True Life Conquests
Copyright© 2016 by hiddenrainbow
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.
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.
And it made sense. As Beth tried to fit her little mouth around my dick, I thought back to Portia and why she hadn’t wanted to touch me. It fitted with what Beth was saying. ‘I think Robin’s dick is about half as big as yours’ she said, pulling mine out of her mouth. ‘I got all of his in my mouth at once. I can tell my jaw is going to hurt later, you better appreciate this!’ For a fraction of a second, I wondered how having my whole dick in Beth’s skilled mouth would feel. Then the world went sideways again as she managed to get the entire head of my cock into her mouth, and the feeling stopped all other thoughts of anyone and anything else. My whole body felt like it was tingling, and my cock seemed the hardest it had ever been. Beth sucked the head and managed to get a bit of the shaft into her mouth, then stopped and slowly slid out, her tongue on the underside of my dick sliding along it as she did so. I almost came right there.
‘And now it’s your turn’ she said. She lay back on her pillow and opened her pale, soft legs. Her pussy was pink and shining below the little patch of hair. It wasn’t a romantic thing to do, but Beth was not a romantic. She pointed at herself and said ‘lick me!’. I was slightly hesitant, one of my friends had told me just a couple of weeks earlier that his girlfriend tasted awful. However, I definitely felt that Beth was due some sort of thanks for explaining that a big dick could be a good thing. I positioned myself between her legs and stuck my tongue out. After a few little licks at random places, I determined that it didn’t taste bad at all. A little like sweat, but less salty. Almost like that salty sweet popcorn you can buy.
Beth taught me how to go down on a girl, in the same almost scientific manner as she had examined me. She pointed out where her clit was, and told me that some girls’ have a very small one, and some have a huge one, which I didn’t know. She would say things like ‘don’t poke it with your fucking tongue’, ‘do it in longer licks, like a cat’ and ‘try sticking your tongue in my cunt, that can feel nice’. The whole time, she lay there with her head propped up on a pillow so she could see what I was doing, and a sort of quizzical expression on her face, like she wasn’t sure about what score to give me. I squeezed her thighs while I licked slowly over her clit, and for the first time she moaned a little. I focused on her clit, and she slid down, her head against the bed, and wrapped her legs around my arms. I scratched her thigh a little with one fingernail, just on impulse, and she moaned louder ‘yes, lick my fucking clit faster’. I obeyed, lightly scratching her thighs up and down at the same time. Her legs got tighter around me and she pushed on my head like she wanted me to increase the pressure. ‘Put your fingers in my cunt’ she gasped. Beth would never use a word like ‘pussy’ when ‘cunt’ would do. I wasn’t exactly sure how to do this, but I slid one finger into her. It was so smooth and slippery inside. I immediately wondered how my cock would feel in there. ‘Another’ she gasped. I didn’t respond immediately. ‘Put another fucking finger in my cunt’ she ordered me. I slid it in, although it was still slippery the second finger was a little more difficult to get in. Beth reached down and slowly pulled my fingers out. I thought I had done something wrong, but then she slid them back in again. I got the idea, and resumed licking her clit while I fingered her with my right hand. The wet noises as my fingers slid in and out of her were something completely new to me, but I enjoyed them.
After a couple of minutes of doing this, Beth tensed up. ‘Faster’ she said, although it was almost like a whistle, her body was so tense, her stomach arched up towards the ceiling. I licked her clit faster, and slid both fingers in and out of her pussy in time with it. A few seconds later, Beth shuddered and whimpered ‘ohshitohshitohshit I’m cummming’. Her whole body convulsed, her legs shaking like an earthquake. She pushed my face out of her crotch and continued to whine and shake for almost a minute. By this time we were both shiny with sweat. ‘Fuck. Ok. Fuck’ she said. ‘That was pretty good. Just give me a minute.’ I moved and lay next to her for a minute or so, then she moved back down the bed again.
She got on her hands and knees next to me in the bed this time, and immediately took the tip of my cock into her mouth. Then she swung her knees over me, so that I was staring into her open pussy from behind. Her thighs were covered with a sheen of sweat, saliva and her own juices. I could feel the heat coming off her. Her left knee was almost against the wall (her bed was pretty small and wedged into the corner of her room), so I wriggled into the middle of the bed. Again she let my dick pop out of her mouth ‘lick my cunt again!’ she said, as if talking to a moron.
Since that time, I’ve had a lot of experience 69ing with various people, and I’ve always found it a bit tricky. I’m not a short guy, and almost all girls are shorter than me. It’s difficult for me to get to a pussy when a girl who’s about 6” shorter than me is sucking my dick, particularly if they can get a decent amount in their mouth. That day with Beth, I remember that I was in a sort of semi sit-up position, resting on my elbows while I licked her pussy again. I learned something else that day too. I had thought that a minute or so of Beth’s talented mouth on my cock and I would immediately cum, but when I was licking her at the same time, I was ... distracted. We went on like this for about twenty minutes, and neither of us came. My neck was sore, my abs were sore, everything was sore. Eventually I pleaded for a break.
‘It’s 6 o’clock, we’ll probably have to have dinner soon’ I said, slumping back on the bed and rubbing my neck. Beth moved around so her pussy was no longer in my face, without letting my dick slip out of her mouth for a moment. She looked up at me and opened her eyes. Again, I nearly came as her big brown eyes met mine, and, while holding eye contact, she slid half of my dick right into her mouth. She held up her right hand with all five fingers extended, then moved it back to my shaft.
Quickly, Beth started to move her mouth up and down my cock. She could only get about half into her mouth, but she was using her other hand to work the saliva trickling down my shaft up and down in time, so it almost felt like she had her entire mouth on me. It was unlike anything I had ever experienced, or even imagined. After only a minute or so of her hungry mouth on me, I knew I was close. ‘Beth, I’m almost... ‘ I managed. Beth just moaned, and for the first time I noticed the wet sounds of her fingering her own pussy. Everything put together: the moan, her fingers in her pussy and her mouth and hands rapidly sliding up and down my hard cock was all just too much. My body tensed, and I started shooting my cum into Beth’s mouth.
Beth slowed her sucking, but obviously she had done this before and was able to swallow most of it. After so much stimulation though, it was much more cum than normal for me, and she couldn’t swallow fast enough. Some of it dripped out of her mouth and onto my sweat-slicked stomach. I was still cumming, and Beth half-choked, gave up swallowing and let the rest fall out of her mouth onto me. Finally she released my cock from her mouth, smiled and swallowed what she had in there. She then gently moved my semi-hard cock out of the way and licked all of the cum up from my stomach. I was absolutely blown away: this girl was filthy and I loved it.
Beth and I ended up dating for most of that year, but we never did have sex. As with quite a few girls of high-school age, she was keen to please her boyfriends (and attract new ones) by doing everything except actual penetration. We definitely had close calls, and some extremely enjoyable experiences together, but she wasn’t ready for sex, and as she put it ‘I’d want some practice with a regular dick before I put that fucking thing in my cunt’.
A few years later, I heard that Robin and Beth (now in their early 20s) were back together. I don’t think it lasted, but we still never got back on speaking terms. I have no idea where Beth is now, or what she’s doing.
Now that I’ve seen quite a few naked men, I’ve decided that penis size is essentially random. It can be proportional, one guy I know is probably 6’5”(195cm) and fairly broad shouldered, he has a big thick cock. It can maybe be related to the ‘skinny guy’ thing, the two other guys I know with what have seemed to me to be above average cocks are both fairly slim, one is just slim and about 5’10” (178cm), the other is very skinny and about 6’ (183cm). I myself am about 180cm tall, and have always been fairly slim. However, I also know a guy I went to school with is 6’3” (191cm) and has a pretty average cock, maybe below average even. Shoe size, despite what many believe, is no kind of indicator. I wear a UK size 9.5 I think, there was a guy at my school who had size 13, and was extremely tall, maybe 6’8” (203cm). I was informed by a girl who had been out with him that he had a 6” cock, which looked small on him, and that he was much too clumsy to do anything useful with it.
So my resolution has been to try and make the best of what I’ve got, as everyone should. I like to believe that for almost everyone, there is another person who fits them perfectly both physically and mentally. I don’t think I have used my size as an excuse to become a lazy or incompetent lover, but there is still a lingering thread of low self-esteem there: to this day, every time I take off my clothes in front of a woman, there is a moment of indrawn breath as a part of me wonders if she’ll scream and run away.