Self Dares

I healed fairly well. I have lost a bit of flexibility in the ankle that I broke, but nothing that affects anything that I need to do. It is also expected that it will improve over time anyway, so I can't really complain.

I messaged Andy as soon as I was physically able again and insisted that he let me take him out for a meal to say thank you. He resisted, but I am fairly persuasive when I want to be so he eventually agreed to it. We didn't go anywhere really posh, I am not exactly rolling in the cash, but the restaurant was nice enough. It was one of the ones where you needed to dress up. Everyone else there would be smartly dressed and not being the same would mean you would stand out.

It took me all day to pick my outfit. There is a very fine line between a slinky dinner dress and where is the rest of it? I wanted to look nice for him and I realise how condescending that sounds. He was under no illusion that it was not a date and it was just a thank you. Not being a bitch, but I really didn't want to lead him on. He fancies me and that is cute and I am flattered, but messing with him in any way like that would make me a bitch, and I am not. I don't think anyway. Well, unless you want me to be, in which case I can be a super bitch if you so wish.

I eventually settled on a black pleated bodycon dress. It was mid-thigh length, so long enough to be sophisticated, but also short enough to be sexy. The front had a bow-type design that wrapped across my chest in an off-the-shoulder design. The back was a low-ish cut around where my shoulder blades were. So no bra, but I didn't need one and the dress had built-in support, again, not that I needed it. It would at least hide perky nipples if I got cold. I opted for black six-inch stiletto heels which had a silver design on the straps which I paired with a silver clutch bag which was big enough for my phone, wallet, key, basic make-up and a mini perfume.

My underwear for the single item I would be wearing took a fair amount of time as well. Which considering my earlier statement of "it is not a date" seems a little silly. Why spend so long deciding on something that he isn't going to see. Good question, confidence I guess. Fake it till you make it as they say. If you feel confident you tend to be confident and cute underwear, even if no one is going to see it goes a long way to projecting confidence. I eventually settled on a pair of bikini DKNY black panties, with the DKNY printed around the waistband of them in white. Cute and sexy, a good combination.

I did toy with going without any underwear on and for a while, I did seriously consider it. The dress though was not long enough to reliably get away with it. I had been to the restaurant before and as they didn't pack the people in you were visible from a lot of shallow angles from the people seated. A clumsy shift of position or something and it was very possible a few people would see up my dress. I did model for Mum and grilled her if she could see a visible panty line. She insisted that she couldn't and after several "are you sure" and different positions I believed her. Further cemented when she said, and I quote, "That dress is way too short and floaty to not be wearing any if that is what you are hinting at."

I showered, removed all body hair, again, a confidence thing and got dressed. I put on a small cardigan as well as it was fairly chilly outside. I refused the offer of a lift by Dad and went and got the bus. I liked catching the bus on a Friday in the early evening. It was the best people-watching time. People on their way out for the night like me, mixed in with people who were on their way back from work. The different dynamics were intriguing. The bubbly ripple of "pre-night out alcohol loaded" partygoers and the subdued "thank fuck the working week is done," people. I took a seat and watched the people.

I got to the restaurant first and put my bank card on the table so there would be no bill presented it would just be debited off my card. I say my card, it was in my name, but it was Mum and Dad's money. I knew what Andy was like, he would try and pay and I didn't want him to. This was my treat to him as a thank you.

I checked the time and I was a bit early so I ordered myself a Vodka and diet coke, took a seat and waited. I checked my phone nervously as the minutes ticked by and wondered if I had been stood up. That would be really annoying if I had been. I don't see why he would though? Maybe his attraction to me was just a big joke and everyone was laughing at me. It had taken him so much time, but the trap had been sprung and here I was, sitting on my own like a saddo. Maybe the bar staff were in on it, maybe they were running a book in the kitchen for how long I would wait. Being a teenager is shit, you have so many stupid hang-ups it is insane.

The door opened and Andy came in. He saw me and smiled. It was 19:31. He was a whole minute late. He came over and I stood up. We had a hug and sat down. "Wow, you look amazing," he said.

"Thanks," I said casually as though my outfit, make-up and perfume hadn't been hours and hours of debate and tough decisions. "You too," I said back. He really did. I only ever saw him in cycling gear or casual clothes. He scrubbed up well. He had short-cropped black hair and was wearing a pair of black trousers with a white skull-printed shirt. I think it is a golf brand, from what I understand anyway. Either way, he looked fairly good in it.

We were taken to our table and seated. "Order what you want," I said, "My treat."

He smiled and we browsed the menu. A pointless task for me as I had pre-picked what I was having days ago. A bruschetta to start and then the seared tuna. If I made it to dessert the chocolate orange torte looked favourite. He picked his and we started to chat.

I will be honest that I was expecting it to be a bit awkward. We only knew each other through cycling and as much as I can geek it up with the best of them with the cycling talk I would struggle for the duration of a sit-down restaurant meal. I had nothing to worry about though, the conversation started off on the cycling via how I was with my injuries, but it quickly progressed to general chit-chat. There was never a lull in the conversation and he was actually really funny. Genuinely made me laugh with his bluntness. Not in an offensive way, or even a bit crass, he was just deadpan honest and delivered the lines well.

He was genuinely interested in me. My life, my studies, future plans for my career and all that sort of stuff. He was in finance which he described as "as dull as it sounds," but he did elaborate when I pressed him and he was indeed correct in his description. The courses of food came and went and were all fantastic. He had soup, which I was fairly impressed with, my food choices were mainly the ones I was least likely to drop down myself. He managed to eat it like an adult though and didn't spill any. His main course was a creamy chicken pasta dish which was really nice as well as he let me try some. Off his fork and everything. I know I know. We should have ordered spaghetti and gone all Lady and the Tramp.

We did make it to dessert and the chocolate orange torte was fantastic. He ordered the same thing. We were invited to go to the bar as we had clearly outstayed our welcome at the table and they needed the table. I had been drinking pretty much all night, but I wasn't drunk. The conversation flowed better than the alcohol and it was nice. The evening was nice. More than nice. His eyes are also very dreamy. They are normally hidden behind sunglasses, but he really does have the nicest eyes.

There was no pressure at all on me. Every time I went for dinner with a guy around my age there was the underlying unasked question constantly hanging in the air, and that question was. "Soooo. When do you put out?" Is "putting out" a common phrase? To be a bit more blunt, when a girl (or a guy for that matter) "puts out" you are getting sexy time. It was strange, for the first time in my life I was out for dinner with a guy and it was me toying with that unasked question. My brain wasn't helping, egging me on and goading me into taking a risk. Comments like, "Oh come on, you like him, he likes you. Are you going to fuck him or what?"

For the first time in my life, I was potentially risking rejection. I know how full of myself that sounds, but I had always been the askee and never the asker. I have never asked anyone out before and yes I realise that isn't helping my case for me being full of myself. "Do you want to go for a drink?" he asked.

"I would love to," I said.

"My treat," he said with a smile.

I protested, but not that strongly. I would have happily gone halves on the drinks, but the meal had been over £100 with the drinks and as understanding as my parents were even I would feel like I was taking the piss slightly if I racked up a further three-figure bar bill. We went to a local bar that he knew and I continued on the vodka. Out of habit, I watched the barman when he poured my drink ensuring that it was a single he had ordered and not a "get her drunk" double, or triple. I caught one guy trying to "loosen me up" with a quadruple. That night ended fairly soon after that and not at all in the way that he hoped.

The bar was a little louder and so it was harder to talk, which I would normally have welcomed. I like a good chat, but several hours with someone you don't really know that well and a louder bar would normally be welcome. It was just annoying though as I really did like him. I liked his company. "Where next?" I asked as I finished my drink.

He checked the time and it was approaching closing time. "Err," he said looking at me nervously. That was the first time he had shown any sort of nerves and it was nice to see. Unerring confidence is a little psychotic. In my mind anyway, to have that much confidence in "first date" situations meant you either had no empathy or you are a murderer so have nothing to worry about as even if you make a fool of yourself she will be dead soon, so who cares. "My flat isn't far," he said.

I smiled at him. That had been the first time all night that he had even hinted at a mere suggestion that we should maybe get horizontal. His confidence cracked entirely and he started backtracking. "I would love to see your flat," I said. Genuinely I would. I was nosey and I did like looking at other people's houses. Although I was under no illusion what the reason for going back to his was. "Back in a sec," I said.

I got up and went to the restroom. I sent Mum a message to let her know I would be staying out for the night. She replied seconds later with just a winky face. I am not sure I would be quite so liberal with my children. She knew who I was out with and why I would be staying out the night. Maybe it was because she trusted me and knew I had been brought up well, either way, we had an awesome relationship. I was fairly selfish in that she would have to break the news to Dad. I am sure Dad trusted me just as much, but in his eyes I was still his baby girl and far too young to be doing "that". I reapplied perfume and touched up my makeup. Gave me a quick once over in the mirror and then went back to him again. "Sorted," I said.

We walked back to his as it was only ten minutes away and there were no taxis outside the bar. He opened the door and told his dog to leave me alone and to go to his crate, which amazingly he did and he stayed there. A well-trained dog. He poured us a drink each and we sat on the sofa. He put the TV on just for background noise and we picked up where we left off.

I started fairly rigid on the sofa but was soon leaning back and even into him. He didn't have his arm around me, but there was definite body contact. "Come on, kiss me or something," I said to myself. "Kiss him. Go on..." my internal voice said.

I looked at him and he looked back at me. I smiled shyly and looked at the floor for a second. When I looked back at him he was still looking directly at me. "Just lean in halfway," I said to myself. I hesitated. Rejection is terrifying, even in this pretty much nailed-on situation there was still the chance he would reject me. "Oh just fucking kiss him you stupid bitch," my brain said.

I leaned in halfway and he leaned in the other half. Our lips meeting we had our first kiss. We pulled back and I grinned at him. "Why did that take so long?" I asked him with a wry smile.

He didn't reply, our lips connected again and this time I opened my mouth for him. His tongue explored my mouth and I returned the favour. Our drinks were empty and the glasses were on the table. He rested his hand on my leg and I turned my body so I was facing him. I let him hold my leg in place as I turned slightly which meant my legs were no longer closed. It hadn't been my intention, but it was a great consequence and I felt his hand slide up the outside of my leg and up my dress.

I moaned softly as his hand ran across the top of my thigh and he stroked his fingers across the waistband of my panties. It didn't actually feel all that nice, definitely not warranting an audible moan, but I wanted to encourage him to take the initiative a little bit. Incidentally, I was glad I was wearing some panties, it would have been a little bit too keen to be without. We kissed while our hands explored each other's bodies. No clothes came off and the most intimate he got was the outside of my thigh and an external exploration of my panties. My legs weren't "come and get it" open, but there was no physical barrier if he had wanted to get more intimate quicker. "Are you sure?" he asked. I looked at him and was pleased I managed to hide my disappointment. We were all over each other, his hands were all over my legs and panties. As being sure goes, this is pretty much as sure as I get. I liked sex and it did it for me being the submissive. Not pinned down, tied up and abused, but I liked the guy taking the initiative, and he wasn't going to. I was horny though and I wanted sex, and I wanted sex now.

I didn't reply, I manoeuvred myself so I was knelt astride him with him on his back on the sofa. He was looking up at me, his eyes all over my body. He was still waiting for a reply. Instead of replying I knelt up higher. His eyes dropped between my legs as he would be able to see up my dress, but that was kind of the idea. I lifted my dress up and over my head dropping it on the sofa out of the way. His eyes scanned my entire body and then stared at my bare breasts. "Yeah, I am sure," I replied as I leaned down and kissed him again. I was only wearing panties and stilettos.

"Wow," he said as his eyes drank me in. He reached up and gently squeezed my breasts then focused in on my nipples.

I could feel him swelling in his trousers as I sat astride him, his erection pressing against me through his clothes and my panties. "Wow indeed," I grinned at him as I felt the power between his legs. He wasn't going to take the lead, I was sat astride him wearing next to nothing and he was still being fairly conservative. I unbuttoned his shirt and let him remove it while I worked on his trousers. Belts always cause me issues. I have no idea why, but I hate them. I eventually unfastened it followed by the button and the zip. I pushed them down and smiled at the boxer tent that greeted me.

I left his boxers on and kissed him again. Grinding myself against his hardness as we kissed and cuddled. The sofa would not be comfortable for having sex on. I hadn't had sex on it yet, but I knew that they are just not comfortable. I lifted myself up and positioned so my nipple was practically in his mouth. He took the hint and my entire body tingled. "Ooo yeah," I said as he sucked my nipples in turn. I started to wonder if I was his first as he was really passive and unsure of anything. I felt that it wasn't polite to ask. "Hey, you are being a big shit mate, am I your first?" Okay, the words could be better selected for his ego, but no matter how you dress it if you are asked if she is your first there is only one way to read that. "Wanna go to bed?" I asked him. It was partially a request as the sofa was not ideal and it was also my way of asking him if he wanted to fuck or if he wasn't into it. Literally.

"Yeah," he said smiling up at me.

I stood up and pulled him to his feet. He lead the way to the bedroom but only because I didn't know the way. He laid me on the bed and climbed on top of me. Kissing me and his hand slid down the front of my panties. "Oh yes," I whispered as I felt his fingers between my legs. I was surprised at how wet I was and I am not sure if it was luck or if he had more experience than I was assuming, but he inserted one and then a second finger. He gently started to finger me and I let him take off my panties. I kicked the shoes off as well after a fair bit of struggle and opened my legs for him. He leaned in and kissed me while he played with me. Two fingers inside me and his thumb teasing my clit.

I reached my hand down the front of his boxers and took hold of him. He felt big in my hand, but I was a little surprised. I expected bigger. I have no idea why, but do you know when you have an assumption in your head about what someone will look like I for some reason had him as being bigger. He wasn't small, I guess he was towards the smaller end of the average, but yeah. I started to play with him in his boxers and quickly picked up the pace.

We were staring at each other while we played with each other. He was good, but to be fair stick anything in me when I am wet enough and I am going cross-eyed eventually. Find my clit at the same time and I am not lasting long at all. He stopped fingering me and I gave him my "What the fuck," eyes as I hid no emotion.

"Sorry," he said as he stared at me.

Was he seriously not into this? Fuck off. At least tell me before we got to this stage. I looked at him puzzled and then felt the pulse in my hand. A wetness coated my hand and I grinned up at him. "Have you just cum?" I asked giggling.

"I am so sorry," he said as he went to pull away.

I didn't let him. "It is fine," I lied, although I did the decent thing and finished him off into his boxers. Was I disappointed? Hell yeah. Was I annoyed? No. Was I mainly relieved he wasn't not into me and he was clearly very much into me blowing his load after 30 seconds with a shit hand job? Hell yeah I was.

"Fuck sake," he said pulling away and standing up.

"It is fine," I said smiling at him. "Honestly, it is fine," I said again. These things happen, apparently.

I closed my legs and sorted out my decency as best I could laying on a bed with no clothes on and a hand coated in semen. He handed me a tissue and I took it. I got up and went to the bathroom. When I went back into his room he was wearing clean boxers and nothing else. Very much underdressed I put my panties back on and gave him a kiss. I could tell that he was beating himself up inside. "Honestly, don't let it bother you," I said. "You could at least have gone down on me to say sorry," but I didn't say that one out loud.

He hugged me and I took the opportunity to fall with him onto the bed. I at least wanted a good cuddle. We landed still in each other's arms, wriggled under the duvet and cuddled. The conversation was a little awkward to start with and I didn't know how to make it not be. I wanted to laugh about it, but I wasn't sure if that was the right approach or not. It was fairly funny, but guys can be sensitive if you laugh at something they are embarrassed about. I nuzzled into his neck and shoulder and let him stroke my back. I felt tiny next to him and that is what I love about cuddles. The feeling of protection and safety. I was kissing his neck every so often and gradually it got less awkward. "Am I your first?" I asked. I wanted to know if I was.