Sissy and His Sister

By secondsamuel.

“EWWW! Can you believe he’s doing that in front of you?”

“So what? He does it all the time. Look at it! You can tell how excited he is to have someone watch.”

“That’s sick. I mean, he’s your brother.”

“It’s not like I want to do anything more,” Jenna said, almost sneering as she spoke. “I mean, have you ever seen anyone that small?”

“Maybe he’s a grower, not a shower?” Stacy asked.

My sister gave a loud laugh at this, her whole body shaking as the noise cut straight through me. Not that it stopped me from gripping my fingers tightly around the small bulge in her pink panties.

“He’s already all the way hard,” Jenna answered.

“How do you know?” Rebecca said.

“It’s not the first time, or even the second, is it, Taylor?”

I nodded in agreement, my eyes barely able to meet the three college girls who stood watching as I stroked myself. I could feel the shame and beet red embarrassment flushed over my face as my sister went on to explain our peculiar situation.

“I first caught him when I came home from school for spring break,” Jenna said. “I had noticed some of my things had gone missing over the years, mostly underwear, but I didn’t think anything of it until I saw him in my room, wearing my bra and panties, looking every bit like the sissy faggot. He was so humiliated that first time. He started to cry and beg for me not to tell mom and dad.”

She gave an exasperated sigh as if to tell her friends that nothing could be done about having such a pervert for a brother.

“So I let him off the hook. I even told him he could keep the pair, but I would be able to use him as a slave whenever I wanted.”

“A slave?” Rebecca said. “Isn’t that a little like junior high?”

Jenna only shrugged her shoulders at this.

“It comes in handy a lot of times. For example, I haven’t needed to write a paper this semester, and it will be even easier once we start college in the fall cause we will have a designated driver. He’s not really a slave, though, and he gets all of my hand-me-downs so he can parade himself around like a girl.”

“You know,” Rebecca said whimsically. “He almost has the build for it.”

“What the fuck, Rebecca!” Jenna said.

“No, seriously,” Rebecca continued, “I know he is your brother and everything, but he would be kind of cute as a girl. He could grow out that blonde hair a little bit, and he’s already got that kind of feminine look to him. His features are really soft. All he really needs are breasts.”

Jenna ignored this, but my cock strained against the fabric of her tight silk panties at this lurid description of what I might be. Even given my small dimensions in that area, I barely fit in the undergarment, even when fully flaccid. I should have been embarrassed, even ashamed at my own arousal. I should have run out of the room screaming. But there was nothing more attractive, more essentially erotic to me, than being discussed in such a dismissive and emasculating fashion.

None of these girls wanted to do a thing with my tiny little dick. Neither did they consider my perversions as threatening or anything other than off-putting. In the same way, someone might consider a dog humping the furniture as little more than distasteful. Had I been a real man, I might have wanted to show them my cock, to display it proud and ready in front of them, aching with the desire to be played with and satisfied. But somehow, each of them knew I didn’t have that in me.

I had never shown anyone my cock. Ever. I had been too embarrassed. Once my sister had seen a part of it during one of these sessions, and she had burst out laughing. Something about that made the taboo even more alluring. My only form of sexual expression (other than masturbating to internet porn) involved taking every chance to sneak into my sister’s room and her clothing.

“It still must be weird though right? I mean he is your brother and everything, does he ever try anything?”

“Never!” Jenna continued. “All he does is play with himself through the panties. He doesn’t even masturbate, right. Most guys grip it,” she made the pantomime with her hands, a terribly vulgar gesture that exaggerated male self-love.

“He just rubbed it around. I didn’t even notice at first. Not until I saw the wet spot in the middle of my panties and that dumb look on his face after he had finished. Like I wanted my underwear back after that. Can you imagine? Wondering if I was feeling my brother’s semen against my pussy as I walked around!”

“You need to burn them,” Stacy said.

“I just needed rules for the little sissy faggot,” Jenna continued nonplussed. “Not that he always follows them, but I have pictures I can share if I need to, all sorts of fun little poses. You know he takes it up the ass like a little bitch? I caught him in the shower one time, with the handle of a hairbrush up his ass, moaning like he was being fucked by a real man.”

I could see all of them only casually watching me, barely making eye contact as if they were ashamed for me. I should’ve felt embarrassed. But, instead, I did in a way that was supplanted entirely by the lustful desire to be shamefully put on display in front of a group of women. The underwear, I imagine, was only part of the allure. And I could picture myself, in a bra and panties, so that when I stood, my nearly hairless body was covered like a woman’s.

I was only conscious of my own sexual satisfaction. But that the girls in front of me were indifferent to my pleasure only made it more profound. Most men wanted to take a girl, to force their attention on him, but I wanted to be ignored. To be treated as though I was nothing more than a slight inconvenience.

The thought of actually showing a woman my penis, which was barely more than 4 inches, seemed more frightening and scary than being caught in such a compromising position over and over again, even if it came at the expense of my sister. Other than my perversions, Jenna and I had a completely normal brother and sister relationship, her teasing me a little bit but never letting out my deepest darkest secret, at least until now. The idea of anyone other than her seeing me this way had horrified me in the past, almost to the point of eroticizing the experience.

That my sister would prop me up as a spectacle, she would point to my penis, barely concealed in that little garment, and laugh with her friends at me as I rubbed at it. This had always been an object of secret sexual imagining. Something that I had only managed to meekly murmur to Jenna when she drew it out of me the last time she caught me masturbating. She had been the only one I dared trust with my secret, and even then, not consciously. Catching me originally had been a mistake, a result of bad timing, largely due to her being home for a weekend during Spring break and me desperately needing to squeeze out one last orgasm in her clothes before she left again for Texas A&M.

I’ve seen videos showing exactly what I was now forced to live out in front of these college girls. My nipples were covered in the pink bra, the clasp fitting neatly behind my back, though the cups were hardly the same size as my sister. She was little more than an A cup, and on the beach or at the pool, she barely filled out the bikini. Like me, Jenna was blonde, though she dyed it to almost platinum color. Conventionally, she was gorgeous, the kind of girl that always looked as though she would belong on a runway, attributes that did not transfer so easily to the opposite gender.

Like me, she was slender, petite, almost to the point of fragility. Her friend Stacy I had known since high school, blonde as well, with the accompanying bosom that most men preferred. Stacy had the traditional hourglass figure that most women possessed, though she had always been covetous of Jenna’s frame. For her part, Jenna had always been more jealous of her breasts. Or at least that’s what I overheard as I desperately tried to be a part of my sister’s world in school, always clinging on, hanging behind, and trying to fit into the group.

Rebecca was new, seemingly much older and more mature than the other two girls, but maybe she was just taller. She wore her brunette hair in a plain ponytail and seemed somewhat fascinated by the entire scenario. While Rebecca looked on in rapt attention as I played with my penis, making dismissive and derogatory comments here and there, Stacy pulled out her phone and seemed to distract herself as I let out a gentle moan.

I moved my fingers around the head of my cock, almost tickling it against the fabric, which always felt so good against my skin. I moved faster and faster, my breathing increasing, my body tensing as I neared the point of no return. As the panties rubbed moved up and down on my cock, my legs crossed almost involuntarily into a feminine pose, my toes curling with expectation. That I was debasing myself, that I was giving up every bit of my masculinity, every bit of my manhood in exchange for this one orgasm that I would never live down only barely registered in my mind. I was obsessed, almost outside of myself, even possessed by a singular focus, an unspeakable need making me into their sexual object.

Unspeakable surely summed up what I was experiencing. Other than the cursory comments made by my sister, I had offered no sort of explanation for my behavior. Once the three accidentally stumbled into Jenna’s room, I had let my sister explain, standing meekly in the center of the room, letting the girls avoid my eyes and treat me like the pervert I knew I was, the shameless sexual slut desperate to please, especially as a punishment. I was barely a person as I neared my orgasm, just a thing, just a base animal relieving his most basic needs like an untrained pet.

And then it happened, something that had never even entered my imagination before. As I moved my cock up and down inside the fabric, the head of my penis popped out of the panties. I shoved myself back inside the garment, truly embarrassed, just not enough to stop.

“Oh my God!” Stacy said.

“Jesus! I can’t believe I saw that,” my sister said, turning her back to me.

“It’s so fucking small!” Stacy squealed.

“I dunno, it’s cute,” Rebecca said.

“It’s fucking pathetic, and I mean, what girl would want that inside of her?”

“Would you even feel it?” Rebecca snickered.

“Oh haha, because you’re such a prude,” Stacy said.

“Is he done yet?” My sister said, turning around and peeking through her fingers in a fabricated shock.

And then, with a small cry, I spent myself in front of them. I looked away from the girls, noticing that no one but Rebecca watched as I finished. My panties dampened as I filled them with my seed, spent as any sissy’s needed to be, only for the enjoyment and amusement of others only, and not because of my own selfish satisfaction at the stupid things that turned me on. I could feel myself spurt, my head pushing back at the sensitivity as the semen couldn’t quite exit my urethra with the fabric pressing down against it. My sensitive head spasmed against the panties, and I squirmed in front of them, clearly showing my reaction.

“He’s done,” Stacy said dismissively, looking back at her phone. “It’s all over his face and his underwear.”

“Okay, Tay-Tay,” she knew I hated the demeaning nickname. “Real girls are done with you. Go clean up.”

The End.


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