Morning Walk, Morning Stumble

I went out for a morning walk, alone, again. My wife and I had gone away for a seaside weekend, hoping we could save our marriage, which had seriously gone stale. We couldn't even muster the energy to argue, and lived like brother and sister rather than husband and wife.

I wanted to smell the sea, she did not. She wanted to lie in til who knows what time, I wanted to make the most of being beside the seaside. So, I went for a morning walk. The sun was out, but as it was a weekday, not many tourists or daytrippers were about. A gentle breeze sent the smell of the sea my way, and I loved it. Nothing calms me down as being near water.

Slightly ahead of me I noticed a female figure struggling to walk in her stiletto heels. I smiled to myself, trying to work out if she would stay upright or not. She had gorgeous legs, and tried to walk with a seductive sway of the hips. I knew this town had a reputation for its appeal to the transgender community, in all its varieties. I wondered if this might be someone trying to quietly practice venturing out for maybe the first time. From behind she, or he, looked very appealing, with a curvy feminine shape. I knew this could be attained with some attributes.

My pace was slightly quicker and I was about to slowly overtake the still struggling person just ahead of me. I must have startled her, because when she noticed me she reacted abruptly, causing her to fall sideways. I had half expected this to happen, and I managed to grab her and prevent her from taking a very awkward stumble. I put my arm around her waist and held her arm, steadying her on her heels.

Some swearing under her breath gave a modest voice to the frustration and embarrassment. I didn't immediately say anything, allowing her to regain some composure and dignity.

"Thank you for catching me, I almost made a proper spectacle of myself there," she spoke.

"First time out on those stilettos?" I asked.

"Yeah, I thought to go early and hopefully get my sea legs as I went on. I don't understand how real women do this regularly and still manage to get from A to B," was the response. "And my secret is out of the bag as well now. I had hoped to make it back home and privately celebrate my first outing."

"Not to worry, I am only here for a few days and I am not local. I don't even know anyone here, and I'm pretty sure we have no common friends," I tried to reassure her.

Dressed as he was, I decided to address him as a woman, also to see how comfortable he was with that. My comment was met with a smile.

"So, are you soldiering on on your own, or do you want to take my arm? You can think of me as your stabiliser," I smiled.

"Are you sure you want to be seen with someone who's obviously a dressed up guy on your arm?" she asked.

"Obvious only because you can't walk properly yet in what, 4 inch heels? You look very convincing when you're not moving," I smiled again.

"Thanks, I think. Do you really think I look convincing?"

"Hell yeah. I love your outfit, your long brown hair suits you very well, your make-up is very good and you smell great," I said.

"Really? You're not just saying that? I mean, even if you didn't mean it, I am still happy to hear it," she smiled.

"Let me buy you a coffee," I suggested. "You can take my arm, practice your walk and stride, and we can chat."

"You're taking me somewhere in a public place as a female companion?" she asked.

"You're not looking to pull a prank on me, are you?"

"I promise I'm not looking to upset you, or rat you out, or embarrass you in public. Just a coffee, a chat, and then we can go our separate ways again."

She hooked her arm into mine, and slightly lent into me. We walked slowly, towards a little coffee shop about a mile down the road. Slowly my companion found her stride, and there were fewer wobbles as we walked. I suggested she worked on her stride, those heels should basically tell her how to walk. She let go of my arm and walked with more confidence. Shorter stride, carefully placing one foot in front of the other, letting the shoes guide her, causing her hips to start swaying ever so slightly.

She looked back as I stood there admiring the view. She smiled at me, and walked on, backside now swaying in the rhythm of her stride.

"You like what you see?" she asked looking over her shoulder.

"I love the view, I could watch it for hours," I replied.

I caught up with her, and we walked on, very comfortable in each other's company. There was no need to link arms again, so we just walked side by side. I explained why I was doing a lonesome morning walk, just to make sure there were no immediate expectations of anything other than a walk, chat and a coffee.

"I appreciate your honesty," she said. "You're quite a charming man if I may say so. You have shown me nothing but respect and kindness, and you haven't made one suggestive comment. I could be forgiven to think you don't find my female persona that attractive at all."

"Oh, believe me, I find you very attractive like this. We've only just met, and I was wondering if I could resist temptation should it present itself. But, I'm easily twice your age, and I think you would sooner look at someone closer to your own age. So, I don't see anything else than being a nice first social contact for you as you venture out," I explained my presumed lack of being pushy and handsy.

"And I appreciate that very much. Both the compliment and your attitude. I imagined my first outing in public would involve all sorts of negative options, like groping or people calling me out," she said.

As we got to the little cafe we decided to sit outside and enjoy the morning sun. The waiter welcomed his first customers and took our orders. He commented that it was a nice morning to take my girlfriend for a walk and coffee. I just smiled and let the comment for what it was.

"Why didn't you correct him?" she asked.

"Are you mad?" I laughed. "He thought I have a beautiful young girlfriend, I am not going to argue with that! My street cred just went up massively," I said with a broad smile.

"I see, I'm your girlfriend now eh?" she smiled. "Well, I could do a lot worse for myself. You are rather dishy, for someone your age," she smiled.

As we laughed and chatted, our coffee was brought over. The waiter smiled, and said how nice it was to see that romance was still alive between us. I grabbed her hand over the table and squeezed it gently.

"You are very special sweetheart, and I love your smile and good company still very much," I said looking her in the eye.

The waiter had walked off, and we drank our coffee in silence for a few minutes.

"What made you do that?" she asked. "You pretended being in a relationship with me? Would you want to be? You don't strike me as a player, so why?"

I sat in silence for a minute, before speaking.

"Maybe I got carried away in the moment. I really do find you very attractive, and very easy to be around. I don't even know your name yet, either your proper name, or your girl name for who you are now. I am sorry for putting you on the spot, I hope you aren't angry with me."

"Not at all. I was, still am, very flattered. And I would love to have a boyfriend this attentive and courteous for real. Not to mention rather attractive. And I haven't really chosen a name yet for this side of me," she said with a little smile.

"Could you use your own name and slightly change that?" I suggested. "Or do you have a female celebrity you really admire, maybe a porn star? I know transsexuals who have modelled themselves on porn stars, even picked something close to their names," I said.

"You know transsexuals, like, really know them?"

"I do. I am more than a bit interested, and I have visited clubs and bars where I would meet them. All before the marriage mind you. With that on its last legs I know I will be going that way again. Unless I wouldn't have to of course," I told her.

She looked at me with her hazel brown eyes, as if trying to bore a hole in my soul or heart. Then her hand reached across the table and rested on mine. She asked if she could have my phone, then put her number in it. I sent a message to give her my number. She then told me a porn star she had always found extremely sexy was Madison Ivy. I looked at her, then decided to pick a name, and sent her another text, including the name.

"Maddy? Hhmm, I like it," she said.

The waiter had come to clear the table, and I paid him.

"Ready to go, Maddy?" I asked.

She smiled at me and took my arm, and we walked off, with Maddy snuggling up against me. We walked slowly, and I felt my heart rate increasing slightly, as I glanced to Maddy. I wondered what else Maddy would wear. Her current dress was very modest, elegant and although it accentuated her fine shape, it was nicely understated, as was her make-up. I asked her about that, and she told she didn't want to be mistaken for a prostitute staggering home after a late night visit.

"Is Maddy prone to dressing like that?" I asked her.

"Only in the safety of her own boudoir," she grinned. "I will link you to Maddy's pages online and social media. If that doesn't cause you any trouble of course."

"I would love that. I hope we can stay in touch, I reckon I will be a divorcee again before long anyway," I told Maddy.

"I might be very shallow and selfish, but I hope you will be. I will make sure that Maddy will be fine tuned and confident to go out with you again. Maybe even dress a bit more revealing," she said.

With that she turned to face me and pressed her glossy pink lips against mine. The kiss was ever so light, and she stepped back. She had to head back home, and I headed back to my hotel room. I could not get Maddy out of my head.

The week after I agreed to a divorce, which was handled swiftly and amicably. We both went our separate ways and I moved out. I told Maddy that if she was still interested, I would be grateful if her offer was still open to get back in touch in person again. Maddy had been good to her word, I had found her pictures, and videos. I had even seen the private ones, that should not be seen by everyone.

Maddy is her boudoir is a rather naughty girl. Latex and leather, thigh high boots, hard make-up, and a totally different image to the girl I saved from falling over. But, there was also a soft and silky Maddy, lots of lace, satin and silk, and seamed nylons. Now, I can not resist beautiful legs in seamed fully fashioned stockings.

"Hi sexy, I am am sorry about your marriage. But, I am thankful we met when we did. I would love to meet you again. When would suit you?" she asked in her message.

We agreed to meet in two weeks, which gave me time to find my own place to live and move in. I looked closer to Maddy, but not in the same town. Maddy meanwhile had upper her game, sending me very alluring and inviting images and videos. She was hardly subtle in her attempts to seduce me. Having said that, our talks over the phone and online were getting more and more sexual.

I had really taken a shine to Maddy, she was spectacularly gorgeous inside her own apartment. All that she needed was to allow that Maddy out. I hoped I would be there when she did. She had really embraced her Maddy identity, almost as if naming her female persona had triggered a sense of self and belief in Maddy as a person. She said Maddy was developing her own personality, almost as if dressing as Maddy pushed the male guise completely to the side.

The morning of our arranged date had arrived, and I got going early. I felt incredibly excited about seeing Maddy again, and to be able to hold her in my arms. Just for this occasion we decided to sort of recreate our first meeting. It was another sunny morning, and I walked slowly along the promenade. It was quiet, the street was empty, apart from one lone female figure.

A short red leather skirt, incredible looking legs, red stilleto heels. And not a single wobble this time. Her long brown hair fell down her back over a tight fitting black mesh top, with a sheer lining underneath. I soon caught up with her, and as I came alongside her, she fell, straight into my arms.

"Oh, clumsy me," she said as she looked at me with a very naughty twinkle in her eyes. "I am so glad you were here to catch me. You have such strong arms, I bet you could sweep me off my feet if you wanted to," she smiled as she looked me straight in the eye.

And I decided to do just that. I picked Maddy up, and she put her arms around my neck. Then her lips found mine, and she kissed me. Kissed me hard and hungry. The world around us no longer existed to us, as we gave into to our lust for each other.

As we broke off our kiss, I put Maddy back on her feet. She smiled, and then we both burst out laughing.

"So, did you enjoy being scooped up like that? You do play a damsel in distress quite well," I smiled.

"Well, I wouldn't want just anyone picking me up like that, but you however can do that to me any time you like," she said as she planted a kiss of my lips.

We walked to the same cafe we went the first time, and we were served by the same waiter. He smiled as I pulled Maddy's chair back and offered her the seat. Maddy made an 'oooh, would you look at that' face to the waiter, who commented that simple good manners had become all too rare. He took our orders, and walked off.

Maddy told me how she dreamed of being treated like a lady, even though she sometimes happily dresses as a tramp. I commented that she pulled off both styles very convincingly, and that I adored her current look.

"Even these?" she asked as she pressed her rather luscious breast forms together and up.

"Especially those," I said. "I love big boobs, and women who dare show them off like that, I cannot resist.

Maddy asked me for a look I loved other than her short skirt and tight top. I told her I loved tight skirts, pencil skirts, with seamed nylons underneath. And that I loved lingerie that just accentuated all of a woman's attributes. But, I also loved a skirt or dress that flared out wide at the bottom. But most of all, I admired a woman with a proud posture. Straight back, head high. And that elegant stride of a woman who knows she looks good, and doesn't need or want anyone telling her, apart from that one special person.

"That's both quite distinct and generic at the same time," she said. "How about a favourite hair colour or eye colour?"

"Not really," I replied. "It very much depends on the woman. Attractive women come in all skin colours, hair colours and eye colours. They sometimes even come with a bit extra," I said with a wink.

Maddy laughed, and agreed with my comments. She was pleased I had given her room to experiment and manoeuvre with hair styles and colours, which then inadvertently meant different make-up styles and shades. I paid our bill and pulled back Maddy's chair. I held out my hand, which she took. The waiter again showed his appreciation.

"She's a lady and deserves to be treated that way," I told him.

"And you're a smooth talker, but I love it. Play your cards right and I'll show you just how much I love it," she said with a wink.

I put my arm around Maddy's waist and she snuggled in to me again. I felt lucky that someone of Maddy's age, more than half my junior, would even be interested in talking to me, let alone throw herself at me, with hints of making this work in the longer run. She told that she felt safe and comfortable, but she was also attracted me.

"You clearly look after yourself, and you dress well. You can hold a conversation, and hold my attention. Even in these heels I am still a bit shorter than you, and I have noticed an invitingly large bulge in your trousers, which tells me you want my body as much as you want my mind or company," Maddy said.

Maddy wanted to do some shopping first, as she needed a coat, with the cooler weather approaching. Although I am not keen on shopping, Maddy promised me to not spend too much time, as she had a good idea of what she was after.

Time flew by, and Maddy quickly picked two coats. One black short furry jacket, one really elegant long coat, reaching just over her knees. I adored how she looked in that coat, very stylish indeed.

I pulled her close to me after we had left the shops, and kissed her. She gave me a fabulous smile and looked me in the eye.

"Is there something you need to get off your chest," she asked.

"Actually, there is. I just want you to know that I am very quickly falling in love with you. You make me feel young at heart again, and I think you are a truly fantastic, lovely and warm person. Not to mention stunningly beautiful, no matter the light or angle, whether you're a lady, a tramp, or even your slutty self from your pictures. I sincerely hope we will be together for a long time," I said.

I hoped my declaration was not going to scare her off. I needn't have worried as it turns out. Maddy started to tear up and just nodded to let me know she wanted this too.

"I like to think that fate intervened when you caught me. You were meant to be there to stop me from falling, and not just physical. I would probably never have ventured out again had it not been for you. And there most certainly would not have been a Maddy, or Madison," she finished.

"And if you stay around long enough today, you might still meet slutty Maddy. Because she is very eager to meet you," she said.

"Well Madison, I could swear you are trying to seduce me," I said with a smile.

"And what if I was seducing you?" she replied, her hands firmly grasping my buttocks.

"Well, I think resistance would be futile. That is, if I even wanted to be able to resist. I would love to meet slutty Maddy. She looks incredibly sexy, and makes me unbelievably horny," I whispered in her ear.

We walked on, with Maddy buying some make-up she 'really needed', before suggesting a visit to Victoria's Secret. Now, I know I said I don't care much for shopping, but, if your sexy girl suggests a trip to any lingerie shop, you are going to like shopping, if it's the last thing you want to confess to.

With the help of shop assistant Lisa, Maddy picked a red corset, with suspender straps, a red miniscule pair of panties, and stockings that looked like sparkly transparent fabric with a red seam over the back. She also bought a black, and a white identical set. I picked up the bill for that, with Lisa commenting I was a lucky man to have a girlfriend with such great taste.

"I know, Maddy is a very special lady," I replied.

"I love your name," Lisa told Maddy. "Is it short for anything, like Madison?"

"It is indeed," Maddy smiled.

"And aren't you lucky your man treats you to this gorgeous lingerie. Mind you, he's probably hoping he's the lucky one later," Lisa said with a knowing smile.

"I am sure he'll love to see me in it tonight," Maddy said, looking at me.

"What more could a man ask for?" I said. "Such beauty all to myself. I am going to enjoy unwrapping my presents tonight, and I will be taking my time."

This earned me a kiss from Maddy and a smile from Lisa. We left the shop, and decided to stop for a drink. Still a bit tentative about going into really crowded places, Maddy clung to my arm a bit tighter. We were in luck with one corner table still available, and again I made a point of pulling Maddy's chair back for her.

The waitress took our order, and we watched the crowd inside the restaurant.

"You seem on edge, would you rather have gone somewhere else?" I asked her.

"I am getting more confident but there are still plenty of places around here where I could bump into people I know, and not all of them know Maddy, or even about Maddy," she said.

"I bet people who have not seen Maddy, would not guess your male identity from how you look and act now. Only someone who really knows you would see past the beautiful woman you are now. And if they don't agree, than that's their problem, not yours."