A Weekend Away Ch. 03

Sydney led me out of the salon, still naked save for the collar around my neck and the bright pink bow around my genitals, and across the hall into another room.

There was clothes rack after clothes rack lining the walls and holding every color, fabric, and pattern you could imagine. Here was a section of pink chiffon dresses, there was a section of black leather pants and bodysuits, schoolgirl costumes, French maid costumes, revealing swimwear, and every other stereotypical "sexy" kind of clothing. In the middle of the room was a table full of different bras and panties like you'd find at a Victoria's Secret and one wall was nothing but footwear -- work boots and stripper heels and sandals and platforms and and and...

The sissy inside of me wanted to run around the room like Julie Andrews in "The Sound of Music" but I played it cool until I could figure out what Sydney had in mind. The older woman from the salon walked in behind us and picked up a fabric tape measure. Sydney took me by the leash and led me to a raised platform in the corner that had 3 mirrors around it.

"Okay, Miss Janet is going to take your measurements and then we'll start putting together your wardrobe," Sydney explained. (Okay, so Janet was the older woman. Good to know.)

This was the first time I'd seen myself since Miss Janet and Miss Cathy had worked their magic. The bow tied around my now limp clitty was a little embarrassing, but the rest of the package was stunning. The large breast-forms glued to my chest didn't look 100% natural, but all things considered they definitely broke up my more masculine lines and gave Chrissy some real curves. The wig and makeup jobs were simply stunning. I honestly didn't recognize myself in the mirror - they had transformed me into a woman. In the past when I had done my own makeup it looked like a newbie crossdresser who had done their own makeup. But this was a work of art. Every highlight and contour perfectly softening my face into that of a woman. I was so happy being fully Chrissy for the first time in my life that I could have cried tears of joy. If only for this moment, the weekend was worth it.

Miss Janet stepped up onto the platform next to me and began to take measurements, calling them out to Sydney who was entering them into an iPad. She even measured my feet with that weird metal foot thing they always have at shoe stores. Once Sydney and Janet reviewed my measurements they began to pick through their abundant inventory. Sydney removed the bow on my clitty and produced a pink satin bikini with ruffles. I quickly put it on, desperate for the feel of lingerie. Next she handed me white thigh highs with pink bows and I put them on as well, feeling electric as they slid up my perfectly smooth legs. Janet came over with a pink plaid schoolgirl skirt and a white crop top blouse. I pulled up the skirt to my waist, my panties peeking out under the short skirt. Janet slipped the blouse over my shoulders and tied it in the front, my giant fake tits straining to bust out of the fabric.

Janet went over to the wall of shoes and brought me a pair of pink 5" platform heels with a strap around the ankle. I stepped into the heels as both Sydney and Janet helped fasten the buckles. I took in my reflection and was overwhelmed. I had been transformed from an ordinary everyday boring guy to a big-tittied blonde bimbo bombshell. It was stunning to see Chrissy in all of her glory, as I'd always imagined her, as I always knew she was inside of me, as I'd dreamed of seeing her looking back at me in the mirror. I twirled and posed and strutted in front of the mirrors, trying to take it all in.

"Well?" asked Sydney.

"It's... I'm just... I mean..." I stuttered and stammered. I was having trouble putting all my emotions into words.

"Easy there, bimbo. It's a lot for your little sissy brain to process all at once, isn't it?"

"Yes, Mistress Sydney."

"It's okay, you're not here to think. With a name like 'Chrissy' you don't really have a future in rocket science or brain surgery, do you? No, Chrissy is a perfect name for a dumb bimbo fucktoy like you, and that's what you want, isn't it? To be a dumb bimbo fucktoy?" Sydney teased.

"Yes, Mistress Sydney. I want to be a fucktoy for men to use. Please." I replied, lost in the image in the mirror. Sydney dipped two fingers into the little cup of my cum she had collected in the salon and held them to my lips. I greedily sucked at her fingers, cleaning up all of my reward.

"Well there's plenty of time for that, sissy, but we've got work to do first. However, it's been a long afternoon and we need to get something to eat. Thank Miss Janet and let's go."

"Yes, Mistress. Thank you, Miss Janet, for all your hard work. I'm so happy!! Thank you!" I gushed.

"Aww, no problem, Chrissy. Have fun this weekend!" and with that Sydney tugged on my leash and traipsed me out of the room.

Sydney led me back down the hallway and across the foyer to a large dining room on the far side of the house. There was a long oak table in the room that could seat about 20, and there were two places set at one end. Sydney sat at the head of the table and motioned for me to sit down next to her. She rang a bell and a cute little woman in a French maid outfit carrying a tray of drinks came through a swinging door at the side of the dining room.

"Yvette," Sydney said, "we are ready for dinner. You may begin service."

"Yes, mistress," Yvette replied with a slight curtsy.

Yvette set a glass of red wine in front of Sydney, and something pink and bubbly in front of me. One sip told me my drink was the usual sugary berry-flavored type of wine cooler I liked to drink when I was dressed as Chrissy. (I felt that beer was too masculine for Chrissy, and decent wine was too sophisticated for her, so I always drank super sweet wine coolers as Chrissy, reinforcing the bimbo vibe. Clearly, my wife had shared this information.) Yvette took her tray and headed to the kitchen without a word.

"Well," Sydney began. "I'm sure you have a ton of questions and want to know what's in store for you this weekend. Let me start by telling you a little bit about us and our work. We are Pin-Up Girl Services, and we provide a vast array of services to members of our community. Take Yvette as an example. She used to be Mike, a boring middle management drone in some corporation. She came to us years ago and was so happy with her sissy transformation, she stayed on as one of our French maids. She serves meals and cleans here, as well as working as a maid in many of our client's homes. Roger, whose cock you sucked earlier, and Dave, who just fucked your wife, both came to us as bouncers from a bar. Now they make their money as our muscle and they get paid to fuck on a regular basis."

Sydney took a long sip of her wine and watched me to gauge my reaction.

"Some of our clients," she continued, "pay for our services outright and some of them work for us to earn their services. Sort of like an internship, if you will. This weekend you will be working for us to earn your sissy transformation, and any amount we don't make back on you will be charged to your credit card. Your wife was very specific about certain fantasies she thought you'd enjoy, but also asked that we not ruin the surprise."

Yvette returned with two salads - basic greens with grilled chicken. I took a closer look and the only tell that she had once been a man was the slight bulge of an adam's apple. Her makeup, hair, voice, and even the way she carried herself was all femme.

"So how much do I need to earn this weekend to pay for all of this?" I asked as I picked at my salad.

"Oh, I'm not gonna tell you that. Worry about doing what you're told, and the money will take care of itself. Besides, dumb bimbo sluts like you don't worry about money, do they? Of course not," Sydney chided.

"What kind of things will I be doing to earn money?" I asked next, hoping for any glimpse of my next three days.

"Nope. Not gonna tell you that either. Now eat your salad -- we've got work to do."

We spent the rest of the meal in silence and although I hadn't eaten since breakfast, I was too distracted about what the weekend held to really eat much. Sydney finished her salad and gulped down the rest of her wine. She pointed to my glass and I drank down the rest of my wine cooler as well.

Sydney stood up from the table and motioned for me to follow her. She led me back across the hallway and into a large study with rows of bookcases, a large leather sofa, and a few highback chairs.

We spent most of the rest of the night in the study in "sissy school," practicing my walk, my voice, crossing my legs when I sat down, and all other manners and habits of a proper bimbo. Every time I screwed something up Sydney was ready with a short black riding crop and a quick swat to my ass, stomach or crotch -- whatever was in easy reach for her. Every time I did good she rewarded me with two fingers of cum. After a few hours I began to get the hang of things -- pelvis forward, one leg in front of the other, hips swaying, voice higher, legs crossed, hands light -- until she was happy with the progress we had made so far.

"Ok, that's good enough for tonight," she finally told me. "Time for a test of everything you've been practicing." She walked over to the wall and pressed an intercom button. "We're ready for Dave."

Sydney went to the bar and poured herself a drink as she explained, "We will see how well you've learned your sissy lessons, and how good you are at pleasing a real man. Blowjobs and dildos in your ass are one thing, but you're going to have to prove yourself now. Stand over there next to the sofa and do exactly as you're told."

I minced over to the side of the sofa, practicing my best sissy walk, trembling slightly with anticipation and nerves. Sydney sat in one of the highback chairs swirling her drink with one hand, and tracing slow, lazy circles in the air with the riding crop with her other.

There was a knock at the door and Sydney yelled "Come in" without ever breaking eye contact with me. She smiled slightly, seeming to enjoy the moment. Dave stepped into the room and looked me over like a piece of meat.

"Is this the one from the parking garage?" Dave asked.

"Yes, I believe you have met her wife," Sydney replied, grinning from ear to ear and enjoying the slight flash of humiliation on my face.

"Damn, Syd, you do really nice work. I wouldn't believe it if I didn't see it for myself," Dave replied as he walked over to me. He loomed over me and let his hands roam all over my body. He bent down and kissed me, gentle at first, but then roughly shoving his tongue past my lips and making it clear that I belonged to him. He continued to grope me and when I was least expecting it he spanked my ass. HARD. I jumped and he broke our kiss, chuckling under his breath.

"That ass is mine, understand?" Dave instructed.

"Yes, sir." I eeked out in my best femme voice.

"Why don't you get our guest a drink, Chrissy?" Sydney suggested.

"Yes, mistress." I answered before turning back up to Dave. "Can I get you a drink, sir?"

"Beer, slut." Dave growled as he sat down on the sofa.

I crossed the room to the bar and found a mini fridge stocked with beer and wine. I crouched down to get a beer when I felt the riding crop slap against my ass.

"Bend at the waist, sissy!" Sydney shouted. "It's your job to put on a show. Let him see that ass."

I straightened back up and slowly bent at the waist, flipping my short skirt up as I bent over to give him a full view of my panties. I even took a moment to seductively shift my weight from one leg to the other to give my butt a little wiggle. I took a beer out of the fridge and opened it for him. I crossed back to him and made sure to bend at the waist to give him a good view of my cleavage as I handed him the beer.

"Will there be anything else, sir?" I asked, still practicing my new femme voice.

"Uh, yeah," he grunted as he spun me around and pulled me down onto his lap. I could feel his erection through his slacks and began to do the best lap dance I could. I tried to remember everything I had ever seen a stripper do in a private dance. I ground my ass against his cock in circles. I leaned back against him and purred in his ear. I jiggled my ass in his face and even spanked myself. I was really starting to get into it when I slid my hands down onto the floor and bounced up and down on his crotch with my legs spread wide. I could feel my own clitty getting harder as it rubbed against his fat cock with each bounce.

"Oh, fuck yeah," he groaned as he pushed me off him and onto the floor. He stood to drop his slacks and boxers, grabbed my leash, and pulled me with him as he plopped back down on the couch. He held me inches from his dick and he absolutely reeked of sex. Not just sex, but I could also smell the very familiar scent of my wife's sweet pussy all over his cock.

"Do you smell Tiffany's pussy on his cock, sissy?" Sydney teased. "You like the way her sex smells on another man?"

"Yes, mistress," was all I could manage. His cock bobbed and bounced in front of my eyes and I didn't need to be told what to do. I quickly took him in my mouth and sloppily licked the mix of his cum and my wife's pussy off of his cock. The more I tasted, the more I flashed back to the image of my wife sucking this man's cock, and then getting fucked by him. I became even more excited and bobbed up and down on his dick, taking more and more of him into my mouth, my saliva mixing with cum and pussy juices.

"It looks like she digs the taste of her wife on my dick," Dave told Sydney as he shoved my head down and bottomed out in my throat. I gagged and my eyes watered as he fucked my mouth. I fought for air, stealing gasps as I could. His pace picked up as he seemed to be getting close.

"Don't you dare, Dave. That's not what I'm paying you for tonight. You know the drill," Sydney reprimanded. Dave seemed slightly disappointed as he pulled his cock out of my mouth.

"I know, I know, I know. She's actually pretty good at that for a sissy," Dave sighed.

Dave pushed me away from him and stood up, kicking off his shoes and removing his slacks and boxers. He towered above me as I sat on the floor, rather unladylike, regaining my breath. Once again he grabbed me by the leash and pulled me up on the sofa, wrapping one giant arm around my waist and dropping me so that my upper half was on the arm of the sofa, and my ass sticking in the air. He roughly pulled my panties down around my knees and knelt on the sofa behind me. He grabbed my ass cheeks and pushed them apart, spitting on my ass crack. He rubbed his saliva around my hole and pushed a thumb inside, pulling and stretching my ass. He pulled up with his thumb and almost lifted me off of the couch, slapping my ass with his free hand. I jerked at the spanking and ended up driving his thumb further inside of me. He fucked my ass with his thumb until he was sure I was lubed enough. He pulled out his thumb and I could feel the head of his cock pressing against my hole.

"Ready to get fucked like the whore you are, Chrissy? Are you ready to get fucked by a real man?" Sydney asked, still sitting sideways in her highback chair.

"Yes, mistress, yes I am," I spit out.

That was all Dave needed to hear. He pushed into me in one quick thrust. Thankfully I had been well-lubed by the dildo earlier or he might have split me in two. He was definitely thicker than any cock I had taken before, and I had never felt so full. He grabbed me by the hips and stayed buried deep inside me for a moment before slowly starting to pump in and out of me. A moan escaped my lips, and then another. I could feel my little sissy clit swinging in the breeze as his giant balls kept slapping against it. I felt like a real, complete woman and I lost myself in getting fucked by this big strong man.

Dave fell into a rhythm, fucking me hard, plowing into me with the same wild abandon he had used on my wife hours earlier. I bounced all over the arm of the sofa, moaning and grunting like a bitch in heat.

"Oh, yes, fuck me. Please, fuck me. Yes, I'm your whore. Please..." I babbled incoherently as I let this strange man own me. I noticed out of the corner of my eye that Sydney had hiked up her pencil skirt and had a leg thrown over the arm of her chair, panties pulled to the side and her fingers lazily probing the folds of her pussy. Apparently she wasn't all business.

Dave reached around and roughly stroked my limp clitty as he picked up speed. In no time I was spilling my seed onto the leather seat cushion below me.

"Remember, sissy, just because you've cum doesn't mean you're done. You're his fucktoy and exist to serve him," Sydney reminded me.

"Aww, fuck yeah, bitch. Take my fucking dick. Take it all you fucking slut," Dave grunted as his speed picked up. "You're mine, whore."

"Yes, please, sir, please use me. Fuck me like a whore!" I was really getting into it and it felt amazing to be used for his pleasure.

Apparently the dirty talk was more than Dave could handle and soon he was shooting his load deep inside of me. He pumped a few more times before pulling out and collapsing on the far end of the sofa. I felt empty, but enjoyed the sensation of his warm cum slowly dripping down my thigh and pooling at the top of my stockings.

"Panties up, sissy. I want all of his cum drying in your panties," Sydney instructed. I pulled up my panties and stood in front of the sofa. "Clean up his cock, slut. Make sure it's nice and clean."

Once more I knelt before Dave and greedily lapped at his cock, cleaning the remnants of cum from him, occasionally catching the slightest taste of my wife around the base of his cock.

"Okay, that's good that's good," Dave said as he pushed me away.

"And now your little cummy mess on the sofa, sissy," Sydney chided.

I started to use my hand to wipe up the cum from the sofa and as the slippery mess slid around Dave grabbed the back of my head, shoving it down onto the cushion and rubbing my face in the puddle of cum.

"Use your tongue, dummy," Dave told me without letting go of my head. "Wow, Syd, this one really is a dumb bimbo."

I finished licking up my cum, and Dave let go, leaving me kneeling against the sofa, spent but satisfied.

"That will be all, Dave," Sydney said as she stood up, putting her panties back in place and smoothing out her skirt.

Dave put on his pants and headed for the door before turning to say "See you tomorrow, slut." He broke into a giant smile and nodded towards Sydney.

"Alright, let's go, bimbo," Sydney said, grabbing the end of my leash and pulling me up to my feet.

I wobbled down the hallway and up the stairs in the foyer as Sydney led me to my room. When we stepped inside the lighting was low but I could see a four-poster bed complete with pink satin sheets and a frilly pink nightie hanging on the closet door.

"Get dressed for bed and get some rest. You've got a very busy day tomorrow." She unclipped my leash but left the collar on. Then she turned and walked out, closing the door behind her.

I sat on the edge of the bed, peeling off my heels, crop top, and skirt, but decided to keep the panties and stockings on. I kinda liked how humiliating it was to have a real man's cum drying in my pink panties. I slipped into the nightie and crawled under the covers, trying to process everything that had happened over the past several hours. Was it really this morning that I had gone to work? Was it only noon when Sydney shattered my world and led me here? It seemed like days. I turned on the TV for some background noise, only to find that every channel only showed porn. Of course. I settled on some blonde bimbo cheerleader who was being double-teamed by a couple of jocks in the locker room. I'd tell you how it ended, but in minutes I was out.