Jessica and I met our junior year at USC in LA. We were both architecture majors and initially crossed paths in an advanced design course. We were randomly paired together to work on a concept project and became close friends almost immediately. For the next two years of school we were nearly inseparable. Our friendship blossomed into a full-time relationship and by the time we were ready to graduate we talked of getting married.

I had been an active member of a fraternity up until we met, but considerably less so after Jessica and I became a thing. Jessi was a member of many academic organizations but never understood the need to join a fraternity or Sorority. She would have been coveted by any sorority, as she was attractive, a great student, and came from a family with real money.

I joined the Fraternity for a sense of belonging. I had no siblings and both of my parents had passed away when I was in High School. My mother had cancer and shortly have she passed my father was killed in an auto accident. I lived my last two years of High School with my aunt and Uncle. They were good people, but the tragedies had taken a lot out of them and those years were hard on everyone.

Fortunately, my father had been a lawyer and had some life insurance. I was financially well enough off to not have to worry about college costs even if I chose to continue on to grad school. I would also have a small nest egg to get started on life when my school days ended.

Unlike Jessica, I don’t think I was high on the fraternal recruiting listed. I felt almost lucky to get accepted to the Kappa Omicron Kappa, which was not one of the elite frats. I didn’t have any legacy connections, special talents, and I was not exactly an Adonis. I stood about 5’7” if I really stretched myself out and while I was fit, my body had not developed much from the stick that I survived through High School. At least I had what was described as an attractive face with fine features. My skin was very fair with minimal facial hair. At the start of college my sandy blonde hair barely covered my ears, though I wore it long in the front. The bottom line is that I might be considered cute, but I looked younger than most freshman. I guess my strong high school academic record and that I was admitted into the honors Architecture program scored enough points for me.

I quickly became an enthusiastic member of the frat. It was something I really needed after all the family tragedies I was trying to get over. I was eager to have the new friendships and brothers. Like most fraternities we drank, partied and engaged in stupid activities, but at least I felt a part of something.

Chapter 2:

In the weeks just prior to our graduation Jessi and I talked a lot about our future. We both planned to work for a year or two and then go to Graduate school. Jessica was going to work for her father’s Corporate real estate firm in the planning division and I had lined up an assistant architecture position at BuilderOne Inc. Both of our positions were in Los Angeles and we managed to negotiate in a couple of months off before starting our positions. I really wanted to work for the Jessi’s family firm too, but I did not even apply to avoid putting extra pressure on Jessi’s Dad. Her father’s firm was super prestigious. Her dad had made a bundle in Real Estate development and in the hedge fund market. The Johnsons were sort of Nouveau rich. They had major wealth, but were the first generation in their family tree to have big bucks.

Jessi and I considered going on some exotic vacation and even contemplated getting married on a beach somewhere. Jessica knew that this would probably not please her parents, because as their only daughter, she would be their one chance to plan an over the top Wedding. I was probably not the ideal they envisioned as her future husband. I am sure they desired her settling down with some big hunk from the upper-crust or other prominent background.

I had met them on multiple occasions, but I don’t really think they saw me as her exclusive boyfriend. I got along with them OK, but it was mostly because we could talk architecture or because I was thought of as Jessi’s good friend. My guess is they assumed our relationship would just fade to acquaintances or that she would eventually meet Mr. Right.

Only a few days before graduation, Jessi informed her parents that we planned to live together and were considering tying the knot. To say they were shocked and upset would be an understatement. The conversations went on over the next couple of days and I was not even given an opportunity to make my case to them. Jessica finally agreed to some of their demands as a possible compromise.

I was basically told by Jessi that upon graduation that we were going to move in to their home for at least a couple of weeks so that they could get to know me better. That seemed reasonable, but Jessi knew that they still were not thrilled. We would have to be on our best behavior and I would need to develop a stronger bond with them. While her dad was the ultimate boss, the key was Jessi’s mother. If I could impress her and make the right connection, she would be able to guide us over any of his remaining reluctance. His mom had always been nice to me, but this was prior to the recent revelation.

Jessica began to focus on the situation as it pertained to us. She was very matter of fact and became unusually controlling. It was not really a two way conversation and it was a side of her that I had not seen very much of. I’m guessing it was a family trait, but I was willing to follow if it made our lives better. Jessi meant the world to me and I wanted what she wanted.

She began to lay out how I was to behave and act while living at their estate. There were many do’s and don’ts and I should not consider it a vacation. How we, and more specifically I, performed over the next couple of weeks could have major repercussions for the rest of out lives. She basically told me that I needed to be totally cooperative with both of them and follow her lead. I could express my opinions, but not be adversarial, and ultimately try and be agreeable.

Jessica wanted me to focus on her mother. First off her dad was not around that much and she was the key. If she could begin to feel motherly around me, then I had a real chance. She wanted me to try and spend as much time with her as possible. In addition to the long list of mandatory suggestions, was as Jessica put it, ‘the need to dress up’. This was my first push back with the house rules that I expressed my displeasure with to Jessi.

“Lyle I’m just saying that you need to dress for the occasion.”

“Occasion? What occasion?”

“Whatever occasion there is. If we go out, I want you dressed in your best threads. At home, neat all the time. Your hair should be shining and your nails well manicured. Basically, I want you to look extra nice all the time.”

“I thought I did look nice.”

“Why are you taking this so negatively? You do look nice, but if I wanted you to wear a costume to impress them, then you should. For now you need to focus on how they want you to look. We need everything to go smoothly.”

“The last time I wore a costume it went too smoothly.”

“Lyle, what are you talking about?”

“Not important. I get your point.”

“No really, what about the costume?”

“Its kind of embarrassing, and I am not sure you would appreciate it.”

“We don’t keep secrets. Please tell. I am sure I will understand.”

“Promise not to laugh at me? Even though admit-ably it was a little funny.”

"Sure Lyle. Now I am very curious."

“Well Jessi, as part of my Freshman initiation into the frat, I had to spend an entire weekend dressed as a cheerleader. I did rah-rah-rahs at all the frat events that weekend.”

“So childish of them. They really made all the pledges do something that ridiculous?”

“Actually, each of us were given different silly activities for the weekend.”

“How come you got that one?”

“They say it was a random drawing, but I later heard unofficially that they picked me for that one because they thought I would make the cutest cheerleader.”

“Lyle, did you have to wear a cheerleader’s skirt or just the sweater?”

“Actually, they wanted the whole nine yards. I was shipped off to the sister of one of the upper-class fraternity brother’s for a full makeover. She was a Pom Pom girl for the football team and she was told to make me as believable as possible.”

“Wow Lyle! How come you never mentioned this?”

“Kind of hard to tell your girlfriend that you made a convincing Cheerleader”

“So, what did she do with you?”

“Everything. My hair was much shorter than it is today, but she provided me with a long wig made from real hair to borrow. I had to completely shave my body and she meticulously did my makeup including false eyelashes. I even had to wear panties and a bra.”

“How did you turn out? I bet you were pretty.”

“That was really the most embarrassing part. I looked very real and according to her and later most of the guys, I could have given the real cheerleaders a run for their money.”

“I bet that felt strange.”

“More than a little. I couldn’t believe it was me when I saw myself in a mirror. I looked like someone that I would have found sexy.”

“What happened after that? This story sounds very interesting.”

“I was scared.”

“I guess it must have been pretty freaky.”

“In so many ways. I was scared that it didn’t look like a costume for one. It also scared me that I took pride in how I looked. It felt kind of cool to look so hot. I never told anyone but I was fascinated by seeing my reflection and even a bit turned on.”

Jessica was smiling ear to ear as she professed, “You really enjoyed it, didn’t you?”

“I’m not sure I would go that far, but it did feel a lot different than my expectation.”

“How did the weekend go after that?”

“The whole weekend I had to remain in the uniform. The guys at the frat called me Lyla instead of Lyle. I didn’t know where that came from, but it stuck all weekend. Someone even left me a nightgown on my bed with a note that as pledge I had to stay in the role all weekend. I’m sure that was just someone’s little joke but I didn’t dare challenge the fraternity rules. God only knows what more they could have made done had I not fully cooperated.”

So you were pretty Lyla all weekend and even when you snuggled in bed.”

“Don’t make fun of me, please. It was hard to put behind me.”

“I’m sorry, it’s just I can’t believe I didn’t hear about this from you or some of your friends.”

“I played along with them all weekend and when I became an official brother, I swore them to secrecy.”

“What was it like being the only girl living with a bunch of guys?”

“JESSI!, I wasn’t a girl. I just looked and attempted to act like one.”

“Act like one?”

“I mean I just played the part of the cheerleader like I was required to.”

“Were you treated OK?”

“Actually, I was treated the best of any pledge that weekend. They pretty much treated me like a real cheerleader living at the house. I think I made a couple of the guys nervous because of the way they looked at me.”

“So before you turned me on, you turned on a few guys. I so wish I could have seen you.”

“Every once and a while some of my brothers call me Lyla to get a rise out of me. Not so much lately, but it went on for quite a while.”

“Do you have any photos? I want to see how you looked.”

“I managed to delete the couple that were taken. I didn’t want them to pop up on FaceBook or someplace even worse.”

“Damn. I really would have loved to have seen how you looked.”

“I hope you are not upset about hearing this.”

“Only that I am hearing it over three years after the fact. Did you ever do it again?”

“What? Of course not. Why would I do that.”

“There’s nothing wrong with it. You obviously had some fun with it and looked great. Didn’t you ever think about it.”

“Sure it popped in my head a few times, but it didn’t seem like a very good idea. I never really had a reason and of course everything but the nightgown disappeared after the weekend.”

“Tell me the truth, did you ever wear the nightgown after that weekend?”

“I stashed it away, It would have been very weird for any of the guys to even know I still had it.”

“What about after you moved out of the house?”

“I did wear it once out of curiosity when I had my own place. I just wanted to remember the silky feeling, Then I met you later in the year.”

“Once? Come on… It felt nice, didn’t it?”

“Ok, more than once, but I haven’t worn it since we have been together.”

“You still have it?”

“Umm, I’m not sure.”

“Really? You either remember parting with it or you still have it somewhere.”

“It’s probably somewhere buried in my closet.”

“Do you ever have the urge to slip it back on?”

“Why are you teasing me? I love you and you are all the girl I need.”

“I’m just fascinated by the learning this. I have always found you attractive, but some of it is your androgynous features. You are handsome, but I can also see how you might be pretty too. I mean that in a good way.”

“So I am not manly?”

I’m not saying that. I love you and have always been drawn to you. It’s just that I am now a little curious to see what you looked like.”

“Well there are no photos, so that’s impossible.”

“Would you ever let me make you up for fun? I think it might be enjoyable for both of us.”

“You really would want to do that? I always thought this would turn you off.”

“Not sure why, but I really am curious.”

“Maybe someday. No promises. We will be at your folk’s house for a while, so let’s forget it for the time being.”

“You are probably right there. Maybe there will be a costume party or something like that down the road that we can have some fun with.”

With that we ended the discussion. I saw an odd gleam in Jessi’s eyes. I knew that this would not be the final conversation on the topic.

Chapter 3:

Nothing more was said about my Cheerleaders experience for the next few days. We were very focused on finishing up school, our graduation and moving in to Jessica’s family estate. Jessica continued to coach me on how to behave around her parents and the importance of building a bond with her Mom.

Despite the fact that our relationship was a bit rebellious against what Jessi’s parents expected for her, she was still very tight with them and wanted to maintain their trust in her. Jessica and her father often talked about his business and I think he saw in her a future star at the firm. There was no doubt he wanted her to work at his company and groom her for a major role when the time was right. She was privy to many of his ideas that even some of the top executives there did not know. On a few occasions he sought her opinion on some concepts before presenting them to his associates. They rarely chatted about feelings or personal issues; that was usually reserved for Jessi’s Mom.

Jessi and her mother were very close in a more personal way. Her Mom did not work for a paycheck, but she was involved in many high-level charity endeavors and managed the family estate. Though Jessica was career driven, she still respected her mother and valued her opinions. She had graduated with a psychology degree from college and shortly after that met her eventual husband. When Jessica needed personal advice or needed emotional support, she always called Mom. The depth of Jessica’s relationship with me was one of the few things that she rarely spoke to her mom about. Mrs. Johnson knew that we were dating, but not that we were basically inseparable.

The first day we were living under their roof, I felt like I was walking on ice. I was trying to be so polite and constantly thinking about all the rules Jessica had established for me. Though I only saw her mom for a short while that day, I tried to be agreeable and make my best impression. I am sure she could see my nervousness.

It was a relief when Jessica told me that she was going shopping and for an afternoon coffee with her mother. I was thrilled to be left alone and have some relaxing private time. Jessi and her mom did a lot of catching up that afternoon. Much of the conversation was apparently about me. Jessica’s Mom and Dad would ultimately let her make her own decisions, but at that stage in our relationship, I don’t think they would have been against undermining me a bit. They did not dislike me, but I was not the vision they had for their only child and daughter.

“Mom, he really such a sweet guy. Once you get to know him better, you will love him like family. He’s not that different than me. We have so many shared passions.”

“We don’t have anything against him. We just want to make certain he is right for you. Is that unfair?”

“No, but you have to be open minded. He would do anything for me and probably for you as well. That is the kind of person he is.”

"That’s good. I am sure he is very nice.”

“Give him a fair chance and he will win you over.”

“Of course we will. I will try and spend some quality time with you both. In fact I promise to spend time with just him; One-on-One. That will let me best get to know him. “

“I hope we can find some time as a family to all be together. Dad’s schedule is always so busy.”

“I Know he is working on the big development deal for a high rise in Chicago. So this week is likely to be challenging for him. At least I know he will be home for the weekend, because the Art Institute costume ball is this weekend. They will be unveiling a couple of new Renaissance paintings that were just acquired. Your father was very much involved in the fund raising for those pieces.”

“Costume ball? Since when does the Art Institute put on a costume ball?”

“Honey, I’m being facetious. Your Father and I like to call these fancy black tie affairs costume balls. People dress up so over the top that you sometimes don’t even recognize them. I think the Art Institute fundraiser is one of the most extreme. I could wear a tux exactly like your fathers and no one would bat an eye.”

A big smile started to cross Jessica’s face. “Maybe you should.”

“Should what?”

“Wear a tux.”

“What’s gotten in to you?”

“Nothing really, just thinking about costumes and things.”

Jessica strange smile was still plastered to her face. Her mother started to look closely at her expression, but inquired further. “What’s so funny. You must be thinking about something, because my costume reference was not that funny.”

“It’s kind of personal. Your comment about wearing a costume made me think about it.”

“Soooo what were you thinking about?”

“I really shouldn’t talk about it. Like I said, it’s kind of personal.”

“I am your mother. We never keep secrets.”

“I know, but its about Lyle and I don’t want to embarrass him at all.”

“Honey, now is not the time to keep things from me about your friend. If you want me to know him better, secrets are not a good way to start.”

“Mom, he’s not just my friend. You know he is much more than that.”

“Understood, so what made you smile so broadly? It has to be something that made you happy.”

“It’s not that simple.”

“It’s you and me here. I think I can understand most things.”

“Well…. I’m not sure about talking about this.”

“Now, I do have concerns. Talk to me….”

“OK, but at least for now, I would rather you not let Lyle know we talked about this. Maybe there will be a time, but we just talked about this recently and I don’t want to look like I came running to you.”

“That’s fair.”

“Your costume comment made me smile because Lyle just told me about a little costume drama he had participated in when he initially joined his fraternity three years ago. He had to spend an entire weekend at his frat dressed up as a cheerleader. It was a 24-7 thing and according to him he was made-up to be pretty convincing.”

“You just talked about it?”

“He hadn’t mentioned it before because he was concerned I might not have liked it.”

"And do you?"

“Its not a big deal to me, but I told him I would have loved to have seen him. He was probably really cute.”

“How did he feel about it?”

“He said it was very strange, but because he actually looked so good it was not that big a challenge. He admitted that the frat gave him the name Lyla and treated him like a real girl all weekend. By hazing standards he said he got off easy.”

“So you never got a chance to see him or her as Lyla?”

“Funny… I did say it would be fun to try something like that again. I asked him if I could make him up some day.”

“What did he say to that?”

“It’s not like he jumped on it or anything, but he did say that maybe we could do it someday or for some costume party. That’s why I smiled. You mentioned the costume party and it clicked that memory into my head.”

Mrs. Johnson obviously was thinking hard about what had been said and trying to figure out what to say. The thought of her potential son-in-law traipsing around as a cheerleader did not strengthen her opinion of Lyle as the man for Jessica. She didn’t want to say something mean or negative, because Jessica might get mad or push back from her. Maybe this was an opportunity to show Jessica that he was not the man for her. It would only work if Jessica felt that she was making the call.

“Jessi, I think that letting him have that fun again would be precious. I bet he was very pretty.”

“You are not teasing me? You really think that?”

“I do. It could be fun for everyone.”

“Everyone?”

“Hear me out.”

“I’m not sure I should, but go ahead.”

“It would be a riot if he went to our ‘costume ball’ as Lyla.”

“Ha Ha. Its not really a costume ball.”

“Your Dad and I think it is and that is enough for me. There will be hundreds of people there and no one will know him. As I said, almost anything goes. In fact my guess is he wouldn’t be the first person to do something like that for the event.”

“Mom, I only suggested he do this for fun. I do not want to embarrass him.”

“I would help make sure he was not embarrassed. It could be a fun thing for him as well as his new family. Ultimately, maybe we could use this as something for all of us to bond over.”

“First, I doubt he could pull this off for something like that and secondly I do not think he would go for it.”

“On your first point, I will help him get prepared and if you don’t think he can pull it off by Saturday, he can wear a tux like your father. As to whether he is up to the challenge that will have to be up to you. You can just call it a Costume Ball until you think he can pull it off or to gauge whether he is enjoying it. It’s up to you and you can tell him whatever you like. I think if he knows you and the whole family are on board he will have fun with it.”

“That seems kind of deceptive. I would hate myself if I hurt him.”

“This is for him and you. You said he might like to re-live the experience and this way it will be guilt free and give him and me an opportunity to spend quality time together.”

“I’m still not sure. The event is Saturday, and only six days does not give me much time suggest this to him and get him ready. That would be even if he considers it.”

“Your father wanted to take you with for his business trip on Wednesday to Chicago. You will be back Friday or maybe even sooner. You have today and tomorrow to propose this to Lyle. If he is willing, I will help him while you are gone. We will get him everything he needs, no matter the cost, and I will make sure he is pampered along the way so he has the maximum fun doing it. If he lets himself, I will make sure he has an even better time than when he was in the fraternity. When you return from the trip, if you don’t like what you see or think it’s a bad idea, we will forget it.”

“Let me think about it. It seems a bit much, but I do have more than a little curiosity as to how he would turn out.”

To be Continued?

Part 2

Chapter 4:

When I saw Jessi Monday evening she seemed very distracted. She said it was just some issues between her and her mother. I knew she was trying to process something. She didn’t look upset, just not all there. A couple of times she began to talk with me only to abruptly interject some random thing she saw while out with her mother. She later decided to turn in early. Before quietly slipping into bed she asked me to plan on having breakfast alone with her. We did that a lot, so it was weird that she mentioned it before bed.

We made breakfast together the next morning and sat out on the deck by the pool. It was always fun cooking with her and I know she had something on her mind she wanted to talk about. It was a beautiful morning even if I sensed something coming. I was clueless, but I knew she had been thinking about it since at least last night.

“Lyle, can we talk about a couple of things?”

“I knew something was up. Of course. Did I do something?”

“No, no … you’ve been great. Just a couple of things came up that I wanted to run by you.”

“Sure, is everything OK?”

“Yes, it’s nothing that serious, but I want to ask you a couple of favors.”

“Anything sweetie. You know that.”

“Well first, I wanted to know if it would be OK if I left you here with my Mom so I could accompany my Dad to Chicago to help him with his big new project. I would probably be gone two nights. I know you probably don’t want to be all alone with just my mother, but it would be a great way for you to have quality time together.”

“I’m not sure she would like that, but if it means a lot to you, I can survive a couple of days hanging with your mom.”

“That’s great.”

“You said a couple of things. That one wasn’t something that should be making you so distracted. What else is on your mind?”

“Lyle, the second one is more complicated. I am not even sure where to start.”

“Wow. I have not seen you this nervous since those four finals in two days during second semester junior year.”

“Try not to say too much until I explain the whole thing.”

“Sure baby.”

“This Saturday is the Art Institute Gala dinner at which time they will unveil two new master artworks just acquired by the museum. This is a really big night for my parents, especially my dad. As my folks describe it, it is a formal Costume Party. Not like Halloween, but fancy ball gowns and stuff like that. People dress in some crazy expensive getups but all appropriate for the important occasion that this signifies. Many of the folks are hardly recognizable in their theatrical looks, but it is always appropriate formal costumes. My folks will be at the head table and my father will even be making a speech and unveiling one of the works.”

“I’d love to go, but I probably need to get something to wear.”

“That’s good, but I kind of talked with mom yesterday and for me I would really like you to wear something extra special. My mother will help you pick it out while I am gone.”

“I said I was good to go. I’m sure she knows better than me what to wear.”

“Lyle, Mom and I talked about a lot of things yesterday and your experience as Lyla came up. I’m really sorry.”

“My God. She must think I am a freak or worse.”

“No not at all. I told her I was totally good with it and my only issue is that I never got to see you all dolled up.”

“She still wants to be help me find something fancy enough and stay here with just me. Did you really need to tell her that?”

“It kind of came up when she referred to Saturday’s event as a costume ball. I began to smile because of our last chat about you wearing your costume. She managed to get me talking and truthfully we keep very little from each other.”

“Should I say anything to her?”

“I was hoping you would say yes.”

“Huh?”

“For me, you and even for my parents, I was hoping you would agree to go to the party as Lyla.”

“You’re joking. Right?”

“I’m not. I told her that I would have enjoyed seeing you all made up and she thought it would be fun too. She was quick to volunteer to help you get ready.”

“You want your mother to help your almost Fiancé dress as a woman.”

“When you say it that way, it does sound a bit crazy.”

“It is crazy.”

“It probably felt crazy the first time, but I know from how you told me about it, that once you got over that is was sort of fun. This time I will be with you and my mother will make sure you are truly pampered. No one is going to laugh and she will make sure everything is perfect for you.”

“That was three years ago. I am 21 now. This isn’t a frat house I will be going to. I don’t want to embarrass myself or even your family. There will be people there looking all fancied up in their ball costumes and you will walk in with your boyfriend looking like a buffoon. “

“That’s not going to happen. First off, I bet you will look very nice and I won’t let you go if I don’t think you can pull it off. I will make sure you have a fancy tux at the house, if when I get back from Chicago either of us don’t think you look great.”

“Your Mom really said she wants to help her potential son-in-law play dress up for a party?”

“It was actually her idea after I spilled the beans.”

“This is getting very surreal.”

“She said she would do whatever it took for it to be fun for both of us. I believe she really wants to help you. She has great taste…that’s where I get mine. I know this is not what you expected, but do t for us. I want to see you looking regal and after you get over the shock, I think you will enjoy it more than you might admit. Dressing up like this will be so much more fun than wearing just a sweater, skirt and keds.”

“Can I think about it?”

“Sure, until breakfast is over. I need to know so I can plan to go with Dad tomorrow on the business trip. It’s probably better that you don’t have to think about it very long.”

“Really? What if I decide later to back out?”

“Beside me being a tiny bit disappointed, I guess that would be understandable. My mother is going to spend more than a few bucks on you, so I expect you to give it your best shot and cooperate. She knows what she is doing. Trust me. If once you have given it fair shot you decide it’s too hard or you absolutely can’t do it, I will understand. Both of you can keep me updated along the way.”

“So?”

I gave her a crooked, but affirmative nod.

“This is going to be spectacular. I am so excited. After breakfast and a quick stop in our bedroom for some closed-door celebration, I will let Mom know Lyla is on board.”

After rolling my eyes at the last comment, I followed her into the bedroom for some very passionate sex. We were both highly aroused as we leaped into bed together.

Chapter 5:

“David, maybe after Jessica see’s him as something less manly than the boy she fell in love with, she will reconsider getting married.”

“Sophia, you know I am less than thrilled at her surprise pronouncement, but I think she should be making her own decisions.”

“I do too. I just think that if we give Lyle a chance to express part of himself that she has not seen, it is possible that we help them both.”

“We both know your plan is geared to more than just help them out.”

“Of course, I had hoped she would marry some important socialite, but I also don’t want to hurt either of them. He is a sweet kid and has treated our baby very nicely. If after the weekend they still feel the same, I will happily welcome him to the family.”

“I still am not sure about this plan to dress him as a woman for the benefit. This is our most important night and I don’t want to make a scene there. It wouldn’t be fair to him and would be embarrassing for us as well.”

“I am already on that. If he cannot completely pull it off, I will make sure Jessica or I pull the plug. I have already lined up some of my friends and called in a favor. You go on your business trip with Jessica and if anyone, including Lyle does not think they can do it, we won’t take the risk. Even if it doesn’t make it to the affair, I will make it a special experience for him. Remember, I plan to pamper and spare no expense letting Lyla have her moment. Even you would probably enjoy some of the attention she will get.”

“Very funny. You already are referring to him as her.”

“Seriously, some of what we go through to be pretty is very enjoyable. Don’t knock it if you never try it. And by the weekend you will need to get used to thinking of Lyle as Lyla. I don’t want you to be the one creating the stir.”

“Ok then, I trust you. If your idea does not go according to your plan, then change it. I mean it when I say I want the best for them. Jessica would never forgive me if we pushed them apart. “

“Remember David, Jessica already is on board with seeing him as her. I am only going to facilitate making it happen. I will be getting started right after you two catch your morning flight.”

We all had dinner Tuesday evening and I felt like crawling under the table. Everyone knew what was on the agenda for Saturday night, and for most of the dinner we all tried to avoid talking about it. Near the end of the meal the first reference to it was breached by Mrs. Johnson.

“So Jessica, I understand you and your father will be leaving the house at just after 7:00 for your flight to Chicago. Do you need any help with anything?”

“Just take good care of Lyle for me while I am gone. He’s going to be family, and just because I am gone he should still be treated that way.”

“Honey, Lyle and I are going to have so much fun. I bet you will be jealous. I promise to take the best care of him.”

“Just do your best to make him comfortable with whatever you two do. I will be checking in with him to make sure everything is good.”

“Don’t fret I will treat him just like I would treat you. I plan to get things in motion tomorrow morning. There is not much time to get him what he needs by the weekend.”

“Mrs. Johnson, do you need me in the morning or will you just be picking up the things I need?”

“Lyle, you will be part of the process at every step. Besides needing you for things like measurements and fitting, I have lined up spa and the full Salon experience. I also want you to be helping make choices along the way. It’s important that you have a say in everything, including your statement dress. Picking things out is half the fun.”

“Ok Mrs. Johnson, I guess I will just follow your lead. I will obviously have to rely on you. I’m clueless on this girl stuff.”

“Please call me Sophia, or just Mom. I am sure you will do great. Just relax and let yourself enjoy it.”

“Ok Mrs. Johnson, I mean Sophia.”

Chapter 6:

I was up for Jessica's departure. I hadn't slept that well full of nervous energy. I was anxious about what was planned. It was mostly a fear of the unknown, but I remembered that the first time it was not totally unpleasant. The idea that I might enjoy some aspect of this made feel an extra level of concern. There was a fine line between going with the flow and having a good time.

Jessica made it clear once again that I should try and bond with her mother while she was gone. Being difficult or challenging her would not help the two of them in the long-run. She wanted me to enjoy the experience, but cooperate. She also told me to become the best girl I could. She was excited to see me when she returned and said it would all be worth it in the end.

The only instructions I had been given the prior evening by Mrs. Johnson was that we would be leaving early in the morning. She also said that I should shower and wear comfortable clothes that would be easy to change in and out of.

When I sat next to Mrs. Johnson in their Mercedes S-class sedan, she gave me a big smile and said, “I bet you are excited?”

“I am something. Not sure I would describe it as excited.”

“Well I am excited for you.”

“Sophia, what kind of shop opens at 9:00am?”

“I know you want to go shopping, but we have a lot of work to get you ready for that first. Don’t worry we will have plenty of time for that later.”

“So where are we off to?”

“We are going to Nine Zero One. We need to start at the top and work our way down.”

“What is Nine Zero One?”

“You do have a lot to learn. Nine Zero One is only the most fabulous Salon in all of LA. They also have a reputation for making blondes into to starlets. I have you booked there for the works. If anyone can make you and your hair look fabulous, it’s them. It’s very private there, but don’t be surprised if you see a celebrity or two sneak in or out.”

“I thought I was just going to wear a wig.”

“We need to do this right. This is not a frat you will be going to Saturday. Anything less than perfect will make you stand out. You don’t want to look campy in your gown, do you?”

“No, but my hair is not super long. I know it is a little longer than it should be, but what can they do with it?”

“Leave it to them. They may ask a few questions, but ultimately LuLu and her team are magicians and will work wonders.”

I felt so under-dressed when we gave the car to the Valet and went inside. Sophia instructed me to check in while she walked to the back.

I made my way to the receptionist. I had never been in a place like this before. “I’m here to get my hair cut.”

“Welcome to Nine Zero One. May I have your name?:

“Lyle Adams.”

“I’m sorry, but I don’t see your name. Who made the appointment?”

“It was probably made by Sophia Johnson.”

“You must be Lyla. She has you booked with LuLu and and her team. Would you like an espresso or something else to drink.”

“Thank you, but I am fine.”

“Let me take you back to her area. You are her first appointment today and with all of your scheduled activities, I am sure she will want to get started.”

LuLu was not what I expected. She looked like a young executive, not a hairdresser. She was dressed in a power form-fitting suit. She couldn’t have been more than 35, but she was obviously captivating and very confident. She approached me and took note of my full image before greeting me. Apparently, hello was not in her vocabulary.

"Lyla is a beautiful name and soon you will have an image to match that. Are you ready to bloom?”

“I’m a little nervous, but ready.”

“Just relax. We will do all the hard things.”

“Cut away”

“In time. First a few questions.”

“K”

“Do you like being a blonde or have you ever thought of changing things up?”

“Never really considered changing colors. I like being blonde.”

“That’s fine, but I could really see you as a red head with those cute dimples you have.”

“Thank you, but lets stick to blonde.”

“How good are you at applying makeup? Do you wear a lot?”

“Seriously? I can put on chapstick. Not much beyond that.”

“Hum… hard to be truly glamorous without makeup. We can help you a bit, so you wont have to do as much on your own, but it will add a little extra time. I have a gal that can give you some private lessons at home. Before you leave I will give you her number.”

“Thank you again, but I doubt that will be necessary.”

“Let’s get started. You tomboy types never understand how much effort it takes to look beautiful. Maybe after today you will appreciate how lucky you are to have natural beauty.”

My morning went on and on. Instead of a cut, I had extensions permanently attached to my hair. Once attached, it was all bleached a golden blonde. Two technicians worked on my eyes at the same time. I thought they were attaching false eyelashes, but the smiling Asian girl called also referred to them as extensions. They were being applied individually. When done with my eyes, they did the opposite to my brows. They plucked away making me worry that they may be taking too many.

Moments after they finished I was swept up into another room and they waxed my sparse body hair. I didn’t think I had much body and leg hair, but it was still very painful. From there I was shifted to a manicure/pedicure location and received a set of summer pink acrylic extensions with matching toes.

I mistakenly assumed I was finished when I was seated at another station for makeup application. During this entire process, I was only able to get partial looks at my progress. I was told that I was finished and that Sophia was ready to take me to lunch. I began to walk into the lobby, but stopped cold in my tracks when I finally had a chance to see their work.

There was no way that anyone would recognize me. I may have had the body of a teenage boy, but my face looked like that of California Beach Babe. I blinked my eyes and watched them flutter. I felt someone tap my shoulders and ask if I was OK.

“Yes, I just can’t believe this is me.”

“We get that a lot. You are a very pretty girl.”

“I just never…”

“Lyla dear. Come and let me see how lovely you turned out.”

“Sophia, they went overboard.”

“LuLu said you picked out the color and asked for Lash Extensions. Jessica will be jealous. She hates applying false lashes when she wants to dress herself up.”

“I didn’t ask for anything. She asked me some questions and then her team went to work. LuLu mostly oversaw the process. All she did was a little trimming of my hair.”

“It looks stunning. You now have almost unlimited style options. It will be fun to pick one for Saturday. You and Jessica can decide after you pick out your gown. You can even wear it up if that’s what you want.”

“Sophia, I am speechless.”

“Lets go and get a bite. I would take you to the club, but your wardrobe is not ready for prime time.”

I never thought Mrs. Johnson would go to a chain restaurant, but she said we only had about an hour. I was afraid to ask why.

END OF PART 2 --- What could be next?

Part 3

Chapter 7:

When I went outside dressed as a cheerleader it was on a college campus and part of a fraternity hazing. Now I was walking into the Bonefish Grill with my future mother in-law looking more like a future daughter in-law. While I was dressed simply in jeans and an Old Navy sweater, my appearance could hardly be confused with a male. My body had no distinguishing shape, but what most people saw was my shimmering hair and makeup. I tried to convince myself that it was a slightly androgynous look, but anyone that saw me would more likely think I was a girl trying to dress down.

Mrs. Johnson could see me scanning the crowd intermittently as I tried to keep my head down.

“Lyla, don’t be so self-conscious. Even in those rags you are as pretty as anyone here. Stand straight and if someone looks at you, look back and smile or nod.”

“Do you really think people can’t read me? Besides probably looking like a boy in makeup, I am dressed like one.”

“It will get easier after you relax and stop thinking like a man. You need to work on how you move and act. I promise to make sure that your clothes won’t give you away. We will start on that task after some lunch.”

“It’s hard to not think that way.”

“You just need more practice. I will give you some tips and help you learn. If you let yourself, I am sure it will become second nature. Don’t fight it.”

“I still can’t believe I am doing this for a costume party.”

“Stop thinking that way. You are doing this for you and Jessica. She wants you to have the full experience and she told me she wants to see how beautiful a woman you make. The more you throw yourself into this, the better that it will be for both of you.”

“It just seems so extreme.”

“I know my daughter, if you don’t give your best she will be disappointed. If you do everything possible to be the best Lyla you can, then no matter how you turn out, she will know it was the worthwhile.”

“I will go all in, but I hope I do not look too authentic for the party. I am sure not many others guys put in such an enthusiastic effort, just for a costume party.”

“The more convincing a woman you can make yourself, the better will be your experience on Saturday. I can pretty much guarantee you of that.”

Following lunch, we made our way down to Rodeo Drive into a very exclusive lingerie shop called La Perla Boutique. Not surprisingly, Mrs. Johnson had someone there that was prepared for our arrival.

“Hi, I am Fifi, you must be Lyla… your mother told me so much about you.”

“Oh Mrs. Johnson, I am not sure what she told you.”

“Enough to know that we are starting from scratch and need to make you look and more importantly feel more girlish. Looking your best, starts with feeling your best and the proper foundations.”

“Your merchandise looks very beautiful, but I really don’t think I will need that much.”

“Sophia, she is so precious. She is on the way to being absolutely lovely, but certainly has a lot to learn.”

“Fifi dear, she needs everything we talked about. She has nothing now. She is even wearing boxers at this moment. She wants to look sexy, but not trashy. She will need the proper garments for casual, nots so casual and of course for evening gowns.”

“Mrs. Johnson!”

“Please, I prefer Sophia or Mom.”

“Ok, but I don’t need that much. Won’t one thing do?”

“Don’t be silly, We are not going to be washing your things every night. The benefit is not for three days, and you will not be wearing the same clothes for all that time. Just let Fifi do her thing. You are in for a treat.”

“Let me take you into the back and get you set up. After you strip, I need to measure you and get started. Don’t be shy, I do this all the time.”

“I am sure you are phenomenal at this, but I am not like most of your customers.”

“Not like most, but you are far from my first for your special needs. If you want, you can leave your boxers on until we find something more appropriate.”

It felt so strange having this strange woman walking around my nearly naked body, measuring me with her tape. She wrote down measurements that meant virtually nothing to me. She even touched me around the waist and at the breast to see how firm I was. Once she had a chance to determine what she was working with she asked.

“Lyla, do you find woman with large breast more attractive than other woman?”

I was a little put off by the question. “I don’t judge woman by their breast size. That’s a terrible thing to do.”

That’s a good answer. I just wanted to know if you had a desire to be oversized. It does not sound like it.”

“Of course not. The last thing I want to be is a caricature of a woman. That would be insulting.”

“Good. I think I am ready to get started.”

The first thing she brought me were a pair of off white panties. She insisted that I replace my boxers. Unfortunately, the silkiness of the panties was to much for me to ignore and I found myself aroused by the time she stepped back into the room with Mrs. Johnson at her side.

“My my, that is going to be a problem.”

“Fifi, we can’t have that happening under his new clothes. It would be very embarrassing and ruin the look.”

“Sophia, I have something that will help, but it is not always perfect. It can also be a little uncomfortable if she continues to get so aroused.”

“Well we need to keep that at bay.”

Fifi return a couple of minutes later with a latex garment that she called a dancer’s gaff. She asked Mrs. Johnson to step out of the room as she showed me how to properly wear it. Tucking myself under and clamping it down with this gaff was not very comfortable. At least for the moment I was no longer in the excited state. She slipped the panties over the gaff and I was now sporting a woman’s flat triangle. Mrs. Johnson was let back in and quickly commented how much better I looked.

Next came a white matching bra that she mentioned was a 36c. Two heavy globs were stuffed into the cups and instantaneously I looked dramatically different. Anyone at that moment looking at my image would without hesitation presume I was a young woman. There was no sign of my maleness. I was fascinated by my appearance, but also very afraid by the convincingness of the reflection.

It didn’t help my psyche that Mrs. Johnson said I made a more natural looking woman than she even suspected. My heart skipped a beat when she exclaimed that she would be proud to call me her daughter. I knew I was more than just passing at that point, I was attractive standing in front of the mirror only dressed in lingerie.

I could feel my hidden manhood trying to pop out which was very uncomfortable. I looked down at my panties with an uncomfortable expression on my face. Mrs Johnson and Fifi picked up on my distress.

“Lyla, if you don’t want the world to know your little secret, you need to stop getting so excited by your transformation. We still have work to do.”

“I’m sorry, this is just very confusing.”

“You just need to get adjusted. It shouldn’t take you very long. The gaff will just have to do until you can get a better handle on that or we can come up with a better alternative.”

I could feel the weight of the breast-forms in the brassiere and cupped them with my hands to get a better sense of the new appendages.

“Mrs. Johnson, I mean Mom… these feel and look almost real.”

“Those are made of silicone. For now, you will just have to settle for those.”

Her comment and the fact that Fifi was taking this all in, made me squirm like a shy girl. I had no legitimate response and standing almost naked, I felt so vulnerable and defenseless.

I thought that we were done at that point, but I was pushed into modeling numerous other matching styles and colors as well as other sexy items. I protested unsuccessfully when the corset was tightened around my waist. Mrs. Johnson assured me that Jessica would love to see me with an hourglass figure. I had trouble accepting that logic, but the physical discomfort it created was offset by the fascination of how it redistributed my body. It was almost like it squeezed any remaining masculinity from my formally shaped frame.

I was grateful that the ordeal was finally coming to an end. Mrs. Johnson and Fifi discussed the choices after they had exhausted the inventory options available for me. I was told to keep on the foundation items I was currently wearing and slip on the items in a bag that I was handed.

I had entered the store dressed in my jeans and baggy sweater, but inside the bag was a bohemian style dress from Free People. I initially thought it was just to see how the lingerie might look under clothing, but as soon as I had slipped it over my head, Mrs. Johnson removed my former clothes from the changing area.

I took the remaining items from the bag before calling out to Mrs. Johnson. There was a purse, and a pair of strappy wedge sandals and nothing more in the bag.

“Where’s my clothes?”

"I am having them sent to the Johnson residence with your other lingerie purchases. No point in you lugging them around.”

“You mean I am wearing this out?”

“Lyla, you look lovely. That dress now fits you perfectly. Inside your purse are some wrist bangles that will add a nice touch. You can step out as soon as you are ready.”

I knew as soon as I agreed to go to the costume party that I would be dressed completely as a woman, but that was not for three days and here I was looking like a college pretty college coed in the middle of the afternoon. There was not one aspect of my appearance that didn’t scream feminine.

When Mrs. Johnson saw me emerge from the cubicle even she paused for a moment to take it in.

“Lyla, you are perfect. Aren’t you thrilled by how gorgeous you turned out. Jessica is going to love her new girlfriend.”

“I think shocked would be more like it.”

“Not at all. She knew you would look beautiful. Remember, she wanted this almost as much as you.”

“I never said I wanted this.”

“Let’s not argue. It takes a very special boy to allow himself to become such a convincing young woman. The next few days are all about fun. Make the most of your Lyla time, so when Jessica comes home you both know this was the right choice. She would be very disappointed if she didn’t think you were making the most of your opportunity.”

“I’m trying, it’s just all happening so fast.”

“You fit in much better now. It would not have been fun with you dressed as a boy when we go shopping for your fancy dress for the Gala.”

“I don’t think I am ready to do that yet. Today has been pretty overwhelming.”

“That’s ok. We are seeing my Stylist at Bloomingdales tomorrow. The dress shopping will wait another day.”

“That’s good. Are we going home now?”

“Soon. Let’s stop at the Starbucks, before our last quick task.”

As we walked down the block, I had to get used to the new sensations resulting from my appearance. It was one thing for the woman to take a glance at me, but it was very disconcerting to get checked out by some men as they walked towards me.

The iced chai latte tasted very good and helped me regain some of my composure.

“Where’s our last stop?”

“The jeweler two doors down. If you are going to be properly accessorized for the Gala we need to pop in there.”

“We don’t need to be buying expensive jewelry for only one night.”

“I agree. You will probably wear something of mine or Jessica’s after we pick out your dress. We just need to stop there so you will be able to.”

I really didn’t follow her logic as I followed her into the Jeweler. Not surprisingly she was greeted warmly by her first name. The woman and her walked around the store for a couple of minutes before Mrs. Johnson pointed to something in the case. The woman smiled and took an item out to show her.

I was finally included in the discussion as they walked over to me.

“What do you think?”

“Sophia, those look like lovely diamonds. I am not a good judge, but they look simple but very classy.”

“See Vera, I told you Lyla had a good eye for this.”

“Thank you, Sophia. Are these for Jessi?”

“You can share them with her, but these are my gift to you. Your first studs should be special ones that you will always cherish. I want you to have a pair that is appropriate for such a pretty woman.”

“Sophia…”

“Please call me mom.”

"Mom, these are way too nice for me and they are for pierced ears."

“Of course. These will be your first pair after Vera pierces your ears.”

“I think I look girly enough without pierced ears. I don’t really think that is necessary.”

“Gifts are never necessary. That’s what makes them special. Having pierced ears is however necessary. You are going to a very fancy party Saturday and all of Jessica’s and my earrings are for pierced ears. If you decide to ever stop beautifying your ears, which of course would be a waste, the holes will fill in naturally.”

“I won’t need these studs then. I wouldn’t want you to waste your money.”

“First off, you will have to wear them for a while to avoid getting an infection and later if you want, you can re-gift them to Jessica. I do hope you decide to keep them. I’m enjoying our time together and this will be a nice memento.”

“Ok then.”

Before I had a chance to rethink anything I could feel the pinching of my ears. I looked at my ears in the swivel mirror on the counter and could see the shimmering reflection coming from my lobes. I felt like it was symbolic punctuation of my total emersion into femininity. The holes might later fill in, but for the moment I felt I had totally abandoned my manhood.

Mrs. Johnson took the opportunity of me transfixed in the mirror as a good time to take out her iPhone for a few photographs.

“I need to take a couple of shots for Jessica. She will want to know how things are going and you might like these as keepsakes too. Stand up and smile for me.”
She had me pose for at least a dozen different shots. A couple were close-ups, and a few were in very staged feminine poses. When she was finished, even I was curious to see them. They looked too good. They appeared to be photos of a pretty girl… nothing more, nothing less. I wasn’t even sure that my Jessi would know they were of me.

Thankfully, our shopping was done for today. I knew tomorrow would bring more new feelings.

Chapter 8:

Back at the Johnson home I retreated for a while to my bedroom. I was emotionally spent by the full day of activities. It was the first time I really had a chance to think about what was happening to me. With each passing hour, I had become more-and-more Lyla and less-and-less Lyle. I was spending quality time with Jessi’s Mom as requested, but I couldn’t imagine it improved my standing as their future son in-law.

I also did not know how I felt about my transformation. When I agreed to this, I used my frat hazing experience as a reference point. That foray in the cheerleader’s uniform was kind of fun, but I never took it that seriously. The current image I was staring at on the closet door was not a gag. It also was not all going to wash off when I hit the shower later. I was going to a costume ball on Saturday, but this degree of preparation seemed way over-the-top.

I also didn’t hate what I saw in the mirror which added to my confusion. The fact that I turned out to be attractive felt like a déjà vu, causing me to re-experience that comforting emotion when I first dressed as a cheerleader. In reality it might have been easier if I looked like a guy in a dress. Instead, I saw what everyone else's had to see and that was of an attractive woman. I kept telling myself that Jessi wanted me to enjoy this time, but I had some guilt about accepting this so easily. I wasn’t even sure what I was going to say to Jessica about today. My anxiety was on many levels.

I was pulled out of my deep thought by the distinctive ringtone on my iPhone. It was Jessi’s jingle. I was always happy to know she was calling, but for the moment I was scared to answer. My voice cracked a little when I finally got the courage to talk.

“Hi Jessi. How’s your trip going?”

“Lyle, is that you? You sound strange.”

I tied to over compensate in a deep voice, “Yes. I just had something caught in my throat. It’s Ok now.”

“My trip is fine. Lots of travel, we had one long meeting this afternoon. The real question is, how is my butterfly doing?”

“Butterfly?”

“I wish I was there to watch my Lyla spread her wings. Mom texted me some photos of you just after you decided to get your ears pierced. You look stunning.”

“I had no idea things would turn out the way they had today.”

“Mother said she had fun with you today. She says it was almost like having a second daughter.”

"She has me calling her Mom.”

“You're calling her Mom now. That’s so sweet.”

“She really insisted. I guess it’s easier under the circumstances.”

“It looked like you were really enjoying yourself in some of those poses. I was worried at first, that this might have been difficult for you, but it’s easy to see from the photos that you are happy. I was a little reluctant at first about you going to the Gala as Lyla, but not anymore. I hope you find a gorgeous dress tomorrow.”

“I’ll try. I had to try on so many undergarments to find the ones I am wearing. Girls have so many more options than guys.”

“Mom told me about some of your new lingerie. It sounds like you picked out quite a lot. Maybe you will share some with your sister when I get back.”

“Ha Ha. You can strip me in bed if you want my new sexy things. I have no idea what if any of the other items your mom actually purchased. She and the sales lady Fifi, had me try on all sorts of different things. I hope she kept the receipts for any extras they might have bought.”

“I think it was a very long receipt. Maybe you can get a job as a Victoria Secret model if you get bored with architecture.”

"Not likely, but wearing these things sure feels a lot different than my plain old jockey’s.”

“Better make sure you don’t like it too much. It might develop a bulge in your otherwise beautiful image.”

“Have you been talking about that with your mother?

“No, but based upon your response, I’m guessing you have been enjoying this even more than I suspected.”

“I don’t know what came over me. It’s embarrassing. Everything just feels so soft and silky. It’s like how I feel with you in my arms”

“Face it Lyla, you're hooked.”

“Stop kidding with me. I’d die if someone saw that bump when I was out.”

“Just teasing you. I’m sure there are ways to keep your little friend at bay or not constantly excited. Maybe we can trade your penis in for a vagina for a few days. Then you could try being a real girl for a few days. Wouldn’t that be fun.”

“Stop that. I having enough trouble being just your girl. Quit making this harder for me.”

“You are my girl. When I get back we will make some great lesbian love.”

“I wish you were here with me now for some lovemaking.”

“I’ve only been gone since this morning and you are already such a babe. I can’t wait to see how far you have come by the weekend.”

“I hope I survive. I can’t imagine it getting any crazier than this.”

”You never know. Just go with it. What do you have to lose.”

“Easy for you to say. Just don’t be surprised if I am pregnant by the time you get back.”

“That’s my lover’s humor I miss. At least my mother would finally have a grandchild.”

“Anything for Mom.”

“Keep that up and she will never let you go.”

“We’ll know soon enough.”

“What are you up to tonight? Do you have a hot date?”

“Yeah, your Mom. We are eating in, thank God. She mentioned that there were things she wanted to show me.”

“I want you to have fun, but right now I have to go. We’ll talk tomorrow.”

“Love you”

“Love you more. Bye”

Chapter 9:

Gratefully, Jessica seemed to be more than OK with how far the masquerade had gone. I knew she had encourage this, but a small part of me thought she might not like seeing her almost fiancé looking so totally feminine. I felt her enthusiastic acceptance relieved a major personal burden for me, and now I was much less concerned with how easily I had let myself be transformed.

Dinner with Mrs. Johnson was low key, but she continued my education into becoming the perfect Lyla. We ate a tasty chopped salad accompanied by a glass of white wine. I was still hungry, but she said as a woman that I needed to watch my figure. I had a hard time with her logic, but did not argue. Throughout the dinner, she coached me so I might better project ladylike table manners and utilize more feminine word choices.

Midway through the meal she even had me working to change the pitch of my voice. Sometimes I managed to sound more girlish, but occasionally I sounded clownish. She said that my voice was nearly as important as my look and could easily be my undoing. It was not something that I could change as simply as I managed with my appearance. I sensed some frustration in Mrs. Johnson.

After the meal. it was more lessons. First it was on my posture, then how I walked and moved and finally even some tips on eye contact. When we were both nearly ready for bed she showed me how to touch up my makeup and then showed me how to remove it all before bed.

When all my makeup had been removed, I was still amazed how feminine my face appeared. It wasn’t just my hair, which had received extensions, bleaching and styling, it was also my eyes. They had plucked my eyebrows into feminine arches and my eyelashes still looked like they had mascara on. That’s when I learned that they had also added to my lashes multiple new hairs. I was told they weren’t permanent but could last for weeks if I took care of them. She said I had requested the lash extensions, because it was not something she had originally instructed the technicians to do.

On my bed was a black nightgown which I simply accepted because I just wanted to go to bed. I actually found it’s softness very soothing as I slipped under the blankets. Just after I had turned off my lights I heard Mrs. Johnson, “Good night Lyla, I hope you enjoyed the day as much as I did.”

“Good night Mom. Thanks for helping me so much today.”

“You're welcome. Tomorrow's we will try and make it just as special.”

“Hopefully I won’t disappoint you.”

“I’m sure you won’t, now get some sleep.”

“You too, nite nite.”

After a restful night of sleep the schedule began the next morning with great pace. I had my shower, some coffee and a yogurt, then Mrs. Johnson sat me down to put on my makeup. She explained everything and told me that she wanted me to practice later when we had more time. We had a late morning appointment scheduled with her fashion stylist at Bloomingdales. I assumed it was for my Gala dress.

Unfortunately, I was instructed to wear the corset again along with a new matching bra and panty. I recognized the set from our shopping excursion. The dress she laid out for me was a simple dark blue, back zip sheath dress, which she said would be easy for me to change in and out of. The dress was paired with black leather shoes that had a narrower and more pronounced heel than the wedges from yesterday. The look was dressier and it took some practice to walk steadily in the new shoes.

We arrived at Bloomingdales and walked around for a few minutes before heading upstairs to meet her stylist Lana. She walked me through the jewelry, cosmetics, and handbag areas. We did not actually shop there, but she wanted me to get comfortable just browsing. Lana was ready for us when we made it to the clothing area. Lana and Mrs. Johnson shared a hug before turning their attention to me.

“Hello Lyla. Your mother told me how lovely you had become, but you are even prettier in person.”

“Thank you. Mom deserves the credit for that.”

“She does have great style. Hopefully we can add to that and pick out somethings that you really love. With your figure, we have many options.”

“I am clueless, and in your hands.”

“Sophia, says we need to work from basically scratch. She says you have almost no appropriate clothing and we need to get you all the basics, and of course something for the Gala this weekend. I bet you turn quite a few heads on Saturday.”

“I just want to look nice for the family, and look the part.”

“Well you came to the right place. We will start with casual and work our way up to dressy.”

“Work our way up?”

Mrs. Johnson interrupted our conversation by explaining the need for a larger wardrobe.”

“Lyla, you have no clothes. When Jessica comes home she is going to want to spend some time with you and see the young woman standing here. The Gala is the big event, but I am sure she will want to have some personal time with you. We will pick out a few things and of course if you never wear them, we can return them. From what I have seen with you and hear from Jessica, I am sure things won’t go to waste.”

“I am not so sure, but whatever. I guess it’s ok if you think Jessi would approve.”

“I am absolutely certain she wants you to be happy, so let’s get started.”

I could not believe the amount of clothes that I tried on. I was beginning to understand why it took woman so long to shop for their outfits. After a quick measuring, I was brought a series of items.

First came jeans, capris, shorts, and a dozen or more different style tops. Some for hot weather, some for the evening, but all appropriate for a casual event or outing. With each piece, I was asked about my opinions and preferences. After a while, I think I Lana and Mrs. Johnson began to understand a little what I liked and didn’t. For the most part I selected preferences that I might have liked on Jessi or on any other woman I thought attractive. My likes were generally more along classical lines and not extravagant.

After each fitting the items were taken out and sorted near the tailor station. Much like the lingerie shopping, I was not privy to which if any items that might be kept.

Trying on the casual clothing took nearly an hour and when that was finished they brought us some iced tea drinks so we could take a breather. Mrs. Johnson made the observation that I had a greater sense of style for woman’s clothing than for men's. I wasn’t sure if that was a compliment or a dig, but I thanked her. Mrs. Johnson smiled when I said that as long I was going to dress as a girl, I might as well pick out attractive styles I like.

After our 15-minute break, the clothing that was brought to me was much more dressy. It started with some shapely dresses from designers like Vince, Halston, Joie, Theory, and Lafayette. Some seemed appropriate for a Friday or Saturday night on the town, but others looked like classy work clothes. I was amazed how wearing some of these things effected me. When I looked at my reflection I felt a sense of pride in how nice I looked. I never had felt that when I dressed up in men’s wear. I began to feel a sense of anticipation when a beautiful dress was handed to me. I shouldn’t have been excited to wear these things, but seeing how well they looked on me began to show through.

When I slipped a lace covered Nicole Miller dress on I began to get noticeably aroused. I was wearing the gaff, but I began to get uncomfortable down below and Mrs. Johnson could see my discomfort and attempts to adjust myself.

“We are going to have to come up with a better solution for that problem. There is another option, but I was hoping it wouldn’t be necessary at this point. We can deal with that later, when we work on your voice.”

“I’m sorry, I don’t do this on purpose.”

“I know Lyla. Don’t fret. I have a solution for later that will be more comfortable for you. “

“What is it?”

“Just a more painless trick so you don’t try and pop out of the gaff. We will deal with that after lunch. Let’s finish up here.”

I thought I was done with the dressy clothes, but now I was trying on silky blouses, skirts, and some matching jackets. One white blouse was a wrap around and we paired it with a Steel Grey pencil skirt and jacket. I looked like a $1000 an hour lawyer and all three of us were impressed by the fit. I had no idea where I would wear this, but I felt sexy in this professional ensemble. Mrs. Johnson placed this in a separate pile from the other clothes.

“Mom, we have been busy all morning trying on clothes and I’m not even sure which of the dresses is the right one for Saturday.”

“That’s because you haven’t tried it on yet.”

“More dresses?”

“Just a few.”

The dresses that followed made me look like a princess. They were all long, fancy and a bit hard to maneuver in. I would not have looked out of place at the Academy Awards in any of them. The last dress I tried on was a shimmering black gown by Vera Wang. When I saw how fabulous I looked in this dress I was slightly overcome by emotions. I couldn’t understand what made me feel such an instant emotional feeling, but I couldn’t hide my mood. I had never been with a woman wearing something as beautiful as this dress and yet here I was wearing it myself.

Jessica wanted me to enjoy the experience, but I can’t imagine that she wanted me to be having this type of reaction. When Lana and Mrs. Johnson saw my reaction to this dress they immediately knew it was the one.

Lana looked me in the eye, “This is my favorite part of my job. I just love it when a woman sees herself in a magical dress and gets emotional. It sometimes takes dozens of dresses to find the right one and not everyone does. However, when that connection materializes like it just did with you, the moment is priceless.”

With that revelation, I was told my clothing shopping was complete.

"Can I get dressed now?”

I was handed the last blouse-skirt combination that had originally been put in a separate pile. I had liked how I looked in the combo, but I thought it was too professional looking to just be out shopping.

“Mom, why so dressy?”

“We are going to our club for lunch, and after that we need to stop by Jack’s office to pick up the Gala tickets. We also need to go shoe shopping and have at least one other stop. The dress you wore this morning was nice, but I think this white wraparound top with the pencil skirt makes you standout.”

“That’s fine, but I really don’t want to stand out to much. I just happy blending in and not drawing much attention.”

“Lyla, you are just going to have to get used to it. You are too pretty a girl not to get noticed.”

My wish was not granted. We made our way to the Brentwood Dunes CC which was the center of Mrs. Johnson’s social network. I must have been introduced to over 20 of her friends. I was grateful that she simply referred to me as her niece. I don’t think I could have handled her telling people that I was her daughter’s fiancé. I was going to really have to chop off my hair and change my appearance if I ever met these people again. I didn't mind that Mrs. Johnson spoke so glowingly about me, because she seemed to be genuinely happy while she did it. My biggest concern was that these were her good friends and I was being introduced as Lyla and soon I might be meeting these same people as Lyle.

Mrs. Johnson only spoke of me in a very positive light. She told everyone that I was also a recent architectural graduate like Jessica. Other than the fact that I was Lyle, everything she said was true. She seemed almost proud to be showing me off. A few of her friends inquired if there was a special man in my life, which caught me off guard and not knowing how to respond. Again, Mrs. Johnson was truthful in telling them there wasn’t and that I was still single and focused on my career.

I spoke as few words as possible as I was still having difficulty sounding as feminine as I looked. When we were alone after the meal, she apologized to me for putting in such an awkward spot before I was prepared to sound more authentic.

“Luckily Mom, I think most of them just assumed I was shy. I’m trying to sound more girlish, but it’s not easy.”

“That’s why we are making our first post lunch stop to take care of your little tells.”

“Tells?”

“I said we need to stop you from popping out of your gaff. I think my friend may be able to help you with your voice too.”

“I haven’t had a problem since this morning. I think I can handle it.”

I am worried about you having that issue at the wrong time, like at the benefit. Wouldn’t that be terrible if you had the problem in your gorgeous new gown?”

“That’s true. So where are we going?”

“I will explain it in the car.”

We made our goodbyes to her friends and hopped back into her Mercedes as soon as the valet brought it around.

_______________________

End of Part 3. What more could be on the agenda?

Part 4

Chapter 10:

Inside the car, Mrs. Johnson began to lecture me. “I am so pleased how easily you have settled into your role as a young lady. I mean this in a good way, because it feels like I have another daughter. I like having you in the family.”

I wasn’t sure how to decipher that. She was welcoming me into the family, but for a second time, hardly focused on a future son in-law.

“I feel the same about you Mom. You have been so nice to me and surely have gone overboard in preparing me for the party. I didn’t have any idea what these last two days would be like, but it has been miles beyond anything that I anticipated. I am beginning to appreciate women in ways that I never expected.”

“I can see that in how you are adapting. It’s a shame that few men have appreciation for what we go through to look our best for them.”

“I certainly have an understanding now.”

“We are almost at the Doctors office and we are right on time.”

“I thought we were getting me a more comfortable gaff so I would not pop out.”

“My friend Dr.Welby has an alternative temporary solution for your problem.”

“A doctor. I’m not sure I like the sound of that.”

“He is a friend and very discreet. If he can help, his method will feel less restrictive and you will not have to worry about embarrassing yourself. He’s just going to give you something that will hold you over for a short while. Its completely temporary, if you want it to be.”

“Of course, I do.”

“Don’t be so defensive. It’s just us in this car.”

“I’m just get a little nervous about seeing Doctors.”

“Dr. Welby is known for his bedside manners. You will like him.”

“I feel so strange going to be seeing a doctor looking like I do.”

“It will be easier if you focus on being Lyla in a completely positive tone. If he does not think you want his help, he will not assist you. If he asks if you feel like a girl, tell him you do. He needs to know that you want this or he can’t ethically do anything for you. He is a doctor and he can only prescribe things if you come across as committed. I told him about you, so just answer his questions without hesitation\ so he knows you are serious.”

“I still don’t understand what he can do, but if it is something to get me through the Gala and is temporary, then I guess I can hear him out.”

Inside the Doctors office I was lead to a private room. Before I had a chance to see the doctor, a nurse came and took my vitals and some blood. She only asked a few basic questions and I never even had to admit to her I was a man.”

I had to wait another 20 minutes before the Doctor came into my room. Mrs. Johnson entered the room with him.

“Sophia, gave me a little background on you Lyla. I can see how pretty a woman you are. I want to help you, but normal protocol is for you to be referred by a specialist to me. Mrs. Johnson is a very old friend, but I don’t like giving out meds unless I am sure it is appropriate. You certainly look very feminine, but I need to know that this is what you really want.”

I was not exactly sure how to answer, but I looked over to Mrs. Johnson. She smiled at me and with her eyes widely opened tilted her head as if to encourage me to answer.

“Yes, I want this. I don’t want anyone to look at me and see anything but a woman. I have come this far, but there are aspects of this that clothes can only cover-up so far. I need some help with… if you know what I mean. I really hope you can help.”

The doctor asked a few more questions which I also responded to positively. A few minutes into his interview the nurse came in and gave him my blood report.

“You are a healthy young lady. I am going to help you today, but I am also going to give you the name of a therapist that works with my gender patients. I encourage you to make an appointment very soon. She will help you sort out your feelings.”

“Thank You Dr. Welby. I still don’t know what you can do for me today.”

“Nothing major, for now. Just something to help you get physically comfortable with how you feel mentally. It should help your body react less like a man and more like a woman. It will not last that long and I won’t continue your treatment and give you any more medications unless I know you have seen the therapist.”

He wasted little time giving me two shots. He also gave me a bag of sample meds.

“What did you give me?”

“The first shot blocks your testosterone production and the second shot was a mild dose of female hormones to replace that. You will need to take the sample pills for at least three weeks. By then I expect you to bring me a referral letter from the therapist.”

I was stunned by what he told me. I didn’t know what he was going to give me, but this was not what I expected to hear..

“What does that mean?”

“I did not give you a heavy dose of the estrogen hormones, because first you need to first slow your testosterone production. In a day or two it should be hard to get an erection, but you can still have sex if you are active.”

“That’s not permanent is it?”

“Sorry, but it’s not that easy for permanent results. You need to be on the medication for months before that is true, unless your therapist thinks you need to speed things up and then you can consider an orchiectomy. That’s irreversible, but I wouldn’t suggest you go that route at this point. Take it slowly, in case you decide being a woman is not what you want.”

I was getting dry in my throat thinking about what I had just received. It may only be temporary, but it was more than just a weekend step.

“Your Aunt also mentioned that you were having trouble with your voice. If you stay on the these meds, that might help a little, but usually that impacts very marginal if at all. A voice therapist can help you work on your pitch if you have trouble on your own. If it is a real problem there are procedures like a Laryngoplasty that permanently tighten your vocal cords. For today, I an just going to give you a shot that will temporarily tighten those muscles. It will wear off in a few days, but you can see how you like that or if surgery is something for you to consider.”

I was still feeling the shock of what had just happened, when he dabbed some Novocain on my throat and then injected me with a short needle. He told me not to speak for about a half hour.

I left his office wondering how I got to this point and how I was going to explain this to Jessica. I wanted to say something to Mrs. Johnson, but she kept reminding me not to speak.

We stopped for some tea and honey before getting back in the car. Mrs. Johnson could obviously sense my concern. She was very careful in choosing her words. Even though I was not yet allowed to speak, she did not say a lot.

As the 30 minutes time-frame was coming to an end, we were nearly at our next destination.

“Lyla, I am sorry if the Doctor appointment upset you. Remember, everything is temporary. When I discussed your issue with him last night, I thought his solution would just be a pill or two for a few days to control your urges. I guess it is a little more than that, but this will still get the job done.”

I squeaked out a terse response. “”A LITTLE MORE!”

“I said I am sorry.”

“I’m scared. I was kind of enjoying all of this, but now I think I have allowed this to go too far.”

“You will be fine. It’s not like you need to be Lyle over the next few days. I will explain what happened to Jessica. She will understand.”

“I hope you are right. I love her.”

“She will always love you… no matter how you present.”

“How can she see me as a man, if I can’t?”

“She wanted you to have this girl time. Doesn't that say enough.”

“Yah, but I doubt she thought I would ever get in this deep.”

“Truthfully, I grown to like you more these past two days, maybe it will have the same effect on her when she sees you tomorrow.”

“If I can face her.”

“It will all work out, just let yourself enjoy your remaining girl time. She would want that.”

“Fine, but no more surprises, please.”

“Just try and put being Lyle out of your mind, you will avoid anxiety and I know Jessica will understand.”

“I even sound funny now.”

“I think your voice sounds much nicer now. No one is going to miss-gender you now.”

“Actually, don’t you mean everyone will?”

“I am glad you are getting your humor back.”

Chapter 11:

I should not have been surprised that she dragged me along into her husband Jack’s office. Since he was the CEO of BuilderOne, she was granted pretty much free rain of the facility. I had always wanted to work there as they had one of the best reputations in Architectural design. This was the first time I had ever been in the executive suite of their huge facility.

While Mrs. Johnson was looking for the Gala tickets on Jack’s desk, one of the young Architects made his way over to me. I had seen him come out of one of the private offices a few doors down. I got nervous as he made a beeline straight towards me.

“Hello Miss. Is there something I can do for you?”

“I’m fine, my Aunt is getting something from her husband’s office.”

“Your Aunt is Sophia! I can’t believe we never met before.”

“That’s ok, I have been at USC in college. I just graduated.”

“I am thrilled to meet you finally. My name is Marc. And you are?”

“I’m Lyla. We will be out of here in a minute.”

“Please don’t rush. What did you graduate in?”

“I studied Architecture.”

“Sophia’s daughter also studied Architecture at USC. Did you spend much time together there.”

“Umm yes. We are very close. That’s why I am here. I am spending a few days with Jessica and her family.”

“Well maybe I will see you around again.”

“I’m spending most of my time with Jessica or her mother. I doubt we will be by here again.”

“Jessica comes over hear a lot, so you never know.”

“If we come back I will make sure to say hello.”

“I would like that. What are you doing while you are here?

“I think my aunt has filled up my schedule, so I am truly in her hands.”

“Any chance you could sneak out for a cocktail or dinner?”

I must have turned red. This almost stranger was asking me out. I don’t think I was ever that aggressive when I first met someone.

“I’m really sorry. You seem very nice, but as I said, while I am in town, I plan to spend as much time with the Johnsons as I can.”

“I completely understand. They are wonderful people. Another time maybe.”

“Maybe. See you around.”

“I am sure you will… I am very persistent.”

At that moment, Mrs. Johnson popped back out of Jack’s office.

“Oh, hi Marc. How’s your family?”

“Great Sophia. How come I never met Lyla before? We were just getting to know each other.”

“She did not grow up around here and until she went to school at USC, she really did not like the big city. We are kind of giving her the crash course on the cultural aspects of LA.”

“Lyla you are very lucky. If anyone knows about the arts and culture of LA it is Sophia and Jack.”

“Yes. I almost feel like I am taking advantage of their kindness.”

“Lyla dear. It is our pleasure. We want you to experience the best of the city. Hopefully you will settle down here soon.”

"Mrs. Johnson, Lyla and I were talking about getting together, but she made it clear that she planned to spend her time here with Jessica and your family. I would not want to interfere with that. However, I had an idea you might approve of.”

I started to squirm as they discussed me and what I might want.

“She did… so what did you have in mind.”

“Next Friday is the grand opening of Hamilton here in LA. It is the biggest new show to hit town in years. I have a friend in the box office and I might be able to snag four seats. I can’t promise that they will be great ones, but maybe I could take Lyla and Jessica to the show with my brother and I. If you approve.”

I was dying to see Hamilton, but certainly not as the date of some guy. I also was just trying to be polite when I suggested that I might get together with Marc down the road. He was a smooth operator.

“You could get those? I know Jessica wanted to see that show badly. I’m sure that she would gladly tag along if you get four tickets. Lyla, I don’t see how I could deny you that. There is certainly nothing on our calendar that matches up to that.”

“Sophia, I just met Marc. That would be too much to ask. Maybe if I came back to town later this summer.”

“Lyla, I can’t promise I can get them, but if I can, I would be honored to take you and of course Jessica. First dates, should be special… don’t you think?”

I was backed into the corner. Mrs Johnson obviously liked Marc and the opportunity to see the opening night of Hamilton was a once in a lifetime opportunity. Maybe, he would fail in getting the tickets. As much as I would love to to see the show, I could only hope they were impossible to acquire.”

“I will have to check with Jessica and get back to you.”

“So that’s a yes if she agrees?”

“If she agrees, and of course if you can get tickets. I heard that even for insiders that show was impossible to get tickets for.”

“True, but you give me incentive.”

“I will talk with Jessi tonight. It was nice meeting you.”

As soon as Marc walked away I headed to the bathroom to regain my composure. I almost walked into the men’s room, but managed to get into the privacy of the lady’s room. I could feel my heart racing. This was all becoming surreal. I knew Jessi would never agree, but I couldn’t believe what had transpired.

Mrs. Johnson followed me into the bathroom to check on me.

“Are you OK Lyla? You ran off”

“No, I am not OK. That guy just asked me out. How could I be OK.”

“Well you made a quite an impression on him. I have known him for a couple of years. He’s a nice man.”

“I am too!!!”

“You can’t blame him. That’s not what he saw. In fact, when I saw you two chatting, it looked like you were both flirting.”

“I was not. I was just trying to be friendly and polite.”

“Sometimes those are the same things. You should be proud of yourself, he is quite a catch and he’s cute too.”

“Sophia! Jessi is going to go ballistic when she hear’s we were invited out for double dates. She will freak.”

"Settle down. I will talk with her and explain what happened. She will probably find it funny.”

“I don’t. Can we go home now?”

“Soon, we just have to go and get you some shoes for the weekend.”

Not surprisingly, I ended up with multiple pairs of shoes. Either Mrs. Johnson felt guilty about what had happened at the office or thought that more shoes would cheer me up. I did like most of the shoes we purchased at Nordstrom, but I hardly saw the need other than for the Gala. I ended up with flats, wedges, booties and sandals. It all seemed excessive.

It was late afternoon before we got home. I had settled down, but still could not fathom the conversation with Jessi that was on the horizon. How do you tell your girlfriend about getting asked out by a guy; or how you ended up with female hormones racing through your blood. I would have to do this with a voice that was probably an octave higher than it should be. I would just have to accept whatever anger she vented. I deserved it.

Mrs. Johnson told me she would call Jessica and take full responsibility. She had lead me along this path, but I had let her do it. We probably both deserved some of the blame. Between my appearance and the temporarily altered timber of my voice, it would be impossible for me to be Lyle for now. How could Jessica think of me as Lyle if I couldn’t? Somewhere over the past 36 hours I had begun to accept being Lyla. It shouldn’t have been so easy.

Jessica would be home on Friday and the Costume Gala would follow on Saturday. She would see the a woman when she returned from her trip, not her boyfriend in a dress. I saw no alternative to change that. I had long ago allowed this to go beyond turning back. I looked and sounded flawless, my body was chemically altered and I had acquired a wardrobe that any girl would be envious of. I could blame her Mother, but I was in this spot because I allowed it..

Chapter 12:

I kept to myself after getting home. At first, I just sat on my bed pondering the turn of events. I tried to replay in my mind what I felt at each juncture and why. I had even noticed a very small nick in my manicure and it bothered me. I was thinking like a woman and apparently responding like one too. After using the bathroom I touched up my lipstick and brushed my hair, as if that is what I should be doing. I even spent a few minutes looking at all of the new clothes now hanging in my closet. I should have been aghast at the sheer quantity, but instead I was mostly curious which items we actually bought.

I was pulled from my deep self-thought by Jessica’s distinctive ringtone emanating from my new Kate Spade purse. I had heightened fear because my first words would be in a foreign voice to her. I knew I had to answer, so I took a deep breath and reached into the bad and pulled out my phone. To my further dismay, I discovered she was calling me on a FaceTime call. Not only would she hear the strange voice, she would see it coming from my transformed appearance.

I answered in a soft voice, "Hi Jessi"

Before she responded, I could see her meticulously taking in my image on her screen. Instead of hello, she spoke in a strained voice.

“Lyle, I am so sorry. I just spoke with Mom. I hope you can forgive me.”

“Forgive you? I was going to ask you to forgive me.”

“I only wanted you to have fun. I thought the party was a good excuse for you to have a little more girl fun. You sounded like the original college experience getting dressed up was a good time and I thought that asking you to do this again with my Mom and me might even be more fun. I never expected you to be put in such a difficult position and aggressively manipulated. I think my Mom meant well but I take full responsibility.”

“What did she tell you?”

“Quite a lot. And hearing your sweet voice now tells me that much of it must be true.”

“Did she tell you what else the doctor gave me or about that guy Marc at your Dad’s office? So much has happened and I am not sure what to think about it. I was a little angry with your mom too, but in reality she didn’t force me to do anything. I really didn’t ask for most of this, but I could have stopped it.”

“Don’t blame yourself. I know about the drugs and our dates for the play. She put you into those positions and its understandable under the circumstances, that feeling so girlish kind of took over. I wanted you to feel some of that, I just didn’t think it completely through.”

“Both of those things came out of the blue. I thought the doctor could help control a problem that occasionally made me uncomfortable and the voice thing happened like it was a throw in bonus. It all hit me when it was over and the interventions were explained to me. I sound, look, and even feel so much like a girl now. I really can’t believe I did all this for a costume party.”

“Lyle… I know you are going to be upset with me. That’s a big part of why this is actually all my fault.”

“Why would that be your fault? This was your Mom and me.”

“It’s about the Costume Party thing. I was a little misleading there.”

“How so? Its not a big fundraiser for the Museum?”

“It is an important thing for the Museum and especially my folks, but the Costume thing was my parent’s slang description of the Gala.”

“I’m not following. Your Mom bought me the most beautiful and expensive dress for Saturday. Is that the wrong kind of costume?”

“I’m sure it is a magnificent selection for the evening. What I mean is…. God I don’t know how to say this.”

“Jessie, I’m getting more confused.”

“OK, my parents have always called these Black Tie events costume parties. Everyone wears the fanciest clothes and many of the patrons go over the top trying to look like movie stars. The Costume description is really only what they call it. It really is just a very very important Black Tie Gala.”

“So why then was I dressing up in a costume?”

“Lyle, I am beyond sorry. This all started right after you told me about your cheerleader dressing up for the frat. You made it sound like you actually enjoyed it and I was jealous that I never got to see you dressed up. This thing just came up, and my Mom thought if that was fun, getting an opportunity to wear some nice things would be even more fun.”

“Jessie!!!! Were you trying to embarrass me at the party! How could you?”

“No. You have to believe I did this for you and for us. I thought it would be enjoyable for you and of course I wanted you and Mom to get to know each other more. We all agreed that the dressing up would stop if any of us thought is was out of hand or if you asked to stop. I was going to tell you the truth before the Gala and of course you would not have to go as Lyla if you didn’t want to.”

I began to get very emotional. I was having trouble processing what had happened and where this left me. I went into this thing without much resistance, but I had been tricked by the people around me that I had trusted. Knowing that the original premise was a ruse, I began to cry. I told Jessie that I needed to be alone for a while and ended our FaceTime call. I felt crushed that the woman I loved had deceived me.

I didn’t even come out of my room for dinner. Two hours had passed and I was still as confused as ever. I received multiple texts from Jessi all stating remorse and apologizing. I didn’t know what to think or what to say. I wasn’t ready to talk to anyone, especially Jessi or her Mom. My first impulse was anger, but now I was just an emotional mess.

Eventually my fit of tears and shock began to wain. I pulled myself up from the pillow on my bed, that was now stained with a rainbow of colors from my makeup. I actually was pleased to see the damage to the fine linen that I had created. After composing myself in an upright position for a minute I entered my private bathroom.

I found myself forming a half smile when I saw the smeared lipstick halfway up my cheek. My image was still all girl, but I looked more like a coed waking up from a drinking bender. Again I paused as I thought out my next move.

The obvious choice was to strip off as much of the past 2 days as I could. I would still be left with pierced ears, meds floating through my body, extra thick eyelashes, wispy eyebrows, a hairless body, long bleach blonde hair, and of course a girls voice for at least a few days. I could remove all the makeup and clothes, but I would not easily erase the feminine appearance. That might be harder than the process of receiving all these makeovers.

As I calmed down, I knew deep down that Jessi would not want to hurt me. That didn’t totally forgive the deception, but at least I could now see it was not some sick game. I had just told her about my cheerleader experience and maybe I came across as too happy about that hazing ritual. Maybe she really felt I needed this experience. I was now wondering if maybe I did.

I didn’t specifically ask for any of it, but my reluctance to pull back or stop the silliness never materialized. I still could remember how mesmerized I was seeing myself in the ball gown. I probably should have been laughing or repulsed, but instead I was emotionally moved. For whatever reason I found myself looking so beautiful, I certainly did not hate it.

The guilt of enjoying aspects of my situation was lessened by the fact that it really was not of my own making. I was responding mostly as they wanted me to. Why they wanted me this way was also bouncing around in my head, but now I simply had to decide how best to cope in the short-run.

Jessi would be returning tomorrow which was a day ahead of the Gala. I figured that I could survive at least another day and have her help me deal with this. My immediate need was to remove my messed up makeup. Mrs Johnson had given me a lesson and tools to do that the previous evening.

After cleaning and moisturizing my face I made another call to Jessi. This time not as a FaceTime call, but rather a regular audio call. Oddly, I did not want her to see me this way after seeing me so glammed up a few hours ago.

She was thrilled that I called and quick to answer. It was two hours later in Chicago, but she said she had been waiting by her phone praying for a text or call from me. Once again, she could stop saying she was sorry.

“Jessi, I forgive you. That doesn’t mean we don’t have issues to work through, but I don’t hate you. I still love you and can’t imagine my life without you.”

“I so love you too! I just want you to be happy. I never should have implied that it was a costume ball. It was an impulsive idea and unfair. I hurt you and don’t know if I can forgive myself.”

“I already forgave you and the only thing that hurt me was you not being truthful with me. Promise you will be honest with me and the rest of this we can deal with.”

“I promise! I Promise! I promise!”

“I assume you will still be home tomorrow afternoon. When you get back, we can sort all this out. I haven’t even spoken with your mother since I learned the truth about ‘The Costume Party’. I’m not sure how to face her. She treated me like a daughter, but I have mixed emotions knowing that is was a ruse. She spent a fortune on my makeover and gorgeous clothes. In one breath I want to tell her off, but in another it was nice to have a mother again. I also still want her to like me.”

“Lyle, I spoke with her for nearly an hour and she also feel terrible.”

“I haven’t been called Lyle in two days. It feels almost strange.”

“Would you rather I call you Lyla for now?”

“I’m not really sure. After everything I have been through the past two days and how I currently look, Lyle just seems incongruous.”

“Ok, then for the moment I will call you Lyla. If you want me to stop just say so.”

“Your mother must think I am a wimp. She probably can’t wait for me to be gone.”

“Just the opposite. Besides expressing her apology to me she told me that she really did bond with you. She didn’t say it, but from the way she spoke, I think she enjoyed her girl time shopping with you more than she does with me. Maybe it was seeing you experience things for the first time. For whatever reason, wanted me to know that she saw much of what I saw in you. She really wants to make it up to you. I hope you can give her a chance.”

“Wow! But having seen me so utterly girlish, how can she ever respect me?”

“Both my mother and I only care about you, not how you look. She liked you before and that has not changed. Despite your assumptions, the last two days have only increased her desire to have you in the family.”

“I felt more like her daughter than a future son-in-law.”

“That’s something to build on. You felt like family. How did you feel being treated like that.”

“What do you think?”

“Be honest… that’s what we promised each other we were going to do. What did it feel like being her pampered daughter?”

“It’s weird, but I had a lot of fun. Even when my parents were alive I never experienced being treated like the most important person in the world. It’s as close to being a future Princess like Meagan Markle as I will ever experience. You probably think I have flipped.”

“I suspected you would have a good time otherwise I wouldn’t have put you through it. I’m just sorry it got a little out of hand. I never got a chance to say it, but you really do look stunning. I hope I will still get a chance to see you in person tomorrow.”

“At the rate I am going, I will probably be pregnant by tomorrow. But seriously, I will try and look nice for you when you get back.”

“Lyla, I love you.”

“I love you too.”

End of Part 4======

Part 5 (Conclusion?)

Chapter 13:

I got up early Friday morning, partially because I was anxious to see Jessi later in the day and also because I was hungry from skipping dinner. I showered and shaved the few facial hairs that were poking out. My next choice would define the rest of my day and possibly even beyond that. Instead of slipping on my jeans and a t-shirt, I elected to keep the masquerade going at least until Jessi got home.

I went to my closet to see if there was something casual, but feminine to wear, Since I had tried on so many things at Bloomingdales I thought maybe there would be something I could wear. I had already put on one of the many bras in my dresser along with matching panties. Upon opening the walk in closet, I was startled to see the mass of items beautifully organized on hangers, shelves and shoe trees. If I hadn’t just tried on most of these items I would have assumed they were someone else’s, but I recognized most of the items. On the far side of the closet was my Gala dress with the matching shoes and clutch next to it. I felt my heart skip a beat when I focused in on it. I resisted the urge to put it on for one last time.
Mrs. Johnson had purchased virtually every outfit I tried on that fit. There were even a few items and accessories that I had not seen before. The wardrobe had everything a girl might need or want. Besides being outlandishly expensive it was enough clothing for a very long time. There was only one pair of jeans and a v-neck top which were the clothes that I wore when I first arrived at their home. Whomever had organized the closet left me the one option if I didn’t want to wear my new fashions. I was given a choice but it was provided mostly as the back door if I didn’t want to continue the feminine mascarade.

I had already decided for now to stay the course, so I selected the Vince Midi Slip Dress in Silver/gray. It reminded me a little of my formal gown and the silky material felt luscious against my skin. I matched it up with a pair of black ankle boots with modest heels. I remembered seeing a similar look on the display at Bloomies.

When I finished dressing and brushed out my long hair I felt satisfied with my appearance. If I had known how to apply makeup I probably would have attempted to further enhance my look. It was as good as I was going to get before heading down to the kitchen. Besides getting some overdue nourishment, I would likely have to speak with Mrs. Johnson. I wasn’t sure if she would be surprised to see me this way. As much as I know she had been a major instigator in my transformation it crossed my mind on the way down that having a good reason to stop dressing she might be upset to see me continuing to present as a woman.

It didn’t take long to get an answer. She was waiting for me in the kitchen with breakfast ready to go. I could smell the aroma of fresh coffee and bacon. As soon as she saw me enter the room she walked right up to me. She stopped 2-3 feet short of me, but her approach was as close as she thought I might be comfortable with.

“It’s my fault. Please don’t blame Jessica. When she told me about your positive Cheerleader experience, I came up with the idea to take it a step further. I never meant to hurt either of you. With each step we took together I became more entranced with how lovely you looked and how happy you seemed to be. I should have thought through the Doctor’s appointment more thoroughly or not at all. I hope you can find a way to forgive me.”

“Mrs. Johnson all of this has been very confusing to me. You know I love Jessi, but its been hard to understand that both of you could have tricked me into such an embarrassing situation. I keeping wondering why?”

“You have nothing to be embarrassed by. First off, you look gorgeous. The only people that have seen you this way think you are a sweet young lady.”

“Maybe, but it still does not explain why.”

“Some of that I am embarrassed to answer. First, let me start by saying Nate and I have always liked you. However, we did honestly have some reservations about you marrying our daughter. That’s why we asked you to spend at least a couple of weeks with us so we could get to know you better.”

“That still does not answer why.”

“I know. We always wanted Jessi to make her own decisions on her future and still do. Wrongfully, we thought that if she saw you from such a different perspective, it would be a major test for her. I feel horrible because looking at this objectively, it appears we were trying to sabotage the two of you. We didn’t just do this to you, we did this to Jessi.”

“Yes, but she knew the truth about the party”

“Yes, but mother’s can be persuasive.”

“Mrs. Johnson, that I won’t argue with.”

“Lyla, Please call me Sophia or if you like Mom. “

“Ok Sophia, I guess while I look like this you can call me Lyla. Whatever the misguided reasoning, can you still see me in the family?”

“Lyla, spending the past two days with you was a joy. This may upset you a bit, but I have quickly grown to love you like a daughter and I mean that dearly. I am sure that I just see the good person that you are and will learn to love you no matter how you look. Right now, I am happy to have a little more time with Lyla.”

“I would be lying if I didn’t say some of this has been fun. This has been considerably different than my fraternity days, but you did make me feel special. I’m glad you told me the truth. I also feel for the first time like I have a family. Let’s start fresh from here.”

“So Lyla are you saying we are good?”

“Yes. All is forgiven.”

With that we had a long hug and then sat down for a pleasant breakfast. My time as Lyla never missed a beat. Mrs. Johnson never asked or questioned why I still was dressed as a woman. She continued some minor coaching on my posture and hand movement. Towards the end of breakfast, she asked if I was still up for some makeup lessons. The woman Lulu had recommended was supposed to come over at 10:00 and in all the chaos, the appointment had not been canceled. I told her that I promised Jessi I would look nice for her return in the afternoon so that would actually be nice. I couldn’t say it, but I guess I was not ready for the girl time to end.

Chapter 14:

The makeup lessons lasted two hours. I was no expert when Christa left, but I certainly knew enough of the basics to look presentable. Before we finished she glammed me up for Jessi’s return. Christa wanted to schedule a follow up. I told her that I would love to but Mrs. Johnson was footing the bill and I didn’t know when I would be available. That seemed like the simplest excuses.

I learned that most of Christa’s compensation came from selling me the products she selected for me. As a result, I now possessed a complete set of brand new makeup products. These included products from, Urban Decay, Dior, Tarte, Marc Jacobs, Clinique, Lancôme and more. I would have put up more resistance to buying all these things, but I assumed I could give them to Jessi.

After Sophia settled up with Christa, we dined by the pool while consuming a very light lunch.

“Jessica is going to be amazed and how attractive you have become. Lots of woman have natural beauty, but you have that special glow.”

“That’s the makeup and the fact you are making me blush.”

“Trust me, a lot more guys like Marc would die to take you out.”

“Let’s not talk about things like that around Jessi. That something I don’t want to even think about.”

“That’s just a price you have to pay for looking so pretty. Men can be like that.”

“Sophia! Remember who you are talking to.”

“I do, but you have a whole new perspective to see things from. Just relax and try and experience the view from the other side. It will make you a better spouse when that day comes.”

It was a little more than an hour later when the limo pulled into the driveway and Jessica and her father piled out. My heart began to race. I wasn’t even sure what kind of reaction I wanted to see from her. I wanted to look great for her, but I also didn’t want her to freak out. Just before they came through the door, Sophia looked at me and told me to breathe.

Nothing prepared me for the reaction I got when she met me only steps from the front door.

“Welcome home Jessi.”

As soon as my words left my mouth it hit Jessica that the person speaking with her was me. She had a momentary stunned look on her face before she fainted.

“Jessi, Jessi wake up are you OK? Please wake up.”

Both of her parents asked me to wait in the living room. I guess they didn’t want to shock her again when she came too. I hated leaving her side but understood. I retreated to the other room.

“Honey are you ok? It’s me, your mother. You just fainted.”

After her father dabbed her with a cool wet towel she began to wake up.

“What happed to me?”

“You came through the door and I think after you saw Lyla you just fainted.”

“Was that really Lyle? I’m sorry, I don’t know what came over me. Let me go see him.”

“Let’s just sit up for a moment. You can see her in a minute.”

“Her? I don’t understand what happened to me.”

“Seeing her or him just must have really surprised you.”

“I knew what to expect, but I guess it all hit me when I saw her.”

“It’s understandable dear. She really does make a lovely woman.”

“I’m ok now. Please I’m fine. Maybe I was just dehydrated from the flight.”

Jessi found me nervously waiting for her on the couch. I stood up to greet her and before we hugged she scanned my image from top to bottom. We embraced before we both sat on the couch. I didn’t think about it until later but we usually would have also kissed after not seeing each other for a while.

“I saw the photos and we FaceTimed, but in person you look even more feminine and beautiful that I imagined. You really are gorgeous.”

“Thank you. I wanted to look nice for your return.”

“My God you even sound like a girl.”

“Are you upset with me? Should I have not dressed up for you?”

“No no. I wanted to see you for myself. It’s just….”
“What?”

“Nothing. I thought you might look pretty. It’s just you really look and sound like a Lyla. You even sit like a woman. I’m still trying to take it in.”

“We can end it right now. I will go and change.”

“No way. I put you through this and we both need to spend some girl time together. We have a lot to talk about and figure out. With your voice and all the rest, my girlfriend is going to be here for at least a while.”

“I think your mother has made certain of that. Not only do I have all the physical changes, she has bought me a whole wardrobe. I guess a little longer until at least I get my voice back won’t kill me.”

“You know what they say?”

“What?”

“Once you wear a bra you never want to be without one.”

“Funny, I’ll try and remember that.”

The rest of the afternoon Jessi and I hung out together. I showed her everything I had acquired the past two days. We had a few laughs over everything and Jessi seemed intent to see how thoroughly I had adapted. When we talked about my clothes she intentionally wanted to know which items I liked the best. This continued until we were informed that dinner would be at the club.

I picked out a simple but attractive Lauren sheath dress along with modest heels. Jessi liked my selection, but she really grew interested when she saw me touching up my own makeup.

“If I knew you had that skill I would have had you help me the past couple of years. Are there any other things I don’t know about you?”

“Stop teasing. Lulu had a makeup artist name Christa give me a lesson.”

“It’s just cute seeing you this way. The way mom has been gushing over you and now seeing for myself, you seem to me enjoying your experience….”

“I’m just trying to make the best of it. That’s what you told me.”

“Of course. I’m now over the initial shock myself. I don’t want to sound cruel, but it’s sort of fun for me too. I mean, I’m an only child and often wished I had a sister to hang out with.”

“Your Mom called me her niece at the club yesterday and you call me your sister.”

“Well at least we all agree you are part of the family.”

“For the moment I guess that will have to do.”

Chapter 15:

“You girls look wonderful. It’s nice to have us all together as a family. Your father and I understand this is not how you planned your stay, but we hope we can all make the best of the situation.”

Before I could speak, Mr. Johnson added. “Lyla, is it ok I call you that?”

“Yes sir.”

“Call me Nate.”

“Yes sir, I mean Nate.”

“Lyla, I also wanted to say I am sorry. I wasn’t involved in planning this, but I was aware of it and could have stopped it. We are all partially at fault. In any event, I am pleased that it doesn’t appear that you are still struggling with your changes. You do make a remarkable young lady. Society has come a long way the past few years and people can now be whoever they want.”

“Thank you Nate. Under the circumstances, I am just trying to blend as well as I can. It would be a lot harder on me if my appearance was less stealthy. Maintaining this image seems like the best course for the moment.”

Jessi also felt the need to proclaim my ability to pass. “Lyla fits in perfectly here. Dad you are lucky to be sitting with three pretty woman. You are the envy of the club.”

I was a bit uneasy by her comment, but it got a smile out of her father.

The majority of the dinner conversation shifted away from me. I was happy to discuss architecture, art and the tasty food we were consuming. Towards the end of the meal the discussion shifted over to the benefit.

Mr. Johnson was beaming about the art that the museum had purchased from a private donor. He wouldn’t tell us who the artists were, but insisted that they were major pieces by world renown masters. It was going to be a special evening for the museum and obviously a big evening for him. We could see he wanted to tell us about the pieces, but insisted that the whole board was sworn to secrecy.

Mrs. Johnson started laying out the plans for Saturday which to my surprise still included me. Under the circumstances I just presumed I would be staying home while they went to the Gala. The costume premise had been exposed and the pressure for me to attend as a woman had been removed. I just assumed they would not want to push the issue by having me attend such an important event dressed like a lady.

“Sophia do you really think it’s a good idea that I attend?”

“Of course. You don’t have to, but it is going to be a wonderful evening and it would be a shame for you not to get to wear that gown you fell in love with.”

“Jessi, what do you think? I don’t want to embarrass myself or the family. If you don’t want me to go or think its not a good idea, then that’s that.”

“Lyla, the whole thing started for the wrong reasons and we are all very sorry. Early on, I also doubted you actually going to the event. However, once I got to see you in this light I lost my biggest reservation. There is no way you will embarrass anyone, unless you cant handle the attention you are likely to receive”

“The only attention I desire is from you.”

“Well at the ball we are not a couple. If people see us as such, then we might have a problem.”

“I guess that right, but that doesn’t mean I will have to give any attention to others.”

“Do you think you can act like a proper society lady for a long evening?”

“Truthfully, I never thought I could have been at a place like this two days ago.”

“Lyla, I just want you to be happy. I will always love you, but I think you deserve the full opportunity to experience the view from the other team at this juncture. I also want to see you on parade in that gown that mom says you swooned in when you tried it on.”

“I didn’t swoon. I was thinking about you wearing it when I saw myself in the mirror.

“Good answer, maybe you can lend it to me some day. Girls do that you know.”

“So I guess I am going then.”

“Girls, I’m glad we got that out of the way. Sophia and I promise both of you that it will be special evening. Lyla, we will keep an extra close eye on you to avoid any issues. It is very nice that we can all be together and hopefully you will have a memorable night.”

Back at the house Jessi and I prepared for bed. We shared the bathroom to remove our makeup and prepare for bed. I was excited to be alone with Jessi after such a stressful day. I had no choice but to wear a cami and my panties to bed as I had no other pajamas in our room. It took me a little longer than Jessi to get ready and when I came to bed she smiled but shook her head.

“What’s wrong?”

“Nothings wrong. It’s just that even without makeup or your breast forms you still look so feminine. If I was a lesbian I would be all of over you.”

“I’m still your guy. The hair extensions, smooth body and and other stuff is just temporary. I can turn off the lights and we can just be us. You can still be all over me.”

“I know you are still the same person underneath the beautiful façade, but I can’t stop thinking of you as a babe right now. I dreamt this was going to be a playful, if not, a kinky sort of thing when we originally talked about it, but you are just too convincing. I don’t see Lyle dressed as a woman, rather I see Lyla. I like Lyla, I like Lyla a lot, but I am not into woman.”

“I didn’t ask for this. I still feel the same about you. What are you telling me?”

“I’m sure we will get back to normal, but until then you will still be my best friend in the world. For the next few days you will have to just live with that. My parents and I consider you family so just think of yourself as part of the family. Maybe we can jump each other’s bones when your new voice and other changes fade away. Until then, I plan to enjoy having a best girlfriend. I haven’t had one of those in years.”

“I guess this is the first time in my life I really wished I had a bi girlfriend.”

“Maybe I will come around to that. You are so pretty. Maybe since Lyla wants to jump my bones she is bi too.”

“I’m getting a headache trying to figure this all out. I guess it is goodnight then. Please make sure I don’t make a fool of myself tomorrow.”

“From now until…who knows when, you are Lyla. You will be fine if you just remember that’s who you are. Night night Luv.”

Chapter 16:

The big day included an afternoon at the Nine Zero Nine salon. Sophia, Jessi and I went from station-to-station getting every possible form of grooming and pampering. Even before Lulu styled my hair, my skin and nails were glistening. My nails and toes had a flawless British red glow courtesy of a fresh Gel coating. My hair was given a romantic Bohemian style with cascading curls. Some of the hair was pinned up to give it a more flowing appearance. My somewhat retro appearance would not have been out of place on a bride. From Lulu’s private station I was ushered to the makeup area. When I was done there it was my turn to get a little light-headed. My intense makeup and f-me hair made me nearly forget my birth gender. I was draped only in a simple peasant style dress but I looked more like a real life princess.

The shop was loaded with ladies getting similar treatments for Saturday affairs so my makeover was not out of place. Shortly before we left I finally got to see Jessica after her beauty regimen.
She looked equally ravishing. I had never seen her so formally made up, but her beauty had always been something I appreciated and was drawn to. We smiled at each other in approval and shared a careful hug.

Even Mrs. Johnson looked gorgeous. She was an older version of Jessi, but still was a very attractive woman. With her makeover she looked younger and quite stunning. The three of us were going to make quite an entrance. Moments before we were to leave the Salon Sophia reached into her purse and pulled out two pills. Lyla, here are your pills. I spoke with Dr. Welby earlier today and because of the injections, he insisted you take those until at least your body can adjust to the jolt to its system. Besides its very good for your skin and hair.

It wasn’t a place to argue and defending my masculinity would have been ridiculous at this particular moment. I swallowed the pills as Jessi blankly gazed at me.

We headed home to change into our Gala clothes. We would have about an hour before the Limo would take us into the city and drop us at the Hilton Grand Ballroom.

Back at the house I was actually excited to be putting on the gown again. I tried to contain my enthusiasm around Jessi, but even she knew that putting it back on would not be a struggle for me. I needed her help to get it on properly without ruining my makeup. I stood there in front of the woman I hoped to marry looking like a starlet at the academy awards. I could see her looking me over and trying to formulate something to say.

“Jessi, what are you thinking about. Does something look out of place?”

“Lyla, just the opposite. You look perfect. I haven’t seen you this confident looking in a long time. That dress was made for you. I think I am going to just have to get used to that.”

“I think it would look better on you, but thank you.”

“I’m not sure you completely understand what I am saying.”

“I’m confused. Does it or doesn’t it look good on me?”

“Good would be an understatement. What I am saying, this transformation appears more like a transition. You don’t just look like Lyla, I think you are Lyla. You have confidence and I can see the sparkle in your eyes.”

“I’m just in a role. This is just acting the part.”

“Method acting. You appear to be in the role of a lifetime. I think you are so convincing because I don’t think you are acting.”

“Jessi! Please don’t think like that. We will just laugh at this later.”

“Lyla. Tell me you don’t love how you feel dressed as you are now and have been the past few days. Be truthful… I will understand.”

“It hasn’t been terrible. I mean some of woman’s clothes feels so much nicer than my male clothes. I guess I have learned to appreciate being all dressed up. That’s it.”

“Now is probably not the best time to have this discussion so lets both just enjoy the evening. I want you to remember we are not a couple tonight. I expect you to respond to me and the other guest as my lovely cousin from out of town. If you do, you will have a lovely evening and maybe even some new sensations.”

“Let’s talk about this more tomorrow when this is in our review mirror. Besides having more time then, we won’t be in our red carpet attire.”

“I agree. Do you think anyone will notice me tonight next to you in your dream dress?”

“Haha! You look stunning. Then again, you always do.”

We were called downstairs to leave. We both took a deep breath before smiling at each other and making our way out.

It didn’t take me long to discover that I was not going to remain a wallflower for the evening. We were met by one of the organizers and lead to a VIP room. I was introduced to the entire Art Institute board and even Mayor Emanuel of Chicago. There were other VIPs to schmooze with before we made our way out to greet the regular patrons and have cocktails. From the time we arrived until I collapsed back into the limo many hours later, I had few moments to myself.

I was much more popular at this gala than I had ever been at a party. I used to have to insert myself in conversation to get noticed, but on this evening I was often the center of the attention. I met a few of the ladies from the club which already knew my name. They all wanted to include me in their conversations and get me involved in future activities. I was surprised how many of these ladies wanted to pry into my private life. It seemed most of them wanted to know if I had a special man in my life. At first, I adamantly said no, but as I thought about it more, I was more vague so I would provide them less of an opportunity to make suggestions. I later started to imply I had someone I met recently.

When I was not surrounded by the ladies, I found that many of the single men saw it as an opportunity to introduce themselves. I received many compliments and was the target of a few creative pickup lines along the way. It was nice to receive all the attention, but strange to be desired by random men.

Shortly before the dinner and presentations, I finally got alone with Jessica. She too had been receiving endless attention, including a lot from men. I wasn’t exactly in a position to stop that.

“Jessi, this is crazy. I don’t know what to do.”

“Looks like you are doing just fine. You are quite the debutant tonight.”

“I thought tonight was going to be all about art.”

“Art is part of it, but these things are social gatherings. People want to be seen with others and make contacts. As you can tell it also is a classy singles event.”

“Looks like you are quite the popular girl Jessi.”

“No more than you Lyla. I don’t like thinking of myself as an object, but we are both quite the catch this evening. Find anyone that you fancy?”

Before I had a chance to respond, we were in the presence of Marc and another man that I did not recognize. When I last met Marc at Mr. Johnson’s company BuilderOne he was trying to get me to bite on Hamilton Tickets. He didn’t have them, but he was using the remote chance at getting opening night tickets as a carrot to get me to go out with him. I had told Jessi about that and assumed since it would be nearly impossible to get them that I would not have to deal with this again.

Jessi was the first to kick off the conversation. “So Marc, I presume your Hamilton offer was puffery. I understand that those tickets are gold.”

Marc smiled and introduced his good friend to Jessi. “Jessica Johnson, this is Jason Kennedy.”

“Pleased to meet you Jason.”

“The pleasure is all mine.”

Marc quickly cut back in. “Jessica, Jason would like the honor of accompanying you to Hamilton Next Friday with Lyla and I. We have four seats 5th row center.”
Jessi nearly screamed. “I can’t believe you really got them. You must have a really phenomenal connection or some great blackmail photos on someone.”

“I have a relative that has an investment interest in the theater. I never asked him for a favor before, but getting Lyla to go with me was a good enough reason to cash in my chips.”

I was stunned. Marc had pulled out the miracle. I didn’t know how I was going to say no. I was hoping Jessica would come up with a plan, but quickly found that prayer dashed.

“Marc and Jason, we would be honored to go with you. Both Lyla and I have wanted to see that show so badly. To see opening night here in town is phenomenal. We can’t thank you both enough.”

I still had not said a word, even as I turned to my overly excited girlfriend. “Jessica and I hardly know the two of you. Are you sure you want to take us to something so extravagant on our first date?” I realized as soon as I said it that, that first date was probably not my best choice of words.

Marc did not hesitate. “I hope this will be a first date that will be hard to top. We can do something more casual as a follow up.”

Jason added. “Jessica, Marc has told me so much about you and your family. I understand you don’t know much about me, but your parents do know my parents and I assure you, I will be a true gentleman.”

Jessica left no doubt on the issue. “We are in! This is going to be so much fun!”

The speakers at the Gala were taking the stage. As Marc looked directly into my eyes, he said, “We can work out the plans later. Enjoy the evening.”

Jessi and I retreated to our table up at the front of the ballroom. I could see that Jessica was genuinely excited about the Hamilton show. I wanted to see it as well, but not on the arm of some man. Obviously, Jessi did not see a problem with that.

“Jessi, do you really think this is a good idea?”

“I think you will be fine. I will be with you and make sure everything is appropriate for a first date.”

“Me going out with another guy is not appropriate. I also don’t like you going out with another guy.”

“Lyla, stop thinking like another guy. It would be ridiculous for you to make yourself so beautiful and stop short of going out on a date. He’s a nice man and will treat you with respect. I will be there if you have a problem. Beside’s you have to admit, both of them are good looking.”

I didn’t dignify a response to the last point, even as I thought about what she said.

I was happy to change my thoughts to the presentations and speeches. Mr. Johnson was correct and they did unveil two magnificent piece of art. They had acquire an original Van Gogh and an even more rare Caravaggio. Mr. Johnson got to do the honors and received a long standing ovation. When all the speeches were over we had a chance to see the art up close. We also had our photos taken with the art and many of the dignitaries. My Lyla name was given to the photographers. Even if Lyla were to fade away she would forever be linked to this evening. Those photos would undoubtedly end up in print or online in many places.

The evening was not over. From the formal presentations the gala turned into a celebration. Dancing was now on the card. It didn’t take long for Marc and Jason to pull us out onto the dance floor. Fortunately, most of the music was oldies and pop so I was able to avoid much physical contact. I was not a great dancer and now I had to dance like a woman. It was almost easier because I could move my body and arms and nothing was off limits. I did find myself holding Marc’s hands a few times, but that did not seem too awkward. Before the evening was over I had even danced with Mr. Johnson.

Back at the house I was ready to crash. Maybe it was the meds, but unlike the previous evening, sex was not on my mind. Jessica did not seem intent on pushing the issue either. She handed me a very sex nightgown, casually explaining to me that I should be wearing something meant for bed. The Gala should have signified the end of my time dressing as a woman, but now I had another even more feminizing experience awaiting me the following weekend.

Chapter 17:

I woke the next morning before Jessi and just sat up in bed wondering what was ahead. My mind was swimming with thoughts about what had transpired and what might be on the docket. Part of my anxiety was not knowing what I wanted to happen. I loved Jessica and always felt she had the same feelings for me. Throughout these past days she treated me with love, but most of the sexual spark seemed to be missing. I was living with the Johnson’s because I was Jessica’s almost Fiancé, but they now were treating me as a female member of the family. My mind was confused, but there was no ambiguity that to the entire Johnson clan, I was now Lyla. If I had any doubt about that, it was eliminated early that morning at breakfast.

When Jessi’s eyes cracked open she smiled at me. I hid my anxiety and smiled back at her. In a soft voice I whispered, “Good Morning Sunshine.”

“Good morning to you too Miss Lyla. How did my beautiful girlfriend sleep?”

“Ok I guess. I woke up a few times with my mind racing, but I got enough sleep. How about you?

“I slept pretty well too. I had some strange dreams, but I don’t think I woke up at all. I can’t remember them clearly but you certainly were in them.”

For the first moment since her return to town, I thought Jessica might be feeling amorous.

“That’s sweet. What were we doing together together? Was it super erotic?”

“I don’t remember it very clearly, but I remember seeing you looking stunning in a white wedding dress. You looked so happy.”

I could feel my stomach drop. That was not what I thought she was going to say.

“Were you also wearing a wedding dress?”

“Like I said, I can’t remember much more than that. It’s possible, but maybe I was just your Maid of Honor.”

“Jessica, what’s happening to me and to us? I’m so confused.”

“You shouldn’t fret. I think you are just a bit overwhelmed by your emerging feelings. You don’t have to hold back anything now. Just let yourself out.”

“It’s just not right. We are supposed to get married. We are only staying here for your parent’s approval.”

“Lyla, you won over my mother big time and even my father has taken a new interest in you. I will always love you, but I think getting married needs to be tabled for a while. I think we both need to figure out a few things before we can even consider that.”

“What are you suggesting? What do you want me to do?”

“It’s not so much about me. You need some time to figure out what makes you tick deep inside. Marriage is a long-term deal, but you need to know yourself a little better before you can marry anyone else. Let’s get up have some breakfast and talk some more later about anything and everything. Make yourself pretty it will help put a smile on you, OK.”

“Alright. We have a lot to sort out.”

Sophia greeted us in the kitchen with a “Good morning girls.”

Most of breakfast was just the three of us. We talked a lot about the gala. Jessica also informed Sophia that I wanted to stay as Lyla for now and sort out a few things. She made it sound like it was totally my decision and something I asked Jessica to accept. It would have been understandable for Mrs. Johnson to ask me to move out at that point, but she was very understanding and said we would all work through everything together. She then surprised me by suggesting I move into the guest bedroom next to Jessica’s room. “It might be better for both of you to have some private space.”

Jessica did not argue the point. “You will both have your own closet. Girls need space for all their pretty things.”

At the tale end of this discussion, Mr. Johnson sat down at the breakfast table. He was informed of the decisions that Sophia and Jessica had made for me. Again, the implication was that all of this was driven by my desires. I was not resisting but everything was moving along so swiftly.

The biggest shocker came from Mr. Johnson. “I have been on the phone this morning with my office. Last nights gala was so successful, I think we got a couple of new exclusive business relationships. I have to say, we all contributed to that last night at the benefit.”

I was the first to congratulate him. “That’s wonderful, your speech last night was so inspiring.”

Nate nodded at me. “Lyla, you made quite an impression on some of the business community too. That certainly had to help as well.”

“Thank you, but I was just trying to be social.”

“Well you impressed some important people.”

“It was an amazing evening, so thank you for including me.”

”Lyla, I have a proposal for you.”

"What’s that Mr. Johnson? I would be glad to do anything you need.”

“When Jessi and I were on our business trip, she couldn’t stop raving about your architectural skills. I know she cares for you, but the way she spoke of your designs and knowledge, it was clearly more than just talking you up.”

“Thank you both, that means a lot to me.”

“Then last night I saw how well you handled what had to be a pretty stressful situation. You managed to impress a lot of people and fit in very well.”

“I was just trying to blend in as well as I could. I met a lot of very nice people.”
“You obviously succeeded. What I want to propose is an opportunity or you, that will also help us all spend more time together.”

I wasn’t sure where he was going with this, until his next statement.

“I know you planned to work across town with another architecture firm, but I want you to work for us. I guarantee you will make more and working with Jessica and my senior team, the position will put you on the fast track.”

I was stunned. I had not even interviewed with his firm. I had intentionally avoided that, so as not to put him or Jessica in an awkward spot with me dating Jessica. It was my dream firm and I was being offered a sweet job. I looked at Jessica with my eyes bulging open and a loss for words.

She smiled back at me before a long drawn out “Well?” emerged from her lips.

I looked back at Mr. Johnson. “Are you really offering me a job?”

“I most certainly am. You and Jessica will bring some knew young blood and energy into the firm. The atmosphere at the firm has always been a little stuffy and is overdue for some diversity and knew thinking. So what do you say?”

“My God, how can I say no. Just to be associated with your trend setting designs and a firm with your reputation, is what I went to architecture school for. I would be honored.”

“Then it is decided. Welcome aboard.”

“Thank you Thank you!”

“I will let Marc know, so he can plan ahead. I’m sure he will be pleased too. You made quite an impression on him too.”

It was at that point it hit me. Lyle was not being hired; Lyla was. I had just committed to beginning my working career as a woman.

“Mr. Johnson, I don’t want to be at all negative, but what about my real gender?”

“First off, please call me Nate. Our firm may be a bit stuffy, but we have very open and progressive human resource policies. To most of the employees, I’m sure you will be treated exactly like any other woman. Being transgender is a personal choice and will be fully supported. We have great healthcare and resources. Besides you are like family. Jessi, Sophia and I will be there to help you with your transition.”

My brain was trying to tell me to back down, but I could feel the emotional support that all of the Johnson’s were sending me. I was being treated as one of them. I had lost my own family and now I was being welcomed into another family. I still had not fully processed my rapid-fire changes, but I was ready to commit to it.

“So when do I start?”

“That’s the attitude! You and Jessi still have a few weeks off before you begin. I’m sure you can use them for a mental break and to adjust a little more to your changes. Not that you have shown any difficulties, you will need to be totally comfortable in your new environment and lifestyle. When you do begin at the office, you are going to be working very hard. Until then, I’m sure Sophia would love to assist you and Jessica in your preparation.”

“I really don’t know where to begin, but I have always enjoyed being a student.”

Until now Sophia had mostly just listened. “Lyla, I think you are a quick study. As far as the world needs to know, you are my niece. Us girls are going to enjoy the rest of the summer helping forget any old ideas or habits. From today on you are Lyla.”

“I’ll try Sophia.”

“You already appear so natural… soon it will feel totally the same way.”

I wanted to talk about it privately with Jessica. After all, I was now going to be living as her cousin. She seemed happy for me, but obviously we now had a very different relationship. I looked her in the eyes once again. “Are you sure this is all OK with you?”

“Lyla, we will always be best friends and family. I know that in my heart. It will just be a new chapter. I’m sure we will both adjust and be happy. We will do this together. I’m excited for you. I even get to go with you on your first date next weekend.”

With that proclamation my mind began to fully absorb my future.

To be continued?