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?