“Well Anna you’ve really done it this time.” She thought to herself as she walked down the empty road at mid-day. It had started when she was out doing nothing more than what so many young women do with free time, look for the coolest places and the coolest people. It was out at a club one night that she met Sarah and her friends. Anna had eyed them earlier when they walked in and felt a pang of both jealousy and admiration for how good they looked. As the night progressed, Anna noticed from time to time that the group seemed to receive a lot of attention but it wasn’t until Anna saw the bartender ignore two dozen waiting patrons to serve Sarah as she walked up that Anna decided to introduce herself. Without much to go one she simply walked up and said “Hi I’m Anna. I think you and your friends look amazing tonight!”. Sarah turned to Anna and eyed her top to bottom before breaking out in a smile “I’m Sarah. You look really hot too! Would you like to join us?”

From there the conversation flowed easily. Anna learned Sarah and her friends were of a similar age range and liked to party it up in their free time. They took shots and laughed. Eventually Anna remembered what made her come over and inquired why Sarah was served immediately despite there being so many other men and women waiting. Sarah laughed and said “Well we’re part of a special club that’s plugged in all over town. It definitely has its perks.”. “A club? What’s it take to join? It sounds pretty awesome to me!” from Anna. Sarah appraised Anna again, “Well there’s an initiation that’s kind of naughty to start. You have to get a boy to send me a picture of your nude body!”

That was the start of how Anna found herself walking down a country road. Sarah had driven her out of town for quite a long time before dropping her off. “You know the rules Anna. You walk about until you see a car you’re willing to hitchhike back in. As payment for his services you’re to strip for him so he can enjoy your perky tits and ass! When he’s had his fill he should send us proof and then any incidental services he requires on the way home is just the cost of a ride for you.” Anna had groaned, partly wondering if getting into swanky clubs was worth this embarrassment and party due to already thinking about the day’s events. What Anna hadn’t expected as she got out of the car was that Sarah would grab her phone and wallet saying “Hey we need to keep you honest. Have fun slut!” “What a bitch” Anna thought as she watched Sarah drive off and started walking.

It hadn’t actually been long before she saw her first opportunity. A truck coming from further out in the country had rolled up behind her and slowed down next to her. It had two older, heavy set farmers that looked every bit the caricature. “Are you ok love? It’s hot today and really quiet out here.” One of them asked. Anna eyed them. She was sure they were well meaning but she could also feel their eyes all over her tits. Reflecting on her task, ‘Nope... can’t do it. Not for these gross men.’ “Yes! I’m fine. My friends and I were just out for a picnic and I’m taking a walk. They’re nearby I’m fine really!” she replied. Having a deep understanding of the surrounding areas, the farmers skeptically ventured again “Are you sure love? It wouldn’t be any trouble to give you a lift somewhere.” “Yep! I’m great but thanks! I’m just going to get some more steps in and go back shortly.” “Well... stay cool out there. It’s a hot one today” they replied as they drove off.

That was at 10am and coming around to 1pm with the summer sun beating down on her, Anna was wondering if stripping for those men would have been so bad. She was starting to sweat through her thin clothing and she’d long past drank the water bottle Sarah had given her. ‘After all, they didn’t seem like bad guys. Would it have been so bad to give them a show with my tits and flash my kitty for them?’ Anna reflected as a bead of sweat ran down her face. Unfortunately the opportunity was long gone. She wasn’t worried per se. She figured she could still get to busier parts before it got dangerous but she still steeled herself not to let the next chance go by.

About 30 minutes after that a black sedan comes up from behind and stops. “Miss it’s almost 32 degrees out here are you nuts?!” She heard from the car as the window rolled down. Anna observed a man in his mid-30s with buzzed hair and a beard to match. He wouldn’t have passed as model but was clearly in shape and had the demeanor of man who spent his time deliberately. Anna instantly thought of her task... “Well I seem to have been caught out. I was on a dare with some friends and I think it got a little carried away.” “I’d say so. Here’s a water bottle I got for the drive back. I haven’t opened it yet and I think you need it more than I do.”

Anna gratefully took the water and observing the seal wasn’t broken decided to do just that and gulped down several refreshing mouthfuls. “Thank you so much sir I’m Anna. What do I call you?” “My name is Jake. It looks like you could use a ride Anna.” Anna eyed Jake. Despite her earlier resolution, she again wondered if she could actually go through with it. Then, thinking more of her desires than her common sense, she replied “Well Jake. I’d certainly love a ride! But I have to finish my dare and my friends were quite insistent on how.” Jake replied “Ok.. I’m not sure what that means but I’m listening.”

“Well Jake, I have to strip and give you a show so you can take pictures. Then when you’re happy you send them to my friend Sarah and I enter the club and can come back victorious!” Anna powered through feeling excitement and embarrassment course through her. She left out the part about servicing him. He would never know and she wasn’t sure she was up for that!

Jake took a second to consider her request and felt his cock stiffening while he did so. He could see her tits through her sweat soaked shirt. He had caught her ass as he drove up and already remarked to himself that he would happily have at it. It had already been good holiday but here was a golden chance for some more play before he returned to work and how could he pass that up. A slow predatory smile broke out and he enjoyed the way it made Anna look just a little jumpy. “Well Anna that sounds like a lovely offer. Take your clothes off for me there. When you’re done I’m going to pop open the trunk. Place them there, grab the duffel bag, and join me in the front seat.”

Anna faltered for a second. If she surrendered her clothing she’d be trapped. She already had no wallet or phone thanks to Sarah. Now Jake was demanding her clothes. She’d be stuck naked, miles from her flat or anyone who’d help her. However, she really didn’t want to risk not seeing another car again and anyway had already started enjoying Jake’s deep voice, especially when giving commands. Sighing, she looked him in the eye and began. Jake enjoyed watching her tits drop out of her white shirt. Her tits swayed slightly as she knelt down and undid her shoes, then her socks. As she stood back up he appreciated as she turned slightly and started peeling off her leggings, leaving just a thong. Having gone this far Anna paused for a second. Jake’s eyes remained focused on her but didn’t waver. Taking the hint Anna then removed her last piece of clothing and walked back to the trunk. As she shut the trunk she felt a surge through her body as it became real that she was truly naked and helpless to Jake.

The car was bracingly cold after being in the heat all day. Her nipples immediately stood out and the feelings running through her weren’t helped by the fact that Jake now felt quite free to run his hand over her body as he drove. “I’m glad I found you Anna. That wasn’t a good spot earlier but I know a grove that’s just the place for a show.” Anna shivered although she couldn’t tell if it was from the cold in the car or what’s to come. After a short while Jake instructed “Open the bag Anna. There are some toys in it. Pull out the ball gag and fasten it in deep. I want you feeling submissive when we get there.” Feeling both scared and incredibly turned on Anna fished the gag out of the bag and tied it around her head. She instantly felt the effects, especially noting that it was big enough it wouldn’t be too long before she lost control and started to drool out of it.

Jake took a side road and shortly after pulled up to a clearing with a single large tree shading a wide area. He ordered Anna out and led her under a thick branch near the base of the tree. He loved it when sluts surrendered to him and especially enjoyed watching gagged sluts drool on their tits as Anna was doing now. ‘Well, time to get her strung up’ he remarked to himself. Fetching a pair of cuffs he fastened her wrists, threaded a rope through them and threw it up over the branch, tying it to the tree trunk. Anna was now just on her tip toes and her tits shook as she teetered, unbalanced but never falling. Being helpless was already doing quite a number on her hot pussy but it was when Jake tied her ankles, knees, and then a vibrator right on top of her clit that Anna started to tremble. Jake flipped the vibrator on low and savored slow groan that escaped Anna’s gagged lips. “Well slut. You’ve gotten yourself in quite the predicament.” “Mmf yeur” “I’m sorry I didn’t quite catch that” “Ye ur m n suck”

“I’m sorry slut I can’t quite hear you through all that gagged drooling. Here let me put some of it back” Jake grabbed a copious feel of Anna’s now drenched tits and rubbed her face. ‘Sluts may act like this isn’t what they need but I know better’ He spun Anna around and grabbed her ass. “Mmm this ass tho slut. This thing was made to be spanked.” Jake wasn’t exactly a sadist, but he had always enjoyed a woman feeling both pain and pleasure and the power it gave him. Retrieving a paddle from the bag, he declared “Ten swats slut. If you want rewarded at the end I suggest you thank me.”

SMACK... Anna felt the intensity of the first hit immediately. “Ow!” She somehow managed to shout through the gag. The steady distraction of the vibe on her clit receded from the pain but was somehow replaced with a deeper burn. SMACK SMACK SMACK... These ones fucking hurt and Anna shouted through her gag to Jake’s delight. He stopped for a second and rubbed his hand over her reddened ass and turned the vibe up ever so slightly. After a second Anna felt her pussy begin to reassert itself and start mewling from the pleasure. Jake listened to the sweet noises and returned to his work. Delivering slightly gentler hits slower that were rewarded each time with lustful groans from the slut as her pain and pleasure mixed “Umph... MMpph.... ERRmph...”

By the time Jake was done Anna felt like her ass was on fire and her pussy was ready to explode. Jake turned her to face him. “Well slut I hope you enjoyed that. Do you have anything to say to me?” “Mm... Ye Ur. Hank u ur” Anna recalled after a second. “You’re quite welcome slut. I think it’s time for the show what do you think?” Anna nodded. She didn’t know what he meant but by now would do anything if it lead to cumming. She watched as Jake retrieved his phone. He returned and caressing her gagged face explained “I’m going to video you now. I’m going to turn this vibrator on high until you cum your brains out and then I’m going to send it to your friend Sarah.” “Mmmph Urhmp...”

“I know slut. I think it’s hot too.” Jake retorted as he turned the vibe on high and watched Anna’s eyes roll back in her head. It didn’t take long before Anna’s breathing got raspy and her tits started to shudder. Shortly after came the halted groans of a woman approaching the edge and Jake enjoyed watching as her eyes lost focus and eventually got rewarded with “ERRHMFP MMPPPH ERRRKMPHSJD!” Jake waited until Anna appeared to be coming down. He turned the vibe off and returned to his phone.

The slut was catching her breath after possibly the most intense orgasm of her life. She couldn’t forget the stars that rolled over her when the wave crashed. She absolutely must feel that again. Her ass still stung and with some clarity she was worried about the situation she now found herself in. But it was when Jake showed her his phone that a bolt shot through her. Jake had texted the video to Sarah and her replies were listed

“OMG! That is so hot. You really used her well Jake.”

“Yes I know. Thanks for sending a pic of yourself. I wish I’d been there to see it.”

“Anyway, when the slut is done servicing you as payment she has somewhere else to be tonight. I’ll text you an address. Drop her off her when you’re done. For good measure make her complete the drive nude, gagged, and add a blindfold. She’ll end up that way anyway tonight.”

“Well of course you’re invited too. You’ll have to pass through security but I want to meet you.”

Anna froze. She had lied to Jake and now he knew she was supposed to please his cock in any way he wanted. In her current mood that was no problem but she didn’t know what he’d do with the lie. Additionally she hadn’t heard about a next stop. She hadn’t signed up for that and didn’t know what it was. Jake interrupted her reverie, “Well slut. It looks like you’ve not been fully honest with me and have quite a night ahead of you to boot. I’ll need to punish you if we continue but first. This is not a rape. If you don’t want to proceed further with me or go to that address I’ll untie you now and drop you wherever you want to go. If however, you’re still in the mood to play shake your head and say Yes Sir.”

Anna reflected for a second. Her orgasm’s aftershocks were still coursing through her. There was simply no way she could turn down a chance for more of that. She slowly shook her head and managed through her gag a “Ye Ur”.

Very good then slut. Let’s begin...