We had planned this trip months ago, and departure day was here. The goal was to pleasure my sub (Kat), so we slept in at home and had a leisurely morning before getting in the car for the 3 hour drive: no need to stress about getting up early. Beside, this meant we could avoid rush hour traffic.
Kat's only responsibility this morning was to pack all of her toys - except the remote vibe I planned to use during the drive. She knows to keep them all charged and clean to be used at a moment's notice. Last night I had already confirmed that her pussy was properly trimmed: we don't wax or shave it because of the ingrown hairs, but we do have a trimmer that cuts the hairs as close as possible. She uses the trimmer at least once or twice per week to keep things neat down there.
We were heading to a beach town and a hotel with a pool, so we didn't need much in the way of clothes, but what little she would wear would be what I told her to wear. I threw in a couple of bathing suits for me, casual shorts, sleeveless tank tops and a couple slightly less casual shorts and shirts for dinners and drinks out. For Kat I packed some sexy beach bathing suits that would still stay on in rough surf - but not too sexy: this was a family beach destination after all. I also threw in a special white bikini with no liner, so when it got wet it was practically transparent. She didn't know it yet, but she would be showing off at the hotel's 21+ pool. I added a couple of miniskirts, some short off-shoulder tops and a couple of mini-dresses. Reluctantly, I added a few pair of thong panties as well: ideally I'd like her to be commando, but panties help the vibe stay in, so it was a tradeoff I was willing to make. We were only staying three nights, but since we were driving it was safe to overpack, and I wanted options.
The car was all packed and we had our morning coffee and were about ready to head out, but Kat was still naked. She knows I will tell her what to wear this while weekend, so she has been waiting patiently for me to give her outfit. She would go out to the car naked if I told her too, but I laid out a neon-pink miniskirt, matching crop-top (no bra) and panties along with the pink remote vibe for her to insert. Kat dutifully put on her outfit, knowing that it was going to be a mind-blowing weekend and I was going to take advantage of her being captive in the car. Man she looked hot: we were both going to enjoy this.
We got in the car and I paired my remote app with her toy and gave it a test buzz as she squeezed her legs together. I set the controls to the sound-mode where the vibrations react to the ambient noises. She loves to listen to podcasts as we drive, so I was curious to see how the varying sounds of the different podcasts would trigger the vibe.
"OK Kat, pick a podcast and let's see how this works. Keep 'em coming for the whole drive. My goal is to keep you on edge but not give you release, so if you feel yourself about to have an orgasm, pause whatever is playing until you come down a bit."
"Yes sir, I'm looking forward to the drive, and the whole weekend!"
With that, we headed out on the road, listening to various podcasts and chatting about the topics, the weather, all the bad drivers etc. I could occasionally see her squirming in her seat, and would reach out my hand and caress her thigh, tracing my fingers up under her skirt, teasing her in addition to the vibe. She made it almost an hour into the drive before having to pause a podcast to avoid cumming.
"I'm impressed pet, I didn't think you'd make it that long. Are you enjoying the drive?"
"Most definitely. I can't even tell you what podcasts we've been listening too, I'm constantly distracted!"
"You've got up to 5 minutes to recover, and then I want to hear more of those podcasts - whatever they are ;)"
Next time she lasted just 30 minutes before pausing, and then another 30 minutes and then it was time for a rest stop to grab a snack and use the facilities. I turned the vibe off while we went in, but just as we were about to get back into the car I turned it on high and Kat's knees practically buckled as the held on to the car door trying to catch her breath.
"Bastard" she said, with a huge smile on her face.
"Just keeping you on your toes my dear. I'll set it back on audio mode. We've got about an hour to go."
~~
We got to the hotel mid afternoon, had the bellhop collect our luggage and gave the keys to the valet. This was a 21+ hotel so I'm sure they saw all sorts of people coming ang going, but they definitely appreciated the outfit Kat was wearing. She acted all shy, but she loves the attention. We were shown to our room by the bellhop and it was fantastic. We had paid extra for an ocean view, and it was worth it. We were on the top floor and could see the beach and water for miles, and no-one could see directly into our room, so we could keep the blinds open all the time and stay naked in the room as much as we wanted - and I love to see her walk around naked, but the rules this weekend were a bit different.
"There are just a few rules for this weekend. It's all about your pleasure, so use your safe-words if you aren't enjoying yourself.
First rule: your pussy is be be filled at all times, either with the remote vibe, some other toy, or my cock, tongue or fingers. Understood?"
"Yes sir."
"Second rule: I want you to cum as often as you like: no need to ask permission. Understood?"
"Oooh, I like these rules sir. Anything else?"
"Last rule: you wear only what I tell you to wear all weekend. Got it?"
"Yes sir. What should I wear now?"
"Nothing! I want you naked on the bed, lying on your back with your knees spread. Take the vibe out because I want to taste you and fill you with my hard cock. I was so turned on watching you squirm in the car the whole way here."
Kat wasted no time getting out of her clothes - not that she was wearing much - and getting on the bed as instructed. I took my time taking off my clothes, watching her watching me as her eyes followed me, waiting for me to take my cock out. She can't keep her eyes off my cock when I'm naked, especially when it's hard and I've promised to fuck her.
I stood at the foot of the bed, watching her hold her knees spread wide for me as I gently stroked my cock. She was practically drooling.
"For Pete's sake, what are you waiting for? I've wanted your cock in me since I got up this morning!"
"Patience, dear. I was just admiring your swollen pussy. You've been teased for hours and are all engorged and your lips are glistening. I want a taste before I fuck you: I love going down on you when you are all wet!"
Without further ado, I knelt down between her legs and approached her pussy, inhaling deeply before touching her. I stuck out my tongue and gently licked her from the bottom of her lips on up, and she shuddered when I got to her clit. Normally I like to take my time and tease her, but this weekend was about making her cum as many times as possible, and my cock was aching and dripping pre-cum as well. I really wanted to pound her with my rod and empty my balls into her, so I gave a couple more gentle licks and then focused on her clit. I pursed my lips around it and sucked gently while flicking my tongue up and down, slowly increasing the pace as her breath quickened.
"Oh god, yes! Lick my clit! That feels so good. Mmmmm. Yes! Right there! Harder!"
I aim to please, so I followed her instructions, happily slurping up her juices, getting my chin all wet as I pushed it between her lips.
"Oh god, don't stop! Finger me! Make me cum all over you!"
I shifted position a bit so I could keep sucking on her nub while also getting one, then two fingers in her. She was so wet they slid right in. I probed around a bit, then brought both finder tips up to her g-spot and pressed. Her hips bucked as she called out "Yes! yes, yes, yes! Stroke me!" I responded by sliding my fingers up and down, side to side, applying pressure to her g-spot and I knew she wasn't going to last more than a few seconds. She raised her hips again and threw her head back, letting out a guttural moan as she squirted all over me. I slowed down with my tongue but still kept up some light pressure on her clit as I gently pulled my soaking fingers from her hole. After a minute or so and several after shocks I pulled my mouth from clit and raised up on my knees, prepared to drive into her. Her eyes were closed and her head was tilted to the side basking in the afterglow. I gently rubbed the tip of my cock against her slit and without opening her eyes she moaned in anticipation.
"Are you ready to get fucked pet? Are you ready for me to pound that pussy and dump my load inside you?"
"MHmm" she murmured, nodding her head yes.