tagIncest/TabooA Strange Request...

A Strange Request...


"We need to talk. I know what you did last night."

I sent this text off to my twin sister; you see, sis has been married for a few years now and her husband is a total pussy. I've witnessed my sister walk all over him in front of family, friends, and even in public; I know for a fact that she doesn't respect him and I know something she thought no one would ever find out.

Last night, I was having dinner at a local restaurant just around the block from my house; it's quite a nice place, especially for a date. It's dimly lit, candles on the tables, very romantic and has a nice selection of wine. I guess my Sis was also a fan of this spot because she was also there last night.. But she wasn't with her husband.

Instead, rather she was there with a friend of her husbands; his name was Marcus. I'd hung out with the guy in a group setting on a few occasions but I personally didn't know much about him. But I do know he's a six foot five, two hundred and forty pound physical specimen; the guy is in tip top shape and he's as black as the night.. Which if stereotypes have taught me anything means he's got a huge black cock.

Sis was clearly blasted on wine as she was all over Marcus before they could even get to his car; his tongue was down her throat and she already had one hand on his semi-erect cock which I could perfectly make out the outline of through his slacks. He slapped her on the ass before grabbing an entire handful of her ass and resting his hand in the crease of her ass crack as he escorted her into the car. I, of course saw that as an opportunity..

With my phone in hand I snapped photos and videos left and right documenting everything I was seeing; I even followed them back to Marcus' place to really get some good stuff on film and boy did I ever. Marcus beat the ever loving shit out of my Sister, choking, slapping, spitting, jamming his cock as far down her throat as she could take it and making her gag all over it. Clearly something that was missing from her marriage as her husband lacked the instinct of being a complete alpha male.

Sis was down on her knees with both hands behind her back and Marcus' 10 inch cock lodged between her teeth; her jaw stretched wide and tears began to stream down her face as he body jerked every time she gagged on his cock. She maintained eye contact and kept his cock in her mouth so long as he pleased. I was shocked with what came next..

Marcus laid my sister down and proceeded to slowly and sensually fill her tight white cunt with his long black rod; he pushed himself all the way inside of her making her take all ten inches of his cock.. But that was that. He didn't fuck her hard or fast, no; this was different. Marcus made love to my sister. Unbelievably so; I certainly have never made a woman moan the way he made moan and I've definitely never had a woman shake and convulse the way my sister did on his cock as he made her cum.

They never switched positions once; Marcus made complete love to my sister in missionary position before filling her up with his black semen. Luckily I was right there in the window filming the entire thing.

That's where this story takes a turn; you've been warned. You're probably thinking this is the part where I'm going to blackmail my sister into having sex with me; you're wrong.

Remember how I said my sister's husband was a pussy? Well, he was more than just a pussy; in fact he was mostly a sissy. Aside from his feminine personality, his body was completely feminine. I'd shared a locker room with him many times and I couldn't keep my eyes off of his smooth body; the way his ass was wider than his hips and bounced with each step he took. His cock although it was always soft, was only a few inches; if I had to guess I'd say he was only putting up 4 or 5 inches rock hard. No wonder Karen was never satisfied with him.

I met with Karen that afternoon to discuss the terms; I sent her one of the pictures I'd taken the night before and hinted at what our little meeting was going to be about.

"I have pictures and videos of you with Marcus last night, Karen." I told her. "This is what I want from you."

I could tell by the look on her face she was thinking exactly what you were all thinking.

"Look if this is some weird black mail you're trying to do to get me to sleep with you.." Karen said, jumping to conclusions.

She and I have always been very close, open, and honest with the other especially about out sex lives; we share a sort of mental bond as most twins do. I'd be lying if I said there wasn't some kind of underlying sexual tension between the two of us and maybe there was.. But that's not what I'm interested in,

"You're sick, Karen. I don't want to fuck you." I told her.

"Then what do you want?" She asked.

"I want to fuck Tom." I answered.

She was silent; at a loss for words.

"Umm.. Excuse me? What?" She was struggling to understand.

I explained to her how I'd noticed his body at the gym and how he's a total bitch; I explained how I've recently started getting into the fetish of tranny's, cross dressers, sissy's, and femboi's. How I wanted nothing more than to fuck a little sissy bitch in the ass and make him completely submit to me and my cock; use him for my own pleasure, as if he was a sex toy built to make me cum.

"How? How do you think I'm going to make that happen? Tom will never do that." She told me.

"I know Tom has always wanted to fuck you in the ass, right?" I asked.

"Yeah, you know I've told you that. I never let him." She replied.

"Exactly." I began, "Exactly. That's how you do it."

"I don't get it." Karen responded.

That's when I broke down my master plan.

"This is what we're gonna do.." I started to explain, "But it's going to take some time."

I explained to her she was going to tease Tom; absolutely drive him insane. Dress like a complete slut in the bedroom, fancy lingerie, rubbing her ass against his cock in bed, etc. Even sucking his cock every now and again but not letting him cum; really get him sex crazed.

"Then one night, I want you to tell him 'I want you to fuck my ass.' Got it?" I asked.

"Got it.. But then what?" Karen asked.

I told her that she was to tease him even further after offering her ass; I wanted Tom to come home to Karen on the bed on her hands and knees like a dog, ass spread wide with a glass plug in her ass. Tom was to come over and remove the plug and put his tongue in her ass; he wasn't allowed to fuck her just yet.. Only with his tongue.

"I really don't see where you're going with this." Karen interrupted.

"Now we're getting to the good part." I told her, "Just when Tom can't handle the teasing anymore, you tell him he can fuck your ass ONLY if you can fuck his ass." I explained.

I went further into detail telling her that she needed to buy a strap-on to fully convince Tom she wanted to fuck him in the ass; next I told her we were going to buy him some nice lingerie and a wig that he would be forced to wear.

"You're going to have to make him into your little sissy bitch in the bedroom, before I can come in." I told her. "Once you've completely feminized him, then you're going to tell him you want to do some sensory deprivation."

"What's that?" Karen asked.

"Sensory deprivation will be where he's blind folded as well as has headphones in his ears to block out sounds." I explained.

"And that's when you're going to come in and fuck my husband?" She asked.


"But what about when he wants to fuck ME in the ass?" She asked.

"We'll worry about that later, for now you've got work to do." I told her.

Weeks went by and Karen would frequently give me little updates on her progress; it only took about two months to fully brain wash Tom into being the little sissy faggot we all knew he was. It was about time for me to finally get what I'd been waiting ever so patiently for.

I purchased the sexiest lingerie I could find online and gave it to Karen; tonight was the night and she was going to present the total package to Tom.

"Come over. Tom is getting out of the shower now." Karen texted me.

Tom was fully prepped for anal and on his way to being fully done up in make up for my own personal pleasure, no matter how sick and demented it was.

"Come upstairs." Karen instructed.

I found my way to their room; it was dark and dimly lit by candle light much like the ambiance of the restaurant where I'd caught Karen with Marcus. Tom was kneeling on the edge of the bed, blind folded awaiting further instruction.. And God damn did he looked good dressed as a woman.

I approached him slowly and with every step my cock grew harder and harder; I placed my hands around his throat and put my ear up next to his. I could hear the loud vibration coming from his headphones; I snapped my fingers a few times to make sure he really couldn't hear anything and I assume he couldn't because he didn't react at all.

I shoved him down onto the bed and turned him around on his hands and knees on the edge of the bed doggy style, just as I had instructed Karen to wait for him all those days she spent teasing him.

Tom had on a red and black school girl skirt; a solid black lace thong and lace stocking to match. He had on a small bra with some gel inserts to appear as breasts and a tiny white t-shirt tied in a knot to accentuate his "cleavage."

I flipped the tiny skirt just over his round bubble ass so it rested on his lower back; I couldn't believe my face was only inches away from this beautiful ass I had watched in secret so many times at the gym. From this point on I will be referring to Tom as a woman. Besides, she looked far too good to be a man now.

I spanked her ass as hard as I could and she moaned; her ass bounced and rippled like a ricochet effect as I slapped it harder and harder each time. It started to get red and hot; I grabbed it with both hands and spread it wide to get a nice look at everything. I massaged it, rubbing it round and round almost as if I was kneading dough. The anticipation was killing me, I needed to taste this ass.

I pulled the thong to the side and to my surprise there was a pink glass butt plug sticking out; I could feel the precum begin to leak out of my cock. This was the same plug Karen had been wearing for weeks now and it was in her husbands ass. God, we were sick. I gently pulled the plug from her ass and opened her mouth wide before placing it in her mouth.

It was at this point I saw Karen sitting in the corner watching my every move; I had forgotten she was in the room. I hadn't even realized she was touching her pussy; I didn't even care if I'm being honest. All I wanted was the ass that was right in front of my face and I was about to have it.

I spread her ass wide once more and allowed her tiny little hole to gape from where the plug was stretching her out, preparing her for my thick cock. I stuck my tongue out as far as I could and inched it as far as I could insider of her; I could hear her moan and her body began to quiver as I penetrated her asshole over and over with my tongue.

Once she was nice and wet, I decided it was time for me to fuck her; I positioned the tip of my cock at the opening of her hole as I spread her ass wide as before. I pushed forward carefully and as I did her asshole opened right up and swallowed my cock; I felt it try and jam shut when I was about half way in and it wrapped tightly around my cock. I froze and so did she; I could hear her take a few deep breaths to relax herself as I slid the rest of my cock all the way inside her.

It took a few strokes for her to really let go and give her body to me but once she did, I was relentless with each thrust. I placed my hands around her waist and pulled her back as hard as I could by the hips, slamming my cock into her at the same time.I could feel her cock begin to stiffen up as her thong began to tighten around her hips; she was enjoying this just as much as I was..

She was enjoying this a little too much; I could feel her ass begin to twitch and seize on my cock. It was wrapping itself tighter and tighter; she was about to cum. The sensation of her cumming was too much for my cock to handle; her ass milked every last drop of my cum and there was nothing I could do about it. I shot rope after rope deep inside of her, Tom.. My sister's husband.

And that was that; she collapsed in a heap in front of me and I fell to my knees beside the bed. I was exhausted, drained, and still incredibly horny. I looked over at Karen in the corner and she was completely naked; her fingers soaked from playing with herself.

"Is.. Is it my turn?" Tom muttered under his little sissy breath.

Karen froze and her eyes went wide; she started to hesitate.

I shook my head and mouthed the words "Don't worry." to her.

I flipped Tom over and place a finger of his lips in order to "shush" him as I made my way back down to the end of the bed. I sat on my knees between his legs as he laid there blindflolded and deaf; I can't tell you why I did what I did.. But I did it and Karen couldn't believe it.

I placed my lips around Tom's tiny limp cock and slurped it into my mouth; I could feel the blood begin flowing as I moved up and down his cock with my mouth sucking it as soft as I could, getting harder and deeper with each thrust. Once his cock was as big and hard as it was going to get.. Which wasn't very big at all, I took it all the way down my throat and forced his hips up and down to fuck my mouth until I was forced to cough and gag all over his cock and balls.

Karen's mouth dropped wide as I stood up and turned to face her while lowering myself onto Tom's tiny cock. I could feel all the spit and slobber running down his shaft as I positioned the tip of his cock with my asshole; with one hand I made sure to hold my cock and balls up to make sure he wouldn't feel them. I sat down completely shoving Tom's cock inside me; I'd never had much more than a finger inside of my ass and it was a completely new sensation.

My body twitched and I shivered with cold chills as I started to bounce back up; sliding the shaft of his cock throughout my asshole. My cock began to come back to life with each bounce until I was rock hard again and leaking precum; Karen and I maintained eye contact the entire time and her fingers were swirling around her clit faster and faster until she reached another climax.

She dropped to her knees and out of the chair she was sitting in; she began crawling her way over to the bed and sat before me as I bounced up and down on her husbands cock. Before I knew it she was suckling on the tip of my cock; I couldn't believe my eyes. Karen proceeded to throat fuck herself with my cock and I could feel her spit slipping and sliding down my shaft to my balls and onto my asshole and then onto Tom's cock.

Karen sucked my cock so well that I ended up cumming within minutes; which in turn made Tom cum inside of me. My ass gripped his cock tightly as he shot his cum as far as he could with his tiny little dick. Karen didn't swallow my cum but instead showed me it in her mouth, placed her mouth onto Tom's cock and slurped up the remainder of his cum and then made her way up to him so she could spit all of the cum into his mouth.

We were all exhausted and at a loss for words; I especially couldn't believe what had happened. I had no intention of letting Tom fuck me nor did I ever believe Karen would suck my cock. A bit embarrassed and ashamed I gathered my things and quickly left Karen's house.

We'd have to talk about the events of this night some other time.

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heartRodimusMike, Snesfan and 33 other people favorited this story! 

by Anonymous

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by RodimusMike07/28/19

Technically its not Gay but Sissy

CD maybe even Bisexual,but the point is this is anything but Gay sex since both Twin Brother and Sister shared the same cum when Sis took Bro's cum and also part of her Husbands cum and fed her Hubby themore...

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by Anonymous03/06/19


5 Stars!

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by Anonymous11/15/18

Okay story. Please stop saying it is miss categorized

For one, if not into gay stuff then stop reading when he says the gay stuff is his 0lan. It is stated half way down and well before gay stuff begins. For two, "sissy" IS a TABOO fetish, so it is in themore...

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by prop6911/12/18

Not into pervert

Post somewhere else

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by Anonymous11/10/18

Wow...a little warning would be nice. Not into the gay stuff! Bad form!

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