True Life Conquests - Cover

True Life Conquests

Copyright© 2016 by hiddenrainbow

Chapter 1

True Sex Story: Chapter 1 - 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 think I was about 14 when I realized my dick was bigger than most boys’. My memory is of a couple of things that happened that year. Now bear in mind that this was before I had seen any kind of porn, or had any sexual experience whatsoever. As a teenager, probably like a lot of teenagers, I was terrified of anything that would make me stand out (so to speak). I was fairly geeky and not into team sports (although I was very athletic), so I was not one of the popular kids by any means, and my self-esteem was quite low.

The first event was probably exactly what you’d expect. I was in the showers after rugby practice (which my school called ‘games’). I hated communal showers, and usually tried to throw on my clothes and leave without having one. This time I think I had probably got very muddy (I don’t really remember), and my teacher insisted. If I had to shower, I generally just faced the wall and got my hair wet so it looked like I’d got clean, then jumped out.

This time though, maybe because I had to stay a few seconds longer to wash off the mud, as I turned to leave I noticed a couple of boys facing in my general direction. They weren’t looking at me, but I could still see their dangling cocks. I didn’t have to look down to know that mine was significantly bigger. As a 14 year old boy I looked at it many times a day. I left the showers as quickly as I could, probably blushing.

The second event was a little later that year, maybe after school had finished for the year. My friends and I were watching a horror movie late at night (I think it was called ‘The Necronomicon’). At one point there were some boobs on screen. I think they stayed visible for a few seconds, which was enough to give me an erection. After they left the screen, my friend Robin looked over at me sheepishly. I could tell from his expression that he had found it exciting too. When I looked down at my crotch, there was a significant tent pole effect. However Robin had barely anything visible (maybe a pup tent pole?). Again I remember being extremely embarrassed.

I remember that I used to get erections at random times fairly often, which I think is very common as a teenager. For me, it was often while riding the bus to school in the mornings. Maybe it was the vibration, but I always found it difficult and awkward hiding my large hard-on from the other passengers. A couple of times I tried fiddling about and securing it under the waistband of my underwear. This hid the thing from other people on the bus, but then was a bit painful to move or do anything. If I bent over, my ribcage brushing the tip of my cock felt good, which just made things worse. Other times I tried pointing it downwards before I left the house, securing it as far as possible using the left leg of my underwear (I always wore tight boxers, a sort of short cycle short thing, so the legs were elasticated). Doing this after I was already on the bus was next to impossible, but if I did it at home it sort of worked, although it was fairly painful when I started to get hard, as things were bending the wrong way. If I was wearing jeans or tighter trousers, I still felt as though my cock was hugely obvious to everyone. I would invariably spend my bus ride (and often a few minutes afterwards) with my backpack or a ring binder clutched over my crotch to conceal any signs of an erection.

For the rest of that year I was convinced that I was some sort of freak, and that no girl would ever want me. Now, that isn’t to say I was completely clueless about sex or women. My father was a scientist (I’m being deliberately vague here) and had several textbooks on human sexuality lying around the house, including ‘Everything you’ve always wanted to know about sex but were afraid to ask’. I had read parts of some of them, or at least looked at the pictures - cough - but I suppose I’d never read anything on the size of the male apparatus or its potential effects. I’m fairly sure this is mentioned in ‘Everything... ‘ but I guess I never read that part. By this stage I’d kissed a few girls at parties, although I’d never been on a date or anything like that. No female other than my mother had seen me naked.

The next year was 1996, although when we went back to school it was still 1995. I think that was the year a kid at school brought in a porn magazine (yes they still had those back then) and I saw a ‘real’ naked woman for the first time. I don’t remember there being any men in the magazine at all, just naked girls spreading themselves in various positions. Although we couldn’t drink legally, my friends and I still had parties. At one of these parties, I met a girl who ended up being my first girlfriend. Her name was Portia, we were both 15 at the time.

Our first ‘date’ was a trip to the cinema, and we kissed for ages at the back, without really seeing the film at all. A couple of dates later I was invited over to her house for a barbecue. Her parents seemed to like me and were fine with us spending most of the time in her room. She was a gymnast, and she showed me some videos of her doing gymnastics. I thought it was pretty impressive, and watching her in a tight one-piece outfit doing splits and cartwheels and things was a bit of a turnon. She loved Friends, so she put on a video with some episodes, and turned the volume up a little bit higher than necessary. We sat very close together, and after a few minutes I looked into her eyes and we kissed. She turned her body towards me and we started making out more passionately.

After a few minutes more of making out, she unbuttoned her shirt shyly and put my hand inside. She was wearing a thin smooth white bra, I could clearly feel her small nipple get hard as I stroked and squeezed it amateurishly. She was getting pretty flushed, her skin felt warm under my hands. A few minutes more and she managed to wriggle mostly out of the bra and I was stroking her tight little nipples. Unfortunately I couldn’t see anything, but I was definitely enjoying it.

‘Is it ok if I touch you too?’ she asked. I probably just nodded, and she moved her hands up my legs (we were both sitting on her bed at the time). After a bit, she got to my crotch, where I had a huge erection. I don’t think she had noticed it before, I may have been subconsciously leaning towards her to hide it a bit. She sort of just stared for a few seconds and then said ‘I didn’t realize it would be so big ... I’m not sure what to do with it.’

If that happened now, I would say something much smoother like ‘it’s ok baby, don’t be nervous, I’ll show you exactly what to do.’ (I’m exaggerating, but you get the idea). Being a 15 year old boy, I assumed she was rejecting me. I remember that we made out for a bit longer, then she put her bra back on and I left. We went on a few more dates, but I never got invited back to her house, and she never again came close to touching my dick (actually much later she did, but that’s another story).

It wasn’t until I was 16 that things started to turn around. By now, my friends and I had started to drink at parties, and I was heavily into goth music and wearing lots of black. At one party, which actually was probably new year’s 1997, I picked up a girl called Beth. We bonded over music (Marilyn Manson), made out for several hours, and soon after started dating. Beth was perceived as something of a slut, she had been out with most of my friends over the last year. In fact, she had dumped my friend Robin to start dating me, something he never forgave me for.

My first time at Beth’s house, we were locked in her bedroom and quickly got completely naked. She had gorgeous little tits with round pink nipples, and a little bit of brown hair covering her pussy. As befitting a goth kid, her skin was very pale. As soon as I took off my underwear, she said ‘holy fuck!’ (I remember exactly because it was something she used to say quite often). I turned my head away embarrassed, I think she could tell what I was thinking. She said ‘do you realize what a huge dick you have? It’s fucking amazing. I can’t wait to get that thing in my mouth!’ I was amazed. I had never had a blowjob, and not only was this girl offering to do it, she seemed excited about the size of my cock, rather than terrified or offended.

‘I sort of thought it was a bad thing’ I mumbled.

‘Are you fucking serious?’ she said. Then she laughed and took hold of it. ‘It’s a great thing. A great big thing!’ She laughed again, and started stroking me up and down slowly. ‘Seriously, most girls would just fall to their knees and suck you off if they knew this is what you had hidden in your pants. If you can learn how to use him right, you can probably have any girl you want’.

‘But ... why?’ I managed.

‘Because it feels good in your cunt stupid’ she responded. ‘A big dick feels good in your cunt.’

I knew already that Beth was a little bit weird, and she had a habit of telling lies, but I could sort of tell she was being truthful this time. Again though, she could sense I was a bit skeptical. She pushed me back onto the bed and got between my legs. My hard cock lay against my stomach. She took hold of it almost like a doctor doing an exam.

‘See, here is where most guys’ dicks would be’ she pointed to a spot about 2 inches below my navel. Then she leaned her head down and licked slowly up my cock from that spot to the tip, slightly below my ribcage. It felt better than anything I had ever felt before. ‘ ... and here’s where you are’ she finished, grinning. ‘I don’t even know if I can get it in my mouth, but I’m going to really try’. She started to put her mouth on me, I almost couldn’t believe it. Then she stopped and got up. ‘Just one sec, ‘ she said, grinning again.

She went over to her school bag and pulled out a plastic ruler. Her dad was a dentist, and the ruler had the name of some drug company on it. She laid it down next to my cock and measured me, then laughed again. The ruler felt a little cold on my stomach. ‘Jesus fucking christ, ‘ she said. ‘I wish I’d measured the other dicks I’ve seen now so I could compare’. At the time I think I was too excited about having her mouth on me to wonder exactly how many dicks a 16 year old girl could have seen. I couldn’t see exactly where the ruler was, and I’ve never really been tempted to measure myself since, although several girls have asked me to. But I think that day made the difference: from then on I pretty much stopped thinking of myself as a horrible freak.

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