A Weekend Away Ch. 04

Story Info
Sissy's training continues and she has her first outing.
2.9k words
4.61
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16

Part 4 of the 4 part series

Updated 06/10/2023
Created 07/28/2020
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"Morning slut! Time to rise and whore!"

I woke to the sound of Sydney's voice and the curtains being opened. The light flooded the room and made me flinch. As I rolled over I could feel my panties pull at my skin, stuck to my ass after Dave's cum dried in them overnight. My wig was askew on my head and I could only imagine what my makeup looked like.

"We've got a very full day today and no time to lose. Lose the wig and then you've got 10 minutes to shower. I'll put your clothes on the bed."

As soon as she had come Sydney went, and left me alone with my thoughts. I began to daydream about what the day might hold, what sexy adventures lay in front of me when I heard Sydney's heels clicking down the hall.

"Nine minutes!" she shouted from the hall and I knew better than to keep her waiting.

I caught site of myself in the bathroom mirror, and I looked like I had been rode hard and put away wet because, well, I had been rode hard and put away wet. I stripped off my panties, stockings and collar, showered quickly and scrubbed off the remnants of yesterday's makeup. The water pouring over my breastforms was a new sensation and made showering both an adventure and a distraction. When I got out of the shower I found on the bed a pink satin thong, a pair of white thigh highs with a white garter belt, and a red and white polka dot dress. There was a cute little pair of 3" mules on the floor, with little puffs of pink maribou across the strap. She had also left a short black bobbed wig.

As I finished getting dressed Sydney returned and put the collar back around my neck, once again clipping the leash to it. She led me from my room to the dining room for breakfast. After that the morning was a blur. Sissy lessons and practice in the study, makeup and wig lessons in the salon, feminine voice lessons that ended with an exam (I had to be a phone sex operator without the men realizing I was not a woman) and finally more sissy practice.

By the time I got to lunch I was ready for a break but it didn't look like the pace of the day was going to lighten up. Yvette served pasta for lunch - Sydney said I should carb-load because I would "need my energy." As we were finishing lunch Sydney turned to me and laid out our next steps.

"After lunch I have some business to attend to, but you will return to the salon to get ready for your afternoon adventure. Once the girls have you ready, meet Dave and Roger in the foyer. Don't keep them waiting. Oh, and Chrissy? Remember that bad things happen to nosy sissies. I'd hate to accidentally send a certain text message."

I shoveled down a little more pasta and then excused myself from the table. This was my first time in the house alone, and as much as my curiosity made me want to explore a little I had heard Sydney's warning loud and clear. I reported to the salon and Miss Janet and Miss Cathy were already there. Miss Janet removed the collar and helped me out of my dress. Miss Cathy removed my wig and touched up my make-up. Miss Janet began to gingerly remove my breast forms and once all of the adhesive was off she applied a light coat of baby powder. I couldn't imagine that I would spend my afternoon as my normal flat-chested self, but it was nice to be free of the weight of those giant tits for a few minutes. Perhaps I had underestimated just how much of a burden fabulous tits could be.

Miss Janet turned back to the counter and it suddenly made sense; she produced a silicone breast plate - the kind that has the breasts built in and covers you from the neck down to middle of the rib cage. It took both ladies to wiggle me into the contraption and when they finally got everything in place I discovered that my newest breasts were even more bimbotastic than the last ones. If the last ones had been D or even DD, these were... well significantly larger. The breast plate was cold at first and made my nipples stand at attention but soon warmed to my body temperature. Miss Cathy applied a little make-up to the breast plate to blend it to my natural skin color. The ladies helped me to my feet and I was surprised at the weight of my new accessory - it took me a moment to find my balance.

"Umm, so why the breast plate instead of the breastforms?" I asked Miss Janet.

"Ha! You're adorable, sissy. Always fishing for information. Suffice it to say that the breast plate will work out better with your outfits and assignments for the day," she replied with a wink.

Outfits? Assignments? Plural? Apparently I would "need my energy" today.

Miss Janet produced a pink floral print dress and slid it over my head. It was low cut, exposing cleavage almost to the bottom of my breasts which were straining to break free from the fabric. Clearly the breastforms wouldn't have worked with this dress. The waist was form-fitting which hid the bottom seam of the breast plate, and below the empire waist it flared out, just grazing the tops of my thigh highs and guaranteeing that the slightest movement would put my garters on full display. Janet zipped me up in the back and handed me a pair of ankle high brown boots with 5" heels. Cathy took a blonde wig from a head form and secured it to my head. This one was more platinum than the first wig and definitely had a more bimbo vibe to it.

"Okay, I think that'll do. Let's get you in those boots and then you're ready to go!" Janet smiled, clearly proud of her work. I needed help from the ladies to steady myself and get the boots on as my new found assets up top made balancing a whole new challenge. Janet handed me a little pink purse that was shaped like a corset. "There's everything you'll need to touch up your makeup and wig in the bag, along with some breath mints and wet wipes. You're good to go! Have fun, slut!"

I made my way from the salon to the foyer, struggling to maintain my balance while remembering everything Sydney had taught me about walking like a bimbo. I'm fairly certain that the sway of my tits mixed with my unsteady gait made me quite a sight as I stepped into the foyer and found Roger and Dave waiting for me.

"Nice! You look like a proper cocksucking bimbo now! You're gonna be a big hit at the..." Dave yelled.

"Dude! Don't ruin the surprise," Roger stopped him mid-sentence.

"Right. Yeah. My bad."

Dave removed the leash from my collar and replaced it with a short length of chain, padlocking it to my collar. I thought that that probably didn't bode well but before I could say anything Dave was yanking me out the front door towards the waiting SUV. He opened the back door and helped me in while Roger climbed into the driver seat.

We drove in silence until we arrived in an industrial area at the edge of town and pulled into a parking lot with a chain link fence. I instantly recognized it as an adult store I had frequented many times, both dressed as Chrissy and as a man. They had a boutique with lingerie, adult movies, and sex toys, video viewing booths on one side of the building, and an adult theater on the other side. I had never ventured into the theater before, but I knew the video viewing booths well.

Dave led me by the chain across the parking lot, the only sounds were my heels clicking on the pavement and a few semi-trucks idling in the lot. It took a moment for my eyes to adjust from the bright daylight to the dim interior lighting, but when they did I was shocked at how busy it was. I'd been here many times and at many different times of day but I had never seen so many men milling about the boutique. Normally there'd be a few men browsing the adult movies, maybe a woman with her man picking out a new sex toy, even the occasional group of women shopping for bachelorette party supplies. But this was 15-20 men, all spaced out around the boutique and the second I was able to clearly see I could tell they were all looking at me.

I stepped into the boutique, led by Dave, as Roger made his way to the counter.

"Hey. What's going on? Viewing booths, please," I heard Roger tell the woman at the counter as he handed over some cash.

"Back again, huh?" she replied. "This one's kinda cute. Slutty-looking, but cute."

They both laughed as Dave led me further into the boutique.

"Hey, sissy, how much is that dildo down there?" Dave asked, as he pointed to a dildo sitting on a corner shelf all the way down by the floor. I knew what he was up to - bending over for his little price check was going to cause my short dress to ride up and expose my garters and possibly my pink thong to the waiting crowd. Figuring there was no way out of it I gave the men in the boutique a good show as I bent at the waist, wiggled my hips a little and spent more time than necessary looking for the price.

"$59.99, sir," I told Dave as I straightened up. He led me up and down the aisles, pretending to browse, and as we walked by each man they began to become more bold. At first they just stared, but soon I was having trouble following Dave as the men began to grope me. Stray hands ran up under my skirt, roughly grabbed at my tits, and clawed at my dress. One man grabbed my hand and put it on his crotch, his erection growing in my hand. I was becoming overwhelmed but also very turned on.

"Time to take this a little more private," Roger called out as he flashed a pair of the cards used to access the private viewing booths. Dave led me through the closing crowd and into the private viewing booth area. He showed me to a corner booth near the door and pushed me inside as Roger went into the booth next to it. There were 2 large gloryholes (about the size of a dinner plate) - one on my left and one on the right with a video monitor mounted up in the corner. Dave dropped the end of the chain through the gloryhole on my left - the booth that Roger had stepped into, and used the access card to start playing porn on the video monitor. It was hard to hear over the sound of the woman squealing on the video screen, but I thought I heard a padlock snap shut.

Dave sat down on the bench in the corner and as I watched the beautiful blonde bimbo getting spit-roasted on the screen in front of me I tugged slightly on the chain attached to my collar. It didn't budge. I pulled harder only to realize that I was indeed padlocked to the inside of the booth next to me. No escaping now, I guess.

A moment later a half-hard dick poked through the hole on my left and I was on it instantly. I dropped to me knees and took the cock in my mouth, swirling my tongue around the head. After all of the practicing, studying, and talking about it all morning I guess I was more eager for cock than I thought. The random stranger began to get harder and I could feel him filling up my mouth. I licked up and down his shaft and began to bob up and down while stroking the base with my hand. He pumped in and out of my mouth slowly fucking my face as I took more and more of his dick in my mouth. I could see the other gloryhole out of the corner of my eye and could make out the shape of a decent beer belly above a smaller cock. I reached up to stroke him while sucking the cock in my mouth for all I was worth.

The man in my mouth pumped faster while keeping a tight grip on my chain, making my forehead bounce against the hard plastic wall. He yanked hard on the chain, pressing my lips to the base of his cock as he unloaded down my throat. As soon as I finished swallowing he pulled out and left my mouth empty. I turned to the cock on my right and furiously started sucking, desperate for my next load. The beer belly didn't last long and filled my mouth with cum moments later.

I took a second to catch my breath and another cock appeared on my left. This one belonged to a Black gentleman, and while not a monster it was the biggest one I had seen so far that day. I slobbered all over it, teasing the head while both hands stroked the shaft. I took more and more of him into my mouth when a hand grabbed the back of my head and roughly began making me face fuck his big cock.

I thought for a second it was Dave but I caught him in my peripheral vision rifling through my purse - I craned my neck the other way and found it was the man to my right, clearly enjoying "helping" me suck this black cock. Too distracted by what I had going on the only thing I could do was concentrate on breathing and not scraping my teeth against the cock in my mouth. Between the hand on my head and the quickening pace of the man I was blowing, I found myself gasping for air and moaning uncontrollably.

Dave stepped behind me and lifted me off of my knees, setting me up on my feet while keeping me bent over and the cock in my mouth. He roughly pulled my thong down and let it drop to my ankles. He then squirted a cold glob of lube against my sissy pussy, working one and then two fingers inside of me. He pushed my hip so that my ass was resting on the wall now behind me, and I felt the hand on the back of my head disappear. Dave put the lube back in my purse and the man now behind me pressed his cock head against my tight hole.

Once his head slipped into me he wasted no time in burying his full length deep inside me. My squeal was muffled by the black cock in my mouth and both men began to pump into me hard, spitroasting me between the walls of the tiny booth. I was lost in the feeling of euphoria and being used like a whore when the man in my mouth began to unload. The first few spurts went down my throat but the more he came the more I couldn't keep up and his cum ran out the corners of my mouth and down my chin. He pulled out and shot a few more pumps of cum on my face, glazing my left eye shut.

I stood up a little bit while the man in my ass continued to pound away, resting my hands on the wall of the booth, and the cum running down my chin dribbled onto my giant fake tits. Another cock soon appeared in front of me and I bent back over to take it in my mouth. The man behind me grabbed my hips and pounded for all he was worth, his balls slapping against mine before I felt him tense up and cum in my ass. He pulled out and was almost immediately replaced by another cock, this one slightly smaller so that he easily bottomed out inside me on his first stroke.

I don't know how long this went on but I must have taken a dozen or so different cocks. Both of my holes stuffed with cock, cum running down my chin, my tits, my ass and my thighs, pooling on the fabric of my dress and coating the tops of my stockings.

Once there was a lull in my clientele, Dave finally spoke up.

"Time for a break, sissy." All I could do was nod.

Dave stepped out of the booth and unlocked my chain from the inside of the other booth. I pulled up my panties and slumped back onto the bench in the room, trying desperately to catch my breath and process everything that had happened so far, a thick film of cum coating my skin, my dress, and pooling in my panties.

"So far so good, slut," I heard Sydney say and my head snapped to the door of the booth. She stood in the doorway with a proud look on her face.

"Get your purse and let's go."

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4Leather4Leather2 months ago

Please finish the weekend, so enjoying the process you’re going with it.

Please next chapter.

JackiemichelleJackiemichelle10 months ago

Couldn't stop reading, wishing I was her. Please finish her journey. Can't wait to keep reading. Great story

AnonymousAnonymousover 1 year ago

The storytelling was very good and as a added reader I can say from experience this is a hot and exciting story but where is the finish product??? Reading a story or a book with no ending is just a waste of time. For that reason I could say the hole story or book is only a 2 star. I am disappointed to no end. Shame on you for your posting it. Chrissy yes my name is Christine/ Chrissy for real.

AnonymousAnonymousover 1 year ago

This ending was much better maybe even great. I like to hear sissies dressed up and getting it both ways. I know I am a dirty old trans woman but sometimes I wish it was me there.. But I never really want anyone to get hurt. Reading is fun and keeps the mind working. Great story keep it up.

AnonymousAnonymousabout 2 years ago

I am so glad you continued the series. It makes me almost wish this could happen to me.

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