Forever Her Sissy - Chapter -5 free porn video

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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 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and emotional with many questions left unanswered. Glancing at Karen I gave a big smile, remembering that she did not want a quiet, cranky sissy. "Mrs. Karen, what did you go shopping for while I was looking for our new purses?" I asked, trying to keep the tone playful and light, not accusatory or nosey. "Did you find what you were looking for?" "Oh yes sissy, I did find what I was looking for," she said with an ear to ear smile. I waited for her to finish and tell me what she had found but there was nothing else, just a smile. "Tony is going to send the order for your makeup to the mall near our house, though I must admit, I think you would rather go pick it up from him in person. You seemed quite smitten with him back at the store." I didn't know how to respond, Tony was a guy, I was a guy, I did not think I was smitten with him. I mean he was very nice to me. It was kind, the way he asked my name and seemed to really care about my feelings. I was still concerned about his comment; 'he wasn't into guys but he would do me'. "Ahh, maybe ma'am, I don't know about that. I mean he was nice but he's a guy and well, I'm a guy...I kind of just like girls," I stammered. Glancing over at me Karen asked, "Honey, do me a favor and pull down the visor mirror and give yourself a long hard looking over and then explain to me how you are a guy, a manly man, a big rough and tuff boy!" she was laughing as she turned her attention back to the road ahead. I just sat there in silence fiddling with her purse straps. "Sissy, I was serious, I want you to lower the mirror and take a long look at yourself. Just remember that I love you." Doing as I was told I lowered the visor and flipped up the cover to expose the mirror. The face looking back at me definitely would not be considered a man's. If I didn't know better I would say that I was looking at a woman, but I knew I wasn't a woman, and I had the chastised, leaking little penis to prove it. "Mrs. Karen?" I asked while still gazing into the small mirror. "Yes Brie, what is it?" she replied, giggling when she called me Brie. "Ma'am, do you love me like this? You know, not normal, a freak." "First let's be clear, you are not a freak honey, and what is normal anyway? Is normal pretending to be something that you aren't, being miserable and unhappy?" Karen sighed and continued talking, "I remember, oh ...it seems so long ago now but I suppose it has been five years, when you first begged me to let you hold my purse, first just around the house but then in the car, and it was so cute, how you thought you were sneaky when you would hop of the car still holding my purse so you could carry it while we shopped," Karen smiled and reached over to gently pat the purse sitting in my lap. "I couldn't understand what you were getting out of carrying my purse as a guy. It took me a long time to figure out that while yes you did have a purse fetish your real need was to be controlled. I noticed how differently you behaved when I commanded you to hold my bag, how demure and submissive you became. Then you started doing things around the house for me, and making me feel special." With a sigh Karen continued. "At first I didn't like it, I thought it was odd but then I realized that if I relaxed and accepted your gifts of service that it was quite nice and I began to enjoy and love you more for the sweet things you did for me." "The real eye opener was just a few months ago when you persuaded me to play chastity games with you. I really resisted this, I kept thinking, 'what would I say if something happened and someone saw that cage on you?' But then, seeing how docile you became when you were in chastity, and how focused you were on my pleasure in bed, that is what started waking up the monster in me." Karen continued talking as she put on the turn signal and steered into our subdivision. "Honey I have grown to love you, the real you, the sissy that is you, I love you so much that it breaks my heart to see you unhappy. I love the sweet things that you do for me, I love it when you hold my bag, I love it when your cheeks turn crimson from being embarrassed. The short answer is yes, I love you like this, I love Brie, I love sissy Brian, I love everything about you my sweet dove, and I love the things that we have yet to explore. You released this dominant from the depths of my heart and there is no putting her back in the cage sissy, do you understand?" "Yes ma'am." With a chuckle Karen said, "I don't think you do but you will." I believe she was going to say more but my phone rang and she answered it using the hands free on the vehicle stereo. "Hello, this is Brian," I said, trying to sound normal. "Hey Brian, this is Penny, I wanted to touch base with about Monday, is this a good time to talk for you?" "Yes ma'am, I have you on speaker, I am in the car with my wife." "Oh, hey Karen, I hope you are doing well, nice to talk to you again!" Penny's cheerful voice came over the speakers. "Same here, it was great meeting you the other night, can't wait to get together again. Oh, Brian and I have spent the whole day picking out some pretty office clothes, you know, like we spoke about over text last night," replied Karen in a happy, bouncy voice. "That sounds delicious, The girls and I can't wait to see her all cute," was Penny's reply. 'What!' I thought to myself, my boss and Karen have been talking about my work wardrobe? I guess it would be silly for me to have thought that Karen wouldn't have checked to make sure that my modified wardrobe would be accepted. Penny continued talking, "So Brian, I was calling to let you know that we are using Monday as a move-in day. I have checked with the corporate move team and all of our personal stuff has been delivered to the office. I was calling to let everyone know that the plan is to get our work areas set up and then do a team building dinner afterwards. Oh, Karen, spouses and significant others are more than welcome to come. It is going to be very informal, I am having it catered at my house." "Sounds great hon, see you there," Karen piped up. "Very good, well that is all, see you at 9:00 Monday morning Brian." "Yes ma?am," I replied. Arriving home it took a couple of trips to get all the packages unloaded from the car. I noticed that Karen carried a few bags in that I did not recognize or remember buying. By the time all of the new clothes were laid out on the bed in the spare room it was almost eight o?clock. I was beginning to feel sleepy and let out a huge yawn while Mrs. Karen was talking to me about my new wardrobe. "I hope you aren?t too tired sissy because I?m not ready to let you go to sleep just yet." Karen whispered in my ear while running her fingers lightly across my cheek. "As much as I hate to do this, we need to take our makeup off and get showers. What do you say about doing the shower part together to save time sweetie?" Her words removed any pretense of feeling tired, the thought of what could happen with us in the shower together made my little clittie work in vain to get stiff. I wonder how many times I might have squirted today if my wife hadn?t been smart enough to lock me up, but now I really wanted to cum. I was hoping that she would release me from the cage, the thought of her and I making love while we were in the shower was intoxicating. I literally dashed into the bathroom leaving a trail of clothes in my wake. "Whoa, hold on tiger! I am glad to see that you're excited but I don?t think you can just strew your clothes all over the place," Karen commented, while undressing down to her underwear and throwing her clothes on the floor. "Why don?t you pick up your clothes, and mine too sweetie, and take them to the laundry room. Just leave the undies on for me, it?s not right for a girl to be running around the house naked." "Yes ma?am, I?m sorry Mrs. Karen." What was I thinking, my desire was messing up my mind. I knew better than to leave a mess or to not clean up after Mrs. Karen. I was glad that she didn?t sound upset, I was determined that nothing was going to mess up our night. From here on out I would concentrate on being her obedient, happy, sissy. After retrieving our clothes and carefully placing her purse next to bed I hustled into the bathroom wearing just my panties and panty girdle. Karen was already at the sink washing her face with a night time cleanser. She pointed to my sink at our double vanity and slid the jar of cleanser towards me. Mimicking her actions I washed my face in the warm water with the cleanser, it felt both refreshing and a little sad to take off the makeup that Tony had worked so hard on. Karen finished first and started the shower. I watched in awe as she slid off her panties and bra, tossing them on the floor in front of our large walk in shower. With a rather seductive look she peeked around the corner of the shower and motioned for me to follow her before disappearing into the steamy waterfall. As I rounded the corner into our shower the hot water enveloped me, ohh it felt so good, and waiting for me was the most beautiful woman in the world. It did not escape my notice that she was wearing her anklet with my chastity key. My gaze was firmly locked on that beautiful key, just waiting for her hand to drift down and remove it so she could unlock me for our play time in the shower. The fantasies about pushing my wife against the warm tile wall and penetrating her with my manhood were interrupted by laughter, not giggles, not a chuckle, but laughter. Looking up I saw Karen plop down on the shower bench seat in a fit of laughter, she was wiping her eyes and even snorting a bit she was laughing so hard. "Mrs. Karen, is everything alright?" I asked, not seeing anything that could be that funny. "Oh sweetie, I?m so sorry, it?s just the way you were staring at the key to your little prison and, well, you were actually thrusting your hips back and forth. Oh that was precious. You are thinking that I?m letting you out of your cage aren?t you?" With a rather sheepish look on my face I spoke quietly, knowing now that there was no way the cage was coming off. "I kinda thought since we were in the shower together and well we are naked and well....Oh Mrs. Karen I?m so horny I think that I am going to die if I don?t get to squirt! Please ma?am, can you have mercy on your sissy, just this once, please ma?am." "Hold on sissy," she laughed, holding her hand up towards me. "I don?t think that it?s safe to release that little beast at the moment," This prompted another burst of laughter from her. "No sissy, you are not getting out of your cage tonight and for the record, every time you ask I will be adding more days to your chastity sentence. Hmm, since this was your first offense I will be lenient, let's say one extra month." My mouth dropped open but I had the good sense not to say anything, an extra month, and she was being lenient. How long was I going to be locked up. I slowly sank down to my knees and then slid into a collapsed sitting position, my face in my hands and began weeping. I would die, there was no way I could survive this. It had just been a day and I was an emotional wreck, how could I go for a month or more. My tears ran freely, mixing with the warm soapy water and flowing down the drain. I felt Karen?s arms around me and heard her voice, soft and consoling. "Shhhhh sissy, it?s okay to cry, everything is going to be alright. I know this seems impossible to you right now and maybe it is but you don?t have any choice in the matter. I am not unlocking you. You will never be able to focus if your libido comes crashing down. Maybe the toughest part of being a sissy, an owned little sissy, is that you don?t get to make these choices but it also means there is no reason for you to fret about it sweetie, it?s out of your control." She began to wash me, gently scrubbing my skin with a luffa sponge while I wept, lifting my arms and moving me about like some rag doll. Eventually I calmed down and began to help her, when my sobbing had subsided she smiled and gave me a kiss. Handing me the sponge and the wonderful soap that smelled like sweet strawberries she turned her back to me. "Now it?s your turn to wash me honey," she said. I began to lather up her back then her front, spending a bit of extra time around her breast. "Okay sissy, I think my titties are spotless now, please move along" she giggled. We finished our shower by standing back to back under the waterfall of steamy water. Karen got out first, reaching back she gave me a bottle of hair remover. "Be a dear and make sure that everything is smooth from your eyebrows down sweetie, I know you shaved last night but I felt a little stubble on your leg." "Yes ma?am," I replied, taking the bottle from her and reading the instructions. After watching what little hair I had swirl down the drain I stepped out of the shower to find two towels, a large fluffy pink one for my body and a smaller pink one for my hair. I had seen Karen do this a million times so after drying off my body I wrapped the larger towel around my chest and the smaller one I used to wrap my hair. Feeling clean and refreshed, but sad because of my locked condition I brushed my teeth and headed to the bedroom. What I saw there took my breath away. Karen was standing by her dressing table. Her hair was pulled back into a tight pony tail. She was wearing a stunning black lace bra, heavily covered in floral brocade, the cups lifting and pushing her breast up while leaving most of the top exposed, just covering the nipples. Following the curve of her body down were matching black panties and a delicate garter belt holding up a set of very sheer black hose. On her feet were a pair of pointed toe stiletto heels that were towering at over four inches tall. The small glint of gold at her right ankle was my key and chain, she must have removed it to put on the hose I thought to myself. Looking back at her, she had re-applied her makeup but it was not the usual light, pretty application. This was sultry, dark, dangerous looking. Her lipstick was a deep red with almost chocolate tones and her cheeks were sharpened with a shade of bronze that also captured the brown and gold hues of her eye makeup. Around her neck was a single strand of pearls, tight against her throat. The affect was incredible and I was speechless. I had never seen her like this, I knew that this woman could do anything that she wanted with me. Even her smile was intimidating, white teeth framed by dark mysterious lips, it was the smile of a carnivore sizing up its victim and there was no doubt who was predator and who was prey in this room. "It?s time to get my sissy dressed now, it?s time for Brie to make herself pretty for her mistress," Karen said while walking, no, more like stalking towards me. Following her pointing finger to the bed I saw my clothes laid out. First she helped me into my bra, the first bra I had ever worn. I held out my arms, the slender baby pink straps slid over them, settling into the valley of my shoulders. Standing behind me she pulled the back together fastening the three small hooks. The feeling was unique, the tightness was snug and made me feel girly, so sexy. Looking down I saw my flat chest under the pretty pink lace bra. My first thought was how silly I looked in a bra with no breasts but that thought was short lived as I heard Karen clearing her throat to get my attention and break me out of my daydream. In her hands were two silicone breast forms. Where had those come from I wondered as she slipped them into the bra cups and slid them around making small adjustments. "These will have to do for now sweetie, but we are going to find proper ones for you soon, breast that can be glued on and that will match your skin tone," she nibbled my ear while telling me this, my poor entrapped dick pressing so hard against the cage that it physically hurt. "With the new ones and a little makeup you won?t even be able to tell were you stop and your new breast begin, won?t that be nice sissy?" I couldn?t answer her, I was breathless. Now she held up a very sexy garter belt of the same lacy baby pink design, brining it up high on my waist and fastening it behind me. The feel of the garter straps dangling around my thighs was insane, every time they would move against my skin it was like an erotic collision. Pushing me down so I was sitting on the padded bench at the foot of our bed, kneeling at my feet she held out a rolled up stocking. "Lift your leg and point your toes sissy." As I complied she began to roll the hose up my legs, first one then the other, finishing by clipping the six garters to the reinforced tops of the hose. Feeling them, the new awareness as a breeze from the fan passed across my legs with the hose, I let out a gasp. Oh god, the sensation, the feeling of the hose agains my calves and thighs, it was like a lovers hug. Standing slowly on shaky legs I let out a low moan when I felt the taught garter straps caress the curve of my ass and gently tug at the hose as I moved, every small action was so sensual. Looking down my cage was actually jumping, bobbing up and down as my entrapped penis struggled to become erect, twitching the weighty little cage around. With a wicked smile Karen reached down with her finger, running it along the tip of my cage, gathering a large shining string of pre-cum and bringing it to her lips. Slowly she brought her tongue out and licked the droplet off of her finger, her deep crimson lipstick set against the dark burgundy of her manicured nail. Next she held up a pair of matching pink thong panties, they were so tiny, sliding them up my legs she pulled them upwards tightly, tucking my cage behind the little front fabric patch while seating the thong string between my cheeks. "Sissy, do you know why a woman puts her panties on over her garters?" she asked in a soft husky voice. "No ma?am," I squeaked, sounding more like a mouse than a person. "It makes her more available, some would say that it is slutty, are you a slut sissy, are you going to be my slut?" Her breath was hot on my face, her lips only an inch away from mine. Oh fuck this was so much. "Don?t get too excited sweetie, we aren?t done dressing mistresses little slut yet." She helped me into a pair of patent white three inch heels. Catching a glimpse of myself in her dressing mirror I was her complete opposite, dressed in soft baby pink with very light tan hose and loose hair falling around the straps of my dainty bra to her strong black daring lingerie, like yin and yang. Still wearing a very hungry looking smile she came up behind me and began to put something around my neck. I expected the pretty pink ribbon choker that Miss Becky had given me but this felt more substantial. Looking in the mirror again I saw a heavy baby pink leather collar, fitted with a large ring in the front and smaller rings on both the left and right sides as well as the back. I heard the subtle click of a lock closing and realized that Karen had locked me in this sturdy pink collar. Pushing me back onto the bed she stood over me holding a matching set of wrist and ankle cuffs in the same sturdy baby pink leather. "It was hard finding something so strong and secure but in this soft pink color. I don?t think that my little sissy would look good in manly black leather. No, for her everything needs to be soft and pink, so girly, so sissy, mmmmmmmm baby." As she talked about the difficulties of finding them she buckled the cuffs to my ankles and then my wrists, securing each one with a small brass padlock. Standing back and looking at me, I saw her smile grow. "My, my, my, what has mistress caught in her web? Look at you sissy, so pretty, so dainty, dressed in your soft pink lingerie, what naughty things shall your wife do to you tonight? Is that a little damp spot in the front of your panties, is your little clittie leaking in her cage?" Fuck, I was mad with lust, fear, and apprehension, I felt so venerable. I began to slide backwards, a little scared when my wife started coming towards me with a small makeup bag in her hands. "Just a little lipstick sissy, no need to do much, you're so pretty already. I think that the fear in your eyes is adorable," she purred as she applied a very soft, pink lipgloss. Setting that to the side she brought a short chrome chain up for me to see, it was maybe six inches long. While looking me directly in the eyes she locked one end of the chain to a ring on my right wrist cuff, then lifted my hand up to my throat and threaded the chain through the ring at the front of my collar. She lifted my left hand up towards the collar then, and affixed the chain to that cuff with an identical lock. My hands where bound up next to my throat. The sensation of complete helplessness overtook me. I couldn?t do anything to protect myself, the feeling of vulnerability was exhilarating and terrifying. With me lying back on the bed she curled up next to me pushing me further up onto the mattress until I was lying near the center of the bed. Karen started at my lips, slow kisses, gentle kisses, tentative probes with her tongue darting into my mouth. Then my neck, kisses and nibbles just above my collar, under my jawline, then below the collar. Her fingers tracing out the lines of the dainty pink bra straps that clung to my narrow shoulders, oh god, the feelings. "Ohhhhhhh," I moaned as her lips and tongue worked towards my stomach, my flat little stomach. All of my muscles contracted, my penis was pressing desperately against the cruelty of the cage that held it in check. Just below my garter belt at the top of the little triangle of material that were my tiny pink panties I felt her kissing, her hot breath floating across my skin, damp from her kisses. "Mrs Kaaaarrrreeeennnnnn, ooooooooo ma?am.....ooooooooo," I cried, this was so beautiful, like nothing that I had ever experienced. I held my eyes tightly shut, my whole body, my skin, had become this sexually charged hyper sensitive playground for her. Retracing her pathway she worked her way back up to my lips as we rolled over, me on my side, my wife embracing me tightly. "Ohhh! I exclaimed as I felt her at my butt pulling my thong string to the side, but my shock came from the cold, slippery wetness that was her fingers. Slowly she ran her finger between my cheeks, and I felt the slippery wetness, cold against my ass, until she found my rosebud. "What, Mrs. Karen, what.....what is happening?" I blurted out. "Shhh, sissy, relax. Trust your wife honey, trust your lover..." she whispered, her breath hot and moist like a tropical summer breeze. As she spoke her finger continued to probe, pushing the lubricant into my hole. First one finger, then a second. "Oooooooo, god, that feels soooooo...oh ma?am...please," I whimpered unable to finish my words. My brain seemed to have lost the ability to function. Slowly she leaned up, rolling me to my back. Reaching over to the night stand she picked up something, they looked like short pink leather leashes. In my confused state I did not understand until she had used them to attach my ankle cuffs to the rings on the side of my collar. I laid in bed, seductively dressed in baby pink lingerie, helplessly bound with my wrists at my throat and my legs held up in the air, the white heels on either side of my head. With a devious smile Karen slid her panties off. Holding them up to my face and leaning over me she pushed them to my lips. "Do you see this sissy? I put these panties on only ten minutes ago and look, just look at them," she said, pushing them against my lips. I could feel that they were soaked, I could smell her on them. It smelled like raw sex, like she smelled when I worshiped her with my mouth. "Open wide sissy," she said while pushing her wet panties, gusset first into my mouth. "I want you to hold those for me sweetie, while I get something put together for us." "wmahat ammre ymffou dommfing," was my muffled reply, and in terror I saw what was next. Kneeling in front of me on the bed I saw Karen lift up a double sided dildo, one end was slender with a set of balls, the other was thicker and curved. Looking me straight in the eyes she smiled as she slid the thick curved end into her wet folds, pumping it back and forth a few times until her eyes rolled back looking at the ceiling. "Mmmmmmmm, this cock feel so good sissy, filling my pussy, filling my pussy like you never could," Karen moaned as she worked the cock back and forth. Before she reached climax she brought herself to a stop and with a wicked smile she lifted up a harness, first one leg, then the other went through then pulling it tight across her waist. Reaching over she came back with a bottle of lubricant, squeezing the tube as she used her hand to rub it across the head of the dick that was poking out from the harness. My eyes were wide with fear, I knew what she was going to do but in my bondage I was helpless. Frantically struggling all I could do was roll over onto my side. With a giggle Karen pushed me back into position. "Well, well, well, what do we have here but a very pretty little sissy all lubed up and in a rather open position. What do you say honey, are you ready, are you ready for your wife to take your sissy virginity?" I shook my head madly and grunted into her panties. "Oh, so you don?t want me to take your virginity?" she looked at me, with her lip rolled out in an exaggerated pout. "Do you want me to give Tony a ring, I?m sure he wouldn?t mind coming over to help out, would that be better sissy, would you like handsome Tony to come take your cherry? I wonder if he has a big cock?" I began shaking my head furiously, this couldn?t be happening. I saw her reach off the side of the bed and lift her purse up, setting it onto my stomach. Digging around she came out with her cell phone. "You would have to stay trussed up like this for a while, I think he lives about thirty miles or so away," she said while scrolling through her contacts. I continued to frantically thrash doing my best to shake my head, which was difficult bound as I was. Karen looked at me with a serious face. "Sissy, if you shake my purse off and spill it I will turn your backside red." Oh shit, I stopped thrashing and began to gently shake my head back and forth. With another predatory smile she leaned over and pulled the panties out of my mouth. "What do I want to hear from my sissy right now?" she whispered in my ear. "Mrs. Karen......." I paused, catching my breath and clearing my mind so I could push beyond the barriers that were holding me back. I knew that she was serious, she had shown me that on multiple occasions today, I had one chance to do this right, to give her the answer that she wanted from her sissy. "Mrs. Karen, will you please fuck your sissy, please, she wants to loose her virginity to you. Please ma?am, please fuck me, please," My words died off into quiet little sobs. "Shhhh, easy little sissy, don?t be afraid. Mrs. Karen will be gentle, are you ready, Brie are you ready to go past where you have ever been before?" "Yes ma?am, thank you ma?am, please, I am so scared, don?t hurt me," I cried softly. "Don?t worry little sissy, I will be gentle, it may hurt just a little at first," she said as she crept up to me, I saw her hand slide down to guide the tip of her cock into my ass. I could feel the pressure, pushing on my opening, I was trying to relax but my body was fighting my mind. Steadily she pushed until the head broke through the first barrier. "Ooooo," I exclaimed as I felt it poke into me, then slowly slide further in. I felt the rhythmic pumping begin, gently working deeper. With steady strokes she drove the cock into me a little more each time. My mind was all over the place, oh how could this be happening. I was crying quietly, feeling the tears run down my face, soaking the pillow beneath my head but there was something else. Opening my eyes I saw her face, gentle and kind, with that glow that she always has just before climax, then it hit me. I was trying to move my hips with her rhythm. Even trussed up I was trying to match her thrust, my body was betraying me. "How does that feel slut?" My wife hissed between clenched teeth as she began to speed up, I could feel the balls of the dildo slapping against me as she pushed it to the base, harder and faster. As she leaned over me, she pushed her purse out of the way to get better leverage, sweat dripping from her face as she exerted herself thrusting harder and faster. "Ohhh ma?am, please don?t stop, please, I don?t understand but it feels so good, uoooouuu, thank you ma?am," I squealed like a little girl. Something was happening, something that I did not understand. Spurred on by my squeals Karen pushed deeper leaning over she forced her lips over mine in a desperate kiss of ownership, she began biting at my lower lip, I let out a little yip of pain. This seemed to electrify Karen, making her thrusting more urgent. I felt her at my ear, nibbling, grunting. "Do you like this sissy?" she said with broken, labored breathing, gasping in-between words, "Do you like being fucked like the little dove, the obedient little sissy slut that you are?" I could?t speak, there was a tremor that was starting in my stomach and spreading slowly like waves, expanding in all directions. I could feel it in my thighs, my lower back, my stomach, my groin, oh my god I could feel it in my balls and even in my caged little clittie. I didn?t understand, I was so confused as the sensations continued welling up from inside me. I couldn?t open my eyes, the feeling was too intense. I could hear Karen wailing, almost screaming and I felt her body begin to shake, and then in perfect rhythm with my wife my whole body began to quiver, waves of pure pleasure were rolling in with undeniable force but when they reached the beach there was only a gentle splash that continued to ripple through my body, not the sudden crash of waves on a beach. I could feel cum oozing out of my cock, my little locked up cock which was pulsing but not throbbing. There was no electric shock with explosions of cum rocketing from a hard dick but instead the steady rising of water, like a spring tide washing over the beach. It continued for what felt like minutes, forever, until there was no more cum to leak from my bound little clittie. My wife, tired from her exertions collapsed onto my body, her plastic cock still buried deep in my sissy pussy. For long moments we laid together, our bodies heaving from exertion. With a soft groan, Karen lifted herself off of me, slowly sliding her cock from my rear. Instantly there was a feeling of emptiness, a void where she had been. "Oh baby, that was nice wasn?t it, are you okay?" Karen asked as she picked up her wet panties and began using them to clean up what must have been puddles of cum. "Oooo, you came so much honey, did you like that?" she cooed, looking at the huge translucent white puddle on my stomach and around my balls. I didn?t know how to answer her. Everything was so confusing to me. Looking down the length of my bound body I saw a woman in soft pink lingerie, with cum all over her stomach, another beautiful woman using a pair of sex wet black panties to clean up ejaculate and in my peripheral vision were my heels trussed up by my neck. "Yes ma?am, thank you ma?am," I whispered, unsure of my voice, unsure of so many things. It was true that the release was incredible, so long and strong but there was something missing. I was hornier now than before, our beautiful act only heightened my needs without satiating them. "Sissy, there is one more hurdle that I need to help you start to overcome before we are done tonight," she whispered as I saw her raising her panties, dripping with my cum, up towards my face. "Open wide." In horror I thrashed about but to little avail bound as I was. Clamping my mouth shut I tried to turn my head, which was impossible with the straps going from my collar to my ankles. Karen reclined beside me, daintily holding the sopping wet panties with her thumb and forefinger. I could see the thick white globs all over them. "Honey, I can lie here all night while you throw your little tantrum, and I can leave you trussed up like this until time for work on Monday morning. This little show isn?t going to get you anywhere." Karen was right, she could lounge around in comfort, go to sleep, anything, while I had no choice but to stay bound. The muscles in the back of my thighs where beginning to tremble and my neck was getting tired from the constant pulling. Being completely honest, in my current state the panties could have been forced in my mouth and there would be little I could do to prevent it. Slowly the realization that I was going to eat cum was becoming clear, I had never tasted cum before, I was a guy. I loved Karen?s juices and took them with gusto but this was so different. Knowing I would be defeated regardless of my resistance, with a trance like motion I slowly opened my mouth and poked my tongue out for her. "Ohhhh Brie, that is so cute. Let me get some video of this," she giggled, lifting her phone up to record my ultimate humiliation. Lifting the panties up so that I could see them she laid down next to me, snuggling against me. "Look at all the sissy cream honey, Brie was very backed up wasn?t she?" Keeping my mouth open and my tongue out I slowly nodded my head as she brought the panties down to my face. I was watching the last of my manhood slip away, after this what was I? As the first glob of the now cold semen landed on my tongue I jerked a little. The thick strand slid down my tongue into my open mouth. I could taste the salty, slightly bitter flavor. Karen smiled as she watched me swallow this first bit, then she placed the panties in my mouth, tucking them down deeply with her finger. "I?m going to clean up a bit while you suck all of your sissy juice out of my panties honey, smile for the camera!" Which was followed by a flash and her spinning away humming some ambiguously happy tune to herself. Watching her skip away all I could do was remain trussed up in bed tasting my own seed. Continuing to cry tears of humiliation I began to work and poke the panties around with my tongue, soaking them with my saliva and washing the cold cum out of the delicate fabric. As I continued to clean the soiled panties with my mouth something began stirring down below. How could I be getting excited while doing this I thought in exasperation, but here I was, my little clittie trying it?s best to get hard inside the cage while I was eating my own squirt. Was I enjoying this, was I turned on by eating cum or was this all just a reaction to so much stimulus today. My thoughts were interrupted by Karen returning to the bedroom. She had removed her makeup and was wearing a cute satin and lace camisole and boy short set in dark blue. I was stunned by how pretty she was, she once again looked like my sweet, loving wife. With a bouncy, happy gait she approached the bed and hopped up on it snuggling in next to me. "Honey, I want to undo your legs because I don?t want you to get too sore, do you promise to be a well behaved sissy if I do?" she asked me while shifting so she was kneeling by my head. I responded with a vigorous nod of my head. Okay, I am going to do this slowly and I will help support your leg so it doesn?t just drop, here we go." As Karen unclipped the strap from my collar she slowly allowed my leg to lower to the bed and did the same with my other leg the relief was immense, it felt so good to be able to lower my legs. She began gently massaging my leg starting at my thighs and working down. "Try to relax, I know that it is hard honey. It?s your fault that your poor little legs had to stay bound up for so long, I didn?t want to have to do that but you were being a naughty sissy weren?t you?" she said while continuing to rub my legs. "Have you cleaned out all the sissy cream from my panties?" "Yemff ma?aaamm," I tried to say around her panties that were still deep in my mouth while nodding my head. "Good, then let's get those out and see," Reaching up, she removed the panties and held them up for inspection. "Good girl!" she told me while giving me a kiss on the cheek. "Brie, I have a question for you, was eating cum really all that bad? You didn?t die from it, I don?t think it made you sick, girls eat cum all the time and don?t have issues, was it worth that temper tantrum and the suffering you had to endure because of it? Be honest with me?" she said while lightly dragging her finger across my abdomen, tracing out some abstract pattern. I was still trying to figure out why I had gotten sexually excited after she made me take the cum drenched panties into my mouth, and her question just made that more confusing to me. Laying with her next to me, gently touching me, the love and care she had shown when releasing my legs, my earlier actions did seem silly to me. "No ma?am, I don?t think it was that bad. I?m sorry for behaving so poorly. I promise it won?t happen again," I replied, my voice a little shaky. "Ma?am, I know I acted very ugly, will I have to be punished for that?" I didn?t want to be punished but I also wanted to know. I was so scared of making her mad by doing something so dumb. "No, I understand that this is a little confusing to you right now. I don?t think that you need to be punished, being tied up a little longer was plenty. We have both had a very long day, what do you say about trying to get some sleep?" With that she slid up behind me, wrapping her arms around my waist and spooning up against me. My hands were still bound up by my collar but that wasn?t so uncomfortable and I decided it was best not to mention it. If my wife had wanted to unlock me she would have. As I felt Karen relax, drifting off to sleep I continued to replay the events of the past twenty-four hours in my mind. It had been an incredible day. I had spent it with the woman I loved, she had let me hold her purse the entire time, I had been the center of attention and thought at times it was terrifying, looking back I had been sexually charged the entire time. I could?t stop thinking about how she had made me orgasm by penetrating me, and how different it had been. Not an abrupt, violent release but a slow, monumental growing of the most sensual and sustained feeling I had ever experienced. These were the thoughts that were bouncing around in my head when I finally closed my eyes. The next morning light streamed in from the partially open blinds and played across the room pulling me out of my slumber. I could feel Karen, still snuggled up against me, her hand had drifted down towards my cage, the soft sounds of her peaceful breathing paired with the warmth of her breath on the back of my neck were heavenly. Staying perfectly still so as to not wake her I just enjoyed our closeness, the warmth of her body against mine, her smooth bare legs against my garters and hose. "Mmmmm, morning honey," Karen said in a sleepy voice, stretching her arms out like a cat waking up from a long nap. "Did you sleep well baby?" "Yes ma?am, I did. I?m sorry that I didn?t wake up early and start coffee..." I started to say. "Shhhhhh, no honey, how could you have started the coffee with your hands at you neck silly?" she giggled, rolling me over and pouncing up, straddling me at the waist then leaning over for a quick good morning kiss, just a peck on the lips. "I was thinking that before we get cleaned up for the day you could give your wife a little treat," Karen was talking while pulling off her dark blue boy short panties and edging up towards the headboard. Looking down at me with a smile she lifted herself up, scooted forward, lowering her temple onto my lips. "This may be the best way in the world to wake up.? I thought to myself as I gave my wonderful wife her morning orgasm. "Oh my goodness sissy, you probably don?t realize this but you?re the absolute best at making me happy down there with your mouth. I swear girl, you have skills," she giggled playfully. "Now let's get you freed up and ready for the day, we have a lot to do!" Unlocked and free, with even the cuffs and collar removed I felt wonderful. A quick shower and I felt even better! Bouncing into the bedroom after brushing my teeth I saw that Karen had laid out clothes for me on the bed, not surprisingly there was a light pink babydoll nighty and a matching pair of the firm control panties, I was very careful to tuck my cage and to put the large overnight maxi-pad where it would catch any dribbles from my leaking clittie. After a careful inspection in the full length dressing mirror I headed downstairs. We shared a nice breakfast with coffee, greek yogurt, fresh fruit, and a half of a bagel each and the conversation was very light. Karen would occasionally slide her foot against my leg under the table and gently rub up my leg, even going as high as my crotch once. This brought on a little moan of excitement from me and a smile from her. Finishing up with our meal I automatically began to clear the dishes and clean up everything. Relaxing at the breakfast nook table, taking a sip of coffee Karen smiled, watching me clean up the kitchen. "Sissy, you are a sexy little thing zipping all around, cleaning, wearing your cute little nightie." Pausing to turn and smile at her I replied, "Thank you ma?am." "Honey, when you get done with cleaning up after breakfast would you come into the den?" "Yes ma?am, I will only be a little while longer," I replied, wondering in the back of my mind what was going to happen, still remembering her telling me earlier this morning that we had a lot to do. I don?t know if I was worried, scared, or excited," Finishing quickly I hurried into the den to see Karen sitting on the couch with my new purse and wallet on the coffee table. "Honey, would you please kneel in front of the table, we need to have a quick talk and I want you to be able to see what I am doing and I want your full attention," she said while reaching over and pulling what I recognized as my wallet and phone out of her purse, I must have left them in there from our shopping trip yesterday. Quickly I knelt down on the other side of the table from her, looking at the very pretty patent pink large shopper Dooney & Bourke purse and matching wallet that I had bought for myself yesterday. Pulling out all the contents of my dark brown leather wallet Karen looked me in the eyes, "Sissy, I want you to throw this nasty boy wallet in the trash right now, do you understand?" "Yes ma?am," I said while rising to my feet, taking my old wallet and going to the kitchen. Tossing the wallet into the trash I paused looking at it on the pile of refuse, as I was about to close the lid the significance of what Karen was having me do struck me. I would not be allowed a boys wallet any longer, this was real, not a game. As the garbage pail lid shut so did the door to my masculinity. Afraid to take too much time to ponder this I rushed back into the den and kneeled in my designate place. "Watch me, don?t take your eyes off of what I am doing," Karen told me as she began to load my new wallet with my license, cards, photos, and money. The significance of what she was doing and how she was doing it was not lost on me. She inserted each item into the shiny pink wallet with a flourish, when the task was complete she closed the wallet and held it out towards me. "You may kiss your new wallet and thank me sissy," she told me. Leaning over I pressed my lips against the wallet. "Thank you Mrs. Karen." Next she lifted up my phone, removing the slightly worn black protective case she lifted up another case, a pink one with glitter. Fitting it around my phone she turned the back so I could see the word ?Sissy? written in bold script letters across the back in silver. Karen sat the phone next to my wallet. "Sissy, would you like to help put all the necessities in your new purse?" she asked while smiling broadly at me. To be honest I was transfixed by what was occurring. Though yesterday I knew I was buying this purse for myself the magnitude of what I was committing too didn?t occur to me. Here I was, kneeling in front of my wife, as we changed out my old masculine every day stuff to my new feminine every day purse. This wasn?t just play time anymore, this is what my life was changing too. Looking up at my wife, sitting comfortably on our overstuffed leather sofa, from my kneeling position I quietly answered her. "Yes ma?am." "Good sweetie I am glad that you understand, now be a dove and run to the spare bedroom and bring me the green bag please." I quickly hopped up and headed upstairs, as I reached the third step, my satin teddy bouncing as I ran, I heard my wife yell out from the den, "Nice Ass!" Pausing I gave her a little wiggle of my behind and a flip of my teddy and then took off up the stairs. Finding the large green shopping bag from upstairs I rushed back to her and once again knelt in my spot, placing the bag on the low table. "You are doing very well this morning Sissy, I am proud of you. Would you like to come sit next to me while we do the rest, I believe that you comprehend what all of this means, there is no going back for you my pretty little pet," she said while patting the couch next to her. In an instant I jumped up and sat next to her, I would never turn down the chance to be next to my lovely wife. First she removed what looked like a large clear makeup bag with a zipper top. Opening it she removed the tissue that had been in it and she set it down in front of me. Now she pulled out a full bag of Always overnight maxi-pads, a box of Tampax heavy flow tampons, and a small tube of KY Jelly. "This is going to be your daily needs bag honey, I want you to fit as many pads in here as you can and at least three tampons and your lube," she said while sliding the items towards me on the table. Almost in a trance I picked up the box of tampons, why tampons? How could I possibly need tampons? Opening them I saw that they were larger in diameter than any I had seen her use. Lifting one up I examined it, in its pretty purple, green, and white wrapper, I could feel the thick end where I knew the cotton absorbent head was, then the slender tube applicator and at last the string. Nervously I removed four of tampons and placed them into the clear bag. Now I understood why Karen had chosen clear, to intensify the humiliation of having them in my purse. If I took the pouch out everyone could easily see what I was carrying. I was able to fit in six of the thick maxi-pads and still have room for the tube of KY. "Good Girl, now set that next to your pretty wallet and phone," Karen instructed me. Next she laid out some slightly more mundane things, two nail files, a small bottle of hand sanitizer, a travel pack of baby wipes, a purse pack of tissues and two large puffy scrunci hair ties, one in pink and one in purple, both adorned with bows. To my complete surprise the next item that came out of the bag was a translucent pink dildo, complete with a set of balls and veins running the length of the shaft. When my eyes got wide Karen burst out in laughter. "Oh yes sweetie, every girl needs a little relief every now and then, yes, that will go in your purse so you will always have it with you. Here is a nice clear baggie to keep it in," she said while handing me another clear makeup style bag but this one had a slide seal zipper at the top. Reluctantly I took it from her, blushing a bright red. "Okay, you may now put all of your items in your purse. Do you notice anything that?s missing?" she asked, tilting her head to the side inquisitively. "Yes ma?am, I think you usually have some makeup like lipstick and gloss in your bag," I replied hoping that I was right and that my attentiveness would be well received. Clapping her hands together in glee she bounced up and down on the couch, "Yes! Exactly! You are such a smart sissy. So, are you ready for a surprise?" "Yes ma?am," I answered, trying to sound exciting but at the same time dreading what she had in mind. "Well, the department store called and your makeup is ready for pickup! But wait, there?s more, they have a hair salon in store and can work you in right before lunch so we need to dress and get a move on! Isn?t that wonderful?" With that she got up off the couch and told me to follow her up to the bedroom so we could get dressed together. We were up the stairs in a flurry! Karen was almost dragging me to the bedroom in her excitement. "Sissy, I am going to give you a choice, enjoy this because it is not going to happen often. You can wear one of your work outfits or I can pick something out more casual and fun but you are going to look pretty either way. What?s it going to be?" I started out thinking which would be less embarrassing for me but somewhere my train of thought became derailed and I actual began to wonder which would look the prettiest. The choice didn?t seem completely fair to me since I really didn?t know what I would be wearing in either situation. We had purchased so many clothes at several different shops and I also knew that Karen had bought some that I hadn?t tried on because she thought they were cute and we could return them if they didn?t fit. Timidly I answered, "Something more casual ma?am." "Interesting Sissy, it took you a while to decide that, what made you choose casual over work clothes?" Karen asked. "Mrs. Karen, at first I was trying to decide which would be less embarrassing for me but..." I paused for a second gathering my thoughts. "But then I thought about what would look pretty and since we were going out and you would be dressed casual and fun I wanted to do the same." It all came out in a rush, words tumbling over each other. There was an instant smile as she hopped up off the bed and gave me a huge hug. "I am so proud of you honey, isn?t it easy when you?re just honest with yourself? Let go, be my sweet sissy, be my Brie, my dove. I love you so much, always remember that, you promise. Even when I have to be a little firm or you think I am being mean please always remember that I love you so much that I would do anything for you." "Yes ma?am, I understand and I love you too. Thank you for helping me, I can say this now because we are in the safety of our house but you are right. I am a sissy and I love the control and the pretty things you are doing to me. I know that I will become scared when it is actually forced on me, the humiliation is real and it is terrifying but even that excites me. I wish I could just accept it and not be so embarrassed all the time," I told her. With a giggle, Karen let me go, held me at arms length and said, "Well, if it wasn?t humiliating for you I just don?t think it would be as much fun for me, I for one enjoy seeing you in the most embarrassing situations! Now let's pick out some clothes for today." Karen was wearing a short, loose skirt in a pretty blue pattern with a lacy, square neck, white top and a pair of flat strappy sandals. It was incredibly cute on her and I was excited to see it paired with her new fun summer purse. I became nervous as she deliberated on what I would be wearing. She ended up settling on a pair of very tight white jeans matched with a thin, off center cowl neck top in an eggplant color. I was conflicted on whether or not I would feel better leaving my bra and breast forms in place but in the end the choice was not mine to make. Karen said that none of my tops would fit correctly with a flat chest and that sissies should always wear a bra. I was given the strand of pearls that she had worn last night, and a set of shiny silver and gold bangles for my wrist. The part that made me most nervous were the shoes. Karen had selected a pair of pink wedge sandals with three inch heels. "Mrs. Karen ma?am, is it okay if I ask a question?" "Yes, what is it," she replied. "Why heels ma?am, you are wearing flats?" I asked. "Three reasons, first I want you to start getting use to heels before you have to spend all day tomorrow wearing them for work. This will give you time to adjust and I can coach you a bit. Secondly I think that the wedge heels will look cute with this outfit and give it a splash of color and sassiness. Thirdly, I like the way your ass looks when you wear heels, the way you wiggle and shake and this is mostly for my amusement anyway. Any more questions?" "No ma?am." As I finished dressing I stood gazing into the mirror, the image I saw looked alien to me. A slim young woman wearing tight white pants, a feminine blouse, heels, and jewelry. Even without makeup I didn?t think anyone would mistake me for a man, but would I be seen as a woman. I was almost wishing that Mrs. Karen would tell me she wanted me to put on makeup, in a way that would be another layer of comfort. I almost asked her but chickened out. As I contemplated the upcoming humiliations I would be forced to endure my wife came up behind me and wrapped her arms around my waist. "Mmmmm somebody looks sexy in their heels and tight pants don?t they?" she asked, not really wanting an answer, just more of a statement. She handed me both her purse and mine and ushered me to her car. Her car, oh shit! Last time we drove an hour away, this time we were going to the mall that was only five miles from our house, it was much more likely we would run into someone we knew. Now I was really nervous. Once again I was wrapped in the comfort of the luxury SUV?s leather seats, heading out into public but now my clothing was not even close to androgynous. Nervously I tried to make conversation so that Karen wouldn?t get upset with me, fidgeting constantly with the straps of the handbags in my lap. "Honey, calm down just a little bit, you are about to squirm out of your seat over there. Is someone a little nervous?" Karen said, giving me a sideways glance and a smile. "I do appreciate that you are trying to keep up pleasant conversation and not being all grumpy like yesterday morning." "Sorry Mrs. Karen, I am trying. It is just that, well....we are so close to home this time, what happens if someone we knows sees us?" I answered her nervously. "Hmm, if it is one of my girlfriends I think that it would be proper for you to get on your knees, kiss the toes of her shoes and ask if she would be so kind as to let you cary her purse for her," Karen stated, this time without the soft smile, she was serious, my stomach did a flip just imagining having to do what she described. How could I do that? What would everyone in the mall think? I would look like a total freak!" For the first time I realized that today could be way worse than yesterday, that I could be exposed to the whole world as a sissy. I began to sweat, and to fidget even more but even more disturbing my clittie was trying to get hard in its cage again. Why would this make me excited down there? This was the worst thing that could happen, if one person we knew saw us I would be ruined, and if it was a woman I would be forced to submit to her. I knew that Mrs. Karen did not make idle threats, if we saw one of her friends I would have to comply with her orders, oh shit. My heart was racing and I was beginning to hyperventilate. "Brie, stop getting yourself worked up right this minute! You are over reacting once again and I swear if I have to pull over you will be sorry!" my wife told me in a loud demanding voice. Closing my eyes I concentrated on breathing, slowly inhaling through my nose and exhaling from my mouth. Little by little I could feel my heart rate begin to slow until it no longer felt like it was coming out of my chest. I kept thinking to myself, ?calm down or it is going to get much worse.? As I felt the vehicle slow and turn I opened my eyes to see us pulling into the parking deck and driving to the lower level. Karen maneuvered into a parking spot near the front of the West end anchor store. Removing her seatbelt and turning to face me I saw that her face bore a deadly serious expression. "Have you gathered yourself Brie?" she asked. "Yes ma?am," I whispered, so quietly it was barely audible, my eyes cast downwards. "Look at me Brie." I lifted my head up, determined not to cry this time. I still could not meet her eyes, instead I focused on her lips, which were pursed into a thin line. "Before we get out of the car let's talk," Karen spoke to me in a slightly kinder voice, not as harsh as earlier. "We have got to work through this honey. Can you look at me please, I want to see that you are hearing and understanding my words." Not trusting myself to speak I stayed silent but adjusted my eyes so I was looking directly at her. This was difficult and I could feel my lower lip begin to tremble. "Brie, I am going to ask you some questions and I want quick, honest answers. Do you see yourself as a man?" "No ma?am." "Haven?t we both confirmed that you are in fact a sissy?" "Yes ma?am." "Whose sissy are you?" "Yours, I am Mrs. Karen?s sissy ma?am." "Now, I want you to think about this for a second before answering and I want you to be honest with yourself. Do you expect me, who has such a delightful sissy who is willing to endure anything for me and wants nothing more than to serve me, to keep you secret, hidden away from everyone? Is it even possible for me to hide you? I intend to utilize my sissy in every way possible. Hell, you are even going to be a sissy at work! Don?t you think that sooner or later everyone is going to know? Why would you want to hide what you are?" Unable to maintain eye contact I dropped my gaze, looking at the pretty Dooney purses in my lap. The questions that she was asking me seemed so reasonable when they were broken down like that. I came to the realization that I wasn?t freaking out about my new work wardrobe because wearing women?s clothes to the office was not right in front of me at the moment. My mind was only processing what the immediate threat to my non-existent ego was, I couldn?t move past what was right in front of me. Reflecting on what Mrs. Karen was asking me I started to respond but my voice broke into a squeak. Taking a breath I tried again. "No ma?am, you are right. I know that it won?t remain a secret forever," With a sniffle I tried to raise my face up and meet her gaze. "I?m ashamed of what I am." "Now we are getting somewhere!" Karen exclaimed. "Yes, you should be ashamed of what you are!" Her words hit me like a load of bricks, ?I should be ashamed!? With my eyes still downcast in a trembling voice I responded, "I am a shameful worthless sissy." "No, you are getting this wrong honey," she replied using her hand to force my face up so she could see my eyes. "Yes, you're a sissy so it?s only natural that you should be ashamed, that is part of being a sissy sweetie. Sissy?s are creatures that are wrapped in shame, they don?t choose to dress like sissy?s they are told to by their master or mistress. The only choice that a sissy has it whether to stay and submit or leave and be free, because they willingly stay and submit they are shameful. They choose to submit and are therefore ashamed of themselves for doing so, but it is the same shame that they embrace and are so excited by." "To be honest honey I believe it is just the way you are wired. Now let me go ahead and answer the next silly question that you are going to ask me. How can I love you if you are a sissy? Am I right, is that what you were thinking?" Karen asked me. I just nodded, she was so far ahead of me mentally. "Don?t you remember me telling you this morning how much I love you? How many times do I have to go over this with you honey, I love you because of who and what you are. At least find some confidence and strength in that. No matter where this path leads us I promise that you have my love, forever," Sealing those words with a kiss she got out of the car, not giving me time to respond. Taking only a few seconds to ponder her words, I gathered my strength and got out of the car. Karen had waited for me and we walked into the store together. I began to realize that with it being before lunch on Sunday that the store was not busy at all, some of the shops in the mall were not even open yet, this did a lot to settle my nerves though I knew my wife was right when she said there was no way my being a sissy could be hidden forever. We walked through the quiet department store towards the back where the salon was. Until now I had not even thought much about the fact we were going to a hair salon. I looked over at Karen and almost asked what she had planned but thought better of it, sliding the four purse straps higher up onto my shoulder I continued to silently keep pace with her. The salon was a bit busier than the rest of the store and there were several ladies either waiting or already sitting in chairs getting various things done with their hair. Karen had me sit in one of the chairs at the front of the salon while she spoke with the receptionist. I couldn?t help but notice that several of the women were looking at me. Did they know I was a sissy or was it because I was sitting with two purses in my lap? I just looked down at my feet, yet again noticing how absolutely ridiculous my plain toes looked in the pink wedge heeled sandals, even sillier than when I was wearing the plain brown flat ones. "Brie?" I heard an unfamiliar voice say snapping me out of my daydreams about toe polish. Looking up I saw a pretty, middle aged lady who was wearing a black smock with the name ?Ella? embroidered in pink script on the left chest and on the other side in silver embroidery was the name of the salon. "Yes ma?am," I answered her. "Can you come back this way with me please," she told me while looking me up and down closely. I got up and followed her to a white salon chair by a wash basin and sat down as requested. "Okay Brie, I have been talking with your wife and to be honest until I looked very closely I didn?t believe her when she told me you were a boy...." the lady told me, but was interrupted by my wife clearing her throat. "Sorry, not a boy, but a sissy," Ella corrected herself. "Anyway, after consulting with your wife she has decided that she wants to keep your hair long but wants it to be more styled so let's have a look ok baby." Ella was walking around me slowly, turning my head with her hands, even running her fingers in my hair. "My word! You have amazing, thick, healthy hair sugar, some split ends and a bit rag tag but wow!" Turning to my wife she continued. "He is too cute to do anything harsh, I would really like to keep the length, I totally agree with you on that. I kinda picture a little bit of a messy, tousled look, a little layering, highlighting will be a must. You could style it using just a blow drier with a diffuser and a round brush and it would look awesome in a half up half down style too so it would be versatile." Moving her hands through the front of my hair and watching it fall she continued her thoughts. "Side part or a gentle wave would be gorgeous and would frame this beautiful face. If you don?t mind my asking, does she ever wear makeup. With those lips and eyes and face structure, holy shit!" Karen smiled broadly. "You have no idea how beautiful my little sissy is when she is wearing makeup." And then she pulled her phone out of her purse and held it up for Ella. "Wow!" was the response from my hairdresser. "Sugar, don?t take this the wrong way but you should have been a woman. I?m still not convinced that you have a thingie!" she said, giggling about the last part. Karen piped up, "Yes, she does have a ?thingie? but it is tiny, so small and pretty just like her. It is also safely locked away in a chastity cage because if there is one thing that a sissy cannot be trusted about it their little clitties, always wanting to get tiny little hard ons and constantly getting excited and masturbating, leaving nasty tissues all over the place." I could have crawled under a rock and died. Both women, as well as a hairdresser and her customer sitting next to us were laughing at me. Why did Mrs. Karen have to tell her all that and embarrass me so much. Just then, I realized that that is exactly what I wanted her to do, because I was a sissy and I needed to be shamed. Summoning up all of my courage I managed a smile and looking at my wife and Ella said. "Thank you Mrs. Karen ma?am for helping me be a better sissy for you." With her mouth in a pretty ?O? shape, surprised by my words Mrs. Karen patted my head. "Oh Brie, you are such a brave little sissy today, thank you for being honest with yourself. Now let's get you looking pretty!" Mrs. Ella went to work, first securing a black cape with pink trim around my neck and then leaning the chair back so my hair fell into the wash basin. I closed my eyes, throughly enjoying the hair wash, her fingers massaging my scalp, the pretty scent of the shampoo. I was a little sad when it was over and I was told to get up and move to her stylist work area. This was a taller chair that she could raise and lower with a foot pedal. For a good half hour she worked with her scissors and comb, clipping, then preening my hair. When she would lean over her breast would press up against me making my clittie excited, once even she pressed her side into my breast form. It felt weird, like an indirect pressure and for a fleeting second I wondered what that would have felt like if I had real breasts. With a flourish Ella put her scissors up and declared the haircut complete and a total success! "Now let's work in some highlights, primarily in the front but I am going to mix them in allover to give you a cute, sun kissed look." With that she began misting my hair with water. "Your hair dried out while I was cutting it, the coloring for the highlights will do better if your hair is a bit damper sugar." After mixing up a paste she began to apply it to sections of my hair using a brush and what seemed to be thin sheets of foil that were wrapped around my hair after she was done with the application. True to her word she started at the front and worked back, doing several layers of my hair. When she was done Ella set a timer and Karen set the purses back in my lap as the two ladies stepped off to the side to talk. Ella returned right before the timer dinged and ushered me back over to the wash basin chair. Next the foil wrappings were removed and she leaned the chair back and applied something she told me was toner to my hair. Rinsing that out she shampooed my hair again, I was excited about that because it felt wonderful, then she conditioned it. After all of that I was once again told to go back to her stylist chair. I had no idea that there was so much involved when women got haircuts. I made a mental note to apologize to my wife for ever questioning how much her visits to the salon cost. "Alright sugar, not much more now. I am just going to dry and style your hair now," she told me. Looking over at my wife she added, "Karen honey, you might want to watch so you can help her till she gets the hang of this." Karen smiled. "Mmmmm sounds delicious, just think Brie, how you can work to repay me for styling your hair in the morning, whatever shall I have you do?" she said and instantly both women burst into laughter. When Ella was finished she twirled my chair around and removed the cape. I was looking into a huge mirror at a very pretty young woman with no makeup on. With the highlights my hair appeared lighter over all, with the front landing somewhere between light brown and dirty blond with well blended light streaks. It was styled with a feathered swoop that went from the left side to the right and strands of hair fell over the right side of my face, even to where the outside corner of my eye started. Unlike how I usually wore my hair when loose, it was now pulled forward so it draped over the front of my shoulders some. Overall it did have a tousled natural look. Holy shit, I was almost beautiful I thought to myself as I continued ogling at my reflection. "Oh Ella, she is beautiful, you did a wonderful job, thank you so much!" Karen said while handing her a credit card for payment. "Any time sugar, consider me Brie?s personal hair dresser for now on. If you don?t mind me adding this, she really needs to do something with her nails as well. The poor girl keeps looking down at her toes, I bet she is trying to decide what color her nails should be." This elicited yet another round of giggles but Karen did respond, "Yes I agree." Walking back into the department store from the salon area Karen wrapped her fingers in mine, holding hands we proceeded to the makeup counter. With very little fuss we picked up a large bag that had been set aside and payed for it. The sales lady noted that Tony, the lead makeup artist at the Northside store had authorized his employee discount to be used and sent his regrets that he couldn?t make it in person. I blushed again, thinking of how considerate he was. With a huge sense of relief I thought that we were done and would be heading for the car but when we got to housewares Karen took a left turn, in the direction of the department store entrance to the mall. "Mrs. Karen ma?am, where are we going now?" I asked while trying to keep up with her. "I think that you need more walking practice in your heels sissy, I want you to go ahead of me a bit so I can observe from behind," she told me. Ever the obedient sissy I began to walk in front of her, I could almost feel her gaze boring into my backside. I continued walking until I heard her call my name from behind telling me to stop and wait for her. "Okay, now I am going to go sit and I want you to walk from the store entrance to the Ulta store entrance a few times so I can see you from the side." "Yes ma?am," I said, watching her go take a seat on a bench to the side. I walked back and forth three times and was beginning to feel a little bit of a burn in my calves by the time she told me to stop. "Not too bad honey but I have some pointers that I want you to incorporate. First you need to stand up a little straighter, shoulders back, poke those pretty breasts out a bit. Try to improve your posture and feel your core supporting you. We will start doing some exercises to help that, maybe a little yoga. Take smaller steps, a bit more heel to toe but when you step down put pressure on the ball of your foot first, just a little before your heel touches. That is going to be something you will have to concentrate on. In your old boy shoes you usually put weight on the heel first. Most importantly loosen up your hips a bit, you?re a sissy, it?s okay to shake that thing a bit for your wife. Now let's try it again. She told me with a pat to my butt for encouragement. Once again I walked the route from store front to store front while she watched. Remembering everything she said I could feel my hips swaying more. My walk just felt sexier then before. I was also very happy that I was in the wider wedge heels, some of the ones that we had purchased had incredibly narrow heels. On the fifth pass Karen stood up and told me that I was doing better and she turned me back towards the department store. "Let?s get you home now sissy, you need to tidy up the house and put away your makeup," she said. With a sigh of relief and a little more sway in my walk I accompanied my beautiful wife to the car.

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3 years ago
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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
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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
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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
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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...

1 year ago
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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
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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
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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...

2 years ago
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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
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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
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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
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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
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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
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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
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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
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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,...

3 years ago
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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...

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