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!