tagTransgender & CrossdressersThe Interview; Number 01

The Interview; Number 01



Many thanks for reading my short story, The 1st Interview! I'm going to let you decide the outcome of this and the 2nd Interview, so please email me and let me know who you would like to work at L/J's!

The winner will be revealed in "L/J's", a short story to be released later this year.

If you have any other ideas you'd like me to explore, feel free to let me know!




"Okay, so I'll start at the beginning, kinda the best place really. I'm not going to do a Memento on you and chop my story up into pieces, jumble it up and try and confuse you. The beginning starts on a plane to Zermatt. No wait, the beginning is, hang on...you want the truth? No holds barred, gospel truth? Ok, cool. I've only just met you, so don't go thinking I'm some kind of perv. There's a point to starting here.

See, I'm about to go on two holidays. Happens every year. I meet Liz at the airport and we take a city break somewhere nice. Last year, it was Barcelona, this year it's Zermatt. I love skiing and said I'd show Liz the ropes. She's been once, so it would be a good chance to catch up and have some fun. We've been friends for years, long as I can remember and we make a point of having some quality time at least once a year. After we're done, I make up some random business meeting and fly off to Amsterdam to see Candy.

Who's Candy? She's my Angel. Every tranny needs to have the good fortune to have an angel. We meet in some chat room or other and get talking. I'm on the Xbox, so she sends her Gamertag and we hit it off, laughing away as we kill zombies in Left 4 Dead. She's the kind of gal who's been there, done that. Lots of confidence and lots of know how. She takes me under her wing and shows me how to dress for my figure, how to walk in heels, where to get my falsies and so on. She even held my hand while I had my face electrolysed. Boy, that hurt.

This isn't the bit where I say we were platonic. We had sex a few times. I'm not really fussed by gender, just how I feel about that person and it was great, but before we could get serious, she was offered the job of a lifetime abroad. I was gutted to see her go, but, by then I spent most of my time outside of work as Jenny and have a good bunch of friends. We do all the same shit other folks do, but we do it as we are. It's great.

Anyways, I'm getting side tracked. Candy is great. We keep in touch plenty and try and meet as much as we can. She says she'll move back in a year or so, but we'll see.

So, I've packed two bags. One for my holiday with Liz and the other for my week with Candy. You can see where this is going, right? Stick with me, it's all in the telling. There's even a few twists on the way, keep you on your toes. Not Sixth Sense style twists, that would be weird. I phone for a cab and have an hour to kill. Knowing that my week with Liz will be fairly vanilla, I decide to have one last sissygasm before I leave.

I have one rule about masturbation. It's hands free or not at all. Have you ever achieved an orgasm through anal stimulation alone? It's mind blowing. Took me a long time to achieve it, but when I did, I made a vow never to simply jerk off. It's too quick. A true anal induced orgasm lasts for ages, your whole body vibrates and you realise, as this immense pleasure fills your whole being and stays with you for a long time after, that it's not about ejaculating. It's about having an orgasm. That's the secret.

First time Candy told me about the sissygasm, she showed me plenty of videos on Tumblr. She'd posted a few videos herself and I was transfixed, determined to try it myself. First time, I made a big deal of it, dressed in this sexy dress, lots of make-up, highest heels, stockings, wig, the works. I'd chosen the wrong dildo and it was just a little too big. I wasn't experienced then and it took ages to even get it in for the first time.

I then started trying out my kinky side, see if that works. There's two parts of me, you know? Jenny is a simple gal, has fun, dresses her age, if a little bit more of a tart! Then there's the other side that now and then loves a satin maid uniform, the tighter the better. Sometimes, I even like some rubber. Anyways, I tried it all. One time I was full on maid. Got close that time. Thrusting up and down on this rubber, vibrating cock, loving the feel of the satin gripping my body, the soft stockings on my legs and the six inch heels as I desperately tried to cum.

Next time, I went even further. Rubber dress, big collar, nipple clamps, gag, all sorts. That didn't work at all. Candy laughed when I told her about it and she gave me some great advice.

"Relax," she said. "Just enjoy what you're doing. Don't make a big deal out of it. Dress to feel feminine and just focus on your body, on how you're feeling. What you're wearing is only a part of that. You're thinking it's some big kinky thing. It's not. Let Jenny have an orgasm."

I thought hard on that, lying in bed later that evening. I was dressed as I was every night, satin negligée and knickers. That was another rule of mine. No matter where or when, a negligee was the only appropriate night time clothing. Unless it was really cold and then I was allowed a satin pair of pyjamas. Or if, I was with someone, in which case, there were other ways to get warm.

As I thought on what she said, I reached into my bedside draw and took out a moderate sized dildo, lubed up quick and simply relaxed, took it slow, closed my eyes and focused on my body. As it was the weekend, I'd glued my falsies on, knowing I wouldn't need to take them off until Monday morning before work and they strained at the soft material of my negligee.

It didn't take long, but boy was it intense. I couldn't stop gasping and then screaming as waves of pleasure rippled through me. My legs kept juddering insanely and I grabbed my satin sheets (another rule for household management -- girly, satin sheets only) with my free hand and sighed loudly as the orgasm eventually passed. It felt like every orgasm I'd ever had until that point had all been combined into one. As I said earlier, ejaculating by jerking off? Takes seconds, sometimes a bit more. Hands free? So much longer and more intense!

Once I'd done it the first time, it got so much easier. First time I did it during sex, I bucked and yelped as strong hands tried to keep me in place. His cock slipped out, spraying me with his cum. My favourite dress too, but I didn't care. Well, not until the next morning when I had to throw it away.

So, here I am with an hour to kill and I think to myself, I'll just have a quickie. I throw off my clothes and grab my satin kimono, loving the feel of the material over my freshly waxed skin. Slipping into a pair of court shoes, I love the sound as the heels clip clop on the wooden floor of the hallway as I get some more lube from the bathroom. Putting some music on, I go back to my bedroom and smother my favourite dildo with lube, using the suction cup on the floor to hold it steady and then get to my knees, shifting over the dildo until I can lower myself onto it.

I take my time, go slow, enjoying the feeling of the silicon cock as it slowly parts my cheeks. I pause and let myself adjust before rising slowly and then slipping down a little further each time. Soon, I have a decent rhythm going and press hard on the floor to keep my balance. My kimono slips from my shoulders, but I didn't mind. I always love the way it does that on women and enjoy the feminine sensation as it gently caresses my skin.

I can feel the orgasm coming so quickly sit up straighter, forcing the cock shaped dildo further into me. I gasp and chuckle, suddenly breathing deeply as I feel my legs start to shake a little. I concentrate on the little rocking motion that tickles my G-Spot and moan deeply as I start to orgasm. After a full minute of sensuous divinity, I feel myself start to cum and look down to find cum oozing from my cock, the occasional spurt splattering the wooden floor as the intensity of my orgasm increases.

It's another few minutes before the sensations die down and I sigh with contentment, simply rocking slowly on the dildo and enjoying the afterglow.

It's then that the doorbell goes and I almost crap myself. Checking my watch, I'd lost track of time and frantically try and organise myself as the cabby outside rings my number to see where I am.

"Be right out," I say on the phone and throw my heels and gown on the bed, rush to the bathroom to clean myself up and then grab my bags, switching on the alarm as I go.

"Sorry," I say to the cabby, who looks less than impressed with my tardiness. He gives me a funny look and it's one I'm used to. When I'm not Jenny, I'm a bloke with a well-paid job that I need to hide Jenny from. That means I gotta push the boundary, but keep it in check. My eyebrows are shaped, but not too much, holes in the ears just a misspent youth. Nails, well-manicured, but not long. No stubble though. Can't deal with that. Some folks pick up on these tells, some don't. He's pissed coz I kept him waiting at the door and now I'm weird to boot.

He tosses my bags in the boot and, without a word, drives me to Heathrow, only about an hour from where I live, traffic permitting.

Pulling up, I pay my fare and pull the bags from the boot, keen to get away from the surly cab driver. He's an arse, but I'm no saint, so I resist the urge to get snarky and pull my bags with me to the airport. One bag for Jenny. One bag for Man Mode. Simple. Been doing it for years. I have a friend works at the airport, Darren the baggage man by day, Daisy, the ever so slightly slutty Queen of Soho at night.

He's waiting for me as I pull through the doors to the terminal and he points to his watch with a pointed look. Too much pointiness for my liking.

"Sorry," I say and he grins. Darren makes a stunning woman, but you'd never know it to look at him.

"When are you ever on time?" he replies and reaches out a hand for Jenny's bag. I look down and realise that the A-Hole Cabby had torn off the labels as he'd tossed them into the boot. They were identical bags, BOGOF, great deal.

"Bollocks," I say and Darren sighs as I explain my predicament. I didn't know which was which and they were locked up tight. I rummage through my pockets to get the keys when Darren gives me a heads up. "Liz is coming through the doors. Pick a bag, I've got to go. I'll have it on the right flight for you in a week." I weigh the bags, lifting each with a grunt. They're both heavy, but one is clearly heavier. That's the tranny bag. I toss it to him, tell him I'll call him and turn to meet Liz.

I see her as she scours the reception for me and waves as I catch her eye. She's a stunning blonde, all legs and bubbly enthusiasm for everything she does. She's trim, with a perky nose and sparkling eyes. She's one of those girls who doesn't know how amazing she is and is all the better for it. I had an epiphany a while back that Jenny's style was based pretty much on her. I also suspected I modelled my personality a lot on her too. As a man, I'm a little quiet and withdrawn, as Jenny, I'm much more outgoing.

Not that she knew, of course. As she scurried over for a hug, I felt a little sad that I'd never told her about Jenny. She told me everything, yet I hid a big part of my life from her. I guess, as I'd never told my family (they wouldn't understand) or work (they really wouldn't understand) she'd missed out. She knew my family well and worked in the same company as me, though she'd been moved to head up a new branch in Manchester.

Dressed in tight jeans and figure hugging sweater that reached to her calves, I envied Liz a little. With her knee high boots and leather jacket, she wore what I would have, had Jenny been taking the flight. Oblivious to my thoughts, she reached out for a hug and I give her a big old grin, happy to see her. She was my best bud. She was the same height as me, so towered over me in her heels.

"Hey short stuff," she says and we wrap our arms around each other. "Missed ya."

"You too," I say back. "Been too long." She agrees and appraises me openly.

"Still too thin," she scolds. "You still running too much?" I like to run. Keeps me trim and able to fit into my figure hugging dresses and skirts.

"I'm the exact weight I need to be," I reply and she sighs.

"Come on short stuff, let's go eat. I'm starving."

We eat and chat and laugh and drink and enjoy each other's company. I love Liz with all my heart and I know she loves me. Never in that way. She's gay and sex only interests me when I can be Jenny. It's unfulfilling otherwise. There's never been a hint of that between us and it made it easier to be close. I'm sure she thinks I'm gay too.

Eventually, our flight is called and we take the plane to Zermatt. You been there? It's a beautiful place, one of the best for skiing. It's like a little slice of heaven nestled in the pit of the mountains around it. Covered in snow, at night, it's magical. Like a Disney film without the talking animals. I'd booked us into a lodge near the slopes and close enough to walk into the centre of Zermatt where we could wine and dine to our heart's content.

The lodge is stunning, has three bedrooms, a large lounge with a balcony overlooking the slopes and far too grandiose and posh for what we were used to. Liz whistles as I show her around, clearly impressed. It belonged to a T-Girl, Lucy, back in London. She has herself a sugar daddy, lets me use it for the price of one favour, yet to be determined.

"How'd you say you got this place?" she asks.

"Friend," I reply vaguely. "She'll cash in a favour someday." Liz arches a perfectly manicured eyebrow.


"Friend," I say and move to the closest bedroom, dragging my bag behind me. I dump it on the bed and go back into the lounge area to find that Liz has taken the room upstairs.

"Drink?" I call up and hear a muffled reply.

"Silly question!" I help myself to some cold beers from the fridge. Lucy won't mind. Sugar daddy will pay for it. Finding a bottle opener proves a little more of a problem and I open all the draws to search for one. This isn't America with twist caps. As I'm looking, Liz pokes her head into the kitchen.

"Left my phone charger at home, can I use yours?" I toss her the keys to my bag and keep searching.

Ping. Text on my phone. It's Darren


I finish reading the text, panic setting in as I realise that the heavy bag, for the first time ever wasn't the tranny bag. A loud squeal in my bedroom.

"I knew it! I fucking knew it!" Liz comes in brandishing my favourite little black dress. She has a big grin on her face and is bouncing around with delight.

"That's not mine," I start saying, reflex kicking in. Deny everything. Mistake at the airport. Classic.

"Bollocks it isn't," says Liz. "This dress here is what I wore last year on our first night out in Barcelona. I saw those looks you were giving me. Turns out you were checking the dress out! Admit it, you rushed home and bought it straight away!"

She badgered and teased and cajoled and I sighed and gave her some beer, the edge of the unit working as a bottle opener.

"Sit down," is say and tell her everything. No stone unturned. Mostly. She doesn't need to know how I pissed the cab driver off. Or that time when my favourite dress got ruined. It takes a long time and the night closes around us as we drink, I talk and she listens, a big grin on her face. When I'm done, she finishes her drink with a gulp and gives me a sly grin. I know that look. She's aiming to misbehave.

"Show me," she says. She's not asking. Before I can reply, she raises an admonishing finger. "You lied to me since the day we met, so no backing out. You owe me." She throws the dress at me and grins, gives me a look that dares me to back out.

"Fine," I mutter and make my way to the bedroom, grabbing another beer from the fridge. I give her one and tell her to get comfortable.

"I'll be a little while," I say and she chuckles.

"Take your time Jenny," she replies and leans back in her chair. "We got all week." I like how she uses my name. Feels right coming from her. There's no judgement, but I know she's a little hurt at never being told.

I make my way to my new bedroom, a large space with lots of mirrors, dressing table and big cupboards. Lucy's trained her sugar daddy well. Perfect tranny space. Even a large four post bed and feminine drapes. Perfect.

My bag is on the bed and I see the lid opened, several clothes strewn on the sheets as Liz worked out the contents. I stare at it for a moment. Two holidays, two bags. Was gonna happen at some point or other, right?

I love getting changed. As a man, I'm a little awkward and uncomfortable. My skin don't fit right. I feel small, like some kind of beta male. Not even that, like some kind of theta male. Eighth in the rung. That's me. Jenny? Doesn't matter whether she's alpha, beta or any of that crap. She's just happy to be there. I don't feel small and my skin fits perfect. I get read, a lot less than I used to, especially since the electrolysis on my face, but it still happens, normally when I draw attention to myself.

Pair of jeans, nice top and leather jacket; I'm just like any other girl, long as you don't look too hard. I know which tops fit perfect, which shops work with which size and which dress fits at the top and the bottom. Took a while and a lot of wasted clothes. Thousands of pounds, I reckon, just to figure out my style and see what works. Still make mistakes though, and always will. I've got enough clothes, I could transition tomorrow and not need to buy anything. I'm just lacking that one thing.


Saying that, I've got one thing in spades.


Sure, I act like I don't have a care in the world, but I'm nervous every time I step out the door. I'm scared of what it will do to my family if I go full time or transition. I know I will lose my job, so I will have to start over and I don't know how. Tranny friends tend to come and go as folks' circumstances change, so I worry I'll be lonely. Every journey starts with one step, but I don't have the balls, ironically enough. Maybe if Candy were in London, perhaps.

Anyways, I'm rambling. I promised a beginning, middle and end. Kinda. We're at the end of the beginning. So here's me getting dressed in a little black dress I bought because my oldest friend looked so great in it last year and now I'm showing her me in it. #fuckmeimscaredhopethisgoeswell

I always take my time getting dressed. Gotta cleanse the male, exorcise the demons! No need for a close shave anymore which is great, so I strip, put on my satin gown and sit in front of the mirror, moisturising my face. Used to be, I had to use this thick stage paint to make sure my shadow didn't show, then powder it, then brush the powder off and apply the foundation. I skip steps one and two, head straight for the foundation, rubbing it in and making sure there were no streaks.

Eyes next and I choose dark, sultry colours, making my eyes look bigger and sexier, long streaks of mascara flicking from the edges of my eyes. Thick lashes to follow. I'd been given some make-up lessons as a birthday present years ago, a joint gift from the Tranny Clan, and I used those lessons every time I did my make-up. Red lips, glossed over and sexy as hell soon followed and then I used some bronzer on my jaw and nose, gentle strokes to smooth away any masculine lines. Make-up done, I sprayed some perfume on my neck and wrists.

The man was banished and the exorcism complete.

I spent a few minutes to stick on some bright red nails, longer than my own. I didn't normally wear stick ons, preferring to paint my nails, but always had these as back up as they were quicker. Job done, I opened a new pack of hold ups and pulled them up my freshly waxed legs. The feel of the silky material as it gently caressed my legs was one I never tired of. I often wore them under my work trousers and loved sitting in meetings as I felt the silicon band at the top grip my thigh every time I crossed my legs.

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byLouise69© 2 comments/ 23346 views/ 8 favorites

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