When Annie made Me Lucy Pt. 03

I join you in the shower and move your hands away and take the barely there costume off. This time I wash you, gently, not with the intention to arouse as I sense its time to be calmer, but I cannot deny how sexy it feels for my soapy hands to glide over your body. Soaping your breasts, lifting, testing them, easing my hands to rub your cheeks, down your legs and finally up and between to lightly clean around and above your still puffy and engorged labia. My cock is clearly standing proud inside my costume which I slip off at last, glancing reluctantly at another new sensational outfit you have shared with me. As we towel off you lead me back to your room where we will spend the night.

"What shall we sleep in?" I ask tentatively, hoping to try another new item of your out

Annie

I look you up and down, tapping my chin. I go to one of my two chests of drawers, open it, and lift out a blue-green satin chemise and pair of matching hi-cut panties. I put the panties on you, tucking your cock down inside the clingy elastic waist. Then I slide the chemise over your head, letting you shift around to get it to slide past your breasts until it is in position. Glancing in the full length mirror, you are struck by how the chemise is perfectly designed to snugly hug your breasts and body, though a little loose where my hips are more curvaceous than yours. The satin hugs your body the way no male clothes ever would and your skin is still so sensitive it feels amazingly feminine.

Returning to my drawers, I pull out a red satin teddy, step into it and slide it up my body. I draw it up over my breasts as I put my arms through the shoulder straps. I turn out all the lights except one by the bed side. "Will you sleep in my bed with me, girlfriend?" I ask as I move on to the bed.

Lucy

As I am beginning to learn, your choice of outfit for me from your sensual collection is perfect. The feeling of the satin enclosing my cock is gorgeous, so light and yet so arousing. The camisole is filled by my breasts... and as I think that I realise I am thinking a little more femme as I stay in this mode longer. I wanted a weekend where I could dress how I liked -- and I can see that will be the case all weekend now -- but I wasn't expecting a weekend where I felt the femme side of me come out so much.

Your teddy looks divine on you, and I know we already know each other's bodies well enough by now, but the way it hugs and clings and shows off your sexy curves still sets my pulse racing.

"I would love to sleep with you, Annie, my new lesbian lover. I asked to be allowed to dress, but you are really making this a little bit more than a weekend to satisfy my own desires... you are teaching me new ones!"

I join you in bed, and roll close, revelling in the sensual nature of our satin enclosed bodies lying against one another. Gently stroking your body, I move my hands lightly over the satin fabric, enjoying its feel under my fingertips but avoiding your more erogenous zones.

"Annie, thank you, this has been a more enjoyable evening than I could ever have expected or dreamt of. All I desired was to feel comfortable in my feminine clothing and you have done that, but oh so much more. I am deeply grateful, and though I am nervous about 'being Lucy' all weekend I think with your help I could get to really enjoy this. So... thank you, I want to take over our play when I am more confident that I know what you like but for now... what plans have you made for you and your girlfriend tomorrow?"

Annie

"I think if you're confident enough, you and I will go out and do a little shopping. I have an appointment for us at my nail salon for a mani-pedi. Grab a light lunch and see how much you enjoy the world of a beautiful woman. But that's for tomorrow..." I kiss your lips tenderly and you realise that I've put in all of this thought, planning, and energy for more than just the obvious thrills. You realise that I've developed feelings for you which are blooming this weekend.

I turn out the light leaving only a very faint glow from my bathroom. I draw the covers up for us and snuggle back into your body to spoon, smiling to myself as your arm slips easily around my waist and your cock stiffens up the crack of my ass like a trooper. I'll definitely be testing your stamina tomorrow...

Lucy

Your words, your thoughts, your actions and planning for our time together have overwhelmed me, and I realise that whilst you have drawn me further into the femme side than I had previously been interested in its had the effect of you feeling ever more close to me. I snuggle around your sexy form, cock growing unbelievably again even after all our play, as the satin nightwear settles around it and it fits nicely in between your fantastic ass cheeks. I feel my breasts press gently into your back -- my breasts, did I just think that?? Mmm, my hand plays almost unconsciously with your nipple as I drift off, contemplating and surprisingly unconcerned about your words for our outside trips the following day.

I wake up first and remember instantly all that we did yesterday, reaching for my new hair, stroking my breasts through the satin cami and realising how nice and different and undeniably sexy this all was. Your breathing is calm and steady so I rise quietly and slip away. This was what I had never had, wandering freely in sexy feminine clothes, not worrying, feeling comfortable and not for it always to be sexy but for it just to be... I slip on a pair of low heels and wrap around skirt on and go find coffee. I want to wake my girlfriend... yes, we each have a girlfriend it seems! ... and plan our day.

Returning with fresh coffee, revelling in being femme I slide next to you, slip my hands around to slowly tease a nipple and lean in. My semi-hard cock feels good inside my satin shorts under my skirt and I whisper, "Mmm, girlfriend, I hope you slept well. I cannot believe how well I did sleep too, and I want you to know that your girlfriend is entirely in your hands today.... though I might take you in my hands tomorrow if I still have stamina."

Annie

My eyes flutter open and I smile easily as I roll over against you and look in your face. My fingers caress your cheek, your lips, your neck. "Good morning, my sweet girlfriend. You look fresh and beautiful. Ah coffee!"

We spend the morning getting cleaned up, talking about our lives, our families, our past and leave fields of possibility for our future. I gently quiz you about times before this weekend that you have felt feminine, the desire to be pretty, the need to put on women's clothing. If you do not wish to speak of it, I will leave it be but I want you to know you are safe with me.

"I've seen the look in your eyes, the wonder, the joy, and yes, the powerful arousal. I can't help but think about the possibilities. There is so much about the feminine you have yet to experience. In my dreams my first date was another girl, my first love, Sara. I dreamt of our dresses, dancing with her, kissing her, going to a hotel together."

"I've had male lovers. And loved them. I have lost myself to lust after cocks and also for pussies, if I might be so crude. This experience, this weekend... I see as a journey for you, one that can take you quite far or be a trivial sex game. You may not have any answers or thoughts of this yet, but think on it. I'm ready if you ever want to talk."

Lucy

I enjoy our morning, just being in female clothes - simple skirt and blouse, shapely ballet flats, my new boobs giving me a shapely but still slim figure. You talk of your first loves and I am intrigued. You have a wider experience than me and your language doesn't offend, if anything talk of pussies and tits and more has an effect inside my satin panties that is barely hidden by the flowing but short skirt. I tell you of some of my female loves including Carla, whose off the cuff comment to you has got us here. If she only knew what she was missing.

"One old school friend was hugely supportive of me experimenting and was for a while a friend with benefits. We were both in relationships that were not quite scratching the itch and we had not seen each other for a while. Sex with her, in her clothes, was my fantasy and we nearly made it. She sent me her skirts and panties, a cami or two and even a dress. I shared pics and we came together online a few times but we never quite hooked up. She got that I liked the sensations, she too was into sensual feelings and had bi tendencies, I know she has since had her first play... but she is a little far away. I will tell her all about this... names changed to protect you of course, but she will be so excited for me!"

"This experience... is new and I don't know what it means. I do know I trust you and find myself hugely attracted to both your mind and your body... a powerful arousal!! I am enjoying looking and feeling feminine more than I expected to, it's never been about being a passable female in public... but now I am intrigued after last night... can I really go out as a woman??"

I look across, I want to know more about Sara, and about what you are seeking, what from all your experiences you are aiming for, but for now I want to feel nice and sexy and... I oh so hope I am going to be able to make love.. fuck... you again

Annie

"From the first time I met you, I saw that you had... ambiguous features, with the right treatment, the right wig, makeup... yes, you could easily pass for a woman and will today," I say proudly.

I help you pick out a purse and put a few necessities in it. We each give Maria a chaste kiss and head out for our afternoon of fun. Head to toe, you feel completely feminine, with the exception of your beautiful cock which seems to have a hard time staying soft. I pull the car into a dark part of the mall's parking garage where no one is likely to notice us.

"We need to settle you down, girlfriend," I purr before kissing you. I hike your skirt and release your cock from your panties. I take my own panties off with some difficulty in the car but then move over to straddle your lap. "I want you to fuck me, girlfriend..." I sink down slowly on your cock, sighing as your thickness spreads my slick folds and pushes inside me. Your cock is enveloped in hot, wet, slick sensations. Knowing you can't move much in the car seat I start to ride you, up and down, enjoying every movement of your cock. It slips out once but you guide it with your hand and I resume the grinding fuck. I don't kiss you knowing we would mess both of our makeup so our eyes are locked as we fuck. Looking down our union is hidden by our bunched up skirts but the simple act of looking past your breasts thrills you with your feminine body...

Lucy

I am finally outside as Lucy, and driving to the mall with you feels both sexy and scary. I know you are comfortable that I can pass and we will be fine, but I am nervous, and touch my hair and stroke my skirt down into place as we drive. I am not surprised by your words, nor our parking space though. IwWas thinking it was more for my benefit of those first steps...

Fuck.. that feels soooo good as you slide slowly onto me, I can barely move and let you ride my stiff cock as each downward slide gets me deeper inside you. I manage to thrust very slightly as you reach the bottom of your descent onto me, driving my cock deeper and deeper until our 'pussies' are grinding against each other and I am fully inside your hot wet pussy. I cannot see the exciting view of my flesh disappearing relentlessly inside you, but when I look down and back up I see two women having sex,. I reach to turn the rear view mirror and confirm that we are two made up, sexy ladies. skirts covering the union of our pussies, our sex.

The slippery nature of your wet, slick pussy is getting too much but I know this was your intent. Not wanting to smear our makeup I look you directly in the eye as you grind down on my cock. Your lips are parted, you are turned on.. how close to cumming? I can't yet tell with you (but I am going to learn...), but you know I am.

"Annie, this is sooo good, but you are going to get a pussy full of my cum soon, is that where you want it?"

Annie

I don't reply right away, holding your eyes with mine as we grind and I work my pussy to grip and stroke your firm shaft inside me. My face and neck are flush, my lips parted as I devour every sensation, every pleasurable nerve ending.

"This time... fill... my pussy... with your cream..."

With that I start grinding faster on you and pulling your cock inside me. I lean forward, my lips by your ear. "Fuck me... cum in me.. I'm.. I'm almost...I'm cumming!"

I didn't need to tell you as you feel my pussy spasm and clamp down on your rigid cock flesh over and over as my waves erupt across my body. Your cum boils up and within a moment, your cock is spraying thick hot cum all inside me. We groan and shake and tremble together in the thoughtless bliss of orgasm for almost a minute before my body falls back, limp to rest with your shaft buried in me. I'm breathing hard and a little sweaty on my neck. I hum with satisfaction as I shift around on your fading cock, feeling your admirable load inside me.

Finally, I remove myself from your lap and put my satin panties back on, knowing they will become stained with your cum soon but better to stay neat. Maybe I'll make you wear them later... It is only at that moment that you glance outside the car and see that three college boys were watching us. They are standing about forty feet away, leaning back against a car, and smiling big grins. One adjusts his cock making it plain to you that they all got quite erect watching us 'lesbians'.

"Sort yourself and then we'll get to some shopping," I say happily, taking the rearview mirror to check my makeup.

Lucy

Your grinding movements, the situation, the whole scenario of 'lesbian sex' in the quiet car park gets me close so quickly, and as we both reach our climax I thrust upwards into you, as limited as my movement is, it's the reaction to the boiling, spurting, pulsing orgasm I have. I know it's a huge load as you milk me, and I lean against you and breathe deeply, whispering a thank you and a promise to fill more and different places later.

The sight of the boys is funny, and I catch your eye and ask you to fix my makeup as well. You touch up my eyes and lips, fondling my breasts with one hand as your other strokes my hair. Getting daintily out of the car I see you smile over at them before taking my hand and setting off for the mall. I try to remember how to walk in my best but not over the top female style, reveling in the feel of the fresh air under my skirt, the click of my low heels as we walk in time into the busy mall. I stop, suddenly nervous, but you squeeze my hand in reassurance, briefly peck me on my cheek in full view of the passing shoppers, and we walk on. You mentioned a pedi and mani, and I see we are heading there first.

My cock has shrunk and is discretely back inside the luscious satin panties we agreed on, but I suddenly realise your panties will be starting to get a little damper as my very full load is worked out of your pussy by our walk. I had forgotten you had chosen a shorter skirt and am already a mix of aroused and nervous about what the ladies at the salon will see when we take our seats. That thought alone gives my cock a little twitch inside its sexy satin confines...