Lost Luggage

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'You've been a very good girl tonight,' she said in a mocking tone. 'So good I've a good mind to dress you as my girlfriend tomorrow. I just can't wait to see you in a tiny bikini. I want to rub sun tan location all over your fair skin and watch all those men stare at us in that bemused way as their wild fantasies unfold in front of them.' She laughs and continues to pump me rhythmically, squeezing me with her strong thigh muscles. It wasn't long before I was squealing like a girl pleading for more. Then I said it. The words just escaped. I didn't mean too. I think it was the drink talking. 'Fuck me,' I screamed. 'Fuck me.'

And she did, bouncing up and down as if her life depended on it. 'So,' she sang merrily' 'You want me to fuck you like a girl?' and to compound my guilt... that's when I came, spurting my load deep inside her. She was delighted and we soon collapsed fast asleep.

In the morning, when I woke, I was still in the nightdress. I swung my legs off the bed and stood up, wondering whether a good nights sleep had produced my lost case or provided a rational explanation for the previous nights pleasure. I look at my dress on the floor and immediately felt my cock begin to stir. I had obviously white-noised the childhood thoughts out of my mind, but now every tiny detail came flooding back like the morning tide.

'Come back to bed my pretty,' Clare calls and keen to exert some masculinity I do as required.

After she had used me for her pleasure I let her shave me. I wasn't a particularly hairy man but as I watched her shave me all over I felt any remaining masculinity removed. Soon I had a smooth silk like body, which tingled with her every touch. My sensitivity had heightened and my nipples ached. I foolishly thought that that would be the end of our fun but no; she refreshed my make-up then helped me dress into a pretty sundress with a pair of sandals. I didn't' even complain going back down to the restaurant as I felt beautiful and confident. The waiters smiled at us and I caught Clare fluttering her eyelashes at her man.

After a light breakfast we popped back to our rooms to slip into our swimming costumes. At this point I was incredibly nervous. I did contemplate just wearing a bikini bottoms but now with a smooth body I looked neither masculine nor male.

'You can't be a man now. It's one or the other'. She giggled obviously enjoying every moment.

And who was I to complain? Who was I kidding? I didn't want to wear a bikini bottom and pretend they where men's trunks. I wanted to dress like a lady. I was just apprehensive as to how I would look with no foundation garments. But I was wrong. Clare made me wear the gaff and my costume had two pockets in the bra, which she filled with two synthetic breasts from the mystery case. With a flaccid cock tucked tightly away and a bra positively busting, my figure was conserved and I looked incredibly feminine.

I still wasn't overtly confident so I wore mine under the sundress and slipped it off carefully while lying on my sun bed so as not to make a scheme. As promised Clare rubbed in the sun lotion, especially round my white bits, and I was soon on my way to getting a tan.

After a few days, like before, in my mind I had become a girl. A happy, pretty girl enjoying her summer holiday. I loved everything any fun loving girl on holiday would enjoy. I simply loved stretching out on my sun bed with Clare in her tiny bikini. It gave me a great thrill to see men watching me with no idea as to my real gender. Clare and I had a scream rubbing oil into each other in front of all our onlookers. The only concern I had was getting too excited and allowing my cock to get too firm. Clare made sure that never happened by milking me dry on a regular basis. We had sex every morning but if she thought I was showing any danger of getting overtly excited she would whisk me back to our room for a 'domm fuck' or the local ladies and wank me off.

A particular thrill was being asked to participate in the hotels weekly beauty contest. I was terribly nervous but Clare insisted I took part. I didn't have to say much just model a swimsuit and an evening dress in front of an audience. Clare helped me get ready and ignoring the obvious cattiness of the other contestants I had a great time. I couldn't believe it when I won and was crowned Miss Hotel Mar September 2006. It was a magical experience. All the applause and the lights -- a holiday highlight. I was sat on a throne and presented with a sash and crown. Plus I won a holiday voucher for another year. Clare was so proud and it was while we where sitting back in the lounge that night that she proposed. She held my hand gently and asked me to be her wife. I thought she was joking initially but soon realised how serious she was when she presented me with a huge diamond ring. It sparkled beautifully as she slipped it on my finger. I was so excited I forgot who I was and my mind ran wild thinking of the church, the guest list and of course my dress. I pictured my lingerie and the long bridal gown and as I imagined all the finery despite Clare keeping my cock milked it leapt in my panties and without warning spurted a dribble of excitement. I blushed and as I felt my panties dampen my fairytale bubble burst. It didn't last long as reality reared its ugly head. I wasn't really a girl; I could never be a bride, have children, raise a family or support a husband. Clare wasn't a man. I began to get upset and Clare took my hand lovingly.

'You'll always be my bride,' she whispered. She had done it again. She'd guessed my mind. This was not right. I was supposed to ask Clare to be my bride not the other way round. What was she thinking? The facade had got out of hand. How could we return back to normal?

Of course much more happened during the holiday but needless to say my case never materialised. We never bought any men's clothes though I did spend my winnings in the boutique on a strapless cocktail frock. It was at the top of their price range but for that I got a beautifully structured dress with a beaded and bonded bodice that gave me a timeless, hourglass shape for our last night. Like before I wanted to be the prettiest girl there.

Our last day came round incredibly soon and I was soon packing to come home. I wore a gorgeous summers dress that showed off my tan. It sounds ridiculous but it never dawned on me as to how we would clear custom control. In Feurteventura the guard looked shocked but didn't seem to mind and we skipped through easily but back in the UK things where very different. The grumpy man looked at me suspiciously when I handed him my passport. The picture was obviously of me but without wig, make-up and not in a dress. I smiled sweetly and hoped my feminine charm would win him over. To make matters worse Clare told him I was Miss Hotel Mar 2006 and showed him my sash. I didn't want to shout out the issue and make a scene so I tried whispering to explain but this seemed to anger him even more and we were both taken into a side room for interrogation. It appeared they didn't believe who we where. Eventually we where seen by a lady for further questioning and though severe she was quite sweet and after about twenty minutes we where allowed to proceed to collect our luggage.

I didn't know what to expect as we wheeled our luggage trolley into the arrival lounge. It certainly wasn't my mum. I anticipated getting a taxi so I wasn't even looking for her. She saw us first and I heard her squeal before seeing her. I by now was so comfortable in my new clothes it wasn't until she ran up to us and threw her arms around me did I remember what I was wearing and blush.

'You look beautiful,' she sobs holding me by the shoulders at arms length scanning me from top to toe.

'I hope you took lots of photos. My, my don't you look pretty. You've got lovely tanned legs and your hair is gorgeous.' She smiled at Clare. 'You both look beautiful.'

'We've got some exciting news haven't we Beatrice.' Clare beams. 'Show your mum,'

'What?' I say.

'The ring stupid.' Clare frowns.

I held out my hand proudly, my nail polish shining under the lights and showed her my large sparkling engagement ring.

Mum sighed 'I'm so happy for you both. And Beatrice you'll make a wonderful bride. I can't wait to see you in a gown. I knew Clare was right for you. Not like those other girls you dated. Clare understands your special needs. She can appreciate you for who you really are. I had to tell all your other girlfriends about the holiday, the lost luggage fiasco and of course show them all the lovely photos of you in a dress. I knew eventually we would find someone who appreciated you and your feminine side. '

I felt I should complain but how could I dressed as I was I wasn't in a position of strength? Now having spent a week as a pretty woman I found it difficult to justify. Despite I wasn't sure if I wanted to complain. I liked the idea of being a woman and a bride and walking down the isle with pretty bridesmaids holding my train.

Mum hugged me again and helped push our luggage trolley as we walked towards the car. 'Claire told me about your missing case. That was unfortunate, wasn't it?' She grinned proudly yet I still didn't get it. 'And you apparently found another case.' She added.

'Yes.' I say, 'if luck is the word.'

She grins again and flashes Clare a knowing glance.

'Did you like the wig and what did you think of the padded panties. I bet they gave you a hourglass figure.'

I nod. 'But its not ours,' I remind her.

'You're not going to hand it in to lost luggage then?'

I look sheepish. 'No, Clare wants us to keep it.'

Mum nods approvingly and scans me from head to foot yet again. 'I think that's a super idea, Beatrice.'

I should have been angry but all my fury was spent. It would be a shame to lose the things since they all fitted so well. It was as if they where bought for me... The penny then drops. 'How do you know what was in the case?' I ask

Mum grins. 'I bought all the pretty things with Clare and swapped it for your case in departures while you went to the loo.'

I wasn't sure to laugh or cry. 'So it was my case after all.' I say, 'I hadn't lost my case at all?'

Mum and Clare both nod in unison as we walk towards the car and realise I had been had.

My see original case still in the boot of her car and as I sit in the back and listened to my mum and Clare talk excitedly about our holiday. It was like a dream. I look down at my feminised form. I smile as I examine my breasts and how my dress hangs so well. My hands are in my lap and I see my legs poking from under my skirt. I'm glad I wore tights, as the weather was much colder in the UK. I had enjoyed myself so much but what now? I felt as if I'd been through a holiday romance but back at our flat would I revert back to my masculine self. Would Beatrice only come out on holiday? Was Clare serious about the wedding?

I knew what I wanted but realistically was it possible? After all I was a guy.

It wasn't a long journey home and as I sat in the car I dreamt of a life that could be. With me as the pretty wife looking after my Clare. Cooking for her everyday. Cleaning the house, satisfying her sexual needs and looking my best for her every single moment of the day. What was going to happen next and as we neared home I felt I was about to find out.

Do you stay in dresses and skirts and begin a new life as Clares' fiancée or do you dress back in your old trousers and revert to the man of the house? You decide.

The end

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21 Comments
AnonymousAnonymousover 3 years ago
Excellent!

I think all guys should have a Clare in their lives. I know I would.

AnonymousAnonymousover 4 years ago
My wife is lawyer in hot pencils skirt .. i want to her skirts

Actully , i start to tell my wife about how i love here skirts and dresses an tights

And how i loved to try them

Step by step

I tryed some and take some pictures of me wearing them

And i send it to her phone on whatsapp

She is very lovely , she lughed alote but never say no

And i send much more

Of photo of me in here pencil skirts and the heavenlly blue blouse of her

With heels and stocking

More and more

And for reall im crossdresser from my childhood

She becoming to be ok... my husbend like to try my pencil skirts

Then she gave me many of her lovely pencil skirts and many blouses and stoacking

And gave me access to all of lengiry and dress and clothes

Now im allowed to have romantic sex with her while im wearing cute pencil skirt and proffissiinal blouses and all outfits of sexy lawyer as her

I wish ican go public insexy lawyer like her

AnonymousAnonymousover 4 years ago
The previous commentator is slow

A nice slow build up makes this a delicious story for those looking for more than a rub and tug.

AnonymousAnonymousabout 5 years ago
Too slow

This story is too slow

DianeRedfernDianeRedfernover 6 years ago
Magnificent story

Made me so wet, sweetie! I adored it. I hope there's more/

xoxo, Di

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