by D. L. Savage
“Of course, sweetie!” she beamed back. “I’d love to help! Hey, you know what? Why don’t you crash here tonight? We can go out tomorrow, buy you some new clothes, makeup, the whole works?”
“Are you sure you wouldn’t mind?” I asked, genuinely touched that she’d taken so much interest in me.
“Are you kidding?” she grinned. “Shopping is pretty much my favorite activity in the world.”
And so it was arranged. Becky made up a bed for me on the couch in the living room, and tomorrow we were going to go out together on a girly shopping trip together. She even gave me a cute, comfy oversize t-shirt to sleep in, and helped me wipe off my makeup using special pads and lotion. And once I was happily snuggled up beneath the covers, I fell quickly asleep.
“Rise and shine, sleepyhead!”
I opened my eyes, for a moment unsure where I was. The room was flooded with sunlight. And then I saw Becky leaning over me, and I felt a flash of excitement at the day ahead.
“How did you sleep?” she asked.
“Really good,” I smiled back. It was true; this was the first night I’d slept all the way through, without worrying about Mistress Cartwright, or whatever crazy punishment she had in store for me. The idea of a whole weekend to do what I want seemed like heaven, and I was determined to make the most of it.
“So, you want me to fix you some breakfast,” Becky grinned, “or shall we just hit the city straight away?”
She looked really cute, standing there in just her oversized tee shirt, no makeup on, and her blonde hair all mussed up. But it was kind of odd – because even though I found her attractive I didn’t actually feel anything sexual. It was more just a friendly warmth towards her, like she was my sister or something.
“Let’s do it,” I grinned back, just excited to get out there and start shopping.
“You wanna borrow some of my clothes today?” she asked. “
“That’d be really great,” I replied, so glad I’d met her.
“Okay, I’ll be right back. This is gonna be so much fun!” she said, clapping her hands together excitedly, as she turned and raced back to her bedroom to pick me out a few outfit choices.
* * *
A little while later, we were strolling through the busy shopping district, arm in arm, dressed in similar outfits: hoodies, vest tops, leggings and sneakers. It felt so different to the kinds of clothes I normally wore on my day off. Sure, these clothes were soft and comfy, but they were so damn tight too. I felt so exposed – especially in the leggings, which clung to my legs and butt almost like a second skin. And because Becky insisted there was no way I should be seen dead with visible panty lines, she’d loaned me one of her thongs too.
To my surprise, we were the exact same shoe size – and her worn in Reebok sneakers were so comfy I wanted to steal them.
Yep, all in all, I was having a great time.
“Say, Penny,” Becky said as we strolled along the sidewalk, “now don’t take this the wrong way, but do you mind if I ask you something kinda personal?”
I felt my stomach flip; what the hell was this going to be about.
“Um, okay,” I said, hoping she wasn’t about to say something cruel.
“Now, obviously it’s totally a ladies preference what she does with her body, but ... well ...”
She tailed off, as if she were still trying to work out how to phrase the rest of her sentence without insulting me.
“What?” I sighed.
“It’s just that I caught a glimpse of you as you were getting changed this morning and ... I think you need a bikini wax!”
“No way,” I shot back immediately. “I’m not having some girl in a salon realizing I still have a ... You know.”
“Well what about a home wax?’ she persisted. “I could do it for you tonight if you wanted?”
“Couldn’t I just shave?” I sighed.
“It’s just so smooth,” she countered. “Trust me, you’ll love it once it’s done.”
I groaned. “You’re not taking no for an answer, are you?”
“Uh uh,” she laughed. “I’m afraid not!”
* * *
A few hours later we were totally loaded up with shopping bags, so many we could hardly carry them all. Becky had helped me pick out all kinds of awesome new clothes – for all occasions. I had sporty leggings and cute t-shirts for lounging around in. I had summer skirts and dresses for when the weather picked up. I had a sexy little black dress for important functions (or dates). And I had a whole bunch more office-wear too: black skirts, white blouses, more stockings and even a figure-hugging trouser suit, just like Mistress Cartwright. I’d been putting everything on the credit card that she’d given me, figuring that most of it was ‘work wear’ ... right?
And now we were on our way to Victoria’s Secret, to pick out some cute bras and panties, and I had to admit, I was getting more than a little turned on at the idea. I guess even in my new feminine persona, I still found women’s underwear sexy – I simply couldn’t wait!
“Okay,” said Becky, taking control as we got into the store, “you’re going to need different things for different occasions, just like the outfits we’ve picked out for you. First, regular everyday underwear ...”
She took my arm and led me off, first towards the bras.
“This is cute,” she said, holding up an electric blue bra. She’d picked out my size and as she handed it to me, I realized the cups had a little extra padding in them too. “What do you think?”
“I like it,” I replied.
“Great,” she said, throwing it in the basket, along with the same bra in black, pink and yellow. “And look, they have the matching panties too!”
She picked up a matching blue thong, in what looked like some kind of stretchy shiny fabric. It certainly looked like it would keep my bulge in place.
“Yeah, those are really cute,” I smiled back.
It was so funny; after a day with Becky, I’d even begun talking like her – everything was ‘cute’ and ‘awesome’.
“Awesome!” Becky chimed, dropping the panties in the basket, too, and picking out the matching pairs for the other bras – black, yellow and pink. “And now onto the really sexy underwear,” she continued, giving me a playful little wink.
She led me over to another area of the store – and I could tell immediately that this underwear wasn’t designed for regular daily activities in mind. “What about this?” she said, picking up a red lacy one-piece teddy, holding it up against me.
“Too see through,” I said, knowing that there was no way in hell I’d actually want my body showing through the fabric. The underwear was supposed to give the illusion of me being even more feminine, not to give away the fact that I was a guy.
“Oh, now this ...” she said, picking up what looked at first just like a tangle of black fabric, but as she held it up I realized it was another teddy, this time with a little more coverage – including a choker neck, which I really liked the look of. I still felt kinda paranoid about my Adam’s apple. I guess I was lucky that, for a guy, it was pretty small, and Becky assured me it wasn’t really noticeable, but the idea of a choker collar like that seemed great.
“I love it,” I said, and in it went into the basket.
We had the most fun, exploring the store, picking out all kinds of cute, sexy things. More panties, more bras, even a silky kimono.
“You can always take things back if you get them home and you decide you don’t want them,” Becky assured me, as the cash register displayed a small fortune on its screen.
For a brief moment, I felt my stomach drop when I saw the total, wondering what Mistress Cartwright might do if she found out just where her company money had been spent. But I quickly put the thought from my mind. After all, it was the weekend now, I reminded myself; a time for relaxing and having fun. I could worry about things like that on Monday.
After we’d finished in the store, we decided to head back to Becky’s. She’d bought a
home waxing kit, and was determined to get started on getting me all smooth and waxed down there. But all of a sudden, half way down a nondescript street, she grabbed my arm and pulled me into a store.
“Where are we going now?” I asked, totally confused.
“You’ll see!” she replies with a laugh.
“I love it!” Becky said a little while later, clasping her hands together, a big smile breaking out across her pretty face, blue eyes twinkling as she stood back to take me in.
“You sure?” I asked. “I feel kinda silly ...”
“Just take a look for yourself!” she replied, nodding over at the mirror I’d so far been too afraid to peer into.
I took a tentative step towards it, leaning forward, and what I saw stole the breath from my lungs. Okay, wow. Beck was right – as usual. This was it. The cherry on top, the missing puzzle piece. I almost couldn’t believe it.
The shop we’d gone into was for hair extensions and wigs, and the thing I was wearing was just that: a black bob wig. It was incredible how much it complimented my skin tone, making me look even paler, bringing out my eyes, my makeup. And it actually looked real too – is if I’d just had a cute new haircut and dyed my hair pitch black.
“You’ve got to buy it,” she urged. “It’s just ... you!”
“How much is it?” I asked, turning to face the woman behind the counter.
“Nine hundred dollars,” she shot back. “A good wig like that doesn’t come cheap, I’m afraid. It’s real human hair, you know.”
“Oh Becky,” I sighed. “I don’t think I can. I mean, I’m putting everything on this company card and ... well, I’ve already gone kind of crazy today.”
“Oh come on,” she grinned back. “I promise you, those company cards never even get checked. Everyone puts things on expenses. It’ll be fine, I swear.”
“Well, if you’re sure,” I said, taking off the wig and turning back to the counter.
And as I offered out the company card to the woman behind the counter, I just hoped to God that what Becky said was true ...
* * *
Later that day, we found ourselves back in Becky’s cluttered apartment, trying on outfits and eating Chinese takeout. Pop music was blaring from her little stereo and it was just so much fun, seeing again how all these sexy new clothes complimented my figure – all now finished off with the gorgeous black wig. I felt like a real girl. And I could tell that Becky was just as excited about my discoveries as I was.
“So where do you wanna go tonight?” she asked, raising her voice a little to be heard over the Katy Perry track that was playing.
“Huh?” I said, puzzled. “What do you mean?”
“Oh come on!” she grinned back. “You can’t get all dressed up and then not show yourself off! Tonight we’re going out.”
And just like that it was decided. We were going to hit the town – first to some cocktail bars and then onto a club Becky always went to.
I felt a sudden thrill of excitement. My first real night out as my new girly self. Was I really ready? There was only one way to find out!
“Hey, you should call that guy,” Becky said all of a sudden. “The one who gave you his number!”
At this, my heart froze.
“Uh, I don’t know,” I said, my face falling.
“Why not?” she asked. “He was cute, right?”
“Well, yeah,” I replied, “but still ... I don’t know. I mean, he thinks I’m a girl. And what happens when he finds out I’m ... You know. Different?”
“Hey, don’t spend so much time worrying!” she laughed. “Just call him ... Come on, Penny. You have his number, right?”
I looked over at the dresser – where I’d put Marcus’s business card for safe keeping.
“Call him!” Becky giggled, picking up her iPhone and thrusting it towards me. “It’ll be fun, I promise!”
“Okay,” I groaned, taking the phone and dialing in Marcus’s number, my heart hammering as I held it against my ear, listening to it ring.
For a moment I didn’t think he’d even pick up, and then all of a sudden I heard his voice and my stomach flipped with excitement.
“Hello?”
“Hi,” I said, trying my hardest to keep my voice high and feminine. “It’s me – Penny. You gave me your card the other day?”
“Penny!” he said, happily, totally taking me aback. “I’m so glad you called. I was just thinking about you.”
I felt another flash of excitement – he’d actually be thinking about me?
“Yeah, well, I’m going out for a few drinks with my friend Becky this evening,” I blurted out, my voice shaking a little, as I looked over at Becky who was making silly faces at me, “and I, um, just wondered if you’d like to come out with us?”
“I’d love that,” he said, totally assured and confident.
“Great,” I said, heart pounding. “We’re going to the ... um ...”
I shot a look at Becky, who whispered back the name of the bar: The Alleycat.
“The Alleycat?”
“I love that place,” he laughed, still totally relaxed.
“Awesome,” I said, “well, we’ll be there at nine. See you later!”
And then I quickly hung up the call, before I could somehow mess it up.
“I can’t believe I just did that,” I said, shaking my head, totally amazed at how easily that had gone. I mean, back in my life as Peter, I’d never just call a girl up and ask her out. And even if I had, there was no chance in hell she’d say yes. But now, as Penny, this was just another thing that seemed so different – so easy.
“You did great,” Becky grinned. “Now come on, let’s make ourselves pretty. We only have a couple hours!”
A little while later, we were sitting in the bar – both dolled up. Becky was wearing a skimpy little pink dress that hugged her figure, and she’d done her glossy blonde hair in curls. She looked so great – her plump lips accentuated with gorgeous peach lipstick, and her big blue eyes framed by long black lashes. And I have to say, I was looking pretty good too! It was all thanks to Becky of course. She’d chosen an all-black outfit for me, to match my brand new wig. I was wearing the tiniest black dress, with matching heels and deep red vampish lipstick. My eyes were encircled with black eyeliner, and beneath my dress, my underwear was black too. A cute little lacy A-cup bra and the skimpiest black g-string, which was holding my sissy cock and balls snugly in place.
We sipped our cocktails and as we waited for Marcus to arrive, I could feel the hungry eyes of other guys at the bar, all checking us out. But I took Becky’s lead and played it cool, pretending I was totally oblivious to all the attention we were obvious drawing.
“What if he doesn’t show,” I said, taking another nervous glance up at the clock on the wall, which announced that it was already a little past nine.
“Stop worrying,” Becky grinned back at me, taking a long slow sip of her cocktail before continuing, “guys always like to play it cool. He’ll be here, just you wait and see.”
Just then I sensed movement behind me and I turned around a little in my chair, just in time to see him strutting into the bar, dressed in a crisp white shirt and chinos, his thick hair shining, his black eyes roving the bar.
I quickly turned back around to face Becky, my own eyes widening and the look on my face must have told her that this was him.
“Holy shit!” she giggled, when she saw him. “He’s super hot!”
And then she actually waved at him, smiling and beckoning him over. I could feel my whole body pounding with nerves and excitement and I wondered all over again if perhaps this was a bad idea – if I was out of my depth.
“Hello ladies,” he said, as he took a seat confidently at our table.
“Hi,” Becky grinned back. “Penny didn’t mention just how handsome you are. I’m Becky!”
“Well, aren’t I a lucky guy to be out with two beautiful women this evening,” Marcus smiled back.
They both s
eemed so confident, so at ease, while I felt totally out of my depth. My heart was pounding and I was practically shivering with nerves. I decided to stay quiet, for fear of messing this up somehow, just sipping my drink and smiling and letting Becky and Marcus talk.
And pretty soon, the talk got kinda flirtatious.
“What’s the craziest place you’ve ever had sex?” Becky said, flashing a naughty smile at us both.
“One time I had sex with this chick on the balcony of my apartment,” Marcus laughed. “How about you?”
“I once blew a guy from work in the back of a taxi,” Becky giggled back.
“Lucky guy,” Marcus grinned. “So how about you, Penny?”
I felt both of them turn to look at me expectantly.
“Oh, I don’t know, I guess I’m pretty conservative,” I said in a small, quiet voice, feeling my cheeks blushing with heat.
“Well, maybe we need to do something about that,” Becky countered, giving me a wink. “Why don’t we all go back to my place?”
“Sure,” Marcus said quickly, obviously not believing his luck at how easy this was.
“Penny?” Becky said, pinning me with her big bright eyes.
“Um,” I croaked, feeling totally conflicted.
I mean, a part of me wanted nothing more in all the world, but at the same time, there were so many things I was worried about. What if Marcus realized I wasn’t a true girl? What if I did something wrong? What if ...
“Will you excuse us for just a moment?” Becky said in a sweet voice to Marcus, pushing herself up from her seat then offering me her hand.
“Sure, ladies,” he smiled back.
I took Becky’s hand and she led me into the women’s washrooms, which were thankfully empty.
“Come on!” she giggled, once we were alone. “He’s super hot. What are you afraid of?”
“I don’t know,” I sighed. “I’ve just ... never done anything with a guy before. I’m a little scared.”
“Oh, Penny,” Becky smiled warmly. “You’re gorgeous, and you have nothing to be scared about. Don’t worry, just follow my lead and this will be fun, I promise.”
