But I'm NOT a Woman!

“But honey, I'm not a woman!”

Of course, the line that I heard after I said that the first time was to be my eventual downfall. When my wife looked at me and said, “Well, you seem to be DRESSING like one!”

Of course, it wasn't like I was planning on getting caught. And I certainly didn't plan on getting caught in the manner in which I was. But those were now things of the past. But I guess that I should explain how it got to this point, where my little line certainly would not explain the way I look NOR the way I dress.

You see, I am a guy. Well, duh, if I'm not a woman I would be a man. Well, sometimes there is that little line that gets crossed and you get what I am. At first I was a cross dressing male, enjoying the feel of feminine underwear. Then I went a little further and started occasionally dressing like a woman. Then I started trying to go out and would end up in maybe the occasional drag bar or gay bars. But for some reason, what started out as just some sort of sexual thrill started to get boring. Oh, I still enjoyed the lingerie and clothes and occasional drives out in the country in my car, but the “thrill” was kind of gone.

Then I realized what it was that I felt I was missing. You would see it occasionally in movies and ESPECIALLY in the adult book stores. I wanted to not only be a damsel but, you guessed it, I wanted to be “in distress” to boot. And when I started researching it, I found out about self bondage. And by experementing I soon discovered that thrill that I seemed to be missing.

But I also enjoyed the company of women and occasionally dated, sometimes seriously and I would do the usual purge when I thought that things were getting to a good point and maybe it was just a passing fad or something. As you can guess, that was a wrong conclusion but also, the girlfriends would come and go. The dressing, however, always seemed to stay with me, along with the damsel in distress scenarios that I was trying out on myself.

Over time, I managed to find some people, mostly professional dominatrix's, who would help me actually take care of the damsel in distress fantasies in a more, shall we say, exciting manner. Of course, I always knew that I would get loose but I still kind of found it exciting when I would find the time and money for such an evening. I didn't do it often and I rarely went to the same woman more than three times, as I would find it boring with them by then. I liked the fresh and new. And even the guys who would do it for pictures and, as we had always agreed, no sexual contact. I did NOT want to be with a guy sexually. Oh, I had occasionally THOUGHT about it but doing it, well, that was a whole OTHER story...

Eventually, I met the woman that I fell in love with and her with me. But I kept that little secret for myself. Since I traveled, I felt it would be fine and I would be able to enjoy my little secret life outside and still be happily married to my wife. Of course, I tried very hard to NOT be careless and only do the dressing and bondage while I was on the road. Since I was gone usually 3-4 nights a week, that was rather easy. And when I came home, I was relaxed and happy and glad to see my wife after all those days gone. We would have romantic dinners and mess around in the house, doing whatever it would take to satisfy each other. Of course, I have to tell you that I was finding my erections not as satisfying for her BUT I could take care of her orally. She never complained to me but...

Anyway, the travel slowed down and I was finding it more and more difficult to take care of those urges that I had. If I wasn't going on the road, there was always office work for me to take care of. But, I looked forward to those trips more and more, but they were coming fewer and farther between. And then my wife told me that she was going to be going over to see the neighbor and go to a movie, since she had a three day weekend and the neighbor had wanted to go to “Crazy Stupid Love” but couldn't get her husband to go. I thought about it and realized that, if nothing else, I could at least enjoy a couple of hours of my feminine self and maybe do a little self bondage at the same time. 2 hours would be plenty of time, since I always kept myself smooth, I would not need to shower and shave. And I could do it without the make up. Just had to go to the trunk of my work car and get my little bag.

So, I gave my wife a kiss, which she returned with passion, and then off she went. I waited until I actually saw them drive off together in her car before I went to the trunk of my car. I picked up my case and then went up to the bedroom.

I quickly peeled off my male clothes and opened my case. Everything still smelled like the cachet that I had in there, a little lavender and lilac so that everything smelled feminine. I pulled out my breast forms, a lacy black bra and put them on. Then I got out my garter belt, also black, and put that on. I looked for and found my french heel, seamed stockings and carefully rolled them up my legs. Then I picked up my favorite panties, black nylon, from Secrets in Lace. I loved their retro look and styles and these always felt so nice when I put them on. Then I got out my short little slip and pulled that over my head. Then I looked and found my tight little black turtle neck and a short plaid skirt that, when I put them on, barely covered my stocking tops.

Then I opened the other side of the bag and found my toys. And I got out my timer and set it for one hour. I put the keys in there and then closed the little door. I got out my handcuffs, ankle cuffs, locks, blindfold and gag. I figured that I would also enjoy a little added stimulation so I pulled out the vibrating dildo and strap so it would stay in place. I put a condom on the dildo, lubricated it and slowly put it inside me. It took a few moments but I got it into place and buckled the straps so that it wouldn't come out. I also put a condom on my cock since I knew that eventually I would cum and make a mess in my panties if I didn't use the condom.

Then I bound my ankles together, using the leather cuffs and padlocks. I grabbed a leather strap so I could put myself into a sort of hog-tie after I had cuffed my wrists and such. I laid down on the bed and finished binding myself. First the gag, then the first cuff went on my wrist. I looked around to make sure that by simply turning on the bed I could get to the lock box, after squirming a little, then I put on the blindfold. Now I was ready.

I quickly reached down and turned on the vibrator. It was one that had a variable speed, determined by some sort of electronic thing, but all I knew is that it would go fast, then slow then some other speed and essentially drive me to orgasm and make me squirm quite a bit in the meantime. Then I put the strap between the cuffs to hold my wrists down and my ankles up and locked the cuff around my wrist. And since the strap had a lock on it as well, I would not be able to open the clasp or anything else until the lock box opened.

Of course, I could feel the vibrator doing it's thing and I was so getting a charge out of it until I felt the sting of something on my ass and the words, “You little bitch!!!”

“You little bitch! I knew that you were wearing panties and such but I didn't realize that you were tying yourself up too! God, you are such a little slut! Martha! Come up here. I told you my husband was a freaky little shit!”

I could hear her coming up the stairs and then the laughing. I was now not only discovered by my wife but also by the neighbor next door. And, to be honest, I wasn't sure which one finding out was worse, since I had occasionally fantasized about Martha.

“Uh, Jess, I think you should look at something!” Then I felt my panties being pulled down and they saw the strap and could hear the vibrator going inside me. Now I was in trouble...

“Well, THIS I didn't expect. Hell, this and finding my husband dressed as a slutty little school girl, bound and such was not what I was expecting, either. It certainly is an eye opener, to say the least.” Then I felt her moving things around on the bed. “Well, I don't see any keys but I see this little box. It sounds like there are keys in it. Are there, you little bitch?” All I could do was nod, which I did.

“Let me see. Since you thought I would be gone for two hours, I think maybe you gave yourself a little time to prepare and then to clean up. So, I guess we have a little time before the keys come out. But, well, I think that I will just let you stay like that for a while until I decide just what it is that I want to do about this.

“And be assured that you are going to be there for quite some time, you little... BITCH!”

With that, I heard her stomp out the door. Then I heard Martha come up to the bed and whisper in my ear. “Oh, I am SO going to love this, Paul. Jessica may be mad now but by the time I finish talking to her, you are going to learn the meaning of, well, femininity, let me tell you.” Then I felt her swap my ass. “Oh, and I think you need to be a little LESS comfortable!” and then I felt my wrists being pulled closer to my ankles and I knew that she had picked up some sort of clip off the bed, making me bend a little more backwards and the vibrator made things a whole lot worse as I was now getting closer to an orgasm...

When it finally hit me, I was moaning and squirming and filling the condom with my cum. Then I started to fall asleep but could never really get there. I was blindfolded, by my own hand, and gagged so I could not call out to ask to be released. And I was afraid to roll off the bed as not only was it a tall bed but falling out might cause me to break something and then I would REALLY be in trouble. I also realized that I was in trouble as the vibrator kept doing it's thing, to perfection as I was getting somewhat hard from it's magic. I knew that it would take a while but I had nothing better to do, being bound as I was. And I had no sense of time so I drifted off.

Eventually, I felt my ankles released from my wrists but that was just so I could then be turned over. I felt my panties pulled down again and the laugh was pure evil!

“See, Jess, I told you that he was going to have at least one orgasm. And he did do the right thing, keeping his silky panties from getting all filled with cum. And you know that this means that he saved his own cum so he could recycle it!”

I heard that and I knew that it was going to be trouble. I started to squirm, trying to get free until I felt something painfully slap my balls!

“Stop squirming, sissy!” It was Jessica. At least she was talking to me. Not nicely but it was something. And I was still feeling the vibrator as they started to pull the condom off, their touch started me to have my fourth orgasm. Luckily, all of it went into the condom and not onto me, though maybe it would have been better if it had.

“We better put a fresh one on his little cock! God, his cock is still semi hard! Jess, is he always this big?”

“No, and now I can see why! It is either the panties and bondage or else that vibrator fucking his ass that is doing this to him. But either way, well, I am not going to worry about it for now.” Then I felt the condom being placed on my cock and my panties put back in place. Then I felt something strange happening to my gag.

As I felt this, I also felt my ankles being bound to the foot of the bed. I was still lying on my arms and was in a little pain. Then I felt each of them grab an arm as my wrists were unlocked. I thought I had a second to free myself but they each had a wrist and pulled it over my head. I was now bound to the bed ankles to the left pole and wrists to the right. Then I felt my blindfold come off. I blinked my eyes a few times and they both came into focus.

Then I saw what was happening to my gag. A small funnel was being pushed into the breathing holes in my gag. I knew then that they knew it was a penis gag. It was my favorite gag of the two I had and now it was to prove to be my worst enemy as I watched them finish putting the funnel in place and then the condom was in place over the top.

“As you can see, sissy, you need to recycle your cum, since we don't want to waste it now, do we? And trust me when I tell you that you had best SWALLOW EVERY SINGLE DROP! If you decide not to, that little swat you got earlier on your cock is nothing compared to the swat your cock and balls will get.” With that, I watched as Jess poured the cum into the funnel and into my open and not very willing mouth.

I let it drip and pour into my mouth and swallowed it fast so that I didn't really taste it. But no matter what, I tasted it and was NOT enjoying it one little bit. And they could see it in my eyes.

“Well, sissy, you might as well get used to the taste of cum because, well, since you don’t want to be a man and you like dressing as a slutty little bitch, you are going to become one, sort of. Slutty bitches suck cock and swallow cum! And since we also know that you enjoy a cock in your ass, well, we have to make arrangements to take care of that for you too!” Then they put my blindfold back on and left the room. This time it was Jessica who whispered in my ear.

“Poor little sissy. If you had not kept all of this a secret, maybe I wouldn't be so rough on you. I knew that you were playing little miss dress-up when I went to your trunk for something a few weeks ago. I didn't see all the little 'toys' you had in there but I did see your undies and clothes. At least you have style and the right style for undies, Paul. But, well, I think I need something more. And now, well, I think I will get it.

“Oh, by the way, Martha's husband... Well, you should see how well he is hung! Well, maybe see isn't the right word... Maybe FEEL...!” I heard her laugh and leave the room as I laid there contemplating my fate. I wasn't waiting long as I felt myself being rolled onto my stomach and my panties pulled down.

“Okay you little bitch, I have decided that I need to vent my anger and this is how I am going to do so...” I then felt her use something on my ass as she started to whip me. And she was calling me every name in the book from “bitch” to “whore” to “slut” and even “cock sucker”. All of these words were nothing compared to the power that she demonstrated on my ass as she whipped me. I was unable to really remember what she was saying, or really yelling at me, but I could tell that she was mad at me for keeping secrets from her.

I would hear or at least make out that I should have talked to her about these things that I felt inside and that honesty would have been much better than for her to find out in the way that she did. And she was telling me that since I seemed to so much want to dress like a little slut that before I was done, I would truly know what it meant to be a slut. And I think I even heard something about her and Martha making arrangements to help me realize my inner slut!

As she was telling me this and whipping my ass redder than a steamed lobster, I was also feeling the vibrator drive me to yet another orgasm. I was suffering pain AND feeling pleasure at the same time and I was getting confused by all of this. I wanted her to stop whipping me and yet, for some perverse reason, I wanted her to whip me more. And I was even getting turned on by the thought that she was going to make sure I knew what a slut felt like. Parts of me were scared but my brain, as well as the vibrator causing me pleasure, were telling me that this is what I wanted.

Finally, she was done whipping me and I felt her doing something to the strap holding the vibrator in place. I felt it stop and then it started back up again, stronger than ever. I realized she had changed the batteries as she told me that she was doing so. Then she patted me on my face and said that I should get some sleep since it was going to be a while before the next step in my punishment. When I heard this, I realized that this was not going to be a simple punishment from my wife. I also realized that what Martha had whispered earlier was quite true. So between the two of them, I had this feeling that I was going to regret not telling my wife about my inner feminine side.

But at the same time, I was realizing that maybe I was starting to actually LIKE this. Then I thought about Jack and how my wife had mentioned “feeling” how well hung he was and I started to panic again.

“Oh, you remembered what I said about Jack, did you, sissy? Trust me, that will be the least of your worries, though I can promise that you will taste his cum at least once before we are through with you. You see, Martha won't give him blowjobs. And you know how much MEN like them, don't you? So, since you should have a very GOOD idea of how one should be given, seeing as you USED to be a man, you should be able to give Jack a MINDBLOWING blowjob. And if you don't, well, we can give you a very evil incentive, like letting him fuck your little sissy cunt!”

She could see in my eyes that she had struck home with her comments and I knew that I was not going to be forgiven easily. In fact, I was afraid that I was never going to be allowed to be her husband and that once this was all done and over, I would be out looking for, if not a job, at the very least a new apartment.

“Now then, since it is late, I am going to let you try to get some sleep.” I then felt a little prick in my ass! “This little shot should help you sleep a good, LONG, time!” And within minutes, I was truly out like the proverbial light, and it was a nightmare filled sleep, thinking about being fucked and sucking cocks constantly and beginning to like it. And something about having REAL breasts and no cock! All of these things, though scaring me, never caused me to wake, so powerful was the sedative that she had given to me. And as it worked it's magic on me, I remembered something even more important about Martha and Jack...

* * *

I really do not remember what had really happened, I had been drugged for such a long period of time. I vaguely remember feeling some pain as well as a great deal of discomfort. But I never really woke up and had no idea of how long I was out when I finally DID wake up. And the headache that I was suffering from when I did was enough to make Bayer a fortune.

I woke up to find myself in our guest room. At least I figured it was, as it did seem somewhat familiar. It was not the former off white but rather a little pink with some other soft pastel hues in the trim and such. But the feel of the room was decidedly feminine, from the curtains to the carpet. And if this was indeed the guest room, then I also knew that this had to have taken a little time, since this was not the way that the room was when I had last seen it.

I was not even paying attention to my own body at first as I was trying to massage the headache away. I did manage to get up and walked to the door leading to the hallway but found that the door was locked. This jolted me a little but then I had this urge to pee so I went to the bathroom that the guest room had. I walked in and reached for my cock, only to find that it wasn't there...

I reached down again and felt something metal between my legs. I felt it and realized that it was indeed locked on and that it wasn't coming off, as much as I tried to pull it off. That was when I noticed the next little problem...

Well, to call it a little problem would be considered a massive understatement. I now had two huge and rather full breasts. I touched them and realized that they were indeed real, since I could feel my touch along the nipple. Of course, that also caused me to feel a little thrill through my spine and this, in turn, caused me to remember that I needed to empty my bladder. So, like a girl, I sat down and after a few moments, my cock realized that, as uncomfortable as it might be, I could relieve the pressure and I finally managed to pee. It was not comfortable and it was not easy. But I did and since I really could not shake it, I took a couple of tissues and dabbed at my cock.  Once done, I got up and flushed.

I walked back into the room and saw the mirror. Then I took stock of myself and my new, well, body. And what I saw scared me and thrilled me at the same time. Because what stared back at me would certainly be confused for a woman until they saw what was caged between my legs.

I had long, blonde hair. Now, this in and of itself was different since I had been balding around the top for years. In fact, I could wear a brown robe and would be thought to be a monk, my hair was that far gone up top. But not anymore. I had full, long, blonde hair with bangs. I pulled lightly and saw that it was there and not coming off. I looked at my face and saw the brows were much more feminine and my face, though not significantly changed, was certainly more feminine in appearance than it was before.

Around my neck was a choker, which I guessed was to hide my Adam's apple. When I tried to remove it, though, it didn't move or even stretch. I decided to ignore it for the moment as I resumed my appraisal. And when I looked and fondled my breasts, I knew that they were implants, not that I cared, but that the nipples were also pierced. There wasn't a ring through them but rather some sort of monofilament line passing through the center of each nipple. Then I looked town further to notice that my waist line was indeed smaller than it had been. And that the metal cage holding my cock was definitely not coming off.

As I looked and touched, I realized that I did not have a single male hair on my body. From my legs, through my crotch and along my arms, there was not a single hair. When I felt my face, I didn't feel the usual scruff from a five o'clock shadow but rather a smooth, hairless face, legs, arms, chest and crotch. When I turned in the mirror, I could see that I also did not have any hair on my back.

I went and opened the closet and inside it, I found the few articles of clothing that I did own that were feminine along with a great many more items. Of course, as I took stock of that, I noticed that the clothes were very few but the fetish clothes were extensive. I could see and counted seven French Maid Uniforms, a couple of very short skirts, some silky chiffon blouses and then I saw the shoes. None of them were shorter than five inches in height and all of them had stiletto heels. Most were pumps but there were a couple of sandals and even some boots. I also saw something that made me a little worried as I saw something that I had only seen in those magazines... Ballet shoes.

The one thing that I did notice is that each and every pair of the shoes had an ankle strap that looked like it could hold a small but effective lock, keeping them on the wearer's feet. I closed the closet and walked over to the dresser, already knowing what I would find in the drawers. But I did have to see for myself.

When I opened the first drawer, I saw several pairs of stockings. I also noticed several garter-belts and realized that the stockings were separated into thigh high and regular stockings. All of the garter belts were satin like the maid uniforms and had eight garter tabs. A couple I recognized as mine but the pink and a couple of other colors were like mine but not ones that I had before.

I opened another drawer and found corsets and basques in that drawer. I only had one cincher and that was not to be seen in this drawer. All of these were new and intrigued me a little. And the colors kind of went along with the uniforms as well. I was beginning to see a pattern here...

The next drawer held panties. There were standard brief panties, all nylon and somewhat amazing to me as there were far more than I used to have. I also noticed the ruffled panties and realized that they too went with the uniforms. I also saw some bras and realized that those must be for the times I was NOT in a corset. I was also noticing that no matter what, everything seemed to match. There were no mixed or odd colors in the drawers. Everything seemed to match with something else.

The last drawer held a couple of slips and several nighties. I sort of figured that would be in the last drawer here but, well, it was still kind of down heartening for me to realize that, well, I certainly was in deep trouble now, seeing as there was no changing back into my former, male self. And though part of me was kind of happy about all of this, there was still that part of me that was upset, scared and a little pissed that all of this had happened to me.

I sat down on the bed and realized that I was naked. And though part of me was sort of unwilling to go into the dresser and get something on, I realized that I really was feeling a little chilled. So, I went to the dresser and picked out some underwear. Then, before I started getting dressed, I took a little sniff and realized that I really did need a shower. Luckily, the bathroom had a shower and I took the opportunity to at least feel cleaner.

When I was done, I dried off and then started to get dressed. I decided that I would go vanilla rather than the kinky route and since I didn't have pantyhose, though I really never liked them in the first place, I rolled on thigh high stockings and got dressed. I picked out what LOOKED like the shortest heels I had in the closet and put them on. Then I sat down at the little vanity table and, in looking at the assorted make-up on the table, decided to spend a few minutes working on my face. It took me a little while and a great deal of experimentation but I finally decided that I had done a decent job and that was when I heard the door open.

“Well, I see my pretty little woman is awake, and dressed to boot. I think I should have told you what to wear earlier but, well, this will work fine for now. Now, I think we need a name for you... I know, we will call you... Tiffany!”

“But Jessica, I'm not a woman!”

“Well, Tiffany, you seem to be dressing like a woman... And since we went to all the trouble to give you rather spectacular breasts and the like, it's the least you can do to accept that you are, if not a woman, a very close approximation to one. Now, come along, Tiffany, we have many things to do!”

I got up and walked out of the room, only to discover that we were not alone in the house. When we arrived in the living room, Martha and Jack were both there, but that was not the worst part of it all.

Also in the room were other neighbors as well as many of the people I worked with at my office. It was then that I realized that I had not even THOUGHT about work. And each and every person there seemed to be, if not laughing at me on the outside, which a couple of them were, they were smiling and laughing at me on the inside.

“Okay everyone, I want you to meet Tiffany. Many of you may remember when Tiffany thought her name was Paul. But, as you can plainly see, Tiffany is now, without a doubt, Tiffany.

“You might as well get used to seeing her like this, or in some other attire, but it will always be feminine. And for those of you from her work, I guess I should warn you that, well, she will be there starting in a couple of weeks. She was permitted to take time off for medical leave and when that leave is finished, in about three weeks, she will be returning to the office.

“And, just so you know, your company has accepted the fact that Tiffany will be working there. And she is not going to be playing secretary, either. She will still have her former position in the company, and that means, Peter, Frank and Tom, that she will still be your supervisor. That should thrill you guys to no end, I am sure.”

I heard the three of them laugh until they saw the look on Jessica's face and then they realized that she wasn't kidding. I smiled, knowing that Jessica was sticking up for me, even though this was all coming as quite a shock. Those three guys, who were quite smart and intelligent, didn't realize that they were expendable, simply because, well, there were others in the company who would want their jobs, just as I knew that there were going to be people who wanted mine as a system manager. We had worked together for so long that I knew, once they got their heads wrapped around this little change, they would see the light and we could all work together.

The neighbors were an entirely different story. Once the guys from work were gone, things got a little more, shall we say, interesting. Everyone asked questions and the like and when finally one blurted out the one thing I dreaded, I knew that my goose might actually be cooked.

“So, is he going to model his little sissy maid uniform for us so we can see what we are going to be experiencing when she comes to clean out homes?” I looked over to Jessica and when I saw the smile come across her face, I felt shamed and realized that though I was now feminized, I was also going to be humiliated quite a bit.

I got up just before Jessica opened her mouth. I left the room without a word and went back to the bedroom. I took off my clothes and underwear and then sat down and cried on the bed. When I didn't return in a reasonable time, I heard a knock on the door and Jessica and Martha came into the room.

“Tiffany...”

“DON'T CALL ME THAT!!! My name is NOT Tiffany!”

In less time than I thought it could take, I felt a slap across my face and felt more than saw Jessica in my face, holding my chin up so she could look me straight in the eyes.

“Tiffany... Yes, that is now LEGALLY your name. Paul is no more! Keep that in mind. And the next time you raise your voice at me, I will remind you that though you may LOOK like a woman, you still have those sensitive parts between your legs that remind you that you are neither man nor woman but rather a sissy!

“Now, you may not like what I am doing to you but I told you that you needed to be punished. Your punishment is not as severe as I could have done, like divorce you and make sure that it all came out, your love of feminine underwear and clothing as well as bondage and other kinky shit. But I decided, after thinking about it, that I might like to have a little girlfriend rather than a husband, since this way, not only can we do things together, but we can also get closer. You may not have been able to truly satisfy me with that cock of yours but that tongue of yours has ALWAYS been good to me. So, since it doesn't do me any good I decided to lock it away so I didn't have to worry about you using it anywhere.

Of course, I do admit that the DD cup breasts might have been a little much, along with the laser hair removal. That did take a little time, let me tell you. Then changing the room up here a little so that you would have someplace for your girlie things. Besides, it gave me more closet space for my clothes, both my regular clothes as well as my, shall we call them my 'bitch' clothes.”

I looked up at her and still trying to come to grips with all of this, felt her lips caress mine and then a whispered, “I am still in love with you, Tiffany!” As I kissed Jessica back, everything started to feel, well, if not better, certainly a little less stressed.

“Now, as far as the neighbors are concerned, it is only the ones who, like Martha, have this affinity for the not so vanilla lifestyle. Martha actually introduced me to these people's other side of life over the last few weeks and I think that you will, if not become friends, will at least become comfortable with them.

“Some of the women like men in panties and other feminine things. If you look under the male clothes, I am sure that their significant others were wearing at the very least panties and stockings. And I can assure you that at least one of them is wearing a chastity device as restricting as yours.

“Some of the men there are dominant and their partners, be they male or female, are submissive to them. Sort of how you will be with Martha, Jack and me. Yes, before you ask, Martha and Jack will, on occasion, want to, well, play with you, and that can and will include sexually.

“Now, what I would like you to do is put on the black maid uniform with white trim, the white petticoat with black trim and black panties with white ruffles. The black corset should work out well. Change over to regular seamed stockings and then the black patent pumps. Once you are dressed, come back out. I am not going to make you do any serving but I want the to see that you will be coming over properly dressed. When everyone else has left, then we will talk about your future”

Jack and Jessica left the room. I was wondering why Martha was still there as she went over to the dresser and pulled out the black corset. She was going to help me get dressed, it seemed. Once I was corseted, pantied and stockings, I pulled up the petticoat and slipped the uniform on. Martha tied the apron in place and then brought me over to the table.

“Tiffany, you really are going to need some practice at make up. It wasn't too bad a first attempt but we are going to have to make sure that you definitely look like a Tiffany.” With that, she worked my make up like a pro and in minutes, I looked far more feminine than I did before. I was absolutely shocked as I looked at myself. Without even thinking, I smiled and said, “thank you, Martha” and got a little hug in return. “You're welcome, Tiffany.”

With that, I left the room and walked back into our living room. When I walked in, the women all clapped and a couple of the guys clapped as well. I felt a little embarrassed but after a few minutes, I started to become comfortable. Most of the women who were there complimented me on my look, which I then pointed out Martha for the face. Then some of them said that they were referring to my ability to look feminine and I blushed, saying that I had a great deal of help in that area, pointing out both Martha and Jessica. I was still a little flustered, as some of the Dom's seemed to want to hit on me, only to see Jack shake his head. When he walked over to me and groped me, he then whispered in my ear, quietly but not so quietly that some of the women there couldn't miss it, “Well, are you ready to be completely feminized, Tiffany?”

I felt myself blush as one woman walked up to me and told me that sucking dick was nothing. Of course, she did tell me that cum would be an acquired taste but that since I seemed to relish in being feminized and feminine, that I would soon enjoy the feeling of strong, throbbing cocks in my mouth and sucking the cum from them.

“Or, did he mean you were going to get your little cunt fucked, Tiffany?”

I didn't know what to say to that one and she could tell that I had just been shocked into silence. That made her laugh as she then proceeded to tell me that the first time it would hurt at first but after, say, fifty or sixty times, it would get easier. Then she laughed and walked away.

The little gathering lasted a few more hours but it felt like it was only minutes, walking around and talking to all of the people there. Sometimes Jack was there with me but most times, I was shocked to notice that Martha was walking around with me. In fact, I noticed that Jack and Jessica would be missing at times and though I wasn't worried about it, I wasn't sure I liked how that felt.

“My, Tiffany, you seem to be getting along with everyone, even the other semi sissy guys. Those other guys, I think, have been fended off by Jack. But I can't be totally sure. If one of them bothers you, let Jack know.”

“Okay, but where is he?”

Martha looked around and then smiled. “I guess that he is fucking Jessica right now, since she seemed to be in desperate need of a huge cock.” She saw the look on my face as I started to get upset when she turned my face to hers.

“Tiffany, you won't be able to satisfy her need for cock anymore and you know it. I don't have sex with Jack any longer because, well, he doesn't interest me, sexually, any more. However, when Jess told me about you and I realized what it meant, I actually had Jack fuck me, I got so horny. It felt okay but, well, I don't like cock in my mouth and, well, he doesn't like to eat me out, either.

“So, in our talks with Jess, I get to keep you for my little slave and Jessica gets Jack's cock to satisfy her cock cravings. You'll also be there to satisfy Jessica's need to have oral sex, as well as Jacks need for a blowjob once in a while. And that wonderful old bitty that teased you about getting fucked... Well... That I am sure you will eventually ask for but, well, it isn't necessary. Though, to be honest, Tiffany, I really would like to use my double ended dildo on you some time or another. I haven't had an opportunity to use it on anyone and, well, it seems to be going to waste.”

I was still trying to wrap my head around the fact that Jack was fucking my wife and yet, I was also wondering what it felt like to be fucked... And here was Martha, telling me that she wanted to...

And that was when I realized that all of the guests were gone. It was just Martha and me in the room. And for some reason, I looked down at her and then, the next thing I knew, I was on my knees before her, looking up at her, unable to say anything. I just looked at her as she looked down at me.

“Are you sure, Tiffany? You don't have to, you know”

I looked up at Martha, realizing that I did, indeed, want it...

“Martha, I'm not a woman but I want to feel like, well...”

Martha took my hand and led me down the hall. I had not realized it until that very moment, but I was actually in HER house, especially when she led me into her bedroom and started to tie my arms behind my back. Then she bound my elbows tightly, almost to the point of touching. I moaned with the pain but was also starting to get into it.

Then she bent me over the foot of the bed and pulled down my panties. I was shocked when she asked me if I wanted a gag to muffle the screams. Part of me wanted to say yes but I actually said no. Then I felt the sting of her riding crop and I could tell that she was the one who had given Jessica lessons on how to handle it. I was crying out and moaning as she continued to lash at my offered naked ass. And then I felt it. At first I felt something a little moist. Then a finger. Then there was something harder! She had started to push the dildo past my sphincter and after a few moments it started to thrust into my ass. I started to cry out as it did, indeed, like the old woman had said, hurt like hell! I even started to beg Martha to stop but she told me that there was no going back on my word.

After what seemed like an eternity, I started to notice that there was not as much pain but that I was actually starting to, well, if not enjoy it, it was at least starting to be less painful and more pleasurable. And after a little while longer, I started to actually push back, trying to get it deeper into me. I even started begging for more, or deeper, or even faster as Martha had her first orgasm, causing my own cock to start feeling the pain of its constriction. And after a while I could feel something building up in my balls as I was nearing my own orgasm as Martha hit number two. As she moaned through her long orgasm, I felt it start and soon, oozing through the chastity and onto the floor was my own cum. But as much as it felt good to have that happen, I was still feeling a little bit MORE horny as she was still fucking me and I had the orgasm but still wanted more! (Usually when I had cum during sex or some of my bondage games, the minute I did, I was ready to stop. But not now... I was craving MORE!)

I felt Martha pull the dildo out of me and I actually cried a little as she pulled out. I felt Martha caress my cheek and assure me that she had just the thing to keep me in the mood. And in just a few moments, I felt something larger and longer enter my ass and then it started to vibrate! I felt some things being moved, and soon it was locked in place using the chastity I was wearing.

“This should keep you all horny and slut-like while I take care of some needed business.” Then she reached over and put a penis gag into my mouth. Then a little swat on my ass and she pulled up my panties. I was squirming as the vibrator violated me and made me mad with a need for something more. I don't know how long I was left there. But when Martha returned, she had brought Jack and Jessica into the room.

“Oh my!”

From the sound of that, I could tell that both Jack and Jessica were, well, not shocked, per se, at what they were seeing. Well, maybe they were because I was certain that I was quite the site, bound and bent over with my ass in the air. I was also moaning and squirming with that large vibrator in my ass and I was sure that they could see the wet spots on my panties as I was literally oozing cum through the chastity.

“So Tiffany, I see that you are still a horny little slut… That is good because, well, since Jack and Jessica have rested up, it is time for you to, well... I am sure you can guess!” I felt my panties getting pulled down and hands working the gag strap. In moments, Jessica was spread out in front of me, pulling my face into her pussy and I could smell and taste Jack’s scent there. And it didn’t take long before I felt his long, thick cock enter my sissy cunt and I was moaning even more, trying to make sure that my wife was pleased. I could tell that Jack was happy with my ass, as each time he thrust into me, I was trying to make it go deeper and harder into my willing cunt.

“Oh Tiffany, you are indeed such a little slut! So much so that I may have to lend you out to some of the neighbors and such, seeing as they all know what you are! And just think about all the husbands and wives out there that will want you to come and clean their homes, and other wonderful things…” I could hear the three of them laugh as I felt Jack unload his cum and my own little cock, imprisoned as it was in the chastity, was begging for release and wanting some kind of attention, just so I could actually feel a true orgasmic release! But it was not to be.

I felt Jessica release her orgasm and lapped it all up and was pulled away by Martha. She led me back to the basement dungeon and explained to me the bad news… the chastity was indeed permanently attached and that I would never be able to have an orgasm in the male fashion. And that from now on, I would ALWAYS have that vibrator locked inside my cunt, only coming out for two things… I knelt there and cried as the reality of the situation finally came to mind and I realized something very telling…

I am not a woman, but… I was no longer a MAN either…

 

 

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