tagTranssexuals & CrossdressersPleasure from Pleasure Ch. 02

Pleasure from Pleasure Ch. 02


Chapter 2: Whores

Helping someone fulfill themselves the way that I had didn't mean that I lost my own desires. There were things that had to be done and though I had my new project, there was still the starvation that lived in my heart to feel someone scream with pleasure. That meant trolling and fortunately, I found the right person from my past to fulfill me.

We reconnected online through a personal ad page. I recognized his information and when he wrote back, I was absolutely thrilled to see that he recalled me too. He gave me the go ahead to visit his house on Friday night for a little role play, the kind that beat all normal forms of foreplay.

I dressed at home, going with a slutty French maid look. The collar was white and lacy over the black of the dress, butting at my throat and slit to just below my bust, giving an ample view of cleavage. The skirt was short and pleated, barely covering my ass and if I moved just right, one could easily see the goods.

My panties were white satin with lace around the top. I tucked my cock neatly between my legs, and pulled them on. They were a touch too small which helped keep everything in place. The pull of my skin at my abdomen was totally natural now, a little stretch of flesh that I had come to really love the feel of. It was a physical reminder of who I really was.

Black stockings crawled up to my thighs with a seam in the back and stay up tops. No garter belt this time, but with the skirt as short as it was, plenty of white skin was perfectly visible. My heels were six inches, strapped on over the tops and around my ankles with silver buckles.

A white apron completed the outfit, short and frilly it was just for show, a way to break up the black and reinforce what I was pretending to be.

I layered on the makeup, not in a subtle way that I might've used to go out and about in the day but full on whore; dark eye shadow, bright red lipstick, a little too much blush...I did my hair up in a bun and secured it with a white ribbon and couldn't help but smile at myself in the mirror. If this guy didn't pop an erection when he saw me, then his dick didn't work anymore.

As a little enhancement to my own excitement, I didn't drive to his house myself but took a cab. I should've been concerned that the driver couldn't stop looking at me rather than watch the road but his gawking turned me on. By the time we arrived at my date's house, I was so aroused I thought I might feint when I got out of the car.

The way the air touched my thighs, chilled the satin surrounding my cock, reminding me that I was wearing hardly anything at all down there...it was enough to make me flush with desire. It took all my willpower not to reach down and touch myself as I sauntered up to the door and knocked.

Xavier, my old lover was a handsome man with short, thick graying hair and strong manly features. His chin was broad, his eyes were crowned with thin brows, he wore a goatee that matched his hair and seemed quite severe until he was in the throes of passion.

He was athletic, dressed fantastically in gorgeous suits, his choice that evening was a black pinstripe with a white shirt and red tie. He looked me up and down and the slightest smile tickled his lips. The twinkle in his eye told me he was pleased and without a word, he motioned me to step inside.

We went together to his living room where he sat in a leather recliner. "Pick up." He spoke with so much authority, it thrilled me to the very core. The place was far from a mess, he had a real maid come through to ensure that but the coffee table had some things out of place and it was just low enough that I'd have to bend over...I loved the way he thought.

I stood with my back to him and bent at the waist, moving his items around the table without any thought to what I was doing. My vision was tunneled from my own excitement, especially when I heard him grunt appreciatively.

His warm fingers tickled my ass cheek, petting me down my thigh. Through my stockings, it was pure heaven. He reminded me I was wearing them. When he cupped my cock and balls without warning, I gasped and stiffened, trying to will my cock to remain soft...a futility.

"I know that you want me," he said. "Get these panties off and do what you have to so you can ride me."

I brought lube in my purse. I dropped the panties and kicked them away, finding the tube of KY and liberally applying it, sticking my fingers into my smooth ass while he watched. I made a game of it, fingering myself like it was a real pussy, plunging them in. I remembered when I didn't have so much practice putting things in my ass, when it was difficult to relax enough to make it happen. Now, I was practically a professional and I could guarantee that the second he was stiff, I could split myself on his shaft.

When I turned to look at him, he had his penis out, stroking it at its full attention. I stepped forward, put my knees on either side of his lap and poised for penetration. He removed his hand and relaxed both his arms on the chair, looking up at my face. This was my cue to guide him into me, to place the spongy head of his cock at the entrance of my body and push....

His cock was hot in my hand and I could feel the heat against me. The anticipation of that being inside me, of filling me up completely made me sigh and that one gesture was enough to settle down and bring him in.

He stiffened and let out a long breath, relaxing as I did the word. It took me three good pushes to get his entire width inside me, working through the initial pain and discomfort until it became ultimately pleasurable. Our eyes were locked as I began a slow grind, a rhythm that kept him inside my ass as deep as I could manage while flexing my muscles around him, milking the lust from him.

"Yeah, like that..." he muttered. "Keep it up...you teasing little slut...you're such a fucking whore, Jesus Christ!"

His talk filled my soul with as much passion as his hard dick filled my hole. Every second he seemed to get bigger inside me, a real man having me debase myself, submit myself to his designs, his needs, his pleasure. This concept unto itself was enough to get my cock stiff but the only friction it received was the tickle of his shirt against my shaft and the occasional brush on the head against fabric.

"Faster you fucking bitch!" He cried, balling his fists. There had been times that he'd grab my hips and fuck me properly but tonight, he wanted no contact, passive orgasm through me. "Don't stop til I'm screaming!"

I picked up the pace, my thighs burning with the motion, my stomach feeling as if I'd done fifty crunches. I didn't stop, didn't allow my physical discomfort to get in the way of the rapture that encased me like an aura. He started to grunt, holding the leather of his seat while I fucked the living shit out of him. I knew he was close and I remembered something he really loved...

Just seconds before I thought he might lose his load, I reached behind me and grabbed his balls tightly in my hand, squeezing as I bounced on him. The motion pulled on them, driving him absolutely wild. He lost control, grabbing my hips and screaming out as he began coating my ass with his cum, spraying massive gobs. the pressure seemed to build in my stomach, and I let out a long moan from how thick he'd seemed to get.

We kissed, hard and passionately, our tongues mingling as I road him slower to completion.

When we were all done, and the panting ceased, we took a break but there was much more sex to be had. He fucked me three more times that night, cumming on my chest, face and feet. Three hours later, I was a mess but he had me put on the dress, leave the panties and get the fuck out.

I left, debased and looking like I had been gang banged by a dozen bikers. This was how I felt alive, this was what made me feel sexually gratified. I had an indirect orgasm through it all but nothing as powerful as with my little sissy. This wasn't necessarily better, it was just different and this kind of different I would never give up.

Still, it all gave me a fantastic idea. When I got home, my plans suddenly fell into place and I was ready for my next adventure with my protege. If he was ready for the next level, I was ready to take him there.


Xavier was a good sport, especially when it came to his enjoyment. I wanted him to be involved with my next little outing, bringing my sissy to another level that would possibly stretch his boundaries. There was something that I thought he should definitely try, especially if he truly wanted to be like me. For that, I needed Xavier's strong touch.

I sent my sissy a list of all the things he needed to do before he came over and the information I needed to prepare him. I had him send me his clothing sizes and ordered him to remove all his body hair from the face down, even if that required some waxing. He was to shave the day he was coming over and I set that date out three weeks.

This allowed me to procure the proper fitting outfit for him for our next adventure which was laid out nicely on my bed when he arrived.

When he stepped inside, he was wearing a pair of jeans, a tee shirt and some white tennis shoes. He was cleanly shaved on the face and hadn't missed any spots. Fortunately for him, he was blond and there was no stubble or dark patches to worry about.

I tossed him a garbage sack. "Take everything off and throw it all in the bag."

"What? All of it?"

"To your bare ass and don't you dare make me repeat myself." I could tell that my words turned him on, the way he flushed and the way his eyes gleamed.

I dressed in a black evening gown, sleeveless with a slit up the right side to my hip. The top swept down to expose plenty of cleavage and my breasts were more than ample enough to hold it up. The back was exposed to my waist and I wore a pearl choker.

Beneath the skirt, my stockings were black and my shoes, another pair of six inch heels, were slip ons this time. I crossed my legs and watched him, putting on my best impatient expression that I had seen in tops so many times in the past.

He kicked off the shoes and socks then went for the shirt. His hands were shaking as he unbuttoned his pants and dropped them to the floor. He hadn't been wearing any underwear and he covered up his cock with his palms, head bowed bashfully.

"You're a dirty little slut," I said. "Not wearing any panties...for shame. Get your sorry ass over here so I can inspect you and make sure you followed my orders. And why the fuck are you covering anything up? Hands behind your back, wrist on wrist! Jesus Christ, what the hell am I dealing with here?"

"I'm sorry!" He spoke quickly, stepping closer so quickly that he nearly stumbled.

"You're sorry what?"

"I'm sorry, Ma'am," he replied quietly, putting his hands behind his back.

"You'll get there I suppose." I turned my attention to his body, running a hand along his smooth chest and stomach down to his bare abdomen. I lifted his cock, holding his head tightly between my forefinger and thumb so I could really scrutinize his balls. I prodded them, moving them around and grinding my palm against his scrotum to feel for any hair at all.

He was totally smooth.

"I'm very impressed," I said. "Did you have someone help?"

"No." He replied. "It took hours though..."

I tapped his hip and he turned. I couldn't help but smile that he was learning so quickly.

"Bend over at the waist." He complied and I spread his ass cheeks, getting a good look at his puckered hole. Even this was void of hair and he'd taken great care, making sure to not injure the goods. His legs were hairless, his feet smooth...my sissy had earned a reward. "Very very impressive, darling. Get on your knees and kiss my shoes...like they are a long lost lover."

He turned, descended to his knees and, keeping his hands behind his back, leaned down to caress the leather of my shoes with his lips. I watched, feeling my heart flutter as his tongue traced the lines of the seams, caressing my heel and the bottom of my shoe.

This went on for several moments as he sucked and kissed every inch of my left heel and I finally tapped him on the head.

"Enough of that, we have somewhere to be tonight, whore."

He looked up nervously. "We're...going out?"

"To a friend's house," I replied. "Your outfit is on the bed. Get dressed quickly so we can do your makeup before we leave."

I had procured his clothes online, the most whorish shit I could come up with. A tight red knit dress with long sleeves but so short it would never cover up his ass no matter how many times he pulled it down, a red lace thong, a pair of four inch reed heels and red stockings.

When he came out, he had gotten them all on okay but as I suspected, he kept trying to pull the skirt down to cover the bottom of his ass and not show off some of his crotch. "It's never going to work," I said. "A fucking whore has goods to sell and you can't sell them if they're hidden. Get over here so I can properly tuck you up."

He came closer, wobbling on the heels. I adjusted his panties and really reefed on his cock to get it firmly between his legs. "Pretend its a tail and it'll help you remember how submissive you are. Makeup is next so have a seat over there."

I layered it on thicker than I had when I slutted up for Xavier the other night. Bright red lipstick, cheap looking shadow and a ton of blush, enough make up to ensure he looked like a serious drag queen. When I was done, I took a picture and it made him look away, embarrassed.

"Oh, this isn't the last photo of our evening."

"I'm not really...comfortable..."

"With the photos?" He shook his head. "Tough shit. You're my sissy now and if I want a documented record of your progress then that's what happens. Unless you want to get the fuck out and never come back?'

He shook his head again.

"Good, then we have someplace to be. Let's go."

This time, I drove us to Xavier's house, mostly so that my newfound property could be a little comfortable. I figured that public exposure could come later because tonight might be a little overwhelming. Xavier knew that I was taking lead this time so when I knocked, he stowed the dominant stuff. He grinned at my sissy and led us into the bedroom.

We needed a bed for my plan.

"I like the dress," Xavier said to me. "It looks elegant."

"You should see what's underneath." I shrugged off the top and let the whole affair fall to the floor. I wasn't wearing a bra and my black lace panties gripped my ass tightly. I'd used a garter belt this time with my panties on the outside. Slipping them off, I smiled at Xavier. "How would you feel about fucking my pussy, baby?"

"I'm a little dry for that."

I glanced at my sissy. "You heard the man, bitch. Get him nice and wet."

This was the moment I was waiting for, the challenge. It's all well and good to suck off a person who looks like a woman but Xavier was a true and obvious man. He had a goatee, his pubic hair was thick and black, and he had that musky male scent that drove me totally wild.

My sissy seemed to hesitate and I gave him a dark look.

"On your knees," Xavier said to him. "Now."

I couldn't help but smile as he complied, crawling closer to Xavier as he undid his pants and revealed his half limp penis. "You ready for a real piece?"

"Yes, sir." God, she learned so fast!

"Then get the fuck to it."

I watched as Xavier's cock touched her lips and she moved her head back and forth to tease him. I watched curiously to see her technique, intrigued as she lashed out with her tongue and coated the spongy head with spit. Xavier hummed with appreciation as she took him inside her, reaching up to hold the shaft gently.

Plunging down, she took in a little more of him each time, even as he began to get harder and larger. I leaned down and offered encouragement through a whisper, telling her to relax her throat, to deep through him and get him nice and wet.

"Be a good whore," I purred. "Make yourself useful for something."

My sissy finally got him all the way in, her lips touching his pelvis before she pulled back out. Spit coated her lips and chin and Xavier was soaked.

"Watch us carefully," I said, crawling on the bed doggy style. "From your knees."

She moved to the foot of the bed, watching as Xavier saddled up behind me and, without preamble, guided himself right into my ass. I threw my head back as he began to really fuck the shit out of me, moving from entry to hard rhythm in seconds. Apparently, my sissy really turned him the fuck on because he rarely dove in with such zeal.

I began to grunt and moan from the assault, barely able to contain myself. Even as wet as his cock was, I had been dry and he was loving every second of fucking me like that. It equaled out after a while but I was going to be sore in the morning. That prospect was less fun than the moment but I couldn't help but get into it, plunging back on him.

He held my hips so tight I thought I might bruise. Every thrust made me yelp and he began to grunt, practically growling until I could tell he was on the verge of coming. It was right there...the swelling of his penis head, the shaft tightening around me. I didn't even have it in me to milk him, I was too busy being fucked to think.

When he came, I cried out too, a loud moan that came from so many parts of me, I couldn't even begin to decide which took precedence. Spiritually because I'd been used and my sissy was watching...the voyeuristic part made me shiver...physically because I loved having a cock in my ass...mentally because I knew the scene had to look hot...it was all so much....

Xavier pulled out and I snapped my fingers.

"Get your tongue in my ass!" I cried. "Don't let any of his cum go to waste!"

Another command my sissy had no idea was coming but to her credit, she moved into position as swiftly as she could in those heels and plunged her tongue deep into my ass. The immediate relief of her cool, wetness in my hole made me sigh and as she continued to tongue me, eating me out and sucking up Xavier's cum, I felt like I might be satisfied as well.

"Oh, wank me," I moaned. "Fucking put your hand on my cock and wank me!"

She complied, tugging my penis while keeping her face buried in my ass. I twitched and moaned, freaking out as Xavier came around and kissed me hard on the lips. It was a deep French kiss, his tongue in my mouth making it hard to breathe and that sent me over the edge. I spurted cum all over his bed, moaning loudly into his mouth, returning his vigor with my own, starved desire.

When I finished, I shifted to bat my sissy's hand away. She had finished getting all the cum out of my ass and I moved aside, motioning to the stain. She wiped her lips, thoughtful of what lipstick remained before cleaning that part up as well, going so far as to suck on the sheets to get the cum out.

"She's a good one," Xavier said. "Great at sucking cock...great at eating you out...great at cleaning. Think you can maid her up?"

"Oh, definitely," I smiled. "But won't you give her a little cash? A whore should get paid, don't you think?"

"She's still new." Xavier went over to his dresser and took out his wallet. He tossed her a ten. "I say you make her take a cab home."

"Maybe next time," I said, noting my sissy's horrified expression. "Right now, I think we all might need another round, don't you think?"

Xavier gripped his cock and stroked it back to an erection. "I think that I've got a few more places I could put this, sure."

That night was going to be a wild ride. My sissy might never be the same. But then again, that was sort of the point, wasn't it? That's why she came to me and we made a deal and when I make a promise, I like to deliver.

She was going to learn that in spades.

Report Story

bydarkestnight© 3 comments/ 33563 views/ 3 favorites

Share the love

Also in this series

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartCadian122, 1qaz2 and 1 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (3 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (3)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: