Sissy Outed Brandon to Brandy
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My CD / Sissy Story And 1st Meet Humiliation free porn video
I recently met up with someone to be a sissy slut for them and wanted to share what happened on my first meet. This is the genuine true story. I use the username indoblu on websites, but my sissy name is Holly so I'll refer to myself from now on as such. I'll mention my history as a sissy before talking about the meet up, skip the first few paragraphs to get to that bit.
I have always known I love girls clothes, lingerie, miniskirts, colourful sheer blouses , anything satin or lace, since a very young age. When I was 18, I finally had a credit card, and bought my own lingerie. I bought clothes off ASOS, packages would have girly clothing inside, but being a unisex shop no one at my home would know. My tight black miniskirt, and the black lingerie with garter belt you see in my profile picture were the first things I bought. It felt amazing, especially as they were all mine to wear whenever I wanted.
The amount of hot CDs / T-girls on the internet increased dramatically around this time, there were hundreds of sissy caption pictures, sissy training videos, hot CD videos and more. Alot of it helped me realise a side of myself that I strongly was. I always saw myself in the girls place watching straight porn, I always wanted to be the dominated twink bottom watching gay porn, and I always wanted to be the passable girl watching TS porn. What started as me expressing femininity turned into me understanding I wanted to be a sissy, and I truly wanted to serve cock.
In my room all dressed up I began pretending I was serving a real man, being on my stocking covered knees and using make shift items as dildos. I came so much faster if I had my panties pulled to the side with something thrusting back and forth in my ass, even though my cock wouldn't be completely hard.
I joined xhamster and many other sites, and shared pictures of myself in my lingerie. I left descriptions here and on sites like CL, saying I was up to meet to be a sissy for someone. I chatted with lots of people, started camming one on one for them and even cammed publicly on xhamster's old cam site. I did all of it with hopes of someone meeting me. It was very exciting, I chatted with many different types of guys.
It can be difficult being a sissy and chatting to guys on these sites. Some think you are a full MTF person, others think you are dressed and smooth 24/7 and some even think you are a real girl!
Out of the ones that understand what a sissy is, you have the married guys, the guys who can barely string a sentence, the ones who log out immediately after a cam session and never chat again until months later, the guys who come off obviously suspicious and of course ...timewasters. The most disappointing though is the overly aggressive Doms, who think being a Dom is about being highly aggressive from the very start, because you know their heart is in the right place, but they are doing it wrong.
If you are a Dom reading this, please understand that a sissy wants to serve you and be degraded by you, but it is something you build up to, let your sissy know you will take charge when the situation is right, not from when you're getting to know each other! Preparing to be a sissy takes alot of time, they can't just cam for you the moment you order, or come round and suck you off the moment you say, although I'm sure any sissy would love to, most times it's just not feasible!
You may think I am picky with guys from those last paragraphs, but I am not. I like hygienic guys with trimmed/smooth cocks is the only thing I look for physically in a man. I am quite a slutty desperate sissy! However, time went by and I couldn't find anyone to meet.
I was finding it hard to balance being me in 'boy mode', and my 'girly sissy mode' Holly. I didn't want to work out too much and lose my girly body, but also wanted to live my normal boy life. At one point 2 years ago, I made the mistake of 'purging' - getting rid of all my sissy stuff,. It is a common thing many sissies go through. I was moving out and it would be difficult to hide my lingerie. I also wanted to get on with being a single straight guy, instead of also being Holly. It was a huge mistake, 4 months later I was buying clothes again, and I still miss so many of my old clothes.
Purging is a common thing sissies do and you don't really hear about anyone who succeeds. It was clear to me that I didn't want to lose my sissy side, that I loved dressing up, and could never live without getting new lingerie. Though I never shared that I was Holly with anyone, I was not in any way personally ashamed of my sissy side. I became very comfortable with being both, although I would not be comfortable sharing it with anyone, simply because they wouldn't understand. It took me long enough to make sense of this side of myself, it would be totally alien to someone not exposed to this world in the slightest (which we can assume most are!).
I got much deeper into my sissy side. I fantasised so much more about being a sissy, and especially being humiliated for being a sissy. My online chats became alot more filthy, and I think most guys couldn't keep up with how much of a sissy I was! I also got a lot more turned on by not being able to touch myself, and using ribbons as a chastity. My cock was now my sissy clit, either to be tucked in my panties or dangling out of them, useless and limp. My ass was my sissy pussy, and would be my prime way of feeling sensation when pleasuring myself.
I got a suitable wig, makeup and many more clothes, my favourite outfit was my purple and black lace set, french panties, bra and garter belt. Worn with hold up stockings, a tight black mini skirt and a black satin cami top. The moment I got that purple and black set I cammed to a group of users on xhamster, they made me feel like a filthy slut, carrying out their commands to pose and touch myself for them. They talked among themselves about how much of a slut I was, and how they'd like to use me and leave me coated in their cum. It was one of the hottest experiences ever.
I cammed, chatted and put out adverts because my sole intention now was to find someone to be their fucktoy. I was using Kik now, and chats got alot further towards a meet, but still not the final goal. But finally I met someone who sounded perfect.
From CL, I got talking to a someone who showed a photo that they had been with a crossdresser before. He was 50 years old, experienced, and eager to Dom a sissy. After asking me all about what I wanted, most of which was simply to pleasure him, unlike many other he understood easily. He quickly understood how as a sissy I was a bottom only and craved humiliation for being such a subservient pussy boy, but he didn't go full Dom until we had got to know each other.
When we had got to know each other wants after that hour long chat, he became my master, and from them I would always refer to him as such. We'd chat for over two weeks, me eager to show off how I would serve my master, how girly I was and how I needed to be made a real girl by his cock. Of course I would never be a real girl, but I would become a true sissy, master would remind me. It was important I knew my place, I was a boy who was such a sissy I would serve men without any concern for my own pleasure.
We arranged to meet at a hotel in a city near me. We would both pay for the hotel. The night before I dressed up and sent lots of pictures, master was very excited to use me. It took along time to prepare for the meet, especially getting shaved and smooth. I won't go into detail but it took extremely long and it wasn't pretty!
I got the bus to the city, with a large rucksack full of lingerie on my back. I was very nervous. Would master want me when we met? Would we get to the hotel room discreetly? Not only that but if things did go according to plan, I would soon be sucking a guys cock and being their bitch for the next few hours. It was going to be my first time, and I was slightly tempted to not go, but master had travelled almost an hour to get there, I had been searching for this for too long, and most of all, I truly wanted to do this.
I went to the hotel lobby, I couldn't see master so went to the toilet, he text me describing where he was. I found him and he greeted me with a smile on his face. I smiled too, I was locked in, this was definitely going to happen. We went straight up to the room - a cleaning lady blocked the stairs and took notice of us as we squeezed past her on the stairs. She had the look of someone who suspected our motives for checking into a hotel next to a railway station at 6pm.
Our room had a large double bed but was cramped. We chatted about our history and master poured himself wine. He offered me something to drink but I didn't fancy it. A genuine thought of 'I only want to taste pure cock' crossed my mind. Looking back I laugh at such a weird thought crossing my mind, even for a sissy, but I was in an extremely sissy mood that day.
Master was tall, stocky, with light coloured hair. He was mostly in shape with a slight belly. Overall he looked better than I was expecting from photos. He liked how even my boy hair was 'pretty girly' and looked at me in a way of 'what are we going to do with you then?' He quickly made me feel desired, and wasn't going to go dom until I was dressed.
He made me show him all the lingerie I bought. There was some pieces he liked, and he made me go to the bathroom to try some on. I modelled a set of pink, a pink bra and pink french knickers wearing pink fishnets. Master was excited at how girly my body was. He then made me try a floral blue set with mismatched black garter belt. The set he settled on was the one I mentioned earlier...
I put on my purple and black lace thong, bra and garter belt, which suited my pale skin. With them I wore opaque black stockings almost up my entire long legs, and attached them to my garters. I put my satin cami with spaghetti straps on for my top, and tucked them into a tight black miniskirt that I wore fairly high on my waist, so it only just covered my bum. Next I put on eye shadow rubbing it in to give a smokey, sultry look to my eyes, and added dark red lipstick. I put on my wig, a brunette one, long with bangs for the fringe. I was excited to be fully transformed for someone.
Master liked what he saw. He brought with him a pair of high heels in my size. They were a white/grey snake skin colour, 5 inches, and surprisingly worked with my outfit. I had never worn heels before and instantly it felt amazing, my legs felt so much girly just wearing them. Master made me parade a little for him, I could feel my thong rubbing hard on my panties bulge and my boi pussy as I moved. It was hard to walk, but that didn't matter, as Master gently pushed me to sit on the bed in front of him.
Here I was finally, a sissy slut ready to serve. I couldn't believe it. Outside of being Holly I had such a normal life, no one in my life would suspect me of being this. And yet I had gone to all this effort, put in all this money buying clothes, buying a hotel room, shaving, practicing being girly... all so I could serve a man so much older than me, because I was a true sissy slut. Because I not only dreamed of serving real men, but actually needed to do it. My thoughts were constantly going between my normal mode, and my sissy mode. It was still not as simple as being 100% sissy. It is difficult to explain. But I was going to do this, I was going to be the best slut I could, I would be as girly a I could even though I could only be a sissy.
Master felt up my bra and down to my hips repeatedly. "You've been a good girl to do all this for your master... so smooth", as he felt the small part of my leg not covered in stockings, under my skirt. "The clothes you buy... you really are a slut.. only sluts pick out only clothing like this. Get on your knees". I flipped over on the bed, on my knees, letting my chest go low so my ass was up, I got into a position than was girly as possible. "Good" He said, and lifted my skirt up, until it was like a belt above my garters, my panty clad ass fully on display. He also let my cami top hang off exposing my lace bra.
As he felt my body my bulge was growing in my panties - it felt so good to be like this already! I was tempted to touch myself, as I reached Master put his hand on my wrist, stopping me. "No, sissy's don't pleasure themselves like that. You're getting excited already aren't you slut." He took some ribbons out and used them to tie up my sissy clit quite tight, before placing them back to be trapped in my panties tightly. "Is that better, Holly?", "Yes Master thank you". He smacked my ass making me say thank you each time. Gently he run a finger on the outside of my panties, teasing my hole.
Master went to the other side of the bed. My head was directly in front of his crotch, covered by his boxers. "Pull them off with your teeth" I did as commanded. "Good girl". Here I was, Master's cock in front of my face, there was no going back after this, I would of proved I am a true sissy. On the way here on the bus, I wondered if at this point, where Master's cock was presented, whether I'd lose my nerve and not be able to do so. In reality though, it was the opposite, I found myself straight away taking Master's cock in my mouth, surprising even myself.
Master could tell I was enjoying this moment, "Ha ha, just what you always wanted, isn't it?", I replied with a muffled 'yes Master' as I continued to feel his cock grow in my mouth. When it was full size, master took it out my mouth and slapped my face with it repeatedly. "You've impressed your Master, this is very good for a first timer. Suck on my balls." I licked them and took them fully in my mouth. I didn't choose to be a sissy, but that's what I am, and even though I was all about my Master's pleasure, I was enjoying myself - despite the humiliation that I found cock and balls to taste surprisingly good. I was made to suck much longer, while Master put his hands all over my smooth body. Sometimes he rubbed my tied up clit in panties like it was a real clit.
He was an expert at treating a sissy exactly like how she should be treated.He'd treat me like a girl but remind that I am not one, which is right, a sissy is not a girl. A sissy is far more subservient, and exists only to serve another's pleasure, not their own. Not only that, sissies are not real girls and more importantly, not real men. Master would make sure to remind me of this, laughing at my tiny clit and asking me if I enjoyed serving a real man's cock, which usually I responded to with a muffled 'yes master'. Outside this hotel room, I'd never admit to such, but I was truly loving serving a real man.
At one point Master was feeling my girly body real good, and I said 'mmmm, yes Daddy' instead of Master, he just laughed at me and then spanked me. He took his cock out my mouth, and told me to stay on my knees, keep my ass raised and hold onto the heels of my shoes with my hands. I waited there for ten minutes, while he drank wine and admired my body. I felt both valued and cheap all at once. He then put a collar on me, and held me on a chain leash. "How is that slut?" "Good thank you Master, it makes me feel more like your property". We hadn't mentioned collaring me at all til this point, I guess Master thought it would suit me.
What a pussy I was. People from the rest of my life were going through my mind. I imagined what my Ex would think of me like this. How humiliating to go from normal relationships to being this sissy slave. I had made no efforts to find a new girlfriend, but I had spent hours in chats and on cam to find a cock to serve. Despite my tied up clit I was loving it. All the sissy captions were true, and living them felt amazing and embarrassing all the same time.
Master was behind me now. He pulled the leash and I was forced upwards by my neck, I was straight up but on my knees. He felt my body, scrunching my nonexistant boobs through my bra, and letting his hand feel down my stocking clad thighs. "Such a good girl" his finger feeling through my boipussy from the outside of my thong, "so tight", his wet finger pushed into my pussy, and he pushed me back down onto my chest. "Another finger please Master, I can take it", and he did so. Instead of three fingers, he got put a dildo, squirted it with lube and pulled my thong to the side. "Do you want this Holly?" "Yes please Master". It filled me up instantly, after thrusting it a few times he let it stay there and made me suck his cock again. "I bet you would love a couple more guys here, you're a true slut, you'd love to be spitroasted here". He was 100% correct, but I could barely reply, he pulled the collar to force my mouth onto his dick. After a few seconds I choked, gagging with tears coming out my eyes, Master just laughed.
He held his cock over my face and looked down on me, admiring his sissy slut, I looked back from underneath the cock, smiling and thanking him, giving it a lick from underneath, base to tip. "You've been a very good girl for you master" he said, while moving behind me and feeling my ass "can you serve your master more?". He was teasing me, he wanted total submission, he wanted me to admit I wanted his cock to fuck my ass. I wiggled my panty wearing bum in the air, my legs spread wider now. "Please fuck me Master, fuck my pussy", "You don't have a pussy, sissy, you have a boipussy" "Master, please make me feel like a real girl, fuck my boipussy please" He held the head of his cock to my tight hole. "Beg for it" he commanded. "Master, please fuck me" but he held it there, "Master please please make me a girl by filling me with your cock" still nothing, "Master I only wish to serve a real man like yourself, all I am is a sissy to serve you" nope, "I love your cock Master, I love all cock, I am a true sissy, thank you for helping me do the only thing I am useful for, I want to do everything to prove how much of a sissy I am, I am so happy serving you Master and you're cock filling me is the only pleasure I need". He laughed, "You really are the most sub sissy I have ever met, you don't have to prove that anymore, just remember where you are right now, how you'll look back on this moment, dressed in lacey lingerie, on your knees, useless dick tied up, collared, serving a real man, admitting how much of a pussy you are, fine sissy, I will fuck you in your boipussy as you desire". "Thank you master, thank you, thank you"
He swiftly pulled my thong down where it stayed suspended between my thighs, "hold your boipussy open sissy", I did so, a cold sensation came over as Master squirted lube on it. "mmm that looks good". It was easy to submit to this after all I'd been through today, I loved the sensation instantly, the slap noise was thrilling to hear as Master pounded me. "That feels good Master, oh my god that feels good", I spread my arms out on the bed and clutched it tight to hold on while Master had his way, pulling my hips to pull me back on his cock. He pulled the collar, him fully inside me, and held me there, upright on his cock. I wiggled on it, I wanted to feel as much of him in me as I could.
He moved under me, and we went from doggy to cowgirl. During the pounding my clit had come loose from the panties, I tucked them back in. The view down to see my bulge in panties while I rode Master was amazing,. I bounced on his cock, it felt so subservient to be the one doing all the work while Master lay on his back. "It feels so good to be your sissy Master, I love serving a real man, thank you, thank you". At this point I heard laughing outside the hotel door, I went silent immediately, whoever it was noticed the change in volume and went away quickly. How embarrassing for someone to hear me like this. My guess was it was the cleaning lady from earlier. Even though I could handle humiliation that was too much for me, to be laughed at while riding and older mans cock really brought me back to reality. I know I mentioned it but this is when I truly realised just how much a sissy I was, I was slightly ashamed. Master offered to take photos of me, but the shame made me say no. I regret that decision.
Master didn't seem bothered by the eavesdropper, but by now he wanted to cum. He pushed me down on my front, held each of my hands down and fucked me fast while lying on top of me. I could only moan in a girly way at this point. I was in sissy heaven. Master was grunting, then flipped me round and took off his condom. He lifted my panties and came all over my ass cheek. He fell onto the bed, letting go off my panties I felt the cum sandwich between the thong strap and my ass cheek. I had done it. I had been the sissy I always needed to be... at least once.
Master wiped up the cum, then made me lie next to him, putting one arm around me like I was a hareem. We chatted normally for awhile after this, about TS/CD experiences and more. He had experience in many fetish scenes and said he was impressed with someone as young as me being so into this kink. We cleaned up, I changed back into my boy clothes but master made me keep on my dirty thong and tied up clit. It was time to say goodbye and catch the bus home. No sign of the cleaner as I left the hotel *phew*
It had been about 4 hours in the hotel room, but there were many people ready to catch the bus. I looked at them wondering if they suspected me in the slightest. I had plenty of time to think on the bus ride home. It was quite a hardcore first time, but very fun. I don;t think I could of had much better experience for my first time sissy serving.
I'd like to try different ways while dressed to, maybe a less sissy more of a loving boyfriend with cd girlfriend relationship where it is less about humiliation, or a hardcore fling but less about the Master / Servant relationship. The ultimate fantasy to live though would be being used and humiliated by a couple. Even though I had fun I still felt some shame, as I mentioned the boy / cd balance is tough for me even after all this, but 2 months later I'm already buying more clothes, thinking about meeting again, and worrying I'll blurt out my secret while drunk. It feels there is still so much of my sissy side to explore still. I also consider less of the sexual side of crossdressing and am thinking about appearing more androgynous in my normal fashion life, but I still doubt I'll do so. Making a cd friend to go out clubbing with would be great.
What I described was the genuine true story. It happened on September 9th 2014. I did this for my own record, for the information of crossdressers, sissies and doms and because sharing it was hot. It's a shame I didn't get pictures, but it really was too much for me at the time with the cleaner listening in, however Im sure many Xhamster users who have chatted to me will know this story is true. I'm interested in everything from friends to more, if you like the sound of me and are a genuine person let me know, if the circumstances are right, maybe we'll make another story! ;)
I have always known I love girls clothes, lingerie, miniskirts, colourful sheer blouses , anything satin or lace, since a very young age. When I was 18, I finally had a credit card, and bought my own lingerie. I bought clothes off ASOS, packages would have girly clothing inside, but being a unisex shop no one at my home would know. My tight black miniskirt, and the black lingerie with garter belt you see in my profile picture were the first things I bought. It felt amazing, especially as they were all mine to wear whenever I wanted.
The amount of hot CDs / T-girls on the internet increased dramatically around this time, there were hundreds of sissy caption pictures, sissy training videos, hot CD videos and more. Alot of it helped me realise a side of myself that I strongly was. I always saw myself in the girls place watching straight porn, I always wanted to be the dominated twink bottom watching gay porn, and I always wanted to be the passable girl watching TS porn. What started as me expressing femininity turned into me understanding I wanted to be a sissy, and I truly wanted to serve cock.
In my room all dressed up I began pretending I was serving a real man, being on my stocking covered knees and using make shift items as dildos. I came so much faster if I had my panties pulled to the side with something thrusting back and forth in my ass, even though my cock wouldn't be completely hard.
I joined xhamster and many other sites, and shared pictures of myself in my lingerie. I left descriptions here and on sites like CL, saying I was up to meet to be a sissy for someone. I chatted with lots of people, started camming one on one for them and even cammed publicly on xhamster's old cam site. I did all of it with hopes of someone meeting me. It was very exciting, I chatted with many different types of guys.
It can be difficult being a sissy and chatting to guys on these sites. Some think you are a full MTF person, others think you are dressed and smooth 24/7 and some even think you are a real girl!
Out of the ones that understand what a sissy is, you have the married guys, the guys who can barely string a sentence, the ones who log out immediately after a cam session and never chat again until months later, the guys who come off obviously suspicious and of course ...timewasters. The most disappointing though is the overly aggressive Doms, who think being a Dom is about being highly aggressive from the very start, because you know their heart is in the right place, but they are doing it wrong.
If you are a Dom reading this, please understand that a sissy wants to serve you and be degraded by you, but it is something you build up to, let your sissy know you will take charge when the situation is right, not from when you're getting to know each other! Preparing to be a sissy takes alot of time, they can't just cam for you the moment you order, or come round and suck you off the moment you say, although I'm sure any sissy would love to, most times it's just not feasible!
You may think I am picky with guys from those last paragraphs, but I am not. I like hygienic guys with trimmed/smooth cocks is the only thing I look for physically in a man. I am quite a slutty desperate sissy! However, time went by and I couldn't find anyone to meet.
I was finding it hard to balance being me in 'boy mode', and my 'girly sissy mode' Holly. I didn't want to work out too much and lose my girly body, but also wanted to live my normal boy life. At one point 2 years ago, I made the mistake of 'purging' - getting rid of all my sissy stuff,. It is a common thing many sissies go through. I was moving out and it would be difficult to hide my lingerie. I also wanted to get on with being a single straight guy, instead of also being Holly. It was a huge mistake, 4 months later I was buying clothes again, and I still miss so many of my old clothes.
Purging is a common thing sissies do and you don't really hear about anyone who succeeds. It was clear to me that I didn't want to lose my sissy side, that I loved dressing up, and could never live without getting new lingerie. Though I never shared that I was Holly with anyone, I was not in any way personally ashamed of my sissy side. I became very comfortable with being both, although I would not be comfortable sharing it with anyone, simply because they wouldn't understand. It took me long enough to make sense of this side of myself, it would be totally alien to someone not exposed to this world in the slightest (which we can assume most are!).
I got much deeper into my sissy side. I fantasised so much more about being a sissy, and especially being humiliated for being a sissy. My online chats became alot more filthy, and I think most guys couldn't keep up with how much of a sissy I was! I also got a lot more turned on by not being able to touch myself, and using ribbons as a chastity. My cock was now my sissy clit, either to be tucked in my panties or dangling out of them, useless and limp. My ass was my sissy pussy, and would be my prime way of feeling sensation when pleasuring myself.
I got a suitable wig, makeup and many more clothes, my favourite outfit was my purple and black lace set, french panties, bra and garter belt. Worn with hold up stockings, a tight black mini skirt and a black satin cami top. The moment I got that purple and black set I cammed to a group of users on xhamster, they made me feel like a filthy slut, carrying out their commands to pose and touch myself for them. They talked among themselves about how much of a slut I was, and how they'd like to use me and leave me coated in their cum. It was one of the hottest experiences ever.
I cammed, chatted and put out adverts because my sole intention now was to find someone to be their fucktoy. I was using Kik now, and chats got alot further towards a meet, but still not the final goal. But finally I met someone who sounded perfect.
From CL, I got talking to a someone who showed a photo that they had been with a crossdresser before. He was 50 years old, experienced, and eager to Dom a sissy. After asking me all about what I wanted, most of which was simply to pleasure him, unlike many other he understood easily. He quickly understood how as a sissy I was a bottom only and craved humiliation for being such a subservient pussy boy, but he didn't go full Dom until we had got to know each other.
When we had got to know each other wants after that hour long chat, he became my master, and from them I would always refer to him as such. We'd chat for over two weeks, me eager to show off how I would serve my master, how girly I was and how I needed to be made a real girl by his cock. Of course I would never be a real girl, but I would become a true sissy, master would remind me. It was important I knew my place, I was a boy who was such a sissy I would serve men without any concern for my own pleasure.
We arranged to meet at a hotel in a city near me. We would both pay for the hotel. The night before I dressed up and sent lots of pictures, master was very excited to use me. It took along time to prepare for the meet, especially getting shaved and smooth. I won't go into detail but it took extremely long and it wasn't pretty!
I got the bus to the city, with a large rucksack full of lingerie on my back. I was very nervous. Would master want me when we met? Would we get to the hotel room discreetly? Not only that but if things did go according to plan, I would soon be sucking a guys cock and being their bitch for the next few hours. It was going to be my first time, and I was slightly tempted to not go, but master had travelled almost an hour to get there, I had been searching for this for too long, and most of all, I truly wanted to do this.
I went to the hotel lobby, I couldn't see master so went to the toilet, he text me describing where he was. I found him and he greeted me with a smile on his face. I smiled too, I was locked in, this was definitely going to happen. We went straight up to the room - a cleaning lady blocked the stairs and took notice of us as we squeezed past her on the stairs. She had the look of someone who suspected our motives for checking into a hotel next to a railway station at 6pm.
Our room had a large double bed but was cramped. We chatted about our history and master poured himself wine. He offered me something to drink but I didn't fancy it. A genuine thought of 'I only want to taste pure cock' crossed my mind. Looking back I laugh at such a weird thought crossing my mind, even for a sissy, but I was in an extremely sissy mood that day.
Master was tall, stocky, with light coloured hair. He was mostly in shape with a slight belly. Overall he looked better than I was expecting from photos. He liked how even my boy hair was 'pretty girly' and looked at me in a way of 'what are we going to do with you then?' He quickly made me feel desired, and wasn't going to go dom until I was dressed.
He made me show him all the lingerie I bought. There was some pieces he liked, and he made me go to the bathroom to try some on. I modelled a set of pink, a pink bra and pink french knickers wearing pink fishnets. Master was excited at how girly my body was. He then made me try a floral blue set with mismatched black garter belt. The set he settled on was the one I mentioned earlier...
I put on my purple and black lace thong, bra and garter belt, which suited my pale skin. With them I wore opaque black stockings almost up my entire long legs, and attached them to my garters. I put my satin cami with spaghetti straps on for my top, and tucked them into a tight black miniskirt that I wore fairly high on my waist, so it only just covered my bum. Next I put on eye shadow rubbing it in to give a smokey, sultry look to my eyes, and added dark red lipstick. I put on my wig, a brunette one, long with bangs for the fringe. I was excited to be fully transformed for someone.
Master liked what he saw. He brought with him a pair of high heels in my size. They were a white/grey snake skin colour, 5 inches, and surprisingly worked with my outfit. I had never worn heels before and instantly it felt amazing, my legs felt so much girly just wearing them. Master made me parade a little for him, I could feel my thong rubbing hard on my panties bulge and my boi pussy as I moved. It was hard to walk, but that didn't matter, as Master gently pushed me to sit on the bed in front of him.
Here I was finally, a sissy slut ready to serve. I couldn't believe it. Outside of being Holly I had such a normal life, no one in my life would suspect me of being this. And yet I had gone to all this effort, put in all this money buying clothes, buying a hotel room, shaving, practicing being girly... all so I could serve a man so much older than me, because I was a true sissy slut. Because I not only dreamed of serving real men, but actually needed to do it. My thoughts were constantly going between my normal mode, and my sissy mode. It was still not as simple as being 100% sissy. It is difficult to explain. But I was going to do this, I was going to be the best slut I could, I would be as girly a I could even though I could only be a sissy.
Master felt up my bra and down to my hips repeatedly. "You've been a good girl to do all this for your master... so smooth", as he felt the small part of my leg not covered in stockings, under my skirt. "The clothes you buy... you really are a slut.. only sluts pick out only clothing like this. Get on your knees". I flipped over on the bed, on my knees, letting my chest go low so my ass was up, I got into a position than was girly as possible. "Good" He said, and lifted my skirt up, until it was like a belt above my garters, my panty clad ass fully on display. He also let my cami top hang off exposing my lace bra.
As he felt my body my bulge was growing in my panties - it felt so good to be like this already! I was tempted to touch myself, as I reached Master put his hand on my wrist, stopping me. "No, sissy's don't pleasure themselves like that. You're getting excited already aren't you slut." He took some ribbons out and used them to tie up my sissy clit quite tight, before placing them back to be trapped in my panties tightly. "Is that better, Holly?", "Yes Master thank you". He smacked my ass making me say thank you each time. Gently he run a finger on the outside of my panties, teasing my hole.
Master went to the other side of the bed. My head was directly in front of his crotch, covered by his boxers. "Pull them off with your teeth" I did as commanded. "Good girl". Here I was, Master's cock in front of my face, there was no going back after this, I would of proved I am a true sissy. On the way here on the bus, I wondered if at this point, where Master's cock was presented, whether I'd lose my nerve and not be able to do so. In reality though, it was the opposite, I found myself straight away taking Master's cock in my mouth, surprising even myself.
Master could tell I was enjoying this moment, "Ha ha, just what you always wanted, isn't it?", I replied with a muffled 'yes Master' as I continued to feel his cock grow in my mouth. When it was full size, master took it out my mouth and slapped my face with it repeatedly. "You've impressed your Master, this is very good for a first timer. Suck on my balls." I licked them and took them fully in my mouth. I didn't choose to be a sissy, but that's what I am, and even though I was all about my Master's pleasure, I was enjoying myself - despite the humiliation that I found cock and balls to taste surprisingly good. I was made to suck much longer, while Master put his hands all over my smooth body. Sometimes he rubbed my tied up clit in panties like it was a real clit.
He was an expert at treating a sissy exactly like how she should be treated.He'd treat me like a girl but remind that I am not one, which is right, a sissy is not a girl. A sissy is far more subservient, and exists only to serve another's pleasure, not their own. Not only that, sissies are not real girls and more importantly, not real men. Master would make sure to remind me of this, laughing at my tiny clit and asking me if I enjoyed serving a real man's cock, which usually I responded to with a muffled 'yes master'. Outside this hotel room, I'd never admit to such, but I was truly loving serving a real man.
At one point Master was feeling my girly body real good, and I said 'mmmm, yes Daddy' instead of Master, he just laughed at me and then spanked me. He took his cock out my mouth, and told me to stay on my knees, keep my ass raised and hold onto the heels of my shoes with my hands. I waited there for ten minutes, while he drank wine and admired my body. I felt both valued and cheap all at once. He then put a collar on me, and held me on a chain leash. "How is that slut?" "Good thank you Master, it makes me feel more like your property". We hadn't mentioned collaring me at all til this point, I guess Master thought it would suit me.
What a pussy I was. People from the rest of my life were going through my mind. I imagined what my Ex would think of me like this. How humiliating to go from normal relationships to being this sissy slave. I had made no efforts to find a new girlfriend, but I had spent hours in chats and on cam to find a cock to serve. Despite my tied up clit I was loving it. All the sissy captions were true, and living them felt amazing and embarrassing all the same time.
Master was behind me now. He pulled the leash and I was forced upwards by my neck, I was straight up but on my knees. He felt my body, scrunching my nonexistant boobs through my bra, and letting his hand feel down my stocking clad thighs. "Such a good girl" his finger feeling through my boipussy from the outside of my thong, "so tight", his wet finger pushed into my pussy, and he pushed me back down onto my chest. "Another finger please Master, I can take it", and he did so. Instead of three fingers, he got put a dildo, squirted it with lube and pulled my thong to the side. "Do you want this Holly?" "Yes please Master". It filled me up instantly, after thrusting it a few times he let it stay there and made me suck his cock again. "I bet you would love a couple more guys here, you're a true slut, you'd love to be spitroasted here". He was 100% correct, but I could barely reply, he pulled the collar to force my mouth onto his dick. After a few seconds I choked, gagging with tears coming out my eyes, Master just laughed.
He held his cock over my face and looked down on me, admiring his sissy slut, I looked back from underneath the cock, smiling and thanking him, giving it a lick from underneath, base to tip. "You've been a very good girl for you master" he said, while moving behind me and feeling my ass "can you serve your master more?". He was teasing me, he wanted total submission, he wanted me to admit I wanted his cock to fuck my ass. I wiggled my panty wearing bum in the air, my legs spread wider now. "Please fuck me Master, fuck my pussy", "You don't have a pussy, sissy, you have a boipussy" "Master, please make me feel like a real girl, fuck my boipussy please" He held the head of his cock to my tight hole. "Beg for it" he commanded. "Master, please fuck me" but he held it there, "Master please please make me a girl by filling me with your cock" still nothing, "Master I only wish to serve a real man like yourself, all I am is a sissy to serve you" nope, "I love your cock Master, I love all cock, I am a true sissy, thank you for helping me do the only thing I am useful for, I want to do everything to prove how much of a sissy I am, I am so happy serving you Master and you're cock filling me is the only pleasure I need". He laughed, "You really are the most sub sissy I have ever met, you don't have to prove that anymore, just remember where you are right now, how you'll look back on this moment, dressed in lacey lingerie, on your knees, useless dick tied up, collared, serving a real man, admitting how much of a pussy you are, fine sissy, I will fuck you in your boipussy as you desire". "Thank you master, thank you, thank you"
He swiftly pulled my thong down where it stayed suspended between my thighs, "hold your boipussy open sissy", I did so, a cold sensation came over as Master squirted lube on it. "mmm that looks good". It was easy to submit to this after all I'd been through today, I loved the sensation instantly, the slap noise was thrilling to hear as Master pounded me. "That feels good Master, oh my god that feels good", I spread my arms out on the bed and clutched it tight to hold on while Master had his way, pulling my hips to pull me back on his cock. He pulled the collar, him fully inside me, and held me there, upright on his cock. I wiggled on it, I wanted to feel as much of him in me as I could.
He moved under me, and we went from doggy to cowgirl. During the pounding my clit had come loose from the panties, I tucked them back in. The view down to see my bulge in panties while I rode Master was amazing,. I bounced on his cock, it felt so subservient to be the one doing all the work while Master lay on his back. "It feels so good to be your sissy Master, I love serving a real man, thank you, thank you". At this point I heard laughing outside the hotel door, I went silent immediately, whoever it was noticed the change in volume and went away quickly. How embarrassing for someone to hear me like this. My guess was it was the cleaning lady from earlier. Even though I could handle humiliation that was too much for me, to be laughed at while riding and older mans cock really brought me back to reality. I know I mentioned it but this is when I truly realised just how much a sissy I was, I was slightly ashamed. Master offered to take photos of me, but the shame made me say no. I regret that decision.
Master didn't seem bothered by the eavesdropper, but by now he wanted to cum. He pushed me down on my front, held each of my hands down and fucked me fast while lying on top of me. I could only moan in a girly way at this point. I was in sissy heaven. Master was grunting, then flipped me round and took off his condom. He lifted my panties and came all over my ass cheek. He fell onto the bed, letting go off my panties I felt the cum sandwich between the thong strap and my ass cheek. I had done it. I had been the sissy I always needed to be... at least once.
Master wiped up the cum, then made me lie next to him, putting one arm around me like I was a hareem. We chatted normally for awhile after this, about TS/CD experiences and more. He had experience in many fetish scenes and said he was impressed with someone as young as me being so into this kink. We cleaned up, I changed back into my boy clothes but master made me keep on my dirty thong and tied up clit. It was time to say goodbye and catch the bus home. No sign of the cleaner as I left the hotel *phew*
It had been about 4 hours in the hotel room, but there were many people ready to catch the bus. I looked at them wondering if they suspected me in the slightest. I had plenty of time to think on the bus ride home. It was quite a hardcore first time, but very fun. I don;t think I could of had much better experience for my first time sissy serving.
I'd like to try different ways while dressed to, maybe a less sissy more of a loving boyfriend with cd girlfriend relationship where it is less about humiliation, or a hardcore fling but less about the Master / Servant relationship. The ultimate fantasy to live though would be being used and humiliated by a couple. Even though I had fun I still felt some shame, as I mentioned the boy / cd balance is tough for me even after all this, but 2 months later I'm already buying more clothes, thinking about meeting again, and worrying I'll blurt out my secret while drunk. It feels there is still so much of my sissy side to explore still. I also consider less of the sexual side of crossdressing and am thinking about appearing more androgynous in my normal fashion life, but I still doubt I'll do so. Making a cd friend to go out clubbing with would be great.
What I described was the genuine true story. It happened on September 9th 2014. I did this for my own record, for the information of crossdressers, sissies and doms and because sharing it was hot. It's a shame I didn't get pictures, but it really was too much for me at the time with the cleaner listening in, however Im sure many Xhamster users who have chatted to me will know this story is true. I'm interested in everything from friends to more, if you like the sound of me and are a genuine person let me know, if the circumstances are right, maybe we'll make another story! ;)
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