Disclaimer: The original characters and plot of this story are the property of the author. No infringement of pre-existing copyright is intended. This story is copyright (c) 2011 Deborah Karen. All rights reserved.
I had an interesting job part 3
I woke up after my first ever date as a girl.
I had stripped off my dress and tights after I got in and lay on the bed in my bra and knickers. I felt so strange. I had really enjoyed my date with Paul and had wanted to invite him in, but knew that was impossible. I just didn’t know how I was going to be able to take things further without him finding out that beneath the makeup, high heels and dress that I was really a boy.
Right at that time though I felt like a girl and a horny girl too! I played with my blackberry in its pink cover. I really wanted to text Paul and let him know... Well, let him know what exactly?
My hand was resting on my knickers and I stroked the fabric idly. I could feel myself stirring under the confines of satin and lace. I went over to my draws and pulled out the black lace top stockings I had taken from Claire’s bedroom earlier in the week. Another rummage produced the suspender belt, bra and knickers.
In about five minutes I had stripped off the underwear I had worn on the date and was stood in front of the mirror admiring myself in Claire’s sexy underwear. I had put on the black suede heels too and I looked critically at my reflection wondering if I actually could convince Paul that I was female dressed like this.
I certainly felt sexy. I knew I felt confused about this feeling when in boy mode, but at that moment in front of the mirror in sultry heels and underwear I wanted to feel wanted by my boyfriend. I laughed to myself; I wouldn’t have imagined thinking that a couple of weeks ago!
So now I was lying in bed with the weekend ahead of me. I was wearing a t shirt and knickers and bra, just simple cotton underwear. I wondered what to do. I wondered what Paul would be doing; would he be thinking about me? I checked my blackberry, but there were no messages.
I went on the internet for a while. I was going to need another wig for this latest scheme dreamt up in chambers for me to impersonate some Italian or Spanish looking girl. I tried to recall the photos that Tommy had shown me. I looked at a few styles, but decided I would be better off waiting until I had a better idea of what this girl really looked like.
After a few hours of surfing with the radio in the background I decided I ought to get dressed. I had a quick shower and shaved all over. It wasn’t quite as nice as having a long soak in bubble bath, but I guessed most girls didn’t have the time to do that every day.
I did my make up and put on fresh underwear, leggings, a long jersey top and some simple jewellery. I fixed a bit of lunch and then flicked through one of my girly mags. I could easily become engrossed in articles about 100 summer dresses under £30 these days!
By mid afternoon I was going a bit stir. Still nothing from Paul. Didn’t he like me? I kept checking my blackberry, but no messages came through. Then around 4 ish a text:
‘Hi... how you doin? X’
I couldn’t play it cool could I? Texted him straight back
‘Hi, I’m ok thanks x’
‘What you up to? X’
I wanted to sound like I was in the middle of great social whirl
‘Thinking of meeting up with some of my girlfriends and shopping x’ I lied
My heart started beating a little faster. I sat on the sofa with my knees drawn up under my chin trying and failing to play it cool.
‘Why’s that? X’
‘Was wondering if you wanted to come over x’
I had NOTHING to wear
‘When were you thinking? X’
‘Soon as you’re ready? X’
‘Might need to get changed x’
Paul replied that was fine, to take my time and texted me his address. I was stripping off my top as I ran into the bedroom. I really didn’t know what to wear. Leggings and Uggs seemed a bit too casual and everything else was too much like work wear. I certainly couldn’t get dressed up like I had for our date. I toyed with the idea of the black underwear and stockings under my long coat, but eventually decided I would need to shop and quickly.
I sat on the loo with the cock squeezed between my legs and my knickers around my ankles. I was flicking through Closer for inspiration. I decided I liked the idea of a little military style skirt, quite short with thick tights and knee boots. I had plenty of tops I could wear, but decided that a little fake fur waistcoat would be in order too.
Primark came to my rescue as before and I even managed to score a pair of brown boots with about a 2” chunky heel and lots of straps and buckle details. By the time I was ready it was getting on for 7. Paul had texted me a couple of times, joking and saying stuff like ‘are you still coming??’ I came over like a proper girl replying that I wanted to ‘look nice for you x x’
At 7.30 I was stood outside Paul’s block feeling the cold through my tights and pulling my fur around me. If I had nipples they would have been hard in my bra and I shivered half in cold and half in delight at the idea of having a nice pair of boobs that I hoped my boyfriend wanted to fondle.
Paul buzzed me in and was waiting on the landing as I arrived. He ushered me in and took me in his arms as he closed the door. I pushed my abdomen into him wanting to feel his hardness as we kissed, letting him explore my mouth with his tongue.
‘You look nice’
‘Aww thank you’ I replied giving Paul a smile and another kiss. Paul led me into a big open plan room with a floor to ceiling window that stretched from one side of the room to the other. I was opened mouthed at the designer sofas (two of them!), huge flatscreen on the wall and the swanky kitchen at the other end of the room.
‘Why don’t you sit down and I’ll get us a drink’ said Paul.
I did as I was told and perched on one of the sofas, smoothing my skirt first and then crossing my legs. Paul came over and handed me a glass of wine.
‘Is red OK?’
Paul sat down next to me. I recrossed my legs to face him, remembering to keep my back straight, hopefully portraying the image of a sexy girl next door type. I could see Paul looking me up and down. I was certainly showing off some leg, although I didn’t feel tarty in the brown ribbed opaque tights I was wearing.
We chatted for a while; Paul kept topping up my wine glass although he was drinking a fair bit too. We were about two-thirds through the second bottle of Jacobs Creek when he looked at me a little sheepishly.
‘You know I think you’re nice don’t you?’ he asked
‘Aww... really?’ He nodded ‘Aww thank you’ I leant over and gave him a peck and squeezed his hand.
Paul moved in closer to me, he began to stroke my leg. I was a bit tipsy by now and could feel something stirring in my knickers. I leant back as Paul leaned in to kiss me, letting him squeeze my ‘tits’ and moaning softly in appreciation as if I really did have a pair of pert C cups nestling in my bra. I had uncrossed my legs and Paul moved on top of me, kissing me. I felt his hand push my legs apart slightly, exploring my inner thigh and moving towards...
‘I can’t...’ I said, sounding sorry and disappointed at the same time
‘It’s OK’ Paul continued to moved his hand up my leg, towards my sex. I closed my legs together trapping Paul’s hand.
‘I do want to... .’ I pleaded ‘But...’
‘I know, I know... you explained last night’ Paul didn’t sound pissed off with me ‘Why don’t you tell me the real reason why you can’t?’ he asked.
‘What d’you mean?’ I pulled back from him, but he still had his hand trapped between my thighs.
‘It’s OK y’know. I really don’t mind. I think it’s perfect to be honest’
I didn’t know how to react. I was going red with embarrassment. What did Paul mean?
‘Listen I think you make a really lovely girl.... for a boy’
‘YOU KNOW!’ I shot back to the end of the sofa.
Paul looked sheepish again.
‘I do... I mean, not from the start... it’s not as if it’s easy to tell... but when I realised it all clicked into place for me’
‘What d’you mean?’
Paul went on to explain that when we had met on the train he had just been concerned for me as I seemed upset. He found me attractive and that was the issue, because Paul had a secret side too. He was gay.
He explained that he came from a very wealthy family who expected him to produce grandchildren just as soon as he had met the ‘right’ girl. Paul’s problem was that the right girl was probably a boy and that ruled out grandchildren and would also result in him losing the lifestyle that was currently being bankrolled by his parents.
As he had sat opposite me on the train wondering what was making him feel attracted to me, he had begun to look at me more closely until he realised that the girl opposite him was in fact a boy. He said it was really hard to tell (which made me feel a little better), but once he had realised an idea had begun to form in his head.
‘I wanted to see if you could carry it off in a social situation like a date’
‘WHY...?’ I asked and then more softly remembering my girls voice ‘Did I?’
‘You did... you were perfect... perfect girlfriend material in fact’
‘What d’you mean?’
‘Look my parents would kill me if they knew I was gay. I’m not suggesting we go on holiday with them, but I reckon we could pass you off as my new girlfriend for one evening’
Paul went on to explain that his parents were always trying to set him up with girls. If he could make them think he had a girlfriend he had met in London they might leave him alone for a while. I wasn’t sure; up until now I had felt confident that I was convincing people that I really was a girl.
‘I’m not sure Paul’
‘Look, I think you’d be perfect. We might need a bit of a back story for you, but no one batted an eyelid last night. Everyone thought we were a couple’
I had loved the date, although now I wasn’t feeling that great. Paul looked at me.
‘When we’re kissing... d’you like it?’ he asked. It was my turn to look sheepish.
‘Did you want more than a kiss?’
I looked at him shyly.
‘Yes’ I said quietly.
‘Have you been with a guy before?’
‘No... Not really’
‘But, you want to..?’
‘I don’t know... I think so... I mean I love it when we kiss and I want it to go further, but I didn’t know what to do about taking it further... How I was gonna explain’
‘Well... now you don’t have to. I mean I fancy you as a girl... if that makes sense... but it’s ok... I mean it’s better that you’re not... underneath kinda thing...’
Paul moved in close to me again, took my hands and kissed me. I felt tears stinging as I yielded to him and allowed him to hold me. I felt his hand exploring my legs again, but this time parted them slightly to allow him to put his hand up my skirt.
I felt Paul’s fingers gently rubbing my knickers through my tights where my ‘pussy’ would be.
‘Is that nice?’ he asked
‘Mmm... Lovely’ I giggled ‘Do I sound like a girl?’
‘Yeh... you do actually’
I could feel myself getting excited by Paul touching me even though I could barely feel it through tights, knickers and Elastoplast. I gently took his hand away and then put both arms around his neck and my leg over him, drawing myself onto his lap. My skirt rode up and Paul put his hands on my legs, rubbing my nylon clad legs. I pushed into him, feeling his cock hard through his jeans. We were kissing passionately now, exploring each other’s mouths. I started to rub Pauls cock while I undid his belt and then started on his jeans. In seconds I was pulling his cock out of his CK underwear and opening and closing my fingers around it. Paul pulled me into him as I played with him. He was so stiff in my hands.
‘Do you want to come?’ I asked him
‘Like this?’ I looked down and indicated my hand with my eyes. Paul looked at me and I cottoned on.
‘I have to warn you; I’ve not done this before’ I said
I let go of him, slipped off his lap and smoothed my skirt down as I stood. My own cock was straining against its disguise, but somehow I still retained a feminine profile. Keeping my knees together I bent my legs and was in front of him. I pushed his legs apart and got between them, brushing my hair back from my face as I leant in to his tip.
My first thought was to have a little taste, so I kissed the bulging head of his circumcised cock gently. I placed little kisses all over the head. Paul seemed to be enjoying the attention, gasping with pleasure if I used a little bit of tongue as well. I think we were both a little shocked (for different reasons!) when I decided to open my mouth and see how much of him I could fit in.
I was careful not to go too far in case I gagged, but sooner I had his cock wet from my saliva and he was slipping in and out of my mouth as I pulled back and forth varying my speed if I felt him pulsing. Eventually I thought he deserved his reward and sped up to the extent that Paul could not control himself. My finger on the base of his cock gave me enough warning and I pulled out quickly enough to avoid swallowing his cum.
Paul leant back on the sofa and threw his head 45 degrees.
‘Are you sure that was your first time?’
I was a little embarrassed now, looking around for something to wipe the hot sticky cum off with.
‘Yeh... was I OK?’
‘Mmm... Oh Yeh... .’
Later Paul and I were sat on the sofa together finishing the wine. I had taken off my boots and was sat opposite him with my feet on his legs. He was massaging my toes through my tights. I had fixed myself up after blowing him and felt nice and girly after satisfying my man. Paul looked over at me a little nervously.
‘There is just one thing’ he said
‘What?’ I asked
‘I feel a bit cheeky asking...’
‘What is it?’
‘Well... look... I think you look nice and everything, but..’
‘But what?’ I asked. I was getting a bit cross at the unpleasant surprises. This was hardly the way to be after your girlfriend has given you a blow job.
‘Come on!’ I said
‘Well... you know I’m from Essex’ I nodded and Paul continued ‘Well, it’s just that my parents will be expecting someone pretty glam... y’know... a WAG..’
‘Oh...’ I thought for a second. Paul was probably right. My look as Leanne had been designed to look convincing, but to blend in. My mousy blonde hair and specs were hardly going to be what his parents were expecting.
‘Well the advantage with me is that I can be anyone you want me to be; blonde or brunette, long hair, short hair. I can even have bigger boobs if that’s what you want’
Paul thought for a second and then grabbed the TV Guide from the coffee table.
‘What about her?’ he asked. On the cover there was a girl, a little older than me I thought with long blonde hair, with a bit of a wave in it. She had a nice toothy smile and was wearing a business dress with black opaque’s and high patent heels.
‘Yeh I reckon I could do a look like that... I would need a new wig though... and some teeth whitening’ I grinned
‘You can have whatever you need. We should get you some nice clothes to wear and few designer handbags, so you look like the kind of girl my parents expect’
I was quite into the idea of some shopping at someone else’s expense. I remembered how much I had admired Malin Jensen’s wardrobe and imagined I could probably find some great dresses in Jigsaw.
Paul and I talked into the night. He decided we would need to flesh out my Leanne back story as his parents were sure to ask him loads of questions about his ‘new girlfriend’ and we would need to get our stories straight. Although I was still dressed up as Leanne I told Paul a bit about my normal life. He was surprised when I said that I had only been dressing for a few weeks as he thought I was so convincing as a girl.
I suggested we go with my being a junior lawyer in chambers as I knew enough about the job to carry off any questions. Paul said that I should be an only child whose parents lived outside London to avoid any possibility of his mum inviting them over for dinner one day! I suggested that we should take some photos of us together as a couple once I had my new look together. Dotted around the flat and as the screensaver on Paul’s phone would make it look like we were like any other young couple.
Eventually I suggested I ought to go home. Paul offered to pay for a cab for me, but then said:
‘You could stay’
‘I’m not sure’ I said ‘You don’t want to see me in the morning with caked on makeup and a five o clock shadow!’ Paul’s jaw dropped at that one.
‘S’ok... was joking... one of the reasons I seem to get away with this is not having to shave much... ‘cept my legs!’
‘Are you sure?’
‘Yeh.. for the best.. I mean I think I want to... sleep with you I mean... but I want it to be perfect... it will be my first time... as a girl’
Paul leaned over and gave me a tender kiss
‘Ok baby.... but soon.... I really want you, you know’ It was my turn to kiss him; I so wanted him right then it felt so natural to feel girly and to want this guy sat next to me.
When I got in I took off my top, skirt and tights and lay in bed in my knickers and bra rubbing my ‘pussy’ through the fabulous feminine material. I was tempted to put on Claire’s stockings again and to bring myself off this time, but soon fell asleep.
The following morning I went online to search for a new hairstyle. We had agreed I was still going to be called Leanne, but would try to get used to using little pet names for each other; he would call me baby or honey or princess. I loved the idea.
Paul had given me a credit card to use and had said that I could get stuff delivered to his place to avoid any chance that the sale would be declined. I was still going to get stuff addressed to me to maintain the illusion.
I managed to find a few styles that I thought would be suitable for my new look. There was a long wavy wig in a classic blonde shade with a few highlights and long ‘bangs’ that would frame my face nicely. I had decided to go for another with a ‘scalp’ as the style had a parting and I wanted to look as real as possible.
I had also found another site that had some really interesting products. The girl on the front of the magazine had a really toothy smile. My own teeth weren’t bad, but in comparison to the girl I just didn’t have the same advantages. I had found a site that could make a denture that would fit over my own teeth and produce similar results. I had no idea if the denture would work for me, but I supposed I might have use for it as one of the female disguises that Tommy seemed to feel would be my line of work from now on.
I also shopped for some new clothes, buying a couple of clingy, but not too short dresses, a few work basics like satin blouses and pencil skirts, a new skirt suit in light grey wool with a pinstripe and then going mad on a lingerie website. I brought matching underwear in satin and lace in lots of colours; sometimes all in one colour or often contrasting like blue satin with black lace. I also treated myself to hold up stockings in nude and black and a few pairs of sheers and opaque’s. I decided that I would need a new pair of patent heels for ‘work’ and also brought a nice plain leather black pair of courts with a sensible heel. My final extravagance was a pair of boots in pull fabric with a 3.5” stiletto heel and pointed toe that I thought would look great with a short dress and opaque’s.
I really wanted to be able to surprise Paul with my new look, but I didn’t know how to be able to work out what would work if I had to go round and try everything on to see if it fitted OK at his place. I was desperate to please him and we had been talking about what I had brought when we chatted on the phone in the evening. Eventually it seemed as if everything had arrived as I had worked out that he should have been expecting about a dozen packages to his flat. The final piece of the jigsaw was my new denture. I had taken a cast of my mouth that the manufacturer had supplied the kit for. I was surprised how quickly they had been able to do it, but I had supplied some cropped photos of the look I wanted and emails exchanged with them had indicated they could do as I asked. Paul gave me a call that evening to say it had arrived.
‘I think it’s here’ he said ‘Small cardboard box from a firm called ‘New Smile UK’
‘Should I open it and check them out?’
‘Noo.. I don’t know if they will fit yet and I want to surprise you’
‘OK.. So are you coming over?’
‘No.. Not tonight.. I need to have a bit of a dress up session first... make sure everything is right. I have to fool your parents remember, so it all has to be perfect’
‘Why don’t I drop a key round to you tomorrow? You can come round tomorrow and have the place to yourself. I can work late and then if you give me a text I’ll come back’
I liked the sound of that. Having Paul’s lovely flat to myself while I transformed myself into my idea of what every guys perfect girlfriend should look like was my idea of heaven right now. I imagined myself taking ages with my beauty regime and then wandering round in my underwear while deciding what to wear.
‘Sounds lovely’ I said
I managed to get out of work early the next day. I told Tommy I had to do a bit of shopping for my au pair disguise which wasn’t exactly progressing as I was currently totally obsessed with Paul.
I raced back to my flat to pick up my makeup and a few other pieces like breast forms and a few items of clothing. I was tempted to dress up as Leanne to go round to Paul’s, but I figured I could sneak into his place without too many people noticing. I really wanted to do the works round there, so I didn’t want the hassle of getting dressed up and made up twice. Besides I had another little surprise up my sleeve.
I got to Paul’s flat and had a look around. The place was really tidy and when I checked the bedroom there was a note propped up against a pile of boxes.
Make yourself at home Princess
There’s wine in the fridge
See you later
Paul x x
I smiled to myself and began to work through opening the various sized boxes on the bed. The larger boxes contained the boots and shoes. I kept the work ones boxed and put them into the suitcase I had brought with me. I did the same with the work clothes, being careful to keep them folded neatly in their tissue paper. The two dresses I had brought I hung up and then I looked through the new underwear and decided on a few sets that I thought could go well with either dress.
The new wig was really nice and great quality. It looked super realistic as I held it up to the light and I was sure it would appear convincing to anyone that looked at me. I carefully opened the box from New Smile UK.
The denture was very fine as it was designed to fit over my own teeth. I turned it over in my hands wondering how it would look when I put it in. There was no time for that now; I had to get the flat ready for my surprise for Paul.
First I would get partly dressed up. I had a hot shower and shaved again to make sure I was super smooth all over. I covered myself with perfumed body lotion and moisturiser and after putting on a body spray, opened up my makeup and brushes and began to put my face on.
I chose a subtle foundation, powder and blush, but went for a quite dramatic statement with my eyes with a darker shadow that blended into my liquid eyeliner and false lashes. I carefully plucked and shaped my brows and then applied a light pink lip gloss after making my lips a little fuller with lip liner.
I decided to wear a clingy shift style dress with short sleeves and a square cut neckline that would cover my cleavage. It was a lovely shade of pinky beige and looked like several blocks of fabric joined together horizontally almost like a bandage.
The underwear I chose was beige satin with cream lace. The knickers were highish cut, but covered my bum nicely and would not show much through my dress. As always I tucked my maleness away and covered it with Elastoplast to prevent me losing my female profile. I checked in the mirror a few times from side and back to make sure that I presented the image of a young woman.
Popping my silicone breast into my bra I padded out to the lounge area and the dining table. I had already put the food I had brought into the fridge and now I set about laying the table for two for dinner.
I arranged the chairs so that Paul and I could sit quite close; I wanted our knees to be able to touch under the table and for him to be able to cover my hand with his as we chatted. I put a couple of candles on the table and some matches ready to light them as a last minute touch.
I went round the rest of the flat getting things ready. I pulled the blinds and put on low lighting. I went through Paul’s cd’s and found a chill out album that I put onto repeat on his hi fi. The food I had brought was quick and easy to prepare; microwave specials, but it looked classy enough. I hoped that he liked lamb anyway!
I estimated it would take Paul about an hour to get home, so that gave me just enough time to get my tights and dress on and try out my new look properly. Back in the bedroom I opened a new pair of nude sheer tights and carefully rolled them up each let and settled them comfortably over my knickers. The dress had a zip up the back, but I was quite practiced at getting into and out of women’s clothing now and it went up quite easily. I smoothed it down and looking down was quite happy with the fit. I didn’t want to look in the full length mirror until I had everything on.
The new boots literally were pull on and fitted easily. I smoothed the fabric on both legs and stood up and walked into the bathroom my heels making a loud click on the tiled floor. I did the wig first, tipping my head forward and then back to get the wig on and then fussing around with it until I was happy it was straight. It fell nicely around my face and shoulders and if I leant forward the long bangs fell forward and I could push it back in a very feminine gesture.
Finally I went for my new ‘smile’. I was surprised at how easily it fitted and it didn’t alter the shape of my face at all. I looked in the mirror and smiled. A row of brilliant white teeth smiled back at me and I played with my hair and posed for a bit as I admired my new look. It was certainly a step on from Leanne as with longer, blonder hair, no glasses and my new million dollar smile I did look as if I could be reading at least the local news!
I walked out to the full length mirror and caught my breath as I saw myself now. The boots looked totally sexy, but I still showed enough leg in my dress that hugged me in all the right places. All of this was topped off with long blonde tresses and a great smile that would charm anyone who met this girl.
I figured I better try my voice as I didn’t know if the denture would alter it. If anything I sounded a bit more breathy, perhaps a little lispy, but nothing too obvious. I heard my Blackberry beeping with a message. It was Paul.
‘I’m about 10 minutes away, are you ready for me?? x’ I told him I was and set about making the flat ready for my boyfriends return.
I tottered around in my heels getting the starter ready and plated up; Parma ham and Melon. I took the wine out and poured two glasses replacing the wine into a cooler. I had chosen white as I didn’t want to stain my teeth! I clicked on the hi fi and adjusted the volume to a suitable background level and then waited in the kitchen as I heard the key go in the look.
As Paul came in through the front door and closed the door I guessed he wondered what was going on with the soft lighting and music.
‘Hello?’ I heard in him call.
‘In here babe’ I replied
Paul walked into the room and stopped as he saw me around the corner.
‘Wow! You look lovely!’
I walked towards him, heels clicking and then smiled.
‘What do you think?’ I asked gesturing to my hair and smile.
‘Wow... you look so good... my dad’s not gonna know where to look when he meets you’
I put my arms around Paul’s neck and tilted my body into what I knew would be a hardening cock. I pushed sensuously and kissed him lightly on the lips.
‘Well, that’s the idea isn’t it?’ I purred ‘You want him to think you have met some sexy piece who looks as if she will go all night. You want him to be imagining me in my underwear. You want him to imagine me riding you, my super hot boyfriend’
I rubbed Paul’s cock with my hand. I had applied false nails of course and I gave him a little squeeze.
Paul looked like a dog with two dicks. I handed him a glass of wine, led him to the dining table and sat him down. I could feel him watching my bum as I clicked back into the kitchen and brought our starters over.
‘I figured I better learn how to be the perfect hostess’ I gave him another big smile and felt his hand on my nylon clad knee under the table.
‘I knew you would be good, but this is amazing’ Paul said ‘My parents will fall for you completely. Don’t be surprised if my mum is suggesting that the two of you go out shopping together and lunches with her friends’
Paul and I chatted over dinner. We talked about his day and I listened attentively like any girl who was totally into her man would do. After dinner Paul took my hand and led me to the sofa. Before we sat down he turned towards me and taking both of my hands drew me close and kissed me. We stood like that for a while, exchanging kisses. I could feel the heat from his cock and knew my own was straining against my knickers through the Elastoplast. I felt so horny.
‘Do you want to stay?’ Paul asked
‘I don’t know.. I don’t know if it’s such a good idea if I stay’
‘I would like you to stay’
‘Well... OK then... I’ll stay’ I smiled at him.
Paul asked me if I wanted to use the bathroom first. I thanked him and went into the bedroom. I pulled off my boots and tights and unzipped and stepped out of my dress. I went into the bathroom and checked my makeup and hair. It had held up well and I still looked every inch the girl. I went back to the bedroom and took my nude heels from our first date and a pair of nude hold ups out of my case.
I carefully rolled the stockings up each leg, smoothing out the lacy hold up tops around my thighs. I stepped into my heels and checked myself out in the mirror. I had pee’d in the bathroom after checking my face and with freshly applied Elastoplast I looked convincingly female from the waist down.
I wondered about how and where to pose. On the bed? Maybe sat on the end, legs crossed? Perhaps on the bed, legs crossed at the ankles and a big smile. I eventually stood away from the door, backlit in the doorway of the bathroom. I put one leg back and pointed the toe of my shoe to the floor. I had adopted the classic pose of the nude.
Paul came in. I looked over my shoulder at him, feeling a little nervous. He stood there for what seemed like ages just looking at me; staring.
‘What’s wrong?’ I asked ‘Do you not like it?’ I indicated my underwear.
‘No... I mean yes... I mean you look beautiful..’ his voice trailed off.
‘Thank you... I didn’t know if you would like me... like this I mean... I didn’t know if you wanted me as a girl... or as a boy’
Paul came over to me and took me in his arms. He kissed me very slowly, exploring my mouth with his tongue while I yielded to him. He gently took my hand and led me over to the bed. I turned and sat down crossing my legs.
Paul undressed but kept his eyes on mine all the time. I smiled back at him, feeling a little shy now but admiring his fit body and the bulge in his Calvin’s. Paul came over to me and gently pushed my back onto the bed. I swung my legs up and we were facing each other with him caressing my legs through my hold ups.
I began to rub his cock as we kissed and fooled around on the bed. I had carefully clipped my wig on, so there was no danger of it coming off or going wonky. I so wanted this to be perfect. Intuitively I knew Paul wanted more and so I slipped down the bed and pulled his boxers off.
His cock was like stone, totally erect and glistening with pre cum as I imagined my own cock would be behind its various layers. I kissed his hard on and licked around the shaft. I took a few inches in my mouth and sucked slowly and gently, but I didn’t want him to cum yet; I wanted that another way.
I came back up the bed and looked at him through the blonde frame of my bangs.
‘I want you’ I said
‘Are you sure?’
‘Yes... I think so... will it hurt?’
‘It might do...’
I looked at him again. I felt so horny. I knew I didn’t want him to do anything else than make love to me. I wanted to be completely passive. I wanted to be the girl.
‘I still want you’
Paul nodded and reached over to his bedside cabinet. He took out a packet of condoms and tube of lubricant. I turned away from him and stood up. I didn’t want him to see any of my maleness. I pulled down the front of my knickers and pulled off the Elastoplast. I grabbed my cock and arranged it in its normal position creating a bulge in my knickers. I got back on the bed gingerly, trying not to give away anything of my true sex and laid on my side with my bum facing Paul. I felt him push my knickers down from each side until he had exposed my hole.
‘This might be cold’ he laughed which took a little of the tension away.
I felt the cold gel around my hole and then gasped as Paul pushed a finger in. Paul leant over and kissed my shoulder, then pulled my hair back to kiss my cheek.
‘Sorry... did that hurt?’
‘More like shock... S’ok’
I was clutching my cock so he couldn’t see it. Paul tried again with his finger and it seemed easier this time, almost pleasurable as he gently pushed one and then two fingers into me. Paul kissed my neck and shoulders as he did this and then eventually when I could take the anticipation no more I said:
‘I think I’m ready now’
I began to rub my own cock in anticipation as I listened to Paul opening a condom and heard the familiar sounds of one being put on. He used a bit more finger and lubricant and then I felt his cock against my crack as he rubbed against me. Pauls arm came over and he began kneading my falsies through the bra, which I loved. I pushed against him, rubbing back. We continued jockeying into position until I felt the tip of Paul’s cock enter me.
I tried not to tense up, but the shock of the size was almost overwhelming. Paul was very gentle though taking things really slowly and only pushing in a bit more if I wriggled more onto him. Eventually it felt like he was in me completely and I tried to relax and enjoy the sensation. I was playing with my own cock as he slipped in and out of me. Paul continued to kiss me in between grunting softly as he pushed his hard cock into my aching hole.
I knew Paul was ready to cum when he speeded up a bit and I pulled on my own cock a bit more urgently. I felt Paul explode into the condom and he held me tightly as he came. I wanted to share now. Paul gripped me.
‘Do you want to cum?’
‘Oh Yeh’ I breathed
‘Like a girl?’ He asked mischievously
I squirmed. I had of course seen movies with sex scenes; I knew what girls were supposed to cum like. I moved a hand up to my head and began to muss my hair. I gyrated on his cock and began moaning softly. It was working; I was beginning to feel so turned on, more turned on than I was already.
‘Oh... Oh... GOD!’
Paul shoved his cock into me.
‘You like that baby’
‘Ummm... Yeh.... Oh... Oh....’
‘Cum for me baby’
I was yanking on my cock furiously and moaning as Paul continued to thrust into me. Eventually I couldn’t hold it anymore.
‘Oh God.... Oh God.... I’m coming...’
I felt cum spurt from my cock over my hand and onto the bed. Paul held me as I shuddered and then held me in his arms.
‘Was that OK?’
I nuzzled back into him as he buried his head in my hair.
‘It was lovely’ I said breathlessly
Paul who admittedly had more experience of these things than I did was pretty cool afterwards. He brought me a towel so I could wipe myself and said he would fix us a drink if I wanted to clean up a bit and check hair and makeup etc.
I undressed and put the hold ups, heels and underwear into my case and took out a fresh set in white cotton. I found one of Paul’s shirts and put this on over my underwear. I cleaned my cock and ass, which by now felt pretty sore, before re tucking my cock and applying more Elastoplast.
I took off some make up, but still left enough on to look fem. I took my denture out as I was ready to relax now. Paul came back in with a glass of cognac for both of us.
‘You look good in my shirt’ he grinned
‘Thanks... hope you don’t mind me borrowing? It might smell of my perfume now’
Paul gave me a kiss. We lay back on the bed with him cuddling me. I felt so feminine at that point I couldn’t imagine having to go back to my normal life again.
Disclaimer: The original characters and plot of this story are the property of the author. No infringement of pre-existing copyright is intended. This story is copyright (c) 2011 Deborah Karen. All rights reserved.
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