Saturday, June 13, 2020

The Absolutely, Positively True Story of Chrissy, part 5: Chrissy Goes Deeper

This is the story of my sissy journey that got me to where I am now. If you're just now joining the fun, it would be a shame if you missed parts one, two, three, and four.

Part 4 left off after a particularly fun time lingerie shopping (as well as a post-script of getting busted wearing lingerie by my ex-wife and her new husband.) Sometime around part 4 or 5 is when I also started this blog and began making sissy captions.

Shortly after my divorce I started seeing someone. Because of a lot of circumstances, we were off and on (and off and on and...) When we were actually together we were good together (and the sex was amazing!), and when we were broken up I spent more time going down the sissy rabbit hole. My spare bedroom closet began to fill with dresses, and corsets, and costumes, and stockings, and heels, and oops! Chrissy had to spill over into the second spare closet. If any of my friends had been the least bit nosy and opened either closet door my little secret would have quite literally been out of the closet!

Around this time I played around with a little phone sex domination and a couple of escorts who were willing to dress me up in person. I wasn't living as a woman full time (nor did I want to), but any time not spent at work was usually spent dressing up and playing online.

This was one of the favorites!

I still had an account on the BDSM dating website and eventually met Bud. Bud loved sissies and loved to go to the local gloryholes to get sucked off by sissies. Eventually we made plans to meet up... at my place. Like I said, my "bachelor pad" was secluded and private without any neighbors. In retrospect I know what a bad idea it was to invite this stranger to my home, but the thought of being his little sissy bitch overwhelmed my better judgment.

It worked out with our schedules that he was able to come over on a random weekday afternoon. I had taken the day off from work to have enough time to get ready. I shaved my intimate areas, and I shaved the upper parts of my thighs so that I would be hairless except for the part of my legs that would be covered by thigh highs. (I was afraid to shave my legs completely in case someone would notice when I wore shorts.) I did my best to follow an online "pornstar makeup" tutorial (I'm sure I looked ridiculous) and I put on my french maid costume,  a blonde shoulder length wig, black thigh highs with little white bows, and pink high heels.

It was this exact French Maid costume (with pink heels)

Bud found my secluded apartment and texted from the parking lot. "Ready yet, slut?"

"Yes, sir. Come on up."

A moment later there was a knock at the door. My hands trembled as I unlocked it and stood behind the door, using it as a shield. He stepped in and shut the door behind him, leaving me exposed to the relative stranger standing in my living room.

"Nice," he said, looking me up and down. "You are a hot little sissy, aren't you?"

Bud was bald and a little shorter than me normally - with my 5" heels I was much taller. He stepped toward me and grunted a little, clearly enjoying what he was seeing.

He began to grope me, grabbing my ass, running his hand up and down my thighs, and lifting my skirt all while rubbing his crotch through his jeans. I was a piece of meat to him and he was busy inspecting the goods.

"Bend over," he said as he pushed on my shoulder, barely giving me time to comply before he was going to make me do what he demanded. I bent over at the waist, sticking my ass up in the air. He grabbed and squeezed and then put his hands on my hips, grinding his hardening cock against my pantied ass.

"Come here," he said as he pulled me towards the couch. He pulled a digital camera out of his pocket and began to snap pictures, posing me like his own personal sex doll.

When he had all the pics he wanted, he unbuckled his belt, unzipped his fly and let his jeans fall to the floor. His cock was about 6" long and straining against the fabric of his boxers. He took my hand and slid it under his waistband. I wrapped my fingers around his cock and it jumped at my touch. He pulled me closer and leaned it to kiss me. He held the back of my head while his tongue roughly probed my mouth. This was not a romantic kiss but rather his way of laying claim to property, and my clitty grew hard in my panties at the thought of being owned.

He let go of the back of my head and began to push me down. "On your knees, slut. Suck it. Suck my dick, whore." The name calling and manhandling made my head light as I dropped to my knees in front of him. He pulled his cock out over the top of his waistband and pushed it towards my mouth as I got to my knees.

I took his cock in my hand and kissed the head, his precum making my lips slick. I slowly licked the underside of the tip flicking my tongue over the end of it. I then began to lick slow circles around the head as he let a soft moan escape from his mouth. "Mmmm that's it, slut. Tease my cock."

I wrapped my lips around the head of his cock and swirled my tongue around a few times. He put his hand on my head and began to push more of his dick into my mouth. I took it as much as I could like I had practiced so many times with my toys. He slowly pumped in and out of my mouth, telling me what a good little cocksucker I was as he worked more and more of his shaft into my mouth.

"Are you a tease or are you a good cocksucking whore?" he asked as he pulled down his boxers and stepped out of his jeans, leaving him naked from the waist down. My only answer was a moan around his cock as he kept pumping. "Huh? What are you? Say it, bitch." He stopped pumping and pulled his cock out of my mouth, turning my head to face him.

"Tell me what you are."

I hesitated for a second as he stroked himself with one hand and held my head with the other.

"Say it."

"I'm a cocksucking whore."

"Who's cocksucking whore?"

"I'm your cocksucking whore."

"That's right. Now prove it." In one smooth motion he guided his cock back into my mouth and pulled my head down, driving his dick all the way down my throat and pressing my face against his pubic hair. I immediately began to gag and my arms flailed uselessly as I suddenly struggled for air. He pulled all the way out again and as I caught my breath he slammed into my mouth balls deep again, gagging once more.

He pulled back again, leaving just the tip in my mouth.

"Look at me, slut. Look at me while I fuck your face."

I looked up at him only to find out I hadn't noticed him pick his camera back up off the back of the couch. CLICK!

I had been able to hide my face in the other pics he took, but there was no hiding now. He pumped in and out of my mouth, pausing occasionally to take another picture or get a better grip on my head. His groans became louder and his pumping faster. He dropped the camera again so he had both hands free to hold my head.

"Oh, yeah. Fuck yeah, you little slut."

He had to be getting close.

"Oh shit. I've got a big load for you - been saving up for days."

All I could do was moan my approval and shake my head yes as this stranger's balls bounced off of my chin.

"Fuck! Yes! Ah FUCK!"

He stopped fucking my mouth and held my head in a death grip as I felt the first wave splash on my tongue and down my throat. He continued to pump load after load of hot cum into my mouth and as hard as I tried I couldn't keep up. His cum ran down my chin and neck and made the fabric of my maid uniform stick to my chest. When he was done emptying his balls into his little cocksucker he pulled out and smeared the cum on my chin around my face with his cock. I finished swallowing what was in my mouth and started to wipe the cum from my face and neck.

"What the fuck are you doing? I put my cum there for a reason. Leave it. You got any beer?"

"Um, yes, sir."

"Then go get me a beer, slut," he demanded as he spanked me on the ass and collapsed on the couch. I assumed I would just give him a blowjob and he would leave but it appeared he was staying for a while. I brought him a beer and he told me to sit next to him on the couch. I sat down and he let his hands roam all over me. As he drank his beer he stroked my clitty through the fabric of my panties and continued to eye me like a piece of meat.

After 15 minutes or so, he very bluntly demanded "Lick my balls."

I paused. Dressing up in lingerie and pretending to be a girl was fun. I even enjoyed giving this man a blowjob and liked the feel of his cock in my mouth. But I had never signed up for licking anyone's hairy balls. Just... ewww... no. The thought had never even crossed my mind.

He pushed me to my knees again as he stood up over me, stroking his cock. He held my head again as he stroked his cock and lowered his balls onto my face. They had a slightly musky odor - not dirty, but also not fresh from the shower.

I wanted to tell him no but he was clearly in charge. I took one and then the other into my mouth while he stroked himself over me. This was a part of being a sissy that I truly didn't like, but the fact that I was completely submissive and not in control was also a huge turn-on. Soon he was hard again and had me alternating between sucking his balls and sucking his dick.

He worked faster this time, stroking hard and fast while I licked and sucked his balls. He slid into my mouth again and began to drive his cock into my throat, making me gag and getting his cock sloppy wet with my saliva. As his pumps, strokes, and grunts became more desperate he pulled out of mouth and stroked his cock over my face.

"Oh, shit. You ready for this, slut? I'm gonna paint your face. Beg for it. Beg me to cum on your pretty little sissy face."

"Yes, sir. Please cum on my face."

"What do you want, whore? Tell me want you want."

"I want you to cum on my face. Please."

"Louder, slut. What do you want?"

After years of jerking off to porn and always fantasizing about giving some hot girl a facial, the realization that I was about to get a facial broke something in my brain. I didn't just want this, I craved it down deep inside and had to have it. I was willing to do anything for this.

"Please please please. PLEASE cum on my face. Please, sir, please."

The wanton urgency in my voice must have done the trick because he began to unload all over my face.

"Please, sir, I want your cum. I want it on my face. Please, please cum on my face."

When he had finished unloading, he pressed his cock to my lips and I licked the last bits of cum from the head, gently sucking to get every last bit of his cum. Then I let it fall out my mouth and onto my chin.

"Damn, you really are a whore, aren't you?" he chuckled as he got dressed. I stood up to see him out the door, and he grabbed my ass one last time. "Next time, I'm gonna fuck that little sissy ass, understand?"

"Yes, sir."

He left, and this time, instead of even attempting to clean up, I left his cum right where it was. I looked in the mirror and looking back at me was a trashy used whore. I liked what I saw.

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