tagTranssexuals & CrossdressersJosephine's First Job

Josephine's First Job


When I arranged for Martin to pick me up at 8 on Saturday morning to take me to Brighton for the job interview I'd forgotten a couple of things. I was reminded of the first when my Mum arrived home, noisily and tipsy at 3 in the morning.

With her in the house I'd have to sneak out, otherwise she'd catch me dressed as a woman. I just had to hope she'd be asleep. That was my second problem. To look at my best I needed to get up about 6 to shave, shower, fix my make-up, do my hair and dress. It's hard when you've got to creep about. Every noise sounds so loud! By half past seven I was ready.

I was wearing the black shift dress Jason and Penny had given me; it looked more suitable for an interview than the red dress Kim had let me borrow thee night before. Underneath I had chosen a matching black bra and panties, along with the opaque black tights. In my bra were the silicon gel falsies, also on loan from Kim.

I was just leaving my room when Mum burst out of her bedroom and into the loo. My heart pounded; had she seen me I wondered? Disgusting vomiting sounds came from the loo as I tip-toed past, holding my handbag in one hand and shoes in the other. Downstairs I waited anxiously, listening for movement from upstairs and watching for Martin's arrival. Mum appeared to have made it back to her bed, judging by the footsteps, but by ten past there was no sign of Martin!

I was just about to text him when a car pulled out and he got out. He looked slightly less nervous than last night, but no taller or thinner than I had remembered. Briefly an unfavourable comparison to Jason's toned body flashed through my mind, but I put it to one side and opened the front door before he could ring the bell.

His smile was huge when he saw me, but there was no time to waste hanging around on the doorstep.

"Let's go, I'll explain on the way!" I said.

Martin, in the role of perfect gentleman, insisted on opening the passenger door for me. I stepped in as gracefully as I could and, a few moments later we were on our way.

"You look stunning Josie," he said, "I wasn't sure what to expect."

"How do you mean?"

"I didn't know if you dressed like this all the time or just in the evenings. You might have come out of the door dressed as a guy." Blushing he added swiftly, "I'm really glad you didn't though."

I hadn't thought of that.

"Stop the car!" I said urgently.

He pulled into a lay-by. I leaned over and kissed him, full on the lips. He looked surprised.

"That was for turning up even though you didn't know what to expect."

I kissed him again.

"And that was for saying I look stunning."

As we drove on I told him the story of my first and only day at school. I explained that I had so enjoyed being Josie that I had began to dress this way whenever I could.

"The only thing is that my Mum doesn't know yet, hence the quick getaway this morning!"

"I see," he said, "so what is this job interview then?"

I explained that I didn't really know much, except that it was in a hotel and that I'd get the chance to be Josie all the time.

"Sounds cool" he replied.

I sensed a tone of sadness in his voice and felt the need to reassure him.

"Luckily it's only an hour drive, so you'll be able to come and see me."

"Really? You'd like that?"

"I'd like that a lot." Curiosity got the better of me. "So what makes a nice guy like you get a girlfriend like me?"

"What, really pretty and exciting to be with?"

"Don't avoid the question," I scolded jokingly, "thanks for the flattery, but, really why?"

He sighed. "You'll think I'm a sad loser."

"I promise I won't, please tell me."

"I was 14. I'd plucked up all my courage to ask Jenny Simpson out. She laughed in my face. That evening at home, on late night cable TV I watched some American chat show. It was all about transvestites and transsexuals; all of them beautiful. I was besotted. Two things happened. I forgot Jenny 'smug-bitch' Simpson and I had the best wank ever. Since then I've wanted a TV or TS girlfriend."

"Wow, thank you for telling me." I said adding, "Next time I'd leave out the wanking part."

"Too much information?"


We arrived in Brighton not long after nine, parked and made our way to the hotel. It felt quite natural to be strolling along by the sea-front, hand in hand with Martin, just like any other holidaying couple.

The hotel was slightly shabby, and one of the smaller ones on the sea front. We went in. a bored looking man, with carefully styled hair, sat at reception. His name badge said 'Liam'.

"Can I help you?"

I explained that I was here for an interview for a job vacancy.

"Oh you must be the tranny, Jessie is it?"

"It's Josie."

"Of course it is," he said smoothly. Picking up his phone he punched a couple of numbers. "Mr. Simms? I've got Josie in reception. For the interview. Right away."

Liam directed me to a door across the hall. "Mr. Simms will see you now. Good luck."

"This is it then," I said to Martin, "wish me luck."

We hugged and kissed.

"Good luck, Josie"

Mr. Simms was a tall thin man who reminded me of a praying mantis. He shook my hand and gestured to the sofa, muttering "far less formal this way."

He went on to explain that he knew Kim from 'way back' and through her Jason and Penny.

"Now they've told me all about your exploits at school that day and I've seen the video of the other night."

I blushed.

"Now the question is do you really want to go full time?"

"Yes, more than anything."


I thought for a moment. Why did I want it so badly? After all a few weeks ago I'd never even cross-dressed. Now here I was 50 miles from home, with no male clothes with me, trying to get a job in hotel.

"It felt right from the first second. I just feel comfortable being a girl and doing girlish things."

"Excellent, Josie," he said patting my knee. "We run several theme nights here in the basement club. Would you be happy to wear costumes or uniforms?"

"Of course, so long as I get to be Josie, I'll be happy."

He went on to explain the job. I'd be on reception, waitressing in the dining room and behind the bar in the club. Some nights I'd be on call for room service. The pay was poor, but that was because it included my room and meals, since I'd be living in the hotel.

"There's one more thing, which is a bit delicate. We like our staff to make our guests feel welcome; go the extra mile, if you get my drift."

I didn't.

"Well let me put it another way ..."

I understood this time. In a nutshell you had to be ready for 'odd' behaviour and requests from the guests; at the hotel things could get a bit wild. It sounded great!

I took the job. I would be starting on this evening and my room would be ready by this afternoon.

Having accepted his congratulations I took Martin shopping. I needed a complete wardrobe, but I was on a budget. I took all I could afford out of a cash machine. We went to a cheap chain store for underwear, tights and stockings, but for the rest of my clothes we hit the charity shops. I picked up some summery dresses, blouses and skirts, and some more shoes. With what little I had left I bought some make-up essentials.

I was quite guilty about having nothing left to give Martin any petrol money, buy lunch or even a drink, but he told me not too worry. In a public toilet I changed out of my best dress and into a white sleeveless blouse and short shocking pink skirt. The black bra showed through so I swapped it for a new white cotton one. I left my legs bare and wore my newly purchased sandals.

We headed to the beach to share a sandwich and a can of drink, then we lay back and sunbathed. I lay close to Martin, but at an angle, resting my head on his chest. As we lay there he began to doze off and I had a naughty idea. Slowly and carefully I undid his trousers and slid down the zip. I managed to free his cock from the confines of his boxers and I stroked it gently. He soon woke up and his hardening cock showed how much he liked my attentions.

"Josie, for fucks sake, someone might see."

"Let's give them something worth seeing then!" I replied naughtily.

I moved so my head was not in the way of his view. Slowly and deliberately I wrapped my hand round his shaft. I slid my thumb and index finger up and down, wanking him, while I licked the exposed tip of his cock. It was glistening with pre-cum and I savoured the salty taste. Martin could see every flick of my tongue and it looked as if his eyes would pop out.

"Josie, you'd better stop, I'm gonna cum soon!" he implored me.

I smiled, Martin later described it as an evil smile, and began to suck his tip into my mouth, teasing his hole with my tongue. The combination of sucking, tongue teasing and wanking made him cum. I felt him twitch and his spunk hit the roof of my mouth; I swallowed eagerly, licked him clean then sat up, washing his cum down with some fizzy drink.

"You're mad," he declared!

"That's why you love me!"

"Who says I love you?"

I slapped his shoulder, rather harder than I intended.

"I think when a girl has just given her boyfriend a blow job he would be wise to say he did love her, otherwise he might get dumped!"

He looked at me sulkily.

I threw him a lifeline.

"So you gonna visit me next weekend?"

"If you want me to," he replied sulkily.

"You'd better!"

We said our good byes and I headed off to work. Liam showed me to my room. On the top floor, in the attic really were the staff bedrooms. There was a key-pad lock on the door to the stairs.

"I've reset it specially for you," he said, "five, one, five, five, four."

For a moment I didn't get it. Then I saw the display. On the calculator style display it spelled S-I-S-S-Y.

"Thank's Liam, that's so sweet of you," I said, more amused than annoyed.

"My pleasure Josie," he laughed, "welcome to the madhouse!"

He showed me round. Every expense had been spared. Once in the attic the rooms didn't have locks. My bedroom was at the back of the hotel, with a view of a brick wall. There was a kitchen with a washing machine and a bathroom which we'd share. There were three of us in all; the third was a girl called Anna.

"The rooms are shite," he commented, adding "that's why we spend most of our time working."

In my room was the 'uniform'. It consisted of three fitted white blouses, a short, black, pleated skirt and a red waistcoat. On the waistcoat was a name-badge; 'Josie'. I changed into it immediately. Liam sat there watching.

"I don't get the whole guy in girl's clothing thing," he said. "If you're gay, you're gay; how does dressing up change anything?"

I fastened up my skirt. I sat on the bed next to him to put on the black over the knee socks I planned to wear.

"I don't know Liam, it just feels right to dress like this" I replied, adding "and I think I'm bi not gay."

"Thank god for that."

We both looked up. A chubby young woman, probably a little older than me, with dyed blonde hair, with dark roots showing, stood there. She was wearing the same blouse, waistcoat and skirt uniform as I was, although her legs were bare.

"I'm Anna," she introduced herself. "So Josie the sissy likes a bit of pussy then?"

"You're so crude sometimes Anna," muttered Liam. "I've got to open the bar, show Josie what to do on reception."

I followed them down to reception. I would be holding the fort there while Anna waitressed the dinner service, with Liam's help. I listened carefully as she explained.

"It's important to remain professional when you're dealing with customers. Some of the sights I've seen! I find the hardest part is the stubbly trucker in a frock; that can be hard to keep a straight face!"

"Do you feel like laughing at me then?" I asked, fishing for a compliment.

"You're kinda cute," she said, "in fact compared to some of the trannies we get in here you're practically Miss World! Well, maybe Miss Seaview Hotel!!"

We laughed.

It was quite busy on reception, but I coped, checking in a stream of men, some of whom were obviously gay, but many didn't fit any stereotype. I managed to fill out all the right bits on the computer system and give every one the right keys.

About 8pm the disco opened up. Liam was behind the bar, while Anna and I acted as waitresses, helping out at the bar if necessary. Some of the patrons were clearly regulars, judging by the number of 'you're new' comments I received. To my disappointment there didn't seem to be any other trannies, it was wall to wall gay guys, the majority of whom had either paired off or were on the pull. Liam came in for a lot of attention.

"That's why we put him behind the bar on Saturdays," explained Anna. "The one time he ventured into the crowd his bum got pinched so many times he could hardly sit down!"

It was hard work, but fun, and to be accepted as Josie made me feel great. It was 2am before we finally closed. Some of the men went back to their rooms, or often, someone else's room. Others went on to another club. I noticed Liam hurrying off with a guy who'd propped up the bar all night.

"He's pulled again!" commented Anna as we headed for the staff quarters.

We reached the locked door and she chuckled as she typed in the code. Inside she took my hand.

"Fancy a shag?"

I thought for a moment. It was 2am; I was tired, hot and sweaty, as was Anna. Her room was a mess.

"Of course I do, if you're offering!"

Our uniforms joined the clothes on the floor. She insisted that I kept my knickers on, pulling my hardening cock out of the leg of the knickers as she pulled me onto the bed. She clambered on top, having pulled off her panties, and her ample breasts jiggled along with her 'buddha-belly' as she lowered herself onto my cock. She was already wet and I slid into her easily, her pussy gripping my cock tightly enough to push back my foreskin. With a surprising amount of energy we made love vigorously to the accompaniment of creaking bedsprings. I came first, but couldn't stay hard long enough to help Anna to her own climax. Undeterred she clambered further up the bed and lowered her self onto my face. Her wet open, cum-dripping pussy smothered me, a flabby sweaty thigh each side of my head. It was so arousing, being enveloped by Anna in this way, I licked, slurped and sucked at her pussy, putting my tongue right up into her cunt as far as it would go, before sucking her exposed clit into my mouth and flicking it with the tip of my tongue until she orgasmed, very, very noisily. Spent we moved into an embrace and slipped into sleep.

Liam woke us when he returned the next morning. Anna got up and, stark naked wandered into the kitchen to chat to him. I gathered up my clothes and tried to sneak back into my room un-noticed. I failed and had to endure five minutes of chat before I could escape. I showered and dressed.

First I was on reception and was quite busy. A lot of our guests only stayed for one or two nights. After lunch the new guests began to arrive. Some of them seemed to have rather a lot of luggage for a short stay. Liam explained that they were generally cross dressers, who had to bring two sets of clothes, one masculine and one for their feminine alter ego.

"Sunday night is tranny-night in the club you see. Some of them only want the room to change in and they won't even stay the night."

Our next duty was to make beds and change sheets in rooms where people were checking out. Judging by the used condoms and empty tubes of lubricant some of our guests had enjoyed themselves!

The afternoon brought me three visitors, Kim, Penny and Jason. Kim checked into a room and went straight up to change, while Penny and Jason waited in the bar. As soon as I could I slipped away from reception and joined them for a chat. I told them how much I was enjoying myself and asked why they were there.

Penny explained that Kim would be hosting the club that evening.

"She runs a really cool club and we always have a good time at it."

They were right, Kim did run a really cool club. The place was filled with glamorous (and some not so glamorous) trannies, mixed in with some of their partners, and admirers. Kim made everyone feel at ease as she mingled with the crowd.

I wasn't quick enough at fixing drinks to run the bar yet, so I was waitressing again. I spent a lot of my time chatting. At first I tried to avoid it, but Mr. Simms, told me that it was important to make the guests feel comfortable, so I mingled too.

After an hour or so, I saw Kim and Mr. Simms talking; they beckoned me over. Kim said that I would be more use helping her than waitressing, so I was sent to change. I put on the red dress I'd worn on my first evening out swapped the over the knee socks for a pair of hold up stockings and hurried back down.

On Kim's instructions I mingled, checking that everyone was enjoying themselves. I helped some of the less confident TVs to take a turn on the dance floor, by asking them to dance with me. I also had to be a dancing partner for a couple of the male admirers, turning their attention away from those who found it unwelcome.

At the very end of the evening I was lucky enough to be dancing with Penny and Jason. She was so graceful I copied her dancing as best I could. He had some good moves too. Then Kim cued up the last slow smoochy number.

Jason pulled me close and said "I believe this is our dance."

He put his arms around me and I rested my head on his muscular chest as he steered me round the dance floor. As our bodies touched I felt myself melting into his embrace. The dance ended and he led me upstairs to his room.

Penny opened the door; she was naked. I looked at her sleek body as she pulled me into the room. Jason joined me on the bed, kissing me.

"I'm ready" Penny announced.

I looked up; to my amazement she was wearing a strap-on cock, it's length shiny with gel! Jason helped me into a kneeling on all fours position and slipped my knickers down. My own cock sprang free, already hard, but this wasn't about me, this was for Penny.

Penny knelt behind me and with Jason's help, positioned the tip of her strap-on by my anus. With no pretence of gentleness she held my hips and thrust forward, her body slapping against mine. She pulled back slowly then slammed forward again, over and over. Each forward thrust clearly did good things for her as her moans and cries became more intense. For me it was less enjoyable, even slightly painful, but, bizarrely, I was just happy to be used by her. Eventually she stopped, trembling as she climaxed.

"Thanks Josie," she said, "sorry if I was a bit rough, but it gets the end of the strap-on to stimulate my clit." She kissed me on the back of my neck and then pulled out.

"That's ok Penny, I'm just glad you enjoyed it." I replied truthfully.

The bed sagged as Jason took her place. His cock was only a bit shorter than the strap-on but he was much thicker. He was also wearing a ribbed condom and, believe me, I could feel every rib as he gently eased his cock into me. He was, surprisingly, more gently than Penny, pushing in slowly as if to maximize and prolong his own pleasure. Gently and rhythmically he began to fuck my arse, pushing in so far I thought it would never stop, before pulling almost right out. I couldn't stop myself moaning in pleasure, pleasure that grew and grew with every one of Jason's thrusts. By the end I was quivering and could feel my own cum, dribbling uncontrollably from me, yet he showed no sign of stopping. He continued for what seemed like an eternity, before he pulled out, still hard!

Collapsed on the bed I watched in amazement as he peeled off the condom and began to fuck Penny, right beside me on the bed! I felt a twinge of jealousy when he came. We said goodnight, but they didn't notice as I pulled my knickers back up and crept out, barely able to walk.

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