What Strangers On The Internet Taught Me About Sex

Straight / Male / 29–34 / North America / Long-term Relationship /


High speed internet access, especially for a teenage boy is a double edged sword. Sure, it does help with homework and technical literacy is pretty much as critical as actual literacy in the modern world, but when you’re a prepubescent, barely contained roiling explosion of hormones with free time, you’ll soon find yourself surfing whatever smut you can find. I was no exception. It was mostly preview images of adult sites at first. I know, I know, it’s barbaric, but back then you had to pay for these things. Video was still a blurry, blocky, and infrequent affair, but still out there and good enough to make a real impression. Oh the kids today, so spoiled with 4K HD video on demand on any BlankTube site you can think of at a moment’s click. When I was their age…

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But I digress. The dark side of this triumph of teenage masturbation was that one day, I, a boy who was far from fully developed, and lacking the knowledge to understand this at the time, would read biting articles and jokes complaining about penises too small to qualify as reproductive organs, and decided to measure myself to see if maybe, just maybe, those scornful missives were about me. Then predictably falling short and being promptly stricken with a sense of existential dread.

With porn as my only real guide, depression seeped in. I thought sex, if it ever was to happen, would be a quick and humiliating affair, and not only would I be scrawny, I’d also be too small to provide any sort of pleasure. The future looks bleak and surely becoming a hermit can’t be all that bad, right? If only the urges weren’t so overwhelming, then it would be so much easier to take. But to have to one day go out and try and impress a woman with a measly five inches? Might as well quit already. But then one day, the web prompted me to take another measurement.

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Wait a minute! It’s a miracle! An honest to goodness miracle. (Of basic reproductive biology that I wouldn’t learn until my early 20s.) Now, almost two years later, it’s six and a half! That’s a little below average according to my porn-based sources, but within the range of passable. Maybe there’s hope after all…

And so while still shy, insecure, and quiet, I started working out, lifting weights, cycling, swimming, and toying around with martial arts. I gained muscle, my shoulders broadened, and I started feeling stronger and more confident. Until it was time to talk to girls. My first few sexual experiences after so much waiting were just fumbling, drunken hookups at friends’ parties. Nobody was really satisfied and two problems immediately brought my self-esteem down to earth.

First, that amazing feeling of orgasm? Yeah, that wasn’t happening at all for me, not even close. Second were the complaints from the girls. Whatever I was doing felt uncomfortable, or even downright painful, and them being only slightly more experienced than me at best, there were no tutorials on how to identify and fix the problem. Clearly I had no idea what I was doing and it would be unrealistic to expect someone to teach me the finer details of foreplay and intercourse. Now what? Back to depression land? No. Not again.

There had to be another way. A way in which I could work up the confidence and lessen the blow of rejection. An online way where I could work on my skills, practice conversation and timing with no real consequences. It wouldn’t happen in a week or even a month, but eventually I’d learn the basics and use them on a real, flesh and blood person. Then hopefully, learn how to enjoy sex from there. To expedite the process, I figured I should learn from an adult hookup site. Conventional dating sites? Going to bars with friends? Talking to prim and proper people about sex? It seemed like a sad half-measure and I was not about to half-ass this, I was going to full-ass it all the way to wherever it lead. It was educational sex with random strangers or bust.

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But being charming is hard in real world conversations and it’s doubly hard in the noise of a chat room. Eventually, I adopted a very deliberate strategy of lurking — or silently watching the chat go by while my screen name was still obviously listed in the room — and waiting for a perfect time to throw in something funny, then go back to lurking. A few months later, it started to pay off. The regulars were recognizing me. People wanted to ask me questions, check out my profile, many wanted to have cyber sex. It did very little for me, but while they enjoyed themselves, I took notes. What kind of dirty talk did people like? What sexual acts did they enjoy and bring up? How did they describe the techniques they imagined would get them off? More than once, I googled things and added them to my bookmarks for future study.

Finally, sexually experienced and wise women were telling me what turned them on and I wasn’t going to do something as stupid as turn them down simply because I wasn’t getting any physical pleasure or sensory stimulation out of it. Phone sex, however, was thoroughly enjoyable because I loved to hear their moans, sighs, breath, the noises their wet pussies made when they fingered them, or impaled themselves on their vibrators and dildoes, or rubbed their hot, swollen clits. And again, most importantly, they were teaching me. Gaining this knowledge at 20 instead of 16 or 17 made me think I was well behind my peers, so all my efforts to learn were undertaken with the same rigor as my final college classes, and my chat and phone partners were treated like my professors.

One of these women, who we’ll call “Carol,” a sweet, curvy lady who started talking to me in general chat rooms and progressed to phone sex, had an idea. ‘Camming’ was becoming widespread. So many people now had broadband connections and cams were so cheap, $40 at your nearest electronics store was all you needed to show yourself off to the world. They were still somewhat jumpy and a bit pixelated, but definitely workable. She showed me her smiling face. Then, her bare breasts. Then, her hand delicately passing over her vulva. Then parting her pussy lips and flicking her clit with her middle finger. Soon enough, I figured it should be me entertaining her. Shaking like a leaf in a hurricane, I bought a cam and hooked it up.

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Before messaging Carol about my new acquisition, the ping of old insecurities set in. What if she worked up an unrealistic image of me in her head? When she saw me, would I be a disappointment? She knew what I looked like, but definitely not without my clothes. Then, a moment of crazy hit me. I could just go get anonymous responses, same as before. That was it. The market of sexually active and wizened people online was going to render its opinion and teach me once again. Choosing a room where chatters were looking for C2C, or cam to cam, cybersex, I pitched myself and waited, knowing it would be a while, but that I could shut everything off and back out at any time. That thought gave me enough comfort to stop the oncoming panic attack.

In such rooms the ratio of men to women would have made a sausage fest look like an estrogen party, but it wasn’t necessarily all bad. The women went through a queue of men they thought they’d like and would often open a session just to close it in seconds. Just fifteen minutes later, a woman answered my pitch. I could see her only from her chin down, sitting in an office chair, naked. Most laptops and cams still didn’t have microphones at the time, so we typed.

“Ready when you are babe,” she rendered my sentence.

Preparing for my slice of humble pie, I flirted, teased, and finally dropped my shorts when I was as aroused as I was going to be under the circumstances. My heart paused.

Her hand immediately dove between her legs while with the other she typed the absolute last words my constantly savaged self-esteem would’ve ever expected to see.

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“OMG, babe! That looks yummy! How big are you?”

I replied that it was just six and a half inches, hopefully serviceable and not too embarrassing.

“No way,” she typed back slowly, almost agonizingly so while she played with herself. “It looks so big. And it’s thick. Mmm… that will give my pussy a good stretch…”

If I could find that woman again and tell her what she did for me with that one, simple, lusty exchange that I bet she’s forgotten about, I would beg for her permission to kiss her, and allow me to wait on her hand and foot for a week. I was far too shy to actually cum on cam at the time. So I simply let her masturbate until she climaxed. After our session, I actually felt decent about myself for once in my life. But this was a sample of one. The result needed to be replicated.

The woman who wanted to watch my second cam show immediately decided she wanted to call me and talk me off while she played with herself. She told me how good she thought I would feel inside her and how badly she wanted to see me explode. Caught up in the moment, I didn’t realize she would get her wish until it was too late to stop. Amazingly, afterwards, she wanted to keep talking, asking me if I would ever be around her town and if I would be open to a meet up. The distance wouldn’t have worked out and I was still too shy to actually meet someone, but listening to a woman turned on by me, flattering the part of my body I always thought was deficient, rejecting my measurements from the past as utter, impossible nonsense… I finally felt alive. One. More. Test run. Fine, two.

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By my fourth show, the woman demanded that I measure my dick to satisfy her curiosity. Grabbing a tape measure, I complied. And holy shit if she wasn’t right. Standing at close to eight inches at full attention in length and more than five inches around, it was average only by porn standards, according to her. With radiating mirth, she told me that I was the real life version of a teenage movie trope, the nerdy kid who was secretly packing. Her primal, hungry adoration finally gave me the rush I needed; another strain of sexual excitement to which I was slowly becoming addicted. It was definitely nice to hear flattery about my size but it was the validation I was after.

Ready for Carol, after making her wait for an entire week, I couldn’t help but blush and smile as I saw her visibly start to salivate. When she asked about others’ reactions to seeing me aroused and naked, I confessed that until this whole camming thing, my impression was that I was very average or even below, after which I was promptly asked if I was “fucking nuts” and warned to use my new powers wisely. Like Spiderman, apparently. Having horny strangers watch you naked and vulnerable sounds like the most bizarre and backwards way of boosting one’s self-esteem possible, but unwittingly, I was actually using a well-known behavioral psychology approach known as exposure therapy.

Being laughed at and rejected in sexual situations was the very thing I feared, and I used the always-there off button on the web as a kind of safety rope while slowly exposing myself more and more to what it was that terrified me. If anything, it turned a fear into a source of confidence. I lived for the compliments, the validation, the excitement on women’s faces and the arousal in their voices.

Imagine if you were afraid of playing football, anxious that you wouldn’t be able to throw the ball straight for more than a few feet, avoiding the game as much as possible, or fumbling because nerves would get the best of you when you do step on the field. Then, after hyping yourself up enough, you manage to start playing the game, make your first real throw, and find that with little effort, you just sent the ball 80 yards in a decent spiral. Suddenly, football becomes your favorite sport and you start looking forward to each game, honing your skills for the sheer pleasure of it. This is exactly how this entire ‘camming’ business felt to me.

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Rather than embracing the flattery and risk coming off as arrogant, I adopted an “aw shucks” manner of exposure. Seeing me aroused on cam would be the trump card, and it would be a drawn out performance where I had to be “convinced” that the woman wanted to see it. On public webcam shows, it would often take at least a solid half hour of prodding before I acquiesced, and even then, I did my best to tease and draw it out, building up the anticipation. My back became straighter, my chest puffed itself out. I learned to be coy and hint at what I had to offer. The women with whom I chatted knew exactly what I was trying to do, that it was just a game and they’d get what they’d want in the end, but that was part of the fun. There was teasing and buildup. They had to put in a little effort before they received their entertainment.

Five or six months after all this began, a woman sent me a message on my favorite site, wondering if I’d be interested in getting together with her in real life. Although we chatted clothed, all that positive feedback gave me the confidence to say yes. My first real world run lifted a huge weight off my shoulders in a series of small but oh so meaningful victories. I actually got her off with my mouth! I spent an appropriate amount of time on foreplay to warm her up! Her silky, wet pussy throbbing on my hard cock felt amazing, and she loudly moaned in my ear and passionately kissed my face! I still couldn’t climax but that night, I went home finally knowing that sex can be good, that I can have a fulfilling sex life, and that I finally had the confidence to charm my way into a woman’s panties.

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It’s at this point where I would love to tell you that I had solved all my problems and everything was going smoothly from there on in. But I would be lying. The problem with getting enough confidence to put myself out there but having little self-esteem when I was finally physically there, was simply the next problem to tackle. One I didn’t know about when my ‘camming’ adventures began. And so, more than I should have, I’d find myself in a darkened room with a woman who was impressed enough by my cam to meet me in person, interested enough to carry on a conversation during drinks, and now was expecting sex. Ready or not, I had to dutifully oblige. Figuring that if I made it this far, it would be rude to just turn around and say “never mind, sorry”.

After building myself up in her eyes, the absolute last thing I should have done is to shirk from the sex, my mind calculated. Some of the women didn’t like ‘no’ for an answer anyway, and had an array of tricks to get what they wanted from me no matter what. But sex with them was the first encouragement and positive feedback I had ever gotten. Even if it wasn’t really what I wanted, it was going to be the only encouraging thing I was going to get until the next encounter. So I focused on how good it felt and tried to enjoy myself.

Over the next few years, I accumulated a decent number of partners, but was only happy about being with maybe half of them. The validation and sex were fun, but as soon as the act was finished, I often liked that we’d clean up quickly so I could get dressed and leave. The mechanics of sex were now something I had down pat, but how to turn these encounters into a relationship… that was something none of my online teachers and meatspace partners ever showed me.

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This changed when I met someone in a way that had nothing to do with hookup sites, cams, or parties. Someone who I just bumped into. Who developed a crush on me as we kept on encountering each other day after day in the same coffee shop.

There was nothing sinister involved. It was purely a coincidence that we had a similar work routine and this was the closest place to get our caffeine fix. One day we spoke to each other. A week later, she was straddling me, our bodies seemingly melting into each other, lost in the flood of new, yet somehow still familiar sensations. My muscles knew what to do, letting my mind focus on how she felt, how she sounded, how she smelled. We’ve been together ever since. I was finally content and thrilled to use what I had learned to please her, grinning like a maniac probably more than a few times when I knew she was just about to come.

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My bizarre, autodidactic approach to learning about my body, gaining confidence in myself, and being able to use that to make myself and my partner happy, absolutely had its bumps along the way. It’s definitely not for everyone, and required a willingness to take risks with the promise of a bizarre and entertaining story and a new skill, not so much the sex, as a reward. But in the end, it did work. I know now that my insecurities were primarily caused by ignorance and being too shy to ask someone who might have known better, and that this ignorance bred fear and doubt.

Comparing myself to adult, fully developed professionals acting out in an idealized representation of sex as a child who just vaguely became aware of his sexual urges set me up with an early inferiority complex. It’s not like I grew up in a household where conversations about sex were taboo and no one ever talked about it either, I simply didn’t know to fact check what I saw in porn, and how to do it. Only after joining hookup sites did women finally tell me what porn gets wrong about the real world, because I asked.

Of course the takeaway on this isn’t that porn is evil either, just that it needs to come with an explanation on what is and isn’t exaggerated to make the act look good on camera, and what’s visually impressive vs. realistic. And if anything, over the years I’ve actually seen more useful fact checking spread across the web and become more easily available. I think that the next generation will be able to start maturing earlier by having more balanced and useful information about what they’re going to stumble across when they inevitably look for porn.

It’s tempting to see this as a tale of a guy bragging about winning a genetic lottery, but really, it’s more of a way for me to retrace my steps in how I found out how ignorant I was about my body and sex in general. In a very convoluted way, I wondered what would’ve happened if someone just told me at 13 that “Hey, that thing you’re worried about? It will grow. Just focus on learning how to be social and make friends. And here’s where you can educate yourself on what sex is and how real people do it.” But with a redo of my teenage years unavailable, I’m glad I took my sex life into my hands the way I did. Nobody else was going to do it for me.

And what of my ‘camming’, the curious stranger might ask, is that still a thing? It’s definitely not a regular thing anymore. Maybe once in awhile, with permission, and half the time, no longer alone…

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