Debra
by Janet L. Stickney
As the sun set, it cast a glow through the trees it reflected in the mirror, and what I saw made me feel a bit better about what was happening. I once again checked myself in the mirror, still shocked at how I looked. The dress was snug but not tight, my legs looked long and sexy, my makeup wasn't overdone, and my hair looked perfect to me. It took a bit to get used to the longer nails and the heels, but after a bit I finally managed to figure it out. "Debra" I had been dubbed by my mother for that night.
"When is Tom coming by to get you?"
"In a bit mom."
"You look quite lovely as a girl, did you know that?"
"Yeah, thanks mom. Just what I always wanted to hear."
"Well, it's true honey!"
Just then Tom rang the bell and mom opened the door. That's when Tom saw me for the first time. "Damn!" he said, then grinned. Mom told us to have a good time, then surprising me, he took me by the arm and led me to the car, opening the door for me! Starting the car, he glanced over at me.
"What are you looking at Superman? Your x-ray vision won't get you anywhere, even if it worked!"
"Maybe, but damn! It's just that you look way better than I expected! In fact, you look great! Nobody will know that you're a guy! No chance at all, especially not looking the way you do!"
"Sure they will! My voice!"
"Just talk a little softer, and who knows? Maybe you'll be able to pull it off, being a total girl I mean!"
"Tom, I don't want to pull it off! This is a costume party, remember? It's only a costume, and I'm only doing this because you said it would be fun! It was my mom's idea to dress this way, not because I want to be a chick!"
Tom had been invited to a summer party, then invited me to come as his guest, telling me that it would be a good way to meet chicks. Fat chance of that now! He didn't say what his costume was going to be, and I never told him what I was going to wear since I wasn't sure, but when I told mom, she suggested going as a girl, then fixed me up so that I looked like I stepped right out of the sixties! I was wearing a pink mini dress with a jacket to match, and a small ugly little pillbox hat. Just about the only good thing about appearing like I that was that nobody I knew except for Tom, was going to be there. In another blow at not only how I looked but also my ego, he took my hand just as the hostess let us in.
"Hi! I'm Christie!"
"I'm Tom, and this is Debra."
"Superman and Jackie! How cute! Come on in! Everyone is out back!"
Still unconsciously treating me like a girl, he slipped his arm around my waist, then he and I went out back and joined the other people there. All sorts of costumes from aliens to mythic figures and superheroes were represented. I did not see any other guys dressed like a girl, although I might not have been able to tell either. Tom took me around, making things worse when he began to introduce me as Debra to everyone! Even though I wasn't sure that was the right thing to do, I didn't stop him from doing it. I did not want to embarrass myself, which probably meant that everyone thought I was a girl dressed like Lois Lane or maybe Jackie Kennedy. So, based on everyone's reaction, and rather than expose myself to ridicule, I decided to take his advice, and started talking softer, thoroughly stunned that so many people simply accepted me as a girl. I wasn't sure that I looked quite that good, but rather than correct Tom's introduction, and I still don't know why I did it, I quickly started paying more attention to my mannerisms. It was okay though, I told myself that it was just to protect myself, especially after he introduced me to everyone as Debra. It wasn't as if we were a couple or anything like that, but the other's might have thought so, and after the reception I got, I found myself unwilling to ruin the illusion. It was a matter of both shame and pride I guess. It was a fun party with some games, food and music, then…
"Say…ah…Deb? Could you give me a hand? In the little girls room?"
"Ah…sure, but…"
"Great! It's right in here." Once we were inside the bath…"Would you untie me honey? This corset is just killing me!"
Not having much choice, I unzipped her dress, she quickly slipped it down to her waist, then I untied her corset. Before I could leave she unfastened it, turned, and yanked it off. She had a perfect pair, trust me on that, but since she thought I was a girl, I couldn't just stare, so ignoring my natural instincts, I looked at the floor instead. I zipped her back up, and the two of us returned to the party. Still shaken by what had happened, I went to get something to drink. I did not see Tom until just before he walked over, scooping me into his arms, leading me to the dance area. Rather than make a fuss, I went along with it, but…
"Damn you look good Debra! Almost good enough to…"
"Tom, get a grip! Remember who I am!"
"Kind of hard, what with you looking like this… the way you do!"
"Everyone thinks I'm a girl!"
"So? What's the matter with that?"
"That girl? I just helped her take her corset off!"
"That must have been fun."
"Yeah, it would have been, if she didn't think I was a girl!"
"Still…"
"Tom!"
"Okay, okay! I get it, but you still make one hot looking chick!"
"Geesh!"
Later that night when we started to leave, the hostess, Katie hugged me, then Tom. As he led me out to the car, I knew for sure that not one person had read me as a boy dressed like a girl! Tom walked me to the front door, and while I thought he might try to kiss me, he merely squeezed my hand and smiled at me before I went in, only to find mom sitting there waiting for me to get home. She asked how it went, I told her it went fine, then I went to my room and undressed, washed off the makeup and went to bed, only to lay there wondering how so many people could be so stupid not to recognize me as a guy! The next day I was back to being a guy, and went to the kitchen to remove the nails. I was busy setting out things when Tom drove up. I let him in, and saw that he wasn't grinning.
"Bad news kiddo. Katie called, She wants to have an all girl get together, friends of hers I guess, and she invited you!"
"So? Tell her I can't make it."
"Ahhh…I would, except that I can't."
"Why not? It's easy! Just pick up the phone and tell her!"
"Like I said, I can't do that, not right now anyway."
"Okay, I'll bite, why not?"
"Well, I sort of…I like Katie, a lot, and I've been trying to find a way to ask her out, but when you and I went to the party together, well, now she thinks we're a couple! That's why I need you to go! So you can tell her we aren't together! That way I can ask her out without getting a lot of flak."
"And that would leave me…?
"Single, unattached, and not there, not after this little get together anyway."
"Let me get this straight. You want me to become a girl again, go to this hen party, then not only try to convince all of them I'm a girl, but then tell Katie that we're not a couple, just so you can ask her out? Have you thought about how crazy that sounds?"
"Yeah, I know, but I really need you to do this for me, and I'll owe you big. Real big!"
Tom's dad had his own company, and having him owing me big wasn't something I could just ignore, so while I wasn't eager to dress up like a girl again…
"When?" I asked sullenly.
"Today. At two this afternoon. Casual she said."
"This is crazy Tom! All it would take is just one girl to figure it out, and I'm done for! But, if I do this…"
"Thanks! I'll be at home. Give me a call when you get back, okay?"
"Yeah, I'll do that, if I go that is."
Tom sped away, leaving me to wonder how I had gotten myself into such a mess and why I even considered doing it again! Me? Going to a hen party? But, since I had almost said I would do it, so I went back in the familyroom to find mom, and tell her what happened. When I told her what had happened the night before she giggled, but when I told her that I had been invited to an all girl get together that afternoon, she quieted right down.
"You do know how dangerous this is don't you? If just one of those girls thinks you're a boy…"
"I know mom, I told him that, but if I can pull it off, Tom will owe me big, and maybe I can get a job at his dad's company later!"
"Well, if you think you can do it, I guess I'll let you do it again, but you don't have anything to wear except that one outfit you wore last night, and it would be tacky to wear it again! You get cleaned up and I'll slip out and get you something to wear. Casual but nice, okay?"
"Sure; thanks mom."
By the time mom returned I had taken a shower and shaved. She came into my room and set some things on the bed, telling me to get something on, then she would help me with the makeup again. When I was ready mom watched as I applied foundation and powder, then eyeliner and eye shadow, a bit of blusher, then she used a blow dryer on my hair to make it fuller. Using some hairspray on it, she waited a bit then brushed my hair in a very feminine coiffure I wasn't sure was even possible before she went and did it. Back in my room, she handed me the bra, the one I used the night before and the twin bags of birdseed I had used to fill the cups. Then came the padded pantybrief, pantyhose, a slip, and finally, the dress that mom held out. It was blue with white checks, two straps, and had a full skirt. I slipped it on, mom zipped it up, and stepped into the white sandals she had bought, then looked in the mirror. The top of the dress wasn't low enough to show anything, but the hemline was above my knees and the dress was tight around my middle. Handing me the earrings, mom watched as I clipped them to my ears, then she fastened the white choker necklace around my neck and handed me the perfume. I used it, then put on the pale red lipstick. It was as good as it was going to get.
"I never knew…what I mean is, I didn't see it before yesterday, but you really are quite pretty…Debra!"
"Me neither mom, thanks."
"It's almost time to leave honey, let me get you my white purse." When she returned…"I also put a wallet in there. You better put your things in that wallet, just in case."
I did what she said, then hugged her just before I stepped of the cliff of common sense, with no idea that I would soon find myself drowning in a sea of confusion, being pulled in several directions at once. Mom should have been outraged that I didn't mind dressing as a girl, and in fact, had willingly agreed to attend an all girl gab fest at Katie's house. I mean, I was her son, and sons don't want to dress up as girls, right? Part of my confusion came from the fact that she didn't get upset, angry, yell, or even shout at me. Quite the contrary. She was helping me and I didn't know why. Trying to forget all that I drove to Katie's house and walked to the door. She let me in, then she and I went out back to sit at a round table. There were no other girls there, and I assumed I was the first, but she dashed that idea rather quickly.
"That was really good last night, when you undressed Jeannie I mean, I almost burst out laughing!"
"What?"
"Oh come on Deb, we both know that you're not a girl, although I don't think anyone but Tom, me and you knew it last night! You look just delicious! Did you know that?"
"Tom told me that too."
"Did he! Well, he should know! Now tell me, is this a…regular thing for you? What I mean is, do you dress up very often?"
"Last night was the first, but…"
"But you're here right now, all dressed up again! Why? If this isn't your thing I mean."
Since she knew that I wasn't a girl, I decided to tell her. Why Tom asked me, how he wanted to ask her out and all that. She giggled when I told her that, but got serious when I told her that I was going to need a job soon, and since Tom would owe me…I figured…why not do it?
"Yeah, I knew that Tom wanted to ask me out, and I will go out with him, but there is something else; the real reason I asked you to come over. My brother thinks you're really hot Deb. He almost asked you out last night, and would have, except he likes Tom, and wouldn't get involved because he thought you two were together."
"You know I can't do that Katie!"
"Sure you can! Guys are so easy Deb! Just go out with him a few times then drop him! He'll never figure it out, especially looking the way you do!"
"I don't like guys Katie! I'm not like that! This was supposed to be a costume, not a way of life!"
"Maybe, but think about this; Jeff is kind of shy, not the kind of guy to force himself on a girl, and besides, you're the very first girl I've ever heard him ask anyone about!" She sat back, obviously thinking, then…"How about this? You, Jeff, Tom and I can double date! That way everyone gets what they want, and nobody gets hurt!"
"Yeah, maybe, but after that…"
"After that you let him down, easy of course, then you'll be out of it!"
"Do you have any idea how crazy this all sounds? Me? On a date with your brother? What if he tries to…"
"You more than anyone should know that guys think with their toy, which means they'll do anything if they think they are going to score; only I don't, and I don't know any girls that do, let a guy very far past putting their grubby little hands on a breast, and that's outside of our clothes! Now, will you do this for me?"
"This is nuts" I said.
"But everyone gets what they want Deb! The guys get the date they dream of, we get to get all dolled up, plus, we'll make them take us some place nice, like….Mario's!"
"What if I don't want to get all dolled up?"
"You say that Deb, but there aren't many guys that could look the way you do, and even fewer that can actually get away with it, so I'm thinking that maybe you're protesting to much! Come on Deb! We'll go shopping, get some sexy underwear and some knock out dresses! Maybe new shoes too!" When I didn't say anything…"How about a trip to the beauty shop? We can get our hair and nails done! We'll look so good the guys will be drooling all over themselves!"
"Katie, why bother with all this? I mean, all I have is the rest of the summer, then it's back to school! If any of the other kids find out about this I'll be dead meat!"
"Believe me, nobody will ever guess who you are, and you know that! What about our star quarterback? Wasn't he trying to get you alone last night? And what about Jeannie? Did she know? No! Quit worrying so much! You look terrific!"
I sat there looking at Katie, wondering if she really realized how dangerous this was going to be. One slip up, one mistake, and my name would be mud, or worse. Then, her suggestion that we both hit the beauty shop! While maybe fun for a girl, that wasn't very high on my list, so my getting all dolled up as she put it and making me look great, would have to fall to my mother. Plus, just the thought of asking mom to help me get ready for another outing, especially a date, really made me queasy. But Katie was right about one thing, I actually didn't mind dressing as a girl at all. I wasn't in love with it, but it wasn't that bad, and making the guys take us to Mario's sounded pretty good to me, which is when I committed my biggest mistake. I nodded my head yes. All at once Katie said that she would set it up for the next Saturday, and make all the arrangements at the beauty shop, but that I should be at her house on Friday, so we could find our dresses!
"If you're not real busy, lets go troll the mall…it'll be fun, and maybe we'll get some ideas for next weekend!"
I felt like I was letting myself get sucked into being a girl, something I never thought possible, and wondered why I didn't object more. Maybe I should have, because as Katie stood up and started towards the door, I found myself unable, maybe even unwilling, to say no, go home and change as fast as I could. Instead, she and I drove to the mall, and started down the huge concourse. I wasn't concerned about being found out, I already knew how I looked, so I concentrated on walking like Katie, and using my hands and arms the way she did. She and I went into a dress shop where I watched her try on some really outlandish dresses, something I knew she wouldn't wear anywhere, but were obviously fun to try on. Then she and I went into a small costume jewelry place. Intrigued, I started looking at all the earrings and so on, and got caught up in all the glitter I think. But almost all of the good ones were post, and I needed clip, so when I asked about that, the girl offered to pierce my ears for free!
"Oh go on Deb! Might as well get it over with, clips are out out out! Be a new century woman! Go for it!"
Caught up in the excitement of it all, and in a fit of unknown femininity, I had my ears pierced, then bought several pairs that I liked. That alone made me feel very much like I fit in with Katie, and I did not say a thing when she commented on what she said was my new attitude. By the time we got back to her house I had to leave, so I dropped her off and went home, promising to call her. When mom saw my earrings, she must have known something was up, because…
"Well! Look at you! New earrings! And you seem to be…really comfortable? Is there something you want to tell me? Like how you came to have rhinestone earrings? And how was that little get together? Did you have fun? Did anyone know that you're…"
"Mom! Hold it! Let me sit down and I'll fill you in."
I told her it was a ruse, that Katie knew that I wasn't a girl, then all about the plan she had concocted, and how I had finally agreed. Why, in my lust to go to Mario's, only the best restaurant in town, I had agreed to go as Jeff's date. Mom listened quietly, then burst out laughing!
"Now you've done it!"
"What? I haven't done anything, not yet anyway!"
"Oh yes you have!" mom said, "but what I can't understand is why you're even considered doing this! I'm not even sure if I should let you go on a date? With a boy? It's ridiculous of course, but Katie has probably told her brother that you'll go out with him, which certainly means that he doesn't know that you're a boy dressed up as a girl!" Mom just stared at me for a moment, then, "If I let you do this, and I'm not saying I will, you'll have to have a nice dress, and depending on what happens after this date…what I mean, is, what if he asks you out again? Have you thought about that? Or what that means?" Shaking my head no, wondering what she was driving at… "It means that you'll have to keep dressing as a girl doesn't it? And if likes you he'll probably want to take you out again, maybe more than a few times! What if he decide to take you to Mario's? Just the two of you…alone? If that happens you'll almost certainly have to, or maybe want to, wear a dress that'll show at least something on top, something that you don't have!" Grinning, mom said, "Maybe, since it seems to me that you've already accepted the idea of being a girl, and if I let you do this, we better find something that's a bit better than those bags of seed you're using!" Then came the laughter again. When she settled down…"A trip to the salon might help too, but depending on what you wear, boobs, and maybe hips are going to be your biggest obstacle!"
Mom was right, which I realized as I thought about the dresses Katie tried on. Low cut, probably tight, and certainly short, if mom was right, eventually I was going to have to be prepared to try on, and maybe wear, almost anything she could! I went to my room to change, but only put on my shorts, which were tight, and a tee, which merely accented my breasts. With a sigh, I went to set the table. That's when mom told me that I could just call it off and nobody could do anything about it, but when I didn't say anything…
"I see!" she said in a shocked tone, "you want to do this! Don't you? You want to go to the salon, do some dress shopping, then go out with this boy! You must like this a lot more than I thought! Is that it? You like dressing up as a girl!"
"Mom, I…"
"Isn't it odd for a boy to want to dress like a girl, other than a party I mean. It seems so…"
"Mom! Listen! It's not like that!"
"Oh? Tell me why! If you took a girl to a place like that, and spent several hundred dollars on her, wouldn't you expect her to be…extra nice to you?" I sighed, and she went on. "I know that you knew that, yet you agreed to this date, knowing full well that just shaking his hand when he brought you home probably wasn't going to be enough, so what else am I supposed to think?"
"Mom, this is Mario's! We never go there!"
"And this is your chance?"
"Katie said that I could just put him off after that, and he would get the hint. She said that guys will do anything if they think they have a chance with a girl, so…"
"So you thought you would make him think he had a chance, spend his money on you, then drop him?"
"Well…"
"No dear; I won't let you do that. I wouldn't let you do that even if you really were my daughter! But you're not a girl, and while I thought it was a good costume at the time, and you certainly seem to like it, I also know that you certainly wouldn't like it if you took a girl out and she did that to you would you? Of course not! Besides, I'm still not even sure that I can accept having you running around wearing dresses!" She had a frown on her face, but didn't look upset. "If I let you do this" mom said sourly, "and I might not, just how did you plan on getting out of it later? Won't that boy and his parents wonder where you just disappeared to? And if he picks you up here like he should, won't he always know where to find you? If, and I say if, I let you do this, then you had better be prepared to try on and buy a lot more clothes because once you go out on a date there won't be any way to quit! And like I said before, if this boy likes you like his sister says he does, my bet is that he'll probably to ask you out again! And what about Thomas? He'll know who you really are, and what's to stop him from telling?" For the first time since I sat down, she smiled. "Maybe you accepted this date because you like dressing as a girl more than you wanted to tell me? Is that it?"
"No Ma! It's not like that, it's just…I don't mind it, not really, and you've seen how I look! You have to know that I look better as a girl than I ever did as a guy! It's…"
"What? Okay? Maybe it's okay for boys to dress like girls nowadays, but I doubt it, so if I let you do this, then I'll expect you to go all out to look, act, and be as feminine as possible at all times, then see this all the way to the end, whatever that turns to be! By that I mean that I'm so sure that this is going to get so confusing that maybe none of us, especially you, will know how to get out of it!" Mom sighed, then… "Since you want to do this I guess I'll go along with it, but I will not allow you let this boy spend all that money on you just so you can go to some kind of fancy restaurant, then drop him! That's cruel and you know it. Maybe you might go have a pizza or something like that first, then you'll know how you feel about this, and I can see how you get by. After that we'll discuss this some more."
"So…you're going to let me go out on a date, as a girl?"
"I think I will! Maybe this will be a good lesson for you! Maybe you'll find out that being a girl isn't all that much fun, and I'll remind you again that I don't think running around in dresses is going to end up being as good thing as you think it will be! I'm warning you, something is going to go wrong, so be prepared to deal with it!"
Mom gave me a lot to think about, which I did, a whole lot! I knew that what I was doing was risky, and I also knew that guys didn't, or shouldn't, want to dress up as a girl. That was fine, except for the fact that that I liked the way I looked. Since I had never dressed up as a girl before this all started, I wondered why it hit me like it did, yet in many ways I didn't want to find out why I seemed to like it! All I knew was that as a girl I was having more fun than ever before, I looked sort of cute, and for the first time in my life I felt a sense of freedom. It wasn't the clothes or the makeup or the hair, it was all of them, combined with a social life that I had never experienced before.
It's not that I didn't have any friends, I did, but I never dated because I just didn't feel like I had to. I had friends that were girls, but no "girlfriend" as such. I was an above average student and tried to attend as many school functions as I could, I just felt out of place most of the time, something I could never understand. As I looked at my reflection in the mirror I thought I finally knew why. That's why I didn't change until I went bed that night. When I got up the next morning I looked at the dress, bra, pantyhose and stuff laying around, and wondered if I should get dressed again, but didn't. Still wearing those nails, I went to make breakfast. Mom didn't look shocked or say much at first, then told me to call Katie and tell her that I wanted to get a pizza or something instead of going to Mario's. After that, she said we were going out shopping to get me a skirt and top to wear as well as some flats.
I made the call, but got Jeff instead of Katie. He asked me to go with him, but I told him that regardless of what Katie may have told him, I thought that someplace less fancy might be better, and he quickly agreed. I went to wash up, looked at the clothes, then my nails, and decided to be a girl one more time. After all, I was going out to buy a skirt, so why not? I did my own makeup, put my hair in a ponytail, slipped on my gym shoes, and walked out of the room.
"At least" mom said softly, "it looks like you have mastered the art of makeup well enough I guess. You have one fancy dress, and one summer dress; now you need a skirt and blouse, but I'm wondering if that's going to be enough! What I mean is, after going out on this date you'll have to keep dressing this way and if this boy wants to see you again, then we'll always be running out to get you things! I'm wondering if we might as well get a few skirts, a some blouses, maybe a pair of jeans, shorts, tops and some shoes in black and white. Can you afford that?"
"Sure, I guess..."
"Are you prepared to carry this out as far as it goes? Dressing as a girl all the time, starting right now?" Having decided that issue the night before, I nodded my head yes. "Okay then" mom said, "lets go."
Mom, while making it clear that she did not like me dressing as a girl, went along with it for a couple of reasons I think. The way I looked was one. The way I looked as a girl shocked both of us because neither of us expected that. Another was because she wanted me to find out that being a girl wasn't going to be fun as she put it. But I think the biggest reason was our mutual confusion about my seemingly casual acceptance in the role of a female. Maybe I didn't put up as much of a fuss as a normal guy should have. Maybe I was meant to be a girl all along and didn't know it. I'm pretty sure that neither mom or I really knew, but for whatever reason, she had decided to go along with it. I had been right when I said that I looked better as a girl rather than a boy, and while mom never said it out loud, I had seen it on her face; she knew it too.
Mom had told me that dressing as a girl all the time, accepting that role and everything that meant wouldn't be fun, and even though I wasn't sure if I could even do it for very long, I was willing to try. What I did not tell mom, because she already knew, was that going out with Jeff would be my first real date of any kind, with anybody, and I was excited about it. Not because I would be going as a girl, but because it was actually going to be my first date. Mom was all business when we got to the mall, heading straight for the store she always went to, and with some help, letting me pick out the skirts while selecting the blouses. In shoes it was just like she said, black and white flats, but added heels in black, red, and white, then on the way out she stopped in lingerie and had me get a package of panties and another bra before I picked up a pair of girls jeans.
"That was a lot of money Debra, but you'll probably get to wear them often enough to make it worth it."
"Maybe."
"It's my guess that you'll more than likely wear them out."
"Mom, I never said…"
"Don't try that honey. I've been watching you all morning, you and all the people around us. Not one person even considered that you were anything but a girl, and you've been acting like a little girl in a candy store ever since we got here! Now, rather than try to lie to me, lets get something to eat and we'll talk about this beauty shop appointment you've been talking about."
Once we were seated and had our meals, mom wanted to know what I knew about beauty shops. When I said that girls get their hair done at a salon, she laughed for a moment, then went down the list of things that most beauty shops offer, like doing hair and nails of course, but also waxing, and makeup among other things.
"If you just go in there and tell them you want the works, you're liable to find yourself spending several hundreds of dollars, so you'll have to pick and chose. Have you thought about it?"
"Well, my hair of course, and maybe my nails, those salon nails you get always look nice, and these…"
"But salon nails are acrylic! That's why they look so nice! Do you have any idea what having acrylic nails means?"
"No, what the big deal? They're just plastic, like these; aren't they?"
"Not hardly! Salon nails are acrylic honey! They are molded to your own nails and fixed in place with some really good glue! That mean they don't come off, at least not very easily, so if you do get them, that would make it almost impossible for you to be a boy again, at least not very soon…is that what you want? Salon nails? So you'll have to be a girl longer?"
"Well…maybe, we did buy all those clothes, and you did say that I would have to be a girl full time, which means that I'll be wearing nothing but girls clothes, so, maybe, why not?"
"I didn't think that you would…what I mean is, if you do get salon nails, then you should think about the rest Debra! If you're willing to live as a girl then you should at least consider having them wax your arms and legs, just to cut down on all that shaving you'll have to do!"
"Mom" I said, "I'm not going anywhere near that place unless you tell me it's okay! You don't sound like you're against it, but you did say that you're not comfortable with me like this, so unless you say it's okay, and tell me right now, I'm done with this! We can take all this stuff back, then I'll call and cancel the date!"
"That would be fine with me honey, except I believe that you've already found out that you like to dress as a girl, which means that you'll probably do it again no matter what you might say right now!" Framing her face by putting her chin in her hands, "You know how I feel about this, so I'm not going to insist that you go ahead with a trip to the salon then out on a date, but if you don't, then how will you…what I'm trying to say is, there are boys out there that have become girls aren't there? How will we know if you are one of them or not unless you try this? Like I said, it's obvious, to me anyway, that you're starting to like being a girl, and it seems to me that this is your best chance to find out if that's true!"
"But I never did this before Tom asked me to that party mom! And dressing as a girl was your idea, remember?"
"True, but the fact remains that you like it, right?"
Mom left me nowhere to turn, leaving me with all those conflicting emotions. I didn't really think that I liked guys like a girl would, but she was right about one thing; I did like dressing as a girl, more than I should have I guess. If I got my hair done, a waxing, then salon nails, I knew, because she told me so, that I would be stuck as a girl for a good long while, unless I was willing to spend the hours needed to get them off. Having my hair done didn't seem so bad, I could always work around that, and not having any excess hair on my arms and legs wouldn't be so bad. It was that other thing. About boys becoming girls that bothered me. I never felt like I wanted to be a girl before, yet everything about it felt so…natural, like it was the most normal thing in the world for me to be dressed that way! We ate, then just before we were ready to leave I told mom that I was going to do it.
"What dear?"
"Have my hair done and get salon nails mom. If you're right, that I might be a…I have to know, and so do you! Right?"
"I suppose, but then, what about your chest? What are you going to do about that?!"
"What's wrong with what I have?"
"Because they don't react to your body quite the way…they look okay of course, but…maybe something else would be better, especially if you're sure about doing this! What about those breast forms women use when they have surgery? Don't they look almost normal?"
"I don't know mom, but they're expensive I'll bet."
"Then why don't we find out?"
That's when I finally asked mom straight out why she was helping me. "Why are you doing all this mom? I mean, I expected you to rant and rave about all this, not help me buy clothes!"
"Oh I wanted to rant a little, but you're to old for that aren't you? Am I happy to find out that you like to dress up as a girl, go on dates with boys and all that? No! Of course not! But you haven't ever had a date have you? What I mean is, and there isn't any way either of us can deny it, you really are quite pretty as a girl. I guess I didn't expect that, but…"
"I never was very masculine guy mom, I know it and so do you. I'm not saying that I want to be a girl, it's just that…I guess, when I found out that I'm better looking as a girl than a guy I was shocked, but I have to admit that I like the attention I'm getting! Nobody ever paid this much attention to me before, and if I have to play dress up to enjoy it, I guess I'll do just that, but I'm not sure about us. How you and I can manage."
"I'll manage just fine honey, you're the one that'll have to adjust! I'll be there to help you, but you got yourself into this mess, so you'll either find a way out or you won't!"
"Adjust?" I asked…
"Ever have to go to the bathroom real bad? For guys, it's in and out. Ever notice the long lines at the ladies room? I can hardly wait to see how you manage that!"
"I always thought it was because you all talked, touched up your makeup and like that!"
"Hardly!" mom snorted, "but you'll find out about those kind of things soon enough. Now then! Lets see what we can learn about breast forms."
We went to a place that sold breast forms for ladies that had had a mastectomy. The lady was very professional, and surprisingly, wasn't put off the slightest when she found out I was a boy. She was very efficient as she showed mom and I everything, from the cheapest to the best.
"If" the lady said, "you'll be wearing them every day, and it sounds like you will be, then our top of the line models will last longer, look better, and are the most natural. They cost a bit more, but they're worth it."
Mom agreed, then said that she would pay for them! After measuring me, the lady returned with a pair.
"These are a B cup, the same as the bra size you had on. Lets go ahead and try them with the bra on before we go any further."
After I tried them on and a few more measurements were taken, the lady made some adjustments, then used a really foul smelling glue to attach them to my chest. She took her time, making sure that the seams were as minor as possible, covering them with a cover stick before she told me to go ahead and put my bra back on. That's how I came to have them on my chest. Heavier than my bags of birdseed, both mom and the lady said that I would get used to them. With every step I could feel them, how they moved with me, and how they reacted to whatever I did. Even with the unfamiliar tugging on my chest, I'll admit that I felt much better wearing them.
"I have a friend" the lady said casually, "that sells things for boys that make them look like girls in other places. I understand that this item also helps in the hip department…if your interested that is."
Mom and I looked at each other, then took the information she offered. By the time we got home I was more than ready to take a really good look at my brand new boobs, which I did. They looked real enough to me, and I grinned at my reflection before I got dressed again. Later, when mom and I were putting things away, Katie stopped by, so the three of us went out back with a soda and sat on the patio.
"You look like the cat that got the extra milk Deb!"
"Katie" mom said, "I want to talk to you about what's going on, and I want you to pay very close attention to what I have to say. Okay?"
"Sure!" Katie said lightly.
"I'm not so sure that having my son dressing as a girl is such a good idea, however, I have agreed to let him try it, for a while anyway. As far as this date goes…"
Mom told her why she had agreed to let me do it, then made it very clear that she wasn't going to let Katie or anyone else put me into any situation that could hurt me. She also told Katie that if she were my friend, she would expect her to help me when I needed it.
"Can I count on all that Katie?"
"Sure! I never…what I mean is, I only asked Debra to do it because Jeff wanted to meet her! I never thought about making her do anything wrong, in fact, I told her that already!"
"I'm sure you did, I just wanted to make sure that you understand how I feel about this."
"I understand" Katie said, "I just stopped by to see if Deb might want to go out tonight, just her and I."
Mom said it was okay, so Katie and I left, going in her car. She and I went back to her house, then into her bedroom. After she shut the door, she asked me if something had changed, telling me that I somehow looked different, only she couldn't put her finger on it.
"It's my boobs" I told her, "I got new ones today."
"That's it! You're…rounder! More natural!" She flopped on her bed. "Jeff almost can't stand waiting for Saturday to get here Deb! I'll bet he's been playing with his toy just thinking about it!"
"Won't do him any good, I'm not…"
"Not what? A girl?" Katie actually laughed at me! "Lets think about that a minute. You're cute as hell, way better looking as a girl than any guy just dressing up as a girl has any right to expect to! When you came over here all dressed up because you thought there was going to be a bunch of girls here, you looked just as normal as any girl I know, then you and your mom went out and bought those? Oh no. You like being a girl, so don't go there Debra, because I won't believe it, and I doubt you do either!"
"I'm not, I'm not sure that I like…"
"Boys? Might as well get used to it Deb, because I'm willing to bet that Jeff is going to be just the first in a long line of broken hearts!"
"But" I cried, "I can't, I'm not sure that I can do what you do!"
"And just what do you think I do? I'm not a whore Deb! Guys don't get into my pants! So just what is it that I do that you can't?"
"Kiss" I said sourly. "I'm not sure that I can kiss a guy."
"Easy! Just pucker up and let them have it! If it doesn't do anything for you, well, then you'll know, right?"
"I guess, but."
"No but's Deb! You have to start thinking like a girl, not just a guy in a dress, not if you want this to work, and I already know that you do, or you wouldn't have spent all that money on new boobs!"
Katie asked if I wanted to meet some of her other friends, then got on the phone and started to call around. About an hour later, five other girls were at her house. Jeannie I knew, the rest I had only seen around school. Katie introduced me, then we all went to the kitchen to get something to drink. Most wore jeans or shorts, only Katie and I wore skirts, but nobody said anything as we all sat at the table.
Cathy said "I hear you got a date with Jeff."
"Saturday" I said, "we're doubling with Katie and Tom for pizza."
"I've been trying to gets Tom's attention since fourth grade! No luck yet." Cathy sounded dejected.
"Try using better bait Cathy, Don't wear a bra!"
"Like I could get out of the house without one! My mom would freak out!"
"Get a push up bra" I suggested.
"And wear something low cut" added Rosie.
"Or get one of those new bikini's." Kim was giggling when she said it.
"You look sort of familiar Deb" Amanda said, "but not from school, I would know…"
"Maybe it's her cousin you know, They look a lot alike" Katie said suddenly. "Deb is spending the summer at his house while he's away for the summer."
"And she lands Jeff without any trouble at all!"
"You never had a chance Cathy, no boobs."
"But I have a fine ass!"
"So do I, and it hasn't done me any good either!"
"What are we going to do tonight" Jeannie wanted to know.
Everyone looked at everyone else, and one word came out…"shopping" they all said at the same time. Katie told everyone to be at her house at six, then after they left, she took me back home. It was enlightening to hear girls talk about themselves and boys like that, comparing themselves to each other and so on. I went to my room to take a shower and redo my makeup. When I was out of the bath, and before I got dressed, I dug out the paper I had downloaded that explained how to use tape to make a guy look like a girl. I sat on the bed, and started reading. Using my fingers I could push things together, but I couldn't manage to get the tape on, and after the third failed try, I knew that I would need help, but the only help around was my mother. If I was going out in a group of girls, I figured I had better look as much like them as possible, especially if I found myself trying things on! I hated doing it, but I called out to mom, who came in my room to see me hiding my very manly parts.
"Yes?"
"Uuuuhhh, I need some help mom."
"Doing what for heavens sake! You know how to dress yourself!"
"No, it's not that mom" I said softly, "it's…it's just that I'm going out shopping with some girls, friends of Katie's tonight, and I thought that it would be better if I looked like a girl all over, just in case! What if they want me to try on something that doesn't hide my…bump? I looked it up on the Internet and tried it, but I found out that I can't do it by myself! That's why I was wondering if you would…help me?" Then I showed her the sheet I had printed out.
"I see! So…now you want to look like a girl there too?"
"If I'm going to do this, wouldn't it be better if I didn't have any…so that I could…wear anything they do, without any accidental… excitements? And like I said, if I'm out with those girls shopping tonight, I might find myself trying things on, and I'd really rather be safe than sorry mom, that's all!"
"Well, okay, I guess, …let me read this first."
Mom read the instructions, huffed a few times, then…
"Are you sure about getting your hair and nails done?"
"Yeah, why?"
"Well, if we follow these instructions, but use something a bit…stronger than tape, I think that I can insure your safety for a few days. We'll use that same glue that lady used on your boobs!"
With my help, mom turned my boy parts into what looked almost like what a girl would have, only she did not use tape, she used that glue. When she was done, nothing hurt when I walked, then she told me to go in the bath and make sure I could eliminate. I could, so she left me to get dressed. It was very strange not to have to try and hide things, but I knew that I would be safe, and that was all that counted. Seeing my naked form in the mirror, all I could do was gasp at the changes that had happened to me in less than a week, and wondered once again why I had let it happen. Then I pulled on my panties and did my makeup. I wore a short skirt with a thin top, my flats, my hair down and basic makeup. Not over done at all. I went out, walked over to mom, and hugged her.
"Thanks mom."
"Do I have a daughter now?"
"A niece. Some of the girls thought I looked familiar, so Katie told them I was a cousin."
"Okay. Have a nice evening. Do you have some money?"
"I'm okay mom."
It was instructive, shopping with a horde of girls rather than mom. She was more deliberate, while every one of the girls was adventurous. Jeannie tried on some very sexy lingerie, and ended up buying it, Rosie looked at short skirts but held back. Katie got me to try on a nice dress, which I bought, then it was on to jewelry, shoes, lots of shoes, makeup, perfume and other stuff. Kim bought some shorts and shoes, Katie wanted new jeans, and I wanted to sit down and take a rest. By the time the mall closed they had completely accepted me as one of them, which was just what I needed if I had any chance of pulling this off. My poor ego needed a boost for sure. By the time I got home I was whipped, and quickly changed for bed. But if I thought it was exhilarating to be out with a bunch of girls, mom was about to raise the bar, except I didn't know that. The next morning…
"Since you seem to have committed yourself to this" she said slowly, "and while I'm still not sure that this is the right thing to do, I have decided that you were right. The only way to find out if this is just some kind of experiment is for you to go all out and become a girl in every way possible. So, right after you get dressed, we are going to the address the lady at the mastectomy shop gave us and get you fitted out. Then we'll go to the salon, just you and I, and you'll get the works! I'll feel much better being there with you rather than letting Katie convince you of something that I might not like. I'll pay for all this, but I'll expect you to keep it up after this, is that okay?"
"Sure mom."
"Good. Lets get your parts undone, then you can get dressed. Don't wear any makeup, they'll just wash it off anyway. Now go get dressed."
Getting fitted for that "other" special piece of equipment was just about the most embarrassing thing I had ever done, but when the guy was done, there wasn't any sign that I was a boy or ever had been! My hips were fuller, my butt rounder, and according to the guy, I was "fully functional" as a girl!
"If you want" the guy told mom and I, "using these will simulate a period." He put a handful on the counter, then…"use the lubricant before any romantic encounter, and I promise, nobody will ever know. I pride myself on my work, and always take special care to assure my clients full satisfaction. Call me if you have any problems Debra."
I thought I knew what to expect with that panty I had on, but after I found out that I could have periods, and even sex, I was at a total loss for words. Mom was smirking I think, but she didn't say a word as we drove over to the salon. I thought that I knew what "the works meant after mom explained it. Foolish me. I didn't have a real clue. First, they had me get down to my bra and panties, then they stripped off every bit of hair on both legs from my ankle to my panty line! Then they did my arms, including my hands and armpits! Aching, I thought they were done, until she started on my face with a laser, removing all traces of my moustache and chin hairs before she started in on my throat, then reshaped my eyebrows. My skin was on fire, but the lady lied to me when she rubbed in a lotion of some kind which, she said, would ease the fire a little. That was a big fat lie. I hurt all over. Then she started putting a mud pack on my face! While that hardened, all I could do was lay there, and later, when she removed the mask, it came off with what sounded like a rip. That's when I knew that I was in a torture chamber masquerading as a salon! Still wearing the gown I was given to wear, I followed the lady out to another chair. Using a small stick and some goo, she trimmed my eyebrows again so they were thinner with more arch. Then came the hair styling.
"Your hair has an auburn cast in it honey, how about we try to match it? It'll look fantastic with your coloring!"
"Yeah, why not."
"How about some curls? Trust me. I can make you look just gorgeous honey!"
"Might as well" I said, already knowing I was already in way to deep to back out.
Two hours later I was sitting at the table as the nail lady started working on my hands. After she removed the fakes, she cleaned my nails and began applying the salon nails. By the time she was done, almost four hours had passed since I first walked in, and as I got dressed and saw my reflection in the mirror, I couldn't help but smile. I did not look like me in any way, except maybe height. My makeup was perfectly done, the nails just long enough to be feminine yet usable, my curly auburn hair fell around my face just right, and my skin was as smooth as any woman's, and even my face had a new smoothness! I waited until mom returned and paid the bill, but her first reaction when she saw me was one of stunned silence. On the way out…
"God! You look…simply gorgeous! I figured you would look better, but…this changes everything, doesn't it?"
"How?"
"You're not going to quit, not now, not after buying those boobs and that panty, and seeing how you look now, well, I'm willing to bet that you can't quit!"
"They did make me look pretty good, didn't they?"
"I'll say!"
As mom was driving, I noticed that we weren't headed home like I thought, so I asked where we were going.
"Okay, what's up mom? You got that look on your face again."
"I was just thinking" she said, "given how you've already gone well past being able to stop dressing as a girl, right away that is, and given how nice you look, I'm going to make sure that you have a drivers license in the name of Debra Elizabeth because I think it's time that you thought about the future honey. Becoming a girl is going to be expensive, and at the very least, until you get more of the things you'll need to have, you'll need to get a job! And since you've decided to be a girl, you'll have to have the proper identification to get a job!"
That's when I found out that I was taking my drivers test! Only I already had a drivers license! Mom had said it was for my own good. I knew she was right. When we were at the counter mom signed a paper swearing that I was her daughter, my name was Debra Elizabeth, and that I was 17. The woman looked up at me, smiled, then handed me the test. An hour later I walked out with a perfectly valid driver license in my girl name! That meant that according to the state, I was legally a female! Mom let me drive home, silent but with a smirk on her face.
"I was thinking" mom said, "that now is the time you and Tom had a long talk. You said he owes you, so call him, have him come over, then make him pay up!"
As soon as we got home, I called Tom, asked him to come over, then went to my room and touched up my lipstick. I briefly thought about changing into something that would show off my new boobs, but decided that I didn't need to do that. I went to the kitchen, got a soda, and sat waiting for him to arrive, and when he did, I opened the door to let him in. When he saw me his eyes almost bugged out.
"Damn!"
"Like it? I had it done this morning!"
"Wow!"
"I'll take that as a yes. Come in, lets sit down."
Once we sat down, I told him that I needed a job, and gently reminded him that he owed me.
"You aahhh…going to work, like that?"
"Sure! Why not? Don't I look good enough?"
"Hell yes! You look great! It's just that…well…" That's when I handed him my new driver license. "That's you! Is this the real deal?"
"Yeah; mom and I went there this morning, I took the test, and voila! They said I was a girl, and now I can prove I am! Neat! Isn't it?"
"Aahhh…What are you doing!? I mean, you look fantastic and all that, but…what the hell is going on?! A valid drivers license? As a girl? That can only mean one thing! That you're going to…..become a girl?!"
"It turns out that I not only look better as a girl, I sort of like it! So…yeah, why not?"
"No reason I guess, it's just so…different I guess!"
"Aren't you the one that asked me to do this for you? So you could ask Katie out? You must have somehow known, even then, that I was good at it, or maybe wanted to, or you wouldn't have asked me to keep doing it! Now, how about it? Can I get a job with your dad?"
"Yeah. Let me call him. Hand me your drivers license."
Tom made the call, gave his dad some information, then looked up at me grinning. Then he told me that his dad wanted to meet me, so if I had the time, he would take me over to his house, and bring me back home later. I told mom I was leaving, grabbed my purse, and followed Tom out to the car.
"Your dad doesn't know does he? About me I mean?"
"Nah, he only knows your name. Relax! You'll be fine!"
"When are you and Jeff picking me up?"
"Six. We'll have something to eat and maybe a show later?"
"Jeff doesn't know Tom, and I don't want him or anyone else to find out, okay?"
"Sure...of course."
Tom's dad was very nice, but as we sat and talked I saw and felt his dad's eyes roaming all over me, a very strange sensation, yet he was always polite, and he gave me a job starting the following Monday as a clerk. When Tom took me home, he reminded me that they would be over at six to get me. I changed into a dress, then sat nervously waiting to go on my first date. Right on time, Jeff was all grins when I let him take me to the car. Tom and Katie weren't there, so I asked why. Jeff told me they were going to meet us. My first thought was that it was fine, then I realized that with only Jeff and I in the car, he might not be quite as shy as Katie said he was!
We had our pizza, went to the show, and on the way home, Jeff asked me out again. By the time we were parked in front of my house, I was ready for what I knew I had to do, and let him kiss me. Then, just as I went in, I said "yes" to his invitation for another date and ran inside. That night as I lay in bed my hand fell to my groin, and as I fingered the changes, I had a serious case of the doubts as I wondered just how long I could manage to keep up the charade. The feeling passed and I began to relax as I once again accepted what I felt inside was the truth. I saw Jeff the next afternoon, we went for a short drive, then I called Katie when I got home. Bubbly as always, she wanted all the gossip, but I held back a few things, although I did tell her that I was starting work at Tom's dad's place on Monday.
The night before I was to report to work, I once again found myself wondering if I had finally gone insane, especially after I looked in the mirror and saw my face covered in green, a home facial I was using. I was wearing a flannel nightgown, my hair was in rollers, and fuzzy blue slippers to keep my feet warm! In the past I had teased mom about doing the very same thing, yet there I was, spending hours trying to look pretty! I know that mom was holding it in, her giggle I mean.
"I seem to remember you teasing me about doing the same thing you're doing" mom said with a grin.
"Yeah, but now…"
"Remember what I said about adjusting?"
"Yeah…?"
"How's it going?"
I grinned back at her and said nothing because there wasn't anything I could say. In the morning I wore a nice skirt and blouse with low heels when I reported for work, assigned to taking care of the inventory tracking system, replacing a woman that had quit to have a baby.
Day by day, living and working as a girl simply became normal. Not one person in the office had a clue that I was a boy, and I was accepted by everyone as just one of the girls. I passed on my first year of college and kept working, saving my money until I could finally start taking the medications to help me gain the actual body I had come to realize I needed, and wanted. Jeff and I broke up, Tom kept my secret, and Katie and I have become very close, almost like sisters. Mom has started dating a fellow that treats her like a queen, so I know that it won't be long before I'll have a new dad, and be moving out to my own apartment. Life is good.
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