Small-steps free porn video

Small-steps The first time I saw them in my drawer, I was puzzled and held them up. They were a plain white pair of women's underwear. A cotton bikini style by Jockey which had been worn before but I couldn't tell if they were my wife's or a pair of my step-daughter. In any case, they did look a little like the male briefs I normally wore. Mine of course were cut for a man, with a kind of pouch in front, but I did have white ones, as well as a few in black, blue, and gray. I never liked boxers and the tidy white briefs seemed designed for boys to be bought by their mothers. Looking at the panties, I just reasoned someone had put them in my pile of laundry by mistake when they were sorting the clean ones. I mean they looked so plain and were the same color and cotton material as mine. So not knowing which female they belonged to, I just dropped them in the dirty clothes figuring they would be sorted out later. Next week they reappeared in my drawer. I seemed to find them only when I was by myself and it seemed silly to accuse my wife or her daughter about not knowing their own underwear. So I repeated the tack from last week and dropped them back into the hamper. The third time they showed up in my underwear drawer, I looked at them a little closer. They really were just like mine, except they were a bit smaller and without the added material in front. It seemed silly to just keep sending back through the wash when they were really clean, so I reasoned I'd wear them first. They fit okay, but were a narrow in front which meant they didn't fully cover my penis. But I just went ahead and wore them as I worked around the house on my day off. It made me feel slightly naughty; a secret sexual thrill, from wearing what was nominally women's underwear. As I dropped them back in the wash, I figured they'd end up where they were supposed to. After the week's laundry was done, I saw them again. This time, I decided I would just put them in my wife's panty drawer. So they were gone for a few days, but showed up again in my underwear drawer. It was beginning to feel silly to be concerned about the whole thing. I mean they looked so plain it was obvious that they could be male underwear as easily as a girl's panty. So I just wore them again only this time, I tried tucking my penis back between my legs, which allowed my balls to slide into my body. They fit much better this way, as the narrow strip of fabric in front didn't need to try to cover my penis or sack. The snug fit that resulted and how my penis felt like it was being tightly held by the fabric gave me a heightened sexual feeling all day. From then on, when they appeared in my underwear drawer, I wore them, with my male equipment tucked away. The smooth front and tight feel always gave me more of the sexual thrill, a kind of secret thrill. It was my own little game. However just when I got used to them always showing up in my drawer; a second pair was there with them. This pair was a similar style, plain cotton bikini, but in black. I was really puzzled now. As I held these up, I wondered whether it was worth going through the same exercises that I had with the white pair. Mulling it over, I reasoned that it would play out the same. I decided I would just wear them like I did the white pair and if they returned okay, if not, okay. So now I was tucking myself twice a week. If the panties showed up in my drawer, I wore them. After a month of this, it was becoming routine. That's when the third pair appeared. They were a smaller cut still, with narrow sides holding the front and back together in white. But they were not made from cotton. They were a silky material, maybe nylon with a bit of stretch, so perhaps some spandex too. Overall they looked quite different from my men's underwear. It was hard to see why they were in my drawer, so this time I just dropped them back in the dirty laundry hamper. But they reappeared in my drawer a week later; this time I put them in my wife's panty drawer. In a few days, they were back in my underwear drawer. Every time I held them, I thought about wearing them, so this time I did. I liked the way the silky material felt against my skin. So from then on, I wore them just I as I did my cotton panties. I should have been surprised when a black pair of similar style showed up, but somehow I wasn't. I did think that I now had four pairs of panties that were routinely showing up in my dresser drawer. It wasn't something that I made a point of thinking about, so it never seemed to cross my mind when I was with my wife and panties weren't a topic I would ask my step-daughter about. Also I was beginning to like being tucked; it kept my sexual arousal at a higher level most of the time. My wife seemed to sense this, as she often initiated sex on days when I had worn panties, although usually she steered me toward cunnilingus for her and her masturbating me to climax, rather than intercourse. That was fine by me; sex is sex to a married couple. When the gray boy shorts appeared in my drawer, I was actually a bit excited. They were more of a spandex material and really held my tucked penis back tightly. I also noticed that some of my regular men's briefs had not made it back to my drawer after I wore them; they just disappeared. Now when I opened my underwear drawer, it contained mostly panties. So I had been more aware of a pattern before that Saturday morning. This morning when I pulled open the drawer as I always did, it contained only panties. Besides the five stragglers that had made their way there gradually, that had been worn previously by someone; the drawer held five more pair. Only these were brand new and were obviously women's underwear. The colors were ones that would be found in only in panties, not men's briefs: a bright coral, a pale yellow, white with a floral print, and soft pastel blue and pink. The styles were also woman's panties. The coral one was a boy short, but entirely of lace. The pastels were a string bikini design, with only narrow triangles of material in front and back, and cut to ride low on the hips. The pale yellow was lace in front, but sheer in back. The floral print was a hi- cut style that had only skinny coverage in front and back. The materials were either nylon or spandex, not cotton like men's briefs. I just stood there trying to decide what to do. That's when my wife walked in. I looked at her in a puzzled way and picked up the floral design to ask what was happening. "Cheryl, what are these doing in my drawer?" "Oh those? Pressley and I thought you might like them. I mean you seemed real comfortable wearing your other panties. Aren't they cute? Panties are much nicer than those men's briefs you used to wear. We were out shopping and knew you only had a few pairs. So we just felt you deserved some new ones and picked a variety of styles. You didn't say anything when we gave you other styles, so we assumed you were okay with a variety of looks. If you prefer one style over the others, let me know. I mean that is why we put the first ones in your drawer to begin with; they were styles that neither Pressley nor me found comfortable. The new ones should all fit. I mean you seemed to be a perfect size 5 in a panty. Of course we couldn't help but get you prettier colors and cute details too." My head was spinning now. My wife and her daughter had been aware of this the whole time and had encouraged it? I didn't know what to do, so I just stood there with the floral ones in my hand. "Those floral ones are real cute, but you'll need a pant with a higher waist to wear them. By the way, Pressley and I saw that Macy's is having a great sale, and I want you to go shopping with me since she is spending the weekend at Janet's house. So just put them on and I'll get you some jeans that should work with them." She said this just matter-of-factly, as if it were nothing unusual. I felt a bit embarrassed, in fact my face flushed and I'm sure my cheeks were glowing. But I didn't know what else to do, but to put them on. I mean, all my male briefs were gone, and Cheryl knew about it anyway. So, I pulled them up; they fit snuggly and clung to my ass due to the spandex fabric. I had just left my penis in front. Cheryl came back out of our walk-in closet holding a pair of jeans. "Aren't you going to put your boy parts away? You know, tuck your stuff? I thought you always tucked when you wore your panties?" As much as I had been surprised by her earlier attitude, this statement floored me. How did she know about that? She had never seen me in the other panties, let alone seen me tuck my penis back. I looked at her with a puzzled expression on my face. Seeing that, she just smiled back at me. "Did you think I couldn't tell you had pulled yourself back? I know you aren't the biggest guy, but it was pretty clear when your boy bump was not present in the front of your pants. I quickly figured out when you were in panties and when you weren't. Honestly, I liked how you wanted to be smooth and flat up front. That's why I started initiating sex when you wore your panties like that. The thought made me want to see you bury your face in my pussy. So go ahead and tuck it back, I think that's where I prefer it and obviously you think that is where it belongs too." I was really blushing now, but she stood there watching as if to ensure I would do it. So I pulled down the panty enough so I could manipulate my penis and balls back between my legs. Once I had them in place, the front of the panty fit as snug as the back. The spandex also kept my penis pressed up against my body. Cheryl smiled as if she approved, and lightly ran her hand between my legs as if to emphasize the open gap now between my thighs. She then handed me the jeans; I put them on. I immediately recognized that they weren't one of my regular pairs. They didn't seem to fit. "Cheryl, these aren't mine. They are too tight in the leg and don't seem to fit." "That's because they are a skinny style. The legs are cut to fit tightly against your skin without the baggy material of your old jeans. The waist and hips are fine. I mean you zipped them up easily. You just need to get used to the feel of a tight style. Here use this top I bought you for your birthday. It is perfect with a high waist jean." I was still a bit skeptical about the jeans, but as I got used to the feel I understood what she meant by the tighter legs. I also knew the top she wanted me to wear. I never quite liked it, as it had no collar, the short sleeves stopped high on my arm, and it was not as long as I normally wore. I pulled it over my head and it came down to the top of the new jeans. At least with these pants it didn't leave a gap. Cheryl hurried me along as she wanted to get to the store as quickly as she could. If you didn't get to these sales soon enough, a lot of the bargains would be gone. She even said she would drive as she knew right where she wanted to park. I grabbed my wallet but as I tried to put it in my pocket, I realized the jeans didn't have rear pockets. "Cheryl, what's with these pants? There are no rear pockets." "Oh they're styled like that so it will have a smooth bottom; shows your rear a bit better. You're lucky to have a more rounded ass than most guys, so it looks good on you. I'll put your wallet in my purse if you want to take it." I was a bit perturbed by this, as I had never worn pants without pockets. Looking at the style I wondered if they were even men's pants, but she was out the door to the garage so fast, I just followed her. I could tell she was eager to go, as she drove as fast as the limit allowed. Inside the store it was pretty busy, with aisles filled with women. Something about a sale really draws them in. Cheryl knew where she wanted to go and we soon were looking through a rack holding skirts. She flipped through them quickly and found one she liked. It was a white jean mini-skirt, much shorter than she normally wore. I assumed it was for Pressley. Holding it up so I could see, she asked what I thought. "It's nice, but isn't it a bit short?" "Well it's a mini-skirt and cut to show a lot of leg. I think it will look cute. I wish my legs were long enough for these little styles, but I guess that's the way life is." I had gotten used to those kinds of comments before. Cheryl always complained that only being 5'2" tall limited her choices in clothes. Pressley was a bit taller like me, so I assumed the skirt must be for her. Cheryl continued to flip through the rack of mini-skirts, selecting one that was a black pencil style, straight with a wide belt and a pleated one in dark blue with yellow, green, and light blue flowers. With each one she seemed happy; looking at the prices, they were all marked 40% off. From the skirts Cheryl went to a section with blouses. Again she seemed to have a plan, picking out a white sleeveless blouse with ruffles cascading down the front, a floral tank top, a pale lemon stretch lace top with a round scoop neck and cap sleeves, and finally a sheer beige blouse with puffy sleeves and covered buttons. Once she had those, she moved rapidly to an area with dresses. She quickly picked out four styles that featured longer skirts, two with V- neck and two with a sheath design. Handing me the skirts and her purse, she headed off to the dressing room. This store featured little dressing room nooks, with only two cubicles for trying on articles. These were spread out in each department so you generally didn't have to go far to try on something. I felt a bit awkward holding her purse and the girl's skirts, so I tried to be as inconspicuous as possible. She reappeared to solicit my opinion on each one. After much discussion and comparing one with the other, she picked one V-neck and one sheath. She seemed really happy with these and mentioned to me that they were an incredible 60% off regular price. Cheryl loved to shop and when she could get a bargain it made it even better. Once she came out of the dressing room wearing her own clothes, she took her purse, but handed me the dresses to hold. It was becoming obvious that I was there as an assistant for her shopping spree. Again we wasted little time, and I followed her to an area with racks of pants. Cheryl plunged right in, flipping through each rack, occasionally finding a pair that drew her attention. She'd pull it out from the others, turn it around and check the style or cut. Just about every pant went back on the rack, but she did find three pairs she kept: a pair of skinny jeans in a dark blue denim with glittery designs on the rear pockets and down the side of the legs; a pair of dress pants in a camel suede microfiber with a side zip; and a pair of white Capri-length pants that featured notched cuffs and a row of three silver button decorations on each leg. Looking satisfied, she headed out of that department across an aisle into a men's wear section where there was a small dressing room. That seemed odd, as there was a dressing nook adjacent to the racks of pants. Once I caught up to her, she turned and motioned for me to give her the dresses and skirts I was holding. She then handed me the three pairs of pants. "Now go try these on. I think they should fit, but with pants you never know. I picked the same size 8 you are wearing, but if they don't fit perfectly we can try the next size up.' Out of reflex, I took the pants but didn't move. "But Cheryl, aren't these women's pants? I thought they were for you?" "Don't be dense; the pant leg is much too long for me. They should be just right for you. Just look at the jeans you're wearing now; Pressley bought them and after wearing them once, decided she didn't like the high waist look. You didn't seem to mind wearing girl's jeans earlier, so why now? Besides, I've wanted to get you some different looks for a while now, and these are 60% off and a great bargain. Just be quick about it, I had my eye on some new shoes and I want to get there before the sizes are all gone. Just come out, so I can see how each one looks on you; start with the jeans." I was really confused now and embarrassed as well, but she was so forceful I just went along. Inside the cubicle, I got even more embarrassed seeing my reflection with my floral panties after I took off my jeans. Pulling up the glittery jeans, I didn't like how they looked and it seemed they weren't a good fit. First they only came up just past my butt, riding real low on my hips, so my panties were showing. Second they seemed way too tight on my legs and butt. Lastly, the glitter look just seemed wrong for me. But I dutifully stepped out, so Cheryl could see. I stayed right at the door to the dressing area not wanting to venture any further into sight than I had to. She seemed really pleased at how they looked, having me turn around several times. She said the length would be just right with a proper shoe. She dismissed my complaints about the tight fit, saying women's jeans are designed to hug the body and show curves. Also, they were a low-rise style and I would just need to wear the pastel panties that Pressley had chosen as they would work with that style jean. As with my other objections, Cheryl just ignored my protests about not liking the glitter design or the fact that the rear pockets were fake and more for appearance than function. She hurried me back to try on the camel dress pants. I could tell they fit as I pulled up them up and they weren't as tight as the jeans. But having the zipper on the side made it real awkward and the flat front design without a fly made the absence of any male bulge very obvious. I tried to tell her I didn't like these, so there was no point in showing them to her, but she wouldn't have it. Once I came out, she gushed over them; the smooth front was just what she wanted and she loved how the microfiber fabric clung to my round ass. I blushed more as she talked, so I retreated back into the cubicle to shut her up. The white Capris really felt weird; they seemed like a cross between regular pants and shorts. Feeling the pant cuff hit just below my knee was unusual. Also, I could see once I had them on, that they were pretty sheer; the floral design on my panties was visible across my rear. This time I just pulled back the curtain on my cubicle and told her that they were too sheer. She just laughed and said it looked like I need a new pair of white panties for those. But she loved the style on me; saying it was just what she wanted. Shaking my head I changed back into my original jeans and joined her outside the dressing room. "Cheryl, I know these pants fit okay, but what do I need them for? I mean when would I wear the dress pants with the side zipper? Not to mention, the white ones; they are not practical at all. " "Well the dress pants are somewhat formal, maybe for eating out at a nice restaurant or if we go out to a play. And personally, I like the flat front. If you are comfortable tucking yourself, then it makes sense to pick a pants design that looks good without bulge; it's not like yours is that big anyway. Besides, they are such a bargain. As for the Capris, they are darling on you. Of course they are a casual look, so they would be good around the house, or for a cook out, or just shopping like this. Or for when you want to kneel between my legs to shower me with kisses and show me how much you love and appreciate me." With that she smiled, winked and leaned in to give me a quick kiss. Her description perfectly fit the last time we had sex; her sitting on the edge of the bed while I buried my faced in her pussy bringing her to several orgasms before she would allow me up on the bed for her to masturbate me to orgasm. After the kiss she gave me the clothes and handed me my wallet out of her purse. "Now do me a favor and take all these clothes along with your pants, and go pay for them over in the ladies department. You can meet me in the shoe department. I want to go ahead and start looking there." With that she headed off. I stood there befuddled with what was happening. I watched Cheryl hurry off toward the next sale. I thought about putting the pants back and not getting them. But I knew she would be disappointed and likely mad. I just reasoned that I would put off wearing them unless we were alone in the house. With that plan, I headed to the ladies counter and paid for the pile of clothes. Funny, even when women's clothes are on sale, they are still expensive. Once everything was paid for and bagged up, I headed over to the shoe department to find Cheryl. When I arrived she already had 3 boxes of shoes in a pile and was holding another pair. As I approached, she smiled broadly. "I'm finding more great bargains and luckily all the styles I wanted were available in the right sizes. The key to shoe shopping is to find ones that will compliment a specific outfit, like these darling yellow strappy sandals, or that are neutral to fit a range of clothes. That's why the first two pairs I picked were the nude pump and the black slingback. They can go from casual to dressy and will work with pants, skirts or even dresses if needed. Then I found a perfect pair of casual sandals. They were a bit trendy, featuring two broad white bands, a cork platform, and high-stack wood heel. I know just the outfit to pair them with. The great thing is the shoes are all a buy-one-get-one-free sale. So I can pick up four pair for the cost of two." She quickly showed me each one. I wanted to ask her if she didn't already have some pumps like the beige and black styles, but I didn't. I already knew she had a thing for shoes, as there had to be forty pairs in her closet. The one thing that really caught my eye was how high the heels were. She normally wore a shorter heel, maybe a couple of inches. The shortest one of this group had to be double that. "They certainly are cute, but aren't the heels a bit high? Aren't high- heels this tall hard to wear?" "I did go for a higher heel, but they really help elongate the leg. Besides it doesn't take that long to get adjusted to them. You just have to be willing to walk carefully until you get used to them. Oh, and you know the best part about this sale? If you buy 4 or more shoes, you can buy a handbag at half-price. I picked out this darling little mini-hobo bag in tan. It will go with almost any outfit and is the perfect size; just big enough for the essentials, like wallet, keys, phone, hair brush, and maybe a little makeup. I made that size mistake with the first purse I bought for Pressley. She loved this large style in pink and white. But after she got it home, she filled it with all sorts of junk and then could never find what she wanted in it and it was like hauling a suitcase around town. So the next few bags I bought her were more petite until she got the hang of it. So given a choice, a small bag is a much better option. Unless you want to look at some shoes, I'm ready to check out. We still need to swing by the lingerie section for some essentials before we can go home for lunch." I shook my head no and we went to the cashier to pay up. Again, even bargains are expensive; I can see why stores push shoes so much. As the saleslady rang up our purchases, Cheryl took the spacer material out of the purse and asked the clerk to cut off the tags. When it was clear of sales tags and packing material, she dropped my wallet into it. Smiling at me she whispered that now I wouldn't have to worry about wearing pants without pockets. We then walked to the lingerie section of the store, me holding my new purse, and all of her purchases while Cheryl chatted away about how much fun this was. Shopping was definitely a woman's hobby. Once in the lingerie section, Cheryl began browsing. She looked first at some night gowns, asking me which ones looked sexy. She finally settled on a white and black lace baby doll with a tiny G-string panty. She whispered that it would be perfect for our new found sex routine. That made me blush a little. I mean, I guess there is nothing wrong about a husband licking and sucking his wife the way we had been doing it lately, but it seemed as if Cheryl now preferred that to having intercourse. Although her masturbating me to orgasm was nice, it did feel as if she was more in control of our sex life than the way it used to be. Once she had handed me the gown to hold, she went over to some racks of panties. Looking at them, she began handling only white pairs. That made me blush again as I imagined they might be for me to wear with the Capris. But she seemed unable to find what style she wanted. Spotting a saleslady, she asked for help. "Hello, we're looking for a panty with a bit of control. Maybe a spandex fabric in white, do you have anything like that?" "Of course sweetie, we keep our control briefs over by the wall with the other shapewear. Most of the styles come in neutral colors like white and nude. Are you looking for a certain size?" "Yes, we need a size 5." "Well you should have no problem with that, are you looking for anything else?" "Yes, I'll need some camisoles as well, but I see the ones I'm interested in. Thanks for your help." "We do have a variety of camisoles, including some that have figure control. Those will be in the same area as the control briefs. Just let me know if you have any other questions or want to try something on." As she left, we headed over to shapewear. I could feel my face start to flush, as I realized Cheryl was looking for a panty for me to wear under my new girl's pants. The racks were filled with a variety of what seemed to me Victorian-looking items. I didn't even know that woman still wore such garments. There were restrictive-looking, long-leg girdles with what appeared to be reinforcing ribs around the waist, body suits of spandex with built-in bras, and a variety of panty-style garments with thick satiny panels for what I assumed to be added control. I could understand why Cheryl wanted a white panty, but wasn't clear on choosing something that looked so uncomfortable. I mean I took great pride in keeping trim. I didn't have a little beer belly like most guys my age or even any love handles. So if this underwear was supposed to keep things in check, it wasn't clear to me why I needed it. But it was embarrassing enough just to be here, so I kept quiet. She browsed liked she had in other departments, slowly flipping through the items on each rack. When she found something interesting she would pick it up, feel the material and even stretch it, as if evaluating its control capacity. Most briefs were rather plain, tending to be a full design unlike the other panties I had already. Cheryl didn't seem interested in these, but she finally picked up a panty that had a wide satin panel in the front, while the back was almost all sheer stretch lace. It only came in black and nude, but she liked the style, so handed me the nude color one to hold. "Do you like this one? I think it will give you a bit more of a smooth line under your new dress pants and it looks kind of cute. I'm sure your little buns will look cute through that lace. Most of these seem suited to older women, but I like this one." I was pretty embarrassed, so I just nodded my head in agreement. I was more interested in speeding up this shopping than discussing what I liked. Cheryl continued to look through the rack of briefs, focusing on the few styles in white. It seemed she had a certain style in mind, and must have found it as a broad smile crossed her face. She turned and held up a white brief for me to examine. It featured a wide panel of double material down the front which also extended around the waist line. However, the rear was reduced to a thong, wider at top, but still only an inch or two wide, which would leave the butt cheeks uncovered. "This is sexy. I wanted something that would emphasize your cute little buns in your Capris and this should do it. The thong design will not show through the white material, but should help shape your butt so it is more prominent and cute. I think there is enough material in the crotch to keep your boy toy flat and smooth too." Again, she handed it to me and went around the rack to where there were some camisole tops in similar stretch material. Flipping through the garments, she came across one in nude color that featured lace bra cups and a center control panel. The lace was identical to the lace on the control brief I was holding. Checking some sizes, she picked one and handed it to me. My head was really spinning now and I could feel my face glowing. But I just looked down and followed her lead as she went over to another area in the lingerie department. I could see that this rack also held camisoles, but these seemed to be made more of nylon or cotton, without any control features. Cheryl seemed to know just what she wanted here and quickly picked out three tops. Looking at them, I could tell why she wanted them. One was white with a floral print, an exact match to the panty I was wearing. The other two included a light pastel blue and a pale yellow lace. All of the camisoles, including the nude control style, featured triangular cups and adjustable straps similar to those on a bra. As Cheryl gathered these, I forced myself to ask her about them. "Honey, I understand why you bought the panties, but I don't see the reason for these tops. Why do we need these? I don't understand the style selection at all." "Think about it. Now that you have some cute underwear, do you think I want to see you wearing those hideous white tee-shirts with them? You need to update all your underwear if you want to look coordinated. Unless you would prefer to wear a bra with your panty, is that what you want? If so, I can get the saleslady to give you a bra-fitting. There are lots of cute bras. We could even get you a contour or padded cup that would give you a bit of shape of top. Is that what you had in mind?" I felt like my face went as white as the thong panty I was holding and discreetly shook my head no. Cheryl smiled broadly and I could tell she recognized my discomfort at this whole process. She handed me the selection of camisoles. "Well if you're sure you don't want to try on a few bras, go ahead and pay for your new lingerie and we can go home." I decided to cut my losses at this point before it got worse, and tracked down the saleslady we had talked with earlier. She rang up my purchases, commenting to me that there were matching panties for the camisoles. I nodded my head and told her that my wife had purchased those earlier. I tried to be discrete as I took my wallet from my new purse. Smiling she handed me the bag and told me to come back if I needed more. Even though I'm sure she assumed the lingerie was for my wife, I still felt awkward about the whole event. Finally we headed out of the store to our car. On the ride home, Cheryl was bubbling and excited about what great deals we found. She seemed like a proud hunter that had bagged a trophy buck, as she relived finding just what she had wanted to get only at discount prices. Back at our house, she told me to take the items upstairs to our room. She came into the room carrying a pair of scissors to cut off the tags. She worked her way quickly through our new clothes, sorting them as she went. There were two piles on our bed, one that had the underwear and the night gown, and a second that contained everything else. She took the shoes out of their boxes and put those on the floor. Going into our closet, she grabbed some hangers and told me to help her put the clothes on them. As I worked with her, most of the items she took into our closet, but she set aside the white miniskirt, the floral tank top, the camisole that matched the panties I wore, and the white platform heels. She then handed me the rest of the underwear to put in my drawers. It felt odd to remove my white tee-shirts and replace them with the camisoles, but I felt like I was on autopilot at this point. Once we had everything put away, she sat down on the bed next to the remaining items. "Go ahead and take off your top and jeans. I want to see how your new outfit looks. I'm sure everything will fit, but I'm dying to see it on you." I was shocked. She had pointed not just at the floral camisole, but the entire assemble of clothes. I shook my head as if to clear my brain. I stared at her with a puzzled look on my face. "My outfit, I thought this was for Pressley? You can't be serious about me wearing a skirt and heels? I mean why would I need these? They aren't designed for men." "Silly, I wouldn't buy anything for Pressley without her being there. She has her own style and is very picky about her clothes. Of course these are for you, but unlike the pants I didn't think we needed to try them on at the store. You seem so comfortable in women's underwear I felt you could easily adapt to these styles as well. I mean you have the long legs that are perfect for short skirts and high heels. Quit whining and try them on." My head was really spinning now, but I felt trapped. I slowly removed my shirt, shoes, and jeans. The camisole slipped on over my head easily and Cheryl smiled immediately, nodding her approval. The tank top and skirt also fit exactly, although it felt really odd to have my legs free without material between them. The shoes were a different matter; they fit, but when she told me to stand up I felt like I was on stilts. She encouraged me to take a step or so, and I did so gingerly. "Darling you look so cute! I love how it goes together so well. Of course, we need to get you looking smooth. Such a tiny skirt means you need to shave your legs all the way up and the same with your chest and underarms. They will look much nicer in all your new things, once we have your body shaved. It probably wouldn't hurt to get you a pedicure too. Oh, but I love this new look. Just seeing you stand there looking all sexy is getting me wet. It will be hard not to put you on your knees all the time. But walk a little more for me. I want to see how you do." I took a couple more steps feeling like I was going to fall over. "Cheryl, I can't wear this stuff. The shoes feel too awkward. In fact the whole outfit is uncomfortable. The skirt is so short, I feel like I'm totally exposed. The top is too skimpy; the straps from my camisole keep peeking out. How can I ever get to walk comfortably in these heels? Why would I even want to?" She laughed and motioned for me to spin around. I did so slowly, tottering on my heels. I felt like I was going to break an ankle. Finally she stood up and came over to me. Sliding one hand up my leg and the other on my waist, she held me a second to steady me. "The key to walking in heels is to take your time getting used to your new position. Take small steps; don't try to take a full stride like you normally do. You need to adjust to the high heel and how it alters your body position putting more emphasis on your hips. You will do fine, once you get the hang of it. I knew as soon as you started wearing panties, when I saw how you tucked yourself, that you would be a natural for sexy skirts and heels. Just seeing you this way is revitalizing my sex drive and desire for you. I know you're going to be spending a lot of time worshiping my pussy and showing me how much you love your new look. Pressley and I talked about it a lot when we decided it was a good choice for you, so she will be expecting to see you in skirts around the house from now on. Of course, we will still let you wear your new pants when we go somewhere, but at home we want you to show off your cute legs and butt. So try some small steps in your heels to get used to them. Just like the small steps you took in adjusting to wearing panties, it will soon be so natural to you that you will wonder why you weren't in skirts and heels much early. Just remember small steps will get you to where I want you to be." Smiling, Cheryl looked at him. His hair was long enough for one of those cute pixie cuts; that style would be a good place to start. Then she could transition his look to a bob cut, tapered from short in back to longer ends in front and full bangs. Maybe she would even get him some platinum blonde highlights, which would look good with his honey blonde natural color. Of course, pierced earrings would be necessary. She wanted him to wear big hoops, or dangling pearls. Something girly that would complement his new submissive behavior. His lips, full for a man, are naturals for lipstick, a bright red, or even a subtle coral would suit his skin tone. She would soon convince him that he looked good with makeup. That it was okay for him to wear some light foundation, blush, a little eye shadow and mascara all the time. Of course, Pressley would help him too. She loved fashion, makeup, and hair styling. She had already told her mom she would love to help him into a more feminine look. So far he had easily taken each small step she pushed him to try. She knew when he tucked himself for her and then tried on the women's pants that he would not refuse her now. So she was going to implement her full plan, one small step at a time. "That's a girl; keep your elbows next to your waist when you walk. Keep taking small steps."