I found spots in my underwear, but I didn’t know what they were, until I caught my brother in my clothes.
At first, I thought there was another girl in my room, until I yelled, “Who are you, and what are you doing in here?” Then, he turned around from the mirror, and even in makeup, I could see he was my own brother.
He ran, and I heard the front door, but he turned a high heel on the stairs, so I caught up. He didn’t really know how to walk in high heels, and I don’t know where he got those shoes, but they sure weren’t mine. He borrowed one of my summer dresses, though.
It was too short, so it barely covered up his butt, and he didn’t have any pantie hose, or tights on, so I saw my underpants stretched tight over his balls before he turned around on the landing, and kept going up.
That reminded me of the mysterious spots I’d found in my underwear drawer. Only the clean ones, but he had good taste. If I weren’t so weirded out by the crossdressing, I could have even seen how pretty he was in makeup, and either he’d found someone to do his long hair, or he learned how to do it himself.
Maybe the same girl that let him borrow her pumps, bra, and inserts so he wasn’t so flat-chested, but then I heard the door at the top of the stairs. We had an elevator in our building, and it was working, but it didn’t go all the way to the top. So, he had to take the stairs (in those shoes) to get out on the roof.
Then, I heard the guys he invited over, wolf whistling, and one said “Hey girl.” Another one called him “Baby,” but then the door closed, so I could follow him up, without them seeing.
Then, I thought he might be one of those tranny girls, that start off as boys, but then they get sex changes. That’s expensive though, and dad was already saying how we couldn’t afford for both of us to go to college, so I was bucking for a Scholarship, and working so hard on straight As that I didn’t really have time to worry about boys, and stuff.
I opened the door carefully, and peeked out, but they were busy looking around the corner, and they followed “Her,” so I could sneak out. The door was open to the hoist room, and they were looking inside, before they went in, and let it shut.
“Huh!” I had some idea what they might go in there for, but I had to psyche myself up to try the door, and peek inside. Sure enough, Marty was standing up on this metal bar, right in front of the big spool of cable, and the hole in the roof for the elivator. My brother had his head in his hands, and blocking the view, but I could tell by the angle he was giving Marty a blowjob.
His dad maintained the whole building, so he had keys for the maintanence rooms, and that’s how they all got up there. 2 more guys were lifting the dress, and touching my panties. One of them even got down to feel “Her” legs, which I just now realized he’d shaven.
“Yeah, you’re such a good girl,” Marty let one of “Her” ponytails flip down, and patted “her” head with a sigh. “Huh! Swallow it, swallow it all.” I could even hear him gulping when he stopped to suck him off. All the way, to swallow the wads as fast as they pumped out.
“Snh, huh!” He wiped his mouth, and turned around, but the hands held the dress up, and even rubbed his tummy underneath. “So, who wants to fuck me fir.” He looked back, and forth, while the leg man stood up to feel his butt, and I could see his boner stretching the waistband of my panties! “You followed me?” He looked right at me, and Marty hopped down. The 2 men pulled the dress down, too late to cover his legs.
“Uh, this isn’t what it looks like.”
“Yeah, she’s a girl.” I shook my head.
“It’s okay, that’s my sister, you won’t tell anyone what you saw.” He looked mean, even through the makeup. “RIGHT?” Threatening me.
“Well,” I pretended to think. “Hm.” Tapping my lips. “It’s a pretty big secret, but if I did something, I’m not supposed to do…” I did a report on sexual predators. Not any one in particular, just in general, but I remember reading that’s one of the ways they get girls to keep their dirty secret. They trick them into doing something naughty, so you think you’ll get in trouble, too.
I can’t believe that I touched it! The crusty drops of dried semen, my brother left in my panties. Either leaking before he pulled them down for anal sex, or pulling them up still sticky from residue of having an orgasm, but we had to have a little talk.
Later, after the men (And they were full grown men) asked me, “Like what?”
“You ever got sucked off by a real girl?” I finally stepped up, and let the door close behind me, leaned up against it.
“How old are you?”
“None of your business, but I bet my dad would ground me for life, if he knew I was up here, sucking dick with my big sister.” For the record, I’m older than 10.
“I’ll race you!” I’d never had a boyfriend, I hadn’t even been out on a first date. So far, my sexual experience began and ended with slapping gropers to let go of my bra cups. Middle school boys mostly, though some high school boys had tried to touch me too.
Then, this guy came over, unzipping his pants, and I could already see his erection bulging. He pulled a condom out of his pocket, and tore it open.
“Huh!” I looked over when my brother took my hand, and squeezed it. “You sure you’re ready for this?”
I shook my head, “No, but can you talk me through it?”
“It’s a dick,” my man patted me on the head, “You just put it in your mouth, and suck it.” I nodded, trying to jack it off with my mouth, instead of my hand. I hadn’t given a hand job, or even watched boys jerk off solo in porn, but I heard about it. “She’s a fast learner.”
“Try touching his balls, he likes that.” He was holding my right hand, so I had to feel in his pants left handed.
“Keep sucking,” He bumped my chin with his thumb, and started stroking it helpfully, but that just left one hand on the back of my head.
“Smup!” He pulled me off by the hair, “Ow!” I shook my head.
“Huh!” His eyes rolled up, and he closed them. “Sniff!” His hand slowed down, gripping the whole thing, and then he thrust his hips with a grunt. “UH!”
It was loud, and eccoey in the small, mostly empty concrete shack on the roof. Above the elivator shaft, but I watched mesmerized when he filled the tip with white gushes of nut juice. “Huh!” He relaxed, and let go. It was still hard, but I kept my eyes locked to it, until it finally drooped, and hung, lose enough for him to squeeze it out of the rubber. A good wad still hanging in the bottom.
“Huh!” I looked over at the other guy, who was already naked. Mary was holding my brother, who turned to look down, and smile. It turns out they were boyfriends all along. My brother was gay, but pretty enough for drag, and it was real easy to find men that wanted to fuck trannies, if you didn’t tell them he’s actually a gay drag queen. “You ever fucked a little girl?” I untucked my top, because it was really getting hot in here with all these men, and teenage boys.
“Not without eating her out first.” He had to pull down his mask, he had a nice mustache, and dagger beard to ride, too. It turns out he was the best at oral sex of all! It was so hot, and sexy there that Marty got it up again first, to bend my brother over the braces to hold the hoist, and bang his butt hard.
They brought lots of rubbers, so I went from being a complete virgin to my first BJ, oral sex, losing my virginity, and even double dicking in 1 day!
It took hours, though. The 2 guys didn’t care about fucking a tranny, once I was the center of attention, but his boyfriend took good care of him, while they watched.
👄This will be the best oral sex you have ever experienced.👅