Spring Break Slave Ch. 02

(I recommend you read the first part of this story.)

I had taken advantage of a drunk girl named Ashleigh, on spring break, and had since found myself paying for it in spades. I don't mean with an STD, or even legal action (either of which may have been preferable, trust me!). She had woken up before me, bound me, and blackmailed me into being her slave for the rest of spring break.

My slavery was not cute little tasks like fetching her drinks. In fact, me fetching her a drink while I had big DD tits glued to my chest, and wearing only a thong, skyscraper stripper heels, and a very slutty party dress, was one of the tamer things she made me do. She fucked me in the ass with a strapon dildo at a wild spring break "Turn the Tables" event. She made me ride her big black cock reverse cowgirl on the breakfast bar of my hotel room, and she bent me over the railing of our booze cruise and fucked me there as well.

She promised not to go to the police if I cooperated, and she made good on that promise. Right now, my problem is that she has video of everything she did to ME over the course of the week, and had threatened (as she jumped onto a plane) to make it public if I did not comply with her future wishes.

Luckily, no one important heard her yell to check my bags, so I just turned around, and headed back through the airport toward the doors. I went out to eat, walked around the mall, and stared at my phone. I had no idea how to get a hold of her, or what to do next. Several hours later, my phone rang, and I answered. It was Mistress Ashleigh! She suggested if I wanted control of my life, to book a ticket to see her, which I immediately did. Oddly enough, she lived in my hometown! Small world!

The trip was uneventful, and she met me at the airport later that evening. We went back to her house, and she told me we'd talk more in the morning. True to her word, the next morning we had a talk.

"I believe you have a bit more that you owe me, so here's what I propose," Mistress Ashleigh started. "This is my house, and I have quite a bit of money, but I need help around here. You have no job since you've graduated but haven't been able to find one, so you can live here, free room and board, in exchange for doing some work. Whatever is needed."

Honestly, I had no prospects, and spent way too much on spring break, and had no idea how I was going to make my rent this month. The deal sounded good to me.

"Ashleigh, that sounds like a good idea," I said.

"Excuse me?" she growled. "It's still 'Mistress Ashleigh' to you," she stated. "Get on your knees, when you address me. We are not equals," she spat. I did as I was told, and got on my knees, and looked at her feet. "Do you wish to take me up on my offer?" she asked.

"Yes Mistress," I said.

"I had a feeling you'd say that, and I've prepared accordingly. We will have all of your stuff delivered here this weekend. I have one more rule," she said. "While you are doing indoor chores, you are to entertain me. Go to your room, and look in the closet. There you will find several maid outfits, put on the black one." I must have paused, because she continued.

"Need I remind you of what you did to me on spring break? You were a pig. You thought women were simply there for your use. You wish to represent women in such a disgusting way? Fine. Then you're gonna live that disgusting fantasy until your last breath and you're not gonna always like it," I heard her yell, as I headed to the bedroom. "Glue on those titties real well," she warned. "That outfit isn't going to help much in supporting them," she added.

I opened the closet, and it was as she said. As commanded, I glued on the double d breast forms, and held them until they set. Next, I rolled black fishnet, stay up thigh highs up my already hairless legs, and added a tie-side g string black satin thong. The silk rubbed against my poor caged cock, and it hurt like hell, but I kept going. I pulled the short, silky black "dress" up my legs, and slid it up onto my shoulders. Of course it was a piece of fantasy lingerie, so it showed a TON of cleavage, but thankfully had underwire support. Sure, the underwire was to make the wearer's tits more inviting, but since I was going to be doing a lot of work in this outfit, I was thankful for the support, regardless of the "cost." The finishing touches of the costume included a black choker, hat, and cuffs, which I fixed into place. I looked around, and the only shoes I could find were six inch plus platform stripper heels. Certainly she did not expect me to work in those, so I grabbed the duster and headed to the living room.

"Where are your shoes?" she demanded.

"Mistress, I wasn't sure you'd want me to work in those, they are very tall," I said.

"Nonsense, of course I want you to work in those, go put them on!" she shouted. I ran down the hall, which caused my knockers to flop out of the tiny maid's outfit. Quickly I crammed them back in, and strapped the towering heels onto my feet. I walked back out to Mistress Ashleigh.

"Very sexy," Mistress cooed. "Now, I have no desire to draw undue attention to us, so while you are outside, you may remove the tits and wear male clothes," she said.

"Thank you Mistress Ashleigh," I responded. "Does Mistress require anything else of me?" I inquired.

"Now, I need a drink, fetch me one," she commanded. Over the course of the day, she had a few other tasks for me as well. She called a company and had my stuff delivered, as promised. It all fit in one room, which was designated as my room.

Over the next several months, I settled into my routine as her live-in maid. Some of my tasks involved manual labor, like raking, and various other home ownership chores, and true to her word, she had me do those in male clothes. I also wore male clothes when we left the house, although my trips out of the house become less frequent, and always to do things like grocery shopping or dry cleaning pick up. Of course most of the work around a house is in the house, and I did all of the laundry, all of the cleaning, and all of the cooking, dressed as a French Maid.

Since most of the work was done inside, I spent most of my time in one of those demeaning and highly feminized "uniforms." So much so, that some of them started to get worn out and had to be replaced, which Mistress gladly did. Being in such a highly feminine and sexualized state all the time has a way of changing a person, and I began to notice changes in myself. The chastity device made it mandatory for me to sit while using the bathroom. I got used to the heels, and the weight, and inconvenience of working around my tits.

Mistress would encourage me with kind words, and it kept me going. She'd also get me gifts from time to time. One morning she left me pretty pink nail polish on my dresser, so naturally I painted my fingernails and toenails before I got into that day's maid outfit. A different day, she left me makeup and lipstick, and a video on how to do them. It took a lot of work, but I finally got the makeup and lipstick done. I looked in the mirror and smiled at how pretty I looked. My hair had begun to grow out, and was long enough for a ponytail now. I pulled it back into a ponytail, since I had so many chores to do, but knew that I'd have to learn how to fix it properly.

Mistress Ashleigh saw to it that I did learn that as well, a few days later. Another thing I had to do, was constantly shave my body, to keep it smooth and feminine. The act of doing so was also very repetitive, but drove home the point as well.My back, legs, and feet were constantly sore, and the amount of work I had to do made me very tired. Once I'd done all the housework for the day, I often had "other duties" to perform.

A good share of what I did also involved servicing Mistress Ashleigh sexually, in whatever way she wanted, and always while feminized. She kept me locked in chastity. Often, she would bend me over and fuck my ass. Sometimes, to humiliate me, she'd have me lick her ass, or spend hours rubbing and worshipping her feet. Mistress also meticulously trained me to lick her pussy exactly the way she liked it. After hundreds and hundreds of oral trainings, I could make her cum as quickly or as slowly as she wanted, depending on her mood. Sometimes, I would get tired, both physically and emotionally, but Mistress expertly kept me going by teasing me. She treated me with a mixture of contempt and kindness. And she always dangled the possibility that one day I MAY get the privilege of entering her divine pussy.

After one particularly long session, filled with multiple orgasms for Mistress, she looked down at me and smiled. "You have made me very happy, slave. I would say you are an expert on my pussy, and I am very pleased. Would you like me to unlock your cock?" she smiled.

At first, I thought it was a trap, so I paused. She'd asked this before, but when I had replied enthusiastically, she'd laugh and deny me. When it became clear that it was a serious question, I replied carefully, "if it pleases you, Mistress Ashleigh."

"Finally, a little self-control and humility," she said. "Yes, since you answered correctly, I will unlock you," she answered. Mistress retrieved the key, pushed up my maid outfit, and unlocked my poor, swollen cock. "Lay down on your back," she said, so I did. My cock stood straight up in the air. Mistress smiled and hovered over it. "Would you like to enter my pussy?" she asked.

"Mistress....I...I don't think I could please you with my cock," I answered truthfully, "but I will enter your divine womanhood if it pleases you," I added.

"Slave, I desire a cock in my pussy, and you will provide it," she stated. "I will ride you until I'm satisfied. You will cum, but only when I say, is that clear?"

"Yes Mistress," I said. With that, she lowered herself down onto my engorged cock. I closed my eyes, and used all of my willpower not to cum immediately. Mistress laughed, grabbed onto my tits, and began to ride my cock aggressively. She must have known that I would not last long, so after a few minutes, she mercifully said, "Slave I bet you're willing to do anything to cum, am I right?"

"OMG Mistress, yes!" I panted. "I will do anything."

"You'll do anything in order to cum in my pussy?" she repeated, as she began to slowly grind on my cock. Oh my God, I was going to get to cum, and cum inside her?

"Yes, Mistress, anything, please Mistress," I begged.

"Very well then, you may cum." she stated matter-of-factly. No sooner had she finished her sentence, then I came harder than I ever have in my life. It had been so long, I flooded her with my seed. Mistress Ashleigh smiled, kissed my cheek and stood up. Most of my cum ran out of her and back onto my stomach, but she scooted up and sat on my face. "Ok, I let you finish, now you need to clean it up. All of it," she commanded.

I was not at all surprised, and began to lovingly clean my cum out of her pussy with my tongue. Once I had swallowed every drop, I licked her to three orgasms, until she collapsed on the ground next to me. "I said all of it," she panted, as she pointed at my stomach. Obediently, I scooped up the remainder of my seed and deposited it down my throat. We got cleaned up and went to bed.

......

I woke up refreshed the next morning, but bound to the bed. Mistress Ashleigh looked stunning in a low cut, tight fitting wedding dress! Before I could say anything, or even close my mouth, she said "We're getting married today! You can go ahead and tell me how beautiful I look."

"You are the most beautiful woman in the world, Mistress Ashleigh," I said.

"Am I making you hard?" she whispered sexily as she got up on the bed and crawled slowly toward me and straddled my chest, her amazing breasts on full display inches from my face.

"Ughhhhh yessssss!!" I moaned. My poor erection was pinned painfully to my chest by her weight.

"I may put that thing to good use later on....if you're good," she promised. "I'll unbind you now, you are to shower, shave and put on the outfit that is hanging in the other room," she continued.

As soon as she untied me, I hopped up, rubbed my wrists and got in the shower. I wondered how ridiculous and embarrassing the outfit would be this time, but I realized I didn't have much choice anyway. I cleaned up, and went to see how bad the day would be. To my surprise, I saw a pair of dark men's suit pants, and a white shirt. There was a matching pink bra and tiny pink g string to go under it all, but at this point, that was expected. Mistress Ashleigh was letting me wear male's clothes to our wedding! After I put it all on, I presented myself to Mistress Ashleigh.

"You look ravishable, slave," she purred. She went to her closet and handed me a pink tuxedo vest and bow tie. I put those on, and we headed to the car. For some reason, I went to the driver's side. She laughed, "Um, no. Really? And pushed me toward the passenger seat. "Of course we have pictures first, followed by the ceremony, this is going to be great fun!" she laughed.

We pulled into a nice flower garden, and got out of the car. A nice looking woman, probably in her early thirties approached us. "Are you Ashleigh?" she asked.

"I am, you must be Sarah," she replied. "This is Ken," she continued. I shook the woman's hand. It was still a bit odd to me to have her introduce me, it definitely made me feel more submissive.

"Nice to meet you," she said to me. "You paid a lot of money, so whatever you want to do," she smiled.

We got going, and Sarah got several good shots of us.

"Let's reenact the proposal," Sarah said. "Get down on one knee," she told me.

"Make that both knees," Mistress Ashleigh said sweetly. Part of me panicked because I knew where this was going, but I did as I was told. I heard the shutter click several times. No big deal. "Go ahead and kiss my foot, while you're down there," Mistress Ashleigh laughed. "This is sooo fun!" she said to Sarah. The camera clicked several more times. "Let's get some of just Ken," she said to Sarah. I stood up. She took a few of me by the fountain, and a few more by a nice flowering tree.

"Ken come over here," she said. "Sarah, we'll be over in a minute," she shouted. "Take off your shoes and socks and bend over that bench," Mistress Ashleigh commanded her back turned to me. Without question, I did as she said, and put my hands on the bench to help with my balance. I heard the click-click of her heels on the pavement behind me. Then I heard a Velcro-ripping sound in the back of pants, followed by cool air on my ass. A split second later, I felt Mistress Ashleigh's (thankfully) lubed strapon push into my ass! "Do you like how I rigged your pants?" she mocked me as she drove forward.

"Ughhh!!! ooooffff," I moaned quietly, so as not to attract Sarah's attention. But that was probably going to happen anyway, so instead I reached back, spread my ass cheeks, wiggled, and pushed back in order to fully accommodate her cock and make it disappear. Once she was all the way in, she rested her elbows on my back. "Sarah come on over, I have a cute picture," she announced cheerily.

"That IS cute," Sarah agreed, and snapped more pictures. "Ken, smile! You're enjoying this!!" Sarah tried to encourage me.

"Yes, SMILE," Mistress Ashleigh said. She ground her elbows into my back and wiggled her hips to burrow her cock further into my asshole. I grimaced, but managed a smile. "Ok, now pan up and get this shot," she said to Sarah. I felt her lean back a bit, but also grab the back of my bow tie, and use it as a collar to pull my head up and back.

My pained reaction was captured in real time by more repeated clicks of the camera. "That's great!! Great reaction!," Sarah exclaimed. "The old ball and chain," she added. I looked up, and I saw her step back and zoom out. There was a moment where her face just froze in a mixture of confusion and shock. "What's...what's THAT?" she asked. My face went beet red, as I realized she must have at least seen the straps of the strapon.

"What's what?" Mistress Ashleigh asked. "Oh this???" she asked, as she (thankfully?) pulled all the way out of my ass. "This is my cock." "THIS," she said, as she pulled me down to my knees, and pointed at the bobbing strapon, which I instinctively put in my mouth, and tapped me on the head, is my BITCH!"

"I...I don't know what to say," Sarah stammered. All I know is that I was happy to not have to face her, and I kept busy sucking Mistress' dick.

"Like you said earlier, I did pay a lot of money, so unless you're truly offended, go ahead and keep going. This is the photo session we want," Mistress Ashleigh stated.

There was a pause, and then Sarah said, in a composed voice, "Ok, let's do this!

"Make sure you get my dick in the picture," she said, as she slowly pulled back, and then slammed it all the way back down my throat! I don't want anyone to think he's just kneeling in front of me, I want them to know he's sucking my dick." "Take your shirt off, but keep sucking," she told me. I unbuttoned the shirt and tossed it to the ground.

"Isn't that a pretty bra?" Mistress Ashleigh asked Sarah.

"It is," Sarah replied. "I have one just like it that I wear when I'm trying to entice my boyfriend."

"Take your pants off as well, same deal," she told me. I struggled, but managed to get my pants off, which left me there, in a bra and g string, on my knees, sucking my Mistress's strapon.

"Oh cute, a matching set! What a proper whore," Sarah said. "From behind, he looks like an above average girl. Can you... do what you were doing before....with the thing?" she said, still uncomfortable, as she pointed to the strapon. I want to get a few more shots."

"You mean fucking him in the ass with my cock?" Mistress Ashleigh said. "Of course I can!" She grabbed me by the bow tie, jerked me to my feet, spun me around, and bent me back over the bench. Again, she grabbed the back of my bow tie, and shoved her cock straight up my ass.

"OWWWWW!! Mistress Ashleigh it HURTS!" I whined.

"Shut up, slave! You took advantage of me at spring break, you don't get a vote in this anymore!" she shouted back. "This is over when I say it is. I'm in control now," she shouted as she continued to pound me. "You're wearing a pink bow tie, bra, and thong, bent over a park bench and getting pounded in the ass by your bride-to-be. You're not only in for a long day...and night, but a long life unless you change your attitude and accept the fate you brought upon yourself. I call the shots now, besides, you've been living as a girl for so long now, it's all you know."

I knew she was right, and I hung my head and took the punishment I deserved.

"He did WHAT?" Sarah said angrily.

"He basically raped me at spring break. He found me outside really drunk, took me inside and had s with me," Mistress Ashleigh responded. "I decided to take out my anger and hurt this way, but he knows if he gets out of line, I'll go to the cops. We're obviously still within the statute of limitations."

"You vile piece of shit," she spat in my face. "I was raped two years ago, but I never had the courage to report it, or get revenge on my attacker. You are scum," she said.

I looked her in the eye, and my face got red from embarrassment again. But there was a subtle change. I wasn't embarrassed by my predicament. I had accepted that I knew I deserved my punishment, and that I was wrong. I was embarrassed by what I'd done, and I began to cry.

"I'm...I'm sorry, Mistress Ashleigh," I sobbed. "I'm truly sorry for what I did to you."

"That's a good start, finally we have a break through!" she exclaimed.

"And I'm sorry...sorry Sarah...for what happened to you. Men can be pigs, we really can," I continued. "I will do whatever I can to make it up for what I've done."

"Shhh,shhh, I know you will," Mistress Ashleigh said quietly. She grabbed my hips and eased back a bit. For some reason, I pushed back to get her cock back in me. She eased back again, and again, I pushed back. "You even wiggled your hips a bit that time," she commented. "It's starting to feel good, isn't it?" she asked. "Once you give in and stop fighting it, it starts to feel good," she continued. Mistress Ashleigh was right. As she moved back some more, I moved back in order to keep my ass full. "You're chasing my cock, it feels good in your ass, doesn't it?" she whispered in my ear. "I can make it feel good, if I want. I've done some reading. Anal sex is a good way to stimulate the prostate, if done correctly. Or, I can hammer away at your butthole and cause you a great deal of pain. It's up to me," she said.