True Life Conquests - Cover

True Life Conquests

Copyright© 2016 by hiddenrainbow

Chapter 2

True Sex Story: Chapter 2 - 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  

Hanna and I met in 1999 through a friend at my high school. She was the same age as me (actually a couple of months older), quite tall for a girl, but not skinny. She had curves, and very large breasts (even now I'm not the biggest fan of breasts, so I have no idea what cup size they would have been, but they were big enough that men would stare at her in bars). She had brownish blonde hair, which she generally kept fairly short, and a pretty smile. Hanna and her mother lived in a small town a short drive from me. We both went to high school in the same town, but lived on opposite sides. By the way, most of the people (boys and girls) in our group of friends lived in a single small town. The girls all went to the same school, which was a girls-only private school (my first proper girlfriend Beth went there too). I went to school in another town close by, along with all the boys from our group. Hanna went to a different school in the same town as my school, but once we started dating she was welcomed into my group of friends (unlike Beth, who they always thought was a bit weird).

We didn't hit it off immediately, or have that 'first-they-hate-each-other-then-they-love-each-other' thing, but somehow and slowly, we just bonded. I think she was the one who asked me out, as I was still quite shy as a teenager. We dated for a while, or what felt like a while in high school. At a party midway through the year, I lost my virginity to her. It's not a particularly exciting story, although it was outside in a forest and my friend (the same one who introduced us) practically tripped over us doing it. After that, we fucked like ... bunnies who fuck a lot. In her house, her bedroom was the attic, so we'd climb up the ladder and just spend all day in bed. She always wanted me to cum inside her, which I did sometimes ten times a day. She also loved to spend ages sucking on me, although she never let me cum in her mouth. She would get me really close, then quickly slide her pussy onto the tip of my dick and take my cum inside her.

Hanna and I talked about sex quite a bit. She loved me to talk dirty to her, and had a skill for it herself. One weekend I was sick, and she asked me to come over so she could take care of me (Hanna didn't drive). She packed me up in pillows and blankets in her mum's bed and made me soup and hot tea (her mum was visiting her sister in Ireland I think). The next day, I was still in her mum's bed but feeling noticeably better. I woke up to her sliding under the covers next to me. We hadn't seen each other before that weekend for over a week, so I hadn't had sex in a while.

'Feeling ok?' she whispered.

I rolled over and kissed her 'much better.'

'Would you like to fuck me?'

I stroked my chin as if thinking about it ' ... ok maybe just a little.'

She grinned at me and slipped her hand into my underwear, stroking me. 'Are you sure it's just a little?'

I tried to suppress a moan. 'A significant amount?'

'That's closer. Do you think my pussy is wet for you already?' she whispered.

'Mmm. I hope so.'

'Maybe you need to make sure, ' I slid my hand down Hanna's legs, around and back up the back. She was wearing a thigh-length nightgown, and as my hand moved up her legs, I realized she had no panties on. I could feel her wetness even before I touched her pussy. She whimpered slightly as my finger slowly thrust into her.

'I think you are a bit wet yes' I answered her. Hanna started moving her body against mine.

'Maybe ... another finger just to double check' she managed. Wordlessly, I pushed a second finger inside her and curled them up against her pubic bone from the inside. She always loved this.

'Ngg fuck baby. Are you feeling better this morning?' She asked again.

'Definitely'

'Good enough to get your big dick working?'

'See for yourself, ' I replied. I pulled down my underwear and moved the blankets off me so she could see my cock, hard against my stomach.

'I need it right now' she panted. 'I need it inside me. Please baby.'

'Get on top of me, ' I ordered. Hanna obediently climbed onto me.

Hanna had been with a few other guys before me, but she was still a teenager and her pussy was fairly tight. As a result, she never liked to take all of me right into her quickly. She couldn't really get all of it inside, but when she was on top she could sort of slide back onto it and take nearly the whole thing. She liked to slide it in slowly and adjust before we could really fuck. This time was no exception, she slid her wet pussy slowly onto my dick, eventually taking almost the whole thing inside her. 'Fuck ... dammit baby sometimes your dick is too big, ' she said breathlessly. 'Just a second, ' she slid off me a little and rotated her hips with about half of my dick inside her. She seemed very focused. After a minute or so of this, she looked up at me. 'Ready?' she said. I nodded.

Hanna slid her pussy back onto me. She still couldn't fit the whole thing, but the feeling was amazing. After months of us being together, I had learned to hold off cumming for a pretty long time. The result was usually that I had a huge orgasm when it happened, but she didn't seem to mind at all. Hanna placed her hands on my chest and started moving herself slowly up and down. Usually when we fucked it was hard and fast, but this time she was in control and going slowly.

'Do you ever think about other people when we're fucking?' she asked me as she rode my cock, her large breasts swinging towards my face. My eyes went wide - even as a nineteen year old I knew that this was getting into dangerous territory. Nevertheless, there is something about having your penis inside a vagina that prevents your brain from working properly, and I opted for honesty.

'Maybe sometimes... ' I managed, as she started to circle her hips. She was obviously very turned on, her face was flushed and she had her lips pressed together tightly, that focused look on her face again. She asked the question.

'Who?'

'Well, ' I said slowly, as if I was being forced to think of someone, 'Maybe Louisa?'

Louisa was a close friend of mine, another of the girls in our group that lived in the little town. She was a year younger than me and extremely attractive: she had a petite frame with pert little breasts, a tight ass, and long hair that was a sort of half-blonde colour. Her face was sort of pixie-ish, with a small nose and wide green eyes. All the boys I knew had crushes on her, but she never showed much interest. We had kissed a couple of times in the past (in our group almost everyone kissed everyone else), but nothing more than that had ever happened. Hanna grinned naughtily at me. 'Oh really? Isn't she still a virgin?' Hanna said as she slid her pussy onto me.

'Mmnm, I think so, she told me she doesn't like any of the boys that like her.'

'Do you think she would be able to take your huge dick in that little tiny mouth of hers?' Hanna asked huskily, moving her pussy up and down faster now.

'Not like you can baby, ' I managed.

'Mm but I bet you could help her learn couldn't you? Just help her take it into her hot mouth an inch at a time?'

'Mhm.'

'Maybe you would give her a couple of drinks and bring her back to your room?'

'Yes ... that could be fun.'

'You'd have your hands on her little tits. She'd probably be very shy and embarrassed, but you'd take control. You'd undo those tight jeans she likes to wear and pull them down her legs... ' I was breathing a bit faster now, and Hanna looked like she was really close to cumming. I didn't know how long either of us would be able to keep doing this. 'I wonder what colour panties she'd be wearing? I bet a little virgin like her would have baby blue ones with little white edges ... Would you pull her panties down nice and slow and lick her little pussy while she's standing there in your room?'

'Fuck yes, ' I moaned. I was getting really close now. 'I would lick her until she couldn't stand up any more.'

'Do you think she would be scared when she saw how enormous your dick is baby? Would you teach her how to suck it, or do you think her mouth would be too small? Maybe she'd be upset that she couldn't do it and ask you to put it in her pussy instead? Would you help her out? Would you lie back on your bed and let her slide that tight little virgin pussy onto you?' Hanna continued as she moved up and down my cock faster and faster.

'Nn ... yes ... I'd fuck her so good.'

'Do you think she'd be loud when she came on you? You might have to put your hand over her mouth to stop her screaming. Then you could roll her onto her back and fuck her hard. Use her like a brand new pussy just for you to fuck? Would you fill her up good with your huge dick until she couldn't take any more? Make her beg for you to fuck her harder? Beg for your cum all the way in her? Make her come back for more and more every day? Make her try harder until she could take your big dick all the way in every hole? Make her a slave for your cum?'

That was absolutely all I could take - Hanna could be dirty but this was something new. My whole body spasmed over and over as I filled her pussy with a colossal load of cum. As soon as my cock started pulsing inside her, she came too, squeezing me with her internal muscles as I kept cumming and cumming. Even before I was done, my cum started dripping out of her, back down my cock and onto my stomach. When she finally stopped moving and collapsed on my chest, she seemed hesitant to climb off. Eventually, she crawled slowly up my body until my dick slid damply out of her, along with a substantial amount of my cum, which all ended up on my stomach too. She crawled back down until we were face to face, her stomach slippery against mine with our sweat and a lot of cum.

'Oh my god, that was insane, ' I said. Hanna just grinned, and rolled over to grab a cigarette. I disliked smoking, especially when she did it in bed (her mother smoked too, so Hanna was actually stealing hers this time), but at this point I really didn't care. She lay there smoking for a few minutes, knocking the ash out into the ashtray next to the bed.

'So would you really want to fuck Louisa?' she asked coyly.

I hesitated again, but given that Hanna had cum so hard a few minutes ago, I figured I was safe. 'If it's ok with you, sure. Why, do you know something?' I replied.

'I may have heard some things. And maybe if I tell her what you've got waiting for her she'll be even more interested ... Or terrified I guess. Hm. I also heard Freya might have a surprise for you some time, ' She stuck her tongue out at me.

I rolled my eyes. 'Well, maybe ... wait, Freya?'

'Yeah, somehow she heard you have a really big cock, she asked me if it was true.'

'Seriously?'

'Yup! And then she asked if I would mind her trying to fuck you.'

'Ok now I don't believe you at all. You're such a liar, ' I laughed.

'I am absolutely serious. I told her if we break up sometime she's welcome to have a ride.'

I stuck my tongue out back at her. 'Do I get any say in this?' I asked, still not really believing how much my thoughts about two of my friends could have shifted in just a few minutes.

'I suppose it's up to you. Sol tells me she's an amazing fuck.'

I nodded. That at least was true, he had told me the same thing. Freya was a redhead, about average height and with beautiful well-developed breasts. Apparently she had been having sex since she was fifteen and now, at the age of only eighteen, was getting quite a reputation as being the best fuck in her school. I had heard from Lily, another of my friends who liked to talk about these things, that several girls in her school had asked Freya for help learning how to take care of their boyfriends. I had even heard that one of the boys from another school in town had broken up with his girlfriend just to get a blowjob from her (I remember that well, but I don't think I ever found out the details, so don't ask).

As well as lots of sex, my relationship with Hanna was full of arguments. I don't think either of us really understood how to have a relationship where we spent so much time together, and both of us were emotional teenagers. Eventually, we broke up, but we stayed close and kept sleeping together on and off (which didn't stop either of us also sleeping with other people, as you'll find out later). After school finished, we decided to go on holiday to Asia together (me, Hanna, my friend Sol and my best friend Simon). It wasn't a great holiday for me: it was hot and sticky everywhere, and the big Asian cities were especially bad. There was no fresh air, and the noise was terrible. Hanna and I continued fucking on a regular basis, which I think annoyed the others who had left their girlfriends/boyfriends behind. Sometimes it's hard to let go, especially when the sex is really good. Basically all we did was argue and fuck, as she constantly reminded me.

Eventually we left the big cities and made our way to a tiny island somewhere in South-East Asia. It was a little better, but I wasn't keen on going in the ocean except to cool off (I don't even remember why, something about the idea of sea urchins and sharks and jellyfish maybe), so I just lay on the beach and observed people. The beaches were packed with young people playing, gorgeous girls sunbathing in little bikinis, and local people walking back and forth selling blended drinks and freshly made snacks for less than the cost of a pack of gum back at home. The evenings were still warm and sticky. The area we were staying in was all wood huts raised off the ground, presumably to stop snakes and various other creatures getting in. On the first night we all shared a huge bed to save a bit of money, then we decided that wasn't good enough, and moved to a much smaller hut nearer the beach. There were two smaller beds. My two friends had to share with each other, and I shared with Hanna.

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