tagTranssexuals & CrossdressersShemale Sister-in-Law

Shemale Sister-in-Law

bysilkstockingslover©

Summary: Man gets massage from sister-in-law with crazy, shocking results.

Note 1: This is a Nude Day 2015 Contest Story so please vote.

Note 2: Thanks to goamz86, Robert, Wayne and Wordsmith1950 for editing this story.

SHEMALE SISTER-IN-LAW

"What is this?" My wife asked me as she opened my suitcase.

'Fuck', I sighed to myself. I had just returned from a business trip where I purchased a butt plug. Truth be told, I felt like I was having my mid-life crisis. Instead of buying a Porsche or Lamborghini, I got curious about my sexuality. I wondered what it would be like to suck a cock, even though I did not find men sexually attractive at all. I felt more and more compelled to be on my knees, to have a cock in my mouth. This became my constant stroke fantasy and what began as a vague curiosity continued to grow into an obsession.

Yet, I wasn't gay.

I'm married... to a lovely wife. Our sex life is okay, not amazing like when we were in our college years, but still nothing to complain about. I still found her beautiful. She still dressed up sexy for me; she role played many of my fantasies and she still gave me head. When drunk she was utterly insatiable, although that too was far less common than in our college days.

Yet, I wasn't sure she was going to be willing to help me with my curiosity.

"Um," I began, not even sure how to explain why I had a butt plug in my suitcase and worrying she may think I was cheating on her.

"That is not going in me," she said her tone clear, dropping the toy back in my suitcase.

"I never planned for it to," I replied, knowing other than one drunk night in college where I fucked her ass, it was 'a don't even talk about' subject.

"Then what was it for?" she asked, looking confused.

"Me," I whispered, looking down and feeling ashamed.

"What?" she asked, maybe because she didn't hear my answer or maybe she was surprised by my answer.

"It was for me," I admitted, looking up to her, worried about her response.

"Really?" she asked, looking surprised, with a sudden smile on her face, that was gone almost as quickly as it had appeared.

"Yes," I nodded, suddenly perplexed by her smile.

"Do you want to be with a guy?" she asked.

"God, no," I answered, that being the truth. Sure I had fantasized about sucking a cock, but always disengaging the fantasy with who the cock belonged to.

"Then what?" she questioned.

"I don't know," I admitted, not sure myself. When I was horny reading gay porn, I'd imagine myself on my knees as the protagonist straight cocksucker in the story. Once my load was shot I immediately scolded myself for having such gay thoughts.

"Have you used it on yourself?" she asked, grabbing it again.

"Yes," I nodded, shame coursing through me. I had originally bought a smaller one. I found it was too small to really do much. I bought a bigger one and that was too big. The one in her hands was the third purchase and it fit just right.

"Did you enjoy it?" she questioned.

"Kind of," I admitted, which was a good answer. Although it filled my ass well, it was too small to hit my prostate and didn't vibrate... which I had already decided would be my next type of toy, having done a fair amount of research online on prostate massagers.

"Kind of?" she asked, her facial expression not telling me if she was repulsed or turned on by it.

"I'm really kind of confused by my curiosity," I admitted, feeling very vulnerable at the moment.

"You're not going gay on me?" she asked smiling again at me.

"No," I laughed, "I still love cunt."

"So, you want cock and cunt?" she asked, sauntering over to me.

"Would you like watching me suck cock?" I playfully asked.

"I don't know," she shrugged, reaching me with a slight smile, "I can't deny the idea got me a bit wet."

"Really?" I asked, surprised completely by the turn of events from humiliation to apparently having sex.

Her hand squeezed my hard cock, as she smiled, "It seems to have gotten you a lot hard."

"Truth be told," I answered, "you being in a skirt and nylons didn't hurt either."

"Well, then this will really help," she smiled, moving to the bed, lifting up her skirt revealing she was sans underwear and her usually hairy pussy, something I had complained about for years, was completely shaved. "Kara convinced me to get a Brazilian."

"I love your sister," I said, staring at her shaved cunt and glistening pussy lips.

"You better not," she countered playfully.

"It seems the idea of me sucking cock got you wet too," I smiled, as I moved between her legs.

"No, I've been waiting for you to get home all day," she admitted.

"It has been a while," I admitted, as I leaned forward and licked her pussy.

"Too long," she moaned.

"Then let's make up for lost time," I quipped, licking her shaved pussy hungrily.

"That's it," she moaned again, "Lick me, baby."

I licked her for a few minutes until her legs stiffened, she grabbed my head and came on my face. "Yes," she screamed.

As she came, she pushed me away like she always did, getting instantly oversensitive.

"Come fuck me," she demanded, always wanting to be pounded hard after her first orgasm.

"Get me ready," I ordered, snapping my finger at my oddly no longer hard cock.

"Just come and fuck me," she demanded, more times than not avoiding sucking my cock after I ate her out, which often annoyed me.

I got undressed and said, "You need to get me ready."

"You were hard talking about cock sucking and now you're soft after getting me off?" she asked, clearly looking offended.

Typical... she doesn't suck my cock and somehow makes me feel guilty; after she got off she just wanted to be fucked and although that was hot, it annoyed me when I wanted her lips wrapped around my cock first.

I shrugged, "You know I often don't get hard from eating you out."

"But you were hard when you started," she pointed out.

"I know," I shrugged, before adding, "I can't explain how my dick works."

"Come lie down," she ordered.

I did.

She kneeled beside me. She stroked my cock, asking, "So, do you really want a cock in your ass?"

I flinched slightly at the surprise question.

"Not a real cock," I answered.

"Just toys?" she asked, my cock beginning to stir again.

"Maybe a strap-on cock," I responded, the idea of being fucked by my wife suddenly a hot idea.

"You want me to fuck you?" she asked, her hand slowly stroking my cock, her tone curious.

Just hearing her say those words turned me on and I admitted, "It makes sense."

"How?" she asked, my cock growing quickly.

"Well, you already boss me around all day, might as well boss me around in the bedroom too," I answered.

"Well, either way it worked," she smiled with a laugh. She got on all fours and said, "Fuck me from behind, baby, you can pretend it's my ass you're pounding."

This was new for two reasons:

1. She preferred the missionary position or being on her side. The last time I did her doggy style was years ago, at a hotel, when she was drunk and adventurous and I banged her on the balcony.

2. She never even liked jokes about ass fucking, never mind talking about it in the heat of the moment.

I quickly moved behind her, and slid inside her wet cunt.

"Oh yes, baby, fuck me from behind," she moaned, as I buried my cock in her.

The different angle, the different position, her loud moans as she put her hands on the headboard, the hard fucking and our conversation all combined to make me ready to shoot my load in less than two minutes.

As I finished depositing my load in her cunt, she quipped, "Holy shit, either the idea of pounding my ass or of me pounding your ass had you revved up."

"Maybe both," I quipped, pulling out.

We both cleaned ourselves up and didn't speak anything else about this for a couple of weeks. I wondered what she really thought of it.

It was just over two weeks later, when I complained my back was killing me, she suggested, "Why don't you go and get a massage from Kara?"

"What?" I asked. Kara was a professional masseuse. My wife made it clear I couldn't ever go to her. She was very voluptuous, unlike my wife who was rather small chested.

"Sure," she shrugged, as she typed on her phone, "there is no one better."

I was about to talk, but she brought her finger to her lips implying I was not to talk as she put her cell to her ear. After a minute, she said, "Hey, Daryl's back is killing him after all his travel of late. Any chance you can squeeze him in?"

I gasped. I really couldn't believe she was going to let her sister give me a massage. Kara was well known in the community for her massages and often having two plus week waits to get in.

"Oh, I doubt he will mind," my wife, Amanda, responded, with a very odd giggle, before adding, "yes, he'll be there."

'OMG!' I thought to myself.

"Thanks, gorgeous, he'll be there at ten," Amanda finished. Looking at me, after she hung up, she explained, "She can fit you in at ten."

"Tonight?" I asked.

"Yep," she nodded.

"That's pretty late," I pointed out, usually I was ready for bed by nine.

"That's when she can fit you in," she answered, in a tone implying the conversation was done.

"Okay," I nodded, stunned after all the years Kara offered me massages and Amanda refused to allow it, she was okay with it.

.....

I drove to Kara's house; she had made her basement into a very nice massage area.

I knocked on the door and after a moment Kara opened it.

To my surprise, she was dressed in a red dress and nylons which instantly made my cock harden. I had a weakness for nylons, a fetish I developed in high school, from cheerleaders. In all the years I knew Kara I had never seen her in nylons... never. Yet, there she was in a red dress showcasing her voluptuous breasts and mocha nylons which also happened to be my favourite colour.

To add to the cock hardening moment, her feet were in full view. Her toes were painted a matching red.

Yet another dick flinching moment was when she pulled me in for a tit crushing hug, something she always did. Kara was a very touchy-feely woman which made sense based on her profession.

She explained, "Sorry, I just got home and didn't have time to change."

"Go ahead if you wish," I said, even though I was enjoying her look I knew it would be hard to not be hard as a rock when she was massaging me if I constantly saw her feet in nylons.

"No, no," she shrugged, "It's already ten."

"Okay," I shrugged, both excited and nervous at the idea of her being in nylons while she massaged me.

"Plus," she added, as she began walking to the stairs, "I know how much you like stockings."

My eyes went wide. Did Amanda tell Kara such things? This sentence, plus the fact she wore nylons, should have signalled something was different today, not to mention the fact that Amanda was allowing this massage to happen in the first place.

As I followed her down the stairs I noticed something else when she reached the bottom of the stairs. Ever so briefly I noticed she was wearing thigh high stockings, as I saw a quick glimpse of lace top... this only added to the aching in my loins.

"Get undressed and call me when you're ready," she ordered, as her cell rang. She added, before answering the phone, "And I mean completely undressed, underwear too. She answered it talking as she went up the stairs.

I couldn't protest or question the completely naked order as she walked away, I got undressed, ignoring the last order, keeping my underwear on, my dick rock hard, and got under the white blanket on my stomach. I called out, "Ready," and waited.

A couple of minutes later, she returned downstairs and said, "That was Amanda, she was making sure you made it here."

"Okay," I said, feeling guilty my dick was so hard because of her sister.

She put a hot towel on my shoulders and started massaging my left leg. She asked, "So, where are you sore?"

"Almost everywhere," I admitted, her hands already feeling great as she worked on my calf.

"Well, then I'll be sure to work you over everywhere," she said, seemingly stressing the word 'everywhere'.

If I didn't know any better, I'd have thought she was implying something sexual, yet she was my sister-in-law.

For twenty minutes she worked my entire upper body before moving to my calves and then feet. She scolded, as she moved the towel off my ass, "You didn't listen."

"I thought it would be weird," I replied.

To my surprise, she moved to my hips and roughly pulled my underwear down and off. "Your wife asked me to give you the full treatment,"

"What is that?" I asked, stunned and feeling uncomfortable, finding it hard to believe my wife would want me nude in front of her sister.

"Oh, that is for me to know and you to find out," she replied, in a tone that only made me worry more. She moved her hands to my ass and poured oil on it before she began massaging.

I stammered, as my dick began to rise, "I-I-I don't think Amanda would approve of this."

"Trust me," she replied, "she made it clear that I should give you the complete thorough treatment."

Her finger slid ever so slowly between my ass cheeks ever so briefly before she continued, "So Amanda tells me you like feet."

"What else does she tell you?" I asked, mostly joking, although curious what these two sisters talked about and wanting to change the awkwardness.

"She tells me everything," she answered, which made my eyes go wide. "For example, you'd rather check out a pair of legs in nylons than a pair of big tits."

"I've never been a tits guy," I admitted trying to act casual, as she continued massaging my ass.

"I've never had a guy not become a tits guy once he got to play with mine," she said. Making sexual jokes was not uncommon for Kara. Somehow this seemed different.

"I imagine that is true," I replied, laughing awkwardly, tightening up.

"Amanda strongly guaranteed that if you had a choice between touching my tits or my legs in nylons you would go for my legs," Kara continued, as her hands worked magic on my ass, while my cock desperately wanted to stretch itself in a very restricted position.

"I can't believe you two would have such a conversation," I said, feeling incredibly awkward in this situation.

"Like I said," she continued, as she gave my ass one hard firm squeeze before she moved around, so she was directly in front of me. As were her stocking-clad feet as I looked down. "We tell each other everything."

"Well, that scares the shit out of me," I responded, my naked ass uncovered making me feel so vulnerable.

She laughed, as she massaged my shoulders firmly, "What an apropos response."

I was about to ask what she meant when she asked, "So do my feet look good in nylons?"

"Yes," I admitted, staring at them, her perfectly manicured toes turning me on completely.

"I wore these for you," she revealed.

"Oh," was all I could muster.

"Do you know why?" she asked.

"I have no idea," I answered, before adding as a joke, "Because I'm on candid camera?"

"Funny," she laughed, as she wiggled her toes. "No, I hate being told I'm wrong and thus I need to test your wife's theory."

My eyes went wide again as I realized what I was sure she was implying.

She took her hands off my shoulders, but didn't move her feet and I wondered, 'is she really going to show me her tits?'

I slyly lifted my ass up so I could reposition my fully erect cock.

She asked, "Are you okay?"

"Just needed to shift a bit," I answered.

She laughed, wiggling her toes in the nylons, "I bet you did."

I couldn't believe what was happening.

I couldn't believe when she said, "Look up, Daryl."

"I'm not sure I should," I replied.

"Don't move," she ordered, and walked away. She said, a moment later, "Hey, Amanda, you're on speakerphone, can you please tell your husband it is okay for him to see my tits."

I heard my wife respond, "Daryl do as she tells you."

"Seriously?" I asked, as Kara's nylon-clad feet returned to my narrow view.

"Yes, I made a bet," she said.

"About what?" I asked, in awe of this whole situation, even though I already knew what the bet was about.

"Just amuse her and prove me right," Amanda instructed firmly.

"You sure?" I asked, feeling I was being set up, as I saw her red dress hit the floor.

"Yes," she sighed, "now stop being a pussy."

Kara laughed, "Maybe he is a pussy."

"Fine," I said, lifting my head up. As I took the first glance up I gasped and froze before my gaze reached her tits.

Kara

had

a

cock

!

!

!

"Surprise," Kara said.

I was speechless.

"What do you think?" Kara asked as her petite hand stroked her big hard dick.

"Um," I began, unsure what to say, even as I stared at my sister-in-law's hard cock, pointing directly in front of me. It was longer but thinner than mine.

"You have been fantasizing about cock for a while. I figured rather than you going on Craigslist or some other dumb ass idea, you can experiment safely," Amanda revealed. I had forgotten she was on the phone as my eyes were transfixed on my sister-in-law's dick.

I was still speechless.

Kara laughed, "He can't take his eyes off it, baby sis."

Which was true. Partly because I was in awe that my sexy sister-in-law had a cock, partly because a beautiful six inch cock was just a couple inches from my mouth and partly because my wife was a willing participant in this strange turn of events.

"Do you want to suck it, baby?" Amanda asked.

"I don't know," I lied, even though I desperately wanted to suck it.

"Go ahead, baby, suck Kara's beautiful cock," Amanda continued, although her voice seemed so much closer.

"Amanda?" I asked, looking behind me and seeing her dressed in red lace lingerie and stockings and nothing else.

"Get over here," Kara ordered, her tone shifting from sexy to firm.

"Mmmmmmm," Amanda nodded sexily, quickly walking to Kara and dropping to her knees.

"Oh my God," I gasped, my head spinning as my wife was suddenly on her knees in front of her sister.

"Tell him," Kara ordered.

"I've been sucking and fucking Kara since I was eighteen," Amanda revealed.

"Actually, it was your 18th birthday present wasn't it?" Kara asked.

"The best present ever," Amanda smiled, flicking Kara's mushroom top with her tongue.

I was again speechless. The thought of my wife and her shemale sister having sex was the biggest turn-on ever, even hotter than my many year fantasy of watching Amanda dyke out.

Amanda added, "It was pretty sweet having a cock available at all times in the bedroom we shared."

"It was also nice to have a live-in cocksucker," Kara added.

Amanda smiled, "You can thank Kara for me being such an eager cock sucking, cum swallowing slut."

I nodded, even as I thought she hadn't been sucking or swallowing my cock much the past couple of years...was that because she was busy sucking and swallowing her sister's? I stared as my wife slid her tongue down her sister's long, thin shaft.

"Thank her," Amanda said, as she tongued Kara's balls. I loved how Amanda worshipped a cock with her mouth, including the balls, the only woman I ever dated who did such a thing.

"Thanks," I weakly said, still in awe of the whole situation and staring at my wife sucking a cock that wasn't mine.

"You're welcome," Kara chuckled, before adding, "Do you want to see your wife suck my cock?"

I looked at my wife, on her knees as she looked up with me with a hunger I often saw in her eyes when my cock was in front of her, and I answered truthfully, "Yes."

"Yes, what?" she asked, as she moved her hard cock to her sister's lips.

"Yes, I want to see my wife suck your cock," I admitted.

Amanda smiled and said, "Watch, cocksucker, you're next."

Report Story

bysilkstockingslover© 44 comments/ 228876 views/ 361 favorites

Share the love

Report a Bug

Next
2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel