A Feminised First....

New year and a new commitment to update this blog a bit more with my ongoing adventures. I've recently moved accomodation and luckily one of the benefits it's given me is that I've been able to dress a hell of a lot more than I used to be able to. Each night, once home from work I would change into female clothing, apply make up, and spend the rest of the day fully feminised. I also spent a lot more time browsing swinging sites which is where I met Sam. He wasn't local to my area, but did regularly visit every few weeks for work and he was keen to meet up with me. I enjoyed the regular naughty messages we sent one another and decided that he was definitely high on list of people I was keen to meet.

Sam was in his late forties, well built, and an occasional crossdresser when he had the time he told me. He had liked my pics and profile and contacted me with an offer I found hard to refuse. He wanted to accompany me outside when I was fully dressed and take me out as his date! I was very flattered with this idea and so we began putting a plan into action where he'd come pick me up and take me out for a walk somewhere relatively quiet. If this went well then we'd up the ante somewhat and go somewhere more daring the next time!

The first night we met he picked me up from my flat. I'd spent the evening getting ready for him and was dressed in a tight black corset, black leather miniskirt, sheer black top, 10 denier sheer black hold ups, skimpy sheer knickers, strappy stilletos, and was wearing a pair of 38 E breast forms. I was wearing my recently purchased short blonde bobbed wig which I hadn't worn in public up until then.

The text then arrived simply saying "I'm here", so I tottered out to his waiting car and climbed in the passenger door next to him.

As soon as I climbed in I saw his eyes immediately concentrate on my long slender legs! I smiled and thanked him for coming to get me and he smiled at me and told me how wonderful I looked! I loomed him up and down and wasn't disappointed. Mature,, clean shaven, shaved head, well built.... I was very impressed by him in real life and told him that he also looked very good. He laughed and we drove off into the night.

He drove me around a few locations where we'd exit the car, walk around, cuddle one another and return to the car. All relatively safe with no problems. In between walks I'd fondle his cock and balls as he drove and I could tell he was very excited! On our final trip he led me down a quiet lane and grabbed me close to him, kissing me hard. I knew what was epxected of me and turned around spreading my legs at the same time. I felt his hands pull my panties down and his fingers began probing my soft warm hole. I felt the coldness of a lubed finger as it pushed and widened my eager fuck hole. He made sure I was fully opened up before he removed his fingers and I felt the familiar push of something much larger make its way fully inside me. I bent over further and allowed him to thrust away inside me slowly building up his rhythm until he finally exploded deep inside me, gripping me tight around my waist and making me feel like the perfect fuckdoll.

After the success of our first date I knew that I wanted to go further than I'd ever gone before and told him what I thought. He agreed and asked me if I'd accompany him to a quiet rural restaurant he frequented on his visits to my city? I was near dizzy with excitement at the thought of it but immediately knew that I wanted to do it. I messaged him back saying yes. Yes, I wanted to be his date in a restaurant whilst fully feminised! Why wouldn't I!

The next few weeks passed quickly and the day of our date came closer and closer. We chatted and discussed the location, what I'd be wearing, and the fact that I'd never been out in such a public place before. He put my mind at ease and told me I'd nothing to worry about. The place was quiet, I was passable, and he would be at my side the entire night. The more I thought about it the more I knew he was right and I had to do this just to prove to myself that I could!

On the night of our restaurant date I took the afternoon off work and spent the time getting ready for the evening. I showered and used my favourite feminine body wash then fully shaved myself from head to toe missing no hair whatsoever. I had absolutely no hair on my body at all once I was finished. I then covered myself in moisturiser, applied deodorant, and sprayed some body spray all over my smooth and hairless body.

I then started getting dressed with my first item being my chastity cage. From previous sessions I knew that if I didn't get it on before dressing then I'd have no chance of getting it on at all! Once I began pulling on stockings then I knew I'd get hard! Once this was on, I chose a six strapped suspender belt along with a pair of ten denier sheer black stockings. They felt so good on my freshly shaved legs and looked so sexy. My breast forms were slipped into the bra and I fastened the corset as tight as I could until I could barely take a breath in it. I wanted to have as femme a shape as possible for my date. I was to wear a knee length lace featured LBD and slipped this on over my feminised body. I was amazed at the shape that the tight corset gave me and stared at myself in the mirror pleased at how feminine I was begining to look.

I slowly applied my make up taking my time to ensure it was as perfect as I could. The foundation was flawless, eye shadow, eyeliner and mascara was second to none and my lips were painted a deep scarlet red. The addition of false eyelashes helped to make me look even sexier than normal! I made sure that I was looking as good as I possibly could. I knew just what it took to achieve the illusion of feminity and knew that tonight I would have to look my best ever for my date.

Next came all the accessories required to compliment my look. A shiny silver necklace, two pairs of clipon earrings comprising of one large hooped pair and a dangly pair of glittery balls. Bangles, rings, and an anklet chain finished off the jewellery. I then reached into my bag of toys and pulled out my largest butt plug. I wanted to feel completely filled tonight so lubed it up and slid it home until it sat tight within my pussy. Finally I sprayed myself all over with my Caroline Herrera 212 perfume so I smelled as sexy as possible.

I pulled on my short platinum blonde wig and winked at myself in the mirror.

"Let's do this Fiona" I said to myself and gave myself a huge smile.

I was no sooner done that Sam texted me that he was there and that I was to come outside and meet him so I grabbed my coat and bag and exited my flat. I spotted his car in the car park and made my way over very conscious of the sound my high heels were making on the pavement. There's nothing that emphasises feminity more than the sound of clicking heels and I was announcing myself to everyone that night. I jumped in his car, smiled at him and we set off with his hand running up and down my stockinged legs as we made our way there.

After around a half hour drive we pulled up in the car park across from the restaurant and Sam asked how I felt? I answered truthfully and told him I was terrified and he smiled at me.

"Don't worry, you look amazing Fiona..... now lets go eat."

I honestly was a bit worried, but knew that I had made myself look as feminine as possible for tonight so shouldn't worry unduly.

We exited the car and he pulled me close to him.

"Don't you worry darling. You're with me. Honestly, you look great." and with that, we started walking towards the restaurant.

Every step I took seemed to fill me with excitement as we neared the front door. I could see through the window that it wasn't exceptionally busy. A few couples scattered about the place and that was it. I could feel his arm around my waist holding me tight against his body and every now and again his hands would wander over my ass and legs, occasionally feeling the outlines of my corset and suspenders. I couldn't help but feel so horny when he did this and I knew there was no going back now.

We walked into the restaurant and were immediately greeted by a young Thai woman smiling profusely at us. She was in her late twenties, petite, and very good looking. An absolute doll dressed very smartly in an Oriental style dress. I began unbutting my coat and she stared into my eyes.

"Hello and welcome. Where would you like to sit", she asked politely looking at us both in turn. I saw her look me up and down. I handed her my coat and stood in front of her fully feminised. Her eyes swiftly ran over my entire body. Had she read me? I honestly couldnt care to be truthful. Her culture knew all about men who dressed as women so what was there to worry about? I felt so confident standing in front of her wearing stockings and high heels under my dress AND wearing a chastity cage as well as having a big plug in my ass! I bet she'd no idea I was wearing that!

I smiled and said that I was happy anywhere and Sam indicated towards a window seat looking out onto the main thoroughfare! There was no way I was going to say anything so just nodded at the woman and she moved towards the table he'd pointed at. We sat down and she handed us each a menu saying she'd be back soon for our order. As soon as she had left I could feel Sam's hand under the table stroking my nyloned leg and running his fingers up and down my thigh. I lifted up the menu in a feeble attempt to blend in with the rest of the customers in the place. Who was I kidding? I was a feminised and chastised male sitting in a restaurant surrounded by normal couples enjoying a normal night out! What was I doing!

" Oh Fiona.... you are so going to enjoy tonight" Sam whispered to me across the table.

I smiled and thanked him for this treat and opened my legs wider so he could move his hands even closer to my chastised clit trapped within my sheer panties. I gasped as he slowly rubbed the cage tugging at it as he stared longingly into my eyes. His fingers reached under the thin material and began rubbing the cage.

"Please Sam..... not here", I implored him, but he carried on regardless.

"Shhhh baby..... just relax and enjoy yourself".

I was in ecstasy as he ran his fingers over my legs as I tried my best to concentrate on the menu in front of me. I looked around every now and again, but thankfully no-one was paying us any attention at all as they were all caught up in their own daily lives. I relaxed somewhat and started enjoying his subtle caresses.

The waitress came back, took our orders, and again left us in peace which allowed Sam to continue stroking me under the table. Then he spoke to me.....

"Fiona.... I want you to go to the toilets and remove your panties for me. Then I want you to come back and hand them to me.... OK my darling".

I knew that I couldn't refuse so just smiled at him, nodded, stood up and walked towards the female toilets. Once in I went into the cubicle, sat down on the seat and hiked my dress up around my waist. I slowly removed my panties listening intently just in case anyone entered the room as I did this. Once they were off I grasped them tightly in my hand and returned to the table.

"Here you go...." I said as I pushed them into his hand.

"Thanks baby".

He looked at the crumpled up black panties in his hand.

"So, how does it feel to be in public with no panties on"?

I couldn't lie and told him that it felt amazing and he laughed and leaned across the table towards me. I followed his lead and our lips met at the halfway mark. We kissed and I felt his tongue push its way inside my mouth. I felt so feminine at that point. Here I was in a public place with people all around me, dressed as a woman, and kissing a hunky well dressed man. I felt so alive at that moment.

The waitress returned with our wine and we sat and chatted about what woud happen afterwards. Sam was keen to use me somewhere in public too and asked me which locations we could get away with a very public display of affection? I suggested a few places and he bowed to my in-depth local knowledge of secluded areas. After a little while our meals arrived so we concentrated on them instead of deciding where we'd go to fuck afterwards!

Once finished he motioned the waitress across and paid the bill - such a gentleman - and we thanked the waitress then made our way outside. Again, Sam held me tight as we walked back to the car. I was dizzy with excitement at what I'd just accomplished. I told him how horny I was and after a quick look up and down the street he pulled me into a doorway and kissed me again, his hands running up my dress and gently cupping my chastity cage. I could feel my cock attempt to stiffen, but the cage stopped me and I knew that was as good as it would get for me tonight.

"Lets go give you a treat" he whispered into my ear as he nuzzled my neck.

As we walked back to the car he was squeezing my bum and telling me how horny he was. I felt the exact same way and couldn't wait to unzip his trousers. Occasionally I'd run my hands over his crotch to feel his manhood and was delighted to feel it growing as we walked. I was guaranteed a good night
 on the end of his cock later on and I knew he wouldn't disappoint me. True to form, he never....

The Ultimate Meet

For the past few weeks I've been trying to get a meeting together via a new friend of mine - George. He is an older retired business man with a soft spot for submissive sissies like me. We chatted online, met, and played together and he was keen to get me further down the rabbit hole and bring to life my fantasy about being a submissive sissy whore for him. He had already told me about his friend Alan who worked abroad and was into all the same things as him. He was keen to get the three of us together and finally a date was put forward that we all agreed on. The plan was that I was to be fully feminised and be brought along by George to Alan's house one Summer morning for me to serve the both of them over the course of the whole day.

George was also keen to show me off once dressed and had said that I'd be taken either for a public walk somewhere or be sent into a shop along the way to Alan's. Both ideas excited and terrified me at the same time. It had been a while since I had been out in broad daylight and the thought alone gave me butterflies in my stomach. I knew I could pull it off but it still scared me to think of where George was going to take me. He also said that Alan wanted me to bring my toys along with a webcam as he wanted an online show. I knew that allowing the both of them to read this blog would give them some very mischievous ideas.

On the Saturday before the meet I nipped into town and bought a new dress, basque, seamed black stockings, panties, and a fresh bottle of poppers especially for use with the men. I wanted to look my best for Alan. I'd never seen him but George said he wanted to impress him and so I knew what had to be done. I wanted to be the sexiest TV that they'd ever seen and I knew just what made men's cocks hard!

Eventually, the day of the meet arrived and I rose and jumped into the shower. I'd hardly slept the whole night. I shaved my body clean of hair then dried myself and applied some gorgeous fragranced body lotion. A douche helped to clean my insides for the men's benefit. Next, I painted my toe nails to match my chosen outfit. I'd packed a bag the night before to save on time and already had some matching long false nails for my fingers. In the bag was everything I'd need to ensure we all had a good time that day. along with my clothes, make up, and underwear, I'd also packed some dildoes, lube, poppers, condoms, and vibrating cock rings.

I drove over to George's in the morning rush hour and it took me an hour to get there. The traffic was a total bitch. I let myself in as arranged and made my way straight to his bathroom. He didn't want to see me until I was fully feminised so was leaving me alone to get ready. I stripped off and pulled on the black basque first before pulling the sheer black seamed stockings slowly up my legs. I did NOT want to ladder them before I left the house. I tucked half a dozen condoms around my stocking tops so that the men knew I was a slut for fucking when they slid their hands up my legs. Next came my chastity cage and a lubed butt plug was slid firmly into place. I wanted my hole to be easily accessible when it was required by my admirers. Breast forms were then tucked into the basque cups giving the illusion of large womanly breasts. I felt my clitty throb with the excitement all of this gave me. I love getting dressed for sex!

I then sat at the pre arranged table and did my make up just as George had asked. He wanted it heavy, very slutty, with lots of red lipstick and eye liner. Plenty foundation, blusher, powder and dark eye shadow. long false eyelashes completed my look. Once finished, I clipped on two pairs of long jewelled earrings  and attached my new purple sparkly necklace. This was to match my very sexy - and very tight - purple dress that I'd bought the week before. I slid myself into it loving the feel of it as it hugged my body. One final addition was a dog collar to show that I was owned. I finally added my wig, brushed it into shape and held it with a good coating of hairspray. I then looked in the mirror and blew the sexy young woman looking back at me a big kiss. This was going to be a very good day indeed. My final additions were the long painted false nails that I carefully glued into place.

George called  me after an hour and I told him to hurry back. His whore was waiting for him. He arrived just fifteen minutes later, pushed the living room door open and his face told the complete story. He stood and started at me with a huge smile on his face.

"Fiona... you look gorgeous darling.... come here...."

He took my hand and leant forward and kissed my cheek.

I blushed as he looked me up and down complimenting me on my look.

"Now, I think you ought to show me how much you've missed me"

I did exactly what every good sissy should do to greet her man and sank to my knees in front of him. My fingers traced the outline of his rapidly thickening cock and ever so slowly I unzipped his trousers and reached inside. He was rock solid when I pulled him free and I kissed the tip of his helmet before sicking my lips and mouth over it and slid down so that it filled my mouth and throat completely. Keeping a tight hold on his balls I began slowly moving my head back and fore savouring the musky salty taste of his pre cum. His moans alone told me I was doing a good job. I sucked hard swallowing his cock as far as I could. I love pleasing a man and can tell when he's enjoying himself. A stiff cock in my mouth tells no lies.

"That's enough now Fiona.... I don't want to spoil things for later" he said mischievously, " Now let's go"

I collected my belongings and my handbag and walked to the front door. George took my hand and led me outside into broad daylight. I was so excited by this and couldn't believe what was now happening. Slowly we walked towards his car my high heels clicking loudly on the pavement.

"Nervous babes"? he enquired...

I nodded my head and he replied that I would be fine and not to worry. He had plenty faith in me.

We drove for around half an hour until we reached a small town and George pulled in. He pointed towards a small shop and told me to get out and go into the shop and buy a pair of tights and some Tampax! He handed me some money and told me not to be too long!!! I couldn't refuse his order and opened the car door aware of the fact that my jacket had ridden up exposing my stocking tops.I quickly sorted myself and jumped out. He shouted after me to remember to thank the staff afterwards and I nodded my approval.

I strode into the store and immediately began scanning the shelves for my purchases. Thank fully I was the only one in there at this time .The tights were easy to find - a 15 denier three pack - but I had problems with the Tampax. I could see the middle aged male shop owner watching me as I moved around the aisles intent on finding them. I wondered if he could tell I was actually a man? I hoped not as I was so nervous with George's upcoming plans for me. After a minute or tow I found them and approached the counter giving the man a big smile. He smiled back and took my goods, rang them through and asked if I needed a bag? I quietly said no thanks and made my way out of the shop knowing full well that his eyes were on my arse and legs as I left.

I climbed back in the car, showed George my purchases, and he smiled at me and asked how it had went? I told it was no bother at all really and he replied that if that was the case then he'd find a more demanding task for me the next time then! I laughed hesitantly as I wasn't sure if he was being serious or not? We drove off again and once we were in the countryside he told me he wanted me to go for a small walk by myself. I nodded and we pulled in by a small country lane. It was a beautiful day, there was no-one around, and the sun was shining so I wasn't concerned at all.As I walked off I heard the snap of a phone and turned round to see George waving at me...

"One for your collection Fiona" he laughed....

I walked up the lane until i was nearly at the top of the hill and then turned and waved at my companion for the day. He beckoned me to come back so I began my slow walk back to the car as he watched me every step of the way.

"That was good.... maybe next time I'll take you somewhere a bit more public. Are you excited Fiona?"

I told him that I was. My clit was straining against the metal casing of my chastity device. A sure sign of my having enjoyed my public outing. After another short drive we reached another town and George scanned the nearby houses before slowing to a stop outside a row of around ten. He pointed to one and told me the number. I repeated it and he nodded his head and gave me some instructions. I was to introduce myself as Jane - not Fiona - and tell Alan that I was there for him to use. I was then to go inside and Alan was allowed to do anything he wanted except remove my plug. He would return at some point and my session would begin properly then, and only then. I repeated everything he had told me back to him before opening the car door and heading out into the street.

My eyes scanned ahead and although there were people in the distance there was no-one close by. I saw the house number I had been told and strode up to the door. My long black seamed stocking clad legs were on display as the front of the coat blew about in the wind. This was so exciting to me.... I reached out and rang the bell. Seconds later, a well built man answered the door and smiled at me. He was in his early 40's, nearly 6 foot tall with a big solid frame. He looked very impressive. I told him that I was Jane and he asked me in pointing me towards the main room.

I stood there and waited until he locked the door and joined me again. His eyes looked me up and down and I knew he wasn't disappointed. I unfastened my coat and his eyes widened when he saw my full attire. A glass of white wine was poured for me and I slowly sipped it as he stood in front of me and began moving his hands over my body. I was under strict instructions to allow him to do anything so did not complain as he lifted my dress up and ran his hands over my panties and caged clit.

"Oh, what's this Jane"?

I explained that I was caged - until it was decided whether I was allowed any release - and he laughed.

"Well, you better be good then, eh girl"?

He took my hand and led me to the stairs and pushed me down so I was sitting directly in front of his crotch. I decided to take the initiative and pulled down his zip. Looking up I saw him smile and nod so I reached inside... and pulled out his massive thick cock. Wow. He was a big boy. It was around 8 inches long and getting thicker all the time. I moaned in delight and closed my mouth over it eager to take as much of it as I could for him. I struggled with the size of it but began forcing my mouth further over it so it invaded my throat. I gagged a few times as I did this and he took a tight hold of my head and held me firmly in place. I relaxed my throat and allowed him to slide deeper inside me until his balls were finally resting on my chin.

"Open your legs slut", he commanded me, so I did as he said allowing him to see my useless chastised clit swinging away as I deep throated him. Saliva was running down my chin from the abuse my mouth was getting and he occasionally pulled himself out and had me lick his massive swollen hard on and balls for him. I lightly tongued his balls and at one point he bent over and had my rim his ass for him as he pulled his cheeks apart. I forced my tongue into his tight brown hole as he urged me on. Afterwards, Alan felt between my legs once more and squeezed my plug. I grunted and started explaining that I wasn't allowed to.... but he told me to shut up and began playing with it, half pulling it out before slamming it back in over and over. I pleaded with him not to, but he didn't care. I was then pulled to my feet and made to kneel face down on the stairs as he hoisted my dress up around my waist and roughly pulled my panties off and tossed them aside. He gave my arse an almighty slap and I yelped in genuine pain.

"Oh very nice..... very fucking nice indeed" He slowly exclaimed.

The plug was then pulled from my pussy and I felt a condom being taken from my stocking tops and heard the sound of it being ripped open. I knew it was useless to try explaining about my orders but thought that I'd try once more.

"Please can we wait... I've been told..."

Just then I felt his enormous helmet push against my pussy hole, force it open, and slide it's way in. I gasped as he slowly filled me and pushed in deeper holding me still on those stairs of his. I squealed and gasped as his member pulsed inside me. He stayed like that a little while inching deeper and deeper as he lay fully on top of me. His huge hands took hold of my waist as he began to slowly fuck me. He'd pull almost all of the way out and then slam forcefully back in again.... over and over again. I fumbled in my bra and pulled out my poppers inhaling six long snorts. My mind exploded with pleasure and I began pushing back against him urging him to use me more. The feelings were intolerable. My body was loving it, my brain in overdrive, and my pussy was being used like never before. Again and again he slammed into me and I felt like I was really being used by him. He was unstoppable. A fucking machine. It felt so good. On and on he went plunging deep inside me, muttering my name, stroking my body and nylon covered legs with his hands. I squealed and moaned with desire as he used me.

Suddenly, the door bell went again and the fun suddenly stopped. I was breathing hard and realised I was in trouble when Alan slowly pulled himself out of me and strode towards the door with his still hard and wet cock on display. I hardly had time to make myself respectable before George walked through the door and stared at me.

"Have you been fucking..... Jane..... have you been fucking"? His question was direct.

I nodded at him knowing I was in trouble. It would have been futile to say otherwise. My face was flushed plus the evidence lay all around me. My poppers bottle on the stairs within reach of me. A ripped open condom wrapper on the floor. My discarded panties. Alan, standing with a huge grin on his face and his huge glistening rubber covered cock ever so slowly going down.

"I told you she was a horny bitch eh", He laughed...

Alan let him know that I'd put up no resistance whatsoever and George laughed again and told him that he knew I wouldn't. The two of them stood over me as I lay on the stairs. Alan was stroking his cock eager to keep it hard.

"Let's get this whore up the stairs and see what she's really made of", Alan said and winked at me.

I was pulled to my feet and led up the stairs and towards the main bedroom. Alan reached under the bed and pulled out a large red padlocked holdall. I hardly had a chance to see it before George lay back on the bed and told me to get to work. Kneeling between his legs I once again pulled out his cock and began sucking on it. Up and down I went  aware of the fact that Alan was slowly lubing up my pussy for more fun. His fingers smeared more and more lube inside me. Poppers were held under my nose and I took some long deep snorts of it. I continued sucking, working my mouth up and down his stiff throbbing cock. Then George spoke...

"Alan.... I want you to spank her for disobeying my earlier orders. She likes it hard so don't hold back"

Alan then began spanking me... HARD. I squealed and writhed under the assault desperate to be shown some mercy. George told me that I was a bad girl and deserved to be punished. The spanking was just the start of it. For a long and painful five minutes I was disciplined by Alan until I could physically take no more. Just as I regained my composure, I was then aware of Alan fumbling behind me and something slowly slid into my pussy. It went deeper.... my hole stretched wider.... and went deeper... and got wider. Oh Lord... it was inflating.... the feelings as it then started vibrating deep within me sent me insane with lust. It was then pulled in and out of me. Slowly to start with then  faster and faster. I moaned as I struggled to maintain my rhythm on George's cock. I wriggled around and positioned myself so that my ass was completely exposed to this treatment. A couple of times I gasped and released the cock from my mouth.

"Keep going you fucking whore" George commanded me... "Don't you dare fucking stop".

This went on for a while before the object was removed and replaced with something else. Again, it started small, then got progressively larger. My pussy welcomed this new addition and I felt Alan's fingers play with my metal encased clitty at the same time. He'd pull at it and gently spank my balls making me moan in both pain and delight. George continued to steadily fuck my mouth using me as nothing more than a fuckhole for his cock.This was so exciting having two men use me like this. My legs spread wide with both my mouth and pussy filled to the brim at same time was heaven. I had never had anything remotely like this treatment before.

Over the course of the next few hours this scenario was repeated. I was nothing more than a piece of sissy meat to them. George and Alan would swap ends... numerous toys were used... poppers were regularly held under my nose.... I was passed from man to man to be used as a fuck toy.... with no let up at all. When one was done with me the other would begin anew. At one point the webcam was set up and I was fucked live on cam with strangers watching me. My humiliation was complete as I was shown off as a submissive sissy whore being used for two men's enjoyment. Alan had set up his television so he could watch the action live on the internet much to my shame. George held the cam and moved it over my body as Alan used me taking great care to show the world my well stretched pussy being fucked deep and hard by his large thick cock. He took great delight in telling me how many people were watching me like this.

Once both men had came - both salty loads shot down my throat - then I was told the session was over and to go sort myself. I made my way to the bathroom and sorted my make up as the men sat and chatted. When I came out George called me over and produced the Tampax and the key to my chastity device. I was then unlocked, handed a small glass, and told to insert the tampax and  bring myself off as they watched. I  did as he asked quickly and without question the Tampax easily slid into my well used pussy. Once unlocked I swiftly grew hard and within seconds was coming into the glass. Without even being told I lifted the contents to my mouth and drained the lot - my third of the day. They both congratulated me on my efforts after this and then began planning another meet with even more people there. Alan was asked if he knew anyone suitable and said he'd definitely find someone else for the next time. Looks like I could be a popular girl amongst the local admirers in my area!

A Sissy Slut for her Mistress

A few weeks ago, I made plans to visit a TV domme for the first time in ages. I was so nervous about it... I don't know why? It's not like I'd never served one before! We had spoken via email about what each other liked and it was clear that we were relatively well matched. She was Dom and I was sub. That's about as well matched as it gets surely! I had told her that I wanted to be totally humiliated and used by her and she had listened and asked that I show up that weekend at 7pm on the dot.

She had instructed me to turn up lightly feminised so on the day I followed her orders and wore sheer hold ups, panties, 2" heeled shoes, women's slacks, along with a feminine white blouse. I also applied a layer of foundation, light pink lipstick, and a coat of mascara on my eyelashes. I never wore a bra preferring to have no apparent breasts to emphasise my maleness. To complete my look I wore a pair of silver dangly earrings... which looked very sissy like when I stared at myself in the mirror... what a complete faggot sissy boy I was. All femmed up and looking like a mix of male and female to anyone who looked closely at me. To complete my humiliation, I coated my pussy with lube then slipped in my largest butt plug I had. Mistress would be so pleased with me tonight!

I pulled on my coat, grabbed my bag and headed for my car very conscious of my appearance and wary of anyone that was walking towards me. Luckily no-one was... on the way out. However, when I parked at her flat which was on a very busy street, I had no option but to brave the stares and walk out holding my bag of sissy playthings clutched tight to my chest. I saw a few people look me up and down as I passed them but I was on a mission and just kept going, oblivious to them all. Being a sissy lends one a certain amount of bravado when out and about dressed. Eventually I reached her address at 7pm prompt, waited until it was on the hour excatly and rang the buzzer.... and waited... and waited.... I was now terrified I had been set up! How could someone do this to me! Suddenly the door buzzer sounded and I pushed my way in. Her flat was the first door I came to so I knocked determinedly on the door.

The door swung open and there she stood. She greeted me fully dressed in a PVC dress, black seamed stockings, black patent stilettoes, and a wicked looking riding crop in her hands! What a Goddess she was. I was taken aback at her beauty and stammered as I introduced myself. She smiled and invited me in. I was taken through into her main room and we chatted for a small while over a glass of wine before she asked to look through my things. She wanted to choose an outfit for me herself. She opened my bag, rummaged through i,t and chose a short tight black dress, sheer dark hold up stockings, 6" high heeled stripper shoes, and black lacy panties and bra. She casually  pointed me towards her bathroom. I quickly changed, re-applied my make up - applying a gorgeous red lipstick to my lips instead - and confidently strode back out.

I knocked on the living room door and announced myself ready to Mistress Nadia.

"Come in sissy" she purred....

I walked in, swinging my hips as femininely as possible. I wanted to look good for her.

"On your knees sissy"

"Haven't you forgotten something sissy"?

I looked up and in her hands swung my chastity cage.

I nodded my head and apologised adding that I'd forgotten to take it to the bathroom with me. Her look of disapproval said it all.

"Stand sissy and show yourself", she demanded.

I raised myself up and lifted the hem of my dress to show my rapidly thickening clitty. I was so excited by the whole session so far and honestly couldn't control myself.

"Oh no..." she said....

"That won't do at all I'm afraid. How am I supposed to get that in there"

I looked at her apologetically and she smiled at me before reaching out and taking a firm grip of my clit, squeezing it tightly.

I gasped and she began a firm steady pull on my sissy pole. I moaned as she slowly and very determinedly made me harder and stiffer than I ever thought possible... then she reached over for a nearby wine glass and held it under my balls. She kept eye contact with me the whole time as she manipulated my stiff rod steadily faster and faster. I couldn't last for much longer.... she was so good at it....mmmmm.

"That's it sissy.... show mistress what you have.... come on sissy.... show me... what you have... do it.... do it for your Mistress... cum for me sissy.... cum for me now.... do it... do it.... you fucking sissy whore"

...and with that my clit began shooting spunk as Mistress directed it into the glass rapidly coating the insides with thick white blobs of jizz. I watched as my clit shot spurt after spurt into the glass. I hardly had time to catch my beath before she had lifted the glass to my lips and commanded me to down it.

"Perfect", and stood watching me compose myself as my excitemnet waned. She then wiped my rapidly shrinking clit with a wipe and then clamped the metal ring around the base of my clit and balls before tucking my soft spent clitty inside the metal tube of my nearby cage.

"Sit down sissy... Mistress wants a picture of her slut....legs wide please"

"Of course Mistress", I purred and lay down and spread my long nylon clad legs for her exposing my chastity cage to take a snap of with my phone.

After that was done she instructed me to put my panties back, crawl towards her, and kiss her heels. I softly tongued the metal heels and toes of her 5" stilettos. It felt so humbling to be at her feet. She knew I was a sub sissy so this was what I craved. To be at her beck and call attending to her every whim. My tongue and lips paid gratitude to her for this opportunity. I kissed and licked her shoes all over, running my tongue over the heels and soles, caressing the soft leather with my lips. It felt great to be in her service. I felt her hands on my bottom as she lifted my skirt more and then a sudden pain shot through my buttocks. The riding crop had found it's target. Three more times it struck hard against me.

"Up you come sissy.... slowly now" she breathed almost silently.

Slowly, ever so slowly, I made my way up her legs enjoying the feel of the nylon stockings on my lips. My fingers ran over her shapely calves and soon I was holding her bum in my hands. I pressed my face against her panties and breathed in deeply savouring the fresh feminine fragrance that her body was covered in. My mouth opened once more and my tongue ran over her rapidly swelling panties. This was heaven.

Her fingers lifted her panties to one side and in an instant she filled my mouth. I set to work immediately. My head bobbed up and down, pushing her deep into my throat. I gagged on more than one occasion as she thrusted into me. Holding my head she began slowly fucking my face. I relaxed my hold on her and allowed her free reign over me. I was nothing more than a receptacle for her now. She fucked my face steadily and slowly gaining in pace every now and again. Saliva ran from my mouth coating my lips and chin. How degrading this was...

After a good fifteen minutes of this I was hoisted to my feet and manoeuvred to a nearby sofa where I was placed face down. My panties were pulled off, my plug slowly eased out, and her big stiff cock swiftly replaced it. I gasped as her thickness filled me. She pushed forward and I moaned in ecstasy still in shock at the suddenness of it. I tried to lift my head but she her hands were on the back of my neck holding me down....and then she began fucking me for real.

One hand was in the small of my back as she held me in position. I moaned louder as each thrust filled me completely. Her hold on the back of my neck relaxed and I felt her pushing something in my face. I opened my eyes to see a bottle of poppers, open and ready for me. I sniffed deeply... twice each nostril... and sank down again.

"Yes Mistress fuck me.... fuck me please......"

I couldn't help myself. I was so horny for her and had to tell her. Again, more poppers were offered and I gladly accepted. Four more deep snorts. I lay there helpless, moaning and groaning, as she used me as ever good sissy should be. Again and again she thrust deep inside me, filling me and stretching me wider. My pussy was being so well used by her. This was the best fucking I had ever had without a doubt. She was relentless in her approach to it. Strong, commanding, domineering..... Then the crop was used again on me. I almost screamed in delight.She rode me so well and used the crop every now and again to keep me in control. My cried of pain and desire made her drive herself deeper into me. On and on my punishment continued with no abate.

Finally, I could tell by her breathing that her orgasm was approaching and urged her to fill me. I wanted her deeper inside me more than ever and pushed back. This triggered her off and she came hard inside me holding my hips tightly and filling me with her thick gorgeous mess. I felt her warmth spread inside me, making me her bitch. She moaned my name over and over as she emptied herself inside me. I had submitted myself totally to this Mistress in a way I'd never done before. I was now her sissy cum dump.... and she knew it.

So true....

So True....

A Daytime Dalliance

Sorry to have been so quiet over the past few months.... I've been so busy with work and a new flat that I've rarely had a chance to get on here.... or have any meets.... until last week that is. I'd been contacted by an older admirer on a TV website asking how I was and if I ever met? Now usually I delete any requests from admirers as I find most are pie in the sky fantasists, but I thought I'd play nice with this one. Something about his style of writing told me that he was at least worth a small conversation with. In the end he was extremely charming, witty, and knowledgeable about the TV scene and the girls who frequent it. I was growing fond of George.

And so it went on for a few weeks, messages to and fro, until he asked me if I would spend some time with him at his place. I was due a few day's holiday from work so proposed a day time meet instead of the usual night time adventures I usually have. He agreed and the date was set for a week's time. I really wish I'd made it sooner as that whole week running up to the meet as I could hardly sleep because I was anticipating it so much. I was running over the various scenarios in my head especially the one where he'd told me had another friend who was also interested in me. I haven't had a group meet in a while... never mind enjoying two admirers at once! I was bound to be a popular girl! Yikes.

His friend was also in TV's and sissies and was very eager to join in the action offering to host our get togther at his place. I'd told George that I would never have arranged such a meeting myself - but since I was offering myself to him as his younger sissy girlfriend - he could then arrange whatever he wanted for me. I would simply turn up at his place, let myself in, feminise myself, and await his return.

We arranged a quick lunchtime meet where he picked me up in his car and drove me around as I stripped my trousers off in his front seat allowing him free and easy access to fondle me as he drove around town. It was very erotic as I was only wearing hold up stockings and panties and became very excited as he stroked me softly whilst telling me everything he was going to be doing with me at our meet. I was so hard for him and could only hold my hard clitty so he could enjoy the sight of it. Eventually he parked up, handed me a small cup, and instructed me to cum in it. Within seconds I was shooting my warm salty jet into it as he looked on approvingly. He nodded at me and I quickly downed the spunk contents for him. Suffice to say we were both even more excited about our upcoming meet after this.

The night before I was due to meet him I packed all my goodies into my bag before running myself a huge foamy bath. I soaked it in for an hour and ran the razor over my body until there wasn't a single hair left anywhere. Once I was happy with this, I stepped out and coated myself in a lovely feminine fragranced moisturising lotion. My toenails were painted a deep red in keeping with my slut persona. Just before bedtime I slipped in a small buttplug....  I wanted my pussy ready for anything the next day... just in case!

I hardly slept a wink and before I knew it it time to get up and go. I arrived at his around 8.30 am and let myself in as arranged. From there I made my way to his bathroom and began the transformation to the woman I was meant to be. Firstly I locked myself into my chastity cage knowing that this had to be done early to ensure it went on at all! Once I start pulling on nylons and applying make up then I struggle to get myself in there. I'm sure most tgirls know what I mean! Once that was done then it was on with the transformation for me. Foundation followed by lip liner, red lipstick, and thick black eye liner. Next came the long false eyelashes, soft brush strokes of eye shadow, mascara, and some blusher for my cheeks. I finished it all off with a heavy application of fine powder to hide any small imperfections that may be left. George had confessed that he liked his girls to be heavily made up so I was really going the whole hog for him.

I rolled the brand new 7 denier lace topped hold up stockings up my legs and I felt my clitty twitch. Some feelings will always feel deeply erotic to me and new stockings on freshly shaved legs remains the ultimate. Bending over I slipped a butt plug into my lubed up pussy  enjoying the feeling as it stretched and filled me. Black lacy panties covered my chastity cage and looked extremely sexy in the mirror. I couldn't wait for him to lift my skirt up and find my clitty locked away out of action and my pussy already filled! A short sexy dress came next - no bra or breast forms - I wanted him to see me a feminised sissy boy NOT a TV. I was there to serve him and his friend and would do whatever they wanted today. I felt such a slut.

I finished off my look with short lace gloves, plenty of sparkly jewellery, a bobbed blonde wig, and lashings of Chanel perfume. Just as I was doing this my phone rang... it was him checking in with me. I told him I was ready and waiting for him and to hurry back. As soon as the phone went down I sat on his sofa and began thinking about what I was doing! I hardly knew this man and yet here I was fully feminised, caged, and plugged sitting in a stranger's house waiting for the door to open. What a bizarre life I lead.

Within ten minutes, I heard the door open and I quickly stood to attention for him. George walked in and his face said it all. He walked round me smiling and telling me how good I looked. I couldn't help but smile back and thank him for allowing me the opportunity to perform for him. It was then that he broke the bad news that his friend had been called away on business just the previous day and so wouldn't be joining us. He hoped to be back the following month where it was hoped that I would be brought to his house fully feminised for use there. I was a bit disappointed but knew that the day was just beginning with George.

He has me pose for him throughout his house as he occasionally allowed himself to softly touch me. the tension was unbearable and my clit was really swollen and uncomfortable within its metal cage. I was ordered up and onto the dining room table where my skirts were lifted up and across my hips. George moaned and gasped when he teased down my panties once my plugged pussy and chastity cage was revealed.

"Oh Fiona... you naughty naughty girl..."

"Yes Daddy.... I am naughty... please can you spank me. I've been so naughty", I gently enquired.

"Of course baby.... of course......" and with that he began spanking me.

"Harder Daddy..... ahhh.... owww..... ahhhh.... harder.... please".

The spanking became more and more intense and I reached into my nearby handbag and deeply sniffed from my poppers bottle. This helped me deal with the pain and I urged my daddy to continue his strict spanking as the poppers high quickly took effect. I sank my head down onto the table as his slaps became more and more intense. My cheeks were stinging and I squirmed on the table in obvious distress.

"That's enough Fiona you slut.... turn around", he ordered so I shuffled round to be confronted with his stiff cock. I didn't have to be told what to do with this so slowly began running my tongue all over it as he moaned in delight. My lips closed around it and sank down filling my moth and throat with his thick stiff member. I kept this up for some time until he pulled me off and ordered me onto the sofa.

"On your back and legs high up whore" he commanded and I took hold of my ankles and allowed him to feast his eyes over me. His cock was rock solid and covered in my saliva as he looked at me.

"Fucking perfect.... now get that condom on me" he said before throwing a condom at me and smiling as I rolled it onto his beautifully sculpted cock. His hands reached down and pulled the plug from my hole and his smile widened even more.

"Lube me whore" he smirked and watched as I squirted lubricant over the condom and wiped the remainder over my loose pussy hole.

"I'm ready Daddy" I lisped and lifted my legs up and over my head.

George stepped towards me and in one swift movement plunged himself deep inside me. I gasped as he filled me and looked up into his eyes. Our eyes remained locked as he pushed down into me sinking even deeper.

"Your mine now Fiona" he whispered as he slowly began his gentle rhythmic fucking of me. He slowly slid in and out as I held my legs up and over his shoulders watching my every facial expression. I felt him p[ush deep inside... hold... then pull out almost all the way.... and then the same again. Over and over. My clitty was growing again adding to the excitement of it all. I had to have poppers again and George smiled as I inhaled deeply four times.

"That's it whore....  you enjoy it... plenty more to come yet. I'm going to have you pleasuring many of my friends. They'll enjoy a submissive whore like you. Dogging.... group sex.... parties.... mmmm... you lucky girl Fiona"

I was really enjoying the way he was using me. His cock continued it's slow sustained assault on my lubed pussy hole as he eagerly watched my every move. Every now and again I'd have more poppers and he'd smile as my eyes clouded over and I began imploring him to keep fucking me harder and harder. It was heaven and he knew it. This went on for a good time before he speeded up and started pushing himself deeper inside me. It was time. I was to become a real woman. A real man was going to come deep inside me. I closed my eyes and revelled in the feelings as he pushed, shivered, thrusted, moaned, and spewed his load deep inside me. He kept fucking me until every last bit of his load was in the condom and only then did he pull out.

I remained in the position as he towered over me and pulled the rubber free from his cock. He dangled it in front of my face and I knew this was a test so I took it from him and poured the warm contents into my mouth. I savoured the thick salty texture as I swirled it round  and opened wide so he could watch it coat my mouth. He nodded and I swallowed the lot knowing full well that I had passed the test with flying colours.

George then helped me up and posed me in his hall before taking a pic of me using my own phone. Here's to the next time when hopefully Alan will also be present for his initiation into another submissive sissy encounter with Fiona Fucktoy.

 

Collared by a TV Mistress

For the past few weeks I've been communicating with a local TV Domme that has been keen to meet me. I'm under no illusions what this will entail as I've let her look through this blog plus sent her some quite revealing pics and emails about myself. What this means is that this blog may be getting updated more regularly than usual with details of our mutual sessions together. There is another bigger change though....

She has intimated that once she has met me, and we have had a session together, then she is keen on slipping a collar around my neck and making me "owned". What this will mean is that I will not decide who I meet any more. She will. I get sent requests on various sites quite frequently and pick and choose who the lucky people are. Not any more.All decisions about my partners will be made by her. She will arrange the date and time and simply have me turn up at hers for it.

I will arrive and dress as she decides before meeting her choice of partner for me. My input will be negligible. I will not know who I am meeting, what they look like or what they are into. I will simply do as I'm instructed and turn up on the date and time that's been agreed. I will dress how I'm told. Suck who I'm told to... and fuck who I'm told to.... as a good sissy slut should.

The future's looking bright....