Viewing Member - sissyboi_medway

My pink strappy 4 inch heel sandals click on the tiled floor as I step back and look at myself in the wall mirror , it usually takes me 30 minutes from arriving at the sauna to being ready to play. The image that I see makes my locked sissy cock swell , today I'm blonde , a curly long haired wig to my shoulders , pink opaque stockings and matching 6 garter suspenders with a pink over bust corset , some make up , my lips glossy pink and eye liner , lashes eye brows shaded some foundation.

I turn and look over my shoulder my sissy cheeks are framed by the pink crotchless panties I am wearing all lace and a frill and I reach for my small pink shoulder purse , in goes the locker key , the key to my cb6000s and I check I have lube and condoms.... I smile and pout and leave the locker room as a sissy slut to wander the sauna looking for cock.....

I love spring it's time to get out and cruise local dogging sites and walk in the woods with my pussy plugged in panties , stockings and suspenders and my lil sissy clit locked in chastity... mmmmm I wear jogging bottoms and a top over lingerie and carry condoms and tissues because I expect to be using them... yesterday I went for a walk in the woods at a local dogging site.

I was stopped by a guy on a mountain bike who asked for directions into Cuxton he was muscular toned and in lycra shorts and a cycle top as I explained the routes I could not help noticing the bulge in his tight shorts, big and getting bigger , he noticed my glance and smiled and then actually brushed his erection with his hand on the way to scratching his knee.

Of course I could not take my eyes off his bulge and as he asked me where exactly the down route into Cuxton began he did it again adjusting his now very obvious erection , I licked my lips and shifted on the sport my pussy was twitching squeezing my plug.

I pointed out the route he needed to take and he thanked me rubbing his cock again through the lycra shorts and I smiled and stared and set off back along the way he had come stopping after a few feet to turn and look back at him my jogging bottoms had slipped down a little they were tied loosely and as he looked I tugged them down a couple of inches so my pink frilly suspender belt was showing and the thong of my matching pink panties.

He looked and I turned and wiggled my sissy bottom at him and walked away slowly , I heard him move and a glance over my shoulder told me he was following.... my pulse was racing and I was swollen in my chastity cage as I led him off on a side path and behind some evergreen bushes by a fence it's somewhere I have used before very quiet and well shaded....I leaned against the fence and he propped his bike by a tree coming over to me he peeled his black lycra shorts down to free his cock , it swung up and out fat uncut and long... I looked up at him and smiled kissing the tip tasting him mmmmm and slid down to squat and suck him holding his big hard cock with both hands as I sucked and bobbed my head..... he groaned and told me to suck like the sissy boi I was... and I did as I was told until he slipped from me and told me to drop my bottoms...

I slid them down and he admired my panties suspenders and stockings reaching for my cb6000s he tugged it making me gasp and moan I thought I would cum but he spun me round and told me to bend over as he fondled my bottom and finding the plug in my pussy called me a bitch and tugged it out....

I handed him and condom and he rolled it over his cock well the top third and told me to bend and spread wide..... I did and he slapped my bottom making me yelp rubbing the tip of his very hard cock over my lubed open pussy I gasped and whimpered biting my lip as he thrust and plunged into me.... pushing me up against the fence his cock sinking half way in....

He fucked me hard and fast holding my hips and ramming in and out all the way each time.. his cock in deep and filling stretching me... all I could do was bite my lip and pant... the sensations were just too much and my swollen aching sissy clit squirted my sissy cum....mmmmmmm then he was snapping his hips and lunging deep cumming.....

He pulled the condom off and told me to suck his cock clean which I did mmmm loving the taste and feel of his cock.... he told me he often cycled through the woods at weekends and that if I was here I might get fucked again... my pussy was feeling very open... and mmmmmm I can't wait to be a bitch for him again....

Just back from a business trip to the North and Midlands, these trips do allow time to play, to dress and meet guys who like sissy boi's. Sunday I was in Manchester in the city centre a nice hotel, after I registered I got my luggage from my car went up to my room and took a nice slow long shower , shaved , fixed my dildo to the tiled wall and after soaping and rinsing my tight sissy pussy I spread my cheeks and pressed back onto it mmmmmm it was sooooooo mmmmm filling me up and I spent 20 mins riding it... and then rinsed my pussy and then spent the next hour or so dressing and making up.

I keep the outfit simple as I'm away from home a pink babydoll nightie , matching panties over my locked sissy cock , stockings , suspenders and heels.... made my face foundation eye brow pencil to darken my brows , lips gloss , mmm sissy pink , then eyeliner and falsies big long lashes.... then a long blonde wig to complete the look , slutty and tarty.

I use kik usually putting up a pic of me and a username... profile nothing too obvious but enough to interest, it usually takes around an hour to weed out the rubbish and sort the wannabees from the guys who are real and wanting to play.

Using a pre paid phone I then txt with the guy who seems most promising , sending more pics of me and asking to see his cock then he gets the hotel address and when on site the room number. The moment of truth comes obviously when I hear the knock and open the door and he sees me and I get to see him , Sunday night it was an asian guy in his 30's clean cut muscular and a very large uncut cock which he had out of his jeans as soon as I closed and locked the door behind him.

From the photo he'd sent me it had looked big and he was fat long uncut 9 inches or so and so very hard !!! I was told to kneel and I did and he rubbed the sticky tip along my lips and I sucked the fat brown head mmmmmm opening my mouth wide as he moaned......

He moved to the bed taking his jacket off and then his jeans and shorts and I sat and sucked his cock as he stroked my long blonde hair.. he slipped from my mouth and took a condom from his jeans and rolled it over his cock and told me to get on my knees and bend... I did and he slapped my sissy bottom cheeks telling me I was a teasing bitch and he was going to fuck me... !

He did slowly and deep for 40 mins ignoring my caged sissy clit until the last five minutes and then as he speeded up he tugged and pulled at the cb6000 mmmmmmmm I felt him lunge and groan and hold my hips and knew he was filling the condom mmmmmm then he was sliding out and telling me to roll over which I did to be presented with his still hard condom covered cock , I gently pulled the cum filled condom off and sucked him clean mmmmmmm then he tookt he condom from me and poured his cum over my locked sissy cock ........

I am often asked by guys why I like to be in chastity , why I prefer to have my sissy cock locked away and I suppose for me it's the ultimate symbol of being a sissy boi , in that my clit (when I am in sissy mode) is of no real use or interest and I lock it away to emphasis that I am a submissive mature sissy boi for use by real men or other sissies and I have a pussy which is for fucking by a cock and a mouth for sucking cock... I am in panties and lingerie because that's part of the fem me I love being a sissy boi a girl for real men....

Working for a large employer in an office enviroment has it's advantages and one is lots of men around , real men who being men like uncomplicated sex and it's surprising just how many will fuck a sissy boi. There's a guy who has in the past week fucked me 5 times at work and I have sucked his cock three times , he approached me having been told by another guy that I was a sissy boi and I would fuck or suck him.

I keep a pay as you go phone for contact usually txt so I was pleasantly surprised to get a txt from someone I did not know saying he'd seen my photos and profile on a website and was I interested , I sent a txt back asking in what ? and got a picture of a large very erect uncut brown cock , of course I replied yesssssss lol , and he then revealed where he worked and I gasped , same place as me , then he suggested I take a break and meet him in the sub basement filing area , I was intrigued and by now horny and then got a txt saying 5 mins sissy boi ....

I left my desk and made my way down in the lift to the sub basement which is divided up into various storage areas , I stepped out of the lift and waited.... a couple of minutes later the lift pinged and out stepped an asian guy , in his late 20's tall and heavily built in a suit and tie , I recognised him and he smiled , I blushed and smiled back and led him down a corridor to a small area that had once been a rest room .. it had a table some chairs and an old leather sofa.

I sat on the arm f the sofa and watched as he locked the door behind him and slipped his suit jacket off hanging it on the back of a chair , he asked what name I liked and I told him Michelle .. the name on the profile and he told me my pics had got him very aroused especially those of me made up and dressed on my knees sucking cock and bend over taking one.... I said thank you and he rubbed the front of his trousers , he was hard and getting harder and I stared at his erection and he smiled asking would I like to see ?.

I nodded and he undid his belt pushed his trousers down and then his boxers freeing his now very stiff cock , he stroked himself and told me he wanted me , I slipped onto the sofa and he moved closer , close enough for his cock to brush my cheek and then my lips I kissed the tip and opened my mouth and holding him with both hands sucked mmmmmm he tasted mmmmm and I bobbed my head gently and played with his big brown balls he groaned and pushed deeper into my mouth telling me to suck and that he hadn't cum for 3 days and that his wife was pregnant and hadn't let him fuck her for a couple of weeks since the test results.

He was soon panting and gasping as I sucked and pumped his cock I knew he would cum quickly and he did holding my head and moaning groaning as his cock flooded my mouth and I gulped his sweet salty cum , there was a lot and I gently milked him into my mouth looking up as he grinned at me....mmmmmmmm.

He thanked me and asked if I would dress for him sometime and I grinned and said of course....

It was Xmas I was 17 and staying at my step mothers sisters with my older sisters and step mother , every year on new years eve they had a fancy dress party food drink music and costumes and this one year my sisters and I would go as a sister and two brothers. They both knew of my dressing and being a sissy and had for years, I protested for form in front of my step mothers sister and her husband and sons but I was very aroused by this opportunity to dress and in public.

My sisters between them sorted out my fancy dress a school girl outfit , white bra and bikini briefs , ankle socks , navy skirt that came to mid thigh , a white school blouse and tie and a pair of low heeled black pumps.

I spent a couple of hours getting ready , I was mostly smooth having waxed what little hair I had and I made sure I was washed and lubed spending some time in the shower with my dildo not that I expected anything to happen but I loved using my dildo and the act of cleaning and lubing myself is a great turn on.

Once dressed my sisters did my hair up in pig tails to complete the look and then added the palest of pink lip gloss and a little eye liner , the final thing was perfume.

We went down together and the party was well under way , we sipped wine and watched the party and got lots of looks and glances and my step mothers brother who was older mid 40's made a great thing of kissing my sisters on the cheek and hugging them one by one and then he smiled at me and did the same slipping his hand under my school skirt to squeeze my bottom cheeks as he kissed my neck , I gasped and wriggled and he laughed and said we made a lovely trio and off he went.

Later on he found me dancing in the dining room which had been cleared of furniture to make space he watched me for a few minutes and I became very self concious , his eyes on me when the music changed he slid up to me and as a slow Barry White number came on he pulled me close and we danced after a minute or so he pulled me closer pressing himself into me , I could feel the large lump of his cock and as he kissed my neck I sighed and pressed back rubbing myself against him.

He whispered in my ear that I was a naughty sissy boi tease and that I was going to get what I deserved and I just giggled and pressed harder against his cock , when that track came to an end he led me from the dance floor and I followed as we wound our way through partying guests.

We slipped upstairs and I led him to the room I was sleeping in where with the door locked behind us he kissed me and I opened my mouth to his as his hands squeezed my sissy bottom and pulling my panties aside pressed a finger to my pussy and it slid in.. I gasped and moaned into his mouth and squirmed as he finger fucked me and soon I was panting my sissy clit was hard and I just wanted his cock.

I broke from him and knelt up on the bed slipping my panties down and looking back at him , he dropped his trousers and boxers stroking his long fat uncut cock telling me I was a dirty lil bitch boi , he teased me grabbing my balls and gently tugging them as he rubbed his cock between my cheeks over my lubed pussy I groaned and gasped and wiggled and he grunted and holding me by my balls pressed his cock to my sissy pussy .... he felt huge... and hard , hot and I whimpered moaning Nooooooo softly as his cock sank inside me filling and spreading me wide.... he got half way in and began to fuck... slowly then faster and deeper forcing all his cock into me as I gasped and panted and moaned...... then I was cumming squirting over my bed sheets and shrieking.... and then I felt him lunge in deep and gasp... he was filling me ... when he slipped my from my now gaping sissy I rolled over and smiled up at him and he grinned and told me I was a dirty lil slut I just giggled and said thank you...

(For a lovely sissy friend of mine who it happened to)

He wasn't sure exactly when it had all started but over two short months a slow change, a transformation from an average if wimpy hetro male to a cross dressing sissyboi. He'd been living with Lisa for a couple of years she was 23 he was 19 they'd met at a mutual friends birthday party hit it off and moved in together a month later.

On holiday in Jamaica he'd walked into their Hotel room to find Lisa being fucked on the bed by an older black guy she was on her back legs in the air screaming and moaning as the guy fucked her with his very large cock , Lisa just looked over at him and giggled and the guy fucking her grinned and laughed and slammed even harder making Lisa shriek louder.

As he watched and listened he was suddenly very aroused , harder than he'd been in ages and as Lisa screamed to another orgasm the guy lunged and groaned and held his cock deep in her as he came , Lisa just lay there panting and gasping sweaty despite the A/C , the guy slid from her he was still half hard his cock was long fat and uncut and sticky with his cum and Lisa's pussy.

He got dressed and left and told her later bitch and smiling left , Lisa looked at him and grinned laying thighs spread the guys cum leaking from her well fucked pink puffy pussy. He asked her why and she just laughed and told him what did he expect with a 4 inch lil dicklet and lasting less than a minute.

She laughed again and Paul just went red with embarrassment it was true he was 4 inches at the most when fully hard and when they had sex he did not last very long which was why he tended to spend a long time eating her pussy and then fuck her because he knew he would cum so very quickly once inside her and a few times he hadn't even got inside her before he'd squirted on her thighs and once on her belly.

Lisa teased him telling him the guy who had just left was a real man and had fucked her twice cumming inside her both times , by now his cock was aching and pulsing and he was afraid he was going to cum in his pants and as Lisa told him to look she pulled her knees wide and spread for him her ravaged pussy gaped and more cum dribbled out.

She looked at him and told him he was useless and a wimp a sissy boi , and as he liked eating her pussy so much he should get between her thighs and eat her now. Paul gasped when she said this he'd been thinking at that moment how she would taste and here she was telling him to get down and clean her up.

To his own surprise and Lisa's delight he climbed onto the bed and kissed her cum smeared clit , then he lapped at her open pussy tasting the cum and sinking down his mouth greedily eating her smooth cummy pussy as she groaned and held his head tight to her. He ate her for ages and at some point he did cum in his pants a massive intense orgasm which when later he took his jeans off Lisa giggled and pointed to the large wet blotch on his blue briefs.

The rest of the holiday Lisa fucked and sucked whoever she wanted and Paul became her cuck , her sissy cuck making him wear a pair of her panties stained with her juices and another guys cum , he was humiliated but also very aroused.

It starts with a txt message maybe Hi or How are you , and then he usually follows it up with a pic of his errect cock, he knows I love it , knows how it turns me on and so even if I'm not feeling particularly in the mood he knows I soon will be. It's true when I get the pic of his cock I'm immediately thinking about sucking him , having him in my mouth , the taste and feel of him and I'm getting aroused my lil sissy clit swells in it's pink cb6000s chastity device. He prefers me in the short version because he likes the way my aroused clit makes the cage stick up and out.

I love the sensations being in chastity gives me the teasing , the arousal it's like being touched and stroked all day but not to the point of orgasm just short of and that's the thing.

Within the hour he sends me his favourite vid clip him fucking me a close up of his cock in my sissy pussy sinking in and out his grunts my whimpering and gasping , panting and moaning begging him not to stop , then him cumming filling the condom and sliding out leaving me gaping open spread and fucked !.

Usually within minutes of him sending the vid clip he tells me what time and by then or minutes before I'm ready , dressed , lubed clit straining stockings suspenders , corset , wig make up heels and I'm waiting , wanting his cock !!!!

I have been a sissy since I was 12 or so and began dressing in my older sisters clothes and then my step moms , I discovered masturbation and then sex with other boys and then older men , I'm bi and had girl friends in my teens as well as boy friends.

Now I indulge my sissy fem side from time to time and love to dress and suck cock and be fucked... quite submissive and into chastity.. when sissy I self lock into a cb6000.