When Annie made Me Lucy Pt. 03

A calming swim and a first public outing

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.

Note - this will always be a story back and forth. Its annoyed some readers, sorry about that but its what it was and it would not do justice to my lovely co-writer to try to only give this from one perspective. If that isn't for you... pass on by.

Lucy

I finally slow my thrusting, feeling the aftershocks and tremors of you as we lay entwined, our kissing so much more soft and loving. Even though you sucked my first cum out of me only a few hours earlier there was a lot of cum saved for my second, your pussy is filled and as my softening cock slips out I cover you to hold it back a little and get your satin panties even messier and wetter than before.

Marie looks like the cat got the milk, and you promise she can join us... us? Mmm, I realise that I will not be in my own room tonight but with you... and now possibly Marie, so maybe sleep will be hard to come by. You ask if we should swim?

"Annie, that would be a lovely idea but for two slight problems," I whisper, all the time gently caressing your back and face as we lie together in our dishevelled lingerie. I see you raise an eyebrow, so I carry on, "well.... there is an awful lot of bodily juices drying on me and you and more still to find their way out... and, I did say I wanted to not have to wear male clothes and have no swimming trunks."

Annie

I smile at your faux protest. "You have all the choice in the world, sweet girl. I have several risque one piece suits and many bikinis. And if you're up for it, I could give you an... upgrade..." I say, playing with your inserted breasts in your satin bra. "And a quick shower will take care of the mess. You could even use my personal hair removal gel if you have any spots to make sure are perfectly smooth..."

With that, I give you a kiss and get up from the bed. I strip off all my clothes, handing them to Marie to be laundered, and sashay into the bathroom, knowing you're looking at my ass. Soon you hear the shower water running.

Lucy

I knew you wouldn't take my protests seriously and it's already late so no one will see me. Besides, I think I might enjoy a risqué costume! strip quickly and follow your example, handing a waiting (and watching!) Marie my clothes. I join you in a quick shower.

"Is it ok to keep my hair in place here or do I really have to go back to my day self?", I ask as I carefully avoid getting my hair wet. Conscious I still have makeup on too, I quickly help soap your fantastic body, marvelling at how responsive you are but knowing it might be a while before I can get hard a third time. "And did you mention hair removing? I think the size of my boobs were just fine, but show me how smooth I can be, then it's costume time.."

I am revelling in just enjoying all things feminine, this is just delicious and Friday evening is not quite over... I shiver a little thinking about what you might have planned for tomorrow...

Annie

"You're okay if your hair gets wet. We have it on properly so you can swim with it and feel what its like."

After you've finished cleaning (and teasing) my body, I turn to you. Work up a lather and soap your body, taking special care with your asshole, genitals, under arms, and all over below the neck. You feel your skin tingling in a very silky sensual way and when you touch yourself as you rinse, you feel silky smooth everywhere and your skin is very pleasurably sensitive.

When you step out of the shower, I have a long towel wrapped under my arms. I towel you off and even the high thread count cotton towel feels amazing on your smooth skin.

"Now wait here... I was going to save this for later in the weekend, but I think you'll really enjoy it..."

I leave you in the bathroom, looking at yourself in the mirror, naturally leaning in to make sure none of your make-up got disturbed and brushing a little at your hair. Returning, I have a box from some elegant clothing shop you guess. It's only a couple feet wide and narrow. I place it on the vanity and turn to you.

"As soon as I knew we would be together like this, I got you something special. Remember when I was taking all those pictures with my phone? That was to help me with this. These are very special and I wanted them to be perfect for you."

After enough mystery, I have you open the lid of the box. You see two large breast forms set in form fitting packaging. I lift one out and show you how realistic it looks and feels. The skin is supple and when I hand it to you, you're surprised at the weight of it. It was tapered in odd ways but I assured you there was a purpose. You also saw a different sort of material in the centre of the inside of each one.

"Let me explain after I put them on," I say and slowly use the remover to get your first breast forms off you. They were good, but these will be something different again. I pull some gel out of the packaging and turn you away from the mirror. I put the gel all over the inside of the left breast form, turn it around in my hand and then place it against your chest. The gel feels warm and in a moment the breast does as well. I shift it a little, getting it just right before repeating the process with the other one. You feel them firmly attached to your skin and their weight pulling a little on your chest. Once I am satisfied, and I am a perfectionist, I let you turn around.

Your breath is taken away. The skin colour match is perfect. The sizing is a little larger than you might have selected but you see how they look perfect with your body. Moving, you see them move just like mine do if a little firmer. With the wig and makeup, it is a struggle to NOT see the woman in the mirror.

"These are temporary. I know you have a life to go back to, at least for now. There is a longer lasting version of the gel in case you're ever interested. These are perfectly designed. Feel your breast and my breast at the same time. Really hard to tell the difference, right? And that weight is what we girls put up with so you get to experience that too! And now for the icing on the cake..."

I lean down and gently take the large nipple from your left breast into my mouth and tongue it. You gasp as you feel my tongue on your nipple! You feel every bit of my tongue and lips sucking your nipple. My hand begins to play with the right breast and its just the same. Everything is transmitted down to your own nipples... sense of wetness, pressure, heat, everything.

"Just a little technology I discovered that was originally developed for other purposes but luckily someone applied it to this situation. So you look like you have a great pair of girls, you feel like you have a great pair of girls, and you feel how good they are when someone plays with them. Isn't that just perfect?"

You glance in the mirror and see how bringing your arms in just a little gives you very sexy cleavage. You also realise that you could go out in public and probably pass all but the most intense scrutiny.

"And now you'll fit all my clothes just right!"

I lead you into my walk-in closet and over to some hanging clothes and drawers.

"Now, my one piece suits are here. I like a very high hip and showing off my cleavage but with good support so I can get a workout swimming... or something... if I want to. They are really flattering with great bright girly colours... pinks, pastels, strong solids like white, black and red. Can't go wrong with them."

I pull open two of the many drawers. "Here are my bikinis. A little less practical for a lot of swimming as some of them are pretty small but ideal for tanning or teasing people. Look through them and pick one out for you and one out for me."

Lucy

I am stunned, what have you done? I know I told you about my desire to enjoy sensual fabrics and not really to be a woman, but you have just drawn me in to trying the whole experience. I cannot believe the feel of the breasts you gave me, barely a join visible unless close and the link to my own nipples is spooky. Whatever you washed me with I want... soooo smooth a feeling, and as we return to your closet I take in your fantastic smooth flesh and cannot wait to try on something more of your clothes.

A warning bell rings when you say 'go back to my old life..' but I know who I am for now and that is a lesbian with a cock that has just satisfied her lover and will do so again before the weekend is out.

"I really want to try a form fitting costume with the high legs, I know my cock will be visible though, I take it no one else is going to see us swim? As for you... I want you... on display... that tiny one, barely covering your nipples and pussy... that might help improve the bulge in my costume!"

Whilst your smooth naked form selected the costumes for us - not that yours was going to cover much - I looked again in the mirror. What HAD you done? They must have cost a fortune and I smiled as I saw you watching me. In the mirror what did I see? A shemale?? I saw a tall, slim, feminine form with larger than average tits and right now a flaccid cock that had just been emptied, cleaned and made smooth. I could not take it in, even without makeup I was still looking so different and feminine, perhaps tomorrow we would go shopping and Lucy would brave the outdoors. First... the costume and I turned to see the outrageously daring one piece you expected me to get into!

Annie

"Hmm, well, you could tuck your cock if you wanted that smooth front but I don't think it will stay soft for long this weekend," I tease, leaving you with that option. "Here, this is a little different from my normal solid colours but I think it is crazy sexy. The button's by your breasts and I think the striping will actually hide the bulge a bit. Very form-fitting so you'll feel every bit of it around your body."

I laugh when you pick the smallest bikini I own. "I haven't worn that in a few years but I think I can still pull it off," I comment as I step into the little bottoms and deal with the lacing. "Good thing I'm bare down there..."

I watch you pull the tight suit over your feet and up your legs. The spandex/nylon feels deliciously feminine, just overloading you with sensations that declare "This is women's clothing! You are putting on Annie's clothing!" It is tight over your bottom and hips and thighs as you tug it up more and more. You look down at your breasts which block your view "south" in a way you've never had to deal with before. Tugging the suit up to get your arms through the holes, the swimsuit material pulls over your breasts and stimulates your nipples delightfully. The breasts are surprisingly... squishable? More than you'd expected and seem ready for robust treatment, firmly attached to you like the wig.

Finally, you get the suit on properly and run your fingers down the edges over your bottom to straighten it out and realise what a girlish move you just made without thinking.

Lucy

What a gorgeous suit you picked out for me, and the feeling of the material pulling up and over my cock, responding again a little already, was amazing. How do I..?? Aah, boobs, fuck this is sexy, for a man to play with boobs this way is soo sexy, so arousing and the bulge this will create will only be seen by you and Marie, so its fine. I smoothe the suit out, and notice you smile at my clearly feminine gesture pulling the suit into place. Your coaching, the outfits, our situation are all combining to move me a little way towards feeling more comfortable with my new feminine figure and hairstyle.

Then I see you in the suit I chose, if you can call three triangles and some pieces of string a suit! Fuck you look hot, and yes, you can still pull it off as the growing bulge in my suit will testify. Good job we are both smooth I suspect, the fabric of yours clearly displays your engorged pussy lips and cleft as the material hugs your sex. The triangles above barely cover your nipples, and your magnificent tits are almost entirely on display. Nipples are growing harder, and I reach to gently stroke one through the tight, wetlook material and you shiver.

"I wonder if we ought to swim now... briefly... to cool us down before I just take you back to bed and try to make you cum again??"

Annie

"We need to swim... an interlude, lover," I reply with a smile, giving you a kiss before I lead you to the backyard.

The pool is large with beautiful blue waters. There's a couple of chaise-longues, a wet bar, and towels. I fix us drinks and then dive into the pool, coming up laughing as I try to get my suit back into position over my nipples. You see that I am strong and graceful in the water, clearly quite an experienced swimmer.

You use steps that lead into the pool. Step by step you feel the warm water envelop your sensitive skin. When it reaches your suit you feel the material cling and pull on your body the way it would pull a woman's body. Pushing off into the water you feel your 'hair' get wet and brush your neck and shoulders.

"I met my first love on the high school swim team," I say as we tread water near each other. "She was a beautiful black girl named Sara. The first time somebody besides myself made me orgasm it was her fingers between my legs as we waited in the pool with the rest of the team nearby. When I couldn't hold back any more, I screamed and came. Had to blame it on a nasty leg cramp to cover up what had happened. We were inseparable all the way to the day we both left for separate colleges, crying without telling anyone why."

Lucy

I love your pool, and the kiss we share before we swim is tender and I sense your calm and relaxation with how we are getting on. I am enjoying the feel of being femme, and the sensations generated go straight to my cock again. I was just a cross dresser before but you have awoken something a little more in me... not a full time desire but certainly now I feel I will want a regular time as Lucy... a lesbian lover to you, maybe Marie too from your hints.

As I enter the water it feels so different, the smoothness of my flesh heightens everything and the gorgeous swimsuit folds tightly over my growing cock... good job this is a private pool. I swim a couple of lengths, my previous agility and comfort in this environment slightly tempered by the new shape I have... When we tread water your recounting of your first love makes me smile, but also arouses me... and I have to ask, "Your first love was a woman... and you are bi, but do you have a preference?? I only ask because you seem particularly intrigued by the combination the Lucy in me is presenting?"

Before you answer I lean over and gently kiss your lips as we tread water, and my hand strokes the warm flesh of your almost exposed breast... "My first love was a woman, all my loves have been women... but no one has taken what I have shared and how I think and understood where I was coming from. No-one has brought me on and aroused me in the way you have in such a short time... and its only Friday night... thank you already."

Annie

I don't respond for a while as we kiss but when we break my arms are crossed behind your neck lightly.

"I've had men and women lovers but I've also been lucky enough to have a few friends and lovers who were sissies or similar. I find the combination of loving a woman who has a cock to be... be suited for me. A girlfriend with a cock leaves open many doors to a relationship if it ever became committed and long-term. But more selfishly, I would miss taking a hard cock and tasting the cum if I settled down with another woman."

We kiss some more.

"I don't want to really talk about much more since this is all so new, but just know that I love how this is going and what I'm discovering about you. Now, prop your leg up on the step, that's right, give me something to use..." I slide over your raised thigh as we embrace tightly, enjoying the feeling of our breasts against each other as you feel me start to grind my pussy against your leg. "We'll have to teach you all the lesbian moves," I say, eyes closed as I feel the pleasure our bodies are making against each other...

Lucy

Your words sink in, your honesty and openness refreshing and arousing. Attraction to me not just as a man but as a woman with a cock, the taste and feel of a hard cock something you clearly desire and which I have already shared and will, no doubt, share again. Your pussy grinding on my thigh sends jolts to my cock, even in the pool I am sure I can feel how wet and aroused you are.

"All the lesbian moves? Mmm, now... I am sure there are a lot so I guess that sounds like I might have to come back again??!! I mean, I am slow at picking things up... you might have to repeat some of them regularly so I really get to understand...", I said, smiling and hoping you detect my bad attempt at humour, I am relaxed and I don't want you to feel concerned for me.

"Annie, sweetie, I don't think I am sissy... not really... but you have awoken something. Let's explore, I am still ready for you to stretch my boundaries this weekend and what you have said doesn't change that, well... it might... but in a positive way... you must be doing something right", I finish and slide your hand onto the front of my swimsuit even as your pussy grinds ever harder onto my smooth thigh

Annie

You watch as I arouse myself further, grinding, twisting less, then more, then less, playing with my pussy and clit against your leg, its special heat moving up and down your skin. As I get more urgent, I yank and pull away the joke of my bathing suit leaving me naked against you. My nipples are swollen and hard as they rub against your breasts. I embrace you and hold on tight, getting extra leverage to drive myself over the edge. You feel me tremble as I get close and then shake as another powerful orgasm overtakes my body and my mind. My moans are loud in your ear as you feel muscles all over my body contract and feel the pulsing of my pussy as I cum.

We relax and I recover in the water. I float with just your hands to buoy me when I dip a little. My breasts are prominent rising from the water and fascinate you. I ask you to walk me around the pool, knowing you'll enjoy the way your swimsuit pulls and tugs on your body, working the material between your cheeks. You pause to correct the situation, remarking on how perfectly useful the "girl's manoeuvre" is.

"I think we have all weekend... and as many weekends as we wish," I decide, clearly tired after such a sexual workout. "Shall we go shower off and slip into something for bed time?"

Lucy

I watched you get yourself all steamed up and aroused on my leg, marvelling at the ways you changed your movement, the thrusts, the slides, the grinding movements, all combining to use my flesh for your own pleasure as I held you close. I revelled in your orgasm, enjoying the feeling of closeness and of you using me for your pleasure, showing me how you can enjoy sexy fun in any position.... and the pulsing as you came was divine to hear and to feel. You might notice it has had an effect on my costume shape.

Floating with you, watching your firm breasts above the surface, nipples still bullet like after the orgasm I am aroused and yet sated, not sure how that works but am sure I am enjoying it. As we walk back towards the house I feel the sensually tight and thin costume sliding into my ass and tweak it out, causing a chuckle from you at how girly I have already become. I smile ruefully, completely oblivious to the wig that gives me a fighting chance of looking femme without makeup. I enjoy the boobs you gave me, the feel as I walk is something else, changing my posture, and I am aroused by my own shape as I catch a glimpse reflected in the glass doors we approach.