by D. L. Savage
I gasped as my fingers clasped around it, and I steadied myself with my free hand against the cool brickwork as I stroked my aching cock, my head spinning with the memories of what I’d just done, the pleasure quickly building to a crescendo inside me, my orgasm rushing up so damn fast it caught me off guard.
With a muffled groan I finally came, my cock pumping a series of powerful jets that spattered against the wall of the alley, my body quaking, as the orgasm flashed through me, more powerful than any I’d ever known.
12
Maybe it was my euphoria, or maybe I was still a little drunk from all those cocktails, but either way, I wasn’t as quiet or as careful coming back to my room as I should have been. I wasn’t even thinking as I walked down the corridor, then paused to get out my key, and before I could even open my door, I heard a voice behind me. A familiar voice.
“Have fun?”
I span around, my heart leaping into my throat, my stomach dropping through the fucking floor as I set eyes on Ashley, standing there in the corridor facing me, hands on hips and icy blue eyes twinkling with glee.
I knew there was no use in pretending I was Lisa, that I had the wrong room or something. I must look a total state now – rumpled wig, smudged makeup. And anyway, I could tell in that instant that she saw through my disguise now.
“This isn’t what it looks like,” I blurted out in my regular voice, but before I could say anything else, she held up a hand to silence me.
“Let’s go in your room and talk about this,” she whispered, and I felt my heart sink yet further, wondering what fresh hell I was in for now. I would never hear the fucking end of this. What if she told mom? What if she told my friends? She could blackmail me forever with something like this ...
I opened my door and slunk inside, with Ashley following in quick pursuit. But once we were safely inside, she said something I wasn’t expecting.
“I knew it was you on the beach.”
“What?” I gasped, feeling my mood drop even lower.
Was it really that obvious? Had I just been making a total fool out of myself this whole fucking time?
“Okay, so not at first,” she added, with a strange smile, pacing up and down the room while I sank onto the edge of the bed, my head in my hands. “You’re actually pretty fucking convincing. It was just later on, as we were all talking. Some phrase you used. It got me thinking, That’s the kind of thing Paul would say. And that’s when it hit me.”
“I’m so, so sorry,” I murmured. “I don’t even know how it happened. It was such a stupid idea ...”
And all of a sudden, I was crying, hot tears spilling down my face and into my hands, only stopping when I felt Ashley sitting down on the bed next to me, and the softness of her arm around my shoulder.
Wait ... what?
I looked up at her, confused.
“Hey,” she said gently, “it’s totally cool with me, you know. It’s nothing to be ashamed of ...”
“Really?” I murmured, unable to believe my ears.
“Yeah,” she smiled, brushing my hair from my face, “I actually prefer having a big stepsister to a brother anyway.”
At this, I actually laughed, and Ashley did too, both of us hugging for a moment.
“So you won’t tell anyone?” I said, still waiting for the old cruel Ashley to spring up and laugh in my face.
“Of course not! Your secret is safe with me,” she grinned. “It’s just a shame you said tonight was your last night. It would have been fun to go out again with you all dressed up like that. Hey, maybe we could do it when we get home!” she added excitedly. “I could do your makeup!”
“Um, okay,” I grinned, my head spinning all over again.
“So did you have a fun night?” she added with a naughty grin.
I nodded and we giggled again, like two girlfriends.
“I’d better get back to the room,” she said, pushing herself up off the bed, “or Kelly and Becky will wonder where I’ve got to.”
“Thank you, Ashley,” I said sincerely as she was almost at the door.
“Oh and by the way,” she replied a hint of the old Ashley returning, “that miniskirt is mine, and I want it back. Now.”
I laughed again, tugging it off and throwing it to her.
“I’d better sneak the rest of the things in too,” she added and I quickly pulled off everything but the swim suit.
“Thank you so much,” I said genuinely.
“No probs, Lisa,” she grinned, taking the clothes and shoes and leaving my room, closing the door gently behind her. I lay down on the bed, my thoughts whirling, unable to believe that had really just happened.
And what’s more, I felt excited, deep down, like some brand new part of my life was opening up. One which I couldn’t wait to explore further ...
Epilogue
“All packed up and ready to go?” I asked, on the last morning of our vacation.
“Think so,” Ashley smiled back.
Since our little talk and our new understanding, things had been so much easier between us. I’d even hung out with her and the girls a few times during the rest of the vacation, as Paul of course, and it seemed that if Ashley was nice to me, then they were too. And now I couldn’t wait to get back home, to explore this whole new part of my life – with Ashley right by my side.
“How about you?” she said. “Got everything?”
I looked down at my luggage and nodded, casting a final glance at my room. I’d deliberated for the longest time whether or not to take that other suitcase with me too, the one with the wig, swimsuit and makeup inside.
But in the end, I’d decided to leave it just where I found it, pushed beneath the bed, ready to discover by the room’s next occupant.
Because who knows? Maybe it would change his life, the way it had changed mine.
White Wedding
Prologue
Every girl dreams of a white wedding, right? To wear a beautiful, shimmering white dress, complete with your hair done to perfection, with makeup, shoes and stockings – the whole nine yards.
Well, let me tell you a little secret.
I dreamed of that too, for as long as I could remember. Ever since I was a little boy ...
1
“Hey, Mike!” my fiancé Jenny called from the hall. “I’m just heading out to the mall. You need anything?”
“No thanks, honey,” I called back from my seat in the lounge, where I’d been watching TV, enjoying a lazy Sunday afternoon before the grind of work started all over again tomorrow.
“Okay, I’ll be back in an hour or so,” I heard her say, before the slam of the front door set a charge of nervous, excited tension straight through me.
Suddenly I didn’t care about the TV show anymore, instead I was just listening, poised, for the familiar sound of the car engine starting up as she backed down the drive, the noise growing dimmer until she’d driven away completely. And as soon as I knew I was alone, I jumped up from my seat, heart pounding, my mood completely changed.
It was so rare that I had any time alone in the house to myself – we both worked long hours, and hung out together whenever we came home from work – and I just knew I had to make the most of every single second of it.
My excitement grew as I made my way up the stairs, straight to our bedroom, quickly turning on the light and drawing the curtains to shield me from any prying neighbors, then making my way to my favorite place in the world, a place I thought of as a kind of treasure chest of pleasures: Jenny’s underwear drawer.
I pulled it open with shaky hands, gazing in at the bright colorful selection, letting my fingers run for a moment through the scraps of fabric, enjoying their soft feminine touch against my skin.
This one large drawer contained all of Jenny’s underwear – her bras, her stockings, her everyday ‘granny’ panties, her slinky sexy thongs and g-strings which she wore for me on special occasions, and even a couple of garter belts too, one: one in white and one in black.
>
I took my time making my selection, choosing carefully, wanting to select things that really worked together, in the end deciding on a simple classic choice: black hold up stockings, the black garter belt and a plain black thong.
I’d been dressing up for almost as long as I could remember – sneaking pantyhose and underwear from my big sister’s room, and from girlfriends, whenever I got the chance – and it always had the same thrill. An illicit secret pleasure that I couldn’t quite explain.
I never dared go further than underwear, even though in my most private fantasies I longed to be fully transformed – in a beautiful dress, perhaps, with long flowing hair, killer heels and full makeup.
But in reality, it was never anything more than a quick thing: something to do in secret, before I got caught.
I felt that familiar charge of electricity as I slipped my foot into the first rolled up stocking, unfurling it over my leg. It felt so good to feel my leg encased like that, and I tried to focus on the sensation and the overall look, not wanting to pay too much attention to the ugly black hairs that showed through the opaque black fabric.
If only men were allowed to shave their legs too!
I would have loved to have soft, smooth hairless legs like Jenny’s but I knew how weird she’d find it; I suspected she preferred ‘manly’ men, which was how I’d always presented myself to her, perhaps to compensate for my secret feminine side.
Next I rolled on the second stocking, adjusting the lace tops of the hold ups until they were sitting pretty around my thighs, just so. Then I stepped into the thong, pulling it up tight and snug, savoring the way the stretchy fabric cradled my cock and balls, already desperate to take a peek at the way it framed my ass in the long mirror Jenny used to dress herself in.
But I held off until the look was complete.
With trembling fingers, I clasped the garter belt around my waist, adjusted it into place, then fastened the clips to the tops of my stockings, so excited to see the finished result.
As I walked over to the mirror, I let my secret feminine side out to play, swinging my hips, moving as sexily and gracefully as I could, feeling the strange yet not unpleasant feeling of that thong riding up between my butt cheeks.
My heart pounded as I turned and struck a pose, arching my back, sticking out my ass, then looked over my shoulder into the mirror – savoring as always the sight that greeted me there. Because the thing was, I had a great figure: a figure that made so much more sense when dressed like a woman.
As a guy, I was just a little on the slim side, hairy sure, but with nothing much to remark on. But in women’s clothes it was like my body sang, like it made true sense, and I just wished there was some way I could dress like this all the time. I felt so much more alive, so much happier.
But of course, I knew it wasn’t to be – that I would never be able to do anything more than snatch a few private moments such as this. Sure I could maybe spend a whole weekend dressed up some time. I’d fantasized about it many times; maybe I could rent a hotel room somewhere, buy some cheap dresses and underwear, a wig even, and spend a few days dressed like that before ditching my stash of clothes and returning to Jenny again pretending I’d been on some business trip?
But I knew in my heart I’d never actually go through with it. Part of me was too scared: scared in case I never wanted to go back to men’s clothes any more. And another part of me knew that the guilt of doing something in secret like that would be too much to bear.
No. This was all I could bring myself do. Just have a little fun like this ...
I turned, stretching out a leg and pushing my hips to the side, striking a classic pose lingerie models often made, again admiring my figure, marveling at how truly feminine and girly I looked, at least from the waist down, and as long as you ignored the fuzz of hair that spilled out from my panties, and of course the large bulge in the front of them.
And I was just turning, about to strike another pose, when I heard something that made my heart skip a beat.
No. It couldn’t be …
But sure enough, there was the sound of a car engine in the driveway again. And a moment later the slam of the car door and a key being turned in the lock.
I was still wearing my regular t-shirt on the top half of my body, but I knew I didn’t have time to take off the garter belt, stockings and panties. So instead I just grabbed my jeans, hurriedly pulling them over the top, buckling them with trembling hands as I heard Jenny calling out from the downstairs hallway, “Hey, me again, I forgot my wallet!”
My eyes darted to the dressing table where, sure enough, Jenny’s wallet lay, and I heard her coming up the stairs as I quickly pulled on my socks over the top of my stockinged feet, just covering the last inch of black fabric before she came bursting into the room.
“There it is!” she said happily, grabbing it from the dresser, then shooting me a look, her brow wrinkling as she added, “Are you okay? You look kind of worried!”
“No I uh, I just,” I stammered, my brain swimming as I tried to come up with a suitable excuse, “I just felt a little off,” I said finally. “I think I might take a nap.”
“Oh sweetie,” Jenny said softly, walking over and giving me a loving kiss on the forehead, only making me feel even worse for lying to her. “I hope you feel better later,” she added in a half-whisper, “because I was hoping we might fool around a little.”
“That would be great,” I croaked, feeling so sick and guilty, just wishing right now she would go.
Don’t get me wrong – I loved her more than anything in the world, and I did want to fool around too. I just felt so fucking guilty for lying to her, sat there secretly dressed in her fucking underwear.
“See you soon,” she said happily, heading once more out of the room and down the stairs.
As I listened to her leave – the slam of the door, the car pulling away, and then silence – this time I felt utterly deflated, falling back onto the bed, my mind spinning, but all the energy and enthusiasm I’d had for dressing up now totally evaporated.
All I felt was sick; sick and sad that I had to keep this part of me so damn secret. Not for the first time, I wished I’d simply told her, back when we’d first started dating. Who knows? Maybe she would have run a mile, or maybe she would have been okay with it. But now, after six years together, it felt impossible to tell her the truth.
With a sad sigh, I finally pushed myself up off the bed and unbuckled my pants, no longer even wanting to look at myself in the mirror any more, simply stripping off the stockings, panties and garter belt, and pushing them back into the drawer, just where I’d found them, wishing – as I did so many times – that I never had these urges.
Just wishing I was normal.
2
As you can probably gather by now, Jenny and I weren’t total innocents. We’d slept together soon after we started dating and moved in after a year. So there was nothing about our upcoming marriage that was going to change anything, other than the fact that we simply wanted to commit fully to each other – to make the vows that would unite us as a team, for as long as we both lived.
And I wanted that, I really did.
Jenny was perfect, everything I’d ever dreamed of in a woman. She was slim, petite, with the most beautiful long dark hair and a pretty face that always seemed fixed in a naughty, playful expression. Her body was incredible, and even better – she was funny too, smart and adventurous in all aspects of her life.
She’d had way more sexual experience than me when we first started dating – having had some pretty ‘wild’ years back in college – but now she was ready to commit, and didn’t seem to mind that I had only slept with a handful of girls, and only ever really done the most vanilla things.
A part of me even knew that Jenny would have been cool with my dressing up – had I simply told her about it back when we first got together, she would probably just have found some way of making it fun and normal. But still, some part of me just couldn’t ope
n up to her.
It gnawed at me inside, a shameful secret.
A lot of this was probably due to my upbringing. I’d had a very controlling, overbearing mother who always wanted to know what I was doing at all times, and as a result it became second nature to keep things secret – to hide away parts of myself from others. Jenny meanwhile couldn’t be more different; always open, always sharing her thoughts and feelings.
I’d grown so much since I met her, opening up a lot – for me, at least.
But just not about this. My big secret.
And the longer it went on, the more I dreaded what might happen if I ever did tell her, how she’d react. I couldn’t bear the idea of her discovering me and thinking what I was doing was disgusting. It would destroy me.
No, I simply couldn’t take the risk …
“So, are you excited for your bachelor party?” she asked one evening, as I was getting ready, buttoning my hair and fixing my shirt, fresh from the shower.
It was a Friday night, a few weeks before the big day, and I turned to look at her with a wry smile and said honestly, “I don’t know if excited is the right world. I have a feeling Jordan is taking us to a strip club. You know him, any excuse!”
“Oh, a strip club, eh?” Jenny replied, in a teasing voice. “And you’re sure this is Jordan’s idea and not yours?”
“Come on!” I laughed, turning to face her. “You know me. That’s the last place I’d wanna go. It’s you I want, baby. I think Jordan just wants to see me squirm as I get a lap dance.”
Everything I was saying was true. The idea of some tanned, oiled up stripper with huge fake breasts held no real attraction to me. I much preferred natural everyday girls like Jenny. She was everything I wanted in a woman, and I hoped she knew it.
“C’mere a moment,” Jenny said, a naughty twinkle in her eye as she looked at me from across the bedroom. “I just want to give you a little present before you leave.”
