Rob, Jacqui and Jenny too

by Alison Barlow

 

I suppose this is the story of how I met my wife, not how I met the woman I eventually married but the person inside that woman and the woman inside myself.

Confused? Well let me explain, you see I already knew Jacqui and we had even dated before whilst we were both Uni. But things had not really clicked at the time so we had simply remained good friends. There was a definite attraction but in all the hubbub of those years stable relationships were not really on the cards.

We had met a couple of times since graduation when we all our old buddies had met up for weekends of nostalgia and drinking, there had even been a few drunken snogs but nothing more. Then on an otherwise normal day I got a phone call that unknown to me at the time would prove a turning point in my life.

Jaq had been having problems with her ex boyfriend and after they had finally split up he had been hassling her almost to the point of stalking. She was down depressed and in need of TLC. We chatted for ages and I tried to cheer her up, talk flowed easily and we decided I should go down to visit her in London at the weekend, her friend was having a party and Jacq needed a little moral support if she was to face the event.

I travelled down on the train, an uneventful journey with British Rail or whatever they have decided to split it into now. Jacq was waiting for me at Liverpool street station and all my good intentions of keeping it as friends and being a shoulder to cry on were shattered when I saw how gorgeous she looked. Jacqui was wearing a flouncy summer dress made from lightweight material and her athletic frame was all to apparent underneath. We embraced and I had to tell her just how good she was looking!

"Thanks Rob, but I have had a shit month, mostly with you men, to be honest if I didn’t know better I would become a lesbian."

One hell of an opening gambit, though we laughed I could tell she was really hurting inside. I apologised for being a man and for the rest of my gender trying to reassure her we weren’t all bad.

Back at her place, I dumped my bag and we caught up over a cup of coffee. She filled me in on all the details of that b@stard Paul, her ex. I offered a sympathetic ear, nodding and agreeing in all the right places.

"Thanks Rob you are a real star, it really is good to see you again," She leant over and kissed me on the cheek, "Anyway, enough of all my misery, we have an invitation to party and I for one need to let off some steam, what costume did you bring?"

"Costume?" I replied blankly

"Yes, costume for the party, I sent you the details in an email, Oh shit don’t say you didn’t get it"

"Sorry no idea what you are on about, no email no costume"

"Oh Rob, it’s Angela’s, my flat mate’s, she is going back to the States next week and we are having a leaving do at the bar in the high street, A private party but it is strictly fancy dress, themed on the States. Angela’s going as Wonder-woman and I have hired a gorgeous Southern Belle outfit."

"You told me about a party, but nothing about fancy dress, sorry, I haven’t got anything, is it too late to hire something? Can’t I just go as I am"

"Not really we have even forced Angela’s old boss to come along dressed up, I can hardly then drag you along in jeans and t-shirt can I, its too late for the hire shop now. Hmm, I wonder of we can cobble something together for you."

As she spoke the door swung open and in came Angela her American flat mate. She was tall and although a little on the larger side a very beautiful curvaceous girl. We were introduced and Jacqui explained the situation.

"Don’t fret my sweets" Angela intoned in her Yankie twang, "I am sure we have something for the young hunk here, Cinderella shall go to the ball"

I blushed as Jacqui giggled and Angela with a dramatic sweep of her hand floated off into her room. A few minutes later Angela called for Jacqui to join her and I was left alone in the lounge. I could hear hushed voices from them and a worrying amount of giggling, I pondered ear-wigging at the door but did not want to risk getting caught in the act so I stayed seated and tried, unsuccessfully, to listen from the sofa.

Eventually Jacqui emerged and sat down on the sofa next to me. Her mood seemed to have changed and she looked deep into my eyes and held my hand "Rob, do you trust me?" she asked

I was a bit thrown by this question, "yeah of course I do, you are a good friend. Why?"

"Well I have been a bit more than that haven’t I?" She was obviously flirting and the atmosphere was electric. "I have always loved the way you were up for anything, always one for a laugh and some fun, I can’t tell you how much this means you coming down to visit"

I smiled "Its nothing, you know I‘d anything to make you happy"

"Do you mean that Rob, anything?"

"Sure" I replied, "except maybe murder!"

We both laughed

"Good on yer kid, I knew you would" said Angela.

I hadn’t noticed she was in the lounge and I was puzzled by what she meant.

"Come on then lets see what it looks like on then!" Jacqui said dragging me off to Angela’s room.

Looking around I could see a number of half packed boxes and half opened draws with their contents spilling out. The posters on the wall were of half dressed male actors and arty black and white portraits. At the top of the bed were a couple of teddy bears and below neatly laid out was what looked like a cheerleaders outfit. It took a few seconds for the cogs to turn in my head but soon enough I realised what was happening.

"Oh no, I’m not wearing that!" I tried to laugh it off

"But you promised, you said you would do anything!" Jacqui looked at me with her special fluffy bunny face, bottom lip jutting out and her big sorrowful eyes glistening with false tears.

"But…"I protested

"No buts, the young lady here is right you did said anything" Angela glared, "or are you going to break you word like all the other men in her life."

"Please, Rob, I’ll love you forever" and as Jacqui spoke her eyes flashed emphasising the words love and forever. All my resistance melted with those words, I was defeated, how could I resist this good cop bad cop routine and I had said ‘anything’, and I meant it. In reality I think my resistance was only really for show, being honest with myself, I wanted to see what it was like to try on the outfit and to be dressed by the two beautiful girls.

I stripped and showered and with a towel around my waist returned to Angela’s room to be dressed. They were both quite animated and excited and I could help be infected by their obvious delight in the situation. Jacqui handed me a pair of white cotton panties to put on. I tried to cover my modesty but Jacqui pulled the towel away "Oh Rob, don’t be so shy I’ve seen it all before and believe me you haven’t got anything Angela hasn’t seen either."

Standing naked and feeling very vulnerable I slipped the panties on. I tried to cover myself with my hands but it was plain to see the decorative edging of the panties and the white cotton stretched over my manhood. Next came a bra.

"We thought your build would suit a c-cup so you can borrow one of mine" Jacqui said handing me a white, slightly padded, seamless bra ‘as it wouldn’t show through my uniform’ I was told. They filled the cups out with scrunched up tights and stood back to admire their work.

"She looks pretty good considering" Angela mocked to Jacqui.

"Give it time we can make her look much better" She replied quite earnestly.

"Erm, excuse me but I am still here!" I protested

"Sush, my sweet, you keep hushed whilst we make you up"

I was sat at the desk whilst they applied my makeup, making me pout and close my eyes whilst they painted my face with strange powders and potions. I kissed a paper towel and saw the brilliant pink of a lipstick mark that had come from my mouth. I desperately wanted to look in the mirror to see what they had done but I had been told to sit quietly. It had gone too far for me to protest now, and anyway I was enjoying all the fuss and attention, which man wouldn’t, with two beautiful girls fussing over him, even if the circumstances were slightly unusual.

"We shall have to do something with those legs, beautiful as they are young cheerleaders do not have hairy legs!"

For a horrible moment I thought they were to shave my legs, try explaining that to the lads. But, to my relief they simply meant I had to put on a pair of opaque shimmering flesh coloured tights. Having no idea how to put them on, Jacqui carefully rolled them up my legs smoothing them out by running her hands up my calves and up over my thighs. What a sensation, was it the tights or the hands, I didn’t know and I didn’t care, it felt divine and I tingled to my very core.

"These knickers will hide the top of your tights and cover your panties from prying eyes"

Jacqui passed me a pair of blue full-cut gym knickers that I dutifully put on sliding them up my nylon-clad legs and wiggling them over my cotton panties. The intensity of the feelings was starting to show in my groin and Jacq did not help by brushing her hand against me.

"My my cheerleaders certainly don’t have bumps there!" she smiled "Perhaps it is time for the skirt to save your blushes"

The skirt in question was blue with white flashes between the pleats, Jacqui zipped me in and fussed at the hem making it straight and smooth. Her hands wandered in the process and I sensed she was having as much fun as I was. Was this turning her on as well? I felt strangely coy having her knelt before me with her hands up my skirt, and I noticed Angela had slipped off to shower and left us alone.

"I never noticed you had such beautiful legs." She said as she ran her hands teasingly over them again. My panties were really straining now, I just wanted to grab and kiss her. She must have sensed this as straightening up to face me she planted a delicate kiss on my cheek and whispered in my ear "Now little girl we mustn’t smudge your lipstick must we."

I meekly agreed and Jacqui helped me complete the outfit with a white tight long-sleeved turtleneck jumper and a cheerleaders vest over the top. I looked down to see my breasts jutting out under the costume, the jumper and vest stretched over them forming smooth feminine lines that ran down to my skirt. I sat on the bed to put on a pair of white bobby socks and slipped on the pair of pink and white trainers.

"Now all we need to do is your hair," said Jacqui holding up a wig made up of wavy blonde curls, "All the sexiest cheerleaders are blonde, and you are surely one of the sexiest I’ve seen."

Jacqui called Angela to admire their work, I still had not seen the results myself but I felt so beautiful and sexy with the two of them admiring me.

"Her nails! You must sort out her nails those scruffy efforts spoil the whole thing." Angela exclaimed dramatically.

So I sat again as Angela attached a full set of false nails to each hand and painted them in a baby pink "To match your pretty pink lips" she told me.

I obediently sat as the nail varnish and glue dried whilst Angela prepared her costume and Jacqui showered.

Jacqui returned with a towel wrapped around her and was delighted with my nails, "Oh you look even more beautiful, I think your ready to see for yourself."

Handed a pair of blue and white pom poms Angela turned the full-length mirror to face me. Or rather to face the blonde cheerleader who was looking back at me. I couldn’t believe it, yes it was me but I hardly recognised myself, I looked, well I looked stunning, I was amazed and secretly very pleased. They had transformed me, my legs looked long and slender running up to the flare of the pleated skirt. My breasts swelled under the jumper and my blonde curls cascaded down onto my shoulders. My masculine face was gone replaced by a much more rounded daintier version, they had done wonders with the makeup. I found myself adjusting the way I was standing closing my legs to a ballerinas pose and arching my back to lift my breasts.

"What do you think," Jacqui asked

I was almost speechless but managed to mumble "Wow"

"Oh I am pleased, you make such a beautiful girl"

My reverie was broken by Angela "Beautiful or not we have to get ready Jacqs or we will be late."

"I’ll wait in the lounge." I offered not wanting to get in their way.

"Don’t be silly you have to help us change, after all that’s what girlfriends are for." Angela patted me on the backside and I blushed. They both dropped their towels and there I was all dolled up as ‘one of the girls’, embarrassed to hell but loving everything about my sexy new self and my doorway into the secret female world.

I fell into the part as though I had been doing it all my life, I zipped Angela into her costume and helped her blow dry her hair, but most of my time was spent fussing over Jacqui, Her costume was beautiful, all pink satin and frills. I lovingly laid her underwear out on the bed, after she had chosen a cream basque set in delicate lace with matching stockings. The material felt divine and I longed to feel it next to my skin, I blushed as Jacqui suggested "Maybe you could try it on some time, a girl never feels better than when she has her sexiest lingerie on."

"Oh my how I would love that" I thought to myself, but said nothing.

Her dress was full length with luxuriant frills around the hem, the white silky puff sleeves were edged with lace which ran around the neckline and it gathered tightly in at the waist. I buttoned her in and straightened the satin over the net underskirts which flared it out from her hips to the floor. She looked so stunning, with lace gloves and a parasol she was every bit the Southern Belle.

We were all set and it suddenly dawned on me that far from everything being done my night had not yet begun. I had been carried away by the mood, enjoying the thrill of being a cute little cheerleader and one of the girls, but I was completely unprepared for facing the outside world. I felt panic rising inside me, I couldn’t possibly go out like this, everyone would laugh at me, I’d get beaten up, humiliated. I looked desperately at Jacqui to save me, to say "don’t worry I wouldn’t make you go out like that, here put this cowboy outfit on, we were only messing you about". But those words were not spoken, instead Angela cracked open a bottle of bubbly and proposed a toast to the three sexiest girls in London. I gulped the champers with haste hoping the alcohol would numb the anguish I was feeling. There was a horn in the street, Jacqui flicked the net curtains and announced "Taxi’s here"

My heart was racing, was there no way out, drinks were downed, lippy checked and we were out the door. Jacqui grabbed my arm and whispered in my ear "Don’t worry, you look sensational!"

The cold of the night whistled around my exposed legs, I clutched at my skirt to stop it lifting in the wind and virtually threw myself into the relative safety of the taxi.

"Where to ladies?" the driver asked having a good ogle at the unusual passengers.

"The Ugly Duckling, on Kilburn Street please." and we were off. Angela was chatting to the driver, explaining the reason for our attire and the party. Jacqui meanwhile flushed from the champagne whispered closely in my ear.

"He has no idea, you’ve totally fooled him, though I think we shall have to work on your entries, nice young ladies keep there legs together and don’t show their knickers to all and sundry, no matter how short their skirts are!"

Again I blushed, but not wanting to be discovered I decided I would need to watch Jacqui more closely and copy her.

I shuffled to the edge of the seat and keeping my knees practically welded together, swung my legs out of the door before standing up out of the cab. Sticking close to Angela I crossed what seemed a mile of pavement to the door of the bar and as ladylike as possible stepped inside. The bar thankfully was lit in a subtle manner and quite empty for the moment, except for King Kong, two cowboys, one cowgirl and an Indian squaw.

Angela squealed and ran over to the group arms out in order to embrace them all, and after dramatic kisses for them all, she beckoned me over. The panic was back, oh god here it comes, the humiliation begins. I walked over with Jacqui desperately hoping for the fabled hole in the ground to open up for me.

"Everyone, you’ve met Jacqui haven’t you, and this is her old Uni friend, Jenny." Angela gave me an exaggerated wink.

Jenny! What the…., oh my god, my mind was racing. Angela had made me a girl for the night and had christened me all in one sentence. I braced myself for the laughter or worse, but none came. Instead King Kong took my hand and kissed it with a muffled "Hi I’m Craig" from inside the rubber mask. The others introduced themselves and I even got a "Fantastic outfit" from the squaw. I couldn’t speak and ended up meekly nodding and offering a weak smile. I could feel my cheeks burning red and my legs turning to jelly.

"Come on Jenny, I think you could use a drink" Jacqui rescued me and whisked me off to the bar.

"Oh fantastic, this is so cool, they actually think you’re a girl, isn’t Angela brilliant, aren’t you the gorgeous one, Jenny is so you." She kissed me on the cheek and patted me on the bottom.

"But Jacqui, I can’t pull this off, what if they find out, how can I speak to anyone!"

"Just soften your voice a bit don’t try to do a falsetto no women squeek like that. Oh, stop fretting you’ll be fine, here you order the drinks. Wine for me please"

The Barman approached "What can I get you ladies?"

Following her advice I spoke as softly as I could and still be heard "A pint of John Smiths and a dry white wine please."

"No Jenny" Jacqui interrupted, giving me a filthy look, "Rob doesn’t want a drink"

She turned to the Barman "Sorry, just two dry white wines please."

As the barman fetched our drinks Sarah whispered in my ear "You’re a lady now and you don’t drink pints of bitter."

The Barman returned and placing the glasses on the bar I saw him grab an eyeful of Jacqui, and then to my surprise an eyeful of me!

"Nice pom poms love."

I blushed not knowing where to look, he didn’t have a clue.

Jacqui chose a table with a view of the door so that we could see the guests arriving.

"See, your doing fine, just stick close to me I’ll look after you, this is going to be such fun."

With a few glasses of wine inside me I began to relax and even started to enjoy myself. A group of Jacqui and Angela’s girlfriends had joined us as the bar filled up with people in all kinds of outfits. I had been introduced, as Jenny, to so many folks and so far no one had showed any signs of reading me as a bloke in a skirt. I had been totally accepted into the confidences of this girly group as they discussed the talent around and the details of their various love lives. I felt a bit of an impostor but Jacqui was looking after me and seemed to be revelling in our little secret. They questioned her about Paul, "Oh I’m off men all together now, they’re all the same. Well most of them anyway" As she spoke she put her hand on my leg and gave me a big smile.

"Jenny and I have decided we shall become lesbians, haven’t we darling"

Blushing again I mumbled "Er yes, yes, men are just not worth it."

Everyone starting laughing, "good for you, sisters I think we may all just have to join you."

The wine had gone straight through me and I excused myself from the group. Walking up to the toilets Jacqui caught up with me and steered me off to the left, "Us girls are allowed to go in pairs my angel and I don’t think we should be going to the little boys room now should we."

Oh god, I hadn’t even thought of that. Fortunately inside the little girls room it was empty, I felt like I had entered the forbidden city, breathing in the heady intoxicating smell of perfume.

"Now my little cheerleader don’t forget you have to sit down and please don’t put the seat up!"

Afterwards Jacqui checked my make-up and her own. She handed me the lipstick helped me re-apply it. I looked in the mirror and examined my female face, the curls of the wig framed my features, the two of them had done a fantastic job. My eyebrows seemed thinner and more arched, my colouration was much more even and my pretty pink lips matched the subtle powdered shades of my eyelids. I looked and felt like the a beautiful cheerleader I was dressed as.

Jacqui suggested a dance, and with my inhibitions loosened by the alcohol I began to really get into the part. The DJ played Hey Mickey for the cheerleader and I shook my pom poms for him, though I resisted trying the splits or a handstand, as I didn’t want to surprise anyone with a flash of the secret under my skirt.

‘Oh what a night!’ driving home in the taxi there was just Jacqui and myself both pretty tipsy giggling like school girls. Angela had disappeared off in the opposite direction with an old flame to, in her words "relight a few fires."

"You were fantastic tonight Jenny, your my special lady" she threw her arm around me and slipped her hand along my thigh. "I love you".

I gently grabbed her hand and stopped her reaching up my skirt, I could see the taxi driver’s eyes almost popping out of his head in the rear view mirror and I thought we might crash. Also she was not helping as her hand had stirred the contents of my panties which, in the tight confines of the cotton were causing me more than a little discomfort. Fortunately we made it safely back to her flat. Paying the taxi driver he gave me a seedy look, "You girls have a nice night now" he offered laden with innuendo. Oh typical men I thought to myself, and smiled sweetly back at him. Inside Jacqui could hardly keep her hands off me, squeezing my padded bra and blatantly groping my knicker clad buttocks. If you can’t beat em join em I thought and with no care for our makeup we fell into a frenzied passion.

 

 

 

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© 2002 by Alison Barlow. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.