Dream Vacation

My legs and ass had obviously not recovered, the water was getting in my mouth and eyes, and was really distracting, and Mistress took great joy in intermittently twisting my nipples or slapping my ass. "That's a good fifteen minutes of cardio," she declared, as she pulled out of my ass. "Running and climbing stairs are so boring. Fucking a slave's ass is so much more exciting and invigorating," she exclaimed. "Nothing beats waking up and raping someone's ass to really get the blood flowing and make you feel like you can take on the day. If you can dominate an ass, you can dominate a day," she said. "I should put that on a t shirt," she laughed. "Plus it's a great ab workout and way better than crunches. Anyway, shower and get out, we have places to go, slut," she directed. We both finished showering and got out.

Mistress Brittany put on a long, flowing purple maxi dress, that was almost a Greek style, and fashionable, but comfortable sandals. She looked amazing! I put on a pair of khaki pants, a red polo shirt and a pair of brown shoes. "Those pants make your ass look really sexy," Mistress said.

"Thank you Mistress," I blushed. It was a little embarrassing to be objectified. Now I have a small taste of how women feel! "You look divine in that dress."

"Why thank you, slave," she smiled. We started to walk down the hall, and trust me, my legs and ass hurt! I walked with a noticeable limp, and Mistress smiled and patted me on the ass. "Walk it off, champ," she said. We walked down the street, and it got a bit better. Since we had not had breakfast, we stopped in a restaurant and got some. I enjoyed the English breakfast, though I thought it was strange they had tomatoes and baked beans with it, but when in Rome, right? Mistress had a light breakfast, and we were on our way. We saw the sights of London, they were amazing.

We had made a circle back to near our hotel, and Mistress Brittany said, "I need to freshen up," so we went up to the room. After she came out she said, "I suggest you avail yourself of the opportunity as well, as there is a real shortage of washrooms in this town." I was thankful that she knew that, and listened to her advice. By and large, the walk had helped my legs quite a bit, though I was still a bit sore in my legs, and definitely my ass. "Go ahead and take care of this, while you're in there," she said, and she passed me in the chunky rubber butt plug. I gritted my teeth, spread my ass, and worked it home. The thong string helped hold it a bit, but the tightness of my pants held it as well. I glanced back over my shoulder in the mirror, and saw that (thankfully), there was no bulge from the plug in the back of my pants. I took a few steps, and wow! There was some pain, but mostly my ass just felt full. I looked back again, to make sure there was no bulge.

I went out and presented myself to Mistress Brittany. Immediately, she tapped my ass to make sure the plug was in place. Then she smiled and tapped it a few more times, to wiggle it a bit and tease me. We left and began our walk down the street. Mistress would, from time to time, pat my ass, which made my face turn bright red. "Relax sweetie," she cooed in my ear. "No one knows you have a big black rubber plug in your ass. Or....do they??" she smiled. "Such a dirty, dirty boy, walking the streets of London with your ass full of big black rubber cock....maybe we should replace it with the real thing," she threatened.

"No Mistress, no," I whispered back.

"We're going to Westminster Abbey," she informed me, as we got there. We walked inside and took the tour. As I looked around, I realized it was basically just a shine to old dead royals. It was very cool to look at, but a bit strange as well. "You sinner," she said into my ear. "This is a house of God, you filthy slut," she continued. She grabbed my ass and gave the plug a hard shove. I bit my tongue so I didn't yell. "I've got a rubber nun's outfit, but it's not with me. Too bad...I could dress you up like a choirboy, bend you over one of these pews....Even better, I could put you in my other rubber nun's outfit, the short one with the ass cut out, thrash you with a ruler and stick my big cock up your butt...." My poor cock strained against its prison, but there was nothing I could do.

She pushed me against the wall in a corner, circled my waist with her arms, and worked the plug a few more times. I felt her breasts mash against my chest, and I closed my eyes and moaned. Mistress took my hand and led me out of the church and into the street. She dragged me into a secluded alley, and pushed me against a wall, face first. Again, she put her arms around my waist, and began to thrust her hips at my ass. When she came in contact with me, it drove the plug deeper, so it was like she was fucking my ass. My face was so red, and I was in sexual agony.

"It's time for dinner, bitch," she said. She took my hand, and led me down the street. We stopped at a nice restaurant, and went inside. The minute I sat down on the plug, my ass cramped. It hurt so badly! Mistress discreetly jiggled my cock cage with her foot, and smiled at me. I bit my lip and almost cried. "Maybe I should have you drop a few pieces of ice down your pants," she whispered.

"Oh my God, please no, Mistress," I begged.

"Very well, young man," she said. "Would you like some relief?"

"Yes please, Mistress!" I whispered quietly.

"You may go into the bathroom and remove the plug from your ass," she replied matter-of-factly.

I quickly got up and walked briskly to the bathroom before she changed her mind. Once inside, I took down my pants, and ejected the invader. It felt so good to have my ass empty for once! I put the plug in my front pocket and rejoined Mistress at the dinner table. "You may place it in my purse," she generously offered. I did so.

We made what appeared to be small talk, but if anyone could really hear us, they'd know it was anything but normal small talk. Mistress looked me directly in the eye and said, "One time I blindfolded a sissy, tied her down and let ten men gang rape her mouth and ass at a truck stop. Would you like that," she smiled and leaned forward.

"No Mistress," I blushed, and kept eating.

"Another time I kept a sissy blindfolded, ears plugged, gagged and tied to my bed with no release for a week straight. I take that back, I put him in heels and cuffed him to the treadmill every now and then. He subsisted off protein paste that he sucked through a wall mounted dildo, and I'd rape his ass whenever the mood struck me. He'd have no idea when I entered the room, so the reaction each time I stuck it in his ass was simply priceless. My record was eight times in one day! It was fucking extreme. Do you think you could handle that?"

"No, Mistress," I whispered. "I'm nothing."

"Not nothing," she smiled. "More adventurous than most of these vanilla souls," she said as she nodded to the room. "Tell me about yourself, a little, slave. What is your ultimate fantasy?"

"This is, Mistress!" I replied.

"Well, sure," she said. "But really? If money wasn't a thing, if real life wasn't a thing...what is your dream?"

I blushed. "Well..." I started.

"Really?" she exclaimed. "You're shy? After all this...come on, you can tell me, young man," she reassured me.

"Part of me obviously likes being humiliated as a male, but if I had my way, and had no family to worry about, or real life, or anything like that, I think I'd like to be made into a total bimbo. Like, if I could be really hot, and just be a total slave bimbo sex object. Have really big tits, and wear slutty clothes, and super high heels, and just take cocks in my mouth and ass all the time. Kind of like your one sissy you said you had."

"I know," she said. "Every single man I've ever ass raped has confessed substantially the same thing: that they wish they were some form of submissive woman. I could probably write a doctoral thesis on the subject," she continued. "But until then, I'll keep taking your money and raping your asses," Mistress Brittany laughed. "Check please," she called to the waiter, as he passed.

I paid the bill, and we left. My ass was so relieved to be empty. Mistress held my hand, and we walked down the street, but not toward the hotel. We walked for several blocks, until she turned into a store. As I looked around, I discovered we were in a very upscale adult store. My face got really red, because I had a pretty good idea what we were about to buy wasn't going to embarrass her. In fact, she walked around with an air of total confidence, which makes sense, given her profession and experience.

Confidently, she strode over to an area of items that initially, I did not recognize. I looked again, and saw every conceivable size of breast forms. "Of course these are too small," she said as she held some Bs up to my chest. My eyes darted around, to see if anyone was looking, and my face burned even redder. "These might be a little TOO big," Mistress laughed, as she held up the biggest size they had. The tag on those said "G." "How about some nice big double Ds?" she asked rhetorically as she handed them to me. She also grabbed a bottle of adhesive, and a bottle of solvent, and pulled me down the next aisle, which contained a wide array of lingerie.

Mistress Brittany must have had a pretty good idea of what she wanted, because she grabbed two tiny thong string bikinis, one in pink and one in baby blue. Next, she grabbed a lacy black garter belt, black thigh highs, black thong (with ties on the side) and silky black babydoll nightie with pink trim. Then, we went over to the shoe section, and Mistress sat me down on a chair, and handed me a pair of platform stripper heels. They were black, open toed, and had seven inch heels. She slid them onto my feet, and grabbed my hands to help me stand.

I stumbled, and almost fell, but Mistress helped me. I took a few wobbly steps. "Heel to toe, sissy," she cautioned me. "And take small steps like a lady, let's not clomp around like a horse," she added. "Nevermind, we'll work on it later, take them off," she said dismissively. I sat down, and took them off, glad to be out of them, at least in public. We walked by several racks of bras, and Mistress smiled, and took a lacy black quarter cup style one and held it up to my chest. "I think that will work nicely with your new tits," she smiled. She checked the tag "38 DD, that should work, but we'll try it out," she said. "Just a few more things," she told me.

The next aisle had tons of corsets, in all styles. "You do need to work on your girlish figure," Mistress said. She held up a serious black leather corset. This was not one of those flimsy costume pieces, this was a serious corset. Mistress handed it to me, and we continued to shop. By this point, my hands were pretty full, and I knew the bill was going to be pretty high, but that did not matter. "One last thing," she said, as we got to the front of the store, and saw a glass case full of butt plugs. Mistress pointed to a medium sized metal one with a pink jewel in it, and told the girl behind the counter that we would take it. I met her gaze for only a moment, and I was so embarrassed!

"Slave, you'll need to go try on the bra," she told me. "Make sure the tits look good too!" she shouted, as I headed for the dressing room. I took off my polo shirt and slid the bra straps up my arms. I tried to close the clasp behind my back, but it was really hard! I looked in the mirror, and finally got it hooked. Next, I unboxed the breast forms, and set them into the cups. The cups really didn't contain them at all. In fact, it really just held them up, the adhesive would probably have to do most of the work to keep them in place. They looked good, though. Just then, Mistress burst into the dressing room.

"Take off the bra and tits," she commanded. As I did that, she pulled the straps of the corset up my arms, and began to lace it up behind my back. She put her knee in my back, pulled the laces REALLY tightly, and tied them. I could barely breathe! Mistress told me to take off my pants and socks, but I could not even bend over, the corset was so tight. I sat down, and Mistress kindly removed my pants and socks. She stood me up, and fastened the garter belt around my hips. I sat back down, and carefully rolled the thigh highs up my legs and stood. I fumbled with the garter straps. Mistress laughed, "Not a very well trained slut," she chided me, as she quickly got all the straps connected for me. She pre tied the thong strings, and handed it to me. Of course, I had to sit down and slide it up my legs, since I could not bend in the corset.

I moaned as the silky fabric worked its way between my ass cheeks. Mistress pushed my poor caged cock down, and re tied the strings on both sides MUCH tighter. I groaned in agony and Mistress laughed. "Just a little bulge still in the front, like a good sissy bimbo," she said. "Put on your shoes, shirt, and pants. You're lucky I'm not making you wear the tits and stripper heels," she added.

"Yes..yesss Mistress, thank you Mistress," I panted. I was seriously dying in the corset.

"In fact, I am being too nice," she said. She tugged my pants down, pulled my thong to the side, and slid the metal plug up my ass!

"Oh my GODDDD!!" I yelled.

"Shut up," she snarled and slapped my face. She adjusted the thong back up my ass, and fixed my pants. "No one can even tell anything's out of place with you," she said. I looked in the mirror and she was right. Maybe my shirt was a bit odd because of the corset, but other than that, I looked normal. No one would know if they didn't know, and I don't think anyone would have reason to believe a random guy walking down the street would be wearing a corset, thigh highs, thong, and butt plug under his polo and khakis. We paid for our purchases and left. The nylon felt good on my legs, and the thong felt strange, but wonderful under my normal male clothes. The corset was another story, it was torture! The plug in my ass was not comfortable either, and I hoped that we were heading back to the hotel, especially because I was carrying a large bag with the adult store's name on it.

Mistress Brittany had other plans, and she took us into a drug store, and into the cosmetics area. She held up various shades of lipstick to my face, so people knew it was for me. She finally settled on a bright red, as well as some mascara and eyeliner. Then she grabbed a self-tanning spray, a few other things I didn't see, and we paid and left. Finally we headed back to the hotel, and I collapsed on the bed once we got to the room.

"Oh we're just getting started, bitch," Mistress snarled. She took off the corset, and I breathed a sigh of relief. She took off the thong, garter belt, and thigh highs as well, which left me naked (except for the cock cage, of course!) Mistress Brittany ripped the plug from my ass, dragged me into the bathroom and tossed me in the shower. "Put on the bikini bottoms," she told me. I unwadded the string bottoms of the pink suit and pulled them into place. Mistress squirted the adhesive onto the back of the breast forms and slapped them on my chest, and pressed hard on them. After about thirty seconds, she let go, and I felt their full weight for the first time! Mistress wasted no time in taking the bikini top and tying it around my neck and behind my back, and then adjusting my new tits in it. She told me to close my eyes, and the next thing I knew, I felt a mist, and figured she was spraying the fake tan on me. I looked in the mirror and saw that I was correct, my entire body was now a glow with a nice fake tan.

"Take a look, sissy," she told me. I opened my eyes and looked in the mirror. She momentarily moved the string on my hip, and on my back, to check my tan. The difference was pretty profound. "I guess you won't be going without a shirt for a while," she laughed. "Sit back down, and put your feet on the edge of the tub." I did. Mistress reached into the bag, and took out a bottle of pink nail polish. "The only reason I'm doing this for you, is to save some time, and so it actually looks good," she said. She painted my toes and fingers a bright shade of pink, which matched my bikini. Next, she pinned a long, blonde wig on my head, and ran her fingers through it a few times.

Mistress reached into the bag again, and clipped large hoop earring onto my ears, and put a few jangly bracelets on my wrists, and anklets on my ankles. "Next time it's real earrings and a belly button ring, slut," she informed me. "Maybe some tattoos to mark you as mine," she added. "Get in the bedroom and put on the heels!"

I staggered into the bedroom, my new tits wobbling and jiggling and bouncing uncontrollably in the tiny bikini top. The earrings bounced against my face, and the jewelry made a fair amount of noise as well. Mistress Brittany swatted my ass as I walked by, and laughed. "All that movement and noise, what a good bimbo," she said. "People will notice you right away....in case those babies didn't get their attention first," she laughed. "Practice walking in those shoes," she told me, and disappeared into the bathroom.

She came out a few minutes later in the matching baby blue thong string bikini. My poor cock tried again, in vain to get hard, but was of course crushed by the chastity device, and I moaned in pain. "You look divine, Mistress Brittany," I said.

"It was lovely to meet you at the beach today, Barbie," she said. "I'm glad you decided to meet me in my hotel room, I think we're going to have a LOT of fun," she continued. "I will warn you, I like things that are a little...different..."she breathed in my ear (from behind me) and took a firm hold of my tits. I closed my eyes and moaned. I felt something cover my eyes, and get tied behind my head, and my world went black. She had blindfolded me. She took my hand and led me across the room until my toes came into contact with the step (that lead up the couch/television area). She spun me around, so I faced back toward the bed. Her foot nudged my legs about shoulder-width apart, and then there was nothing for about a minute. My mind raced with anticipation! Maybe she had left. Maybe she would return with someone else. Maybe she was setting up her video camera.

Then I felt rope around my ankle, and a slight pull outward. This also happened to my other ankle, and I assumed she'd tied me to the rail posts of the railing that ran from each side of the stairs to each wall. Then I felt rope around one wrist, and pulled outward, and then the other, same thing. Mistress had tied me spread-eagle to the posts! There was no movement and no sound for a few moments, which again, built my anticipation. "Do you like butt sex, Barbie?" she whispered in my ear.

"I'm...I'm a virgin back there...ma'am," I replied.

"You can call me 'Mistress Brittany.'That's adorable, Barbie. No really? A big titted bimbo like you? I don't buy it. I like butt sex, Barbie, but I don't take it, I give it!" Mistress cooed. "So I thought I'd be nice and get your tight little ass ready for me so it won't hurt so much later."Her delicate fingers pulled my thong to the side....and she slid the metal plug back into my ass. I thrashed at my bonds, but the held fast.

"Ohhhh my GAWWWWDDDD!!!," I shouted, as the cool metal found its way into my rectum. "That's like soooo big in my poor virgin ass!!" I cried.

"Stop it with the 'virgin ass' thing," Mistress laughed.

"Ohhhhh....soooo...cooollld! And I swear, ughhhh, it's virgin!" I repeated, as I swayed in my bonds and tried to get the plug situated as comfortably as possible in my butthole. "So like, ummmm...OHH!!!!...I see I'm like your sex slave now, that's cool. I've done some of this with an old boyfriend. But um...how do YOU give butt sex? You're a girl," I asked innocently.

"With THIS!" Mistress Brittany replied as she pulled off my blindfold and pointed to a six inch strapon she wore over the bikini bottoms.