I love a good power negotiation in BDSM – setting up limits, designing a “scene,” making it seem completely insane, then actually committing to it.
That’s why when I found a cute little kitten type in a city I was flying into, I floated this idea to her – she would pick me up from the airport and serve as my “Assistant” for the weekend. She’d drive me around, be my fucktoy as needed, and run basic errands. I didn’t know it at the time, but this young woman was perfect for my needs.
She was slightly taller than I was used to, but small enough that I knew I could throw her around a lot. Her nipples were pierced and she had no problems with exhibitionism or rough play. And the thought of her giving over COMPLETE control to me was enjoyable for both of us.
As part of the foreplay, I also broke one of my main rules for meet-ups. Normally, when planning a scene, I limit the amount of plans to three points guaranteed. I’ve learned that if you make a wish list for 10 items on it and you only get to eight, you regret the two you didn’t do. But if you make a wish list for three things and you get to those same eight things, it feels like you went above and beyond those wants.
For the Assistant, though, she got a detailed itinerary. I’ve included most of it here (removing identifying details).
**Thursday**
*Clothes:
Valet outfit (white blouse, dark pencil skirt, thigh-high stockings, garters, panties, butt plug, bra (optional, must match your panties), any shoes).*
*5:15 p.m. – Be at the airport in the Valet outfit with a Mr. Casey sign ready and the butt plug in. I will get my bags, then find you. I will be touching your face, and inspecting you. If you’re acceptable, I will inform you of that. You will take me to the car.*
My flight got in a little early, and she was still parking. I headed over to the baggage claim and started keeping an eye out. I barely had any sleep, and I was hungry. But right now I felt like a predator, stalking and waiting.
I spotted her, holding the sign and stiff with nervous energy. I strode over to her, standing closer than I normally would. I had about seven inches of a height advantage on her, and I wanted to remind her that she was small compared to me. I “inspected” her like she was a horse being bought, tilting her head up to the side, then running my thumb over her lips. I could see her nipples through the white blouse, she clearly opted for no bra today.
“You’ll do,” I said. I did my best not to grin as I thought about what the other airport patrons were thinking.
I had her lead the way to her car. On the escalator and on the moving walkways I took the occasional opportunities to grope her ass.
*Parking lot – Here I will finish your inspection, starting from behind. I will be touching your shoulders, waist, hips and ass. I will lift up your skirt to verify you have the plug in. I will walk around you and repeat the inspection of your face, as well as a closer inspection of your mouth, tits and pussy. When I’m satisfied, you will drive us to [the hotel].*
I had to wonder if she thought I was joking, or if I would chicken out here. There are probably some security cameras that saw me pushing up her skirt and feeling the plug between her ass cheeks. I could feel the heat from her crotch, she was desperate to be fucked right now.
I took a moment to go through my luggage, pulling out a dog collar. I adjusted it to her neck and snapped it in place.
Repeating the inspection of her mouth, I had her suck on my finger for 10 seconds. Then I squeezed both of her tits, unbuttoned two buttons of her blouse, and walked her over to the driver’s seat. I buckled her in, then pushed my hand between her legs to feel her wet pussy drenching her panties.
“Are you ready to be a good little fucktoy?”
*In the lobby, I will order you to Sit, and to Come.*
*6 p.m. to 8 p.m. – Dinner and Room Play – depends on if I’m more hungry or horny. We’ll find out.*
As it turns out, hunger won. I had her pull through a drive-thru on the way to the hotel. I pushed her skirt up again, showing the tops of her thigh highs and the clamps of her garters. Waiting to place our orders, I ran my fingertip over her hard clit. As a bonus, the drive-thru was two lanes wide. I’m not sure if the other lane noticed.
With our food, we headed to the hotel. I let her adjust her skirt a little and button one button, but the collar stayed on. Walking into the lobby, I pointed at a chair and ordered her to sit. I checked us in, then ordered her to come. We grabbed our luggage and moved to the room.
The second she was in the room, she started to attend to her belongings – unpacking, adjusting things, normal human stuff. So I had to make it clear this is not how things will be going. I grabbed her by the hair and threw her across the bed. I gave her ass a bare-handed spanking, listing off the details she was failing to take care of. And I started asking her what she was going to do to make it up to me.
She was confused, and clearly forgot what her main use was. I pulled her up by her hair, then made her get on her knees. I pulled my cock out, and she instinctively began sucking.
The Assistant had suggested in our messaging that she was a good cocksucker. Now she was proving it. I took a seat on the room’s sofa, then had her continue. I took some pictures and video to later show my wife, and debated letting her make me cum. She probably could have. But I wanted to give her pussy a feel.
I took off her blouse and my pants, then pushed her skirt up. The plug was still in her ass. I figure it had been there for about two hours, if she’d been following instructions, so I removed it.
Her pussy was a good fit for my cock, and her face lit up when I wrapped my hands around her neck. She was going to be a good fucktoy.
I can remember the first time she made me cum. Those ropes were impressive, streaking from her belly to her hair. Some got in her eye. I dragged my hand over the cum streaks, scooping up as much jizz as I could, then forced my fingers into her mouth. She licked my fingers clean, then my cock.
I sat back down on the sofa to finish my food. She came to sit next to me, so I put her food on the ground. She curled up at my feet and quietly ate.
When I felt she had eaten enough, I ordered her to suck my cock again. Blowjobs rarely make me cum, but a good blowjob does get me nice and hard. And she proved very useful for that. I let her get me hard, but instead of fucking her again, I decided I wanted to show off. I pulled her lips off of my cock, then threw her on the bed. I started to slowly tease her pussy with my tongue, and then my fingers. She had warned me that she was a squirter, and I wanted proof. I started to get rougher and rougher with my fingers, pounding and spreading her. She started to quiver, and then she started to beg.
“Please Sir, please,” she said.
I was so focused on trying to make her cum that I nearly didn’t realize what she was begging for. This little fucktoy needed permission to cum. I granted it, and she started to gush for me.
There’s something about pleasing a woman that really turns me on. Sure, she may have been a little raw and sensitive from that overly rough orgams, but I didn’t care. I forced her legs to open wide, and pushed my cock inside of her. I fucked her hard until I needed to cum again. This time I managed to pull out and cum directly in her mouth.
*8 p.m. – Drive me to [my work]. You may also be tasked with picking up some supplies. I want you back at the hotel room at 10 p.m.*
*10 p.m. – Shower or take a bath. You will send me a picture of yourself after you’re clean. Put back on your makeup, the thigh-highs, the garter belt and the white blouse.*
*11 p.m. – Begin edging. You may use your dildo, your vibrator and your plug. DO NOT CUM.*
As it would turn out, I caught my Assistant breaking the rules. She was expecting me back at midnight. I got back a little earlier, around 11:40. I was quiet outside the hotel door, and didn’t hear any tell-tale sounds of masturbation.
I pushed open the room door and stormed it. She was watching cartoons. She had the outfit on and her toys nearby, but she was clearly not edging. I dipped into my rage.
Now, was I really angry that this lovely 22-year-old woman wasn’t following my instructions perfectly? Not really. But was I going to use this excuse to pretend to be livid, to push her fear buttons and unleash on her? Yes, absolutely.
I can’t even remember what I did to her that time. I know I literally tackled her and dragged her around the room. I had her in a headlock and I smashed her face against the mirror, telling her to look at what a little slut she was. While she was standing there looking at herself, I started to rub her clit until her legs started to give out. She was close to cumming from the hand on her pussy, and slowly choking herself out against my arm.
When I felt she was properly punished, I moved on to hurting her for fun instead.
*Midnight-ish – Rope, forced orgasms, light spanking, slapping, choking, hair-pulling, face-fuckings. I will use your dildo, plug and vibrator on you. I will also you my mouth, hands and cock.*
*Then some cuddling.*
*Sleep – If at any point I wake up in the middle of the night, I will fuck you.*
That night I wasn’t exactly a sexual beast. After cumming three times, I started to use the toys to give my cock a break. The lack of sleep leading up to my trip was catching up with me, but I still enjoyed overloading her pussy.
I tied her wrists to the bed posts. Every time she came, I started to wonder if she was going to snap one of the banisters off.
She had a spiral-glass dildo that ALMOST fit in her pussy. It was about a half inch too long, which meant that all I had to do was push that dildo like a button and it would hit her cervix. I mixed that and a slender pink vibrator on her. And eventually her pleasing little moans and whimpers made me want to cum again. So I used her pussy until I was done, cumming entirely on her belly.
We then snuggled up and passed out.
Waking up next to a stranger in a hotel is a bit disoriented for me. The bed wasn’t nearly as comfortable as my home bed. And it took me a good 10 seconds of freshly woken-up brain to place who she was. When I finally remembered that she was my fucktoy, I grinned. I took a moment to stroke my cock hard, then I ripped the blankets off of her.
The rush of air woke her up, and I was already between her legs. She was having that same 10 seconds of disorientation, only her disorientation was accompanied by me rubbing my cock against her pussy.
I’m not sure if she had a fight or flight reaction. There was a brief struggle against me, but then a sudden bolt of submission. It was a good start to the day.
**Friday**
*One-piece swimsuit, Bikini, Red and White onesie, 2-3 cute but casual dresses, Shorts or jeans, Casual shoes, T-shirt, Bra and panties must match.*
*Post-morning sex: Dress-up.*
*Breakfast – Vanilla Time.*
You might notice that there’s a ton of outfits listed for Friday. That’s because we decided I would want to play dress-up with her. I told her to get a dress on, and I hopped in the shower. I was a few time zones off and slept late, so we were already past breakfast time for the hotel.
When I came out, she was in a cute striped dress that looked adorable on her. This annoyed me, because I wanted her to have to try a couple times to please me. She also had just finished brushing her hair, and I got a wicked thought.
Her hairbrush had a nice, wide back to it, like a 3-inch by 4-inch rectangle. It felt good in my hand. I bent her over, pulled up her dress, and started to let her have it. Hearing her scream made me hard, so I fucked her. When it came time to cum, she managed to pull her dress out of the way. I was still annoyed, so I made her change her dress anyway.
She went with a flowing white sundress. I decided she would have no panties and a butt plug, and we went to go get crepes and eggs. Just before walking into the diner, I took her collar off. She was to have vanilla time now, giving her a mental break.
We chatted a bit and enjoyed our breakfasty lunch. Leaving the diner I collared her back up, and took a moment to run my hand up her dress in the parking lot. I’m certain people saw us, but I’m also certain we were long gone before anyone that might have been offended by public nudity could have stopped us.
*11 a.m. – Cumdump*
*2 p.m. – Pool play and lotion rubbing. Collar.*
Her mouth was doing wonders getting me hard, and her pussy was perfect at getting me to cum. I’d completely lost count as to how many times she had made me cum at this point. There was more brush spanking, and more dildo play.
I had her try on one swimsuit, then the other. I decided I liked the first one better, so I fucked her in the second one and came on it. I had her suck the cum out of the fabric and put on the cum-free suit.
At 2 in the afternoon on a Friday, no one was using the pool. We casually enjoyed the chance to cool down and relax. A dip in the pool does wonders for my libido, regulating my body temperature and getting me ready for more.
With no one around and only one noticeable, badly-placed security camera, I fingered her in the pool until she couldn’t muffle her moans anymore. We went back upstairs and peeled off our wet swimsuits.
*4 p.m. – Rough spanking and rough sex.*
I never gave her permission to remove her collar. That was partially a dirty trick. Because with her collar dripping wet from the pool, she popped it off with her swimsuit. Again, I let myself dip into a faux rage, letting myself pretend that this incident had me livid.
I went hard with the spankings, making her ass glow red. I made her gag on my cock, over and over. I spat on her face and slapped her. I made her lick my balls, as well as my asshole and taint.
It felt amazing.
Afterwards, I dialed it back and made sure she was OK. She was loving it, and clearly wanted more. But I was at an impasse – I needed to take a break to get some work emails done.
I put her in the middle of the bed and started to play with her pussy, adding in the glass dildo. I tied her hands together over her head. Then I locked her ankles together with her feet sole-to-sole. Her pussy spread open, I pulled the Hitachi magic wand out of her toy bag, along with a couple other things I noticed.
The wand was a beast, and I’ve had fun breaking sluts with one like it before. I pulled some duct tape out of my bag and strapped the wand to her inner thigh, making sure her clit was perfectly covered by the magic end. With a flip of a switch, she started to squirm and moan. And when I pushed the double-speed button, she would squirm so hard it would push the dildo out of her cunt.
Her bag also had some fun little clothes pegs. I grabbed two, and clamped them on her nipples. I love that they sting when you put them on, but hurt worse when you release.
I calmly opened my laptop on the bed next to her and got to work. I’d answer an email, then push the dildo in again. Or maybe all the way in, to her cervix. Or I’d change the speed of the Hitchachi. She was making a mess of the mattress.
When my work was done, I ripped the tape off her thigh. She had a mix of relief from no more wand and pain from the duct tape. That gave me an evil though, and I pressed the duct tape against her clit, letting the remaining glue cling to her. I teased her with my fingertips, letting her know I was about to rip it. Then with a yank, she let out a delicious yelp of pain.
*6 p.m. – Order Pizza. Do not forget breadsticks. You will answer the door.*
When we started to get hungry, I started to dress her up for the pizza man. Thigh highs, panties, collar. I grabbed my paint-pen and drew a S L U T between her little tits. It was about then that she realized this was ALL I was planning on letting her wear.
But in a surprise twist, it was a pizza lady delivering our food, not a pizza man. We made sure she had a nice tip, then we ate and relaxed a bit.
We rounded out our time with a little more spanking, another load of cum or two, and making sure she was all packed up. I was pleasantly drained, so I had her drop me off at my work, and she headed back home to her partner.
Source: reddit.com/r/gonewildstories/comments/cmo4mp/the_assistantfucktoy_and_her_itinerary_mf_bdsm