An Unforgettable Lesson ❤

John followed Vanessa through the door. What greeted him on the other side was what looked like a living room, one that was larger than his. There was a huge tv on the wall and two extremely comfortable looking couches in front of it. There was a desk with a computer and a large bookshelf on one side of the room, there were also four chairs which hung from the ceiling around a small coffee table, then there were three archways with thin curtains leading to other rooms.

Vanessa didn’t say anything and walked towards the closest arch. John followed into her bedroom which had a modern-looking canopy bed with satin curtains. The rest of the room was mostly plain, and John was kind of surprised that she didn’t have a TV in here too. She walked over to a wall that had three mirrors covering it and slid the middle one to the side opening up what looked to be a very large walk-in closet.

She walked to the very back and unlocked an antique-looking wardrobe. Inside, John was completely shocked, there were so many different toys and not only that but bondage stuff too. He should have expected that due to what Frank had been wearing, but he couldn’t have imagined this stuff.

He walked over and looked at the shelves. He spotted a few things that he could use. “Do you have a bag or something?” He asked.

“What for?” Vanessa huffed.

“You want me to get you off, don’t you? I think I’m going to use a couple of toys to do that,” he said matter of factly.

Vanessa took a deep breath and grabbed one of her old handbags, handing it over to John. He opened it up before turning back to Vanessa. “Could you get me a drink?” he asked.

Vanessa huffed and walked away, leaving John to pull things out of the wardrobe and put them into the bag he’d been given. Once he’d gotten a few things, he walked out into the living room area. He placed the bag down by the hanging chairs before looking at how they hung, he smiled as he saw how easy it seemed to unhook one of them.

His attention was cut short as Vanessa came from one of the other rooms with two glasses of cloudy lemonade. John took a glass and had a sip. His eyes widened a little, and he involuntarily moaned. “Wow, that’s really good. Where did you get it?” he asked.

Vanessa rolled her eyes, “It was my grandma’s recipe, I made it.”

John was shocked not only that the princess could do something for herself but also because he couldn’t think of ever having lemonade as nice as that before. But that wasn’t what he was here for. He took the other glass from Vanessa and placed them both on the coffee table where the hanging chairs were before taking a seat in one. “Since I’m helping you. Would you mind, I mean, can you s-strip down to your underwear for me?” John hesitated.

For fuck’s sake, did she really have to do this with this loser? She took a deep breath, she was going to have to take her clothes off anyway and it was not like the virgin had ever seen a girl get undressed in front of him anyway. She could just shake her ass and tits at him while taking off her clothes and he’d get to have a great view. He was going to be watching her as she took off her clothes and she was going to be showing off her body, this was going to be humiliating and she couldn’t do anything about it. So why was she getting wetter?

She closed her eyes and took another breath, then slowly began awkwardly unbuttoning her shirt before tossing it to the side and shaking her large tits from side to side.

She saw how John almost drooled over her. Of course he would. She had an amazing rack, and her skin was flawless, he would have to be gay not to, and even then, she was sure that more than a few gay guys would stare at them.

Next she ever so slowly unzipped her skirt before turning around and slowly pulling the skirt down as she pushed her ass out, giving John a nice view as her toned ass swayed from side to side.

She stood back up and turned to John before walking over and placing her foot on the chair between his legs. She then hooked her fingers into her knee-high socks, but before she could pull them down John put his hand on her knee. “Keep those on, they look hot,” he said. Vanessa was kind of taken aback by how forward the nerd seemed to be but shrugged. She pulled her foot back and placed it on the floor before her hands and arms covered her boobs and crotch. John cleared his throat. “Can you put your hands up and slowly turn all the way around for me?”

She grumbled but crossed her arms around the back of her head and slowly turned. Once she was looking at him again, she sighed, “Okay, is that enough for you? You know you are lucky about this bet because I wouldn’t do this otherwise.”

John stood and walked past her going towards her bookcase. He grabbed the folding step ladder and walked back to the hanging chair before climbing the ladder and unhooking the chair. “Hey, what are you doing?” she asked.

“You’ll see in a moment,” he said as he put the chair down. He took the ladder back and then rummaged through the bag she had given him, the bag which she’d forgotten about until now. She worriedly tried to see what he was getting until he pulled out a pair of high heels and a blindfold.

“Put these heels on and stand where the chair used to be, please,” he said, handing them over.

Vanessa rolled her eyes but did as he asked purely because of her need to get off. John walked behind her and wrapped the blindfold around her eyes. John had gone silent but she could hear him as he walked towards the bag and she could hear him rummaging through it.

Not much later she yelped as his hand pulled both of hers in front of her and she felt something around her wrists. Before she had the time to process what was going on, her arms were pulled up over her head. Then Vanessa felt him tapping on her chin. “Open your mouth, please,” he said. Vanessa had to cringe a little thinking that he didn’t know how to kiss and he was going to try his first one on her. Tentatively she opened her mouth and soon she let out a muffled yelp as a piece of cloth was pushed into her mouth.

She let out yet another muffled yelp as she felt his hand graze against her inner thigh and down until he pulled off one of her high heels; she couldn’t even ask what the point of putting them on was since she had something in her mouth. He then pulled the other one off, and that was when she realised that she was unable to put her feet flat on the ground, she was standing on her tiptoes as her arms had been hoisted up above her head.

“Sorry for the theatrics, but I thought it would be more exciting if you didn’t know what was going to happen,” John explained before pulling her blindfold off. She looked up to see that he’d put thick leather handcuffs on her and had tied a length of rope around it, then attached it to the floating chair fixings above.

John moved closer to her and she shuddered as he stroked her inner thigh, then her eyes went wide as he showed her his sopping wet fingers. Had she been teased that much over the past few days she didn’t even realise? Or was it this situation? She’d never been on the receiving end of this before, she felt so helpless and **** but even just thinking about the position she was in made her shudder slightly. Maybe it was a combination of both?

John smiled at her and then asked, “I need to use your bathroom really quick, where is it?”

She couldn’t help but groan, he had a hot girl literally tied up and he wanted to use the bathroom? She nodded to the door next to her bedroom, and before he left he pulled out her small finger-sized vibrator, turned it onto the lowest setting and pushed it down the front of her panties.

She tried to plead for him to come back. She knew that the amount of vibration that thing did would never get her off, and she needed so desperately to cum right now. John had vanished into the bathroom, and she tried rubbing her legs together to add extra stimulation.

John got into the bathroom and couldn’t help but let out a quiet chuckle. He’d managed to get her into a situation she would never normally experience and he needed to leverage this. He splashed his face with water and spent five minutes looking at his phone, being able to hear Vanessa’s muffled moans, however, caused him to quickly move from looking at memes to internet models.

Before going back out, he unequipped his clothes, pulled them out of his inventory and held them in front of himself to hide his now eight-inch erection.

Moving into the room, he found Vanessa looking at him with pleading eyes. He smiled and walked over, pulling out the small vibrator, turning it off and putting it to one side. Next, he peeled her panties down, the moisture from her pussy created webs of girl cum which stretched the further down he pulled her panties before finally breaking.

John knelt looking at Vanessa’s pussy. She was completely hairless and John could tell how turned on she was from her dripping cunt. He blew on her clit which caused her to twitch. He then stood and took out the clean panties he’d stuffed into her mouth.

“Please, I need it. I need to cum,” she begged.

“I guess I don’t have to ask you to beg me. What would you want me to do?” John asked.

“I, uh, eat me out, please,” she requested.

John smiled and stood back dropping his clothes, Vanessa’s jaw hung open and her eyes widened at the sight of John’s erection. “What the fuck, that thing is huge,” she exhaled. “All of Frank’s cronies said you had a small dick... what the fuck! That’s bigger than Frank’s easily.”

John just smiled before walking closer to her again. He crouched and picked up her soaked panties then pushed them into her mouth as she was about to say something again. “Shh, and thanks.”

He grabbed his dick and moved ever closer to Vanessa, rubbing the tip up and down her pussy. Her eyes widened, and the look in them was a mixture of pleading him to push into her and pleading him not to. Her pussy radiated heat, and John wanted to push in, but that wasn’t his goal today. As he pulled away, he cast Trigger Emotion focusing on her being trusting.

He kneeled down and pulled one of her legs up onto his shoulder before pushing his face between her thighs, her scent was extremely thick almost making John dizzy, and although she wasn’t sweet like Lani, the flavour of her pussy was still something John savoured.

He began running his tongue up and down her lips, parting them slightly and flicking over them, making sure not to stay in one spot too long. It didn’t take her long at all until her body began twitching and she let out a loud muffled groan. Her eyes became half-lidded and her chest heaved.

John smiled then stood, he untied the rope which held her arms up then guided her to step through her arms so that they were behind her. Then he pushed her shoulder down, making her go onto the floor. “I made you cum, it’s only fair you return the favour, right? Oh and that won’t be the only time I make you cum today.” John smiled as he pulled her soaked panties out of her mouth.

She continued to breathe heavily and John pulled out his phone before resting his dick on Vanessa's face. The look of ecstasy on her face was evident as he took several pictures. He pushed the tip of his cock into her mouth, and she lazily used her tongue to play with it. Soon she was bobbing her head as John videoed her. She moaned, then her eyes widened realising what she was doing. She stopped for a moment then seemed to shrug and doubled down causing John to let out his own moans.

She managed to get around half of his dick into her mouth before having to pull back, and he resisted pushing her head further down. He could feel his own orgasm coming. “Vanessa, I’m about to cum.”

She pulled back so that only his tip remained in her mouth and continued to suck and toy with it until he couldn’t hold out any more. The first shot went right into her mouth, but she backed up a little and let out a single cough. The next three shots covered her face and chest; she looked like a few guys ran a train on her.

John stopped the video and took several pictures, and to his surprise, she pulled his cock back into her mouth sucking the last of his load out before swallowing. “Don’t expect this to happen again, but your cum actually doesn’t taste half bad. Now I need to cum again,” she admitted, blushing through the thick coating of cum on her cheeks.

John smiled and helped her up onto her feet, and she shakily followed him as he headed into her bedroom, grabbing the bag as he went.

John stood next to her bed and pushed her panties back into her mouth before helping her yet again step over her bound hands, he guided her to the bed and used some rope to secure her hands to her headboard. He then opened up the bag again and pulled out two more pairs of thick leather handcuffs. His fingers danced down her legs, teasing her ever so slightly before he grabbed one of her ankles and attached one of the cuffs. He traced back up almost to between her legs before going down the other and attaching the other cuff.

“You are flexible, right?” he asked.

She looked at him confused but nodded slightly. He smiled before taking one of her legs and pulling it up above her head and attaching it to the headboard, then moving across and doing the same with the other side.

John knelt below her; the position she was in left her completely exposed. And she couldn’t do anything but leak onto her bed. John reached over to the bag again and pulled out a buttplug; it was about the size of the tip of his dick, that is, before he’d gotten the temporary size increase. He didn’t let her see it and inserted it into her pussy pulling it in and out rapidly, coating it generously in her fluids before pulling it out and showing it to her.

She tried to say something. John assumed that she was protesting but he pretended not to know what she was saying before gently pressing it against her puckered hole. He didn’t just push it in all at once, instead he teased it slightly while using his other hand to touch and toy with her pussy. Soon enough, it went in enough that it was suddenly sucked the rest of the way in.

John smiled and leaned back, taking a nice picture of her, her top half covered in his cum, her bottom half fully exposed and with the red jewel prominently on display. He took his dick and began teasing her again before he started to move back and forth easily, sliding his dick across her pussy lips. It didn’t take long for him to get to the edge again, and he fired several more ropes of cum onto her, creating a nice puddle on her stomach and leaving streaks up her legs which he needed to get a few more pictures of. “I hope you are ready for the orgasm of your life, give me a nice big smile,” John promised as he pulled her panties out of her mouth. She did as he asked and he took one last picture.

Once he’d had his fun, he decided to use Augment Body to temporarily alter her pussy. Her clit became more prominent, and her insides seemed to tighten slightly. He quickly dove in using his tongue to pleasure her.

“OH FUCK! OH MY GOD! OH SHIT! YES! YES! YEEEEEEEES!” Vanessa cried. Her whole body trembled, her mouth opened into a soundless scream before… she passed out. Her head fell back and her body, for the most part, seemed to go limp other than a few twitches here and there.

John couldn’t help but laugh, he’d managed to make her cum so hard that she passed out. After catching his breath, he got to work tidying up and then wrote a note:

Vanessa,

You kinda passed out and I didn’t want to just leave you lying there tied up with cum all over you. Don’t worry, I didn’t do anything else once you had passed out. I got you cleaned up in your bathroom and changed your sheets since they were kind of soaked in our cum.

I didn’t know what you usually wore to bed but I saw a nightgown while putting all of the toys back, so I decided to put that on you in case anyone came to check on you.

Don’t worry about the pictures, I won’t share them on the internet or anything and I don’t plan to use them against you. If you want me to delete them, just say and I’ll do it right away.

This was quite different and I enjoyed it, I don’t expect it will happen again but I’m glad it did and I hope it ended up being the best punishment you’ve had to do after losing a bet.

John

After that, he silently exited the room and made his way out of the manor.

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