The Looking Glass Sissy - Part 1 free porn video

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. The Looking Glass Sissy - Part 1 Watching the flickering screen as the beautiful sissy danced in a tight wiggling motion I reached down to rub myself through the old worn panties I had found a couple of years ago in the laundromat where someone had left them in the dryer. As the sissy twirled and jiggled I began to rub faster and harder until unable to stand the tension anymore I moved my hand to quickly pull the front of the threadbare panties down so I could begin jacking off for real, desperately needing an orgasm. There was a sickening sound of fabric ripping, looking down I saw that in my haste I had torn the old blue cotton panties. Unable to stop now I grasped my dick and began pumping while returning my focus to the dance on the computer screen. It was only a matter of a few seconds before I had to reach for a tissue to capture the eminent eruption. Quickly covering the head with the thin white paper just in time to capture the spurting cum I leaned back in my chair, giving a couple more pumps to take me completely over the top. With a heavy sigh I turned off the computer, looking down at the torn panties and the white cream that escaped the poorly placed tissue in disgust. 'Why did I do this?' I thought to myself, what perversion makes me want to wear women's underwear. I always felt this way after a climax, I would be 'normal' for a day or two and then the urges would begin to gnaw at me until the need would be too great and no longer suppressible. With my libido at its lowest point, and generally disgusted with myself, I nonchalantly threw the ripped panties in the garbage, swearing off my perversion. So, that is why I now found myself sitting in my car outside of the mall trying to build up the courage to buy a new pair of panties, and maybe even a bra if I could ever bring myself to get out of the car. I had chosen a place that was an hour away from home, and it was ten in the morning on a Tuesday so hopefully there would be fewer shoppers. I already had my story arranged in my head, 'I was out running some errands and my girlfriend had texted me saying that she needed me to get her some new underwear.' It sounded simple enough. I had an idea of the size panties I would need but didn't really understand bra sizing. I was hoping I could just casually look and make an educated guess. This was nerve wracking. If I hadn't torn the panties, if I'd been a little more careful. Or if I wasn't a perverted weirdo, this wouldn't be happening. For a half hour I sat in the car unable to make myself walk into the mall, then an idea struck me. What if I picked a small store, where I didn't have to go around a lot of people. It might cost more but that was worth it. Pulling out my phone I began to search for a women's boutiques that also sold lingerie. Bingo! Looking Glass Ladies Boutique showed up in my search, it was about fifteen miles back towards home. 'For the discriminating young lady,' was their motto saying that they had fashion for the younger lady, not to expect the standard 'stuffy' boutique experience. Pulling out of the mall parking lot, very relieved that I would not have to walk amongst so many people with a bag from a women's store I drove towards my new shopping adventure feeling a little bit better about being able to actually do this. My erotic need was so strong, I needed to find some undies so badly. Turning down the street the shop was located on it was definitely different from what I had imagined. I had thought that it would be in a small, maybe even run down strip mall but it was in a pretty downtown area that looked very well maintained with shops and restaurants lining the narrow street. All of the buildings where older brick shops that look to have been restored and the wide sidewalks were lined with flowers and there were several areas where small tables, resting under the shade of green canvas umbrellas could be seen grouped together for outdoor seating at the many small cafes. Finding a parking spot on the street not far from where the GPS indicated the shop would be was easy as it was only eleven in the morning and it was not that busy. I needed to hurry because I could picture this place as a bustling area for lunch with all of the places to eat. Not giving myself a chance to develop cold feet I opened my car door and started walking. The shop was a brick two story building with large framed glass windows, each having a dark green painted flower box on the sill overflowing with pink and purple snap dragon's. The sign over the door was in pink, written in broad script letters, 'The Looking Glass.' Pushing on the door I was immediately greeted by a soft ringing sound, looking up I saw a small brass bell mounted above the door with a thin spring steel bar that was activated by the door swinging open. The inside was cool, and the decor was soft with neutral colored wall paper and beige carpet. The clothes were displayed neatly on racks and the smell was intoxicating. I had never given much thought to smells being erotic but the air was laden with the most delicate feminine fragrance. It was a struggle to not get an erection and I was about to bolt, to turn and run back out the door but then there was a voice. "May I help you sir?" came a soft voice from one of the prettiest women I had ever seen. She was about my age, maybe younger, say early twenties. Her long brown hair was pulled back into a loose bun and held in place by a wide tortoise shell colored barrette. She wore a soft, silk sleeveless blouse in a light beige, a long, pleated maxi skirt in an almost rust color with light beige heels. Just her tone and her voice alone were beautiful, there was something so captivating about her. I was standing there staring like an idiot unable to speak. "Sir, is everything alright? May I help you with anything?" she repeated in her soft but clear voice while taking a small step towards me. "Oh, I am sorry ma'am," I said blushing and looking past her towards the lingerie display. "This is really embarrassing but my girlfriend needs me to pick up some clothes for her," I stuttered in a squeaky voice. "Of course, but that is a hard thing for someone else to do, pick out clothes for a woman I mean," she replied. "What are you looking for?" "Ahhhhmmm, I need...She needs I mean! She asked me to pick her up some underwear, you know a pair of panties and...well, and a bra too," Shit, this was harder than I expected. Why did the sales lady have to be so pretty. I could feel my face burning, my ears could have been steaming for all I know they felt so hot. "What size do you wear?" she asked with a sly smile on her face then corrected herself as I began to stutter, "Oh, sorry I mean what size does she wear?" I was so flustered and confused, my response was broken and even sounded weak to me, like a lie. "Ummm, she well, she is around an eight I think." With another smile the young woman looked at me from head to toe. "That would be around a twenty-six inch waist with the hips being a bit more, you and your 'girlfriend' must be similar in size." I didn't have an answer for her, not only was she seeing right through my lies but in a very passive aggressive way she was calling me out. I wanted to leave and started to retreat back towards the doors. As I began to turn I felt her take hold of my wrist in a firm grip, I was a little surprised at her speed and strength. "No, please don't leave, I just hate missing a sale and my manager will be quite upset with me if I don't make my quota for the week. Besides," She said while looking directly at my groin where my khaki pants were formed into a very obvious tent from the erection that I had developed in the last few seconds. "It looks like you are enjoying your shopping experience so why run away now mister....?" Though I may have been able to tear away from her grip there was something stronger holding me in place. It was as if she had woven a spell over me and I was trapped like a fly in a spiders web. I was trying to calm myself down, to at lest get my uncooperative member back under control but everything I tried to think of just seemed to make him get harder. "Lets start over," she said. "My name is Alessandra." "Oh, yes ma'am...I am, well...everyone just calls me Sammy," I croaked out, glancing down at her pretty hand that had hold of my wrist. She had on an oversized bangle in a copper color that laid beautifully against her tanned skin. "Ma'am? That is so polite, I like that in a boy. So Sammy, tell me about your girlfriend, what is she like?" I was caught off guard, all I had planned was saying I a girlfriend, I had been on line to figure out what my panty size would be and had decided that my bra size would be close to a 34C or maybe 36C. I hadn't thought of coming up with details for an imaginary girlfriend. I had never had a girlfriend to speak of, never been with a woman, ever. Twenty-two years old and a virgin, how pathetic, I thought to myself. "Sammy, what is your girlfriend like, it will help me pick something out for her or do you already know what color and style she would like?" Alessandra asked while still maintaining her grip on my wrist, leading me towards the back of the store where the intimate's section was. "Ummm, I guess she is real nice, I mean of course she is nice but...maybe you were right, we are probably about the same size. I, well I had never thought of that," I mumbled, being tugged deeper through the maze of beautiful clothes. "No silly, what colors does she like, is she flirty or plain, are these for a gift, something very special, or just underclothes. If you want really plain stuff it is less expensive to go to a department store. We carry nicer things here, lingerie meant for special occasions. Are you and her doing something special? Is that why she sent you to our boutique?" Her barrage of questions seemed never ending and I didn't have answers for any of them. She was staring right at me, looking directly into my eyes. It was so intense that I found myself having to turn away, unable to face her while I tried to come up with my next lie. "You do have a girlfriend don't you Sammy?" she asked in a whisper. "It's okay if you don't and you just want to buy something pretty for yourself." I was shocked to the point of speechlessness. I stood gasping like a fish out of water, I could feel my erection begin to grow even more if that was possible, almost to the point that there was an honest fear of an explosion. Using my free hand to try and hide the shame protruding from my thin khaki pants I continued to stutter as Alessandra leaned in a little closer to me and whispered in my ear. "I think a little boy like you wearing pretty panties would be cute." Slipping out of her grasp I took a tentative step back. My face was red with shame. As she whispered those final words to me it was more than my oversexed mind could take and I exploded into my boxers. I could feel the wetness leaking through my pants with the hand I had covering myself down there. "I'm sorry ma'am, I...I just remembered, I have to go, I am sorry!" I stuttered like a fool, turning and running out of the store almost tripping in my haste. Behind me I heard her sweet voice. "Please come back when you are ready to shop again Sammy." After leaving the shop I ran back to the safety of my car, doing my best to hide the small damp spot at my groin. I was so frustrated that I don't even remember all of the drive home, I couldn't get her last whispered words to me out of my mind, she said that boys wearing panties could be cute.' I was an absolute wreck the next day, all I could think about was Alessandra and lingerie. She was the prettiest girl ever and she actually spoke to me, she knew I was buying girls underwear for myself and didn't throw me out of the store. It was beginning to become difficult to distinguish between what actually occurred and the hundreds of fantasies that I continued to fabricate where she and I were lying in bed together, both only in lingerie doing naughty things. It was on the second night after my experience at 'The Looking Glass' that I made a decision. I had to go back, if nothing else to see Alessandra and apologize to her for running away so rudely. For the past two days I had even abstained from masturbation because it felt like cheating. My mind was mush, I couldn't focus on my work, something had to be done. Those were the last thoughts I had as I drifted into a dream filled sleep. The next morning found me waking up before my alarm clock even went off. It was a combination of nerves, excitement, dread, and joy that swirled around me as I fixed my coffee and a very light breakfast. First I would go for a run to calm my nerves. Running was my favorite exercise and was responsible for me being in pretty good physical shape, even if small. Sliding on my running shorts I glanced at myself in the mirror, my stomach was tight with no flab, my legs were reasonably well muscled, but my upper body strength just wasn't there. No bulging muscles to boast about. My face was unremarkable, maybe a little androgynous, definitely not the epitome of chiseled masculinity. I blamed it on the fact that I had my mothers cute little rounded button nose and full almost cupid bow lips. Returning home sweaty and tired, the clock on the wall showed seven thirty, still plenty of time to shower and get ready. Stepping out of my stinky shorts and t-shirt and walking into the bathroom I turned the shower on hot to begin warming up. Staring at my face in the mirror I rubbed my chin, not really feeling any stubble but deciding to shave just to be safe I pulled the razor and lotion out of the cabinet. After shaving I pulled my fingers across my baby smooth face, dropping my gaze down to my legs, which weren't very hairy to begin with. A stupid thought popped into my mind, 'What would they look like if I shaved them?' Not fully committing to doing it I still carried the razor and shave lotion into the shower with me. As always the hot water falling across my muscles after a hard run felt great. I washed my short blonde hair and after finishing with the bathing portion I picked up the razor and sat staring at it for a few seconds. 'What the hell,' I thought and began to shave my legs, arms, and under arms. As I dried off the sensation was amazing. I had hardly any body hair to begin with but the difference was crazy, every little breeze that wafted across my bare skin made me have goose bumps. It was a nice, almost sexy feeling. Looking in the mirror I was trying to decide if it looked ridiculous but eventually came to the conclusion that even if I was wearing shorts, no one would really notice unless they took a closer look. Today I decided to wear jeans in an effort to not show an erection if that happened again, just thinking of it was humiliating. I also picked a nice black long sleeve silk shirt with a small mandarin style collar, but did not button it all the way to the top. I liked the way it hung on me, loose and flowing and black looked good against my tanned arms and face. I didn't want to do sandals, flip flops or tennis shoes because they looked to dressed down so I picked a pair of black loafers and finished it off with a black belt. If I ever had a chance to go on a date I would have called these 'date clothes,' I thought with a smile. It was just before ten in the morning when I parked a couple of stores down from 'The Looking Glass.' I don't know why but I was afraid to park directly in front, maybe it was just in case I chickened out and didn't go in. Nervously I sat in the car, watching for any activity while staying a bit slumped down in the seat. Some people were having coffee at a cafe adjacent to the store I was staking out but there was no activity or people going into the Looking Glass yet. Noticing some movement inside the shop I sat up a little in the seat. It was Alessandra, she was turning the closed sign to open! There was another woman that she was chatting with who looked a little older but it was hard to tell through the glass of the door at the angle I was viewing her. Just seeing Alessandra again caused my breath to be caught in my throat. The immediate reaction was a bout of nerves, my hands began sweating and shaking. How could I go in and face her after my first visit, that was the second most horrific thing I could imagine. The worst thing that I could imagine was not seeing her again. Taking several calming breaths to settle my shaking body, with no real plan of what I was going to say to her I opened the door and began to walk towards the boutique. Out of the corner of my eye I caught the sight of a small market, the owner just opening, setting bouquets of flowers out on display. In a burst of inspiration I made a sharp left turn, walked across the street, and purchased a beautiful bouquet of white daisies, with sprays of tiny yellow roses. It was incredible and helped give me the mental strength and at least a conversation starting point. I held my breath as I pushed the door open, once again hearing the soft tinkle of the little bell announcing my entry. With my knees actually trembling I was forcing myself not to turn in terror and run away, then I caught a glimpse of movement from the back of the store. Straining to see, my anticipation growing with every step, it was her! Alessandra was walking towards me, almost gliding, moving like a graceful angle. Today she was wearing a cute yellow sundress that stopped at her knees, her long, dark brown hair was partially pulled back in a half up half down style and she wore high heeled sandals of light brown leather with a delicate ankle strap. Her toes were a warm red-brown color and her finger nails had a delicate French tip manicure. She wore several rings on her fingers and one on her right thumb but I was careful to note that she did not have on an engagement or wedding ring. "Sammy, you came back! Are these for me?" she asked in her sweet, soft voice while reaching to take the bouquet of daisies from me. As she did her hands brushed mine and I swear I felt a jolt of electricity, like static shock going through my body. Standing so close to her I could even smell the delicate floral perfume that she was wearing. I tried to meet her eyes but I was too bashful, in a quiet voice I replied, "yes ma'am, these are for you. I just wanted to come by and say that I was sorry for running out of the store on you and being so rude." I didn't know what else to say, though I dreamed of meeting her again I had not been able to work out what should happen or what I should do after apologizing so I just stood their like an idiot. Saving the day she smiled. "Let me get these in some water, they are so beautiful. Come with me Sammy, I don't want you running away again." Like a puppy following his master I trailed after her, embracing her fragrance as it wafted behind her like summer wildflowers caught in an afternoon breeze. For the first time I also noticed that she had a slight accent and reminded me of the way someone from the UK would speak, very proper and educated sounding. What was I thinking, there was no way that this gorgeous girl would ever consider going on a date with the likes of someone like me. "Mrs. Gloria, this is the boy that I spoke about with you," I heard Alessandra say as she turned the corner. Behind the counter was another lady, I suppose she was the manager or owner of the store that Alessandra had referred to the other day. She was older but attractive, standing at around five foot six inches she was a little shorter than the very lithe and leggy Alessandra but still an inch or so taller than I was. Gloria was wearing dark navy pants that had wide legs, a white shell with a navy three quarter sleeve blazer. On her feet were a pair of medium height, kitten heeled pumps in black. Her hair was worn in large waves and went to just below her shoulders and was jet black. She was striking and beautiful, but her appearance was a bit on the 'no nonsense' side. "Hello Sammy," Gloria said to me with a smile that was warmer than I had expected, her accent was a bit more pronounced, it was so beautiful and refined. "Ahmm, Hello Mrs. Gloria," Returning her greeting tentatively, not knowing if I should also be using Mrs. or if I should call her Gloria. "Alessandra told me about the interesting exchange you and her had on Tuesday, did you eventually find the bra and panties you were searching for?" she asked boldly, cutting right to the topic, very no-nonsense indeed. "No ma'am...I, I didn't finish my shopping," I mumbled. Putting her hands on her hips she gave a bit of a huff, "Speak up boy! I detest mumbling and poor posture. I also detest lies, even little ones. Alessandra tells me that she doesn't think you were shopping for your girlfriend and that she believes you made all of that up. Is that true?" Finding it impossible to meet her gaze I glanced over towards Alessandra and found it unusual the she too was not looking at Mrs. Gloria but instead seemingly her eyes were focused on her nails as she fiddled with a set of silver and gold bangles that adorned her wrist. "No ma'am, I don't have a girlfriend, I made that story up," I said, trying my best not to mumble but my voice was still quiet and full of shame. "I see that we need to get down to the bottom of this. Regina!" she called out turning to the back of the store. "Can you manage things for a bit while I sort out a bit of an issue that Alessandra had with a customer?" From the behind a shimmering burgundy curtain came another female voice, "Sure mum, just be a jiffy." "Well, let's go discuss this over a cup of tea instead of standing here where customers may come in and disturb us. Alessandra, please grab my purse from the back when you get yours," Mrs Gloria instructed what I took to be her daughter now. "Yes ma'am," Alessandra responded and quickly darted to the back returning with two bags, an iconic Louis Vuitton "Never Full" in the monogram pattern and a smaller pink quilted Channel bag with a shoulder strap that was matching pink leather woven through the links of a gold chain. I wasn't a women's handbag expert but I knew that both of these were very expensive. Both Alessandra and I followed Mrs. Gloria out of the store and down the street just a short way to a small tea shop. Going past the wrought iron tables with their wooden shafts and dark green canvas umbrellas we ventured into the shop which smelled of tea, honey and pastries. The older lady working behind the counter came out to greet us. "Oh Gloria, it is good to see you so early this morning and you too Alessandra, would you like your usual seat? Where is Regina, minding the shop?" The lady gushed while taking us to a small table that sat next to one of the three large windows facing the sidewalk. "Oh Elizabeth it is so nice to see you, yes, the usual table and tea's, young master Samuel here will take the same as well," Mrs. Gloria responded cheerfully while standing by her seat. Realizing what was expected I quickly stood up, holding first Mrs. Gloria's chair for her, sliding it in as she sat and then going to the other side and doing the same for Alessandra, as she sat in the most ladylike and demure manor, smoothing her skirt as she sat and making sure that her knees were together and her legs slightly angled. "I am sorry ladies, I...well I guess that I am not very cultured," I said with a smile while sitting and following their suite of placing the white linen napkin in my lap. Mrs. Gloria gave me a broad and friendly smile, "You are forgiven Samuel, and I give you credit for reacting to correct your fault and for freely admitting your ignorance." At the reference to my ignorance I looked down in shame, there was no way that she would let me associate with her daughter in any way if I was ignorant, I felt as if this entire discussion was going to be her lecturing me and then dismissing me, forbidding any contact with beautiful Alessandra. Patting me on the hand in a motherly way Mrs. Gloria continued, "I didn't mean to crush you dear, I meant ignorant in the ways of how to properly behave around ladies, which I will add is a rampant problem in your country, though I do love it here and understand that it is proper for people to be less formal. I will insist however, that in dealings with me or my girls you will treat them with the respect that I demand, on that I am unwavering." "Yes ma'am," I agreed with her, nodding my head to emphasize my acquiescence with her statement. "Now, let's not pussyfoot around the topic anymore. You admitted earlier today that you did in fact not have a girlfriend and were lying about that being the reason for needing to purchase lingerie, am I correct? She asked me, shifting her gaze from Alessandra to me. My head bowed in submission and my nerves all bundled up, the humiliation of my answer reflected in the redness of my face I whispered, "Yes ma'am, you are correct. I am sorry." "So then, the next logical point of question is, Who are the panties and bra really for?" she said while taking a sip of tea. Glancing at her daughter, wishing that she was not here so that my humiliation and my fetish would not be exposed to her I saw that Alessandra seemed nervous, shifting and fidgeting in her seat, not drinking her tea. I pondered on how I could answer her question without looking like a pervert or weirdo but everything that came to mind was another transparent lie. Looking up at Mrs. Gloria with tears in my eyes I gave my answer in a quiet voice on the verge of breaking into sobs. "Mrs. Gloria, they....the panties and....and the bra, were for me ma'am. I'm sorry, I shouldn't have lied, and I shouldn't have bothered you at your store. But when I met your daughter I had to come back to see her again. I understand that you don't want me around, I apologize for all this. I have a problem, I just can't seem to help myself ma'am, I'm sorry," Looking at Alessandra I continued. "I am so sorry, I would quit this weirdness for you, I would do anything for you. I know that sounds silly because you don't know me and we have only spoken a couple of times but I promise, I would....I would die for you," Everything came out in a rush, followed by tears and shaking. I was loosing control of myself but I had no more pride, nothing really mattered anymore. With a motherly touch Mrs. Gloria reached out and took my hands in hers across the table. "Sshhhhh little Sammy, try not to cry. Doesn't it feel better to just be honest and to tell the truth, there is no glory in hiding the truth or who you are. I want you to calm down, drink your tea, and we will go from there. We can start with a clean slate as you say, now that we aren't going to have anymore fibs from you." "Yes ma'am," I replied and began to sip my tea. My crying subsiding to sniffles. It was easier to focus on the dainty cup with the cloudy tea and the sweet taste of the cream and sugar. It helped to ease my anxiety. The minutes ticked by as we sipped our tea in silence until Mrs. Gloria spoke again. "Alessandra, I expect you will be the one helping to fit Sam for his lingerie this morning. I believe that seven sets would be the minimum to allow for him to go almost a week with laundry, wouldn't you agree darling?" "Yes ma'am," Alessandra answered her mother, but did I detect a tremor in her voice? Then the enormity of what Mrs. Gloria had just said hit me. Seven bra and panty sets, fitted, enough to go until laundry day? What? I was confused. "Ma'am, I don't understand," I asked quizzically. "I don't believe that there is anything to not understand, if you would like to stand any chance of seeing Alessandra you will stop your lying and at least begin wearing panties. We can move on to address the rest of your issues after that." she told me in a curt voice that left no doubt of her sincerity concerning the topic. I could feel my face turning red again, looking up at Alessandra trying to gauge what she thought of her mothers statement I was met with her eyes diverting down to study her pretty French manicured nails, her tea sitting mostly untouched. I had just been given an ultimatum by her mother. In order to even speak with her daughter I would be required to wear panties. I didn't know what to do. Deep down I knew that I liked wearing panties, and I liked girly things. I usually masturbated while either watching or fantasizing about being a sissy for a beautiful woman but never in my wildest dreams believe that I would be in a situation like this. Was Mrs. Gloria just testing me to see if I would concede to her wishes to be allowed to at least ask her daughter out. My mind was trying to process all of this information, I was so absorbed that I had lost sight of all my surroundings. When I felt someone's hands reach out and take mine I jumped, startled by the human contact, by the warmth and softness of the hands that held mine. Looking up I saw Alessandra's hands wrapped around mine, her large, dark eyes, moist with soft tears looking into my soul. "Sam, I think you would look cute in panties," she whispered to me, breaking down any resistance that I could have mustered. "Mrs. Gloria ma'am, yes I will do that, I will do anything," I said, my voice a little firmer, bolstered by the soft touch of Alessandra's hands on mine. "Lovely, then let us return to the shop and get to know our sweet Sam a little better shall we?" Mrs. Gloria decreed in a happy voice which was met with a chorus of "yes ma'am" from her daughter and I. After returning to "The Looking Glass" I was taken directly back to the intimate apparel section where Alessandra and her older sister Regina oversaw the removal of my jeans and t-shirt. Standing in only my socks and boxers I felt so exposed and embarrassed, mostly I was concentrating on not getting an erection. Regina stepped forward until she was right next to me, running her hands along my arms and then my legs she let out a little laugh, "You are shaved aren't you Sam?" "Yes ma'am, I did it this morning, I don't know why but it seemed right," I admitted, hanging my head, my embarrassment continuing to unfold. Regina looked at her sister and smiled. "Isn't that sweet sister?" she asked. Something seemed a little off but I could understand it, Alessandra was having to measure a boy for women's underwear, that in itself made this a very awkward situation. With kindness and professionalism she wrapped her seamstress tape measure around my waist, hips, and thighs. Calling out measurements which her sister Regina recorded in a little notebook. Blushing she even took a measurement that went between my legs from the front of my waist to the same height on by lower back. Both this and the measurement for the inseam that ran from the inside of my groin to my ankles seemed odd for panty and bra fitting but I did not know much about these things. The measurements for my bra included taking readings at several points around my chest, my shoulders, and my neck. Alessandra also took measurements around my wrists and ankles also saying that they may be useful later and that she wanted to do a thorough job. After being prodded, probed, and measured in ever way I was left alone with Regina while Alessandra began selecting items from shelves and racks. "So Sam," Regina began, "do you see yourself as petite or buxom when it comes to your chest?" Quizzically I responded, "I...I don't know if I understand." "It is quite simple really Sam, mother is going to have you in a bra eventually, do you see your chest as being large or small? In other words, on a woman do you prefer larger or smaller breasts?" Regina asked me. Stuttering, ashamed of any answer that I could give I replied, "I guess it depends on the woman. Every guy likes larger breasts but some women look better with smaller ones. I think it is all about proportions," Blushing I continued, "Your sister is thin, tall and very lithe, she seems to have smaller breast but she is so beautiful." "Well, we have to make a decision, your bra size depends on it." Turning towards Alessandra Regina smiled and said, "thirty-six...double D." Alessandra pulled in a sharp breath and her hands went to her cheeks in what looked like surprise. "Yes ma'am," she said. As the final stack of lingerie was set on the small table next to the dressing room Mrs. Gloria appeared. "Thank you Alessandra, you may go look after the storefront while Regina and I finish here," Gloria told her. The answer was a quick curtsy and my beautiful angle retreated to tend the store. Deep down I was happy about this, I wouldn't have to experience the humiliation of trying on these garments in front of her. Turning her attention to me Mrs. Gloria smiled, "Sam, Have you been cooperating with Regina?" Before I could answer her older daughter spoke up, "Yes mum, little Sammy has been very obedient throughout the entire process with the exception of selecting a cup size. For some reason he continued to give silly non- answers, even involving Alessandra's breast size. I chose double-D for him, I hope it serves as a reminder to be more compliant in the future." Giving her daughter a hug Mrs. Gloria told her how proud she was of her and what a wonderful manager and owner she was going to be. I simply stood silently, in boxers and socks, feeling quite silly the whole time. Turning to me Mrs. Gloria began, "Sam, I am happy to hear that you have been polite about having your measurements taken. We have a few more things to do. I need one more measurement and then we can do a fitting," Pulling out a cloth tape she stretched it out. "Can you please lower your underpants and stand at attention for me." I'm almost sure that my eyes popped out of my head in surprise. I was prepared for having to change into panties but I always assumed that I would do that in one of the dressing rooms. "Ma'am...I mean, I don't..well your a lady and Regina is here too," I stuttered. With shocking speed her hand went straight out, delivering a fierce slap to the side of my face and then to the other. "That is Miss Regina to you Sam! You will always refer to her with the respect she deserves, do I make myself crystal clear?" she hissed at me, her hand now pointing at me, her face flush with anger. I was in shock, I didn't understand what just happened. My cheeks were stinging in pain from her slaps and I was speechless for a bit. All I could manage was a stammering "Yes ma'am, I understand ma'am," Not wanting another series of slaps I began to lower my boxers. To my horror my member was standing at full attention. I had already been aroused having my measurements taken and by the thought of being made to try on panties but it seems that the slap to my face was the final straw and now I had a raging hard on in front of a woman who was beginning to scare the hell out of me. "Ma'am, I am sorry. I can't help it, there has been so much happening this morning. I will try to get this under control," I stammered, red faced and naked save for a pair of black cotton socks. Her warm smile returned, "It is quite alright Sam, actually it is helpful." she said while walking up to me and then kneeling down to eye level with my erect penis. What was going on here? "Sammy," she continued, "I am measuring you for a chastity cage, do you know what that is dear?" I knew exactly what a chastity cage was, I had seen them in so many videos, captions, and illustrations. I had even thought about ordering one. "Yes ma'am," I admitted, the shame visible on my face. Pulling the cloth tape against my erect member Mrs. Gloria read out numbers to Mrs Regina. "Erect length 8.5 cm, erect circumference 10 cm." Instantly both women burst into laughter. I knew that I wasn't big, ever since middle school gym class when I saw other boys parts. Hanging my head in total shame and humiliation I was at least glad that Alessandra wasn't here for this. Regina, trying to speak through her laughter asked her mother, "Mum, is there any reason to even get a limp measurement? I mean really?" "Yes," Mrs. Gloria responded. "It is even more important, something that small could get tiny and slip out of most cages. I am afraid that we must see this little devil in its smaller state. Regina, be a doll and go fetch me the rubber dish gloves and a tissue." "Sure mum, be back in a jiffy," she said, still laughing as she walked away. When Regina returned she first handed her mother a pair of pink dish- washing gloves that came up to just before her elbows. I watched in horror as Mrs. Gloria pulled the gloves onto her hands looking at me the whole time. "Now Sammy, this should not be an unpleasant experience for you if you will just relax. I am going to help you get soft so that we can get your new cage measurements right." she said while gesturing for me to come to her. In a trance I walked over to stand in front of her, this beautiful and refined older lady wearing pink latex gloves. She turned me around so I was facing away from her and reached out with a gloved hand to touch my erection. "Hold your hands behind your back please Sam," I was told. "If it helps you to finish you may look down at my pretty pink glove as I play with you." she giggled, then the stroking began. It was hard to focus, I had never been in a situation like this. I don't think I had ever even imagined a situation like this. I desperately wanted to cum and get this humiliation over with but it felt so weird, having someone else tugging at my penis, and the feel of the glove against my skin. My penis seemed to be refusing to come to a climax but it also was refusing to get soft. I was stuck in some semi-rigid state. Looking up at Miss Regina didn't help any, she had a semi amused look on her face as she stood holding a box of tissues. "Oh dear, this is just not working well is it honey," Mrs. Gloria said. "Regina, I think that we need a bit more stimulation, something more suitable. Would you run and get Alessandra's purse for me." Setting the tissues down on the table that was covered in lingerie that I still had to try on Miss Regina left only to return a few seconds later with the baby pink quilted leather Channel bag. "Look inside, there should be a small tube of lube. Please hand me that," Mrs. Gloria commanded. I blushed even more as I saw Miss Regina open up Alessandra's purse, besides a small pink wallet and what appeared to be a makeup bag, there was a small translucent ping dildo in there as well. With an air of accomplishment Miss Regina retrieved a small clear bottle of "Adam & Eve Forbidden Anal Lubricant" and handed it to her mother. Not bothering to put the contents back neatly in the pink quilted bag, Miss Regina casual tossed the expensive purse on the floor, its contents, including the small pink jelly cock, spilling out onto the floor. I wanted to voice my displeasure at her poor treatment of her sisters possessions, it was bad enough that she went through something as private as a woman's purse but to treat the property of others so badly was not nice. I was about to say something when in shock, I felt Mrs. Gloria's well lubricated gloved finger at my rear entrance as her other hand, also coated in the slick, clear gel began to pump my now fully erect penis again. "Wait mum!" Regina cried out urgently. "Can I have him put on his lingerie first? I think that would give us more to work with." Pausing and holding her slick, gloved hands up in the air like a surgeon Mrs. Gloria grinned, "Yes dear, you are so smart, that would be perfect. Can you manage that, my hands are a bit gross at the moment." As Gloria stepped away from me Regina approached with a bright purple pair of panties which she held out for me to step into. I looked at them, then back up at her. "Miss Regina, please don't make me do this," I begged her. "It is too humiliating, please not in front of you and your mother please." She disregarded my pleas with a laugh. "Weren't you the one who came to us looking for panties, for yourself, not for some fictional girlfriend? Are you not the person who said that they would do anything to be able to visit my sweet Alessandra? No Sam, panties, and a bra are a must for you. Now if you please," she added, while once again holding the panties open for me to step into. Shaking in my humiliation, my motions stiff and robotic I lifted my foot and placed it into the leg hole of the panties, and then my other foot. Miss Regina slowly pulled the silky fabric up my legs. First she lifted the back of the bright purple, high cut brief panties so they fit snugly on my butt, then she adjusted the front so that my balls and penis hung over the top of the waistband. Next she lifted up the matching bra, like the panties it was bright purple in color and the fabric was so soft and thin. Sliding my arms under the thin straps Miss Regina began to talk. "Sam, this style is called a Balconnette bra, the sides, or wings, as they are properly called, are a very thin delicate material while the cups have an underwire and multiple layers of silk to form a more supportive cup. This bra will look very pretty on a little boy like you." she said while pulling the wings closed and fastening the three little hooks into the corresponding loops. "Now sissy, come here and get back in position," Mrs. Gloria commended me. Sissy, she called me a sissy. My knees almost buckled when the word hit me. How many times had I watched sissy porn on line or masturbated to captions about cruel or humiliating things being done to sissies but now, just now, Mrs. Gloria had called me a sissy. As I stood in shock, trembling, on the edge of a breakdown, I felt her lubricant coated gloved hands turning me into the correct position. One hand began to slowly stroke my rock hard little penis while the other slid over the back waistband of the panties. I felt the cold wetness of her finger as it entered my virgin butt hole and began pumping in and out. Looking up I saw Miss Regina with her phone out, recording my humiliation on video. Hanging my head I began to sob, hot tears of shame, embarrassment, and sexual frustration streaming down my cheeks all the while my body continued to betray me. When I would try to pump my hips to make Mrs. Gloria's movements faster she would scold me, telling me to stop. At certain points Miss Regina would ask me questions and demand I answer with certain words. It was really all just a tear filled blur. Slowly I felt the building of my orgasm but this one felt different, stronger. I wonder if by keeping such a slow, teasing pace for such a long time instead of the rapid rush of masturbation that I always succumbed to if this orgasm would be different. As the feeling continued to build I began panting, then I heard a high pitched squeal, "Ooohhhh...eeeeeiiiee." Oh no, that was me, I was crying out like a little girl. Instantly Mrs. Gloria stopped stroking my little penis, and reached for a tissue, but her other hand began pumping in and out of my ass with furor, her finger curving until it hit something and I felt like electricity had been shot through my balls. Keeping her finger in that position she now began to push and rub in that single spot. Totally out of control I began to spurt into the tissue she had placed over the head of my little penis, shooting squirt after squirt of cum. I was moaning out loud, if anyone was in the store they would surely be hearing this. Opening my eyes I saw the Regina still had her phone out, capturing my degradation. As the squirting stopped Mrs. Gloria slid her finger out of my rectum, removing her hand and soaked tissue, pulling the waistband of my panties up over my butt. "Now we should be able to get a good limp measurement she said, while throwing the soiled tissue onto the soft pink quilted purse that was lying on the floor next to me. After quickly taking the measurements and having Regina record them she pulled the front of my panties up, tucking my very small, very placid penis back to remove the visual of a bump on the front panel of the silky material. "Alessandra, come clean up this mess!" Mrs. Gloria called out. "Yes ma'am," came the quick answer from just the other side of a display of night gowns. I saw my sweet Alessandra running back towards me. Her face turned flush when her eyes fell on the strewn contents of her purse. I blushed and began to reach down to collect her things, but also to remove the disgusting tissue soaked with my seed. "No Sam, please leave it, I need to clean this up." she said blushing and lowering to her knees. She gingerly retrieved her purse, placing the wallet and makeup bag in first, then the pink dildo and lubricant, then to my shock she also picked up the tissue and placed that in her bag as well. To be continued....