The Total Humiliation of James

[Beckster89]

James shuffled uncomfortably out of the doctors door with his dick still dripping with cum. It was visibly smeared all over his thighs and pubes which not only felt unpleasant and gave off a very distinctive smell but was an awful look to be out in public with, seeming to transform him in an instant from a naturist to a sexual degenerate. It didn't leave much to the imagination to the people in the waiting room as to what he had been up to in the surgery. The temptation was to use his hands to try and smear it away but the reality was that would likely only spread the mess and he definitely didn't want to get his cum on the receipt.

The walk to the pharmacy was mercifully short and it wasn't overly crowded but those who were there were likely to linger. There were three female employees behind the counter, two young and attractive and the third older, larger and with the stern look and manner of a strict head teacher. Rebecca's plan to humiliate James by forcing him to buy drugs for erectile function while naked may not have been sophisticated but it was certainly effective. He at least wanted to clean himself up first. He went for a packet of wet wipes and opened them, earning a public rebuke from the older, stricter assistant.

"You need to buy them before you use them" she scowled "although it appears you don't think the rules that apply to everyone else apply to you"

She made a point of staring down sternly at James's dick while the other two store workers giggled like school girls. James walked sheepishly over to the counter and gave the old, unattractive woman hid prescription. She may have been the least pleasant to deal with of the three but he wouldn't want one of the cute girls thinking he suffered from erectile dysfunction on top of everyone else. Having handed over his prescription the horrible worker looked at it briefly before passing it to her cute blonde colleague to process. The cute blonde looked at it and couldn't help giggling before sneaking a look back at James's very much flaccid penis. She then flashed not as subtly as she hoped at her equally cute brunette coworker who also giggled, albeit a little more guiltily.

Everyone behind the till now aware of his imaginary medical issue James paid for his goods and was finally able to open the wet wipes.. He took the only spare seat available (next to a very wholesome looking elderly woman - James was glad the photography student from earlier wasn't around to capture the surreal sight) and lifted a leg up to get the wet wipe where he needed to be cleaned. The woman behind the counter frowned at such an indecent and probably unhygienic display but declined to say anything.

Soon the only thing standing between James and his date with the lovely Holly would be a naked trip to a sex shop in the rough part of town.

In a strange way, being naked in the rough, run down part of town felt less uncomfortable than in the more affluent town centre. People were less judgemental here. While nudity still wasn't exactly expected it seemed less jarring in an environment where many were down on their luck in one way or another or lived an eccentric lifestyle. Strangely, as he approached the sex shop where he was tasked with buying a butt plug, this was probably the least uncomfortable he had felt all day. Until..

"James? Is that you?"

James turned to see a familiar face, one he would have been happy to see under normal circumstances but definitely not right now. Lisa was an old friend, one he had always enjoyed a somewhat flirtatious relationship with though they had never quite taken things beyond there and nowadays she was a married woman. For a brief moment James considered pretending this was a case of mistaken identity or even putting on a foreign accent. But he knew he was rumbled and that would only make him look even worse.

"I didn't expect to see you in this part of town" James said by way of a greeting.

"My office is round the corner. I didn't expect to see you here naked" Lisa wasn't one for holding back. She glanced down and took a long unapologetic look at James's penis, having never seen it before today.

"Yeah, I was just running some errands and I took a short cut"

"And you didn't bother dressing to save even more time" Lisa quipped.

"I lost a bet" James lied "So I have to do my shopping naked today

"Well, I guess that makes sense. You didn't exactly look pleased to see me " Lisa laughed "For a moment I thought seeing you naked in the creepy part of town you may have been a secret pervert"

"No, definitely not" James looked nervously ahead of him to the sex shop where he needed to buy a butt plug.

"Well, it's been great catching up but I have errands to run..."

"Oh, it's fine I'll come with you" Lisa smiled linking arms with James teasingly "It's been ages since we saw each other and I really like looking at your dick. I'm going to commit it a hundred per cent to memory. In fact, do you mind if I take a photo?"

"Cut it out Lisa!"

"Hey you know I'm kidding. But I will keep you company" Lisa grinned affectionately "So where are you taking me?"

[Beckster89]

"James" Lisa prompted her friend as the pair continued to walk arm in arm down the street in the direction of the sex shop it seemed he was going to have to take her into.

"What is it now?"

"I can still see your dick!" Lisa grinned mischievously.

Before James had time to respond he could feel a buzzing coming from the shopping bag he was carrying his belongings in. He reached down and grabbed his phone. Just as he had feared, it was a message from Rebecca.

I am liking this Lisa so far! I really don't want to put any nasty spells on her but I will do if you don't ask to try out at least three butt plugs in the sex shop. Don't worry, I'll make sure the staff accommodate your request

"Who was that?" Lisa enquired.

"Uhh, just work"

"So where are you taking me?" Lisa still wanted to know.

"I'm going into the Pleasure Emporium" James had to admit!

"Oh my goodness!" Lisa gasped "You are such a perv these days! Walking around naked, going into sex shops!"

"You don't have to come!" James told her, desperately hoping she wouldn't want to.

"Are you kidding, of course I'm going to come. I can help you choose...wait, what is it you are going in there for? Wait, don't tell me, it can be a surprise. Maybe I can even help you choose?"

If James had thought masturbating whilst being filmed at by his hot doctor was the most humiliating experience of his day, he was quickly realising that wasn't going to be the case.

James and Lisa entered the shop which, as far as sex shops go, seemed surprisingly respectable. James had never actually been in a sex shop before and going in naked was a huge leap out of his comfort zone. Lisa, on the other hand, seemed giddily excited to be taking her naked male friend to buy sex toys. She had a real bored housewife vibe about her these days and as much as she was joking around it seemed like her unexpected encounter with James today had sparked something in her.

"Hello, how can I help you guys?" a pretty blonde walked over and greeted the pair attentively as they entered. She was not thrown by James's nudity and he wasn't sure if this was down to one of Rebecca's many spells or her line of work.

"Hey, this is my friend James. You can see his dick. Take a look!" Lisa smiled. James new this was partly teasing but he also couldn't help but feel Lisa was getting a kick out of constantly referencing how his penis was on display.

"Very nice!" the store employee smiled politely as she glanced down at it before looking back up at James "Might I suggest a penis piercing would suit you? It won't hurt a bit and can actually increase stimulation during sex. For both of you!"

The assistant smiled at Lisa who didn't correct the understandable assumption that she was James's sexual partner.

"Thanks but I was actually here to buy a butt plug"

"A butt plug!" Lisa giggled in surprise "I feel like I never really knew you before today James!"

"Well, that is no problem Sir, we have a wide range here if you would like to try some out?"

"I can do that?" James had hoped the shop would not allow him to stick their products up his bumhole but apparently that had been dealt with by Rebecca.

"I want to pick! Let me choose for you James!" Lisa was almost jumping up and down with excitement.

"It would probably best for his partner to insert the plug for him if you are up for that?" the assistant asked Lisa. For a moment even Lisa seemed a little thrown by this but, giggling and blushing a little she nodded.

"Sure, why not?"

"Okay, I'll get you some lubrication, you choose a plug for your partner and we can begin!"

James was starting to wonder if he got a say in any of this but it appeared not.

"Okay James, bend over!" Lisa ordered enthusiastically.

[Oopsydaisy]

Fun story!

[Beckster89]

James hesitated but Lisa was insistent.

"Bend over James!" she instructed with a sharper tone "I'm about to stick something up your arse do you want me to be gentle with you or not?"

Just wanting to get this over with James did as he was told. He heard Lisa start giggling behind him.

"What's so funny?"

"I'm sorry, I just can't believe you are doing this! Honestly, you think you know someone!" Lisa replied "I'm gonna need you to spread your cheeks so I can get this in you!"

In a day full of indescribable indignities this had to be the lowest point so far. Nonetheless he did as he was told.

"James..."

"What?"

"I can see your bumhole and your bum and the back of your dick!"

"Just stop messing around and get on with it will you?"

"Ooh, someone's keen!" Lisa teased some more "No, I'm sorry, I'll try and be serious now. Okay, brace yourself!"

Within seconds James could feel something cold and hard and uncomfortable slowly entering his rear. It certainly felt unnatural, not as unpleasant as he may of imagined but he couldn't imagine ever enjoying this.

"Okay, it's in!" Lisa informed him "Now for the cool part!"

Suddenly there was a buzzing sound and an intense vibrating sensation inside James's rectum. He was completely unprepared for this. And the worst part was, it seemed to be sending his body into a state of arousal.

"Okay Lisa, take it out" James said with as much authority as he could manage in his position, his voice reverberating and changing in pitch a little as he tried not to let the vibrating sex toy achieve it's intended aim of pleasuring him to the point of ejaculation.

"Why? you are obviously enjoying it!" Lisa walked around to take a good look at James's throbbing hard dick "I mean reeeally enjoying it. I think you're starting to dribble!"

That was enough for James who reached round and pulled the thing out of his butt before he did more than dribble. He was flushing red with a mixture of humiliation and intense sexual arousal.

"I'll take your cheapest butt plug and nothing that vibrates!" James told the shop assistant before accepting Lisa's offer for a tissue to clean himself up.

"Well, that was actually incredibly fun and I'm not going to lie, you got me a little turned on!" Lisa giggled as the pair left the shop, before catching herself "I shouldn't have said that. Definitely forget I said that."

"I'm going to try and forget the whole experience" James assured her,

"Ah, don't be like that. I think it's actually pretty cool what you are doing. Just walking around naked in public like that. And also kind of hot. But I'm a married woman so you are going to forget I said that too"

"I'll try"

"Okay, bring it in!" Lisa stood with her arms stretched out waiting for a hug.

"Are you serious?"

James was sure Lisa was blushing a little as she nodded. James walked to Lisa and pressed his body up against hers. He couldn't deny it felt good.

"I always knew you liked me" Lisa smiled as she looked down at James's hard again cock, though he couldn't help but notice how perky her nipples were under her blouse. "I'll see you soon!"

For a man who was unwillingly naked in public having just experienced the most humiliating experience of his life James felt surprisingly happy in that moment. Then, of course, his phone buzzed.

James, James, James. I told you if you didn't do what I told you to in that shop I would have to take it out on your friend. And I clearly told you to try out three butt plugs not just one. And, you know, I'm a real stickler for the rules!

There was a sudden scream just a few feet down the road and James looked up to see a shocked and highly embarrassed Lisa desperately trying to cover her completely naked body. Rebecca had struck again!

[Beckster89]

James ran over to his friend wondering just how he was going to even begin to explain this to her. While this was hardly his doing, if Lisa hadn't run into him that day she wouldn't have come into the crossfire of a batshit crazy witch who seemed to love making people naked.

"James, what the fuck?" Lisa was stood in the middle of the street her face red with shame as she used one arm to cover as much of her boobs as possible and the other was guarding her pussy from being seen. She was crouching a little as if trying to make herself smaller and harder to see. It wasn't exactly working as the number of wolf whistles and cat calls clearly demonstrated.

"It's what happened to me. I know it sounds crazy but it's this fucking witch I dated"

"A witch?" Lisa would normally have instantly dismissed such an impossible sounding claim but someone had just made all of her clothes vanish into thin air. And not just her clothes "Shit! My purse is gone! My cards! My house and car keys!"

"My place is ten minutes from here"

"Well, let's go then!" Lisa told James in uncertain terms.

As James watched Lisa running, or more accurately shuffling ahead of him as quickly as she possibly could while keeping her private parts covered, and in between guilty glances at her really quite fantastic arse, James remembered how he had felt when he had first been out in public naked. He had seen a confident, assertive and successful young woman instantly reduced to a humiliated mess. It wasn't like being out in public in the nude ever got easy, but what Lisa was experiencing now was an initial burst of shame and self consciousness more intense than any other feeling he could think of.

He would leave it a bit before breaking it to her that she probably wouldn't be wearing clothing again any time soon.

---

As soon as James had opened the door to his place Lisa ran through shouting "Where's your wardrobe?" back at her friend.

"There's a closet in the bedroom right ahead but..." James tried to warn Lisa but decided to at least let her try at least. Maybe the curse wasn't as severe as the one Rebecca had placed on him. He walked through slowly to give her a chance to dress and when he arrived in his room she was wearing one of his t-shirts, which was far too big for her and looked kind of adorable. She was scratching her head with one hand and looked to be in a state of shock.

"God, that was the most humiliating experience of my life" Lisa breathed a sigh of relief her time being naked in public had been mercifully brief at least "Aren't you going to get dressed? What? What are you looking at, James?"

Lisa looked down and let out a squeal as she realised she was fully naked again. It took her a couple of seconds to compose herself enough to cover her body again. It was the first time James had gotten a full frontal naked view of Lisa, brief as it was. She had shaved herself that morning, it seemed. But that wasn't her biggest concern right now. She was looking at him with a mixture of fear and confusion.

"Go and have a seat. I'll get you a cup of tea" James told her as kindly as he could.

[Beckster89]

Lisa was sat fully naked in the armchair in James's front room, a warm cup of tea in front of her. She had adopted a cross legged position with her arms reaching down in a V shape to cover both nipples and pussy quite effectively. However, when she took a sip of tea she left her right breast completely exposed for a few moments but seemed comfortable enough with James to allow him that occasional treat. Besides, he was completely naked too and had adopted a similar posture more out of a sense of decency than a need to cover himself at this point.

"So we can't wear clothes at all?"

James shook his head.

"For how long?"

"I honestly know as much as you do Lisa. This whole situation is insane!"

"Fuck, what would John think if he saw us here like this?" Lisa realised "How am I supposed to explain it to him? Some perverted witch bitch put a curse on us?"

"I'd be careful what you say about Rebecca, she is watching us most of the time, I think" James warned.

"Watching us!" Lisa blushed as James's phone buzzed and a pained expression came across his face as he read the text.

"Is that her? I'm not going to apologise!" Lisa said stubbornly before starting to worry what might be about to happen to her "What does it say? Tell me!"

"I'm not quite sure how to say this"

"Just say it, James!"

"Until further notice you can only pee and poop outside"

"What!" Lisa exclaimed "Seriously?!"

"There are plenty of bushes nearby" James attempted to console her.

"I'm not a dog, James!" Lisa retorted angrily "Fuck, what are we going to do?"

[Beckster89]

"Fuck it! I can't go! What am I supposed to do?" Lisa stormed out of the bathroom and was stood back in the television that James was trying to watch. By this point she had given up the near futile act of constantly covering herself around her friend and was allowing him to see her fully naked which was still taking a little getting used to for James "I need to go but it just won't come out. Hey, eyes up here! Are you listening to me?"

"I'm really sorry Lisa. Hopefully it's only temporary" James felt sorry for his friend but wasn't exactly sure what help he could be here "Like I say, there are plenty of bushes around here and it should be pretty quiet now. You should go soon though or it will start to get busy with people coming back from work!"

"Shit, I can't believe I am doing this. I swear, if you get any funny ideas about locking me outside!"

"Why would I even think of doing that?"

"Ugh, fine. Let me in the second I buzz you, okay? Be standing right next to it. And NO looking out of your window until I'm back!"

As Lisa ran back to the bathroom then, clutching a roll of toilet paper, from the apartment while covering her boobs and pussy once again, James figured this would be a good point to text Holly and postpone his date with her. It was a shame but now was really not a good time and he had no idea how he would explain having a sexy, big-titted naked woman in his flat. Lisa had explained to him that her husband was away for a few days on business and that she really had nowhere else to go so James had offered to give her his bed and sleep on the couch. She had used his computer to email John and explain she was staying with a (female) friend and had no reception on her phone. If this curse hadn't been reversed by the time John returned James really had no idea what she could do. His phone buzzed right at that moment. It was like Rebecca could read his mind!

I actually really like Lisa, you know. But what is Holly going to make of her? And don't even think of cancelling your date or there will be serious consequences! I really can't wait to see how this all plays out!

James tried his hardest not to think about the humiliating car crash his evening would inevitably turn into and unpaused his show. A while later there was a a buzz on his intercom. Shit, Lisa was back. She had taken longer than he had expected. James hit the buzzer to let her back in and she burst back into the room. Her face was flushed red with embarrassment.

"I thought you said there would be nobody out there!" Lisa shouted accusingly "I've never been so humiliated in my entire life"

"I said it would be relatively quiet now" James corrected her "Anyway, you can stay here as long as you need to and apart from when you need to relieve yourself you won't have to go outside at all. But there is one slight complication."

"What kind of complication?" Lisa asked, not liking the sound of this already.

"I have a date coming over soon"

"A date?" Lisa repeated incredulously "You don't think perhaps that, under the circumstances, this might not be the best time to schedule a date?"

"Our witch friend wants me to go through with it" James offered by way of explanation. Lisa clearly wanted to say something very unflattering about Rebecca but thought better of it. She was going to be pragmatic here.

"So I assume you aren't going to be taking her to a restaurant, unless they have an extremely lenient dress code!"

"I thought we would stay in"

"And what about me?"

"You can stay in my bedroom. I'll give you my laptop, snacks, drink. You can just chill out. You'll need to keep quiet though"

"You are hiding me?!"

"Well, it's not going to look good if my date comes round and I have a hot naked woman in my bedroom would it!" James snapped in exasperating.

Lisa smiled and gave James a mischievous look "Who knows, maybe she would be into that. And since you think I am hot.."

James wished Lisa wouldn't flirt with him right now. They both knew she was off limits but it was very hard to view her purely platonically when she was constantly naked in front of him.

"Look Lisa, just do me a favour and I'll make it up to you okay?"

"Fine" Lisa sighed before once again adopting a suggestive tone "But what if you need the bedroom?"

"It's our first date. I'll cross that bridge if and when I come to it"

"Okay, what about when I need the bathroom. It's not like I can even use yours"

"We're on the ground floor and my bedroom window is big enough for you to squeeze in and out of"

"You have got to be kidding me!" Lisa exclaimed "Like a fucking giant cat flap!"

"We can call it a Lisa flap" James joked back. Lisa was about to retort to this when there was a buzzing sound. Holly was here.

"Okay, that's her. I'll stall her while you grab whatever you want from the kitchen. My laptop is there already and it is unlocked"

"Okay, James" Lisa agreed "But you really do owe me one!"

[Beckster89]

James stalled Holly on his intercom for as long as he could while Lisa hurriedly grabbed a bottle of wine and some snacks from the kitchen. She was certainly taking advantage of his offer to help herself to whatever she wanted but he could hardly deny her under the circumstances. As she scurried to his bedroom James buzzed the door to his block open and walked the short distance from his own front door to greet Holly. She was just as gorgeous as he remembered her from their crazy encounter at the supermarket and was clutching a bottle of wine. She didn't seem at all phased by his nudity this time.

"Wow, do you just never wear clothes?" Holly joked.

"You don't know the half of it" James deadpanned back "You should come through, I probably shouldn't linger in the stairwell like this."

James followed Holly through to his apartment when his date let out a gasp of shock. James followed her in and his eyes widened in shock as a very visible, very naked Lisa was stood just a few feet away from them, standing completely still mid stride as if that might somehow make her invisible.

"Hi, I'm Lisa!" she smiled at Holly after a few moments of deafening silence "Wow, James, I didn't think you would rush back in here so quickly!"

"What is a naked woman doing here James?" Holly looked at her date accusingly.

"Er, Lisa explain yourself!" James demanded of his friend. He wasn't even entirely acting - what the fuck was she doing out of the bedroom.

"Well, I was getting a corkscrew for the wine" Lisa responded, equally annoyed that James had rushed Holly through so quickly and placed her in this position.

"That's right!" James suddenly became animated as an idea hit him "Lisa is going to be our waitress for this evening! Our naked waitress!"

Holly looked a little uncertainly at James then turned to Lisa.

"Is that true? You're a naked waitress?"

James shot Lisa a pleading look, desperately hoping she would do him a solid here.

"Yep, that's me, I'm a naked waitress!" Lisa smiled through gritted teeth as James mouthed his silent thank you's to her.

"So what, you'll be serving us all evening?" Holly asked excitedly.

"It looks like it" Lisa nodded.

"Wow, a naked date and a naked waitress!" Holly seemed quite excited "You know, that's actually kind of hot!"