When Annie made me Lucy - Pt. 01

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...

"Go on, sweetie, this sounds like we could be having fun soon".

John

For the first time I sensed a little nervousness in Annie, as if this was a step for her too and that relaxed me a little. I felt now I could go with this and see where it took us.

"Well, a couple of things I have always wanted to say, try, do... whatever..." I started, a little hesitant but getting more confident.

"I would like to be able to spend the weekend wearing only female attire when indoors at your place. No male clothes from when I change on Friday night to when I leave on Sunday unless we go out..." There, that really has told her I like feminine clothing! "And... no tights, hose or whatever they are called here. If either of us wear nylons then it's thigh highs or a garter belt."

I wondered if I could push for a third, but instead asked "Do you have any ground rules or shall I just pack what I have and meet you at yours after work on Friday?"

Annie

I smiled bigger as I listened to your ideas. This was going to be delicious!

"I agree... hate pantyhose. I only wear thigh highs because I love the way it makes me feel sexy every day," I bubble back happily.

"No ground rules, I guess. We can just take it slow and if either of us is uncomfortable with something, just say so. I think we can be great... friends and don't want anything to ruin that. So just bring what you have. We're basically a similar size so I should have lots of choices for you as well. I would like to go shopping with you Saturday if you're okay with that."

I watch your eyes and expression trying to see how much you want to just feel safe and how much you might enjoy testing the boundaries of your comfort zone. Liam got very aroused when we'd go shopping together. He seemed to crave being a little embarrassed if I told the salesgirl we were buying for him or even got him to use the dressing room in the lingerie store. I hope you're open to such things and would enjoy it as intensely as he did...

John

As Annie smiled and agreed with my suggestions I breathed out, and smiled back. This was sounding almost too good to be true. Here was a very sexy woman in a tight leather skirt (which my mind has already decided I want to try on) and a great figure, and who wants, no, desires to see me when dressed! The idea that I can just put on a skirt and flats and be relaxed as we spend time in her house sounds just what I want, though I already know we will be doing much, much more.

"Annie, that sounds just perfect, and you promise you won't laugh at me dressed?", I checked, that last remaining doubt in my mind. She shook her head and smiled again.

"Then its a deal, I am already looking forward to it... Friday night, your place and I will only pack femme and change as soon as I get to your place. Shopping Saturday sounds good though I will have to change back to drab - my term for male clothes - to go out!"

The choice was made, I could not wait for Friday night!

Annie

The next two days dragged on like torture, the heaven of our special weekend just out of reach like an oasis. I could see that for you it was distracting, and I felt more comfortable about the risk I had taken in talking to you about it, about my own experience and desire. We both persevere and finally get away from work Friday afternoon, leaving you time to pack and prepare yourself.

John

Through the week Annie and I found occasions to be close and almost alone and I snuck the occasional stroke of an arm and her fantastic ass in one of her tight skirts, feeling the top of her stockings through the tight fabric. Finally I left work early on Friday and went to collect my small weekend bag. I knew what I wanted to wear when I got changed, nervous though I was.

Annie greeted me with a long hug and steamy kiss, our first and the promise of something more to come. I broke it off and slightly shyly asked where I could change. Annie smiled and showed me to a bedroom, and said to come for a drink when I was ready.

This was it, someone positively waiting for me to be dressed. I changed quickly having showered earlier and shaved smooth all over. I slipped on silky feel black panties and opened a new pair of sheer, barely black thigh highs, the feel as their fine fabric encased my legs was delicious. A fine lacy camisole under a simple white feminine t-shirt and a short, black skirt that swirled around a little, the brushing against my stockings making me shiver. Finally my patent black 4 inch strappy heels. Ready...

I walked out, nervously, and went into the kitchen area where Annie was waiting, looking stunning and sexy. Did I?

"Hi... erm... will this do??"

Annie

I look you up and down with a wide, warm smile. Walking up to you, I motion you to turn around slowly. I lift your skirt to examine your stockings and panties, reaching a hand out to cup the front of your panties and see if you're aroused... and smile again. Delicious, so much potential already.

John

Annie smiled and I relaxed, this was going to be ok. I turned around for her and she lifted my skirt, my skirt... how nice does that sound?

Her hand stroked around my panties and slowly caressed me... and the sensual feel of her light touch through the silky material made an already arousing experience even more so. I think the nerves had kept me from showing any excitement even though the outfit always aroused me when I wore it... but the touch, mmmm.

I reached out to pull Annie towards me for a kiss, her lips looked so inviting and welcoming. As we hugged my hands roamed down her back to her tight skirt, wanting to find out if she too was wearing stockings...

Annie

I enjoy our kiss, at last after weeks of flirting. I try to lead you, show you how a woman kisses, more sensual, less urgent... so far. When you try to pull up my tight leather skirt, I smile and step back.

"Eager, eager, aren't we!" I say with a wink. "I have some ideas for this weekend that I wanted to see what you thought of them," I explain, holding your hand as I lead you into the kitchen where the wine is waiting.

"We have a private backyard so I thought we might want to put on our bikinis and sun bathe together. Of course, you can wear one of my bikinis if you need to. Or take a dip in our pool together. There are some sales at some of my favourite stores tomorrow so I thought we'd go shopping together. I'm pretty sure that you'd like to explore my wardrobe. Girlfriends share clothes so you can wear anything in there that you like."

You smiled wide at that, and my guess was right - you have been looking at my skirt all week!

" I even have some things way in the back I've kept from my time in high school with my next door neighbour. He got into some wonderfully kinky and fetishy stuff that I got to see before he stopped coming home from college. And of course, we can do each other's nails and makeup."

I pause to enjoy the feel of your erect cock through your panties and skirt after my last sentence. "And I'm sure we'll find plenty of time to explore this many, many times..."

John

Annie's words were just what I needed to hear, though I was really enjoying the feel of her body too. As she passed me some wine she stroked my cock through my skirt, a sensation I never thought I would feel.

She was offering me a chance to dress in different clothes, her clothes! She really wanted this, and I was excited to explore with her. There was a niggling doubt as her words sunk in... nails and makeup? I remember clearly saying that Clara was wrong, I didn't want to be a woman, and I thought Annie understood? Still, I was sure that was just an idea I could deal with later. My cock grew under her attentions as she continued to stroke it through the sensual fabrics.

"I am very eager to see and feel the same clothes and fabrics on you as you feel on me, I find your mind and your body a perfect arousing combination", as I drew her in again. I felt her firm, full breasts push against me as I stroked her ass again, this time allowed to knead her flesh through her skirt. "If you are going to have fun with what's in my panties I am going to try to have as much fun with what's in yours."

Annie

"My turn first," I grin, my eyes flashing with lust when we finally break our groping embrace. I unzip my skirt and let it fall off, stepping out of it in my thigh highs and heels. I caress your body through the women's clothing and sink to my knees. My fingers run up and down your calves and thighs, moving closer and closer to your panties. I bunch up your skirt to your waist, fully revealing your panties and your throbbing erection tenting them.

Leaning in, I begin to nuzzle your satiny bulge with my nose, cheek, and lips. I glance up at your face to make sure you are fully focused. My fingers run across the panty material, brushing your cock and moving around to squeeze and grope your ass in the panties. Finally, I peel them down just enough to tuck under your balls, displaying your full cock glory!

John

Annie slipped her skirt off and revealed gorgeous legs in her thigh highs and barely there panties... I couldn't tell what was hidden away but I was hoping to find out. Right now I felt the most amazing sensations as a stunning sexy woman played with me in my feminine clothing, immediately sending electric shocks to my cock in its silky black thong style panties. I was bulging, her hands and lips driving me wild as she teased and sucked and nibbled, finally releasing me.

My smooth shaven cock and balls were on display and I was so aroused, Annie kneeling in front of me in my heels, her own sexy body making me more aroused than ever. I am no judge of cocks, but friends with benefits have described mine as a little above average length and a perfect girth... well, Annie was about to find out as the 7+ inches was revealed, clearly I was aroused as the small pearl of precum showed.

I stroked her hair as she stroked my legs and licked her lips. All pretence of getting to know each other slowly now gone, I felt I was almost her lesbian plaything with a real cock

Annie

My first kisses were like whispers of breath, then teases of my tongue as I got more and more intimate with your cock. It was large in my experience but if I wanted to go porn star on you I might achieve it. As my mouth, my soft moans and my breath caressed your cock and balls all over, my hands wandered up to your ass. I worked your ass in a very specific way, enjoying the way your thong would tug this way and that, waist band stretched down across your hips to reach under your balls. I squeeze and caress your ass cheeks and spread them eagerly making you feel remarkably exposed, open to my desires. When my fingers gently caress your asshole, you gasp and I feel your cock swell in my mouth. I moan and smile. We'll be having a lot of fun as girlfriends.

Holding on to your ass I refocus on the blowjob, getting more serious and firmer. My free hand grasps your shaft and begins to jerk you up and down as my mouth sucks and tongues your tasty head. The stream of precum is delicious and I'm impatient to taste your true cum. My own panties are wet, arousing me for the playtimes to come later. I want to indulge myself by making you cum and also to calm your arousal a bit while we play dress up.

Pulling out my trump card, I look up and lock gazes with you as your hips start to thrust in and out, your cock plunging in and out of my mouth and teasing my throat. My mouth is a firm, tight, wet round hole which feels amazing on your flesh, urging you to let go, to explode, to fill my mouth with cum.