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Re: The Total Humiliation of James
Posted: Fri Nov 01, 2024 8:04 pm
by Beckster89
"Okay, why don't you both take a seat and I'll get you some glasses. You're probably going to need a drink, Holly!" Lisa joked as she walked to the kitchen.
"Wow, a naked waitress - such an interesting job! Where did you go to hire her?" Holly asked.
"She's actually a friend" James admitted "I guess this is kind of a new sideline for her"
"A friend?" Holly suddenly seemed a little defensive "Are you sure there is nothing going on between you and Lisa? The way you look at each other is a little..."
"Okay, here are your glasses, I'll just go and grab the wine!" Lisa smiled dutifully as she came back into the room and put the glasses on the table before heading to James's bedroom to fetch the wine bottle she had taken in there earlier. James wondered if she had heard Holly's comment. He hoped not. It wasn't like he could help looking at Lisa a little lustfully while she was fully naked right in front of him. He had thought he had caught her looking at him a few times too and Holly seemed to think the same.
"She's married" James answered Holly's concern once Lisa was back out of earshot.
"And her husband doesn't mind?"
James just shrugged as Lisa came back, set the wine bottle on the table and unscrewed the cork.
"Would sir like a taste first?" Lisa sarcastically overplayed her role.
"Um.."
Before James could answer Lisa leaned over so her boob was right in his face. She lingered there for a moment or two longer than she needed to before standing straight again and gesturing for James to sip the wine, which he did.
"There, was that nice?" Lisa asked suggestively, James nodded with as neutral an expression as he could manage.
"Good, then you can have some more!"
Lisa leaned over even closer this time so her nipple was practically brushing against James's lips. Why was she doing this? Was she fucking him or competing with Holly for his attention? Either way, he had a raging hard on under the table and it hadn't been caused by his date. She eventually moved round to Holly.
"Madame?"
As she filled up Holly's glass Lisa shot James a look. It was a wicked smile that told him she knew he wanted her. Quite why she wanted to make that point right now he wasn't sure. She then walked out of the room and turned and winked at James with Holly unable to see her.
James thought about the two women for a moment. Holly was beautiful, single and seemed to have an amazing personality. He couldn't remember the last time he was this excited about a first date. Lisa was married and out of the question anyway. Thinking hypothetically if she were single, James had always had great chemistry with her and she was a lot of fun to be around. She was definitely attractive, but less so than Holly in his opinion.
But Lisa was naked. And not only that, she was starting to lean into it and act sexy and sassy too which James found extremely hot. She was absolutely right that James wanted her. Right now he wanted Lisa more than anyone, his actual date included. But he also knew that her constant nudity gave her an impossible advantage over Holly. James was going to have to ignore Lisa as best he could and get to know Holly, who was starting to feel a little like a third wheel already, if this date was going to be a success.
Re: The Total Humiliation of James
Posted: Sat Nov 02, 2024 12:12 pm
by Beckster89
James quickly fired off a text to ask Rebecca what she had done to Lisa before getting back to his date. It was weird being on a date with a fully clothed woman while completely naked. It felt more natural when it was him and Lisa hanging out naked together. But she was married and he could hardly ask Holly to strip off so for now he was just going to have to make this dynamic work. His phone buzzed. It was Rebecca.
Huh? I haven't done anything to your friend except the nudity and toilet outside curses. Whatever else she does is down to her - for now at least. What is she doing anyway? Honestly James, it's not like I don't have a life beyond watching you 24/7!
He could never be completely sure but it sounded like Rebecca was telling the truth here. It wasn't like she had anything to gain by lying about this. So Lisa was shoving her breasts in his face of her own accord. That was certainly unexpected.
"James?" Holly asked as her date gazed, lost in thought, in the direction of the kitchen "Am I boring you? If you prefer I can leave and you can hang out with Lisa?"
"No, no, I'm sorry!" James apologised "I was just wondering about what I had in for desert.."
That seemed to placate Holly for now at least. She and James talked for a while and it was obvious they had a lot in common and that Holly was just as gorgeous on the inside as her outward appearance. Things were going well when Lisa poked her head from around the kitchen door.
"Um, James, can you come and test the sauce?"
James excused himself and walked through the kitchen where Lisa pounced and pinned him against the wall.
"So what do you think James, is this hot enough for you?"
"What are you doing? Why are you trying to fuck this up for me!" James whispered as angrily as he could manage to sound, though his sudden erection betrayed his true feelings.
"I can't help it. I feel naughty when I'm naked" Lisa whispered seductively in James's ear while she tickled his balls "Besides, weren't you having more fun with me before?"
It took all his willpower but James managed to pull himself away from Lisa and walk back to his date.
"Wow, it looks like you really liked the sauce" Holly raised her eyebrows as she looked down at James's rock hard dick.
Lisa then emerged from the kitchen as if to showcase the sexy, naked body that had done that to James and smiled triumphantly at Holly "It won't be much longer now!"
Holly could see exactly what was going on here. She didn't even blame James for having a natural physical reaction to a hot, naked woman. Lisa was trying to steal her date and probably felt Holly had no chance against her while she was fully clothed. Well, perhaps Lisa had underestimated her apparent rival.
"You know what James?" Holly smiled as she leaned over and placed her hand on his "I'm feeling really over dressed here. Would you like me to get naked too?"
Re: The Total Humiliation of James
Posted: Sat Nov 02, 2024 1:49 pm
by Vader
This is going to be one wild first date.
Re: The Total Humiliation of James
Posted: Sun Nov 03, 2024 11:15 am
by Beckster89
It was a completely stupid question. OF course James wanted Holly to get naked too! But he couldn't make that too obvious and he didn't want her to feel like she had been pressure into it by the weirdness of the situation.
"I mean, sure, but only if you want to. Don't feel like you have to.."
"I do want to" Holly smiled at James as she began pulling off her tights. She wasn't sure if it was her natural competitive nature that was making her do this or that the idea of having a naked date while a would-be rival waited on her was kind of hot. But in the moment it felt completely right. She wasn't messing about either.
"Is it okay if I just put my clothes on the armchair there?" Holly asked before whipping off her skirt to show off her beautiful, shapely legs.
"Sure"
"You know, it is actually kind of good to get this part of the date out of the way quickly" Holly unbuttoned her blouse and let it hang open, her black cotton underwear fully visible as she spoke "It normally creates such anxiety and the anticipation kind of overshadows everything else."
"Uh, yeah.." James could barely form a thought as Holly threw off her shirt and began unbuttoning her bra.
"Once we've both seen each other naked we can just forget about it and get on with our date, right?"
James nodded enthusiastically as Holly pulled off her bra to reveal a firm, larger than anticipated pair of boobs with the cutest little pink nipples.
"Okay, there!" Holly slid down her panties and stepped out of them before giving James a twirl. She had a peachy little butt and a tight, freshly shaved pussy "Now you have seen it all. Happy to carry on?"
"Yes, definitely!" James tried not to sound too excited. It was at that point Lisa walked back into the room.
"Okay, just a couple of more minutes and.." her face dropped as she saw just what she was up against.
"That's great. Thanks for doing all this cooking and waiting on us Lisa. The date is going really well!" Holly smiled back with mock innocence.
Re: The Total Humiliation of James
Posted: Sun Nov 03, 2024 10:27 pm
by Vader
I think Rebecca is in fact messing with all three of them and having some serious fun doing it even though she claims she is not.
Re: The Total Humiliation of James
Posted: Mon Nov 04, 2024 9:30 am
by Beckster89
Vader wrote: ↑Sun Nov 03, 2024 10:27 pm
I think Rebecca is in fact messing with all three of them and having some serious fun doing it even though she claims she is not.
I think you are probably right and she will continue to do so!
Re: The Total Humiliation of James
Posted: Mon Nov 04, 2024 9:31 am
by Beckster89
Lisa walked back into the kitchen starting to feel more than a little resentful of Holly. She and James had been having so much fun being naked together before his date showed up and she had even enjoyed playing naked waitress until Holly had brought James's attention away from Lisa back to her just now. She was so incredibly bored in her relationship and, for someone with such a high libido living in a practically sexless marriage was crushing her spirit. Being cursed to be naked by a witch would have actually been a pretty hot roleplay idea (though she would have left out the part where she had to pee and poop outside). It was fun living that out with James until Holly went and spoiled it. But if Holly wanted to see if she could upstage Lisa it was game on!
"Here you both are!" Lisa walked back into the room with two plates of spaghetti bolognese, her face a picture of innocence "Enjoy!"
She then took a seat on the large armchair which was in James's direct line of vision while Holly had her back to her. James was clearly struggling to concentrate on his food and not Holly's beautiful, big tits that were just right there in front of him. Lisa was sure she could get his attention back to her though.
She began by opening her legs, putting her inner vulva on display. She knew James hadn't seen that before and it was clear when he next looked up at her that he liked what he saw. Lisa wasn't surprised. She knew she had a pretty cunt. But it still might not be enough to completely overpower the allure of Holly's admittedly gorgeous breasts. Lisa winked at James, placed a finger either side of her slit and began to massage her inner and outer labia. She was a little shocked that she was doing this but everything was so crazy by this point she just didn't care.
As Lisa got more into it, so did James whose stolen glances were longer and more obvious. Lisa had slipped her fingers inside herself now as she was ready to climax, touching herself just how she liked it best. James was transfixed as Lisa let out a moan and began to dribble over her fingers and onto his couch. Naturally, at this point Holly had turned around to see what was going on.
"For fucks sake aren't you supposed to be married?"
"Marriage is boring" Lisa pouted unapologetically as she licked her fingers clean.
Holly looked at James who now couldn't take his eyes off Lisa and wasn't even making a secret of that anymore, while Lisa smiled like she had won already. But while Holly may not have been as sexually adventurous as Lisa she was incredibly competitive by nature, plus she had a kink or two of her own. Holly leaned back and poured most of what was left of her meal over her chest. Her breasts were now covered in spaghetti and bolognese sauce which was quickly running down her stomach towards her immaculately shaved pussy.
"Oh dear James, Look how clumsy I am!" Holly exclaimed in her cutest voice "Do you think you can clean me up?"
But Lisa wasn't about to let her get away with that without putting up a fight.
"It's okay James" Lisa crawled towards Holly, full of grudging respect for her rival by this point but still determined not to be outdone by her "I'm the waitress. I should clean this up!"
Re: The Total Humiliation of James
Posted: Mon Nov 04, 2024 5:00 pm
by Vader
This is a very entertaining competition
Re: The Total Humiliation of James
Posted: Fri Nov 08, 2024 3:21 pm
by Beckster89
As Lisa crawled towards Holly the latter was suddenly wondering whether her impulsive decision to pour her dinner over her naked body had completely backfired. She had hoped the sight of James licking it off her would be enough to convince Lisa to fuck off and stop trying to steal her date with her outrageous and slutty behaviour. She could, of course, tell James to lick it off her instead but he seemed more than happy just to watch this play out. If she backed out of this game of chicken now she would look like a spoilsport and Lisa would win. She wasn't having that.
"Fine, go and get a cloth" Holly lay on her back for easier access to her upper body, knowing what Lisa really had in mind.
"I have a better way" Lisa grinned and she stopped on her hands and knees next to Holly and began lapping the bolognese sauce from Holly's belly button as if she were a cat lapping milk from a bowl. It tickled Holly a little but not in an unpleasant way. Lisa then ran her tongue up from Holly's navel towards her breasts. She wasn't really cleaning up so much as adding her saliva to the mess on Holly's stomach but cleanliness was far from the point here.
Lisa's tongue made it up to Holly's right breast and she began licking around her areola before sucking and flicking her nipple with her tongue. Holly had never been into girls at all but one tongue was much like another and Lisa certainly knew how to pleasure a nipple far better than most men. Holly inadvertently let out a little moan. It wasn't much but it was enough to encourage Lisa to move along to her left breast and apply the same technique there. Holly turned her head and saw that James was watching them both with a rock hard dick that he could not seem to keep himself from tugging.
How had a first dinner date descended to this?
Re: The Total Humiliation of James
Posted: Fri Nov 08, 2024 3:51 pm
by Vader
Beckster89 wrote: ↑Fri Nov 08, 2024 3:21 pm
As Lisa crawled towards Holly the latter was suddenly wondering whether her impulsive decision to pour her dinner over her naked body had completely backfired. She had hoped the sight of James licking it off her would be enough to convince Lisa to fuck off and stop trying to steal her date with her outrageous and slutty behaviour. She could, of course, tell James to lick it off her instead but he seemed more than happy just to watch this play out. If she backed out of this game of chicken now she would look like a spoilsport and Lisa would win. She wasn't having that.
"Fine, go and get a cloth" Holly lay on her back for easier access to her upper body, knowing what Lisa really had in mind.
"I have a better way" Lisa grinned and she stopped on her hands and knees next to Holly and began lapping the bolognese sauce from Holly's belly button as if she were a cat lapping milk from a bowl. It tickled Holly a little but not in an unpleasant way. Lisa then ran her tongue up from Holly's navel towards her breasts. She wasn't really cleaning up so much as adding her saliva to the mess on Holly's stomach but cleanliness was far from the point here.
Lisa's tongue made it up to Holly's right breast and she began licking around her areola before sucking and flicking her nipple with her tongue. Holly had never been into girls at all but one tongue was much like another and Lisa certainly knew how to pleasure a nipple far better than most men. Holly inadvertently let out a little moan. It wasn't much but it was enough to encourage Lisa to move along to her left breast and apply the same technique there. Holly turned her head and saw that James was watching them both with a rock hard dick that he could not seem to keep himself from tugging.
How had a first dinner date descended to this?
One word Rebecca and what a first date she has created.