Dream Vacation

"You remember Preston and Scott," she began. Preston's been in your mouth for about ten minutes, and Scott has been in your ass," she continued. Preston had on a specialty condom, and Scott still does, that's why you couldn't tell. I flailed and moaned and thrashed, but to no avail. "Shhhhhhh, Bimbo Barbie.....shhhhh" she cautioned, and waited for me to calm down. "You're safe here, you're safe. You're just doing what bimbos do, tied on all fours, skirt flipped up, thong pulled to the side, knee high socks, skyscraper heels....big fake tits hanging down, cock in your mouth, cock in your ass...." she trailed off. "Stop worrying, enjoy your bimbo hood. Enjoy...." she said as she removed my blindfold. I blinked a few times, and saw Preston smiling in front of me. A glance over my shoulder confirmed that Scott was indeed behind me.

She was right. It's what bimbos do. I relaxed and began to bob joyfully on Preston's cock, and rock back and forth on Scott's. I moaned as I felt the weight of my tits below me, and I smiled to myself at what I'd become in such a short time, and how masterfully Mistress Brittany got me to where I'd needed to be all along.

"I'll be honest, I'm a bit confused myself," Preston said. "He has a cock. It's small, but it's there, so he's male. But those fake titties are nice. A mouth is a mouth though, and this one is a natural cocksucker. Barbie, go ahead and lick the balls a bit, sweetie," he suggested, so I did. Clearly, he kept himself fully shaved, which was nice. After a few minutes on the balls, I went back to tongue bathing and deep-throating the shaft.

"Ohhhhh...ohh Barbie," Preston started to shutter and thrust in an irregular manner. "I'm...I'm gonna CUMMM" he shouted. "I'm gonna dump my load on your whore face," he kindly warned, and instant before he did just that.

"Thank...thank you for warning me," I panted gratefully. "And thank you for shooting your cum on my face," I smiled and batted my eyes. "I'm glad I pleased you." The cum began to run down my face a bit, and I instinctively swirled my tongue around my lips and caught as much as I could. I was so lost in my new-found bimbo hood that I'd somehow forgotten about the cock in my ass! Scott was getting pretty worked up behind me though, pulling my hair and slapping my ass, and I could tell he was close as well. Then all of a sudden, I felt him pull out and heard him grunt. Then I felt his sticky cum all over my lower back and ass. He thumped his cock on my ass cheeks a few times and got off the bed.

"Thank you for dumping your load all over my ass," I winked at him.

He ignored me, and began to make out with Preston. He stopped for a moment and said, "You're a nice hole to get off in, but I prefer my man," he said, and went back to kissing Preston. I looked over and saw Mistress Brittany on her phone, I assumed she'd taken pictures and was posting them. I assumed correctly, as she brought her phone over and showed me, as she'd done before. This one was a montage of me as I'd 'progressed' during the trip. There was a picture from the beginning of the trip labeled "Boring Brian." The next was labeled "Bend over Brian." The third was labeled "Bimbo Barbie" and was of course the most recent one, of me fully feminized with cum on my face and ass. #anotherconversion #gentlemantobimbo #weskippedlady #definatelynotalady #needspermanenttits #bimbotits #cocksucker #cockrider #cumguzzler #likesfacials #asstomouth #makememoney

"Mistress I..." I started, but didn't know where to go. The cum had dried on my face, and left it stiff and crusty. I wiggled my hips a bit, and discovered some of the cum had run down my ass cheeks and dried on the backs of my thighs, while the rest dried where it had initially landed. It was all true.

"Gentleman, thank you so much for donating to my project," Mistress said.

"It was our pleasure," Preston said. "It was an honor to work with the fabulous Brittany Andrews, OMG!"

"If it's not too much trouble, I'd like to ask you for one last favor," she said, as she untied my wrists and ankles.

"Anything," said Scott.

Mistress laid down on the bed, with her cock jutting menacingly up in the air. "Reverse cowgirl," she snapped her finger at me and pointed to her cock. "You may rest on your knees this time, instead of squatting," she kindly offered.

"Thank you Mistress Brittany," I said, as I parted my ass and lowered myself all the way down onto her cock. It slid all the way in with ease.

"Bimbo Barbie needs to learn to use her hands," Mistress stated. I looked up, and saw Scott and Preston still kissing, right next to me, and I took each of their cocks in my hands, and began to slowly stroke them. I picked up speed a bit, and Scott's erection began to fade, but Preston's picked up. Mistress laughed as she began to plow me harder.

"Ride my cock better!" she commanded. "Squeeze it with your ass muscles, milk my cock like it's a real one, all good bimbos are proficient at cock milking," she informed me. I leaned back, and squeezed, which pleased her, but I forgot to stroke Preston, so he began to fade. "Yes, this multi-tasking is hard on your little bimbo brain," Mistress mocked me. "Clearly more practice is in order, until it becomes routine for you. Also, a reduction in your responsibilities will help as well. Cock riding, cock sucking, and cock stroking are the only three things you'll have to worry about, so you damn well better get good at them," she informed me.

I stroked the cocks at their preferred speed, and worked Mistress's cock with my ass. I bounced up and down like the wanton slut that I was, and I knew it. I was exhausted, and to speed things up, I put Preston's cock in my mouth. Then I decided to try something I'd seen in porn one time. I opened my mouth even wider and tried to stuff Scott's cock in my mouth as well. Problem is, I found out quickly, that is not an easy trick to do! I gagged, but they both pushed forward, and slid to the back of my throat! I could not breath, and began to panic. Scott held my head there for a few seconds before generously letting me go. I gasped and panted and tried to catch my breath, but I kept riding and stroking.

Finally they both began to moan, and I knew they were close. (Holy shit, who knew it took so long to finish someone with a handjob?? I must get better at it!) First Scott, then Preston, shot their second loads. Scott hit my face, while Preston unloaded on my tits. Mistress Brittany pulled out of my ass and pushed me off, so I landed on my back.

"Thank you for a wonderful evening, gentlemen," she said, as she stood up.

"Would you mind getting a picture?" Scott asked.

"Not at all," she replied. They each took a picture of the other with Mistress Brittany. "Get one of all of us," Mistress commanded me. They each handed me their phones. Mistress stood between them and put her arms over their shoulders. They each cupped one of her glorious breasts with one hand, and grabbed hold of her cock with their other hand. I took a few pictures. Then she invited me into the picture. I set the camera timers, and knelt in front of all of them.

Mistress kissed them both on the cheeks, and they got dressed and left. I was a cum-crusted mess, but Mistress made no indication that I was going to get to shower or change, and I didn't bother to ask. She handed me the phone and told me to upload and caption the group picture. I went with "I love gays. Fun evening with my sissy bimbo and these boys. They really broke her in." #threecockstwoholes #twoinmouthoneinass #nexttimetwoinass?#bimboslovecum #cumcoveredbimbo #ridingsuckingstroking

"Very good Barbie!" she exclaimed. "We'll get two in your ass, you slut" she growled. "In fact, when we get you fully trained, both anally and orally, that'll be double oral, double anal, one in each hand....that's six cocks at a time. I'm a smart business woman, so in order to maximize profit, you'll need to get your finishing time down much lower as well. Three minutes oral, five minutes anal, seven minutes stroking are reasonable goals. At that rate, you can make me a shitload of money. You'll have new tits in no time!" she continued, as she grabbed me and stood me up in front of the mirror.

"Mistress, I ....." I started. "My family...my life...money...diseases...job..."I stammered.

"Stop," she said. "Look at yourself. What do you see?"

I stopped and looked in the mirror. "I see a big-titted bimbo slut with long blonde hair, a slutty skirt, and stripper heels. She's topless, her ass is gaping, and she's covered in dried cum," I said.

"That's what I see too," Mistress said, as she gently ran her hands down my shoulders and cupped my tits. "I noticed you didn't even mention your locked little dicklet," she continued. She was right! I'd been so focused on getting off cocks that'd I'd totally forgotten about mine! "Next time I fuck you, I'll hit your prostate and make you cum without you even getting hard. In fact, you'll learn to cum when I let you, and only with something up your ass. For the most part, though, you'll be getting others off way more than I let you get off," she informed me.

"But I..." I stammered.

"Oh yes," she said, as she refocused. "You. What about you? When I asked you what you see, you answered honestly. I've seen many men over the years, as a porn star and especially as a dominatrix. Some men come to release stress and get slapped around a bit. They like the loss of control, the power exchange, but only for a bit. Some come in, and are truly submissive, but they are submissive men. They enjoy serving a powerful woman. Some are born into the wrong body, and I feel as though that's where you are, does that seem right?"

"I'm...not sure...I'm so confused right now," I said.

"Sure, that makes sense. The only question you have to answer is 'what makes you happy?' The rest is just taking steps to accomplish that goal. It's as simple as that," she said. "So, what makes you happy? Are you happy right now?"

I paused. After the experiences of the last several days, had I really changed? Or had she carefully led me where I really had always wanted to be in the first place? I think it was the latter. I'd always identified with the sissies and bimbos in the stories. I'd crossdressed and put things in my mouth and ass for a reason. "Yes...Mistress Brittany. The past several days have been amazing! I'd love my whole life to be like this trip."

"And it can be," she said. "Most of your concerns are really very minor. I don't let gutter trash fuck my girls, my client list is elite and highly tested, so diseases are not an issue. You won't need to worry about money or a job, because your job will be to exercise and keep your body in flawless shape, and then of course the sucking, fucking and stroking of cocks."

"Here's another thing," she continued. "You're not much of a man, honestly. Like, physically, it wouldn't take much work to make you into a really pretty girl. That has to factor into the decision. All the hormones, and surgery and makeup in the world don't matter if you aren't cut out for it, but you are, that's a gift as well," Mistress said.

I was so overwhelmed still, but I managed to repeat, "But my family?"

"Yes, them," she stated coldly. "That one can be a bit tougher. There are a few ways to handle that. As part of my patented bimbo training process, I send you home for six months with hormones that you must take daily. I don't follow up, and I don't beg. You either take them or don't. It allows me to see who is serious, and for the bimbo hopeful to see if she has the dedication to the life to follow through on her own. It also gives her a chance to see some gradual changes, and get her life affairs in order. It gives her an opportunity to have discussions with her family, or however she wants to handle it."

I looked at her in the mirror, as she continued. "Oddly, what I've found, that those who want to go from meek little man to brazen slut, and take all these meticulous, and sometimes painful, and definitely permanent steps...have trouble telling those around them that it's their life and their happiness, and they are doing what they want to do. I mean, it sort of makes sense, they are also extreme people pleasers and don't want people to be unhappy with them, but still....I mean, I get it but I don't." At this point, I felt compelled to drop to my knees and start sucking her cock, so I did.

"There we go...." she cooed. She gently guided my head up and down on her cock.

"Anyway...there are ways we can handle that. I can pose as your therapist, and we can have a meeting with those involved. I can call or e mail those involved. Basically, I explain that Brian has been unhappy as a man, and has always felt he was a woman trapped in a man's body, and that he is transitioning to womanhood. I explain that it is important to Brian to have everyone's support, and basically the choice is theirs, how they want to respond and what their relationship will be with you going forward. I say that Brian is moving forward with her life, so she can be happy, and she'd like you in it, but will be ok if you are not. In this case, we'll call you "Barbara" to your family, but of course you'll be my 'Bimbo Barbie,' she continued.

"Most of the time, the gradual changes set in, and the girl decides to bring it up when it becomes too obvious to ignore. Sometimes those around her start the conversation. Other times, I do have to step in, as I said above. I had an extreme case where the girl was having a tough time with her family, and we just went ahead with the surgeries and let her heal up. Then I put on a business skirt suit, and I dragged her into her parents' house on a leash in nothing but a thong and high heels. Oh, and nipple clamps on her brand new double d titties. And a ball gag in her mouth. And her hands cuffed behind her back.

And I told them, 'you didn't like that your son wanted to be a woman, you intolerant twits? Then you're really going to hate the full truth, that's he's now a she, despite your wishes, and that she's now my bitch!' Then I dropped her leash, and told her to hand it to me, if that's what she wanted. I watched her parents shocked and horrified expressions as their former son flailed around and tried to catch his leash and hand it to his new mistress with his big tits flopping around and his hands cuffed behind his back. It was quite amusing. She finally grabbed the leash and handed it to me, and I led her out, and she's been one my stable of sluts ever since. As you can see, we have many ways we can handle it," she concluded.

"Ytthhhh ttthhhhrrrssss," I replied.

"Well, you say that, but I'm not convinced just yet," Mistress Brittany said. "This is a major life decision, not to be taken lightly. Think about it tonight, and roll it around in your little bimbo brain for the rest of the trip. Now it is time for bed," she said, as she withdrew her cock from my mouth and patted me on the head. "You may clean up, if you wish," she informed me.

"Thank you Mistress, but I'm good," I said. I stood, adjusted the thong back into my ass, and smoothed down my skirt as best I could. My knee high socks had slid down a bit from my rough treatment, so I pulled them back up as well. Lastly, I pulled the thong strings up over the waist band of my skirt and shifted my hips a few times, so the skirt sat lower on my hips and exposed the thong in the back as well. "I have a feeling I'm going to fall asleep like this a lot. I love how I feel and look right now, and besides...I hear dried cum is good for the skin," I said with a wink.

Mistress Brittany smiled back. She got cleaned up, put on a stunning red babydoll nightie, and laid down in her bed. I laid down on the couch and fell asleep as well. Around six, I stumbled to the bathroom (damn heels again!), and took care of business. I was getting used to sitting down to use the bathroom, that's for sure. An idea struck me, and I decided to do it. I took a wet washcloth and scrubbed the dried cum off of my body. Then I snuck quietly back into the room, and managed to find the garter belt, thigh highs, and black babydoll. As quietly as I could, I took off my heels, socks and skirt, and put on the garter belt and thigh highs.

The stupid garter was impossible to fasten to the thigh highs, so I skipped that part, and refastened the heels to my feet. Lastly, I stepped into the babydoll, and slid the straps up onto my shoulders. I walked quietly to the bathroom, closed the door, and turned on the light. The garter was still really difficult, but the light helped, and I finally got the thigh highs fastened. I pulled up the babydoll in the back. I loved how the garter belt, thong, and garter straps looked and felt! I pulled the babydoll back down as much as I could, but of course it was a few inches too short to cover the tops of the thigh highs.

Next, I turned around and looked in the mirror. I adjusted my tits into the cups as best I could, but they were really big, and the cups were really flimsy. LOL, oops! Haha! My hair was a mess, so I ran my fingers through it a few times, and teased it out so it fell lightly over my shoulders. My face was also not up to par, so I put on some mascara, blush, and of course a nice coat of pink lipstick. Then, I shuffled quietly into the bedroom, and knelt on the floor next to Mistress Brittany. After a few hours of patiently waiting, the sun began to come through the curtains. My knees were very sore, but that was inconsequential. I rose, walked around the bed, and lay down quietly next to her. Slowly, I pulled the sheet away from her perfect body, and took a moment to stare at my sleeping Goddess.

There was a faint outline around the hem of her nightie, and I was in luck. She had worn her strapon to bed! I pulled up the hem, opened my mouth, and began to suck her magnificent cock. My head went further and further down, until I'd taken the entire length and my lips rested on the base. My long blonde hair fell in my face and on her red babydoll as well, the blonde on red looked good. I brushed my hair behind my ears, and kept sucking, and Mistress Brittany began to stir.

"Morning Barbie..."she mumbled. "Good...girl. Sucking dick...." she mumbled some more. At this point, I was just laying on my stomach sucking her, but I thought of a better idea. Without missing a beat, I scooted my knees up closer to my elbows and stuck my ass high up in the air. The motion flipped my babydoll up onto my back and the garter straps stretched deliciously over my ass. I moaned at how sexy it felt (and I'm sure looked!) Mistress must have felt how much closer I was to her, and she opened her eyes and saw my ass invitingly close to her face.

I can't explain how sexy and slutty I felt, I just kept sucking and sucking. Then I began to sway my hips and wiggle my ass in Mistress Brittany's face. My tits were smashed into the mattress, and I wondered how much better they'd feel if they were flesh and blood (and silicone) rather than just rubber glued to my chest. The silk of the babydoll rubbed against my smooth, hairless body, and Mistress brought hand down lazily on my ass.

I momentarily took my mouth off her of her cock (but kept stroking it) to say, "You can spank me as hard as you want. I can take it. I'm here for your pleasure." I buried her dick back down my throat, and the swats intensified. My ass warmed up quickly, but true to my word, I kept it high and available for whatever she wanted. I'd gotten her cock good and lubed, and my ass was itching for a pounding, so I said, "Now that I've gotten your big fat dick nice and hard with my whore mouth, would you like me to put it in my ass?" I offered, as I wiggled my ass a bit more to entice her. I reached back and spread my ass cheeks. I bet that looked awesome, my pink fingernails next to the black of the thong, thigh highs, and garters.