My Sissy Older Brother
Taboo/incest Story

My Sissy Older Brother

by Roastnox 6 min read 3.8 (8,800 views)
long hair sissy
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Hello, my name's Kiera. I'm a 19 year old woman with a single mother and a 21 year old older brother, Jim. I'm the favorite child, and he's been very jealous of me for years, though we're very close.

To tell you where it all began, Mom and Dad got divorced when me and Jim were just toddlers. She's hated men ever since the divorce occurred, and only wanted custody over me. However, Dad did not want Jim, so he had to stay with us.

Mom wanted Jim to be a female for years, but gender reassignment is not legal in our area. So her plan was to raise Jim to be feminine and look feminine. Mom would control how Jim turned out by homeschooling him, while I went to public school all my life. The only friends that Jim has ever had is me and my friends, who are all women. And yes, I hate men as well, probably since Mom taught me to, and eventually I grew up to help mom take care of Jim.

We do not allow Jim to have short hair or any facial hairs. To give you a description, both me and mom have very long light-colored brunette hair that is straight, thick, and beyond waist length. This is also the case for Jim, since we've forced him to have that type of hair. We'd brush his hair, force hair care products on him to keep his hair thick and healthy, and made sure his skin is soft and feminine. This has a bonus effect of helping him stay submissive. When people say that me and Jim look alike, they don't mean our similar faces, but also our nearly identical hairstyles.

While Jim doesn't mind that, since he's used to it from growing up, he never liked my mother's preferential treatment toward me and that she likes to spoils me when possible. So while Mom doesn't have much money to support both me and Jim, the ratio of how much presents she would give me to Jim, for example, is that he would receive two inexpensive presents while I've received the more expensive presents. I would always get like the video game devices, and Jim often BEGS me to share my presents with him. It's annoying but I love it, since it helps us have control over Jim. Sometimes I'd receive two of the same gift from mom as another way to help keep Jim submissive.

Sometimes Mom would do things at Jim's misfortune even if he's not misbehaving. For example, one time I asked Mom if I could turn Jim's bedroom into my own television room, and she immediately allowed it without any hesitation or second though. Jim was very upset and lost his temper over that, for sure, but we allow him to use my new television room as a bedroom if he misbehaves, else he'll have to sleep on the floor in the hallways, the bathroom, or some other place of inconvenience. Again, just another way to help him stay submissive. To be honest, I've felt bad for Jim all my life, and sometimes I get the feeling that I love him more than Mom does.

Speaking of which, even though I hate men, I'm heterosexual, since I get horny of getting laid by a man. There was too much tension for me since I'm not allowed to have a boyfriend and too much tension for Jim since he's not allowed to have a girlfriend. A year ago, at age 18, I asked mom if I could be in an incestuous relationship with Jim, and she allowed it.

After Mom allowed it, I went into my television room, where Jim was lying on the couch. I began trickling my fingers through his long hair, admiring how straight and nicely combed it was, and rubbed my face against it. "Mmmmm... so soft...." I said. "You have literally the best hair out of anyone I know, and your gray eyes are so glittering and pretty."

"I feel the same about yours," Jim replied to me. "Both of us have beautiful long hair covering our entire back."

"Please never cut your hair or get rid of your feminine appearance," I said. "You're literally so beautiful and the only male in this world whom I love and care about. The rest can all go to hell!"

"I have no plans to," Jim replied. "Mom would force me to be homeless if that happened, and I've been like this for as long as I can remember."

I had Jim flip back his long hair so my entire body could feel the softness of his hair. I did the same to Jim, and he began to become erect. Without asking, I pulled down Jim's pants and began to lick his penis. It was my first time having sex with a male, and it was great. he didn't have any pubes either.

"Wait, I didn't--"

"Mmmmm, love the cock." I interrupted Jim. "I don't need your permission. You've grown up into becoming my submissive sissy man and I will do with you as I please."

I grabbed Jim's shoulder and leaned against him. I leaned against Jim, feeling safe and protected that a taller young man was wrapping his arm around me and leaning his head against my face. He has no facial hair, just soft, feminine skin to accompany his soft long hair. I felt the best parts of a female and apparently also a man at the same time. Perhaps if men looked convincingly like women, I may reconsider my opinion towards them.

"Wait, put on a leather jacket, I want to see how it feels while you hug me with a leather jacket on while I sit on your erect sissy cock," I asked Jim.

"Aren't you going to get naked as well?" Jim said.

"Mmmm, maybe later, hehehe," I replied. "I just wanted to get a feel for sissy cock."

Jim sat down wearing only a t-shirt and leather jacket, as I had ordered him to. His dick was rock hard. Jim clearly wanted me to be naked with him, but I only made him hornier by refusing. I began stroking his cock until he blew his load on my face. I froze in shock briefly before licking in all the cum surrounding my mouth.

"Looks like I'll have to go wash up," I said.

I slept with Jim that night, wanting to feel the comfort of a man in bed with me. I refused to be naked, though I forced Jim to sleep without bottoms on.

"From now on, I want my sissy brother to have his cock exposed while at home all the time. You're a sissy, and your dick is the only immediate indicator of that. You look so hot while your dick is exposed." I said.

Jim didn't respond but didn't argue against it. He's so used to being submissive to me and Mom that he usually stays quiet.

I put my hand on Jim's penis and felt it harden as I said, "Perhaps I can show off your sissy dick to my friends and we'll take turns sucking on it."

Throughout the year, Jim became an official sex servant of mine and having a dick to show for it. We practiced missionary, anal, doggy, and all other types of sex. I once invited seven friends over and showed off Jim to them as some of us played with his hair while also having sex with him. I urged my friends to try out that experience with a sissy. As you'd expect, lots of cum went flying during that session.

Now in the present day, like I've said, I'm 19 and Jim is 21. I'm preparing to move out, with help from Mom. She wasn't prepared to help Jim move out, presumably as a plan to kick him out of the house soon, but I decided I'd take Jim under my wing and let him move out with me, under the condition that he stays a sissy.

"To be continued..?"

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