tagTransgender & CrossdressersLast Friday: First Sissy Experience

Last Friday: First Sissy Experience


Been a lurker for a little while, and thought it was time I contributed with a post!


Title: Last Friday

"You ready for your surprise?" she asked me coyly.

"Yes!" I said excitedly, thinking of the possible toys we had been looking at online, or perhaps a striptease. We had our eye on a Bad Dragon dildo as our starter strapon kit had grown my interest in more pegging play, while Katie also wanted a new more powerful and cordless Hitachi magic wand.

She had a few minutes earlier gently slipped my cock into the new chastity device we had gotten a few days before. This was the first time I had worn it, and the restrictive sensation was a little bit of a tease as she closed the little brass lock through the little pink cage. She had slipped the key around her neck on a thin silver chain she had bought for it, the key dangling between her perky tits.

We had been experimenting with a little bit of "dress-up" recently, and I was dressed in a bright pink garter belt connected to matching sheer pink stockings. My body was smooth, having been shaved earlier that evening. Katie ran her hand down my thigh to the garter strap and snapped it smartly against my leg and licking her lips. My face was done up with understated makeup, an earth tone eyeshadow, Kylie Jenner nude lipstick, and my eyelashes were long and thick with mascara.

She was wearing a tight, almost-too-small black bustier which served to push her small breasts together and give the illusion of cleavage. Just the tops curves of her nipples poked over the top of the garment, leaving them partially uncovered. She paired this with a garter belt and lace stockings. Underneath was a lacy thong, dark purple and hinting at her tight little pussy underneath. Her dark hair and light blue eyes contrasted starkly, and her dark red lipstick was vivid against her fair skin.

She had told me to lay down on the bed to relax on my back and blindfolded me, making out with me just a bit playfully as she pushed me back across the foot of the bed width-wise. I had just zoned out as she walked into the other room to get herself a glass of wine and then heard her feet pad back into the room on the thick rug on the floor.

I felt something soft barely brush against my lips, which were just partly open. It tickled them just slightly. I felt Katie remove my blindfold and my entire vision was obscured. My jaw dropped open when I saw it was obscured by a huge, thick black cock. I looked back further and saw the heavy black balls hanging down below, then realized that they were connected to a muscled black stud. He was completely naked and perfectly formed.

"Like your surprise?" she asked. "He came at a pretty penny but he's a professional. For the duration of the night, he's silent and follows only my orders. I know you've been fantasizing about this for a while now."

She traced just her French manicured fingernail along the top of his cock and then around my lips. I felt the same electric sensation as when the cock was gently rubbed against my lips. Katie slowly slipped her finger into my mouth and wet it with my tongue before dragging it over my nipple. My cock strained against its cage and my balls pulled tight to my body.

Katie grabbed my hair and guided me to the cock with my mouth wide open in surprise, causing me to take the big black cock into my mouth. Just the head took up the entire space inside my mouth, and I started to gag immediately. Katie forced me further down on the cock and a single tear ran down my face from the deepthroating, stained by my mascara. Katie let me come up for air but then said, "On your knees, slut." I complied and assumed the position on the bed. The Bull came up behind me, and I could almost feel the heat of his hot black body.

He took his hand and grasped his cock at the base, raising it straight up in the air before letting it fall down to smack my little pink hole, which contracted at the sting of the contact.

Katie leaned over me, her perky breasts hanging down and barely grazing my back as she hovered with her mouth about six inches above his cock and slowly let her saliva drip down in a long strand, first pooling on his shaft and then dripping down between my ass cheeks. I felt the warm saliva run down the crack of my ass and across my anus. The air felt cool against the wetness until the Bull's thick black cock slapped again against my ass, this time covering my whole crack with Katie's slick spit.

I heard a loud SLAP and felt my ass sting as I realized Katie had spanked my ass. The Bull slowly started thrusting his cock between my round ass cheeks, Katie's handprint starting to form in red as he rubbed back and forth. As he pushed forward, his heavy balls would gently bump against my tight, smaller balls and my locked sissy cock. The movement sped up and his balls began to steadily, slap, slap, slap, slap against my sissy package as his huge cock head would barely bounce away from my asshole, keep from sliding into the tight ring and instead follow along the valley of my ass cheeks until he would reach my balls with his again.

"You ready, baby?" she asked.

"Yeah" I said slowly, almost unsure of myself. I felt my asshole pucker involuntarily under the friction of his shaft sawing back and forth over the ring of sensitive skin.

Katie barely placed one finger on the shaft of his cock and gently pushed down with the next thrust forward. Instead of bouncing past my asshole, his huge, thick cock head slid straight into my butt with an overwhelming stretching sensation as the wide shaft followed.

My asshole squeezed his cock helplessly as Katie cooed. "Yeesssssss babyyyyyyy...Take that fucking big black cock for me. You know I want to see your sissy hole filled with cock."

"Fffffuuuuuuck baby!" I said as he partially withdrew from my ass and thrust just millimeters deeper than before. "His dick is so big! I'm completely stuffed!"

"We haven't even started yet, slut" Katie said with a knowing grin.

The Bull withdrew and slowly thrust again, his cock starting to widen about halfway along its length to stretch my hole to near its breaking point. The fullness in my ass was like nothing I had ever imagined. Katie leaned over again and a string of spit dripped down from her pouty lips to the shaft of the big black cock that was over half buried in my ass. By this point I had about six inches of thick black dick inside of my ass, and Katie wrapped her thumb and forefinger around the Bull's cock and spread her spit down the last five inches down to the very base.

My cock strained against its cage as Katie said, "My God baby, feel the size of this thing," as she slid her thumb and forefinger up and down his cock to distribute the lubrication evenly. "Maybe he'll have to fuck me next time...it looks like he would wreck my tiny white little pussy, and remember I'm not on the pill right now." Her eyes were magnetically drawn to the sight of the Bull slowly sinking the rest of his eleven inches into the unbelievably stretched ring of my asshole. She smiled mischievously and bit her lower lip. His big black cock was thickest at the base, and I moaned unconsciously as I felt my pink sissy hole convulse around his rock hard girth. It was easily as thick as an aluminum can, and the veins coursed and bulged along its surface.

I looked back and saw Katie lick one of the Bull's nipples while she rolled the other between her fingers, and I felt his cock somehow swell larger and my breath caught in my throat. He rocked back and forth, drawing back an inch then burying it in my asshole, his cock feeling like it was in my tonsils. My locked cock was leaking a steady stream of precum which was dripping into a puddle on our soft gray sheets. Katie caught the precum on her finger and wiped it on my outstretched tongue. The taste was salty but somehow also sweet as it made my tongue slick over the roof of my mouth.

"You gonna gape for me sissy?" asked Katie. "I think our Bull here has turned your asshole into a sissy pussy! You're all turned out!"

"Uhhhhh huhhhhh," I moaned as drool started to leak out of my mouth and pool on the sheets.

She spanked my ass again, harder this time, as the Bull pulled his cock back until just the head remained inside my hole. He thrust once more, balls deep into my ass, then completely withdrew as Katie placed both hands on either side of my ass spreading me wide. My hole was left gaping open, just as wide as the cock which had stretched it. Katie released a glob of spit from her full lips and it dropped a foot straight into my gaping ass. Katie reached around and pinched my nipple playfully and my asshole winked closed then opened again to about half its previous width. My cock strained against its cage and my balls pulled even tighter to my body.

"Awww someone can't even keep his asshole closed anymore!" she exclaimed happily as she used her other hand to insert a finger in my asshole, able to insert the entire length without her finger touching the sides of my ass. Then she twirled her finger around the rim of my asshole and traced down my perineum to my cock cage which she tugged on playfully.

Katie grabbed the big black cock still hanging lewdly in front of my upturned ass and gave it a quick pump as she winked at me. She aimed it at my hole and said, "Beg for him to put his cock in your sissy pussy again, slut! We both know you love it, look at all the precum below you!"

It was true, there was a large puddle of precum that had now accumulated below my caged sissy cock. "Please baby, please put him back in my sissy pussy!"

"Please put WHAT in your sissy pussy, whore?" Katie asked with a smirk.

"Please put that big, thick, hot, black cock in my slutty little white sissy pussy! I need it! I need to be filled up!" I said as Katie gently rubbed the rim of my ass.

"That's better." Katie said, satisfied by my transformation into a cock drunk sissy whore.

She stroked his cock once more to make sure it was rock hard, and slid it past my sphincter by pulling the Bull forward by his big balls until her hand and those black balls met my own, which were starting to ache from being bound by the ring of the cock cage.

The Bull then began to long stroke me, picking up tempo and slapping balls deep into my ass while coming out completely for Katie to appreciate my ever widening ass gape. Every time he withdrew there would be a faint "pop" sound as my gape was exposed, and soon it remained gaping.

Katie had the Bull pause for a moment and had me try to squeeze my sphincter around her finger, but my feeble anal ring barely even contracted because of the ruining it had taken at the hands of my new black cock stud. She got to three fingers before my asshole even brushed against her finger.

"Maybe a little more work to do!" Katie said as she giggled and patted my gaping asshole. "Pick him up, big boy."

The black stud hooked his hands underneath my knees from behind and picked me up easily, leaving me limp like a ragdoll hanging from his arms. My locked cock dangled down helplessly as Katie used the back of one finger to lift the Bull's cock vertically and lined up with my ass. The Bull lowered me down onto his cock and I moaned out loud.

"Uuunnnnnhhhhhhhh," I uttered as I felt my asshole stretch around the girth of the big black dick I was impaled upon. There was no escape as he slowly lifted me up and down, fucking me on his dick and acting as though I weighed nothing.

He then looped his arms through behind my knees at his elbows and wrapped his hands from there behind my head and locked them, resulting in a full nelson of sorts, and forcing my gaze down to look at his huge cock pistoning in and out of my asshole as my sissy cock bounced up and down to the rhythm of his thrusts. Katie knelt down and stuck her tongue out wide. She broadly licked the Bull's balls, causing him to groan palpably - I felt the vibrations of his voice in his chest against my back. She sucked one of his balls partially in her mouth (she couldn't fit all of one in as they were swollen and full of black cum), and a loud smacking "pop" sound echoed through the room as she released it from her full lips.

He fucked me deeply, until the base of his cock sunk into my ass with every stroke, and his heavy balls bounced up and struck my little locked ones. The outline of his cock could even be seen in and out through my stomach as his cock reached the depths of my ass. My eyes at this point were losing focus as I leaked uncontrollably from the tip of my locked sissy cock.

Finally after almost ten minutes of hard fucking hanging from his arms, he lifted me completely off of his thick dick and Katie grabbed it by the base. She looked my directly in the eyes, opened her mouth and went down on that big black cock, her lips stretched to wrap around it completely. She didn't stop until she was almost 9 inches down, near the base, and she gagged deeply and her thick spit escaped from around her lips. She forced herself deeper and got within half an inch of the balls but couldn't make it and drew back, gasping for air as his big dick dripped her thick saliva and tears streamed from her eyes.

"Well I think you're good and broken in now, sissy." Katie said as she tickled my balls with her fingertips and pushed down on my prostate with her fingers in my asshole. The precum came streaming out of my cage as my cock pulsated. "I think it's time to get in my favorite position now."

She instructed me to lay on my back, then flipped my legs back so that my ankles were next to my ears and tucked a firm pillow under my lower back to keep me from flipping back. She pulled our soft cuffs from under the bed where they were connected to the bed's legs and tied my ankles in that position with my stockinged legs back.

The Bull stood over me and she briefly slurped on the head of his cock, a mixture of her saliva and his precum dripping down and hitting me in the face as I whimpered meekly. Her tongue lolled over and around the head until it was dripping and ready.

The Bull lined up his cock, which was now as hard as a steel girder, with my gaping asshole. He drove it in swiftly and began to fuck me without mercy. My own precum was surging from my prostate and balls and dripping (as Katie made sure of) from my cage into my mouth. Katie pulled the new cordless Hitachi wand from the drawer of our bedside table and flipped the switch. It hummed to life as the big black dick piledrove my asshole fucking me like a machine.

Katie barely touched the Hitachi to the head of my cock through the cock cage and instantly I went from cock drunk to a cock frenzy. My cock, balls, prostate, and asshole felt like they were one huge bundle of nerve fibers connected from Hitachi to black dick. The Bull hammered my ass harder as I desperately begged, "Please fuck my sissy pussy harder!" SLAP SLAP "Fuck me!" SLAP "Fuck me!" SLAP "Fuck me!" SLAP "Fuck!" SLAP "Me!" SLAP "Fuck!" SLAP "Me!" SLAP "Fuck!" SLAP "Meeeeeeeeeeeee!"

And with that my asshole and cock convulsed together, rope after rope of hot cum dripping from my cock cage to my open mouth and all over my face. Katie laughed as the Bull kept fucking me as my asshole squeezed tighter around the black cock but gaped in between thrusts. The noises made by my asshole and his cock were lewd and obscene, and Katie loved it. The Bull was breathing faster, then grabbed my ass cheeks and fucked me deeply as he released his huge load into my used sissy asshole. He came for at least a full minute, filling my asshole with pump after pump of hot cum from his full black balls.

When he pulled out, Katie peered into my ass and smirked again as she said, "Push out that load you slutty little pussy boy! I want you to taste every drop of that Bull's cum, and don't you waste any or I'll spank your little ass red!"

She stroked my tight emptied balls with her manicured fingertips again as I uncontrollably squeezed my ass and the hot cum came running down my perineum and over my balls, falling straight into my open mouth. The bull's load was at least three times as much volume as my own, and I literally had to gulp it down to keep it from spilling out of my mouth. His load was salty and thick as it slid down my throat.

Katie gave my cheek a slap and said, "Good sissy, now we'll have to use that sissy pussy every Friday night! I hear our new friend here has more than a few colleagues who would be interested in joining our get togethers! Now get some sleep while I walk our Bull to the door, I'll be back to snuggle you soon!"


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by Anonymous

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by garter200010/13/18


Sissy dolled up in pink lingerie... Chastity ... leaking sissy cream.... my favorite sissy story

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by zazrix909/15/18

Wish my wife

was that GGG, and could find an 11 inch cock to ravage my ass to super pleasure.

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by Anonymous02/20/18

I was pinching my sissy clit

And also came. Now I have a wet sticky spot on my chair that I have to suck out. I need to be gaped 4yourpleasureiam

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