tagAnalExploring Sexuality: A Pegging

Exploring Sexuality: A Pegging

bysilkstockingslover©

Summary: Husband is pegged by sister-in-law with wife's permission

Note 1: Thanks to Robert, goamz86 and Wayne for editing.

Exploring Sexuality: A Pegging

I was almost in the city when my cell rang.

I glanced at it and saw it was my sister-in-law Sabrina.

I sighed.

I loved Sabrina, but since her divorce she had been as exciting as a Nicholas Sparks movie.

Yet, obviously my wife had told her I was going to be in the city for meetings and if I ignored it I would get it from both her and my wife... I mean, seriously, the invention of the cell phone ended up being a digital ball and chain.

On the fourth ring, I answered, "Hi, how are you, Sabrina."

"Hungry," she answered. "How far away are you?"

"Twenty minutes," I answered, knowing I had just passed the last town before the city.

"Can you meet me for dinner?" She asked.

Truthfully, I wanted to get to the hotel, get undressed, take out the butt plug currently lodged in my ass and use one of my prostate massagers (I had three).

For the past nine months, I had been questioning my sexuality.

No, I'm not gay. I don't find men remotely attractive.

But, the idea of sucking a cock... well, that had become more and more of an obsession.

It started by accident when I read a story about a guy who was convinced to suck a cock in front of his wife.

It had never occurred to me that such an idea would even remotely turn me on, but when my cock stirred, then hardened, I got confused.

I jerked off to lesbian stories, group sex stories and the odd incest stories...but never had I even be drawn to read a gay story.

Before I knew it I was shooting my load as the wife ordered, "Swallow every drop, cock sucker."

That triggered a door deep in the closet I had never known even existed... one that would not allow itself to be closed no matter how much I tried.

Then for a month I tried to ignore that new subtle temptation in the back of my conscience and yet every time I started reading porn as I got hard and more excited I ended up searching gay stories.

Each time after I came, I felt guilt and shame as I questioned why I was having these feelings... my dad would disown me if he had a clue I was having, what he would call, faggot fantasies.

I read online about straight guys who sucked cock.

I read about the research and different theories that almost all men at some point consider sucking a cock and many consider being topped.

I read about married guys who would never cheat on their wives with another woman but regularly sucked cock, and some who even took it up the ass. Yet, their rationale was simple: they only did things they couldn't do with their wives.

I read more and more.

Then... I learned about pegging. The idea of a woman fucking a guy in the ass with a strap-on.

This really became my obsession as it kept my gay cock sucking fantasy at bay.

I didn't want to suck a guy's dick... not really. I mean, I did, a lot... when horny... I mean so much so that I even watched some gay porn of guys sucking cock and even taking it in the ass... even the idea of getting spit-roasted, taking a cock in both ends while on all fours, turned me on when I was rock hard.

Yet, it wasn't something I ever seriously considered doing.

But pegging....

I loved my wife and would never cheat on her... but suddenly the idea of my wife pegging me was now implanted in my mind and my fantasies.

Now, originally that was all it was... a fantasy.

I was the man and there was no way I was going to tell this fantasy to my wife.

But what it did do was get me curious about anal toys.

I spent hours online reading reviews of anal toys for men. Initially I was shocked at the plethora of toys made for men. I had thought there were just blow-up dolls and butt plugs.

Besides the toys for the penis, such as the Fleshlight I ended up buying (which is almost as good as a real pussy, I quickly discovered), there were so many anal and prostate toys I really didn't know where to begin.

I ended up spending an entire evening at a hotel one night researching, reading reviews and so forth on dozens of toys.

In the end, I bought a three butt plug starter pack and a small, thin vibrating prostate massager.

I won't go into the vivid details of my first butt play solo experience other than to say the smallest butt plug was too small and the biggest was too big... I kind a felt like goldilocks testing out the three bowls of porridge.

The second one felt slightly uncomfortable at first, but then as I used my fleshlight I came harder and more intense than I did with just my hand.

Of course, as I lay on my hotel bed, with a butt plug in my ass I felt shame course through me.

This cycle would follow for a few weeks as I experimented with more toys.

Eventually, I felt the butt plug wasn't enough as it didn't do anything but fill my ass which, after I got accustomed to it, I wanted more.

So I bought a vibrating prostate toy.

The first vibrating prostate toy felt good for a while, but eventually I wanted thicker.

So I bought a bigger one.

Then, wanting more, I finally shelled the bigger bucks and bought a Nexus Revo Stealth.

That device, once I got used to its girth and variety of the rotating head that directly stimulated my prostate, I was in heaven. My orgasms were the most intense I could create on my own and often, truth be told, more intense than when having actual sex.

And that was what I was looking forward to using once I got to the hotel.

Alas, instead I was going to have dinner with my sister-in-law while a butt plug was lodged in my ass.

"Sure," I agreed.

"Great, meet me at Brooks, as soon as you get into town," she said.

"Sounds good," I agreed.

For the record, I did have a talk with my wife about pegging.

Originally, I did it by sending her a literotica story called "Kinky Tales: I Pegged my Husband," that seemed to parallel in many ways my own self discovery of a sexual perversion I didn't know I had.

Unfortunately, she wasn't as supportive as the character in the story.

She texted me: We can talk about this when you get back home.

A rush of excitement coursed through me at the idea that she may have read the story, got turned on from it and was going on surprise me with a strap-on when I returned home.

Alas, my fantasy was just that... a fantasy.

Once home, she asked rather bluntly, "Are you gay?"

"What? God, no," I responded.

"So where did this come from?" She asked, as we lay in the bed.

"Honestly, I don't know. Just an idea that was triggered by a story I read and then it just kept getting more and more intriguing," I explained.

"The story you sent me?"

"No, that is just the one that most relates to us," I answered.

"With the incest undertones?" She questioned.

"What? No, no," I said, although the idea of Sabrina and my wife in a 69 was fucking hot. "I wanted you to read about the intimacy of pegging."

She asked after a pause, repeating the question but now with a vulnerability, "So you're not gay?"

"No," I protested. "I have no interest in guys."

That was mostly true, although the idea of sucking a cock never completely left me. I wondered what a hard cock would feel like in my mouth, what it would feel like to bob back and forth and, although rather gay I suppose, I wondered what it would feel like to swallow a load of cum or take a load on my face.

"But you want to take it in the ass?" She asked, clearly confused.

"I know, weird," I nodded, not able to fairly do my thoughts and feelings justice.

There was another pause, before she said, "I don't think I could do that."

"Oh," I said, suddenly deflated to have my fantasy crushed in just one sentence.

"It's just, that's not me," she said.

"But, it could be."

"How?"

"You get the power, to be in control," I explained.

"But it's not me," she repeated.

"I thought you would like this," I said honestly.

"How so?" She said. "You know I'm kind of vanilla when it comes to sex."

"I just thought you like to be in control in all other aspects of our home life," I said, thinking how bossy and in control she was in regards to the house.

"It's not the same," she said.

"I guess," I shrugged, trying to think of a way to make her reconsider.

"That said," she smiled, "I wouldn't mind a cock in me."

"I don't know," I playfully teased.

Once in the bedroom, I did what I always did, I got her off with my tongue. It was the only way she came.

I loved her taste, I loved giving oral satisfaction, but even as I licked her I wondered what it would be like to have a cock in my mouth.

After she came, I rolled onto my back and she asked, "Are you going to come and fuck me or what?"

"Maybe once you get me hard with that wicked mouth of yours," I responded.

She said, opening her mouth, "Can't, cold sore."

"Always with the excuses," I teased.

"Plus, shouldn't you be hard? You just ate my pussy," she pointed out as her hand went to my completely flaccid cock.

I shrugged, "I really enjoy eating you out, especially hearing you moan and your legs stiffen, but it usually doesn't get me hard."

She began stroking my cock. "And what gets you hard?"

"I don't know," I shrugged.

"Is it the idea of me fucking your ass from behind that gets you hard?" she asked.

"Oh," I groaned, her dirty talk exactly what I had hoped she would say when this conversation happened.

"You could be my little girl," she purred, "maybe even wear the thigh high stockings you like me wearing."

"Shit," I moaned, my cock growing.

"Or maybe you want some guy's hard cock in your mouth," she continued as my cock suddenly was standing completely at attention.

She laughed, "Well, that worked. Now come and fuck me."

And I did, even as I wondered what this strange interaction meant and why hearing her say those words got me so fucking hard.

A few minutes later, I deposited a load in her pussy and then nothing.

We never talked about it again.

We had sex a few more times over the next month, but she didn't say a word and I was too insecure to bring it up again.

Which leads us back to today. I arrived at the restaurant realizing I was actually quite hungry.

I went inside and as was the usual, even though she lived here, just five minutes away, I got there first.

I sat down, ordered a drink and got comfortable, the plug still in my ass. I considered taking it out, but decided it would be slightly exhilarating to have it in my ass as I chatted with my oblivious sister-in-law.

When she walked in a few minutes later I was shocked. She was in a tight blouse, short skirt and nylons, something I never saw her wear... not even at her wedding. (Yes, I'm that big a pervert or stocking fetishist to check and remember).

As she sat down she apologized, also a first, "Sorry I'm late, I had a job interview."

"For what?" I asked.

"An upper management job," she answered.

"Well, you look amazing," I complimented, my cock hardening, not caring she was my sister-in-law.

"Thanks," she said, before adding, "if I recall from my sister, you have a nylon fetish."

"My wife told you that?" I gasped, surprised that such a thing would ever come up.

"First, we tell each other everything," she said.

"That is a terrifying thought," I joked.

"Second, she told me when I started noticing her wearing them when we hung out together. She and I both have always hated pantyhose," she said.

"Yeah, yeah, a man made invention to sexualize woman... blah, blah, blah,"

I said, having heard my wife say that exact same thing many times.

"Actually, I like wearing them," she smiled. I was about to say I had never seen her in them before when she added, "in the bedroom."

"TMI!" I joked, knowing tonight I would be jerking off to my sister-in-law in nylons. I wouldn't cheat on my wife in real life, but in my fantasies I was quite a wild guy.

"What? It's not like I'm telling you I like taking it in the ass," she continued, her wicked tongue both a raging turn-on and also a complete shock.

"Are you telling me you do?" I asked.

"I do what?" She asked, teasing me relentlessly... suddenly I felt like I was on a date and not having dinner with my sister-in-law.

I wasn't going to play into this weird game that could only get me in trouble. I laughed, "Things I probably don't need to know."

"You don't want to know about your hot sister-in-law's anal sex life?" She asked.

"I'm not going to ask questions," I countered, "but you are welcome to tell me anything you want to tell me."

Before she could respond the waitress arrived and we ordered our food.

Once she was gone, Sabrina continued talking, but about her job interview, the disaster that still is her divorce and the house changes she was making. It was then she asked, "Any chance you could come over and help me move a couple of things before you go to your hotel?"

The answer was no, 'I want to go to my hotel and jerk off about you as I use my Nexus on my prostate.'

Of course, that wasn't what I said. I nodded, "Sure."

"Awesome, and I promise you I'll make it worth it," she said.

I laughed, "That I'm looking forward to."

We ate dinner, we chatted, we flirted in a way we never had before and then I followed her back to her place. I still got lost as I had only been there a couple of times.

As I followed her in, I couldn't help but notice how amazing her legs looked in the mocha coloured nylons and my already hard cock flinched as I noticed she was wearing thigh highs as she went up her steps.

Once inside, she slipped out of her heels and I stared at her beautiful nylon-clad feet in mocha stockings... and her toes painted red, which had me completely mesmerized.

My wife knew that the best way for her to get me hard instantly was:

A) nylons (my favourite colour being mocha or tan... Although white and black were also very cock stirring... Actually, truth be told any colour of nylons would awaken my cock in seconds).

B) Painted toenails (especially red and more especially red in mocha nylons).

Other things worked, like talking dirty, sucking my cock and teasing my nipples... but nylons and painted toe nails were my sexual kryptonite.

As she wiggled her toes, as if tempting me, she laughed, "Kendra wasn't kidding."

"Pardon?" I asked, not actually taking my eyes off her feet as I feigned taking my shoes off.

"You really are a nylon-clad foot guy," she said.

"She told you that?" I asked.

And for the second time that day she stressed, "Like I said earlier, she tells me everything."

"And for the second time, I'll admit that scares the hell out of me," I joked, finally breaking my stare at her perfect feet.

I was worried she would go change into something more practical, but she said, "What I need moved is downstairs."

"Okay," I nodded, again watching her great ass and amazing legs as she walked in front of me.

"And stop drooling over my legs," she joked as she turned around and caught me doing just that.

"Sorry," I shrugged.

"I bet you are," she quipped as she kept walking.

We spent the next ten minutes moving a few things and when done she asked, "Want a drink before you head out?"

Not wanting to leave when my sister-in-law was in sheer nylons (I assumed they were sheer nylons based on how her legs literally shined in them) and yet knowing I should. I wasn't worried about cheating on my wife, but with all the clear innuendo that had transpired between us today it was definitely the most tempted I had ever been.

"I should probably get going," I said, even as my eyes were drawn again to her feet.

"Would it be too weird for me to ask you to give me a foot massage?" She asked out of the blue.

My cock flinched.

I loved giving my wife foot massages when she was wearing nylons. Being slightly submissive, I liked giving my wife foot massages whenever she asked, truthfully.

"I don't see why not," I shrugged, thinking I had given my sister foot massages and thus it wasn't anything inappropriate.

"Great. Kendra tells me you give the most relaxing foot massages," Sabrina said, as she sat on the couch.

I joked, as I joined her on the couch, "I'm usually doing that with an ulterior motive."

"Oh, and what would that be?" she smiled wickedly, pretending to play dumb.

"I plead the fifth," I joked, as she spun her body around and put her feet on my lap.

I took one nylon-clad foot, and indeed they were sheer silk like my wife wore, and began massaging it.

"Oh, that feels nice," she said, giving out just the softest of moans... which made my already hard cock flinch in my suddenly too right trousers.

"Your sister makes me do this all the time," I said, as I massaged each toe individually.

"You are her little bitch," Sabrina quipped.

"And what does that make me to you?" I questioned as I finished her last toe and moved to the sole of her foot.

"My bitch-in-law," she answered.

"Can't say that is overly flattering," I said, although I was so turned on by massaging her stocking-clad feet she could call me whatever she wanted.

"Just do as you're told and I may just reward you," she said, so seductively that my hard cock again flinched and yet for the first time I seriously wondered about my sister-in-law's motives.

"Yes, ma'am," I saluted with my free hand, hinting at my submissiveness.

"Keep working," she said.

And for a few minutes I massaged her feet. I was moving to her calf, when she asked, "So you want to get pegged?"

"What?" I gasped.

"Your wife tells me everything," she reminded me.

"Apparently," I said, my face going beet red.

"I told her she should just bend you over and fuck the shit out of you," she said rather matter-of-factly.

"Oh, God," I said, almost as a groan, the idea of exactly that being my fantasy.

"You really want to get ass fucked, don't you?" She asked.

"I can't believe we are having this conversation," I said, mixed feelings coursing through me again.

On the one hand, shame and embarrassment at someone knowing I had such a fantasy.

On the other hand, relief at finally having someone to talk to this about... even if it was my hot sister-in-law.

"Answer the question," she ordered. "Do you want to get ass fucked?"

"I prefer the term pegged," I countered, that made it somehow seem less gay than her phrasing.

She smiled, "That's just semantics."

I retorted, as I continued massaging her calf, "Maybe, but one makes me sound like I'm gay and the other seems romantic... or at least more intimate."

"Fair enough," she nodded, as she moved her other leg to my hands. "Do this calf too."

"Yes, ma'am," I nodded, attempting to be playful and also hinting at my submissiveness again.

"So, you want to be pegged?" She asked.

"Yes," I admitted.

"Interesting," she nodded.

"Why is it interesting?" I asked, her tone hard to read.

She shrugged, "It's just I was very surprised that Kendra wasn't excited by this."

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