Our Gay Apparel

By Nocti Raven
[email protected]

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This story is intended for ADULTS ONLY. It contains explicit depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.

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I looked pretty good in that new suit. And don’t you dare call me arrogant, because it wasn’t just my opinion. My mom and dad and my Aunt Helen all agreed that I was filling out very nicely for a 14-year-old (joining the football team probably had something to do with that). And I had confirmation from outside the family as well: several girls at school had asked me out, and I’d said yes to more than a few. I enjoyed playing the field . . . and experimenting. I didn’t really see the point of going steady.

So as I stood in front of that mirror, adjusting my jacket and straightening my tie, I wished with all my heart that I could go to school or to a café, to anywhere with girls to woo. It was probably the best I’d ever looked, and it was wasted on this damn family Christmas.

There were girls there, of course, and some of them were pretty cute . . . but they were my cousins. Personally I wouldn’t have had a problem with it; if all we do is fool around naked, it’s all in good fun. But they wouldn’t see it that way; they were uptight. I guess it was no big loss. The only really hot one was Ariana, and she was 17 at the time. Older ladies weren’t quite as incredibly easy for me to seduce.

“Oh James! You look absolutely dashing!”

Okay, maybe some older ladies were pretty easy to seduce. That was Aunt Helen, who definitely wasn’t so bad for a lady her age. Before I start to sound repetitive, I’ll explain that we’re a very attractive family. It started when a handsome economist roped in a stunning model. They had four children, one of whom had me

“Thanks, Aunt Helen. Are people here yet?” My grandparents’ house was so big that a party could be raging just a few rooms over and you’d never hear it.

“Ah, no. Not yet. Most people won’t get here for a few hours. I just came to find you to ask a favor.”

Now this was unexpected. Usually all I did at these reunions was play with the cousins in a kids room while the grownups schmoozed and got liquored up. I guessed I was finally grown up enough to do a little more.

“Name it,” I said, craving responsibility.

“Well, James, you seem to have matured into quite the responsible young man. Sadly . . . my son has not.”

I couldn’t help but smirk. Helen was probably very taken with me because I compared so favorably to her own son. Tyler was my age, but he never once acted like it. See, we cousins all ended up together on holidays and reunions, and back in the beginning Tyler would always play with Daniella, who was two years younger than him (the youngest of all the cousins, actually). Later Daniella grew out of him and started playing with the rest of us. Tyler played alone then.

Sometimes he tried to play with us, play whatever game the rest of us thought up . . . but it never worked out. He was a sore loser, whiny and annoying. And he always lost because he refused to play by the rules. We all scolded him, from little Daniella right up to her sister Ariana, and eventually he’d get the message and run away. Or he’d do something stupid, like hit one of us. Then his mommy would come and spank him, right in front of all of us. Yep, he never seemed to grow out of a good spanking. Last time I saw him get it, naked and screaming, he and I were eleven years old. We always laughed at him while he got it, but that time I didn’t laugh. The others laughed, of course, because it was funny. But I just felt . . . angry. I hated Tyler for making 11-year-old boys look stupid. He was a disgrace, still getting spanked at that age.

And from the way Aunt Helen was talking, it sounded like Tyler hadn’t changed a bit.

“Yeah,” I said. “I remember him having some . . . bad behavior.”

She nodded. “I need to help set up and cook Christmas dinner, so I can’t be watching Tyler to make sure he doesn’t get into trouble. If it’s not too much trouble, I’d like you to keep an eye on him until everyone arrives.”

So now I was Tyler’s babysitter. Not exactly the important duty I’d expected, but at least it was responsibility. It was a dirty job, but someone had to do it.

“Of course, Aunt Helen. Anything I can do to help.”

She led me through the massive house. She, my dad, and their other two siblings were the only people who could navigate the place. They’d grown up here, learned the layout while they were kids. No one else could get around without a guide or a map. Even my grandparents got lost on the way to the kitchen, and they owned the place.

We passed through the big main room, with the towering Christmas tree and the cavernous fireplace and half a dozen couches. That was where everyone would gather on Christmas morning. I hadn’t spent Christmas with the whole family in a couple of years, but I imagined Tyler would be as bratty as ever. He’d rip open his presents and forget to say thank you, then brood while everyone else got their turns.

Down what felt like a mile of wide corridor, past what felt like a hundred ornate wooden doors, we stopped. Aunt Helen put a hand on my shoulder and smiled awkwardly.

“Just so you’re not surprised, James . . . I should tell you that Tyler’s trying out a new look.”

“Like a new haircut?”

“No, not really. Not at all, actually. You know how he is, always acting up. You’ve seen plenty of times how a spanking is the only thing that gets the message across. Well, I got to talking to some friends of mine, and they had some interesting theories on exactly why that was.”

“Why he gets the message from a spanking?” I laughed. “I’m no expert, Aunt Helen, but I used get spanked when I was little. It’s been a while, but I remember it pretty well. I think it gets the point across because it hurts.”

“Well, yes, certainly. But I think there’s more to it, especially for older children like Tyler. It’s embarrassing, James. It humiliates him. It strips him naked, so there’s that. And then he get’s bent over and beaten like a little child.” She looked down, a little sad. “Sometimes I feel bad about it . . . but he deserves it every time. He brings it on himself. And I think it’s that . . . that degradation, more than any pain, that keeps him in line.”

Something clicked in my head. “Wait a minute . . . a new look! You don’t mean he’s . . . naked!”

Aunt Helen chuckled. “No. I considered that, but that would make it awfully difficult for us to go out in public. So I did some research and came up with an even better idea. It keeps him humiliated pretty much all the time, which keeps him out of trouble. But he’s only humiliated if someone sees him, so he can’t be left alone too long.”

Suddenly some 80’s song was playing. For a second I thought the house had an intercom I hadn’t known about, but then Aunt Helen took out her cell phone and the ringtone stopped. She read her text.

“It’s from your mother,” she said. “I’m needed back in the kitchen. Well, you’ve been warned. Just keep an eye on Tyler. It shouldn’t be too challenging. Oh, and don’t just comment on it; treat him as if he really is the way he looks.”

That was when it hit me. With that comment I’d figured it out. I nodded as reassuringly as I could, and Aunt Helen scampered down that endless hallway to help cook dinner. I straightened my tie and adjusted my jacket one last time, just to look as dashing as possible for my new lady friend.

I opened the door and walked in; it was a sitting room with a huge window, letting in plenty of natural light. And Tyler was standing at that window, looking out into the courtyard. I struggled not to laugh.

Tyler had certainly not filled out as I had; he was still skinny, and a few inches shorter than me. And he was dressed as a girl from head to toe: in his hair was a headband, and on his feet were glistening black Mary Janes. In between was a dress--one I’m certain I’d seen on some of the sluttier girls at school dances. It was hot pink, matching the headband, and it was very, very short, not even reaching halfway down his thighs. And . . . and it was tight, designed to show off a girl’s figure. Tyler’s figure was vaguely girlish, tapering at the waist; the dress flared out to make up for his lack of round hips.

I cleared my throat to announce my presence, and Tyler spun around so fast that his dress fluttered up, flashing a hint of red panties underneath. Now that was interesting. He was speechless, eyes wide like a deer in headlights. I began walking toward him to get a better look.

The illusion was actually quite spectacular. Tyler’s hair was long for a boy’s, which was barely even short for a girl’s. And his face and legs (exposed as they were) had no hair to speak of. In fact, with his boyish features and even more boyish body, he looked just like an 11- or 12-year-old girl. And pretty cute, if I do say so myself.

“Hey, Tyler. Long time, no see.” Almost two years, actually.

His eyes got wider as I got closer, and his lower lip was visibly trembling. Up close I could see more details. He had a little heart-shaped gold locket around his neck. His nipples made little points in the dress. His lips were actually the same hot pink as the dress and headband.

I realized I was grinning from ear to ear. Not very dignified, but I couldn’t help it. This was just too priceless, too precious.

“So you’re a girl now.” I put a hand on his bare shoulder. He cringed.

“Uh, well . . . I don’t . . .”

“Aw, you’re all flustered. Don’t worry; lots of girls get that way around me.”

“What?” he said. “No! I’m not . . . it’s just . . .”

I couldn’t help but laugh. “Wow. Boy Tyler never seemed to run out of annoying things to say, but girl Tyler can’t even get whole sentence together. Better not let Ariana catch onto that; it might offend her feminist side.”

His face was approaching the colour of his dress and lips.

As I waited for him to mangle another attempt at responding, I realized that this was more than just funny. I had never in my life felt so confident, mature, masculine, powerful. Here was a guy the same age as me, but without the deep voice, muscles, and body hair. Girls ripped off their dresses for me, and his mom had stuck him in one. I felt very big, very tough.

In fact, one part of me was actually getting bigger and tougher. I guess it made sense: I was alone with a cute girl in a very short dress. Tyler’s mom had specifically said to treat him like a girl, and it seemed my dick had gotten the message.

Suddenly those hot pink lips looked very interesting.

I slid my hand down from Tyler’s shoulder, over an almost nonexistent bicep, a knobby elbow, and a hairless forearm . . . and I took him by the hand. (That was when I noticed his nails—guess what color they were painted.) I interlaced my fingers with his dainty girly ones, and led him over to a sofa. He followed without too much trouble.

We sat down side by side, much closer than male cousins usually did. But Tyler wasn’t my male cousin anymore. He wasn’t even a female cousin. He was just a girl. Maybe a bit of a late bloomer with that flat chest, but a girl nonetheless. I draped my arm around her shoulders, evoking another cringe.

“So you were a bad boy,” I said. “So bad that your mommy made you into a girl.”

She seemed to be holding her breath. I pulled her just a bit closer.

“Are you gonna be a good girl . . . or a bad girl? Or maybe both?”

She looked at me with her big blue eyes. They were wide with fear, and oh so pretty. Tyler had certainly inherited the family attractiveness, but he’d gotten the female brand. He made a childish-looking, mediocre boy, but a waifishly sexy girl. Aunt Helen was trying to punish him, but this was the nicest thing she could have done. It brought out the beauty of his feminine side.

I wondered if Tyler had known about his feminine potential. He always tried so hard at being a proper boy, obsessing over sports and things like that. Maybe he was trying to distract us from the pretty little girl he was meant to be.

“I . . . I . . .” she stammered adorably, “I don’t know . . . both . . . no, good. I’ll be good.”

“Are you sure?” I said, giving her shoulder a squeeze. “I think you can do both.”

She made a pouty little frown. I’d seen that frown, that little pursing of the lips, a thousand times. It was what he did when he wasn’t getting his way. It had always annoyed me . . . but with that lipstick, it aroused a very different feeling.

“No . . . I won’t be bad. Only good. I promise.”

Her childish speech made me chuckle. “Okay, okay. But being a good girl means doing what you’re told. What if I tell you to do something that makes you a bad girl?”

The fear flashed in her eyes again. But I’m pretty sure she had no idea what I was thinking. It wasn’t the fear of a boy bound for a spanking, or of a girl about to get taken advantage of; it was the fear of a keen little first-grader who doesn’t know the answer to the teacher’s question.

“It’s okay,” I said, placing my free hand comfortingly on her bare thigh. Her skin was warm. “You can be bad and good at the same time, and you won’t get in trouble.”

She looked down; her cheeks were flushed. Was she starting to figure me out? Or was she just embarrassed that she couldn’t follow my line of reasoning?

I decided to put things to the test. I slid my hand slowly up her thigh, inching closer and closer to those little red panties. It took her a moment to notice the motion, but I felt her leg and her shoulder tense up when she did.

“James,” she murmured plaintively.

“Shh,” I said. And then, very softly in her ear, “Be a good girl.”

My fingers slid under the pleated fords of the dress . . . and brushed the soft fabric of the panties. She leaned forward, probably some male instinct to protect the balls from harm. I pulled her back.

With a couple of questing fingers, I got a feel for what was under those panties. It was a little big for a clit . . . but small for a dick. And it was a soft little nub, not at all happy to see me. I gave it a little squeeze.

Suddenly Tyler shot right to his feet, and took a nervous step away from the couch. His balls felt pretty small, but I guess they worked for just a second.

I was hard already, but seeing her upright, eyes wide and cheeks red and the dress hugging her skinny little curves . . . I went from hard to rock hard. And I always had a thing for reluctant girls; they line up to date me, but then I ask for a BJ. If they’re down with that, I say we fuck. If they’re down with that, I go for anal. As a rule, I never come until we’re doing something I had to talk her into . . . or pull her into.

I leaned forward and grabbed her skinny wrist. I held her tight.

“Okay, now you’re being a very bad girl.”

She took in a breath. “No . . . I’m . . . I’m not a girl.”

I jerked her wrist toward me, and she fell back into place on the couch. “Yes,” I said firmly, “you are a girl. You’re a very pretty girl. So pretty that . . . even when you’re a bad girl, you’re still better than when you were a boy.”

I released her wrist, which made her relax just a little. Then I slipped my arm behind her back and held her by the waist. It was a comforting gesture, and she looked at me with an emotion I couldn’t quite place.

“But you were still a bad girl, Tyler. You need to be punished.” I slid my hand down from her waist, giving her butt a playful squeeze. “I think a spanking is in order.”

“No!” she said, finding her voice. “Please, no. I’m sorry. I’m really sorry . . . I’ll be good.”

I almost laughed again. This was too perfect. I leaned in and gave her a little peck on the cheek. She winced.

“Like I said, Tyler, you’re very pretty. How would you like to be my girlfriend?”

“Your . . . your girlfriend? No, I can’t. I’m not a girl.”

I gave her butt another squeeze. “Oh, I think you are. If you’re not a girl, then you’re just my dumb cousin, and you need a really hard spanking. But if you’re a nice, delicate girl, I might go easy on you. And if you’re gonna be my pretty little girlfriend, I won’t have to spank you at all.”

Her eyes darted back and forth, like big blue searchlights frantically seeking something. An exit, I guess. But there was no way out.

“Oh . . . okay,” she muttered. “I’ll be your girlfriend.”

I began nodding. “A good, obedient little girlfriend.”

She slowly nodded with me. “Obedient.”

“You’re my girl. You do what I say.”

She continued nodding dumbly.

“Say it,” I said. “You’re my girl. You do what I say.”

She gulped, and I noticed yet another boyish femininity: Tyler’s Adam’s Apple was pretty much undetectable.

“I’m your girl,” she said, barely louder than a whisper. “I do what you say.”

With the hand on her butt, I shoved her forward, right off the couch. She stood awkwardly in front of me. Once again I took a moment to appreciate her. She really reminded me of a twelve-year-old I’d gone out with for a week, the youngest girl I’d ever fucked. But Tyler was prettier. That little upturned nose and those huge blue eyes, and the silky smooth skin and the tight little butt . . . she was downright adorable.

And she was so fucking reluctant . . . she could barely admit she was a girl. That thought got my heart racing like a jackhammer.

“Get down,” I said. “On your knees.”

She did, although kind of slowly. I don’t think she was quite used to those Mary Janes yet.

I gestured to the left, and she inched over until she was right in front of me. I beckoned her to come forward, and I opened my legs wide so she could come right against the couch.

Grinning like an idiot, I kept my eyes on Tyler’s face while I unbuckled my belt and unzipped my pants. I didn’t want to miss the moment when those deep blue eyes saw what was about to happen.

When they did, it was glorious.

I’d have to retuck my shirt later, but that was a small price to pay. I tossed my tie over my shoulder so it wouldn’t get in the way. Then, last but not least, I pulled down the waistband of my boxers, and let the iron rod loose.

Seven and a half inches. That’s my length when fully erect. But judging by Tyler’s reaction, I’d guess his wasn’t half that. Her face was a good foot from my dick, but she looked like I’d slapped her with it.

“Paint it pink,” I said. She looked at me with scared confusion. “Suck on it. Like a popsicle.”

I didn’t need to remind her to be a good girlfriend. She slowly leaned forward, planting a cold, wet kiss on the tip. I shuddered with pleasure, and she took me in as deep as she could. I decided not to force her to deep throat me; that could wait till our relationship was a little bit stronger.

It took her a moment to get into the rhythm, but she got it. She’d been a fourteen-year-old boy recently enough, which meant she’d seen her share of porn. I’m sure Tyler had never received a blowjob, but she’d seen enough on the internet to understand the basics. She was even careful not to let me feel teeth.

She was good for an amateur. It was one of the best blowjobs I’d ever had. And there was this one perfect moment, near the end, when I looked down and she looked up, and there was this dreadful understanding in her face. When our eyes met, I looked deep into her liquid blue peepers, and I could tell what she was thinking:

“Your dick is huge compared to mine, and it’s inside my mouth.”

That little sense of size envy made me remember for a second that this was actually a guy. But to my surprise, that didn’t make it any less sexy. I’m not attracted to guys, of course, but seeing one as pathetic as Tyler, reduced to my cocksucking girlfriend, was overwhelmingly erotic.

I reached forward and ran my fingers through her hair, then gripped her head like a basketball. She tried to lean back, but I held her down. She made a kind of wide-mouthed yelping noise, full of alarm, but she figured out what was coming. And she knew I was stronger than her; she couldn’t struggle.

I shot my load right to the back of her throat; her gagging noises would have made me laugh if my whole body wasn’t bound in the orgasm. I’d been with enough girls to know that I was a prodigious blaster: I shot it out hard and fast, and in gratuitous quantity. I let Tyler withdraw as I filled her mouth with fluid, but I kept the tip in her lips until my prostate had squeezed it all out. Then I let her lean back and swallow it all in one massive gulp.

A lot of girls need to be told to swallow, or at least asked. But Tyler was a good girl. She knew her place.

I had an old-fashioned handkerchief in my suit’s pocket, and I used that to mop the excess saliva off my dick, then to wipe a dollop of my sperm off the corner of Tyler’s mouth. I made sure to fold the handkerchief so that none of the fluids would touch my suit when I pocketed it.

Still panting lightly, I said, “Stand up.”

She was wobbly as she got to her feet, like one of them had fallen asleep while she was on her knees. But she stood before me, pretty as a picture, with her hands behind her back.

Almost as an afterthought, I stuffed my dick, still fairly stiff, back into my boxers, retucked my shirt, zipped my pants and closed my belt. It takes some skill to do all that sitting down, you know.

That done, I leaned forward and lifted the front of my little girlfriend’s dress, exposing the front of those silky red panties. She made a plaintive little yelp, like she was holding in an objection.

“Good girl,” I said, for good measure.

With my other hand I pulled down the front of those panties, exposing Tyler’s pitiful little package. His whole body tensed up with fear, or with the effort of not bolting from the room.

The little bastard still wasn’t happy to see me. It must have been cold in that skimpy little dress, because Tyler’s flaccid pecker had shrunk to about an inch in length, looking very much like the slightly oversized clitoris I’d compared it to. And those little balls were almost invisible in their wrinkly little sack. And, of course, his pubes were so downy and sparse I could barely see them.

“You’re a good girl now, but you were still bad before. I won’t spank you because you did so well just now, but you still need to be punished.”

I stuck three fingers in his scrotum, practically reaching inside his body to get ahold of his little testicles. When I found them I gave them a gentle squeeze. Tyler doubled over, stifling a cry of pain, and I withdrew my hands from his groin. The panties snapped back into place and the pleated hem of the dress fell down to cover them.

I got to my feet. Slowly Tyler straightened up, and looked me in the eye. I gave him a wink, and he turned his gaze noncommittally to the floor. Smiling, I reached over and adjusted his headband, which I’d dislodged when I grabbed his head.

“Tyler,” I said, “I think this’ll be the best Christmas ever.”

The End