A little touch of paradise
I had managed to catch the neighbourhood fox dead to rights in a trap de coeur. In return for not blowing the whistle, I was going to get to wear her pretty clothes and indulge in a little T-girl petting.
Let’s face it: finding someone to dress you up is no small challenge. It’s especially hard when you’re a college-age high school student still living at home with your parents in a conservative, middle-class part of town. There was no way I could tell my mother what I craved: she’d have me on the psychiatrist’s couch before you could say “garter belt”. I had no sisters so my mother was the only female whose clothes I could safely “borrow” for a little TV fun. Sadly, when it came to pretties, she was pretty conservative – her dresser was full of ugly cotton panties, utilitarian bras and thick pantyhose. Yuk! Her wardrobe was even less tantalising: not a fabulous flouncy silk frock or pair of stiletto heels in sight. Then there were the nasty oedipal overtones of wearing mother’s clothes – and the thought of Anthony Perkins in Psycho - and I very quickly lost interest.
That’s not to say I had abandoned the idea of finding someone for a little drag dalliance. But it would require a little scheming. I first needed a woman, older and stylish, to take me by the hand and make me over – that was clear enough – but no female in her right mind would have anything to do with the local weirdo teenager and his strange predilections. It was a dastardly dilemma and seemed insurmountable. But I was nothing if not sneaky and creative and I eventually lighted on the solution: Blackmail.
I wasn’t envisaging a criminal shakedown – I’m a tranny not a mafiosa - but I figured if I could find a woman with a deep, dark secret, she might just be prepared to do my bidding in return for me not ratting her out.
So how exactly to do it? First I had to find my mark. That meant watching and waiting. It was school holidays so I wouldn’t appear suspicious wandering around the neighbourhood, looking for lost footballs in various neighbours’ front and back yards or knocking on doors asking if anyone needed jobs done, garages cleaned out, garbage carted away. In just a few days, I had the whole neighbourhood sussed and under surveillance. Even if this didn’t pan out, I told myself, there was undoubtedly a future for me in criminal investigation (I could just picture myself in a sweet policewoman’s uniform with tight blue skirt and black stockings).
There were a few possibilities. I spotted Mrs Merrywidow, who lived in the big white house on the corner, stealing the morning newspaper off her next-door neighbour’s lawn. But she was a bit dowdy for my tastes. Further down the street, Cindy Trueheart – now she was a fox I could happily play lipstick lesbians with – was using too much water on her lawn, especially as the region was in drought. She compounded that offence by failing to pick up her doggie’s droppings from the grass verge on their regular walkies. These were all, unfortunately, misdemeanours and I needed a felony. Orange is the new little black dress and all that.
And then one mid-morning I noticed some odd activity at No. 36, the neat and tidy address of the Pulaski household, Lily and Michael. I knew them only to look at; they had moved in a few months before. They appeared to be a fairly normal, c***dless couple in their early 30s. He wore a suit to work in the morning; she stayed home. She appeared to be the adventurous one, favouring short skirts and red lipstick when she ventured out in her frisky blue Corvette. After the first stakeout, I had almost crossed them off my list: him being boring and her slightly ravishing were no crimes. And then I noticed a silver Camaro pulling into the driveway, almost exactly an hour after Michael had left for work. A handsome young man alighted and was quickly ushered inside. It could have been anyone, I first thought. Especially as he was in there for no more than an hour and a half. But then two days later, the exact same thing: hubby off to work, young stud arrives, two hours inside, and then gone, only this time I’m sure I caught a surreptitious look about him as he slipped into the Chevvy and sped off. A week later, I was sure. Lily Pulaski was having an affair. And I may have found the answer to my prayers.
Now came the hard part. I couldn’t just appear at her front door and say I’m going to tell your husband you’re banging your boyfriend unless you let me wear your clothes. That would be stupid – and dangerous. The poor woman would have every right to ring my mother and tell her I was perverted or mad or both, and I’d end up in a military boot camp in Tierra del Fuego. So subtlety became my watchword.
(In retrospect, I often wonder if all my byzantine strategising, people-reading and stealthy stalking were a function of my transgenderism; those qualities are generally attributed to “the wily female”, although I doubt that’s one of the more attractive of the feminine arts. Still, as they say, a girl’s gotta do what a girl’s gotta do even if she’s temporarily stuck in a boy’s body.)
After much thought on the matter, I decided the indirect approach would work best. Somehow, I would have to insinuate myself into her confidence, show her what a wonderful person I was, act all vulnerable and misunderstood, then innocently hint at the fact I knew what she was up to. Then, I hoped, she would need to barter for my silence. And, bingo! I would get a sweet transformation and maybe even some girl-on-girl action. It was almost perfect. Machiavellian, in fact. The only serious problem I could see was if she was already planning to ditch her husband and run off with her lover. But I’d cross that bridge when I got to it.
I’m such a sneaky bitch!
*******************
Now that I was certain Lily Pulaski was ripe for plucking, I put my plan into action. Before dawn on Wednesday - lover boy only visited on Tuesdays and Thursdays – I slipped into her carport, whipped open the hood and pulled a bunch of electrical leads. Around 10am, while I was nonchalantly riding my bike up and down the street, Lily appeared in her trademark pencil skirt and clinging sweater and hopped into her car. As expected, the engine whirred and grunted but wouldn’t start. Inevitably she got out, clearly annoyed, and, cracking the hood, started searching for the problem. Right on cue, I rode up beside her.
“Hi there,” I said brightly. “That’s a really sweet car you’ve got.”
She looked up from the engine. “Oh hello. Yes, I love my little Corvette -usually. Today, however, it’s decided to go on strike. And I have a really important appointment to get to.” She paused. “I don’t suppose you know anything about cars, do you? I’m hopeless with machines.”
“I know a little bit,” I lied. “Do you want me to have a look?”
“Oh please do. I’m Lily by the way.”
I heaped on the polite charm. “I’m Patrick – pleased to meet you, Lily.” She backed away from the car to let me at the engine bay. I pretended to study it part by part. Then “I think I know what the problem is.” I covertly reattached the leads I’d pulled earlier.
I bade her get back in the car. “Try it now.”
She hit the ignition and the motor turned over first time. “There you go,” I said.
“Thank you so much, Patrick.” She waved to me from the driver’s seat. “I have to get going but let me make it up to you; come over for afternoon tea – say, about three. I’ll bake you some cookies. Bye.” She dropped a lead high heel on the accelerator and sped off in a light, blue cloud.
Just after three, I was standing on her front porch. I dug a finger into the doorbell, and soon heard her heels clattering down the hall. Her smiling face greeted me.
“Patrick, I’m so pleased you came. I can’t tell you what a lifesaver you were this morning – anyway, come in.”
I followed her svelte body to the kitchen where the table was set and the smell of coffee wafted aloft. “I hope you like espresso.”
“Grazie! Coffee’s fine,” I laughed.
“Come and sit down so we can chat.” She had me sit on one of the wooden chairs then parked her pert behind in its next-door neighbour.”
We talked for a while: little of significance. Then I butted in. “Can I ask you something very private?” I said.
“I guess so,” it probably seemed a little inappropriate. “Now what’s this all about?”
“I don’t want to sound threatening,” I began a practised patter. “But I happen to know what’s been going on in here for the last few weeks with a young man who isn’t your husband.”
I could tell she was boiling over with embarrassment. “What the hell are you talking about,” she shrieked.
“Look, don’t get angry, I need you to help me with something and I’m pretty sure the only way you would do it is if you had to. I know that you’ve been having an affair and I doubt that you’d want your husband to know about it. I wouldn’t tell him, I promise. I just want to be able to talk to you about something and I can’t have you rejecting me or telling someone – like my parents.”
“You’d better explain yourself,” she said, a little quietly now. “I certainly don’t want Dan [her husband] knowing what’s been going on but I don’t know what you want that’s so curious or how I could possibly help you. So start talking or start walking”
‘It’s simple but complicated,” I said. “You see I have this desire to dress up as a girl, to actually be a girl – at least for a little while. I certainly can’t tell anyone, my friends, my family … I need someone who could be sympathetic, even if it’s only because they have to be.
“I just couldn’t think of any other way of doing it – I need you to help me be a girl because I think you’re beautiful and adventurous. But I couldn’t just ask you out of the blue because you could easily have simply told my mother and I would have been in real trouble. This way we’re equal: I know something you don’t want anyone to know too.”
“What an odd boy you are,” she said. “Let me get this straight. In exchange for not telling my husband about my affair, I help you dress up like a girl. Wow, it’s actually quite amusing.” She smiled. “I hope I’m going to be able to carry on my other extra-curricular activities.”
I nodded.
“Good, well that kinda sounds fair. So when do you want to do this thing? My husband comes home at 5.30 like clockwork.”
“How about today?” I said, becoming quite excited now. “It’s holiday and no one is at home at my place right now so no one’s going to come looking for me.”
OK, Patrick – I can do that. But there’s going to have to be some ground rules. You do what I tell you, no arguments, and you behave yourself, like a good little girl. Speaking of which, I better give you a name.” she paused. “How about Debra. Debbie for short?”
I loved it. “I thought you would make me be Patricia or something obvious cos of my name,” I said. “But Debbie’s perfect.”
“OK, Debbie, into the bedroom with you.”
****************************
We didn’t go into the master bedroom, for which I was rather relieved. I didn’t want to be crowding her sexual life and I didn’t want to be near where her husband and boyfriend did their thing. Instead Lily led me into her spare bedroom. It was furnished with a single bed, covered with a red and white quilt, a dressing table replete with make-up paraphernalia and a wide built-in wardrobe.
“This is my dressing room,” she explained. “Which is ideal because it’s going to be your crossdressing room.” She smiled and I giggled. It was a nice ice-breaker.
I had relaxed enough now to take in Lily’s appearance. She was probably 32 or 33 – past that unlined teen-twenties radiance but gorgeous and supremely sexy. She was neither slim nor chubby but statuesque in the classic sense: tall – almost my height – proud bosom, round bottom, curvy legs. Her prettily oval face was set off by strawberry blonde curls and shining blue eyes. I had always thought her beautiful from a distance and was ecstatic to find her even more radiant close up.
She sat on the edge of the bed and had me take my shoes and socks off, then surveyed me with a practised eye. “I’ve done some modelling work in my time,” she told me. “This is only going to work if you have the goods, so to speak. I think you’re probably pretty enough, definitely slim enough, and padding will take care of the curves.” She traced an hourglass with her hands. “First thing for you will be to lose any body hair and have a nice perfumed bath.” She motioned towards the en suite bathroom. “In you go – and don’t be too long.”
I ran a hot bath and foamed up my legs and underarms – a woman’s shaver was at hand. I was young enough to be girlishly smooth but sc****d a layer of fuzz from my legs, arms and underarms. No one would ever notice. Fortunately I had shave my face that morning, so I was soon completely hairless and luxuriating in a scented pool.
When you’re ready, Miss Debbie,” was my call to arms. I dried off with thick white towels and wrapped another around my torso, girl-style, before emerging.
Lily was impressed; she smiled and clapped her hands. “Oh yes, you can certainly be a pretty girl.” I blushed a little.
I was pleased to see she had used the intervening time to change her own clothes. Such finery: a dark blue silk dress, white lace slip peaking from the hem; shiny strapped black high heels; nude silk stockings – seamed I would soon discover. Elegant but not overdressed. “I thought I’d get in the mood,” she explained.
“I suppose we should create a scenario of sorts,” Lily decided. “You can be my nephew, who I’ve discovered yearns to be a girl, but is too shy to say so. Then I discover you gazing longingly at the models in a glossy fashion magazine – I can tell what you want. You confess your desires; and I decide to help you make them come true.”
“Perfect,” I said.
“You know what comes next,” she commanded. “Get ’em off.” I allowed the towel to unravel from my body, and then slipped off my white shorts. “Hardly appropriate,” she declared.
“Panties first.” She produced a pair of high-cut white nylon panties, lace edging, lace waist band – they were gorgeous, I’d only ever dreamed of the like. I slipped my feet through and slithered them up my legs. The bulge spoilt the effect so Lily helped me tuck myself away. The panties were stretchy enough that they clung tightly and I soon showed a feminine mound.
“Boobs now.” She seemed to be enjoying herself immensely, and produced a bra. It seemed to be of the same set as the panties, daintily silky and lacy. She had me slip my arms through the straps and spun me around, hooking the eyes at the back. She turned me around again; she had two large breast forms to pad out the cups. Because the bra sat flat on my chest, you really couldn’t tell they were not real breasts. I was starting to feel very sexy and girlish now.
“You know, there’s loads of things girls get to wear,” she was teasing a little. “Especially underneath. We can wear tight girdles and silky panties, garter belts with lots of lace, silk seamed stockings – like mine.” She pirouetted to show me. “Bustiers, corsets … I’d bet you’d like to try some of those on, wouldn’t you.” I could only nod.
She went over to the chest of drawers and rummaged around among the flimsies. “Here we are.” She produced a white open-bottom girdle, with tight elastic panels and six suspenders.
“I think little Miss Debbie will love wearing this – stand here and we’ll slip it on.”
She held me by the arms as I carefully stepped into the garment and began shimmying up my legs. When I finally had it tight around my waist and thighs, she helped me straighten out the bottom edges. It was so tight and restricting – I felt a little faint with ardour.
“Now for nylons.” From the same drawer came a pair of sheer black stockings with seams and Cuban ankles and toes – very elegant. I sat on the edge of the bed as Lily showed me how to roll and unroll them up my smooth legs. Once in place and the seams nicely straight, she snapped the garters to the top of the hose.
“Stand back, pretty thing. Let me have a look.” I wiggled away and modelled my lingerie. I could tell she was enjoying it - her dress was hitching up around her thighs and I could see she, too, was wearing garters. “You actually make a very pretty girl, just in bra and panties. Better get you into a nice dress – no, a skirt and blouse.” She fished out a gorgeous white lace blouse with high neck that buttoned up the back, but first she helped me into a long slip, its lacy hem reaching just above my knees. I was feeling very grown up. After she had me buttoned up, she found a tight grey wool skirt and helped me slip into it. It seemed to cling rather nicely to my waist and a wide leather belt cinched me in even tighter.
“OK, you’re almost there – but mainly from the neck down. That face is a bit of a giveaway but we can definitely do something about that.”
She took my hand lightly and led me to the dressing table. I sat down in the plush velvet chair … but in ladylike fashion, keeping my legs together. I could feel the girdle smooth out my bottom as I sat, also restricting my thighs. It was a supremely pleasurable sensation.
After first assessing my facial features – lots of “oohs” and “aahs” and “very prettys” – she got to work with the makeup. Foundation first, a smell I knew from watching my mother paint her face, then eyeliner, eye shadow, rouge and a deep red lipstick. She also managed to glue on a heavily mascara’ed pair of false eyelashes, in spite of my blinking and twitching. The “oohs” and “aahs” became more trill. “Oh yes, this is a very pretty girl we have here,” she decided. “But you definitely need a cute hairstyle to set it off.”
My mother and sister didn’t own wigs so I had a great fascination for the idea of instant long hair. My dress-up sessions at home had been rather limited as a result. But Lily was a fashion plate and had four or five in boxes at the top of her wardrobe.
“Try this one.” She produced a honey blonde wig, medium length, with a sweeping fringe. My own hair was very short and Lily quickly had the wig in place, using her fingers and a tapered comb to give it style.
“Hey, what happened to that silly boy,” she joked. “All I can see is a comely young girl, with very sexy curves.”
Finally I tried on a pair of light grey high heels, with a thin strap across the ankle. It took some practice to become steady but I soon had the “heel, toe, heel, toe” rhythm working.
Lily appeared very impressed and grabbed me by the arm and led me, clacking away on the wooden floor, into the master bedroom where a long cheval mirror stood in one corner. “Check yourself out, babe.”
I almost swooned when I saw my reflection. Instead of a lanky young man, a svelte young girl was staring back. She was all elegance in lacy blouse and tight skirt, high heels, seamed stockings and glamorous blonde hairdo. I pouted and pirouetted, absolutely fascinated by my transformation. And while I could see the gorgeous clothes, I could feel the tight and frilly underwear clutching me. I kept hitching up my skirt to see the lace and nylon beneath.
Lily seemed transfixed herself. She came over and held me by the waist – as we danced slowly, she whispered in my ear. “Such a glamorous Debbie: I can feel you shaking. I’ve never met such a poised and pretty young lady. “Don’t you simply adore your clothes and lingerie; don’t you wish you were a girl all the time”. I lisped agreement. She held me tighter; and I could feel her breast heaving and her hot breath on my face.
“How would you like a little pussy action,” she whispered, stroking my hair, her perfume wafting over me. I groaned again; I was getting just a little dizzy.
She held my hand and pushed it between her legs. I traced a line up her nylon-clad legs, felt the taut garters, then brushed up against her lace panties. Her hand now guided mine down the waistband and into her V. She helped me rub her clitoris, which seemed to be dripping moisture. I took over, tracing rhythmic circles over her pussy. Her arms tightened around me and she moaned. “Oh God, yes, you painted little whore, you nasty little vixen, make me cum.”
As my hand caressed her faster and faster, I could feel her body bracing. The moaning rose in sound and then she grabbed me hard, kissing me roughly, and a shattering orgasm ran through her. “Oh sweet Jesus, yes.” Her mouth crushed mine, her tongue crammed inside, licking and tasting mine. I could not believe how excited I felt. I had been turned into a ravishing girl and was kissing and caressing another beautiful girl.
As her orgasm petered out, Lily looked lovingly into my eyes. “I had no idea I could get that turned on,” she marvelled. “I’m no lesbian but turning you into a lady has pushed my buttons. You are an exciting, exotic creature, Debbie, and a fast learner. Come and lie down with me.”
She lay back on the bed, flapping her skirt to cool us down. I knelt beside her and she pulled me closer, again kissing my mouth hard. “Girl sex is wild,” she whispered, and as I lay beside her, she began tickling me; I squirmed. “Ooh, a bit sensitive, are we?” She worked her way down to my knee, then began to run her hand up my leg, caressing me through the silk stocking, then slipped it under my skirt. “Such pretty lingerie for such a pretty lady,” she purred. “Ooh, and a tight little girdle – are you a virgin?” We both giggled. She was able to run her fingers beneath the tight panels of the girdle and gently tugged my panties down. My member jumped from its silky prison and very quickly hardened. “Aah, a hard little clit,” she said, her hand slipping around my erection. “Now, what would you like to hear about?’ she teased.
“I bet you would have liked your mummy to dress you up as a little girl!” I moaned. “I know I’d like to take you to the mall and the Little Miss boutique. I’d have you try on all sorts of frilly party dresses. We could dress as mother and daughter in big flouncy velvet gowns and petticoats. I could take you to the theatre and show you off.
“This is a dream come true, isn’t it? Do you go to sleep at night, praying you would wake up with pert little breasts and a tight little pussy? You’re almost there. You love the cool silk panties, and the lipstick and the girl kisses.
“Or do you fantasise about being reborn a female: first a baby girl all in pink, then a pretty little girl in pink party frocks and frilly panties and white lace socks and shiny mary janes. Next you’re the cute young teen, I’ll buy you skirts and jumpers and a whole dresser of glamorous lingerie. Sweet sixteen and just loving being kissed.”
I was delirious – all the exciting images were burning in my head. I’m sure Lily sensed this and resumed the deep kisses, her fingers now gently flicking my hard-on – “Feel that, you little harlot” – and I suddenly came in a shattering orgasm. My lips came free and I cried out: “Oh yes, I’m a pretty girl.”
As I fell back on the bed, I realised we were both out of breath.
“You know, I was quite shocked when you told me you wanted to be a girl. I didn’t understand what the attraction was. But I can now see why a boy would want a little taste of the wild life. I hope you enjoyed yourself.”
“It was the most thrilling experience of my life,” I told her breathlessly. “I really hope we can do it again.”
“Oh yes,” she replied “ I can think of many adventures for Debbie and Lily. You can be my pretty little secretary, my leather-clad love slave, my lingerie model, my latex lesbian …” She paused. “So what time can you come over on Friday?”
The end
Let’s face it: finding someone to dress you up is no small challenge. It’s especially hard when you’re a college-age high school student still living at home with your parents in a conservative, middle-class part of town. There was no way I could tell my mother what I craved: she’d have me on the psychiatrist’s couch before you could say “garter belt”. I had no sisters so my mother was the only female whose clothes I could safely “borrow” for a little TV fun. Sadly, when it came to pretties, she was pretty conservative – her dresser was full of ugly cotton panties, utilitarian bras and thick pantyhose. Yuk! Her wardrobe was even less tantalising: not a fabulous flouncy silk frock or pair of stiletto heels in sight. Then there were the nasty oedipal overtones of wearing mother’s clothes – and the thought of Anthony Perkins in Psycho - and I very quickly lost interest.
That’s not to say I had abandoned the idea of finding someone for a little drag dalliance. But it would require a little scheming. I first needed a woman, older and stylish, to take me by the hand and make me over – that was clear enough – but no female in her right mind would have anything to do with the local weirdo teenager and his strange predilections. It was a dastardly dilemma and seemed insurmountable. But I was nothing if not sneaky and creative and I eventually lighted on the solution: Blackmail.
I wasn’t envisaging a criminal shakedown – I’m a tranny not a mafiosa - but I figured if I could find a woman with a deep, dark secret, she might just be prepared to do my bidding in return for me not ratting her out.
So how exactly to do it? First I had to find my mark. That meant watching and waiting. It was school holidays so I wouldn’t appear suspicious wandering around the neighbourhood, looking for lost footballs in various neighbours’ front and back yards or knocking on doors asking if anyone needed jobs done, garages cleaned out, garbage carted away. In just a few days, I had the whole neighbourhood sussed and under surveillance. Even if this didn’t pan out, I told myself, there was undoubtedly a future for me in criminal investigation (I could just picture myself in a sweet policewoman’s uniform with tight blue skirt and black stockings).
There were a few possibilities. I spotted Mrs Merrywidow, who lived in the big white house on the corner, stealing the morning newspaper off her next-door neighbour’s lawn. But she was a bit dowdy for my tastes. Further down the street, Cindy Trueheart – now she was a fox I could happily play lipstick lesbians with – was using too much water on her lawn, especially as the region was in drought. She compounded that offence by failing to pick up her doggie’s droppings from the grass verge on their regular walkies. These were all, unfortunately, misdemeanours and I needed a felony. Orange is the new little black dress and all that.
And then one mid-morning I noticed some odd activity at No. 36, the neat and tidy address of the Pulaski household, Lily and Michael. I knew them only to look at; they had moved in a few months before. They appeared to be a fairly normal, c***dless couple in their early 30s. He wore a suit to work in the morning; she stayed home. She appeared to be the adventurous one, favouring short skirts and red lipstick when she ventured out in her frisky blue Corvette. After the first stakeout, I had almost crossed them off my list: him being boring and her slightly ravishing were no crimes. And then I noticed a silver Camaro pulling into the driveway, almost exactly an hour after Michael had left for work. A handsome young man alighted and was quickly ushered inside. It could have been anyone, I first thought. Especially as he was in there for no more than an hour and a half. But then two days later, the exact same thing: hubby off to work, young stud arrives, two hours inside, and then gone, only this time I’m sure I caught a surreptitious look about him as he slipped into the Chevvy and sped off. A week later, I was sure. Lily Pulaski was having an affair. And I may have found the answer to my prayers.
Now came the hard part. I couldn’t just appear at her front door and say I’m going to tell your husband you’re banging your boyfriend unless you let me wear your clothes. That would be stupid – and dangerous. The poor woman would have every right to ring my mother and tell her I was perverted or mad or both, and I’d end up in a military boot camp in Tierra del Fuego. So subtlety became my watchword.
(In retrospect, I often wonder if all my byzantine strategising, people-reading and stealthy stalking were a function of my transgenderism; those qualities are generally attributed to “the wily female”, although I doubt that’s one of the more attractive of the feminine arts. Still, as they say, a girl’s gotta do what a girl’s gotta do even if she’s temporarily stuck in a boy’s body.)
After much thought on the matter, I decided the indirect approach would work best. Somehow, I would have to insinuate myself into her confidence, show her what a wonderful person I was, act all vulnerable and misunderstood, then innocently hint at the fact I knew what she was up to. Then, I hoped, she would need to barter for my silence. And, bingo! I would get a sweet transformation and maybe even some girl-on-girl action. It was almost perfect. Machiavellian, in fact. The only serious problem I could see was if she was already planning to ditch her husband and run off with her lover. But I’d cross that bridge when I got to it.
I’m such a sneaky bitch!
*******************
Now that I was certain Lily Pulaski was ripe for plucking, I put my plan into action. Before dawn on Wednesday - lover boy only visited on Tuesdays and Thursdays – I slipped into her carport, whipped open the hood and pulled a bunch of electrical leads. Around 10am, while I was nonchalantly riding my bike up and down the street, Lily appeared in her trademark pencil skirt and clinging sweater and hopped into her car. As expected, the engine whirred and grunted but wouldn’t start. Inevitably she got out, clearly annoyed, and, cracking the hood, started searching for the problem. Right on cue, I rode up beside her.
“Hi there,” I said brightly. “That’s a really sweet car you’ve got.”
She looked up from the engine. “Oh hello. Yes, I love my little Corvette -usually. Today, however, it’s decided to go on strike. And I have a really important appointment to get to.” She paused. “I don’t suppose you know anything about cars, do you? I’m hopeless with machines.”
“I know a little bit,” I lied. “Do you want me to have a look?”
“Oh please do. I’m Lily by the way.”
I heaped on the polite charm. “I’m Patrick – pleased to meet you, Lily.” She backed away from the car to let me at the engine bay. I pretended to study it part by part. Then “I think I know what the problem is.” I covertly reattached the leads I’d pulled earlier.
I bade her get back in the car. “Try it now.”
She hit the ignition and the motor turned over first time. “There you go,” I said.
“Thank you so much, Patrick.” She waved to me from the driver’s seat. “I have to get going but let me make it up to you; come over for afternoon tea – say, about three. I’ll bake you some cookies. Bye.” She dropped a lead high heel on the accelerator and sped off in a light, blue cloud.
Just after three, I was standing on her front porch. I dug a finger into the doorbell, and soon heard her heels clattering down the hall. Her smiling face greeted me.
“Patrick, I’m so pleased you came. I can’t tell you what a lifesaver you were this morning – anyway, come in.”
I followed her svelte body to the kitchen where the table was set and the smell of coffee wafted aloft. “I hope you like espresso.”
“Grazie! Coffee’s fine,” I laughed.
“Come and sit down so we can chat.” She had me sit on one of the wooden chairs then parked her pert behind in its next-door neighbour.”
We talked for a while: little of significance. Then I butted in. “Can I ask you something very private?” I said.
“I guess so,” it probably seemed a little inappropriate. “Now what’s this all about?”
“I don’t want to sound threatening,” I began a practised patter. “But I happen to know what’s been going on in here for the last few weeks with a young man who isn’t your husband.”
I could tell she was boiling over with embarrassment. “What the hell are you talking about,” she shrieked.
“Look, don’t get angry, I need you to help me with something and I’m pretty sure the only way you would do it is if you had to. I know that you’ve been having an affair and I doubt that you’d want your husband to know about it. I wouldn’t tell him, I promise. I just want to be able to talk to you about something and I can’t have you rejecting me or telling someone – like my parents.”
“You’d better explain yourself,” she said, a little quietly now. “I certainly don’t want Dan [her husband] knowing what’s been going on but I don’t know what you want that’s so curious or how I could possibly help you. So start talking or start walking”
‘It’s simple but complicated,” I said. “You see I have this desire to dress up as a girl, to actually be a girl – at least for a little while. I certainly can’t tell anyone, my friends, my family … I need someone who could be sympathetic, even if it’s only because they have to be.
“I just couldn’t think of any other way of doing it – I need you to help me be a girl because I think you’re beautiful and adventurous. But I couldn’t just ask you out of the blue because you could easily have simply told my mother and I would have been in real trouble. This way we’re equal: I know something you don’t want anyone to know too.”
“What an odd boy you are,” she said. “Let me get this straight. In exchange for not telling my husband about my affair, I help you dress up like a girl. Wow, it’s actually quite amusing.” She smiled. “I hope I’m going to be able to carry on my other extra-curricular activities.”
I nodded.
“Good, well that kinda sounds fair. So when do you want to do this thing? My husband comes home at 5.30 like clockwork.”
“How about today?” I said, becoming quite excited now. “It’s holiday and no one is at home at my place right now so no one’s going to come looking for me.”
OK, Patrick – I can do that. But there’s going to have to be some ground rules. You do what I tell you, no arguments, and you behave yourself, like a good little girl. Speaking of which, I better give you a name.” she paused. “How about Debra. Debbie for short?”
I loved it. “I thought you would make me be Patricia or something obvious cos of my name,” I said. “But Debbie’s perfect.”
“OK, Debbie, into the bedroom with you.”
****************************
We didn’t go into the master bedroom, for which I was rather relieved. I didn’t want to be crowding her sexual life and I didn’t want to be near where her husband and boyfriend did their thing. Instead Lily led me into her spare bedroom. It was furnished with a single bed, covered with a red and white quilt, a dressing table replete with make-up paraphernalia and a wide built-in wardrobe.
“This is my dressing room,” she explained. “Which is ideal because it’s going to be your crossdressing room.” She smiled and I giggled. It was a nice ice-breaker.
I had relaxed enough now to take in Lily’s appearance. She was probably 32 or 33 – past that unlined teen-twenties radiance but gorgeous and supremely sexy. She was neither slim nor chubby but statuesque in the classic sense: tall – almost my height – proud bosom, round bottom, curvy legs. Her prettily oval face was set off by strawberry blonde curls and shining blue eyes. I had always thought her beautiful from a distance and was ecstatic to find her even more radiant close up.
She sat on the edge of the bed and had me take my shoes and socks off, then surveyed me with a practised eye. “I’ve done some modelling work in my time,” she told me. “This is only going to work if you have the goods, so to speak. I think you’re probably pretty enough, definitely slim enough, and padding will take care of the curves.” She traced an hourglass with her hands. “First thing for you will be to lose any body hair and have a nice perfumed bath.” She motioned towards the en suite bathroom. “In you go – and don’t be too long.”
I ran a hot bath and foamed up my legs and underarms – a woman’s shaver was at hand. I was young enough to be girlishly smooth but sc****d a layer of fuzz from my legs, arms and underarms. No one would ever notice. Fortunately I had shave my face that morning, so I was soon completely hairless and luxuriating in a scented pool.
When you’re ready, Miss Debbie,” was my call to arms. I dried off with thick white towels and wrapped another around my torso, girl-style, before emerging.
Lily was impressed; she smiled and clapped her hands. “Oh yes, you can certainly be a pretty girl.” I blushed a little.
I was pleased to see she had used the intervening time to change her own clothes. Such finery: a dark blue silk dress, white lace slip peaking from the hem; shiny strapped black high heels; nude silk stockings – seamed I would soon discover. Elegant but not overdressed. “I thought I’d get in the mood,” she explained.
“I suppose we should create a scenario of sorts,” Lily decided. “You can be my nephew, who I’ve discovered yearns to be a girl, but is too shy to say so. Then I discover you gazing longingly at the models in a glossy fashion magazine – I can tell what you want. You confess your desires; and I decide to help you make them come true.”
“Perfect,” I said.
“You know what comes next,” she commanded. “Get ’em off.” I allowed the towel to unravel from my body, and then slipped off my white shorts. “Hardly appropriate,” she declared.
“Panties first.” She produced a pair of high-cut white nylon panties, lace edging, lace waist band – they were gorgeous, I’d only ever dreamed of the like. I slipped my feet through and slithered them up my legs. The bulge spoilt the effect so Lily helped me tuck myself away. The panties were stretchy enough that they clung tightly and I soon showed a feminine mound.
“Boobs now.” She seemed to be enjoying herself immensely, and produced a bra. It seemed to be of the same set as the panties, daintily silky and lacy. She had me slip my arms through the straps and spun me around, hooking the eyes at the back. She turned me around again; she had two large breast forms to pad out the cups. Because the bra sat flat on my chest, you really couldn’t tell they were not real breasts. I was starting to feel very sexy and girlish now.
“You know, there’s loads of things girls get to wear,” she was teasing a little. “Especially underneath. We can wear tight girdles and silky panties, garter belts with lots of lace, silk seamed stockings – like mine.” She pirouetted to show me. “Bustiers, corsets … I’d bet you’d like to try some of those on, wouldn’t you.” I could only nod.
She went over to the chest of drawers and rummaged around among the flimsies. “Here we are.” She produced a white open-bottom girdle, with tight elastic panels and six suspenders.
“I think little Miss Debbie will love wearing this – stand here and we’ll slip it on.”
She held me by the arms as I carefully stepped into the garment and began shimmying up my legs. When I finally had it tight around my waist and thighs, she helped me straighten out the bottom edges. It was so tight and restricting – I felt a little faint with ardour.
“Now for nylons.” From the same drawer came a pair of sheer black stockings with seams and Cuban ankles and toes – very elegant. I sat on the edge of the bed as Lily showed me how to roll and unroll them up my smooth legs. Once in place and the seams nicely straight, she snapped the garters to the top of the hose.
“Stand back, pretty thing. Let me have a look.” I wiggled away and modelled my lingerie. I could tell she was enjoying it - her dress was hitching up around her thighs and I could see she, too, was wearing garters. “You actually make a very pretty girl, just in bra and panties. Better get you into a nice dress – no, a skirt and blouse.” She fished out a gorgeous white lace blouse with high neck that buttoned up the back, but first she helped me into a long slip, its lacy hem reaching just above my knees. I was feeling very grown up. After she had me buttoned up, she found a tight grey wool skirt and helped me slip into it. It seemed to cling rather nicely to my waist and a wide leather belt cinched me in even tighter.
“OK, you’re almost there – but mainly from the neck down. That face is a bit of a giveaway but we can definitely do something about that.”
She took my hand lightly and led me to the dressing table. I sat down in the plush velvet chair … but in ladylike fashion, keeping my legs together. I could feel the girdle smooth out my bottom as I sat, also restricting my thighs. It was a supremely pleasurable sensation.
After first assessing my facial features – lots of “oohs” and “aahs” and “very prettys” – she got to work with the makeup. Foundation first, a smell I knew from watching my mother paint her face, then eyeliner, eye shadow, rouge and a deep red lipstick. She also managed to glue on a heavily mascara’ed pair of false eyelashes, in spite of my blinking and twitching. The “oohs” and “aahs” became more trill. “Oh yes, this is a very pretty girl we have here,” she decided. “But you definitely need a cute hairstyle to set it off.”
My mother and sister didn’t own wigs so I had a great fascination for the idea of instant long hair. My dress-up sessions at home had been rather limited as a result. But Lily was a fashion plate and had four or five in boxes at the top of her wardrobe.
“Try this one.” She produced a honey blonde wig, medium length, with a sweeping fringe. My own hair was very short and Lily quickly had the wig in place, using her fingers and a tapered comb to give it style.
“Hey, what happened to that silly boy,” she joked. “All I can see is a comely young girl, with very sexy curves.”
Finally I tried on a pair of light grey high heels, with a thin strap across the ankle. It took some practice to become steady but I soon had the “heel, toe, heel, toe” rhythm working.
Lily appeared very impressed and grabbed me by the arm and led me, clacking away on the wooden floor, into the master bedroom where a long cheval mirror stood in one corner. “Check yourself out, babe.”
I almost swooned when I saw my reflection. Instead of a lanky young man, a svelte young girl was staring back. She was all elegance in lacy blouse and tight skirt, high heels, seamed stockings and glamorous blonde hairdo. I pouted and pirouetted, absolutely fascinated by my transformation. And while I could see the gorgeous clothes, I could feel the tight and frilly underwear clutching me. I kept hitching up my skirt to see the lace and nylon beneath.
Lily seemed transfixed herself. She came over and held me by the waist – as we danced slowly, she whispered in my ear. “Such a glamorous Debbie: I can feel you shaking. I’ve never met such a poised and pretty young lady. “Don’t you simply adore your clothes and lingerie; don’t you wish you were a girl all the time”. I lisped agreement. She held me tighter; and I could feel her breast heaving and her hot breath on my face.
“How would you like a little pussy action,” she whispered, stroking my hair, her perfume wafting over me. I groaned again; I was getting just a little dizzy.
She held my hand and pushed it between her legs. I traced a line up her nylon-clad legs, felt the taut garters, then brushed up against her lace panties. Her hand now guided mine down the waistband and into her V. She helped me rub her clitoris, which seemed to be dripping moisture. I took over, tracing rhythmic circles over her pussy. Her arms tightened around me and she moaned. “Oh God, yes, you painted little whore, you nasty little vixen, make me cum.”
As my hand caressed her faster and faster, I could feel her body bracing. The moaning rose in sound and then she grabbed me hard, kissing me roughly, and a shattering orgasm ran through her. “Oh sweet Jesus, yes.” Her mouth crushed mine, her tongue crammed inside, licking and tasting mine. I could not believe how excited I felt. I had been turned into a ravishing girl and was kissing and caressing another beautiful girl.
As her orgasm petered out, Lily looked lovingly into my eyes. “I had no idea I could get that turned on,” she marvelled. “I’m no lesbian but turning you into a lady has pushed my buttons. You are an exciting, exotic creature, Debbie, and a fast learner. Come and lie down with me.”
She lay back on the bed, flapping her skirt to cool us down. I knelt beside her and she pulled me closer, again kissing my mouth hard. “Girl sex is wild,” she whispered, and as I lay beside her, she began tickling me; I squirmed. “Ooh, a bit sensitive, are we?” She worked her way down to my knee, then began to run her hand up my leg, caressing me through the silk stocking, then slipped it under my skirt. “Such pretty lingerie for such a pretty lady,” she purred. “Ooh, and a tight little girdle – are you a virgin?” We both giggled. She was able to run her fingers beneath the tight panels of the girdle and gently tugged my panties down. My member jumped from its silky prison and very quickly hardened. “Aah, a hard little clit,” she said, her hand slipping around my erection. “Now, what would you like to hear about?’ she teased.
“I bet you would have liked your mummy to dress you up as a little girl!” I moaned. “I know I’d like to take you to the mall and the Little Miss boutique. I’d have you try on all sorts of frilly party dresses. We could dress as mother and daughter in big flouncy velvet gowns and petticoats. I could take you to the theatre and show you off.
“This is a dream come true, isn’t it? Do you go to sleep at night, praying you would wake up with pert little breasts and a tight little pussy? You’re almost there. You love the cool silk panties, and the lipstick and the girl kisses.
“Or do you fantasise about being reborn a female: first a baby girl all in pink, then a pretty little girl in pink party frocks and frilly panties and white lace socks and shiny mary janes. Next you’re the cute young teen, I’ll buy you skirts and jumpers and a whole dresser of glamorous lingerie. Sweet sixteen and just loving being kissed.”
I was delirious – all the exciting images were burning in my head. I’m sure Lily sensed this and resumed the deep kisses, her fingers now gently flicking my hard-on – “Feel that, you little harlot” – and I suddenly came in a shattering orgasm. My lips came free and I cried out: “Oh yes, I’m a pretty girl.”
As I fell back on the bed, I realised we were both out of breath.
“You know, I was quite shocked when you told me you wanted to be a girl. I didn’t understand what the attraction was. But I can now see why a boy would want a little taste of the wild life. I hope you enjoyed yourself.”
“It was the most thrilling experience of my life,” I told her breathlessly. “I really hope we can do it again.”
“Oh yes,” she replied “ I can think of many adventures for Debbie and Lily. You can be my pretty little secretary, my leather-clad love slave, my lingerie model, my latex lesbian …” She paused. “So what time can you come over on Friday?”
The end
6 years ago
