My Transformation

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A story of one person's feminisation.
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It all started during puberty as these things often do. I can distinctly remember watching a TV programme about a shop that would dress men up as a woman and getting really turned on by it but not really knowing too much more or what to do with myself.

These feelings occasionally came back over the years but with the restrictions of living with parents there wasn't too much opportunity, plus I'd convinced myself I was fully straight and went down the usually girlfriend routes. It was then that I discovered that I loved to lick pussy and be the partner who does all of the work, the feeling of devoting myself to my girlfriend in the bedroom was incredible, that was until we broke up just before I moved away to go to university.

So it was then that I decided I needed a fresh start and moved to the other end of the country and with the extra freedom came the almost nightly porn and masturbation sessions. I just couldn't get enough of all the porn that was out there and I'd end up wanking over almost anything I could find. It was in one of these sessions that I came across a man being turned into a maid before sucking a big cock until "she" was covered in cum. It brought back all of the feelings I had watching that TV programme and I couldn't take my eyes off it and I ended up having my first real orgasm and went back to the same video night after night.

Shortly after this I was walking through my halls and I walked past a female roommate's door which had been left unlocked and there, in the middle of her floor, were a pair of stocking like the sissy in the video was wearing. After this I waited a few days when I knew that if I skipped a lecture I could get a good few hours free to have a go in the stockings. It was then that I sneaked into her room and stole a pair and the fever kicked in and I spent ages looking through her clothes, working out which outfits I thought was cute and would go together. Up until then I'd never realised how sexy her underwear was, she looked so unsuspecting from the outside but I knew that underneath she wore the tiniest thongs and silkiest panties imaginable. After rooting through, and smelling, her lovely panties I decided I would choose a pair for me to take away and play with. I chose a pair at the bottom as I thought they would get noticed less and picked some gorgeous lilac satin panties and the seamed stockings I'd seen left on the floor as few days before.

I waited till everyone was in bed to try them on and I was shaking with excitement. I started with the stockings, placing them over my feet and slowly pulling them up my legs. The feeling was electric, I felt so womanly just doing it, especially making sure I had the seams straight. Next came the panties and the feel of the silk against my stocking covered legs made my head spin; I could feel my body shake as I pulled them up over my already hard cock.

Looking in the mirror I was amazed at how feminine my slim body looked and how elegant my legs seemed, even with the bit of hair. I felt like a real girl stood there apart from the bulge in my shiny panties but even that was turning me on making the bulge bigger and bigger.

After watching myself for what felt like hours I rubbed my cock through the panties I can't describe how good it felt lying there on my bed feeling my rock hard cock through the satin, thinking I was that sissy in the video sucking a big cock, until I exploded like never before. My body shook and there was cum all over my silky panties, more than I had ever produced before.

I woke up in the morning, still wearing my panties and stocking but panicking as I was late for my lecture, the same one I missed to go through my roommates clothes so I had to be there. As I was in a rush and I was still turned on by the sight of myself wearing the panties and stockings I decided just to leave them on under my clothes, not even bothering to put any socks on and I ran out the door.

I thought I'd got to the lecture in time but sadly I missed the first half hour which made my lecturer ask to see me in her office after the lecture, probably as I'd been late a quite a few times. I hardly paid any attention to the lecture, all I could think about was the cum stained satin panties I was wearing and how it made me feel like such a slut although I did wish it was another mans.

After the lecture I knocked on her office door, I was so nervous as I'd not been in this position before and I didn't want to get thrown out as I was loving my newly found freedom. I sat there listening to her talk to me about the importance of attendance and I'd never noticed how stunning she was. She was in her early fifties with shoulder length brown hair but her figure was more like someone in their late thirties, the thought of it was making my cock strain against my cum covered panties again. By the end of the meeting we agreed that I would need some extra tuition and I would meet her at her house for some extra help the next evening, I thought it was a little odd having to go to her house but she explained how it was so the head of my subject didn't find out I was struggling which seemed reasonable.

I took a while to get to her lovely suburban house the next day on the bus but it really was a peaceful spot, really secluded and quiet as the sun was just beginning to set. She opened the door to her pristine house and as usual she looked stunning still dressed in her knee length pencil skirt and white satin blouse, the kind of outfit I had come to wish I would wear.

We sat in her home study for some time going through the work I had missed over the past few weeks and it was a great help. I couldn't help but think about how much I wanted to be like her, to wear those heels and have a figure like hers.

"Would you like to relax with a glass of wine?" she said in her sultry voice once we had finished which I obviously agreed to as I was quite exhausted and I thought it would be nice. After I watched her gorgeous ass walk away I started looking around her living room and I thought it was strange that there we no personal photos, like a husband, but I guessed that she must not me married.

"Please take a seat" she said as she re-entered the room with our wine so I sat on the sofa. She then handed me my glass and sat surprisingly close to me, to the point where our knees were pretty much touching. It felt a little weird at first but once the wine kicked in I relaxed a bit more.

"You do know why I brought you here don't you?" she eventually said.

"To help me not to fail?" I replied, wondering why she'd asked such an unusual question.

"Not just that" she said as her perfectly manicured hands moved onto my knee. "I also wanted to spend a little more time with you as you are such a promising student and I don't want you fail. Plus you seemed like such a cute young man that I thought it would be nice to spend some more time with you."

I didn't really know what to say so I just nodded as she leant further in to me, her pink lipstick covered lips looked so inviting I just couldn't resist so I went for a kiss. They tasted so smooth, my previous girlfriend has never really worn lipstick and the feel of them on my lips drive me wild.

Her perfume flooded my nose and I was totally intoxicated as her hand moved up to my head to hold our lips closer and closer. I could hear her breathing heavier and heavier as we continued to kiss for what seemed like forever.

Just as her hand was moving up my leg to my now rock hard cock she pulled away from my lips.

"Why don't you pop up to my bedroom and make yourself comfortable and I'll slip into something more comfortable. It's the first door on the right upstairs" she said as she gave me one final peck on the cheek, immediately leaving the room, obviously showing her sexy ass to me.

Alone in the living room I still felt more than a little confused, nothing like this had ever happened to me before outside of my fantasies but I was more than happy to go along with it. I got up from the sofa and made my way upstairs nervously. Opening her bedroom door I was once again amazed at the size and cleanliness of the place. The large bed in the middle of the room seemed really comfortable as I sat down to take all but my boxers off, the black satin sheets felt lovely against my skin and I made a mental note to try and buy some for myself.

After a very short while she entered the room wearing what just looked like a short, pink satin robe. I had never seen someone look so stunning in real life before, my mouth just dropped.

She slowly undid her gown as she walked towards the bottom of the bed and when she was there removed it entirely to reveal the sexiest pink camisole set I've ever seen. My cock was the hardest it's ever been as she crawled her way up the bed, straddling me as she went.

Once she'd crawled all the way up her soft smooth lips planted the sweetest ever kiss on my lips before we both instantly bust out in passion. Our hands were all over each other, the feeling of the silk next to her body was amazing, I couldn't believe I was about to sleep with someone so gorgeous as I began to squeeze her arse.

This continued for quite a while, so much so that my cock was almost popping out of my boxers with the thought of it being next to her juicy pussy.

"You don't mind if we try something a little naughty do you?"

"No, of course not" I replied somewhat nervously and immediately she leant over to her bedside table and pulled out four sets of fluffy pink handcuffs and my jaw dropped. I was so surprised that a lecturer of mine was about to cuff me up and fuck me senseless that I couldn't say anything as she fixed my wrist either end of the metal headboard. After this she took my boxers off and tied my ankles to the foot of the bed.

"Is that comfortable?"

"Very" I replied. I felt like I was about to cum without being touched, I felt so helpless against this satin covered beauty as I was tied up, spread-eagled on her sheets. "You seem to have me exactly where you want me".

"Of course I do sweetie, it was only ever going to be this way" she said with a naughty grin. "Now let me just get some ice and we can have some real fun". Once she had left the room I tried to move but she had tied me up too well, I was lying there with my solid cock out waiting for her to tease me.

To my surprise she returned with a whole bag but I just kept quiet, knowing I was the submissive one. She took out just one ice cube, rubbed it on her sexy lips and then placed it in her mouth. Seconds later she kissed me and the mixture of hot lips and cold ice were incredible. I'd never thought that something as simple as ice could be so seductive.

"Now I've got something even naughtier if you'd like to try"

"Anything you want" I replied "it's not like I can stop you"

"Of course not babe" she said with a very mischievous grin as she fetched two things from her bedside table, one was something I couldn't see down between my knees and the other was a bright pink ball gag which was obviously park of the handcuff set. Before I could even stop her or say anything she had shoved it in my mouth. Not that this stopped her kissing me, the sensation of the ball moving my mouth was incredible, especially as I could do nothing to stop it or make her kiss me properly.

She plucked another ice cube from the bag, placed in her mouth, and started to bite and suck my nipple. The feeling of my nipples being bit felt so good, I tried to moan but nothing more than a murmur came through the ball gag. Even the sound of myself not being able to moan turned me on more.

"If you don't want my pussy on your face just say so now" she said with a smirk on my face as I murmured back at her. This wasn't to say no but more to show how in control she was.

"Well as we're both in agreement you'd better get to work".

With that she slowly moved up my body her satin shorts moving closer to my face. I could see every detail, each strand of shiny satin, all the gorgeous lace trim and of course the wet spot in her crotch. Then she started rubbing the wet stop on the ball gag, slowly moving it up and down as if to tease me before she sat on me forcing my head further and further into the bed.

She kept on humping my face through the ball gag, I just felt like I was a toy to be used for her pleasure as her cum soaked through her shorts and onto my face. It was so wet and tasty; I just wish I could have licked it up. Once my face was covered in her cum and my drool she pulled her dripping pussy off my face, much to my muffled protest.

"That's it baby" she said one she had turned around so her back was to my face "moan for me while I put the ice to good use on your tasty cock". With that she put another cube in between her luscious lips, sat in my chest and bent over so all I could see was her stunning ass. I could almost see her asshole the shorts were so short and I even tried to touch it with the ball gag but I was tied up too much.

She bent over more and more till I could feel her breath on my ready to explode cock. She just kissed the tip and the coldness of her lips was almost enough to tip me over. Then, in one move she took the full 6 inches all the way, no gagging and gave it huge suck until she came up for breath, the best feeling I'd ever had.

Then suddenly in one quick move she grabbed the whole bag of ice and forced it onto my cock and balls. I tried screaming and stopping her because of how cold it felt but was tied up far too much, her weight was on my chest and her gag filled my mouth too much. She kept the bag on for what seemed like an age; so long it felt completely numb.

I couldn't see, hear or feel what she was doing to my cock until she stood up and revealed what she had hidden from me, which was now tightly attached to my cock and balls... A chastity device.

"Do you really think I would be attracted to someone as pathetic as you?" She said as she sat on my chest, towering over me. "When you came to my office I saw your silky, girly panties when you bent over to go into your bag and do you really think that I couldn't see your stocking over your shoes?

"I really did want to give you help with your studies but when I saw those I couldn't resist a little fun. As you can tell it's not my first time being in control but I think this is going to be something else entirely.

"Now you'll see that I've locked you up nice tight so there's no way you'll escape unless you come back to mine to serve me. Once a week will be enough to begin with but we'll see how much fun I can have.

"I haven't fully decided what I've got in store but just know that if you don't cooperate then it can get very rough for you, especially with the photos I'm going to take of you like this in a minute.

"All you need to know for now is that you must come here at exactly 7pm next Monday, wearing your panties and stockings, for your first lesson and if you don't there will be consequences".

I couldn't believe what she was saying, why had she chosen me? How could she be so mean? Did I really need to wait a whole 5 days to get this chastity device off?

"Now I'm sure you're more than a little confused at the moment but all will be revealed in time. Your little clit will now be my property and I will do as I please with it. Not that I'll have much use for it being a lesbian"

I tried again to talk but I couldn't, every time I struggled or murmured she would just laugh. It was also starting to get painful in my crotch, I must have been getting an erection but because of the device it was hopeless.

"That's right honey" she said once she stopped laughing "you're going to be a cuckold bitch of a lesbian Mistress. Doesn't that sound like fun? Knowing your serving someone who has no sexual attraction to you? Knowing that no matter how much you please me you're never going to turn me on like woman? Now let me go get my camera so that I can show all of your friends the pictures should you not turn up next week."

She left the room, for some reason taking my clothes with her. I didn't even bother to escape as I'd tried it so many times before. All I could do was to look as my padlocked cock, bulging against the chastity device more and more, as I lay there helpless.

When she returned, now wearing her satin robe again, she immediately started taking photos, much to my unintelligible protests. Making sure she took plenty of pictures of my locked up cock and the pink ball gag in my mouth with her cum all over.

"Now when I let you go you are to leave immediately, no questions are to be asked or these get sent to your uni friends. I have all their details through work so it'll be no problem for me at all. Is that understood?" I nodded my head as it was all I could manage.

"Good.

"Your clothes are on my doorstep so put them back on and I will see you on your return next week. You must not try and contact me any other way."

And with that she started by unlocking my ankle restraints, then the ball gag and finally my wrists. My jaw really ached it felt like it had been so long and I couldn't help but rub my wrists to try and get some feeling back, I'd always thought being tied up would have been kinky but I never really thought about the consequences before.

"Hurry up and get out bitch!" she shouted at me and I begun to make my way downstairs, head hung in shame as I didn't really know what to do with myself. When I got to the front door I tentatively opened it, fully aware that all that was protecting my modesty was a clear, pink chastity device and a padlock. Before I could look around fully to see if the coast was clear she shoved me in the back, forcing me fully outside as the door slammed and locked behind me.

I saw my pile of clothes a short distance away and quickly moved before somebody saw me naked and locked up. I started with my bottom half to help retain some modesty but it wasn't until I'd put my shoes back on that I realised the remaining clothes weren't my t-shirt and hoodie but was in fact a woman's coat. It was a shiny, almost satin like trench coat with a pale pink trim. I almost went back to the house to get my male clothes but I was afraid what would happen to those pictures if I did. I had no choice but to wear it if I didn't want to catch the bus half naked.

The coat somehow fitted perfectly, and it at least covered me up, but once I saw myself I couldn't help but slump to the floor and cry.

I eventually picked myself together, walked to the bus and waited so that I could get home and this night would be over. I felt so self conscious as I bought my ticket, although from a distance the coat could have been a man's it was possible to tell it was a woman's and I felt like every single passenger on the but knew it and was staring at me when I walked past.

Thankfully none of my roommates were in when I got back and I locked myself in my room and cried myself to sleep, hoping it would all turn out to be a dream.

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  • COMMENTS
20 Comments
slavetobyslavetoby5 months ago

This was an incredible start to what should be a fabulous story !!

4Leather4Leather7 months ago

Great start, Love were this is leading, just wish it was me being controlled in this manner. Please chapter two need to see we’re this is going.

jennifurzoejennifurzoe9 months ago

The joys of chastity and forced out into the public eye wearing some decidedly female clothing, can't wait for a number two.💜

AnonymousAnonymousover 1 year ago
New Sissy

I am new to the world of cross dressing.I now in joy dressing and making my self up as a woman.I have been going out in public for some tine now.I have met other cross dressers and they have helped me to in joy being a woman.They have shown me how to suck cock and to deep throat and swallow loads of cum.I now can take cock in my ass with out pain.I have now had my first black cock gang bang and loved it.I must say i really love black cock both in my ass and mouth.I have taken over eight inch cock in my ass and now in my mouth.How i love black cocks

Veronica_E_DayVeronica_E_Dayover 1 year ago

Very good storyline and well written, especially for a first story. The story is over six years old so it appears that there will never be an update. It’s too bad as the story has potential. 💋

Veronica

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