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Old 11-13-2016, 04:52 PM   #1
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Default My switch partner's revenge

I wrote this story years ago, but never edited it. I'm going to go through it, edit it, and post it here. I'll do it in chunks to allow for suggestions.

I marked this as fiction, but really this is an exaggerated telling of a real bet/challenge that I experienced pre-transition. At the time, I was heavily suppressing my gender, but these events opened me up. It will contain bondage, sex, and crossdressing.


My name is Allen. I grew up next door to a girl named Katie. We had been good friends, but it wasn't until I left for college that we became more than that. Despite years of summer afternoons sitting in the park talking as teenagers, it took an internet conversation as twenty-somethings to discover we each had a kinky streak. So we did they only thing that made sense at the time: we were now long distance fuck buddies.

Don't get me wrong, I was loving our arrangement, but I felt she was holding back quite a bit. She normally has an edge to her, but it was lacking during playtime. After my second trip home I risked the awkward response and asked her why her bite didn't quite live up to her bark. She claimed she didn't feel confident bringing the kink factor up - she was afraid of doing something I didn't like. I assured her that she should just go for it and I would tell her if I didn't like something she tried.

Then I came up with the idea that would come back to haunt me: I created a challenge for us. The next time I came home, we'd have two nights of play. Both nights would dedicated to testing each other's limits and seeing how far we'd go. We would make a game of it - our goal would be to find what makes the other one utter their safeword. She asked if I would be the dominant one the first night. She thought me establishing the boundaries would make her feel more at ease doing the same to me. I agreed to.

A long couple of months after that conversation, I made a trip home for ten days and my first full day back was spent with Katie. I really hadn't done any planning of what to do with her. I have fun playing dominant, but my submissive streak is what drives my fantasies. However, I knew the more aggressive I became, the more comfortable she'd be when it was her turn to dom. After a little bit of small talk and catching up, I attempted to flip the switch.

"Alright, Katie, if we're going to do this, I want to know you want it, and words aren't going to be good enough. You're going to volunteer to be my bitch for the night by looking the part. If you want to play tonight, you're going to go to your room, put on your sluttiest outfit and these cuffs behind your back. When I open the door in 15 minutes if you are slutted up and on your knees, we will have some fun. Otherwise, I will be spending the night at the bar."

She looked a little shocked, but after only a moment's thought she went to her room. While she was in there I ran out to my car to grab my toy bag. When I walked in 15 minutes later, I was pleasantly surprised to find her as I asked.

"Very good, Katie. Now I don't want a word out of you unless I ask you a question or you want me to stop. If you let me push you I think you will have fun, but I want you to know that if you say stop I will. Now that we have that out of the way, I believe you missed a couple things. First, that top screams sexy, not slutty. Let's lose it."

As I pulled it up over her breasts, she made the bra choice I was hoping for.

"Hmm, no bra. Well, I'll give you half credit on the top. Now get on your feet, Sweet Tits. Let's pull down that skirt and grade your underwear choice. Well the skirt was short enough and the thong was the right way to go, but I couldn't see it while the skirt was on. Let me fix that for you."

With that I grabbed a firm hold and pulled up, giving her a wedgie that was a little more extreme than I originally meant to. I never intended to literally lift her off the ground, but oh well.

"And I just spotted another miss that I can fix for you."

After throwing her face first on her bed, I made the first mistake that would come back to bite me: I pulled out a pack of colored sharpies.

"Every slut needs a tramp stamp and you are about to get one, you can thank me later."

Now it didn't look quite as artistic as I thought I could do, but a few minutes later she had a heart book-ended by cocks that read, "Allen's Little Slut."

She didn't seem happy, but let me keep going, so I went on to make my next big mistake.

"One last touch is needed - where do you keep your makeup?"

I proceeded to do my best to give her a whore's makeover. Really, I made her look like a six-year-old playing with mom's makeup, but it had its desired effect. I could feel her steaming while I did it.

To be continued with the rest of Allen's night in control. Feel free to make any suggestions for what you'd like to see Allen do to Katie. Just know that it might come back to haunt him when it's her turn.
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Old 11-14-2016, 03:26 AM   #2
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I may be the first to read the story. But I will pass your dare to the next reader.
Thanks
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Old 11-15-2016, 10:49 PM   #3
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Default Part 2

The rest of the night I tried everything I had ever wanted to do.

I was already very hard, so I helped her to her knees and told her to suck. With her hands cuffed, I grabbed the back of her head and pumped her face. I didn't mean to get this rough this early, but I was already full of lust. Feeling a rush of domination like I never had before, I pulled out and finished on her face. She looked stunned - we had discussed facials as a fantasy before, but I don't think she expected me to do it.

I used my finger to transfer the globs of my seed from her face to her mouth, while leaving plenty of residue. After getting her to her feet, I blindfolded her, uncuffed her hands, had her lie on her back on the bed, and cuffed each wrist to an ankle. I left her there for about 30 minutes. I needed to catch my breath, and I assumed she could use a mental breather.

When I came back, I flicked a lighter close enough to her to hear it and lit a candle. This was one of her strongest fantasies, so I wanted her to know it was coming. I gave her just a quick drip on her upper chest to let her experience it and give her a chance to stop me. When she bit her bottom lip I knew she was all in. I started slowly dripping wax around the edges of her breast, very slowly moving inward. Each drop elicited a moan that sounded more lustful than painful. When I reached her nipples, she was in absolute heat. I set the candle down so that my tongue could get to work.

She has a bit of a foot fetish so my mouth spent a bit of time at her toes before working its way up her legs. Once I got to her inner thighs, she started thrusting the air. After finally reaching her clit I gave the tiniest nibble and stopped.

I watched her squirm for a minute before pulling out her vibe. I held it a foot above her and enjoyed watching her arching desperately to reach it. I let her get just a graze of it across her dripping wet clit before I removed her blindfold and threw her vibe to the other side of her bed.

The visual of her inch across the bed to start humping the vibe is to date the most enjoyment I have ever gotten out of being evil.

By the time I grabbed some lube she had almost reached climax and I had to dive to take her vibrator back. While I gave her a moment to come down, she got up on her knees and I couldn't wait any longer. She was in the perfect position. With her wrists still bound to her ankles, it left her with her ass up, head down.

Since she was so kindly presenting, I gently introduced my cock to her backdoor. In an attempt to condition her to enjoying anal sex, I reached around with the vibe to also stimulate he clit. I was gentle until I fully enter proceed to ravage her. It didn't take long for both of us to explode.

I unbound her and let her go shower, but as soon as I was ready to go again I burst in, pushed her against the wall, and entered her sex from behind.

The rest of the night involved all the bondage positions I ever wanted to try on her. We were spent and I didn't have energy for much else. It was actually a little sweet, I took care of her and she looked adorable bound. However, when we retired for the night, she only wore a pair of cuffs. I wanted her to sleep knowing that I owned her tonight.

Next time: part two of the challenge begins, and Allen finds out why going first may have been a big mistake. Any desires for how Katie exacts her revenge?
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Old 11-18-2016, 11:03 PM   #4
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Default Part 3

After I uncuffed her in the morning, I asked her how that was for her. She said that the first part moved a lot faster than she expected, but she was determined not to be broken. Once she made it through that, she had a lot of fun. Then a wry smile crept across her lips as she said she looked forward to night two, where she prove to be the better dominant.

It took five whole days before it was time for night two of our challenge and it was all I could think about in the meantime. When the night finally came, she wasted no time getting started.

"You are going to volunteer just like I did, except you are going to be wearing nothing but these."

She handed me a pair of leather wrist bands with D-rings attached. I tried to contain my excitement as I stripped and fastened the cuffs.

"Alright my little bitch, on your knees, close your eyes, and put your hands on your head."

As expected, I felt her pass something through the D-rings, but I was surprised when I felt a gag pushed into my mouth and quickly secured. I opened my eyes to find she fed the straps of a ball gag through my wrist restraints, gagging me while also binding my hands to my head. To finish my current outfit, she added a dog collar and a leash before informing me how I went wrong five days ago.

While Katie may normally have a confident sass to her, she does have some body-confidence issues. She also absolutely loves makeup. So when I gave her that Sharpie tattoo and a butchered makeover, I had unknowingly created a monster.

Her tone suddenly got more threatening than I expected from her: "I know you were expecting some teasing and rough sex, and I suppose that will come in time, but before you get anything resembling pleasure some revenge is in order. You know how hard that tramp stamp was to get out? Well you're about to find out because you are going to get cock tattoos all over your body. And don't even bother looking for soap tomorrow morning because you sure as hell aren't leaving this apartment without your new body art. I'm also going to return the favor on the makeover. Honey, we're going to make you prettier than a pageant queen in Texas, so lets get to work."

To be continued. What humiliations await Allen in part 4? Comment with suggestions.
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Old 11-19-2016, 04:44 AM   #5
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Nice story so far I hope there will be more parts.

But there is one thing you could make better: Be more detailed when it comes to the kinky stuff. I read a whole day/night in just a few minutes
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Old 11-21-2016, 10:13 PM   #6
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Default Part 4

As she dragged me by a leash to her bathroom, my erection ran away so quickly, I thought it was going to go inside my body. I was hoping she was going to unleash her evil side, but I was picturing it in a sexier way.

She made me stand in the shower and reached for a bottle of Nair. While she let that burn my skin off, she shaved my already trimmed pubes into a very sexy, yet feminine, landing strip. When she washed off the rest of my hair, she only used cold water. I was not having any fun, but she didn't care.

With a firm slap to my ass she ushered me back to her room and pushed me on her bed, and I knew what was next. It felt like she worked for hours and later in the night I would see what took so long. She started off nice enough and gave me a traditional butterfly tramp stamp. However, the rest of my body didn't fare well. "I <3 COCK" was written across one forearm, a gay slur on the other. "Property of Katie" and "USELESS" were written on my inner thighs, framing my cock. My chest read "CUM DUMPSTER" and my stomach "SLAVE." My nipples were enlarged with a red marker to look like hearts. One ass cheek had "Insert Cock Here ->" and the other "USE ME." And in elegant cursive, the back of my thighs read "Katie's Bitch." She finished it off with about a dozen penis drawings in empty space throughout my body.

"Alright, Darling, now that we got you inked up like the dirty little slut you are, let's tart you up."

She started by dressing my lower half. Soon enough I was wearing fishnets, and a mid-thigh length, tight black skirt. I never got underwear because I was a "naughty little [trans slur] slut." Before removing my binds, she sat me in a chair, locked my legs to the chair's, and gave me a warning that I'd regret making a noise or movement that she didn't allow. And with that, the gag was removed, freeing my arms. In short order, I was wearing a stuffed black bra and with a tiny, white blouse that was tied below my chest. My chest and stomach tags were left visible.

Now that I was dressed, she bound my wrists to the arm rests of the chair and pulled out her makeup. I lost track of all the powders and liquids she attacked my face with. When she got to my lips, I didn't follow her instructions to pucker and she dug her heel into my thigh. That ended of my meek resistance.

I made her job easy by keeping a nose-length, hipster-style haircut which she was able to pin back and finish off with a ribbon. After some lashes were glued on, she finished the look with a Sharpied on, Monroe beauty mark. When I finally saw a mirror, I saw that I had smoky eyes and overdone cherry lips.

I got healthy doses of perfume and glitter before she moved onto my nails. While she glued on and painted my new 3/4" nails, she really turned up the bitch in her like I never thought possible.

"Wow, look at you. You do realize you volunteered for this, right? And you never even fought back. What kind of a man are you?"

I had no response. I was in shock - she had broken me. I thought I could not feel more defeated. However, once she pulled out her camera, I realized she still could do a lot more damage.

To be continued. I'll gladly inject suggestions into part 5.
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Old 11-22-2016, 12:19 AM   #7
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I'm loving the story. Hope you incorporate some public/semi public stuff
also, can't wait for the update!
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Old 11-22-2016, 09:41 PM   #8
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Default Part 5

After taking plenty of pictures of me, she unbound me from the chair only to push me on the bed. With two sets of leather cuffs, she quickly hogtied me. From there, it was more pictures.

"Mmm - your debut as a bondage model is a success. I need to transfer these now for safekeeping."

While she left to go to her computer, I had nothing better to do but wonder how this happened. All I had wanted was her to try something a little more than just handcuffs. Boy, did I get so much more and the night was only halfway over. I had to start to wonder if she went too far, or was I starting to enjoy this?

When Katie returned, she sat in front of my face, spread-eagle and pantyless. She lifted my head off the and planted herself under it. It was clear what I was to do so my tongue got to work.

She started laying into me with insults again. It was a non-stop barrage of reminders about how weak I was. I went to town on her with my tongue just to try to get her to stop talking. Not to brag, but her insults started turning to moans and my chin was covered in her juices.

After she caught her breath, she announced, "It seems you messed up your makeup while you were whoring it up. I'm going to let you go, but if you even think of doing anything without my permission you will regret it. Got it, Ali? Hey, slut! When I ask you a question I expect an answer."

"Yes."

"Yes, what?"

"Yes, I got it," was my reply, which earned me a stinging slap to the face.

"Try, 'yes, Mistress Katie.'"

"Yes, Mistress Katie."

"That's better, now go fix your makeup."

I gave her a lost-puppy look for a while before I replied that I didn't know how.

"Well you're about to learn, honey."

As she instructed me through it, the camera reappeared. She now had pictures of me voluntarily applying makeup.

Despite my good behavior, she reached for the bondage gear once my makeup was repaired. This time she laid me back on the bed and bound me exactly as I had done to her days earlier: each of my wrists bound to its respective ankle, leaving my legs to naturally open up for her.

To my surprise she started kissing the front of my hips, which drives me insane in a good way. She unbuttoned my blouse and slowly worked her way up my torso. Her hand worked her way underneath my bra and began to tweak my nipple, as I had done to her many times before.

She gave me a couple ear nibbles before she whispered, "remember when you gave me a hickey and I had to wear a scarf in the middle of summer? You think you can pull that look off?"

I didn't even try to fight it and she went to town on my neck. There would be no hiding that one, but I strangely wasn't worried about it. Instead of being self-conscious of her marking me, I was so horny that I could only think about getting relief.

With me hot and bothered, she predictably stopped and demanded that I beg for her to let me cum. Although I quickly ditched my dignity and begged for it, she had something else in mind.

"Why don't you show me what you want?"

My heart sank as she pulled out a large, floppy dildo, complete with a flesh tone, veins, and balls.

"Open wide, slut."

I never clenched my jaw tighter in my life. Even as she started slapping me across the face with the cock, I refused to open up.

"Alright, you little bitch, if you want to play that way, fine."

She pulled out a bottle of lube.

"You have two choices: you can suck it or get fucked by it."

I opened my mouth, but that wasn't good enough now.

"You were so resistant to it before. If that's really what you want now, I want you to convince me that you want to suck my cock."

"Please let me suck your cock."

"Wow, that's not convincing at all. I want you to prove to me that you are a filthy, cocksucking, cum-dumpster. Otherwise, I'm going to pound your ass"

"I'm such a slut, I need to suck your cock."

She started to pour lube over her hand.

"I'm a dirty cocksucker, I need your cock."

Her hand started to enter my ass, lubing it up.

"I want to suck you cock so bad, please let me."

She started to probe my ass with just the tip of the dildo and I panicked.

"I AM SUCH A FILTHY SLUT WHO IS ADDICTED TO COCK! PLEASE TREAT MY LIKE THE CUM-DUMSPTER WHORE I AM! FUCK MY THROAT, I BEG YOU!"

"Well, you have me convinced that you're a cock-gobbling slut, but I think the world needs to know."

I then received two more tattoos: a cock, jizzing in the direction of my mouth on my left cheek and an "deposit cum here ->" on my right.

SNAP! Another picture.

She exchanged the camera for the dildo and teased me by holding it over my head to make me reach for it. Not wanting to anger her more, I played her game. As I stretched my neck to reach, I was just able to reach it with my tongue.

Just as I was able to touch it, she slammed it into my mouth and gave me a violent throat-fucking. I was doing all I could just to not choke. As my eyes began tearing, she gave me just a second to catch my breath before she inserted it again.

"You better not spit it out unless you want round two."

Of course, she took more pictures before she left for what I can only imagine was another picture upload. How much blackmail material did she need on me?

To be continued. The night comes to a close in part 6. How else should Allen be abused?
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limits: pics with face, messing with sleep, public, heavy blackmail, videos, permanent, scat, extreme pain Note: I transitioned years ago - wearing women's clothes isn't a dare. If you give me a sissy-themed dare, I will ignore you.


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Old 11-23-2016, 11:29 PM   #9
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I just want the rest of the story. I'm loving this so Hard right now!
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Old 11-24-2016, 10:09 AM   #10
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Ally likes! <3
I look forward to the next part!
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Old 11-26-2016, 06:53 AM   #11
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Please post the next part <3
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Old 12-01-2016, 08:03 PM   #12
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Default Part 6

"Just to let you know, sweetie, I had only planned on teaching you how to suck a cock, starting with gently working the tip before you gradually went deeper. Since you wanted to act like a cunt, you got throat fucked like one. Now even though you don't deserve it, I am still going to give you relief, but that cock ain't coming out of your mouth for your misbehavior."

She thankfully went down on me and didn't stop this time. With how long I had been used without relief, I was ready to cum in what seemed like seconds. She could sense it and dipped her arms under my legs. She used her shoulders to lift my legs over my head. I could tell what she was doing when she started jerking my cock over my head, so I tried my best to resist.

I thought of baseball, old people, anything to distract myself from reaching orgasm, but it was no use. When I started to cum it felt like it was never going to end. Splurt after splurt splashed against my face, with a lot of it pooling in my eye socket.With my face covered, I was sure that I looked like the picture of the cum dumpster whore she had called me, even if I couldn't see it myself. And there are, or course, now actual pictures of me in this state.

While she left to make her final picture upload, I was left to let my own cum dry on my face. The sight must have aroused her because we had a round of conventional sex as soon as she returned - if you can consider her riding my bound, feminized, and defiled body in a reverse cowgirl to be conventional sex.

When she was satisfied, she removed the cock and let me wash my face before bed, though I couldn't get the sharpie completely off my cheeks and my hair still felt caked with cum.

When I woke up thinking the game was over, she did follow through on one last humiliation. She graciously let me change back into my boy clothes, but that was the only luxury I was allowed. I left her apartment with red talons, glittered up like a stripper, and smelling of sex and perfume. As promised, I was still covered in cock tattoos, including an only slightly faded one on my face.

This is where what really happened comes to an end. "Katie" kept the pictures and would occasionally email me one as a tease, but we never approached a night like this again. Years later when I came out as transgender, she was completely supportive but tragically straight, so our games ended.

However, I labeled this story as fiction for a reason. So in part 7, a "what if" fantasy - Katie blackmails Allen into servitude!
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Old 12-02-2016, 02:08 AM   #13
Sydney_sub
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Thanks s much for this story, looking forward to part 7 I wonder if any of her girl friends will be involved ????
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