James' New Job Ch. 02

I drove home in a bit of a daze, the last hour or so swirling around in my head.

I'd just signed on to be a crossdressing sex worker. Part of me was filled with such a nervous energy that I was barely keeping a lid on it, mostly though I was having some serious second thoughts.

Who were these people?

Who were 'the investors?

Were they connected to a criminal organisation?

Would I make a hot girl?

Ok, the last one just randomly popped up, couldn't help but wonder though.

The drive home took just over half an hour and when I went inside, everyone was there. My sister, Lucy, who was three years my senior, her boyfriend, Jack (bit of dick if I'm honest), Mum (Joan) and Dad (Barry).

As I walked in my Dad piped up first, "ah, our intrepid wanderer returns, no doubt from another days fruitless job hunting."

I'd rehearsed this in the car. "Actually, I've had a big success, got myself a great job and I'm starting right away."

This got their attention, they all gathered round. "You know that new, very upmarket hotel, just off the bypass? I'm their new head of marketing and social media advertising." Obviously telling them the truth wasn't possible yet and I needed to come up with something decent to account for all the money I'd be about to be earning.

Unfortunately Lucy was excited for an entirely different reason. "I know that place, oh wow, we've been trying to get a table at the restaurant there for ages." A manic gleam entered her eyes, "hang on, this is awesome, you can totally fix us up."

Fuck, the last thing I needed was my sister hanging out round work, "I'll see what I can do. Look, it comes with accommodation and because I'm management I have to live on the premises for emergencies."

Jack interrupted me, "emergencies? What emergencies do you get in social media marketing?" My Dad guffawed, he loved Jack.

I ignored him. "I'm sorry, I'm only here to freshen up, pack a few bits and then I'm off." I looked over at my Mum, who so far hadn't said a word, "don't worry Mum, I'm only half an hour down the road, I'll be round all the time."

"I know love," she replied, "just my little boy all grown up." She touched me tenderly on the shoulder, "I'll still miss you though."

I went upstairs into my bedroom and closed the door, taking a moment to sit on my bed. Other than the drive over, this was the first opportunity 'd had to really reflect on what I was about to commit to. I wasn't a virgin but neither was I exactly setting the world on fire with my sexual prowess. I'd thought about what it would be like to have sex with another guy once or twice but I can honestly say I'd never thought of crossdressing.

I resolved to give it the week and then see what happened from there. What was the worst that could happen, right??

I undressed and went into the bathroom, making sure to lock the door behind me. Grabbing some shaving foam and a fresh razor, I stepped into the shower and lathered up my legs. Taking my time, I methodically and precisely shaved both legs, swiftly moving to my arms, chest and armpits, leaving my groin till last. When it came to that area I took special care and left a small one inch wide and two inch long 'landing strip' just above my dick.

When I was done I showered and got out, once I was dry I looked around for some of my sisters moisturiser, Samantha had advised me to make sure I applied this to the areas I'd shaved so I did so, leaving my body feeling as fresh as I could ever remember.

As I was getting ready to leave the bathroom I noticed the lid was off the laundry basket and some of my sisters clothes were overhanging the top. I walked over and just under a jumper were a couple of pairs of her panties and a pair of tights.

I ran one of the pairs of panties through my hands, they felt so beautifully soft and delicate compared to my cotton boxers. The ones I was holding were a thong and I held them out in front of me to see which way round they went.

"Fuck it, here we go," I said quietly to myself, sliding them up my legs. Where the silk and lace came into contact with my skin, my whole body fell electrified. I slid them all the way up and adjusted them so they were sitting right. The thong part felt a bit weird, going up the crack of my arse but not uncomfortably so.

I finished off with some hair wax, deodorant and putting a towel round my waist, ensuring it covered the panties, I walked through into my bedroom.

After I got dressed and packed a few things into a hold-all I went back downstairs to say goodbye to everyone. Now my mind was made up I wanted to get back to the hotel and start my new life.

I promised to call and reminded everyone I was only going half an hour down the road, hence my small bag, I'd be popping back in regularly.

I went outside, got in my car and drove away.

"How was it?" Samantha poured me a glass of wine from behind the bar to go with her own and sat down opposite me at a table in the corner, away from the few daytime customers.

"Pretty easy really, I was in and out in an hour."

"Good, grab your bag and your drink, I'll show you your new home," as she said this, she got up from the table, gave me a conspiratorial wink and went back through the bar, through a door I hadn't seen before which opened out to a space outside set in a beautifully landscaped garden. About twenty metres away were half a dozen cabins lined up next to each other.

"We get the VIP suites," she laughed, "we bring in the big bucks, it's only right we get the best accommodation, plus we usually use these for our entertaining. You did shave, didn't you? I am so looking forward to getting you out of those dreary jeans." She grabbed my arse as we approached the door to the cabin marked with a '4'.

"Come on in Jenny, let's get this party started."

I wasn't expecting to walk in and find another woman inside and I recognised her as the lady I'd seen earlier on reception, I think her name was Rebecca. She turned towards us as we entered and smiled at us both. "You made it then, hi, I'm Rebecca. I'm very pleased to meet you," placing an emphasis on 'very'.

If Samantha had the body of a porn star, Rebecca had the body of an athlete. At least five foot eleven, legs that seemed to go on for miles and a lean but smooth upper body that seemed to exude physical prowess. Her breasts were much smaller than Samantha's, I'd say a B cup but they were perfect for her build and size. Her hair was a luxurious brunette that cascaded down over her shoulders, stopping just short of the middle of her back.

Samantha took my bag off me and dumped it onto the bed, she was suddenly all business and was taking charge. "Right, strip off and go and stand in the shower cubicle, we need to see what kind of a job you did with your shave."

It was then I remembered what underwear I was wearing.

"Right, strip off. Right, I'll do that right now." I was floundering.

"Well go on then, we don't have all night, " Rebecca was growing impatient. I groaned inwardly and went for it. Their reaction to seeing me in a sexy silk thong wasn't what I had expected.

As I slipped my jeans off, standing in just the thong, Samantha looked first at the knickers and then up at me. "Turn around," she said simply. I did so, "slowly," she added. "Your arse in that thong is quite magnificent, you are going to be a very popular young lady, now get them off and we'll get you a fresh pair."

When I'd stripped completely Rebecca produced some clean panties for me to put on as well as a short silk gown that came to about mid thigh. While she did this Samantha explained how things were going to be.

"We're going to do your hair, make up, a manicure and a pedicure. We'll then get you dressed ready for a night out on the town, happy?" I nodded.

"Good, while Rebecca's doing all that I'll go through what you're going to be doing as part of our team from here on in." She stopped to take a drink of her glass of wine and then carried on. "You'll have a day job within the hotel, just so we can have you registered as an employee, you need that for this cabin for a start, any idea what you want to do?"

"I did media studies at Uni, how about marketing or something like that?" I looked from Rebecca to Samantha.

"That could work," said Rebecca. While she said this she'd been filing and buffing my fingernails, they'd never looked so healthy.

"Ok," said Samantha, "you'll do eight hours a week in that job, the bare minimum really, the rest of the time is yours to a certain extent, but you will be expected to keep yourself in shape," she gestured to Rebecca and herself, "we do at least an hour a day in the gym, you'd be more than welcome to join us. For you, for the first couple of months at least we'll have make up, hair, all the girly shit that we take for granted, you'll have to learn."

Samantha leaned in close, "lots of girly time to bring out your inner slut."

While Samantha had been talking, Rebecca had been diligently applying creams and foundation to my face and having finished with that had moved to my eyes and was currently applying mascara to my lashes. "It's a cliche I know, but why do boys always have the best lashes?" She nudged me, "yours are fucking gorgeous."

Samantha watched her while she finished with my eyes then helped her pick out a shade of lipstick and some lip gloss.

"Not quite bright red but a nice girly pink," she declared and applied the lipstick then the gloss, applying several layers.

"Right, the crowning glory, literally," she squinted at me, "big, long blonde curls, cute, preppy strawberry blonde or seductive brunette?"

Three wigs were sat on the table, I was expected to make a choice, "the, er,, strawberry blonde one I think."

Rebecca beamed back at me, "right choice." A wig cap was secured to my head and then the wig was put in place and after several minutes of adjusting this way and that the two girls seemed happy and finally let me see myself in the mirror.

Holy shit, I was hot. I mean in a cutesy, butter wouldn't melt, girl next door kind of way. I stood there admiring myself when I saw, in the mirror, Samantha come up behind me and slide her hands over my bum and then up along my hips up to my chest, where my breasts would be if I had any.

"You're so beautiful," she whispered and slowly turned me around so I was facing her. She leaned in for a kiss and our tongues met and we kissed passionately while our hands explored each other's bodies.

She manouvered me so I was back up against my bed and then gently pushed me onto my back. As I laid out on the bed, Rebecca took over from Samantha and straddled my chest.

While she was doing this I felt Samantha gently slide her hands down my legs and over my feet, she then slid them back up my legs, wrapping both hands around my cock and balls, gently massaging my cock until it was fully erect, she then licked the top before sliding the whole length into her mouth.

Meanwhile Rebecca had moved up my body so her pussy was directly above my mouth, "you know what to do," she said as she lowered herself over my mouth. I probed her with my tongue, gently at first then more urgently, keeping time with her hip thrusts as she gyrated and ground herself against my face. "Mmmm, fuck, oh yes, keep it like that baby," she reached down and grasped the side of my head as she pushed herself down harder over my mouth, my tongue went deeper inside of her and I could taste her juices, she was obviously extremely turned on as she very quickly started breathing deeply as she neared her orgasm.

Rebecca gave out a long shudder and gripped my head tighter as she came, "oh fuck, yes, yes, yes." I savoured the taste of her as she came multiple times, eventually she regained control and peeled herself away from my face and climbed off me.

Only then did I go back to appreciating the fantastic blowjob I was getting from Samantha, unlike the several I'd had in the past where my partner had been definitely rushing and trying to get the job done as soon as they could, Samantha was taking her time and clearly relishing the task in hand as she alternated between long, slow, deep sucks and then licking my balls, sliding her tongue along the length of my cock. She also knew when I was getting close to cumming and she would slow down.

Rebecca leaned over me and gave me a long, sensuous kiss, tasting herself on my lips. She looked over my shoulder at Samantha, "Hey, Sam, let me have a go there, you've got to let Jenny go down on you, I haven't cummed like that in ages, she definitely knows what she's doing."

We moved around on the bed so I was on my front facing Samantha's opened legs and I started by kissing Samantha's thighs, slowly moving up to her pussy. I slid my middle finger in and then played with her clit with my tongue. While I was doing this I felt Rebecca manouver herself underneath me so my cock was above her mouth and she angled her head so my entire length slid effortlessly down her throat. I wasn't ready for what she did next. Having lubricated her fingers by playing with her soaking wet pussy she slid one, then two fingers up inside my bum. The sharp, unexpected pain soon gave way to the most wonderful feeling as she quickly found my male g spot and my cock grew impossibly harder.

Samantha was now guiding my mouth, letting me know exactly what she wanted and I could tell by her rapid breathing and gyrating that she was close to cumming. She pulled me against her harder and then came, just as intensely as Rebecca had, again covering my face with her cum.

The combined sensation of Rebecca deep throating me and fucking my arse with her fingers was pushing me towards my own orgasm as well, "Oh, god, I'm cumming now," I just about managed to give Rebecca some warning before I came like I never had before, what felt like gallons of semen erupting from my cock, straight into Rebecca's mouth.

When I finally stopped cumming, Rebecca extricated herself from underneath me and drew herself up to eye level with me then, pulling me in for a lovers embrace, kissed me passionately, swapping my own cum into my mouth. "Swallow it Jenny," I heard Samantha say. There was so much but I did as instructed, it tasted salty and the consistency was a bit slimy but it wasn't too disgusting.

I opened my eyes to see the two girls looking at me, smiling, "I think we need to redo your make up," said Rebecca, then the three of us burst out laughing, "you total slut."

Rebecca fixed my make up while Samantha laid out my clothes, this time round Rebecca got me to do some of my make up myself, applying my own lipstick and gloss. All the while I was keeping one eye on the clothes that Rachel was laying out on the bed.

Once the make up was done and the wig was brushed out to Rebecca's satisfaction Samantha led me over to the bed.

I took off the robe and thong I'd been wearing and standing there naked in front of these two incredibly sexy and beautiful women I started to get dressed.

First came the black, silk panties that caressed every curve of my bum as I smoothed them into place. Then the silk thigh high, hold up stockings. This was a first for me and the way they felt as they glided up my smooth legs was one of the most erotic feelings I'd ever had.

Next was a black, lightly boned corset that I was able to tie up myself but was tightened up using the efforts of both my helpers, by the time they were done, I had a wonderfully sexy and waspish waist. Samantha produced some breast forms that she inserted into the cups of the corset. "You, my dear, are now a very curvy and seductive B cup. Not too big, not too small." She winked at me. "A nice handful, as they say. Once we know you're staying, we'll make the investment in a decent pair of silicone, glue on titties for you, but for now, these will do."

Next came a red, satin skirt that was tight enough to accentuate what both girls thought was a great arse and would also encourage me to take smaller, ladylike steps when walking. A cream coloured blouse was next and was tucked into the skirt. Again, the blouse was just tight enough to highlight my curves, Rebecca undid enough buttons so my cleavage was nicely on display. Rebecca had contoured in my false breasts to my skin tone to make them seem more natural and the effect was rather amazing.

Some jewellery and I was almost done. Samantha sprayed me with some perfume, dabbing some on my cleavage. "Poison, darling, never leave home without it."

I'd been eyeing up a pair of spectacular looking heels that had the distinctive red sole with some trepidation.

Rebecca saw me and laughed, "don't worry, we've got plenty of time,we'll have you walking like a supermodel before you know it."

I looked over at her with a mix of scepticism and disbelief but nonetheless took a few tentative steps and at least stayed upright.

The tight skirt helped as well as the advice from the two girls and sure enough within ten minutes I was walking quite naturally.

"Right," said Samantha, "Rebecca needs to get back to work and I need a drink. Let's go over to the hotel bar and see how we get on, there's normally a couple of randy old goats in there we can test you out on."

Rebecca gave me a quick peck on the cheek then left. Samantha and I took the short walk over to the bar, I was obviously nervous which she picked up on and linked her arm through mine, "don't worry, you look stunning, just act naturally and we'll have a blast."

We walked in to the bar which was about half full and I sat down at a booth while Samantha went to get a drink. Before she got back, a middle aged man sidled up to our table. He wasn't bad looking, decent body and dressed quite stylishly, I could do a lot worse. Hold on......what the fuck? Why was I even looking at this man as a potential sexual partner.

Before he even had a chance to speak, Samantha appeared, "oh, hello Terry, meet Jenny, just started, heading up our online and digital marketing, bit out of your league though, wouldn't you say?"

He stammered a hello, quite clearly flustered then disappeared. "You're going to have to get used to that, I'm afraid. Every single man in here watched you walk in." She sat closer and whispered in to my ear, "just think what they'd pay for a night with you, to feel those luscious, full lips wrapped around their cock, to slide themselves balls deep into that fantastic arse and then to cover your beautiful face in their cum. That's what we're selling, a dream, a fantasy, and you, you sexy little bitch, are every dirty, sordid, forbidden fantasy they've ever had."

She turned and poured two full glasses of wine from the bottle she'd bought over and handed one to me and winked, "cheers, let's enjoy this drink then we'll head out."

"Is that wise? What if I get, well, you know, made?"

"Really? You're hotter than most of the real women in here, so stop panicking. We need to show you off, it won't be a late night anyway, couple of hours, tops."

Over the next half an hour we finished the wine and got ready to leave, "where are we going, anyway?" I asked.

"Georges, it'll be just the right level of busy and quiet and the standard of clientele is pretty decent." Georges was a fairly upmarket wine bar in the town and Samantha was right, it should be perfect for my first proper venture out as Jenny.

We took an Uber and was there in fifteen minutes, we went inside and I was totally unprepared for the reception we got. Everyone obviously know Samantha and greeted her warmly. Attention was soon turned to me with everyone demanding to know who I was. As I was introduced around I felt more than one hand linger a second longer than necessary on my waist and once, directly on my bum. It was a whirlwind and I had to admit, it turned me on. As James I would never elicit this kind of attention but it appears Jenny was suddenly the girl everyone wanted to know and be seen with.