The Interview; Number 01

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Louise69
Louise69
327 Followers

When she's done, she pulls out a new wig from a bag.

"This is from me. I like your old one, but this will frame your face a little better. It's a closer match to what your hair would be like long too. Looks a different shade when it's shorter. She slips it on and then shows me how to try different styles, pulling at the fringe to come down in sexy waves and giving me a pony tail that whips at my back.

She hasn't changed much, but those small tweaks added up to a big difference. That deep wave of emotion again.

"Can I cry now?" I ask and Liz chuckles.

"No you bloody can't. I like you more as Jenny, but if you start getting emotional, I'll change my mind. Get your ski kit on, we're hitting the slopes."

Best. Day. Ever.

There are moments you mark in life as something special. It could be the day you get married or the day you become a parent. It could simply be a promotion or new job or even the day you buy a house. For me, it's when I first called myself Jenny. It felt right. It's when I first went for a walk at four in the morning as Jenny and then when I went out to Pink Punters. It's when I first sucked cock and accepted what I was. It's when I went to the cinema or shopping for the first time as Jenny.

This day beats them all. We went skiing. Simple as that. We spent the whole day out on the slopes, had lunch at a busy restaurant, giggled and laughed and tried snowboarding, fell over and hurt ourselves. I dressed in the skinny jeans and jumper dress Liz chose and we ate dinner with a bottle of wine. I slipped in my too high heels, but Liz caught me and we had some more wine before going to our separate beds.

So why so special? I was Jenny. No strange looks, no discussion or focus on it. I simply was. No one paid us any heed and, as I lay in bed, drifting off to sleep, I had an epiphany. I wasn't a crossdresser or transvestite or whatever labels you want to give. I am Jenny.

And Jenny can be a bit of a slut at times! The next night isn't nearly as mundane. I'm straddling Sean grinding on his cock as he arches back, pushing it deeper into me. We're both covered in sweat, laughing as I start to cum for the fourth time that night.

My dress is ruined, but it's not my favourite one, so that's ok. It's in a corner, all crumpled and I'm in a red satin corset with suspenders, thong that's pushed to one side to let my cock out and nipple clamps underneath my silicone falsies. Sean is reaching up and pushing against them through the satin of the corset and I can feel myself losing control again, thigh high leather boots a creaking backdrop to our groaning.

I place my hands on his flat chest as I start to cum, gobbets of fluid splashing on his chest as he laughs, his own cum filling me. It's the third time he's cum inside me and I can feel it dribbling down. It's a very long time before our breathing slows and a lean down and start to lick my cum from his smooth and freshly shaven chest, the tight corset making it more difficult than it needs to be.

Oh, wait, hang on, back up a moment. Sorry. Sex with Sean was something else and I went all Christopher Nolan on you in a rush to get there. Let's rewind a bit. Forget waking up, skiing, blah blah blah. Done that. Let's start with getting out of the shower that evening, Liz in my room, grin on her face.

"You've got a date," she says. I don't get a word in edgeways, she's off like a rocket. "His name is Sean and you'll be meeting him at seven." Hands held up to placate me. "I downloaded an App, thought I'd see if there was anywhere we could go for you and there's all kinds of dating things and he's here, all good to go. Thank you Liz, it's fine, don't thank me, just go have fun!"

"No way," I say. "I'm not meeting a random stranger and this is our time." Liz smiles.

"I'm having an early night. Those slopes have worn me out. I'll be no kind of company."

"What if I'm tired?"

"Like you ever need more than a few hours' sleep. Go out, have fun and I'll be bright and fresh tomorrow. I've chosen your outfit. C'mon, you've got to be there in an hour."

She always does get her way.

So an hour later, I'm walking up the cobbled streets in a pair of strappy sandals, shivering in the cold as Liz tells me to girl up and suffer for my wardrobe. Liz has bought me a leather dress that has jumped right up to the number two spot on my list, maybe number one if someone puts a gun to my head. It's tight in all the right places, not too low cut so I can hide my lack of real breasts, and sleeveless. The leather is soft and satin lined, every movement I make giving me the shudders. Liz had chosen well, but she had also chosen for warmer times. The skirt reached to my mid-thigh and was so tight I was forced to walk on a tightrope. I was sleek and elegant and I was in love.

I borrowed Liz's fur jacket (fake, obviously) and held it tight against the wind as we approached the bar. I had my long, dangly earrings in and bracelets on my wrists, jangling around in the wind. Liz had done my make-up and given me the sultry look, all dark hues and smouldering eyes. If I'd done it, I would have looked a little sluttish, but Liz showed me there was plenty left to learn.

The bar looks warm and inviting, but I pause briefly as we near the entrance. Liz pushes me on.

"Get in or freeze to death," she mutters and I almost trip through the door. Sleek and elegant. That's me. Liz scans the bar and waves at someone sitting at a nearby booth. He's alone, and I'm dragged there before I can register what's happening. Sean stands, much taller than me and twice as broad. He looks like Thor from that Marvel movie when he has his hair cut to fight the Hulk. Didn't know I had a thing for Thor, but my heart is beating fast in my chest as he smiles, all twinkling eyes and gleaming teeth.

"You must be Jenny," he says, voice all warm and smooth. Like honeyed butter. I'm blushing and Liz is grinning.

"Need me to stay?" she asks.

"She'll be fine," says Sean and I wink at her.

"I'll be fine."

I was more than fine. I liked Sean a lot. He was Swedish but his English was good and he helped me relax soon enough. His eyes roved my outfit and I saw him watching my butt as I slid out the booth to go to the toilet. Getting back in the booth was hard, but I slid in next to him and he rested an easy hand on my hip. I nudged closer as we chatted about all manner of inane things. He travelled a lot and regaled me with various outlandish tales, some of which I believed, some of which I didn't. Either way, I laughed and so did he.

Feel free to judge me, but it was only a few hours before we were heading back to my place. I was tipsy and so was he. I was horny and so was he. No hiding my cock this time either. The house was quiet and I pulled Sean quickly to my room, my cock straining to be released from the tight knickers I wore.

Sean throws his clothes on the floor and I chuckle at the Thor image again. Not an ounce of fat. I tug at his trousers and yank them off as I sit on the bed, shoes and fur coat still on. I pull his pants off and grin at his huge cock as it quickly erects before my eyes. He's huge and I lean forward to kiss it, one hand pulling my hair back over my shoulder to get it out of the way.

I tease the sensitive shaft with gentle kisses before opening wide and seeing how much I can take. About half. Sean reaches down, strokes my hair as I kiss and lick and tease, adjusting the angle of my throat so I can take more in. About three quarters. I feel it against the back of my throat, my gag reflex kicking in. I override it and take more in, groaning as it fills my mouth and throat completely. I'm rewarded with a matching groan from Sean, hands reaching up to grab the top of the four post bed, stretched out but standing up.

I grab his hard thighs with my hands and use his strength to push all of his cock in. He thrusts in and out, gently at first and then faster as he begins to cum. I tease his balls with one hand, the other grabbing his toned arse and scratching gently with a lacquered nail. When he cums, I'm expecting it, but not prepared for how much there is. I almost choke, but remember I'm wearing Liz's fur jacket, so can't spill any. I gulp it down, streams of hot, warm, salty fluid as Sean cries out in ecstasy.

Panting, he leaves his enlarged cock in my mouth as I gently rock back and forth over it. He tastes divine. Finally pulling free, he leans down and kisses me deeply, tongue probing my mouth. I reach behind his neck and pull him down over me.

"My turn," he says and repays the favour. Twice. He sees the thigh high leather boots poking out of my bag. I was going to wear them to a club with Candy. He felt now would be a good time. He had me lie on my back and ravaged me as I wrapped my legs around him, one of his hands tugging at my cock so we came at the same time. Dress ruined.

He turned me over and took me from behind as I urged him to push harder and faster, bringing me to orgasm once again. He lay on his back and I knelt over him, lowering myself over his insatiable sex. I collapsed after that, too exhausted to do anything else and slipping into a deep sleep.

Hours later, I woke to find that Sean was kissing my cock and coaxing it back to life, ready for another round. Like I said; insatiable.

Later that morning, I kiss Sean goodbye and wave him off before grabbing a quick shower and changing into some skinny jeans and a knitted jumper with long sleeves that had the shoulder section missing. I loved the look even if it was too cold for that. Liz is on my bed, holding a large mug of coffee as I put my make-up on. She's slept well and looks refreshed, dragging all the sordid details from me.

She gives a sad shake of the head at my new and ruined dress and I tell her I want to go and buy a new one. She agrees that's a good idea and we hit the streets of the resort, wandering through the beautiful town with the mountains standing over us in silent reproach. I ignore their demands to be conquered with ski's and enjoy the experience of shopping with Liz. She has me try all manner of clothes and shoes on and I soon lose my nerves as we visit shop after shop, not caring how much we spend. I'm due a bonus soon, so figured I'd put it all on this.

I get read a few times, but no one seems to mind. The whole atmosphere is relaxed and friendly and I don't care. I see the odd puzzled look as if they know something isn't right about me, but can't figure out what. Liz ignores them all.

"You need to grow your hair," she says. "That'll help seal the deal, maybe get your Adams Apple trimmed a little. Not that you really notice it anyway." A shout from across the street and I see Sean rushing over. He looks good in his ski outfit and I find myself blushing like a silly school girl. He leans in and kisses me on the cheek.

"Good afternoon," he says and Liz invites him to lunch. He shakes his head. "I am off to enjoy the snow, slopes and sun. Later tonight maybe?" We agree to meet him at the same venue as before and he asks if it's ok to bring a friend. I say, sure, no problem and we head off to finish our shopping.

"It's meant to be a holiday for just you and me," I say as we sit down to eat. "You ok with us going to see Sean later?" Liz grins as she sips her wine.

"After what you told me you got up to last night? I'd be disappointed if you didn't!"

We meander back to our house with our shopping and go for a lazy afternoon ski on the slopes. Enough to build up an appetite but not enough to wear us out. We shower quickly and I put on an electric blue dress that reaches passed my ankles and has one strap on the shoulder. I spend half an hour gluing my breasts on first as I can't wear a bra with it and have a giggle with Liz on the bed as I lie down, holding them firmly against my chest, waiting for the glue to dry. Liz helps glue all the edges down before going to change herself.

The dress I wear is made of a stretchy fabric that allows some movement of my legs, but not much. The long length means I have to wear five inch heels just to stop from tripping on it and the narrow skirt has little leeway for movement. I feel great wearing it. Sometimes an outfit just feels right and I put in some large hoop earrings and toss a few essentials into my handbag as Liz enters the room. She is wearing the same dress but in crimson and looks stunning. It's easy to forget how beautiful someone is when you've known them for so long, but she took my breath away.

"You look gorgeous," I say and she reaches out a hand to clasp mine.

"You too Jenny. Shame you're not a real girl. We'd make quite the pair." I lean in and kiss her softly on the lips.

"We'd make a heck of a pair," I reply and she gives me a sad smile. I tuck a stray blond hair behind her ear and pull her to me. She has only recently split up with someone she'd been with for years. Pain still raw.

"You're beautiful in all the ways that matter," I say. "You'll find someone else soon." We hug for a while and it feels good.

"Come on," she whispers eventually. "Let's go get some jiggle juice."

I always think the second time you have sex with someone is the best. No awkwardness. Not that we were last night, but tonight, Sean is even more insatiable. We have a fantastic evening. He brings a few friends along and they are easy company. Liz even gets lucky and winks at me as she is led from the bar by a stunning red head. Sean makes a lame excuse and drags me from the bar back to my house. As we get through the door, he's kissing and fondling me, breath heavy with lust. We make it as far as the table in the hallway before I'm leaning on it, pushing back on his throbbing cock as he takes me from behind, knickers round one ankle and dress pulled up over one arm.

It doesn't take long for him to cum and I grip the top of the cold, wooden table as I feel him fill my arse with his cum. As he's finishing, I start to orgasm, my legs juddering with pleasure as my sphincter closes repeatedly round his cock, forcing him deeper into me. I can see myself in the mirror and laugh as waves of wondrous rapture engulf my body for what seems like hours. I almost fall, but Sean holds me tight.

Before I have chance to recover, Sean turns me around, still impaling me with his cock and lifts me to the kitchen unit, high enough for him to stand and thrust upwards from below, his cock reaching deep inside. I wrap my legs around him, hands tearing at his shirt to get to the hard muscle beneath, kissing him deeply as I feel him start to cum again, my balance on the kitchen top precarious to say the least. As he cums, he loses balance and falls back. I fall with him and he thuds onto the wooden floor with a crash, laughing as he manages to stay in me. I grin and quickly straddle him, letting him finish as he moans with pleasure.

When he's done, I kiss him gently on the lips and stand up, holding his seed inside me so I don't leak on him. I don't know why that's important to me.

"Beer's in the fridge," I say. "Make yourself comfortable."

I hop to the bedroom and strip, hanging my dress back up and kicking off my shoes. I take a few moments to adjust my make-up and reach into my luggage to pull out some clothes. I'd seen a film once where the woman put on some stockings, black satin basque with suspenders and matching thong. She wore a matching dressing gown that hung loose over one shoulder and high stiletto heels. I was entranced by how sexy she looked. All I wanted to do was be that woman and whenever I could, I would wear something special like that for my man.

I took my time and lit some candles in the room, their faint glow shimmering in the mirrors and lay on the bed, adjusting the gown to be both provocative and sensual. Pose adjusted, I called for Sean and he arrived in moments, bare chested and muscles rippling in the light. My own private Thor. I pat the bed as I see his eyes rove over me, lust clear on his face and curl a beckoning finger at him. He doesn't need to be told twice.

Second time was definitely the best.

I woke up sore in all manner of places and crusty in all manner of others. I felt completely satisfied, however and snuggle up to Sean. He's in a deep sleep and I hear the front door open and close softly, a gentle light coming through the door as daylight scampers in. I sneak out of bed and tie my gown closed, loving how the material stretched over my breasts.

Liz is in the kitchen and looks about as satisfied as I feel. She smiles as she sees me and holds up a pot of coffee. I accept the offer and we sit at the table to compare notes. She's smitten with the red head, that's for sure. They only live a couple of hours apart too, which is great.

"Flying back tonight," she says and shows me her arm. There's a mobile number written on it and we chuckle with contentment.

So, by this point, you must be wondering why I'm here for an interview, right? Everything seems cushy. I've told my best friend about my deep, dark secret and she's more than just cool with it. I'm living full time as Jenny for the week and will probably do it next week in Amsterdam. Just had some epic sex and all is rosy in Jenny Land.

Except Sean comes out of the bedroom, says he has a flight to catch and just leaves. No empty promises to meet up again or kiss on the cheek, no hug goodbye, just a wave of the hand and fare thee well, have a nice life.

We'd not done much but have sex and get drunk for two nights, but I felt some kind of connection with Sean. He didn't feel the same obviously and I had no right to think he had any attachment beyond sex, but I was a little upset, put out maybe. You feel things like that more as a transvestite. You think it's the way you look, not good enough, maybe he's ashamed of you. It's fine for a night getting pissed, but not when you have to walk the streets with them in daylight. Relationships are hard enough without extra baggage.

Anyway, I feel upset, so Liz promises a fab day to get over it. Foot massage at a nearby parlour, followed by toe and nail care. I'm wearing a denim skirt for the occasion and silk blouse to cap it off. Knee high boots with a towering wedge heel are a must in this weather and thick socks that I can peel off quickly for the massage and cuticle care. I've never had this before but it feels great to be pampered. The staff either know I'm male or don't care. Either way, they don't discuss it and make me feel at ease.

After we're done, I pull on my boots, zip them up and put on the coat Liz gave me and tug a ski cap over my wig. A howling wind chases us through the street and we buy a few pieces of jewellery in a nearby store. I start to feel better and suggest a light meal followed by an afternoon on the slopes.

"Good plan," agrees Liz. "We can go somewhere expensive for diner too, celebrate being half way through our holiday."

"Worth celebrating," I reply with a wink and we head off to eat and drink and ski and laugh.

You see, this is where it goes wrong. I'm like a lost school girl, Liz feels bad and suggests a swanky restaurant. So we're sat in the restaurant and I'm shitting myself. It's more than I can afford but Liz insists on paying. I'm in a dress so tight, I'm not sure I can breathe in it, let alone eat. It's deep purple, with a high collar and a strap that goes across my upper arm instead of over the shoulder. It pinches in at the waist and then loosens out below, all billowy strips of satin and silk that wrap around my legs as I walk.

It's my new favourite dress. I know, I'm fickle.

I'm wearing matching shoes, patent purple strappy shoes with a five inch heel that's more a spike than anything else. Liz has shown me how to wear my hair up and it feels strange, yet wonderful. Necklace, rings, earrings and bracelet complement the outfit and I feel a million dollars. Sat next to us are two men who asked to join us for coffee once we'd finished and Liz, brazen as anything, says yes, winking at me.

Louise69
Louise69
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