When Annie made Me Lucy Pt. 02

Part 2 - A friendship develops further

Authors note: This is best read in the right order, Annie and John (ie me!) have met at work and found we both share the pleasure of sex in lingerie, something John was wary to tell Annie. Having gone to spend the weekend at Annie's and dress fully in front of a woman for the first time the story starts again after the two have just come down from their first orgasms.

Annie

As I recovered slowly from the pleasures your amazing tongue gave me, I watched you opening my blouse and saw the desire and glee on your face. We were really a matched pair and I could not stop smiling at what luck.

"Well, we have time for all that but I thought I'd let you explore my wardrobe and play dress-up for me this evening. Tomorrow morning, we will get cleaned up and make sure we're properly shaved because we have some appointments." I left it mysterious and lay back, leaving myself open to your exploration. After a very short while I sat up to lose my blouse and later my bra.

I also make sure this is mutual so I stop you from time to time, nudging you to lay back, stripping you down to stockings, panties, and camisole, and exploring your sensitive skin, nipples, and lips.

"First," I say as you suckle my right breast eagerly, "we need to eat." I realise that much more attention from you would make me demand more orgasms and the way your cock is tenting your panties again, I know you're recharged but we can let our anticipation build. "I'd like to go out to eat but I can save that for tomorrow night. I know you're enjoying being dressed here in my home."

Finally, I move you from fondling me and get up from the bed. You watch as I re-dress and I see the love in your eyes, love of femininity and perhaps for each other someday. "Dinner will be ready soon so when you're put together, come down. Take your time, use whatever you need from my rooms."

John

As Annie came down from her high we spoke quietly about plans she had for eating out and a secret trip that we both had to be totally smooth for. I love the feeling of smooth moisturised flesh, mine or hers, so I was relaxed about what that would mean. I explored her breasts gently, stroking lightly around their firm fullness and pulling occasionally at her hardening nipple before I got my first taste of her delicious bud. Annie stripped me of my skirt and blouse and treated me to some arousing foreplay of her own and it was clear from the growing bulge in my panties that I was getting hard and recharged again, but Annie had different ideas. Leaving me with instructions to help myself she quickly slipped on her skirt and blouse and went to start dinner.

Her wardrobe and drawers were amazing, such sexy clothes in them as well as ones I had seen her in at work, less obviously sexy but smart and hinting at the character of their owner. Where to start? I stroked the sensual fabrics seeking something to enjoy wearing, the arousal all the more for me because I would be wearing her clothes not mine, and with her encouragement - such a turn on. At the back of one closet were some more interesting items - almost fetishwear - which I noted and felt I might return to another time. A couple of drawers I opened had some interesting items too... and confirmed my thinking that Annie is a kinky lady right along my lines and I was more aroused than ever.

I took off my remaining clothes, determined to enjoy the first of what I hoped would be many outfits I could wear for Annie from her own wardrobe. I selected a black a satin thong I felt would hold my growing bulge and would match the one item of my own - my bra, as my forms were not the size of Annie's magnificent orbs. I selected a deep red garter belt and slipped it on, threading the straps under the waistband of the panties, and then picked out sheer black seamed stockings. I must ask Annie where she gets these from, they feel soooo nice! I had that red dress in mind, and it was soooo tight, sheer, slinky, it clung to even my limited curves as I pulled it on. The material rubbing against my stockings as I walked around felt amazing, and I discovered my feet, small for a tall male, were able to slip into a pair of stiletto open-toed sandals. I looked in the mirror, and from the neck down was a very slim and sexy looking figure, though my face was clearly male... I hoped Annie would be fine with this as I walked back into the kitchen and shyly said, "Hi, I hope I do this justice.."

Annie

Your words are barely out of your mouth when you realise it is not me you are looking at. A buxom young woman in an elaborate satin French Maid's uniform is busily putting the finishing touches on a dinner that smells heavenly. She smiles widely and warmly at your appearance.

"Bonjour, Madame! Mistress Annie awaits you in the dining room. I will serve dinner in moments. Please have a seat."

Peering past this lovely bouncing confection of a girl, you can see into the dining room where I am sitting with a glass of wine, motioning you to come join me.

John

I stare, probably a little rudely, at the bouncing vision who just welcomed me. Annie never mentioned she had a maid, though the outfit once I looked at it closely was a little more showy than perhaps it needed to be. I blushed, caught very obviously a man enjoying his feminine side but she smiled and I could see Annie beckoning me through.

My brain slowly processed this more as my heels made that oh so sexy sound across her kitchen floor... Mistress Annie? Bonjour Madame?

I reached Annie who was smiling and opening her arms to give me a hug and we kissed again. Then she stood back and let out a low whistle, suggesting that I had selected well.

"Annie, darling Annie, what is going on? I am slightly embarrassed as I only just got used to you finding me attractive in these delicious clothes... having another woman see me now... I am a little on edge!"

Annie

"Calm yourself, my dear," I say, giving you another intimate hug. "Marie is a special friend of mine. I thought it would be nice if we got a little pampering this weekend, a complete girl's weekend. If you're too uncomfortable, I can ask her to leave."

At that moment, Marie entered with a large tray of dinnerware. Smells of a delicious meal wafted past as she brushed past you to put the tray down and put the food at our place settings. In doing so, she gives you a beautiful long look down her cleavage nestled in the low cut satin dress.

"Thank you, Marie," I say, giving her a quick kiss and holding her hand a moment, our fingers entwined.

John

Annie reassured me as the maid, who she called Marie, brings in delicious smelling food. The more I see the more I realise Marie is not really wearing a straight maids costume, the view down her stunning cleavage as she passed by was surely deliberate, the outfit now seeming to display rather than hide her enviable assets.

"Pampering? Mm, I like the sound of that, would you care to tell me more over dinner?", I said, deciding that I just had to go along and see what Annie's plans were. I saw the kiss, the slightly longer than necessary hand holding and recalled Annie telling me she was bisexual... mmm, I seem to have found a soulmate in sensual fantasy land!

"Marie, a lovely name, does Mistress allow you to dine with us?"

Annie

"If she so desired, but I understand this evening and weekend are for you two to be together so I should not intrude," says Marie demurely. With every movement, every smile, every swish of her dress, you feel what a nubile and sexual being Marie is.

"She might join us later, Lucy," I tempt you, giving you a perfect girly name to see how you respond. "We'll see."

Dinner begins and Marie stays in the kitchen unless changing the courses of the delicious meal.

"I want us to have a beautiful girlfriends weekend, Lucy. Having someone cook and serve us is just part of that plan but we don't have to worry about anything mundane this weekend. We are free to be ourselves and I must say you chose a very hot outfit tonight. Did you want to go clubbing together?" I tease. The thought of going out in public as a woman is both arousing and terrifying and you blush. "It wouldn't be that hard, really... to get you to pass. The right makeup, maybe a choker, the perfect wig... the rest is attitude... learning how to walk like a woman, owning your curves, how to sit properly, how to dance... there are many things I could teach you that you missed not growing up a girl. The deeper you feel in the feminine, the more comfortable you are as your female self, your desires will intensify and you'll want to do everything girls do." I let that last comment hang in the air as Marie brought in dessert. I look at you as we nibble, watching your reaction and if you have anything to say.

Lucy

Dinner is delicious, as is Marie, the potential for her to join us clearly there if we want. She is different to Annie, sexual in a different way and I can see why she would be attracted to Marie.

As we dine I hear Annie explain how we can be girlfriends this weekend... and I take a while to process what she called me, and is saying and hinting at. I think on the name and realise it helps me relax more into my feminine clothing. I am loving the sensations of the dress, the garter belt tugging at the sheer stockings but...

"Clubbing? Haha, nice try but I don't think even in male mode I make a good club goer"... and even as I say this I am blushing. "Annie, I am loving the relaxed nature of our time, the choice of dress up clothes... the sex, god your pussy tastes so amazing I just can't wait... but I don't think I can pretend to be a woman... really? Do you think I could pass outside your house?"

Even asking that question opened the door I guess, it was intriguing to think maybe I could fool some people, but there were hints from Annie that sounded a little too far?

"Shall we see how much fun we can have tonight and how smooth we can be for tomorrow, you haven't told me why yet??"

Annie

"I have a few surprises in store, darling, don't you worry."

I turn to Marie. "Thank you, dearest. It was delicious as always! We'll have to all find a way to work off those calories, hee hee." I give Marie a tender kiss and then take your hand as she begins to clean up the dinner dishes. My free hand grabs a bottle of wine and two glasses.

"I want a fashion show and you are going to be my model! Come with me," I say happily, leading you back upstairs to my bedroom. Once there you see that someone has laid out several outfits on the bed complete with underwear and shoes.

I step up close to you, giving you a hug and then slowly helping strip you naked. "I want a good show so tell me how they make you feel as you're putting on my clothes..."

I tuck my feet under me as I take a seat in a plush seat with a full view of the room. The first ensemble appears to be a little black dress, black thigh high stockings, a black satin garter belt, black satin bustier with c-cup inserts inside, and a black satin thong. A pair of 4" ankle-strap stiletto heels sit with the clothes and you notice that the heels have a place where little locks hang. If they were to be closed when you put the heels on you wouldn't be able to take them off

Lucy

As Annie slowly strips me of her own dress and garter belt, sliding stockings down my legs and removing my panties I cannot help but become a little aroused, my cock engorging and rising as the full impact of the next outfit hits me. Annie seats herself in the best seat to view... well, I did want to spend the weekend en femme...

I start with the garter belt, noting it's six straps so a proper belt and not just for show. The satin feels nice against my skin but as I slide the sheer black stockings on Annie raises an eyebrow as she sips her drink.

"Such a sexy feeling, I love the feel of sheer quality nylons as they enclose around my legs," I say as I attach the straps to the top of each stocking, framing my now almost erect cock. "Knowing they are yours and you are watching me put them on really arouses me and even more that you chose them"

I add the bustier with it's fitted forms and twist it around before slipping the straps over my shoulders.

"Oh my, this feels sooo nice, very full breasted and more than I am used to but it feels so good to have the weight and feel of these boobs. And feeling slightly more enclosed than a bra, very feminine, am loving this.."

The satin thong slides over my stockings and barely covers my erect cock... a lewd bulging pouch of silky feeling material on my hairless balls. The dress is short!

"Wow, this is short on me, you can almost see the garter straps if I even as much lean slightly," I say and I reach to zip myself in. "Fuck, Annie, these feel amazingly erotic to wear, I don't know I look to you but looking down at my figure, wow!"

Finally the heels... I slip them on and note the locks that are clearly there to make the wearer keep them on. Standing up I walk around, parading in front of a sexy woman who smiles at me and offers me my glass.

"Gorgeous, daring and... why would you have locks on your shoes Annie??"

Annie

"I've had very close friends before like you who sometimes would enjoy the feeling of being feminised and trapped, out of control. I have lockable dresses, high heels, teddies and of course the play time restraints all can be locked." I get up and walk around you, straightening the dress a little there, adjusting a stocking so the seam is perfectly straight. "Don't these silk stockings feel amazing?" I let my fingers dance against your throbbing, panty-covered cost until you gasp and then step back.

"Lucy, do you trust me? You can say no and I won't be offended but I would like to take boudoir photos of you. Maybe after we do your make-up and pick out a wig? What do you think?"

Lucy

The sensations coursing through me were electric as Annie played with me, straightening and primping until she was satisfied. So, she has played before, that was what she said anyway, but they liked to have the choice taken away? Mm, sounds a little scary but there was no denying her words sent a twitch to the bulge in the tight black dress that Annie was lightly stroking.

Then she asked about pictures, fully feminine pictures.

To give me time to process and think carefully about my reply I leaned forward and kissed her gorgeous lips again. She melted in towards me, I felt the bulge of my cock press against her through our sexy fabrics as our tongues twirled and danced in each other's mouths. My hands stroked and kneaded her ass cheeks as she ground her pussy towards my bulge. I was getting really hard again, her body and her suggestions, her clothes, even her maid are all combining to overload my senses and I was loving it.

I break the kiss and stroke Annie's hair as I frame my reply.

"Annie, you are the sexiest woman I have ever met, and you are testing, nicely, my boundaries. In femme mode I guess I am lesbian, I do still only love a good pussy and sexy figure... but..."

I paused, and decided to be straight with her.

"I trust you... and I hope you trust me. I will try to be fully transformed and have the pictures taken but I'd like to ask a couple of things?"

Annie nodded and smiled, encouraging me as she stroked my ass through the sexy short dress before sliding her hands under..

"I would like to turn the tables at some point, I saw your playthings and your position as I tasted you and I think there is an Annie that likes to let go too... and I want to play with her as well. And, whilst I will try anything femme you ask of me... ", I paused, "please understand I really don't want to pick up or do anything with a man. If I can have a safe word of amber to slow down or red to stop... then let's have some fun"

Annie

"That makes perfect sense, Lucy. Trust me, I wouldn't bring a man into our new world unless you asked me to. There are plenty of ways to get the cock experience that most women crave," I say with the grin of a deliciously held secret. "Now to your other request... I think this is becoming something where we might go there. To be honest we need to go a bit further before I can agree to it.".

The way you are kneading my ass is definitely having an effect on me. You see my eyes get half-glazed for a few moments as I moan.

Finally I pull back leaving you with a blistering kiss. "Okay, we need to find you a wig and do your makeup!". I lead you to a shelf in my closet where I have several wigs on display heads. "See one you like?"

Lucy

Annie's final kiss left me wanting more, her words reassuring and holding out the promise of a little switching occasionally. For now that made sense, she was leading me into a world she clearly had some experience of, and liked a lot. Our embrace had got me hard again, the bulge a little visible in the tight short black dress she had chosen for my first outfit of the night... first, fuck, that was such a sexy thought now.

As she opened the closet and asked me to select from a variety of wigs, talking about make-up I was taken aback... thought my cock belied my reticence as it twitched when I saw the collection. I shivered a little, this was happening. I had never pushed for this, but Annie was taking me, carefully and sexily, further than I had been before... what did she mean about ways to get a cock experience??

"I think a shorter, bob style would suit my frame best", I hear myself saying as I feel Annie stroking my ass and playing with my garter straps as I survey the choices. "Perhaps this one, do you think its sexy??," I said, choosing a scruffy blond bob. I realised I was feeling aroused and comfortable in her presence now and sure that we would be fine, I could relax and let her see if she could transform me.

Annie

"Ooo, so cute! I love it! Hold still."

You close your eyes as I work with your hair, working the wig, clipping it carefully, adjusting it and then kissing you.

"Eyes open!"

You look, see yourself in the mirror and for a moment, see a woman. Your hand moves to touch the hair, draw it from your face in a perfectly feminine gesture.

Lucy

I do as I am told and close my eyes, feeling Annie place the wig on my head. I stroke her smooth nylon covered legs as she makes adjustments and then..

Fuck, that's scary. It's me, I know my face hasn't been changed, yet, but... with the first outfit Annie selected and the wig there is no doubt that I look, well, almost like a woman. Even as I touch my new hair I see Annie smiling at me and the gesture I just made. My cock has responded and is filling the satin thong she chose for me as I stand up and reach again for her.

The kiss is sensual, gentle, her hands roam my dress covered body as mine stroke and knead her ass cheeks again and then hold her head as the kiss becomes deeper. Breaking away, slightly dazed, I nod, smile and say, "Never would have believed it... you better finish the job.."

Annie

"Of course, my lesbian lover..." I breathe after our kiss breaks. My body wanted to melt into yours and grind against your hardness but I forced myself to be patient. This was certainly a little different. Before, my sissy friends were very submissive, almost apologetic for having a cock, 100% focused on being feminine. With you, I could feel that animal lust lurking beneath the dress-up play. I wondered which would win out... and if you could be one without giving up the other...

I sit you down at my personal vanity, put a towel over your shoulders and get to work. I'd learned several tricks interning as a make-up artist for a local film production company a few summers ago so felt very confident that you would be amazed. I covered the mirror to let you be surprised. Slowly, each touch, each oil, or cream or powder came to your face and you closed your eyes, enjoying the feel of my fingers and the make-up tools. It seemed to take a long time which made you chuckle, thinking how long it has taken girlfriends of yours to "get ready to go" and now you understand a little better.