Go Home with Him

You text Jeff as soon as you can to let him know you won't be coming straight home. You text Megan next and ask her for a ride.

After school, you find yourself in a position that's becoming far too familiar for you - begging the popular girl for something humiliating.

"Please? I just need to borrow some makeup and a pair of panties!"

Megan crosses her arms in distaste. "Ew, I do not want your sissy germs in my panties. Especially when I literally just helped you pick out like a ton of new lingerie at the mall. You're a big boy, why don't you just wear what you have on now?"

You shrink as she scowls down at you. You've already explained the situation to her a few times, but you get the feeling that she likes watching you grovel. "I just... I feel weird not wearing them now, and Lucas knows I wear panties so if I don't..."

"So what?" She cuts you off. "Are you planning on showing him your underwear? I didn't know you were such a slut, Aiken."

You blush. "It's not like that! Come on, Megan, I'll do anything! Just one pair and I'll wash them before I give them back. Please!"

She pauses and pretends to think about it. "Hmm... anything, you say? Anything at all, just for a pair of my underwear? You know you aren't the first boy to beg me for that, right? You might be the first sissy though."

You gulp. She never goes easy on you. Calling you a sissy so casually - it always makes you shiver and feel that much less masculine. In a way, its almost comforting on that day. Almost normal, or whatever normal has become for you.

"Yes, anything! Anything at all!"

She sighs and relents, putting on a show like it's a huge effort on her part. "Fine. I guess I'll do you this favor this time. But don't think I'll forget the deal. You will do anything I say from now on, and you'll thank me for it too, got it sissy boy?"

"Yes, yes thank you, Megan! Thank you so much!" you whimper pathetically as she goes to her panty drawer and fishes out a purple and pink striped thong to dangle in front of you.

She smirks. "Good sissy! Now go put your panties on and come back. Don't bother putting anything else on - we're gonna have some fun together while I do your makeup."

You feel a pit form in your stomach. Fun for Megan usually meant humiliation for you.

You look into Megan's phone camera as she rotates it around you, snickering at the faces you're making. You're wearing just the skimpy thong she gave you and nothing else. She's tied your hair into two high pigtails and made your face up into a smoky sultry look with bright red lipstick.

She slaps your ass hard.

You wince and suck air in sharply through your nose and say "Thank you Miss Megan!" to her infinite amusement.

"Good boy!" she laughs condescendingly. "Or wait - are you even a boy?" she furrows her brow in mock contemplation - a drama for the sake of the camera.

You know your lines - though saying them makes your skin prickle and face go totally red. "N-no Miss Megan, I'm a sissy. Please spank me harder."

She obliges and slaps your other cheek with enough **** for the sound to echo around the room and leave a hot sting that lingers for several minutes. She snorts with laughter while you **** a smile as instructed.

"Good gurl, Aiken!" she offers the humiliating praise before turning the camera off and tucking the phone into her back pocket. "I'll be saving that to the cloud with all the rest of my Aiken sissy pics as soon as I can. I hope you remember how much material I have on you before you think about breaking our deal. Anything I say, right sissy gurl?"

"Yes, Miss Aiken..." you shake and flush and avoid eye contact, staring at the floor instead.

She giggles, "Hehe, that's what I like to hear. Enjoy the panties, slut."

You try to empty Megan from your mind for a while, and instead focus on the fun day you have ahead of you. It's easier once you're dressed again and out of the lion's den that is Megan's room.

Hanging out with Lucas at his house! You couldn't wait for it. You needed his easy, calming demeanor now more than ever.

You knock on his front door after Megan drops you off, and wait. You let your hair down and tousle it out. You wish you'd brought a brush or comb with you, but you make due with your fingers.

His mom answers the door.

"Aw! You must be Aiken! Aren't you cute! Lucas talks about you all the time, I've just been so excited to meet you. Come on in!"

You smile. She's as kind as her son, and has that gentle, nurturing quality that makes you feel right at home no matter where you are. You can feel her touch in every aspect of the home as you step inside. From the smell of warm cookies, to the cozy blankets and plush pillows on the couch, to the walls that are plastered in family pictures from floor to ceiling. You can't help but appreciate how much work it must have taken to craft such a comfortable space.

"Mom!" Lucas calls from the top of a small staircase. "I told you I'd get the door!"

He comes down and shoos his giggling mom away with a blush. "Sorry about her... Um, my room's upstairs. Wanna come up?"

A few minutes later you're standing in Lucas' room, looking around at all his stuff. Old rock band posters hang from the wall. Medals and trophies from past years cover every inch of the dresser. A bed with a plaid comforter looks like its been very hastily made. You can see piles of dirty laundry peeking out from under the bed and closet door. He must have kicked them under to try and give the appearance of a tidy room before you arrived.

"Nice room!" you smile, sitting on the edge of the bed.

"Yeah? You like it?" he asks, sitting on the opposite side. "I uh, figured we could do some gaming like last time. Maybe some CoD or Forza or something if you're up for it."

He hands you an Xbox controller that looks pretty new. You wonder how many other people have been in his room and how many have played games with him.

"Sounds fun! I won't go easy on you though just cause it's your house though," you say playfully.

He smiles and laughs. "I wouldn't want it any other way!"

A few minutes later, you're racing through the streets of Mexico in Forza 5. You start off strong, taking an early lead, but slowly fall behind. You swear you keep glimpsing Lucas looking at you out of the corner of your eye, but each time you turn to meet his gaze, he's staring at the screen, gaming as intently as you are.

"Hey, um..." he says at one point, "It's okay if I call you 'dude,' right? 'Cause if not, I don't mind. I just call everyone that. You know, girls and guys."

You glance over at him, but he's still glued to the screen. You think you catch his eyes flicker your way for just a second though.

"Sure, why would I care?" You shrug.

You both go silent for a while after that. You're worried it might even be a little awkward with just the sounds of digital engines racing through virtual tracks. But he finally breaks the silence.

"Your makeup looks really good today. I kind of missed it at school... Not that you don't look cute without it, too."

You careen off a cliff and crash spectacularly in the game.

"R-really?" You have no idea how to respond. You fall to last place as your car respawns. Lucas is way ahead in first.

"Yeah. Um... Hey, this might be weird to ask, but you crossdress sometimes after school, right? Like, wear girly clothes and stuff?"

You gulp and stumble through your words, face on fire with embarrassment. "Wh- who told you that- I... I mean maybe I've um... might have worn something like that, I guess, yeah..."

Damn Megan must have said something to all her girl friends. Like wearing panties wasn't bad enough, you were sure she must have told everyone that you crossdressed too.

You catch Lucas smiling a little as his car crosses the finish line with plenty of time to spare before second place even gets close.

"Cool. I was just thinking it would be cool to see you like that sometime. You know, if you were okay with it."

"Uh... well..." You could barely think, much less form a coherent sentence. A timer on screen forces the race to end before you even make it to the finish line, cementing your last-place finish. "S-sure... yeah, why not," you manage to stutter out in the end.

"Cool," he says again. "Only if you're comfortable with it though." His grin has an unsubtle tilt of excitement.

You brush your hair back behind your ear as he sits down right next to you and looks into your eyes.

"Now, what's my prize for coming in first place?" He leans his head towards you and brushes a hand over your thigh.

You feel like your heart is going to beat out of your chest as you gulp and meet his gaze. Should you lean in too? Was he inviting you closer? Why was his hand on your thigh making you feel so... giddy?

There's a knock on the door. "Lucas, honey? Do you and your friend want a snack? I have cookies and sandwiches. Dinner's still hot if you're hungrier," his mom calls from the other side.

Lucas yanks his hand from your thigh and sits back on the bed in a flash before she opens the door all the way. "Y-yeah, just playing a game!" he laughs, even though his response didn't really fit her question.

"Okay, well... I'll just leave this here if you want anything. Make sure Aiken's parents are okay with him staying over this late."

She leaves a tray of cookies and crusts-cut-off sandwiches on a cluttered desk beside the door and closes it on her way out.

Lucas lets out a long sigh after he hears his mom's footsteps descend the stairs.

"Sorry about that. Next time I'll lock the door," he says apologetically.

You nod and smile, trying to be casual. "No worries! Your mom is awesome."

Next time. He said there would be a next time...

Your panties are wet by the time you get home that night.