The Photo Shoot

I had always wanted to try a photo shoot. Of course, models do it and even nowadays, women were doing those boudoir shoots as well as just about anything else. And, of course, there is also the pin up shoots. Of course, the key component of those things is the fact that it is women who are being photographed, not guys like me. Oh, I have the wardrobe and all, I would guess, but the ability to get the desired results, well, hard to find someone willing to do that, take a guy like me and make me not only look like a sexy woman but then also get the poses… Or at least so I thought… Of course, sometimes you get more than you bargain for and, well, other times you wish you were, well, prepared for the outcome…

Now certainly, we all like to fantasize about things and, well, I would have this fantasy about being that damsel in distress that we all saw in the magazines of old and the bondage magazines. Heck, even Lois Lane in the OLD Superman show got tied up several times. But of course, THOSE kinds of photo shoots are something else entirely.

But one day, I decided that I needed some girl time, as it were. It had been a stressful couple of weeks at work, travelling and such and, though usually an excellent opportunity to at least find a few hours for some girl time, etc, I found that by the time I got back to the hotels, I was just plain stressed out and could not relax. But after three weeks, I found myself with not only a day off but a three day weekend so I knew then that I was going to go whole hog.

I got up early in the morning and took a nice hot shower. I normally keep myself shaved but, well, I had been neglecting some so I had to make sure I got it all… Nothing feels better on the legs than beautiful stockings on freshly shaved legs! I made sure my arms were clean as well as making sure that my face was smooth. Once I was out of the shower, I decided to sit at my little table and spread out my make up, trying to figure out what kind of a look I wanted. The problem usually is that I tend to look like a train wreck OR a drag queen version of Tammy Faye Baker, which means I look like hell… But I keep watching You-Tube videos that people suggest and, well, while I might believe I am getting better, I usually feel that I either go too far or way too short. But I was trying.

So, once I sat down, used some which hazel on my face to clean any remaining oil from the face and start to work on the foundation. You would think that this would be easy but nope… But I started there, then spent maybe 30 minutes just to get the false lashes on my eyes. Why do these things have to be so difficult, right? But I get them in place, start to work on eye liner, trying to get it just right, taking my sweet little ole time. Once the eye liner is done, I look and think not too bad. Eye shadow and such take a little less time and then I work on the other little things. Since I have somewhat trimmed by eye brows so they are no longer large and bushy, it at least appears to be less masculine. I finish up with my lips and then grab the wig cap. Since my hair is kept kind of short, I have to do the wig thing. While I know it isn’t much, I do like the two that I have. My red wavy look is nice, since I am rather pale as it is and somewhat red haired naturally. Of course, I like the blonde one for other reasons but today I decide to be the red head.

Once I get the wig cap in place, I pull out my wig to make sure that it is somewhat clean, brushed and presentable. Then I go to the drawer to choose my undies. While I love the basic colors of white, black and beige, I also have some in red and blue. But today I want to be in black so I pick out my black 8 strap garter belt. No pantyhose for this girl. I may not be a product of the 40’s and such, I do so LOVE the thought of these vintage styles. Once I have that around my waist, I pull out my waist cincher and put that on. Being a guy, you gotta tuck that waist in to fit in these clothes right. Once those are on, I open the stocking drawer and pull out some beautiful black seamed stockings. I love these because the stockings have a pretty red seam down the back to match my heels that I love to wear. Once the stockings are rolled on and attached to the belt, I pick up my panties. Sorry girls but I also don’t like the little things you call panties and thongs either… No support. So “granny panties” are the thing. Of course, since I want to be flat in front, I have to spend a couple minutes getting tucked in and between. Once that is complete and I have my panties in place, it is time to get to work on the top half.

So I pick out my pretty lacy black bra, pick up my breast forms and take the spray and lightly spray the back. I put the bra on and then insert the forms in so that it holds them in place. It also allows me to not have to hold onto them while the adhesive takes hold. I walked over to the closet and search through until I find a nice black blouse and a red skirt to wear with it, and reach up to get my favorite heels, black patent with a red patent stiletto heel. Of course, I have these in a high heel at 5 inches but have discovered that it is easier for me in higher heels than in smaller ones. Then I walk back to the lingerie drawer and pull out my pretty nylon slip. A proper lady wears a slip, don’t they? I don’t care, since I love wearing a slip and it makes me feel more feminine.

Once I have the slip on, my clothes in place, I reach for my wig and get that into place. I take a peek in the mirror and while I don’t think I have done a great job, I feel better about my effort this time. Then I look at the clock and realize that I have been wasting time. It has taken me all of three hours to get dressed. Not that I was planning on going anywhere, it did take me longer than I thought. But I was done and I could do a few things around the house and enjoy the morning and afternoon.

I decided that I would take care of some of my paperwork that I had to complete so sat down and started to get it done. I didn’t realize that there was so much to complete until I actually started to get it done and poof, it was finished and much quicker than I expected to finish. I guess being relaxed and in girl mode helped me. But I was starting to get that little itch I also have to indulge. So, I went back to the bedroom and pulled out my little bondage bag. I looked at the time and knew that I had plenty of time to enjoy a little self bondage before I went out. And I wanted to really feel like that damsel in distress.

So first I took out my ankle cuffs. I like these because they also lock on your heels. And while walking in 5 inch heels is childs play for me, I also have a pair of seven inch heels that I love to wear for bondage play. Of course, first I have to make sure that my key for the locks is available so I go to the freezer in the kitchen and pull out the small ice block. Normally it would take about 3 hours for the ice to melt so I knew I was okay. I take the block and put into the container and bring that back up with me. Now it is time to change the shoes out and I get the cuffs on and lock on my heels. I take another set of cuffs and put them on my wrists so I can do a hog tie. I also wanted to be a little more uncomfortable. But first I need to remove the blouse and skirt since I don’t want to damage them as I squirm. Then I take out my vibrating dildo and roll a condom over it, lubing it a little to make it go into place easier and pull down my panties. Since in the past I have had little “accidents” I also roll one on my cock so, well, if I have another accident, I don’t ruin my pretty panties. Once I manage to get it into place and my panties back into place, I take out a leather strap and place it around my waist. Then I take the crotch straps, pull them between my legs and snug against my dildo to keep it in place as well as keep my cock in place. It is something like a poor man’s chastity. Then I pull the slip back down.

The dildo has a time delay and variable speeds. All I have to do is turn it on and it will do its thing, usually for up to six hours on the good batteries. And where it hits inside can, sometimes, bring me to a climax, though usually it just torments me. Then I decide that I want the blindfold and gag. I have a harness for this so I put this on. The gag is a penis gag. It took a while to find one that was not too long and didn’t make my mouth burn and have a strange taste for a week. Once that was in place, I laid down on the bed. I could feel the vibrator starting to work and knew if I did not hurry, I would spoil the effort. So I grabbed the chain and locked it on my ankle cuffs, pulled my ankles back and then reached up for the harness. I found the d-ring on the top of my head and clicked that into place. All that was left for me to do was put my wrists in back and lock them onto the chain between my head and ankles. I clicked the first one to the chain and then, with a little bit of fear clicked the second lock into place!

I was effectively muted and in a hog tie. And with my head pulled back as tight as it was, the gag was uncomfortably snug but not too much. The vibrator was starting to speed up and my cock was getting VERY painful as it was essentially locked down between my legs. I couldn’t really move my arms. And with all of that, I could feel that delicious feeling of helplessness and submission. Since in all those wonderful stories and such, the damsel in distress struggles in their bonds, that is what I did! Each time I moved, I could feel the vibrator work it’s magic and the discomfort in my crotch was certainly reminding me about the straps holding me all tight there. But the mental picture in my head was so nice, and the internal feelings made me actually struggle more. And when I shifted I could feel the container with the key fall onto the floor!

Here I am, hearing the plastic container fall onto the floor and the ice cube sliding away. They say that when your senses are taken away, the others will try to make up for that one you lost. Being blindfolded, even for a short time, I would swear I could hear it slide far away, though it could also be playing a trick on me. Since there is nothing I can really do as it is and now, because I was really getting into the idea of being bound and gagged in my underwear, testing my bonds, I was now in trouble! I really was going to be that damsel in distress! And the floor is some 2 feet below the bed so getting to the floor is going to be tough as it is. But that fear is also powering the fantasy and with the reality of having to find that key as well as the fear of the NEED to find the key, the vibrator doing its thing as I struggle to move to the edge of the bed, I can feel myself starting to go over the edge. I slow down the struggling since I don’t want to have an accident as well as wanting to be coherent while I search. After a couple of minutes, I regain some of my composure and start to work my way down. As I start to work my knees over the edge, I realize that I can’t bend that way as my head is pulled back and it is not going to work that way.

So now I have to work my way across the bed to the other side. I realize that I have a couple of pillows on the floor over on that side and that should, I hope, make the fall a little less painful. NOPE! I thud onto my side and while I am down and on the floor, I now have to struggle to get off the pillows and try to get over to the other side of the bed. And as I struggle, I start to get excited again and have to stop as now, while I am down on the floor, My ass is now kind of up in the air as I try to get off the pillow and that is making the vibrator work its magic inside me. And as I struggle, I realize that I am enjoying this far more than I would have expected. But try as I might, not only could I not get off the pillow fast enough but I was REALLY feeling good and as I unloaded into my condom covered cock, I was still feeling needy. That vibrator was really doing a number on me. And now I was feeling a little tired. I fell asleep on the floor, my ass in the air, gagged and helpless.

When I woke up, I knew I was in trouble! I was no longer on the pillows but on the floor. I was still blindfolded but I could feel the floor underneath me instead of the pillows. But I could now HEAR someone was in the room. And I could hear what sounded like a camera clicking as several pictures were taken. No words but lots of clicks. And there were clicks as the person moved around and I knew that those clicks were someone who was going to make me pay for this little adventure.

The Photo Shoot - Part 2

While I was unsure as to how long I was there, I had a feeling that I KNEW who it was, as I was supposed to meet up with her before we went out. And while I certainly like this gal, it felt like all we would ever be was friends. All I could think, now, is that being friends had just gone out the window!

“So, sweetie, you like to dress up like a girl, do you?

I could tell she was near me but not really which side she was on. All I could do was mumble and try to nod my head.

“It also seems like you are into bondage, sweetie. Not that you need to answer with words since, well, you ARE all tied up! But I wonder just how slutty you might be…” With that, I felt a tug on the slip and heard her laugh.

“So, I wonder what this strap is holding in place? Could it be a dildo, sweetie?

I mumble and nod, feeling the heat in my cheeks get hotter and hotter.

“Are we feeling a little embarrassed, sweetie? You don’t need to answer that either, since, well, your face is beet red right now. But I bet you are very uncomfortable right now, right?”

I nod.

“Well, I bet that the puddle of water on the floor held some keys, maybe even these keys I have in my hand. But before I unlock anything, I want to lay the ground rules. First, no talking. I am going to release your head from that chain, then take off the blindfold. Then you can sit there and answer some easy yes or no questions.”

First I feel the chain disconnect from the head harness. I moan a sigh of relief. When she pulls off the blindfold, I can see that it indeed Karen and that she is dressed to the nine’s. We were supposed to go to the bar and celebrate her upcoming birthday tonight, as I would be gone for her birthday. Some of her friends would be there as well. Since I don’t drink, well, I usually would be the DD (Designated Driver) for her and her friends. I didn’t have a problem with that as I got to spend some time with some really fun people (mostly women but there was a couple of guys on occasion) and, well, to be honest, I tried to pay attention to how each of them looked and dressed. I know, bad, right?

Then I was rolled onto my side and when she looked between my legs and saw the way the strap held me in place, she lifted the side of my panties at the leg and noticed the cum filled condom. I watch as she snickers, shakes her head and then walks out for a second.

When she gets back, I see that she has brought one of my folding chairs. She sets it up and looks at me.

“I am going to release your wrists from your ankles. BUT, your wrists will stay behind your back. Since you really can’t walk bound like that at your ankles… Oh my goodness… Those heels are GORGEOUS! And so high! Can you walk in those?”

I shake my head a little. I have maybe taken a total of 10 steps before I can’t do it any further. Seven inch heels (at my height, they actually hit at 7 ½ inches in height, which REALLY makes me tall!)

“Well, lets get you up and sitting in this chair. I want to talk to you and trying to squat down to talk to you is getting annoying”

I feel my wrists being released from the chain and she helps me get to my knees. Then I crawl over to the chair and with her help I get into the chair but I have to put my arms behind the backrest. Then Karen takes the chain and pulls it under the chair and then reconnects my wrists.

“Just so you REALLY know who is in charge, sweetie” Then she walks around in front of me and as she walks out of the room, I pay attention to the fact that she was REALLY dressed up tonight. Her black dress was rather short, though all I could ever remember was that she ALWAYS wore a short skirt. She also was wearing stockings, which was curious, as usually she didn’t wear nylons at all and now she was wearing stockings. And those stockings were held up with a garter belt or something as I could tell that these were the REAL nylon stockings, not the “new” style, and in those heels she had on, her legs looked LONG! She was already tall but this was something else to behold. All I could think of is that I was REALLY going to pay for this now. The only thing is that I was wondering if I REALLY wanted to pay whatever that price might be…

A couple minutes later, I watched as she came back into the room. She had her cell phone out and clicked a couple more pictures of me, now sitting there on the chair in my slip. It was then that I realized that the vibrator was starting back up again and I started to squirm.

“I saw the remote over on the table. I didn’t realize at first what it was for until, well, I hit the button and there you are, squirming like a little worm. I forgot that you had that vibrator inside you too until just now. I bet that right now, then, you are feeling a little more uncomfortable, huh?” I nodded. “Good. You deserve to be uncomfortable. But I think that I have some questions that need to be answered by you. Because now, I am kind of wondering a few things about you, just as my friends were. Of course we didn’t want to embarrass you or humiliate you by asking some rather pointed questions but now, well, embarrassment is the least of your concerns, right?” I nodded again.

“So you know, a couple of the girls are going to come over in a little while. What kind of position you are in will depend on, well, you. Right now, well, they don’t know anything about why you were not there to pick them up. I said, honestly, that you had been tied up but should be free in a little bit. So I invited them here and we could take it from there.
“We have been wondering, and now I kind of know why, you hung out with us. Oh, I know that you pay attention to us and do indeed take care of us. I know that there have been opportunities that you could have taken advantage of any one of us but, like a good friend, you didn’t. We THINK you like girls but, well, now, not too sure. Are you gay?” I shook my head. “Okay, you like girls, but, well, are you, well, bi?” I shrugged my shoulders. “Interesting…”

She walked over to the closet. I watched as she walked over and saw her rummage through the closet.

“Well, look at what I found here!” I looked as she pulled out my prized possession. A satin maid uniform in white bridal satin with black lace trim. Under that was my petticoat in black with white trim. Then she pulled out the other uniform, exact opposite of the white uniform. Each had an apron in matching colors. She held them both up and looked at me. I think that this solves the problem of what will happen when the girls come over, sweetie!” I don’t know if I could get any redder but I certainly felt the flushing in my face. “But, of course we are going to have to make sure you can walk. You DO have heels you can walk in, right sweetie?” I nodded and with a nod of my head I directed her to the box under the bed that held all my heels.

She walked over and pulled it out. “Oh dear, you DO love stiletto heels, don’t you?” She then pulled out a pair of black patent heels with a five inch heel and ankle strap. She put them on the bed and then laid the white uniform on the bed as well.

“Okay. I am going to give you a very interesting proposition. I will let you out of this little predicament that you are in, allowing you to change your clothes into boy clothes and we can all go out and spend time celebrating my birthday as we had planned. But I have a feeling that, well, you might be more than game for what I have in mind. What I have in mind is that you clean up and then I will do your make up. Then we will dress you in this maid uniform and make sure that you are all properly done up. You will have your ankles cuffed holding those heel in place but I will let you walk around. Your wrists will be cuffed in front of you so that you can serve a drink and such. If you are a good girl for me and the others, maybe we will give you a little something more as a reward. If you are a bad girl, well, we can punish you as well. Your choice. However, if you take the boy route, when we are done, since I am going to make sure you STAY locked in those panties and with that vibrator locked inside you, I will make sure that you get punished when we get back here. AND that you will be locked up over night.”

She walked around the back and unhooked the harness around my head. I felt such relief at having the gag out of my mouth but I had also been drooling so Karen wiped my face. “So, what’s it going to be, sweetie?”

I could not decide if I was willing to go all out. “I don’t know, Karen.”

“Sweetie, from now on, it will be Mistress Karen to you!” After she said that, she slapped my face and it stung! “Sorry, Mistress Karen.”

“I think you need a good spanking then, don’t you!” With that, the harness was put back in place and the gag in tight. I felt my wrists get unlocked from the chain and I was told to stand up.

I was then led to the bed and made to bend over it. I felt the strap being undone from my back and the strap holding the vibrator was pulled out of the way. I then felt the vibrator come out and I started to shiver and sigh!

“Oh sweetie, that sigh of relief is going to be very short lived.” I looked around and realized that this was not going to be something pleasant. I heard her walk out of the room and return a moment later.

“Sweetie, I guess that, well, you should know a couple of things about me that you might not have known. First of all, I do not normally like men. In fact, while I like men for conversation and such, most men are, well, PIGS! But they are, indeed, useful for some things. Sex is NOT one of them. I am not into guys in that way. Which is why I had some difficulty in regards to you all this time. Something about you interested me. My girlfriends were the same way. You might not have known it but we talked about you behind your back a whole lot. But I don’t know if they caught what I did one time while we were out, playing pool. You bent over to make a shot. They were in front of you but I had moved around the back and I saw your cute panties. I noticed the waist band from Secrets in Lace and since I have a pair like them, I knew you were wearing panties then! I didn’t say anything to the other girls but I knew. I just didn’t know how much… Now, I know you like bondage. But I wonder if you like the other side of the equation, but since you seem to NEED a little discipline, I think we can help there as well!”

I watched as she put a saw horse on the bed and then felt her lift my arms up and secured them to the horse. I was in a sort of poor man’s strappado! Being bent over the bed gave me support but it was certainly NOT comfortable.

“Of course, if we were at MY place, we would certainly be able to do this the RIGHT way! Because, sweetie, I LOVE to tie up men, and women, and discipline them for being bad little boys and girls. And so many men LONG to be punished by a pretty woman, don’t you?” With that, I watched as she took off her dress and stood there in her underwear. I had been right about the stockings but MISSED on the garter belt. She had on an overbust corset that really looked great on her, pushing up her breasts and nipping in her already tiny waist. And the panties she had on were just like the ones I had on.

“I don’t like thongs as some other gals do. And since, well, I don’t dress to impress men, except when I am paid for it, I wear what I like. I dressed like this, not because I was expecting to find you as I did but because, well, I like dressing like this. And I can see that you appreciate it, too.” Then I watched as she took the vibrator and changed out the batteries. With the gag in my mouth, well, I wasn’t going to be able to beg her not to put it back in. And I still had that condom on my cock and I was starting to get hard with the strap loosened.

“So, I think, to start off with, maybe 100 lashes!” I started shaking my head trying to tell her that I was not ready for that! “If you keep whining, sweetie, I will make it 200!”

When that first one hit, I could feel the fire in my ass and screamed into the gag. But I also noticed that as each one hit after that, I was actually starting to ENJOY the pain that was assaulting me. Instead of crying, I started to moan!

“Oh sweetie, such beautiful music coming out of you!” and once she was finished with those 100 lashes, she leaned over. You want MORE, don’t you?” I nodded my head, lost in that moment. “In a couple of minutes, sweetie. But first…”

I felt my cock being grabbed and the condom pulled off. Then I watched as she poured the contents out of the condom into a glass. Then she walked back to me and pulled it back onto my cock. Then I felt her tuck me all away and then the vibrator went back into my ass. It wasn’t so hard now as it had been in there for a while plus my ass was still on fire. I felt the strap pulled back into place, though my panties were NOT pulled up. When the vibrator was turned on, it was like my insides were on fire.

“Oh, I guess I should have warned you that, well, I put a little something extra onto the condom on your vibrator. I did tell you that I wanted to make you a little more uncomfortable, didn’t I? Oh yeah, I didn’t, did I. Well, now you know. The heat should last maybe a couple of hours… Seriously, maybe an hour.” Then I felt the slash of the crop again as she administered another 100 lashes to my aching ass cheeks. And with the vibrator working its magic and such, plus my new found masochism, I could feel my cock strain to get hard and after a few minutes, I could feel another orgasm coming up inside me. And with me struggling as my arms were pulled up and my ass was getting whipped, I was indeed a damsel in distress! And all I could tell was that I was enjoying every minute of it, as painful as it was.

When she was done, she pulled the buckle on the strap and then removed the vibrator. The sign of relief was very pronounced. I could even hear her chuckle again.

“I think I know what you are going to do. So, I am going to release you and you are going to clean up. When you are done, you will get dressed in what I have put onto the bed and then we will take care of the remainder of what is necessary for this evenings activities. Oh, and so you know, I videoed all of this, as well as the pictures I took. I think you would be very photogenic. And since I see you have some bondage magazines and LOTS of pictures on a couple of thumb drives, well, I know what you like… And I even know someone who would LOVE to take REALLY good pictures of you. You do too, in fact. But more of that later.” I felt her release my arms and unlock my ankles. When she took off the harness, like I knew I should, I knelt and said, “Thank You, Mistress Karen” She looked down at me and smiled.

“Get cleaned up. The girls will be here in 45 minutes. You need to be dressed and ready to go in 30 minutes. Get moving!”

Off I went to get cleaned up. For some reason I had a skip in my step and something just started to feel, well, RIGHT! And while my backside was nice and red I was sure, it was the feelings inside my head and my heart that really caused me to wonder what was going to happen. And it was not with fear nor trepidation but rather excitement and wonder that I went into the bathroom and got all washed up again, shaved my legs and such and dried off.

When I walked into the bedroom again, I saw that she had laid out white underwear for me. Since my breast forms were still stuck on me, as I didn’t want to spend the long amount of time it took to take them off and put them back on, I figured I was good to go there. I saw the corset, also custom made for men (a little longer as we have that extra rib, ya know) and the white SIL panties. I put the panties and then the petticoat on. Then I pulled the corset around me, attached the busk and then started to lace the corset as tight as I could. It was then that Karen entered the room. I stopped and knelt.

“Okay sweetie. Lets get that corset nice and tight.” With that, Karen pulled the laced tight and then tight again. This corset was designed to be tightly laced and reduce the waist by some 5 inches. I had never done it that tight but this day, I was sure that it was tighter than the 5 inches. “Holds you in nice and tight, doesn’t it, sweetie? I saw what you had and decided that you needed one size smaller. And I just happened to have one size smaller in my little handy, dandy discipline bag.”

With that, she pulled out a penis gag without the harness. “Open wide!” Then she pushed it in nice and snug and I heard a click behind my back as she locked it into place. “That should help to keep you quiet,” she snickered and then had me sit down. It is NOT easy wearing a tightly laced corset, let me tell you. Especially when you learn that this is NOT the corset you had but a SMALLER one! Then Karen proceeded to talk to me as she described what she was doing to my face. How she put on the foundation, then eyes, blush and all the rest. She was even able to put some red on my lips as this penis gag filled my mouth but left my lips, at least where the strap didn’t cover, exposed. When I looked in the mirror, I could see someone who definitely looked slutty and feminine at the same time. “In time, you will be able to do that yourself. But I wanted to make sure you were all made up. Now, put on your uniform.”

I got up and walked over to the bed. I took the uniform and pulled down the zipper. Once I had it down, I pulled it over my head and started to zip it up. In no time, I was all zipped into the uniform and then Karen took the apron and tied it around my waist. I looked like a little, slutty French Maid. Okay, not so little but I was certainly dressed like one. Then I picked up the shoes and put them on. Karen then handed me the ankle cuffs and I sat down and put them on. She handed me the locks and I put those on and now I was not going to be taking these off for however long she decided.

“Pull down your panties, sweetie!” I lifted my petticoat and worked to get my panties down. Karen then took something else from her little bag and as she put it on my cock, I realized that it was a chastity device! It was COLD! And it was metal and not plastic. I felt the collar go around my sack and then the tube was put into place and I felt the lock go in place. It wasn’t super uncomfortable but, well, she wasn’t done yet! “Bend over now, sweetie!” I did and then I felt her put some lube at my opening just before she thrust in a new vibrator. This one FELT larger and longer than the one I had used. It was not really bad yet but I could feel that there was to be more. I felt Karen take my belt and put it around my waist and then the straps pulled between my legs, pulling the chastity down as well as strapping the vibrator in place. Once that was done, I heard another click for a lock in back.

“This vibrator is very nasty, sweetie. It runs on a battery that will last up to 24 hours. It is designed to be operated by Bluetooth, where ever I am as long as I can get a signal to it. Or, as they say now-a-days, ‘there’s an app for that’. It is connected to your phone, not for control but for relaying instructions when I am not with you. If you are a good little gurl, it will just buzz and give you nice feelings inside you. However, if you are a BAD gurl…”

The pain I felt in my groin was pure evil! While short lived, like maybe a second or two, it felt like more. And the pain was in my ass, balls and cock! It was a very distinct shock and I did not like it one little bit!

“That was just a taste of it. If you are bad, the first time will be like maybe 5 to 10 seconds worth, not all at once, mind you. And couple that with maybe the leather strap going across your now rather sensitive backside, sweetie and you will learn better.” I nodded, knowing that I would do anything NOT to have her punish me, especially after feeling that jolt. But the other problem was that the vibrator was sitting right in a really bad spot. Not bad painful wise but rather, well, even though I had cum twice from everything, I could feel the stirring of an erection as that vibrator was working its magic far more intensely than my little one. But, of course, with the chastity in place, all I was feeling was, well, more than a little discomfort. I had a feeling that this discomfort was going to be a real problem later on.

“Now sweetie, pull up your cute little panties. Don’t want to subject the ladies to, well, your little bad boy bits. Not that you could do anything with them right now but these ladies don’t really want to see those things, even if they are locked away. Besides, we have to make sure you are there to greet them when they get here.” Then she walked over to her bag, picked it up and as she started to walk down the hall towards the living room she stopped. “Something is missing… What could it be?” she looked at me, smiled and then reached into her bag one more time. This time, she pulled out a pink leather collar. I knew what that was for. And when she showed it to me, I saw what it said on the front. “SISSY BITCH” As she pulled it around my neck, she whispered in my ear, “Well sweetie, for now, you will be called sissy bitch, but I think, if this relationship grows and blossoms, we will have to get you a SPECIAL collar. But of course, you will have to earn that, as well as the other things you need.” I heard the lock click and was then led down the hall into the living room. What greeted me there surprised me even more than Karen and her demeanor had.

The Photo Shoot - Part 3

When I was essentially led to my living room, I learned that the other two girls of the bunch were already there. But more interesting was the fact that one of them was, well, dressed similar to me. That was Susan, who was a rather, at least when I had seen her in the group, frumpy and demure. Of course, with her standing there in a black satin maids uniform, almost matching in details to be the exact mirror image of what I was wearing. She was wearing high heels, which I had never seen her wear in all that time. But I noticed was that she was wearing a metal collar around her neck. I could not see how it came off and I began to understand why she would wear high collared shirts or sweaters. It was to cover the collar when she was out in the real world.

Also as astounding was that the other woman, Nancy, was dressed pretty much as Karen was. But I also noticed that while very refined and such, it was all leather that she was wearing, and she was holding the end of a leash, connected to Susan’s collar. In her other hand she was holding a riding crop.

Nancy looked up towards us as we walked into the room. “Oh my goodness, THIS is Chris? She looks so… I would never had guessed. So now I have to ask, was she REALLY tied up like you said at first?”

Karen laughed. “Let me show you.” She led me over to them and then pulled out the phone and started to scroll through the shots that she had made of my struggles and such.

“Damn, she likes being tied up then, doesn’t she? Sort of like my little bitch here, right slut?” Of course, Susan could not say a thing as she was tightly gagged. Then she moaned loudly as Nancy hit a switch which, I learned later, controlled a vibrator locked inside her. “See, she LOVES to be tied up. Maybe even as much as your little sissy bitch here. But, well, how receptive is she to being your little bitch? And does she KNOW what we do for a living?”

Karen smiled. “Not EVERYTHING that we do, though I think that she MAY have figured out that I am a dominatrix. And I think she may realize that you too, sweetie, are a one as well. And I think she knows that slut over there, is your partner, slave and lover. Though I don’t know if she KNOWS everything about Susan, especially since all she has ever know is that you, Susan and I have been getting together for the last several months, sometimes with some other gals and some other guys.”
“What you decide to tell Chris, who REALLY needs a more femme name, like Christy… Yes, I think that will be her NEW name, what you decide to tell Christy is up to you and Susan. But you know as well as I do that she will need to know eventually. Because I do think that Christy will stay this way for quite some time.”

I listened to their conversation and was really curious. I remember the times, and there were many since I moved out here, that I had seen her in the halls and such. Living in an old warehouse, with all the apartments here, well, you tend to meet everyone. While I did travel a great deal, I also seemed to be one of the few with a big enough car to haul people in. I have a minivan (or what some call the replacement for the old station wagon, which I would have preferred, IF they still made them) and everyone else seemed to have these LITTLE cars. I even remembered it was Karen who had asked me, when she saw me in my van getting ready to leave for the week, if I would be interested in helping out her a couple of her friends that weekend. When I looked at her with a questioning look, she explained that they needed a ride to a party for her friend, which turned out to be Susan I later learned, as it was her birthday and they were going to go bar hopping and I was invited. Karen and Nancy lived in the same building and I had seen them enough to say hi and such. I had never really seen Susan before though. But I was happy to be asked and that was where the friendship started. But now I was REALLY curious about what was going on.

“Well, how about we head over to your place, Karen. Then we can, well, take it from there. She CAN walk in those, right?” Nancy pointed to me in the heels and looked at ME. Since I too was gagged, I nodded “yes” and was rewarded with a little more speed in the vibrator and started to moan through the gag. “Oh, these two are going to be SOOO much fun, Karen!” I wondered what that meant but realized that for right now, I really had no choice.

I was led to the door, with Nancy and Susan behind me. As I walked, I felt really odd. I had never really left my place while dressed. Well, I had but not when people would notice me and I usually, since my apartment was right by the elevator, I could get to the basement and into my car quickly. I had never been caught (or so I thought) and thus realized that this would be a first leaving in the maids uniform. I would say that the feeling in the pit of my stomach was killing me but the feeling in my groin with the vibrator doing its thing was making my cock get into discomfort, what with being locked in that chastity. All I could think was “how long with this go on?” But I also wondered if this was some kind of dream…

Karen’s place was two floors up. I had never been there before and realized that she had the ENTIRE floor. The place was huge, though just the area we walked into was not that large.

“Welcome to my home, Christy. I will give you a tour later. But first we have to discipline you for your bad behavior. And Susan is getting disciplined as well for something that she did earlier.” I was led through a hallway and I noticed that it got darker in the back of the floor. I also noticed that after we got past the living space, there were only two doors. One door was open and I saw a large bathroom. The other door next to it was closed. I guessed a bedroom of some sort, figuring that it was going to be a huge room. When we got to the end of the hall, there was a doorway on the other side of the hall and we passed through it.

As far as the eye could see, this was a really HUGE and professionally done room. When you think of a dungeon, THIS is what you would imagine. I had fantasized about what one would look like and this one even blew that idea away. There was a small stage in the center of the space, with a St Andrews Cross on one side, a padded bench with eye bolts on the other side and in the middle a long padded table. As I looked up, I could see that the ceiling here was high, like over 10 feet. I realized that this would be interesting as I saw the chains hanging from the ceiling and cuffs attached to those chains. I also saw eye bolts in the floor with small section of chain and cuffs there as well. There was a thick post, some 10 inched in diameter with eye bolts as well. In between them was a small table. On the table were additional cuffs, gags, clamps and other little doodads to inflict a little pain. Hanging on the side were several crops and paddles.

We went further down the space and we found ourselves at a pair of padded benches. I could see a chain hanging down as well as more bolts in the floor. When we stopped, I knew what would probably come next.

“Okay,” Nancy said, “Time for slut to take off her uniform since we don’t want to damage it, now do we slut?” Susan nodded and after having her cuffs removed from her wrists, reached behind and pulled down the zipper of her uniform and took it off, along with her petticoat. She was now standing in a very tightly laced corset, stockings and her breasts were on display with barbell piercings through her nipples. I looked down a little further and saw that she was pulling down her panties and that was when I learned something else.

Susan was wearing a chastity device, but NOT a female chastity. Hers was a metallic version of the one I was wearing. Well, not QUITE like mine, as I could see that her cock was pulled down between her legs and that her balls were hidden. Once she had her panties pulled down but not off, as her ankles were still cuffed, she was led to one of the benches and I watched in rapt wonder as she had her ankles uncuffed from each other, her panties removed and then cuffed to the floor so she could not kick out.
Once that was done, I saw Nancy pick up an armbinder glove and start to slip it over Susan’s arms. Once it was all the way up, Nancy pulled the straps under and over Susan’s shoulders and then started to lace the binder tightly. I started to get a little fidgety as I watched Susan get laced into the armbinder.

“Are you feeling a little excited, Christy? You want to be bound like that, don’t you?” All I could do was nod as I had ALWAYS wanted to be tied like that. And as I watched, I started to get more excited.

Once the armbinder was laced tightly, I could see that Susan’s elbows were really tight, though I wasn’t sure if her elbows were touching. Then I watched as Susan’s arms were lifted behind her back and she was placed in a really strict strappido. Watching this was making me even more excited. “You’re next, sweetie!” Karen whispered into my ear. Then I felt the vibrator speed up and I squirmed like a little girl. I was getting all antsy and was confused by these feelings.

Once Susan was in place, I watched as she squirmed, just about as much as I was squirming. Then her head was pulled back towards her elbows and then Nancy picked up a cane and administered the first lash. At this point the vibrator inside me was adding to my excitement and I could feel my cock hurting me as I was becoming really excited. Karen noticed and laughed, catching Nancy’s attention.

“Oh dear. It seems that Christy is about as horny as a virgin on her wedding night!” Nancy laughed. “I guess maybe we should take care of her and let her take her place, don’t you think, Karen?”

With that, I had my wrists released and I removed my maids uniform and petticoat. Then I pushed my panties down and walked to the other bench. In minutes, my ankles were locked to the floor and I felt the leather armbinder slide up my arm. I had never felt an armbinder on my body before and was a little nervous. As the straps were pulled around my shoulder, I heard Karen whisper, “I will tighten the straps as tight as you can stand. Since you are gagged, shake your head when you are in too much pain.”

I felt my arms being hugged as my arms started getting pulled together. At first the feeling was nice, as I liked tight bondage. Then I felt the pain start but didn’t want to start out like a wimp. But after another minute of lacing I started to shake my head as my shoulders were starting to feel just a little too tight. “Good girl. Now bend over at your hips since that corset is not going to let you bend at the waist.”

I started to bend over and then felt my arms start to be lifted up. Part of me started to moan and wanted to scream but another part of me ignored that as the discomfort was also wickedly delicious. In no time, I felt my head being pulled back as a harness was placed over my head, forcing me to look straight ahead. As I looked, I saw the cameras that were there on tripods. Then, just as I realized that those cameras were going to take my picture, the blindfold was placed over my eyes and I was now in the dark. Then the vibrator started to speed up and I was starting to feel good. Then the first lash of the cane hit my ass!

“Does that feel good, Christy?” I could not really tell if I loved it or not but I also knew that I wanted more because part of me was really happy! I heard Susan get another lash and then I received one. It continued as Susan would receive a lash followed right behind hers with mine. And as each lash landed on my ass, I started to feel more and more like I wanted it to keep going. And each lash told me that I was really enjoying this. Oh, I was screaming after a while, since it was indeed painful. I didn’t realize until then that I might just be a masochist at heart. With the lashes of the cane hitting my ass and upper thighs, the part NOT covered by my nylons, and as they hit my naked and abused flesh, I would flinch, causing my arms to pull upwards, adding to my pain, discomfort and the longing I was starting to feel. When it came to an end, all I could do was sigh, though with relief or longing, I didn’t even know.

The blindfold was taken off and I could see over to my right that Susan was also relieved of her blindfold. Out gags were still in place and then I caught sight of a naked man coming in our direction. I was fearing that maybe another “thing” on my curiosity list was going to get taken off my list, wondering how it felt to be fucked like a sissy, or even worse, even before I had said anything about it to ANYONE! But I could just make out that he was headed to Susan and I could see her start to squeal with delight as I guessed that the naked man had entered her ass. Then Karen and Nancy came up to me, one on each side of my head.

“Well now, seeing as you really seemed to enjoy that, Christy, I wonder what else you might be wanting to experience. If you’re anything like little Susan there, who after I started her transformation I learned wanted to be a real slut, it wasn’t long before she was begging for the cock!” Nancy snickered and I could hear Karen chuckle as well. “But, of course, before we let her experience the cock, well, we had to make sure she could handle the cock. A good old fashioned dildo fucking was all it took for her to be begging for the real thing. And since she is going to be busy being fucked by a couple of guys for the camera, we can take a little time seeing how much you want it” Karen knelt lower and whispered into my ear quietly, “And I KNOW that you REALLY want it. I can smell it. And your body was telling me that you wanted his cock inside you. So, in time, sweetie, you will get what you want. But I want to watch you show me how MUCH you want the real thing!”

I could feel the vibrator being pulled out of me and as it did, the vibrations hit me and caused me to moan into the gag. They both laughed a little and first Nancy came around in front of me, showing me the dildo that she would use on me. After the vibrator that she pulled out of me, that dildo she had on didn’t look quite so bad. But the problem was that I didn’t see Karen’s dildo as she slowly entered my ass! I started to scream into my gag, even as she continued to enter me. “You know you want this in your little sissy cunt, Christy! And here it comes!” Karen then thrust deep into me and I could feel myself, as she started to thrust in and pull out, slowly at first, start to get into the rhythm of her penetration. I was moaning in moments and started to thrust back onto the dildo, escaping the reality of who I was and taking the new reality of who I was becoming.

I then watched as Nancy reached behind my head and removed the gag in my mouth. When she did that, my moaning became loud and guttural. I heard the guy pounding into Susan laugh as I moaned. Then I watched as Nancy came up to me with her dildo and as she grabbed my head, she politely said, “open up those pretty lips and take my ‘cock’ Christy like a good little slut!”

I didn’t even have a chance to CLOSE my mouth as Karen kept at my new found cunt and the glorious feeling I was experiencing from her fucking me. But the dildo entering my mouth woke me up to the fact instantly as I was now trying to take her long dildo into my mouth and throat. It must have taken almost ten minutes before she was able to get it fully inside me as I learned how to STOP the gagging I was doing as she trained me. Being unable to stop anything at this point, I realized that I was starting to, heaven forbid, actually ENJOY it! Part of my head kept telling me that I was a MAN and that this was NOT something a man would be enjoying. But another part of me, the part that was starting to SCREAM rather than whisper as it had for many years, told me to stop listening to that voice and to listen to her voice and let her out! I was at the point where I could stop it if I wanted to, and I DIDN’T want it to stop! But it did stop and when Karen pulled out of my cunt, Nancy pulled out of my mouth, I actually started crying…

The Photo Shoot - Part Four

There I was, crying while still in bondage, not really knowing WHY I was crying. I felt my arms being released and felt myself being laid onto the floor. I could see that Susan was now released and was kneeling there next to me. Karen and Nancy knelt down next to me and Karen pulled my head towards her shoulder and started to soothe me, telling me that everything was alright and okay.

However, in my head, NOTHING was alright and certainly not okay. My mind was having a fight that I had never expected to have in my wildest fantasies or dreams. I had just found myself captured, bound, gagged and fucked and I actually LIKED it! That was just not right to me… Or was it just TOO right FOR me??? And I was sitting there, next to this woman whom I really didn’t know I had any kind of feelings for her OR Nancy and Susan and now, because of what had happened these last few hours, I had STRONG feelings for all of them.

“What we will do is let you rest, Christy. You have had an eventful evening, to say the least. And right now, your mind is taking so many different turns that, well, you might say something and then say something else and not know which way you are going. Susan was the same way over a year ago.” I felt Nancy and Susan help me up and then Karen led me to one of the beds in another part of the house. Hell, this room looked like it was used for boudoir photo shoots as I could see all the equipment for taking photos and the bedroom just SMELLED of lingerie and femininity. Even the comforter on the top of the bed was satin. I lied down and was instantly asleep.

When I woke up, I was still in that room. I could see a little table on the side that held a bottle of water and a note. I took the bottle and as I rolled I could feel pain in my ass, or would that be in and on my ass, and it stung a little but I also kind of relished that pain for a second, as it told me that this was real. I opened the bottle and drank the entire bottle down. Then I picked up the note.

Dear Chris (ty),
I know that this evenings events are a little tough to comprehend let alone come to grips with what you experienced. If we went too far, then I am sorry and I accept the possible consequences of MY actions. I don’t really know what it was that made me act in this manner towards you because, well, in all the time you never really showed an interest in either me, other than as friends, which was fine, or anything resembling what you feel inside about yourself.
I became curious that night about a month ago while we were playing pool and I saw those panties you were wearing. Like I told you, I have a pair just like those, but if you are anything like me, you probably have many pairs. But when I was that, I was thinking that maybe, just maybe, we could be more than friends.
Yes, sweetie, I am normally a lesbian. Oh, I like guys and all. Most of my Domination clients are male, though I do have a couple female. Many of the guys are just into being dominated. I would say a couple like being dressed up and treated like a girl though. Some may even qualify as sluts, truth be told.
But something about YOU was different. The only other GUY I was attracted to was also a cross dresser. However, he was not so much submissive but VERY butch. And he was not really into girls but into submissive guys too. He became a Trans Domme, with the breasts and all but kept his cock, which was, honestly, kind of big! Oh, he could be feminine but her attitude was definitely DOM!
Nancy loves her Susan. Susan has been Susan for 18 months. She will never have the final surgery and willingly lives in chastity and does earn some really good money, both through working in the real world as SUSAN and through the photo shoots we do with her for various magazines and such that cater to the special people who like those kinds of photos. She is becoming popular on the web for taking guys bound as she was. She seems to REALLY enjoy it too.
I stopped fucking you because, well, I was starting to feel that you needed it stopped before you lost control of yourself. When you started crying I knew I was right. I want you to ENJOY things and experience things as you. Maybe a little on my terms but also on your terms as well. But that, sweetie, is up to YOU! I can not make that choice for you.
So, I am giving you this out. You can go ahead and head back to your apartment and never have to worry about me again. Yes, I will miss the time as friends but if you are not comfortable, then it won’t be any fun for either of us.
If you go home, you can make up your mind easier there. If you decide that maybe you want to go along and see where this goes, then come back here after cleaning up and we can talk.
I hope that I am right…

Karen

I sat there pondering this note for maybe five minutes. Then I got up, noticed that she had brought over some of my boy clothes and I pulled them on. I noticed that my femme clothes and underwear were nowhere to be found. I got up and walked out the door. I found the entryway door in seconds and went out and down the two flights of stairs to my floor. I opened the door (it was unlocked) and there was when I broke down for the second time. I saw my underwear folded and cleaned, as well as my uniform hanging on a hanger next to my closet door. I walked to the bedroom and saw that it was just as I had left it how ever long ago it was before I had gone through the series of events.

Then I saw the envelope there on the bed. I opened it and there I saw a stack of photos, all of me, from many angles, as I was caned, fucked and everything else, including when Karen had found me in self bondage. And when I looked at the photos, especially the ones I could see my own eyes and my face, I saw a totally different person than I had thought I was. I was not seeing Chris but rather I was seeing Christy and DEEP inside me, I knew that was who I wanted to be… But I didn’t really know HOW to be Christy. But I also knew WHO could help me become Christy… It didn’t take me too long.

I hopped into the shower and washed. Then I went to my dresser and instead of finding a whole lot of my underwear, I found NOTHING! Then I remembered that there was everything I needed sitting in the living room. I rushed there, not really caring where the rest of my stuff was and in moments I was dressed. I went back to the table and found my cosmetics and spent a great deal of time putting my face together. Once that was done, I walked back out and picked up the uniform. As I picked it up, I saw the gag, ankle cuffs and wrist cuffs sitting there too. I put on the uniform and petticoat, then my heels. Locked them in place, put the gag in my mouth and then put the cuffs on my wrists. Without thinking for even a second that I was being stupid, I walked out the door, went to the stairs and walked up the two flights of stairs, rang the doorbell and waited.

When Karen opened the door and saw me, she smiled. I smiled as best I could with the gag in my mouth and I was ushered into the home. Oh, I was still a little scared. But Karen was there and would guide me. And when I got into the living room, Nancy came up to me and smiled, saying “you will make a nice addition to the family, Christy” and even Susan, though gagged, came up and hugged me, even though she was cuffed as I was.

Karen hugged me and then informed me that it was time for you to have the RIGHT chastity on for my new role in their life. I nodded, knowing that I was going to be chastised permanently. But I also realized that I was actually looking forward to not having to be who I really wasn’t any longer. As I lied down on the table and Karen strapped me down, she washed my cock with alcohol and then with a piercing gun, pierced my cock twice, which did cause me to scream a little. Then a couple of ear piercings later, I felt the tube pushed through my cock and then the chastity tube was pushed down the length of my cock. There was pain involved and I was squirming like a fish out of water as it was indeed painful. But once it was in position, that pain stopped and then I felt the tube being pulled through. At the end of the tube I could see a small barbell shaped post and as it passed through my cock and the chastity, I realized that THIS is how this was locked on. And when the soldering iron, flux and solder came out, I knew what was going to happen.

It took only about ten minutes to solder the two barbells permanently closed and thus, I was now permanently chastised. The chastity pulled my now chastised cock between my legs and I found it rather interesting that there was what appeared to be two raised mounds on the chastity. This thing was going to give me the look of having a camel toe! But that was not the end.
Karen then undid the straps holding me in place and then told me to bend over. I did as I was told and then felt a good sized dildo/vibrator being pushed inside my cunt. Once it was in, rather deeply, I felt a tug at my chastity and then heard a little click.

“Now, Christy, you are chastised. You will not be able to be ‘manly’ any longer. That chastity will make sure of it. That vibrator inside your tight little cunt,” she paused as she hit a button on her phone and instantly I was feeling the vibrator take hold of me and the good feelings were coming back to me fast and loose. “will remind you of what you are as well. In a couple of weeks, after we make sure that you are good and ready, we will take care of your needing those little… Well, in your case not so little, breast forms. But I think some D cup or maybe DD cup breasts would be great on you. Then we can work on your nipple piercings…

“I want you to know, Christy, that I was REALLY hoping that you would return. Nancy kept telling me that you would and even Susan said that she could see that you would come back. But I felt like I had gone too far that first time…” I shook my head at her. I was gagged so I could not tell her that I was wanting MORE! Karen saw me shaking my head. She reached for the gag and removed it.

“Mistress Karen, I didn’t know what I wanted. That was until you found me and took me on this journey. Hell, I was crying because I was, well, I think I was too happy… I wanted this and MORE! Oh, I had fantasies and such but, well, I didn’t KNOW what this would really feel like until, well, I got back into the my apartment and, well, saw my uniform there sitting and waiting for me…” I couldn’t help it, I started to cry a little more.

“Christy, we will take this as slow as you want. As long as you know that this is what you want…”

“Mistress… Please fuck me again!”

Mistress Karen was more than willing to oblige me, and as she did, I begged for more and more. And I got to have many pictures taken of me. I made some good money that way, doing bondage shoots and the like. Oh, I should say that I did get to experience having men enter my mouth and cunt. But at least those using my cunt wore a condom. Of course, the ones I learned to suck I swallowed like a good little slut. And those who gave me what I needed I would be fed their cum. I guess you could say I became a cum whore. All I can tell you for sure was that the doctor who gave me my DD implants had a very LONG cock and I sucked it happily as I enjoyed my new, real breasts. And let me tell you…  CLAMPS on them feel SO deliciously evil!!!

As for our life together, Karen has brought me very far. I was taught how to worship her as her slave, which is remarkably similar to how a woman would love another women. Okay, the dildo I might wear is on my mouth as I am gagged but still. And I do get my cunt fucked as often as I need.

My apartment was rented out to someone else. I didn’t realize that Karen and Nancy OWNED the building.

Nancy and Susan actually live on the floor below Karen and I. Oh, we see each other a great deal as the bondage sessions that they hold are done on this floor. Susan and I wear different colors each day, always a maid uniform in satin, stockings and heels. We answer the door for their clients, whether they are there for Discipline sessions or regular photo shoots. That is where Karen and Nancy get our (Susan and my) cock sucking dates. Once a month, they will host a party and that usually turns out to be where we get put on display, in more ways than one. And it was at the first party that I was introduced as Mistress Karen’s slave. I received my collar then. Where Susan’s said “SLUT” on it, mine was a little different. My collar was pink patent leather surrounding a steel collar. Lettered on the front of the collar was the phrase “SISSY BITCH”.

Of course, going out into the vanilla world it was not so easy to hide the collar. It was only 1 inch high and was riveted around my neck. But a good blouse could cover it up as I went out into the vanilla world, knowing the entire time that I was Christy to anyone who met me. My breasts gave me confidence and the chastity, collar and vibrator inside me at all times reminded me that Mistress Karen owned me.

I was a very happy girl now. And I was, indeed, Mistress Karen’s sissy bitch and damned happy to be that… All from an UNEXPECTED photo shoot because I knocked over my escape key… Who would have figured!