Spring Break Slave

"You fucking bitch!" I exclaimed for about the one hundredth time as I saw her holding up a DVD as she boarded the plane. A week ago, I had landed in Mexico, a regular college guy looking to blow off some steam on spring break. What I am now, and will be in the future, entirely depends upon the devious mind of the girl who just boarded the plane, whom I know only as "Mistress Ashleigh."

I met Ashleigh my first night in Mexico. Returning to the hotel after a night, I saw a beautiful blonde haired, blue eyed coed, sitting hunched over on a bench. We made a bit of small talk, and I determined that she was extremely intoxicated. I helped her stand, and generously walked her back to my room. She mumbled that she liked it rough, so I threw her onto all fours, grabbed her hair and railed the shit out of her. By the time I was done, she had scratches down her back, and her ass was so red that I doubt she'd be able to sit for a week. Just for good measure, I fucked her in the ass as well.

The next morning I awoke groggy and confused, and had a sizable amount of weight on my chest. I tried to rub my eyes, but found that I was tied spread eagle to the bed. Looking up, I saw the D cup breasts, and then the face of Ashleigh. "Rise and shine, slave boy," she cooed as she playfully slapped me in the face. "In case you're wondering what's going on, here's the deal: I have a tape of you raping me last night. In exchange for me destroying the evidence and not pressing charges you will be my slave this week."

"Fuck you," I spat back. "You don't have it. Besides, you said you liked it rough."

"Is that so?" she countered, as she moved aside, to let me see the DVD of last night playing on the TV screen. "If the DVD isn't enough, I'm sure I can just strip down at the police station and let them decide. Face it, I have you by the balls, and that's 'Mistress Ashleigh' to you." With that, she walked over to a suitcase and took out two pink string bikinis. She came back over to the bed, and untied me. "Put this on, slave," she commanded me.

I knew that she had me, and I figured I would make this whole thing as painless as possible on myself. I tied the strings on the bottoms loosely, so that my dick would fit inside. As I was putting on the tiny top, Mistress Ashleigh had managed to tuck my cock between my legs, and tied the strings on the panties much tighter, so that my crotch appeared smooth. She tossed me six inch platform sandals, which I put on as she snapped a collar around my neck and attached a leash. She changed into the other bikini, threw on a similar pair of sandals, and out the door we went.

The heels were very hard to get used to, and I fell several times as she dragged me down the hall of the hotel. Several people came out to see what the commotion was about, and made sure to point and laugh at the guy on a leash in a bikini.

Soon, we got to the beach. I noticed we had passed a sign that said "Come join us for sex on the beach. FREE BEER," but didn't think much of it. The beach was set up for a contest of some kind, with bleachers and a stage. I assumed it was just another wet tee shirt contest, though I wondered why there were four contraptions on the stage that looked like large blocks with four loops hanging from each of them. "Well, it looks like we're early," Mistress Ashleigh stated.

"I guess it would be a good idea to get some practice in beforehand," she said, as she pushed my neck down so that I was bent over one of the blocks, and only my upper chest was supported. Suddenly I felt cuffs closing around each of my hands, so that they were spread, with one on each side of the block. Then my feet were cuffed to a platform behind the block, so that my ass was in the air, and all my weight was on my tip toes and my chest.

I looked up, expecting a nice upward shot of Mistress Ashleigh's tits, but what I saw was a large black strapon dildo fastened to her waist. "I suggest you suck this, because it's going in your ass," she stated matter-of-factly. Clamping my lips closed and turning my head, proved to be futile, as Mistress simply grabbed the back of my head with one hand, and pinched my nose with the other. As soon as I ran out of air, my mouth opened, and she jammed her cock inside. She continued to force me down on her cock, which caused me to gag frequently, and which left a trail of drool running down my face. After about ten minutes, I got into a rhythm of breathing and bobbing that made me look like a deep-throating professional.

"Looks like someone's a quick learner," Mistress Ashleigh giggled, as she withdrew from my mouth and walked behind me. As she stepped away, I had a chance to look up, and I noticed that bleachers had filled with other spring breakers. A quick glance to the side revealed three other guys in my exact predicament, although I was the only one dressed as a girl. "Apparently these girls have very kinky boyfriends. They all volunteered for this," Mistress informed me. "In fact, they've all done this before, so they can take bigger cocks than you. You'll simply have to make up for it with enthusiasm and endurance. Unless you want me to go to the police..."

The announcer kicked off the festivities. "Good afternoon, ladies and gentlemen, and welcome to our first annual 'Turn the Tables' contest. Ladies are you tired of the men always having control? Have you ever dreamed of turning the tables on your boyfriend? Well, that's exactly what is going to happen today. These four ladies are going to wear the cocks and show the boys what it's like to bend over and take one. I understand our first three couples are real life couples, who enjoy this on a regular basis. Our couple on the end, I've been told simply, that they met a few nights ago, and he is paying off a debt to her! So this should be interesting!! Remember, the winners get $10,000 in cash. Ladies, on the count of three: ...one....two...THREE"

"YEEOOOOWWW," I screamed as Mistress's cock tore into my virgin ass. This elicited a huge laugh from the audience, as apparently the other guys had taken the initial thrust with no problems. In fact, I heard the slapping of their girlfriends' hips against their asses, as my Mistress had to withdraw and take another shot at it. Her second attempt was true, and again, I let out a pained scream as she buried it to the hilt this time. Each thrust felt like it was tearing me apart, and I thrashed in my bonds as she continued to fuck me with hard, fast strokes. She leaned forward, held my head down and dug an elbow into my back, further showing her dominance of me. She went at it for awhile, and I continued in vain to escape from my bonds.

All of a sudden, my ass felt empty. I took the chance to glance to the side and saw the other couples chatting with each other, and the audience, each of the girls with their hands on their guys' hips, thrusting away and talking like they were watching a football game. My rest was brief, however, and suddenly I was slammed with what felt like a baseball bat. I screamed. Mistress Ashleigh laughed, and announced to the crowd, "That's the advantage of having a girl cock; you can change sizes whenever your whore gets too loose." "Ok, slave; I really want you to humiliate yourself. Let's all hear how pathetic you are," she whispered to me. "Or you can get it in the ass from a guy in prison, it's your choice."

"Please, Mistress, not that Mistress. Please," I begged. "Please fuck me harder, I'll be a good little bitch, I promise," I said, as I heard the audience laugh. "I'll be your slave for the rest of spring break, please. I'm sorry," I whined.

"Did you hear that?" Mistress Ashleigh asked the crowd. "Do you think he should be my slave for the rest of spring break?" The crowd roared its approval, and I continued to thrash in my bonds. "Do you want to see her little titties?" she implored. Again, the crowd roared to life, and the triangles of fabric that covered my nipples were pulled to the side. She cupped my chest and pinched my nipples. I screamed again. "Awww, the poor girl doesn't like having her titties exposed, does she?" Mistress taunted me.

"I'm just ashamed that they are so small, Mistress," I answered.

"Wow!! I've really broken her, haven't I?" Mistress Ashleigh said. "Face down, ass up, bitch," she growled as she plowed my ass. I'm not sure how much longer it went on, but I do recall looking up and being surrounded by the other ladies in the contest, who had come over to watch us and congratulate Mistress Ashleigh on her victory.

Finally, long after everyone had left, Mistress grew tired of fucking me, and released me from my bonds. I staggered and fell to the ground. "Looks like I wore you out, you little bitch," she laughed, as she picked me up off the ground. "We have one more place to go, and then we can go home," she informed me, as I wobbled after her in the heels, my ass throbbing.

We soon entered a women's store on the beach front. "I remember what you said today, about feeling ashamed that your titties are too small, so we came here to remedy that," she said. I want you to tell the nice woman behind the counter that you want big titties so that you can please your Mistress," she said.

I was too worn out to argue with her, so I approached the woman at the counter. She looked at me a few times, and then broke into a fit of laughter.

"I'm here because my titties are too small, and I want to please my Mistress," I said to her, my face burning red.

"How big does your Mistress want you to be," she asked.

"Oh, as big as possible," I said. "I want them to really sway beneath me when I'm bent over, or on all fours, getting nailed doggie style. I want something to grab when I'm riding her cock reverse cowgirl, and I want them to slap me in the face when she's pile driving me." Both women erupted into laughter, and the sales woman came back with a pair of enormous gel breast forms.

"These are the biggest ones we have, and they are DDs. I would imagine you want them on now," she said, as she pulled my bikini top to the side and stuck them to my chest. "This glue is water resistant, and only comes off with a special remover. Let me go get that for you."

"Actually, we'll come back for it later in the week, if she's good," Mistress Ashleigh laughed as she paid the woman and hauled me out of the store. We walked toward the hotel, my newly acquired "assets" along with the heels and my sore ass, made for quite a spectacle. I staggered around like I was drunk. "Wow, look at how big your new titties are," Mistress remarked. They are bigger than mine! You know, with you staggering around like that, you're making quite an inviting target for the guys around here. Perhaps I should walk on ahead and see what happens."

"No, Mistress, please!" I begged, as she hurried up ahead. I ran to catch up, which caused my titties to bounce uncontrollably in the skimpy string bikini, and brought more stares in our direction. We finally got to the hotel room, and I stripped out of the bikini and collapsed on the bed. Mistress Ashleigh tossed me a lacy white thong and a short, satin and lace white babydoll nightie to wear.

I stood up to put on the attire, and was surprised by the weight of my unsupported titties. The babydoll barely covered my tits or my ass, and I looked over at Mistress Ashleigh, who had changed into a wife beater tee shirt and sweat shorts. I noticed a large bulge in the shorts, as she handed me a pair of white 7 inch platform stripper heels.

"Guys always say it's much hotter when she leaves her heels on, and I would say that I agree," she said. "Put those on, and leave them on. You are to please me at ALL times," she reminded me. I did as I was told, put the heels on, and lay down on my side, which was all my new titties would allow. Mistress Ashleigh lay behind me in the classic "spoon" position, with her hands on my titties and her cock resting against my ass. That's the last thing I remembered as I fell asleep.

I awoke to the feeling of cock in my ass. The sun and breeze were coming in through the open window, and apparently Mistress Ashleigh was feeling horny. "Slave, thank you for taking care of my morning wood," she taunted me, as she grabbed me by the neck and put me on all fours. Obviously the babydoll had bunched up around my waist, but the pounding I was taking caused my titties to spring free of their flimsy confines and bounce wildly beneath me as my Mistress hammered away. She reached around me and cupped them. "Wow, these puppies are enormous!" she exclaimed. "I'm glad I don't have to carry them around. Now stand up, and march over to the breakfast bar." I tottered over and immediately bent over it and rested my chin on top.

"Look at how submissive you've become!" she said. "But you are wrong. Hop up on the breakfast bar, bitch!" she yelled as she hopped up to join me. She lay down on her back, her cock pointed menacingly toward me. "Now flip up your little nightie, turn around so I'm not looking at you, and take a seat on my cock!" she commanded. I did as I was told, cautiously lowering myself onto Mistress Ashleigh's big black cock.

It must have been too slowly for her liking as she grabbed my shoulders and pulled me down, rapidly impaling me on the monster, and causing me to lose my balance on the heels. "Bitch, you are fucking worthless, now get up and start bouncing" she screamed. I quickly regained my balance, got up on the heels, and started bouncing away.

Mistress reached up and grabbed my arms, and pulled them behind me, which enabled her to slide her cock further into me. Once she tired of that, she pulled my legs out, so that I was now resting on my knees and her stomach, so that she could get all ten inches into my ass. I bounced up and down and grabbed my own titties, moaning like a whore as I did so. Then I heard a knock at the door, but I was so lost in the moment, that I just kept going. "Oh that must be room service," Mistress said. "Come in," she shouted. I quickly leaned forward on my forearms to hide my face, but kept fucking her cock.

"Oh, I'm sorry to interrupt," the woman said as she sat down the food. "I'll just drop this off and be on my way. Have fun with your girlfriend."

"This is my slave," Mistress corrected her, as she pulled me back up to sitting position. The woman laughed and left the room. "Don't worry; she's been watching us on video for quite some time now. Now we have a cruise to attend, so get off my cock and get changed. Your dress is the first one in the closet."

I waddled over to the closet, and took a long, champagne-colored, sequined skirt off of the hanger. Upon closer inspection, the skirt was slit to just below crotch-level, and it had two pieces of material hanging off an O ring at the navel. I let the babydoll fall to the floor, and then sat down on the bed and worked the skirt up to my hips. When I stood up, the skirt clung to my ass like a second skin, and the two pieces of material continued to hang down in front of me. "Mistress Ashleigh, where is my top?" I inquired.

"Right here, silly," she laughed as she reached in front of me, pulled the thin strips of material up over my titties, and tied them in a bow behind my neck. She laughed at my horrified expression, and added, "Those white shoes look horrible with this color, and tossed me the same type of shoes, only clear. She poured herself into a sexy, but classy, long black dress, handed me my matching purse, took my hand, and pulled me toward the door.

We exited the hotel, and made our way to the docks where a boat was waiting for the afternoon cruise. There was no shortage of catcalls along the way, and it was quite clear that I was going to be the center of attention every where I went in that dress.

"Now stand behind me, keep your eyes down, and only speak when spoken to," she instructed me, as we boarded the cruise. We went straight to the bar, and Mistress ordered herself a scotch on the rocks, and a Cosmo for me. Drinks in hand, she mingled with the other couples there. I kept my head down, and blocked out most of the conversation. Many of the men just laughed at how pathetic I was, but to my surprise, many of the women were very curious. They poked and prodded me; many of them were fascinated by my outfit, and in awe of how big and realistic my titties were. They mauled them freely, treating me like a mere object on display.

Soon, we had quite a gathering of women around us."You'd be amazed at how quickly you can break them," Mistress informed them. "Two days ago, this loser would have been up at the bar with your loser boyfriends. Now he wouldn't dream of leaving my side or disobeying me. There is something about dressing them up like a bitch and fucking them in the ass that really does it. Ten minutes into his first anal pounding, he moaned like a girl and admitted he wanted bigger titties to please me. Ten minutes!"

"I'd like another drink, take care of that," Mistress directed me. I opened my purse to check for cash, and to my horror, all that was inside was a big black strapon. "Typical girl move, not bringing any cash to the bar," she laughed. "Apparently, she prefers to pay with her ass, isn't that right, slave?"

"Yes, Mistress Ashleigh," I said.

Mistress went up to the bar, and returned with her drink. She grabbed me by the wrist and dragged me out onto the deck. "Bend over bitch," she growled, and I dutifully bent over the railing as I heard her quickly pulling on the strapon. The skirt, slit as it was, was easy to roll up to my hips, which I completed just as I heard the last strap tighten into place. Mistress grabbed a hold of me, and with one quick stroke, was balls deep in my ass. By now, my only reaction was a grunt.

I was aware that it was mid afternoon, so any frantic movements or wild noises that came from us would grab the attention of other boaters, which I hoped to avoid. From a distance, it just appeared that I was looking down into the water, and Mistress Ashleigh was behind me, rocking back and forth.

She must have thought the same thing, because all of sudden, I felt a sharp "CRACK" on my ass. I screamed. It was followed by another, and another, and another. Mistress spanked my ass repeatedly, and I felt it burn. My cries just encouraged her to slap harder, and more frequently, as she drove the dick into me. She reached up and untied the bow behind my neck, and my big titties sprung free as the pieces of material fell to my waist. I looked up and saw that my screams had also encouraged quite a gathering of boaters, who had pulled up to see the spectacle.

I looked back over my shoulder and grabbed my ass cheeks with both hands to spread it further and also to shield if from additional blows, which left my titties to bounce wildly over the rail. After a few minutes, the tugging became unbearable, and I reached forward to cup them as Mistress Ashleigh continued to spear me. My legs were also very tired from the heels and the position, and finally she pulled me upright, only to push me down on all fours.

After she impaled me yet again, she pulled me backward and tried to make me ride her reverse cowgirl, facing the inside of the ship. I looked up briefly to see the other cruise goers gathered around the window, and my legs burned as I rode her cock to the best of my ability. My big titties bounced, and I finally collapsed because my legs wouldn't support me anymore. By then the boat had docked, and Mistress withdrew from my ass, and left me there on the ground, as she said her goodbyes to the other passengers.

I rolled my skirt back down and retied the strips behind my neck. I stuffed my titties back inside as best I could, and staggered off of the boat behind Mistress Ashleigh. We entered the store we had visited before, and Mistress purchased the adhesive remover. "I bet those are getting heavy and sore," she said. "Do you want me to take them off?"