stopped me.

"I want our fun little relationship to take a different shape," she told me. "I want certain things to happen tonight. Some new experiences for you. I think it will be more fun if you are in the dark. It will... build anticipation. There might be certain things that might make you feel... different. But here's the deal." She paused to put her hand on my cheek. My whole body flushed. "If you genuinely do not want to proceed, then just say 'Miss Lucy I would like to stop please.'

Her name was Lucy, but this was the first time she insisted that I add 'Miss'. This took me aback, so I ended up just staring at her.

"Repeat it once for me," she said.

I stuttered when I tried to say it. She grabbed my shoulders and looked me in the eyes.

"This is important," she said.

I breathed once, slowly, then said, "Miss Lucy I would like to stop please."

"Good boy. Anytime you want to stop, say that. When things start to happen, you might blurt out 'no' or 'stop' out of impulse, but not really mean it. So I need to know that you know the magic words. Do you understand?"

I nodded.

"Say 'I understand.'"

"I understand."

"Now, once more, say "Miss Lucy I would like to stop please."

"Miss Lucy I would like to stop please."

"Very good boy." She kissed me. Hard. She pressed her body against me and forced me to lie back on the couch.

"Now, if you are ready, say "Miss Lucy I am ready."

"Miss Lucy I am ready."

"Good," she said. "Now stay put." She got up off the couch and left the room.

After a few minutes, a young woman entered the living room. She told me that she was an assistant to Miss Lucy and that she would be helping me prepare for tonight. She told me that she was aware of the 'magic words', but, unless those were spoken, Miss Lucy expected me to do exactly as I was told. The assistant then told me to follow her.

I followed her to a wing of the house that I had not been in before. We went into an enormous bathroom, larger than my dorm room back in my college dorm. She told me to take off my clothes. I was reluctant.

"No need to feel rushed," she said. "Miss Lucy said that we can take as long as we need."

After collecting myself, I stripped down to my underwear. I tried to protect a last shred of dignity by covering my bulge with my hands.

"I'm afraid that it is necessary to remove all your clothes," she said.

This young pretty woman seemed to be unfazed by all of this. She was forthright and professional. Unlike me. I was literally shaking with nerves. I was also terribly turned on and my hands couldn't entirely hide it.

"Again we can wait," she said, "Or I can help things along."

A gave her a confused look. She approached me. Gently grabbed my hands and pulled them away. Then yanked my underwear down to my ankles.

"I can see why she likes you," she said, as she inspected my hard and now unconstrained dick, "Though you won't have much use for that tonight, I expect."

"What?"

"Hold your arms out."

I did as I was told. She pulled a measuring tape from her pocket and took measurements of my arms, chest, waist, legs, and such, like a tailor.

"I'll need to do some more measuring when you... relax downstairs," she said, "but that can wait." The assistant collected all of my clothes and left me standing, naked and confused, in the oversized bathroom.

A few minutes later, though it felt like an eternity, Miss Lucy entered the bathroom. She came right up to me and embraced me.

She spoke into my ear. "You're doing well so far." She started lightly stroking my dick. "So, so well." A tiny moan exited my mouth. "Do you want to be the best boy for me?"

"Yes," I gasped.

"Ok, my good little boy, continue to do everything my assistant says." She gave me a peck on the cheek, turned swiftly, and walked out. Leaving me hot, bothered, confused, and flustered.

Her assistant came in and I soon understood why Miss Lucy came to give me some extra encouragement. Her assistant put me through what I can only describe as an intense feminizing procedure. Though I was not exactly a hairy young man, she first shaved all of the hair on my body. Even though this still felt erotic, I went soft at some point and the assistant took the opportunity to quickly measure the length and girth of my flaccid dick. This was much more embarrassing than earlier. I'm a grower, not a shower. And when I haven't grown, little is shown.

Then she said it was time to 'get clean'. The assistant gave me an anal douche and showed me how to use it. She made me fill my ass up multiple times. After that, she told me to shower. She observed me as I did, saying that it was her job to make sure I didn't touch my dick. When I got out and dried off, she had me sit in a special chair with straps on it. She strapped my wrists and ankles to the chair.

"Do you have any magic words for me?" She asked. I shook my head.

While I was strapped in, she painted my nails and did my makeup. I confess that I was more turned on now than I think I had ever been in my life. I was hard the entire time. I was not sure if it was the process itself, or simply the fact that a beautiful blonde was giving me so much attention. Regardless, this unlocked something inside of me and there were moments where I felt I would burst even without any stimulation at all. The final touch was fitting me with a wig. It was medium-length with wavy brown hair not too dissimilar in color from my own hair.

"Be right back," she said. I don't know what was more cruel, the fact that I was strapped in, so I could only squirm in response to how turned on I was, or the fact that the chair I was sitting in was pointed toward a wall instead of a mirror, so I could not even see what I looked like.

The assistant reentered with some things in her hands. She then got on her knees and grabbed my junk.

"Close your eyes please," she said. I obeyed. She wrapped some kind of band around my waist.

"This is going to be cold," she said, "But I need you to calm down." Right when she said that, she placed some kind of cold pack on my dick. I writhed from the cold. It took longer than I would have liked, but eventually I went soft. When I did she put my dick into some kind of contraption. A chastity cage is what she called it. To prevent me from getting hard, masturbating, etc. The band around my waist held it firmly in place.

She then unstrapped me and guided me out of the bathroom into an adjacent bedroom. Clothes were laid out on the bed. A pink thong and lingerie set. A black dress to cover the lingerie. And high heels.

"Go ahead," the assistant said. "They'll fit perfectly."

She watched me awkwardly put on the clothes. She was right, they did fit perfectly. When I grabbed the heels, I noticed little locks attached to straps that go around the ankles. The assistant locked them in place with a small key after I put them on. She adjusted my clothes slightly and gave me a tip on how to walk in heels. Then she led me to a full-body mirror.

I looked hot. Pretty. Sexy. A wave of heat flowed through my body. I felt my dick strain against my cage, but it was held firmly in place by the waistband and thong. Miss Lucy was right. I was certainly having new experiences. And I liked these new experiences.

"I think that's it for me," she said. "Good luck." And she left the room.

I kept admiring myself in the mirror. I felt my skin flush all over my body. The chastity cage was frustrating me like crazy. If not for it, I probably would have masturbated right then, watching myself in the mirror as I did it. But I couldn't. The cage was like a cap on a shaken bottle; sealing in all the sexual desire that was desperate to be released.

After what felt like ages, Miss Lucy came into the bedroom. She was wearing sexy, tight, latex lingerie and oversized high heels. She looked intimidating, but her demeanor was different than it had ever been. She had always been smart and kind, but there was certainly a kind of distance and professionalism that had been present in even our most intimate moments. That seemed to disappear when she saw me fully transformed and fully feminized.

"Well, well," she said, "Aren't you such a beautiful young woman?" She approached me and embraced me. "I knew you would be. You've been such a good boy for me many nights. Not it is time for you to be a good girl for me. "

She held me as we both looked into the mirror. She then had me repeat words of affirmation. "I am so pretty", "I look sexy in my new clothes", "I am a beautiful woman", and so on. This was clearly a kink of hers, because the more I affirmed what she told me, the more turned on she got. She started feeling me up and kissing my neck. She even gave me light scratches and bites. I was so turned on and pent up that I started shaking and shivering by the end of it.

Eventually, she took me to the bed. I laid on my back and she got on top of me and kissed me deeply. It was just at this moment that I noticed a mirror on the ceiling of the room. I saw myself, dressed in a sexy black dress, with a beautiful, sexy woman on top of me. Kissing me. After a long make out session, she took off my dress so my pink lingerie was exposed. She left the bed for a moment and I stared at how sexy I looked in the ceiling mirror.

Miss Lucy came back and cuddled with me as we both looked into the mirror. She had added something to her outfit. A harness that held a large purple dildo in place. While she cuddled me, she had me repeat more things back to her. This time it was not affirmations, but requests. "Please, Miss Lucy, let me touch your big cock." "Please, Miss Lucy, let me suck your beautiful dick", and so on.

Little did she know, this was actually where I was more comfortable sexually. I had sucked and fucked real dick before. (Or, maybe she did know, and I didn't realize that she knew). This would be my first time with a silicon one, though. For some reason, I tried to hide my experience as I licked and sucked her purple dick. Miss Lucy shoved her dick down my throat and told me what a good girl I was.

Soon enough, it was time for the main event to start. She had me bend over in doggy style and slid my thong off. She went to work lubing up my ass and my dildo. She massaged my asshole a bit, telling me to relax. When I had relaxed myself to her satisfaction, she turned me over and laid me on my back.

She got on top of me and locked her hands with mine. I felt her dildo tease my ass. She slowly maneuvered it into place and lightly pressed against my asshole.

"Tell me how much you want this," she said. I told her I wanted it so bad.

"Please, Miss Lucy, please," I begged, "Please fuck me. Please, I want your cock inside of me." I looked at the ceiling and started shaking and shivering again. I was so turned on seeing this beautiful woman take control of me.

"Look at me," she said. "Look into my eyes. Don't break eye contact. I want to watch your eyes as I press myself inside of you." I did as she told me. I locked on to those pretty dark brown eyes of hers. Her face was domineering but full of anticipation. She squeezed my hands harder and stared at me more intensely as she pressed herself harder against my ass. I relaxed and felt her slide into me. This caused me to gasp.

"Good girl," she said. "Keep looking at me. There you go." She slowly started moving back and forth. Each gentle thrust went a little bit further into me. Every time she deepened her thrust, I instinctively closed my eyes or looked away, but each time she commanded me to look at her. I was able to maintain eye contact when she finally eased her way all the way inside of me. The eye contact made me feel so submissive and vulnerable. When her hips pressed against my ass. I was hers. She owned me. She knew it. And she was going to make sure that I affirmed it. Over and over.

We had fucked hard many times. I had heard her scream when I fucked her. I had felt her whole body tense when she orgasmed around my dick. Yet it was obvious that this moment was her sexual high point. As she started thrusting harder and harder into me, she had an intensity and fervor in her eyes that I had never seen before. Now her true desires started to break through. She made me say that I was hers, that she was my owner, my mistress, my mommy, my domme. I repeated everything she asked. She started fucking me really hard. Relentlessly. I couldn't hold back. I started gasping and moaning and squealing. Every time I closed my eyes or moved my head away, she grabbed my face and brought my gaze back to hers. I inadvertently let out a pathetically high-pitched moan, and it was like a bolt of lightning hit Miss Lucy. She grabbed my arms, pinning them to the bed. She dug her nails into my skin.

"You are such a dumb little slut aren't you?" She said, as she rammed herself deep and hard in me. "Say, 'Yes, mommy'."

"Yes, Mommy."

"Tell me. Say 'I'm a dumb little slut.'"

"I'm a dumb little slut."

This pattern repeated over and over. I affirmed to her that I was a slutty bitch. A mindless whore. A desperate fuck doll. A submissive sissy. I told her that she owned me. That I loved her cock. That I wanted to be her slut. Her slave. Her fuck toy. Forever.

I couldn't believe how long she was able to maintain her pace, all while questioning me, commanding me, and demanding me. After many, many self-degrading affirmations forced upon me, she went quiet and finally allowed me to break eye contact. She let me close my eyes and lean my head back as she continued thrusting. She moaned and grunted as she kept up her perfect rhythm.

The friction. The thrusting. The rhythmic motion. The constant pressure on my prostate. All this felt so fucking good. My caged cock bounced pathetically in unison with the thrusts from her large purple cock. She started kissing and sucking my neck as she kept fucking me deep.

Then I felt a new, strange sensation wash over me. It was warm and tingly. I felt it flow and dart all through my body. It started to take my breath away. I didn't realize what was happening until I was already on the precipice.

"Oh fuck, oh fuck, oh fuck!" I yelled when I finally realized what was about to happen. "I'm going to cum!"

When I said that she grabbed my face with both hands and pressed her face right into mine. Our noses were touching as she stared intensely into my eyes.

"Yes, baby," she said, "Be a good girl and cum for me. Be my perfect baby girl and cum for mommy." She gave me one last deep thrust and held it there.

I came. Even though my cock was still tightly locked in its cage, I ejaculated ropes of cum out of my dick. I was in disbelief as it was happening. My eyes must have been as wide as they could possibly have been. I didn't know something could ever feel this good. I shook and writhed as it happened. Unlike my ordinary orgasms, this one seemed to keep going and going. I was moaning uncontrollably. I could even feel tears start to streak down my face as I was overwhelmed with pleasure and sensation.

She kissed me hard, then. Passionately and with urgency. Then she bit down on my neck and maintained her bite there for a while. I knew it would leave a mark, but at the moment I didn't care. I was still riding high on my blissful anal orgasm. She then released her bite, and aggressively wrapped her hands around my throat.

"Don't panic. Don't be scared baby," she said and she tightened her hands around my throat, "Just keep looking at me." She started fucking me hard again. Her hard thrusts hit different post-orgasm. It still felt good, but whereas before any coherent thoughts were drowned out, I now was more conscious of the fact that I was dressed up as a girl and getting railed by an older woman. I felt so used and pathetic.

Her thrusts were far more frantic and less rhythmic than before. She tightened her grip and started to moan. Loudly. Incoherently. I confess, despite what she urged, I did start to get scared. I started to panic and I grabbed her arms. For a tiny moment, the magic words flashed in my mind, but I didn't let them escape my mouth. She squeezed even tighter and rammed her dick as deep inside of me as she could. She held it there and tensed up her whole body, all while strangling me with her hands. Right at the moment when I felt like I was going to lose consciousness, she collapsed. Her whole body started to shiver and shake. I could see her muscles spasm, and her legs and arms quivered. She tensed and gasped and moaned as shockwaves of her orgasm kept hitting her over and over and over.

When the orgasm finally subsided, she slowly slid her dildo out of me. She cuddled me and pressed my face into her chest. I could feel her twitch as aftershocks of her intense orgasm continued to hit her. She grabbed my wig and took it off, tossing it across the room. Then she stroked my real hair and kissed my forehead.

"Good girl," she said. "You were such a good girl for me."

We stayed in that position for a while, as we caught our breath and let the evaporating sweat cool our bodies. My brain was overflowing with dopamine as I basked in a post-sex bliss I did not previously think was possible. Her soft strokes, gentle words, and warm body soon lulled me to a peaceful sleep.