The Perils of Being Too Trusting Ch. 05

"Fuck Sir!" Heather hissed at him, "This is crazy. They could totally tell!"

"Stay calm slut, people will see you, but most people will either do nothing, or just make a few comments. Besides, I think you're almost to the spot for a change in pace. There should be a trailhead at the next creek you cross. Pull in there, you're going for a little walk."

Heather's heart was racing by the time she pulled her bike into the trailhead, and not just from the strenuous climb. He had her grab a small wooden spanking paddle and a dildo before walking up the trail. He told her to find a place she could get off trail and find a log or rock to sit on. A little less than a quarter mile in she was able to leave the trail and walk several hundred yards to sit on a boulder dappled in shade. She felt much less exposed here than she did walking naked on the trail with both her holes stuffed and holding sex toys, but it still wasn't that far from the trail, and if someone was looking they could still see her.

"Okay slut, lets pull that vibrator out and put it on high. Rub it on your clit for me, I want to see you squirm a bit."

Heather spread her legs wide and traced the vibrating egg up and down her pussy lips, buzzing it against her clit, then winding it down her pussy, across her perineum, and bumping it against the plug in her ass to send vibrations deep inside herself. She moaned, louder than she meant to, at the pleasurable sensations rippling up and down her body. Between all the teasing leading up to this, the naked bike ride, and now masturbating out in nature, she knew she was on a hair trigger.

"Oh Sir, that's so good. May I please cum, Sir?" Heather didn't hold out much hope, but she wanted an orgasm so badly she just had to ask.

"Maybe in a bit if you are good," he came back, "but right now I want you to keep edging. Get as close as you can with that vibe on high. I like watching you right on the edge, it's so sexy."

She smiled at the thought of putting on a sexy show, and kept on teasing her clit with the vibe. She bit her lower lip, and began pinching her left nipple to hold back the pending orgasm. A couple times she had to pull the vibrator away from her clit, and pinch her nipple especially cruelly, even digging her thumbnail in a bit to distract her from how close she was to orgasm. Her legs tensed up, lifting her hips off of the boulder. Soon there was nothing she could do to hold it back any longer.

"Please Sir, I need to stop, I can't hold it back any more," she moaned after a particularly harsh nipple twist. Her legs were shaking from the exertion.

"You may stop for now. I want you to use that paddle, and I want you to spank your cunt 50 times. I want every one of them to be a good firm spank, and you need to thank me for each one."

Heather was speechless. Fifty spanks on her pussy was more than double she had ever done at once before, and the thought of it, especially now that she was all wet and open, terrified her. She briefly contemplated arguing, but experience had taught her that would only make things worse. She would just have to trust that he wouldn't make her permanently damage her vulva. She grabbed the paddle in her right hand and began lightly tapping her crotch, trying to desensitize it. She screwed up her courage, lifted her arm, and brought the paddle down soundly on her pussy lips.

"Aaaaaaowwwweeeee.." Heather shrieked as the pain spread out from her clit and labia. Her thighs snapped together involuntarily for a couple seconds before she could slowly open them.

"One. Thank you, Sir. Aaaah... Two. Thank you, Sir."

Heather's breathing became strained as she slapped her vagina over and over again. By the mid teens she felt herself tearing up some, and her voice got higher as she counted. It wasn't just that it hurt to hit herself like this, although it was getting quite painful, but also all of the experiences were so intense that the emotions overwhelmed her. She was openly crying by the time she got to thirty strokes, and all she could do was sob out the numbers and the thank yous.

As the count got higher, she became less aware of her surroundings, the burning, painful throbbing in her crotch consumed all of her attention. It was almost like she entered a trance as she sobbed through her spanking. Finally she shouted out fifty, dropped her paddle, and clamped her legs together around her hand cupping her pussy. She rocked back and forth, sobbing as she gently rubbed herself, and the pain slowly transitioned into a warm sensation in her core. Soon she was surprised to find herself even more turned on than when she was rubbing herself with the vibrator.

"Oh my fucking God, Sir," she sniffled as she wiped the tears. "This is too much. Please may I cum. Please let your little slut cum. It's been so long, and you're driving me crazy..."

"That was very good, slut. I guess you've earned a chance at it. If you can make yourself cum in the next 4 minutes, then you may. The only rule is you can only fuck yourself with the dildo. No vibrator."

Heather whined a little at the no vibrator rule, but the truth was in her current state, she could probably orgasm dry humping her bicycle seat. She quickly picked up the dildo, and tentatively placed it against her lips. Her crotch was so sore from the spanking that for a second she wasn't sure she could bear inserting the dildo. But her desperation at wanting to climax meant that she had to push past the pain. Once it was in, the pain wasn't quite so bad, and she worked it up and down in her slippery cunt. Slowly at first, then faster and faster as she tweaked and flicked her nipple. On top of the soreness from the spanking, she had worried that she would be too stuffed with both the butt plug and the dildo. But while she felt extremely full, it was not nearly as bad as her sore clit and lips.

The palm of her hand bumped her clit with every stroke of the dildo, and even through the pain, or maybe even because of it, she was getting closer and closer. Finally she rolled onto her side, laying on the boulder, diddling her clit with her right index finger as her left hand pumped the dildo into her pussy. With a sudden spasm the orgasm hit her like an explosion, making her twitch and jerk as she came. She closed her eyes, screamed loudly, and clamped her thighs together tight around her hand and the dildo, rocking as the orgasm went on and on.

Finally she opened her eyes, and noticed the phone was laying camera side down on the ground.

"Hey! What's happening over there?" SpareRod's voice came from the phone

"Sorry Sir, I must have knocked you over. Holy shit, was that an orgasm!"

"I guess," he chuckled, "I heard you scream, saw you start thrashing, and the next thing I knew I was flying through the air."

"I'm sorry, Sir," Heather grinned sheepishly. "And thank you, Sir. That was... it was... just amazing. My mind, I think it's shot, and it's like my whole body is on fire."

Heather stretch languidly, and let the dildo slide out of her sex. She couldn't help but grin at the camera. On impulse she put the slick phallus up to her lips, and began licking it clean, finishing with a deep throat blow job. She could hear his appreciative sounds as she liked and sucked it clean.

"May I take out the butt plug too, Sir?" she asked once the dildo was clean. "I'm feeling very stuffed."

"No keep it in until you get home, I like the idea of keeping your ass ready. Let me look at you though, your paint looks a bit of a mess."

Heather looked down at herself, and realized he was right. With all her pulling and pinching, her left nipple no longer had any paint on it. She had also lost a little paint on her ass cheeks from sitting on the boulder. And her entire pussy was totally exposed now, she had literally spanked the paint off her vulva.

"You are definitely more exposed, but there's nothing to do until you get back to your bike. I guess once you're there you can put your t-shirt back on. But no shorts. I like the idea of that freshly spanked pussy pressed against the saddle"

"Oh fuck, Sir. I didn't even think of how long the ride back will be," Heather was genuinely frightened. "My crotch is so sore now, and I'm not so turned on now and it will be harder to bear. Plus Sir, people will be able to see my butt where the paint has worn off."

"Well, it's their lucky day. And I like the idea of you suffering with all your weight on your sore pussy. No putting on anything below the waist until you're home and have removed all the paint. In fact, I want you to leave the butt plug in until then too. Unless you want to argue some more and then I might make you put on some nipple clamps too."

Heather did not want to argue, so she picked up her sex toys, and prepared to walk back to her bike.

She just hoped that Anna wouldn't be home when she got there, or she'd have a lot of explaining to do.

*

Brad sat at his desk staring at his screens. He felt like the prisoner that had to pick between two doors, one which led to a princess and happily ever after, the other to a tiger and an agonizing death. Except that here both doors probably led to an agonizing death, and he had no chance at the princess. One screen had the video he had edited of Heather's fantasies about what she had wanted Keely and Anna to do to her. His idea was to make Heather show this video to Keely, and push Keely to do more perverted things to her. From what Brad could tell, the girls had played with a tiny bit of watersports, but otherwise they had mostly just been having Heather be naked around the house. Not that it was bad, but Brad felt like he needed some way to keep ramping things up for Heather. He was running out of ideas for things she could do by herself. So he kept thinking that he should move Keely into being his proxy, taking over more of the role of domming Heather. He had edited out the most perverted things Heather had said about the O'Donnells and their young daughter, but it was still enough to humiliate Heather horribly.

Which was one of the real problems. He couldn't be sure this would make Heather submit to Keely, maybe it would just make the two of them shut him out and call the police. He was sure deep down Heather hated him now, and if he did a thing like this that hate would rise to the surface. Taking this step might result in some hot scenes, but it would probably be the beginning of the end for him and Heather.

The other real problem was that he didn't really want Keely, or anyone to be his proxy. He wanted to be the one there, pushing Heather, doing all the kinky things that flitted through his brain. Which led to the window on his other screen, ready to book airline flights. He had often fantasized about just showing up and sweeping Heather off her feet, but he knew better than to fall into that trap. Once he was in front of her, all his power would be gone. Right now he had power because he could embarrass her tremendously, but if he went to her, she could ruin him completely, having him sent to prison for a long time. And she had plenty of reasons to want to see him suffer.

And yet...

It just came down to the fact that he really wanted to take this experience to the next level directly. Even if it worked with Keely (an unlikely outcome he had to admit) it would still leave him wanting more. He just had to find out what it would be like, and trust that Heather would keep doing what he said. Whether out of habit or fear of being exposed, it didn't really matter. He just had to try.

He deleted the video he had created for Keely, and then deleted it from the recycle bin. He opened up the instant messenger, and typed a quick note:

Slut - I will be arriving at the Denver Airport from San Francisco at about 10:30 tomorrow. Meet me just outside security. Bring your make-up, a couple pairs of high heels, and toiletries for 2-3 days. I will take care of all your clothing other than what you wear. Be sure to follow your dress code. I will send you a detailed email with the sex toys I want you to bring as well. Do not disappoint me.

He clicked send on the message, and then went to work on the travel arrangements. His heart was pounding as he did it. He was terrified, but he also felt a great weight lift off of him. One way or another, he was taking his destiny in his own hands. He would just have to trust that it would work out.