Dream Vacation

The next morning, Mistress woke me up and told me to strip completely naked and get in the shower. She took off my wig, and to my surprise, the glued on tits. Immediately, my back felt relief! The hot water felt amazing, and I finally felt clean! My entire body (including my asshole and especially my poor cock) was still in pain, but I felt refreshed and ready for the day. For some odd reason (that I was not about to question), Mistress directed me to wear the black thong and my normal khaki pants and polo shirt. I was suspicious, but did as I was told. We took a taxi to the train station, and rode the train four hours to Edinburgh, Scotland.

The scenery on the ride was beautiful. We talked on the way there. She would occasionally change the topic to sex, or her work, or subtly rub my cock cage to torment me, but for the most part, it was an easy ride (I guess it's all relative to what I'd already experienced!) When we arrived in Scotland, it was cloudy and cold, and very hilly! I dragged all our luggage into our hotel room. The view was amazing, and the room was very nice. Mistress told me to relax, and she left with my credit card. About an hour later, she came back, with a rather large bag in her hand. I trembled with anticipation, but not for long. She took out two kilts, two pair of knee socks, and two kilt shirts.

Once she unfolded them and laid them out, I saw the problem. They were both women's kilt sets. One had quite a bit less material, and I assumed it was mine. "Put this on," she commanded. I stripped out of my clothes, and put on the short kilt, shirt, and knee high socks. "Put on your regular black dress shoes," she said. Oddly enough, she also had me wear a pair of snug boxer briefs under the kilt.

"Thank you, Mistress," I said, truly relieved I did not have to wear the heels.

"You're welcome slut," she replied. "Do a nice little spin for me," she continued. I did as she said, and looked in the mirror as I did so. The kilt was a few inches above my knee, definitely too short for a male, that's for sure! Mistress changed into the matching outfit. Her kilt was a few inches above the knee as well, though longer than mine.

"You look amazing, Mistress!" I complimented her.

"Let's go," she said. She took my hand and led me out the door. The Scottish sky was cloudy, and the air a bit nippy, especially in the lightweight shirt and kilt. Mistress strode down the street confidently with me in tow. We stopped at a souvenir shop, and the shopkeeper gave us a questioning twice over.

"A wee bit short eh lad?" he observed.

"Yes, it is," Mistress answered for me. "I bought both outfits," she continued then stopped.

"Aye," he replied politely, and went about his business.

We left, and continued to walk around the city. I caught several strange looks, and several people made mention of how short my kilt was, and how it was more suited to a woman, or that we should switch. Some of the people got on me a bit more, and after one particularly embarrassing encounter with a few teenagers, I'd had enough. "Mistress, please. This is sooo embarrassing!!" I complained. "I'll do anything, please!" I added.

"Anything? I like the sound of that," she said. "We're going back to the hotel," she stated, and soon we were back in the room. She had me take off the shirt, and put on the familiar black bra. Next, she glued the fake tits back into place, much to my chagrin. The long, blonde wig was affixed to my head, and Mistress applied full makeup to my face. I was also commanded out of my male underwear and to replace them with the black thong, which I did. I stood in front of Mistress Brittany silently. She pulled me over the mirror and did some adjustments.

She loosened the ties on the shirt, which gave an even better view of my cleavage (and the black bra under the white shirt didn't too much to preserve my modesty!) The kilt was already pretty short, but Mistress went one step further and rolled the waistband once, to shorten it a bit more. The shirt did not quite make it to my waistband, so when I moved one could occasionally see a band of exposed skin around my midsection. Mistress reached under the waistband and pulled my thong strings up over the waist band, so now THOSE were occasionally visible as well!

I looked in the mirror and my face turned really red. "Mistress, Mistress please, no!" I begged. "I really don't think I'm ready..."

"You're fucking ready, stop whining," she stated. "I really wanted you to go out in the heels, but it's so hilly I don't want you to fall and break your fucking ankles, otherwise your ass would be wearing them," she continued. "Besides, if you think about it, you look like a hot girl. The outfit covers you, it's just sexy. It's no worse than what a lot of girls wear all the time. It's less embarrassing than going out as you were this morning, that shit looked ridiculous," she laughed. "Buck up, baby, we have some more shopping to do," she said. She handed me a rather large handbag, which I threw over my shoulder, and we left.

We left the hotel and hit up a few more shops. People noticed us, that's for sure! No one said anything, but I had a sneaking suspicion they were looking. How could they not? I know I'd be looking if I saw two girls dressed like that. It didn't help that Mistress held my hand and tried to make it look like we were a couple. After a bit, I began to own it, and my embarrassment faded. Mistress noticed the change. "Now you're starting to get it," she whispered. "Now you're accepting it like a good girl."

I looked up and saw that we were in front of a pretty nice restaurant. Mistress led us inside. The man at the front greeted and offered to seat us. "I'll go ahead and sit down, but Barbie here needs to use the ladies' room, if you don't mind?" she informed him.

"Very well ma'am," he said to her. "It's right that way, ma'am," he said to me. I did not try to speak, but rather, nodded politely and headed in the direction he indicated. Mistress looked back and pointed to my purse. Once I got to the bathroom, I looked inside and saw what she meant. She had packed my stripper heels in my purse, and obviously wanted me to wear them to dinner! OMG!! I sat down on the toilet and my heart raced. Logically, I'm not sure why, considering everything else I'd done, and my current outfit. I removed my dress shoes and put them in my purse. Then, I took a deep breath, and slid one foot into the heel. My hands shook as I fastened the thin black strap with my pink-painted fingers. Once both heels were fastened, I took a timid step, and then another. After a few laps around the bathroom, I walked confidently out to meet Mistress Brittany at dinner.

"Something's not right," she said. She looked in my purse and shook her head. "I could tell by the way you walked, you forgot something," she said in a low voice. "I'll give you the benefit of the doubt, that you didn't see it, but go back and put it in," she finished, with a wave of her hand. Immediately knew there was some kind of butt plug in there, damn it! I stood up and walked back to the bathroom, and went back in the stall. My suspicions were confirmed, and in a big way! It wasn't the cute jeweled butt plug, but rather, a medium-sized black chunky rubber one. With no lube options, and not wanting to keep Mistress Brittany waiting, I slid the plug into my mouth and got it as wet as I could as quickly as I could. Then I put the toilet seat down and set the plug on top. Squatting on the heels was uncomfortable, but I had to, and I bit my tongue, spread my ass cheeks and slowly lowered myself down onto the plug. My ass was so sore and stretched from Mistress' abuse of it over the past few days that each progressive inch was agony. Finally, I got the entire thing buried to the base, and I fixed the thong to hopefully help hold it in place.

I stood up and gritted my teeth. That thing was pretty uncomfortable. I swayed my hips side to side to at least seat it a bit better, and that did help. I smoothed out the kilt, and took a few ginger steps. Mistress and told me heel-to-toe, so I took a few steps like that. I also found that if I swayed my hips side-to-side that helped as well. It was a pretty womanly stride, if I do say so myself! I sashayed my way out to the table and sat down with a pained, but confident smile.

"Such a good girl," Mistress cooed, as she patted my leg. Then she took the toe of her shoe and jiggled my cock cage with it. I put my napkin to my face and turned away, it was such a painful tease! Then she stopped and smiled. Our table was very close to a table with two well-dressed men, who were clearly gay. They kept looking at us. One of them finally spoke.

"I really hate to bother you," he said politely, "but are you the fabulous Miss Brittany Andrews?"

"Why yes I am," Mistress answered politely.

"We are big fans of all your work," he replied, and shook her hand. "That's all I wanted to say, is we love you. I'll let you get back to your dinner," he said.

"Well thank you very much!" Mistress said. "No, no, pull up your table, you can eat with us," she offered generously.

"OMG!! Really? Of course!" he said, and they pulled up their table and sat with us. "Who is your friend?" the first one (Scott) asked.

"Funny story about 'her'" Mistress emphasized the pronoun. "'Barbie' here is really 'Brian.' He's a businessman, a great young man, really. He and I are vacationing. It was his idea," she continued.

"OMG!! No wayyyyyy!!" the other one (Preston) almost shouted. "You look fabulous!" he said.

I was able to mutter out, "Thank you..."

"Yes way," Mistress Brittany countered. I was so humiliated, I just looked down. "You boys want to see what we've been up to? Pull up my social media accounts," she said. Both men pulled out their phones, and I could tell the moment they hit her sites.

"Her dick looks pretty big, I hope you had some practice beforehand or I bet that shit hurt," Scott said.

"Sweetie, how is your ass?" Preston asked me.

"It's pretty sore," I admitted.

"It's pretty in use right now," Mistress added. I looked down and squirmed uncomfortably in my seat, but knew better than to say anything. "She's sitting on a pretty big butt plug so that her ass is ready for me later," Mistress clarified.

Preston lightly took hold of my hand, and I looked him in the eye. "Sweetie, it might not seem like it, but that was pretty nice of Mistress Brittany. A lot of times I do the same thing so I'm ready for Scott when we get home, it makes it so much better for both of us. Plus wearing it out in public makes me feel a bit horny and naughty, you know?" he winked.

I have no problem with gay people at all. I'm pro-gay marriage. I think everyone is equal. I was still very uncomfortable having this conversation with Preston, and Mistress Brittany could tell. "Barbie, what would you say if I invited these fine gentlemen back to the hotel with us, and let them spitroast you like the whore you are?" she cooed.

"I'd...I'd be very uncomfortable, Mistress Brittany," I started.

"I'm sure you would be, these two look like they are packing some good sized dicks," she laughed.

"Not like that Mistress. Please, Mistress Brittany. No offense guys, you are very handsome gentleman, but I'm just not ready for it yet," I replied. Oh shit! Talk about a Freudian slip! Mistress caught it.

"Well boys, it seems as though Barbie is not ready for it YET!" she laughed.

"Oh it's totally fine," Scott said. "Sounds like she'll get there, under your excellent tutelage," he continued. "It was a pleasure meeting you both, have a wonderful evening!"

"You as well," Mistress replied. They left, and Mistress addressed me.

"Barbie, I feel as though you've changed since this trip started," she began. "Would you agree?"

I thought for a moment. "I think I would agree, Mistress."

"In what way have you changed?" she continued.

"Well....in the beginning, I simply wanted to be fucked in the ass with a strapon and controlled and humiliated by you, a strong, beautiful, womanly Goddess," I said. "I guess I saw myself as a submissive man, at first. But of course I'd dabbled in cross dressing on my own, and in the course of this trip, you've certainly enforced that most severely....and it's really intensified my feelings of submission, and enjoyment of what we've done. I'd say, right now, that I more accurately identify with the submissive female role in sex, does that make sense?"

"It most certainly does," she said quietly. "Think about who you're talking to, sweetie. I've been doing this for years. I've met so many so-called men like you. It always starts out the same, and it usually ends up the same. I simply lead you where you want to go. It's a journey to self-actualization, and I am the guide. You mentioned you are not ready for those two men 'yet.' What is your hang up?"

"Mistress, I am not gay," I started.

"I hear that so much," she cut me off. "First of all, these terms are so outdated. They are based on some old fashioned definition of sexuality. We're liberated now, we're free. Stay safe, but do what feels good for you. Barbie, you're big titted slutty bimbo whore. You love dressing like a whore. You love being sexually used. You love offering up your mouth and ass, ideally at the same time. And you can do that with women like me, but really if you identify as a woman, then doing that with women is gay. Women like you need to be dominated by large cocks. Cocks that squirt cum. Does that make sense?"

I paused again. I couldn't really argue with her logic. "But I..." I stuttered.

"But you still have this ingrained hang up," she said. "You said you weren't ready 'yet.' I heard you say it. Freudian slips happen for a reason," she continued. "True honesty happens when you're unguarded and just say what's on your mind. Mistress Brittany looked me directly in the eyes. Have I been right so far on this trip?"

"Yes Mistress," I said.

"Have I pushed you past your boundaries a little at a time?" she said.

"Yes Mistress," I replied.

"Are you happy to be sitting here in public, with big tits, towering heels, a tiny skirt, and a plug in your ass?" she asked.

"Yes Mistress," I repeated.

"Barbie, are you happiest when you're being used like, and exposed as, the bimbo whore you are?" she asked.

"Yes Mistress," I said again.

"Do you trust me?" she said.

"Yes Mistress," I said, without a pause.

"I believe it's time to go," she said. She paid the bill (with my card) and led me back to our room. I collapsed in a heap on the bed, because the walk in those heels, and with that plug was fucking difficult! I took what time I could, because I figured (correctly) that Mistress was not done with me yet.

She slipped a blindfold over my eyes, and I immediately slipped off into subspace. "I'm going to grab my dick, get up on all fours," Mistress said, and I obeyed. "Let's make you a little more comfortable," she offered, and I felt her slide a few pillows under my stomach for support.

"Thank you Mistress Brittany," I cooed. No sooner had I said it, then I felt the fabric of my kilt lifted up off my ass cheeks and land on my back (as my position had caused my shirt to slide up my back quite a bit). Mistress ran her hands over my smooth ass, and raked it gently with her fingernails. I subconsciously wiggled my ass toward her, in anticipation, and felt her long, cool, rubber cock brush up against me. She leaned over me, and I felt her large, beautiful breasts against my back, and her hands grab onto my tits and massage them over my shirt and bra. Her hips and cock ground against the plug, and drove it in deeper.

"Mistresss.....Mistress Brittany pleeeeasseee," I moaned, as writhed and ground my ass back against her. "Please take your slut," I begged. "Please fuck your slutty bimbo Barbie in the ass with your cock," I continued.

"How should sluts be treated?" Mistress asked, as I felt her hand grip, and slooowwly remove the plug from my ass.

"Ughhhhh!!! Sluts should be treated like sluts, Mistress. Oooooo....sluts should be fucked by big cocks," I continued.

"What makes a bimbo happy?" Mistress asked, as she slowly worked her cock into my ass, until I felt her bottom out, and the front of her thighs rest against the back of mine.

"Ughhh!!! Bimbos are happy when they're getting fuuuckkkked!" I squealed.

"That's a good girl," Mistress sang, as she sawed in and out of my ass. "Act like you want it. Don't be a 'do nothing bitch.' Bounce back on that cock, grind on it, fucking earn it!" she shouted.

"Ughhhh...oooooofffff...yes MISTRESS!" I cried. She continued slamming my ass, and would occasionally reach up and maul my tits over my shirt. I was so hot and bothered, and wanted her so badly...I reached up and pulled my shirt off over my head. I leaned back a bit and grabbed my own tits with both hands, but Mistress roughly shoved me back down. I felt her latch onto my bra strap, and use it as leverage to power fuck me even harder. "OMGGGG!!!! FUUCCCKKK!!" I growled, and slammed back to meet her thrusts. Then I felt her undo the strap and the bra fell onto the bed, and my tits began to bounce, now totally unencumbered.

Right as I was reaching a peak, I felt her pull out. "Ughhhh Mistress PLEASSEEE!!" I whined. "PLEASE, your bimbo Barbie is so horny, I'll do anything!!!" I cried. I felt her tie my legs (in their current spread, on all fours position) to the corners of the headboard. Then my hands were tied to the posts of the footboard, so I was still in the same position, only secured, quite spread out, tits mashed into the pillows, and ass arched high in the air. My pleas were met though, as I felt a rubber cock push its way back into my ass. "Ahhhhh, thank you Mistress. A cock back in bimbo Barbie's ass, thank you Mistress," I said.

"You're welcome Barbie," Mistress said. But something was wrong. The direction of her voice indicated that she was no longer behind me...which means someone else was! OMG!! I panicked and tried to pull off the cock, but a pair of hands gripped my hips firmly and did not allow that to happen.

"Mistress?" I asked questioningly.

"Yes Barbie?" Mistress asked, as I felt another rubber cock push into my mouth.

"MMMPPHHHH" I gagged, as the cock filled my mouth.

"Yes Barbie?" she asked again. Clearly Mistress was not in front of me either, so there were at least two other people in the room.

"I'll answer for you, since your mouth is full," she stated. "Yes, Barbie, I invited over a few friends, I knew you wouldn't mind. You said you wanted to be double teamed by two cocks like a true bimbo, so I made that happen. What do you say?"

"Thhhnkkk yuuuu iiithhrssss," I mumbled.

"Anything for you, Barbie," she said. "Let me adjust you," she said. I felt my hands untied from the end of the bed, and tied together. Then they were tied to the middle of the footboard, so I was again on all fours. The assault on my mouth and ass continued, and I began to rock back and forth in rhythm with the thrusts. "Are you enjoying yourself Barbie?" Mistress asked. "Let her answer," Mistress added. The cock in my mouth was momentarily removed.

"Ughhhh....yes Mistress Brittany. Bimbo Barbie is ughh....ooohh....ooooo, loving the cocks!" I cried.

"Real bimbos don't just teases cocks, though Barbie. Real bimbos make cocks cum. Right now, you're being a mean cock tease. You don't want that, do you Barbie?"

"No....no Mistress. Bimbo Barbie wants to be a real bimbo," I answered.

"Real bimbos get covered in cum," Mistress continued. "I think that would be so fucking hot, to see your face, and tits and ass plastered in cum. Would you do that for me, Bimbo Barbie?" she cooed.

At this point I was so worked up, I'd have agreed to anything. "YESSS!!! Yesssss Mistress Brittany, Bimbo Barbie would do anything for you!" I shouted. The cock in front of me re-entered my mouth, and I went to town on it again, but this time it felt different. It was real!!!! I panicked again, and tried to pull back, but a pair of hands folded together behind my head, and prevented me from spitting it out. The hands on my hips held me fast as well, and I heard Mistress laugh.