This morning, Master ordered me to report to his apartment immediately after work. I wasn't entirely sure what was going on; we hadn't set up any plans. But knowing Master, I was sure it was going to be a pleasant surprise. So I spent the entire day totally distracted and not getting any work done, and yes, leaking precum into my briefs. The cold, sticky wetness only served to deepen my humiliation, making me hornier by the second.
It felt like forever, but the clock finally showed 5:30 and I practically ran out of there, at least as fast as anybody with a hardon attempting to escape his underwear could run. I sped to Master's apartment and knocked on the door. As he opened the door and saw my face, I could see his lips form the smirkiest of smiles. He said, "I've thought of something fun to do today. Now strip."
I tried to enter his apartment, but his hand blocked my entrance. "Oh God," I thought, "He wants me to strip out here. But what if somebody sees me." I looked around, hoping I wouldn't see anybody else. I'm a white collar professional earning good money; I couldn't bear being arrested for obscenity. But to my shame, my cock twitched at the thought. I knew deep down inside, this was what I wanted, so I set to my task.
I take off my shoes, jeans, and shirt and hand each item to Master, leaving just my briefs. The wet spot from the day's precum cools and chills my cock as it is exposed to the dry autumn air. I give Master a look and his brow furrows in response. He says, "Those too. I've got something better for you to wear." As I look around again, my briefs get tighter as my cock tents the fabric, only adding to my shame. I quickly take off my briefs, offer them to Master, and attempt to rush into his apartment. Yet again, his hand stops me. He points at his mouth. I quickly stuff my briefs into my mouth and he lets me in, just as the sour taste of sweat and precum floods my brain.
Master has me stand at attention just inside the doorway, but to my wonder, he leaves the door open. I feel the outside air chill my butt as it rushes into his apartment. Master disappears for a second and returns with something in his clenched fist. He tosses them at me and they land over my cock. "Put these on," he says, just as I realize these are women's panties.
The understanding of what's about to happen rushes through me, causing my cock to bob up-and-down with each heartbeat. I slowly slide on the panties and find that they're rather tight. My junk is tucked up awkwardly next to my taint and things don't feel right. Master slips his hand down the front and makes a few adjustments. I sigh as I feel his strong hand roughly manipulating my cock and balls, digging out them out to the front and producing a large well-rounded bulge.
Then Master disappears again and comes back with a paper bag containing the rest of my outfit: the slutty schoolgirl. I begin to dress, first putting on the thigh-high black socks. Next, I put on the white shirt to find that it barely covers my midriff. Finally, I put on the grey schoolgirl's skirt only to find that the bottom barely covers the bottom of my bulge. Much to my chagrin, the skirt seems to sway in time with my throbbing package.
I can almost hear the whole world yelling "tart!" at me just from wearing this outfit, but somehow Master isn't satisfied. He pulls the socks higher and lowers the skirt, until the gap between them shows just a hint of my smooth moisturized skin. Goosebumps rise on my skin. I can't tell if it's cold or if it's because I'm so turned on by my thoughts of what will happen next. After all, there's no way we're playing dress-up just for his private pleasure.
"Almost perfect," Master says, "Go get your heels on, we have to go soon." I put on the heels and take a few small steps unsteadily, causing my skirt to sway. I imagine that my panties are surely being exposed by this. The thought causes a jolt of pleasure to flow through me and all arriving at the tip of my cock.
Master studies my face and says, "No, that just won't do. Let's get you looking a bit nicer." What. Both of us are guys, regardless of how I'm dressed. Neither of us have ever put on makeup before, and I'd much rather look like a woman than a clown.
Master pulls out a bullet vibrator and a small bottle of lubricant. I know what comes next. I turn around to face the door and bend over, lifting up my skirt and pulling down my panties. I spread my cheeks and await his move. Master lubes the vibrator up and it slides in easily. He tucks the control into my stocking, and turns it to a lower setting. I feel it buzzing away, occasionally hitting my prostate, causing my butt to clench. Master keeps me bent over as he cups my package and feels my cock jerking as the vibrator does it's duty
Master calls towards the door, "We're ready for you now." I begin to feel a few initial tugs of panic. He says, "I don't know about you, but I've got no clue how to do makeup. So I got a friend to help." A woman who looks like half my age fills my vision. Where did she come from?! I didn't see anybody out there when I was stripping. She grabs me by neck and leads me to a chair set up in front of a mirror. She stands me up and pushes me down into the chair.
"Ugnhhhh," I moan as the action pushes the vibe up against my prostate. I shudder as I feel some wetness in my panties. I must be leaking precum all over my underwear. The woman fiercely grabs my shoulder and pushes me down into the chair. "Don't ever move when I'm working. Ever," she says.
With another evil smile, Master ramps the vibrator up another setting. "Anhhh," I moan even louder as I jump up in the chair. "I can't deal with this," the woman says. She reaches into her bag and pulls out a few zip-ties. "Arms on the armrests, legs against the chair," she orders. Master and the woman make quick work of the bindings. Then she takes my briefs out of my mouth and jams a ball-gag in there instead, holding my lips apart so she can apply lipstick more easily. When she finishes the rest of the makeup, Master compliments her work, saying "Almost perfect. No one will know the difference." I look in the mirror and am shocked at how much ahs changed.
As she packs up her things and leaves, Master undoes the gag and zipties. He sets a bright pink wig on my head, saying "I think this looks much better. I'm sure you noticed, it's bright pink so as to catch everyone's attention."
"Oh and before I forget," he says as he reaches between my legs and turns the vibrator up another notch. "Now let's get going." My breathing becomes labored as each step I take causes the vibrator to shift and bump up against my prostate. In my ass and in my cock I feel each step on the staircase down to the street. The wind rushes up under my skirt and I can feel my precum soaked panties cool my cock and balls.
Master seems to be loving this as much as I am. He keeps his arm around my waist, every so often sneaking his hand downward to give my ass a quick squeeze. As we walk down the city streets, he hails a cab. We get in and Master directs us to some intersection I've never heard of. "I was thinking," Master says, "it's been awhile since we went somewhere nice. I found a lovely little place. I think you and the other people there will get along very well." "Other people?" I ask. "Don't worry," he replies. It's no one you need to be afraid of."
"Now we've got a little trip ahead of us, so let's spice things up." He unzips his pants and says, "How about a little taste of things to come?" I loosen Master's belt, unbutton his pants, and open up his fly. I go fishing for his cock with my mouth and tongue, smearing lipstick all over his boxers. I finally find it, wrapping my tongue around his hardening cock and pulling it out of his boxers. I take his cock in my mouth and his cock springs to attention, filing my mouth. I swirl my tongue around the head, then plunge all the way down to the hilt in one swift stroke. Master gasps and I grin inwardly knowing I can still surprise Master. I swallow a few times, letting Master feel my throat on his head. "You know just what your Master likes," he sighs. I go up and down, slow then fast, then slow, then down to the hilt and some more swallowing.
It's almost too much for him to bear. I can feel his cock throbbing the way it does when he's close. He takes another deep, shuddering breath, gripping my head with one hand, the seat with the other. I pull up to let the cum flood my mouth so that I can taste my Master. I use my tongue on his head to try to push him over the top.
To my surprise, nothing happens. He doesn't cum. Instead, he breaths sharply in and out, then gently pulls me off his cock. He says, "We're here." Feelings of disappointment and need flood my brain. My mind is blank with shock for a few moments. Master pays the driver and says, "Lets' go."
I find myself looking at a nightclub. But to my surprise, Master doesn't lead us to the door. Instead we end up in an out-of-the-way alley and to the back of the nightclub.
"Pull down your panties," orders Master. I look around to make sure nobody is around, then give Master a look while I pull down my panties. He reaches in with one finger, slowly easing out the still vibrating bullet, taking extra care to push it against my prostate as he's sliding it out. A long loud moan escapes my throat and my cock jerks several times as a steady stream of precum escapes my urethra.
"Don't cum yet," he warns. He reaches into his bag and produces an enormous rubber dildo. "Here, use your mouth. Get it nice and slippery before it goes inside." I enthusiastically start deep throating it, imagining it is Master's own cock from a few moments before. My mind is so completely occupied with this fantasy that I don't even notice Master suddenly plunging his cock into my ass.
He pushes me into the wall and begins to fuck me. He pulls almost all the way and drives deeper with each stroke, right to the base. I try to say "yes! yes! yes!" but with the dildo in my mouth, all Master hears is "Mmph! Mmph! Mmph!" I work my ass muscles to clamp down on Master's cock, making my rectum express my primal need to feel every last millimeter of his cock. I hear Master moan, softly at first, then louder and louder.
One of Master's hands slips over my cock and he begins to ever so gently rub the tip. I start bucking back and forth, trying to get more cock in my ass, trying to get more of Master's touch on my cock. My mouth and throat become useless as they simply open up to accept the dildo. Master continues to tease my cock with a gentle touch, getting me close but not letting me cum. His own thrusts start to slow down; I can feel he's on the edge too.
Then, he suddenly pushes in all the way to the base and grinds me into the wall. He feels my rectum spasming on his cock. This seems to satisfy him, so he finally grips my cock and gives it a full stroke. I desired him to grip it as if he were gripping a climbing rope, but alas, he only gave it a soft stroke. Nevertheless, it was enough to push me over the edge.
I start to cum all over the wall. Spurt after spurt after spurt splashes against the wall and splatters against my legs. The wave of pleasure seems to go on forever and I lose track of how much cum has exited my cock. The spasms push Master over the edge. He grips me tight, body pressed hard to my own, trying to push even deeper as his warm gooey seed fills my ass. I can feel each jerk of Master's cock, each one pumping more fluid into me.
It feels like minutes, but our heart rates seem to slow down and orgasmic wave seems to subside to a low buzz. Master pulls out, leaving a thin strand of cum as if my ass is still trying to keep some kind of hold onto his cock. But no sooner has he pulled out then he grabs the dildo and shoves it in me, sealing his cum within and causing one last spurt of cum to dribble out of my cock.
Master pushes me down to my knees and presents his erection to me. "Clean it off," he orders. I suck it rather lazily, still lost in the haziness of orgasm, but Master doesn't seem to mind. He pulls me up into an embrace and we lean against the wall, breathing hard.
He looks at my panties, soaked in cum, and says, "I don't think there's much point in you wearing those anymore. Give it here." I slide the panties down my legs, shivering as the panties leave trails of wet sliminess. "Open wide," he says, as he stuffs the panties in my mouth. I lick my tongue all over the panties, seeking out cum from every nook and cranny. "Does your cum taste good?" I can only nod my head.
"Well, I think we're ready to meet those people I mentioned." He zip-ties my hands in front of me and leads me through a door in the alley. A couple people are inside chatting, and upon seeing me, they share a knowing smile. I look where they're looking and realize they have a perfect view of the alley. Turns out Master and I were fucking on a piece of one-way glass. They saw everything. A jumble of emotions flood through my head. Some shame and embarrassment, but even a little pride for bringing pleasure to their day.