Forever Her Sissy - Chapter 4 (of 6) free porn video

This is a FigCaption - special HTML5 tag for Image (like short description, you can remove it)
This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke quietly. "Yes honey, what is it?" "What else do we need to shop for, I'm really exhausted, it's just that it has been a really big day and I was thinking we could go back home and enjoy the afternoon, just you and I." "What else do we need to shop for! You must be kidding me, you have zero underwear and you are a little bit smaller than me so mine don't fit you just perfect, and I think that you need a slightly different style than I wear and we need some very firm control panty girdles because I don't want to see that silly bump at the front of your panties in your new work clothes. Let's see what else do we need? Maxi pads, you need pads because without them you will leak your little sissy tears and stain your panties, I'm afraid that you're going to have to wear overnight pads all the time because you can't control yourself. It's not my doing sissy, I can't help it if being a sissy makes you so excited that you leak constantly. And you did say that I needed a new purse for summer right? Don't you want to find your wife a pretty new purse? You just love picking out bags for me. And we need to find you a new computer bag, you're not going to mess up your outfits with that frumpy old back pack you use now," Karen said in a huff. "Now what else have I left out, oh yes I almost forgot. Did you notice anything about your new work clothes when you were trying them on honey? "Besides that they were women's clothes?" I asked in a timid voice. "Yes, besides that sissy," Karen responded, her tone getting a bit more harsh. I could tell that she was beginning to get upset with me. "Honestly sweetie, you are so dense sometimes, did you notice that there aren't pockets in any of your new clothes? So we need to get you a new, more appropriate wallet and a bag to keep everything in." "Yes ma'am, I'm sorry, I just, well I am afraid of bumping into those ladies. They might put lipstick on me again," I mumbled looking down at my toes wiggling in the strappy little sandals. A funny thought popped into my head while I was looking down, it occurred to me that I looked silly in such pretty sandals with boring toenails. Anyone else wearing these would have pretty polish on their toes. Shit, what was I thinking of, my mind was going to sissy mush and I could feel my poor little penis dripping more tears into the thick pad. I was actually happy that I was wearing it because if not I would surely have a damp spot on my shorts, well on Karen's shorts. I was so horny, so confused, and just felt ditsy. Karen spoke, breaking my thoughts about what color nail polish would look best on my toes. "So you are being all pissy now because you are worried about those three lovely ladies putting lipstick on you again and that is why you are moping around mumbling and wanting to go home?" "No ma'am, I mean yes ma'am, I don't know Mrs Karen. I'm just, well maybe, I'm sorry if I am being difficult, it's just that wearing the lipstick was embarrassing." "They were nice enough to use a light pink shade which didn't even really show up and it wore off on your first kiss, they were just having a little fun with you. I think that you loved it and wanted to wear lipstick. You wanted to wear lipstick because you are a sissy!" Karen's voice had risen, not to a yell but to a tone above her normal speaking volume and I could tell that she was frustrated with me. "I bet you almost squirted when she was applying it, even with your little clit locked in that tiny cage? Well sissy, is that what this little tantrum is all about?" Somewhere I must have picked up a little bit of backbone, or more likely I just didn't think about what I was about to say to my wife, but the moment the words came out I regretted them. "No! I am not throwing a tantrum Mrs Karen," I said putting a bit of emphasis on her name, "I don't really like lipstick on me! I'm a man!" As I said this I punctuated the end of my statement by huffing, straightening the straps of her purse on my shoulder and stamping my pretty sandal down on the tile floor of the shopping mall. Her disapproving gaze fell on me with eyes that were cold as ice. There was no expression on her face and her lips were pursed together tightly, what had I done. This was so bad. Her hands clenched and unclenched repeatedly so tightly that I could see little marks where her manicured nails had dug into her palm. Even her cheeks were a bit flushed. For a second I thought she was going to turn and walk away, leaving me behind but she didn't. In a calm, almost dead voice she held out her hand and said. "Brian, hand me the makeup bag from my purse." Shit, when she used my name like that it was always because she was really mad at me, like the night after dinner with my co-workers. Trancelike, with stiff robotic motions I opened her large black Michael Kors hobo bag and found her makeup bag. It was largish white bag with cute light pink strawberries printed on it with a pink zippered top. I lifted it up and held it out to her, silently following her orders because there were no words that I could say at the moment that would improve the situation. Taking it she unzipped the bag and rustled around in it for a few seconds and came out with two slender tubes, one all white and the other was a pretty rosy pink brownish with a white cap. She handed them both to me. "Read what is on the colored one first sissy, read it out loud to me," She said, her voice full of quiet rage. "Ma'am, I am so sorry Mrs. Karen, I didn't mean to talk ugly to you like that, it just came out wrong, please ma'am," I was almost whimpering. "Read what is written on the outside of that lipstick Brian," She hissed. "Umm, it is, well it says Cover Girl Outlast All Day Lip Color, in, ahhh Brazen Raisin color ma'am," I whispered. "Okay then Brian, right here, right now. Are you my sissy or are you just pretending. This isn't a game to me, is it a game to you?" I couldn't answer her, I knew that I had been wrong to talk back so strongly to my wife but it had happened before I knew it, the words came out before my addled brain could stop them. Standing in the crowded mall, wearing women's underwear, a maxi pad, chastity cage, my wife's shorts and t-shirt, carrying a purse, standing only a few feet away from where my wife had my ears and nose pierced and fitted with very feminine jewelry and I was going to make a huge scene over having lipstick put on me over two hours ago. The craziest thing is that I should have been furious, foot stomping mad at her humiliating me like this. I should have refused to come out dressed like this but I hadn't. Not only had I not fought back but as I stood there withering under her gaze I began to understand that I had been having the time of my life and that my beautiful wife was going to all of this trouble for me, because she knew that I craved the control, the humiliation and her love and I was acting so ungrateful and selfish. I thought back how years ago when we were dating I had to beg her just to let me hold her purse for her. It must have been embarrassing to be seen with a wimp husband who got off on carrying her pocketbook but she did it because she loved me. And now, she had finally come to grips with it, and had taken up the reins of control, even found that she was incredibly turned on by asserting dominance over me and I was acting like a complete ass. I should have been eager to do anything that she asked, that is what I had always wanted, but instead I was fighting this every step of the way. "Aheeem," Karen cleared her throat, "are you going to answer me Brian, are you going to tell me that last night you lied to me after your tantrum in the parking garage when you pledged to be my sissy forever? Has a little bit of lipstick broken your resolve? I don't know what is going through your little head right now but if you are telling yourself that you are a real man then you are lying and I can't help you if you can't even be honest with yourself. We are not going to keep having these constant relapses honey, it just isn't productive." With a trembling voice I quietly spoke, "Mrs. Karen ma'am, may I please borrow your compact mirror?" For the first time since this conversation began a hint of a smile began to show on her otherwise stern face as she pulled out the small round mirror and handed it to me. My hands were shaking so badly that I feared dropping and breaking the mirror which would not have been good at all. Before I changed my mind I opened the compact, holding it and the bottle of liquid lipstick in one hand I unscrewed the applicator and using the mirror carefully applied the lipstick that I knew would remain in place for at least eight hours. This was much darker and had a red color which would be extremely noticeable, even from a distance. This was the first time I had worn a long lasting liquid lipstick. It went on differently and as it dried I felt a slight tightening of my lips as well as the sensation of a thicker coating than regular lipstick. Next I applied to gloss from the all white tube, smoothing it across my lips made them feel better and they looked very shiny. More than that I felt my cheeks warm with flushness and I knew that they were blushing red and my little clittie was straining against the unyielding steel bars of the chastity cage. "Mrs Karen, I am sorry for my behavior and my outburst. Yes ma'am I am your sissy, but like many sissy's I don't always know what is good for me. Thank you for letting me wear your lipstick and I am sorry for resisting or doubting you before. Are you mad at me ma'am?" I said while looking at her with pleading eyes. "Yes, well maybe just a little mad but what you just did for me, means more than your words. Sissy's will say many things to get their way, to try and escape punishment, they can be manipulative little creatures. Why did you put on the lipstick sissy? I did not tell you that you had to." Sheepishly, still blushing, "I...well...you had taken it out and I was being obstinate about wearing lipstick earlier so... you were going to ask me, no tell me to put it on." Karen didn't answer me, she only stood looking at me with an impassive expression on her face. "No, wait, what I said just then was a lie Mrs. Karen, I am sorry. What I meant was, well I, I put the lipstick on because, I did it because I am your sissy and I want everyone to know that I am your sissy and because I thought you would enjoy the humiliation of me wearing lipstick, and.... Well... and... I..." My words got quieter until they were below a whisper. "Go on sissy, speak up," She said while handing her makeup bag to me to be placed back in her purse. "Because lipstick is pretty and I want to be a pretty sissy for my beautiful wife," I replied in a gasp, so ashamed of the truth looking up at her through my eyelashes, I felt so bashful, like it was a first date. I had put the lipstick on because I thought it would look pretty and Karen would like her sissy to be pretty. I wasn't even close to being a man, how could she think that I would be pretty, why was all of this happening. In exasperation my shoulders slumped in defeat, I didn't know what I was doing anymore. I cast my eyes towards the floor, once again struck by how boring my toes looked in the sandals. I felt Karen grab my hand and then we were walking quickly through the mall, I was being pulled along behind her, stumbling a bit, loosing my balance with all of the packages swinging about as we dashed around the corner. We cut across the front of a store and turned down one of the service hallways but instead of slowing down she pulled me along even quicker. Ahead were the bathrooms, never glancing back she swung the door to the family restroom open and threw me in ahead of her before following. What had I done, was she mad at me, I had been rude and then I may have also caused a scene in the mall with my silly babbling words that could have also embarrassed her. In a fluid motion she locked the door and spun me around pushing me against it with so much force that I dropped some of the shopping bags. Gasping I saw two pairs of shoes tumble out of their boxes, a pretty pair of black suede heels with a open design and a wide strap at the ankle and a pair of patent taupe cork wedge heels with a sling back strap and a cute open toe, I made an attempt to reach down to pick them up but Karen pressed me back against the door and then with a force that surprised me, with an animal violence she kissed me. Not a tender kiss of compassion but one that made no doubts about who was in charge. All the while her other hand was wrapped in my hair, tilting my head back while she probed with her tongue, finding mine and sliding across it, caressing my mouth. Now her hand was pressing down on my shoulders pushing me to my knees. As I knelt on the cold white tile floor, I looked up at her, my eyes wide with shock. In a fluid motion she pulled my long brown hair up and slid a peach colored silk hair tie that was on her wrist around it, securing my tresses into a ponytail high on my head. Satisfied that my hair was tied back she reached underneath her dress and slid off her panties. "Smell these sissy!" she said frantically while pushing them into my face. The crotch panel was soaking wet and smelled like sex. "Do you see what the fuck you have been doing to me today. Sashaying around, swinging those sissy hips, batting your eyes at me, those big soft brown eyes that most women would kill to have. Even without makeup you look like you are wearing mascara, big soft doe eyes. Always saying, "Yes ma'am Mrs Karen," holding my purse so sweetly and so obediently. Do you see, fuck, do you smell and feel what that has been doing to me all day?" She gasped, while still pushing her soaking wet panties in my face. The pink color darker around the gusset from her dampness. "Then you batt you eyes and tell me that you wanted to wear lipstick because you wanted to be pretty for me, because you wanted to feel the humiliation that I crave for you to endure." Grabbing my hair by the pony tail she pulled my face to her folds and pushed her hips towards me. "Now sissy, right now, I need relief!" I did not wait to be told a second time but wrapped my hands around her waist and pulled her into my tongue and lips. I heard her gasp and then, glancing upwards quickly saw her hold her hand over her mouth in an effort to muffle her whimpering cries. She was biting into the side of her palm and I could see sweat beading on her forehead. Immediately I began to lick her with urgency, I knew that this was not a tender moment that she wanted to savor but a release that she had to have. As I continued to serve her she began to talk to me, though muffled through her hand she had held over her mouth. "That's right sissy, give your mistress the orgasm she demands, provide for her pleasure while yours is denied by the very woman that you are pleasing. I want you to concentrate on the frustrations of your caged sex. How does it feel sissy, do you want to cry because your wife loves you too much to let you cum! Ugggggggmmmm fuckkkk. Lick it sissy, mmmmmm!" I could feel the muscles in her lower back and her abdomen begin to flex and tremble, her thighs shaking, tremors coursing through her body. My hands were both pulling her firmly towards me and keeping her from falling over. Plunging my tongue deeply into her folds by pushing my head to and fro while wiggling back and forth, faster and more franticly until there was one last great shudder and I felt every muscle in her body tense, then came the sound. A low pitched moan that trembled and wavered on the air; a sound so primal that it was the personification of what pleasure should sound like. Her other hand, the one not vainly attempting to muffle her cry of glory was wrapped tightly in my hair pulling me in deeper, to the point that I could no longer find even the occasional breath. Loosing myself in her lust I dove deeper pressing harder and faster, moving my tongue with a force born of desperation until her body finally released all tension and I felt her cum, like the bursting of a dam my face was flooded by her womanly gift as I swallowed all that came to me, a beautiful treasure from my wife, from my mistress, my goddess. For a long moment we remained there, pressed against the door with only the combined sound of our labored breathing in the tiny room. I was weeping, both because I was so happy for what I had just been able to do for my love but also because I was looking down at the small key that hung on a delicate gold chain that rest loosely on her ankle. My tears were for the love of the joy I had just given my wife and for the sorrow and anguish I felt from being caged and frustrated by that same loving woman. I remained silent, afraid that my voice would break the spell that had enveloped us. I could still feel her hand in my hair, her fingers wrapped deeply as she supported herself. With a sound falling between a sigh and a whimper Karen stretched her other arm out to lean on the door and slowly untangled her fingers from my hair, gently drifting her grip down to my chin. Using her hand to guide my eyes up to meet hers I could see that she was flush and her eyes were glittering with moisture. "Oh sweet, sweet, sissy," Karen whispered. "Your face is a mess honey, but your lipstick is still there," She giggled. Pointing at the sink, "You can set your packages down and get cleaned up." The cool water felt good on my face and between a baby wipe from her purse and a fresh splash of water I looked presentable again. I also touched up the gloss on my lipstick while I had the large bathroom mirror to work with. "Hang on sweetie, there is something that I just have to see, do you mind?" I paused as I was putting the slender tube of gloss back in her makeup bag which I had sat on the side of the sink. Reaching in she came out with her Loreal Paris waterproof mascara. She held this up for me to read, "Sissy, do you want your mistress to make your eyes even prettier than they are, do you want to have long pretty lashes?" Karen was standing very close to me, with the mascara held up for me to see, teasing me with another step towards my humiliation, away from my manhood, another step towards being more feminine for my beautiful wife. "Do you want me to look pretty for you? You want me to look more feminine?" I whispered. "Oh god yes, I do," was her breathless reply. "You want me to be more feminine? I don't understand?" "Honey, I can't explain everything either but every time you submit to a new humiliation or feminization, every time you demurely accept my dominance, it makes me love you more. Don't take this the wrong way but it wasn't your prowess as a man that made me fall in love with you and agree to be your wife, it was your sensitivity, your loving nature, all the little things you did to show me how much you care for me. Any guy can tell me he loves me but you show it in every action, every moment, of every day. Now that we are slowing stripping away the lies, the pretend macho and bravado, and bringing your true submissive self to the surface you are becoming so beautiful, so pretty, so soft." With my voice hoarse with emotion I softly spoke, "Mrs. Karen, would you please help me put on some mascara, I don't know how to and I don't want to mess it up. I want to look pretty for you. I want to be your soft, pretty, sissy." My words were met with a soft passionate kiss from my wife, but she pulled back abruptly. "No you don't you little tramp, you're not going to get me all hot and bothered again," She said in a giggling, happy tone. Unscrewing the cap and pulling the applicator brush from the mascara bottle she made a silly face rolling her eyes up. "Now open your eyes like this sissy and look up at the ceiling." After she had finished and I put away her makeup bag Karen turned me back towards the bathroom mirror. "Look at yourself and tell me what you see," she said. As I studied the person in the mirror I definitely did not see a man, but I knew that I was not looking at a woman either, I mean the lipstick and the thick dark eyelashes were very feminine but there was something a little off. "I see a sissy," I said in a quite high pitched voice, it sounded a bit silly the way I said it. "That't right, you do. You know, with a bit more makeup everyone would see you as a woman, and a very, pretty one at that." "Yes ma'am, I can see that. Are you going to finish making me up like a woman?" "No, sissy. I want you just like this right now. Stuck, somewhere between male and female. I want you to know that everyone sees you as a sissy, a little purse holding, pussy-whipped sissy bowing down to his wife. How does that make you feel? Am I being too mean?" "No ma'am, you could never be mean," I replied. With a dangerous smile Karen said, "Don't be too sure of that sissy. Now let's get this stuff picked up and enjoying our day of shopping. There is still quite a bit we need to get done, and I have some surprises for you yet." Leaving the family bathroom I glanced around to see if anyone had been waiting or near the door. I was somewhat self conscience about how long we had stayed in there but to my relief no one standing outside with an annoyed look on their face tapping their foot. As we walked down the mall, once again butterflies began dancing in my stomach and I could feel everyone drilling into me with laser focus, the sissy wearing women's clothes and makeup. I was thinking about what Karen had told me in the bathroom, could I really be passable as a woman? She had said that I could be pretty, and that she liked me pretty, and that she loved me for my submission to her. That made me think of how embarrassed I was when the three ladies stopped me earlier and how I was so submissive in accepting their dominance over me, and what my wife's reaction was, how she fed off of my humiliation. Remembering my feelings when they were ridiculing me I drifted mentally, replaying the smooth glide of the lipstick as it slipped across my lips and the total loss of control and submission to women I had never met before. My clittie began the futile struggle to get hard in the small confines of it's cage and it started crying "chastity tears" again, the feeling of pre-cum oozing out sent a perceptible shiver down my spine. What was wrong with me? Being so distracted I had failed to notice that Karen had stopped walking and I had wondered away from her. Turning quickly in a frantic search I saw that she had paused in front of the Victoria's Secret store and was looking at the window displays. Without hesitation I ran back to her, apologizing for my lack of focus. "It's ok sweetie, I should have let you know I wanted to stop in here, we need to get you some new undies, I'm sure you have already figured out that boxers are out of the question for you and if you are going to wear panties for me I want them to be pretty....and we will need some girdles and shape wear to prevent that nasty little bulge from ever appearing again. Ohhh, and some sexy little things to sleep in would be nice too." With that statement she actually bounced into the store with an excited stride. "Oh, sissy look at all the pretty things you are going to get to wear!" she called back loudly. Several ladies in the store turned to see Karen with me behind her, if I could have shrunk myself and hidden behind the clothes display I would have. For the umpteenth time today my face burned red with shame but now it was even worse. With her loud comment drawing attention it was clear that everyone was looking at me; a guy wearing what were very obviously women's sandals, questionable gendered clothes, an armful of packages from women's clothing stores, a purse, pierced ears with pearl studs and a nose ring with a pretty enameled flower, dark red lipstick and thick lashes. The shaking began slowly in my knees and spread throughout my body until I could not physically move. The pounding of my heart was so loud, all I could hear was thump, thump, thump, and the sound of blood rushing to my head. Everyone in the store had turned to stare at me! By now several of ladies were watching with great interest. Seeing she had an audience Karen smiled demurely. "You see, my darling husband loves to serve and please his wife. Nothing like the average man who huffs and puffs with their chests poking out pretending to be all gruff and tuff. I have a sweet servant of a husband, a dove, soft and obedient, willing to do anything for me. It wouldn't be fair to let a little flower like this pretend to be one of those harsh alpha males. No, he is tender and only looks out for my pleasure and needs, ignoring his own," There was a bit of a pause while the ladies pondered her words. It was a young woman with short blonde hair wearing a flouncy, floral top and black leggings with flats that picked up the color in her top who broke the silence. "That is sweet, and I think his sandals and jewelry are so cute. You have to tell us, is he wearing panties too?" Giggling Karen said yes, and a pad to boot! All of the women gathered near us started to laugh out loud but then the stopped, looking at each other like they had done something wrong. The lady, whose name I just heard was Melisa started to apologize for laughing at me. It was then that maybe I started understanding what my wife had been trying to explain to me about what it meant to be a sissy and how I should be happiest when I was serving or adding to the enjoyment of women, I just couldn't stand seeing someone feel bad because she had rightfully found humor in my situation. With a smile I reached out and touched Melissas hand. "Ma'am, please don't feel bad for making fun of a sissy. My wife has been helping me through this and I don't understand everything yet but I know that I am a sissy and I should be ashamed. This is my place, what I am. Please feel free to laugh at me and humiliate me, I should be embarrassed. I should be made fun of, it's okay really, I love serving my wife." Karen patted me on the bum in a playful manner, well maybe it was a little harder than playful but it got my attention. "Now ladies, we originally came in here because my sissy needs some pretty undies; panties, bras, something fun to wear to bed so I can cuddle up with him feeling all silky," Smiling at me she whispered in my ear. "Honey I know you have had a very tough day but we really need to get this done while we are here. I will make a deal with you. If you can be a little soldier and let the sales lady help up get you some pretty lingerie I promise to protect you a little if we see those three ladies that acted so mean to you earlier today." I perked up, smiled, slid Mrs. Karens purse higher up on my shoulder from where it had begun to slip down and readjusted all of the bags and packages I was holding when the sales lady stoped me. "Dear, don't worry about toting those packages around while you shop, you need to be able to look and handle the pretty fabrics. We can put them behind the counter for you." I was just so shocked at how nice everyone was being towards me even though I was nothing more than a sissy. "Thank you so much ma'am." This was the signal for Karen to take charge again. "If you can help us we need very firm control panties to keep her little chastity cage and clittie mushed down smooth. I just don't want to see a bump on my sissy" she told the lady. I was mortified, now everyone listening knew that I was locked in a chastity cage and was already wearing panties! The sales lady gave me a curious look and with a smile replied, "Yes we can help with that. Can I recommend our firm control thongs in a mid waist. Not very comfortable to be honest but it gets rid of panty lines in the back while it should keep her little cage pressed down quite well, especially if we stick to a size smaller than she would normally wear that is as long as what is caged up is fairly small." "Tiny," my wife replied and both women busted out into laughter. Next came a similar high waisted control panty in periwinkle pink with a matching bra. The sales lady, Mrs. Beverly, was able to find a matching padded underwire bra for the first set of panties in the perfect dark tan color. I was confused about the bras, my wife had not mentioned me having to wear a bra. Panties could be easily hidden and unless something happened, like my wife telling everyone in the lingerie store that I was wearing one, it was discrete. I started to question her about it but just as I was going ask Karen spoke first. "Yes sissy, bras, I have decided that I want you to wear a bra in addition to your panties." The confusion on my face must have been so clear, but she had been several steps ahead of me all through this. "I wasn't originally going to make you wear one just yet but once we started shopping and I saw how pretty they were and how absolutely submissive, how demure you became when Beverly held the first one up for you to see I decided right then that I wanted you in a bra no matter what. Just imagine how sexy it will be, cuddling with your wife, her soft fingers tracing the outline of your dainty little bra strap," With a gleeful lilt in her voice she exclaimed, "We can get matching lingerie, won't that be sexy honey?" As we continued to shop for underwear Mrs Karen required that for each set I was to hold them up and comment on what I liked about each. After we had at least ten bra and panty sets my wife shifted gears to sleep wear. Mrs. Beverly asked what my wife would like for me and the reply was, "Something sexy, we aren't really worried about comfort, she will learn to deal with whatever we pick out, I want sexy so I won't be able to keep my hands off of my little sissy at night and I'm not worried about seeing her little bump in her night clothes. In fact I think that it will be cute to see the little sissy bump that I control." We were shown several options but Karen really like the ones with garters and hose. Mrs. Beverly questioned if I was expected to wear hose to bed and with an air of confidence Karen told her that, "Yes, I think that I wold very much like her to wear stockings to bed." With that statement several very intimate sets consisting of tiny thongs, hose, and gartered bustiers were selected for my night time wear. To be honest, I had never worn anything like this before and nothing looked very comfortable, I couldn't imagine having the thong strings in my butt crack but I did not dare say anything negative. The entire day seemed very surreal but I did like what Mrs. Karen said about us cuddling, I suppose that wearing pretty lingerie was a very small price to pay to be with the woman that I loved. Looking at all the pretty things we were buying gave me goosebumps! What would it feel like to wear stockings? I was thinking to myself when once again Karen caught me unawares in the middle of my daydreaming about her and I lying in bed, our arms and legs intertwined. "Sissy, get these bags, thank all of the sweet ladies and let's take this first load to the car. I don't think you could hold another package, I swear sissy this shopping trip for you is getting expensive, you are going to have some serious work ahead of you to pay me back for all of this!" My shopping trip! I thought to myself, but I didn't want to come shopping, she did. Thinking about it though almost everything we had purchased was for me, Mrs. Karen had only gotten herself a few bra and panty sets that matched mine so I guess she was right. It was my shopping trip. "Thank you Mrs. Karen, thank you for all the pretty clothes and my new earrings." My words came out in a bashful way, as I spoke I twisted a little, biting my lower lip and looking up at her through my lashes and a few errant strands of hair that had slipped down from my girly pony tail. "Sissy, you better stop teasing me like that, you remember what happened just a little while ago. I need to hold it together for two more stops, we need to get you a super girly wallet, a purse for you and for me, and you need to buy maxi pads, a lot of maxi pads," she told me in a stern tone. "Why a lot of maxi pads ma'am?" "Because your need for them is different, your little sissy drip is constant where my period is only once a month and I hardly ever wear the huge overnight pads because they feel so bulky and uncomfortable. I like the thiner absorbent foam ones, they are almost like not wearing anything." "Mrs Karen ma'am?" "Yes sissy what is it?" "Why can't I wear the thin comfortable pads too?" "Silly sissy, you can't wear them because they are thin and comfortable!" She laughed. "I want you wearing the thick bulky pads, I want it always on your mind that you are wearing a thick overnight pad to catch your sissy chastity tears. This is a small price to pay sissy, us girls have had to deal with pads bunching up in our panties and rashes, and how hot and uncomfortable they are from our first period to our last. If you don't mind your manners I may just make you wear two of them so you have to waddle!" She ended with another round of giggles and a stiff swat on my ass. Honey, I am going by the coffee shop, run and drop off our packages at the car and then hurry your little sissy ass back to me, understood?" "Yes ma'am," and I was off. Walking through the mall without my wife was very different, I didn't have her strength to hold me together and I could see people pointing and laughing at me. I walked as quickly as I could and tried to stay next to the walls to attract less attention. The journey to the car was agonizing but it was a relief to finally have no packages to carry. After closing the hatch and using the key fob to lock and set the alarm on her SUV I made a plan for my trip back to the coffee shop to meet Karen. I would walk quickly, stay to the sides, and keep my face lowered. Without the huge bundle of shopping bags I would attract much less attention and could move more naturally. Passing through the back of a department store to gain access to the mall I became very conscious of how I was walking. I was trying to remember what Mrs Karen and Miss Tori had taught me earlier today to make my walk look more feminine. Even though I was not wearing heels I concentrated on walking more feminine and how I held my body and arms. At the least it was a distraction and gave me something to focus on. With relief I saw the cafe up ahead, at the edge of the food court, I had made it back to my wife without any major incidents or humiliation, I was elated. Entering the cafe I looked around for Mrs. Karen, it took me a little while to find her, and my euphoria came crashing down when I saw her at a table with the three ladies that had stopped me earlier. They all had drinks and were sitting around the table laughing and talking, mostly laughing. With a deep sense of dread I approached the table, keeping my eyes down and trying quietly slide next to my wife. Karen, with tears in her eyes from laughing so hard, patted the seat next to her. "Come here and have a seat sissy, we were just talking about you." With that comment all of the ladies at the table burst out into laughter again. "Now sweetie, don't be mad at me but we just started chatting and I was telling them how since you were so, well you know, small down there that we decided it was better to cage that little tiger up so it couldn't disappoint any other women," She giggled. The taller blond lady almost sprayed her tea out in a fit of laughter. The dark haired lady who had so sternly warned me about keeping her friends lipstick on set her cup down and put her hand out to touch mine. "Sissy, your wife told us that you felt so bad about loosing the lipstick we let you wear that you begged her to allow you to put on her long wearing liquid lipstick. I think that is just adorable and I believe that it is a suitable punishment for you. Well, and I can't believe that I am saying this, but it looks damn good on you, not slutty but nicely put together. It matches your darker skin tones." "Thank you ma'am," I said, not knowing her name that seemed like the most polite way to answer her. The blond patted Karen on the hand as she rose from the table. "Oh honey it was so nice talking to you and I can't wait to see you two again. We have to be going, sorry to run off but ta-ta." And with that the three ladies excused themselves and walked out. I was dying to ask my wife what they had been talking about and what she meant by "seeing us again" but I didn't dare interrupt Mrs. Karens obviously good mood. Before I could screw up the courage to actually ask the question a waitress arrived with a half sandwich and a small ramekin of fresh fruit and placed it in front of me with an unsweet ice tea. I looked at my wife. "Honey, you haven't eaten all day, I thought that a little something would be good for you. It isn't healthy to starve yourself and with this lipstick your safe to eat," she said while unfolding the white cloth napkin and placing it in my lap. It was an avocado sandwich with fresh ripe tomatoes and a very nice white cheese. On the first bite I realized how famished I was but I worked hard to maintain my composure and eat with proper manners. The next stop was the large anchor department store at the end of the mall. We took the escalator to the second floor arriving at very large handbag section. There were so many purses; leather, straw, cloth, microfiber, expensive designer purses, and pretty ones that were affordable. I truly had a purse fetish, it was the most feminine of all things. Purses were pretty, they were a very personal item for each woman, every lady having her favorite styles and types. I knew that my wife liked over the shoulder bags that had enough drop on the handles so that the bag would sit comfortably beneath her arm. She preferred larger bags for every day because they held all of the things that she liked to keep with her and she pointed out that since I usually carried her purse having a heavier bag wasn't a big deal. She also like fun, medium sized cross body bags, even though when she wore them it was usually only over one shoulder. On the rare occasion she was carrying her own bag, if it was one of these cross bodies with a long shoulder strap, I loved to watch the way the bag would swing and tap agains her hip and butt, it sounds strange but it was so erotic to me. "Well sissy, we need to find you a purse don't we?" "Yes ma'am," I replied happily, having re-dedicated my spirit to be the pleasant, happy sissy that my wife wanted to spend the day with. "And a wallet, and a fun summer bag for you too Mrs. Karen." "Well, it seems that someone has perked up now that we are looking for pocketbooks, you really do love them don't you sissy?" my wife asked me. "This is what I like, a perky, fun, sissy husband. Honey will you be okay picking out our bags on your own. You are usually better at finding a bag for me than I am so I have total confidence in you. Honestly I like it better when it is from you and I didn't choose it, there is something sweet about a sissy buying his wife a purse. I have a couple of things that I need to do while you shop, I will even pick up your pads for you since I need to go by the drug store. Do we have a deal, just give me a call when you are done here." "Yes ma'am," I pertly replied, "I can do that. I have an idea of the purse I would like to look at for you but do you want me to just get an inexpensive one for me, I mean I'm just a sissy and I hate to spend money on something for me like that." "Oh honey, that is sweet but I think that my pretty husband deserves a nice bag of his own. This is a very important purchase, it is your first purse, the first one that is just for you. Make sure that is large enough to hold some stuff, you are going to be carrying makeup, pads, a wallet, and all other sorts of kinky and girly stuff. Now hand me my wallet and phone, you have your silly boy wallet with your debit card right?" "Yes ma'am I do, and my phone. I promise to call when I am done. Oh, Mrs. Karen," I said as she had begun to walk away. She turned back towards me, waiting for what I was going to say. "Ma'am, thanks for letting me hold your purse while I shop." With a smile and a naughty wink she turned and hurried away. I began to browse through the huge variety of purses, stopping to pick one up and sling it under my arm to check for the drop length, looking at the stitching closely. I was focusing on Karen's purse first, I really wanted something fun, and flirty for summer. She was always wearing the most beautiful sun dresses or shorts with loose blousy tops that seemed to just drift across her tanned skin and the shoes! Ohh she always had the prettiest sandals, some flat, some with wedge heels that showed off her sexy feet, perfectly painted toes, with cute little toe rings that always seemed to glimmer and catch the sunlight just right. Lost in my thoughts about how beautiful Karen was I let out a little gasp of surprise when the sales lady next to me spoke. "Excuse me miss, errr, sir...I'm sorry," she said blushing a bit. "Can I help you find something?" "Yes ma'am," I said after recovering from the mild shock of being surprised. "Ma'am, you don't have to be sorry, I know I'm a bit confusing and I can see where it would be hard to tell if I am a miss or a sir. I....well I don't think I'm either, I don't mean to babble, I just wanted you to know that you didn't have anything to apologize for." The lady looked a bit more confused with my explanation and I was beginning to see I was making her uncomfortable. "Ma'am, I am sorry, I know it is weird, me standing here dressed like this with lipstick and such. If it is disturbing you or upsetting you I am sorry, that isn't my intention. It's okay if you don't feel comfortable helping me." With an uncomfortable laugh I added, "I promise I won't hold it against you." She returned my uncomfortable laugh with an uncomfortable smile. "Well, no....I can assist you, but...if you don't mind my asking, why? Why are you, well... why are you dressed like this?" Blushing and finding it impossible to look her in the eye I sighed, "I can't help it ma'am, I am a sissy." That last word seemed to stick in my throat but I had to say it. "I am married to the most wonderful woman in the world and she is helping me understand myself, I thrive on obedience to her, well to all women. I want to pick out a summer purse for her. I also need to get a purse and wallet for myself, the new clothes my wife picked out for me don't have any pockets." Just hearing it out loud it sounded ridiculous even to me. "I'm so sorry to have bothered you today ma'am, I know you have better things to do than talk with a freak." I was starting to get upset because I was responsible for making this nice lady uncomfortable. With tears beginning to well up in my eyes I quickly turned to run away and stop bothering this wonderful lady. As I began to pivot away I felt a hand on my elbow. "Please don't go, I didn't intend to hurt your feelings, you are quite a delicate little thing aren't you. I would be glad to help you pick out your bags," She said, this time with a pleasant smile. "I have never met a sissy, would it be okay if I asked you some questions while we shop, I'm just curious." With a sniffle and a quick wipe of a tear from the corner of my eye, damn I was such a sissy, crying over everything. I blamed it on the frustration of the chastity cage. "I don't mind ma'am, I will do my best to answer any question you have." "The first question is what are you looking at for a purse, do you want to look for yours first or your wife's?" "Can we look for Mrs. Karen's purse first, I want something fun and sassy!" "I believe that I have the perfect idea follow me," she said, while walking over to one of the designer counters. "Just looking at your very tasteful bag I am assuming that your wife and you prefer nicer bags, but if you would like to look at some non-designer options I will be happy to show those to you as well." "My wife believes that quality is worth paying for, she keeps her bags a long time and I take very good care of them, keeping them cleaned and orderly when stored." "Well then I have the perfect bag," she said leading me over to the Dooney & Bourke Collection counter. I saw it before she even pointed it out. A beautiful Hydrangea monogram domed satchel. The floral pattern of pinks and blues with a dash of bright green. It was so cute, it had handles but there was also a long crossbody shoulder strap. It was a little big for the average crossbody bag but it looked so summery and fun! The sales lady saw my eyes light up when she lifted the bag and passed it to me. I quickly put it over my shoulder, although the crossbody strap was thin is was heavy leather and was comfortable. Opening the bag it was very roomy and Dooney quality has always been great. Looking at me with the first genuinely warm smile she gave a little laugh. "You really do love your wife don't you?" "Yes ma'am, with all my heart, she will adore this bag, it is like nothing else in her closet!" "You know, if being this sweet and caring is what a sissy is then I think your wife is a very lucky woman," she said in a thoughtful tone. Blushing but with a huge smile I replied, "Thank you ma'am, that was very kind." "I would really like to meet your wife one day, she must be a special woman." "She is, she is the most special woman in the world. I don't mean to imply that you aren't too ma'am, I mean, you are very pretty and so nice, I mean, well...ummm..." "It's okay, I understand what you are trying to say. So you will take this one for your wife, now what would you like for yourself?" "I need something larger, my wife told me I would be carrying a lot of stuff, and, well I really want to surprise her and make her happy with my choice. I have been a bit of a pain in the tush to her today, so I want to get something that is really feminine and sissy. Pink may be the best color for someone like me," I said, ashamed of the words, even as they came out of my mouth, but knowing that they were true. "Hmmm, something tells me that you need a large bag but one that screams sissy and is the most embarrassing thing you could carry while still being classy," She turned and walked to the other end of the Dooney counter and picked up the Large Shopper in patent pink. The bag was large and structured, in the classic shopper shape. The shiny patent pink screamed sissy and was accented by the light tan shoulder straps, zipper and Dooney & Bourk patch on the front. The bottom had four small, rounded feet to keep the base of the bag from getting so dirty. "This is a very pretty bag....for a pretty little sissy boy," She added in with a mischievous smile that almost made me swoon. "Oh ma'am, that is perfect. I think that is exactly what my wife would want me to have for my first purse," What in the heck was I saying, this was the most feminine, girly bag I had ever seen. Part of me was overjoyed, it was so pretty and the pink was bright and shiny. Part of me was shrinking in horror at how humiliating this bag would be. My little penis began a series of vain attempts to get stiff, to no avail as the cage held it in check but this action triggered a flow of pre- cum that I could feel just oozing out. My face must have shown some of what I was feeling because the sales lady began to smile again. "So....sir, if you don't mind, you did say it was alright to ask you anything correct?" "Yes ma'am." "So...does this excite you?" Then leaning in closer she whispered, "Are you getting hard?" "Ahhhh yes ma'am and no ma'am, I mean well it is hard to explain." Reaching under the glass case she came out with a large wallet in the same beautiful glossy pink with the same light tan accents. "Oh, do try to explain," she said while handing me the wallet. "That is a very pretty color pink isn't it, does that excite you too?" "Yes ma'am, it does excite me," I told her quickly, hoping she would forget about making me explain about not being able to get hard. "You only answered half of my question sissy, you are suppose to explain to me if you are getting hard, you said yes and no." Turning as pink as the wallet I was holding and averting my eyes down to my feet. "I'm in, well my wife put me in, well she has the key....its a...do you know what a chastity cage is?" I mumbled. "You're locked in a chastity cage," she gasped in astonishment. "Oh this is too much sugar. Did you let this happen or did you get drugged or something?" "No ma'am, I willingly allowed it to be locked on. Mrs. Karen owns my pleasure now, like everything else." "So you gave up your orgasms for her?" she asked incredulously. "No ma'am, they were always hers but I am weak and I would have cheated, I would have been naughty and done things when I was excited. You know, by myself." As I spoke my whole body flushed in embarrassment. Looking up at her "It is really difficult, my mind is going to mush, I can't think, everything seems to have sexual overtones, I'm glad I don't have the key because I know I couldn't resist. I'm so pathetic." I hadn't realized it but I had been looking up through my mascara thickened lashes and I was biting my lower lip while looking at her. "Are you flirting with me sissy?" she asked. "Or are you just a little tease?" "No ma'am," I said in a rush. "You know, you are too pretty to be a boy, if you were mine and I had you all locked up I can guarantee that with those pretty little lips and that sneaky little tongue that I would not be the one going without orgasms!" She could not have known, but I am sure my expression gave everything away. I was fire engine red and could not meet her gaze. "Ohhhhh you naughty little boy, does she make you use your tongue to please her while you stay locked up? Where you wearing that lipstick for her? Were you batting those big doe eyes, glancing up at your wife while she commanded you to bring her pleasure?" Her voice was getting more excited, here breathing a bit heavier. "Let's try a little something, call it my gift for you in exchange for helping you pick out bags today and you introducing me to your wife." "I don't understand ma'am." I trembled. "Don't play coy with me," She said while taking my bags and ringing them up. When I looked at the amount before paying I saw that it was too low. "Ma'am, I don't think you charged me for something, did you miss ringing up the wallet?" "No, but I appreciate the honesty honey, I am giving you my employee discount but there is something that I want you to do for me." "Yes ma'am, what is it, I will try my best." "Great!" she exclaimed in an excited voice and grabbed me an my shopping bags. She led me across the second floor towards the cosmetic area. The pretty smell emanating from all of the cosmetics, lipsticks, and perfume were intoxicating. If I had a second favorite fetish it was this. Some mornings I would help my wife with her makeup by handing her brushes and closing bottles and tubes just so I could watch her put on her everyday makeup. It was such a sensual process and sexy as hell. Gazing at a display rack of lipstick I thought back to how it felt when the pretty blond lady made me stand and suffer as she applied lipstick to me. I say suffer but all I could remember was the smell and how wonderful the smooth waxy coating felt as it gilded across my lips. My clittie began leaking again as I recalled the sensual kiss that Mrs. Karen and I shared, our lipstick coated mouths sliding together. Shit I was loosing my mind. We arrived at the Lancome counter and she sat me down on one of the high chrome and white stools. Leaning over the counter she waved at someone in black pants and a black lab coat with a white shirt underneath. As he approached, his hair cut short but very stylish, swooped to the side in a purposeful messy arrangement, my sales lady and tormentor spoke up in an exuberant tone. "Tony!, Tony! Oh have I got someone to introduce to you!" "Whatcha got here Bec?" He said in a mellow baritone voice that sounded smooth and soft, like running your hand over crushed velvet. He walked over to us, no he sauntered over to us. "Well hello there," he said when he saw me sitting at the counter. I didn't know how to respond, I didn't know what the sales lady, or Bec as he called her, had in mind for me. "Hello sir," I responded quietly, avoiding eye contact to help hide my embarrassment. The handbag sales lady spoke up breaking the small slice of uncomfortable silence, "Tony, this adorable little creature is a sissy and is literally owned by his wife, who he is totally dedicated to. I have also just learned that she is locked in a chastity cage and her wife keeps her sexually frustrated, not allowing any private "playtime" if you know what I mean." I wish I could have melted into the floor and died, my face was red, my whole body was flushing. Never before had I been so embarrassed, and this was worse because it was in front of a man. I started looking franticly for a direction to flee, my eyes must have been wild with fear because the lady reached out and held my wrist. "No, no, you're not going to be running away, did I embarrass you? I thought that you enjoyed that? Well anyway, I want you to sit right here and to exactly what Tony tells you to." Then turning to the dark haired man she continued. "Tony, take a look at this, have you ever seen a boy with eyes like this? Look, no Adams apple, silky smooth skin, really, what do you think, do you have time to do her makeup. I want it as a gift to her wife." Taking a small step back Tony put his hand under his chin, index finger across his lips. "Hmmm, Becky you have a point, he is absolutely beautiful, I agree. Good bone structure, silky skin with a lovely complexion and those big brown eyes do just scream tie me up and fuck me senseless don't they. Yes, I will make time for this pretty little thing." "Oh Tony you are so sweet," Mrs. Becky told him. "I need to run do one quick thing and let Sue know that I'm going to take a longer than usual break. Sissy, Tony is by far the best makeup artist I have ever known, relax and trust him okay." "Yes ma'am," came the usual quiet whisper. "Oh Tony, I really want a pretty look, maybe a little sultry but please not slutty or over done. I really think she is a demure, pretty little creature and anything gaudy just wouldn't be right," she said before dashing away. With a genuine smile full of brilliant white teeth he gave a little chuckle. "You know Bec, I agree with you, pretty, demure, maybe a little bit extra for the eyes but keep it classy. This is going to be fun!" Turning to me he gave a reassuring smile, "What is your name, I can't just keep calling you sissy, that seems rude." "Brian," I said in a voice so quiet that it was barely audible. "Well Brian" he said while removing the mirror that was sitting beside me. "Don't worry about a thing, I promise I won't do anything weird or ugly, have a little trust and let's have some fun. Remember, everything I am doing can be taken off with a little cleanser okay?" "Yes sir, thank-you sir," I replied actually relieved at how friendly he was being. He was right, it was just makeup, I could wash it right off. With that he went to work starting with a moisturizer that he told me had 50 spf sun protection and that even if I didn't wear makeup in the future, which he said I should because I was to pretty not to, I should wear the moisturizer to protect my face from the sun and to keep my skin in good shape. Next was a light primer, foundation and just a dab of concealer around my eyes. His hands were gentle as they adjusted my face to allow him the right angles and the soft brushes fluffing against my skin felt pretty. He spent a lot of time around my eyes and had me look up, down, left and right while he worked in certain areas. Towards the end he worked on my lips which surprised me since I already had on lipstick but Tony explained that he was lining them with a pencil to reduce feathering and then he went in with a warm, burnt raisin colored lipstick all over, then a lighter tone, but that was just in certain spots, he said it would give my lips highlights and make the front of them come forward more giving the illusion of plumper lips as the dark raisin hued colors sank into the background and the shimmering highlight color popped to the front. Before he was done Becky had returned with something in her hand. Tony teased her and told her that no one could see my face until he was completely done. The last thing after applying powder to set everything was a sprits of Morphe Continuous Setting Mist, Tony told me that would keep my makeup fresh looking longer. Stepping back to observe his work he began to smile. "Wow! I don't know what to say. Becky you have a great eye for a pretty face. Brian, no I can't use that name for you with the way you look right now. Do you mind if I call you Brie?" That seemed to be an odd request so I didn't answer him immediately, why would he want to call me a girls name. "I chose Brie because it is a little similar to Brian, but calling you a man's name is an injustice. Brie sounds soft, demure, fragile, but a little exotic, it fits you. I won't call you that if you really don't want me to but I promise you, it would be a crime not to. Would you please consider it, at least take a look and then give me your answer," With that Tony indicated that I should turn around and look at the larger waist high mirror at the side of his makeup counter. Slowly I slid off the high stool, dreading what I was going to see. I full expected my visage to be that of a clown, a silly man wearing makeup, a freak. I approached the mirror head down, looking at the floor. As I slowly lifted my face I heard Becky gasp which shocked me a little and I jerked my head upright. The person looking back at me from the mirror wasn't me. I was looking at an absolutely beautiful woman, glowing soft skin, with soft bronze cheeks, full sensuous lips and large expressive eyes that seemed so deep and brown that you could loose your soul in them. Slowly lifting my fingers up and gently touching my face, I half expected not to feel them because it could't be real. "Holy smoke!" Becky exclaimed. "Tony, how did you, I mean, I didn't expect this. Oh Brie you are so beautiful, I got you a little gift that I thought your wife might like." Still stunned I saw her trembling hands reach up and pull something across my throat. It was a pale pink ribbon with a little bow on the front and a small metallic heart charm dangling from the center of the bow. She fastened it snugly around my throat, a choker, a pink choker with a little bow and heart. "I thought that since you said your wife owned you and you were so pretty that others would try to take you away that you needed a little collar, but nothing harsh, it had to be pretty. Oh you are so, so beautiful." I was so confused, she was right, if I had seen me I would have been smitten, how could this be? How could I be pretty. In a daze I reached into Karens purse and pulled out my phone. "I...I need to call my wife, she told me to call her when I was done." Looking at Tony and Becky I asked, "Should I take this off before she gets here, I don't know what to do, she didn't tell me to get a makeover." Tony spoke up first. "No please don't take off your makeup. I think your wife will be astonished, if she gets upset I will take responsibility, I promise." "Yes sir." I began dialing the phone with shaking hands, when my wife answered she sounded a little flustered. "Where are you at sissy, I have been walking around the handbags looking you!" "I am sorry Mrs. Karen, I ended up in the makeup department after I bought our purses...." I began to explain. Miss Becky indicated that she wanted to talk on the phone and then she reached out and took it before I could even make a decision. "Hello, This is Becky from the handbag department, please don't be upset with your husband, there was something else that I wanted him to see and it took a bit longer than expected..... Yes, yes of course. I was able to give him my employee discount... yes, oh you're welcome. No.... Well, yes I agree. We are at the Lancome counter, just walk straight down the aisle past the Coach display and keep going. We are close to the center of the makeup department. Yes, I know, ok bye bye." With that she hit end on the call and handed my phone back to me. "Well Brie, she sounded a bit flustered at first but I think you will be okay, I was clear that you had done your shopping as you were suppose to and that I forced you to come over here. I did not tell her that we had done your makeup so let's sit you back down facing Tony so we can surprise her." I climbed back onto the tall stool and sat looking at the makeup artist, the whole time I was petrified, so worried that I was going to be punished for being bad. I didn't want to have my little balls spanked again but most of all I didn't like it when Mrs. Karen was upset with me, that made me sad. The anxiety and fear must have been clearly displayed on my face because Tony stepped in close to me and took my hands in his. "It's going to be fine Brie, you are so beautiful there is no way that your wife will be angry with you, try to relax and stop biting your lip, you're going to mess up your lipstick before she gets to see it," His words were deep and reassuring, his voice was so calming. Taking a deep breath I vowed to be brave. "If I were you I would try to relax and be the soft, obedient, sweet sissy that you are and she can't do anything but love you." "Yes sir, thank you sir." "Damn, do you know how hot it is when you look up with those eyes and say, "Yes Sir," you are a dangerous little thing and you don't even realize it," Tony said with a smile while taking a moment to remove the scrunci Karen had placed high on my head, dropping the ponytail and adjusting my hair by tousling it up and then pulling some of it forward to better frame my face and sliding the hair tie onto my wrist. "You are a confusing little creature Brie, I am usually only attracted to women, I know you're a guy, but damn, I would do you in a heartbeat." Those last words scared me, it was the first time that a guy had ever told me that. I mean, I was married, I wasn't into guys, but here I was dressed fully as a woman now, how had all of this happened in just one day! I would have continued to go down that rabbit hole of total confusion if I hadn't heard a familiar voice behind me. "So you must be Becky, have you been hiding my sissy from me?" Karens voice did not sound as angry as it had been on the phone. "Yes, and you must be Mrs. Karen, your husband has told me so much about you it is so wonderful to meet you, he did a fabulous job of choosing your purse and you should have seen his eyes light up with joy when he was telling me how pretty you would look with it." "Oh he is such a sweetie, speaking of which, honey what are you doing sitting there looking away from me, is everything alright?" Taking in a deep breath and trying my best to relax and act somewhat normal I slid off the stool once again and slowly turned around to face my wife, tugging the straps of her purse up on my arm in the process. There was a prolonged silence as I looked at her, dammit I was biting my lip again after Mr. Tony told me not to. I did not trust myself to speak. Looking at my wife, her eyes wide with disbelief as she stared at me. Karen finally broke the silence "Oh sissy," she gasped. Was she mad, was she happy, I couldn't tell so I remained quiet, dropping my face down and looking up towards her, twisting my foot a bit but trying to remain still. She took two long strides towards me and I instantly dropped to my knees as she reached me, I bowed down before her. "Mrs. Karen I am so sorry, please don't be mad. I didn't resist but Miss Becky thought this would please you, it's not her or Mr. Tony's fault ma'am. I'm just not very good at being forceful or telling people no. Miss Becky gave us her discount on our bags and it would have been rude to have said no..." I was babbling almost incoherently, my speech was rapid, breathless. I felt gentle hands lift my face up and I saw my beautiful wife looking down on me with the warmest smile. "Little sissy, don't you dare cry and mess up that makeup or you will be in trouble, do you understand?" "Yes ma'am, are you mad at me, am I going to be punished?" Karen looked over to Becky and Tony, "you two must think that I am a horrible woman the way he is caring on about being punished, I really do love him, well maybe her. You did a phenomenal job with the makeup, I swear she is beautiful, so soft, so sexy, so I want her in the bedroom right now. Thank you," Looking back down at me she smiled. "Oh Brian...." Tony quietly interrupted by clearing his throat. "We kinda started calling her Brie, Brian just sounded silly considering how pretty she turned out." "Oh, well that is a very pretty name," she said with another smile, looking down at me still on my knees. Karen took my hands in hers and began to lift, helping me stand. She slid her hands down around my waist and held me out at arms length distance, looking directly into my eyes. "Honey, you are stunning, I knew you would be pretty in makeup but I never in a million years thought it would be like this, no I am most certainly not mad at you. Maybe a little hurt and disappointed that I wasn't the one who got to be there first person to do your makeup but I must say, Tony has very good taste. Now little sissy, what am I going to do with you? I'll tell you what is going to happen, we are going to go home and you are going to try on one of those pretty sets we bought at Victoria Secrets, and we are going to have some very intimate private time." With a pat on the butt she told me to wait over by the makeup counter while she spoke with Tony and Becky. As I walked away I paused to pick up the shopping bags with the two purses and wallet in them and managed to pick up a little of their conversation. Something about having Tony put together a makeup bag for me and all of them exchanging phone numbers. Nervously I hustled to the counter where I had been told to wait, not wanting to get caught listening in on my wife's conversation. Standing quietly, and being alone without someone scrutinizing me for the first time all day I realized how exhausted I was. Leaning back onto a stool near the Mac counter I put my hand gingerly to my head to rub my temples as the first signs of a headache began to emerge. It was only a moment before Karen was once again standing next to me, with her arm in mine. Leaning over she whispered into my ear. "Let's go home sweet lover, just you and I for a long quiet evening together." And with that she led me out of the store to the soft leather seats and air conditioning of her car.

Same as Forever Her Sissy - Chapter 4 (of 6) Videos

4 years ago
  • 0
  • 23
  • 0

Forever Her Sissy Chapter 3

Forever Her Sissy - Chapter 3 This is a work of fiction for your enjoyment, all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. We were driving west, the sun was shining and the morning was warm without being hot. Although it was a...

2 years ago
  • 0
  • 23
  • 0

Forever Her Sissy Chapter 2

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 2 (By Purse Sissy) The drive home was uneventful and quiet, when we arrived I carried her bag in as usual...

3 years ago
  • 0
  • 30
  • 0

Sissy Sex Therapist

SISSY SEX THERAPIST by Throne "But honey," Darren said in a whining tone. "You can't mean that. How could I be a... a sex therapist?" His wife Kelly smirked at him and said, "You have to understand, Darla, that a sissy like you could be very valuable in helping some men to deal with issues they have in their sex lives. For instance, the new guy I just started dating, Brad. He doesn't understand the whole sissy mindset, and how useful a weak feminized husband like you can be in...

4 years ago
  • 0
  • 56
  • 0

Sissy Stepson Part 4 Stepmothers Test

Part 4 - Stepmother's Test She crossed her legs and began dangling her high heel again and Carl became excited. His sissy stick started to stick up as he watch the dangling show and fashion models prancing on the run way. He had no where to escape and his stepmother noticed her panties bulging with his sissy cock. She nonchalantly let the shoe fall on the carpet and said, "Well, missy are you going to pick my shoe up and place back on my toes or can't you get up!" "Yes, ma'am, I...

4 years ago
  • 0
  • 50
  • 0

Mothers Sissy Teachers Pet

Mother's Sissy, Teacher's Pet By Sandy Brown January 15th, 2012 Dear Ms. Brown, I am Sandy's homeroom and science teacher. I thought I would mention to you that I noticed that Sandy had a small amount of nail polish on the base of his fingernails today. I assume that he was having some fun with you over the weekend, and that before he left for school you used nail polish remover, but inadvertently left some polish on. The color is very pretty, and I'm sure he looked adorable, but...

3 years ago
  • 0
  • 35
  • 0

Sissy Therapy

Sissy Therapy by Kate "Great practice, guys! If we keep working hard, we have a real shot at the conference title," Coach Jones addressed the thirty or so high school boys gathered around him. The boys were sweaty and tired, but the coach's praise momentarily raised their spirits. "Smith nice passing out there. Keep up the good work." Fifteen year old Billy Smith grinned cockily. "Sure, Coach. After all, I am the greatest!" The other boys moaned at Billy's arrogance. Coach...

2 years ago
  • 0
  • 46
  • 0

Heathers Sissy

Heather's SissyMy husband, Bobby, is standing with his nose in the corner, quietly sobbing, as he contemplates the ill-advised temper tantrum that he threw this afternoon. His sobbing is due to a very sore bottom, for which I take credit foróalthough to be fair, my favorite wooden paddle should also take some of the credit too.I'm not sure what it was that finally sent Bobby over the edge today. It could be the fact that I arbitrarily extended his sentence of chastity for another month, or it...

3 years ago
  • 0
  • 21
  • 0

Forever Her Sissy Chapter 1

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 1 It was It was quite an opportunity to be on this special team dedicated to a multi-year market research...

3 years ago
  • 1
  • 31
  • 0

The White Sissy Slave Society A Walk into Sissyhood

The White Sissy Slave Society: Sold into Sissyhood By Meeah Soo They were standing in a small group, drinking beer, smoking, and laughing. I could hear the rap music thumping aggressively from their boom-box. I could see them watching our car. It was late, well after midnight, and this particular park was no place for a white sissy to be at this hour. I've never been a physically or mentally strong person. I'm very easily intimidated. And there I was in a tiny plaid mini and white...

2 years ago
  • 0
  • 35
  • 0

Sissy Stepmother

Sissy Stepmother A Pantyboy Profile INTRODUCTION Cheryl here. You remember me. The 20-year-old pantyboy extraordinaire. Every man's naughty, secret, wet dream. Raconteur without equal. In "Service" and "Test Driven," I told you about Amy and Judy, two of my lovely roommates, fellow pantyboys and like me, covergirls for "Panty Boy," the only publication worth buying, besides some of those Spermco comic books about us "special boygirls" and the "Sunday New York Times." And Panty...

4 years ago
  • 0
  • 30
  • 0

Sissy Mission 4 Southern Belle Sissy

The Sissy Mission series consists of short-short stories designed to give ideas for domme/sub play, solo "outings," or just for your reading enjoyment! The goal is to have a dozen vignettes. --CA Sissy Mission 4: Southern Belle Sissy By Cheryl Alison Mistress believes in community service. So when she dropped the ad on my desk at home, I knew that I would be a faithful community servant within a short while. The ad read: Southern Belles Needed The Ladies' Auxiliary needs...

3 years ago
  • 0
  • 36
  • 0

Mothers Sissy Teachers Pet Part 3

Mother's Sissy, Teacher's Pet, Part 3 "Sandy's Diary" By Sandy Brown January 15th, 2012 Dear Diary, This is my very first entry! When Mom bought me this diary for Christmas, well, to be honest, I thought that only girls wrote in diaries. It didn't help that you are pink. Mom told me it's just a pale red, but you look pink to me. She also told me that lots of boys write in diaries, but the only kids I know who have...

3 years ago
  • 0
  • 26
  • 0

Sissy Therapy

My advertisement read: MEN Interested in sex with other men but don't know how to proceed? Looking for a safe, friendly way to find out if this is for you? Obsessed by online bi/gay/sissy/crossdressing porn but frightened to meet someone? Is your marriage at risk because of your desires? I can help! One four-hour sexual therapy session will help you to decide if this is right for you, and will help you to understand your desires. Don't suffer alone, I can...

3 years ago
  • 0
  • 29
  • 0

My Stepmothers Sissy Daughter

My Stepmothers Sissy Daughter By Malissa Madison The dream was so real, she was being chased by some evil thing that thirsted for her blood. She was cornered with nowhere to hide. She felt its hot breath on her as she tried feebly to squeeze through a hole too tiny to fit. The hot breath as it pushed its nose against her bottom. It felt hot and wet, Wet? She woke with a start in full panic unable to stem the flow. All she could do was lay there and cry in silence. She'd had this...

2 years ago
  • 0
  • 26
  • 0

Forever sissy

This story is based on something that really happened to me. Yesterday i cam out of the shower and, as always, looked at myself in the mirror. i always get pleasure looking at my soft little impotent cock resting on top of my ball sac. My fat titties bulging out to the sides and my rolls of flabby fat!! i've always said i look like i'm pregnant!! My pubic hair is gone and my underarms are smooth too. However my wife will just not allow the rest of my body to be smooth. Anyway, getting back to...

3 years ago
  • 0
  • 51
  • 0

Stepmothers Sissy Schoolboy

One-Handed Reading: A Step-mother's Sissy School-boy This is a one-sided conversation between an (evil?) step-mother and her delinquent step-son. ------------------------------------------ Author's Note: This is not some attempt at a Pulitzer, or to make some earth shattering literary statement. Nope. If you are looking for deep characterization or nuanced subplots, move on. This tale is not for you. I love exploring verbal humiliation alongside being dressed. This is what I call...

4 years ago
  • 0
  • 44
  • 0

Sissy Stepson Part 1 Stepmothers Trap

Sissy Stepson Part 1 ? Stepmother's Trap Carl Monet was a shy boy of about 15 when his widowed father married Rita Parker. Mrs. Parker was 20 years younger than Carl's father Larry. Carl was very shy and sheepish toward his new stepmother and the new Mrs. Monet was rather cold and distant towards him. Carl's father was gone quit often on trips abroad for weeks at a time and Mrs. Monet was often gone shopping with her sister Maryann and her mother Regina. Carl was...

3 years ago
  • 0
  • 32
  • 0

Sissy Therapy Case Study 2

Sissy Therapy - Case Study 2 Shelly's latest client is John who is obsessively addicted to smooth, shaved men's asses, ideally covered by skimpy women's panties. Shelly helps him to come to terms with his desires and learn a lot about himself as well. Oh, lots and lots of sex as usual... ;) Hi, I'm a sexual therapist. Sort of. No qualifications, my only experience is what I've gained on the job. This is my second 'case study' which took place a few months after I started. To recap...

2 years ago
  • 0
  • 47
  • 0

Crowd Sourced Sissy Spin OffMothers Milk

NOTE: This story stems from an incidental bit in the "Crowd Sources Sissy" story that a couple of readers seemed to be interested in having me explore further. It's just a starting off point. You do not need to read that story first to understand this new work, but of course feel free to read it to get the full effect. Enjoy! Crowd Sourced Sissy--Mothers Milk I knew that my husband had a sissy fetish long before I married him. For many, that would have been a bridge too far,...

3 years ago
  • 0
  • 50
  • 0

My Young Sissy brother for Mens Cum today

sharleesisterboyMY Young SISSY brother in Heat for Men's Cum, today!You used to prance around the house in your white underware, when Mom was gone, shaking your cute ass at me till I caught you, roughly, in My Big brothers arms and carried you to my bedroom floor. You giggled all the way, till I tossed you down on the dirt floor and you tumbled and smiled up at Me and lay on your tummy with your legs spread wide for Man-Cock. You know what I like to do to You, but, instead, I tie your wrists...

2 years ago
  • 0
  • 24
  • 0

My Stepmothers Sissy Daughter part 3

My Stepmothers Sissy Daughter, part 3 By: Malissa Madison I woke up early, my wet diaper urging me awake as I opened my eyes. Mommy was watching me sleep, and I realized her hand was resting on the crotch of my plastic panties pressing the wet diaper against my skin. "Did Mommy's baby girl wet her diaper," she smiled at me. "We can't have you in a wet diaper now, mommy's just going to have to change that," she helped me out of bed and I climbed up on the changing table, putting...

4 years ago
  • 0
  • 26
  • 0

A Sissy and Four Brothers

A sissy and four brothers -What is it like? Mother is very strict about separating me from 'the boys' but they've never experienced a 'sister' in the house before so there seems to be a lot of snooping around. A few of my readers have asked me for some additional information about farm life and living as a sissy with four brothers, and I'll respond to the question about seeing Jack again. Jack's mother called me and told me that I'd done wonders about boosting his self-esteem and she...

2 years ago
  • 0
  • 40
  • 0

Sissy Julian Chapter III Further Development

Just when Julian's Lake Orenda experience seemed perfect, even if he is not about to admit it, circumstances change. But then Julian and the twins were very naughty boys, and we all know what happens to naughty sissies. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to...

2 years ago
  • 0
  • 38
  • 0

Teaching the Sissy Maid Workshop at the MVP Chapter Four Daisy Training Prepares Her for the Workshop

Teaching the Sissy Maid Workshop at the MVP, Chapter Four: Daisy Training Prepares Her for the Workshop Synopsis: Flashing between Daisy's training before the seminar and the seminar's beginning, more is learned about how Daisy trained to be ready as Ms. Rebecca's sissy maid example and how the Sissy Maid Workshop is run to insure the transformation of the submissive male candidates into the sissy maids and cuckolds wanted by their owners. I loved the look on Daisy's face as...

1 year ago
  • 0
  • 100
  • 0

Preachers Daughter Chapter 13 and Preacher Sucks

My wife, Charlotte, thought it was very nice and thoughtful for Jaimie, the 23 year old preachers daughter now moving with us, and unknown to my Mrs, Jaimie was carrying my baby, "Jaimie, thank you for all you did around the house today, but you know, you are not our slave, are our guest!" If my wife only knew, that Jaimie was "my slave" and number #1 cum slut.Charlotte was always wild in bed when alone or away in a hotel or when our k_ds were not home, date night always got me plenty of hot...

2 years ago
  • 0
  • 15
  • 0

We got us some sort of sissy fag here

Check Your Taillights It all started pretty innocently, at least by my standards. For many years I have been a closet crossdresser and like most, I thought there must be something wrong with me. The usual bag of emotions and guilt. One day I did an online search to see if there was a forum for crossdressers and sure enough there was. My whole world changed. Not drastically but change it did. I found there were many others who felt and dressed as I did and I finally found out I...

4 years ago
  • 0
  • 28
  • 0

Being Sissy To My Brother In Law

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...

2 years ago
  • 0
  • 26
  • 0

Being Sissy To My Brother In Law

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...

Crossdressing
2 years ago
  • 0
  • 33
  • 0

Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

3 years ago
  • 0
  • 51
  • 0

Sissyboy Conversion Therapy

One The ProblemI know I have high standards, Doc, Matt Studley said to his ther****t, Dr.Freudist. But it s more than that. Dr. Freudist nodded and said, Um hum. Can I be honest with you, Doc Matt asked.They always ask that, Dr. Freudist said to himself. I ve been listening tothis guy ramble on about his issues for seven weeks, twice a week, andNOW he s going to be honest But Dr. Freudist merely nodded and said, Of course. This is a safe place. And then he waited.And waited.Finally,...

1 year ago
  • 0
  • 56
  • 0

Sissyboy Conversion Therapy

One The ProblemI know I have high standards, Doc, Matt Studley said to his ther****t, Dr.Freudist. But it s more than that. Dr. Freudist nodded and said, Um hum. Can I be honest with you, Doc Matt asked.They always ask that, Dr. Freudist said to himself. I ve been listening tothis guy ramble on about his issues for seven weeks, twice a week, andNOW he s going to be honest But Dr. Freudist merely nodded and said, Of course. This is a safe place. And then he waited.And waited.Finally,...

3 years ago
  • 0
  • 31
  • 0

My Stepmothers Sissy Daughter part 2

My Stepmothers Sissy Daughter, part 2 By: Malissa Madison I lay there sleeping peacefully, feeling safe for the second time in so long I couldn't remember. I heard voices and I woke up, I was facing toward them on my side. A woman I didn't recognize but looked a lot like the girl in the diner said, "I think she's so sweet. I'm glad Dave brought you here last night. I was afraid to say anything about the bruises on your face, I didn't want to scare you." "Thank you Monica," mommy...

2 years ago
  • 0
  • 26
  • 0

A sissy in her early 20s begins a cyberrelationship with a Master

It started innocuously enough with what seemed like a harmless exchange of private messages on a friends- based porn site. A person identifying as a male sent a note to a young sissy whose profile expressed some fantasies about being made into a full-time sissy, perhaps involving some forced feminization and even surgical “enhancements.” The young sissy, April, responded openly and eagerly, and the conversation developed into one in which more and more of the sissy’s fantasies...

3 years ago
  • 0
  • 33
  • 0

An Online Sissy Lives Her Dream

(Dedicated to a hot little sissy here on xhamster, Sluttish, whose looks and fantasies inspired this story. Her fantasy name is April. That’s where this story starts.)It started innocuously enough with what seemed like a harmless exchange of private messages on a friends-based porn site. A person identifying as a male sent a note to a young sissy whose profile expressed some fantasies about being made into a full-time sissy, perhaps involving some forced feminization and even surgical...

2 years ago
  • 0
  • 34
  • 0

Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

3 years ago
  • 0
  • 30
  • 0

Becoming a Sissy Maid for Mark and Rebecca Part Three Ms Rebecca Shares Her Sexual Research of Sissies

Becoming a Sissy Maid for Mark & Rebecca, Part Three - Ms. Rebecca Begins Sharing Her Sexual Research NOTE to Review Writers: Thank you so much for the incredibly positive feedback. It is definitely motivating me to write more and write faster. Now to part three of our story. "Tell me what you know about males who are feminized so completely they are transformed into a sissy, changed from the less than manly person she had been before coming under the control of a strict...

4 years ago
  • 0
  • 64
  • 0

2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

3 years ago
  • 0
  • 47
  • 0

Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

1 year ago
  • 0
  • 54
  • 0

Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

2 years ago
  • 0
  • 44
  • 0

Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

2 years ago
  • 0
  • 43
  • 0

The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

4 years ago
  • 0
  • 50
  • 0

Teaching the Sissy Maid Workshop at the MVP Chapter Six Another Sissy for Ms Rebeccas Household

Teaching the Sissy Maid Workshop at the MVP, Chapter Six: Another Sissy for Ms. Rebecca's Household? After the workshop ends on day one, Ms. Rebecca stays to speak with some of the women attending the class and gets an unexpected offer that offers her some incredible rewards if she can take ownership of another young male submissive who is displaying sissy tendencies. After the workshop ended for the day, I stayed for a while to give me a chance to speak with some of the women...

3 years ago
  • 0
  • 26
  • 0

The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

4 years ago
  • 0
  • 34
  • 0

A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
  • 0
  • 32
  • 0

Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

3 years ago
  • 0
  • 40
  • 0

How my girlfriend turned me into her sissy bitch

Her Perfect Ass And Evil Sexy Dirty Looks Mind Fucked Me Into Wanting To Be A Girl Rather Than Fuck One......as this naive, innocent, christian, bible believing 20 something gave me the best sex of my life with a reach around, as I would cum, she would whisper "Not bad for a cock sucker. LOSER!" and then push me away, stand up, look at me in disgust with those evil sexy eyes that would become so powerful as she threw me the meanest, 'fuck you, loser' look ever, then she would leave, her perfect...

2 years ago
  • 0
  • 34
  • 0

Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
  • 0
  • 45
  • 0

Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
  • 0
  • 33
  • 0

Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

3 years ago
  • 0
  • 24
  • 0

Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
  • 0
  • 38
  • 0

Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
  • 0
  • 41
  • 0

Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
  • 0
  • 43
  • 0

She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
  • 0
  • 31
  • 0

100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
  • 0
  • 46
  • 0

Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
  • 0
  • 29
  • 0

Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
  • 0
  • 31
  • 0

A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

4 years ago
  • 0
  • 51
  • 0

407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

Porn Trends