A Weekend Away Ch. 02

Author's Note: Thanks for all the kind feedback & comments on chapter 01. This chapter does a lot to set up the rest of the story, so there isn't a ton of sex. Please hang in there with me and there will be much more sex in the chapters 3-?? I hope this one is sexy enough to keep you interested!

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I'm not sure how long we drove in silence. All I know is that by the time we turned down the long, wooded driveway most of Roger's cum had dried to my face and was pulling at my skin. We drove into a clearing in the woods and pulled up in front of a large home with a circle drive out front. It wasn't a mansion by any stretch of the imagination, but rather an old farm house that had been added on to and renovated many times over the years, mixing different architectural styles and giving it its own unique look.

Roger got out first and walked around to the passenger side, opening the door for Mistress Sydney. She grabbed her purse in one hand, the end of my leash in the other and stepped out, pulling me out behind her. She walked briskly towards the front door, her heels loudly clacking across the paver stone driveway. She stopped when we got to the front door.

"Phone," Sydney demanded while holding her hand out. I reluctantly handed her my phone, assuming that at some point I'd get it back. "Passcode?"

"Um, why do you need my passcode?"

"How about you do what you're told and don't question me, slut?" she spat back.

I sighed and cringed at the same time. I'd recently had to reset my passcode and I hadn't come up with a good secure number yet. "1-2-3-4-5-6."

She looked over the top of her glasses at me. "1-2-3-4-5-6? So not only are you a whore, but you're a dumb one at that. We'll definitely be doing some dumb bimbo work with you."

"Strip," she said as she absent-mindedly scrolled through my phone.

"Here? On the front porch?!? In front of..?" I gestured across the front yard. Roger was standing beside me, I could see the driver was still watching us, there was a man on a riding mower in the yard, and two women were unloading some things from a van near the garage on the side of the house.

"Yes, and all of them saw me lead you across the driveway in a bright pink collar. And Roger here recently blew his load on your face. I'm fairly certain you left your dignity at the office. Do not make me tell you again," Sydney answered while giving the leash a firm tug.

I couldn't really argue with that logic, so I took off my shirt while kicking off my shoes. I let my slacks fall down around my ankles and stepped out of them. I pulled off my socks and stood in front of her in my boxers.

"Boxers, too, sissy. Strip naked. What do you think 'strip' means, you dumb bimbo whore? We're gonna leave the last little shreds of your masculinity out here on the porch."

I relented and dropped my boxers to the porch, now naked except for the fuzzy pink collar around my neck. She slipped my phone into her purse and pulled out a pink satin ribbon, about 1" wide and probably 2 feet long. She crouched down in front of me and tied the pink ribbon in a ridiculous bow around my cock and scrotum, causing them to stand slightly at attention and drawing all of the wrong attention to my "manhood."

Sydney took my phone back out and snapped a few quick pics of her handiwork.

"Let's see, contacts, contacts, where are your... oh. Found them." I worried why she'd be accessing my contacts and I was seriously regretting handing over my phone without a fight.

"Diana is your boss's name, right?" she teased as she scrolled through my contacts.

"Please... please mistress, please, I'll do what you tell me. Please I'll do anything. Please don't send those pics to my boss."

She ignored me and continued to scroll through my contacts. "Ah, here she is. Diana... new text message... add photo..." She leaned next to me and flipped the phone around so I could see that she had indeed opened a new text message to my boss and had indeed added several of the pics she took. All she had to do was hit the send button and my career would be destroyed. Or - at the very least - made incredibly awkward.

Instead of hitting send she locked my phone and dropped it back into her purse. "You see, I have ways of making you compliant. VERY compliant. And you will be compliant, won't you?"

"Yes, mistress. I will be compliant." My heart was beating out of my chest.

"I thought so. Let's go inside."

Roger opened the front door and we stepped into the foyer which was larger than I would have imagined. An intricate wooden staircase curved up to the second floor on my left, and the foyer was open to the second floor. All over the walls in the foyer were pieces of art framed in ornate gold-trimmed frames. But this art was different. Instead of landscapes or portraits, each print was a scene of some sort of hardcore porn, photoshopped to make them look like paintings and printed on canvas. There were gangbangs, cumshots, bondage, and every other type of depravity and hedonism. I couldn't help but think this foyer would make the Marquis de Sade blush.

I was transfixed by one in particular. It was a cute young woman in pigtails wearing a pink gingham dress with layers of petticoats that made her skirt stand out sideways. She had big firm tits, pink thigh highs clipped to a pink garter belt, pink heels, and was carrying a tray of drinks. She was surrounded by several naked men with cocks in hand who were crowding around her and beginning to grope her. When I looked closer I noticed that there was a slight bulge in her panties. Oh. I realized what it was -- sissy porn.

"I figured that one would grab your attention. Did you notice her neck?" Sydney spoke up behind me, snapping me out of my trance.

I took another look and noticed that she was wearing a pink collar, just like the one I currently had on.

"But let's not get ahead of ourselves. Chrissy, it's time to start your makeover."

Sydney tugged on the leash and led me out of the foyer and towards a long hallway leading to one of the many additions that had been cobbled on to the original home. The walk was quiet except for the click of her heels on the marble tiles and the embarrassing jingling of the bell on my collar. There were doors on both sides of the hallway and Sydney opened one on the right and ushered me in.

The room looked somewhat like a salon. It had a large shower stall in one corner, a small kitchenette in another corner, a barber's chair with a beautician's station in another corner and a pedicure chair in the last corner. There was a door to what appeared to be a small bathroom. The barber's chair almost looked like it had some homemade hydraulic system for raising and lowering the chair, and I noticed that it was plugged into a nearby electrical outlet. In place of the mirror over the beautician's station, there was a large flat screen TV.

The two women who had been unloading near the garage were putting away the last of their supplies when we walked in. Both were dressed simply and wearing aprons. They didn't bat an eye to see me led into the room with a fuzzy pink collar around my neck and a bright pink bow wrapped around my genitals. Apparently, they had seen this kind of thing before. One woman was older -- probably mid 50s -- and the other had to be in her late 20s or early 30s. They looked similar enough that they could have been mother and daughter but I wasn't really in any position to discuss their family history.

"Ladies, this is Chrissy. Chrissy, this is Miss Janet and Miss Cathy," Sydney began as she circled me. "You will respect them in the exact same way you would me, and if there is any deviation from my expectations there will be serious consequences. Do you understand?"

"Yes, mistress Sydney."

As if to drive her point home she spanked my left butt cheek hard enough to throw me off balance, the sound reverberating off the walls.

"Good. I'd hate to hear that my new sissy toy is malfunctioning. Ladies, you should have the completed questionnaire and any special requests from Chrissy's wife in your packet. Call me if there are any questions and let me know when you're getting close to finishing with her."

The two women just nodded and Sydney handed the end of the leash to the older woman. She led me towards the shower stall in the corner, removed the bow and the collar and motioned for me to step in. They wasted no time getting to work. They washed the remnants of Roger's cum from my face and shaved me, showered me, removed all my body hair, and toweled me dry. They applied lotion and moisturizer and who knows what else but I smelled like a stripper and felt fabulous.

The younger one said "Follow me," and I followed her into the bathroom where she administered an enema. Once she was done she led me back into the room where she put the collar and the bow back on. She took me to the pedicure chair and started to work on my feet while the older woman applied acrylic nails to my fingertips. I was enjoying my mani/pedi (a ridiculous shade of bright pink nail polish for those of you wondering at home) and for the first time since this ordeal started I let myself relax and be thankful to my loving wife for this gift.

I was concerned about how much this must have cost, and I was a little worried about getting my phone back without any texts getting sent, but for the moment I was enjoying myself.

Once my nails were sorted the women led me to the little kitchenette area where the younger one (Miss Cathy? Miss Janet? I never did find out...) opened her makeup case and started on my face. The older one was working on something but I couldn't tell what it was. I found out soon enough as she turned around with a piercing gun in her hand. My eyes widened as she grabbed my right ear lobe and I pulled my head away.

"Listen, sissy," the older one started, "I have it right here in the file that your wife specifically requested 2 piercings in each ear. If you can't sit still you're going to screw up your makeup and I'm going to have to get Miss Sydney back in here. Now... do you want to do this the easy way or the hard way?"

I hesitated and she reached down and grabbed everything wrapped up in the bright pink bow, squeezing hard and digging her nails into my flesh.

"Easy way, please. Please please please, easy way. Easy..." my voice trailed off as she released her grip.

She turned to her compatriot and smiled, "See? This is why I love the sissies. Even when they put up a fight it doesn't take much to get them back in line. I'm really looking forward to the finishing process on this one."

She had barely finished her thought when she put the first pink-jeweled stud in my right ear. Then a second. Then two on the left. Next she applied a temporary tattoo of a pin-up girl (this one was blonde and looked a lot like the girl in the print that had caught my attention in the foyer) to my upper right thigh, with the word "sissy" written under it. She then turned to the cabinet and produced a pair of large silicone breast-forms. She glued the first one in place, checking the alignment, and then the other.

"Hold, please," she said as she lifted my hands to keep each one in place. She stepped back to double check her work and nodded. "Yeah, Chrissy. Those are gonna be perfect. A definite bimbo vibe."

The younger woman worked a little while longer and finished my makeup. They stood me up and the weight of the breasts on my chest made me feel even more feminine. I looked down to see my hands with bright pink nails holding my new big tits and I felt my cock jump.

"They should be dry by now. You can let go. Try bouncing up and down a little," the older woman instructed. I bounced up and down and the breasts bounced along with me. I had worn breast-forms before but always in a pocket bra, so the sensation of my breasts bouncing on my own skin, and the inside of the forms rubbing my already sensitive nipples made my cock grow even more.

"Ok, those look secure, and your little sissy clitty is telling me that you like them very much, right?"

I nodded enthusiastically and they led me to the beautician's chair. I can honestly say - even after everything I had already seen that day - I was in shock when they spun it around to sit me down. There, in the middle of the cushioned seat, was a small opening and peeking out of the hole was a pink dildo. The younger one put on a pair of gloves and lubed the dildo. She then turned to me and slid a well-lubed finger in my ass. I jumped a little, but she was able to eventually work 3 fingers inside of me and began to slowly finger fuck me.

I was up on my tiptoes and began to moan, when she said "Yeah I think you're ready. Have a seat." She pulled off her gloves and the two of them helped me into the chair and lined me up so that I could feel just the tip of the dildo poking at the opening of my sissy pussy.

The older woman grabbed an iPad from the counter and began to scroll through the screens.

"Just need to make sure we're lined up good," she said, clicking buttons on the screen, and I felt pressure as the head of the dildo began to press its way inside of me. I felt the head pop past my sphincter and I nodded to her.

"Good," she said. "That'll do for now."

She set the tablet down and produced a shoulder length blonde wig out of a cabinet. The younger woman applied a wig cap and then started fitting the wig on my head. The older woman picked up the phone in the room and dialed.

"Yeah, it's me. Chrissy's ready for the finishing process." Finishing process? This was the second time she had mentioned that and now, with a dildo partially inside of me, I began to wonder what the finishing process might entail.

As the younger woman was finishing the wig and making final touches, Sydney walked back into the room.

"A Look at you, sissy. You look much better now that the ladies have taken care of you. I hope your spa day was relaxing, but we've got work to do tonight. Lots of work. Only one last item to take care of here and then on to other things!"

I was getting more and more nervous about this "finishing process" and "one last item." Sydney picked up the iPad and after a moment the large flat screen came to life. There was a giant screen saver that simply read:

***********PIN-UP GIRL SERVICES************

**Your Wildest Fantasies... Come to Life!**

"Ok, just a quick equipment check and then we'll begin."

I jumped as the head of the dildo vibrated sharply.

"Ok, vibrate is working. Now let's test... this," she continued as I felt the dildo bury itself deeper inside of me. The pressure rose as it slowly filled me up and continued to go deeper. "Say now when it starts to get uncomfortable."

"Now. Now now nownow," I protested as she let it go a little past where I was comfortable. I was trying to stand up to give my sissy pussy a little relief but couldn't support myself properly in the chair.

"Okay, that's a good baseline," she said as she slowly withdrew the dildo from my ass.

I couldn't see what she was doing with the iPad, but I heard her speak as if she was on a phone call.

"Are you ready on your end?" I heard her ask. "Okay, let me check the signal on this end and we should be ready to go." The screensaver disappeared from the screen and was replaced by an image of a bedroom. It took me a minute because the angle wasn't one I was used to, but I very quickly realized it was MY bedroom. This could get interesting...

"Looks good here. We can start when you're ready." Sydney confirmed.

My wife Tiffany walked seductively into view, looking especially hot. She was wearing a black sheer babydoll nightie I hadn't seen before. She didn't typically wear lingerie as she was much more practical than me ("Just gonna have to take it off to fuck anyway, right?" she used to tell me) but occasionally her lover would ask her to wear something so I wondered if maybe this was a nightie he bought for her. The top hugged her well and made her tits stand up fantastically. The fabric dangled from the empire waist and fell softly over her sexy belly, splitting down the middle and opening to reveal that she wasn't wearing panties.

She sat on the edge of the bed and massaged her left breast through the fabric, letting her other hand drop between her spread legs as she began to play with her pussy. The dildo beneath me pulsed lightly, simulating the pulses I knew were starting to flow through my wife's body. The camera zoomed in, giving me a better view and as she slowly slid two fingers into her pussy the dildo slowly slid inside of me. I watched as my wife's fingers penetrated her pussy, and marveled that the dildo in my sissy pussy matched her rhythm. I assumed Sydney was controlling it from the iPad but at this point I didn't much care. If this was the finishing process then so far it was working out fine for me, and seemed to be working out for my wife, too.

Something off camera caught my wife's attention and she moved off the bed to kneel on the floor. The camera zoomed out a little and a very muscular, very naked man stepped into view. Ok, I was not expecting this, but I was intrigued. She must have had her lover come over to help her out with this part of the surprise. I had never met him - and the only picture of him I'd seen was just his cock in her mouth - but I could honestly see why he turned her on.

The video screen switched to a second camera angle (how many cameras did she set up??) and now I was looking at my wife from the side, her lover's cock dangling half-hard just inches from her face. The older woman (Miss Janet? Miss Cathy? Still no clue) opened a drawer and pulled out a realistic dildo with a big set of balls and I had a good idea what was coming next.

As Tiffany took his cock into her mouth, the older woman held the dildo against my painted lips. I didn't need to be told what was expected of me and I did my best to match the action on the screen. When my wife licked the head, I licked the head. When she ran her tongue down his shaft, I did too. When Tiffany stroked his cock, took his balls in her mouth, or moaned in pleasure, I did the same. And when she took as much of him as she could in her mouth and started to gag, so did I.

Soon he was fucking her mouth and the older woman matched his strokes in my mouth. My new breasts swayed gently with the motion. He reached up to hold the back of Tiffany's head and that's when I saw it. A tattoo. On his forearm. Of a pin-up girl. Very quickly it dawned on me that this was not my wife's lover but rather the man who had taken my car from the parking garage. This complete stranger had not only taken my car (and apparently made it to my house safely) but was now going to take my wife, too. I could see the drool running down Tiffany's chin and as she reached down to play with herself and the dildo pressed at my hole buzzed sympathetically.

Mr. Tattoo pulled out of my wife's mouth and helped her to her feet as his big rough hands pawed at her breasts, freeing them from the nightie. He wrapped an arm around her waist and lifted her onto the bed like a ragdoll, laying her down on her back. The video switched back to the first camera angle and as he climbed on top of her he took her left nipple into his mouth. The older woman put the dildo she'd been face-fucking me with down while the younger woman groped my left breast and ground it against my nipple underneath. In my heightened state bolts of electricity shot from my nipple straight to my crotch and I was now incredibly hard. I whimpered and closed my eyes for a second and as the dildo trained on my sissy pussy slowly fed into me, I knew that my darling wife was also being impaled.

Sydney handed the iPad off to the older woman and stepped up next to me. She grabbed a cup from the counter in front of me and began to tease my cock. The dildo inside of me kept up at the same rhythm as the cock fucking my wife on the screen in front of me. As the man mashed my wife's breasts and fucked her pussy, all of the sensations of my body -- the dildo fucking me, the younger woman kneading my tits, Sydney playing with my cock -- sent me into a sissy frenzy. It's hard to describe a sissy frenzy. Everything feels electric and all I want to do is suck all of the cocks, and fuck all of the pussies, and drink all of the cum, and and and and and... When I'm in a sissy frenzy Chrissy truly takes over and I can no longer control anything.