Self Dares Ch. 08

Hanna came back with another round of drinks and placed them on the table. "How is he doing?" she asked as she sat down, "Oh," she said as she looked at the stage and saw he was not doing well. He was still on the first row, had just got one wrong, was back to the start and was only wearing his boxers.

"Not well," I replied, "Another dick is about to be on show," I added with a grin.

"Good good," she replied smiling at me. Even if you aren't attracted to the owner it is always nice to see a penis. They are amusing and funny to look at. Messy in a sexy sort of way.

"So how much?" she asked me.

"For what?" I replied.

"To get up there," she said.

"Not enough money in the world," I replied.

She grinned at me knowingly. "One million dollars?" she suggested.

"Well, yeah, okay I would do it for a million," I replied. Everyone has their price.

"500 grand?" she offered.

"Well, yeah," I said, "But realistic offers, there is no fucking way I am getting on that stage. You?"

"Oh absolutely fucking not," she replied.

"What if it was capped at undies?" I asked her.

"So even if I lose I keep underwear on?" she confirmed to which I nodded. "Underwear being bra and panties? Or just panties?"

"Bra and panties," I said.

"Yeah, I would do it for $100 to just my underwear," she said nodding.

"Just panties?" I offered.

She shook her head after a moment's thought. "No, prob not," she said, "I would have to be very drunk to get my tits out."

"If there were guaranteed no cameras?" I asked.

She grinned at me as she took a sip of her vodka and coke through the straw. "If there were 100% no cameras or any sort of video evidence then yeah, fuck it, I would do it for $100," she said.

"Nude?" I asked.

"Yeah. Naked," she said nodding her head. "You?"

"Oh yeah abso-fucking-lutely," I said, "Full-on fantasy that."

She laughed and clinked her glass against mine. We cheered as the guy on the stage became another victim of the game and joined in with the overwhelming chant of "off off off." To his credit he did and unlike a lot of the others, it wasn't a shy and reserved strip and scurry off stage with hands firmly cupped over the good bits. He stood for several seconds with his arms by his side taking in the cheers. It must have been electric being up there. Hundreds of people cheering for your nudity and a few more vodkas would put me at serious risk of my inhibitions losing their inhibition. Looking around the crowd there were actually very few phones being used. Okay, any number higher than zero was too many, but I would have expected it to be a sea of camera flashes, but it wasn't It was the same for the female losers as well, yeah a few people took pictures, but the crowd reaction of jeers and boos at the people taking the pictures was almost self-policing. Almost, but not quite. I had no desire to be in someone's personal wank bank and even less desire for that bank to be a wider audience. Even Andy doesn't have nudes of me, and neither is he getting any. You just never know.

"Wanna go and get some food?" Hanna asked at around half 9.

"Yeah, defo, before I get too brave," I replied.

"Ooo are you tempted?" she asked smiling at me.

"No," I lied, "I am not at all dressed for it," I added, and that was probably the main reason. Shoes counted as one item and so I was wearing two things, one of which was a dress. So I would go from fully dressed, to bare feet, to full nudity in two losses. That was a little too risky even for me.

"No underwear?" she asked with a coy smile. I didn't reply, I just gave her a look that removed the need to answer the question. She knew I had no underwear on. "Yeah, that would be a very short game. Come on," she said as she finished her drink and got up.

I got the usual email the next day for feedback on the evening before. They always sent them out and I usually ignored them. This time however I replied. "You need to eliminate any sort of cameras being allowed into the venue. I am not sure how you would achieve that and provide any sort of reassurance, but as the organiser that is your problem. No camera guarantee and both me and my mate would have played, I bet there were more like us in the crowd."

An auto-reply came back instantly, and then the next day another reply came back. It was clearly a group email by the wording. It simply read, "Yes, common feedback that one. We are working on it. Keep your eyes open on the events board for the next event."

It was a Wednesday night the next time when it was only Mum and myself in the house for the evening. I wanted some girl advice and as much as Dad would make himself scarce it just felt less intrusive if it was just Mum. She knew something was going on the second I went downstairs, invited myself to watch TV with her and helped myself to a glass of her wine. She didn't say anything or ask what I wanted. We both knew I wanted something.

"Are you still seeing Andy?" she asked as the film we were watching ended. She simultaneously flicked through the Netflix options and selected another random one. We weren't really watching them, they were just background noise and to fill any silences. We were just having a nice mother/daughter chat on a random Wednesday.

"Uh-huh," I nodded.

"Still loved up?" she teased as she smiled at me.

"Uh-huh. He is dreamy," I said over emphasising both the words and the mannerisms of the reply. There was sarcasm in my response, but the underlying meaning was genuine.

"Cute," she said, "When do we meet him?" she asked.

"You have," I replied.

"I am not counting you in a hospital bed as meeting him." she replied, "Invite him round. We aren't that scary."

"Dad is," I replied with a smile.

"Well, yeah, your Dad is," she conceded, "But he means well. What are your intentions with my daughter," she said using a mock male tone. He has never actually asked that of any ex-boyfriend, but the underlying question is never that far under the surface. Unfortunately for him at 18 their intentions are usually just to find better and more fun ways of ejaculating into or onto me. If I get an orgasm during the process then that is a bonus. Of course, he doesn't need or want to know that.

"Yeah, will do," I replied non-committally.

"Another?" she offered as she pointed at my empty glass.

"Er... yeah, one more," I said.

She disappeared into the kitchen and came back with two full glasses. She sat down again and looked at me. "University going okay?" she asked to which I nodded. "Any interesting events recently?" she asked.

I smiled at her. "There was a strip higher or lower game the other day," I replied.

"To what?" she asked. My blank confused expression promoted her to clarify the question. "Nudity?" she asked.

I nodded. "Oh yeah. If you lost you were getting 100% naked," I said and then explained the rules they were using.

"Fucking hell. How did they get the license for that?" she asked I assume rhetorically. How the fuck would I know?

I shrugged. "Dunno," I said, "They probably don't," I added.

She grinned at me. "Did you play?" she asked.

"Absolutely fucking not," I said matter-of-factly.

"Wimp," she goaded.

"But a wimp with clothes on," I retorted not rising to her bait.

"Yeah that is true," she agreed.

"Too many cameras," I said.

"Arr shit yeah, didn't think of that," she said, "Would you have played with no cameras?"

I wasn't expecting that question. I opted for honesty after a little bit of vocal stumbling. "Er... yeah, I would have been tempted," I said.

"Damn, to be a teenager again," she said ruefully.

"I guess strip games transition the generations in their allure," I said.

"Hell yeah," she said.

"Have you played any?" I asked.

"In my youth I did, yeah," she said.

"Lose any?" I asked grinning at her.

"One or two," she said. The way she said it seemed to indicate that one or two was a very low estimate, but she didn't give me a chance to question her further. "You?" she asked.

"I have played a couple," I said.

"Lose any?" she asked.

"Only at parties and as a girl I have the right to call the game off long before it gets interesting for any observers," I said. I then told her about the game we had played at the bar.

"Any cuties?" she asked.

"No such thing as a bad one when just for entertainment," I said which caused her to laugh out loud. I rolled my eyes. "Not in that way. Just viewing entertainment."

"Hey, whatever floats your boat," she teased.

I took a sip of my wine and looked at her. She was watching the film. Or at least looking at it. I have no idea what was even on. "Andy wants to try anal," I said.

"I bet he fucking does. Dirty bastard," she giggled. Her face quickly changed from joking to serious as she realised it wasn't a general observation it was the reason I had been sitting downstairs for the last 3 hours drinking her wine. "Oh, erm... okay," she said as she looked at me.

"Does it hurt?" I asked her.

"Before we get there," she began, "The first question is do you want to try it. Because if that answer is no then that should be the end of it and he should respect that."

I shrugged. I didn't want to be that candid. "Yeah Mum, I do, I wanna get properly fucked up the ass. Is it fun?" She waited for a response though. "Kinda," I replied after a few seconds.

She smiled warmly at me. She knew my response of 'kinda' was a very toned-down and edited response to the question. My tone was quizzical, but the underlying message was a fair bit more

enthusiastic. I wanted to know what all the fuss was about. Every guy seems to want it and really enjoy it, yet every girl seems to be indifferent and a lot less enthused over the idea. Maybe the girl is less enthusiastic about it because it is her ass getting fucked, or maybe it is just purely dominance and submission and you have to be really into submission to enjoy it? I have watched a few porn videos where the girl really seems to be enjoying it, but maybe she was paid to enjoy it?

"Kinda will do as a start," she said. "To answer the question, no, it shouldn't hurt. It feels really fucking weird and can be a little uncomfortable, but no, it shouldn't hurt. If it is hurting then he is either going too quickly, or more lube is required. Or probably both."

"Uncomfortable?" I asked looking at her.

She nodded as she sorted out her words. She was always open and honest about this sort of stuff, but I am sure some mental editing occurs. "Yeah, like you really need to go and you are having a very messy and embarrassing accident," she said. I looked at her as I picked my words. I think I know what she means, but in these situations, you kind of need to hear it, just for clarification. She obviously read my expression. She shrugged and took a deep breath. "It can feel like you are shitting yourself," she said with a grin.

"Eww," I said with a teenage giggle. I thought that is what she was getting at. In my previous experimentations with it, I had both of those sensations. Pain and the needing to go one. So the pain was wrong, we were doing it wrong. My next question directly leads on from that sensation. "Do you?" I asked.

She knew what I meant. "It can happen, but as long as you prepare beforehand it is unlikely," she said. I just looked at her horrified. They don't show you that in the porn videos. Okay, they do, but I assumed that was on purpose and a niche that I have absolutely no interest in. Her tone changed from sympathetic to matter-of-fact. "Hey, what do you expect? You are going to have a dick thumping in and out of your ass."

"Yeah... but eww," I protested.

"As long as you are 'empty' and clean it is unlikely," she said anticipating my next question. I nodded my head in reply to that. That was enough detail for that side of it.

"So... how?" I asked.

"Short version. A fuck ton of lube, very slowly, and a considerate boyfriend," she said.

"And the long version?" I asked.

"Are you still using condoms?" she asked. I wasn't expecting that question, but I shook my head in reply. She grinned at my reply. It was serious if we had the trust for no protection. Birth control was assumed, she didn't need to ask that. Although the ultimate birth control is anal so not really relevant to this conversation. "I would recommend you do. There is some literal nasty shit back there," she said with a wry smile.

"Okay," I said nodding my head and ignoring the implied grossness.

"Position is important as well," she said, "You don't want to give him control over depth or speed. Laying on your side with him behind you is probably the easiest. You can control his speed and depth by reaching your arm behind you with your hand on his stomach. You also have an escape if he gets too enthusiastic. You can just pull away and off him."

"Okay," I said nodding my head again.

"You on top gives you good control as well, but you don't want to slip and land on him. Plus if he wants to he can still thrust into you and when it comes to the final moments a guy has zero fucking control. Pun intended," she said. I grinned at her. "Don't do doggy to start with, even though that seems like the natural position for it. Flat on your front can be okay, but again, he has too much control and you have nowhere to go if it starts to get painful. If you both like it and once you have built the trust and experience then try whatever position you want, but for starters, I would recommend spooning."

"Yeah, makes sense," I said smiling at her.

"And the rest of it is a fuck load of lube and him going very very slowly," she said. "Water-based lube. Get a good, known brand of it and don't scrimp on it. Lube him and yourself and keep reapplying as and when you need it. Then go really slowly until he is in and it is comfortable. Once he is in and you are used to it as long as he doesn't hit an awkward angle he can have some control back."

"Yeah, okay," I said nodding my head. "Will I enjoy it?"

She shrugged. "Some girls love it, some hate it, some are somewhere in the middle and reserve it for special occasions for him," she said, "The key is you shouldn't NOT enjoy it. If you are uncomfortable or anything like that you tell him to stop and if he doesn't you have my full backing to castrate him. I will stand up in court as a character witness," she said with a grin.

"Do you like it?" I asked. That caused me to blush. That was very much an internal question that I didn't mean to verbalise. Too late now though.

She smiled at me. The question took her by surprise a little bit, but she didn't mind. "I am somewhere in the middle. I don't love it, but I'm more towards the enjoying it side than not," she said. I pushed the fact that it was Dad she was talking about out of my head. No one wants to imagine their parents having sex and for some reason, Mum taking it up the ass somehow felt even more weird.

"Will I c..." I began, but the last word stuck in my throat. I looked at her, but she waited for me to finish the question. I dropped my tone to barely a whisper. "Will I cum?" I finished.

"Possibly. Probably not the first time as you will be too nervous, but yeah, it is possible," she said confidently. She recognised my insecurity and knew if she mirrored my insecurity it would make it worse for me. Treating it like normal makes it normal, which it is. It is just... so personal. She also anticipated my next question. I was never going to ask it, but she answered it anyway. "I do very occasionally. It actually feels really nice when he cums," she said.

"Eww," I said. Images of my Dad cumming up my Mum's bum flashing through my head. "Thanks though," I added. Her advice was invaluable. I could ask girlfriends or Google, but Mum's advice is just more reliable.

"No problem," she said, "Enjoy it and as difficult as it is, relax, it is a lot easier if you are relaxed," she added.

"Yeah, you do hear that," I said to her. It was no surprise I researched it online a little bit.

"Oh, and also," she began. "He may not like it. Don't be surprised if he isn't into it. It feels weird for him as well. Just because you have started doesn't mean you have to finish. Take the condom off, don't be tempted to suck him and it is a good idea for him to wash before he goes in the other place. Or just use your hand, or watch him, whatever you are into."

"Yeah, eww," I said about the sucking.

"As some general advise. Get him really worked up beforehand. The more turned on he is the shorter he will last. He is most likely going to love it and it is one time when him being a 30-second wonder is a bonus," she said.

"That is very true," I said giggling.

"Sexy dress, stilettos, sexy underwear, or even no underwear and make sure he knows well in advance. Proper dirty talk. I am sure you know the drill," she said with a smile.

"Be a slut... got it," I said grinning at her.

"Is he.. er... big?" she asked. She wasn't being pervy, it was a genuine question relating to my chances of enjoying it or not. I didn't answer verbally, I just held my fingers indicating his rough size. She nodded her head. "Yeah, you will be fine." At that moment in time and for only a second I wondered how big Dad was. Weird, and eww, but hey, it seemed relevant. Not that I asked.

We finished the film and were drinking when Dad came back from the bar. He came in and looked at us. "Wow, what do we owe this honour?" he asked when he saw me sitting there.

"She is drinking our wine," Mum said.

"Figures," he said, "Do you need a refill?"

"I am okay," I said, "Gonna go to bed anyway," I said. Leave them to it.

"Yeah I will have a refill," Mum said as she handed him her glass. He took it and went into the kitchen. I had intended to make myself scarce, but he came back quicker than I expected and sat on the sofa. He gave her a kiss and sat back with his wine.

"Eww," I protested at their public display of affection.

"Oh shush with your eww," Dad said jovially. He was ace when he has had a drink. "Anyway, shouldn't you have some clothes on?" he asked looking at me. No filter when he has had a drink.

"Shorts and t-shirt," I protested holding my arms out in demonstration. It was barely a t-shirt, with super short arms, just about long enough to meet the shorts and when stretched tight without stretched arms it did a very poor job of hiding my nipples as well. The shorts were a far cry from actual shorts as well and were probably closer to what you would wear under a gym skirt. I wore them to sleep in or for lounging around in. I had nothing on underneath them, so I guess technically they were underwear.

"Barely," he grumbled.

"Oh shush grandpa," Mum said, "Leave her alone."

"Yeah, leave me alone," I said, "Anyway, gonna go to bed. Thanks, Mum," I said as I got up and gave her a hug.

"Fucking hell," I heard Dad mumble. Not at us hugging, that would be a weird fantasy, but I was wearing what was effectively underwear and a t-shirt that was short and not fitted, even if it wasn't a couple of sizes too big for me for comfort. To achieve the cuddle I had pretty much just bent over in front of him. It would be a fairly good view of my barely covered ass and as a bonus, he probably saw straight up my t-shirt (no bra) as well, even if I am his daughter. As I said, no filter.

"Soz Dad," I said as I ran my fingers around the elastic of my shorts. I probably should have done that beforehand. Cheeky and probably read my lips from that angle. "Night," I said.

"Night love," he said and watched me leave the room. Or watched my ass anyway. "Everything okay?" I heard him ask as soon as he thought I was out of earshot, but I waited for her reply.

"Yeah, all good, girl stuff, not anything you need to concern yourself with," Mum replied. I trusted that she wouldn't tell Dad, but reassurance is always nice. "Wanna blow job?" she asked. Now that I didn't want to hear. I heard the zip of his jeans and his sharp intake of breath as I assume her mouth surrounded his cock. I made myself scarce upstairs. Fucking hell, give it a few minutes before you rip each other's clothes off.