Sissy in the City part 1. My first regular

Hi my name is CJ. This is meant to be a multi part fiction/fantasy series based in part on some of my real life adventures. Any resemblance to real people is purely coincidental.

This is my first published story. Constructive criticism is very welcome. Please be kind. 💋

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I was a 30-something male working in Downtown in a high rise and riding the train into the city each day. My (hetero) life was rather boring filled with work and commute and a drab cheap apartment.

I had been dressing as a sissy and looking for a daddy for a couple of months mostly enjoying the flirting and finding i liked the dick pics (and o boy were there many!) This progressed as i got more and more confident in being in public in my sissy personna and got more and more attention from men.

This will be the story of my first Daddy that I serviced regularly.

I had met an Alpha online and we begin flirting. He was a construction lead on a high rise several blocks from where I worked. We can call him Craig. He had a nice cock, a chill but dominant attitude and was looking for a sissy to suck his cock on the regular. And hey that is me.

We decided to meet up on a fall night after work. We both worked late and thought we could meet discreetly at his jobsite.

I spent the weekend getting my legs shaved, my bikini area waxed, and buying a new outfit and perfecting my ability to change from my guy self to my sissy self in a public restroom.

I was to meet him on a Tuesday. I was smooth, caged, plugged, and pantied under my boring guy clothes that morning in the train. I had my sissy gear in a medium sized duffle bag on one shoulder and my satchel under my other arm.

I continued to tease my construction worker Daddy, sending pics and flirty texts all day. He fired back with pics of his hard cock, and talk about binding me and fucking my face for as long as he wants to. My response was a meek and lusty 'yes, please'.

Finally it was time to leave work, I headed to a local bar about half way in between our places of work. I duck into the womens restroom and begin my transformation. I came back out about a half hour later looking like the sissy slut i really am. I was wearing pink lace thong panties, a matching pink bra with falsies inside. I am still caged and plugged. I have on a short pleated skirt with fishnet tights and a pair of pink doc marten boots for a kind of goth slut look. I was wearing a skimpy crop top that said Daddy across the chest and showed my bra underneath. I had a pink leather choker that matched my boots and lip gloss. I had a blond wig with hair that i had pre fixed to match my goth slut look as well as the requisite heavy eye make up.

I walked out to the bar with a small purse and my large duffel bag. I approached the barkeep and asked the 20 something female dressed in a concert t shirt and cutoffs. I asked for 2 shots, an energy drink and if they would store my bag while I ran 'an errand'. She yelled my request across the bar to the older (50 ish) barman and he looked me over once and with a surprised and then devilish grin said 'sure, but as long as you return and drink with us for the remainder of the night'. I said sure trading eye contact with the girl. She took my bag and i downed the liquid courage, leaving a $20 for the drinks and a $20 in the tip jar. I stepped out of the bar feeling the chilly air find its way up my skirt and remind me that my caged clit has been leaking in my panties all day.

I found the building and messaged Craig. He let me in a secure side door and before i knew it. I was on my knees in an unfinished conference room that looked like it was his makeshift office.

Craig let me fish his cock out of his pants as well as his big full meaty balls. He was taller than me, by several inches, older than me and probably had a hetero relationship that didn't keep these big balls drained. I sucked those big balls in my mouth and licked each one individually. I worked my way back up to his cock and swirled my tongue around the head and then begin working his increasingly hard and thick cock into my throat.

Craig had given me free reign and control up to this point. Craig puts both hands on my head and pulls me down his cock till i can't take any more. I can feel slobber dripping down my chin. Craig asks if I am ready to be face- fucked. My cock lust has taken over fully. I nod my head up and down looking up at Craig's full beard and brown eyes.

He chuckles to himself and says that i am such a sissy cocksucker. This makes me leak more and pushes me further and further into my submissive place. He pulls out his phone points it to my face with his cock still between my lips and takes a pic. He turns on the video and says "hey my little sissy cocksucker, are you ready for your first face fucking? I promise to not go easy on you". I continue to suck and nod my head up and down as he films while i look dead into the camera. (He showed me this vid later and it is my favourite and hottest pic of me as a sissy).

He reaches over me and grabs a bag of indusreial zip ties. He tells me to give him my hands. I place them over my head and he wraps each one with a tie then uses a third to tie them together. I focus on sucking and am surprised when I hear a drill then feel my arms stretched over my head as i am simultaneously pushed back by Craig's strong thighs while keeping his cock in my mouth. I feel him lift me by my arms before falling back to my bare ass on the dirty concrete floor. My arms are now bound together stretched and secured over my head. I feel his heavy boot find my balls under my skirt and his toe simply rests against them.

Craig refocuses on the task at hand. He keeps talking to me about it in a low manly whisper. 'Little sissy wants her face fucked, Daddy is gonna fuck little sissy's face.... we'll see if you really are worthy of being my sissy cocksucker'.

He feeds me his hard cock pinning my head against the wall. He begins a slow and deep rhythm, bouncing his big beautful balls off my chin. He hammers away at my throat for a solid 10 minutes. I feel his cock swell and his balls tighten. He pulls out, and I gasp for breath. I had only been concentrating on keeping my teeth from his incredibly thick cock, moving my tongue, not puking and finding a way to breathe. I have spit and throat spit and precum all over my face now, Craig notices and takes another pic. He then pulls his belt off and drops his jeans to his ankles. He wraps the belt around my neck and pulls me to his cock. The belt tightens around my throat as he pulls me down to the base of his cock. He now has both feet in between my legs with his pants around his ankles. His boot has moved forward and is now pressing down into my balls. He begins to pull my head up and down his cock while he braces himself on his front foot that is halfway ontop of my trapped balls. Half of my brain is in sissy bliss. The other half tries to breathe while choking on his rock hard thick dick, is being choked by the belt wrapped around my neck and is supporting a man standing partly on my sissy balls.

I lose track of time, but after several minutes of being pulled up and down his cock. I feel him grab me by my head with two strong hands and impale my throat with his cock that swells then spasms and shoots a warm gooey shot, he pulls back and holds my face under his cock as he sprays me down with ribbon after ribbon of cum. He finishes by pushing the head of his cock between my lips and letting me suck him dry. I swallow and he lets me and begins redressing while i am still bound and breathless. .

He pulls my arms off the hook in the wall, cuts the zipties and then asks me for my panties. I struggle to my feet and take off my lacy pink thong, he uses it to wipe my face and then shoves them in my mouth, telling me to keep them there till i get home. His last remark to me was 'good job cocksucker, see you Thursday' as he walked away from me and toward his truck

I remember stumbling out of the side door and working my way back to the bar. The bar is now fairly crowded. Its a clientele I feel comfortable with. I make my way to the bar and end up being served by the old man. I fear he is going to make me blow him to get my stuff back but instead he appraises my situation, and says tonight you will flirt with my customers and be friendly and drink girly drinks. I spit out my underwear, and he recognizes what they are and takes them and pushes them in his pocket. I make nice and flirt with the college boys and the older professional men. I do get groped and many looks are exchanged between men as they explore my underskirt.

I would go on to see the construction worker many more times and each time was more intense than the previous time. I also made a sort of friends with the older perverted bar man. I did suck him off in his office more than once in exchange for being able to change in his office. He did eventually get me a good mirror in there that I am sure also had a video camera in it. Anyway, I was young and enjoying exploring a new and way more fun side of myself so I did not mind.

End Part 1