tagTransgender & CrossdressersJosephine's First Evening Out

Josephine's First Evening Out


After the wonderful experience of spending a day at school dressed as a girl I didn't get a chance to repeat the experience. I wanted to, very much, but the following week the examinations started and it was important for me to do well as I was going onto college. Miss Stone and Mr. Graham told me that was no way I could do my exams as Josephine, as it would cause too many problems, so reluctantly I had to accept my school days as Josephine were over.

However they were as determined as I was that the end of my time at school was not to be the end of Josephine. One evening they took me to their house. I wondered what was going to happen, feeling an odd mixture of worry and excitement at being alone with them, but this visit was all about preparation. Miss Stone, who told me to call her Penny, had taken my measurements the previous day after one of my exams. That evening she had bought me some things to wear, so I didn't have to rely on the lost property box at school. I watched in mounting excitement as she unpacked a bra, some knickers, stockings and a suspender belt, a simple black shift dress and a pair of black high heeled shoes, all in my size. There was also a make up bag containing an assortment of make up and a book of beauty tips and ideas.

"We want you to do some homework for us" Penny explained, giggling slightly. I nodded, lost for words at the wonderful array in front of me. "Whenever you get the chance at home we want you to dress up, try doing your make up and get used to wearing the heels and the clothes. Will that be possible?"

At home there was only my mother. Deserted by my father when I was a toddler, she had a philosophy of 'work hard, play hard.' She had a reasonably well paid job as a personal assistant, but wasn't going to let being a single mum cramp her style. As soon as I was old enough to work a microwave she had started to go out and now I was 18 she went out on a very regular basis. In contrast I rarely went out and in any case, for the next few weeks had exams to prepare for each evening. This meant there would be plenty of chances for me to practice being Josephine at home, undisturbed.

As so it began. As soon has mum had been and gone for the night, I would change, slipping into my new clothes. I have to admit I loved the feel of the stockings and suspenders and I also loved the feeling of wearing the high heels. They gave me more poise and grace, making my walk and my stance more feminine. I would walk around the house, very carefully on the stairs, ending up at the dining room table. There using mum's make-up mirror I would experiment with different styles of make-up, following the guidelines in the book. Sometime I would go for a natural look, others as if I were going to a night club. Occasionally I would go for a totally tarty look, even though it didn't really suit me.

I always gave myself plenty of time to change and clean off the make up as I didn't want to get caught and have any explaining to do. Also I developed a bit of a routine. Wearing the clothes made me very aroused; sometimes it took every ounce of my self control not to cum in my pretty knickers. After undressing, I would shower, washing carefully, but taking care to keep myself aroused. Then I would go to bed, retrieve my tub of Vaseline from its hiding place and prepare to give myself a treat. As I lay there on my back, with my legs bent at the knee, I would massage a scoop of the gel around my bum-hole, circling it and gradually increasing the pressure until the tip of my finger penetrated. The feeling was so intense the first time I had to bite my lip to stop myself from squealing out loud. The gel eased the movement of my finger and soon I would have it sliding in as far as I could reach before sliding it out almost all the way. After a few moments of this my cock was hard and I could roll the tip between my thumb and forefinger, exposing the tip. Soon my whole body was trembling and I would cum, all over my tummy. The first few times I just mopped it up with a tissue, but the next time I decided to taste it. I rolled my finger through the sticky mess and then nervously brought it up to my lips. I forced myself to lick it off, the dipped it again and again, making myself suck the finger clean, swallowing every drop I could manage. It had a salty but not unpleasant taste. I would wonder if all cum tasted the same or not.

Soon I began to reward myself by wearing a pair of the knickers to school, under my trousers instead of my usual pants. They were only pink bikini briefs, nothing too sexy or uncomfortable, but I felt great knowing that I was wearing them.

Eventually my exams were over. Penny and Jason (Mr. Graham) were waiting outside the exam hall. They acknowledged all of the students leaving but they subtly handed me a note. Inside was the address of their friend, Kim, and the instruction to be at Kim's at 2pm the next day, which was a Friday. The note said that if everything went to plan that weekend there was a possibility of a job opportunity for the summer, before I was to start college. There was a mobile phone number for Kim that I was to ring to check the details.

I dialed the number on my mobile. A low, sexy voice answered.

"Hello, Kim speaking."

I became flustered. How should I start the conversation, I wondered.

"Hi, um, Penny and Jason gave me your number and told me to ring you."

"Oh hi, you must be Josephine, they said you'd be calling to arrange coming over to mine tomorrow. Is two o'clock ok?"

"It's fine."

"Super it'll give us time to get to know each other and get you ready for going out."

A thought struck me. Was Kim expecting Joseph or Josephine? Unsure how to ask I added "Um, how should I dress?"

"Well," she giggled, "would you be comfortable traveling to my house dressed as Josephine?"

I thought for a moment. "Well I've only been out of the house once, at school, and everyone knew what was happening, so maybe not yet, I guess."

"Fine then come as you are and bring all your girly stuff with you. See you at two!"

"Ok, Bye."

That evening I made sure all my stuff was ready, even using the washer-drier to make sure I had clean knickers! The next morning dragged by and I was hanging about the bus stop long before I needed to be. Even with a short wait I was still nearly half an hour early arriving at Kim's house. It was a nice semi-detached house in a leafy road. I went up the drive and rang the door bell.

A man's voice, quite like the one on the phone called out "Who is it?"

Maybe Kim has a brother I thought. "I'm here to see Kim, its Joe." I cut the name short, slightly confused. I hadn't expected a man to be there.

The door was opened by a man a little taller than me, but just as slim, wearing a bath robe and rubbing his hair with a towel. "You're early" he said accusingly, adding with a smile, "I was hoping you'd be late."

I followed him into the lounge and sat where he indicated on a sofa. "Is Kim going to be late?"

"In a way" he chuckled. "You see I'm Kim."

"Oh" I said. From the voice on the phone I had assumed Kim was a woman! The surprise must have shown on my face.

Kim smiled. "Give me a few minutes to start my transformation then I'll call you up. I hope you don't mind watching me dress?"

Five minutes later I was perched on the end of a bed, watching Kim finishing getting dressed and made-up. Now that she had finished drying her hair, I could see that she had long fair hair, pulled back from her face by an Alice-band. She was wearing a pretty blue dress. I watched as she smoothed stockings onto her long, slender legs, attaching them to suspenders that hung from the corset-like body she was wearing. As she began to apply make-up she told me that she had been dressing like this since she was at school. I told her about my first time as Josephine, forced to dress at school by the PE teachers Penny and Jason.

"Yes they told me all about that, I was quite jealous when I heard. I always dreamt of being able to go to school dressed as a girl!" Kim answered. "Tell me all about it."

I told her the whole story, interrupted occasionally by a question or two, or for Kim to explore how I felt or ask what I would have done if this or that had happened. By the time I had finished she was fully dressed and made up. She looked stunning.

"Right, my little princess, it's time for your magical transformation! You shall go to the ball" she announced dramatically adding in a less grand voice, "well 'The Rose and Crown' on Clifton Street anyway."

First she went through the contents of my bag, all of my feminine clothes, apart, of course, from the knickers I was wearing. There was much humming and tutting. In the end she announced that it 'wasn't too bad' but that she had some stuff I could use this weekend, until I had expanded my wardrobe.

Shyly I stripped down to my knickers and my transformation began. I slipped on my bra with no real difficulty and Kim produced some silicon inserts to pad them out. Then I pulled on a pair of opaque black tights. Kim selected a red dress from her wardrobe. It had long flowing sleeves, a figure hugging body which flared out into a short skirt. A borrowed pair of red stilettos finished the outfit.

Kim supervised my make-up, going for a quite sultry look. Finally she styled my hair using straighteners and putting in a little flick at the ends. I felt great and Kim assured me that I looked it too.

We sat chatting for a while, and then Kim said it was time to go.

This was it then; my first trip outside as a girl! At school everyone had been in on the joke, or soon knew about it. Now the object was to pass convincingly in public.

I had butterflies in my tummy as we left the house. To my amazement no-one seemed to notice us as we walked the couple of blocks to the pub Kim had mentioned. It was just after five and people hurrying home from work paid us little attention. I loved the feeling and the whole experience. On the way Kim explained that the pub was a gay pub that also welcomed the transgendered.

I looked blankly at her.

"Boys who want to be girls, like us," she explained, adding "and vice versa in a few cases."

The pub was already quite busy with, mostly, men, who had popped in on their way home from work. I sipped a diet cola while Kim explained a few points.

"Men who like TVs (that's transvestites), CDs (cross-dressers) or transsexuals are called admirers. Not all gay men fancy, like or even approve of us. Some admirers would even deny that they were gay at all. If a pretty girl sucks his cock, does it matter if she's got a cock of her own?"

It was all a bit confusing. I decided to go with the flow. As we sat Kim told me lots of stories -- I'll try to get her to write them down for you -- as the pub filled up. I saw a couple of boys I recognized from school who had been in the year above me. I didn't interrupt them.

After a while a DJ set up a small sound system and part of the pub became a dance floor. He was playing cheesy disco hits and the floor soon filled up with same sex couples.

"Excuse me?"

I looked up. A short chubby man a little older than me stood there. He looked nervous.

"Hello Dear," replied Kim, "What can we do for you?"

He looked at me.

"I wondered if you'd like to dance," he said "um, with me?"

"We haven't been introduced" I replied coyly. Kim nudged my leg under the table. I glanced at her.

"You flirt" she whispered.

"I'm Martin" he said. "You're very pretty."

I actually blushed as I said "Thank you."

Then Kim stood up and said, "Look after her while I'm gone, Martin, I'll be over by the bar, I've just spotted a friend I need to speak to. Be good!"

Martin took the chance to put his pint on the table and slip onto the seat next to me.

We chatted, I told him my name; that I didn't come here often, it was my first time here, and no, I didn't have a boyfriend. He was sweating.

I put a hand on his leg, and said "Do I make you nervous, Martin?"

He nodded, "A bit, yes, Josie, I've been coming here every Friday for the past month. You're the first, um, girl I've had the courage to speak to."

"I'm really flattered, Martin, thank you." I said, squeezing his leg and gently kissing his cheek. "I think such courage deserves a reward. Do you still want that dance?"

Amazed by my own flirtatiousness I led him onto the crowded floor. The song, an up-tempo number, finished, replaced by a slow love song. With a confidence I didn't feel I stood close to him and whispered in his ear "How perfect; hold me close."

I could feel his trembling hands. He was very nervous, but not too nervous to move his hands down to squeeze my bum. I didn't stop him; it was actually quite nice. I exchange smiles with Kim, over his shoulder. She gave me a thumbs-up sign.

"So Martin," I whispered, pulling him close to me, so close I could feel his erection pressing against my leg, "am I your first girl friend?"

The trembling increased. I pressed my thigh against him, managing to move so that I was rubbing his cock. More trembling.

Then abruptly he let go of me and moved away.

"I need the loo!" he muttered.

Five minutes later he returned. Kim and I were back at the table. Poor Martin came out of the Gents looking very embarrassed, trying to hide an obvious damp spot on his light coloured jeans. I went over to him.

"You okay, Martin?"

His mumbled reply was hard to hear in the noisy pub. I led him outside where it was quieter.

"No, Josie, I'm not okay. You know what just happened don't you?"

I resisted the temptation to say something funny or cruel. Instead I said, "Martin, I'm flattered."

He looked amazed. "Why?"

"It was because you fancied me wasn't it?"

"Yeah, but, um..."

I slipped him a kiss and a slip of paper.

"My mobile. Ring me or I'll be upset."

We kissed again and he scurried off home. Back in the pub Kim said it was time to go to see Penny and Jason.

We took a cab to their house. Penny opened the door.

"Well look at you Josie, aren't you pretty."

"Thanks Penny."

Kim wasted no time in telling them all about Martin and the events in the pub. Penny listened with interest.

"What was it about him that attracted you?"

"It wasn't his looks," I began, thinking about it for the first time, "it was when I thought about how much courage it had taken him to come over and talk to me; I guess I related to that and didn't want to be unkind."

Penny gave me a hug and a kiss on the cheek.

"That's so sweet Josie."

Jason wandered in. He had been in the shower. His hair was still wet and tousled and he was wearing only a towel wrapped round his waist. His muscular body glistened.

"Hello everyone," he greeted us. "I'd have put something on if I'd known we had company."

"Oh don't bother on my account," joked Kim.

Penny and I moved apart on the sofa and she indicated that he should sit between us. As he went to sit down, she reached out and grabbed the towel away. Unconcerned he took his place between us wearing just a big smile. He leaned back and put an arm around us both.

"So, which of you wants to suck my cock then?"

I giggled and looked at Penny. She smiled back and said, "I think we'd like to share that job. I'll start."

She bent forward and ran her tongue along his rapidly stiffening cock. I watched then Jason began to kiss me. After a while Penny sat up and said that it was my turn. She took over snogging her boyfriend, while I bent forward for my first taste of a cock. It was still wet from Penny's licking. Nervously I licked it, just for a moment, then for longer. He twitched appreciatively. Licking turned to kissing then I found myself sliding my lips over the exposed tip of his cock, taking him into my mouth.

"Good girl!" Jason moaned encouragingly.

"Go on Josie," added Penny, "make him cum."

I wasn't sure of exactly what to do. I mean I knew that a blow-job didn't involve any blowing, but apart from that I was making it up as I went along. Jason seemed to enjoy it when I sucked hard as I teased the tip with my tongue. He also liked it when I bobbed my head up and down with my lips wrapped tightly round it. I'd just bobbed down, so his cock filled my mouth when he came with a moan.

"Don't swallow it all!" instructed Penny,

I did swallow some, but with the rest in my mouth, I sat up. She kissed me and used her tongue to scoop some of his cum into her mouth.

Kim had videoed the lot on her mobile, so I got to watch a replay of my first blow-job! She sent me a copy to watch over and over.

When I got home, having changed back into boring everyday Joe, I checked my phone. I had two texts.

One was from Martin. Very sweetly he thanked me for being so nice and asked me out on Saturday.

The second was from Penny. It read as follows: 'fancy a job where you're Josie ALL the time? Ring me if you're interested'

I rang Penny straight away. She explained that a friend of theirs ran a hotel in Brighton, a seaside resort about 50 miles away. The resort was well known as a gay-friendly town and the hotel owner would be interested in a transvestite to fill a vacancy.

"He can interview you on Saturday."

I thanked her for the tip and promised I'd be there. Then I texted Martin, telling him I'd love to be taken out on Saturday, but that I had to go to Brighton. He texted back saying he'd love to take me and that he'd pick me up at 8am!

I could hardly sleep...

To be continued...

Report Story

byMisslexia© 4 comments/ 43110 views/ 7 favorites

Share the love

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

hearthawken333, algolfcrazy and 5 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (4 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (4)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: