4 comments/ 106319 views/ 12 favorites A Sissy Shopping Trip Ch. 01 By: cwsissy My wife, Cindy, and I were in the bedroom getting dressed for a party at Tim and Karen's place. They were good friends that we had known for even before our marriage four years earlier, with whom we had shared a lot of good times, including many a camping trip and tipsy card game, always with plenty of hot talk rife with innuendo. Well, technically, Cindy was getting dressed and I was lounging on the bed, clad only in my panties, watching. I always enjoyed watching Cindy get ready to go out. I love her body, with its perfect, curvaceous ass, full breasts and long legs, all perfectly matched with pouty full lips, beautiful green eyes and perfectly arched brows. Always, though, I felt an undercurrent of envy. If anything, this time I felt it more than ever. She had bought new things for the party and they were the hottest I had ever seen. I wanted them for myself. I wanted to wear the short skirt, the low-cut top with no bra and the stiletto's and to show off a perfectly formed ass, breasts and legs. I would never have the shape but I loved to dream. I felt my cock stir and begin to tent my panties. Cindy, seeing me staring intently laughed a bit and asked, "What do you think, dear? Is it working for you?" With a knowing look at my crotch, "Looks like it might be." It seemed like I was in a trance and came out slowly, stuttering, "Uh, I love your new clothes. When did you get them? They're so sexy." "Sorry Sweetheart, I know you love shopping with me but I wanted to surprise you. I got new makeup too. How do you like my eyes?" she asked, fluttering them at me. They were outlined darkly, with long mascaraed lashes and, with the hazel and golden eye shadow, they exuded sexiness. With feelings in a jumble of pride, lust and envy I whispered, "I love them. I love you. You are so sexy. I just wish ..." "What's that, my little sissy? You wish you could go to the party all dressed and made up sexy too?"she interrupted. "Uh..." I muttered. "I guess so." "Sorry my sweet, I don't think Tim and Karen are ready for that yet, do you? Much less all the other people that'll be there. Sorry, you'll just have to go in your man clothes and try to look the part." I could see the clips from her garter hanging down. She always leaves her stockings till last so they won't get snagged as she gets ready. This was no exception but, as she turned to open her top drawer, my breath caught and it came back to me with a lurch, what I had forgotten to do. I had been home alone while she worked the late shift for the past couple of weeks and had dressed up as sexily as I could, in my own lingerie, mini skirts, tops and high heels. I loved to take pictures and dream about going out all dressed up. Unfortunately I had run out of stockings and borrowed a few of hers. In fact, all of hers. She had nothing left except her backup pantyhose. I felt my face grow hot as I watched her rummage around. When she turned to express her frustration guilt was written all over my face. "Ahh," she exclaimed as understanding came, "So what happened to them?" As she made a beeline for my lingerie drawer I tried to intercept her but she had the drawer open in a flash. They couldn't be missed. The well-worn stockings in all of the colors she likes to wear, including the bright red ones she wears out for our hottest dates. All were noticeably well-worn. She turned slowly to me with hands full of stockings and a scowl on her face. "What is this?" she demanded. "I know you like to dress up but we agreed that you wouldn't wear my stuff! Didn't we? Well, didn't we? So, you spent that last couple of weeks wearing out my stockings? Couldn't you just go get some of your own?" "I,m really sorry, Sweetheart," I whined. "I was all dressed up and I didn't feel like getting changed." "Well," she scowled, "That's a bad excuse for the first time but what about after that? You've obviously been at it a lot! Couldn't you have bought more after that? You just thought I'd let it go, didn't you! You selfish pig. Even while you're dressing up like a sissy you still act like a selfish man don't you!" "I'm sorry, Sweetie. I... Well, I... I just forgot and they were... Well, they were just there." I finally blurted out. Embarrassment overwhelmed me. I always taken a kind of of smug pride in the thought that I was more sensitive and thoughtful than a typical man. My feminine side. It was how Cindy and I had explained my desire to dress up in sweet and sexy women's clothes. She clearly doubted that now. She looked daggers at me. "Well," she hissed, "That's not going to help me now is it?" I cringed as she continued, "I think my little sissy is going to have to be taught a lesson about borrowing without permission." Then, with an evil smirk, "I have just the thing. We're going shopping tomorrow. Don't make any plans." I always enjoyed shopping for sexy things with my wife so I breathed a sigh of relief. I loved the feel of the sexy things and, as I helped her find just the right sizes and styles. As I watched her try them on, I would imagine them on myself. She always ordered me to join her in the change room in the stores that would allow it and gave me an extra thrill by ordering to to find her different sizes and styles to try on. Somehow she never seemed to get just the right size in anything and found many excuses to send me searching. Did the sales people have any idea why I went with such enthusiasm and looked through every rack for just the right thing? Always, so far, I had been too afraid of being caught to actually put anything on myself but usually managed to get some things in my size out of the deal. I thought no more of it as she picked through the used stockings to find the least worn pair. To me she looked as sexy as ever but she complained bitterly about having to wear dirty, worn-out clothes and about how they were baggy and no longer fit her properly. "I have to pull them up to may waist to keep them from looking like sacks," she complained. I felt bad and could hardly wait for the night to end. It was, as I would find out, only the beginning. At the party my wife looked radiant and, as she drew stares from every man there, I was totally proud and thrilled to be with her. She, on the other hand, threw me dirty looks at every opportunity. Finally, Karen, our hostess, caught up with us during one of the few dances when Cindy wasn't out on the dance floor being fondled by yet another guy. "Are you guys all right?" she asked. To my wife, "You seem really upset." It seems that Cindy was dying for the opportunity to talk about her frustrations and proceeded into a litany about how she was forced to wear old baggy stockings and how they were so gross. Then, to my horror, she explained, in detail, why she had no fresh stockings to wear, "My little boy, here, sometimes likes to play at being a little girl. You should see him. All dressed up with his heels, his panties, corset, sexy skirt and stockings. Even makeup, believe it or not. Five pairs of stockings worn out in this past couple of weeks. Maybe, someday, I'll have to show you his pictures." Karen was almost speechless. She turned red and giggled. She blurted out something to Cindy that sounded like, "You poor thing," and made a quick escape. Minutes later I saw her laughing quietly while talking to her husband, Tim. Tim, big, burly Tim, was looking over at me and smiling. I wished I could sink into the floor. He winked and turned back to Karen. He was saying something and shaking his head. I only hoped he was trying to persuade her not to tell everyone at the party. Tim came over later and, smirking, spouted some clever innuendo about having a girls night out sometime. I felt myself turn beet red and blustered about how it was just something I did for fun once in a while. He just winked and left it at that. The rest of the party was uneventful except that I couldn't string two words together and everyone, I'm sure, thought I was stoned or something. Thinking that the storm had passed I thought I might get a good night's sleep but found myself lying awake with fantasies running through my mind all night. Dreams of shopping, parading around in my new purchases, trying on everything in sight with salespeople helping find just the right thing and Cindy encouraging them the whole time. Other dreams of dressing up in my sexiest things and doing my best impression of a slut for Tim. Again, with my wife offering encouragement and giving advice on how to perform just right. Always, though, the specter of my upcoming punishment loomed, adding a touch of fear, as an extra spice, to the tension I was feeling from head to toe. In the morning I dragged myself out of bed and sat down with a pot of coffee to clear my head. When Cindy hadn't yet gotten up I went out to do some chores in the yard, not wanting to incur more wrath by leaving them any longer. About an hour later she stuck her head out the door and I waited with a bit of pride at a job well done for her to exclaim how pleased she was and was shocked when she yelled, making sure the neighbors could hear, "Come on Sweetie. Time to get cleaned up so we can go shopping. We need to buy you your own sexy things." I felt my face get hot and raced into the house before she had a chance to repeat it. I started to complain but she hushed me, saying, "Get ready to go my sweet little sissy. This is your punishment and you had better take it and do what you're told or there'll be no more dressing up in this house. You are either a sissy or you aren't!" I hesitated for a second but I could see that she was dead serious so I headed for the bathroom. After I had shaved and showered Cindy followed me into the bedroom. I started to get my clothes out. Panties as usual but with typical man socks, baggy jeans and t-shirt. I had always wished I could dress up in more feminine clothes but was horribly afraid of what people would think. I always wore typically male clothing outside of the house, even staying away from anything that fit too well for fear that it would give away my inner desires. Today was different. As I started to put the clothes on she stopped me, "You can't wear that horrible stuff to shop for sexy things. What'll the sales people think?" She proceeded to get out my sexiest lacy panties, one of her stretchy scoop-neck tops and the least worn pair of white stockings she could find in my lingerie drawer. After I had put on those things she pulled out a pair of her jeans from a couple of years ago, before she had lost ten pounds, and said, "I think these might fit, Sweetie. Try them." A bit stretchy, they fit perfectly, framing a nicely rounded ass and showing of my panty lines perfectly. A shiver of excitement went through me and my cock hardened perceptively. I started to complain about going out that way but, again, she hushed me, saying "That's enough Sissy. Do as you're told." She pondered having me wear my 5 inch stiletto's but decided that, for now, I would just have to wear my best loafers. "You just won't be able to walk around enough in those. Maybe we'll see what we can find while we're out. You need something new anyway." Just before we left, Cindy said there was one more thing to do. She had me close my eyes and I heard a phhht sound. She came around behind me and reached into the front of my jeans and down my panties, gently caressing my cock and balls. The aroma of her favorite perfume wafted up. Another phhht and I felt a light spray on my neck. "Now," she said, "You're ready." I felt another shiver from head to toe and had to admit to myself that this was a dream coming true. "OK, Sweetie, lets go!" she exclaimed and I started toward the garage door, carefully walking on my toes, one foot carefully placed in front of the other and with an exaggerated wiggle. "Nice," she said, "But you're going the wrong way." At my look of confusion she pointed out that Tim and Karen had borrowed our car for party preparations while their was in the shop. "Remember, Sweetie? We have to pick it up from their place." "No," I thought, in a panic. Fear, humiliation and pure excitement took over and, as my knees threatened to collapse, I almost fell. I turned to my wife pleading, "Not Tim. Please, Baby. I can't do it." "Oh yes you can," she snarled. "Its not like Tim doesn't know anyway. Besides, I heard you last night. Tim, Tim, Tim, over and over again. Oh, I think you can all right!" With that she gave me a push toward the door. "And lets see that sexy walk again." Even as I resisted I was thrilled and proceeded to the door. Just as I stepped out she stopped and said, "You head over there. I said we'd call first so I'll give them a quick call and catch up with you." With that she closed the door in my face and all my hopes of sneaking up unnoticed by Tim evaporated. As I walked down the driveway I saw the curtains pulled back in our front widow and Cindy watching, phone in hand. She did a little upright wave with her hand to signal that she wanted to see me wiggle while I walked. I grimaced but proceeded down the street with my behind swaying, secretly hoping our neighbors were watching. Excitement at being out in these even slightly sexy clothes was winning out over the humiliation. I wanted them all to see. As I expected, I sashayed up Tim and Karen's sidewalk alone and I saw them standing behind the window, watching me every step of the way. They waited for me to ring the doorbell and made me stand there for minutes, drawing out my humiliation. Then, as the door finally opened, I saw Tim standing there alone and in his underwear, with a hardon pushing them halfway up his hairy belly. "Sorry," he said, "Didn't have time to get dressed. Hope you don't mind." He chuckled, "Mind you, from what I hear, you probably don't mind at all." I felt myself blush brightly and could only mutter a muffled, "Uhmmm," while I stared at the ground. "That's a really cute outfit," he said, grinning. "Turn around, lets see all of it." I turned and just as I was facing the street he dropped the keys on the ground in front of me. "Sorry," he said. I bent to pick them up and felt his hand on my ass lightly rubbing back and forth, "Looks like sexy panties you're wearing. What color?" Startled, I turned and straightened quickly, rubbing my face up his protruding cock in the process. "Oh," he exclaimed, "What's this. Is there something you want besides keys?" Suddenly the smug grin disappeared from his face and he looked embarrassed. I heard Cindy's voice behind me, "Mmmm, Tim. Looking good! Maybe we can both try some of that some day." Tim turned bright red as I felt the same familiar flush myself. "Not today, though. My little sissy and I have some things to do." With that, she grabbed the key from me and headed for the car beckoning me to come along. A Sissy Shopping Trip Ch. 02 At the car, I headed for the driver's side as Cindy opened the passenger door. Before I could take more than the first step her almost shouted exclamation, "Excuse me!" stopped me in my tracks. I looking warily at her, wondering what was wrong. "Come on," she smiled tightly, "girls ride over here. I'll take care of the driving today." My macho pride rebelled at first and I tried to stare her down. It wasn't to be and I finally slunk over and got into the passenger seat. As I did I knew that this was submission and a wave of deep satisfaction went through me. While I was lost in the sensation Cindy went to the driver's side, lowered the top and, in her best imitation of a macho man, squealed into traffic. As we headed out of town, Cindy explained that we would be going to the mall on the outskirts of the nearby city, pointing out that it might not be good for her career to be caught hanging out with an obvious girly man. I mumbled a grateful acknowledgment, at the same time realizing that she had not, in fact, said anything about my own career. She went on to warn me, "Sweetheart, I realize that you might feel a bit uncomfortable today but I really want you to accept what happens and do as I tell you. Are you willing to do that?" I looked at her, a bit shocked that she was giving me this warning now, after all that I had already been through. It gradually dawned on me that this might be only the beginning. "I don't know. Could it be any worse than humiliating me in front of Tim?" I whined. "Oh, my little sissy baby, I probably will get more interesting but you can handle it. In fact," she said, leering at the lump in the form-fitting jeans, "I suspect that she doth protest too much." As I turned bright red, she continued sternly, "Now how about if you just admit that you are a sissy and that you get off on being treated like a sexy little lady. How about if you just stop with playing at the protests and resistance and we just have some fun with this." I was shocked to hear her sum up my innermost feelings so bluntly. I still wasn't ready to acknowledge them and sat stone-faced for miles, trying to get my feelings sorted out. Whether to give in and find out where this roller coaster of sensations and thrills would take me or to hold onto what dignity I could. I realized that once I crossed the line there might be no going back. The control was Cindy's now and once I said yes it would most certainly never come back to me. It seemed like a dozen times that I almost said yes but each time pride or fear won out and I said nothing. Finally, Cindy grew impatient and, slamming on the brakes, swung the car into a screeching U-turn, saying, tensely, "OK, babe, I get it. Lets call it off." It was an immediate and terrible sense of loss. It came to me abruptly that it was now or never and I whispered, "Yes." Then, at her questioning look, louder, "Yes, I would love to do whatever you want." I tried to smile but just managed a grimace. "OK, Sweetie," she said. "Are you sure? If you are, you'd better smile like you believe it right now and beg me to turn around. Is this something you really want?" Pushing my fears aside I managed a winning smile and said, "Yes, Sweetheart, it is absolutely what I want. I want you to take me in hand as your little sissy and I will do whatever you tell me. This is a dream come true for me. Please turn around." She slowed and pulled over. After carefully scanning my face she abruptly swung the car into another U-turn. As we traveled I tried to wheedle out her her plans for the day but she would have none of it. "You'll find out when we get there," was all she would say. As we pulled up in front of the doors to the department store at one end of the mall I felt a rush of adrenaline as the fear and excitement welled up. Looking curiously at Cindy, I wondered why she had pulled up here instead of just parking the car like we usually would. She looked back at me, speculatively. "I think you can manage it. Girls do every day," she said thoughtfully. "OK, I'm going to find parking," she said, looking out over the packed parking lot. "I might be a while. While I'm gone I want you to go to the lingerie section and get a bra. Not just any bra but a pretty one that fits. Pink would be nice." "How do I pick the right size?" I stuttered, "I don't know what size I am." "You are such a naive little sissy, aren't you. You have to get it fitted. You find a salesperson and ask her to help you. Now go!" I felt my face turn beet red but got out of the car. As she drove away, I stood on the sidewalk trying to ignore the stares from the people going by but still noticing the mixture of leers, scowls and furtive smiles. Wondering how I could do this and knowing I had to. I needed to keep going. This was what I wanted and I was dying to know what the day would bring. I forced myself to walk through the doors. As I walked into the lingerie department I looked desperately for a salesperson who might be willing to help me and not throw me out on my ear. Try as I might I couldn't tell. Finally I simply resorted to browsing through the bra's. Taking a couple from their hangers and holding them against myself. One salesgirl cruised by. I looked up hopefully but she quickly looked down and walked on, ignoring me. I saw her go back to the counter and talk to a couple of others hovering there. I could see her giggling and pointing in my direction and I felt my face grow hot. As I watched, though, the oldest of the group, curvaceous and perhaps in her late twenties, left the group and headed my way. I was terrified. She would throw me out. Have security take me away. Report me to the police. And then, she was in front of me and smiling, "Can I help you? I see that you've found our prettiest bra's. Do yo need help getting the right size?" "Uhhh," I mumbled. She chuckled lightly, "It's OK. I see that you're checking them out on yourself. Is it for you?" Her gorgeous smile was infectious and I found myself smiling hesitantly. "Uhhh, yea," I muttered. "OK, lets get you measured up so we can find some for you to try on," and off she went to get the tape measure. As she did, I saw her say something to the other girls and they hesitantly joined her as she returned. She measured around my chest, under my breasts and announced "38! Now tell me, do you want something to fit your breasts as they are or do you plan to wear something to make them bigger?" "Uhhh, I'm not sure." "Well, I think we could try for a B cup with a bit of padding or, we have these cute little breast forms that we sell to some of our less endowed customers. Would you like to try those?" As I hesitated she asked one of the other girls to get the forms, "The larger ones. I think those would fit his... oops," giggling, "Or should I say, her, chest best." To the other girl she said, "Hey Jill, how about finding some 38C's." To me, "Do you have a color in mind? A nice baby blue would look sweet or dark red would be so sexy. Maybe pink for a really cute look? Or, do you want cream to match your top?" I hesitated, caught between pink as Cindy had suggested and all of the other wonderfully sweet, or cute or sexy colors. Finally, after what seemed like ages, she broke in with, "I tell you what, why don't we just try a bunch of them and you can see what you like best." As she nodded at Jill to carry on, she grabbed a couple of bras from a nearby rack and, with the forms in hand, led me across the store to the mens changing rooms, pointing out as she went that men weren't allowed in the womens' and they would be fired immediately if they allowed it. "Sorry dear but we just can't risk it." My face grew hot as she walked up to the young man attending the change rooms, saying, "Can we borrow one of your rooms? He, uh, she isn't allowed in ours but she wants to try some things on." He chuckled a bit, "Sure, why not?" and opened a door just out of sight of the sales floor but near enough to his station that he could easily see it. I saw him watching closely as I entered. The girl passed me a bright orange bra and told me to put it on and come out so she could see how it fit. I took off my top and put the bra on as I'd seen my wife do many a time, snapping it together in front then turning it around and pulling the straps up over my shoulders. I opened the door and came face to face with the young man. He grinned, "She had to go away for a minute. She asked me to give you these and tell you to put them in. She said to look for the L and R on the back." We looked together and he stood and watched as I slid them into the cups. "Hmm," he noted after I had them positioned in what looked like more or less the right place, with some amusement and obvious interest, "That would be almost sexy if it weren't for the hairy chest. Are you going to shave or something?" A familiar voice came from around the corner, "Of course. She can't run around all hairy like that, now can she." Cindy and the sales girl came around the corner, both wearing big smiles. "But first lets pick out the right things for her." Jill came around the corner just then with an armload of bras and, I noticed, quite a few matching panties. What followed was like a dream, me trying on bra after bra with the ladies all looking on, offering opinions, adjusting here and there, chatting amongst themselves and discussing the merits of each bra. I was thoroughly enjoying myself, getting lost in the look and feel of the silk and lace in an amazing range of colors and styles. Spinning around to show off and to see them from every possible angle. Every once in a while blushing brightly when I caught the young man's eye as he watched closely throughout the process. As each bra was removed the girls decided together, with frequent comments from the young man, whether it was a keeper or not. Finally there were none left to try and there remained only five bras in the keeper pile. Three panties were also on the pile, having been added when the matching bra hit the pile. "OK," Cindy smiled, "Good job, Sweetie. Now we just have to go through these few again and make your choice. You might as well try the panties on too. Matching panties are so cute so I really want to see you in them." I felt myself turn red yet again but took the first of the sets. Closing the door, I undressed, leaving on only my garter belt and stockings, and put on lacy pink panties and the matching bra. After a moment to catch my breath and work up my courage I took a deep breath and swung the door open. All were watching, including the man. Through a haze of excitement and humiliation, I heard the comments, "He's so cute." "So sexy." "Look at the stockings and garter. What a sissy." From him, "Wow, looking hot but the hair has to go." I looked at him and blushed as I saw him staring at my rock-hard cock, plainly visible and tenting out the lacy panties. I scanned downward and saw a hard lump in his pants and the tiniest bit of wetness at the top. I smiled, feeling a thrill at the thought of having that effect on a man. "OK, you two," Cindy took control again, "Save it for later." To me, "Go! Try this one now," handing me a deep red set." Finally, after trying on and modeling my way through the second stack and after more chattering among the group we settled on two sets, lacy pink and cute baby blue with pink flower embroidery. Thinking that the task was done I started toward the exit carrying the two panty and bra sets and breast forms but was stopped mid-step. "Hold it!" Cindy commanded. "You might as well put the pink ones back on while we're in the changing rooms. You'll be wearing them for the rest of the day." I turned to her, shocked, realizing that the bra would be obvious under my cream top. She was adamant "Do it, Sweetie. You know you want to. In fact, why don't you thank these nice people who have helped you so much and tell them how much you want to wear the clothes and be a girlie." Hanging my head in shame, I mumbled, "I do love to wear girlie clothes and I really want to be a sexy girl. Thank you for your help." "Hold your head up, Sweetie, and say it so they can hear you." I put on my best smile, held my head high, looking straight into the young man's eyes and said it again. He winked and leered. I changed quickly, putting on the lingerie and adding the breast forms, giving myself relatively small but distinct breasts. I glimpsed myself in the mirror and was thrilled at the girlish figure I saw. As we left the changing rooms, my wife grabbed a piece of paper and pen from a nearby counter and I watched her write my cell number on it. She handed it to the young man and said, "Call her some time. She'd really like to help you with that." As she did so, she grabbed my hand with her free one and pulled it down to stroke the lump in his crotch. It was huge and I couldn't help myself as I continued to fondle it and stroke it. Finally, my wife pulled me away, "Le's go my little sissy, lots more to do and you have an appointment to get to." Expecting to head to the checkout counter, I was surprised when we headed in the opposite direction. Just as I started to ask why we entered the cosmetics area and I found myself being pulled toward a couple of expectant looking people behind one of the counters. One was a lady in her 30's and the other was a young man in his early 20's, wearing unisex clothing and heavily made up. He greeted us, "Hi, I'm Matt and this is Julie." I went to shake his hand but he pulled me close to give me a quick peck on the mouth. "Hi, darling, no need for formalities here. I assume you're the one your dear wife told us about." I was at a loss for words but Cindy jumped in, "Yes, this is her. You can see that we have a bit of a challenge." Cindy had me sit on a stool in front of the counter, "OK dear, I'm going to leave you with Matt and Julie. They promised to take good care of you. I think I'll wander around the store for a bit. Maybe see if I can help that young lad in menswear out with that little problem he had." She winked and grinned lasciviously. For the next forty-five minutes Matt and Julie took charge. They held different types and shades of makeup to my face, argued about the best colors and products, applied huge samples of all sorts and finally came up with a selection of products. They next proceeded to apply them, explaining as they went, "...concealer under your eyes to hid the puffiness..." "This is foundation. You use it to make your skin tone even. This is a special one that'll help hide your beard." "...darker beside your nose to make it look narrower..." "...blush just below the corner of your eye and back..." On and on it went, through eyeshadow, eyeliner, mascara, lip liner and lipstick. A number of customers came by and gawked. I heard many manly snickers, ladylike snorts of disgust and a few oohs and ahs. I tried to see the source of some of these but after having my head pulled back around non too gently and getting scolded several times I gave up and just absorbed it. The snickers and disgust just as thrilling for me as the oohs and ahs, driving home the humiliation that I craved. I drew back briefly when Matt picked up some tweezers and approached my eyebrows. I knew that there would be no hiding them later. He was determined, though. "You just can't go out with those big caterpillars on your face. I won't let you and your wife won't let you. Now, sit still," and again my head was pulled around. As Julie held my head still from behind Matt proceeded to pluck and trim. I forced myself to relax and, finding that I could ignore the pain I gradually began to look forward to the end result. Finally, it was done and they brought a small mirror over. I couldn't believe it. I looked like a different person. I exuded sexuality. I turned this way and that to get the full effect. There was no way I would pass but I was clearly a sexy looking ... something. I looked at Matt and Julie and whispered, "It's wonderful. Thank you so much." Julie gave me a quick hug. Matt, though, seemed to be almost in tears as he said, "Oh, Baby, you look so sweet." He gave me a hug and another kiss on the lips this time pushing his tongue into my mouth. I hesitated momentarily then started to suck hungrily on it and then pushed my own tongue through. I couldn't get enough and attacked his mouth with my own. Pushing deeper, sucking him into me and playing with his tongue with my own. Distantly, I heard my wife chuckle, "If you girls are just about finished." I pulled away and turned to see my wife standing there, her hair disheveled and her lipstick smeared. "Oh, my little sissy, you look so lovely," she cooed. "It looks like we both need our lipstick fixed but before we take care of that come here, I've got something for you." With that, she pulled me in and kissed me deeply, pushing her tongue halfway down my throat. I tasted cum and knew that she had been back to mens wear. Finally, she asked Matt to help us with our lipstick. After he was done she again wrote my cell number on a piece of paper and stage whispered to Matt, "Call her. She would love to finish what you started." I heard snickers from the onlookers behind me and was overwhelmed with embarrassment and with love for my wonderful wife. And then, abruptly, Cindy was off and running, dragging me along to the checkout, "C'mon, Sissy girl, we have to get moving if we're gonna get to our next appointment on time." A Sissy Shopping Trip Ch. 03 We were quickly through the checkout and on our way again. Cindy dragging me by the hand toward the mall entrance. "C'mon, lets go. We have some more stops to make and we haven't got much time." Our next stop was a high-end shoe store just outside the department store. I had lingered outside that same store many a time, admiring the sexy heels on display in the window and imagining myself prancing around in them. As we approached, my wife paused suddenly. Feeling a surge of disappointment, I had to ask, "What's up? Isn't this where we're going?" "This is it all right. You just go on in. I'll be right there." She grinned and, as I surveyed the store, with the handsome salesman with his perfect, chiseled face, broad shoulders and sparking blue eyes hovering in the men's shoe section and watching me, her intention became clear. "Go now. Over to the mens side," she whispered. Nervously, I wandered in and started looking at the assortment of mens' loafers, sensing the salesman approaching and feeling a growing tension in my gut. Then he was beside me. With a scowl he greeted me, "Yes..." a pause follower by, "Sir," in the most skeptical of tones. "Can I help you?" And then, from behind us, in her sweetest voice, Cindy piped up, "She'd like a nice pair of heels. Can you help us?" She smiled her most winning smile. As he eyed her gorgeous body with its short skirt and low-cut top, I could see his expression change as his interest in Cindy won out over his distaste at having to deal with me. As she bent over in front of him, supposedly to look at some shoes low on the display case, he could see her stocking tops and, I'm sure, got a glimpse of her smoothly shaven pussy, I could see that the decision was made and a flush of shame overwhelmed me. "Well, I'm not supposed to sell shoes to women, but this might kind of be an exception, wouldn't it," giving me a big smirk. "She'd like something in cream to match her top. And, I think, at least a five inch heel." As he looked skeptically at her on the latter, she assured him, "Don't worry, she thinks its her big secret but she's been practicing to be a little sissy for a while now. " I was stunned. She knew. How much did she know? Did she know about my whole secret stash. The little ballerina shoes, the six inch heels and everything in between? "You should see her in the six inch heels. She's pretty wobbly but she can get around OK. She can do just fine in the five inchers." Well, after ten more minutes of her flirting and him leering we finally settled on a gorgeous pair of cream colored stiletto's. I was quietly thrilled at how they showed off my brightly colored toenails. As he prepared the box for our new purchase I started to pull on my loafers Cindy asked, "What are you doing? Put them on. We didn't go through all of this just so you could carry them around in a box." To him, "You can keep the old ones. Throw them out. She won't be needing them again today." Then, with a wink, "Probably never." As we left the store, me tottering on the unfamiliar heels, he followed, clearly not wanting to let Cindy get away. She grinned and, looking over her shoulder, winked broadly, stage-whispering so that all could hear, "I'll be back. Next time she can wait at home for us." A surge of jealousy washed over me but, as I turned to complain she pulled me forward roughly. "Come on sissy. Look at you. Do you think you're in a position to complain? Just consider yourself lucky if I let you clean us up afterward." As my anger turned to humiliation I turned my glowing face away, wishing I could run and hide but knowing that, despite Cindy's observations, the best I could do would be to wobble away on my new shoes. The next stop, a fashionable store filled, it seemed, to capacity with teenage girls, was at the other end of the mall. The hike there was filled with, the now familiar, stares and whispered comments, but was otherwise uneventful. Inside, Cindy was all business. After selecting a couple of short skirts in pink, pale blue and black she led me to the changing rooms. In response to the attendant's questioning look she asked, "She's got to try these on," showing the skirts. The attendant laughed a bit but shrugged and opened a room. Cindy had me try each skirt on and come out to show her. Then, when none fit to here satisfaction, had me stand in the last one outside the changing room while she went to get some more. It seemed like she was gone for hours and the embarrassment of being stared at by a steady stream of teenagers and their mothers was almost more than I could bear. I felt eyes boring into me from all directions and it was all I could do not to run and hide back in the changing room. I knew I couldn't, though. Cindy, I was sure, would find a greater punishment if I did. Three more to try on followed by two of them for a second time before she chose a cute little hot pink one with a frilly band of lace around the bottom. I knew what was to come and, on my final return to the changing room, removed the tags but put the skirt on. I bundled up my slacks and returned to where Cindy was waiting. As we headed toward the checkout Cindy dragged me aside, to a rack of tiny party style purses. Grabbing a bright pink one, "To match your pretty skirt," she proceeded to empty the pockets of my slacks into it. Then, after paying for my purchases, it was back into the mall and again, Cindy was dragging me along, almost pulling my off my heels as I stumbled along. "Come on, Baby. Last stop now but we're already late. Come on!" A few minutes later, after what seemed like a hundred miles in my new heels, we arrived at the day spa the had just recently added in the mall. It was decorated beautifully, mostly in pastels and honey colored wood and featured a two story waterfall. The hostess was gorgeous, with long legs I would die to have and the shortest skirt I had ever seen. We hurried in, Cindy apologizing for our lateness as we approached the reception counter. "No problem," the hostess replied. "Matt told me about you and told me to call him when you arrived. He said he wanted to help you personally." She winked, and scanned Cindy from head to toe, lingering briefly on her low-cut top and micro skirt. "I think I see why." She transferred her attention to me, all business. "So this is the one we have the appointment for? Lets get you registered while we wait for Matt. Les'll be your esthetician. He, uh ... has his own way of doing things but I think you'll enjoy it," she said, with an emphasis on the "you,ll", and a broad wink. "I see that we have you down for a full wax with a Hollywood, a pedicure and manicure." I must have looked confused and she looked at me questioningly. "Uh, Hollywood?" "Yea, Hollywood." Then, whispering so that the other women in the waiting room wouldn't hear, "Your cock and balls." "Wha ..." Cindy broke in, "You'll love it. Its a bit painful at first but its the price of being a sexy girl." Seeing a hint of rebellion she made it clear that there would be no discussion, "You'll do it! I don't want to hear any more about it." "Ah, here's Matt now," from the hostess. I watched as he swaggered over to us. He was over six feet tall, perfectly proportioned, with a face from a roman statue, slightly curly black hair and intense blue eyes. He wore dove gray suit that fit his broad shoulders and tight body perfectly. There was a substantial bulge at his crotch. He didn't even glance my way, though. His attention was completely on Cindy, looking her up and down, obviously taking in her long legs, great breasts and gorgeous face. "Hi gorgeous," he said, and finally sparing me a glance, "So this is her, eh. I'm sure Les can do something to make her presentable. Lets get her in and you and I can go somewhere and get to know each other better." With that, he put his arm around Cindy's waist and guided toward one of the rooms in the back, leaving me to follow in their wake. They paused in front of one of the rooms and Matt ushered me forward telling me to get undressed and take a seat on the huge chair in the middle of the room. It reminded me of a dentist chair except for the towel across it and the big basin built in under the footrest. The only other furniture was a small stool and a massage table on the other side of the room. I waited for them to leave but they just remained, watching me. As I started to say something Cindy fixed me with her best glare. I gave in and, hanging my head in embarrassment, removed my clothing until I was standing there naked under their watchful eyes. Matt chuckled, "OK he really does need help, doesn't he." Just then, the door opened and a short pudgy man who must have been in his forties walked in. "Ah, Les," Matt said, "We have one of your favorites for you." He gave a brief smile that didn't reach his eyes and looked me over. "It'll be a while," was all he said. "Take your time. Cindy, here, and I'll get to know each other better," Matt said with a wink in my direction. "Call me in my office when you're done." "Much better," Cindy smiled broadly up at Matt, pulling him tighter and running her free hand over his growing bulge. To me, with a smug grin, "Do as Les tells you, sweetheart. If not, I'll hear about it and you'll regret it." With that they left, closing the door behind them, ignoring my embarrassment. Les turned to me, "Lets start with getting all that ugly hair off you, darling. Get up on the table there. Face down, please. We'll start with your back" I climbed up and lay face-down with my forehead resting on the the built-in support and facing the floor through an oval head-sized opening. "I feel so exposed," I said, trying to ease my embarrassment and hoping for a bit of sympathy. He chuckled harshly, "Don't they all. Just do as you're told and we'll both enjoy this. Stay there while I get ready." I heard a rustling and assumed that he was putting something like a smock over his clothing. Then I could sense him beside me and saw bare feet and hairless calves come into view through my little head opening. I started to lift my head but a push on the back of it changed my mind. Remembering Cindy's warning I decided not to resist. "Just lay there. There'll be a bit of pain but nothing you can't stand." With that, I felt him roll something warm behind my shoulder. That was followed by a patting sensation followed quickly by a rip and smarting pain. I jumped and moaned a bit but stayed where I was. "Ah, the price of beauty,"he crowed, applying the next strip. And so it went, as he covered my whole back and down the backs of my legs, leaving my butt, "for later." Next he had me flip over and that's when I saw, as I already half expected, he was completely naked. He was sporting a small but very hard cock with a dribble of precum down to his balls and a drip just about to fall from his sac. He looked at me checking him out and grinned broadly. "Later, baby. We've got work to do right now." With that, he started applying wax to my chest. The process continued down my chest, my legs and my arms until I was completely hairless except, that is, for my pubic area and top of my head. "OK," he said, giving me a smug smile. "Now for the fun part." He reached under the table and I felt it slowly dropping. When it was about thigh high it stopped and he pulled his hand away. "OK, off." As I clambered down he threw a pillow across the bottom and told me to bend over it, positioning me so that my upper half was laying on the table, my feet were on the floor and my butt, supported by the pillow, was high in the air. His help consisted mainly of standing behind me, pushing and pulling me, with his crotch buried in my ass. Several times I felt his penis pushing at my opening. Almost involuntarily, I found myself pushing back and doing my best to open myself up to him. He was teasing me and each time, just as he started to enter he would pull back. I felt like a complete slut and knew I would do anything to have that cock inside me. Finally, he pulled back and I felt the now-familiar sensation of wax being applied as he started on the cheeks of my ass. I was beginning to get used to the pain and relaxed until I felt the warm wax being applied inside the crack of my ass and over the opening itself. I tried to stand but was pushed roughly back into place. I tensed up and, as I felt the usual patting I felt fear. I knew the pain was going to be intense He giggled. "Ah, its OK. Wait until we get to to your balls. Besides, just think how much sexier you'll be for the next guy you want to give your little pussy to." With that, he gave a violent tug. I saw stars, the pain was so intense. He laughed again and proceeded to apply more wax on either side then strip my crack completely clean. He let me rest for a few minutes but while I did he came over in front of my face, blatantly standing up against the table with his cock almost touching my lips. I couldn't help myself and opened my mouth, hoping that he would give me a taste but not having the courage to lick the precum up and take him into my mouth as I so dearly wanted to do. "Ah," he chuckled, "Does the little girlie want a taste of cock?" With that he pushed forward a bit more, allowing his penis to just brush against my painted lips. I pushed my tongue out to taste him but got only the sweet saltiness of the precum left on my lips as he quickly drew back. "Alright, flip over and get up into the middle," he demanded. I did as instructed and there was no disguising the rock hardness of my cock. He smirked, "Ohhh, our little girlie is really enjoying this, isn't she? Is she into the pain do you suppose?" He smacked my ass hard. "Or, is it the thought of being my little playtoy that has her all hot?" he asked as he climbed up and on the table and ran the head of his cock from my forehead down to my chin, leaving a trail of precum. I was desperate to taste him and when his cock came over my mouth I opened up wide and pushed my tongue out to capture it as it went by. That obviously pleased him and he smiled wickedly as he lifted it up to just graze the tip of my tongue. As he climbed back off and prepared to work on my pubic area I contemplated my own responses. Why was I so turned on by this pudgy, unattractive man? Why did I ache to taste his semen? Why did I so love it when he teased and tormented me? Finally, the questions gave way to a simple and overwhelming desire to be his. At that moment I wanted nothing more than to be Les' slut, to be used by him in any way he wanted. I lay half dreaming, only vaguely aware, as he trimmed and ripped off the bush above my cock. Then, suddenly he was holding and lightly caressing my cock and it felt like a jolt of electricity went through me. I spasmed and almost came but a harsh pinch to the head brought me back to reality with a jolt. "No, no, no! Not yet my sweet," he laughed. He proceeded to remove the hair from my cock efficiently and with surprisingly little pain. My testicles were another matter entirely. The pleasure of his touch on my balls followed by the erotic warmth of the wax was abruptly dispelled by the excruciating pain as he pulled the strip free. It felt like my balls were being pulled off and then like they were on fire. The cycle was repeated over an over until I thought it would never end. Finally, he stopped and held my balls in his hand, muttering almost to himself, "Ahh, so pretty now." Then he gave them a smack and commanded, "Up! Over to the chair. Time to finish making you beautiful." As I convulsed and my stomach went into knots and I and I stared daggers at him. "The price of beauty, Baby." was all he said, with a wicked grin. I traipsed over and collapsed into the seat, feeling an odd combination of dread and anticipation at what might be in store for me next. But I was surprised and not a little disappointed when, as any other ethetician would, he simply pulled the stool to the bottom of the chair and started to fill the basin. Very matter of fact, he washed and massaged my feet, giving me only a brief thrill when, during the massage, he rested them one at a time on his small hard cock, obviously giving himself a thrill and, in the process, smearing precum all over my feet. In every other respect it was all business, at least until he had finished working on the nails of my toes and finger. Cleaning up my toenails, filing them to nice smooth arcs, applying fresh, bright pink, nail polish, sticking long plastic nails on my fingers and painting them bright pink to match my toes. With a vague feeling of loss I resigned myself to the thought that this was it and there would be no more fun today. I was wrong. As soon as he finished, he picked up a remote control unit and hit a button. I felt the top of the chair dropping as he ordered me not to move, "or you'll smear your polish." When it felt like my head must touch the floor and I was looking up at my cock standing proud above me it stopped. "You'll love this feature," he laughed as he came and stood over my head where it lay on the narrow headrest. I could see his balls with the trail of precum and felt a drip hit the side of my nose. As he raised the chair again I didn't need to be told and opened my mouth wide until his balls were completely enclosed in my mouth. "Go ahead, sweetie, suck them." And, as I sucked them deep, "Lick them too." "Gently now," as I nipped them a bit. I savored the taste and smell of him. The slight smell of sweat, the slightly salty but sweet taste of the precum that formed a slippery coating on his hairless balls. I was in heaven. He pulled forward then, commanding me to lick all the way back to his ass. Moaning as I did so, "Ahh, it feels so good. Keep it up, Baby." "Now push in deep," as I pushed my tongue deep into his opening. I couldn't get enough and, as he slowly moved back and forth I licked and sucked his balls and back to his opening over and over. His balls and hole and everything in between were my world and I was aware of nothing else. When the chair dropped again I was shaken and, lifting my head, I tried to follow them as they hovered just out of reach. "You really like that, don't you sweetie," I heard his voice come to me seemingly from a great distance. "You'll really like what comes next." With that, he backed away and pulled at the headrest and I felt it drop away. My head dropped back to the lowered rest and I found myself, mouth wide open, looking at his thighs. Looking up I could see his cock hovering just above my open mouth. He raised the chair again and as he did I felt his cock land first on my chin then slant up as the base came hard against my mouth. At that he stopped the chair and backed away. "Time for us to talk, Baby," he said as I lay staring at his cock. "First, what do you want most in the world right now?" He ran his cock lightly over my lips. I moaned, "Your penis." "What do you want to do with my cock?" "I want it in my mouth. I want to taste it and lick it." "And...?" "And I want you to fuck my mouth. I want you to push it into my throat." "Do you want my cum?" "Oh yes, pleeease," I hissed, desperately. "I want you to fill my mouth with cum!" "What does that make you?" "I don't know. Please let me suck your cock." "How about a sissy cumslut? Tell me you're a sissy cumslut and I'll give you at taste." I could hear the laugh filed with scorn in his voice. "Yes, I'm a sissy cumslut," I moaned. "Please." And then, Cindy's voice, "That's fantastic Les. Perfect!" She came into view behind Les, with a video camera in hand. As I struggled to get up, desperate to get the camera from her, she laughed evilly. "This should be great to put on the web. I bet you'll get thousands of hits." As Les moved forward, trapping my head in place, she continued, "Settle down. Just do as you're told and I won't send the link to all of your friends." "Oh, and wouldn't Steve love to see this," referring to my older brother. "Well, maybe he'll see it anyway. Sue tells me she's caught him looking at sissy videos a few times now." A Sissy Shopping Trip Ch. 03 "No," whispered. Knowing that I couldn't take the humiliation of my brother seeing me like this. "Oh, well," she snickered, "Its a chance we'll have to take. He'll probably just want some for himself anyway. You should be able to handle that." She handed the camera to Matt, saying, "Put it somewhere safe," then turned back to me, suddenly all business. "Well much as I would like to watch you suck Les' cock, you'll have to save it for later. We've got plans and I don't want Les all worn out." She pushed Les out of the way and, took his place, saying, "I've got something else for you, though." As she moved her pantied pussy in place over my mouth I smelled semen and knew it had to be Matt's. Her panties were soaked and clumps of creamy cum had collected here and there. I found myself licking desperately, trying to get every bit. I wanted all the cum I could get. I loved the thought of being used to clean up after a real man. After a few minutes she was moaning, "Oh that's so hot. You really are a cumslut, my sweet little hubby." She moved back briefly and I moaned, wanting more. While Les adjusted the headrest back up, I saw Matt standing by, watching me with a mocking grin on his face, "What a pussy," was all he said. And then Cindy was back pressing her, now pantyless, smooth pussy onto my mouth. "Lick it all out of me now, pussy. You know you want it." I reached in as far as I could tasting his cum, trying to get every bit. She rode my face, rubbing her clit back and forth over my tongue, getting more and more violent until finally she erupted in an huge orgasm. Her legs collapsed and she fell over on top of me, pushing her pussy hard onto my mouth. I felt a huge warm wet load pushed from her pussy and tasted cum. Matt's cum. She rested, laying over me for a few minutes, while I cleaned every drop from her pussy. Finally, she roused herself, moaning, "That was fantastic. I think we know what you'll be doing from now on after I have my fun with the real men." Then, "Now get up and get dressed. We have to get ready." As I raised myself, looking around at Matt and Les, both with big grins on their faces, I had to ask, "Get ready? Get ready for what?" "We're going out on a double date tonight my little sissy husband. I'll be going with Matt. And..." She paused. "Who am I going with?" I had to ask. "Why Les, of course."