A journey of transformation

I was frequenting gay dating sites for many years now, but it was only a curiosity of mine, to see other men naked and read stories about their encounters. I began returning more and more often, absorbed by gay fantasies, to the point I imagined myself in them.

I was hoping to meet someone just to talk about my curiosities, but one guy caught my attention, with a friendly message. He was 43, so about 13 years older than me, tall, average built. His profile didn't reveal anything more, but he introduced himself as a doctor, well mannered, clean, and that he would like to know more about me. He was curious if I managed to meet someone online, as he was ready to give up because he either couldn't have a meaningful conversation with someone or they were too vulgar for him. I confessed that he was the first that approached me in a pleasent way, all the other messages being too upfront.

We kept talking the following days, mostly about trivial things and I could tell he was a great conversationist.

After a few weeks or so, he mentioned that he will be attending a seminar next week, and he will be in town for the weekend and would very much like to meet for a chat at the hotel he was staying.

I nervously agreed although I was aware of how some of these type of meetings tend to evolve.

I arrived at his hotel room a little after 10 in the evening and knocked on the door., but I almost froze as I entered the room. He reassured me that I was there just for a friendly chat. He started to talk a little about his day and that he was interested to know more about me. We gradually progressed into a casual conversation and I finally got the nerve to sit on the corner of the bed, as he was sitting next to it, in a chair.

       The conversation slowly steered towards our intimate life, and I started to feel more at ease to talk about my desires as I was comforted and told that I can use him as my confident, and that he is happy and finds me very brave for starting to open up.

'I started to take an interest in men before I was 18 and slowly build up my fantasies to the point where I began imagining how would it be like to be the woman in the porn movies. I started to feel an overwheling feeling when I saw women in pleasure having sex with men, and being dominated and constrained to the point that they eventually surrendered their will and became obedient. I grew fond of the feminity of women and a few months ago I went so far as I bought some lingerie..and...something realistic.. like a man's...I'm ashamed to say it'

He smiled. I paused for a second, thinking about what I just said. But his look was inviting, like he was on the edge of his seat, wanting to hear more. I still can't belive that I've said so much, but he made me fell very at ease, and I liked how he encouraged me to go on with my story.

' It was a very strange and new feeling for me opening the package. Although I lived alone, I opened it in the bathroom with a candle on the floor, and the lights turned off . I felt a churn in my stomach, my heart was beating wildly, and my palms were sweating. I don't think it was excitement. But the minute I started rolling up the lace stockings, I enjoyed very much what was happening to me. I then put on a pair of panties that left my tiny ass uncovered and a white lacey body that felt incredible on the skin. The final piece was a collar choker, which I thightened to the point I could feel it was bothering me. I turned to look in the mirror. My eyes took a few seconds to adjust in the dim light, but then I started to see myself. It was nowhere near that feminine sight I had in mind. I saw myself in lingerie and felt ashamed. I wanted to take everything off. I looked in the mirror for a few moments, but then I started saying to myself that there is nothing to be ashamed of, that I am not the first one doing this, that nobody sees what I'm doing, that I'm safe.. I turned around, trying to see how I look from behind, but then I set up my phone to take some shots in different positions that I would like to see me, as a woman, in. It was everything from doggy style, to me lying on my side looking over my shoulder, to my back arched, and one of my favourites, while on my knees.

I couldn't believe what pictures I took. I had a sense of fulfillmet, in a strange way. I definetly liked how I looked when I was with my back turned, but you could tell in the others that my face looked guilty of something. I had mixed feelings about what I was doing, but I finally decided that I should go all the way, to try something new, that I always wanted and fantasised about, and that if didn't like it, that would be it, nobody would ever know. So I took out from the package one last thing.. a realistic dildo. It was the first time I had seen up close something similiar to my own penis. I felt aroused right away, just by touching it. It was of average lenght, a little bit bigger than mine, and very soft to touch. I put it on the wall in front of me, at my penis height and started rubbing myself onto it, trying to cover it with my precum, to give it an authentic smell and taste. I was doing this for a few minutes, with many thoughts running through my mind, when I eventually stopped and saw myself again in the mirror, this time with different eyes : "Can you do it, or not ? This will change you from this day on ! You went too far this time. Boys don't do this! Are you a girl ? Are you a sissy girl ? Are you a sissy ? ... are you a coward, that can't go through ? Are you gonna back down in the face of something new ? You are here because of you . Just close your eyes and imagine that this beautiful being here has a name and wants to do something that will set her free. She waited all these years and now she wants to be free. Set Emma free !! Let Emma be what she wants to be.."

I felt a shiver up my spine, of pure arousal, excitement and joy. With the phone recording, I wasted no time in dropping on my knees in front of the phalus. I always dreamead that this is how it was supposed to be, with me looking from below in the eyes of my first before taking it for the first time in my mouth. I had no option but to close my eyes and imagine that I am aproaching his cock with my virgin mouth....

I swallow half of it, just to get a feeling from it. I am flooded with arousal ! The smell, the mouthfeel, the fulness, the salty taste got me dripping furiously like I never experienced before. I was afraid to touch myself as not to cum from the excitement. I am on my knees on the cold floor, eyes closed, a flash in my face, filming myself going back and forth, each time trying to take a little bit more. And Ioving it !

My imagination runs wild while I see myself pleasuring men in my submissive form. My knees start to hurt but I see that only a couple of minutes have passed. "What would I do if I must continue to pleasure a better man until he is satisfied ? I would never quit"

With my knees burning , I continue sucking my 'man', with no objection. With the chocker getting tighter around my neck, I put my hands in the back, and imagine being tied and coerced into sucking. My 'man' knows how long this journey has been, to reach this moment, to be brave enough to look him in his eye while I swallow his manhood, to offer myself to him dressed in womens clothes and to fell powerless in front of him.

I snap back from this perfect dream, put the dildo on the floor and get into a riding position, carefully positioning the moist tip on my tight pink hole. I lean a little to the back and slowly let the tip penetrate me. I get a sense of pain and arousal, but before i know it, I feel opening up and getting filled with pure pleasure. I get drunk with this feeling and ride it like there is no tomorrow. I start to touch myself to get even more pleasure, but after two strokes I eventually cum. I completly froze after this.

Guilt. I couldn't be and feel any lower. I was on the floor in a bathroom, just off from riding a dildo, dressed as a sissy. Emma was gone.

A few days later I briefly looked at some shots from my phone, the next week I watched the whole video and by the end of the week I was mouning with a sock in my mouth, hands tied behind my back, riding a dildo in a cold and dark room.'

'I never imagined you would share this with me. It seems like you've been building this desire and having these thoughts in you for quite some time.'

I smiled, we paused for a few seconds, and then he continues :

'I would like you to stay for a few more minutes, and if after that you decide you got all you came here for, then you can leave'.

I nod to let him know that it's okay and had no idea what could change in the following minutes. He got up and turned off all the lights, except the one in the bathroom, leaving the door slightly ajar.

'Is this comfortable enough for you?'

He put on some music, at a low level, and before siting down, he asked if I mind if he took off his pants and boxers. He knew I was to stunned to speak, and after a brief moment he did it anyway, sitting only in his tshirt.

He then continued, telling me that he never heard such a fantasy in this much detail.

'I'm glad you decided to share this with me. It's not everyday I get to meet someone who so honest about his feelings and insecurities. 'You've stepped a lot of boundries to be here right now, even done things you said you'd never do, I'm sure. I have no expectation for tonight, nothing has to happen. I just want you to try to be yourself.'

All his soft and gentle talk finally paid off, as I decided to take my jacket and shoes off and stay a little longer. I was conquering my fear.

I started to adjust to the low light and my eyes were curious to see what I only imagined. Close to me was a man with a semi erect penis, gazing at me with a warm smile, hoping to catch me take a glimpse at his crotch. It was an akward silence, with me often looking at his manhood, but pleasent thoughts started to invade my mind, and I was relaxing by the second, but at the same time breathing more and more heavily, as in anticipating a climax.

'I want you to be yourself, or let me convince you that you can be yourself when you are here with me. All that you beautifully depicted is a normal part of who you are, and you shouldn't have any doubts that you are different in any way. I am here support you in any way, in trying to discover yourself.'

I felt an even more sense of calmness in my body. His words were soothing and were telling me everything I needed to hear to wash away any last doubt that I was in the wrong place.

'If you want to try something, I am not going to stand in your way. You don't need to worry about anything, I won't think any less of you, regardless of what you want to do. I'll let you decided when you are ready. But don't think too much about it, sometimes you must act on instinct or listen to your feelings.'

My instincts were telling me to turn around and leave as soon as I entered his hotel room, as soon as I started talking, as soon as I layed on the bed, as soon as I took my jacket off. It was a constant signal that I have to get away, but somehow I was fighting it. This state slowly faded away, as I was being comforted by a man who kept reassuring me that I can keep an open mind about everything and that I cand leave whenever I want.

Seeing that I had to be pushed a little bit more, he adopted a more relaxed position in the chair, put his arms on the armrests and slightly opened his legs a little more, almost like an invitation, guiding me with a nod that this is the next step that I need to take. I asked if he could close his eyes for a few minutes, as I still felt a little scared to make the next move. I got down on my knees between his legs and reached for his cock. I couldn't believe how good it felt in my hand ; warm and slowly growing as I started massaging it like it was mine, rubbing my thumb over his tip that was oozing with pre cum.

He suggested that we move to the bed so I can be more comfortable, but as soon as he got up from the chair, I felt and intense arousal while seeing his cock almost touching my face. I stopped him, and asked him to look at time. The moment I only fantasised about was finally there, and at that point I didn't need any more convincing and I was ready to pleasure a man with my mouth.

I first touched his tip with my lips, with my tongue circling around it. I then looked him in the eyes while I slowly swollowed his knob and was making my way down his shaft. I was changed right then and there, and had no doubts that this who I wanted to be from now on. It was the most intense and intimate feeling of having a juicy cock in my mouth, a pleasure that I never thought I could ever experience.

He left out a few moans and I could see that he was happy with what I was doing. He put his hand on the back of my head and started to control the motion I was sucking him. I liked how he was very gentle and kept telling me what a good job I was doing.

We then move over to the bed, with him laying on his back and me to his side, resting my head on his stomach, looking at his beautiful penis. He then put one hand under my chin and was using the other to play with his cock on my lips. I just couldn't resist and started sucking him off again, licking, kissing and stroking his cock.

I could feel his hand slowly moving on my back, to my waist and then eventually entering my pants, touching my ass cheeks. There was a moment of pause, but I think he had a nice surprise when he noticed I wasn't wearing ordinary boxers, but panties. I really like how he was touching me and I think my body was really giving him signals that he should continue doing this. He kept squeezing my ass cheeks and moving his hand around them until he eventually reached my hole with his finger. Although I was prepared for anything that night, all cleaned up and lubed, I hoped he did not notice that.

He then told me to take my pants off as he lifted up my shirt over my head. I had reached another definitive moment in my life, as I never Imagined I could be almost naked near another man, wearing women lingerie. I wore what I enjoyed most while crossdressing : over the knee stockings, my favourite panties and a white lace bodysuit, that was covering my crotch but left my hole and ass uncovered. It was what I imagined a man would want to see.

He did not say anything at this point, but put me on my back an started to play with his hand on my chest and nipples, putting his thumb in my mouth, then gentle squeezing again my nipples. He continued to feel my body, constantly moving his hand up and down. I had a sense of freedom that was intoxicating, starting to moan and twist my body as he was gently caressing me. I didn't want him to stop.

Having so much pleasure from him touching me, I slowly turned to one side, with my back towards him. His slid his hand down my waist, gently pulliny my panties under my ass cheeks and then squeezing them with force.

I hadn't noticed until then, but there was a big mirror on the doors of the wardrobe, and I could distinguish myself in the low light. I had always hoped to be in such a position, dressed like this and moaning as I was being touched by a man. I knew I surrendered completly to him when he first put a finger in my hole, then two, and started to go gently in and out. His motion kept sending shivers in my body and I felt like I was losing my mind. I turned over my shoulder to look at him, and my hand reached for his cock, wanting to stroke him some more. I was having shortness of breath, my eyes were rolling back and I was practically beggin him to pop my cherry.

I saw him reach under the pillow and take out a condom, and sliding it over his erect cock.

Not more than an hour ago I was fearfully entering the hotel room of a man I hardly knew, and now I was about to be fucked like a woman.

I arched my back in preparation for his cock, that shortly pressed against my pink hole. He swiftly put one hand under me and grabbed me by my throat in a lock, while he was sliding his cock up and down between my ass cheeks.

I could see he was getting pleasure from being dominant, and I realised how horny I can get from having no control over my body. He then gripped both my wrists with his hand as not to put up a fight, and slowly began pushing his cock inside my hole. It was like I was briefly awakend from a beautiful dream and being flooded with even more pleasure. Feeling a real cock inside me for the first time was a feeling I could never forget.

I was moaning, almost in pain, as I didn't think my hole could stretch to allow his cock to penetrate me. He went slowly, back and forth, patiently and slowly entering me. I felt my body resisting this invasion, but I kept telling myself how badly I wanted to be fucked. I barely finished my thought that I felt him sliding inside me, letting out a deep moan of fulfilment.

My body instantly relaxed and I felt I had no power to move or make a sound. I was still feeling pain from being streched to the limit, but luckily he pulled out. He then proceeded to penetrate me again and again, just a stroke and then pulling out, so that I would adust to my new role.

I was letting signs I started to enjoy his cock entering me, and he quickly switched to faster thrusts while going deeper and deeper in my hole.

I started to enjoy being pounded, to the point I was realeasing high moans and was moving my hips towards his every thrust.

He then turned me on my stomach with my hands underneath me, locked my neck with his arm, and put his whole bodyweight on top of mine.

His cock quickly found my hole and slid a little bit easier inside me. He started slow, letting out big moans, and the gradually increased the speed he was fucking me.

The fact that I couldn't move or dare to speak, or that I couldn't object to anything he was doing fulfilled my desire of becoming submissive and I began swearing to myself that I would like to take up cock all my life. This was as close as I had ever been to him, hearing him breath right near my ear. This was such and intimate feeling, and although I never fantasised about kissing a man, I was anticipating the moment when he would slid his tongue in my mouth while he was deep in my ass...but that moment never came..

After a long and deep pounding, he turned on his back, dragging me at the same time on top of him while he was still inside me.

Now, in an overturned position, he held my waist as I struggled to find balance on my legs and arms, but after a few thrusts, I collapsed onto him. He quickly found my hole again, folded my legs to my chest and ferociously started to fuck me again. After he slowed down a little, I begged him not to cum just yet and got on all my fours in a doggy position, waiting for him to come and take me from behind. He could see that I was taking glimpses of myself in the mirror, and that I enjoyed getting fucked.

He then put me on my back, spread my legs and slowly entered, this time watching my expression as he was going in and out. He started going faster and faster, leaning towards me. I could feel him getting more and more aroused and I was pretty sure he would cum any minute. I put both my hands around him, pulled him on top of me and wrapped my legs around him. He must've enjoyed having me like this because he soon pulled out, took off the condom and cummed in succesive loads on my chest.

I laid on my back for a few moments while he went to the bathroom. My hole was still pulsing from being fucked like this for the first time and I still found it hard to move. The feeling of excitement was slowly staring to ware off, and the reality of what had happend started to flood my mind.

I began to search for my clothes and to whipe his cum of my chest. When he came out of the bathroom I was completly changed, almost in a state of panic. He must have known what was going on as I excused myself and told him I had to leave.