Self Dares Ch. 08

We were out for some dinner. Just at the local bar near Andy's house. It was nowhere special so I was just wearing my usual jeans, a T-shirt and my trainers. I had been nervous and tingly all day. He had advised me a few days ago that the lube had arrived. I dismissed it as a throwaway comment and made sure he realised just because he now had lube didn't automatically give him access to my back door. I wasn't as blunt as that, but he knew he wasn't getting bum fun. Today however I had woken up horny and despite two early morning self-administered fairly incredible orgasms my body just wouldn't let up. I had done all the prep as advised by Mum and was sitting picking at my mac and cheese. That sounds like some sort of euphemism, it isn't I was however to be blunt, horny as fuck. I was going to let him fuck me up the ass. Or at least try it, it may quite literally end in tears, most likely mine, but you never know, I may enjoy it.

We finished our food and ordered a couple of drinks. I was sat next to him in the booth that we had and there had been disgraceful displays of public affection throughout the evening. I was currently sipping at my vodka, while he teased his fingers between my legs. The booth offered privacy, but I hadn't stopped him when he was doing it through my jeans, I also hadn't stopped him when he bypassed the jeans and stroked me through my panties. They had been pushed aside and he was currently fingering me in public. My eyes were glassy with pleasure and I was more chewing the straw than sucking on it. If my teeth were clenched I wasn't making any involuntary noises.

"Fuuuuuuuuuuck," I said, barely a whisper and looked at him. My eyes flickered and blurred for a second before I blinked them back into focus again. "That feels so fucking nice," I whispered and grinned at him biting the straw seductively.

The waitress came over and collected a few empty glasses and our plates. I swatted at his hand and crossed my legs when I saw her coming over. Recovering a shred of composure I sipped my drink and smiled at her. "Thanks," I said as she collected everything.

"No worries," she said, "Do you need anything else?"

Yeah, I need a dick in me, but I am sure she neither wanted to know such detail nor be in a position to offer such a service. "No ta," I said.

She disappeared into the kitchen and I uncrossed my legs. Andy didn't need an invite and he resumed where he left off. I stared at him in surprise as I felt myself losing the battle with my own body. I closed my eyes and fought the tingle that was rising up inside me, but I was losing this one, I was going to orgasm in public. He has watched me orgasm enough to know the signs that I am close and he just smiled at me knowingly. I shifted my position slightly on the bench, but I was beyond controlling this. "I'm gonna cum," I whispered. My eyes crossed at the same time as orgasm rippled through me. I managed to control the shaking signs of climax and instead just stopped breathing while staring into my vodka glass like it was the most interesting thing in the world at that moment in time.

He let me finish and then adjusted the angle of his hand and fingers. He was going to make me cum again. "Ah ah," I said shaking my head and crossing my legs. "Fuuuuuuuuuuck, I can't do two quietly." I grinned at him. I felt like I had wet myself, my panties felt physically wet as I crossed my legs.

"You are so cute when you cum," he observed. I just blushed.

I composed myself and sat up straight again. I swapped the straw out of my vodka as the one I was currently using was a chewed mess. "I am going to suck you dry later," I whispered as I took a sip of vodka.

"Promise?" he grinned at me.

"Promise" I confirmed. We continued with the drinks and he ordered a final round for us. I excused myself to the restroom and slipped my panties off. I say slipped them off, there is no slipping possible with jeans on. I stripped from the waist down then put my jeans back on. I was actually surprised that the panties weren't dripping wet. I had been creaming them most of the day and he had just fingered me to a fairly good orgasm. They were clearly not dry, but they weren't wring them out levels of wetness.

I palmed them and went back to the table. They were a tiny thong so I could easily hold them invisibly in my hand. I rested my hand on his under the table and when he turned his palm upwards to hold my hand I opened my hand and dropped my panties into his open palm. He knew instantly what it was and a smile spread across his face. He closed his hand around them and the grin spread a little wider. He knew how wet I was, his fingers had just been inside me, but feeling my excitement in panties that I was no longer wearing was a massive turn-on for him. "I am so horny," I whispered. "Wanna fuck me up the ass?"

He looked at me for a second while my words registered. "Really?" he asked when he had processed what I had just said.

"Uh-huh," I nodded, "I want you to fuck me up the ass," I said again.

He downed his drink and I followed suit. We paid the check and practically ran back to his. He let us in and manhandled me into the bedroom. Throwing me onto the bed he was actually naked before I was for a change. He was keen, give him that. He took my t-shirt off, I wasn't wearing a bra, and moments later my jeans were gone so I was naked. He lowered his face between my legs and licked me. My body exploded with pleasure as he went down on me. He licked me to another orgasm, lapping at my excitement as it flowed out of me and into his eager mouth. We swapped positions and I returned the favour, Although he stopped me short of his orgasm. "I am gonna cum if you do that," he said.

I smiled at him and pulled him up for a kiss. I fumbled around on his bedside table and found a condom. I put it on him while we kissed. "Boring stuff," I said to which he pulled back and listened. "Stop means stop. I want you behind me, on your side. I have full control."

"Of course," he said.

We resumed the kissing and after a while, I rolled onto my side and he cuddled in behind me. I felt the lube on my bare bum and jumped at the coldness of it. He stroked himself to apply the lube to his cock and then cuddled into me. I pushed my bum out and reached behind my back. I guided him towards my wrong hole. He pushed and actually slipped inside me. "Ooo fuck, ow," I said. It didn't actually hurt, it was just a surprise to suddenly have a dick up my bum that easily. I pulled away from him, "Let me," I said.

"Sorry," he whispered.

I took the lube off him and added, as Mum put it, a fuck ton of it. I guided him back and gently pushed myself back onto him. He slipped inside again distressingly easily. Surely anal should be way harder than this? I pushed back onto him as slowly as I could waiting for the pain. It never arrived. I felt fuller and it was quite possibly the worst sensation I have ever experienced when not just in my own company in the bathroom. I let go of his cock and rested my hand on his stomach. I pushed back onto him again and he slipped deeper and deeper up my bum. "That feels so fucking weird," I said softly. I trusted Mum unconditionally, but I will admit I doubted her when she said it shouldn't hurt, it just felt weird. She was right though, it didn't hurt, it just felt really really odd and then I felt his balls press against me. That was it, he was all in.

"That is fucking incredible," he gasped behind me.

"Feel good?" I asked.

I felt him nod behind me. "So fucking good," he whispered, "Does it hurt?"

I paused for a second to confirm that it really didn't hurt. I shook my head. "No," I said. "It feels really fucking weird though," I said.

I held him inside me for a few moments as my body adjusted to the invasion. I tensed a few times, just to feel it and that did hurt a little bit. Maybe hurt is too strong a word, it just ached a bit. I slid my hips forward and felt his slick cock slowly start to slide out of my ass. "Oh fuck," he gasped as I started to slide my ass up and down his cock. He was a considerate boyfriend. He was laying statue still and it must have been torture as I am sure he just wanted to hammer away at me. I shifted my hips slightly and pushed back onto him until he was balls-deep again.

I moved my hand away from his stomach but held it close by just in case. "Slowly," I said.

He gently pulled out of me and overestimated his length and the desire for my ass to not have a dick up it as he fell out. I reached behind myself and guided him back in me again then felt him slowly feed his dick back into my bum again. He quickly adjusted to the different angle and didn't fall out again. I gradually moved my hand further away from his stomach as I gave him control.

It really didn't feel nice, but equally, it wasn't horrible either. He picked up the pace and I slowly moved my hand further away from him. I was waiting for the pain. I could feel how deep he was. He wasn't the biggest in that department, but even so, at this angle and position, he was his full five inches in me. He felt huge, like really big as he took me up the wrong hole. I fully retracted my hand and rested it on the bed next to me. It actually felt okay, I wouldn't pick it over pussy or even my mouth, but it felt okay. He seemed to be enjoying it and was going faster and harder. The position of him being on his side was not the best for him to properly fuck me, but that was kind of the idea. He shifted and the angle changed slightly which sent a pang of discomfort through me and I tensed which made it worse. "Sorry," he said as he felt my body change from relaxed to fully tense. He also stopped instantly, although he didn't pull out.

"It is okay. Keep going," I said. He did, slowly at first but gradually getting faster again.

"Does it hurt?" he asked.

I shook my head. "Not really, it just feels really really weird," I said. I wouldn't say that it didn't hurt as I was very much aware of a dick being where it shouldn't be and my body was not overly amused at my decision. It was just an ache, a sensation of being too full. It was a nice discomfort though. It felt so naughty. He didn't reply he just kept going, firmly, but with an element of care. "Can you cum like this?" I asked.

"Uh hu," he nodded, "It feels... just... wow," he said.

I looked over my shoulder and grinned at him. "Cum in my ass," I teased.

He cuddled in behind me and went a little deeper. He pulled me close and held himself deep in me for a few seconds and then tension left his embrace. Was that it? I looked over my shoulder at him. "Did you just cum?" I asked him.

"Yeah," he nodded, "Fucking hell... wow," he added. That was disappointing, even when using a condom it feels really nice when a guy cums in you, but I barely felt that. It was more his body action that alerted me to it. I guess with no condom I would feel it, but I doubted it would feel anywhere near as nice as it does in the correct entrance. Plus the fact I don't think I want cum up my bum.

I reached behind my back and held the condom on his cock as I pulled off him. The sensation of emptiness was so strange after feeling so full. The second he was out of me I let go of him. I knew where that had been. Eww. He was soft before I pulled him out of me and I rolled onto my back. We kissed and cuddled with an intimacy that I have never experienced. Not just with him, but ever. I felt closer to him at that moment than I ever have with anyone else.

The buzz of sex faded and he let out a few single snores as he started to fall asleep. "Back in a sec," I said as I got out of bed. "Take the condom off," I said to him as he was still wearing it. He just nodded and then I went to the bathroom. I decided to just have a shower, it was easier. Lube was everywhere. My ass felt weird, but I guess it is allowed to feel a little odd, I have just let a guy fuck it for pretty much the first time. Yeah, I have dabbled in anal, but that was the first time I have ever taken a full cock up there.

I went back into his room, still naked, and to his credit he had taken off the condom and I couldn't see it, so he must have at least binned it. I cuddled up to him and went to sleep.

The next day Mum asked how my night had been and I replied with my usual wry smile. "You were right," I added. She would know what I was referring to.

"Never doubt your mother," she replied.

"Although it didn't feel nice when he... you know," I said to her.

She just shrugged. "Yeah, it is personal to you, everyone is different," she said. "Did you like it?" she asked.

I hesitated as I wasn't sure if I wanted to be that candid or not. My hesitation probably answered the question for her. The reply was either an instant, hell no, or it was a consideration of taboo as to whether I admit to enjoying bum sex. I just went down the middle. "I didn't dislike it," I replied. Which I guess was truthful. It was my least favourite option, but it wasn't that bad. She didn't continue the conversation and left it at that.

Hanna was at mine a few days later and we were just chatting while laying on my bed and listening to some music. "Oh yeah, have you seen there is another strip night at the weekend?" Hanna said.

"No," I replied, "Same as the last one?"

"Actual security to get in with scanners and all mobiles will be taken off people," she said.

"They listen to feedback then," I said.

"Seems that way," she said. Then paused for a few seconds before asking, "Fancy it?"

I smiled at her. She wasn't asking if I fancied going as a spectator, she was asking if I fancied playing. She clearly did, or she wouldn't have mentioned it in the way she had done. "Do you?" I asked. I did, but I didn't want to sound too keen and have misread her.

She nodded. "Yeah, maybe," she said. Social taboo is a funny thing, isn't it? Both of us were very much interested. We had said as much on the first night and our concerns had been addressed. Yet public nudity was still taboo, and putting yourself in such a situation was still potentially a faux pas.

"Awesome, me too," I replied, "Let's try to keep our panties on?" I suggested.

"Well I was hoping for a little more than that," she replied with a grin, "But yeah, at the bare minimum, let's try to keep our panties on."

The Saturday came around and Hanna was at mine getting ready. After reading the extensive rules on the website we were allowed six items. There were a load of small print on the items which I won't bore you with, but basically, you can include shoes and socks as a total of four items, but they can't be removed sequentially. So you can't go, shoe, shoe, sock, sock for your first four losses. You had to go shoe, shoe, top, sock sock, or similar. It was to stop people from having six unimportant items and then one main item. Additional terms prevented any workaround to achieve the same goal, so we were allowed six items and for the final item, we had to be topless or bottomless and uncovered. So you couldn't wear a long T-shirt as your last item, but you could wear a vest. If your last item was your bottoms, they had to be underwear, they could be any type of underwear, but it had to be underwear and visually recognisable as such. This was to stop the last item from being a skirt, or an underskirt or something like that. Basically, it is a strip game that is being watched by people there for entertainment. Don't be a dick, take your kit off if you are losing and give the audience something to cheer for. Which was fair enough.

I was wearing shoes, a skirt, a T-shirt, a bra and panties. That would also be my undressing order. Hanna was the same except she was wearing jeans instead of a skirt. I was freshly waxed all over, Hanna was neatly trimmed down there but did have pubes. Neither of us were intending of losing, but assuming the promise of no mobiles was delivered we were both playing and so in a game of chance there was a real possibility that one, or both of our panties could hit the deck. May as well look cute.

"Sorted?" I asked Hanna.

"Yep," she nodded.

We went downstairs and popped our heads into the living room. Hanna's parents were there as well as they were having a meal and drinks as they do every so often. "We are off," I said.

"Have fun," was the chorus of replies. Except for Mum.

"Good luck," Mum said, "Try to keep your panties on."

I just smiled at her bluntness. Hanna's Mum would know what we were doing, but neither of our dads needed such information. I didn't reply, I just nodded my head and left the room. I would let Mum explain that one to them. I checked I had my phone and my money and then we headed off to the campus.

As was promised our mobiles were taken off us and put into secure lockers, which we were given the key for. They also checked our watches that they were not capable of photography or video and then let us in. The checks were fairly thorough and as the night progressed there wasn't a mobile in sight. Security was everywhere, but there were no incidents. Except for when a drunk guy got kicked out for punching a guy who was "looking at his girlfriend's tits." Sorry to break this to you mate, but she was up on stage playing the game, a few hundred people were looking at your girlfriends' tits. If she lost a few hundred people would have been looking at her pussy as well why pick on him specifically?

"Signed us up," Hanna said when she came back from the bar.

"Er, what?" I said.

She grinned at me as she sipped at her drink. "Signed us up," she repeated.

My heart fluttered at her words. It was very different talking about playing and actually committing to it. "What game?" I asked.

There had been a few games through the night. All card games, but High Card, Black Jack, a simplified quick Poker type game, Snap, amongst others. Some were against the house, and some were people playing each other. "Simple high card," she said, "Me vs you. One of us is getting naked."

"Really?" I asked to which she just nodded with a mischievous grin.

"You wimping out?" she asked.

"Oh fuck no," I said instantly. I was terrified but there was no way I was wimping out. "I just feel bad for you that you are going to lose your panties."

"We will see," she said dismissively. "Wanna make it interesting?"

"Go on..." I prompted.

"My revenge for the other week," Hanna said, "Same deal, but instead of my brother, our parents."

"Loser gets naked in front of our parents?" I said looking at her. She just nodded. "What if they have gone home?" I asked.

She just looked at me like I was stupid. "Yeah, that is never going to happen," I said laughing. Once they had had a few drinks they would be there into the early hours of the morning.

"So same rules. Go in dressed and undress. Stop when they say stop," Hanna said.

"Deal," I said offering her my hand.

I was so nervous. There were a lot of people here. Like, a lot. My usual displacement of nerves was to mess with my phone, but that had been taken off me. I felt naked without my phone, there was potential that I was going to be actually naked soon.

"Sophie and Hanna," echoed out of the speakers.

"Ooo, let's go," Hanna said as we stood up.

I was buzzing. My entire body was tingling. It was a perfect mix of nerves and pure adrenaline. I had drunk enough vodka to quell the inhibitions and I was looking forwards to this. I was feeling confident, which is a little illogical as we were about to play a game of pure chance. A deck of cards would be shuffled by a shuffling machine a number of times that would be picked by us and placed face down. We would pick who went first and then one at a time we would turn over a card. The lowest card loses, and whoever turned that one over removes something of her choice. If there is a draw then we both remove something. Jokers are included in the pack. If you draw a joker you automatically win. Your opponent removes something and you can put one item of your choice back on. If two Jokers are drawn on the same hand then they are cancelled out, nothing comes off and nothing goes back on. A simple and clean game.