Blossoming Sissy

By Scott Kimball

Published on Dec 28, 2018

Gay

I knew I looked like a slut and I loved it. If the wet spot on the back of my cutoffs was not a dead give away, I am sure that the trickle of cum running down my thigh left no doubt as to what I had been up to. Sure some people looked at me in disgust, but most stared and my bubble as and smooth thighs with intrigue and desire. While waiting at the crosswalks more than one semi-hard cock brushed against me and even one well dressed shaved had businessman had the audacity to slip his hand up my shorty cutoffs where a couple fingers found my swollen cummy hole and slowly rotated around it testing its tightness. Just enough stimulation to remind me that I did not yet get me release and I needed an orgasm soon.

Fortunately, I knew place a few blocks away. In the basement of am investment bank was a private employees' cafeteria with an adjacent public restroom. Almost no one knew about it. At lunch there was a steady stream of suit and tie daddy's and it was totally empty any other time. Many a noon hour had been spent at the urinals stealing peaks at the big meaty cocks getting pulled out of $700 slacks. Something about a thick semi-hard cock lurking inside and expensive suit makes my mouth water and boy pussy tingle. If they catch my looking and turn a little to show me more a quick four fingers held up and then index finger pointed down, let them know when and where we could get it on. Many afternoons had been spent with stressed out power brokers pumping my face full of their cum in a way their wife would never let them; but those are other stories. Right now I just wanted to get down there alone and take care of myself.

Down the side staircase and past the cafeteria I slipped in to the vacant men's room and claimed the furthest stall. I dropped my shorts, propped my feet on either side of the closed stall door and reached between my legs to find my wet hole. It had finally started to close up from the fucking Daddy had recently given me, but was still wet enough to allow easy entrance for my two fingers. I was surprised by the thick globs of cum still inside me in spite of how much had leaked out to stain my shorts and drip down my legs. As I started to move my fingers around the wet pussy sounds sounded so erotic I pulled my hand to my mouth to taste the mixture of sweet salty cum and musky bitter boy juice. Then relished the sexy taste as I resumed my finger fucking, this time curling my fingers so that each thrust pushed them across my g-spot bringing me closer to the orgasm I needed.

A shuffling sound brought me out of my trance and I opened my eyes to see a face against the crack in the door enjoying the show. Without thinking I unhooked the latch and let the door swing open the reveal the perfect cock already hard in that angry purple headed way that says resistance is futile. A nicely thick cut head swelled to impossible girth in the middle only to taper back a bit at the base making it real life version of a 7" butt plug that was easily 7" wide at its apex. This dream cock protruded from a perfectly smooth groin. Though I don't mind a hairy daddy the kink of an alpha who shaves smooth is a big turn on. As my gaze travelled up the body it finally arrive at the face of the shaved head dude who had fingered me on the street. Seeing his 6' frame, large but not obese torso, expensive clothes and thick hard cock put me on auto pilot. Instinctively I spun around and bent over, grasping the back of the toiled and exposing my boy pussy for him to use however he wanted.

I was both scared and aroused by a cock of his girth but prepared for an immediate assault. Instead he commanded me to "pull your cheeks apart so I can get a good look at your pussy" I straightened up, arched my back and reach both hands to my ass spreading it as wide as I could. "Fuck" he says, "That wet pink hole is the sexiest thing I have ever seen" "Tell your boss what it needs".

"Please push your big dick inside me, let me feel it stretch my boy pussy wide open."

"Good boy" " You are fucking whore that needs cock all the time, aren't you"

"Yes I want it deep inside me making my little pussy quiver, make me explode in a girlie orgasm when you fill me with cum. OH god give it to me now I want it so badly"

But then instead of his thick hard cock I feel his hot breath on my hole and his tongue working its way from my balls to my cum covered hole. Slowly his tongue circles the rim licking up my daddy's cum. The sensation cause my muscles to loosen and I push back pleading for more. Happy to oblige my handsome "Boss" begins to tongue fuck me with deep hard thrusts, his face smashing against me ass as his big tongue goes deeper and deeper into me. As he pulls back he remarks. " I can taste that you have already been fucked today. That's good it will make the next part easier"

Then he stands and I can feel his cock positioned against my pink hungry pussy. The head pops in fairly easily though the sensation makes my knees buckle so that he has to grab my hips to keep me from falling. Normally once the head pops past my ring the rest can slide right in. But this is different; each tiniest push stretches me further. Finally, when I can take no more he pulls out leaving me wide open and empty, it is then I know that in fact, more is all that I want. "please put it in me again, oh god please fuck me I need to feel every inch of your big cock buried inside my pussy."

"Good girl, you will"

Again it is at my entrance, slowly sliding in and out, each time pushing my limits at bit further until again I can take no more. This time though he reaches around and pinches my nipples, rolling them between his thumb and forefinger. The tingling runs straight into my pussy and feel it start to throb and open, sensing my desire he pushes all the way in. As the thickest part passes into me, my pussy walls clamp down pulling the rest of him in and locking down on the base of his cock. I cannot believe that his massive thick tool is actually fully inside me. But I feel it filling every inch of me and throbbing against the walls of my boy cunt.

Rather than the pounding I am used to getting. His cock moves slowly inside me, never pulling all the way out, just far enough that my outer ring grips the thick waist of his cock. Then back in he goes so that the waist presses over my g-spot making my thighs quiver and shake as I squeal and moan in delight. My own clitty is like a steel shaft with a constant trickle of leaking precum. I know my orgasm is imminent. He pulls back one more time and my pussy dilates fully as my orgasm begins. One final hard push over my prostrate sends me over the edge. He is now fully swollen and cumming too. Our pulsing muscles matching each other, as his semen pours into me my ass cunt spasms and squeezes every drop from him. I am thrashing wildly unable to control myself, squirting my own cum all over the floors and wall. I have no idea how long this goes on, but I realize that my clamping pussy is acting like a cock ring not allowing his erection of subside. Finally, he pulls back. Pulling out is as hard as pushing it in was and feel just us good. As the last inch of him drops out of me I have another small orgasm, my pulsing hole actually squirting his cum out in small spurts.

I hear him zip up, leaving me half dazed and covered in both of our cum. Before he goes, he leans over to whisper in my ear. "You have the hottest pussy that I have ever fucked". Then he drops a card on the floor. It lands face down in a wet sticky pool. When I turn it over, I see a phone number covered in the cum that he just forced out of me.


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