by D. L. Savage
If only there was a world where people could dress however they damn wanted, I thought to myself sadly, imagining some crazy scenario where I strutted into work as Hailey, turning heads wherever I went, and maybe getting a few cocks hard in the process.
And as I dressed in front of the mirror, pulling on my shirt and suit pants, I fought off the urge to put on that cute pink Victoria’s Secret thong – the naughty little item that had started this whole sequence of events – underneath my regular clothes.
* * *
Just as I was stepping out into the driveway to get into my car to drive to work, I saw Caroline’s shiny red car racing up the road, pulling to a screech at the end of our driveway.
“Hey Henry!” Caroline called, waving from her open window, as Jenny got out and unloaded her luggage from the trunk.
“Hey!” I called back. “Hope you had fun?”
“We had a blast!” Caroline laughed back. “Anyway, gotta dash or I’ll be late for work. See you at the wedding!”
With that, the car went speeding off, leaving Jenny standing there facing me on the sidewalk. I don’t know why, but I felt a pang of awkwardness as I walked towards her, not to mention guilt too, at that thing I’d done in the dressing room. I guess you could call it cheating, right?
And maybe I was just imagining it, but I swear Jenny looked a little sheepish, too, kind of avoiding my gaze as I walked up and kissed her.
“Hey, how are you?” I asked, trying to sound upbeat.
“Pretty good,” she said quietly, but I could tell something was wrong.
Oh no, is it that obvious? Can she somehow tell I’ve been unfaithful to her? Is it written all over my damn face?
“Listen, I’d better go or I’ll be late for work too,” I said apologetically. “But we’ll catch up as soon as I get home tonight.”
“Sure,” she mumbled, quickly turning and carrying her bags towards the house.
And it was only as I was pulling out of the driveway that I realized neither of us had said, I love you.
* * *
I spent that first day back at work feeling so damn guilty. Every spare moment, my mind flashed back to what I’d done – and that weird cold look on Jenny’s face – and my stomach lurched, as I wondered and worried. Had I screwed things up between us forever? Should I tell her what I did? Or does she somehow already know?
Before I knew it, the day was over, and I was getting ready to drive back home again, my guilt and worry increasing with each second. I just knew we’d have to talk about things once I got home, there was definitely something weird going on, but what?
I wasn’t quite sure I was ready to let Jenny in on all these new emotions and urges I was feeling – and I have to admit, I guess deep down, a small part of me was even hopeful that we might break up. Because then I could start again: a whole new life, a life as Hailey, 24-7. I’d quit work and just live at Sissy School and ...
No. It was crazy. I wasn’t thinking straight.
I knew that what I needed to do right now was man up and confront this head on. When I got home that evening, I would just talk to Jenny and find out exactly what the hell was going on here – what it was that had made her so upset.
After all, I might just be blowing this whole thing out of proportion.
* * *
“You’ve hardly touched your food,” Jenny said that night over dinner.
“Neither have you,” I said gently, noting that her plate was still almost as full as mine. “Listen, I think we need to have a talk.”
She nodded, putting down her fork, then letting out a big sigh.
“You’re right,” she said, quietly, looking down at the table, not meeting my eye. “There’s something I should tell you.”
I felt a pang of shock – for some reason I’d not imagined that she had anything to feel guilty about. I kept quiet, holding my breath, waiting for her to continue.
“So, last night,” she said quietly. “We all got pretty drunk. And then ... the stripper came over.”
She paused, still not meeting my eye, and suddenly I felt like I knew exactly what she was going to say.
“So he starts dancing and taking off his clothes and then he brings out this lotion and he starts going around the room, getting us all to rub it onto his body ...”
Again, she paused, her face growing red with embarrassment, her voice trembling a little as she continued.
“He wasn’t even my type, he was just this total beefcake. But we were all drunk and it was just silly fun and ... Well, things went a little further than we’d planned. He got naked and his ... his thing was hard and he was going around the group getting us all to touch him there. It was just supposed to be fun, right? But then Caroline ...”
By now she looked so ashamed, like she was about to cry, and I reached out and put my hand on top of hers, squeezing her fingers.
“Hey, hey,” I said, gently. “I understand. It’s okay. Just tell me, I’m not going to get mad, I promise.”
She took a deep shaky breath and then continued.
“So Caroline started ... sucking on him. And well, then we all did. I only took him in my mouth for a few seconds but still. Oh Henry, I’m so sorry. It didn’t mean anything, I promise. But I felt so fucking guilty I just had to tell you. God. You must think I’m such a slut.”
And with this she burst into tears.
I quickly pushed myself out of my seat and ran around to her side of the table, throwing my arms around her, cupping her face in my hands, stroking the tears from her cheeks, forcing her to look up at me.
“I don’t think you’re a slut,” I said. “And I’m not mad. Not at all. I totally understand.”
“Really?” she said, shocked and confused. “I thought you’d go crazy when I told you.”
“Really,” I smiled back at her. “I totally understand.”
And I did, didn’t I? I knew exactly what she was talking about.
“You’re amazing,” she said, drying her eyes and shaking her head. “I’m so lucky to have a husband like you ...”
Oh, if only you knew, I thought to myself, guiltily.
* * *
That night, we snuggled in bed and it felt good to have cleared the air a little. But I guess I still felt kind of guilty that I hadn’t been totally honest with Jenny about what I had got up to while she was away. And I was still thinking about this when she started running her hands over my chest, and kissing my neck.
“So, did you miss me while I was away?” she whispered.
“Of course I did,” I replied, turning to face her. “You know, what you told me earlier? About what you did?”
“Henry, please. Do we have to talk about that again?” she said, her hand pausing on my chest, her eyes growing sad.
“No, you don’t understand,” I smiled back at her. “I guess, well, I found it pretty hot.”
“Really?” she said, totally surprised. She’d obviously never considered this an option, and I could tell she wanted to ask a whole bunch of new questions.
“Yeah,” I continued. “The thought of you and Caroline and all the girls playing with that stripper, getting turned on ...”
“You’re silly,” she grinned, but her hand had moved down beneath the sheets, her slender fingers wrapping around my cock, which was already growing hard at the thought of her sucking off the stripper. “Wow,” she gasped, “you really do like it, don’t you? Hey, what’s all this about?”
Her fingers were brushing around my newly cropped pubic hair and hairless balls, investigating.
“I was just messing around in the shower,” I said, feeling a little sheepish. “Do you like it like that?”
She stroked my cock and massaged my balls, then nodded. “Actually I kinda do. It feels so ... silky.”
“I want you to tell me more about that evening, Jenny,” I whispered, my voice trembling, as she began to slowly stroke my dick. “Tell me everything. Every little detail.”
“Well, there’s not that much to tell,”
she began, stroking me so slowly and sensuously, but I could tell that her voice was charged with a strange new excitement as she spoke. “He was this total beefcake – all oiled and muscley, just some dumb kid really. And he was only wearing a g-string. So all the girls took it in turn to rub lotion into his muscles.”
“Did you?” I asked, my voice trembling, as her hand continued stroking my dick.
“Uh huh,” she whispered, nodding.
“And did it get your panties wet?” I replied.
“I don’t know, I guess so,” she giggled, growing a little embarrassed.
“And then what happened?” I said. “Tell me everything.”
“Well, then he took off his g-string and we all gasped. He was like huge. Huge and thick, and he wasn’t even totally hard yet. So anyway, he started dancing, swinging that big thick dick around in front of all of us, one by one, thrusting it right up in our faces.”
“And did it turn you on?” I whispered.
“Of course it did,” she whispered back. “It was just so ... big. I couldn’t help but stare at it. It made my clit tingle just looking at it.”
“And did you want to suck it?”
“I don’t know. Maybe?”
“So what happened next?”
“Well, next he brought out this canister of cream and sprayed it on himself, on his abs and on his, you know ... his thing. And then he stood in front of Caroline, because it was her bachelorette party, and he got her to lick the cream off.”
“And did Caroline enjoy doing it?”
“Oh my God, yeah!” Jenny giggled. “She’s always telling me how small Glen is, you know, down there? So you could just tell she was getting hot horny, staring at that big old dick in front of her. And soon, well, she was just going for it, you know? Really sucking on him, right there in front of all of us.”
“So what happened next?” I said, my voice trembling, as Jenny’s hand continued to work my cock with slow sensuous strokes, her other hand cupping my swollen balls.
“Well, we all made a show of being shocked, y’know? But I think secretly we were all wishing that we could suck on him too. And pretty soon he’d made his way around the whole group, letting us each have a turn. And when he got to me, I don’t know, I guess I just couldn’t help myself. Oh, Henry, he was just so big. He filled up my whole mouth, and he was so damn hard, and it just felt so good in my mouth that I kept sucking and sucking until ... well ... I haven’t told you this part.”
She became shy, her hand pausing on my cock, her breathing growing a little heavy.
“What? Tell me,” I urged her.
“I kept on sucking until he came.”
When she told me this final detail, it was just too much. All of a sudden I groaned and stiffened and then I came too, my cock spurting hot creamy cum all over Jenny’s fingers, and she continued to stroke me until I’d finished, my whole body trembling and shuddering now.
“Holy cow!” she giggled afterwards. “That really did turn you on, didn’t it?”
“I love you, Jenny,” I grinned, pulling her tightly to me.
“I love you too,” she replied, snuggling into me, both of us happy and content.
And even though I hadn’t told her about my experience yet, I somehow felt like maybe I could – that one day soon, I might actually be able to open up to her completely, and that together we might start a brand new chapter in our lives ...
* * *
“So? How do I look?” Jenny asked, a few weeks later.
It was the morning of Caroline’s wedding, and we were staying in a fancy hotel room near to where the ceremony was taking place.
I took a step back to look at her, standing there in an elegant figure-hugging blue dress, her makeup immaculate, her long legs shown off perfectly by a pair of matching blue heels, her long brown hair done in the same kind of flowing curls as my Hailey wig – and I have to admit, as well as feeling the usual pride and attraction to my beautiful wife, I felt something else too.
Envy.
Even though it had only been a few weeks since my trip to Sissy School, I just couldn’t get the memories out of my head, and I wanted nothing more than to be dressed up again in a cute, sexy outfit, feeling confident and feminine and free.
I’d snuck glimpses of Jenny as she’d been putting on her outfit, and I knew that beneath the dress she was wearing a cute black bra and matching thong. For her, a thong was just a way of eliminating panty lines, but even so, I wished I was wearing one too.
“So, are you all set?” she asked me.
“Almost,” I replied. “I just need to go to the bathroom one last time.”
“Henry!” she smiled. “You went like five minutes ago.”
“I know, but I have a feeling the ceremony is gonna take quite a while.”
“Okay, well hurry up!”
As she turned back to the mirror to do some last minute primping to her hair, I quickly headed to the en-suite bathroom, my heart hammering in my chest. Because I couldn’t fight back the urge any longer.
I locked myself in the small mirrored room, then set the taps running so that she wouldn’t hear anything, and then I grabbed my wash bag and rooted around in it, recovering the small bundle of bright pink fabric that I’d snuck in to the hotel room with me.
Jenny’s pink Victoria’s Secret thong – the little item that had started this whole mess in the first place.
I don’t know why I’d even packed it; maybe I was hoping to sneak it on at some point, just to have five minutes of pleasure, but now I had an even better idea.
With shaky fingers I quickly unlaced my dress shoes, then took off my suit pants and boxer shorts, bundling them up and stuffing them into the wash bag. Then I quickly pulled on the thong, feeling that shiver of excitement and satisfaction as it snugly slid between my cheeks, the stretchy fabric tightly cupping my balls and dick.
As I pulled on my suit pants again, tucking in my shirt and lacing my shoes, I could hear Jenny getting impatient outside.
“Come on! We’re gonna be late!”
“Almost ready!” I called back, buckling my belt and then standing up.
As I unlocked the door and headed back through to the bedroom, I could feel the tightness of the thong – the way it slid between my ass cheeks as I walked – and there was something so sexy about that feeling, that little secret that only I knew.
I figured I’d quickly sneak it off again before we got into bed that night, and nobody would be any the wiser ...
* * *
The ceremony went without a hitch. Caroline looked beautiful in her amazing white dress and even Glen looked pretty handsome. But as they said their vows and everyone smiled and clapped and took photos, I couldn’t help by think about Jenny’s story – about how Caroline had sucked that stripper’s cock, because it was so much bigger than Glen’s. I looked around at some of the other girls who’d been at the bachelorette party, all looking gorgeous in their sexy dresses and perfect makeup, and I felt my cock get hard, straining against the tight silky fabric of the thong, as I imagined them all taking it in turns to suck him, their cute little panties getting soaked right through.
Eventually the ceremony was over and we all took more photos outside the chapel, before heading over to the reception – a lavish affair in the function room of the hotel we were all staying in that night.
The drinks flowed and everyone started dancing, and pretty soon Jenny and grabbed my hands and pulled me up to dance with her.
“I can’t wait to get you back to the room tonight,” she murmured in my ear, as we slow danced to some sexy r’n’b song.
“I can’t wait either,” I murmured back, my hands sliding down her body, cupping her ass for a moment, knowing just how she must be feeling right now – her cute black thong so tight between her ass cheeks as she ground against me, just like mine was as I moved my hips, each motion sending a little tingle of excitement through me as the silky fabric brushed against my asshole.
“Com
e on,” she said, all of a sudden, grabbing my hand and leading me off the dance floor.
“Where are we going?” I replied, confused.
“Where do you think?” she grinned back, totally taking charge now, striding ahead of me, pulling me through the crowds and out into the corridor that led from the function room to our hotel suite.
As we headed back to the room, I realized just how drunk I was. I’d tried to take it easy, but there was so much free booze and suddenly I felt pretty lightheaded. And it seemed like Jenny had had a few drinks herself – she was normally so shy, waiting for me to take charge of things like this, but tonight she seemed focussed on just one thing.
We’d barely made it into the room before she was all over me, kissing me, grinding against me, breathing heavily.
“Wait,” I said, suddenly remembering the thong, my heart starting to pound at the idea of being caught wearing it. “Let me just freshen up first ...”
“No way,” she grinned back. “Come here.”
And before I could stop her, she’d fallen to her knees in front of me, tugging at my belt frantically, desperate to free my cock.
“Wait, Jenny,” I said, trying to stop her, but before I could she’d pulled open my trousers, the bulge of my cock in that bright pink thong right there in front of her face.
Her eyes widened and she looked up at me in total shock and surprise.
“But that’s my ... Wait, what the hell, Henry?” she said, in a mixture of shock and anger.
Suddenly I felt totally sober, watching as Jenny got back to her feet, and for a moment the two of us just remained in silence. We both took a seat on the edge of the bed and when I reached out to take her hand, she pulled it away.
“I don’t understand,” she mumbled. “Why are you wearing that?”
I took a deep breath. It was now or never. I had to confess.
“Until a few weeks ago,” I began, my voice shaking a little as I spoke, “I would never even thought I’d be into anything like this. But, well, while you were gone that weekend, I just saw the underwear lying on the floor and for some crazy reason I tried it on and ...”
