The Wedding Date (Gay SPH)

By Max Swan.

“You fucking asshole, Kyle,” Janice’s voice screamed from the living room.  “I knew you were cheating on me.”

“Babe, babe, she means nothing to me, honest,” Kyle said, trying to soothe his girlfriend.

In a bedroom not far from this loud argument, a recent new flatmate to Kyle’s apartment, a skinny white college student named Daniel Lewis, stirs.  He groans as the fight has been going on for about thirty minutes now, and the poor teen has early lectures.  It doesn’t surprise Daniel that his charismatic black man has been caught cheating, it seems like every night he has a different woman in his room.  Daniel’s just grateful their respective bedrooms are divided by other rooms, and so he doesn’t hear the sexual activities.  However, the main living room is close to his bedroom and so tonight, the sophomore is getting it full blast.

“How could you, Kyle?  You know how heartbroken I was when Devin cheated on me,” Janice shouts again, her sobbing prominent.

Janice, it was nothing, I promise,” Kyle said, sounding somewhat smug.  “I was drunk; she was drunk, it just kinda happened.  You know what the bitches are like when they get wind I have a big black cock.”

“Ooh, you egotistical jerk,” Janice shouts.  “Do you think I don’t know about you?”

“Whatcha mean?”

“I know you have a booty book you use to fuck around with.  You promised me you’d stop.”

Kyle growls.  “I ain’t promised you anything, aiight.  I got bitch’s that need my cock, and I give it to them whenever I can.”

“Ah, you’re an asshole,” Janice groans.  “OK, it’s over then.  Consider yourself dumped.”

Janice grabs her bag and heads for the front door, and Kyle grabs her arm.  “Janice, you can’t…  You promised me you’d be my date at my sister’s wedding next weekend.”

The woman laughs coldly.  “Why don’t you call one of your ‘bitch’s’ from your booty book, I’m sure they’d be happy to put up with your shit.”

The front door slams shut, making Daniel groan.  Finally, there’s silence.  The sophomore knows Kyle’s a playa with women, yet he somehow feels a bit sorry for his flatmate and decides to go see if he’s OK.  Daniel finds the handsome black man sitting on the couch with his head in his hands.

“Hey, you OK, Kyle,” Daniel asks with a slight grimace.

Kyle’s head shoots up, and eyes bulge staring at Daniel dressed in his pajamas.  “Daniel, shit, man, did we wake you?” he asks wide-eyed.

“I think you probably woke the whole building,” Daniel said with a chuckle.  “That was brutal, man.”

“Yeah, I really liked Janice too.”

“Not enough to stop sleeping around on her, though?”

Kyle frowns and stares at Daniel with cold eyes.  “You gonna dis me, Dawg, after what I just went through.”

“Sorry, I didn’t mean that the way it sounded,” Daniel said going and sitting in the armchair in front of Kyle.

“Sure you did, and you’re right, I’m just too addicted to pussy to settle for one woman,” Kyle said.  “It’s a sickness.”

“You can get help these days, they call it sex addiction.”

Kyle stares at Daniel for a moment and then bursts out laughing.  “Oh, Dawg, you cheered me up with that one,” he said then laughs again.  “Sex addiction … Oh, that’s great…”

The laughing continues.  Daniel smiles but feels himself blushing, his comment wasn’t a joke, but it seems easier to go along with Kyle.

“Well, I’m heading back to bed since you seem better now,” Daniel said, standing and moving away.

Kyle suddenly stops laughing, and shouts, “WAIT…”

Daniel turns to face the black man with raised eyebrows.

Kyle frowns for a moment, looking Daniel up and down, a slight smile forming on his face.  “You look like her, you know that?”

“Don’t be stupid…”

“No, I’m not shitting you, man.  You’re like a doppelganger or some shit…”

Daniel rolls his eyes.  “Dude, I’m a man, how can I look like a woman?”

Kyle pulls out his phone.  “Here, come and look at a picture of her,” he said, waving Daniel over.  “See for yourself.”

With a sigh, Daniel goes and sits beside Kyle, who holds his phone out to show the picture of Janice.  The woman is a pretty blonde with blue eyes; Daniel had met her only a few times since he moved into the apartment.

“See…” Kyle said.  “You could be like her twin brother or something.”

Daniel takes the phone and stares at it.  He has to admit Janice does remind him of his sister Susan, maybe there is some eerie similarity here.

“I suppose…” Daniel said, handing the phone back.  “But there’s one big difference between us that makes your claim dubious.”


“I’m a man, and she’s a woman.”

Kyle laughs and slaps Daniel on the thigh.  “Dawg, we live in the age of gender fluidity, right?  People can be whatever they like these days.  Are you one of those right-wing preachy boys?”

Daniel smiles and shakes his head.  “No, I have nothing against people being whatever they want.”

Suddenly, Kyle gasps and his eyes go wide.  “I just had a fucking crazy idea…”


“My sister’s wedding is in a week, and I promised her I’d bring Janice along to meet the family,” Kyle said, gazing at Daniel, “So how about it?”

Daniel frowns; a growing sense of uneasiness makes him draw back.  “How about what?” he asks.

“Look, I’ll pay you, I know it’s a big ask, but I really need to take Janice to this wedding,” Kyle said.  “My family has been riding me for not settling down, and I bragged my new girlfriend is long term.”

“So get one of your booty bitches to take her place?”

“I showed them a picture…” Kyle said, and then holding out the phone, “This picture.”

“Pay Janice then,” Daniel said, trying to avoid the looming conclusion to this conversation.

“The problem is even if she agreed, I know she’ll just use it to make me look bad,” Kyle said.  “C’mon, Dawg, it’s only one day.  Do it for me…”

Let me get this straight…” Daniel said, trying not to laugh.  “You want me to dress up as a woman and pretend to be Janice at your sister’s wedding?”

Kyle nods.  “It’s perfect, Dawg.  I’ll even pay you for your time.”

“How much?”

“Hmm…” Kyle said, twisting his lips.  “Tell you what, I’ll let you live here rent-free for the next year if you do it.  It’ll save you a lot of money.”

Daniel guffaws.  “You’re batshit crazy, dude.  No one is gonna buy it, they’ll just think your dating a trannie.”

“Tell you what; I gotta homie who’s a drag queen performer.  I’ll get him here tomorrow night to dress you up as Janice, and if it doesn’t look right, I’ll forget it.”

“I don’t know?”

“And I’ll pay your next month’s rent just for trying,” Kyle adds.

Daniel sighs.

“C’mon, Dawg, help a brother out.”

A year’s rent free, Daniel thought, that would be amazing.  “Oh alright, I’ll let your friend dress me up as Janice to see if it’ll work, but no funny shit,” Daniel said frowning.  “I’m not a fag.”

Kyle smiles and raises his hand palm out into the air.  “No, funny shit, I promise,” he said.


Daniel is studying in his room the next night as he has an assignment due in a few weeks and wants to get on top of it when there’s a knock on the door.  His head pops up out of a book and turns toward the door.  The man’s stomach suddenly churns because he knows what the knock is for and has spent most of the day regretting he agreed to this silly scheme.

“Yeah?” Daniel shouts.

The door opens, and Kyle is standing there with another dark-haired white man behind him.  The man has noticeably trimmed eyebrows in the way females do, his hair is short, and his face has a feminine bone structure.

“Hey, Daniel, this is my friend Tony I told you about,” Kyle said, stepping into the room with the drag performer following.

“Oh, hey, Daniel,” Tony said, holding his limp-wristed hand out.

Daniel stands and shakes his hand.  “Hi, so I guess we’re going through with this crazy plan,” he said.

“Like we agreed last night, if you don’t look right we won’t do it,” Kyle said nodding.  “If you do look like Janice and agree it’s a year rent free.”

Daniel grimaces.  “OK, I guess.  But this stays between us.”

“I won’t tell a soul, darling,” Tony said, throwing his head back.  “You have my promise.”

“Me too,” Kyle adds.

“Alright, let’s get this over with…” Daniel said.

Tony turns to the big black man, shoos him out of the room, and gets a large case in the hallway and returns, shutting the door.

“OK, let’s see what I’m dealing with here,” Tony said with a finger to his lips, looking Daniel over.  “Strip for me.”

“What?  I told Kyle no faggy stuff…”

“Oh pull-ease, I need to see you naked so I can see what I need to do to turn you into a woman…” Tony said, throwing his hands forward.  “I’m not interested in having sex with you.  I have to build it from the skin up.”

“I-I don’t know…”

“Jesus, haven’t you ever stripped in a change room in front of other guys, just think of it like that.”

Truth is Daniel avoided change rooms all his life, but he never told Tony that.  If he ever found himself with no other option, the college student would find a corner so he could hide in plain sight.  The way Tony is staring at him makes Daniel feel ashamed, and his heart beats fast in his chest.  With a sigh, he starts to take his clothes off.

“Good, now we can begin,” Tony said then turns to his case and opens starts opening it.

The dark-haired drag performer gets some items out of the case and put them on the bed and stands just as Daniel pulls his underpants down.  Tony’s eyes go right to Daniel’s groin, and a slight smile plays at the corner of his mouth.

“Well, at least I don’t have to worry about taping your dick back,” he said, still staring at Daniels groin.  Then gazing at the red-faced student’s eyes, Tony said, “You don’t have too much hair, which is good.  How often do you shave?”

Daniel swallows.  “Um, once a week,” he said.

Tony steps forward, runs his hand over Daniel’s face and nods approvingly.  “Turn around for me so I can see the back.”  Daniel does and stands silently for a moment.  “OK, turn around again.”

When Daniel is facing Tony, the dark-haired man is rummaging in his case.  He pulls out a tube of something.  “Here hold out your hand…”  As Daniel does, Tony squirts some white cream onto his hand.  “Rub this cream on your chest, underarms, groin, and legs.  I’ll do the back.”

“What is it?” Daniel asks, staring at the white cream.

It has a chemical smell to it.

“Hair removal cream,” Tony said slapping on some rubber gloves.

“What do I need this for?  No one’s going to see my body.”

“I told you, we have to build this from the skin up.  Now get to work, I haven’t got all night.”

Daniel sighs and starts rubbing the cram on his chest while Tony does his back.  Reluctantly he rubs it over his genitals, and the dark-haired drag performer does the students legs.  Eventually, Daniels covered from his neck down in the slippery hair removal cream, and he can feel it burning his balls.

“It feels like it’s burning me,” Daniel complains.

“It is…  Your hair anyway…” Tony said then Daniel’s eyes bulged.  “Don’t fret; you’ll wash it off before it affects you badly.  Now go shave your face for me.”  Daniel sighs and goes into his bathroom and shaves.  Tony soon follows with some scissors and tweezers.  “Turn here and let me fix your eyebrows.”  After Tony’s satisfied Daniels’ eyebrows appear more feminine in style, he orders the man into the shower.  “Make sure you wash that cream off thoroughly, give everywhere a good scrub, especially your balls.”

After the showers over, Daniel returns to his room to find Kyle is sitting on his bed, talking to Tony.  Kyle turns to see the naked college student, and immediately, the black man’s eyes fall to Daniel’s groin.

“Shit, man, you got a real white boi dick, eh?” Kyle said with a smirk.

“Stop it,” Tony said, waving his hand in the air.  “Daniel is obviously a grower, not a shower.”

“I hope it grows a lot, Dawg,” Kyle said, still smirking.  “Cos I’ve seen bigger clits than that, Dawg.”

Tony slaps his shoulder with his limp wrist.  “Get outta here now, we got work to do.”

OK, OK…” Kyle said, getting to his feet and leaving.

Tony turns to the blushing Daniel after Kyle is gone.  “Don’t mind him, like all black men with big cocks they think it gives them a right to be assholes.”

“Yeah, toxic masculinity,” Daniel whines.

Tony just smiles and grabs some panties from his case.  “Try these on and see if they fit…”

“Panties?  Why do I have to—” Daniel stops reading the expression on Tony’s pinched face.  “OK, from the ‘skin up,’ I get it,” and he puts them on.

Tony next hands Daniel some sheer black stocking and after those are on, the drag queen hands the student a bra with fake silicone breasts in the cups.  Daniel stares at himself in the mirror, thinking how bizarre this all is, standing there in women’s underwear and stockings.

“Now sit down, and I’ll do your makeup,” Tony said gesturing to a chair.

As Daniel sits, he thinks this is where the whole thing will fail.  He’s seen pictures of men online wearing makeup in the female style, and it just seems to highlight their masculinity, not mask it.  The student thinks despite all the underwear, and clothing, Tony will make him wear, there’s no way makeup will hide what he really is—a man.  It takes a good fifteen minutes for Tony to do all the layers and add the final additions like mascara, lipstick, and eyeshadow.  The dark-haired man steps back with pursed lips considering his work.  Then his face brightens, and he goes to his case and retrieves a long blonde wig.

“This should complete the transformation,” Tony said and put the wig on Daniel, positioning it just right.  “OK, go and take a look in the mirror.”

Daniel stands staring in the mirror in his bathroom, feeling his stomach churn.  He feels funny already with all this junk on him.  As the sophomore stares wide-eyed at his face in the mirror, he gasps.  Tony had styled the wig to be precisely like Janice’s hair, and the makeup didn’t highlight his masculine features, in fact, quite the opposite.  For the first time in this bizarre venture, Daniel has to admit he looks like Janice, at least dressed like this.  Tony stands behind him with a smug grin playing across his face.

“I have to admit, I didn’t believe Kyle when he said you looked like Janice, but like this, I’d say he was right,” Tony said with a slight grin.  “You really do have a feminine face.  I know men who’d kill to be like you.”

Daniel spins and stares at Tony with a deep frown.  “I’m no fag,” he said harshly.  “I’m doing this to get a year’s free rent, that’s all.  Once I attend Kyle’s sister’s wedding, that’s the end of it.”

“Hey, I’m not judging you, Daniel,” Tony said, throwing his arms in the air dramatically.  “I’ve done worse for free rent.  It’s no big deal.  We all gotta do what we gotta do.”

“So what’s next?”

“You have to finish getting dressed, darling.  If Kyle sees you like this, he might just want you in the biblical sense.”

Soon Daniel is wearing a tight, sleeveless red dress that ends just above his knees.  The dress doesn’t show any cleavage because Daniel doesn’t have any, but instead the material goes to his neck in front, but leave his back exposed.  After putting on some clip-on earrings and a pearl necklace, the last item is some flat black shoes, Tony didn’t think Daniel was ready for heels.  Last, Tony sprays some perfume into the air and makes Daniel move through it.  The transformation is complete, and Daniel appears for all intents and purposes a woman.

“You look amazing,” Tony said then giggles.  “It’s some of my best work.  Kyle is going to get a boner when he sees you like this.”

“Kyle can keep it in his pants,” Daniel said then sneers.

“Hmm… Try to speak like a woman, your voice will give you away,” Tony said.  “Trust me as one who’s experienced this, if a bunch of straight men are drooling over you and then find out you’re really a man…  Well, let’s just say it can get pretty ugly.”

“How’s this?” Daniel said in a higher pitched voice.

“Not bad.  OK, let’s go show Kyle.  Something tells me you’re going to the wedding to the weekend this weekend.”


Motherfucker…  You look exactly like her, I told ya, Dawg,” Kyle said, wide-eyed staring at Daniel.

“I don’t think I look exactly like her…” Daniel said, then grimaces.

“Close enough.”

“Do you really think people are going to buy this?”

Tony said, “Why don’t you test it?”


“Yeah…” Kyle said, nodding.  “What’s that club you always go to with your friends?”

“Um, ‘The Forge’ down on Washington road,” Daniel said.  “Why?”

“Let’s go there now since you’re all dressed up for it,” Kyle said with a grin.  “Let’s see if people who know you recognize you dressed as a woman.”

Daniel gasps.  “No way,” he shouts.

“We can just say it’s a college prank…”

“I don’t know…”

“Look, if anyone starts giving you a hard time we’ll come home immediately,” Kyle said with a smile.  “Have some fun with it, Dawg.”


“Good, I’ll get my stuff, and we can go,” Kyle said, breaking into a big grin.  “Are you coming, Tony?”

Tony glances at his watch.  “Sorry, I gotta get downtown for my show soon.  But please tell me all about it,” he said to Kyle.  The black man nods and heads to his bedroom to change.  Then to Daniel, Tony said, “I left a purse in your room with some makeup in it.  If you get sweaty, just go to the female toilet, pat your face with some paper towel, and apply more foundation if you need it.  That should get you by.”

“I have no idea how to apply makeup,” Daniel said with a shiver.


I’ll be around Saturday morning to help you dress for the wedding.  Use the hair removal cream again that morning before you shower, I left a tube in your room.  I have a cute outfit all ready for you to wear that’ll make Kyle’s male relatives drool, and his female ones hate you.”

Daniel sighs.  “Thanks, I guess.”

“It’s a pleasure, darling,” Tony said.  “Cya, don’t do anything I wouldn’t do tonight.”

“I told you—”

Yeah, yeah…” Tony said, heading out the door waving his hand.  “You don’t do no fag shit…bye…Janice.”


This is an excerpt from this 27,500+ word eBook. If you want ready every sexy, nasty word — THEN BUY IT! — You won’t be sorry.


Leave a Reply

Your email address will not be published. Required fields are marked *

Translate »

You cannot copy content of this page