Lost Luggage

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When your luggage goes missing, you wear a dress.
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Tomsparty
Tomsparty
646 Followers

As usual my mum took great delight in telling my new girlfriend the lost luggage story. I took Clare to her house for Sunday lunch and told mum specifically not to embarrass me with any of my childhood stories or old photographs. She was on her best behaviour during the meal but afterwards as we sat down in the lounge for coffee she was true to form. She quickly began talking about my schooldays and previous girlfriends and egged on by Clare, keen to learn my past mum was soon showing those embarrassing baby and early school photos.

The holiday to Spain was inevitably mentioned and I shivered with apprehension. Why she had to keep choosing that story I never knew. If only she could remember how I scored a goal in football, was top of my class in maths and English, caught the biggest fish at the young anglers competition or how I was incredibly popular and liked by everyone. No, she had to rake up the Spanish lost luggage story.

With her old holiday photo album on Claire's knees, mum began flicking through the pages as if we had just returned despite it being over fifteen years ago.

I tried to stop her but it was hopeless.

'Who's that?' Clare asks pointing to a photo of two cute young girls on park swings in pretty summer dresses.

'Why shame on you. Can't you guess? That's Lucy,' mum says pointing to the little girl in canary yellow. '...And the beautiful girl in bubblegum pink is...' she paused as if gathering dramatic effect, 'someone very close to you.' Mum looks at me and grins proudly. A hot sweaty feeling washes over me and I turn beetroot red. I look towards Clare dejectedly as a paralysing sense of decorum stops me from defending myself in anyway.

'You're kidding me?' Clare squeals. 'That's you, all pretty in pink.'

I nod, blush and consider bolting for the door but if left alone there is no telling what my mum will tell. Clare's intrigued and holds the album closer for a better look.

'My goodness,' she says, 'you do look like sisters. I can see its you easily now.' she giggles sweetly but to my surprise Clare doesn't laugh meanly as most of my girlfriends had done in the past but touched me reassuringly on my arm and smiled.

'Yes,' mum explains excitedly. 'I knew the moment he was born that he should have been a girl. '

I wince and wish she would shut up but to my amazement Clare seems genuinely interested and her eyes egg my mum on.

'The dress is gorgeous. I would have loved to have worn it myself.' Clare gushes. 'You must have felt so special, like a princess.'

'I felt a total prat,' I grumble but the ladies weren't listening.

'I have to ask,' Clare says turning to mum as if I wasn't there, 'how on earth did you manage to get him to wear this beautiful dress.'

She laughs. 'It wasn't easy despite the obvious look of joy on his lovely face. The dress was his sisters,' mum adds flicking casually through the album pointing out all the other shots of me wearing her clothes. I squirm forgetting she had taken so many. There was me in short skirts, pleated skirts, underwear and tops and countless pretty dresses. They even had a picture of me playing on the beach in a flowery bikini. Not one picture showed me unhappy. In fact I looked totally comfortable in my new wardrobe and knew I was going to have some serious explaining to do.

Mum taps a photo of me in a pretty sleeveless dress that finished just above the knee that made my legs look incredibly long and slender. 'We where lucky in a way that his sisters clothes fitted otherwise we would have had a problem.'

Clare looked confused and went to ask a question but mum continued.

'I stupidly put everyone's things in separate cases. Mine, Lucy's and his, three cases in all. I thought they could help carrying them. The airline stupidly lost his case on the way out. Things have improved now but back then it was a miracle anything arrived at all. They promised to forward it on to our hotel when it was found. I assumed it would only be a day and I couldn't afford to buy him a new wardrobe.' She looked at me like a mother does to a son. 'To make matters worse he had spilt dark chocolate ice cream all down his only pair of trousers on the plane so he had to borrow something from Lucy. I wasn't going to sit in our bedroom waiting for his things when we where only there for a week.'

Clare smiled understandably. 'When did your case turn up?' she asked.

'It didn't.' I growled, 'not until a week back in the UK and...' I wanted to explain more but

Mum laughed and cut me dead. 'That's why there's so many pictures of him in Lucy's lovely clothes. He spent the whole week as a gorgeous young girl.' She sighed. 'He took to it like a duck to water and he assumed another personality altogether.' She sighed as

every tiny detail came flooding back like the morning tide. 'It wasn't all plain sailing. He behaved like a spoilt little girl initially. He stamped his feet and yelled so loud I thought the hotel might complain. But once in that dress and he felt the skirt brush against his thighs and the cool air blew round his legs he was a convert. He not only dressed as a young girl his total persona changed. I do believe for the seven days we where in Spain he mentally became a beautiful young girl. He spoke sweetly like girl, walked daintily like a girl, played gently like a girl and of course dressed beautifully like a girl.

Clare now laughs but not in a cruel way and again she touches me reassuringly.

'I'll never forget it.' mum continues, 'He was beautiful. They complemented each other so much. It was like having two pretty daughters.'

I cringed at the memory and looked at Clare who to my horror was sparkling with interest like a student at her favourite lecture.

'He didn't like it at first.' mum continued. 'The first evening meal was the most painful. I had to literally force him into a dress. He put up quite a struggle, yelled real loud and cried like a baby but I managed eventually and dragged him kicking and screaming downstairs.'

As mum talked I began to recall the events. Slowly at first, but as she went on more and detail became clear like a lifting fog and with the clarifying memory my cock began to stiffen with excitement. I remember vaguely feeling reeled in, like a fish exhausted by its battle against the angler.

Mum points to another photo of me holding an ice cream, wearing a light green A-line dress and tiny-heeled sandals. I have a huge smile on my face and it wasn't because of the ice cream.

'Lucy, his sister didn't help either she was most put out having to share her clothes with her brother but after a day or so she grew accustomed to him in skirts and they played together quite happily.'

Clare looked at mum aghast. 'You kept in skirts for days? The hotel didn't notice and the other guests said nothing?'

She grinned almost proudly. 'Why should they. He looked so angelic and pretty. In fact from what I can recall Lucy and Beatrice, as that's what I called him, made lots of little girlfriends and they where both incredibly well behaved. I got loads of lovely comments from other parents. I can remember one family who had two little boys; the mother was so envious. She kept cuddling Beatrice, telling me how she wanted girls instead of boys. I almost told her about Beatrice's real gender but I decided it wasn't fair on him. Besides it was our holiday secret.' She laughed and throws me another smile. 'But can you imagine her face if she had known the truth. I wonder to this day what would have happened if she had dressed her two young ruffians in dresses.' She laughed again, this time louder. 'What would they have thought?' She poured us all another coffee and I put my head in my hands in dismay.

'It was a real adventure and I have to admit I didn't want his lost case to turn up. I liked him as a girl. Having two daughters was fun. It was a new experience for me as it was for him.'

Clare nodded as if in agreement and I felt beaten and unable to comment.

Mum oblivious to my discomfort went on and on in painful detail, nauseas detail recounting how I experimented with her make-up, wore her high heels and paraded about like a little madam as my confidence grew and grew.

Clare was fascinated and asked question after question extracting intricate detail. Wanting to know what I wore when, what I looked best in, how I wore my hair, what colours suited me and whether I showed my knickers in public. I couldn't believe she asked so many questions and as the evening came to a close I saw her in a frighteningly new light.

Clare was particularly interested in how I reacted when back in the UK.

'He was a little awkward at first.' mum recalls. 'The first night, he wanted to wear a night-dress and the following day as he and Lucy got ready for school he begged me to let him wear one of Lucy's pleated skirts.' She smirked. ' I couldn't of course, I don't think his all boys school would have approved but as a compromise I let him wear her frilly party knickers under his school trousers.'

Clare stared at me aghast her jaw almost touching the floor.

'I couldn't remember such detail. It was a long time ago.' I stutter.

'And when he got home,' mum added, 'he ran straight upstairs to Lucy's room. Then while I was getting tea ready unbeknown to me Lucy helped him undress and wear her uniform. The full works - skirt, blouse, tights, tiny bra and even her school knickers. Lucy thought it was hilarious. And from what I remember he found it terribly exciting.' she raised an eyebrow and the two women smirked knowingly.'

I blushed and my cock began to twitch as I felt blood rush into it like a raging river.

'Weren't you worried?' Clare asked.

'No, not really.' I explained that he couldn't wear a dress because he was a boy. I felt guilty for dressing him up like a girl on holiday but again I did sympathise.' She sighs and plays with the hem of her own dress. 'You must know how nice it is to wear pretty feminine things, to be treated as special and to flirt. So again, as a compromise I would dress him up at the weekends or for special occasions. To be honest I assumed it was just a passing fad that he would grow out of.'

'Ok,' I say, 'moving on,' but the girls weren't interested and Clare lent forward eager to learn more.

Mum smiled. 'If you ask him nicely I'm sure he will tell you how he was a beautiful bridesmaid for a friend of mine at work or how he won the Easter bonnet competition and how he dressed up as a gangsters moll for the school play. That was a favourite.' She flipped through the album as if searching for photographic evidence. 'I'm not sure if I kept the photo but he looked so convincing in a flappers dress with a headband, feather boa, expanding cigarette holder, fish-net tights and long white gloves. From what I can remember he drew quite a crowd and a couple of the gangsters couldn't take their eyes of him.'

I threw her a glance. 'Mum,' I cried. 'I can't remember any of this you're making it all up. Clare don't listen to her.'

Mum smiled but I could tell the damage was done. Why was she doing this? If mum liked Clare so much why did she jeopardise our relationship by telling her about the lost luggage and embellish the story so much?

Back at our flat Clare couldn't stop talking about what my mum had told her and she teased me cruelly by calling me Beatrice. Later in bed She wanted to know if I enjoyed the experience. She was determined to learn if I was disappointed when we got home and had to go back to school as a boy? She even asked if I'd worn my sister's clothes since. Did I want to dress as a woman now or had I had sex with a man. I was horrified. Yet there was a plus side. As she talked she became increasingly excited. She talked and talked about boys in dresses and my feminine side then to my horror she showed me an old photograph of Lucy and I dressed in our Sunday best dresses watching some theatrical show at the Spanish hotel.

'Where did you get that?' I ask. As if it wasn't obvious.

'Your lovely mum gave it to me.' She replied cheerfully, 'She gave it to me as a keeps sake.'

I winced and looked at the photo. It was particularly good. I was sitting demurely on a chair next to Lucy sipping a juice from a straw. I wore a pretty pink party dress, tiny court shoes and sparkly tights with a long pink ribbon in my hair.

'Nice tights!' Clare points out. 'I suppose you wore frilly knickers too?'

'It was cold in the evening,' I said justifying the tights.

Clare looked doubtful and laughed. 'Try again, Beatrice,' she said teasingly.

I shrugged and bit my lip. 'It was cold at night and I wasn't used to wearing nothing on my legs.'

Clare laughs. 'Oh darling! Your mum told me the truth. She told me how you wanted to look as pretty as your sister for the last night of the holiday. Apparently you wanted to be the belle of the ball. She said you had quite a tantrum until she dressed you in the same sparkly tights, training bra and panties.'

I stared at her in disbelief and shook my head.

'It was a long time ago,' I confessed, 'I, I, I really can't remember. '

But I could. The memories came flooding back. The dress with all its sequins, frills and underskirts. It was if I'd worn it yesterday. But what concerned me most was my over riding pleasure. I could clearly remember enjoying being a girl and wearing all Lucy's pretty things but now as a mature young man something else stirred deep within my loins.

Clare smirked knowingly took my hand and practically dragged me to the bedroom. 'Show me you're a real man,' she smirks.

Now there's an invitation and normally I would have jumped at the chance but somehow after being paraded in a dress and my past feminine exploits dragged up I felt my masculinity deflated. This did nothing to deter Clare as she stripped me down to my briefs. Almost naked she then pushed me backwards onto the bed and undressed herself in front of me in a provocative stripper way, swirling her discarded clothes to one side while singing at the top of her voice -- but my cock still remained flaccid and dejected. 'Oh dear,' she chirped, 'don't you want to play or would you rather be Beatrice?'

I gulped and felt myself blush but she didn't give me chance to reply as she pounced on me like a wild animal, thrusting her hand down my briefs as if digging for gold. Her nimble fingers were soon on my cock, massaging it gently.

'Tell me all your secrets, Beatrice,' she teased. 'I want the truth. Do you really enjoy being the little girl? Do you want me to dress you like your mother in a pretty party dress?'

'N, n, no,' I mumble but my rigid cock was telling her something completely different and as she teased me about my girlish experiences she pulled my briefs to my ankles and mounted me like a horse. 'Perhaps I should throw away all your underwear and make you wear pretty panties like you did in Spain.'

I shake my head but I didn't really care she felt incredibly wet and excited as she bounced rhythmically up and down. She seemed to love sitting on top and during our play she sat on me so that my cock looked as if it was hers. 'Look at me,' she cry's 'I'm the one with the cock.' And she then slides over me holding my cock guiding it into her sopping hole. I lie there giving in to her animal passion. I suggest that we turn over and do it in the normal way but she so excited she can't stop and she's enjoying fucking me. 'I'm the one with the cock and 'm fucking you,' she screams. 'I'm fucking Beatrice.' I open my mouth and let out a girlish scream as I spread my legs I imagine she has the cock. This makes me as rigid as iron but sensing my excitement she quickly pulls back so that I spurt cum everywhere.

Clare screams with excitement. 'I'll call that my Domme fuck,' she says climbing off me, 'and I'll reserve it for boys like you who want to be pretty girls.' She gives me a sly wink and disappears into the bathroom leaving me to lie exhausted on the damp bed feeling very femme.

No more was said about the incidence nor did she do her 'domme fuck' again and neither Clare nor my mum raised the subject again yet something had changed in our relationship. I noticed how Clare kept the photograph of me in a dress in her special memories box under the bed and she seemed to be forever recording programmes on the television about cross dressers. That said, as a couple we got on more and more and I thought this was the one. Summer came and we booked to go on our first holiday together. We spent days pouring over holiday brochures but eventually chose a hotel on one of the quieter Canary Islands, Feurteventura, in the hope that we could have some quality time together. In fact we where getting on so well I decided to take the holiday opportunity to ask her to marry me. I told mum before we went and she seemed delighted.

'I could tell she's good for you,' she said. 'I knew from the moment you introduced us. Such a good judge of character, such a well mannered and good natured girl.'

Mum kindly offered to drive us to Gatwick airport and was as excited as us. She parked in the 'short stay' and followed us in. I thought at one point she wouldn't go but as I left her with Clare at the check-in desk and popped to the loo, she disappeared. Clare met me outside the gents and alone at last we walked into the departure lounge hand in hand.

The enhanced security caused long delays and the flight to Feurteventura was slow and tiring, neither of us slept on the plane. The meal was predictably unpleasant and to make matters worse Clare knocked the air stewardesses hand when collecting the dinner empties and spilt bright red lasagne all in my lap, ruining my cream chinos. When we eventually landed, four hours later we where exhausted, dishevelled and in my case messy. Passport control was slow and baggage collection crowded. Clare's bag came through as one of the first but mine was slow to arrive. We waited patiently as the other holidaymakers collected their luggage but as they collected their bags a stab of panic shot through me - surely my luggage had not got lost.

Soon the belt was empty except one lone suitcase that sadly wasn't mine. It looked similar but it was newer than mine and had lost its tag. The tour rep grew impatient. The bus driver apparently wanted to go. With my luggage seemingly lost the tour rep offered to look into the matter the following day and Clare suggested I take the mystery lone suitcase since its owner had probably taken mine and we could swap at some later stage.

I was needless to say furious but Clare and the tour rep didn't seem to be worried.

'It often happens,' the rep said, 'your case will turn up in the morning. Don't worry. I'll get it delivered to your room.' She was so convincing I began to relax and gazed out of the coach widow and looked forward to reaching our hotel.

We where the last couple to be dropped off and our Hotel looked magnificent and to our delight we where just in time for dinner. The tour rep looked at me sadly as we clambered off the coach.

'A word of warning,' she said, 'this is a five star hotel and they have quite a strict dress code.' She looked at my lasagne stained chinos. 'You wouldn't be allowed in with those trousers. I'll arrange for some food to be delivered to your room.'

Clare's full lips curved very slightly into the ghost of a smile. 'No don't worry,' she said. 'We will improvise.'

She looked me straight in the eye and reminded me uncomfortably of how mum used to speak to me in my youth.

I should have known then what she meant by 'improvise' and predictably as I showered she laid out two pretty dresses, one for her and one for me.

She was already wearing clean lingerie I walked into the bedroom and as I spotted the dresses on the bed I saw an evil glint in her eye. She smiled broadly and held out a pair of her panties. 'Come on love it will be just like old times. Show me how you can dress like a pretty girl.'

Tomsparty
Tomsparty
646 Followers