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Back again to add some more to my little story.
She was wearing a dress the other day, she walked with her overcoat open so I saw the plan blank fabric as clear as day. Nice fitted dress with a pencil skirt ending at her knees. Bare legged today, must be the sun I thought as I noticed a faint tan, either natural or bottle. Her heels were the same as the other day. I needed to know where she bought them as I wanted a pair myself.
I saw her again today and again we walked back, I asked her why she was wearing an overcoat in this weather "you must be roasting! I'm stifled in this shirt" I confessed as I hoped there were no sweat patches. "You're right! The things a girl needs to do! I didn't bring a blazer or cardi today and didn't want to wander out in a sleeveless dress" she said as she peeled back her coat to show me the sleeves cut short at her shoulders.
"lucky you can have bare arms, my office has no aircon and I'm sweating up a heat." I joked. "Im surprised all you lads aren't walking about with your shirts half open" she laughed. I could feel my face blush. I remembered a time I dared to wear a satin camisole under a shirt as the shirt itched me. win win I thought at the time. It was bliss!
She had noticed my flush "getting hot out here? or are you all indeed wandering about with your shirts open for the girls"
I blushed even more. she was flirting with me I thought and I thought hard to angle the conversation back to her outfit.
"yes, getting too hot" I stammered.
might see you next week, it's nice to chat to someone with more than a single brain cell" she said.
"yes, more than likely. I'm a creature of habit I'm afraid".
I needed to get back, I had bought some new pants that morning when the shops first opened and my current pair were getting far too wet from pre-cum. I loved wearing panties every day for comfort but now my almost daily erections because of Imogen were getting difficult to keep under wraps.
my phone went off, "oh excuse me, I'll take this and get off" I said as I scrambled in my bag pocket to get it. She said bye and turned and as she did my bag slipped open too much and the rest of my shopping peeked out. I cancelled the call and grabbed my messenger bag in a mess and walked out the small doorway which we'd gone into.
Later I got a text, "you're brave not taking a bag for your shopping, trying to save the environment in plastic". It was Imogen, we'd exchanged numbers the other day as I had a friend looking for a contract she thought she could have a lead on.
"hahah yes. might as well save the seas!" I thought about making some half assed excuse but wanted to keep it short.
"They look nice from the glimpse I got, your girlfriend has good taste..."
The dots were deliberate. they must be. I had never mentioned an other half because frankly I had been single for so long past random dates via Tinder.
I left it until I left work, which was a later than I normally would annoyingly, to reply. "Thanks, I think they look nice as well" was all I could muster.
I left the building. That's it, I needed a new lunch spot. I had been dressing for years and never mentioned it to anyone, even the odd guy I'd hooked up with had no idea. I was a mans man. except when I got dressed up and I was the classiest, most stylish woman in town.
I turned the corner and heard the click of heels. I love that sound, most of the time I don't snap my neck round to see them any more, the sound alone is enough and helps me plan my evening outfit.
"Is your bag fastened this time?" I froze. Swallow me up ground, it was her. Of all the days to pass her going home. This was the only day. Had she stalked me, pure coincidence?.
"Haha yes, all locked up now" I joked, trying to muster a casual face.
She had her coat tied at the waist. the fabric belt pulled tight against her frame put me into over drive. Why was I such a sucker for details like that? Stitching on heels, coat belts, asymmetrical slits of a dress or skirt. wild.
She didn't answer for a second or two, enough to make me sweat.
She looked away for a second, then struck back so nonchalantly it took me by surprise "Wearing something similar then?"
I blinked. oh.
"I'll take the rising colour of your face to mean yes. or was it that I don't care and have straight out asked?"
"both." I answered honestly.
"That's cute, I only saw the pattern, the black lace on white, what are they?"
"Brazilian, full lace back, the front is the pattern." I couldn't stop myself. it was like someone was controlling my speech as we walked along the road.
"So comfortable aren't they?" she asked, still utter deadpan, but her lip slightly raising in a warm smile as she ended
"Yes and this is very odd. I'll just say this and please don't mock me, I'd rather not, it's my personal private choice. I'm not a raging sex fiend, I like to wear woman's clothing partly for sexual pleasure and partly as I enjoy it for comfort"
She laughed slightly. "What?!" I said offended.
"Nothing, I'm not judging. I saw pants in your bag and was very curious, like I said, because you didn't have them in a plastic bag"
"Well I didn't think anyone would look in my bag!"
"that's true, cross dressing fascinates me, from afar, I don't care either way. I'd like to her more if you feel comfortable".
This was so flippant I didn't know what to think. "Eh sure" was all I could muster.
"No pressure, but do you have plans now? Since we're chatting we could go back to mine for a bit? I'm just along the road a bit more"
"Sure, still a bit odd. it feels like I'm about to be interviewed for a documentary" I replied.
She giggled. "Well this isn't going public so don't worry about that!"
We walked back to her flat, a small one bedroom and kitchen/living room place close by town. She listened as I explained what I liked and didn't, what I'd done (or rather hadn't) while dressed ("Have you ever gone out all dressed up?!" no!). It was a rush to fantasise but also to enjoy being able to chat to a girl about fashion.
"Have you ever wanted a partner to enjoy this with you?" She asked as we got to her door "To just get it out the way, that isn't me asking you, I'm interested".
"Sure, it would be easier not to hide it all the time but I've got used to the fact it isn't happening". She nodded in some form of solitude with my solo experience.
"what would you like to drink?" I asked for a coffee and she made two mugs. She offered her sofa while she took up the armchair. whilst I wanted her so badly I was also enjoying the "distance" that she was creating. letting me share my secrets with her.
"We should have gone back to yours, so you could show me your vast wardrobe" Imogen joked. "Maybe another time?" I offered with a slight hesitation.
"You're assuming I'm not going to ignore you after this" (she noticed my widened eyes) "I'm joking! relax, I said no judgement, I like this conversation we have, I'd like at some point to see you all dressed up. maybe I could do your makeup" she said and stuck out her tongue cheekily.
I relaxed. Just go with it, I told myself. "Well I look like a clown the few times I've tried so having a personal makeup artist would help. do you charge hourly?" I joked back. "Smooth" she replied.
I showed her the pants in my bag, and a few stock images from retailers of outfits, shoes, and lingerie I had.
"none of you all dressed up?" she laughed. "knowing my luck someone would pick up my phone and somehow find them in the office! no way. just mirrors at home" I replied.
She was playing with her heels, dangling one from her toe, the way woman do when they're relaxed (or I believe from what I had observed). "As I said, I like looking at woman to pick out new outfits rather than think, oh you're a hot piece of stuff!" She snorted. "Was that how you thought of me then, some nice tits on legs or whatever" she was playing with me I could tell. "Oh yes, in fact it was your heels I noticed first. I love the open side they have, lovely shape to them".
She paused and looked at her heels, one off and the other balanced on her toes. "I did wonder why you kept looking at the ground when we chatted. I thought you were shy so tried to make you comfortable.... do you want to put them on? I'm a size 7"
"I... I... thank you yes I'd love to, are you sure, is that weird? I normally wear a 7 or 8"
"No, it's flattering. what I think of as annoying and needed for work, you are admiring. I try to dress well, and I'm happy it's getting notice not just as a skirt, or whatever the lads call smartly dressed women".
She took of the other and reached over and gave them to me. I took off my own shoes, and socks, rolled up my trouser leg slightly and slipped them on. I stood up, wobbled for a second then took two steps across the room.
"functional and gorgeous" I said "I like the padded insole. Oh they feel amazing. sorry. this is awkward"
She gazed up at me from the sofa. "Not at all" she smiled.
I walked about, hearing the click on her kitchen tiles as I crossed from the living room part into the kitchen part.
"You like them, then?" I nodded. "They are fast becoming my favourite style of heel, well, behind those platform soled type ones"
She smiled and walked out the room "back in a second, don't fall and break anything!" she called. "I'm used to heels!" I replied, laughing. So casual and so. fucking. horny! my cock was flipping between rock hard and limp.
She came back, "like these you mean?" She held up a paid of dark grey suede heels, with that platform base. my jaw literally dropped. "Want to slip them on" she asked so causally.
"YES!.. I mean, sure, whatever. this is still so odd"
She laughed and gave me them as she passed and sat down on the sofa again.
I changed shoes, and then I realised why I loved this style so much. My legs stretched, I could feel my calves become so obvious, my legs were literally showing off under my trousers. She giggled "Clearly you're enjoying it" and eyed at my crotch. "Fuck! sorry, I didn't mean to..." "relax!" she cut me off. this is flattering and surprisingly enjoyable. Not every day you get a guy who wants your clothing more than he wants your body".
"I like your mind as well as those other two" I blurted out. Then collapsed on the seat. "I know what we said, I'll head off, I appreciate you chatting with me but I don't want you feeling awkward" I said.
"You're not. This isn't what I expected when I slipped on those heels this morning to go to work and I'm glad you're not focused on fucking me with that bulge in your trousers but I think if you want to, we can relax and see what happens. completed no pressure".
"I'd like to enjoy this and not spoil it." I said. She smiled. "Don't over think it, let's enjoy this. Seeing you in my heels is doing weird things with my head". She wanted it too. I could tell. but I was about to blow my load and I didn't want to ruin even a one time fuck by being too quick.
"Here, stuff these in your bag for when you get back" she handed me the second pair of heels. "But you have to return them, and matching something more than your trousers. as stylish as that look is" she giggled.
I nodded. A girl had just given me her heels and told me to get dressed up for her. "I'll see you next week" she said at the door, then pecked my cheeky. "Bye".
"yea, next week. bye" I managed as I keep her gaze while I opened the close door behind me.
Back home I was dressed faster than I ever had been. I needed to spend the weekend trying different outfits. Of the very few I had. Had I made it sound like I had a full femme closet? I hope not.
I lay in bed with Imogen's heels, a new pair of the pants, and the satin camisole on. cock limp from cumming twice.
"Well that was an experience" I said to myself