Butt Plug Training Stories

Butt Plug Training Stories
Butt Plug Horror Stories (As Told By Really Embarrassed People)
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By Rebecca Jane Stokes — Written on Feb 09, 2017
Butt plugs are hand's down one of the best sex toys around.
If you haven't used one, let me just tell you, you are SERIOUSLY missing out.
For men, butt plugs are a great way to explore the fast and sexy unknown (you know, the prostate) .
For women, butt plugs can heighten sensation during orgasms and make for a great tool if you're into being teased, and let's face it, we all love a little teasing now and then (and I refuse to hear otherwise.)
But if you're new to butt plugs they can be a little, well, scary.
Why's that? Well, because unlike your vagina, your butt isn't designed for stuff to go INSIDE.
If you're playing around with butt plugs and you use the wrong tool, a butt plug can actually get LOST inside your body making for one of the world's most awkward ER visits.
Also, a lot of people rush into using their butt plug. I don't mean they make the decision lightly, it's not that big I deal.
I mean they literally rush in, minus lube, and cause themselves a world of hurt.
I think these sorts of fears keep people from exploring what can be a totally bomb sex experience.
To that end, I rounded up stories of butt plug sex toy horror from my friends (who because they all have real jobs and parents have asked to remain anonymous).
You should know that none of the people here QUIT using butt plugs because of a bad experience. Instead, they learned, moved on, and got better at embracing the butt plug!
And here's a bonus story. It's not about a butt plug, but it's definitely about a butt!
"My story isn't really about a plastic or even glass butt plug. It's about my ex-husband's real penis tho!! Lol. We were in his parents' camper and long story short, he took my ass virginity. The hilarious thing about it is that as he pulled out, I couldn't stop farting! Yes, I had uncontrollable gas!! What I thought would be an embarrassing moment turned out to be extremely hilarious to BOTH of us!"
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on Sep 17, 2017

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Our sex life had pretty much returned to our regular routine, except for the addition of anal sex, when I was aroused enough to ask for it explicitly. Then one night I again awoke to the feeling of massage oil being rubbed around my entry hole and a finger slipping in and out of my ass.
I smiled sleepily waiting to feel my husband press up against me. Inst...

He told me my training for the next several weeks will be intense. Why? Because He can and wants to. i get scared and excited. When things get intense with Him, He really means it. As His anal submissive slut, i endure what He wants for his pleasure and my instruction. He says He will give me details later on what will be expected of me. Knowing Him, He has...

First let me tell you a bit about ourselves. My name is Kurt. I am 5'9" tall with a closely shaven head. I pride myself in my ability to keep my body toned, but I am by no means a gym rat. As my love of my life, my wife, Kala has measured many times before, my cock is 7.5" long when fully hard with a nice engorged bulbous mushroom head.
My love, my companio...

For as long as i can remember, the thought of Him sharing me with anyone else terrified me. my love is an all-encompassing one and the thought of either of us being with someone else is revolting to me. When He says it, i feel as though He doesn't really care. That i am disposable, able to be given away at a moments notice. my security and comfort as His sub...

It all began with Him telling me we were having a party for the Superbowl. To most that would seem like nothing out of the ordinary, but to me, it made my mind race.
Maybe I should back up a bit and explain the relationship so you might understand. You see, He is my Dominant and I am his anal submissive slut. That means that He directs what i do daily and...

I didn't need the money, but I made a profile on the sugar daddy website anyway. In the about me section, I wrote "Young female slave looking for master. Inexperienced, needs training". It wasn't long before I got a message in my inbox from a tall, attractive man with an incredible smile.
"Saw your post. I'd be interested training you, and I'll pay you $100...

Michael sat in the chair as she entered. Powerone had described her perfectly, long black hair, green eyes, pale skin, very small hands and fingers, DD breasts and small hips. She had a gothic look to her, the black clothes standing out dramatically to her white skin.
"What am I doing here?" Violet questioned, but she already knew the answer. Powerone had o...

As soon as Hank and Anastasia are outside, his grip on her arm tightens just the tiniest bit as he lead her into the parking lot. Hank walks them to a far deserted corner of the lot, where he has parked his motorcycle. When they reach the bike, Hank turns Anastasia towards him and kisses her passionately. As his tongue snakes its way into her mouth, Hank's h...

We decide to meet at a hotel, as both of our houses are busy lately with the kids being at home and our spouses off. It's been a while and both of us are anxious to get together. You've been using your butt plug trainer for a few weeks and now think you're ready for the next phase. I know I'm ready to take you there.
We meet in the downstairs lounge for som...

Hello pet. Welcome back.
Are you ready for the next stage in your training?
Good.
You're such an eager obedient pet aren't you? Such a slut.
Today you are going to need the following items
- Bra and panties
- Stockings, ideally with suspender
- Butt plug
- Vibrator/dildo
- Lipstick
- Perfume
You will also need plenty of time. I'm not going to...

In parts one, two and three, I told you how my wealthy father used bribery to keep me a virgin until my eighteenth birthday. On that happy day, he handed me the keys to an expensive imported car and a letter of acceptance from the finest university in the country. Both bribes had cost him dearly. After my fabulous birthday party, Daddy called me to his study...

Naughty New Neighbors: Ass Training
Summary: Rick begins Chrissie's ass training with a little help from sex shop sales girl Zoey
Note 1: Thanks to Jasmine, and LarryArcher, for their helpful suggestions and wonderful editing of my story. I can't thank you enough.
Note 2: Special thanks to Jasmine whose stories have inspired me to write.
The next morning...

II. Training for anal intercourse
How many times have you heard of this scenario played itself out. Perhaps it's an experience you have had. A man pleads with a woman to try anal sex. With some misgivings, she consents because he wants it so much. Excited, he tries to thrust his penis into her ass, causing pain when her inner sphincter is forced open and th...

Little Karen realized that her experience dominating Emily's sisters had given her wonderful preparation for the challenge of disciplining and training her own mother, Marian, now that the latter had come to live with her after burning all of her other bridges of support.
Karen, who was all of 25, and Emily, only a year older, had begun the training process...

Not for nothing are "Ghost World" and "The Doom Generation" my favorite films. I was made for a stark black bob long before I ever got one, before I saw those movies and even before I discovered black hair dye. Without it I might have ended up looking something like Lotte Lenya in "From Russia With Love." Goddess bless Manic Panic!!
It's more than the hair,...

Today was to be like any other with Mistress Mona except that when I arrived at Her dungeon home, I saw a beautiful tall blonde woman there. Soon I learned that this was Mistress's new friend and a new Domme. New to the art of Domination that is!
Mistress informed me that I was to address this new woman as Lady Denise until She had sufficient training, than...

Chapter 2 - The Following Week
After You leave, i'm left with one dildo humming in my ass and another grinding away against my cock. i cum with a great sensation, my anus contracting around the dildo in my ass and pushing it out as my cum explodes from my cock. i lie there for a bit, relishing the wonderful training You have given me. Then i remember the li...

CHRONICLES OF THE "SPECIAL" YOGA STRETCH
My boyfriend/ live-in lover/ best friend of three years had mentioned anal sex many many times. We had tried it 2 or 3 times and had to stop because it was VERY painful for me! A few weeks ago, I had a short discussion with him that I didn't know if we'd ever be able to have anal sex unless I went through some "anal...

This is all fiction. This is all improbable. That's the point. Thanks for reading.
Porn is a dimension as vast as the expanding internet and as timeless as a firm spank on the ass to make her jump. It's the naughty ground between mind and words but never deeds. Between a world that sucks with many horny men and one that looks like our own. It's comes from...

I'd been flirting with a guy that I had met for some time, trading raunchy texts back and forth. He would come up with all sorts of nasty things he wanted to do to me and I'd always respond that I would. He would get bolder and bolder but nothing ever scared me off. I thought he was hot and got a feeling that he was a confident guy but I wondered though if h...

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Kinky sex over sixty, mature man enjoys older woman.
Sissy Adam trained to accept nectar.
Past butt plug pearls pussy lips punishment.
Professor helps airport security inspect her intimate parts.
Deciding to go drag one last time he wants his man!
Becky's blackmail continues as Steve trains her for anal.
Denise's high stakes dinner for Joey with special dessert.
Secret romance between a ponygirl and her handler.
Kitten decides to surprise Daddy with “lunch”.
Crossdressed at a party he has to decide, gay or straight!
I came at work and showed a coworker too much.
A gf's end to a complete slut experience of the night.
First time called a sissy and serving at a party.
Yasha escapes the church then runs into a meal on two legs.
Having beaten me at wrestling, my friend proceeds to fuck me.
More bondage adventures in the attic.
August has another surprise for Jules!
Mistress and Charlotte having a much needed play date.
Callum matches with Alima on a dating to try to fulfill her.
Plug play and a young lover gives his first facial.
Meanwhile, at the Princess Asshole Hospice…
A wife knows almost too much about her husband's fantasies.
When Jen lost a drunken bet I had to step in to help.
Bored, my best friend proposes we play a novel, kinky game.
Day 4 and Diana is Harry`s sub plus fun in the sauna.
Rachel expands her horizons and one of her holes.
After all that's happened, can Alison and Eva be reconciled?
Joseph tries to be helpful, but gets pegged instead.
A man finds true love at the cost of his freedom.
An unexpected person from Ava's past arrives.
A woman submits to a professional acquaintance.
Three women kidnap man to harvest his sperm in a cruel way.
Scott and Anna continue to explore their hidden desires.
His girlfriend can’t fall asleep without sucking on a dick.
A couple experiment with a new dynamic.
The sissy training intensifies as Adam learns his place.
Another gift, another game as the woman finally reveals all.
My nude daughter, her friend, and I get riskier.
Richard prepares to welcome Master James home.
What to do on a one year anniversary? All sorts of things.
Welcome to Briarton, where most everybody enjoys BDSM.
Young sub recounts her bondage face fuck dream to her Master.
I wore a vibrator and butt plug at a family dinner.
The Pool Party gets a bit out of hand.
Sissy gets tested and Crystal gets a strap-on.
Jen's discovered trying a plug the first time while shopping.
BDSM fantasy with spanking, rectal thermometers and more...
Star and Joe make babies. Zephyra and Myrine await visitors.
He's a family man... with a pretty slave-boy in his basement.
Our shopping spree continues and more.
The shopping spree begins and humiliation continues.
A gf's slut pussy tenderized as her past-fuck visits present.
The pretty son of a mob boss becomes his rival's plaything.
A disussion leads to a mutually beneficial punishment.
A mistress writes one final message to her loyal slave.
Our night of fun continues and things get crazier.
An enslaved couple embraces their submission.
We continue our new way of life with a new surprise.
Liz becomes the pet of a young and hungry power couple.
My daughter reveals her secrets to me.
Jane remembers their first time with a cane.
His plug leads him to some steamy sex in the car park.
A gf's crazy sexual past unwraps when she gets slutty.
A need for the toilet leads to unusual camming encounter.
My bitch disobeys the rules and is severely punished.
Richard is given his new schedule as Mistress' sissy maid.
Their first night together, and Emily is punished.
Max's Master invites a special guest.
Mistress, Charlotte, Juliet, and a change in family dynamics.
High Heels, Butt Plug & New Schedule For Sissy.
Mistress buys Richard high heels & a butt plug
She enjoys a full filling walk alone in the park in bondage.
A spanking assignation takes a surprising turn.
Third story in "Lindy my slut wife" series - sub wife
Public play in park with a butt plug.
Hanna has a first face to face session with her new mentor.
Kelly's friend-zoned buddy Mark gets his revenge.
Marjorie Taylor Greene gets punished and dominated.
Her dreams of being double teamed come true.
One mistake leads to Lisa's punishment and gangbang.
She volunteers as a sex ed subject to reduce her sentence.
My girlfriend puts her ass on the line.
The party continues and my ex learns a lesson in control.
Lisa takes a butt plug then is forced to squirt.
I can’t help but go back for the final hole.
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Thoughts I Had While Wearing a Butt Plug for the First Time For anyone who’s curious about what a butt plug feels like for the first time.
Thoughts I Had While Wearing a Butt Plug for the First Time
Thoughts I Had While Wearing a Butt Plug for the First Time
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Butt plugs may not sound glamorous to some.
My ass is on my brain because my lover has requested I arrive to his place with the butt plug he purchased for me already inside me. I don’t mind the request, it’s kind of our thing. He’s the dom, I’m the sub. But this is much different than the “garter belt and heels” requests of the past. Not only that, I have to be there at six, which means I have exactly 10 minutes to get to his place if I want to stay on schedule.
I have no idea how to actually put a butt plug on (in?). I’m running out of time and who knows how long it takes to watch a freakin’ butt plug tutorial. Come to think of it, who knows where to even find a butt plug tutorial?! I know I could Google it but, ugh, do I really want to see the results of ‘Quickest way to put on a butt plug’?
Oh wait! This thing comes with instructions! Beautiful, beautiful, search history-less instructions in seven languages (Did you know “butt plug” in Dutch is “butt plug”?)! Okay, something about a 45 degree angle (Geometry?!) and using lube. “I have lube!” I shout to no one. ‍
I stick my finger ever so slightly in my asshole and immediately start having flashbacks. Not “finger in butt” flashbacks, but flashbacks of my, yes, more than one trip to the gynecologist with tampons stuck inside me. I know this is a different hole, a different time. But still, I worry.
Wow. It’s in! That was easier than expected. I’m still breathing, and hey! I can walk! And kick! I’m like a kinky Sally O’Malley !
Uh-oh. I forgot to walk the dog. Shit. No. Don’t say that word! Darn. If I walk the dog, I will officially be running (waddling?) late. He’s giving me the eyes, poor thing. I have to.
Thank God, all he had to do was pee real quick. My sweet angel pup gets me and my tardy ass. I reward him with treats.
When I signed the lease to my apartment, I felt blessed with a .2 mile walk to the subway. But suddenly these four minutes walking to the train feel like a hike. It’s not that I physically feel the butt plug inside me but mentally it is screaming. I remember to relax my face.
Okay. I’m officially on the train. Whew! Although, do I sit? Stand? I’ll sit. Slowly.
I’m holding a magazine although I haven’t read a word for three stops. I wish I paid more attention in the dozen yoga classes I’ve been to. Knowing how to properly breathe would be good right about now. Is it through the nose out the mouth or the other way around?
I feel like I’ve been sitting too long. I sit up straighter. Even though my lover can’t see me, I pretend he’s watching. I think I’m smiling too much. Reign it in, Carolyn. Nothing to see here, people. Just your average Sunday evening commuter...who is starting to feel warm. No, hot . How can you tell the difference between summer heat or butt plug heat? Shit. No! Darn! What if it’s like some sort of butt-Toxic-Shock-Syndrome-thing? The weather app says it’s 86 degrees out. Summer heat.
We’re off the train. We’re off the train. Butt plug and I are apparently a unit now. We’re connected, we’re attached, we’re...about to fart. Is that allowed? Of all the days to drink a pot of coffee and eat broccoli. Always self-sabotaging, Carolyn! No, stop! I can’t be negative. Negative is... clenchy. Positive thoughts only. Note to future self: Next time, I’m asking for a full, 12-hour notice before butt plug requests.
The walk from the train to his apartment is usually my favorite part of the night. It’s just long enough to listen to a sexy song so I arrive wet and aroused. But I’m deciding against my usual routine tonight because it just hit me that I’m wearing a dress with no underwear. If I’
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