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The Bachelor and the Stripper

The Bachelor and the Stripper

by Tvdude17
19 min read
4.75 (31500 views)
first time gaycross-dressingbest friendsgay anal sexstraight
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Angel.

That's the name I give her as he looks back at me in the mirror. Unlike me she has no beard, no body hair at all. My flat brown hair hidden under long locks of white that drape across her shoulders.

Her face looks thinner, helped by the make-up my younger sisters taught me to put on. Foundation, blush, mascara. Now Angel's lips were a dark purple, like the eyeliner. Her eyelids covered with silver sprinkles.

Her body no longer emphasizing my toned muscles, thanks to a silver sparkling dress that accentuates her big fake breasts in a big white bra. And her hips with the dress resting on her fat ass, with straps down to her silver stockings and golden heels.

I'd fuck her if I saw her at a party.

All week I've been practicing walking in these shoes, with help from my sisters. I'd carefully ordered the lingerie to fit a man's body size. The huge silver wings on Angel's back were somehow the easiest part to find. Now I saw the total picture of my preparation, I was in trance.

Angel felt different. Another person entirely. She rested on her hips, plopping out her big cheeks for all to see. Her shoulders were relaxed and crouched down, to add to her meek pose. She was shy, I could tell, insecure perhaps if this was a good idea at all. If people would think of it as the joke it was, or perhaps could see, stare down her soul, and know she felt good in these clothes. Sexy even.

It all started a couple of months ago, when I started planning my best friend's Jake's bachelor party. I'd rented a nice lake house down state. Remote enough for twelve blokes to get absolutely fucking wasted and party all night. As any best man is obliged to do, I of course rented strippers to appease us boys. Until Jake's fiancΓ©e Melanie found out and the fun was soon cancelled.

Jake, however, had whispered in my ear to get a dancer, a professional dancer. She didn't even need to strip. But he needed a girl. One last girl. And I would've, except I know Jake.

We've been friends since college. Roommates who shared everything, including the occasional girl. We spent most nights talking endlessly over beer or scotch and cigarettes. About girls, life, relationships, our past and our future.

Jake is more sensitive than he pretends to be, underneath that professional and always crisp exterior. He doesn't want to cheat, especially not the week before his wedding. He wants an emotional connection, a love, not some meat bag he puts his dick in and regrets the next morning. Not hiring a dancer is the greatest gift I could give him for his wedding.

So instead of putting him in a compromised position, I myself have taken up the mantle of stripper. That will surely get him to laugh his ass off. At least I hope so.

And now it's here. The moment of truth. An hour ago, Jake, already slurring his words, took me apart to ask me where the dancer was. Was she still coming? Did I forget? I promised she was on her way and snuck out to the bathroom where I put on everything, from make-up to the stockings.

Outside I could hear the laughter and yelling of a dozen former frat boys getting shit faced. Let's see what Angel can do to them.

Angel shakes off the last existential thoughts and walks into the living room. A few men are playing poker and are deeply focused on the game. Others are on the balcony chilling by the lake.

One by one the faces look up and drop. And the noise stops.

A moment of absolute silence. Angel swallows nervously but it's too late to back out now. Instead, she smiles and pushes out her boobs.

"Anyone asked for a stripper?" Angel says. And she walks to the stereo and puts on the sexy pop song she has been rehearsing on.

And then a roar of laughter.

"HAHHAHAHA HOLY SHIT!!!" "THAT'S AMAZING!!" "BRO LOOK, LOOK!"

The men all jump and yell or fall over from laughter. Some come from outside rushing in to see. Others grab their phone.

Angel giggles. She loves the attention and gets into position, her back turned to her audience, booty out. One, two, three!

Under loud cheering as if they're in a football stadium, Angel performs her routine. Hair flips, heel kicks, arms waving through the air. She worries if her wig will hold but the dance goes perfect. She's got this.

She winks confidently at a guy next to her, who pretends to be hit in his heart. Another takes out his wallet and throws bills at her. Angel is loving it. And grows more confident and seductive.

With ease, as if she's had them all her life, she pushes her arms against her breasts, making them pop. She twerks her ass, revealing her thin white thong underneath her dress. And her wavy locks bounce on her shoulders and breasts.

And in the small crowd of jumping and laughing and cheering men, she sees him. The groom.

Angel steps on the table to even louder cheering and pushes the other men aside. Jake shakes his head in disbelief but surrenders to the bit.

Angel pushes him in his chair and stands over his legs. She bends over and gives him an air kiss.

Camera's flash and the audience goes wild. One guy touches her hair, and Angel quickly slaps him away. She belongs only to the groom.

Seductively she takes off her wings and gives them to a man, who pretends to smell them, to laughing of the others.

But it turns more serious when she also pushes down a strap of her dress over her shoulder.

Jake throws his hands in his face, shaking profusely.

"What are you doing man?" He laughs.

Angel doesn't care. She knows she's sexy. She knows they all want her. And with that confidence she pushes down her dress.

It gets stuck on her boobs and so she grabs them and massages them. She backs up and shows Jake her booty, shaking and bouncing on the tunes of another song that has started.

Jake slaps the ass hard and then squeezes in it.

"WOOO you like that don't you!" One of the guys screams.

Skillfully Angel pushes down her dress without messing up her boobs and exposes her bare back to him.

And when she has reached her private parts, she turns back around and shakes her boobs in his face.

Jake motorboats them and holds them tight. And for a second Angel wonders why it feels so good. They're plastic, not attached to her. But him massaging them sends tingles from her chest to her brain and down to her dick.

She grabs his hands and pushes them over his head, forcing him to surrender. Jake almost cries laughing. The men keep cheering and some have turned their phones into flashlights, spotlighting the action for all to see clearly.

Angel steps out of her dress and sits almost down on his lap and starts to ride the air.

A guy slaps her big smooth butt, but she throws him an angry look.

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"Oeeeeeeh" the men jeer.

She takes one of Jake's hands and puts it on her boobs again, wanting that feeling once more. She looks down at him and sees hungry eyes staring back.

She's never seen him like this before. This... horny.

Jake has a jaw like an anvil, smooth and muscular. His face is manly, with big lips, big nose, square cheekbones and deep blue eyes. He is still built like the farmer's son he grew up as. Broad shoulders, but toned, not like those fit boys from the gym. His arms are huge but without visible biceps. His belly is flat but without visible abs. A man's man through and through. Though he's always dressed in blouses or suits to compensate for his modest upbringing.

And in his lap, Angel feels... small. Pretty. Feminine. Safe.

But his eyes are like a mountain lion sees a prey. Filled with deep, dark, carnal urges that cannot see the light of day. It makes Angel feel meek, vulnerable but above all... sexy as fuck.

She pushes his hands down her shaven stomach and over her naked waist to her ass.

It's all fun and games until your best friend's hand is holding your naked ass cheek.

Angel gets hard in her panties. The feeling of this big manly hand, a hand she's seen for years but never felt, not like this, on a sensitive part makes her horny beyond compare. She's being held by him, grabbed by him, owned by him.

The blood rushes through her body to her dick which starts to swell in her panties, and she quickly continues her performance, by turning around and sliding her ass up and down his body.

Another mistake. Feeling his chest, his stomach and finally his crotch sends her into overdrive. The heat radiating from his pants to the heat coming from her ass connect through the fabric. It makes her stop in her tracks and wish to push it down further. Makes her want to feel his cock against her ass. But she can't. This is a joke. This is supposed to be a joke.

Angel throws herself back to enhance the joke and it works. Jake laughs and so does everybody else. She goes the extra mile to make everyone uncomfortable and dance badly. She throws her leg up in the air, but she's not nearly flexible enough and it only goes halfway. She jumps on his lap with her knees, almost kicking him in the nuts, and waves her hair round and round.

Everybody dies of laughter and Jake's eyes look normal and boy-ish again, laughing at his stupid best friend.

The wig falls off and Angel worries about one of the guys choking in his beer and falling on the ground laughing.

She can't help but laugh herself.

The second song ends, and Angel has no more dance moves left. Instead, she crawls off Jake's lap and takes a deep bow.

The men applaud her as she picks up her wig, but another guy takes it and puts it on, pretending to be sexy.

I let it go. Angel had her moment. I feel the masculinity rushing back into my body and soul. My shoulders lock backwards, my chest raised high, my back straightened, and my butt arch lowered. I feel like myself again. And I let myself fall into the couch and gratefully take the beer handed to me as the men applaud.

I snicker as Jake locks eyes with me.

"Naughty girl!" He jests as he takes his whiskey and sits down next to me.

"I told you I'd take care of it," I sighed.

Jake rubs my hair like he always does and lets his arm rest on my shoulders like he's done a million times. And still, a wave of tingling heightens every nerve in my arms. This doesn't feel like normal. It feels like a girl would feel if a guy was hitting on her. It feels like he's claiming her.

I sip my beer to shake Angel off of me.

"Well, that's all I got, old man. It's still you and your hand tonight," I say, embellishing my low voice to sound more manly. Like his friend.

It seems to work. Whatever tension I felt with this embrace, is gone as Jake sits up straight and retrieves his arm.

"It was hilarious man, I really appreciate it. It's the best bachelor party I could've imagined." He smiles grateful and I nod appreciative.

"Come on, sexy lady, can I get a lap dance!" Thomas says as he thrusts his hips in the air.

"I can touch you?" I replay and raise my hand and slap him hard in his crotch.

"OOOOEEEH she bites!" The others laugh while Thomas grabs his crotch.

Jake takes the wig from Karim's head and gives it back to me.

"Put it back on," he breathes, inebriated and with a desperation I can't quite place. I oblige and put the long hair back on.

I suddenly realize I've been away an hour preparing this and everybody else has continued to drink. I'm easily three, four drinks behind if not more. This pack of men, my friends, some I've known for years, all gather around me and look at me like I'm not me. I thought the wig toss would break the spell, but to them I'm still Angel. I'm still a woman, a stripper, and they want what they ordered.

Angel feels threatened. No girl likes to be alone in the woods, surrounded by a group of horny, drunk men.

"Let's play a game," she says.

"Yes, let's!" A tall black dude says excited as he inches closer on Angel's other side on the couch.

"Spin the bottle!" Angel says, ensured that a group of all men will immediately turn off when they have to kiss each other.

"Great idea!" The guy who tried to touch her yells from the opposite side of the table. "Whoever it lands on can kiss this hot piece of ass!"

The group laughs but nobody seems to turn away. Instead, a few share a bottle of rum and take deep sips. Angel starts sweating.

The guy who stole her wig empties a wine bottle and puts it on the table to spin.

"I'm not sure if this is a good idea..." Angel protests.

"Come on, it was your idea!" Jake replies.

Angel nods and takes Jake's glass and downs the whiskey. It burns in her throat, but it'll help later on, she's sure.

"Here's to the lucky fellow!" The guy yells as gives the bottle a whirl.

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The bottle spins only a bit before landing on a big guy. He's sweaty and nervous and doesn't seem to have a lot of experience with women. His egg-shaped face lifts up his wet lips. Angel has to turn on her professionalism and crawls seductively over the table.

"Big boy wants a kiss?" She says as sexy as possible.

"Wooooooh!!" The men yell.

The guy licks his lips, and Angel throws herself at him, kissing him quickly before pulling away.

The watchers burst out cheering and laughing, spilling beer and knocking each other. Everybody laughs and pushes each other.

Angel laughs and shrugs, wiping her lips. She throws a look back at the guy who seems to be blushing.

"Who else wants?" Angel says commanding as she spins on her heels.

The big guy turns the bottle, and it lands on a handsome tanned man with a black beard. Angel feels her dick jump in her panties. The man blushes and pretends to not want it, but his friends urge him to not be a pussy.

Angel thankfully makes use of this by stepping forward with her legs in stockings and heels and making a big show of it.

She steps over Jake to get to the man and leans on his chest. His pecs are rock hard and broad. She wants to use them as a pillow.

Angel feels how he instinctively holds onto her waist, like he's done to girls probably a million times. She smiles, feeling safe and sexy but lets him come to her.

The kiss is warm and intense, his big lips pressing hard against hers. Angel represses a moan as she sinks into his embrace.

The guy makes a smooch sound and pulls back and looks at the other men with pride.

"What are you gonna do? Huh? None of you got shit on me!" He laughs as he raises a glass, and the others cheer him on. Some guys bend over laughing. Others pretend to vomit. More than one has their phones out, laughing, recording this absurdity for future reference.

Angel looks a bit flabbergasted as she's pulled out of the moment, this intimate moment with a man. She starts laughing. Of course. This is all a joke.

The guy flexes his arms and steps forward, almost knocking Angel over. He spins the bottle again and it points to Angel, who is a bit relieved she doesn't have to endure this again.

Except, everyone starts jeering at the guy she's standing in front of. Angel turns around and sees Jake sitting on the couch.

"I can't, I'm promised to another!" Jake waves apologetically.

"Shut the fuck up!" A man yells. Someone throws an empty beer cup at Jake's head.

Angel sees his resistance and gets cocky. She sits down on his lap and slides to the side, her legs draped over him.

"Are you sure you don't want this, daddy?" She says exaggerated, commanding more laughs and cheers from the audience.

Jake nods, accepting his fate.

"Come here," he sees as he lunges forward, grabs her head and pushes their lips together.

The kiss is harsh at first, Jake pressing hard to make a statement, to get it over with. But as soon as their lips lock and the kiss begins, their mouths are glued together. Their whole bodies are. It turns into the softest, realest, most hungry kiss Angel has ever felt.

At first, she doesn't move, too stunned. But then she feels herself push forward and suck his lips in, holding them tight to never let go. While he takes control and massages hers, pushing them open to make way for his tongue.

Angel's mouth is invaded, conquered, by him. She lets herself be taken by his tongue, searching through her mouth, licking everything in sight. She sucks on it, rolls her own tongue against it, but it is unyielding, locking their mouths together, pushing deeper into her. Before it pulls back.

The kiss lasts maybe a few seconds, but it has disarmed Angel beyond repair. She has never felt more like a woman, more submissive, more belonging to Jake.

Jake retracts much like the other guy did, pushing her away and looking to the others for approval. The men all yell and cheer, as Jake chugs someone's left over beer and raises his arms.

Everybody carries on partying like nothing has happened. Beer and hard liquor flows, some start dancing, others continue playing poker. Jake gets up and leaves. But Angel, Angel sits on the couch and touches her lips. Wondering if she'll ever feel as amazing as she did just now. And if women always feel like this when they're kissed, truly kissed, by a man. So... in love?

She gets up and finds her dress to put back on and wanders around. She notices men are a lot more handsy now. Hands slap her ass and linger, touch her back and waist. There's something magnetic about a man's hand. It's so firm, so commanding, so large. Angel feels alive every time one touches her. She feels wanted and sexy.

The night continues with many more drinks and Angel feels the earth spin. They're all outside laughing and drinking and Angel makes her way through the crowd. Suddenly she feels a hand slide over her back. It touches longer than any before and makes its way down her ass. It slips under her dress to her bare ass. It's the most erotic feeling. A man's hand where it shouldn't be. And just briefly, she feels a fat manly finger part her cheeks and touch her warm hole. She jumps at the strange sensation and looks around. It could've been any of the five men huddled together, talking and drinking. Angel blushes and gets out of their way.

The sensation was by no means unpleasant, but this is too much even for her. She's not out for sex. She's too professional for that. So, she plants herself on the swing next to the house and empties her beer bottle by herself.

Angel gets lost watching the stars and it's not until an hour later that she notices the party went quiet.

"Pretty girl like you shouldn't be out alone late like this," a firm voice says. Angel jumps and looks behind her. Jake walks down like the dapper gentleman he is, with a glass of whiskey in his hand. He walks around her and flashes a bright white smile.

From down here he looks tall, handsome, the perfect man. Angel understands why a girl wants to lock him down.

I shake my head to get rid of the thoughts. This act must stop. Angel isn't real. She was a joke. And it has gone on long enough.

"Shut up," I say, as I always do to him. Jake looks away and his demeanor changes. More relaxed, more like he usually is with me. The gentleman evaporates in front of my eyes along with Angel in front of his.

"Are you enjoying yourself on your last free night, bro?" I ask polite. Jake nods and takes a sip. He missteps and I only now notice how drunk his eyes are.

"It's crazy right. One of us married," he says as he takes another sip.

"Not that crazy. I always knew you'd leave me for a woman," I jest. Jake grins and we lock eyes.

"I appreciate your last stand," he says, cheekily. For however serious, intellectual and posed Jake is to the outside world, he is always that dumb college jock with me. Always looking for an adventure. And his eyes beg for one now.

"I didn't want you to do something stupid," I said honestly, getting off the swing and stepping towards him.

Jake nods, downs his glass and throws it away.

"Like this?" He says before he attacks me, grabs my head and plants his lips on mine again. I almost moan at feeling his mouth again, our lips massaging each other again, the taste of whisky seeping over into our spit. I can't not open my mouth again and let his tongue drown me.

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