Dream Vacation

By evening, I was in quiet agony, my cock being simultaneously stimulated by the silk panties, and crushed by the chastity cage, and of course the tits glued to my chest. I had my head on a swivel, always checking to see if anyone was giving me strange looks. I looked down a lot, and tried to adjust my coat to make myself look more shapeless. After dinner, we started to walk, but not in the direction of the hotel. "Mistress, can we please go back, I'm dying," I said.

"We have one more stop," she said. A few minutes later, we were back at the adult store. Mistress walked right over to the paddles, picked up a wooden one with "SLUT" carved into it, paid for it, and we left. Once we got back to the room, she ordered me to strip to the bra and thong, and fasten the stripper heels back onto my feet. Next, I was to put on the corset to the best of my ability. I got it around myself, and again she slipped the blindfold over my eyes.

"Bend over the ottoman, slut, and spread it wide," Mistress Brittany commanded.

I folded myself over the round ottoman so that each arm and each leg were spread wide, and my tits were crushed against the top. My caged cock was smashed into the side of the smooth, cool leather. Her knee pressed cruelly into my back, and she pulled so hard on the laces that I thought she'd split me in half! She affixed the wig back onto my head as well.

"OWWWW Mistress!" I whined. The next thing I knew, Mistress grabbed my head and forced it my mouth down on a rubber cock.

"Suck on that, loser. That'll fucking keep you quiet," she said as she tied off the corset and got off my back. Next, I felt my legs tied to the neared legs of the ottoman. Since it was round, my legs were only about shoulder-width apart. My arms were tied to the further legs, so they were spread out a good deal. Mistress grabbed the back of my head and rammed my head up and down on the ottoman-mounted dildo which caused me to sputter, drool and gag. She finally let go, but the dildo was long enough, and I was tied tight enough, that I could not spit it out. The corset was already greatly restricting my breathing, and then this forced deep throat cock sucking!

"MMMPPHHHH!! OOOOOFFFFF! GLURRRGGG!" I gagged.

Sucking cock isn't as easy as girls make it look, is it?" she asked rhetorically. "Especially in those pornos where men just face fuck us, we do a damn good job, I'd say," she continued. Sweat and drool poured down my face. Strands of the wig had fallen out and gotten stuck to the dildo, and I gagged some more on the hair that was in the way. "There, there," she cooed. "Breathe around the cock, breathe through your nose, there you go!" she encouraged me. Once I slowed down and began to listen, her advice really did help, and things got a bit easier. She let go of my head. "Keep practicing, baby, I'll be right back," she said.

"MFFFFF!! Nnnnghhhh!!" I moaned, to no avail. I heard the door open and close, and then there was silence, and darkness. I made peace rather quickly with the fact that I was stuck in my current situation until Mistress Brittany felt like changing it. I was completely at her mercy, and was ok with that. It was what I'd wanted my whole life. As commanded, I continued to bob up and down on the dildo, even though I knew she was not present.

What I'd not anticipated was the amount of pain I'd have to deal with. I'd watched the videos, and read the stories online, and I'd assumed the pain would come from being spanked, and tied, and fucked, and wearing uncomfortable shoes...and that once I was out of those situations, the pain would subside. Sure, there'd be some residual pain from spanking or fucking, I'd even expected that. But after just a few days, my whole body was sore, it was as Mistress Brittany said "a wholly female experience."

Her methods were subtle, but genius. The removal of all my body hair and the application of the spray tan, while not noticeable to others, definitely put me a feminine mindset. The nail polish WAS noticeable to others, and very much embarrassed me and kept me on my toes while out in public. The large fake tits she'd glued to my chest, and forced me to carry around in private AND public made me very self-conscious. What if people were looking at them? I'm sure people were! Also, they were so HEAVY, and hard on my back, and hard to sleep with as well. Only being forced to wear them 24/7 gave me an appreciation of how large breasted women feel, emotionally and physically. Oddly, though, they also made me feel really feminine and sexy. Now, I see why women have a love/hate relationship with their boobs.

The chastity cage was a real pain. I knew it would be, but again, I had no idea how much! I figured it would be part of the deal for Mistress Brittany, so I offered it, knowing it would not be my favorite part of all of this. Having my cock locked away, and totally controlled, allowed me to focus more on what Mistress wanted, and also had the effect of making me feel more feminine as well.

The clothing aspect was pretty much what I'd expected, but not totally. As an avid crossdresser, I knew all about the feeling of dressing sexily, and how much that aroused me. Again, though it was the length of time, and lack of control I had in the situation. Sure, I'd worn thongs before, but never for so long! And never in public or for entire days! It really made me feel both sexy, and kind of self-conscious wearing one just shopping in London. And the bra, caressing my big tits, was amazing! The silk of both, against my hairless tanned skin felt so sensual, but against my poor caged cock was torture. Lastly, the heels and corset were both very uncomfortable, but made me feel sexy and feminine. As women say "beauty is pain," and now I totally get why women have a love/hate relationship with their fashion as well. The fact that I had no control over any of these things, added to my feelings of helplessness and dependence on Mistress Brittany.

There were the humiliation and sexual use aspects that I'd experienced thus far. My humiliation in front of Helly, and online were immeasurable, and a bit unexpected. Still, they were ultimately a huge turn on, and again Mistress Brittany is a genius.

The combination of the blindfold and the repetitive nature of me bobbing my head up and down on the cock had had a hypnotic effect, and I had totally lost track of time and my surroundings. Apparently, Mistress had re-entered the room at some point, because I was jolted back to reality by a FREEZING sensation on my caged cock and balls.

"OHHHHHH!!! MFFFFFFHHH!!!FFCCKKKK!!!" I cried. I thrashed and pulled at my bonds.

Mistress just laughed, and waited until I calmed down. "Are you quite finished?" she asked. "Yes, those ice buckets and ice machines are VERY handy," she cooed. Clearly, she had set my chastity cage in full bucket of ice. "Let's go ahead and chill the champagne as well," she added, and set what I assumed was a bottle in the bucket as well. The next thing I knew, the light flooded into my eyes again, and I had to blink a few times to adjust.

I looked back over my shoulder and saw Mistress Brittany. She looked radiant as usual, this time in a short, white, silk robe that tied at the waist. In her hand, she held the paddle, and tapped it menacingly against her hand a few times, with a cruel smile on her face. Without further ado, she wound up, and wacked me on the ass with it! I bore down on the cock to muffle my screams. WACK! WACK! WACK! WACK! I lost track of how many times the paddle hit me, but it was a lot, and it felt like it was all on the same cheek! It started to burn, and I closed my eyes and hoped it would be over soon. WACK! WACK! WACK! WACK! My one ass cheek got a bit of a reprieve, at the expense of the other. Now both ass cheeks were on fire, and tears poured down my face.

Mistress switched back to the first ass cheek, assaulted it a few more times, and then switched again. Just when I thought I couldn't take it anymore, I was overwhelmed by a cold, soothing sensation. She'd grabbed a few pieces of ice from the bucket and had begun to rub them on my poor burning ass cheeks!! "MMMFFFF! THNKKK UUU TTTHRSSS!" I mumbled.

"You're very welcome, young lady," Mistress replied. She stepped in front of me. "I think you deserve a reward," she said, as she loosened the tie on her robe and flashed me her beautiful breasts! I thanked her again, and she smiled, and grabbed a glass from the bedside table. The bottle was quickly opened. Mistress poured herself some champagne, laid down on the bed, and turned on the TV. I kept sucking the cock, because she had not told me stop, but I could hear moaning coming from the TV. I briefly looked over at the TV, saw one of Mistress Brittany's old movies, where she was being pounded by a very large cock, and clearly enjoying it, but then returned to what I was doing.

"No, no, slave, keep watching," Mistress said. "See how his big cock is filling my pussy? See how much pleasure he brings me with his dick? He's a real man. You are not. The only way you can bring me pleasure is the way in which you currently are...which is being at my mercy and used for my amusement...which does get me off. She was right, and I knew it. It was painful to think of how real men had gotten to fuck, and please Mistress Brittany and how I never would be able to do that. My only hope was to be a good slave for her. "How are your balls, slave?" she asked.

"MFFFF!!! UGHHHHH!!!!OWWW!" I moaned.

"That's what I thought," she laughed, and took another sip of her drink. We continued to watch Mistress's past work. The stud ran her through all the positions, and seemed to do a really good job, that's for sure! He was strong, and really manhandled her. "Man, those were the days..."she reminisced."I was young, and just into the business, and really enjoyed my work...the sex was fucking amazing, and I had the energy to do all the hard positions," she continued. "I'm getting so fucking hot watching this...." Mistress stood up, and walked toward me.

She pulled her trusty strapon into place, untied my hands and legs, and pulled my face off the cock. Then she took my hand, and helped me to my feet. As we walked past the mirror she said, "Look at your ass, each cheek says 'slut' just like they should," she observed, and she was right. A few more steps, and I was pushed down onto the bed. Mistress laid down on her back, propped up a bit by the pillows, and pointed at her cock. By this time, her robe had fallen to the ground, and she was naked except for the strapon.

"You're the bitch, you do the work," she commanded. I gave her cock a few quick sucks, to at least get it wet, but I could tell she was not interested in much foreplay. "Since I have such large breasteses directors always want me to do reverse cowgirl, but it's fucking work," she complained. "You have large titties, you do reverse cowgirl. Dutifully, I turned around, spread my ass cheeks, and lowered myself slowly down onto her cock. The heels sunk into the mattress, so I turned my feet out to the side, and tried to sit down and back on her cock. Mistress Brittany would have none of that! She slapped my ass and said, "Get back up on those heels and squat on my dick!

Her request seemed impossible, but I knew I had to try. Awkwardly, I slid my feet back to where the heels of the shoes were upright, and again, sunk into the mattress. Mistress put her hands under my ass and pushed until I was in a deep squat. She gave me a moment to get my balance and adjust, but then she moved her hands away. "Very good, now get riding!" she growled. "Get those big titties bouncing!!"

I began to work her cock as I'd see women do in pornos, and I quickly discovered how hard it was on my legs and thighs. My tits began to bounce, and the whole experience was very sexy, but a lot of work! Mistress grabbed a hold of my bra strap, and unfastened it. I knew what she wanted, so I reached up, slid the straps down my arms, and tossed the bra to the floor. Then my titties really began to bounce!!

"Oh my God Mistress!!" I shouted. "Please, please pound my ass!!" I cried. Then I felt her hands on my severely constricted waist. She latched onto the sides of corset and used it to lift me up and down, as she simultaneously began to thrust her hips up and down. So, whereas before, she was content to let me ride her cock, she made it clear that now it was her turn to fuck me. My thighs and calves were on fire, and my back hurt as well. My locked cock was in sheer agony, and of course my ass cheeks still burned from being paddled, and my asshole burned from being fucked.

"Mistress....Mistress...I can't....I can't!!!" I cried, as my legs gave way, and my ass crashed down on her thighs. "OWWWWW OHH FUCCKKK!" I shouted, as the remaining few inches of cock shot straight up my ass.

"Your legs are fucking shot," Mistress observed, "but you're not done, because I'm not done. Grab those long sexy heels and start rocking," she said. Tentatively, I reached back with one hand, then the other, and grabbed each heel. This arched my back, and thrust my tits even further forward. "Very good, now just bounce your ass up and down, there you go," she said. I raised my ass a tiny bit, and dropped it back down. Then I did it again. Then I raised it a bit higher. I was limited on how high I could go, so Mistress encouraged me to go faster. Once I got into a rhythm, it started to feel pretty good. It was probably rubbing my prostate, which I'd read about in articles. The short, rapid rhythm also got my tits bouncing a ton, and that made me feel really sexy as well.

"Ohhh....ooooooohhh," I moaned in pleasure. I closed my eyes, tossed my hair, and reached up and caressed my tits, and then put my hands back on the heels. "What else can I...ooohhhh...mmmmm...doooo for you, Mistress Brittany," I cooed. I looked back over my shoulder, bit my lip suggestively and winked at her.

"Now we're getting somewhere," Mistress said. "Once we get through the pain, there is pleasure. Pleasure for both of us, such a good slave," she smiled. "It would be sexier if you could multi task a bit more..." she offered.

"Oooo..OHHHH!" I exclaimed. For some reason her cock hit me just right at that moment, but I continued. "Yes, anything to please you, please Mistress," I said.

"Well, you could pretend those heels are two more cocks," she suggested. "It would be super fucking hot if you could keep bouncing on MY cock, but stroke your heels like they were cocks as well," she said. No sooner had the words come out of her mouth, than I began to slowly run my hands up and down my heels, like I was giving them a hand job. "Oh that's very sexy. Your pretty little fingers with adorable pink nails wrapped around those long black heels, stroking them like they're big black cocks...." she observed. "A big black cock up your ass, and two in your hands. We just need one in your mouth. I take you back to my place in the States, have you grow out your hair, get you some nice big titties and a slutty wardrobe, and you could make me some serious money taking four cocks at once," she said.

By this point I was so lost in bliss I just started to moan, "Yes Mistress. Yessss Mistresssss Brittany," over and over again. "Mistress I'm...I'm....." I stuttered. "May....may I?? PLEEASSSE" I cried. She wrapped her arms around my waist and pulled us into position so that she was seated with her back against the headboard, and I was seated on her cock.

"You may," she replied. I leaked cum out of my soft caged cock onto her waiting hand. It was strangest orgasm I'd ever had. I didn't even know that was possible! "You came like a girl," she laughed. "But now you know what girls have to do," she said. Though I was exhausted, and in pain, and still seeing stars from my orgasmic bliss, I knew what I had to do. Gingerly, I raised myself up off her cock, rolled over onto my stomach and positioned myself between her legs. Directly in front of my face, her big black cock stood menacingly erect and still ready for action. I folded my arms beneath my tits, rested my elbows on the mattress, and took Mistress' cock into my mouth. Immediately I sputtered and gagged, and Mistress Brittany began to laugh.

"You forgot that was just in your ass, didn't you? That's ok. That's very hot, all the girls get used to it," she reassured me. She reached over, grabbed her phone off the bedside table, and snapped a photo. "I wouldn't fucking do it anymore, because I don't have to, but you do," she informed me, as she took a hold of my hair and the back of my head with her free hand and guided my mouth slowly back onto her cock. Once I got past the taste (or rather, licked all my ass off of it) and began to breathe through my nose again, I did fine.

Mistress let go of my head and furiously typed on her phone. I could only assume she was updating her social media accounts with my debasement. It turns out, I was correct. She turned her phone around so I could see the picture of me with my mouth stretched wide around her cock. The caption was "Sissy's first ATM. #asstomouth #ATM #allthebitchesdoit

She continued to type, and I continued to suck. The problem was, that because of the angle, I could not get very much of her cock in my mouth. "Bring your knees closer to your elbows, but make sure you keep sucking," Mistress offered, still busy on her phone, and not paying attention to me. It was a bit awkward, but I was able to scoot my knees up kind of close to my elbows (my movement was restricted by the corset), which thrust my thong covered ass enticingly into the air right in front of Mistress Brittany. This also changed the angle of my head, and allowed me to take the remainder of her cock into my throat. I felt the balls of her strapon rest against my chin, and I smiled to myself.

I looked her in the eyes (she had put down her phone), and began to slowly lick up and down the shaft. Next, I spent some time on the balls. I glanced back up for split second, and saw strings of my cum stretch from her hand to the shaft of the strapon. Mistress got tired of waiting, rubbed the rest of my cum onto the shaft. I'd already eaten my cum a few times, and sucked a cock that had come out of my ass, and at this point I was so far into subspace that I dove forward and greedily licked off all of my seed. Clearly, I'd gone too fast though, as some of the cum ran out of my mouth and down my face. Mistress pulled her cock out, caught the cum, and jammed it back in my mouth. Then she pulled out, slapped my face a few times with her cock, and jammed it back in my mouth. I could feel some of the cum still on my cheeks and lips, but there was nothing I could do but keep sucking.

I sucked forever, and finally Mistress Brittany pulled out of my mouth, and patted my head. "You're such a good slut," she complimented me.

"Thank....thank you...Mistress," I panted. Her hands went around my back, and she mercifully began to loosen my corset. "OMGGGG, thank you Mistress Brittany," I gasped, as the air rushed into my lungs. After I caught my breath, I moved my jaw a few times and realized a decent amount of cum had dried to my face. The look in my eyes must have asked the question for me, as Mistress simply smiled and laughed.

"You absolutely may not wash that off," she stated. "Good sluts like you wear the fruits of their labor. You should be proud. Besides, it's good for your skin," she said. "Now take care of your needs in the ladies' room, and get to the couch, we have a big day tomorrow."

My legs shook badly, and almost gave way, as I took a step off of the bed. My hands flailed wildly, and caught the wall. I took a few moments to gather myself, then wobbled as best I could on my shot legs, and skyscraper heels, over to the bathroom. Holy shit, my body was in pain! I sat down and peed, then staggered back, and collapsed onto the couch, and fell asleep.