Hi Mommy ... Chapter 5
"Well darling, how do I look? I think I look almost as good as you do, dammit", Linda said with a smile and laugh to her voice.
"You look gorgeous", I said. "I love what you did with my hair, but I swear I'd kill to have hair like yours, Linda."
It was full and luxurious, slightly waved, and almost unbelievably shiny. As she moved her head ever so slightly, her hair slid over itself as if it was silk - in sheets - to fall around her face, shoulders, and down her back to her shoulder blades. Her pearl drop earrings peeked through her hair and the simple but elegant single strand of pearls around her neck set off her beautiful skin.
I walked slowly towards Linda as she stood silently smiling. Reaching her, I reached for her hair with my hand - lifting it and arranging one side over her shoulder. I took her in my arms and kissed her lips softly so her makeup wouldn't smudge, and breathed in the smell of her hair. "Did my hair smell this good?", I thought. My emotions were running wild - trying to understand these new feelings I had. I could not understand why I felt so at peace dressed and made up as I was. I had known this woman for barely 24 hours, yet here I was in her apartment, transformed into a woman. A beautiful woman, and I allowed it to happen with barely a thought.
"Now you went and mussed yourself, darling Monica. Go touch up your lipstick and fix your hair. Let's see if you can make yourself pretty without my help." she whispered breathlessly.
I turned and walked to Linda's dressing table again, and remembering every woman I'd seen - ran my hand behind me and smoothed my skirts before sitting.
"You did that beautifully, darling", I heard Linda say behind me. "I set up a purse for you - your lipstick is inside there."
Opening the dress purse on the table, I reached inside and looked through the complete set of makeup, hairbrush and perfume Linda had placed there. Finding the lipstick, I removed and opened it, and stared at myself in the mirror remembering how this was done. My lipstick was only slightly mussed - the lip line was still intact - and brought the tube to my lips.
"No no, Monica", Linda whispered from close behind me. "In order to do makeup properly, you must use a lipstick brush to get the right coverage and line - especially if you don't use a lip liner pencil. It's that small silver tube in your purse. Just open it and wipe it over the end of your lipstick, then use the brush as if you were painting a line."
I did as she said, and touched the brush to my lips. It was actually easier, I mused, to do it this way than using a bulky lipstick. Much easier to make an accurate line.
As I fixed my makeup, Linda stooped peering over my shoulder whispering encouragement.
"Why don't you get some practice and touch up the rest of your makeup, darling" she whispered, "then give your hair a quick brush and we'll be off. You're doing beautifully - you may have missed your true calling."
Looking through my new makeup kit, I found what I knew was an eyebrow/eyelash comb. Holding very still, I ran the comb through my lashes so they were separated and natural looking, then carefully ran it through my eyebrows. I didn't see any problem with my foundation or finishing powder, so I used the large brush and smoothed out my blusher - adding a little on my chin and forehead as Linda did shortly before. I was careful not to get makeup on my bangs. Tipping my head from side to side so my hair was away from my neck, I sprayed a bit of perfume behind my ears and into my hair.
I sat motionless for a few seconds, staring at myself in the mirror, then lifted my chin and gently shook my hair evenly over my shoulders as I've seen so many "other" women do. I stood to face Linda and whispered "I think I'm ready, love."
"Yes", Linda whispered,"I think you are indeed. Let's go drive some lucky guys crazy!"
Being a warm summer night we needed no coats, so we walked out the door and decided to walk a few blocks to a club Linda frequented. The doorman greeted Linda warmly and shook my hand gently, welcoming me to the club anytime in the future as a friend of Linda.
"Always happy to have another beautiful lady on the premises", he laughed, "especially if she's a friend of Linda's."
I offered Mike - the doorman - my thanks, and we walked in the door into a reasonably quiet club with huge dance floor. Happily - the music was of the big band and smooth jazz genre. My kind of music, I thought, as we walked around the floor and found a nice private table.
A waiter appeared almost immediately to take out drink orders.
"Good to see you again, Linda! And who is this lovely lady you've brought with you tonight?"
That cleared up my fear of being discovered. It was bright enough in the club that he could see me clearly, and he had no suspicions at all.
"Hi Brian" Linda said. "This is my friend Monica. Monica, this is Brian. Cute isn't he?"
"Yes, he is" I said, feeling my face heat up in a blush. "Hi Brian - nice to meet you", I said in as feminine a voice as I could manage. It came out as a throaty whisper. Rather sexy, I thought to myself.
"Very nice to have you in the house, Monica" Brian said. "I know what Linda is going to have. I'm betting a very classy lady like yourself would like something simple like a white wine spritzer?"
This was a very charming guy indeed, I thought. "Actually, Brian, ths is a rather special occasion, and I would prefer something a bit more ... ohhh ... hearty? How about a Wild Turkey on the rocks with a touch of water."
"WHOA!", Brian said with a big smile. "My kind of lady! WT Rocks it is for the beautiful brunette! I'll be back in a flash, ladies!"
Linda was laughing at our exchange. "Well! You certainly made an impression on Brian, my love! Did you notice the bulge in his pants?" As a matter of fact - I hadn't. Did I have that effect on a guy?
"Stop it, Linda" I said. "You're having delusions"
"Oh really!" she answered. "Well I'll tell you what, darling, when Brian comes back you just drop your eyes to his lap while he's talking to you and see what happens. He's got it for you bad." she said laughingly. "The question is ... what are you going to do about it!"
"Linda." I said softly, "for te first time in my life I am dressed as a woman. I admit I'm enjoying myself, as disturbing I find that to be. But if you're thinking I'm going to get involved sexually with another guy, you are mistaken!"
Linda laughed and said "Sex? Who said anything about sex, darling! If that's what you're thinking ... it's YOUR idea - not mine!"
I was forced then to ponder the fact that Brian did have some appeal to me. Strange thought that was, I felt an attraction that left me questioning my orientation. I've never had any kind of attraction to males before, as James anyway. I loved women. I was puzzled and somewhat alarmed at this feeling I was having. Brian returned.
"Here we are, ladies. White wine for you, Linda, and for the beautiful Monica ... WTRocks! If there is anything else I can get you ladies - just holler, okay?"
I decided to test Linda's theory some, and caught Brian's eye.
"Brian?" I said, while dropping my eyes to his lap, "would you be a dear and bring us some kind of snacks or something? Nothing heavy, though - we girls have to watch our figures, you know"
Linda nearly spit up her drink seeing how Brian reacted.
"Sure thing, hon! I'll have the kitchen put a tray of goodies together for you!"
He was practically falling over himself, and just as Linda said - a very visible bulge showed in his slacks hat he had very little success hiding. It was very obvious he was breathing in Monica's perfume and getting as close to her as he dare.
"How about you, Linda. Anything I can get you?"
Linda laughed openly. "That's okay, Brian - you take care of Monica. I'll steal something from her plate if I get hungry."
As Brian walked away, Linda looked at me with raised eyebrows.
"Well?" she laughed. "Still think I'm crazy?"
I sat quietly for a few seconds considering what to say. "I guess you were right, Linda. I don't know quite what to say or do now. I don't understand what I've been feeling with all this. I'm very confused, actually." And I was. VERY.
"I know you are, darling, and I understand completely. You've had a very stressful day, emotionally and physically. I know it's difficult for you with this newest complication. Look ... all I can say to you is to do what you feel comfortable with at the time. I'm not suggesting you should experiment sexually. That is something only you can consider. I agree that would be a big step for you, and one that may have repercussions you're not equipped to handle emotionally. But ... and I say this with an open mind ... there is no harm in flirting with a guy or dancing if the opportunity presents itself. Even a little cuddling is not a big deal as far as I'm concerned. I want you to understand something at the outset. I've grown very fond of you in a remarkably short time. I don't think it has ever happened to me before, so you need to understand that. That said, I happen to be very open-minded about life, and if you should decide to go a bit further with this, I will understand and support you. I give you my word on that, my darling. This was my idea. I encouraged you to do this - originally as a fun thing, but them more seriously when I saw how great you look as a girl. This is no accident, I don't think. You pass too well for it to be an accident of nature, and you have picked up the mannerisms too easily. There is something deeper at work here, and we have to acknowledge it. Are you up to that, darling?"
I sat quietly and considered the situation as Linda posed it. I was seriously torn. I was totally unprepared for the feelings that had surfaced since I had first dressed in Linda's clothes, been made up, and had my hair done. This was something new and alien. Now that I appeared for all intents and purposes to actually be a woman - I was playing the part by flirting openly with other males. Playing the part maybe too well and too easily. What was happening to me, I wondered. I could feel a wetness in my panties - I was aroused without realizing it. I was actually enjoying myself as I flirted with Brian. Could I really go further? Could I - would I - actually get physical with another male? What did that say about my sexuality? Rather ... what did the ease at which I even considered such a thing say about me?
"I don't know, Linda - I really don't know. I'm very confused right now."
"Okay look" she said softly, putting her hand on my arm for support, "you have fun with this and let things go where they will go. Whatever happens and wherever you wind up, just come back to my apartment, okay? I would very much like to have you with me. In fact ... I would welcome it if you were to decide to move from your little place to mine. Lord knows I have enough room! You know I do very well, so money isn't an issue - you can live with me and put your money in the bank. I wish you would consider my proposal."
I sat quietly with my head down as I considered Linda's proposals and support. Brian had apparently noted my somber mood from his station and came up behind me. I was slightly startled when he appeared, crouching alongside my chair.
"Something wrong, pretty lady? You don't look quite as perky as you did when you ladies came in." He put his hand on my shoulder as he spoke softly, and leaned close. I could hear his breathing. His face was so close my hair moved as he exhaled. "Is there anything I can do to cheer you up again?"
I surprised myself at how "girly" I responded to Brian's questions, but I put mu hand over his on my shoulder and squeezed it gently, and tilted my head to the side so it rested against his. "No ... it's okay, hon. I'm just feeling a little confused right now. I'll be okay. But thank you for caring."
Without any thought at all, I turned and kissed Brian gently on his cheek, and touched his face with my fingers, stroking gently. Out of the corner of my eye I could see Linda taking it all in - her face revealing a knowing yet peaceful smile.
"Listen ... I get off in about an hour. Would you be interested in going somewhere for a cup of coffee or something? I'd like to get to know you better, and Linda knows me well enough to tell you you'll be safe with me. Think about it and let me know, okay?"
"Thank you, Brian. I'll think about it." I said. Linda merely nodded her head and mouthed "go".
As he began to leave, I put my hand on his arm again and said "Okay, Brian - I'd be happy to go with you"
"SUPER!" he said brightly. "I'll come fetch you shortly! Rest easy, Linda - I'll have her home at a decent hour." And he walked off with a big smile.
I glanced at Linda. The question didn't need to be said. She simply smiled and nodded her head in agreement. "Go have fun and see where this takes you, darling. Should I wait up for you? I'd love to hear how you make out."
Linda could see the fear and concern in my eyes. Also - the confusion.
"Scared?" she asked gently. "Don't be, honey. It will work out one way or the other. I'm not going anywhere. Relax and have fun. Brian is a nice guy, so you don't have to be concerned about anything. He knows me pretty well - at least well enough to know I'd cut his balls off if he messed with you. But like I said, he's a nice guy and you don't need to worry about it."
Before I knew it, Brian was at my side. "Here I am, pretty lady! Are you ready?"
I looked at Linda, then at Brian, and nodded my head. "I'm ready, Brian."
Brian took my arm and we said goodbye to Linda for a while, then with his arm around my shoulders, we walked towards the door, and a new chapter in my life.