Listen, I know you're not going to believe me. I'm going to say it anyway: my childhood was normal.
Trust me, there are days when I don't believe it myself anymore.
I'm laying on my queen-sized bed, exhausted, wearing nothing but panties. My cock is limp inside of them, because today, like every day for the past three years, a gallon of cum and pre-cum has been milked out through it. Strangely, my ass isn't sore, even though it really ought to be. I think my hole has been trained. It's a weird thing to write. It's a weird thing to think about.
I'm not gay. I'm not even bi, I don't think. I'm not trans, or a femboy or a sissy. I'm just a college-aged guy, living at home to save money, who's being milked and fucked nearly to death every day by his mother and her new 'special friend.'
I guess when it comes to being a femboy or a sissy, what's important right now is that Mom hasn't decided that I'm either of those things. Her house, her rules. If she decides I'm one or the other, then either I find another living situation, or I go along for yet another wild ride.
You're not going to get any arguments from me; all of this is insane.
My mom's 'special friend' is named Kara. They met a year after Dad died - at a yoga class, of course. She's fifteen years younger than Mom, and ten older than me. She's hotter than the fucking sun. If you ask her, she'll tell you she's a lesbian. If you're caught in a position like mine, you won't even have to ask. She'll insist.
The lesbian doth protest too much, methinks. I mean, come on: she's milking me and fucking me practically every day. I'm not some three-hundred pound gorilla, but I'm a man. I also take decent care of myself; Mom and Kara make sure of it.
My bedroom door slowly opens, and Kara walks in. She's barely visible against a distant kitchen light, but even her silhouette is sexy. It's also a little scary.
She's nearly six feet tall, and she's not just another suburban yoga mom. Her body telegraphs strength and flexibility even when it's completely still. Plenty of women get their ten thousand steps in these days. Kara looks like she does it casually, in a half hour, before a protein shake breakfast. Dear god, does it give her an ass. I'm sure all the fucking she does helps too.
Tonight, like every night that she comes to visit me in my room, her B-cup breasts are contained by a sports bra. Trust me; I'm a guy, and I can tell even in the near-darkness. You might as well ask me how I can tell she's wearing a strapon dildo.
I can't make out her hair color yet, but I know it's still the same dye-job dirty blonde from this afternoon. It's already up in a pony tail. It's business time, after all. Likewise, I can't tell exactly what kind of panties she's wearing under the harness. She's pretty predictable, though. It's either full-support boy shorts or boxer briefs. It's not like she needs a control top, or any help for her ass. She just wants to be butch.
I don't tell her that she completely fails at it because she's just so deliciously feminine. I'm a little more diplomatic than that, especially prior to an ass fucking.
Kara reaches over and slowly twists the dimmer switch on my lamp. She's weirdly considerate about so many things. I blink a few times, then get a better view. It's incredible, even when sexy becomes scary, right there at the waist. The big can of lube in her hand finishes telling the story of what's about to happen to me again.
The sports bra and boy shorts are matching black, just like the harness and the strapon. It's a striking contrast to her lightly tanned skin. Kara's face is classically pretty. Her hazel eyes are kind -- sympathetic, even. Her dark eyebrows give them an extra edge, though, well-sculpted though they may be. I bet she could do 'crazy eyes' really well if she wanted to. I guess I'm lucky she doesn't want to.
"Hey, Gil," she says. Her voice is another failed attempt to butch up. She sounds like a tomboy, and a feminine one at that. I never had a strong opinion on tomboys growing up, but Kara's been making quite the sales pitch.
And yeah, my name's Gil. My sister's name is Rose. Educated parents. My given name is Gilchrist, not Guildenstern. I don't know if that's better or worse. Rose got off easy. She's just Rose.
"Kara," I reply curtly.
She smiles. Just like her eyes, it's sympathetic -- wistful, even.
She gets on the bed and gives my leg a friendly pat. Her strapon bounces a little, just an inch away from the bulge in my panties.
"I'll try to be quick," she says.
She puts down the lube and hand towels, and then begins inspecting my body. She lifts my legs and my arms. She traces along my chest and stomach. She acts like a trainer, or a physical therapist. These first touches would be plausibly deniable, but for the glaringly obvious.
"Any soreness?" she asks. "Is the workout regimen getting too easy?"
"My asshole and rectum are just as sore as they always are," I lie. "The other workouts are fine, though."
She ignores my complaint. She pats my leg again.
"Panties down," she commands.
I stare daggers, but I comply. Kara has Mom's permission to spank me if I don't. I lift my legs and slide the panties down. Kara finishes the job, leaving them around one ankle. I drop my legs and let Kara execute Mom's standing orders.
This is when I can take a little bit of power back. I know it sounds ridiculous, but you'll understand soon.
Kara inspects my cock and balls. She tries to be clinical. I try to force her to stop bullshitting. I sigh and moan. I spread my legs.
"That feels really good, Kara," I tell her. "Keep going. Use some of that lube. Give me a hand job, at least."
My cock gets harder, but it's not a full erection. I'm too sexually exhausted. It's enough to keep Kara moving along, though. She can't get caught appreciating my junk.
Every session, I scan her face for a sign that she really is bullshitting me -- and herself. I feel like I see it sometimes. Maybe it's just because I want to see it.
"Well, I think we can get through the usual questions quickly, in any case," she says. "I still have to ask."
She stops 'inspecting' me. She grabs a spare pillow, and gives me the look. I give her a dirty one back, but I lift my hips. The pillow goes under. My asshole is further exposed.
Kara snaps the can of lube open and coats her fingers. She starts massaging my hole. I make a show of wincing. She doesn't take the bait, but she's slow and gentle.
"You're not gay or bisexual, right, Gil?" she asks. "You're looking for a girlfriend, not a boyfriend."
I roll my eyes.
"Take off all that gear and let me prove it, Kara," I say, "and don't give me that shit about my cock. You milk a gallon out of me every day. Tomorrow morning. Let's make it a date."
She chuckles and shakes her head.
"Okay, okay, fine, Gil," she says. "You've got a point. I really should be asking you that question when you're full up. Talk to your Mom. Convince her."
I scoff. It's the same dodge, every night. There's no convincing my Mom of anything anymore. She's a goddamn sex maniac. She's obsessed with all of her rules, and she barely tries to hide the fact that this whole sexual circus under her roof is about turning her on and getting her off.
The first finger glides in. I grunt and wince again. Kara keeps going. It's just bullshitter versus bullshitter now, down to the wire.
Kara sighs.
"You know Gil, I like you," she says. "You're a good kid. If you tell me you're not a femboy or a sissy, I'll take your word. Then you can just admit that you like getting fucked in the ass. Girlfriends peg their boyfriends. Wives peg their husbands. Some of those bottoms are femboys and sissies, sure. Some of them are in the closet. Not all of them are, though. Some of them just love it in the ass. It's a brave new world."
She adds a finger. She finds my spot. Kara's not just hot; she's skilled.
I stare her down again. It's more difficult now, because my eyelids want to flutter. My mouth wants to go slack. Even though my prostate is either swollen to the size of a grapefruit, or drained to the size of a pea, Kara's attention feels good. Even my overworked asshole is starting to warm up. Maybe I should ask a pre-med on campus what kind of shape my prostate is in after these sessions. I'll figure out a way to pose it as a hypothetical.
Kara's not totally wrong about me. I like it in the ass. I like P-spot action. I like pretty much everything, except dudes and pretending to be a chick. It's not an unreasonable line.
"Cops are allowed to lie to suspects during interrogations," I retort.
I'm not pre-med, but I am pre-law.
Kara chuckles again.
"Yeah, Gil, that's why I like you," she says. "You're funny. You're clever. You're not wrong that we're at an impasse. Your Mom's in charge. I'm just following the house rules.
"So, here we go," she continues. "Are you a femboy, Gil? Are you a sissy? Do you want to really fem up, wear the cage, wear the plug, get some titties? You know, if you go all the way, your Mom would definitely let you be my third girlfriend. I'd probably be really attracted to you then. I'd probably get something out of these sessions. Wouldn't you like that?"
"I think you already do get something, Kara," I answer. "And no, I'm not a femboy or a sissy."
Kara shrugs. She acts like she's not invested.
"So, you interested in anybody yet?" she asks -- and. just like that, she sounds like she actually cares.
I really want to lie to her, but I can't. Mom will insist I bring the girl home almost immediately, or give her an update on how and why I got shot down. With how obsessive she is about literally anything having to do with sex, I can imagine her playing Sherlock fucking Holmes and rooting out the lie. Seriously, she'd go on campus. She'd do the "hello, fellow kids" routine. She'd also probably eat thirty-seven pussies in a row on the way back to the parking lot.
There's no power play here. I decide on another tack instead. Is it honesty? Well... it's not an outright lie. Let's leave it at that.
"It's just so hard," I answer, without really answering. "Girls who are passionate about their classes seem like they've got no time for a relationship. They aren't even thinking about that. It's not like I have time to go to a lot of parties, either."
"You're not really a party guy, Gil," Kara says. She's not making fun of me. She just gets me.
She's also stretching my ass out for a fucking while we have this sweet little Mom-mandated heart-to-heart, so, you know. Keep it in perspective.
"Yeah," I agree, "but you know, you gotta make some sacrifices to meet people. Not everybody goes to parties because they're obsessed with partying. I might meet somebody."
"Maybe," Kara concedes. "It's worth talking to your Mom about. She'd be even further up your ass about drugs and alcohol, though, for sure."
I give her a look. She tilts her head, recognizing the irony -- and the pun, I guess. It's Kara's fingers right now, but sometimes it's Mom's.
