CHAPTER 10
Meet Ashley

As I walked out into the world again, I was in an emotional high. It was now mid-January, and the weather was cold. But I didn’t feel cold. I felt ecstatic. As I walked down the garden path that led towards the main house, I tried to catch a glimpse of me anywhere I could... in the swimming pool reflection, in any bay window I passed... etc.

I was enjoying being outdoors. It was like a drug. The wind was hitting my face and playing with my hair. It seemed like the colors were brighter. I felt free. Renewed.... reborn.

But as I approached the main entrance, I started to feel extremely nervous. After all, I had never been dressed as a woman in the presence of anyone else. The incident with the cheerleader uniform in the locker room and Martha’s Vineyard don’t count, because I was HIDING. But I had never been dressed as a woman in a public, social event. And that thought crept into my head as I approached the door.

I stopped at the door wondering what should I do? Should I go back to the bungalow and wait for John? Should I go inside and just go with the flow? I was nervous and scared, but at the same time I was ecstatic and confused. All at once. Up to this point in my life I had been Ashton. The minute someone else saw me like this... there would be no turning back.

Suddenly the door opened. It was one of the cleaning ladies. She startled me. I froze. She simply came out of the house carrying a broom and a dustpan.

“Excuse me,” she said casually as she walked into the garden. I just stared at her. She hadn’t reacted strangely. She didn’t stare at me. Except that she suddenly stopped and turned around to look at me. I thought... “here it goes... she knows I’m really a guy and she’ll say something...”. But instead, she simply said, “It’s awful cold out here, miss. Maybe you would be more comfortable inside.” Then she smiled and walked away.

Her words began echoing in my head... “miss”... I took a deep breath then relaxed. A soothing feeling washed over me. It gave me strength. it gave me courage. So I stopped fidgeting, opened the door and walked inside.

It was the first time I stepped into the main house. I didn’t know which way to go. So I started to make my way across the hall towards the living room. I could hear John’s voice coming from there. I stopped quickly by a mirror hanging near the entrance and checked my hair and makeup. I still couldn’t get over myself how pretty and feminine I looked. I kept staring at my eyes. They were still MY eyes. But the rest of my face had become the face of a girl. I took a deep breath and made my way into the living room.

John was standing by the bar pouring himself a drink. Sitting on a chair, was his business associate. A tall, black, former NBA player called Kevin. They were talking shop... something about investment banking, stocks and stuff like that. But as soon as I came into the living room, Kevin suddenly fell silent. John looked up and suddenly he fell silent in mid-sentence. He was so taken by surprise, he actually froze. He didn’t notice that he was still pouring whisky into the glass and it was spilling over the bar.

There was a deafening silence hanging on the living room. Both men simply stared at me. Kevin was calm and curious as to who I was. But John looked like he had seen a ghost. His face went pale and his eyes widened like dinner plates. He quickly tried to regain control of himself. He noticed he was spilling his drink and began fumbling behind the bar. “Shit!”

I was incredibly nervous. All of my confidence suddenly flew out the window the second I realized I had become the center of attention. I tried to say something, but I became self-conscious that my voice would still sound male, so my mouth was just open and no sound came out. Finally, I was able to stutter, “I’m sorry... I didn’t mean to interrupt.”

Kevin immediately stood up to greet me. He was very tall, about 6.5 and lean. He had a Denzel Washington air about him, only taller, much taller. “That’s okay. We were finished talking about business.” His voice was deep and soft... It sounded a little like James Earl Jones.

I started to back away very shy. “I... guess I’ll leave you two alone”. Kevin suddenly looked at John. John had managed to get a grip and bolted from behind the bar towards me. “No, no. Please join us.” He grabbed me by the arm and led me into the living room towards Kevin. “Kevin. I want you to meet...” His voice trailed off as he examined me. Kevin was curiously awaiting the answer... “Yes?” he asked. John snapped out of his stupor when he heard Kevin. “Ashley! Sorry I was just... Um, she’s... my... a very special person...”.

Kevin held out his hand and I shook it. His grip was strong, but gentle. I could feel his strength through his hand. Suddenly I felt John’s hand go around my waist and I blushed. John seemed very nervous. And the way he put his arm around me when Kevin shook my hand was almost... possesive. As if he was jealous or something. He led me towards a sofa chair and invited me to sit. I sat down putting my knees together because I was very self conscious of what still lay inside between my legs.

John walked behind the bar once again. He was rapidly regaining his composure. When he talked to me, he seemed totally in control once again. “What’ll you have, Ashley?” I meekly replied, “club soda...”. John smiled as he began fixing me a drink. “Club soda? What’s the matter? Don’t you remember Martha’s Vineyard?” The memories of that summer at Martha’s Vineyard suddenly cascaded into my head and I blushed once again. John went on, “what was it that we drank that night?” I blushed. I was incredibly nervouse. I looked away and softly said, “margaritas...”.

Kevin just stared at me.I could tell right away that he was into me. But I didn’t know how John would react if I met Kevin’s gaze. So I kept avoiding eye contact with him. John handed me my drink and I started sipping it to calm down. Kevin finally asked John, “So, John. How did you to meet?”

John laughed. Then stared right into my eyes. “Well... we met last year. Through some very good friends of mine. I invited her last summer to Martha’s Vineyard. That was some summer, wasn’t it, Ash? Lot of new discoveries...”

I simply nodded. I kept drinking the club soda in order to avoid speaking. Kevin smiled and looked at both of us. “So.., are the two of you... dating? What’s the story John?”

John didn’t even look at Kevin. He kept his eyes on me. It was like he was taking in the way I looked. After all, I hadn’t given John any heads-up regarding my appearance. “I’m not sure, Kev. What do you think Ash? Are we dating?”

I looked directly at John. I had just finished a glass of club soda, but my mouth was suddenly parched. I looked at Kevin and then back at John. It was obvious that John was putting me in the spotlight and I wasn’t going to be able to sneak out of that question. I took a deep breath, put the glass aside, managed to grab on to all of the courage I could muster, and turned to Kevin.

“I’m not sure, Kevin. You see, John is a very, very special person. When I met him, I had to face some hard-fact about myself. As it turns out, John knew me better than I knew myself. I don’t know what we are... yet. But I can tell you something...” my voice trailed off, then I turned around and looked at John straight into his eyes. “I haven’t stopped thinking about him for the past six months”.

John never imagined I would face him like that. Suddenly, he was nervous again. And he had trouble swallowing. I stood up and walked towards John. His nervousness gave me the courage to push on. “I think I’ll have that Margarita after all...”. Then I slammed the empty club soda glass on the counter. As I stared into John’s eyes, I said, “what about you, Kevin? How long have you known John?”

“Since we were in college. I was the jock. He was the brains. We were roommates. So John. Ashely is your girlfriend, then? Certainly looks that way.”

John quickly regained his composure. He stared into my eyes and replied, “No. She’s not my girlfriend... yet. She’s just... a very special friend”. John put the Margarita in front of me and I drank it with one gulp. Suddenly I felt... safe. I finally relaxed. “May I have another?” John smiled and fixed the drink. I grabbed it and calmly walked back into the chair. John looked at me and winked. Kevin kept staring at me, but now, I felt safe enough to look back at him.

I looked down at my pantyhosed legs. I couldn’t believe it. Here I was in one of the most feminine outfits ever, looking like a million bucks, totally comfortable and feeling incredible. I ran my empty hand up and down my thigh totally ecstatic about the way I looked and felt. John said, “another Scotch, Kev?” “Sure!” Kevin stood up and walked over to the bar.

As John fixed Kevin his drink, I simply allowed myself to enjoy the evening. John and Kevin continued to talk about all kinds of stuff through dinner and I kept touching myself very discreetly enjoying my skirt, sweater and pantyhose. Kevin would stare at me from time to time and that would make me a little self-conscious about my makeup. So occasionally I would retouch it to feel more confident.

John would also keep staring at me. But unlike Kevin, every time John looked at me, I enjoyed it.

Kevin excused himself to go to the bathroom and John took advantage of the opportunity to finally talk to me on a more personal level. “Jesus Christ! You look amazing! I never imagined you would become such a gorgeous looking woman. I thought that you wanted to go back to...”.

“I know. But when you brought me my old clothes, suddenly they felt... wrong. I guess you were right all along.” I said.

“How do you like Kevin?” he asked.

“I think he’s great. But... he makes me a little nervous” I said. “Why?” asked John. “Well, he’s gorgeous and I don’t want him to know that I’m a... “ Suddenly, I couldn’t finish the phrase and I covered my mouth with my hands. John simply stared at me in disbelief. I couldn’t believe that I had made a reference about another man as “gorgeous”!

John said, “gorgeous? I... He... Of all the things you could’ve said, the first thing you say is ‘gorgeous’?” John suddenly stared at me without saying a word. I didn’t know what to say next. I felt exactly the same way as when I saw that video of me wearing John’s ex-wife’s clothes at Martha’s Vineyard. I tried to say something, but John simply put his hand up. A mischevious smile suddenly appeared across his face.

Kevin returned to the table. “Sorry... I had to take care of some personal phone calls. So... what were you talking about?”

“Well... “ John began to say, “it seems that Ashely has a little crush on you...”. I gasped and covered my mouth with both hands. Kevin suddenly whipped his head around to look at me. John simply smiled. Once again, his dark side had appeared. He was like a puppet master playing with me and Kevin. John looked at Kevin’s reaction. I wanted to crawl under the table and die. Then suddenly I noticed Kevin begin to blush and get very nervous. We all sat in silence.

John stood up and walked over to me. He began pulling the chair from under me, very gently but firmly as he spoke. “Excuse us for a minute, Kevin. I need to have a word with Ashley.” I stood up and literally raced out of the dining room. I could hardly look at Kevin anymore.

As John entered the next room he closed the door. I felt humiliated, angry and nervous. “Why the hell did you tell Kevin that I had a crush on him?” John suddenly grabbed me gently by the arms. Then he firmly sat me down and pinned me to the chair.

“Look. I never... and I mean NEVER imagined you would become an incredible-looking girl. Well... almost girl. I’m really, really glad you look like this. Because deep down, I know you’re mine. That means that I’m about to get my wish... the perfect woman. So don’t speak like that to me again, ok?” I calmed down and shook my head. He went on, “As I told you before, I need you to be 100% certain that this is what you want. I take it, you want to me MY woman. But... you’re not a woman yet. There’s one last test you have to pass. And your little remark gave me the perfect opportunity to put you to that test.” John backed away and sat in front of me. He smiled warmly again.

I looked at him curiously. “What are you talking about. What test?” I asked.

“You see... there is one slight problem about you becoming my girl. What if you don’t like it? I mean, I can see you enjoy looking like a woman. But... you still need to FEEL like a woman. And in the end... you’re a virgin. You’ve never had sex. Not as a boy... And certainly not as a girl... So... I want you to have sex. For the first time. I want you to have sex with Kevin. You said yourself that he’s gorgeous. So... you’ll spend the night with him. And after that... we’ll discuss the next steps. I will talk to him about what you have between your legs so you don’t have to explain anything. So... let’s go back in there.” He stood up and walked towards the living room.

I was shocked. I couldn’t move. I couldn’t say a word. I stared into space and let John’s words ring inside my head: “...I want you to have sex with Kevin...” I couldn’t believe it. How could he say something like that. As he got to the door he turned back to me. “Don’t take too long... I know I said I would support you in your decision. But like I also said, don’t cross me.”. Then he left me alone.