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WHEN ANNIE MADE ME LUCY - PT. 01
STORY INFO
A sexy colleague finds my secret dressing desires.
5.7k words
4.7121.8k409
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LucyCanyon
LucyCanyon
43 Stories190 Followers
Part 1 -- A new friendship with a difference

Author's note: This was an offline role play between myself and the
delightfully sexy Lit member, who throughout the story will be called
Annie. She is no longer a regular on Literotica. We often spoke of
trying to turn our email fantasies into a story and its taken me a while
to do so. I have kept the format - a back and forth message-response
which we did for almost two years (and several stories and scenarios!)
It will take me a while to even get this story down, it will start slow
to build the scenario and characters, and I hope you enjoy it as much as
the lovely Annie and I did creating it.

Annie

I was watching you working away in our office in the city. You're doing
well and have made friends at work, including me. I am Annie, a buxom
manager of a development team but not yours. We've always seemed to have
a spark when we chatted but never acted on it. I know you have dated
other women but very recently your last girlfriend, Carla, broke up with
you after discovering your feminine clothes...

"Hi John, do you have a minute?" I lean by your desk wearing a low-cut
blouse, my favourite tight leather skirt, and my typical 4" heels. They
are all very tasteful so I don't violate any company norms but they do
push the boundaries a little bit. "I received a strange email yesterday
from Carla in acquisitions. Do you know anything about this?"

John

I was doing well at work and thought I had a good set of work
colleagues, some of whom I could call friends. I am not one of those who
use their position to predate on the women in the office, though I had a
few relationships with women who were not in my team. That would be too
close. Sadly the latest, Carla, has just decided I was persona non grata
when I thought we were really hitting it off. One of my interests
clearly wasn't for her and she made it very clear.

I had chatted with Annie many times, a very striking and attractive
woman who seemed to flirt just a little with me but never enough for me
to feel confident to follow it up. I found her very sexy, always on the
edge of our conservative clothes rules. Today she appeared and leaned
over, mentioning an email from Carla! Shit, I thought we parted friends
with differences.

"Hi Annie, not sure what that could be about, I never thought Carla was
strange... hope it didn't involve pillow secrets", I replied, trying to
look her in the eye and failing. "If it's work related perhaps we should
ensure we are private before talking about it"

Annie nodded but didn't move. "So it's true?" she asked me, clearly curious.

"Sorry? I'm not sure what she told you?" I responded, wondering what
Carla had said and why she would think of sharing something about us?
"Is this work related? I am a little busy so if it's personal perhaps we
could catch up at lunch?"

Annie

"Not really work-related, so yes, let's do lunch. I'll swing by around
11:30?"

I did just that, and we walked for a good 15 minutes away from the
office, passing typical places our co-workers would grab a bite from and
ended up at a small bistro. I suggested an out of the way table for us
as I knew what we were going to be talking about. We got our table
service and made our orders before things got down to conversation. At
first, I just talked about office gossip, definitely flirting a little
bit with salacious topics about other people.

John

As we walked to lunch I stole discreet glances at Annie. She was chatty
and smiling as we walked, and I hadn't really noticed her figure and
clothing choice... it really suited her and got my mind wandering.

As we sat in the bistro I realised I was rather enjoying the chat,
especially as she was sharing a few naughty items of office politics. I
relaxed, she was definitely flirting and I made sure she knew I was
enjoying that. I started to make it more obvious I found her attractive,
her leather skirt hugged her hips and ass in the most delightful way and
her blouse seemed to have another button open now. This conversation was
very definitely not work related and I had almost forgotten why we had
walked so far from our colleagues.

Our conversation went quiet while the waitress delivered the check,
which Annie took, slipping her card on it to pay.

"So, I have to ask... is what Carla said true? You want to be a woman?"
she said quietly.

Annie

I heard John draw a sharp breath in when I asked the question I had been
so interested in. Carla had shared that she and John had been getting on
fine but she discovered something she couldn't deal with.

"That's what she told you?" John smiled as he checked with me, but
inside I could see he was a little nervous. After all, we worked in the
same firm. "No, it's not true, I am very happy as a man... but... I do
like a little alternative clothing and Carla put two and two together
and made 5. Does that explain things?" he concluded, clearly trying to
move the topic on.

"Oh, that is, fascinating. I hope you feel comfortable enough with me as
a friend to tell me a little more of what you mean..."

John

Mmm, did I? My mind was in overdrive even if I tried to be calm. How
well do I know Annie? My interest is not understood by everyone and I
needed to know it won't be shared even more widely. We have got on well
of late and the lunch conversation was definitely a little more
personal... I took a breath and decided to share a little more with this
intriguing woman.

"Well, Annie, I would like to share my interest with someone, it's not
always welcome or understood.... and I don't want this known more
widely. You aren't worried or turned off by the idea of a man enjoying
wearing more feminine clothing?"

Annie

I tried not to show my real feelings about your reply but in truth I was
very interested and not at all worried..

"Friends keep each other's secrets, honey. So don't worry about that.
And I have to tell you that my next door neighbour growing up, Liam,
loved girly clothes. I discovered it when we were making out and I found
him wearing satin panties. I learned to really enjoy how sexy he looked
in them and lingerie is pretty erotic by itself. I loved dressing up
with him until we couldn't stand it and had some pretty hot fun together."

I paused and watched, satisfied to see you relaxing a little.

"And while we're sharing secrets, I'm bisexual so I think that makes a
guy who likes looking and acting like a girl especially erotic to me. So
I'd call us a couple of rare birds, but I'm glad we found each other."

John

Wow, that's a whole load of new, and frankly rather exciting
information. I studied Annie again as she stood smiling at me. I liked
what I saw, I hoped she did the same. I am very fit, slim to the point
of wiry which helps me no end when I am choosing my clothes in private,
but my shape as a male is not the typical macho man.

"Well, that puts a whole new light on it... and yes, I love wearing
feminine clothing but so many women don't understand. For me it's the
sensuality of the fabrics combined with the naughtiness of it being a
little taboo in our society. I have no interest in men, but sexy women
who actually might like to see me in feminine clothes... "

Annie barely hesitated. "Would you like to come to my home for the
weekend? I've already thought of a few games for us," she replied with a
mischievous smile.

I was stunned and went silent for a while as we walked back to work, but
then reached out to stroke the tight leather of her skirt as we stood
waiting for the lift.

"My instinct says yes... that would be amazing... even though I don't
know what the games would be! My reticence is natural I think, no woman
has encouraged this side of me. So... if I say yes can I make two
suggestions to start us off?"

Annie

"All ears, honey," I said with a smile. You can sense that I am truly
open and fascinated with you but recognise that I am as nervous as you.
I've played the bold statements but I do have my own worries... have I
crossed a line? Do I know where this is going? Do I want to get involved
with a sissy man when everything around me says no? I remember those
warm afternoons with Liam, our fingers tracing each other's bodies and
lingerie, kissing, fondling his cock in his satin panties, talking to
each other like we were girlfriends but also opening myself to him and
loving him inside me. I do want that again. I'm willing to take the
risk. All these thoughts go through my mind before I take your hand in
mine between us and listen for your suggestions...