It wasn’t one day where I thought, ‘Hey, I want to get ass fucked’. No, it was a lengthy growing curiosity.
I grew up in a homophobic home where my dad used the word ‘faggot’ liberally and actually pulled an earring out of an employee who came to work with one in his ear.
Thankfully, I never considered myself gay. I have, even to this day, never thought of a man sexually, even though I have slowly become intrigued by cocks.
Anyway, I’m an ex-NHL’er, no Crosby or anything, but had a promising career until a knee injury ended it. I lingered in the minors for a few more seasons before retiring. I then had the opportunity to do some public speaking and it took off, creating an accidental new career. I have since travelled 46 states, 6 provinces and 11 countries with my message of perseverance.
In case you are curious (pun intended based on what this story is really about), I’m 42, 6’2, 230 pounds, with blonde hair and blue eyes. I’m still well built and very athletic. My cock is only 5 and a half inches, but thicker than most.
I’ve been married to my beautiful wife Dani for years. She is 5’3, 150 pounds (not fat by any means, but well-built and in great shape), with big 36D boobs and a nice ass I love to squeeze. I love her completely and our two boys, so I would never cheat on her… even though my curiosity has indeed grown over the past few months.
We still had good, if not great sex, but, like most married couples, the burning insatiable passion from our younger years had dwindled somewhat and our sex life had become rather predictable.
Of course, I was partly to blame. I was gone a lot. Often tired when I was home. And lastly, I had become less aggressive.
Dani, on the other hand, liked sex, but had become much less wild as the years went by and I would argue we both knew we were in a rut.
So, as I traveled I read a lot of erotica, watched a lot of porn and my fetishes changed slightly. I originally searched for lesbian stories, group sex stories, and stories with nylons included. I also watched nylon porn scenes like Housewife Kelly, especially the Real Estate scene, Holly Heart who often wore nylons and Alura Jenson who had a wicked tongue, huge knockers and almost always wore thigh highs.
Yet, after reading all the best stories, I began reading some of my favourite writers… even stories in categories I usually wouldn’t read like incest, transsexual and gay.
It wasn’t like I just instantly became curious. But over a few months, I began to wonder. What would it be like to suck a cock? What would it be like to cross dress? What would it be like to have something in my ass?
I resisted my growing curiosity for a few more trips before I finally went to an adult store while in San Francisco (it seemed like the right place to explore my anal curiosity). I ended up buying a three pack of butt plugs and lube.
Back at the hotel, after a few beers, some erotica stories and a porn scene starring Phoenix Marie, who often wears beige thigh highs in her stories and takes it in the ass, I lubed my butt and the smallest butt plug and put it in my ass.
A slight burn occurred, but barely, and after fifteen minutes of slowly stroking my fleshlight (a man’s best friend) while watching Phoenix be violently dominated in a nasty lesbian scene as a bridesmaid dominated her anally, I shot my load.
My next trip, I tried the medium plug. It was a lot wider and longer and created a more intense burn… yet also a more intense orgasm when I got off half an hour later after watching three hot and mean episodes, the last one called Ms. Boss where a hot blonde bitch dominates an employee.
As I explored my prostate and anal male pleasure, I wondered what it would feel like to have a vibrating toy in my ass as I wasn’t ready for the massive third plug.
So I bought a vibrating curved toy that had a variety of vibration speeds and patterns. Over the next month I tried every pattern, every speed. The orgasms were better and I began to get addicted to having it in my ass.
I also watched a lot of rough anal porn like:
Ashley Blue being blackmailed and roughly sodomized.
Bobbi Star taking two or three cocks in almost every scene she did
Of course, I then wondered what it would be like to be fucked, to be feminized a bit. So, first I ended up buying pantyhose and started wearing them while I had the vibrating dildo in my ass and even under my outfits while I spoke at conferences.
Yet, the porn I watched also got nastier:
Like Sarah Shevon as a teacher in a five guy gangbang scene where she took two cocks at once in her pussy and ass or Veronica Avluv as a female reporter who is gangbanged by players in a locker room or the MILF Allison Moore getting gangbanged by a bunch of men at her wedding. Of course, I couldn’t not watch my favourite Phoenix Marie as a feminist who is taken, humiliated and ass dominated by a reporter trying to prove she isn’t as innocent as she appeared.
The reality was the kinkier it was, the more it turned me on. I suppose this was because my own sex life could never be that kinky.
I tried to bring it up on the phone with Dani many times and in person… but I couldn’t. She saw me as the man. I just couldn’t tell her. I couldn’t ask her to fuck me. So, I figured I would fuck myself.
I bought myself a dildo that suctioned to the wall so I could literally fuck myself. Like all the other toys, it was very unique and exciting at first, but in the end it was awkward and frustrating. It only made me want to tell Dani even more.
I googled best anal toys for men and bought yet another toy… a rude boy. I was trying it for the first time when my wife finally returned my text, a couple hours after I had texted her (which is very unlike her). I was in my hotel room, in only pantyhose, boxers and the rude boy in my ass vibrating at full speed with a unique pattern that also teased my scrotum when her text came.
Her text was oddly ominous and unlike her:
I’ll give you a call in a few. I have a surprise for you!
My newest video and erotica fetish was having the guy watch his woman get fucked. I wasn’t sure I could ever allow another guy to fuck Dani, but in fantasy it really got me off. My fleshlight was nearby and already lubed as I tried not to come before she called. Yet, a few became fifteen and I was just reaching for my fleshlight, the new anal toy really making me feel good, as was the scene I was watching: : Zoe Holloway getting fucked in tan thigh highs outside while her husband watched.
Suddenly, my phone rang. I turned the volume on my computer to mute, but kept the scene running as I reached for the phone.
Answering it, I made a joke about my earlier text, as I acted overly dramatic, “Thank God, you weren’t kidnapped.”
“I was,” she replied, her tone equally as dramatic, “by Bethany.”
“Oh God,” I said, Bethany, her youngest sister by 15 years, and my wife never getting along.
“Actually, it was rather interesting,” she admitted, which was surprising.
“How so?” I asked, curious, as their time together usually ended up in yelling matches.
“Well, she decided I needed a makeover,” she revealed.
“Oh God,” I said, immediately worried, trying to be supportive I added, “I can’t even imagine what that could mean.”
“It definitely wasn’t a normal makeover,” she responded, her tone confusing to read.
“Okay, this is getting cryptic,” I pointed out. I then joked, a fantasy I had often had before I started getting more sick and twisted (Bethany was ridiculously hot and flirty), “What did she do, turn you into a lesbian?”
She responded with a laugh, which at least helped me with her tone, “Yes, I’m a raging pussy muncher now.”
“That is hot,” I said jokingly, even though quite frankly my cock stiffened, which made me glance at Zoe, who was sucking the cock that had just been in her pussy, while her husband watched.
Her tone definitely sultry, she was clearly in a rare playful mood, “You’d like that, wouldn’t you? Watching your wife between the legs of another woman?”
Knowing this was a tricky question, like when she asks if she looks fat in something, I paused. I then played the safe card, “I plead the fifth.”
She quickly read through me like she always does, “I’ll take that as a yes.”
I heard a buzzing. Was she playing with herself too? I asked, “What is that?”
“One of my new sex toys,” she answered.
“One of?” I asked, knowing her toy box was rather limited.
“Bethany also felt I lacked in the self-help department,” my wife explained, which added to this strange conversation. We both were using sex toys on ourselves. Although, unlike her, I wasn’t letting her know.
I was about to speak when she let out a moan.
Turned on and curious, I asked my usually tame wife (our phone conversations were usually about the kids, her family or other mundane things), “Did you just put it inside you?”
She didn’t answer the question, instead asking me, “What you wearing?”
I wasn’t going to say pantyhose, so I lied. “Just a t-shirt and shorts.”
“I’m completely naked,” she revealed, before adding after a moan, “even my pussy is completely naked, Bethany made me get a Brazilian.”
“Oh my,” I groaned, as I slowly rubbed my cock in my pantyhose as I envisioned my wife’s pussy completely shaved.
“Join me,” she ordered.
“What’s gotten into you?” I joked.
Her naughty side coming out, she answered wittingly. “At the moment, a six inch vibrating rabbit.”
My cock flinched.
She moaned the question, “Are you getting undressed?”
“Indeed,” I answered, even though I already was.
“Good,” she moaned again, before talking dirty to me. “I want that dick nice and hard for me.”
“Already done,” I replied, which was true. My cock was iron hard. The video I had been watching, mixed with the powerful vibrations of the bad boy inside me and my wife’s continuing shocking revelations and I was ready to blow… literally.
“Was it the lesbian talk?” she asked, then added before I could respond, “Do you want to see me with another woman?”
The obvious answer was ‘God, yes’. Yet being the smart husband I answered again, “I again plead the fifth.”
She said, not digging deeper, “Too bad they don’t make toys for boys.”
I had to hold back a laugh. I had one in me, a bunch more in the bag, not to mention the fleshlight I was about to use on myself. Yet, instead I answered with a joke. “They do, they’re called inflatable dolls.”
She quipped. “In theory the perfect woman. She never says no, she doesn’t want to cuddle after sex and doesn’t nag you about leaving the seat up.”
I laughed, my wife often funny, “All true, I suppose. But you can’t underestimate the touch of a woman.”
“Any woman?” she asked, which surprised me. What was the purpose of that question? I had long learned to try and read past the seemingly harmless way a question was asked. Almost always, a question from a woman had a purpose. And almost always, there was a right and wrong answer.
“Only one,” I slyly answered, not allowing myself to get in trouble. I was a veteran at answering the right way; years of experience answering the wrong way and sleeping on the couch, getting a kick in the shins or the icy glare that meant ‘we will talk about this later’ finally paying off.
She purred, her tone back to sultry, as she promised, “Good answer, and you’re going to get very lucky when you get home.”
I teased back, having heard this when we were out, but then finding her too tired to follow through once we get home, as I moved the fleshlight to my cock and allowed the pussy lips to lower on top of my dick, “Promises, promises.”
“I plan to make your biggest fantasy come true,” she said with a moan.
I joked, both of us in love with Miranda and Blake, “You are going to allow me a night with Miranda Lambert?”
She responded, “Only if you make it a threesome with Blake Shelton too.”
Another odd statement, as she had never used the word threesome ever. I joked, “Whose fantasy are we having now?”
She asked, “Are you pleasuring yourself?”
“Just slowly stroking,” I answered, which was true. I loved the feeling of using the fleshlight slowly. Allowing my orgasm to build. The anal vibrating toys only seemed to enhance the slow build and also the pleasure at eruption.
She whispered, her breathing seeming to get heavier, “I want to come together.”
“Me too,” I agreed with a groan, glancing at the video and realizing it had ended. I moved the mouse to part way through the scene and pressed play. I watched Zoe ride the guy’s cock, her beige thigh highs only enhancing the scene.
“Tell me your biggest fantasy,” she requested as a moan, which was hot.
I had many. This was yet another opportunity to mention my fixation on getting ass fucked. Yet, I didn’t want to ruin the moment. Instead, I just said the obvious truth of every man, “I have a lot.”
She insisted, “Tell me one.”
I was tentative. I had so many. Being ass fucked by her; taking her ass; quite frankly, anything to do with the ass. Watching her with another man; watching her get gangbanged; watching her in a lesbian 69. The scene I was watching now come true would be incredibly hot. Yet, I couldn’t choose any of those. I tentatively said, “Okay,” trying to save time.
She said, “No judging,” which immediately made me ponder telling her my fantasy of getting ass fucked by her. Yet, before I could seriously consider this she shocked me again, this time to the core, “But just so you know I currently have a small butt plug in my ass.”
I didn’t believe her. Anal sex was a clear no-no. The ass a strict outie only… her words. I called her bluff, even though I was praying she wasn’t lying, “Now I know you are playing me.”
She asked, continuing to play sexy vixen, “Want to see a picture?”
I asked, beginning to think she wasn’t pulling my leg, even though it still seemed far-fetched and unlikely, “You’re serious?”
“Deadly,” she responded, before adding, my cock instantly flinching in the fleshlight, “Both my holes are filled right now.”
“Holy fuck,” I groaned, just the vague possibility that was true enough to make me want to come now.
She said, “Give me a second.”
“Okay.” I agreed, wondering what she was doing. I quit stroking my cock, not wanting to come yet. Instead, I went to my videos and chose a new one.
I loved the relatively new porn star Jillian Jensen. She looked like the girl next door who could be nasty as hell, but whose eyes alone could get me hard. I had a few of her videos: lesbian, interracial, anal, bukkake, but I chose a lesbian one with Abbey Brooks as her step-mom. Incest had also begun to intrigue me and in this one Jillian is a stuck-up bitch who uses her hot body to get herself a job that turns into a hot threesome.
I pressed play and watched the beautiful Jillian use her beauty to get what she wanted.
It was a couple of minutes, enough time to watch Jillian slip off her shoe and rub the manager’s cock through his trousers with her black nylon clad red painted toenails (which was my fetish). Her sexy lips, her innocent smile and her sultry voice were easily the hottest in porn, maybe in all of acting.
I was entranced by Jillian’s seduction as Dani asked, “Like?”
I was confused, as I had lost focus as I drooled over Jillian. I checked my phone and saw no new messages. Confident I didn’t miss anything, I said, “I didn’t get anything.”
“Oh fuck,” she said, sounding concerned.
“What?” I asked worried by her tone, as I watched Jillian lean over a desk, fish out the guy’s cock and begin sucking. I wished I could hear her words and moans. She was a porn star who really seemed to enjoy whatever she was doing: sucking cock, eating pussy or getting fucked in her pussy or ass.
“Fuck! Fuck! Fuck! I sent the picture to Bethany,” she admitted.
“Oh, shit,” I said.
She didn’t answer at first and I just waited as I watched Jillian worship that cock. She took her time, using her hands and tongue to pleasure the dick.
Dani returned a moment later, her tone back to sexy, “Sorry for the delay, do you like?”
I grabbed my phone and gasped, “Holy fuck!” It was a picture of my wife with a vibrator I had never seen in her pussy and a butt plug in her ass. She wasn’t lying.
She asked, her tone sultry, “Is that a yes?”
I answered, still staring at the picture of my wife, “I can’t believe what I’m seeing, but a million percent yes.”
She explained, “Bethany convinced me to stop being a prude and experiment.”
Still wanting to stress I loved her regardless of her sister’s assessment, I said, “Well, I never want you to do something to prove yourself to someone else, including me.”
She countered, “But what if I want to?”
I said, with a big smile she couldn’t see, “Then the luckiest man on earth, just got luckier.”
She said, “I love you.”
“I love you too, sweet pea,” I said back, loving her for who she is and also who she was being tonight.
She said bluntly, “Now let’s phone sex.”
I asked, still staring at the picture of my wife with both her holes filled, “Do you like the toy in your ass?”
“Actually, truthfully, I kind of want to switch to the bigger one,” she admitted, which made my cock flinch.
I said the obvious, “Shit, I wish I was there,” as I glanced at the video and saw the step-mother had joined and was sucking cock, while Jillian sucked on his hairless balls. I wondered if I should shave my downtown area.
She shocked me again with a blunt question I never, ever thought I would hear come out of her lips, “Do you want to fuck my ass?”
I wanted to scream yes. I wanted to tell her it was one of my biggest fantasies. Yet, not wanting to sound like a pervert, I lied, “I truthfully never considered it.”
“Really?” she asked, sounding insulted by my answer.
Immediately in fix mode, I explained, “I don’t mean that in a disrespectful way. It’s just not something I imagined you would be interested in doing.”
“And if I am?” she asked.
I answered, as I skipped ahead in the video wanting to see Jillian ass fucked, even though I couldn’t remember if she was in this one. Thankfully, there she was, taking it in the ass on his desk while her step-mom felt her up. I watched the scene, and then glanced at the photo of my wife as I said, meaning it, “I would do anything with you.”
She pointed out playfully, “Anything is a pretty big word.”
I said, thinking maybe one day she would fuck my ass, giving just the slightest hint of my own growing submissiveness, “And I mean it.”
She moaned, “Good to know, but now I need to come, baby. Please tell me a story… a naughty, naughty, story.”
I pondered a plethora of stories before deciding to do one of my old fantasies… the slutty cheerleader. I began, “Well, I return home from a long week to find my wife in a cheerleader outfit and thigh highs.”
She moaned, ever so softly as I continued, “You’re waiting at the door, pom poms in hand.”
She asked, through moans, “Am I on my knees like a slutty college cheerleader?”
“Oh yeah,” I groaned as I began using the fleshlight again, the image of my wife on her knees in a cheerleader outfit turning me on. I quipped, “On your knees and ready to please.”