Dream Vacation

"OMG! There's no way that's going in my butt!" I cried. "It's sooo big, you'll tear me open!" I protested.

"It IS going up your ass, and there is a way. It's called 'I keep pushing'" she informed me. "And it very well might tear you open, but I guess we'll find out," she laughed. With that, she untied each of my arms from the posts and re tied them to the posts, only much lower, so I was bent at the waist at a ninety degree angle. I am not very flexible, and almost immediately my thighs and calves began to burn. My new tits tugged heavily on my chest, and helped pull me forward as well. It was an odd feeling, to say the least.

Mistress Brittany stepped right in front of me and her strapon brushed against my face. "Certainly you've sucked cock before, Barbie," Mistress said.

"Ohhhh yes Mistress Brittany, like OMG, and like I'm pretty good at it," I giggled. "I'm a good bimbo cocksucker," I looked her in the eye and licked my lips seductively.

"We'll just see about that," Mistress snarled. "I'm not sure I like that attitude, although it makes sense that a slutty whore like yourself would be proud of that. Anyway, your incentive here is that my cock is going from your mouth to your ass...and probably back in your mouth...but...you determine the amount of lube you get, so get sucking sweetie," she said as she stepped forward and crammed her cock in my mouth. The initial push caused me to gag, but I quickly got my breathing under control and started to give her a pretty good blow job. I closed my eyes, and felt her cock glide smoothly in and out of my mouth. My hair started to get in the way, and I shook my head to try and move it, but to no avail. Mistress generously pushed it back behind my ears.

I looked her in the eyes, and noticed that even Mistress was impressed. "Do you like sucking my cock, Barbie?" she cooed as she grabbed the back of my head with both of her hands and began to skull fuck me. "Do you like me fucking your whore mouth?" she asked, as she momentarily pulled out.

"OMG, yes Mistress Brittany, I love how you rape my mouth with your big cock. I'm such a cock sucking slut," I moaned, as she stuffed it back down my throat. Not satisfied by my lack of humiliation, she pulled out completely, slapped my face a few times with her cock, and jammed it back home. She roughly pushed her cock around my mouth, which made my cheeks bulge, then she pulled back out, and began to quickly and violently stab in and out, which caused me to cough and gag.

Mistress laughed and pulled out. I gasped, and coughed, and drool ran down my face. She got behind me, and stood on the first small step up to the landing, which gave her a good angle to fuck me, which obviously was what she was going to do next. At that moment, I whined in pain. "Mistress, my legs hurt," I complained. I guess while I'd been sucking her cock, I'd forgotten about the pain, but in those few seconds where my holes were empty, I became acutely aware of the tough position in which I was tied.

"Too bad, sweetie," she smiled. "I bet you're one of those lazy sluts, who is used to just flopping down on her back and taking the dick. All you hot little pieces of ass are the same, lazy. And men usually soak that shit up, but I don't," she growled, as she ripped the plug from my ass and jammed her cock inside me.

"OMGGGGG!! OWWWWW HOLY SHITTTTT!" I screamed.

"This should keep you quiet," Mistress commented, as she reached around my head and shoved the plug into my mouth. I felt the warm metal fill my mouth, and I gagged when I realized it was warm from my ass! It also tasted like my ass! Mistress put her hand over my mouth to hold it in place. "Breath through your nose, slut. Just like you're sucking cock. Breathe. Breathe. It's not too big. It is pretty fucking gross that it just came out of your ass, but that's what sluts do," she laughed. Once she was convinced I wouldn't spit it out, she put her hands back on my hips and continued plowing my ass. "Let's get those big titties bouncing," she said, and began to ram me extra hard. True to her word, the breast forms really began to tug and pull on my chest. "How does that feel slut, does it feel good? I bet that's why you got those big fake titties, so you could feel them bouncing around as you got fucked in the ass," she continued.

"Yeettthhh Mttthrssss" I muttered around the plug.

Just then, Mistress' phone rang. "This phone call is more important than you," Mistress said. "Besides, you'll still be there for me when I'm done, it's not like you're going anywhere," she added. She pulled out of my ass, strode across the room, dick bobbing, and answered it.

"Hi Helly," Mistress said. From my research, I figured it had to be Helly Hellfire. She and Mistress Brittany toured as DJs under the name "Blonde-Tour-Age." "Yes, I made it to England just fine. The slave is a wonderful young man....well currently he looks more like a young woman, hahahaha! You know how it is with these sissies," she continued. "Sure, yeah, I've got a few more dates I wanted to run by you, see if you were available for some shows," Mistress continued, as she walked back toward me with the blindfold. "Just a quick second, Helly. I've got her tied up, let me blindfold her, and get over to the desk here so I can grab my calendar."

Mistress tied the blindfold behind my head, which left me in darkness again. I heard her sit down at the desk, and tap away at her calendar as she and Helly hashed out performance dates. My poor calves and thighs were on fire! My back hurt from the weight of the tits, my asshole burned from her brutal treatment of it, and sweat poured down my face and body from the physical exertion.

"Ughhhhh!!! Oooooohhhhh!!!!" I moaned. For some reason, I tugged at my bonds, obviously to no avail.

"Do shut up, Barbie. I know you're getting impatient for more cock, but I'll get to you when I'm done," Mistress said. I felt my face get red with embarrassment for like the one millionth time. I get that Mistress is a well-known porn star and dominatrix, but I just couldn't fathom this being so "normal" to her that she mentioned it on a business phone call with a friend. I heard a noise, like a chair being moved across the rug, and then I felt Mistress' foot gently rub my poor imprisoned cock through the bikini bottoms.

"ARRGGHHHH!!!!! OOFFFFFF!!!MMMPPFHHH!!" I cried.

"Awww doesn't it feel good having that silk rub against your caged cocklette?" she teased.

Mistress was so close that I could hear Helly on the other end of the phone. "Brittany, he's a loud one, what the fuck are you doing to him?" she asked.

"I've fully feminized Barbie. She's actually a very hot little piece of ass. I've fixed a nice blonde wig on her head, but have her totally hairless other than that. She's currently a very busty young lady, with some nice big DDs glued onto, and pulling tantalizingly on her chest. Barbie's also rocking some serious six inch platform stripper heels, which I'm sure are killing her legs and back right now. I've decked her out in a smoking hot pink string bikini. Tie side, thong, so very sexy and slutty. She's loving the feeling of the strings running up her ass, I'm sure. As some finishing touches, I went with clip-on dangling hoop earrings, anklets and bracelets, and a nice spray tan, in the bikini, so she won't be going without a shirt for a while, hahaha!" Mistress laughed as she continued to rub my chastity device with her foot.

"You're fucking twisted, I love you," Helly replied. "The spray tan is a brilliant touch," she added. I couldn't help it, and cried out again. "Do you have her gagged?" Helly asked. "Sounds like she's gagged. And still so much noise..."she faded out.

"Yeah, gagged, tied up bent over...could be that. Could be that I'm rubbing her caged cock through her bikini bottoms with my foot...." Mistress Brittany stopped rubbing me, and it sounded like she had gotten up, and moved away from me. She was still on the phone, but I could not make out what was being said. After a few minutes, I sensed that she was close to me. There was more rustling on the chair, and she must have bent down to do whatever she was doing, because suddenly I felt her ass in my face. My mouth was still occupied by the plug, so I couldn't do anything, but Mistress did not waste the chance to torment me, by wiggling her divine ass (which I could not see, but could feel) in my face.

"I think we're good," Mistress said. (I had no idea why she said that)

"Get ready, Barbie, it's going back in," she whispered in my ear. "Don't worry, I'll use lube this time," she promised.

I felt a slimy coolness running between my asscheeks, followed by her hands spreading my cheeks, and some pressure on my sphincter. It quickly gave way to Mistress' cock, and slid slowly into me until her hips rested against my ass. She set something down on my back, probably her phone.

"Thhhnkkkk uuuuuu Mtthrsss," I mumbled.

"You're very welcome, Barbie," she replied. "I want to get a lot of enjoyment out of your ass on this trip, so I don't want to ruin it. That wouldn't be smart of me to ruin my toy," she added. "And I've certainly fucked enough sluts in the ass to know what I'm doing," she continued. For some reason, she reached around and pulled the plug out of my mouth, and tucked it into my thong string, at my side. "Let's keep it handy for later," she said. "I want you to confess everything to me, starting at the beginning" she whispered in my ear.

"My name is ...ugh!!!....xxx xxxxx," I moaned. "All my ...uhhhhhhh!!!...life, I've dreamed of being ...holy shit....feminized and fucked in the ....ughhhhh...fucked in the ass by Mistress Brittany Andrews. Right now, I'm tied up...Oh My Gawwwdd... in a hotel room in England, getting fucked ..ooooooo....by the goddess of my dreams," I continued.

"Is getting ass raped by me everything you dreamed of, Barbie?" Mistress cooed in my ear.

"Ughhhhh...Oh.My.God.Mistress! YESSSS!!" I screamed, as she picked up the pace and began to pound my ass harder and faster. She also began to spank me, which really fucking hurt! Within a few swats, my ass was on fire, and I began to cry. "Please Mistress, please....please my ass is on fire!!" I cried.

"I will do as a please with you, as long as I please, is that clear, slave?" she asked. It was a rhetorical question, as she continued to smack and hammer away at my ass. Plus, I was tied up and blindfolded, so I didn't have a choice. Honestly, at this point, if it wasn't for the rope that held me up, I'd be on the ground, my body hurt soooo badly! The amount of time I'd been blindfolded was beginning to have an effect on me as well. It was really weird, and unexpected. Simply put, I was a mess at this point.

Mistress Brittany changed up her assault, and instead of long, hard, fast strokes, she rammed her cock all the way in, and then began to take shorter, slower strokes. She leaned forward, latched onto my bouncing breasts with both hands, and used them as leverage for her shorter thrusts. "Such nice soft big titties on such a pretty girl," Mistress said. Then one hand slid lower, and began to rub my caged cock again. "Except for this tiny little thing," she laughed. "You're not a woman, but you're sure as hell not a man. Look at you! Just a feminized bimbo whore taking it in the ass from a divine goddess. What would your friends think? Fucking pathetic!" Her verbal abuse was spot-on, and that, combined with her rubbing my cock, the sheer tiredness and pain that enveloped my whole body, and the psychological effect of the partial sensory deprivation was just too much for me, and I broke down and cried. Complete sobbing and wailing.

"I'm...I'm not a man.....I'm...not a man..." I cried. "I'm a set of fuck holes for a dominant goddess. My mouth and ass are yours, my body is yours," I sobbed.

"I can't hold it in anymore," I heard a female voice declare. I was immediately confused, but my hearing sharpened, as I still could not see. The voice seemed to emanate from the chair...but I really did not think anyone else was in the room. It did sound a lot like Helly....

At that moment, Mistress removed the blindfold, and light flooded into my eyes. It was very overwhelming and it took me a moment to adjust. I blinked a few times, and the voice said, "I have to hand it to you, Brittany, you are a top domme bitch. You just broke him. I've never seen that before," she laughed. I looked up, and found out I was right. The voice was Helly, and it was coming from the chair.

Mistress Brittany had showed her my entire violation on Facetime! "I do believe some introductions are in order," Mistress declared. "Helly, this is Barbie." "Barbie, this is Helly," she said as she grabbed my hair and forced me to look directly into the iPad. "Do. Be. Polite. Barbie," Mistress said accentuating each word with a short thrust into my ass.

"Hello.Hello....Ms. Helly," I stammered.

"Why hello Barbie," she smiled. "You sure take it in the ass like a pro," she complimented me. "And you make a pretty hot looking girl...I might be interested," she continued.

"Thank....thank you Ms. Helly," I replied. I was so embarrassed. And overwhelmed. Mistress Brittany hammered away with no mercy, and my asshole was on fire.

"You're welcome, Barbie," she replied. "How did you two love birds meet?" she inquired.

"Well, Helly, this sissy contacted me online with a great proposition, that I found appealing. It was refreshingly original. He offered to pay for a trip to England and in return he'd serve me the entire time. It was a win-win situation for me, that's for sure. You should have SEEN the things I did to him on the plane ride here," she laughed.

"Ughhhh!! UGHHH!!!! OMG!!" I cried. Just then, there was a knock at the door.

"Hotel security, is everything ok in there, ma'am? Ma'am are you ok?"

Holy shit!! We were in for it now! Mistress Brittany handled it like a pro. "Thank you for your concern, sir, but I'm totally fine, we'll keep it down. Sorry for the inconvenience" she said.

"No problem ma'am, thank you," the voice replied, and left.

"That's fucking rich," Mistress snarled. "See the problem with the male dominated society? He assumed the Poor. Powerless.Woman. (again with the thrusts to emphasize her point) was in trouble. He had no clue that the genetic male was the one getting raped," she laughed. "Do keep it down, Barbie," she growled, as she slapped me in the back of the head.

"Good point," Helly interjected.

"I'm already recording this, but let's get a few selfies for my scrapbook," Mistress leaned over my shoulder, stuck her phone in my face and snapped a few pictures. She pulled it back and laughed. "The look on your face is priceless!" she said. "I need to share this one," she continued. Her hands were no longer in contact with me, and I heard her typing on her phone. "And there we go," she said with finality. "Shared to instagram, tumblr, and twitter, do you want to see?" she asked. Before I could answer, she shoved her phone in my face again, with my humiliation uploaded to the internet.

"Sometimes I Facetime my friends while I'm ass raping my sissies with @hellymaehellfire." #multitasking #strapon #assraping #feminization #futureboobjob? #bimbo #bigtittysissy #bigfaketits #stripperheels #humiliation

"OMG Mistress!!" I cried. "I'm...I'm ruined!!"

"Fucking amazing!" Helly laughed. "Yeah, no...it's totally on all Brittany's social media feeds now. You're ruined, bitch," she laughed.

"Relax and enjoy this, Barbie," Mistress advised me. "This might be the beginning of the rest of your life," she said, as she lightly ran her nails down my back. "But for now, I'm pretty exhausted, so we're going to wrap this up for the night," she said, as she pulled her cock partially out of my ass, snapped another picture, and then withdrew the rest of the way. She spread my ass cheeks and snapped a few more pictures. I sniffled and moaned a sigh of relief. "Say good night to Ms. Helly," she told me.

"(snif)(snif) Good night Ms. Helly," I panted.

"Good night Barbie," she laughed. "Sweet dreams!" she said and blew me a kiss.

"Chao for now, baby," Mistress said to her, and ended the Facetime conversation.

She came around in front of me, typing away on her phone. "I uploaded those last few as well," she informed me. Mistress shoved her phone into my face again, to prove that she wasn't bluffing. There, on social media, next to the other pictures, were the pictures of my poor ass and asshole with the caption "Post ass-raping" and the tags #girlyass #womanorman? #bubblebutt #aftermath #gaping

She untied me, and I collapsed onto the floor at the foot of the bed. Mistress kindly tossed me a pillow from the couch, and an extra blanket. It was clear she wanted me to sleep on the floor, so I curled up and got as comfortable as I could. It didn't matter, because I was asleep within minutes. I woke up a few hours later because I had to pee so badly! I tried to stand up, but stumbled and fell over because of the heels, and the strange center of gravity that my tits created. As quietly as I could, I made my way to the bathroom, sat down, relieved myself, and went back to sleep.

Mistress woke me up at some point the next morning and told me to get ready. Still shaky and sore from last night's treatment, I staggered into the bathroom and looked at myself in the mirror. Mistress was already dressed in a nice summer dress, and sensible but sexy heels. She removed the wig from my head, and took a step back. "Your ass does need a break," she said thoughtfully. "But...I don't want you to forget your place..."she continued. "And I really love how those titties look on you. I do have the solvent to take them off, but here's what we're going to do," she said. "We're going to continue our sightseeing, and the only thing in your ass will be your thong. That should make you feel nice and sexy."

"OMG, thank you Mistress Brittany!" I exclaimed.

"I'd hold off on that," she cautioned. "Because you're leaving the tits on," she finished with a cruel smile.

"Mmmmm....Mistress?" I gulped.

"Why yes, slave," Mistress responded as she removed my bikini top and replaced it with the black bra and thong set I'd purchased last night. "Told you to hold off on thanking me," she laughed. "Here's the thing, I don't want to draw attention to us, so we'll have you wear an oversized raincoat, so it just looks like you're fat. It's not ideal, as I'd prefer not to be seen with you like that, but it'll do. You'll be amazed at how feminine you'll feel with a thong running between your ass cheeks and your tits bouncing all day. And your back will be sore, that'll be a real female experience for you," she said. Mistress had me put on my polo shirt and khakis, as well as the rain coat, and I looked at myself in the mirror.

I was super nervous, because I knew what was going on underneath my clothes, We left the hotel and stopped to get breakfast. The waiter asked to take my coat, but I politely declined, which I'm sure looked a bit odd, though the alternative would have been much odder. He did give me a strange look when I took out my card to pay, and I looked down and saw the nail polish on my fingers!! I almost died of embarrassment! Mistress got a good laugh out of that. The rest of the day, I was very self-conscious about my fingers, and tried to hide them when I could.

We saw the many sights of London, which were wonderful, and Mistress did a decent, but not obscene amount of shopping on my credit card. Of course, I had to carry all her bags around like a pack mule, and I was to stay two steps behind her as well. By mid-morning, my back had begun to hurt from carrying around those big heavy tits, Mistress was right! The bags were heavy as well. It rained almost all day, so the coat came in handy, and my hands were full of bags anyway, which I tried to hold in front of my chest, just in case. Mistress immediately saw though that, and did not allow it. "Oh sissy, good try. Are you afraid someone will see your tits?" she smiled, as she pulled my arms down to my sides.