-Seven Days Earlier – 9 p.m.-

Sarah’s knock came exactly at nine. I of course knew she was coming as I had been peeking through the peep hole since about…oh seven…and pacing…and worrying.
Was she going to show up with the police and have me arrested? Or some boyfriend I did not know about and beat the shit out of me? I went over scenario after scenario in my head, but none of them really seemed to match what happened that afternoon and what I had seen in her eyes, her face.

None the less, I was flushed and shaking when I opened the door to her, managing a weak “Hi” and gesturing for her to come inside. She was dressed smartly in studded jeans and a flower print blouse that hung down over her hips in soft ruffles, her dark hair loose and flowing down her back.

I had taken a shower and was in chinos and a button up shirt. Seemed appropriate to meet whatever came that night clean and in the best clothing I could muster.
As she came in she held up a bottle of wine and two glasses, smiling and saying “I didn’t know if you drank wine or had glasses, but today seems to be a day for new experiences…soo….”

Her eyes lit over me and she frowned slightly “You look nice.” She said. I was not convinced either.

“Yea..uh…I mean Yes, so do you.” I stammered as we shared an awkward moment.

Finally I remembered myself “Uh…come in, let me take those.” She relinquished the bottle and glasses and swung a bag off her arm moving into the kitchen seating area.
“Here are your clothes.” She said putting the bag on my small kitchen table.

I said “Thanks…uh…” I pointed to the dress hanging on the door to my bedroom. “There is yours…”

She nodded and her eyes moved about my small apartment, taking it all in and murmuring “Nice place…” I wasn’t convinced either.

Looking at the wine, I said “I uh…don’t have a bottle opener.”

She made a gesture and said “Twist top. Only the best! ”

She turned and walked into my living room, looking around and picking small items up for examination.

“You uh…you want wine now?” I asked and she replied “Sure.”

I opened the bottle, poured out two glasses, and joined her in my small living room.

She took the glass from me and clinked it to mine. “Cheers…” she said, a sly look on her face.

“Cheers.” I replied simply and tasted the wine. I generally didn’t like wine, but smiled and made a yummy noise anyway.

She said “Thought it might take the edge off, so drink up sweetie.” And she plopped down on my couch.

I began “Sarah…I really am sorry fo-” She held up a hand and stopped me.

“No, we are not going to go there Andy, at least not yet.” She gestured “Sit.”

I sat. “Here it comes…” I thought.

Sarah looked around again and remarked “I imagined your place would be at least a little more feminine feeling…this is…very ‘guy’…and kind of ‘sanitized’.“

I groped for a response…”Well, um…yea, I am kind of living that way…” was all I managed.

“Why?” she asked frankly.

When I appeared lost again, she continued “I mean, transgendered people are not exactly mainstream yet, but Christ we have like six on campus, several are friends of mine, and my high school even had two people in transition….so, why not you too?”

“It’s a long story.” I replied stiffly.

She noted my tone and replied “Well, given what you did today, I think I deserve to hear that story, don’t you?”

After a few seconds, I reluctantly nodded, and haltingly began…”Not much to tell really.”

My parents both died of alcoholism when I was young. My dad when I was five, my mother at eleven. I was passed into foster care, where “fitting in” and “not making waves” was required if you wanted to stay with people. I was struggling with the experiences of living with an out of control adult from age 5 to 11 and it was all pretty tumultuous with the trauma of that AND the dysphoria I was feeling about my gender.

Sarah asked about some specifics, and I reluctantly shared. We talked for almost two hours.

“So…” she said when I had finished. “Not a lot of time or space to deal with feelings of being a girl?”

“No.” I replied and felt hot tears come. “Not…until the past two years…once I finally got on my own.”

She put her hand on mine and squeezed. “What about your parents…I mean, your foster parents? Don’t they know?” She asked.

I shook my head. “No. They….we don’t talk much...anymore.”

“Whooo….that’s heavy.” She said and was silent for a few moments.

She took another sip of her wine and asked “Have, or are you talking to anyone about all this? Any sort of counseling?”

I nodded. “I go twice a month. Because I was a ‘ward of the state’, they pay counseling fees until I am 25.”

“And, how much do you tell your counselor?” She asked. “Do they know that you are trans? Do you talk about that with them?”

I nodded. “Yea…”

She nodded back “Good. What are they telling you to do?”

I looked at the ceiling and sighed “They…she…is telling me that I should explore it…come to ‘grips with it’…stop…what she calls the ‘hide, deny, and repress’ mentality that I learned under foster care.”

Sarah nodded again and gestured. “Yea, looking your place I never would have guessed that you weren’t ‘just another guy’. Kinda’ wondered about what you told me earlier…”

“It’s, how I’ve learned to live…” I said.

“And now?” She asked. “This is an important moment in your life Andy…today changes things…it has to. Don’t you think?”

I blew my breath out. “Yea…probably…but…I don’t know…I don’t know how.”

She smiled and squeezed my hand again. “Well, for starters, we have to get you out of sneaking into girl’s bedrooms.”

I looked abashed and she continued with emphasis “By getting you your own bedroom filled with girl things…and the freedom and confidence to enjoy it.”

She stood and stretched, shaking off the heaviness of the past minutes. “Speaking of bedrooms, show me yours…and your girl things. I want to see what you have.”

As we passed into the hallway towards the bedroom, Sarah fingered her pink dress hanging on the door and said “You have an iron…good.”

She grabbed the dress down and spun on her heel, holding it up to me. I turned red and backed up a little but she moved with me holding the dress up to my body.

“You are a little taller, so it comes shorter on you, but it is a nice look. You should keep it...the panties too.” She said handing me the dress.

She turned back, opening the door to my bedroom and going in like she owned the place. She said over her shoulder “You will need them again I think.”

I stammered “Thanks…uh, what?” and followed her in.

My bedroom was one place that I felt safe enough to have some girl things out and I had left my pink comforter on the bed and a few items out even though an actual girl was coming over.

Sarah looked around “Now, this is a bit more like it.” She said running her finger over the coverlet and looking at the dark purple curtains covering the blinds.

She turned and reclined back on my bed and said in a sultry voice “So Andy…show me what you got…”

I turned beet red and I froze, my mind trying to determine what she meant.

Sarah giggled and said “Your clothes, Andy, show me your girl clothes.”

My closet contained just a few things I had ordered off the internet with what little money I had – skirts, blouses, rhinestone girl jeans, and two dresses. All of them were, to be honest, overtly feminine and I felt none of them fit me like they should. I pulled them out one at a time, and Sarah asked me to hold each up to my body.

When I was done, she asked quizzically “Is there a maid’s outfit in there somewhere too?”

I flushed and after a second, nodded. “Show me.” She said simply.

I reached into the far back recesses of the closet and produced said item. It was satin, black and pink and very short and very frilly. She gestured as I held it out and I put it up to my body, flushing in embarrassment.

She looked at me pointedly and said “There is no shame in that Andy. Christ I have a ‘fucking machine’ in my closet!” and laughed. I laughed too, and tension seemed to drain away.

She patted the bed. “Bring that over and sit down .”

I did and she took the outfit from me, removed it from the hanger and put it up against my sitting body, spreading the skirt out over my legs.

“You hold the top up.” She said as she sat back and regarded me.

I felt the soft cool satin and the lace as I held the bust to my chest feeling foolish and at the same time, liberated.

Sarah sat back and said softly “So…this is all at least a little sexual for you, isn’t it? I mean, why would you try out my fucking toy if it weren’t? Yes?”

I nodded slowly looking down at the shiny black and pink ruffles cascading over my pants.

“And, do you have fantasies about anal sex…sex with men? Sucking cock?” she continued.

I nodded again feeling flushed.

“There is no shame in that.” She said and I looked into her face and saw that she meant it.

“And what about women? Are you attracted to women?”

I nodded and said softly “Mostly I’m attracted to women really.“

“But you fantasize about guys too? Are you a woman in those fantasies?”

I nodded, glancing up to see her reaction. A soft sympathetic smile played across her face.

She considered for a moment and asked “If I could snap my fingers and make you female right now, would you do it?”

I looked up sharply and said firmly “Yes.”

She sighed and considered…at that moment, I actually wondered if maybe she could…

She turned back to me, very serious. “Will you explore being a girl with me, Andy? Is that something you want?”

My fears quailed, my limiting beliefs all clamored for attention, but my heart and my mouth instantly said “Yes.”

“You know what that means?” she asked. I shook my head “No...”

Sarah smiled. “Well, we can explore what it means together…”

Sarah took the maids outfit from me and laid it on the bed between us, then stood up motioning for me to stay.

She went to my dresser and pulled open drawers till she found panties, lingerie, which she inspected, closing the drawer. She turned back to me. “Makeup, jewelry?” she asked.

I pointed to my adjoining bathroom. She went in and I heard her opening drawers and rummaging. Clearly she found it as she came back out with a set of 4 inch gold hoop earrings.

These she held up to my ears, looking at my lobes and commenting “You should get your right ear pierced…these would look good on you.”

She set the earrings on the bed next to the maids outfit and gestured for me to stand up.

I…was so uncomfortable and turned on by this…all this…I was trembling. Sarah noticed, but did not do what I hoped she would do.

She took my hands in hers and said “We are both going to take a week to think on this.”

My disappointment showed clearly, but Sarah pursed her lips and nodded, leading me back out into the front room.

She stopped in front of the door and turned to me. “I need a week to plan things out, and you…you need a week to decide if this is –really- something you want. And if you want me to be an active part of.“ She put an emphasis on the word “active”.

“So you need to really give this serious consideration Andy. “ she stressed looking me directly in my eyes. “Do you understand?”

I nodded.

“I would like to begin next week…unless you put a note under my door saying ‘No’. That’s all I need, and we will never discuss this again.” She said. I visibly paled.

“If you decide you want this, then go get your ear pierced as a gesture to me that you are up for what we will do together…and remember, you are getting involved with a girl who has a fucking machine and a bondage harness. she said that last forcefully.

She looked up into my face and kissed my cheek. As she opened the door she got a wicked grin on her face and said “I am a dangerous girl with plans…you should be a little scared.“

And then she closed the door and was gone.