I lost a Bet, Now I'm a Girl 💋(Crossdressing Stories) PART 2

hey there you're looking kind of cute please consider subscribing and check out our patreon for exclusive content let's have some fun I turned in the direction of under it all and walked slowly in the direction stopping before I reached the door there were a pair of mannequins one dressed in a burgundy bra and panty set and one in a Teddy made out of the same burgundy material with some black lace accents through the glass I could racks of nightgowns bras teddies slips and God knows what else the store wasn't empty either there was a woman

shopping with her teenage daughter a couple of women in business suits an older woman by herself and a young mother with a toddler in hand I also saw a tall trim middle-aged woman in a flowery dress who looked to be running the place and a couple of girls in their 20s who were probably the shop assistants as I was standing outside the door losing my nerve the woman in the flowery dress poked her head outside the shop glanced at the shopping bag from Laura Brown's that dangled from my hand and said you must be the

gentleman that Catherine just called about coming coming I followed her as she walked to the counter at the back the store was tightly packed and everywhere I went I plowed through wisps of softness I felt like the proverbial bull in a China closet a couple of the customers glanced at me but I couldn't tell what they were thinking now then how can I help you I told her about the BET and that I'd already purchased a skirt and sweater and that I needed some underwear do you know what you're looking for sir I just shook

my head not really no I guess I'll need a bra and a pair of underwear I just couldn't bring myself to say the word panties well that's still all right you probably don't know your size right I think she considered my blushing nod a sign of agreement I didn't think so take off your jacket and raise your arms I did as I was told and she took a tape measure and measured around my chest I was glad my back was toward the store because I couldn't imagine what anyone who saw this may have been thinking

looks like a 40 she said to herself then she raised the tape measure up a couple of inches up and measured again only this time she just wrinkled her nose and grunted softly were you planning on having breasts sir she asked I suppose I should do you have any preferences small large although she was trying desperately to keep a straight face I could see the traces of a smile dancing at the edges of her lips how could I possibly answer a question like that I felt like every time I took a breath I was falling

deeper and deeper into a hole I don't really know I hadn't thought about it I guess I'll go along with whatever you think is best you were going to say something like that she said almost to herself the hint of a smile was working it's way open now too I need to measure you again she said as she drew the tape measure around my hips and then again around my waist you're a seven or an eight in undies she turned around to one of the shop assistants Linda could you see if we have either lace

fantasies or pretty all day in a white soft cup 40b and 40c and matching undies in seven and eight for this gentleman she turned to me and excused herself I'll be back with you in a moment after I help these ladies I saw the woman with her teenage daughter doing their best to stare at me without appearing to even look at me I looked around for a hole I could drop into after a couple of minutes Linda tapped me on the shoulder and Spilled an arm load of white lace on the counter arranging it for

me I couldn't find a 40b in the Styles Andrea asked me for but I picked a few other things out these are really pretty she said as she arranged one of the bras over one of the undies she was right they were the undies had a delicate stretch lace V pattern in the front that was repeated around the legs the bra had a matching pattern on the top half of the cups and I deliciously imagined Carol in an outfit like this Linda smiled sweetly and said I'm sure whoever you're giving these two is going to

love them and at that point Andrea returned picked up the undies and held them in front of my pants to gauge the size I could see Linda blush a bit and stifle a giggle a still can't tell she picked up the other pair of the same style in a different style and held those up as well then shook her head well anyway you'll need to try this on to check the size she handed me the bra and started to steer me to the dressing room well this was going just a bit too far I thought

it was bad enough that I was going to wear a bra with my wife in the privacy of my own home but in a store in a mall no way I started to object but Andrea would have none of it don't be silly the dressing room is private use that one on the right she said as she pushed me towards it with the bra in my hand I closed the door behind me and took off my shirt and undershirt I slipped my arms through the straps as I'd seen Carol do a thousand time but I

was darned if I could reach behind me to hook it up as I struggled I heard Andrea explained to Linda what was going on that's so cute I heard Linda squeal so he's already got like a skirt and stuff I didn't hear Andrea's reply but Linda must have approved oh wow that's so neat I decided to cheat I took the bra off then turned it around so the hooks were in front of me I hooked it up then Twisted it back the right way and started to try to get my arms inside the straps again

you know though Andrea if he's going to wear tights how did she know that did the sales lady from Laura Brown's tell them what I bought these like pretty undies are going to be wasted and since he's a guy he doesn't have like hips or a waist right maybe he'd be better off with these I wish I knew what Linda was showing her but I was having a devil of a Time on my own I think you're right Linda these probably would work better I wonder if he's having a problem in there I heard her

muffle a giggle too maybe I should check she knocked on the door and walked in without waiting for me to answer oh my you seem to be having some difficulty here let me show you the first thing is that you haven't adjusted the straps properly you're going to need as much length here as you can get she fiddled with this little buckle-like thing and then pulled the cups down a bit uh that should be easier she said as she helped guide my arms through the straps usually you'd put your arms in first and then hook

it up but I'll bet you hooked it up in front first right I just nodded I thought so you'll get better with practice what did that mean I thought she smoothed out the straps tugged on the cups tugged on the back ran her finger around the back this fits well here so I think we have the right size we don't have this size and a smaller cup though what are you going to hear she asked as she tweaked my empty cup I'll probably just stuff it with something I mumbled socks don't work very well she

said they get lumpy and they just don't look right we have mastectomy forms but they get very expensive I blanched what you can do though is to buy a pair of knee-highs and fill them with about a cup and a half of bird seed or you could even do the same thing with a baggie and about the same amount of water both will fill these out nicely stay right here I'll be right back she didn't close the door to the dressing room behind her so I lunged toward the doorknob just as that teenage girl walked

past me towards her own dressing room I could have died after a couple of minutes Andrea knocked are you decent she said but she didn't wait for an answer before she came in this is called a waste Nipper she said it's a girdle with a high waist wear your tights under it and they won't sag but more important it will give you a little definition here and she put her hands around my waist and here this is an XL and it should fit but I think you should try it on you'll have to leave your

underwear on here she gave me the girdle and left again without closing the door I was out of my league not only could I not figure out which end was the front I couldn't imagine how I could put these on over my boxer shorts I just held them stupidly until Andrea knocked again and opened the door problems she explained they go on this way she explained knowing me which Whitney was the front wiggle them up your legs and when you reach the top pull up the waist then hook all these Hooks and you're all set

by the way these will never work with the undies you're wearing now I brought you some panties you'll have to buy them but they're on sale and I'll discount them when we ring up the sale let me know when you're all set the panties were simple white briefs for which I was grateful after she left I slipped out of my boxers and put on the panties which seemed to fit like a second skin then I slid the girdle up my legs pulled up the legs and hooked the hooks just as instructed it took some effort

to attach all those hooks but when it was all done it didn't feel all that uncomfortable in fact I was more than a little excited and I'm not sure that this wasn't obvious when Andrea came back into the dressing room this time without knocking I think this is just about perfect she exclaimed as she tugged a little on the legs and then ran her fingers around on the top band don't you think so I nodded mutely oh don't be such a fuddy duddy this will give you a nice girlish figure and who knows you may

enjoy it get dressed and bring your things to the counter and we'll ring you up as soon as she left I got out of those things as quickly as I could which frankly wasn't all that quick as I was still having some problems with these hooks eventually though I was back in my flannels and jeans and standing in front of Linda at the cash register with my new Treasures she took the bra girdle and undies from me and elaborately folded them while placing them back in their boxes will that be all sir she asked um

yes would you like to join our bra and underwear Club buy 10 panties or five bras and get one free I just stared at her it's a promotion we're running right now and I have to ask she said with a conspiratorial Heir but it is a really cool deal if you're interested I don't think so I replied she rang up the sale and handed my purchases thank you very much and we hope to see you again soon sir she positively beamed I mumbled my thanks and tried to get out of the store as quickly as

I could without knocking anything over I left the store and took a deep breath while I felt some relief I don't know whether I was more relieved that it was over or that I didn't die from embarrassment I didn't think I could do what I just did but I did and Catherine Andrea and Linda were all nice and my Essential Parts hadn't dropped off when I tried my new skirt or my bra this may not turn out to be as bad as I thought I assessed what I still needed to do I needed shoes and

I needed to do something about my hair and makeup I didn't remember if Catherine recommended any shoe stores so I just started to circle the mall the first shoe store I saw was all athletic shoes and the next one had a clerk who looked like Al Bundy leaning on the counter I just couldn't see asking him for help so I walked on a few more stores down I saw a store that looked promising all the shoes in the window were women's both casual and dress and both of the clerks were women in their 20s one

had short black hair and the other longish brown hair pulled back in a ponytail there were customers in the store right then I went into the store and started looking around while the two women continued to chat with each other after what seemed like an eternity the one with black hair asked do you need some help I walked over to the counter I think I do I had a bet with my wife and I have to watch this Sunday's game in drag right now and I raised my two bags all I need is shoes oh

really the black-haired one said raising an eyebrow this could be fun she remarked to her associate do you know what you're looking for why did everybody ask that question I thought not to myself uh no not exactly whatever fits and whatever goes with what I've already got I guess can we see she asked sure I suppose I gave her the bag from Laura Brown's she pulled out the skirt and held it up against my waist I wasn't expecting this there were no racks to hide me just a big wide glass storefront that was open to

the entire mall I quickly backed away but she reached out and put her hand on my shoulder I'm sorry I didn't want to embarrass you I just wanted to see what we have to work with Okay I nodded that's a pretty skirt and we've got lots of things that will go well with it what else are you wearing I pulled out the sweater and the brown tights oh that's very smart you're gonna look great honey don't you think he'll look cute Susie she asked her partner absolutely they were talking to each other as if I

weren't even there what do you think penny loafers might work or faux alligator loafer maybe Susie picked up a couple of shoes from the display and held them up for my approval they both looked fine to me but what did I know they're a little plain Susie the black-haired woman said I think an outfit like that needs something with a little more character she turned to me why don't you have a seat sir as I was doing what I was told she reached into a little box on the counter take off your socks and these

on or we'll never get a proper size she handed me a couple of little balls of nylon that I found out later were called pian's it took me a second but I got them on I felt like an idiot by this time Susie had gone off to help another customer who was looking wearily at me my sales woman squatted down with that Contraption they use for measuring foot sizes and after fiddling around a bit told me I was a nine and that she would be right back and that I should relax how many times had

I heard that today just as promised she came back with an arm load of shoe boxes as she tried on shoe after shoe on my feet she kept chattering away at me and I didn't hear a word I was Frozen with fear that someone I knew would see me trying on women's shoes over ped covered feet in this glass enclosed shoe store in the middle of a popular Mall she tried on big heels and little heels and shoes with straps and shoes that covered my toes and shoes that didn't cover my toes and some of

them fit and some of them didn't but at this point I was Dazed so what do you think she was expecting me to make a decision and my mind was absolutely blank I looked down at my feet and for reasons I'll never understand like a bolt out of the blue what I saw made sense I was wearing left foot only a two inches clunky heel with a big Brass Buckle and an open toe and I liked the way it looked and I like the way my foot felt in it I think those will be fine

I squeaked I thought so these will look really nice with your outfit they really do go together she put the other shoe on and told me to stand up I did and shook a little when I got upright but then felt fine I thought the shoes looked great and my feeling of weirdness completely disappeared until I saw one of Susie's customers grinning at me I sat down in a hurry and my black-haired sales woman smiled and said don't worry about anything you'll never see her again and besides you've chosen a really great pair of shoes

she took off the shoes and put them back in the box and headed back towards the register I couldn't figure out what to do with the pns so I put my socks on over them and followed her after she rang up the sale she asked will there be anything else oops sorry force of habit took my credit card and finished up I thanked her and as I was leaving she gave me a wide smile and told me to have a real good time okay by the way we'd love to have a picture if you're okay

with that must have blushed a dozen shades of crimson as I walked out but to tell the truth I wasn't sure if I was blushing because I was embarrassed or because I was beginning to realize that I starting to like the idea of what I was doing the last thing on my list was hair and makeup I knew that if I went into the local drugstore and bought a bunch of stuff and did it myself that I'd look more like Bozo the Clown than anything else but I had no idea of what else to do

I knew I needed help but a beauty salon the idea seemed ridiculous but having already tried on a skirt a bra and three inches heels how much more ridiculous could I get thanks for watching check out patreon if you want to have early access to the other parts if not it will be online in a couple of days