Learning from Older Men Pt. 01

This tale is a partially fictionalised account of my first time having webcam sex with an older man, an event which eventually led to my first time with a man.

Names have been changed as well as locations but the following story is based off of real events. All characters are 18+.

It was the spring of 2013, I had just turned 18 and I was extremely horny all the time. I'd finished all of school and started college and I'd still never slept with a girl. For a long time I'd thought that this was due to my shyness and lack of experience as I was a good-looking young man, but as time went on I came to realise that as much as I was attracted to some women I was also attracted to some men. The first time I ever really accepted this part of my sexuality was on an online chat website. I was one of many horny young guys trawling such sites looking for some girl or woman to jerk off with if I could convince them to, and given enough persistence you sometimes could find what you were looking for. Since this was the only outlet I had for my sexual urges it became a nightly ritual. After I finished at college I would retire early in the night and spend hours watching all different genres of porn and going on webcam chat websites. It was only after I had been using these sites for a little while that I realised there was a certain percentage of users who were not girls looking to show off or young guys just looking to get off. I very quickly realised that there were also a lot of extremely horny older men who logged on every night trying to get off with young guys like myself.

The first few times I was in such a situation I just laughed it off. The good thing about an anonymous webcam site like this is that you can just cut communication any time and because I generally tried to be polite about not being interested I would just decline their advances and continue to the next user.

However one fateful evening, after trying to find someone to talk to for hours and winding myself up to an extremely horny state, I was accosted by one older user who somehow took control of our chat and convinced me to try getting off with a man if it meant reaching satisfaction for the evening. I was just about ready to call it an evening when a new user connected to me and I was suddenly staring at the lower half of a large older man, wearing only boxers and rubbing himself through them slowly. I was sitting on the floor of my bathroom as per usual wearing only a t-shirt and already wanking myself feverishly. I stopped and began to type out a boilerplate response before cutting the connection when he started rapidly typing to me.

Partner: Oh fuck yeah you look good, skinny and sweet. Take off that shirt slut

This shocked me and for a moment I didn't know how to reply. In the pause he pulled his boxers down and revealed a truly massive cock that he started wanking hard. I'd never been talked to like this before, being called a slut shocked me but what shocked me more was how I was responding to it. This dirty talking man was actually turning me on for reasons I couldn't then understand. Even the sight of his large dick was suddenly kind of arousing. Still I was immediately in denial and the safest response seemed to be to just cut off the contact and work out why I was getting horny with a guy on my own later. I began to type out my standard polite rejection message but he wouldn't let me go.

You: Hey sorry I'm not really into guys, have a good night

He immediately jumped to his keyboard and started typing a response before I could log out.

Partner: Don't you log off on me sexy boy, Daddy's not done with you yet

Again for some reason when he called me 'sexy boy' I felt a strange thrill. It was nice that someone was so turned on by my body and as I stared at his large dick I realised that at least for some people this man could be considered pretty attractive as well. My eyes were glued to the word Daddy, this man was one horny and kinky partner and part of me started to wonder if it might be interesting to listen to him and see where this was going.

Partner: I'm going to make you come your brains out show me that sexy body

That did it, I was already super horny before I was connected to this guy but now I realised that I just wanted to get off. If this was turning me on then why not get off with him? The benefit of an anonymous chat site like this is that you can have an encounter like this and it's truly discrete, I could explore having a bit of webcam sex with this man and the only two people who would know about it were me and a random stranger who had no way of contacting me afterwards. I hesitated for a long time, torn between confusion and lust, during which time he resumed wanking himself to the sight of my slim body. Finally I slowly typed a hesitant response.

You: What do you want me to do?

At this he became super excited and began to type instructions to me rapidly.

Partner: Take off your shirt

I slowly raised my shirt above my head and dropped it to the side. I felt a strange thrill as I realised I was now completely naked and exposed to this horny older guy. I also noticed that he began to stroke himself very hard at the sight of my naked slim body.

Partner: Oh yeah you're a good boy look at that sexy body. Jerk your cock boy

I was already rock hard but at this instruction I realised I'd just been sitting there holding my dick and staring at him mesmerized. I started to wank myself slowly and found that I was really turned on.

Partner: Oh yeah you horny little slut, turn around and show Daddy your ass

I don't know how he did it but this man had somehow seduced me in a few short minutes from breaking off the connection to stripping down and exposing myself for his pleasure. I'd never considered myself gay or even bi, I genuinely hadn't found another man attractive before that night, but something about how he looked and talked was making me wildly horny. I timidly got to my knees and turned around, careful to keep my face out of the shot. I got myself at an angle in which I could see the screen but my own camera was recording a full shot of my ass and then instinctively I bent forward and pushed out my bare ass towards him doggy style. Looking at the two screens I realised with some satisfaction that the sight of the two of us looked like something out of a porno. His long, thick cock pumping to the sight of my smooth ass bent over submissively.

Partner: Oh wow what a great ass, shake it for me. Dance for Daddy

And I did. I began to shake my hips as seductively as I could, thinking about how the girls moved in the porn I'd watched online and trying to replicate it. He responded by going wild on his dick, jerking the thing like he was trying to pull it off.

Partner: Sweet little bitch, turn around on your knees and lick my cock

I was hypnotised by now, following his instructions without question and just staring transfixed at his huge cock that seemed to swell each time I did something he ordered. The whole time I was also stroking myself but gradually getting to the point where I couldn't control myself any more. Without putting my eyes in the shot I kneeled forward and held my open mouth to the camera. He stopped and removed his own shirt revealing a large hairy chest which he started rubbing with his other hand.

Partner: Oh yeah you little cocksucker, I bet you want this big old cock fucking that pretty little mouth

This was hotter than any porno I'd ever watched, this man was so horny and the dirty things he was saying and getting me to do were turning me on more than I'd ever experienced. I'd never thought about a man sexually and now here I was naked on my knees willing to do anything this horny old bastard ordered me to do in order to get off.

Partner: Keep jerking it boy, lick my balls

At this he stood up above the camera and his large heavy balls swung down into the full shot. The sight nearly sent me over the edge.

You: I'm really close.

Partner: Don't fucking cum until I tell you too

Oh fuck, he was so controlling it was making me melt and I didn't understand any of it but I knew I loved it.

Partner: Lean back, you're going to cum all over yourself for me

Partner: I want you to put a finger in your fucking hole

I understood what he wanted immediately, I'd had the same experience convincing women to do the same thing for me on camera and I suddenly understood that this was what I was to this man, a submissive hole for him to fuck and cum over. I'd never thought about my asshole as being an erogenous zone before but as I tentatively stroked my finger against it I felt a strange thrilling sensation.

Partner: Put it in

I tried to force it in more but simultaneously realised two things; that I was too tight to take my finger very deep and that if I did this I was going to explode.

You: It won't fit and I'm so close

Partner: Okay just push it in as hard as you can and jerk it fast until you cum

Partner: I want you to cum all over your sexy body for me

He knew exactly what to say. All I had to do was try to force my finger inside and I could finally cum. I knew it was going to be a heavy orgasm and I could already feel it building. Then I felt my finger pop inside deeper than I'd even intended and I saw him jerking like a madman and I knew I was going to cum. The first cumshot hit my chest and I stifled a cry, it felt like my asshole was burning where my finger was inside. I kept shooting again and again all over my chest until my orgasm finally subsided and I was a sticky mess. I slowly removed my finger.

Partner: You like that? Fuck you look good covered in cum

You: That was so good thank you

Partner: Okay turn around and bend over

Partner: I want to come over your hot ass

I dutifully bent over and poked my small smooth ass at him. I began to slowly gyrate my hips like a sensual dancer, I knew he'd like this and at this point I wanted to make him come as hard as I had.

Partner: Oh yeah dance for me you little slut

Partner: You want my cum? You want this big cock to come all over your slut ass?

You: Yes Daddy I want your cum

I don't know why I said it but I knew it's what he wanted to hear and it felt so kinky and submissive which I was rapidly learning I liked for some reason.

Partner: Oh yeah I'm going to be your Daddy

Partner: Shake that ass whore, here it comes

When he started cumming I saw his mouth come into the shot for a moment, a bellowing but handsome unshaven mouth. His huge chest heaved and his cock began to explode, huge white jets of cum shooting out as he jerked it like crazy. I couldn't help but wonder where all the cum was going, it looked like he was shooting it straight onto the floor, maybe he just didn't care. It seemed to go on and on. Finally he was just squeezing long sticky threads from the end of his engorged cock and then he collapsed into his chair spent.

Partner: That was great boy, we should do this again

Partner: Do you have Skype?

As much as I'd unexpectedly enjoyed the last fifteen minutes or so I was still wary of giving this stranger my actual contact details. And what if my family or friends somehow found out I was having webcam sex with this much older man? I wanted it but I just couldn't take the risk.

You: I don't have a Skype no sorry

Partner: Okay my name on there us olderdad4son, get Skype and add me

And with that he just disconnected. I was left well and truly dumbfounded. In no time this horny older guy had seduced me, had me strip and expose myself to him. Shake my ass for him like a girl in a porno and finger myself. Now I was sitting on the floor of my bathroom covered in my own cum, my asshole still throbbing and all I could think about was his dirty talking and his huge cock. I did have a Skype account but I wasn't going to share it with a total stranger no matter how horny I was. But now the clever bastard had put the ball in my court, in retrospect he must have known after that experience I would definitely come back to him for more.

I spent the next few days mulling over the experience. I saved the log and reread it, finding myself so aroused that I could use it as masturbatory inspiration. I went over the words he'd used, names that he'd called me. "Sexy boy", "Horny little slut", "Sweet little bitch", "Cocksucker", "Whore" and found that they turned me on like crazy. I started to explore gay porn to see if I was really interested in men or if I'd just been super horny in the moment and came to the conclusion that maybe I liked men and women, and that I had a definite submissive side. I especially became interested in transexual porn, watching transexuals and feminine boys dressed up in lingerie pleasuring these great big hunks was my particular favourite.

Before the end of the week I'd created an anonymous Skype account and added him. His first few messages suggested he was expecting me to contact him and after that I began a whirlwind of sexual exploration. Almost every night I'd lock myself away for marathon wanking sessions with this horny older man. He had me steal my sisters underwear and wear it for him which drove him absolutely wild. He taught me to take various increasingly large objects in my virgin ass, another sight which turned him into a wild man. I couldn't talk during our conversations for fear of waking up my family in the night but I got a pair of headphones for my laptop so that he could give me verbal commands. His gruff voice commanding me strictly and the animal noises he made whenever I drove him to orgasm were some of the sexiest things I'd ever heard. I have no doubt that if he'd lived in the same country as me I would have already found myself pinned down and being fucked in his bed, but he lived on the other side of the world, not a plane ticket a fairly poor student could afford.

In time I began to add other men I found online and in forums. It was a very hit-and miss process, some of the partners I found were exactly what I was looking for but I always stayed wary of giving away too much information or allowing myself to be recorded. Still, it got to the point that by the end of 2013 I was becoming more confident in my sexuality and interested in meeting men physically. However I knew better than to trust meeting a stranger through the internet, any number of things could go terribly wrong. And despite the numerous offers from men on my Skype to collect me and take me to theirs or pay for a ticket so that I could visit them I wasn't able to actually physically try the things I was learning about and becoming fascinated by. That all changed the day that I was unexpectedly taken and seduced by my old history teacher.