Who Dares Sins

"If you must know, yes," he replied, rolling his eyes, his cheeks reflecting the colour of the hair of those he had a thing for. "I always have, ever since I became interested in girls - redheads are just so striking."

"Why thank you, I do try," Scarlett quipped, flicking her hair amusingly. "Am I striking?" Tom shot a look at her which told her that she was breaking the rules of the game again, though Tom did think that she'd knock all 10 bowling pins down - Scarlett was no spare, and nothing less than a 10.

"I'm pretty sure it's my turn," Tom said, and Scarlett used the muscles in her face to frown playfully. "Truth or dare?" he asked.

"It's about time we did a dare, I think," she responded, despite the threat of a soundless dance still looming.

"Feeling bold, are we?" Tom replied, and he pondered what to have her do.

"How's your dancing?" he teased, though he knew how good she was and was sure that she'd make dancing without music look effortless, so as much as he wanted to see it, it wasn't much of a dare for her. "I dare you..." he started "...To let me look at your browsing history." Oh, that was a good one. Scarlett's complexion suddenly got warmer, the confidence she had while goading Tom about him finding her attractive and having a thing for redheads suddenly diminished. "Pass me your tablet," he said, yet Scarlett was frozen with embarrassment.

"Ahem," he not so subtly prompted her, Scarlett having not moved a muscle. "You chose 'dare'," he teased, "Now pass it over." He held out his hand expectantly and Scarlett moved like a snail, but even a snail reaches its destination eventually. She was simply delaying the inevitable and prolonging her suffering by taking her time, but take her time she did. She picked it up and entered the passcode, then tentatively handed it to her prying housemate. "Thank you," he said cheerily, basking in how embarrassed she clearly was.

"Right, let's see here..." Tom propped the tablet up on his lap and opened Scarlett's web browser of choice, and he immediately saw that there were a number of tabs open. "Let's start with these tabs, shall we?" Tom opened them up and glanced at the titles of some of the tabs, and several caught his eye instantly. He opened the first one, and his eyes seemed to get larger, like those in a cartoon. "Oh my..." Tom chuckled, his jaw dropped, the next few seconds passing in silence. Scarlett knew exactly what he was looking at and she hid her blushing face from him, covering her eyes with horror and bowing her head to the floor.

"Been doing a spot of shopping, I see? This explains all those parcels addressed to you!" Her history and, not only that, the tabs she currently had open were populated by online retailers of adult toys, some of them even open on specific toys that she appeared to have an interest in. Tom browsed through the tabs and the toys, wide-eyed with fascination and intrigue. "How much?!" he shrieked with shock, bringing the screen closer to his face and his wide eyes with disbelief at the figure he was reading on the screen. "Gee whiz, I hope that's bloody good for that price."

Scarlett shrunk farther into herself, waves of shame and embarrassment washing over her. Tom was giggling to himself, enjoying every second of it, and enjoying learning about the sort of sex toys and things that Scarlett appeared to enjoy using and doing. "I could spend all day looking through these - no wonder you do the same," he said, "How many of these do you have?" Scarlett blushed, though realised that Tom was essentially asking a 'truth', and that would be breaking the rules of the game given he was basking in the dare that he'd not long given her.

"Excuse me, Mister," she replied, "That sounds an awful lot like a 'truth'." She was right and Tom knew it, his interest in Scarlett's sex toy collection getting the better of him, though perhaps there would be an opportunity to investigate it further yet.

"Sorry, and thank you," he said, passing Scarlett's tablet back to her with a grin on his face.

"How about you show me your browsing history, if you found mine so entertaining?" she suggested.

"That would do you no good I'm afraid, I'm familiar with incognito mode and I don't leave such tabs open anyway - you won't find anything incriminating in my browsing history. Growing up sharing computers with siblings makes you learn." Scarlett didn't have any siblings so had not had to hide her browsing history from them like Tom had his, and Tom had learnt from experiences that she simply couldn't. "Besides, that's not how this game works - you have to ask me the question."

Scarlett sighed with a hint of dejection, hoping to get her own back at him. "Okay okay - truth or dare?" Wary of what Scarlett could dare him to do even if his browsing history wouldn't incriminate him, he opted for a 'truth'.

"Truth," he answered, and Scarlett thought something up quickly.

"Do you own any sex toys?" Tom should have expected that and not presumed to have gotten off lightly following his exposé of her proclivities.

"Touché," he said, "And yes, I do, thank you." Scarlett raised her eyebrows and a gentle, inquisitive smile emerged on her face.

"Oh yeah?" she responded, "Like what?" Tom looked at her silently, smirking, and Scarlett realised that she was asking another 'truth' - the pesky rules of this game foiling her inquiries. She sighed and waited for Tom to take his turn.

"Truth or dare?" Given how her last dare went, Scarlett perhaps wisely opted for a 'truth'.

"Truth," she answered. Tom pondered what to ask her, pondered what he wanted to learn about her, and soon settled on a question. Given the nature of the last few questions and dares and what he was learning about his housemate and her interest in such activities, Tom kept the momentum going.

"Have you ever masturbated in public?" he rather forwardly asked.

"I've masturbated on a train before," Scarlett candidly responded, not ruffled by the question whatsoever.

"Where? In the toilet?" Tom queried with a hint of surprise.

"No, in the coach itself," she clarified.

"Oh my God!" he replied in giddy disbelief, "With people around?!"

"Yeah."

"Scarlett, you are SO naughty! How did you get away with it!? I couldn't imagine doing that - how would I clean up?" Tom said, contemplating how improbable it would be for a man to do such a thing without being caught.

"It's easier as a woman - you can hide your hand beneath your clothes and slowly use your fingers without arousing suspicion, and then you can just suck your fingers clean, like this..." Scarlett slowly put two fingers into her mouth and began to suck on them, slowly, sensually, and tremendously provocatively.

Scarlett realised that Tom had asked several questions and broken the rules of the game, but she didn't mind because... it was fun... and it was rather hot talking about these things. Tom watched her suck her fingers, uncomfortably noticing his body react to the suggestive motion and the mental image of Scarlett sucking her fingers clean after they had just been in and around a certain place. "You couldn't wait until you got home?" he queried, not aware of how high Scarlett's libido was.

"I tried, but I was too horny, and the carriage wasn't full so I thought I could get away with it. I was quiet."

"It seems like fingers don't quite do it for you anymore?" Tom asked, referencing Scarlett's shopping habits which might suggest that her sexual aspirations had grown since that episode on public transport. "I still use my fingers sometimes," she replied, "But toys do things that fingers can't, and using things like hairbrushes wasn't really doing anything for me."

"Hairbrushes?" Tom questioned, thinking in his head how that would work, before it occurred to him.

"I've used stranger items," Scarlett said nonchalantly.

"Such as?" Tom queried, curious to the unusual lengths Scarlett's sexual desire had taken her.

"You know, candles, that sort of thing."

"Candles?!" exclaimed Tom, both with a degree of shock and a degree of admiration for the lengths she had and would go to for sexual gratification. "No wonder you've been shopping," he quipped, hinting at her supposed collection of purpose-built tools.

"And how about you?" Scarlett clapped back, "You said that you have sex toys - do your hands not do it for you anymore?"

"They do, but like you said - toys just offer something different. Not just physically, but psychologically they feel naughtier and it makes it more pleasurable when I'm, you know, using something that looks like it does. Hands are, well, handy when I just want to do it quickly and without the hassle of cleaning toys."

"Tell me about it!" Scarlett exclaimed, all too familiar with the cleaning quandary that using toys brought about, though also familiar with the psychological pleasure garnered from using something that looks the way it does.

"I dare you to show me some of yours!" Tom said, and Scarlett didn't even think twice.

"Oh my God, yes!" she gleamed and jumped up onto her feet, "I'll be right back!" Tom watched her leave and listened as the sound of footsteps excitedly raced up the stairs, then the sound of drawers opening and who knows what else being moved, before those same footsteps raced back down to stairs. Scarlett dashed back into the room, bringing with her a few toys that she could carry in her hands.

Tom looked at her and what she had in her hands as she sat back down, eyeing up the selection of different toys. "My goodness - a butt plug?" Tom said, noting that she had brought one down with her and had at least one in her collection - "I guess I don't need to ask you whether you like anal or not."

"Tom!" Scarlett gasped at his crude comment. "But yes, I do like anal," she said with a blasé tone as though it was by-the-by, "Is that so wrong?"

"Certainly not to me it's not," he replied, glad to discover that he and Scarlett were singing off the same hymn sheet when it came to utilising every available orifice on a woman's body.

"And this is only a few of the toys you have?" he jested, the selection before him impressive and naughty enough as it was.

"You're welcome to go and get some of your own," Scarlett replied, "In fact, I dare you." Like Scarlett before him, Tom didn't need to be asked twice to partake in a spot of raunchy show and tell with his gorgeous and clearly rather naughty housemate. Tom himself hopped onto his feet and rushed out of the room and up the stairs to his room, his long legs taking two steps at a time, and he rummaged through his own storage and collected a few toys of his own to bring back down with him.

He bolted down the stairs and back into the room where Scarlett was waiting, and he reassumed his place. Scarlett was most intrigued by what toys Tom had and her eyes were fixed on them as he sat back down. "Is that a vibrator?" she questioned, familiar with the general design of one of his toys as it looked a lot like one of hers, though it was slightly different.

"It is!" he said gleefully, popping his toys down but keeping the toy in question in his hand. "I used to think that they were only for women, however, they really do work on men too - they feel great and are really effective. Judging by your browsing history, I assume you know how these work as I believe you may have one quite similar to it". Tom held the vibrator up and showed Scarlett, and indeed she did have one very similar to it. "Though I imagine yours doesn't have this bit here?" Tom pointed out the silicone head of the toy and the flexible silicone arms protruding out from it, creating an incomplete circle for use around a certain something.

"I wonder what you put in there..." Scarlett teased, yet she was genuinely interested in it. "Is it better on the head or on the shaft?" she questioned, curious to learn more about how it worked.

"I can only speak for myself, of course, however, it feels better on the head itself, though it still feels plenty nice on the shaft - it's quite good to use this on the shaft while using one of the other toys." 'One of the other toys' that Tom mentioned included the other things he'd brought down with him, and Scarlett put two and two together.

"You mean one of those?" she pointed at the other toys beside him - a fleshlight and a masturbator.

"Yeah," he replied, "You can use one of those - in an obvious way - and use the vibrator on your shaft. It can be a little awkward, but it's worth it."

Tom imagined that it was a man's version of a woman - perhaps even Scarlett - using a dildo for penetration while using a clitoral vibrator. "How do you get on with the fleshlight?" Scarlett queried, "I've always wondered what they're like - do they feel real?" Tom picked it up and passed it to Scarlett for her to investigate. Scarlett went to take it from him but hesitated, for reasons Tom was sure he knew.

"Don't worry, it's clean," he assured her, then Scarlett took it from him and unscrewed the cap.

"Ehh, they're okay - they're not my favourite," he said to answer her question. "They're not the most versatile, and I find that using them is just like using my hands with extra steps and it doesn't feel that much better, if any better at all. Masturbators, on the other hand..." Tom picked up the weighty masturbator beside him, which was like a torso complete with a pussy, an arse, and even a usable arsehole. "I find these are hotter and much better to use because there's more of it, more weight to it - it feels more real. The issue I have with fleshlights is that they're just disembodied pussies, or arseholes, or mouths, and as lovely as those things obviously are, I just can't quite get on with them. With a masturbator, however, there's more for me to hold onto, I can put it in different positions and use it hands-free and make it feel like I'm fucking it, rather than having to hold it with my hand like a fleshlight."

Scarlett was learning a lot about male sex toys and she understood what he meant about it being better when there was more. Dildos were great and she loved them, though she did also encounter the same feelings toward them as Tom did with fleshlights - that they were just disembodied cocks. She wasn't referring to the size, length or girth of a dildo when it came to there being more, but rather she'd had her eye on another toy for some time, one of the ones she'd left a tab open for on her tablet, that was like one of Tom's masturbators - a torso dildo, though she hadn't gotten one because of how dear they were. She imagined that using and riding one of those would feel infinitely psychologically hotter than using a dildo for the same reasons that Tom mentioned - that she could sit on it, straddle it, fuck it and have something to hold onto while she masturbated hands-free.

Speaking of dildos, Scarlett had brought one of hers downstairs with her, and Tom asked her about hers and how she got on with it. "How about you? How do you get on with dildos?" he asked.

"I love them!" she responded happily, "I just love how versatile they are and how many different types and sizes and materials they come in." The one that she had brought downstairs with her was one of her glass ones, though she loved suction cup dildos too as they were like torso dildos just without the torso, and you could stick them to things and use them hands-free to an extent. "I can't get enough of them - the glass ones are just so beautiful, and they're super easy to clean and dry because they're not porous," she said, holding it in her hand and admiring it, her mind wandering to the idea of using it later on.

"And what about that... vibrator? I assume?" Tom gestured toward a somewhat large, pink toy that Scarlett had brought to the party, and Scarlett knew exactly what he was looking at.

"Oh my God," she said, putting the glass dildo down, "This is my favourite!!" It was smooth on one end and had an unusual, suction dome and tongue-like appendage at the other, and it wasn't like anything Tom had seen before.

"You can either use this end for penetration or like a vibrator," she explained, talking about the smooth end, "Or you can use the other end to simulate oral sex. But..." she said, leaving Tom waiting with bated breath. "The best thing about it is the heating feature - it feels fucking incredible, both inside and out."

"Is it heated, or does it just overheat because of how much you use it?" Tom jested, teasing Scarlett about how frequently she masturbated. He didn't actually know how often she did or didn't masturbate, but it was fun to imply that she was a horny little slut who did it often.

"Har har," Scarlett sarcastically replied, "It is actually heated, thank you." Tom smiled back at her, and Scarlett turned the toy on and enabled the heating setting. She passed it to Tom for him to see and feel for himself, and like Scarlett had hesitated when he passed her his fleshlight, he likewise hesitated now. "It's clean," she commented, returning his words back to him and gesturing at him to take it, and then Tom took the toy into his grasp.

"Oh, my goodness," said Tom, "You weren't kidding."

"See!" Scarlett exclaimed, "I told you."

"And this feels good?" Tom asked, curious to understand why it was so good.

"I don't know for sure," replied Scarlett, "But I think it's something to do with heat increasing your blood flow, which increases sensitivity?"

"Hmm, that makes sense," he acknowledged.

"All I know is that it makes me cum super fucking hard, and I am a big fan of that."

"I don't doubt it!" Tom laughed, and Scarlett joined him. After their laughter had settled, Tom inquired further. "Does that give you your best orgasms then?"

"Yes and no," Scarlett answered, "My best orgasms happen when I have something up my arse, like a butt plug, but doing so while using this toy is the best."

"Scarlett!" Tom laughed again, her honesty and candidness infectious, admirable, and jolly.

"You asked!" she laughed back at him.

"Something 'like a butt plug'?" Tom specified, his observant ears picking up the fact that she had merely said 'something like a butt plug'. "Anything bigger than a butt plug?" he asked, subtly gesturing toward the glass dildo beside her.

"Sometimes," she winked, and they giggled together.

"You are something, do you know that?" Tom complimented her.

"Well, I certainly hope I'm not nothing."

Their clever and witty back and forth had lightened the already playful mood considerably, and there was a good chance that the thoughts running through their heads were shared.

A brief moment of awkward silence fell over them as the sexual tension between them got more palpable, Scarlett brushing her hair behind her ear, Tom coyly looking anywhere but at Scarlett - all this talk of masturbation and sex toys had gotten them both feeling quite frisky and very curious about each other. Scarlett was the one who broke the silence, and she kept the conversation on topic. "When was the last time you used that masturbator?" she asked, gesturing toward the silicone arse and pussy beside him.

"Two weeks ago? Maybe? I'm not sure."

"Do you use it often?" she followed up.

"Not really, no - it's too much of a faff to clean it and dry it secretly with you lot around," he laughed.

Scarlett knew exactly what he was talking about, encountering the same issues when it came to deciding whether to use her toys to masturbate or not, or simply go with the same method she used on the train that time. "Well, don't let me stop you," she said, inviting him not to feel self-conscious about her potentially seeing him carrying it back to his room or finding it drying in the bathroom.

"Thank you," he said, "And likewise don't let me stop you from using your toys - I'd rather you used them than let them gather dust. They're too dear to buy and not use!"