Feminized by My Brother

So at this moment I'm nervous as fuck, with five minutes until noon. I turn up the radio, playing Spiritbox loudly over it to try and psych myself up. When the clock hits 12:00 I'm gonna walk into this apartment, and we'll see what happens. My first time is gonna be me getting sucked off by a stranger, which is a bit weird but fuck, teenage hormones are awful things, dangerous too. I am self-reflective enough to know this. I don't knock the teachers when they preach abstinence or the dangers of premarital sex. I get it, okay? I'm just DUMB for fucks sake.

Now this situation has been enabled because I've turned 18 and can now lead a secret life. I can go places, I can buy things, I have a part-time job and a little money, and I'm HORNY.

I say this so before you judge me you'll know that I know how dumb I am. I just feel like maybe you'll understand though, maybe you were horny once, and by once I mean ALL THE GODDAMN TIME. I can't stand it, and masturbating doesn't help much, sure it's a relief for like, an hour, but then the problem reappears. My body is too old to be fooled by my hand, it knows it's getting a placebo.

I want a girl but, I'm a scrawny wimp, a nervous ninny, and well, a loser. I listen to metalcore but I don't really have the style, I just dress in dark shirts and pants. I haven't even got much in the way of friends. My brother Matthew doesn't have this problem, he isn't a jock but he works out as a hobby and has great looks, hair, and a decent job for a college kid. He's a few years older and already escaped the house to live off campus, what a waste of money! He only did it to have a fuck pad.

For my part, I've been rejected so many times I don't even start a conversation with a girl, even though their cute faces and bouncy tits drive me crazy. Hopefully when I'm in college... or maybe after...

Anyway, I came to this idea, you see gay dudes get tons of sex. They have no problem getting it, they are lining up to suck each other's dicks. Which just makes sense really, I mean they can't get pregnant, men are all down to fuck, of course they get laid anytime they want.

Now I am not gay. Not that I have a problem with the gays! (My dad does, big time) But no homo here. Even so, it has occurred to me (as a scholar) that a gay dude might be willing to suck my dick. I noticed this as I was looking around at dating sites, hoping to find a lady friend. Out of curiosity I clicked on the guys for guys button and saw there are a lot of men looking for 'suck buddies' and some even want to actually just suck on a straight guy.

Bingo.

I could get my dick sucked, with no strings attached. Yes, it would be a guy, but I could just close my eyes, and finally, I'll get some relief that might last a fucking day.

So late Wednesday evening I went to the gay personals. Lots of guys wanted something "now," come on can't these dudes plan ahead? I needed 2 things, a weekend meet-up and for them to host. I couldn't very well have them showing up at my house, I'm 18 here man!

I saw several ads that looked promising and sent messages. Then I waited, desperately, for replies. As the minutes passed, I refreshed my browser again and again. My dick was getting hard thinking about being sucked on, God what's it gonna be like? Nothing came after an hour and in order to not sit there giving myself blue balls I had to take a break, cleaning my room to distract myself, but checking every hour.

Finally, a response! It read, "18yo huh, r u serious I ain't stupid."

What a fucking dick. Even the gays are rejecting me, cause I'm too young??? Is this a thing???

Back to chores for a while and then another response, "I can do you so good," it began, "Can you bring 50 roses?"

Roses? I thought, what kind of... oh. A prostitute, great.

I sighed in frustration because this was not going to be as easy as I thought. I widened my search parameters because I was in fucking need here and I'd clearly have to comb the sands a bit harder. 'Straight guy needs his dick sucked' messages went out across several sites. It wasn't until I woke up the next morning that I saw some promising results. One guy was down but lived an hour away, another said for sure but only with condoms, now I'm dumb as I said and I wanted raw fucking lips on me, not safe sex!

There was a third promising reply, from '123MarioSki,' he lived close, and identified himself as a 'little sissy bottom for hard cocks,' which sounded reasonable enough to me! His sissy nature included him dressing as a girl, which was just a huge bonus for helping me pretend this wasn't as gay as it was (which I guess was 100 percent gay). There was one hiccup, he wanted to suck off two guys at once. He already had the first guy lined up, just needed me to agree to come to his place at noon on Saturday.

Having another guy getting sucked off next to me sounded super awkward, especially since there was no way I was gonna be the more masculine one. I mean I know they'd be gay, but they'd be what the gays call a 'top' and probably a 'bear' or some such. They'd probably get turned on by me and think I was some 'twink.'

Hey, I didn't come up with these gay ass names you gotta talk to the queers if you got a problem with them. At any rate, I agreed, and I think you can understand that this was no homo, right? 0 percent homo, on my part.

I was nervous as fuck though when I pulled into the apartment complex. There's an element of unreality to the situation, as I sit here seeing that it's 11:59. I resolve to put one foot in front of the other, apartment 119B, let's-a go Mario.

I'm glad there's no one in my immediate vicinity to see me, I feel like I'm doing something criminal as I hurry to find the right door, knocking so softly I realize they might not hear me, but the door opens.

I'm face to face with a guy in his mid-20s, who has done his damnedest, short of surgical intervention, to look feminine. He hasn't quite succeeded, since I recognize him as a guy immediately, but I think to myself, I can work with this. His full blond wig, his bright make-up, his dress which is surprisingly not slutty but includes what I assume is a stuffed bra... I'll have my eyes half closed; it'll work.

He speaks and his voice is great, "Good afternoon, I'm Brenda, why don't you come in?" Brenda sounds feminine as fuck but who chooses to be called Brenda?

"Ethan," I say, adding, "Your voice sounds really sexy." I figure I should drop some kind of compliment for the person who is about to be sucking my dick.

"Awww, thanks sweetie," he says. "Our third should be here in a few minutes." Brenda is immediately very handy, I guess that's how you break the awkwardness in this situation. He's touching my arms and chest, taking my hands and putting them on his sides.

This is a lot for me, and Brenda can tell, "No need to be nervous straight boy, I'm gonna take good care of you." I nod, clearly nervous. "God you're so sweet I could eat you up, umm I'm gonna suck you so hard," Brenda says, his hands rubbing me through my pants. I feel my legs shivering a bit.

Brenda feels it too, smiling at me. "Is this... your first time with someone like me?"

"It's, ah my, first time... ever," I confess.

Brenda smiles, REAL big, and says, "Ohhh lordy." He licks his lips, "You sure you're straight?"

"Uhhh, yeah," I say.

"Well, we will see if you can say that after I'm done with you." Brenda is loving this, but this fucking crossdresser is suddenly intimidating the fuck out of me. He leads me to the couch and sits me down, kneeling between my legs, which shake even harder.

Brenda pushes his face into my pants, inhaling, "Ahh, maybe we should start without-"

A knock sounds from the door, Brenda giggles, standing up.

I wait on the couch as the third guy enters, I'm curious what he'll- holy fuck.

"Huh, how did you...?" I stammer over my words, standing up. I assume, immediately, that he has found me out and followed me.

"Well, well, well," my brother says, eyeing me up and down. "You here trying to steal my sissy, bro?"

We both eye each other, thinking, realizing, that this is pure coincidence. We just happened to have the same idea, getting sucked by a queer, sure, it makes sense to me and it made sense to my brother. No big deal except-

I stand up, "I guess I'll beat it and let you ah, have this one to yourself." I say, part of me relieved now that I wasn't going through with it.

"What? Why?" my brother replies. "I mean this isn't a threesome, Brenda can suck us both, no problem. This is great man, we can have a lot of fun together."

"I don't know..." I say, bewildered.

"Not like together man, but think. You can use my pad too, if I'd known my little brother needed a place to get his dick wet I'd have invited you already. Brenda has a lot of love to give don't you baby?"

Brenda laughs at this, "That's right Master, two brothers? Of course, I'm down!" Then he leans in and kisses Matthew, full on the lips. My brother returns the kiss, not only without hesitation, but passionately, grabbing the back of Brenda's head and pulling his hair, it's no wig I realize.

I'm shocked, my whole world is spinning. I was already dealing with the nerves of getting my first bj (from a dude in drag) now my brother's here and he is full-on gay! HE IS THE BEAR!

Now he's stripping, acting like this is no big deal, which I guess to him, it isn't. He causally tells me how he told 'my sissy' to find a third to fulfill Brenda's fantasy of sucking off two guys. Matthew has been fucking this sissy dude for months and other guys since he went to college! Even though he is literally coming out to me, it's done without any fanfare, after all, he now thinks I'm into this scene.

My brother tosses his boxers aside and I see it, my brother's cock. I'd seen him naked when we were little, but A LOT has changed. "Holy fuck," I whisper.

"Whip it out, Ethan," he tells me, as I look him up and down. Not that hairy, so maybe not a bear, but definitely muscular, a toned, fit young man.

"Okay..." I say meekly, and Brenda comes over, helping me remove my clothes. I tremble a bit as my tightie whities, are revealed, Matt laughs.

"Bro you can't wear God damn briefs out to get your dick sucked," Matt laughs. "But Brenda can't really judge." He finds this whole thing hilarious, but he's right that Brenda isn't judging, instead staring lustfully at me.

"I love your soft body..." Brenda says, running his hand over my nearly hairless chest. I didn't really want all this touching from him but, fuck it, if that turned him on to suck my dick go ahead.

Matt has moved next to me, we're all in front of the couch. "Stand or sit bro?" he asks me nonchalantly. I'm eyeing his cock, which is hardening as he watches his sissy play with me. His cock is ridiculous, and now I realize when my dick, which is perfectly fine but just ah, low end of normal, comes out he is certainly going to compare us, but, so far he hasn't been hostile so maybe it won't be too bad.

"Let's sit," I say. Standing is making me feel more exposed, so I sit on the couch next to him. Our legs are uncomfortably close, but I can deal with this. "Start on Matt first," I suggest, procrastinating.

"Yeah, give old familiar a kiss you little slut," my brother agrees. Brenda isn't hiding his excitement, a stupid huge grin on his face as he contemplates sucking two brothers off. I stare at his red lips as they part to begin tonguing my brother's cock. Brenda's excitement doesn't make him rush, this is a delicacy for him, and he savors my brother's erect dick like the last icicle pop on a desert planet. My eyes are fixed on my brother's cock, I've seen a couple of other guys naked in the gym before, but never like this, and never... well to be honest a cock that's this magnificent.

My brother lays back, completely relaxed, and lets Brenda go at it. I'm not forgotten though, as the horny minx reaches over and starts rubbing my dick through my briefs. My brother is completely motionless and quiet, as though meditating, so I feel less nervous about openly staring at the action in front of me.

Brenda is in heaven as he slurps up and down my brother's staff, murmuring things like, 'Oh Master your cock is so tasty...." but the one thing I can tell he wants now is my dick out, as his fingers try to get under my briefs. I raise my ass so he can pull them down, my 4 inches popping out. Painted nails wrap around me, pumping slowly up and down.

I moan as I'm touched for the first time, still nervous but fully on board.

Matt opens his eyes to glance down when he hears this, and we look at each other for a moment, Brenda working on both of us. He gives this little smile as he looks at my dick, and then lays his head back, taking a deep breath.

I try to just pretend he isn't there and close my eyes. A few moments later I feel Brenda switch sides, his breath on my nuts.

It's a girl. I think to myself. Imagine a girl.

Her hands are pretty strong as she rubs my legs, spreading them a bit. Her breath is hot, her tongue touching my balls gently, stroking each one.

"Fuuuck," I moan, it's incredible.

She sucks my left nut into her mouth, gross slurping noises filling the room. She's unrepentant and whorish. Pushing her face into my crouch with abandon. I know the spit is dripping off her chin, her makeup smearing all over my testicles. Her fingers play with my shaft, and the feeling is intense, God it's too intense, she starts to lick her way up my member, just like she did to my brother's cock, his hard, throbbing cock...oh fuck!

I cum, squealing like a little girl throwing a tantrum, as my cum shoots onto my stomach, she reacts quickly, swallowing my head to drink the other spurts, gulping down the rest of them. As I lay there panting, she licks my stomach, cleaning up every drop.

I open my eyes and watch Brenda licking drops of semen off his hands, smiling at me. I almost want to apologize, for causing his fantasy to be so short-lived, but he isn't complaining, just moving back to suck on my brother's cock again. As my brother puts his right hand on the back of her head he says, "What was that bro?"

I'm embarrassed but, fuck him. "It's my first bj," I say by way of explanation.

"Well fuck," he replies. "That's not a get outta jail free card, you owe my sissy a bj."

"Nope," I said, eyeing Brenda's lips bobbing on his beautiful shaft. "I think I'll head out..."

"You'll what?" my brother says, anger in his voice.

"Yeah, I'm done so I'm gonna just go now," I start to stand up, but he grabs my arms.

"Hold up, you don't do that to my girl."

"Do what?" I said, concerned. He was much bigger than me.

"Pop your rocks off like a schoolgirl and leave her that's what. She was supposed to suck your dick and you blew it, you gotta make up for it." All the time Brenda is just gurgling on his cock, gagging and choking as he forces it down his own throat. I start to imagine myself doing the same, what would that be like? I couldn't say that I've never thought about it but I've never seriously thought about it. Brenda looks like they love it.

I sit there watching, inaction allowing me to delay further conflict with my brother. I wonder, what does Brenda normally do to get off? I can see both his hands, they are focused on my brother's pleasure.

"You suck her now, it'll be easy," Matt says. "She's all rev'd up. Think, you're gonna wanna do this again right? Cause we could do it, same time next week, but not if you leave her hanging."

Fuuuck he has a point. God damn son of a bitch it isn't gonna be easy to find a sissy like Brenda again... maybe just this once. Maybe I can cheat and use my hand a lot, keeping it out of my mouth.

Brenda lifts his dress, exposing his ass which is bare, with nothing under the gown. I gulp and crawl under him on my back. Brenda's dick is a lot like mine, maybe 5 inches though. I reach up, chest tight, and start to rub it. Brenda coos in joy at the feel of my hand on his dick, and I wrap my fingers around it. I feel uneasy seeing another dick this close, but I also realize my brother can't see me, and I don't think Brenda is going to complain if I only use my hand, so I start stroking, spitting on my hand some to expedite the process.

There's something about a hand job that is quite erotic. Rather than think about myself jerking off some weird stranger, I decide to pretend I'm watching a girl's hand give a hand job. This quiets my discomfort, and I jerk Brenda, much to his delight, while I listen to the wet noises he makes going down on my brother. Because that was not my hand stroking him I make a show of it, massaging the dick and enjoying how the skin moves along the shaft, the angry purple head bulging as Brenda's gasp becomes louder.

I realize too late that, while I have avoided the sucky sucky, I am in the blast zone for the cumshot. Brenda's ass shudders above me as the ropes of sticky opalescent cum rain down onto my face, my surprised mouth caught open, with a few drops landing on my tongue before I can react. I taste it, oh God I taste his cum. It is the slimiest, most pervasive flavor. There's the salty, immediate sting, alongside a touch of sweetness and tang at the same time. It spreads around inside my mouth so that there's nothing to really spit out, it's a greasiness that coats my tongue and lips.

I stand up, mortified as my brother sees my cum coated face. "Nice!" he shouts, at me, or at his orgasm, which came at that moment, I don't know. I just watch in shame as I wait for Brenda to finish drinking his load so I can ask to use the bathroom.

* * *

Over the last week, I marveled at how the world went on. I had met a stranger off the internet for sex, yet my parents knew nothing. The chink in this charade was the fact that my brother had been there, but as he did not live at home, it wasn't so bad. I was worried about what he might say though. Matthew has escaped my father's roof, but I still need it. This aspect of my strategy to get a blowjob had honestly not occurred to me until after the fact when the threat of its discovery became real.

But even though I now feared this threat, other hurdles had been overcome. I knew the plan worked, I had the cock sucker lined up, the time and place set. I choose not to masturbate on Thursday and Friday, to be more ready to enjoy Brenda's services.

I was surprised this morning to have a text from my brother; "My place today."

I knew immediately what it meant. So now I'm walking into my brother's pad, which I guess is more comfortable than a stranger's apartment, although I haven't really been here much. Walking in I see all the trappings of what I figure are common college student artifacts, ramen noodle boxes, cardboard and plastic boxes used as furniture, walls without any décor... a drab place. I prefer Brenda's apartment actually.

My brother leads me to his bedroom and it occurs to me...

"Other people live here, right?"

"Yah," he confirms.

"Don't they see you, ahh, with Brenda?"

"And know I like fairies? Yeah, so what? They don't know you or the family."

This makes me slightly nervous as we wait for Brenda.

"So when did you meet this guy?" I ask.

"I met this girl at a frat party, she snuck in looking for cock and I gave it to her."

I thought about this for a second, saying, "Dude really likes to suck dick huh? How long have you known you're, ah..."

"God, you're such a bitch," Matthew said. "We aren't at Dad's house anymore. I've been gay forever man. Anyway, stop calling Brenda a guy she doesn't like it, and you better not mess up the shit I got going with her because in case you didn't notice she fucking sucks cock like a pro, takes it in the ass like one too."