This story has a bit of a build-up to it. If you’d like to skip forward to the sex, hit CTRL-F and search for BUSINESS TIME.
Technically, this is a SoCalr4r success, even though things didn’t go as planned.
I was looking for someone to play with me and my good friend, Mr. Scarecrow – a nasty piece of wood, chain links, a dog collar and some wrist straps. When Mr. Scarecrow is strapped to you, you have only one choice: Keep your arms straight out and let me do whatever I want to you.
I was very clear in what I wanted from a play partner, and I was very honest about who I am (but not self-deprecating).
And then I got this one response from a redditor we’ll call Miss Kay. It really stood out, with the subject line, “Any chance you’re in LA longer?”
*Hi! I saw your post and it turns out I’ve read some of your stories before in the past. I’m definitely really interested, but am out of town right now unfortunately.*
She went on to describe herself – younger than me, significantly shorter than me, and with an emphasis on nice boobs. She noted that she didn’t have a lot of kink experience, but really wanted to give Mr. Scarecrow a try.
To be honest, I thought there was an 11% chance this was a real person, and maybe 89% chance of a catfish. I’m skeptical, but polite in these situations. To be fair, I’m this way with almost ALL of my online chats. I get to know people and see if we click on a sapiosexual level. I poke through their post history, and I flirt. I limit the amount of personal information I give until we build that trust up.
Miss Kay had a decently aged account, and a really well-written success story about another meet-up. I’m intrigued. The flirting intensifies, and we’re chatting about anal hooks, CNC and other kinks. Then she point-blank asks me if I’m interested in playing with her when she’s in LA.
Dumb, horny me would probably have set up a meet-up then and there on the spot. Slightly experienced but still horny me took a deep breath and talked about how I like to do verification. I listed off a few options, including one of my favorites, her holding up a little sign that says, “Hi Casey.” This is where a lot of these chats can go sideways. Catfish make up fascinating excuses, and shy girls tend to ghost out.
Miss Kay sent three different versions of the photos I mentioned I liked, all with a half hour.
My first thought was she had amazing lips. Lips that said, “Kiss me, then facefuck me.” She wasn’t lying about her tits. Her body was stunning. It was at this point that I was dead certain I wanted to fuck her.
Our conversation ramped up, and eventually spilled over to a chat app. We swapped more pics and went over fucket lists and kinks and limits. I mentioned how I’m looking forward to hearing her moan, and she had an idea: I would text her instructions, and she would masturbate on the mic for Daddy.
It had been a while since I’ve done anything phone sex-related. But right away I was into it. I had her give me a run-down of what toys were available, and what clothes she had on. I had her strip down, insert a butt plug, then tease herself with the dildo. She started to beg like a good little girl, so I let her start using a dildo and vibrator combination.
Within the first two minutes, her moans slid into begging. She was already needing to cum. I almost didn’t believe her, but hearing her cum for Daddy made my cock throb. I made her lick the dildo clean, then had her go back to teasing herself until I heard the cues I needed, the cues that suggested she could take another orgasm.
What I found out about Miss Kay was that she was a special kind of freak. She had no problem cumming fast, and cumming over and over and over again. We lost count how many times she asked me permission to cum, but it was roughly 10 times. I could hear her pound her cunt with the dildo harder and harder, the distinct sloshing sounds as her squirting and pussy juice made a mess of her bed.
I wanted this fucktoy.
Two days later, we were both in LA, and made arrangements to meet at a coffee shop. We agreed beforehand, nothing sexual except for one discreet grab of her ass as I said hello (it’s a good luck charm that goes back to my first sub). We had a delightful chat, and I did my best to not stare in the direction of her tits too much. It helped that I also enjoyed looking at her eyes and lips. And yes, I guess it also helps that she’s a smart woman and interesting to talk to. I hesitate to write that, because I know she’s reading this right now and feeling like a smug little brat.
Walking her to her car and saying goodbye, I leaned my head down and whispered in her ear that I wanted to grab her tits right now. I noticed as I was leaning down she was tilting her head towards mine, she was wanting a kiss. She gave me permission to grope her. I gave her a squeeze and a kiss, and felt a soft moan escape her lips.
That night, we had a more traditional bit of phone sex, with me whispering orders directly into her ear as she begged me to cum repeatedly. Sometimes I was nice. Sometimes I was mean, waiting and waiting as her pleas became more and more desperate. And I knew, she was going to be a good little fucktoy.
We set the date and time, and waited three more nights.
The build-up was intense. I didn’t let myself cum for 48 hours. I gave her one last 2-hour long period to masturbate, followed by 24 hours of abstinence. I picked out her clothes and which toys we needed to pack.
BUSINESS TIME
It was intense. The stress was building. On the way over, I had her rewrite all of her hard limits and soft limits.
And 15 minutes before I was at her hotel door, she asked for me to not go into it right away, to take a moment to warm her up.
I needed every minute I had left to calm down. The past few days, I had been visualizing storming through the door, ripping her blouse open, choking her, pushing her to her knees and fucking her face. Sometimes I even visualized closing the door.
Now I needed to start in Gentle Daddy Mode. She was too nervous. She needed me to be kind, at least for a bit. At one point I had decided she needed to be spanked 60 times. I made a note to maybe set that punishment aside for another scene.
I opened the door, and she was gorgeous – a black pencil skirt, a sleeveless white blouse. Thigh-high leggings, and slightly slutty makeup (smokey eye, lash extensions, and a vulgarly red lipstick). I knew what was under that outfit, too. Because she was a good girl and did exactly as I told her.
I gave her a hug, as non-sexual as possible. I could feel that desire to throw her on the bed bubbling up. I had her sit on the edge of the bed instead. I slowly started massaging her shoulders.
Miss Kay started to relax with my touch. I had her lay down face-first on the bed, and continued my massage. As she breathed slower, I let my hands occasionally wander to her ass. I gave her a “stoplight,” which is my not-so-subtle way to remind her of safewords and asking for consent. She gave me a green.
I started pushing her skirt up, then rolled her onto her back. Unbuttoning her blouse, I could tell she was worried I was going to rip it. She tried to unbutton it herself. I grabbed her hands and pulled them away. I gave her a stern, “No.” Then I grabbed her neck, squeezed, and looked right into her eyes.
“No,” I repeated.
She understood that I was in charge.
I took a moment to pull the edges of her bra away from her nipples. I already knew that she was wearing a sexy bright-red bra that had bits of red rope woven in and wrapped around her neck. The red perfectly matched her lipstick, and was exactly what I wanted.
While she was stifling her moans as I choked her, she couldn’t hold back as I started to suck on her nipples.
I pushed her skirt up further, exposing her lacy red panties. At first I pushed them aside – I was aching to see her cunt and taste it. It was the only part of her I hadn’t seen yet. I love all kinds of pussies, but I do confess to having a favorite look (puffy lips all day). Hers was perfection.
I pulled off her panties and gave her a nice, slow licking, occasionally toying with her butt plug. I started to slide a finger inside of her tight little cunt. It didn’t take long before she was fully into fucktoy mode, begging me for a second finger.
And with two fingers in, she nearly instantaneously cummed. It was going to be a fun night.
As I took my time moving around her, kissing her, sucking her nipples, and fingering her pussy some more, my cock was throbbing hard. I would take off my pants, then rub her clit. Then I’d remove my shirt, and give her nipples a bite.
Miss Kay reached for my boxer shorts and pulled my cock out, moving her lips down on it quickly.
Two things about Miss Kay that are important here – she’s a massive cumslut, and she has bragged about her cock-sucking prowess. Feeling her lick and suck my shaft, she was not lying about the cock-sucking. I was tempted to just let it happen and cum in her mouth immediately. But, she’s a cumslut. And I wanted to give her a big load for that first shot. I needed to edge a little more.
Also, I was not ecstatic about her trying to take control. She was naturally bratty, and I knew if I gave her an inch (well, more than an inch), she’d never let me live it down. I pulled her lips off my cock and held her by the hair. I gave her a relatively soft slap on the cheek, and it stunned her. She was back in a submissive mindset. I slapped her other cheek, and let her know she was at two of the 60 needed spanks.
From there, I gave her pussy three spanks, and each tit one slap. Then I kissed her to make her feel better, adding extra kisses to anywhere she might be hurting. I kept my mouth between her legs and let her have two fingers again, and again she came nearly immediately.
Legs spread and pussy wet, I couldn’t resist my little cumslut any more. She begged me to fuck her. I grabbed a condom.
Her pussy was a perfect fit for my cock. Each thrust, I could feel myself wanting to just unload a massive shot of cum inside of her. I pushed myself to the edge, pulled out, and pulled off the condom. A couple strokes and I was going to paint her face – only to have her ask me to hold off.
I could feel my fingers go slick with pre-cum – a lot of pre-cum. I held it back, barely. She needed to take the blouse completely off (she had an important work meeting in the morning and didn’t want cum on it. Once she was dressed only in clothes I was allowed to cum on, I pushed her back onto the bed. It didn’t take long to get back to that edge.
I pulled out, hands shaking. It took some effort to get the condom off. I could feel myself already cumming. About three shots before I got the damn condom off. Then another three ropes of cum splattered on her bra and skirt.
It was a surprisingly intense orgasm, to the point that I needed a breather. I grabbed her dildo off the desk and started to work her.
There was a rhythm to her being a slut for me. I would pump her little pussy with the purple dildo for about two minutes. She would start to go stiff and moan a long, “Daaaaaaddyyyyyy,” at me, and then she would beg to cum.
Again, sometimes I would let her cum right away. Other times, I forced her to hold it back for 10, 15, 30 seconds. Sometimes I would let her catch her breath after cumming. Other times, I would work the dildo harder, and demand that she ride it, to keep cumming for me. Sometimes I would tease her clit or her nipples as she recovered.
To mix it up, I took her little lacy panties and shoved them in her mouth. I worked the butt plug into her tight little asshole, occasionally taking a couple licks of her ass or her clit.
And at no point did I feel like Miss Kay had cummed enough. She was a freaky little cumslut.
One of the things I had promised her was to leave my mark on her ass. Particularly, too nice red hand-prints to start. She was a trooper, taking each spank. But immediately after the second one, she sheepishly told me “Yellow” and said that was a little too hard for her. I gave her a moment to recover, and got Mr. Scarecrow. Carrying a four-foot long pole into a hotel room gets some odd looks. Having cuffs and a dog collar attached to it gets more, and Miss Kay requested discretion. So some assembly was required.
She had amazingly small wrists, to the point that one of the straps had some slack. As I strapped in her other wrist, I saw her slowly getting free on the other side. So I grabbed the duct tape, wrapping both wrists.
As an added punishment, I stuffed her panties back into her mouth and taped her mouth shut. In true brat form, she used the panties as leverage to spit the tape off her mouth. I took the panties out, and this time made sure the duct tape made as much skin contact as possible. I could see the promise of future pain was already annoying her.
I went back to the dildo. This was partially to continue her overload of cumming, and partially for me to adjust to the sound of her taped-up moans. At this point, I think I’ve made her cum over 20 times. It was truly insane what this little slut could do. And every time I choked her, or pulled her hair, or bit her nipple, she moaned even harder for me.
The only downside is I couldn’t hear her beg. I ripped the tape off her mouth, and was rewarded with a “FUCK!” as she took the sting. Between her being trapped and her begging again, I had to fuck her for a bit. The only problem was I was still a little drained from my first load. After she came on my dick and the dildo a couple more times, I had to get her back to her punishment.
I grabbed her by her collar, which forced her entire body forward until she spilled face-down on the mattress. With her ass in the air, I gave her three quick swats on each cheek – far lighter than the first two, but hard enough to make her complain.
I grabbed my paddle. Normally I like to use the paddle to increase the amount of butt bruising. But the paddle I use is light and short and wide, making it also good for quick, light, stingy-slaps. I gave her three on one cheek, and three on the other. She cursed me, but I could tell she was handling it. Again, I gave her three and three. I asked her how many times I spanked her.
“Um, 12?”
Now for those playing at home, obviously the answer was 18, along with another nine that I had given her earlier. If she said anything under 27, she would have gotten a big punishment. But not even coming close to 18 gave me a chance to be faux-angry, suggesting that she didn’t even count the six from my hand. To be fair, at this point she was deep in a mindless slut state, so it was quite amazing she was able to count over 10.
Still, I ruthlessly mocked her inability to add (and we’re ignoring the fact that I’ve completely lost count of how many times she’s cummed). I repeated the 12 from the paddle, and asked her if those didn’t even count. I pulled out her brattiness. I pushed her to 60 spanks – the punishment she owed me. She let out a sigh of relief – she made it! And just to be a mean Daddy, I swatted her ass a couple more times, just to remind her that her body was for my pleasure.
I gave her a break and removed Mr. Scarecrow.
At this point, we’d been going at it for about two hours. The final hour was a bit of a blur. I kept making her cum. I started toying her ass – she had never had a man play with her asshole before, and wanted me to eventually be the one to first fuck her ass. But even as she started to handle me teasing her with the plug going in and out, she was still too tight to take my cock without a LOT of pain. So for now, her asshole is safe.
Every time she came, her face got more and more expressive. She goes slightly cross-eyed when she cums, and her tongue slips out of her mouth. Eventually, I felt she needed to see this. So I dragged her by her hair to the full-length mirror. I pushed her face against the mirror, spread her legs, and started rubbing her pussy. I put her in a headlock and told her to look at what a slut she was. She could barely stand. I flexed my arm, and she moaned even more as her face started to redden.
I came two more times – both times immediately after making her cum with the dildo, I pulled a condom on, grabbed either her hair or neck, and pounded her cunt as hard as I could. Both times I came, pulled the condom off, and drained it into her mouth. The final time of the night, there wasn’t a lot of cum in the condom, so I made her lick my cock clean.
For our final bit of aftercare, we swapped back massages and hand massages. She brought some lotion, and rubbed it into my arms and back. It was a strange and warm primal feeling, her rubbing her scent onto me. We stumbled out of the hotel room and back to our cars, her a good little cumslut, and me a sore but happy dirty old man.
Source: reddit.com/r/gonewildstories/comments/c750wx/mf_bondage_spanking_choking_and_using_mr