Mary's Journey Pt. 02

Story Info
What happened when Harry met Mary.
58.4k words
4.85
3.2k
7

Part 2 of the 2 part series

Updated 05/22/2024
Created 05/19/2024
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This is part two of Mary's Journey. As always, all characters engaging in sex are over 18.

In Part One, Michael had slowly developed into Mary. After a successful holiday with her dad, where she had her first romantic experience, confirming her attraction to men, she now awaits the arrival home of her best friend Harry. She wants to tell him first, before coming out to the world.

Chapter 6 - Discovery

The two weeks before Harry came home, flew by. Life and my education continued unabated. I took Sally's advice and learned about anal sex, buying the necessary supplies and even a six inch vibrator. I had tried it out a number of times with plenty of lube, and found myself comfortable with the length and minimal girth. It was these self exploration sessions, backed up by memories of what might have been with Peter and a raft of other fantasies that I had, that supercharged my libido.

I found myself exploring my body almost every night and very much looking forward to that time of the day. I guess I was experiencing a compression of years of being a horny girl. I came to realise that I REALLY loved that part of who I now was.

A few days before Harry arrived, I had the final exam of my chef's apprenticeship. Among other things, I was required to plan and serve a complete meal, choosing a French inspired five course menu. That took most of my mental and physical capacity and energy to plan and execute - all while still working my normal days at the restaurant. I just killed it though, getting over ninety-five percent on the assessment. Ecstatic but exhausted, I rewarded myself with a spa treatment. Massage, facial and a body scrub, leaving me feeling like a million dollars. I had to have my nail polish removed and nails shortened a little more than normal though, so I had normal length, but very well manicured nails.

I had arranged to have a week off starting on the Thursday of Harry's arrival.

After he had planned to arrive mid morning, Harry and I met at the golf course at about midday on Thursday. Daddy had dropped me over about thirty minutes before Harry had said he would arrive, wishing me luck. I planned to get an Uber or taxi home. We were going to be going our separate ways anyway and I wanted to perhaps have a drink at the club after the round, so that excluded me driving myself. Before leaving home, I laid out my clothes and prepared the makeup etc in the spare room, ready for dinner with Sally and the girls later that night.

I was super nervous, as I planned to tell Harry about me being Mary, as we played our round.

I had done a short warmup, and when I saw him arrive we waved and I walked over. When I got close I was stopped in my tracks. Harry looked incredible. Since I had seen him last he had put some bulk on and it was very well toned. He had shorts and a t-shirt on, both of which highlighted an obvious increase in physicality.

Smiling and laughing, we shook hands, greeting each other like long lost brothers, as we came in for a manly hug and a slap on the back. He had just had a hair cut and his cologne was both new and divine. The school was obviously training him well. I noticed a stronger handshake and almost missed matching it, remembering that I needed to be Michael for the next little bit. His hands were a little calloused from all the golf most likely.

Fortunately, the weather meant that I was almost justified in wearing light long men's pants and a light jacket, to hide my hairless legs and arms. I had worn a very tight boob tube under a darker t-shirt, to flatten my a-cup chest. I thought it might not be too noticeable, if I had to take the jacket off. I had my hair tied in an attempt at an androgynous pony tail.

Harry went straight into tease mode, ribbing me for wearing pants and a jacket and having long hair. I retorted with, "Well at least my stuff still fits. You look like you've taken steroids or something, busting out of that shirt. What the hell are they feeding you over there?"

We laughed and the banter continued, like we'd only seen each other the day before. Harry got his gear out and we made our way to the course. I claimed that Harry would have to spot me at least ten shots, as my handicap had blown out to between five and eight, but that I hadn't been playing more than once or twice a month for ages.

Early in the round the sun came out, and by about the sixth hole I simply had to take my jacket off. Doing so, I put some sunscreen on my arms. I saw Harry looking strangely at me and kept my arms moving so he'd hopefully not notice the complete lack of hair. I also made sure to put myself in a position that would hide any chest bumps that might show. Laughing, he walked over to me and asked, "What happened to the hair on your arms Mike?"

Blushing before going with my backup plan I said, "I started cycling a little while ago and got told that, in order to stop bad gravel rash when I come off, I should shave them." I got a 'huh' in reply and we left it for a bit.

I was feeling pretty self-conscious as we came to the tenth tee. Harry had been looking at me weirdly, as we had walked the course. He wasn't just looking at my arms. I saw him several times, looking all over my face and at my hair and even my ears. I even noticed him looking at me when I had walked ahead. I was making sure that I was walking with as much male swagger as I remembered having. If he noticed my piercings, then he didn't say anything. I thought I'd seen him looking at me more generally too, but again he never said anything.

For my part, I was starting to REALLY appreciate Harry appearance. He was his usual confident, relaxed self. Always happy and ready with a quip after a bad shot or putt. We talked about everything that was going on with our lives. Harry congratulated me on my exam results as I did for his engineering and golf results. Harry said that he wasn't going to make it as a professional golfer, but had worked extremely hard to maintain a great academic result and equally hard at his golf, to ensure the continuation of the full scholarship for the last year.

As we walked off the seventeenth green, there was a bit of a walk to the eighteenth tee. Walking beside me, Harry turned his head to me and said, "Its so good to see you Michael. You seem happier than I've ever seen you. More relaxed and confident. Looks like we're both killing it eh?"

I turned to him, replying with, "Thanks mate. I am really happy. I'll be crowned a chef in a few weeks, when the results are released, and you've only got another twelve months before you become an engineer. Yeh, we're killing it together."

I chickened out on telling Harry that I wasn't actually Michael, that instead I was Mary and proud of myself. I just couldn't do it. I was scared that telling him would potentially ruin the friendship that Harry and I had shared for well over a decade.

We finished the round and after a quick drink at the clubhouse, we walked outside. "Come on mate, throw your stuff in the back and I'll drop you back at your place."

I agreed and as we got home, I grabbed my bag and Harry my buggy and we put them in the garage. There were no bikes hanging up in the garage though and I wondered if he'd notice. Harry didn't look around, but he asked if he could come in for a cup of coffee. I agreed and we went up stairs.

While I put the coffee on, Harry excused himself to go to the toilet and before I knew it he was half way down the hall. I looked up at him just as he approached the spare room, which he would have to pass on the way to the toilet. And all of a sudden it hit me!

I had laid all of my clothes for the dinner with Sally and the girls. I had left the outfit, negligee and accessories all out on the bed and as Harry got to the door to the room, the light emanating from it, told me that I had left the door to the room open.

Please don't look in, Please don't look in, Please don't look in, I pleaded to myself as he got to the door of the spare room.

As he arrived though, I saw his head turn left to look in. I could see the side of his face change ever so slightly, as the image of what was on the bed, registered with him. He remained facing that way, until he'd past the door and with a barely noticeable pause, he disappeared into the bathroom. Panicking, I ran down the hallway and silently closed the spare room door.

I was finishing making the coffee when Harry came out of the bathroom. I saw him look at the now closed door and there was another flash of recognition. I was hoping beyond hope that he wouldn't ask.

We chatted about plans for the next few days, up to and including a dinner at our place with Harry, daddy, Sally and I on Sunday for my birthday.

About ten minutes after I gave him the coffee, Harry said that he'd better go. Trying to act normally, I walked him out to the car. Getting in, he started it and wound the window down. He paused before turning to me and looking me in the eye. With considerable confidence and as if it was a forgone conclusion, he said, "We need to have dinner tomorrow night. And you should dress in what you really want to." My mouth opened and I was left silent, staring at nothing but the road, as Harry drove off.

"Harry knows." Repeated in my head, long after his car had left sight. I walked like a zombie, back into the house and sat for a bit. My first reaction was to call daddy, but he didn't answer his phone. He had left on a business trip out of town, after dropping me off, so I called Sally.

She was busy with a client, but came to the phone when I said it was urgent. I told her that Harry had seen the clothes on the bed after he unexpectedly came inside. She got out of me that he didn't appear to be worried and I told her exactly what he said. "That means he knows and wants to meet Mary love. The way you explained it, it sounds like he was firm with you? Almost like an order?" After i indicated it was, she briefly added. "This is actually really good news Mary. I'll come over a little earlier than planned so we can talk some more, before we go to dinner."

After she arrived, we talked as I finished getting dressed. I went over exactly what had happened during the day; from our greeting in the car park, to our collective stolen glances, all the way to Harry driving away. Sally was convinced that Harry was not put off. Laughing as we walked out to the car to go to dinner, Sally said with a cheeky laugh, "Oh. Maybe he was firm with you because.........Mary and Harry, sitting in a tree, K I S S I N G?" She sang the last bit in the age old teasing way.

I said, "Don't be ridiculous Sally. He's my best friend and he's straight."

Laughing, Sally replied, "I know love. But Mary, so are you, remember?"

I was lost in the list of endless possibilities, for quite a while. Later, at dinner, I was sitting next to Christine, one of Sally's closest friends. She enquired after what had me so distracted. I told her, "I caught up with an old friend today and it may have opened up a romantic possibility."

Smiling, Christine said, "Oh how lovely for you Mary. Don't hesitate lovie. You go for it, grab it with both hands and give it your best. You're so young and old friends are reliable because you already know each other."

With a worried look on my face I replied, "Yes, but I'm not sure that he knows me any more, Christine. Plus I wouldn't want to ruin our friendship."

She put a hand on my cheek and lovingly said to me, "Nonsense Mary. Our friends know who we are inside... at our core. That part of us doesn't change. What you do and how you look may change, but who you are doesn't."

I took some solace in what Christine had said.

Another great dinner! I was really starting to enjoy these. Sally and I drove home and after giving me some more praise, as she was dropping me off, she suggested, "Cook for him Mary. Let him see the beautiful, confident, accomplished, sexy woman you've become in a setting that you are comfortable in. At the very least he will continue to be your best friend. I'm sure of it. And, if you find that there's mutual attraction, then welcome it and see where it takes you."

I was wracked with doubts and fears as I undressed, took off my makeup and got into a dark green satin nightie with spaghetti straps and matching panties. Collapsing into bed, I fell asleep almost immediately.

That night I dreamt of the island resort holiday. Only instead of seeing Peter doing all the things we had done, I saw Harry. Harry was better looking and had a body that was more yummy than Peter's. My waking thought, with those images clearly plastered in my mind, was "If I could feel the attraction for Peter that I did, then was what I was seeing and feeling about Harry yesterday not the same?" After a little bit, I concluded that it might be. Further, that I didn't think I'd get weirded out if the attraction was mutual"

After a light breakfast, I called daddy. It was about eight in the morning his time. He had just finished his breakfast and had an hour before his first meeting. We talked for about twenty five minutes. I gave him an abridged version of what I gave Sally and he pretty much gave me the same answers. His were a little more brief though. "I've always liked Harry. He is a great guy, a good man and if you two have a chance of being a thing, I say go for it."

But daddy added his typical sage advice next. "Just treat the man you know with respect. Be honest with him always. I trust you to listen to both your heart and your head. Above all, do what's right for you Mary."

At about nine o'clock on Friday, I got a text. Looking at it, it was from Harry. My heart started racing and I opened it with trembling hands "Pick you up for dinner at six-thirty tonight?"

He was still straight forward, and there was nothing I could read into it, more than he just confirmed his request.

I responded with, "I'd prefer to cook for you. Would here at seven be ok?" I instinctively let him made the decision.

I got a heart emoji in return and I almost had kittens. "Hold your horses Mary." I said out loud. After a few minutes contemplation, I rose and spoke confidently to myself. "Ok then Mary! If you're going to show Harry who you are, then let's REALLY show him."

First things first. A Plan. I sat down, planned the menu and my outfit, the later requiring that I call Sally and make an appointment to do my hair. With those things in place, I decided that I needed to do some shopping.

First I went to the same fresh food market that we used at the restaurant. Speaking to Otto, my favourite grocer, I asked him for his very best of the day. He gave me wonderfully fresh, top quality meat and vegetables. I stopped at the nut shop, a wine shop and at the shop that we got our coffee from, to get fresh beans. On the way home, I also stopped at our local florist and bought some flowers.

I went home to have a small bite to eat. After changing into Mary, I decided that I needed to go to a couple of the best ladies clothing speciality stores. I picked up a few things, rushing in and out, not really paying any attention to what anyone might think or how they might look at me. I was on a mission and I was running out of time.

Sally styled my hair and did my nails between one thirty and three. From there I rushed home to start the meal. I hadn't left too much time in the schedule, so what I was able to do, was what Harry was going to get. I can remember only a few times in my life, where I was as happy in the kitchen, as I was that day - humming and singing to the music I had on.

At six o'clock, daddy and Sally texted me to ask if there was anything they could do. When I said no and that I was on schedule, they both sent their love and wished me good luck.

Chapter 7 - Zero Hour 7PM

At precisely seven o'clock, there was a knock on the front door. As I went to open it I thought, "Other than daddy and Sally, this is the first time in my life that I am presenting as Mary, to someone that has known me previously as Michael."

I was wearing a form-fitting, mid thigh length black wrap dress that accentuated my modest curves. It was off the shoulder, with a plunging neckline that brought into view, the edges of my breasts, with a gentle swelling outward. There was subtle matt black lace edging on the sleeves, if you paid attention to them. The back had an oval shaped cutout that extended from just above the hip line, to just below the piece across the back of my shoulders. It indicated that I was not wearing a bra and the satin and lace high cut thong gaff, left no noticeable indentation in the dress and of course, prevented Mr Mary from affecting the front of the dress.

I was wearing skin coloured nylons that gave my legs a little shimmer. I had bought a new pair of, nude coloured, two inch high pumps that helped accentuate my calves and lower thighs. I was wearing a delicate gold pendant of an angel on a chain that left it just above my breast line. Complementing the pendant were heart shaped earrings and a simple gold belcher bracelet.

On the advice of Sally I had chosen smoky eye makeup with defined lashes, along with a bold, dark red lipstick, with matching nail polish on my new nails. She had styled my hair in loose waves, that reached down over my shoulders. I had selected Chanel No5 and had dabbed a little under my ears and on my wrists.

Internally, I knew I needed to be my true self and let that confidence carry me for the night. I wanted to act with all the grace and poise I could muster, letting my inner beauty shine through.

It would appear that my choices and eventual appearance had Harry's complete and undivided attention, because after opening the front door, he stood like a stunned mullet, looking at me from head to toe and back up. He didn't say a word and I let him process it at his own pace. I needed to give him the space to be his own true self as well.

With a little jolt, he came back to the land of the living. Smiling broadly at me, he gently extended his hand to shake mine. I daintily took his and he said, "Hello, I'm Harry Walden." His hand was warm, softer than I remembered from the previous day and he held mine like he was holding a rose petal. I was stunned with the change in Harry's demeanour.

He was wearing a suit without a tie. It was clearly his best suit and it matched my after five outfit, very nicely. It was a light grey Prince of wales check with royal blue bordering on the check and he wore a white shirt that was clearly new on. Also new were his black lace up leather oxford style shoes and a matching belt. He was wearing the same cologne as the day prior. He had just shaved and his hair had product in it, styled in a trendy left part with a wave at the front.

He was so handsome and still probably five inches taller than me, even with my pumps on. Dressed as myself and feeling every bit as feminine as I looked, I found the height and weight difference quite alluring. It gave me a warm flush which, combined, was a little distracting.

I answered Harry's introduction with Mary's soft, quiet voice, "Hello Harry. I'm Mary. Mary Slattery. Its lovely to meet you. Won't you come in?" Standing back, Harry passed me and closing the door, I led him into the lounge room, where you could see the table, set already, in the dining room. The flowers were arranged nicely and there was some soft music on - slow eighties ballads that I had always loved.

Standing in the centre of the room, I pointed at the bar, and in a waving motion, said, "Would you mind making us a drink please Harry? I need to check on some things in the kitchen. I'll have a glass of the Sauvignon Blanc please. It's in the ice bucket."

Turning to walk to the kitchen, I took a few steps before looked over my shoulder to see Harry's eyes make their way down the back of my dress towards my arse. I made sure to maximise the sway of my hips. As his eyes came up, he saw me smiling at him and as I turned the corner, I saw his face flush crimson red.