What Have I Done To Deserve This?

by Colin Sigfried

    

This is a continuation from part one whereby I have to disguise myself as a schoolgirl to get passed my girlfriend's mother. She has seen me and asked me to go out for a meal with the family. She has asked my girlfriend, Becky, to find some suitable girly clothes for me to wear.

The story continues….

So, rather reluctantly I trudged up the stairs behind Becky. "What am I going to do?" I asked.

"My mum is quite formidable and won't take no for an answer. We'll have to go along with it but it's only for the evening and you'll get a free meal. You did a great job of convincing her you were a girl, it's a shame it seems to have backfired. Do you need to call your mum and let her know?" Becky said.

What, let my mum know that I am going out with my girlfriend dressed as a girl, wearing her underwear in front of her family, that will go down well I thought. Besides, my mum was a single parent and decided at 17 I could fend for myself. She would be out with one of her men friends tonight anyway. I explained this to Becky.

"Right" said Becky, "I'll get you something to wear then."

"Nothing too girlie, please" I replied, feeling rather deflated.

"As I said earlier, Colin, I'm a girlie girl. I only have girlie stuff, that's what attracted you to me, wasn't it?" she said.

"Yes, true, let's get it over with then. I don't have to wear a skirt do I?" I retorted.

"I think it would be more convincing if you wore a skirt and besides, you're wearing one now and you seem at home with it!" she joked.

She rummaged through her wardrobe and pulled out a variety of clothes. "We haven't got much time so you'll have to trust me!" she exclaimed "I need to find something to wear too. Here, try these on, keep the bra and knickers on though."

She passed me a pair of patterned tights, a black satin flared miniskirt and a black off-the-shoulder jumper. I removed the school uniform and started to try on my new outfit whilst she was in the ensuite getting ready herself. She came out and looked stunning in a white lacy top and white mini skirt.

"You look nice, Bridget" she said mockingly "My clothes fit you perfectly, I'll get you a pair of my black boots and a little black handbag."

"Oh great, now you're calling me Bridget and giving me a handbag! Could this get any worse?"

Becky helped me on with her suede boots which I must admit were very fetching and I was reasonably okay walking in them. "You can hang onto me, Bridget. You'll be okay but remember to behave like a lady!" Becky said.

"Will you stop calling me Bridget! I'm Colin remember!" I said sternly.

"Not dressed like that! You're supposed to be a girl called Bridget. I can't keep calling you Colin can I? Anyway, I have to add a few finishing touches to your appearance so you will be fully en femme."

Well, she did have a point. I was wearing her lacy underwear, black tights, satin miniskirt with delightful suede boots and an off -the-shoulder jumper. Not only that, I was in full make-up and had a girl's hairstyle. I was Bridget Fonda. Even I couldn't call myself Colin.

"What finishing touches?" I asked nervously.

"Well, Bridget, I need to do something with your nails, look at them! And you need to accessorize love!" she exclaimed.

Becky quickly filed my nails and gave them a quick touch up of some strong smelling varnish, "Don't worry that'll try in 2 minutes Bridget". She then presented me with bangles and dangly earrings. "Here, put these on" she said. I had holes for earrings and nervously put these dangly objects into my ear. Finally, she sprayed me with perfume.

"Done. You look wonderful, Bridget. Let's go downstairs and knock 'em dead! Oh, remember to fix your skirt every time you sit down and do everything daintily!"

The Meal

Here we go again, I thought. I have to spend the evening with a bunch of strangers pretending to be a girl so that I don't get killed! What have I done? What turned out to be a very nice day with my girlfriend turned into a nightmare. I hadn't worn girl's clothes before let alone pretend to be a girl. I had to make sure that I didn't give the game away, I had to remember that it would only be for a couple of hours and Becky would help me, wouldn't she? Fear started to pass through me, what if I didn't get to sit next to her? What if I had to sit next to one of her thuggish brothers and make polite conversation? Surely, up close someone would see through my deception. Anyway, this was the situation I was in and I just had to get on with it.

"Wow, look at you two!" Her mother said in amazement as we walked down the stairs. "You both look lovely girls, now into the car and we'll set off."

I tried to walk like a girl, gripping onto Becky's arm, and when I went into the car I was careful of my short skirt and sat properly. Her brothers then joined us. "Oh, who are you? I don't think we've met. I'm Alex" said the eldest brother rather nervously I thought.

"Pleased to meet you, Bridget" I said in my girlie voice and shook his sweaty hand in a very ladylike way.

During the journey to Pizzahut I started to get more into character. I had studied the way girls move and gesture in Drama and we have had classes where we had to behave as members of the opposite sex, of course, whilst wearing our own clothes. Dressed as a girl actually made it slightly easier for me to behave like one. I even started to be a bit coy with the boys and play with my hair.

The ordeal at Pizzahut wasn't too bad, I managed to sit next to Becky which was great and we really kept ourselves to ourselves. I tried to eat like a girl, eating very daintily whilst the brothers attacked their pizzas like I would have done, like a lion devouring a wildebeest. Fortunately one of her brothers was in a bit of bother at work and Becky's parents were intent on discussing this with him. However, at one point I needed to go to the toilet when Becky reminded me I was posing as a girl so had to use the Ladies. She also said that it was etiquette for ladies to go together. What an experience that was! The toilet was pink and actually smelt okay, not the urine stenched facilities I was used to. What was also weird was that Becky re-applied her and my make-up. She said that I was a star for going along with this charade and that it wouldn't be much longer now before we got home.

"What do we do when we get back to yours, Becky?" I asked.

"We'll revert back to Plan A. This time, instead dressed as a schoolgirl, you'll be dressed as you are now – a hot chick! We'll go to the toilets and I'll sort you out. No problems" she explained.

"I must admit, I'm looking forward to being a boy again. Although this experience has taught me a lot."

With that we went back to the table, having finished our meals.

"Right, young ladies have you finished?" asked Ann.

We both nodded, as I tried to say as little as possible.

"Sorry we didn't get much time to talk to you dear. But we've had a few problems at home. I hope you understand dear" she directed at me.

I smiled sweetly and said "that's fine, thank you for taking me out for the meal. It was very good of you."

"Becky, you haven't forgotten that we have the dress fitting in about an hour's time have you?" Ann said.

"Tonight? I thought it was tomorrow!" said a very worried looking Becky.

"No dear, it's tonight so we had better get home now. Would you care to join us Bridget dear?" she asked.

Becky interrupted "Mum, can't we do it tomorrow instead? It's the last day of term, I just want to relax tonight."

"No, dear, it's been planned for a while now. Sophie and Louise are coming over to ours especially for this and Margaret is coming over with the dresses. It shouldn't take long but has to be done tonight" replied Ann.

Becky then told me that her cousin, Sophie, was getting married next month and had asked her to be one of her bridesmaids along with her other cousin Louise and tonight was the dress fitting.

Well, what was I going to do I thought. If Becky couldn't accompany me outside to turn me back into a boy I was stuffed. Sure I could go to the park toilets on my own, remove the make-up and get changed but my hair was still like a girls! I couldn't go home either because mum might be there, it was too risky. I was totally reliant on Becky to get me out of this.

"Well dear, do you want to join us?" she asked me.

"Erm, yes, okay" I hesitantly responded.

Bridesmaid Fitting

We got back to Becky's about 7:30 and went into her bedroom. Becky said, "Don't worry, the girls will be here at 8:00 and we'll be done by 8:30 then we can revert back to Plan A and get you back to being a boy again."

"Yes, this just seems to be going from bad to worse. I just want to go home and see you again as a boy. Not as Bridget but as Colin" I explained.

"You're doing a great job Colin as Bridget. You've really fooled everyone. I even think Alex fancies you. I saw the way he kept looking at you."

"Oh please! I just want to get out this situation as soon as possible" I said.

"You should feel flattered, anyway your disguise has worked. Listen, you'll just need to sit in the lounge for half an hour then it will be over. You'll be able to see me and the other girls undress and in their underwear. That should be worth it surely" Becky replied.

Shortly, the doorbell rang and Margaret, the dressmaker arrived, shortly followed by Sophie, Louise and Sophie's mum.

"Come down, girls, everyone's arrived" shouted Ann.

I was introduced to everyone as Bridget and just sat down and watched them undress and dress. All the men were banished from the room. I couldn't help but get quite aroused by these girls undressing in front of me. I was watching idly by until Sophie's mum said to me "Have you ever been a bridesmaid Bridget?"

"No, no I haven't" I replied.

"Oh, that's a shame dear. Every girl should get the chance to be a bridesmaid." She then looked at a spare dress and said "Here, try this dress on for size I think it's the same size as Becky's."

My stomach turned, here I was sitting with a bunch of women pretending to be a girl watching them get dressed. Now it was my turn to try on a bridesmaid dress! I had gone from being a schoolgirl to a hot chick to a bridesmaid, this was quite a lot to bear in one day.

"Well, no thank you, I'm fine" I replied. Becky looked at me in her dress and didn't know what to say.

"Nonsense! We're having all the fun here and you've been such a good girl sitting there. I think its only right you have a turn. You can feel what it's like to be a bridesmaid dear. Go on, give it go, we're all girls together, no need to be shy" Ann replied.

Being a bridesmaid was not something I had ever dreamed of being or wanted to be. If only my friends could see me now.

"Honestly, I'm fine, just watching you is fine" I replied, knowing that if I got undressed I would have trouble disguising my erection.

"I know dear, I think you're a little shy. Why don't you get dressed in Becky's room and we can see what you look like" and with that Ann gave me this pink satin dress to try on. "Becky, take these white stockings with you for Bridget to try on and this tiara for full effect" Ann added. "See you in a minute girls."

With that Becky and I trundled up to her bedroom holding a pink bridesmaid dress. "What have I got myself into now? Dressing as a bridesmaid!! Is this ever going to end?" I said.

"Oh I don't know, I'll think you'll look cute!" she laughed.

"It's not funny, Becky, can't you see what's happened today? I've had to pretend to be a girl, wearing your clothes, your school uniform of all things and even your sexy underwear. Now I have to pretend to be a bridesmaid, this is too much! Let's go, come on!" I started to get angry.

"You know my mum won't let you go without trying on the bridesmaid dress, so we might as well get on with it, and then we can go. Come on, try it on and I'll fix this tiara in your hair."

So I undressed yet again and replaced the black tights with the white lacy stockings. "This is just perverted Becky, look at me!" I said.

"Well, we haven't got you into the dress yet or fixed your hair!"

With that, she laid the bridesmaid dress on the floor and asked me to step into it. As I did, she pulled the dress up through my body and around my shoulders then zipped it up. It felt rather weird being surrounded by all this material but I must admit it did feel comfortable. It was fitted around my body and trimmed with lace around my chest and shoulders. She then carefully placed the tiara into my girl's hair.

"Look" she said "We look like a couple of bridesmaids at a wedding."

I looked into the mirror and boy did I look good as a bridesmaid, very pretty I thought, I would fancy me. The dress was a perfect size and no one would ever know I was a boy. "Come on, let's go downstairs and get this over with." Becky said, "Mind you, Bridget, I think you're starting to enjoy this now!"

"Well, I wouldn't say that but I must admit it has been quite an eye-opener."

With that, I gathered up the dress as I found it quite hard to walk in and went downstairs to be examined by the ladies.

"God Bridget, you look beautiful!" said Sophie. "You would look lovely down the aisle with me. Wouldn't she girls?"

Everyone agreed and then commented on how good I looked and how it had been shame that I had never been asked to be a bridesmaid. I took the praise and then sat down waiting for this torture to end. I had had enough, and wanted to be a boy again now.

"Have we finished now as me and Bridget want to go out" Becky said, sensing my uneasiness.

"Oh, Becky its gone 9 o'clock now you can't go out, it's dark! Give me a few minutes dear and I'll give Bridget a lift home. Your mum must be worried dear, do you want to call her?" questioned Ann.

"That's okay, Ann. I text her to say I would be late. I must be going though." I replied. Then it dawned on me that there was no way Ann was going to let 2 girls out on the streets on their own, and again, I was reliant on Becky to get me out of this fix.

"Bridget could stay the night mum, you don't mind do you?" asked Becky.

I thought what is she playing at, prolonging my torture like this! Then I suddenly realised it was a stroke of genius. Becky knew I needed her to get me looking like a boy again and if she wasn't allowed to go out with me, I would be taken straight to my home dressed as a girl. How would I explain that to mum. Also, Ann was the sort of person who would probably insist on seeing me in and might want to chat to mum. All our hard work would have been blown and we both would have been in deep water. No, all I had to do was keep up the pretence until tomorrow morning then we could both slip out and I could be a boy again. Plus the fact I would get to sleep with Becky! This would be worth it.

"Well, yes, no problem, if that's okay with you Bridget. You'd better call your mum and let her know" Ann said.

I looked at Becky, smiled and said "Yes, that's fine she won't mind. Thank you for letting me sleepover."

"Have you finished now Margaret, can we get changed?" asked Becky.

"Yes, dear, all done now, that's fine" replied Margaret.

So off we trundled back upstairs amidst wolf-whistles by the brothers.

"You were brilliant Becky thinking that up so quickly about me staying the night. I can keep my head down here for the night and we can revert back to Plan A in the morning. I love you Becky" I said with delight.

"I love you too Colin, despite looking every inch a girl!" she laughed.

"Let's get out of these bridesmaids dresses and relax in my bedroom for the night" she said.

We both undressed and she removed the tiara from my hair, she then slipped on a very sexy nightdress and dressing gown. "I must return these dresses, you stay here. Oh, you'll need something to wear in bed won't you."

"That's alright Becky, I'll wear the T-shirt I had on earlier and my boxers, remember when I was a boy?" I joked.

"You can't wear them, what if my mum comes in or we go down to breakfast in the morning. Let's not blow your cover at the last minute. Remember you've just got to be convincing til morning, after breakfast" she replied "I'll find something for you in a minute."

Becky went downstairs and I was just about to remove her underwear when I heard a knocking at the door, it was Alex asking for me!

"Just a minute" I said in a high pitched voice. I frantically rifled through Becky's drawers and found a white lacy nightdress, that will have to do and slipped on a white satin dressing gown. "Come in" I replied. Then I remembered I hadn't removed my stockings, I must have looked a real tart. Alex came in nervously, looking me up and down, he was obviously interested in me then started to stammer "Bridget, I er I was thinking…"

Then all of sudden Becky arrived "What do you want Alex? What are you doing in my room with Bridget, eh?"

"Oh nothing, just came to see if everything was okay. I'm off out now, bye" and he quickly scurried away.

"Thank God you arrived when you did. He was making a pass at me" I said nervously.

"I'm not surprised looking like that you tart! That's enough to turn any teenage boy on" she laughed.

"It was all I could find!" I replied.

I removed the stockings and dressing gown, leaving the lacy nightdress and underwear. "I'll be glad to get out of these" I said.

"What do you mean? We have to keep up the pretence til tomorrow remember? What if we get caught by Alex again, eh? You need to keep the underwear on, otherwise you won't have breasts and you don't want anyone to see your willy do you? Except me of course!"

"You're right as usual but I can't wait for tomorrow morning to get back to normal."

"What? You can spend the night with me and you can't wait until tomorrow morning? I can't believe I heard that right."

"You know what I mean! It's been a long day and I want to get back to normality" I said.

Becky had a big double bed, we lay on the bed watching TV and cuddled. It did feel strange though wearing her underwear and nightie whilst doing that but at least Becky had removed the make-up. As we thought, Ann checked up on us before she went to bed, asking if I was okay and reminding me how stunning I looked as a bridesmaid and checking that I had my mum's permission to stay the night.

We both slept in the double bed and had a night of passion, it was wonderful and well worth the torture I had been put through.

The Great Escape

We awoke about 10 o'clock and Becky told me that I would need to wear girl's clothes and look like a girl until we could get to the park as we would have to have breakfast with her parents or at least see them. Unfortunately, Becky couldn't transform me back to a boy in her bedroom because there would be people about, being a Saturday.

"I'll just wear what you gave me last night" I said.

"You'll do no such thing" she said "A girl has at least one new outfit every day, I'll get you something nice to wear."

This time around it was a pleated denim miniskirt and a gypsy-style top. She applied a moderate amount of make-up to my face because it was coming off soon.

I went through the charade at breakfast then at last Becky said "Right, pack up you stuff, let's get out of here." Alex kept his distance, probably too embarrassed after last night.

We made our way to the toilets, ladies of course, at the park. Becky removed all the make-up and gave me a severe haircut. There was no mistaking this time that I was a boy, except I was wearing a gypsy-style top, short, pleated denim miniskirt and her underwear. I stripped off which seemed to delight Becky so we didn't waste a moment's passion. I then got dressed into my boy's clothes, what a relief I thought, not to be encased in all that satin and lace! We cautiously left the toilets one by one making sure no-one would see us. We met up in the park as though we hadn't seen each other for a while. Which was fortuitous as Alex was there. He came over and gave me a funny look. If only you knew, I thought!!

  

  

  

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