Working Vacation 2

(story continues from Working Vacation)

Part Two

Nicole looked down at me and smiled. “Get up, head over to the bathroom. And yes, you are to use the one marked for “sissy's”, as they do have one for you. When you get back, sit down on the chair and eat something food related. Then we can have a little chat”

“Yes, Mistress!” I got up and walked over to the restrooms. I found that there indeed was one marked “sissy” and went in. It was bright pink (YUCK) but it definitely had everything a sissy would want, including small individual bottles of mouthwash (YEAH!) and other little things to help you clean up. I opened my pocket book and pulled out my lipstick and touched it up. That was the only part that was really bad. That and I had to use the facilities.

Once I was finished, I came back out and walked over to our table. I sat down and the waiter brought me over a wonderful salad and a glass of wine. I looked over at Nicole who smiled and pointed to the food. “Eat while I explain some things that you now need to understand.” I started eating as she started talking. I ate slowly so I didn't miss anything.

“Okay Lynda. In case you were wondering, Sheryl was, or is, like you. She came to work for us as a man and worked for three years, as a man. It took us that long to discover her hidden feminine needs. That was when we offered her a different position and she worked her way to First Assistant to Ms Tress. It was because she also had a dominant side to her rather than a submissive side that she ended up as First Assistant to Ms Tress. Her other assistants are ALSO like you in that they were men. Since they were trained and feminized, they live their lives as females, since you really can't say women. They have their chastity harness on 24/7 and in their cases, they are permanently attached to their penis, keeping them under control at all times. Sheryl is different in that she has one like you are wearing but it cannot be removed without the key locking the device to her penis. She went to visit Frank, Mr Jenkins, to, well, dominate him as he had requested. She has done that for him several times and seemed to have enjoyed it greatly. However, his VP, Jennifer, caught them and, well, took matters into her own hands.”

I looked at Nicole and showed I had a question. “Go ahead, Lynda, you can ask?

“Thanks, Mistress,” I smiled... “What I am wondering is I thought we sold products, not, well, domination and discipline... Though you did mention that this chastity is something that our company makes, I don't recall seeing something mentioning this or anything like it, in the past year I have been here. So???”

“Yes, I know you haven't seen anything like that. Part of that is because it is handled by Ms Tress' three other assistants. Your job was to take care of the little things as well as occasionally monitor the vanilla side of the business. We have several others that handle that as well and they were all sending their information to you so that you could give it to Ms Tress. But the thing that you need to understand is that Sheryl had a contract with us as a First Assistant. That was a long term contract and there were three years remaining on that contract. Mr Jenkins company buys many of our products to resell in his stores. He has just given us a 5 year exclusivity for many of those items at a slightly increased margin, making us back some of the money we lost from Sheryl leaving us”.

“What I understand is that this Jennifer gal wants to remove the chastity on Sheryl or use her to gain control of the company from Frank. I am not sure but it will be interesting to see if when Frank meets with Ms Tress next month who is wearing the chastity harness. I have a feeling that Jennifer will have it on him by then and both Sheryl and Jennifer will be the ones running that company.”

I realized at this point that I was being told things that maybe would not have been my business. But I also realized that all of this was leading up to something. I wasn't sure what it might be but I knew it was going to be either climatic or anticlimatic.

“Now, seeing as you are finished with your salad, I am sure that you would like to complete the last part of the little deal I made with you on the plane. Since you seem to like that 'damsel in distress' idea, I think it is time that we let you know what that feels like, don't you?” I could see an evil glean in her eyes as she said it but the smile on her face made me realize that either I was smiling too or else I was just thinking that it would be kind of cool being tied up. Little did I know what I was walking into as we left the little club and arrived back at the hotel suite.

“Well, Lynda, you have a choice. We can either do a little with you dressed as you are or we can have you change into something a little more or less lingerie like. And I think a few pictures would be a nice thing to have so you can have a reminder of this little time. What do you think?”

“Yes, Mistress. Pictures would be nice. And maybe we can start with this and go further later???”

“Sounds like a good idea, Lynda. Take care of anything that you need to and then come into the parlor where we have a little more room.”

“Yes, Mistress.” I then walked into my bathroom and cleaned up. I realized that my panties were a little damp and realized that I had some pre-cum seep onto them. So I went to the dresser and found another pair and pulled them on. I touched up some of my makeup and went into the parlor room. I walked up to Nicole and knelt at her feet.

She was standing there in her corset and stockings, wearing higher heels and holding several long ropes. I also saw some other things laying on a rolling room service cart and realized that this could be interesting.

“Okay Lynda, that was good. I want you to kiss my shoes and thank me for taking you in for training.” I kissed her red patent leather stilettos, saying “thank you, Mistress, for taking the time to make me a better and more obedient servant.” I heard a chuckle from her as I continued to kiss her feet.

“Oh, Lynda, you need to understand something. You are not my servant. No sweetie, when I put that collar around your neck you went from servant to slave. You are my property now. That collar is permanently attached around your neck. That lovely little satin cover around it comes off.” I felt her hands around my neck as she removed the cover. Then she showed me what the collar looked like and I gasped.

“Yes sweetie. That is a stainless steel collar covered with black patent leather. Of course, this time you really can't miss the word “SISSY” in pink patent leather right on the front of it. Any time we are NOT in the public eye, that is the collar that you will be showing to everyone. When out in the public eye, the satin cover will be placed on it so that they would have to REALLY look to see it say sissy.”

“The chastity harness you have on is not the permanent variety. If you behave improperly, you will find yourself wearing one of those. I would highly suggest you behave because, quite honestly, once you have that permanent one on, you might just as well plan on being bent over quite a bit. I know that Ms Tress three other assistants are whipped on average of three times a day and, well, Ms Tress does seem to like her strap on quite a bit. I think her assistants are coming to love it as it is the only sexual satisfaction that they get now.” I saw the gleam in her eyes as I realized that was nothing that she would like better than to put me into THAT chastity and that scared me!

I looked down at the floor as I realized that I had definitely gotten myself into something that was starting to frighten me. And it just kept going...

“Now, the first thing I want you to do is stand up and spread your legs a little bit. Not like you are going to be frisked by the police but just to steady yourself.. Now put your hands behind your back.”

I did as I was told and felt leather cuffs being wrapped around my wrists and above my elbows. Then I felt the same cuffs going around my ankles but these had a chain between them. Then I heard a click and noticed that not only were the cuffs on my body locked in place but that my ankles also had a strap that held my shoes on. I was not going to be taking them off any time soon.

“Okay now. Let me see. I think that I want to make sure that you wig doesn't move so instead of just a blindfold and gag maybe I will use this harness. Yes, I think that will work. Lynda, open your mouth so I can put this ring in there!”

I opened my mouth and this huge ring gag was placed in my mouth. As she fastened the first strap around the back of my head, she placed other parts of this harness around and over my head. Soon my head was cased with leather and then the blindfold was placed on and snapped into place. Then I felt another gag being placed in my mouth and I heard her voice, laughing, “you should be used to this shape, Lynda, seeing as you sucked one this evening!” and then snap, it was locked in place.

Before I could do anything, I felt my wrists being pulled tight and locked behind my back. Then I felt something being placed near my elbows and suddenly I felt them being pulled back. I moaned and pleaded as I felt them being pulled night and tight together. It felt like my arm was going to pull out of my socket as she pulled the strap tighter. Then I heard something else. I felt a tug on my neck and I realized that I was being led on a leash and was forced to take small, apprehensive steps, as I could not see anything and could only move my feet in small steps.

“Good little slave. Trusts his Mistress correctly. So I guess I won't have to discipline you too much. But I think you will need a little discipline as well as some punishment for not doing what I said quickly enough. Not that I need a reason for punishing my little slave now, do I? I could just be having a bad day and I could punish you just because, right slave?”

I tried to say yes but with this huge penis gag in my mouth, I couldn't say anything. I felt a lash hit my exposed thigh, “Well, answer me, slave!” I nodded yes VERY enthusiastically and was rewarded with another lash across my other thigh. “Figured it out, did you? I guess that tonight and tomorrow it will be time for you to learn and experience where your place is.” With that, I felt myself being led to someplace and we stopped. I then felt myself being pushed into a bent over position and felt a table of some sort, realizing that it was the rolling cart that I was bending over. Then I heard a click, another and finally a third. I tried to figure out what had clicked when I was told.

“Now slave, you have been essentially locked to the rolling cart. Your feet are locked spread open and your collar is now locked so you can't get up.” Then I felt my head being pulled back, forcing the gag deeper into my mouth. Then I felt a tug as my arms were pulled up and back towards my stretched head and another pair of clicks. “Now your arms are hooked to your head, putting you into a modified strapido. A little uncomfortable, isn't it?” I could not even nod really, though I tried really hard. “Hmm, not tight enough, I guess.” and I felt her tighten the straps at the side of my face a little more.

“Now, this should keep you quiet for a little while. Besides, I have to take care of something that needs to be done.” I then felt my skirt being hiked up a little and my fresh clean panties being pulled down. “Interesting, slave. I see that you changed your panties. Did we make a little mess in them with your little pee-pee??? Well, something more to punish you for. Good slave!” Then I felt the strap holding my chastity loosen up and I thought that I was going to have it removed. That was just wishful thinking.

I then felt the sharp and very painful sting of something going across my stretched ass cheeks. It was followed immediately by another and then, another. I tried to count them as they fell but I was soon crying and moaning like a little baby as each powerful stroke placed another lash across my ass and upper thighs. I tried to move but if I moved the cart the lash just struck somewhere else and then I would get yet another one more vicious than the one before. “Don't move and make Mistress REALLY upset with her slave!” and then another lash would hit me, reminding me that this could indeed hurt worse.

Eventually, I found that the lashes weren't hurting me so much as they were making me feel really, well, relaxed might be a strange word for it. All I knew is that I was starting to really ENJOY the whipping and would actually try to raise my ass more, in essence begging for more. This would, of course, bring a more vicious lash to my ass, though it was usually accompanied by a little laugh. “Does my little sissy enjoy this? I guess I may have to add a little something then” and then she stopped.

By then I was sweat soaked and feeling something between horny and sleepy. I was actually feeling sexually excited but I was feeling tired. That feeling soon came to a screeching halt as I felt her start to penitrate my ass with a dildo that felt as if it were going to tear me in half. I moaned and screamed into my gag, begging her NOT to do this as she kept pushing it in, little by little until she got past my resistance and slowly started to thrust it in and out of me, causing me to cry anew and beg for... I didn't know what I wanted... Did I want her to stop or NOT to stop. All I know is that she was fucking me and I was starting to really enjoy it and this frightened me even more.

“Does my little sissy like being fucked by her Mistress? I can see that you are enjoying it so you can't tell me you don't, slave! In fact, I think that you want the real thing buried deep inside you here instead. But I think that this will work for now. Because I can see that your little pee-pee is starting to ooze cum, you little slut! You like being fucked like a little slut, don't you??? Yes, you do... I can see it as you are trying to get it deeper into your little sissy cunt!!! Oh, I guess I got myself a real slut!!!”

And it was true. I was so enjoying her rhythmic thrusts into me and I was so starting to enjoy it as she would go slow and then speed up and then slow down again, changing the rhythm every so often and I would try to get it deeper. I was hurting but I was also loving it. And then she thrust one more time and I felt my cock just start to hurt as I started to feel an orgasm causing me pain and yet pleasure as the pressure relieved itself. But then I felt something else as I felt a tug on the chastity and then I realized that the huge dildo was being locked inside me! And then I felt something else as it turned out it was a vibrator and it was locked into place hitting me in a place that caused me to buck and moan like a whore!

“Ooh, it seems that sissy REALLY loved this!!!” Then I felt a lash applied to my ass! “I think that this will be...” Another lash struck me! “A great deal of fun tonight...” Another lash, this time going up and down, as if she had moved and was stricking me from directly behind. “And I can not wait until tomorrow, slave! Just imagine your humiliation when housekeeping comes in tomorrow to clean the suite and here you are, bound, gagged and with a sign begging to be punished. That should be priceless...” Then I felt more lashes strike my ass, causing me intense pain as well as pleasure as the vibrator would occasionally be moved just a little and make me buck like a little slut, begging for more.

Eventually, she stopped whipping me but the vibrator stayed in place, running. I hoped that the battery would eventually die but then I heard, “By the way, slave. That lovely vibrator you have fucking your sissy cunt is there with a power cord. So the wonderful little torture device will be fucking you until it is unplugged. Maybe you will get one of the housekeeping staff to release you from your torment but, well, I know some of these lovely little ladies and they might just enjoy seeing a little sissy begging for more whipping. And some of them may actually whip you, just because they can. And they know you can't see them.”

“Oh yeah, and just so that you know. The vibrator inside you is something you need to keep in the back of your mind. Because the one that you are going to be wearing permanently with your chastity, well, let us just say that it is a little larger than this one and does run on a rechargeable battery, which can last up to 3 days without recharge! Unless, of course, you want to volunteer for the OTHER chastity. Not that it would be any better.”

“I will see you tomorrow evening. I am going to leave you here to contemplate your future...” With one last vicious lash across my ass and a soft caress on my cheek to wipe away a tear she saw, I heard, “Don't cry, slave, because this is what you wanted, isn't it? To become the little sissy slave to a demanding and occasionally sadistic Mistress who would make you do all sorts of things that you wouldn't normally do yourself? I know that is what you wanted and fantasized about, seeing as Ms Tress and I have all the writings you have done on your little fantasy blog. Now, of course, you have to learn that fantasy and reality sometimes are not best when put together. Not that you will be escaping your new reality anyway...”

“And yes, slave, I am seriously going to let you suffer humiliation when housekeeping comes in. Maybe, if you are lucky, they will try to release you, though with the locks it might be difficult. But then, they will find the collar and the chastity something that will tell them much more. Or maybe you will get one of the other ladies who even enjoy finding sissy slaves bound for whatever reason in the rooms and become excited when there is a little sign actually asking that they whip you with the riding crop and invite other like monded people to do the same. Maybe, if you are good, I will even let you thank me properly for training you...”

With that, I felt the floor move just a little as I heard her walk away, the heels of her stilettos clicking on the floor. I never heard another thing as I was bent over, feeling the vibrator do it's thing and the thought that this was just the beginning swirling in my head. My arms were aching and my neck was straining, as they were both connected. And the taste of the penis gag in my mouth was burning my mouth as all I could taste was latex. And I was learning that latex does NOT taste very nice for extended periods of time.

I heard a laugh, the door open and “sweet dreams, slave!” and then, the door closed. I was trapped, bent over a cart that I could try rolling around. That is until I realized that the wheels seemed locked now, dressed up in a skirt and blouse, fuck me pumps and tied in such a manner that anyone would think that I either wanted fucking or whipping, or, with my luck, both! And there I waited for how long, I did not know...

* * * * *

“Housekeeping”

Oh shit! I must have fallen asleep! And now, what she had promised had happened. Housekeeping has arrived and is going to find me all bound here and either will scream and get me some help or will shriek and run away. Or even worse, she will come in, find me here and whip me or something. No matter what, the second that door opens, I am going to be found out and suffer...

Sure enough, I heard “housekeeping” again, along with another knock on the door and then the door opening. It wasn't much of a shriek but I could tell that there was indeed someone walking in and a little chuckle from someone with a hispanic accent.

“Well, what have we got here? A little sissy boy all tied up, it seems. And what does this little note say? Do you know? I bet you don't, seeing as you have been tied up here for a little while. Plus the note says that all you know is that you are being punished for being a bad sissy and need to learn you place.”

“Gee, I know a couple of boys who could probably do with this kind of punishment, though I don't think they would be too thrilled having a big vibrator fucking their little ass like you seem to have. Your Mistress even asks me to NOT unplug that monster inside you. But I have to wonder if you made a little mess in your panties like she seems to think you will. And from that wet spot on your panties I would guess that you are enjoying yourself, even though it seems you are straining to either get out or not to enjoy this.”

“Unfortunately for you, I seem to like little boys all dressed up like sissys. And I see that your Mistress left behind this wonderful riding crop to let us punish you. And I am going to enjoy punishing you with this, since you really can't stop me. And I also know some of my friends would love to come in here to whip you. But maybe you want something a little more than just a whipping??? Like maybe a real cock to suck and some man-cum to swallow, maybe??? I can help you there as I know a couple of cute, well hung guys who would love to get a good blowjob from a cute little sissy like you! Would you like that? I bet you would!!!”

Suddenly I felt the sting of the riding crop on my ass and all I could do was suffer as she seemed to know just how to wield that crop to inflict the most pain in a split second. And as each lash struck bare flesh I knew that this was not going to be the end but it would be just the beginning of a very long and painful day!

“Oh, I just LOVE red sissy butts! And it seems that you really ARE a sissy, seeing as I can see all this cute lingerie sitting on your bed and all the cute little slutty outfits you have. But best of all, I saw that cute little satin french maid uniform hanging up. And no heels shorter than 5 inches tells me that you may be here for longer than a day or two. I wonder if maybe, just maybe, we can make arrangements for you to work here for a day as a special little maid. If your Mistress has plans for you this week. Because I know a couple of the guests here would just love the opportunity to play with a sissy maid! Besides, why work hard if I can find someone else who I can punish if they don't work. I may just have to stop by later on and maybe talk to her.”

“Now, don't go anywhere, sissy. I am going to bring a few friends over during our lunch break and maybe even when we clock out for the day. Since there seems to be a room key sitting here, I will just borrow it. See you in a little while, sweetie”

She patted my sore ass, pushed her cart through the door and left. I could feel the tears rolling down the side of my face and I was sure that there was a load of drool sitting there on the floor beneath my head as all I could do was drool. And I could tell that my ass was hurting even more than it had been.

I don't know how much longer I was there, and I probably had fallen asleep somehow but I heard the knock on the door without anyone announcing that they were housekeeping, so I was HOPING that maybe it could be Nicole and that she would release me. I was so sore. But that was not to be.

“Oh my! Maria was right. And this sissy is so cute, what with the short skirt and the fuck me pumps on! And I just bet you give good head too, don't you sissy? You had better give good head or else I will just have to whip that cute little panty clad ass of yours. All I have to do is get this gag off you and... There we go!” I heard a snap pop and the gag came out of my mouth.

“Oh my, you have had a little practice sucking, haven't you sissy! Well...” I heard a zipper and suddenly I felt a cock enter my mouth. Before I could say or do anything I felt a sharp sting on my ass as I was told to suck the cock in my mouth. It took a couple of additional lashes before it sunk in that he was going to whip me if I didn't suck him off, so I started to work and it didn't take long before he was grabbing my head and forcing himself deeper into my mouth and down my throat. When he grabbed my head and shot his load into my mouth, I swallowed it and started to gag a little.

I was expecting the gag to go back into my mouth but instead I heard something scary! “Your turn, James. And sweetie, he can suck good once he realizes  that it is suck or whip! But I wonder how good he will be if you whip him WHILE sucking!”

Well, needless to say, I was sucking this James guy and the first guy started to whip my ass. At first it was slow and spaced out, sort of like how James was fucking my mouth. As he sped up, the lashes sped up and soon I was crying and screaming from the whipping as well as sucking as well as I could. Within minutes, I had yet another load of cum shooting into my mouth and my ass was so red and inflamed from the whipping that I was trying to beg them to stop.

The gag was replaced in my mouth and I heard them leave the room. I was starting to realize that this was not anywhere near the fantasy that I had created in my head about being forced to serve and service. This reality was far more harsh, as I was starting to realize as my cock was screaming for release from it's prison and I was needing to move body parts.

I heard the door open and the stiletto heels of Nicole entering the suite. Then I heard her voice and part of me just smiled.

“Well slave, I can see that you have had a couple of whippings today. I also see that you sucked at least one guy's cock and that is a good start for you. I also know that one of the maids wants to use you as a real maid in that little outfit of yours in the room. I may just honor that request, seeing as you might like to learn how to be a GOOD little sissy maid as well.”

I felt the cords binding my head and arms release and I could move my head down. It hit a pillow and I could feel the pain and strain start to fade away. Then I felt my arms get released and the harness come off my head. Lastly, I felt the ankle cuffs come off and I was able to kick off my heels. I was tired and I could smell myself and it was not a pleasant smell to say the least. I could also taste the latex from the gag and the cum from those two guys who I sucked off in my mouth and I NEEDED to clean myself up.

“Now, I want you to jump into a nice bubble bath and clean up. You will then put on your SLUTTIEST outfit in your wardrobe, not counting the maid uniform. Six inch heels and seamed stockings. Whatever undies you wear, they must be slutty. Maybe the red set. And I want your face to look like you NEED someone to fuck you, repeatedly. Be ready in 90 minutes. Every minute you keep me waiting will mean an additional punishment. Now, get moving, slave!”

“Yes, Mistress!” I ran as best as I could into the room and stripped off everything. I put it all into the duffle bag I used for dirty clothes and hopped into the bath, running the water and adding bubble bath into the water. Then I hopped in and stared to relax a little and washed up. I was feeling pretty good and didn't realize that I had been in there a while when I noticed that the water was cold and the bubbles were pretty much gone.

I rushed out of the tub, getting dried off and went and started to do my make up. I noticed that the clock was NOT in the room so I had no idea how long I might have fallen asleep in there and was worried that I was in DEEP trouble. I hurried but made sure that I didn't mess up my make up. Then I went into the bedroom and put on my red bra. Dug out my red garterbelt and some black seamed stockings I got from Fredericks of Hollywood. These were beautiful black stockings with a red lace band at the top and a red seam down the leg. Then I put on my red patent pumps with the ankle strap and my red panties. I was starting to feel cramps and knew that I needed to use the bathroom. But with the vibrator inside me there was no way I could, well...

I looked at my clothes and saw the sexy little red dress that I had found at Fredericks and put that on. It barely covered my stocking tops and if I moved in any way I was sure that they would see my panties. I put on the wig and stepped out into the parlor of the suite to find my Mistress sitting there with a glass of wine in one hand and her riding crop in the other. I went to her and knelt on the floor, scared that I was late.

“Not too bad, Lynda. You managed to get in here with one minute to spare. I was so looking forward to punishing you for being late, especially after I put that bubble bath in your room. It is designed to relax you and I was sure that you would fall asleep. You did but you managed to wake yourself up in time. Now stand up and let me see what you think a proper slut should dress like!”

“Yes, Mistress!” I stood up and twirled around a couple of times, slowly, so that she could look and inspect me. Then she told me to hike up my hem and bend over. I did so and she pulled down my panties and I felt a tug and the strap holding the dildo was released.

“Now, I am sure that you need to use the facilities. So go ahead and take care of that and clean that dildo while you are at it. When you are done, leave the dildo there. But I want you to give yourself an enema so that you are clean before you come back in here. You need to hurry or else I may have to do something to you that you may not be ready for...”

“Yes, Mistress!” I said, walking kind of funny as I tried to make sure I didn't drop this thing on the floor. I reached under and pulled out the dildo, dropping it into the sink and sat on the toilet. It didn't take long, seeing as I had been stretched quite a bit from that plus inside my ass. When I was done, I found the enema and used it, doing as best as I could to hold it in while at the same time cleaning the vibrator that had been inside me for almost an entire day. Finally I was finished and went back into the parlor. Sitting there now was not only Nicole but several other people who I didn't know but who seemed to know who I was. This told me that at least one of them was the maid who came into the room that morning and one of the men there was James, maybe. I came into the room and knelt at Nicole's feet, waiting.

“Good sissy, Lynda. Now, before we continue with tonight's activities, we need to take care of one little thing.” She opened a box and pulled out another dildo and motioned for me to turn around. I crawled around, reached behind and pulled down my panties, prepared for the pain of that dildo going in. And it did, indeed, hurt. I knew it would as this one was, it appeared, not only a little longer but also a little wider. I moaned as it went in and started to feel that now familiar sensation of the thrust and retreat of being fucked by it. And it took far less time this time to start to enjoy the sensation as I started to buck and moan like a bitch in heat as she fucked me for almost 20 minutes, making my cock sore from the constant desire to reach an erection as well as the pressure of the orgasm that wanted to be released.

All that time, however, the guests in the room were laughing and pointing out such wonderful things as how slutty I was, how I seemed to NEED to be fucked and, best of all, that they wanted to stick their own cock inside me and show me how it REALLY feels to be fucked by a big monster. That shamed me a little, as they kept it up the entire 20 minutes I was being tormented like that. Then I felt the final push in and the locking of the strap, signaling that the dildo was in for however long I was going to have this one in. Then I felt the vibrator start up and I started to buck a little as Nicole pulled up my panties.

“Okay, Lynda. I want you to stand up and walk around for the next hour. I want you to get used to that lovely vibrator fuck you while you walk around. Seeing as you are going to be wearing that 24/7 from now on. Oh, and at the end of the hour, you will be whipped 100 times plus, if you stumble at all, an additional 100 for each time you do. You will do this for several hours as you will be walking around tomorrow, working with Catherine and her crew. Oh, and these nice young men are expecting wonderful little blowjobs from you tonight so you can plan on that. In fact, I think you met James here. So go ahead and give him a much better blowjob than you did this afternoon. I want to hear him moan and scream from the pleasure you give him. And if he cum's without enjoying his blowjob, you will be punished even harsher than you have been so far.”

“Yes, Mistress!” I knelt back on the floor in front of James and reached up to undo his zipper. I opened his button and pulled out his cock, realizing that his cock was fairly large and was already hard. I closed my eyes and said a silent prayer as I bent over, wrapping my lips around his cock and started to lick and suck his cock as if my life depended on it.

Within minutes, I had James moaning lightly and I started to work a little faster and longer. Soon I had him sounding almost louder than the first man I had sucked off the day before. And in almost no time at all I had his cum shooting into my mouth and I swallowed it all.

“Oh my God, Nicole, your sissy is fantastic! Guys, you are going to LOVE the way she sucks dick!”

“What do you say, Lynda?”

“Thank you, sir. I am glad you liked it. I liked it too!”

“Such a good little slut, don't you think, James?”

“Indeed. Well, I have to be going anyway. Thanks for the interesting evening. I look forward to tomorrow more than ever. Lynda, it's too bad you are Nicole's property. I would have loved to buy you for my own slave. Still, I guess that it could have been worse. You could have been a BAD cock sucker and then I would have been paying for crap.”

“Buy me?” I thought! HOLY SHIT!!! I was going to be sold??? No, wait a second. He said I was Nicole's property... But I am not... Or am I... She said that the collar is permanent. She even said that the chastity was permanently attached! And that my male self, Paul, was no longer. I am now Lynda Christine... And...

WHACK!!!

“Slave, what are you doing, kneeling there? Get up off your knees and start your walking. And right now, it will be 500 lashes just because you knelt there for so long, knowing you had things to do!”

“Sorry Mistress. I promise not to be so stupid!” I got up and started walking around the parlor room, feeling the vibrator do it's thing and as I walked I could feel it start to cause more and more erotic feelings and making me NEED to cum even more! And as I was walking around the room, I knew that this was just the first day of this vacation that I had been planning for years. Not that it was turning out to be the vacation I had originally planned. And I was not too sure what was going to happen to me as the week went by.

Then I realized that not only was I going to be here for the rest of the week's vacation that I was on but I had to go BACK to the office. And I had a collar around my neck that was not going to come off any time soon, plus the chastity! Flying home now seemed like a non-option. Hell, I didn't even think I was going to be going to the home that I knew. I was going to be... Somewhere, though I didn't really know where that was.

“Okay, slave. Come over here and bend over the chair!”

“Yes, Mistress.” I came over and bent over. I felt my panties pulled down and the first lash struck my ass. I soon lost count as I realized that I was going to be punished for being an idiot and it was going to be 500 lashes! And as each one fell I cried out, begging for mercy.

“Silly slave. It is time that you understand that there is no such thing as mercy for a slave. You must come to accept any and ALL pain and punishment handed out. So I think I am going to have to add an additional 100 lashes for your begging for mercy. But, to be kind, I will add those 100 to the next stop!”

I could barely utter the “thank you, Mistress” as she continued to redden my ass. Eventually I made it through the 500 lashes and started to straighten up. I felt a hand hold my head down and saw a cock in front of my face. Without thinking, I opened my mouth and felt the cock enter my mouth and I started to give yet another blowjob while my ass was stinging. Then I felt the strap loosen up and the dildo start to move out. I was expecting it to start some sort of thrusting motion but soon I felt it come completely out and something different and entirely frightening enter my ass as I felt hands grip my hips! I tried to get up but the hands holding my head and more holding my hips down kept me there as I started to feel the fear of being taken.

Part of my brain was screaming that this could not be happening and yet another part of it was telling me that this is what I REALLY wanted. To be used and abused like a whore!

“Yes, my little sissy slave. You are now a little whore who wants to be fucked all the time, don't you! You want cock or dildo all the time, taking and making you all horny and slutty! And just wait until you feel a man shoot his load deep into your little sissy cunt, you little sissy whore! And this is just the beginning. Wait until my boyfriend gets his shot at your ass! He just loved my former assistant. Hell, he would come to the office every once in a while, usually when I couldn't satisfy him so he could fuck her ass or get a fantastic blowjob in the middle of the day! It was so much fun to watch as that little sissy would just bend over and let him fuck her for an hour all the while having to dictate a memo for me or some other little thing that I needed her to do.”

“Oh, and by the way, you are going to be going home with me via our company jet. Can't quite take you commercial any more, what with the collar and such. Besides, we will be flying with several male guests who you can entertain by giving them a little taste of fucking a sissy while in the air. Sort of an intense initiation into the mile high club, you could say!”

“Oh, and tomorrow, make sure you do a good job of cleaning or else Catherine and her co-workers will have to punish you. And I think you can count on some customers desiring some additional services from their maid tomorrow. Actually, maybe for a couple of days, seeing as I have to take care of some other matters. All of them involving you and something about a legal name change, as well as some other matters. And I think that on Friday, we can go see your plastic surgeon so that you can get the right sized breast implants. I was originally thinking that maybe just an average “C” cup would do but I seriously think that maybe some DD cups would be better... Or maybe even F cups! I think I can find you some bra's that will hold that size cup...”

I heard her laugh as I started to buck from all the sensations I was feeling and in moments I felt the flow of cum shoot into my mouth and I was fearing the same was going to happen into my sore ass. Then I felt whatever it was in my ass pull out and the vibrator get shoved back in and strapped even tighter into my ass! Then I watched as Nicole walked around from behind me with her huge strap on dildo harness and I realized that it had been her fucking me! I was so thankful at that moment until I realized that I would soon be really fucked by someone.

BREASTS??? Oh God... And I felt my cock start to ooze cum as I realized that I was actually turned on by having breasts and being fucked!!! All I could think of was the fact that she was turning me into a horny little sissy slut with all that she was doing to me. And it was only Monday!!! I was fearing the rest of the week while at the same time looking forward to what might happen!!!

 

18.09.10

story continues in Working Vacation 3

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