True Life Conquests
Chapter 5

Copyright© 2016 by hiddenrainbow

True Sex Story: Chapter 5 - This series is a retelling of various sexual exploits I have had through my life. I have done my absolute best to record things faithfully, and base the dialogue on what I remember of the people involved (unless I have an email, a letter, video or whatever that records what they actually said). I have changed the names to protect myself, and also left out some details that might allow someone to figure out who people are otherwise.

Caution: This True Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   Teenagers   Consensual   Heterosexual   True Story   First   Oral Sex   Anal Sex   Exhibitionism   Voyeurism  

I remember exactly where I was when Louisa asked me about her virginity. It was just after we’d got back from Europe, and we were in the pub in town for an evening of casual drinking. It was a pretty big pub, with space for playing pool and a jukebox closer to the door. I was standing next to the jukebox trying to pick a song when Louisa came over. She was holding her usual drink, an Archer’s and lemonade. The others were gathered around the pool table, where Chris and Sol were trash talking each other without actually playing much pool.

‘Queen or Queens of the Stone Age?’ I asked her as she came up to me. ‘Both queeny, but one more classic.’

‘Can I ask you about something?’ Louisa said.

‘Sure, of course darling.’

‘It’s a bit ... private.’

‘Ok one sec, ‘ I selected “Don’t Stop Me Now” by Queen, which resulted in assorted cheers and boos from my friends. ‘You have my undivided attention. Want to sit over here?’

We sat together at a table next to the pub window facing out onto the street. ‘What’s up?’ I said, sipping my own drink.

‘Ok. Well. We’re all going off to university at the end of the summer, and I was sort of hoping I’d have a boyfriend, but I don’t.’

I made a face at her. ‘Everyone I know would go out with you in a second. Plus, unless they go to the same university as you, there isn’t much point right?’

‘Don’t be silly. Anyway, there’s nobody I really like that way right now.’

‘Are you sure? Because if that’s true, why are we talking about this?’

Louisa paused. ‘Ok I guess maybe there’s one guy.’

‘I’m listening, ‘ I said. A part of me was hoping it would be me, but I thought that if it was, we wouldn’t have been having this conversation.

‘ ... it’s Mika, ‘ she said quietly.

‘Mika from my band?’

‘Of course yes. He’s interesting!’ she said a little defensively. ‘And he’s a really nice guy when you talk to him. Kind of shy.’

‘No no, I get it. He is a great guy for sure. So do you want me to talk to him?’

‘You think he might be interested? I just ... I’d like to try ... doing stuff before I start university and I have to make all new friends.’

Everyone knew Louisa was a virgin. She’d not really ever had a serious boyfriend. She had dated the guy next door (I mean literally he lived next door to her), but that had never seemed more than a distraction. And she’d sort of dated Sol and I think Chris too when she was 15 or 16. But I never thought she’d be asking me to help her lose her virginity, even indirectly.

‘He’d be crazy not to be!’ I said, looking her up and down. She blushed. Louisa was absolutely the most attractive of my friends. In fact, she was probably the prettiest girl I knew until I was in my mid twenties. Unlike most of my friends, she’d never gone through any type of image makeover, and had been dressing exactly the same and had the same hair since I first knew her. Somehow, this added to her down to earth charm. She almost always wore tight blue jeans and tank tops, with little sweaters or cardigans. She had small but beautifully shaped breasts, and a little round bottom. Her hair was always very long (almost to her waist) and straight, and she hardly ever wore obvious makeup other than a little mascara when we went out. I suppose thinking about it now, she had the ‘girl next door’ thing down without really trying. And that was part of it. Lily was quite happy to wear clingy short dresses to parties and dance like a stripper on the dance floor, and Freya too had her selection of revealing clothes. Charlotte was more tomboy-like in her dress sense, but Louisa just seemed to dress like she wasn’t trying to say anything, just putting on some clothes she liked.

She was also vulnerable, if that’s the right word. Her mother and father had married for money (his money), or at least that’s what I always assumed. When we first met, she had been living in a huge house outside town. It had a tennis court, and her dad had a collection of cars, including a yellow Lamborghini and an Aston Martin. She had probably been the richest person I knew. Not too long later, when she was about 16, they got divorced; Louisa and her mother ended up living in a small townhouse. If she wanted a relationship, she probably needed someone who would take actual care of her, and I resigned myself to the fact that Mika would be better for her than I would.

‘Anyway, I’ll definitely talk to him about it, ‘ I said, smiling at her.

‘You’re the best, love you, ‘ she said, hugging me.

‘Love you too, ‘ I said. She smelled so good, like the sort of fruity perfume teenage girls tend to wear.

Our band was made up of myself, Mika, Sol and Evan. We practiced every weekend, typically in Evan’s garage, and usually during the week if there was time. During a break in a weekend practice, I asked Mika if he liked Louisa. Mika was very shy for someone who was a lead singer.

‘She’s very sweet, ‘ he said.

‘Would you go out with her?’

‘What? Well, you know man ... I mean ... yeah sure. I mean ... if she wanted to. I don’t know if I can ask her out though.’ ‘She wants to go out with you man. She told me about it.’ I tended to say ‘man’ and ‘dude’ a lot when I talked to Mika or Evan. I couldn’t help it.

‘What? Serious?’

‘Yup. I can set you guys up if you want.’

‘Well ... yeah man ... that would be ... yeah amazing.’

Long story short, I set up a date for the girl I had a crush on and one of my friends. This seemed a little unfair to me, because by this point, I hadn’t had actual sex in over a year. It seemed like everyone else was getting some except me. Sol and Lily were dating again, and Freya had found herself a guy from the year above us at school who was already working on an economics degree. Charlotte was dating someone from the town who I didn’t really know. I did feel happy when Mika and Louisa’s first date went well though, and they started properly dating. It was nice to see two of my friends in that blissful honeymoon period you get at the start of a brand new relationship. Mika lived pretty close to Louisa, so it was easy for them to see a lot of each other. It wasn’t too long before Louisa and I had the talk I’d been expecting. It was almost right after the school holidays started that summer. We spent a lot of the summer sitting together in an Italian cafe, eating chocolate wafers and drinking glasses of hot chocolate while we chatted about everything and nothing. A lot of people weren’t around, so we spent time with each other. That wasn’t to say we weren’t close ordinarily, but we definitely got closer our last summer together.

‘I have some news, ‘ she said in a shy but excited voice.

‘You and Mika finally bonked?’ I said immediately.

‘Ugh, don’t be horrible ... but yes I suppose.’

‘Congratulations!’ I said, raising my chocolate wafer in cheers, then dipping it in my hot chocolate. ‘So?’

‘So what?’

‘So how was it? Don’t tell me I’m the first person you’ve told?’

Louisa blushed crimson. ‘It was very nice. We lay in bed and talked for a long time afterwards. It was ... special.’

‘And the actual ... you know, ‘ I said, making circular motions with my hands. ‘Event itself?’

‘I enjoyed it. Sure. Freya said it takes a while to enjoy it after your first time, so ... you know. And I haven’t had a chance to tell Lily or Charlie yet.’

‘I’m surprised Freya can remember her first time now!’

‘You are such a bitch, ‘ she said, slapping me on the arm playfully. ‘Anyway ... I’m sure we’ll have lots of time to practice, ‘ she said, sticking her tongue out at me. It was a small tongue, and just for a moment I had a mental picture of Louisa running it up and down my cock. I blinked and looked down at my glass.

‘I’m happy for you, ‘ I said. ‘Does your mum like him being around so much?’

‘She thinks he’s very nice. She said he’s a bit scruffy and mumbly, but he’s very sweet.’

August finally came. I was counting down the days until I started university, and all of us were spending as much time together as we could. There was a definite sense that after we started university, we’d never all be together again, or at least not in the same way. All of the guys (including me) had taken a year out, but some of the girls weren’t, so a lot of us were starting university at the same time. Lily was going to Oxford, Charlotte was off to Southampton, and Louisa was going to a university close to home, so that she could be near her mum. We were back in the pub again, having a midday celebration. Evan and Mika hardly ever came out with us as a group, I was never really sure why. It was just the usual suspects: Lily, Charlotte, Freya, Louisa, Sol, Martin, Simon, Chris and Robin.

‘So Mika and I aren’t together any more, ‘ Louisa told me. We were standing at the bar together getting drinks for the group.

‘Really? What happened?’ I said.

‘Oh nothing bad. It’s just ... we’re both going to uni and we talked about it. We decided it was best to end things now as good friends. Then there’s no awkwardness or guilt or anything. I’m fine. We’re both fine.’

‘Wow. Well I suppose it sounds like a good plan, are you really ok?’

‘I think so. I’ll miss him though.’

‘Of course. A new start then, ‘ I said, raising my glass to her and smiling.

We took the drinks back to the others. I put them down and gave Louisa a big hug. She rested her head against my chest and squeezed me tightly. ‘You’re the best, ‘ she whispered.

‘Save it for the bedroom you two!’ Sol yelled, laughing. Louisa rolled her eyes at me.

A couple of weeks later, it was finally time for our last ever party, and everyone would be there. It was at the house of a girl called Sally. I didn’t really know her that well, except that she was super into horses. I’d never been to her house before, but it was enormous. The house itself looked big, we weren’t allowed inside anyway. But the land around it was massive. There were fields on all sides. Two of them looked empty, and a couple more had horses in. Our party was happening in and around the barn, which was probably almost as big as my house. It wasn’t like a farmyard barn, full of hay and horse dung. It was a sort of conversion, with a big barbecue outside, heating lamps and floodlights, and a loft area with a couple of couches. Sally’s parents obviously entertained there a lot. The barn was across a courtyard from the house. Apparently Sally’s parents were home but had promised to keep out of the way as much as possible. The party was restricted to the barn, the courtyard, and a big RV that was parked in the driveway. Within an hour or so of the party starting, drunken teenagers were climbing all through the RV and doing god knows what unspeakable things on the furniture.

Mika and I were drowning our sorrows together in a bottle of Jack Daniels. Actually, neither of us was really particularly sorrowful, or even talking that much. We were just trying to avoid the general awkwardness around us. Lily and Sol were obnoxiously making out everywhere in a final pre-university fling; Charlotte and her new boyfriend were holding hands constantly, and all in all the party seemed to be fragmenting into couples and people who were there to make out with other people, but weren’t ‘official’ couples. Mika and I didn’t really fall into either group, so we hid behind the barn and got drunk to escape the awkwardness of being third and fourth wheels.

After a while, Mika staggered off to find Evan and Sol, so that we could do some drinking as a band. Or maybe some drunken harmonizing. I came back around the side of the barn so I could watch the party without actually taking part. Charlotte was sitting on her boyfriends lap in a chair, and Freya’s boyfriend was mixing drinks for people using the barbecue as a bar. Louisa peeked her head around the corner, taking me by surprise. ‘Hey you, ‘ she said. ‘How are you feeling?’

‘Fine I guess, ‘ I said. ‘Just sort of relaxing. So many couples here.’

Louisa turned and looked over where I had been looking. ‘I suppose so, ‘ she said. ‘I wonder how many will still be couples in a few weeks?’

‘Good point, ‘ I replied. ‘Still, it’s not my favourite thing to look at.’

‘Let’s go somewhere else then, ‘ she suggested. I smiled at her and took her hand, completely forgetting my promise to drink with Mika and the others. We walked around the other side of the courtyard, where not much was happening, and stood on a little slope very close to the house.

‘Are you going to miss all this?’ I asked.

‘All these parties?’

‘Haha, no. Well, the parties are ok. I meant all this, ‘ I said, gesturing rather clumsily out to the dark countryside around us. ‘You’ll be a city kid soon. Me too I guess. All of us really.’

‘I can’t believe you’ll be living in London, ‘ Louisa replied. ‘I bet it will be amazing.’

‘You’ll be in a much smaller, nicer city.’

‘It might be fun. But I’ll miss the quiet I think.’ Louisa said. She turned to me, and suddenly we were kissing. We had kissed a couple of times before at parties, but this felt a little different. Before when we’d kissed, it was fairly chaste, even though some alcohol had probably been involved. This time, it wasn’t even a little chaste. After only a couple of seconds, Louisa was pressing her body against mine. Her tongue felt hot, and her arms wrapped around me tightly. She rubbed against me, and I slipped over on the slope, Louisa falling next to me. She laughed, and we looked at each other, then went right back to kissing. If I hadn’t been drunk, I probably would have been amazed that this was happening at all, but it didn’t seem to bother me. Louisa continued to move her body against mine, and even with all the clothes between us, it was enough to bring me to an uncomfortable hardness.

For a moment, I nearly laughed at the absurdity of it all. Only a few minutes earlier, I’d been moping at all of the couples making out, and now here I was rolling in the grass with the more gorgeous girl I knew. Louisa took my hand and placed it over her left breast. She was wearing a button-up shirt and her breasts were pretty small, but I could clearly feel a small hard nipple as a little bump through her clothes. Our legs were wrapped around each other, and she was gently grinding her hips against my leg. I remember thinking that even her grinding was done in a sort of proper way. I thought back to earlier in the summer when Freya had been rubbing up against me, and a bit earlier again when it had been Charlotte (a lot of girls rubbed against me that summer!). Both of those times it had conveyed the message that they wanted to fuck. Louisa wasn’t like that, it seemed like she was just doing it because it felt nice. My hands were at her waist, pulling her into me. And that’s when it all went bad.

‘Who’s that?’ said a voice I couldn’t identify. A torch shone on us, and we quickly pulled apart. It was Sol, grinning. I frowned at him. This was just the sort of thing he would do, and endlessly taunt me about later. Behind him were Mika and Evan. ‘Hi Lulu, ‘ he said, still smirking. I could see Mika’s face in the torchlight, he looked unhappy.

It turned out Sol wasn’t being exactly as obnoxious as I thought he was. The guys had been looking for me to have what would maybe be our last drinks together as a band. As a group, we made our way to the loft in the barn, Louisa making an excuse and leaving.

‘I’m sorry about that, ‘ I said to Mika as we walked.

‘Nah it’s ok man. Lu and I are over each other now.’ he paused. ‘I was a bit surprised though, I never knew you liked her ... in that way.’

‘For a while, ‘ I said simply. Mika just nodded. ‘Life is complicated huh?’ I said. He smiled at me.

‘I’ll drink to that.’

‘Lighten up boys, the clock is ticking, ‘ said Sol, putting his arms around us. ‘Partyyyy!’ he yelled.

‘Dude, that was right in my ear, ‘ said Mika.

The rest of the party passed pretty uneventfully, at least for me. Sally apparently had been seen giving a blowjob to some random guy in a field, which all the girls were stunned by because she’d been very shy and quiet up until now. Freya’s boyfriend had been making out with someone else, and she was now considering dumping him and going to university in a different city. Lily and Sol had spent a lot of the night talking, they also were going to different schools: Lily was off to Oxford and Sol was heading for London along with a bunch of the others (including me). Really it was the usual party stuff, with the difference that we might never have the chance to do it again. That added a certain amount of desperation, which probably resulted in more craziness and more drama than any other party that year.

I actually didn’t see a lot of people after that. With only a couple of weeks until university started for most of us, people were busy packing and moving and planning. Some people had to go down to school early to sort out accommodation and stuff. A couple of people were desperately calling schools trying to get a last minute place somewhere. I’d talked to Louisa and Sol and a few others on the phone, but I think Martin and Simon were the only people I’d actually seen after Sally’s party. So I was a bit surprised when Louisa asked me over for lunch a few days before I was due to go down to London.

When I turned up at Louisa’s place, her mum was out. Louisa said she’d gone to a charity meeting and was then going shopping, so she wouldn’t be back until dinner time. Louisa was wearing another casual button-up shirt in a sort of pale blue colour and her normal tight blue jeans. She wasn’t wearing socks and I noticed she had perfectly shaped little feet.

‘I thought I could practice some cooking, since I’ll have to cook for myself all the time soon, ‘ she said, smiling at me. ‘How about it?’

‘So I’m your culinary guinea pig? I’m slightly afraid, ‘ I replied.

‘Shush, come and help me, you’re the chef after all.’ I’d had a job in a kitchen earlier in the year, and if nothing else I’d learned to chop and prep things properly. Louisa put me to work cutting vegetables, and we both drank cider while we cooked. It was strange for me to be alone in Louisa’s house with her. My own house was always full of people, and the only other times I’d been to a girl’s house alone was when I was dating Hanna.

I don’t remember what Louisa made for lunch, but it was pretty good. We talked together just like we had all summer, and I think we both said how much we’d miss each other at least ten times. It felt like a grown up thing to be doing, which sort of seemed appropriate since we were both moving out of our parents’ houses.

After lunch, Louisa asked if I wanted to come upstairs to watch TV for a bit. I was still putting off doing my packing, so I happily agreed. Louisa put on a video tape of Friends, and we settled down on her bed to watch. Her bed was fairly small, but we were also quite comfortable cuddling. She lay with her head on my chest for a long time. I think the first episode was almost finished by the time she moved away.

‘You going somewhere?’ I asked. I sat up and stretched. I had almost fallen asleep. Louisa didn’t answer, but sat next to me on the bed. She wasn’t looking at the TV any more, she was looking at me. I turned to face her. I couldn’t really read her face, but she was definitely thinking about something. ‘Everything ok?’ I said.

Louisa smiled and nodded. We looked at each other for what felt like a long time, I couldn’t really hear the sounds of the TV in the background any more. It wasn’t uncomfortable or awkward in any way though. I felt relaxed. ‘Would you kiss me?’ she said. I nodded and leaned towards her. Our lips touched together gently. Her lips were so beautifully small and soft, it was more like kissing a dream than a real person. It wasn’t a tongue kiss, just lips touching, but it went on for a while. Everything seemed so quiet. Louisa was breathing heavily and I was feeling a little dizzy. She leaned towards me, and I figured that she was trying to push me backwards. I lay back on the bed, holding her shoulders and pulling her down with me. Then her tongue was inside my mouth, exploring mine. I couldn’t properly remember a lot of our previous kisses, alcohol having been heavily involved in most of them, but this one was special. I’d have expected Louisa to kiss shyly, which she mostly did, her tongue moving back as if she was afraid of me biting her or something. But she had been more aggressive already than I thought she could ever be, and I remembered she wasn’t a virgin any more. She’d had a cock inside her, just like all her friends, and now things were a bit different.

The thought of Louisa getting fucked and the feeling of her soft skin against mine had already got me fully hard. Louisa was rubbing herself against me subtly, a little like she had at Sally’s party, but slightly more restrained. I didn’t even notice at first, but as she speeded up a little her kissing became more intense, she pushed back against me as if she was trying to fuck me just with her mouth.

Again Louisa pulled away from me, sitting back on her knees between my legs. Then she climbed off the bed. She unbuttoned her jeans and peeled them down her legs. Louisa didn’t really wear dresses or skirts much, and I don’t think I’d ever seen her legs before. She was breathtaking. Her skin was fair but not too pale, and her legs looked so slender and sleek. Even though she was obviously a woman aware of her sexuality, she still had the body of a young teenage girl. The shirt covered her panties, but she reached under it and pulled them quickly down. I was absolutely focused on Louisa’s body, and I saw a brief glimpse of a little hair under the shirt as she moved. The panties were white and lacy, and she stepped out of them quickly.

‘Do you want to take your shirt off?’ I asked. It was the first thing either of us had said for several minutes.

Louisa looked down at the ground. ‘I’m a bit shy, ‘ she whispered. ‘A bit ... small.’

I frowned at her. ‘You look so incredible, ‘ I said. ‘Please?’ I smiled at her. She smiled a little back and looked down at the ground for a moment. She unbuttoned the top of the shirt, but instead of taking it off she climbed back onto the bed and moved towards me. She unzipped my jeans and pulled them down; I lifted myself off the bed to help her. She unceremoniously pulled down my underwear too, and my cock sprang out. Louisa stared at it for a moment, then lowered her head to me. I braced myself, but still the feeling when her little tongue gingerly tasted my cock for the first time was incredible.

 
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