Medway_sissyboi's Blog

After seeing some pics online I bought some sissy stuff for an outfit and there are new pics posted , I was soooo horny taking the pics I nearly squirted wearing my rose pink glass dildo but I managed not too and to wait for a friend to arrive and he made me cum so very hard !!

I'm a mature mid 50's sissyboi and have recently started indulging my sissy side once again , I seem to always have done this be very sissy for a period then deny it and then come back to it

I'm returning after being away for work , returning to here and other sites and also to being what I am a cross dressing sissyboi cock slut .... a recent experience

Like most New Years resolutions mine faded a little towards the end of January but a dare one night on a chat had me up bright and early (still dark) and after a quick shower and 5 mins with my dildo in the shower I was in track suit trainers and out , I confess to cheating a little by driving to the place but I parked up warmed up stretching all the time my mind racing wondering if he would even turn up never mind would anything happen. It was a lil chilly but I jogged off into the woods 5 mins or so before we'd arranged to meet and as I rounded a corner in the path I saw a figure in front of me in a small clearing , I smiled as I passed him not knowing if this was him or just another jogger.

Turned out to be him because as I passed he followed and I glanced back and he smiled , I moved off the main path and into the brush following a smaller trail around several clumps of bushes and trees and then through a stile in a wooden fence and into the heavily wooded section. I stopped by an old tree trunk , he slowed and stopped walking up to me , I was trembling partly the cold but more excitement than anything my lil sissy clit was swollen in it's small metal chastity cage , aching and swollen I was nervous until he said 'Sissyboi' and smiled and I blushed and smiled back then his jogging bottoms and boxers slid down and I caught sight of his cock sticking out , thick uncut and big !!!.

I leaned down and kissed it he pushed my head down and told me to suck , I did , it made my jaw ache but I managed to suck him well the first inch or so as he squeezed and slapped my bottom cheeks and pressed a finger to my lubed sissy pussy , I groaned around his cock as his finger sank inside me and sucked harder , then he was tugging my bottoms and panties down and turning me around forcing me over the old tree trunk , his hands spanking my cheeks hard , I yelped and squirmed but I bent over and felt his fingers rubbing my slick tight sissy ring. I was very excited and unable to think of anything else except his gorgeous big cock and where I wanted it. I needn't have worried he spread my cheeks and I felt the tip rub over my pussy and then back down and he thrust hard inside me , I gasped and groaned he felt so big so hard my clit pulsed and ached and as he moved deeper and thrust in and out I had a sissygasm my clit straining and squirting my sissy cum despite being locked in a small metal chastity cage.

All I could feel was his cock inside me , not the cold or damp or even any fear that we might be seen by another early morning jogger , after 9 months of no cock I was in heaven and back in submissive sissy mode being a dirty lil bitch for a real man and I loved every second !!!

Must be the heat but I'm so horny this past week or so and so it seems are a lot of guys I was down in the basement at work three times yesterday with different guys , all wanted the same thing to cum one in my mouth and two fucked me over the table.....

Growing up and knowing I was a sissy from age 12 on I developed what I have heard other sissy men call sissy radar a very quick intuition about other guys who like sissy men. I never called it that but I picked up very quickly on guys that were interested in me because I was a sissy teen. The looks , the smiles which I returned the knowing glances and eyes and then I learned if I led they would follow and then finding somewhere quiet enough for me to suck their cocks or bend over to let them fuck me.

It was a game I used to play , spot the sissy lover and wherever I was I got very good at it and my craving for cock was satiated for at least a short while. Most of these guys I had never met before and most I would not meet again a few became regular meets.

I tended to wear tight faded jeans or jeans cut offs over pink panties and a pale coloured tee purple nearly pink was my fav over a AA bra my hair which was long to my shoulders and I often used a very pale pink lipstick which was pretty daring for the times in public so I tended to apply it when I was at a known cruising spot.

I work in an office and go to work in panties over my chastity device a cb6000 usually a pink thong because they push the cb6000 down and back and it's more comfortable like that. There are a few guys in the office who know I am a sissy boi , one guy I met via a chat room and when he turned up we recognised each other. I was a bit apprehensive at first but it turned out well I sucked his big cock and he fucked me and we have met several times since.

The others I met at a local cruising spot they saw me and of course I ended up sucking their cocks and being fucked , now they have me at work we have a basement filing and storage area for records which is a nice quiet place to spank and fuck a sissy boi at work these guys are all married but they are guys and guys want uncomplicated sex and a sissy boi provides that no other involvement , available , dosen't say no and loves cock.

The youngest in his late 20's his wife is pregnant and has gone off sex entirely so he is giving me what he would be giving her which means I am getting his cock most days , he sends a txt telling me a time and I go down just before and wait for him in one of the small rooms there , one has an old leather sofa and some chairs and a table in it and we meet there.

I wait and when he arrives he locks the door and drops his trousers and boxers his cock is gorgeous fat but not too long 8 inches and uncut he watches as I kiss and lick the tip and depending on how desperate he is to cum or fuck me and cum I will suck him for a while and then he tells me where he wants me and I unroll a condom over his cock and then lube him and bend over and spread for him...... I love the sensation of his fat cock pressing my lubed sissy pussy and then he sinks in and fills me stretching me wide and I'm whimpering because he is so hard and fat and he slaps my bottom and tells me to be quiet and take it like a bitch , but he loves my whimpering and then begging and moaning and gasping sometimes he tugs my chastity cage and holds me by it as he buries his cock all the way inside me and slams harder.

I always cum sometimes very quickly sometimes I manage a few minutes before squirting , sometimes I am still soft sometimes I am swollen in my cage but either way it's so exciting and I either squirt softly or dribble my sissy cum away as I am used like a bitch.

When he cums he slips out and I roll over and pull the condom off his softening cock (he dosen't stay soft for long)and he likes me to pour his cum into my panties so I am wearing it for the rest of the day .... he also expects to have his cock sucked clean before he leaves and then I do ...... with his cum coating my sissy bottom and clit and balls...

Anticipation when meeting a guy is so very exciting , getting ready showering and shaving , washing my sissy pussy clean , lubing myself with my dildo , pressing my plug in to keep me open and teased , dressing , stockings , basque , tight g string pulling my caged sissy cock down and back between my thighs , then my wig some make up lip stick and heels...... then the messages if it's someone I have never met before wondering what his cock will be like to touch and kiss and suck and how he will feel in me.....

So by the time he has me on my knees and spread or just bent over I'm so excited , my sissy clit is tingling and I'm about to squirt hands free , then his cock is pressing my lubed ring and sinking in making me moan and gasp and pant and I'm there in the dream being a bitch being fucked by a Man and then I'm squirting and cumming in my chastity cage and whimpering like a slut in heat ........

I have been a bi sexual sissy boi/gurl since my early teens when I first slipped into a pair of my older sisters panties and looked at myself in the mirror. That day I spent the morning as everyone else was out dressing up and playing with my very hard cock I'm not sure how many times I spurted but it was several and I fell asleep on my bed in a pair of pink cum soaked cotton briefs.

It developed from then on and progressed to dressing as a girl and then I discovered my sisters dildo and then my step mothers vibe and when I was sent to prep school and put into a dorm with 6 other boys I had my first sexual experiences with other boys.

I am bi sexual and married etc but there is this feminine side of me that has always been there , I'm a passive deeply submissive cross dressing sissy boi now currently locked in chastity for a younger Dom guy who uses me when he wishes as a slut orally and anally , he also spanks me when he pleases.

The idea for locking me in chastity came from a friend of his after they had both used me at his house (his wife was away) and my friend Bob had watched me with his friend Kevin and Kevin had been calling me a real slut for sucking his cock and taking his cum on my face and then teasing me because despite being fucked and sucking both their cocks I was still soft but dribbling.

Kevin said I belonged in chastity locked away as my lil clit was useless and I did not need it to be their bitch , Bob sent me a txt a few days later with a link to a website which was advertising the cb6000 telling me to buy one and when I had it to let him know.

I checked the link and ordered one not know quite what to expect but when it arrived in the post a few days later and I unpacked it I knew I wanted to wear it , I shaved and moisturised my cock and balls and fitted it using the largest ring and it went on ok and I put the lock on and realised I was very excited and soon aching and trying to get an errection.

I txted Bob to say I had the cb6000 and was wearing t and he asked for a pic which I sent and he txted me back he was coming over to see for himself. By the time Bob arrived I was dressed and so horny my sissy cock was swollen and aching in my new cb6000 and Bob had me drop my panties and show him as soon as he was in though the door.

He grinned and tugged me I gasped and he told me I was going to be wearing it for him , then I was on my knees and sucking his big fat 9 inches and then a few minutes later he was fucking me over the back of the sofa and I was having my fist sissygasm in my cb6000 it was so intense........

This has confirmed my role as a passive submissive cross dressing sissy boi an anal and oral slut..... my clitty soft or swollen in it's cage..... until a Man fucks me like a bitch.....