The answer to Blake's question had of course been a yes, in no uncertain terms. So quickly he found himself wearing nothing but the panties and bra he had been given to borrow as Liz left the bathroom. The sense of bliss from just jerking off still filled him, but like all of the emotions he had felt this day it was mixed with much more, making him feel conflicted with his own body. He had been instructed to change his underwear while she was gone and to make sure her favorite part of his anatomy was tucked away, nice and safe. The comment had been accompanied with a flirty wink, the type that often made him want to kiss the young woman. Looking through the bag with his new underwear in it showed him that he had more than a few options, but not a one of them was a good option. Closing his eyes he grabbed one piece of fabric, just leaving it up to chance. One thing was just as bad as another and this way he could tell himself he didn't actually pick out panties to wear.
When Liz came back into the bathroom with a red halter dress and a box with a pair of shoes in it she gave her boyfriend a sly grin when she saw the pair of panties he chose. While she had shown him the video on how to tuck and had helped him the first time, it still felt a little amazing that Blake looked flat as a girl. Her little man wasn't endowed, but still it didn't feel right that a boy's manhood could just vanish from sight. "Good choice, now lets get you changed!"
Getting changed didn't take long, it was just a dress, a snap button behind his neck and a piece of cloth to tie around his waist. The entire thing made him want to maybe die, but not die in the dress, he was sure that would only bring him back as a ghost with things left undone and knowing his latest round of luck he would be wearing the stupid dress even as a ghost.
The first thing he wore was a new pair of panties, the random choice he made hadn't felt like a good one and tucking his dick was not comfortable. Pushing his balls back up into his body was the worst of it, but there was no actual pain involved like he originally thought there would be. So with his dick pulled back between his thighs he had everything in place before his girlfriend got back. The panties were the same type as the last ones he held in his hand out by the van, cheekie panties, but these were black with white polka dots and a white lace band around each of the garment's three holes. The dress itself was a red halter type dress that covered himself all the way up to his neck, but left his shoulders and upper back completely bare. The thing didn't even come down to his knees, leaving him feeling more than a little exposed. That was when he felt a snap and a sting on his back as the bra he wore was used like a rubberband. "Ow!"
"We should have changed your bra, this dress leaves your bra exposed, but I guess it will be fine for just a little fashion show," Lizbeth said, completely ignoring his cry of pain, that she was sure it was more from shock after having it done to her so many times growing up, like every other girl. "Now we just need you to try on your shoes, a girl trying on her first pair of heels is an important moment. I just wish I had my camera to remember this moment, my little Blake growing up to be a beautiful young woman."
"Liz... please don't and do I have to wear those?" The shoes in the box weren't some six inch stilettos that would turn him on instantly if Liz was wearing them. The ones he was about to wear were two and a half inch white heels, with a buckle strap that would go across the middle of his foot, with the heel itself being something between a stiletto and a block, he wasn't really sure what it was called, but he knew he didn't want to wear them.
Flipping up the back of the dresses skirt Lizbeth gave a single hard smack to the back of her feminized boyfriend's rear. "That is Miss Liz to you young lady."
Quickly putting both hands over his butt as he spun to face his girlfriend Blake didn't feel anger, just shock and a tiny amount of pain. "Did you just... spank me?"
"I did and there is more coming if you don't act like a good girl for me. Now put on your shoes, we have a few outfits for you to show off."
The fashion show was mortifying to Blake, he was positive the blush on his cheeks was evident as he went down the stairs, careful to hold the guard rail. The heels weren't high, but he still felt like he was going to tip forward and fall down the stairs to his doom. Once down there Heather, nor David sudden pointed out that he was a man in a dress, a fear that really hadn't gone a way, but the way the older woman gushed over him, how cute he was, turning to prod her son to agree amped up his other fear... that him as a twenty year old man passed so completely as a teen girl.
"Blake." Heather said, looking the brunette haired girl up and down. The teen girl was far from graceful, but she did look cute as a button and clearly embarrassed with her rosy cheeks. "You look so pretty!" she said encouragingly, wanting the girl to feel confident, remembering her own body image issues when she was younger and didn't understand her own worth. "David, is't Blake pretty?" she said turning to her son who sat on the couch, the phone in his lap, forgetting the second he noticed the girl he was crushing on descending the stairs.
"You are beautiful Blake, I love your... outfit, you look amazing!" David almost said your everything, and wasn't sure he had actually stuck the landing on the compliment.
The compliments weren't doing anything for his self image, the outfit made him feel exposed, the shoes were tight on his feet, the strap wasn't digging into him, the fit was correct, but it still felt wrong. The extra height was nice, but not at the feminine price. "Thank you.. And Mrs. Mauro, thank you for buying me clothes. I really..." His words grew softer as his mind grew louder. 'Hate them, you should be wearing them, Liz should be wearing them, any one really but me!' While the words he thought were firm, the mental tone made even his own thoughts feel like he was whining, but despite what his inner monologue thought, he still played the part Liz needed him to, but he wasn't sure how much he could take, blow job or not. "Really, just feel so overwhelmed, thank you."
"You are so very welcome dear, I'm glad to help. I just wish you could have gone shopping with us." Heather turned her head only slightly to look at her son, knowing he would have hated going on a shopping trip and she was equally positive he was glad the pair had gone to the movies over giving the girl up to her mother.
"Mmm, maybe another time," he said uncomfortably thinking it sounded like something she would want to hear.
The entire time he was downstairs Liz, who followed her dress wearing boyfriend, just stood there silent, enjoying every second of the Mauro's reactions. Wanting more she walked up to Blake, putting one hand on the small of his back, the thought of snapping his bra strap a second time entering her mind before she dismissed it. "That is outfit number one, let's try on another!"
When he changed into his next outfit he got a new undergarment that he hated more than the current bra he was wearing. Blake found out he was the not so proud owner of what Liz called a magic strapless front buckle push up bra and the way it pushed on his pecks, making them appear feminine seemed like a rather dark kind of magic. He still found the bra stuffed with the flesh colored filets that he had in the last bra and when he got fitted into the next dress he really hated how it made him look. The dress itself was white with black polka dots with ribbon like straps that came up from the bust to tie behind his neck, another type of halter dress that had yet another black ribbon that tied around his waist and of course he still had to wear the white heels.
"You look cute enough to just eat!" Lizbeth said with a large toothy smile. "Now remember this is one of the dresses Mrs. Mauro picked out, so when you get down there you need to do a little spin on the ball of your foot and give her a big smile, thanking her for the pretty dress. You can do that for me? Right?"
"Yes..." he said in a small voice. "Liz..." he said before he was cut off by his girlfriend pointing her index finger in his face.
"Blake, honey. You need to remember that I'm an adult and you are a teen girl. You know what to call me," she said with steel in her voice. It wasn't her normal character to be bossy or really talk with a commanding tone but the change in their relationship dynamic with the role changes had her enjoying the feeling of being in charge. She had some freedoms, but felt like so much of her life was still controlled by her parents. They treated her like a kid, she was twenty one and they still had a curfew for her. Sure they allowed her to work, but she worked from home and wasn't allowed to move out if she wanted them to pay for college. They said it was so she could still enjoy being a kid without having to worry about bills and other adult things, but that didn't change how much it irked her. While Blake got to go off to college, be on his own and meet other people. She didn't think he would cheat on her, but it didn't change the moments of insecurity she felt when he didn't get back to her till the next day after she texted him. She really cared for him and tried to soften what she had just said by speaking in a softer voice, and touching his forearm. "Honey, you need to stay in character. You don't want to slip up in front of others and give yourself away do you? I'm only being hard on you to protect you."
While he had been about to tell her he wasn't sure he could do this any complaints he was about to say died on his lips, first from the sudden physical reaction Liz gave him and second from her concern, he really didn't want to be found out. "I get it... thank you Miss Liz."
The second trip down the stairs was about as harrowing as the first and the reactions to what he was wearing this time only made him blush more. Moving to the living room he did as his girlfriend said. Teetering on one foot he did a little spin and gave the biggest smile he could manage without looking like he wasn't the massive phony he really was. "I just love this dress Mrs. Mauro, it is just so perfect!" Without really thinking about it he bent his ankle to the side, bending his foot to try and adjust his heeled foot to be more comfortable, an action that didn't help at all.
"You look just lovely Blake, I'm so happy you like it." Heather said, taking notice of how she was moving. "Don't worry about your heels honey, they just need to be broken in, but if you like I can show you a trick that can help them feel more comfortable."
"You can do that?" His very short time in heels wasn't bad, but it made Blake appreciate why Liz didn't wear them often.
"Sure, I'm sure your mother could tell you all this, but since I'm around , I don't mind filling in a bit," she said with a smile. "We are going to do two things. First we are going to put them down on a towel and use my hairdryer on them, not long, just around ten to fifteen seconds. Then you will put them back on, but you will be wearing two pairs of socks and will walk around them for ten minutes. Then we just repeat a few times and when we are done you will be able to feel the difference."
"Oh..." Blake said realizing he had somehow volunteered himself to wear the feminine footwear for longer. "Great, just what I need."
The second outfit felt worse than the first to Blake, but he thanked his lucky stars that they at least kept David from speaking. He had gotten enough compliments from the dark brown eyed boy, so he at least had that going for him. Though it hadn't stopped the teen from staring at him, Blake had been keenly aware of that. While Blake felt lucky the boy hadn't said anything, downstairs David was feeling like an idiot from being tongue tied. By the time he could speak, to tell the girl what he thought about her outfit it seemed like the moment had passed, her and his mother had been talking about secret tips only girls knew about how to break in heels and he felt stupid for missing his chance.
"Okay Blake, we only have one more thing to try on and I think you will be happy about at least one part of the change," she said motioning her boyfriend to sit down on the bed so she could unbuckle his shoes.
Seeing the shoe box in her hands Blake whimpered, thinking he was about to change into another pair of heels, this time probably higher, high enough that he was going to break his neck. "Miss Liz... can we not?" He said this time using the correct moniker for his pretend babysitter.
"Honey I know you love what you are wearing, but part of a fashion show is changing. So we need to take off your heels for something more comfy."
The change in shoes ended up being a pair of slippers with little bunny faces and short floppy ears on the front. They were a world of difference in comfort for Blake, but he wasn't really sure they were much better. What he changed into for his outfit on the other hand felt so much worse. It wasn't a dress, it was a nightgown, or nightie as Liz put it. The purple satin thing had a ruffled lace collar and at least felt like it didn't even cover the panties he wore. Blake put it on, tugging and holding the bottom down as his embarrassment felt like it was at a critical mass. The fact that the soft, silky, fabric felt so wonderful gliding across his shaven body, making his skin practically feel alive wasn't mixing well with his recently endangered self image. "Do... do I have to go downstairs like this?"
"You do honey, best to get it over with now. Besides this is what you will be wearing to bed tonight," Lizbeth said, running her hand down her boyfriend's side, feeling the satin garment and the magic strapless pushup bra still underneath. "I thought you would like this, you can hardly keep your hands off me when I wear something like this."
Blake wanted to tell her this was different, very, very different. The problem was, he did like touching his girlfriend when she wore silky garments like this. Blake of course almost always wanted to touch her, feel her smooth and supple body, but he particularly liked touching her when she was wearing things just like he was wearing and despite his protests liked how it felt on his own skin. "Okay... please tell me this is the last one," he said pleadingly.
"No more changes after this. You can stay in that till the morning and hopefully whatever dress you wear in the morning will be your last." She of course wasn't hoping that to be true, she wanted to help her boyfriend get out of the situation with both of their reputations intact. The thing was though, that she hoped that dressing up continued as a little bedroom game in the future. Blake had so many cute outfits, it would be a shame for her princess to never get to wear them.