But I quickly snapped out of my unwanted justifying. I only did it the first time because I was drunk and stupid. Now I was sober. Now I had to remain sensible.
She reached back and grabbed my hand. I became stiff, stopping her from pulling my hand over her petite, warm body. “I got all dressed up for you,” she said.
“I told you: I’m not gay,” I said, hardly even whispering.
“Let me ask you a question then: is it gay to let a girl suck your dick?”
“Of course not,” I said, my heart now pounding in my throat, trying to silence me. I wanted to clear my throat but I was worried the slightest cough would be enough to alert my sleeping family.
“Good,” she said, spinning back around. She looked into my eyes and smiled, and then she disappeared under my covers.
“What are you doing?” I asked. She had her face down near my crotch before I could process what was happening. I felt her fingers toying at the waistband of my pyjama pants. I tried to squirm to stop her. I had the urge to kick my legs and throw my knees, but I didn’t want to hurt her. Had she not been dolled up, I probably would have kneed her carelessly. But with her lingerie and her heels and her perfume and her makeup—I couldn’t possibly kick a girl in the face!
She managed to wrestle my cock free. I felt her fingers touch my bare flesh. I gasped. She giggled at my gasp. And then I felt her wet, warm tongue touching my tip. I became frozen, worried any more struggle would be enough noise to wake everyone up. At least with her under the covers, if anyone came in, I could pretend to be asleep. The extra lump under the sheets could easily pass as a pillow. But I still had a big problem: I still had my stepbrother under the covers, sucking my cock.
CHAPTER VI
I kept my gaze glued to the doorway. I wished he would have closed the door on his way in, though the closed door might have been even more suspicious, seeing as I rarely slept with my bedroom door fully closed. I kept looking down, trying to decide if Nathan’s body did indeed look like it could be a pillow or a the blanket all bunched up, or if it looked like my cross-dressing step-brother sucking my cock.
But my anxieties started fluttering away once Nathan plunged my cock through his lips, sliding the underside of my shaft along his tongue. He sucked and slurped quietly while his hands explored my thighs, my ass, and my ball sack. I had to admit that it felt nice. His lips felt genuinely feminine—not that I knew what genuinely feminine lips actually felt like, seeing as I’d never even kissed a girl before.
I reached down with both hands and found her head. I slipped my fingers into her hair and then I massaged gently, pushing her head down so more of my cock would push into her throat. I made her gag at one point, so I released her, worried her gagging would wake up the house. But she got better as the minutes passed, sinking deeper on her own, allowing my cock to push down her throat without much trouble. Occasionally she would slip the whole cock out from her mouth so she could tickle my tip with the tip of her tongue while she massaged my balls. It felt nice—as long as I kept her female image in my mind. As soon as the memory of her male face crept into my head, the euphoria would fade.
But it was hard to picture a man as those soft lips explored the length of my shaft. And it was very hard to picture a man when she let those soft, cute whimpers out. I was rock hard in her mouth. I reached down again and pushed her head firmly into my crotch, making my whole shaft push down into her throat. This time she took the whole thing without gagging. She coughed a bit, but managed to remain quiet.
Then I succumbed to another urge: the urge to pull her up and kiss her lips. She didn’t resist. She let me pull her up to my eye-level and then she let me stick my tongue into her mouth. I could taste my own cock on her lips, but I didn’t mind. I liked the way she sucked my bottom lip and pulled it back playfully with her teeth. And I even kind of liked the feeling of her warm, hard shaft grinding against mine—though I didn’t even notice it until a couple of minutes had passed and she started moaning.
I couldn’t see with the covers over us, but I could feel her foreskin pulling back so her bulbous tip could rub against mine. And then I could feel as her foreskin pulled back over her tip so it could happen all over again. I didn’t stop, but a chill did run down my spine. It was an unwanted reminder that I was making out with my stepbrother. I just wanted to imagine that I was with a woman for once in my life. Was that so wrong?
Nathan’s body trembled and she let out a loud groan. I covered her lips with my hand, and then I felt a warm spray against my abdomen. Then I felt another spray, and then another. She was coming and each blast was coating my torso. I lifted the covers to look, just as the last shot was spewing out from her throbbing dick. My skin was covered in long strands of shiny white jizz. She took her cock and spread the cum around on my abdomen. She laughed while she did it. And the sight was strangely arousing. I wasn’t able to hold back. I ended up coming, but I was on my back, so I ended up coming on myself. Nathan didn’t waste a moment. She started rubbing my cum in with hers, all over my chest and abdomen. It felt nice, until my sensibilities returned to me and I realized the reality of what was happening.
“I need to get cleaned up. You need to get changed before anyone sees you,” I said, jumping back and slipping out of bed. I needed to take a shower—a long, long shower. I didn’t want any of her cum on me. I didn’t want any reminders that I’d now fucked my stepbrother twice: once drunk and once bone-sober.
Nathan giggled as she pranced off to her bedroom. My heart didn’t stop pounding through my whole shower, and it didn’t stop pounding once I was in bed, trying to fall asleep. As I stared up at the ceiling, I tried to convince myself that it had all been a dream, but I could still smell that incredible perfume on my bed sheets. Had it not been so late I would have ran them through the wash. But I was stuck with them for the night—so I got no sleep.
In the morning, Nathan was in the kitchen. He was dressed as his normal male self. He looked at me and nodded his head. “Good morning,” he said as I stood frozen in the doorway. He had a coffee in his hand. “Coffee?” He was acting as if nothing had happened, as if he had no memory of our sober romp together. He looked at me strangely with that tilted gaze, as if I was the one who was acting off.
“Uh, sure,” I said. I watched as he poured me a coffee. My hands were trembling slightly but he was as cool as ever.
“You just take it black, right?” he asked.
I nodded my head as I accepted the mug of steaming coffee. He looked into my eyes but I couldn’t look back into his, so I looked down at my coffee. “Thanks,” I said. I wondered if he was bi-polar, or if he had split personality disorder. How was he acting so cool about the whole thing? Why didn’t he look even a little bit uncomfortable about the fact I could tell his minister father that his son liked to dress up like a girl and suck men’s cocks?
I sipped the coffee. It was good, and it was needed seeing as I’d only gotten a couple hours of sleep. “Thanks,” I said again
“It was my pleasure,” he said with a slight grin that only lasted a second. But it was enough to send my heart into another pounding frenzy.
CHAPTER VII
It happened again a few nights later. It was a Wednesday night and everyone was getting a good night’s sleep before another workday—everyone except for Nathan and me.
She slipped into my room around midnight, wearing my sister’s old cheerleader uniform, from when she was in the eighth grade. It was green and white, and she was even wearing the pom-poms around her wrists. She was already giggling when she came into the room.
I tried resisting for a few minutes, but I knew that there was no point. I knew that Nathan was determined to get exactly what she came for. Plus it was hard to resist after she pressed her lips against mine, and teased the tip of her tongue into my mouth. It didn’t seem worth resisting seeing as I’d already indulged twice. What else did I have to lose?
She kept the outfit on while we fucked. The skirt did a good job of hiding
her cock, even once she was erect. I lay on my back and she straddled me cowgirl-style. She bounced up and down, getting slightly more than half of my cock into her body with each little hop. Her skirt danced from side to side and her pom-poms rustled constantly—but this time the bedroom door was closed, so I was less worried about waking up the house.
I tried pulling her hips down so I could get more of myself inside of her, but she stopped me. “Ouch. Not to deep,” she said. I didn’t want to hurt her, so I didn’t push it. Her tight butthole massaging half of my cock felt good enough. I ended up bursting a nut inside of her body. She got up and sat down on my chest, letting my creampie flow out. It was warm and wet, but strangely I didn’t mind. She tossed up her skirt, revealing her erection, and then she beat it with her tip pointed at my face. “Open wide,” she said quietly.
I’m not sure why, but I followed the command. I opened my mouth and ended up tasting her cum. Only two blasts actually got into my mouth. The rest ended up on my cheek, nose, and chin. After she pranced away back to her room, I looked down and saw the mess she’d left on my chest: my own cum recycled through her bum, in a small pool right on my sternum. I took another late night shower before heading off to bed. And this night, I actually slept deeply and peacefully.
On Sunday, Nathan’s dad made the whole family come to church. There was some big fundraiser after the service, and apparently it was important for all of us to be there. So we all got dressed up and went to church together.
Nathan got dressed up funny, as if he didn’t take it seriously at all (because he didn’t). His pants were puffy as if he was wearing pantaloons, and his dress shirt was far too tight. But Nathan’s dad was too busy preparing for the service to fix his son’s appearance.
The service was boring, and the fundraiser was shaping up to be boring too. There was one heart-stopping moment when Nathan’s dad got up to make a small speech as everyone was crowing around a table covered in free baked goods. “I just want to address a new issue in this town that’s come to my attention,” he said. “Supposedly there are many male students in our schools who believe that they are females. I’ve had a number of parents coming up to me to ask if this is normal or okay in the eyes of God, and I just want to say now, to everyone, that there is nothing normal or okay with acting as the opposite gender. I’ll remind everyone here: A woman shall not wear a man’s garment, nor shall a man put on a woman’s cloak, for whoever does these things is an abomination to the Lord your God. Deuteronomy 22:5.”
My hands became cold and started trembling. My heart skipped a beat before beginning to pound without a discernable rhythm. And then I overheard a couple behind me talking about a rumour that had been going around. Apparently, one of the regular churchgoer’s sons had recently come out as transgender. I felt relief knowing that Nathan’s father wasn’t talking about Nathan and me.
I looked over at Nathan. He was grinning, as if it was all a big joke to him. He came up to me a few minutes later. “Having fun?” he asked.
I shrugged my shoulders. “It’s not exactly how I wanted to spend my Sunday.”
“This is how I’ve spent every Sunday since I can remember,” he said. He laughed. “Maybe that’s why I’m so keen on rebelling. Maybe that’s why I keep putting on a woman’s cloak.” I let a small laugh slip before looking around to ensure that no one had overheard his risky joke. “You want to see something cool?”
“Sure.”
I followed him away from the fundraiser, into the back of the church and then up a narrow flight of stairs. “No one really knows about this. No one’s been up here in years.” The stairs led to a single, small room with a small window looking down at the altar. There were multiple old piano keyboards stacked on top of one another. “It’s the old pipe organ,” he said. “It doesn’t work anymore. They have a digital one down at the altar now. See?” He started mashing keys, but there was no noise. “They left all the pipes in because they thought it looked better.”
“Yeah, I guess that’s neat. Is that what you wanted to show me?” I asked.
“No,” he said. And then he reached down and undid his belt. I became tense, looking out the window at the altar. There was no one on the altar, but I could hear the nearby fundraiser, not even thirty feet away. “What are you doing?” I whispered.
“Just relax,” he said, suddenly using his girly voice, which he could apparently turn on at a moment’s notice. He slipped down his pants, revealing a long, bunched up skirt. He gave the skirt a shake—but it was still badly creased and wrinkled from being stuffed under his pants. I guess that’s why his pants looked like pantaloons. He reached down and unbuttoned the bottom few buttons of his dress shirt. Then he tied it up around his sternum, showing off his flat abdomen. He then pulled the hair elastic out from his bun, letting his hair fall down over his face. Finally, he kicked off his dress shoes, revealing his bare feet and red-painted toenails.
“How do I look?” she asked.
Shockingly, she looked good, even without makeup. Or maybe I was just getting used to the way she looked. Her body was surprisingly curvy and her long, smooth legs did most of the work in completing the illusion. A bit of makeup would have been nice, but even without it, with her hair framing her face, she looked like a girl.
“How long have you been doing this?” I asked, keeping my voice as low as possible. I looked back out that small window at that little altar.
“Doing what?” she asked.
“Dressing up.”
“Well,” she said, looking up at the ceiling of the small room. “I only started after I moved in, but I’d always thought about dressing up before. I would sometimes put on my mom’s clothes, but she had the worst taste. It wasn’t until I had access to your sister’s room that I really started—and even then, I was only able to dress up when I was home alone. But I’m starting to get a bit more comfortable now. Your family seems to sleep pretty heavily, so I’ve been able to get dolled up at night—as you know.”
I looked at her again and wondered if her legs had always been that smooth, or if I’d ever seen her bare feet before. Did she always keep them painted? Is that why her hair had always been so long?
“So are you going to fuck this naughty church girl or are you just going to stand there staring?” she said, turning around and placing her hands down on a small ledge. Her skirt was long and conservative, but the fabric was soft and light, easy to lift up and throw over her back.
“You’re sure no one ever comes up here?” I asked.
“Not that I know of. But you’d better be quick, just to be safe.”
I pulled aside the white lacy thong that covered her asshole and then I spread her soft cheeks and watched as that tight hole puckered and begged for my cock. I did one last look around before pulling out my cock and moistening it with saliva. I pressed the tip up to her hole. She let out a euphoric whimper before I even penetrated her tush. She swayed her bum slightly.
I took a deep breath and I pushed my cock into her body. She managed to stay relaxed as I sunk my rod in, just past halfway, a little further than the last time we’d fucked. She was getting better at taking it, far more confident, but she still said, “Not too deep,” before letting out a long, elated groan. I started pumping her ass. I had both of my hands on her hips until she grabbed one of my hands and brought it around to her crotch. She pressed my fingers against her cock and I figured out quickly what she wanted: a reach around.
I hesitated at first, wondering if it was a line I wanted to cross. But that line had already been crossed. We’d already fucked multiple times. We’d already mashed our cocks together until orgasm, so was it really that weird to give her a wank? I curled my fingers around her girth and I started jerking her off while pumping her tush with my own cock.
She looked cute in that long church dress, especially with it flipped up onto her back, exposing her rosy butt cheeks. She stood up on her red-painted toes to make up for her short height. Usually her heels would have done the
trick, but we didn’t have that luxury up in the church’s organ room.
I sunk my cock in a little bit deeper and she didn’t protest. I looked down and saw that there was only about two inches of left of my cock that wasn’t inside of her—not even enough for her to reach back and jerk off. The inside of her body felt night and warm and tight. I watched as her tight hole suctioned to my girth as I pulled back, and then I watched as her rim disappeared along with my rod, into her body as I pushed in.
“Cup my tip,” she said with a sharp breath.
“What?” I said, whispering.
“Cup the tip of my dick with your other hand. Quick.” So with my left hand I reached around and cupped my palm in front of her rod. Not even two seconds later, the palm of my hand was filling with her warm cum. I guess she didn’t want to spray the church wall with her sin juice. I ended up wiping it off on her skirt, seeing as she would be putting her pants back on to hide it.
She clenched her bum, making her tight hole even tighter, but I kept pumping. She was still groaning as if her orgasm hadn’t stopped, and maybe it hadn’t. She moaned, “Don’t stop. Right there. Don’t move. That’s the spot. Oh God, right there!” I used my cum-stained left hand to muffle her mouth as a group of kids ran out onto the altar. A parent chased them, shooing them away from the holy spot. Thankfully no one looked through that small window to see the beautiful blonde’s reddened face as I pumped her from behind, because the pleasure was too great to stop.
I didn’t take much longer. A few more pumps and I was filling her tight hole. After I pulled out, she quickly reset her panties to catch the warm load that was rushing out. “That was fun,” she said with a big smile. And a second later she had her dress shirt buttoned properly and her pants back over her legs. As she reached up to tie her hair into a man bun, a chill crept down my spine. I’d just fucked a man in a skirt and red-painted toenails. He wasn’t wearing makeup and he didn’t have his hair curled and styled. He wasn’t even really wearing girl’s clothes, aside from that skirt. His top was just his usual church top, tied up like a cowgirl at a nightclub.
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