Cybersex Ch. 04

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Tue, Mar 9 at 5:59 PM

So far, this story is how it all really happened, and I haven't really embellished much, if at all. It's fun to think of alternate versions, though, and maybe sometime if you were in the mood, you could tell me if there was anything I could add to make the story more exciting. I love the idea that reading my story makes you so horny that you want to jack off thinking about my words.

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Wed, Mar 10 at 4:37 AM

I would suggest sticking to exactly what happened ... hot enough that it doesn't need any artistic license.

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Wed, Mar 10 at 4:44 AM

Damn, you can WRITE!

This is super hot. Reminds me of a guy I used to know who would deepthroat me while buttfucking me with his finger, touching my prostate with each thrust. Best fucking blowjobs in my life.

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Wed, Mar 10 at 5:20 AM

Thanks! I just got up and was so excited to see your replies, I worried that I'd written too much and scared you off...

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Wed, Mar 10 at 6:37 AM

Aaah, I was just busy yesterday. Can't spend all my time reading what a fellow pervert wrote. ;)

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Wed, Mar 10 at 5:40 AM

As I glanced over at the TV, seeing yet another girl with big tits getting her brains fucked out, Theo moved closer to me, until he was standing between my bare legs, looking down at me as he worked his stiff cock.

"You're good at sucking my cock, boy." His hand sped up. "Has anyone ever fucked you before?" I guess my eyes must have gone a little wide as I shook my head no, because he chuckled a little, and then winked at me. "Don't worry, I'm not going to fuck you tonight, Sean."

I felt a little nervous all of a sudden.

He groaned low in his throat. "Here it cums, here it cums!"

It made me jump as the first load of cum shot out of the big, angry looking tip of his cock. I felt it splatter onto my tummy, all hot and thick, and I moaned softly as he kept going, shooting over me again and again, a real heavy cummer. His cum went everywhere, all over my torso, even a little onto my face, and his body shook a little as he finally finished, looking down proudly at the mess he'd made all over me.

After he came, Theo walked naked to the bathroom and started washing off his hands.

I started getting my clothes together, and Theo came back in, in his sweatpants again, and tossed me a towel to clean myself up with. I wiped all the sticky cum off my, blushing low, feeling embarrassed and in shock as the reality of what I'd just done started to sink in, and I started sobering up quickly. Before anything else could happen I mumbled "Thank you," got in my car and took off...

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Wed, Mar 10 at 6:49 AM

You might want to do a second chapter about anal sex ... assuming that wasn't a one time thing, seeing how you want to stick to what actually happened.

You might want to insert your thoughts about what was going on a bit more, structured like this, no quotation marks:

Holy fuck, he just took my virginity, I thought. Sullied the fuck out of me.

I start cleaning off his sticky cooling jism ...

P.S. Your internal life here is really hot.

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Wed, Mar 10 at 7:02 AM

Wow that's really great input, thanks! I can totally go into more detail about my thoughts and feelings.

I was physically shaking when I first took Theo's cock into my mouth, sitting on the edge of his grey couch, my legs trembling as his cock slipped past my lips, knowing that now I was really doing it, I was really sucking another man's cock after so many naughty secret thoughts about it.

I could also do more detail about how I felt while he was fingering and rimming me, he was super into it and it made me feel so hot and sexy and desired and naughty. Such fun feelings!

Here's a few things I like role playing about. I haven't really played with anyone in a couple years, when Yahoo Messenger shut down I kind of lost touch with the people I'd played regularly with, and online chat rooms make me increasingly nervous about internet security. Sketchy Java based chat rooms were how I first had cybersex, I think the site was a adult chat network, or something very similar. That site shut down, a few similar ones popped up, but I slowly lost interest.

I also think any or all of these plot ideas would make fun stories. Like I mentioned, I've never published anything, anywhere, but I'm warming up to the idea. I started emailing you because I loved your stories, and I thought you'd be a fun person to chat and maybe exchange fantasies with, that kind of thing. I've also never told anyone what happened with Tom, and it was both exciting and liberating to finally tell someone.

Anyway, back to the plot lines:

1. A loving wife, to use Literotica's terminology. I've had fantasies about sharing my wife with another guy for a long time. Some scenarios I like are my boss coming over for dinner one night, and telling my wife that I'll lose my job if she doesn't let him fuck her in front of me; our teenage nephew stays over at our house for a weekend and my hot wife decides to service him; my wife pays for a male model to pose privately for her figure drawing hobby; my wife visits a photographer for some sexy photos for me, and ends up sucking off the photographer while he shoots it. She shows me the pics, then admits that the guy wants to see us together ...

In all of these scenarios, the husband is pretty actively involved with encouraging the naughty wife to please the other guy. I also really like playing the wife. In these fantasies, I've had fun using pics of really well endowed men as visual aids, playing into the fantasy of the hot wife being all excited about a guy with a bigger dick. The "teens like it big" websites were the source of a lot of pics for these fantasies, and also work well for the schoolgirl categories.

2. Schoolgirls, to use a generic term. It's fun to play hot younger girls, mostly innocent ones that get seduced and taken advantage of by naughty older men. I have few limits here and I've played some pretty kinky stuff with other guys. Not so much that the super naughty ideas were mine, but I played along with them. It's fun to use links to porn pics for fantasies like these, picking a cute model to be the schoolgirl so visual aids can be introduced to the role play. Inspiration for some of these roles has also come from the girls I dated as a teen. Coed cherry was a website that provided plenty of visual inspiration for these fantasies, and some of my fav models to "play" were Teen Kelly, XOXOLeah, and girls like that.

3. A bisexual, married man. This is kind of a new category for me in role play, but I find myself more and more interested in it, and I've had fantasies about men since that first time with Theo. I've had some more real life experiences with men after Theo, though not very many, and certainly not as many as I would like. "Realistic" fantasies are exciting in a different way, because there's always the remote chance of them coming true someday. There's a remote, distant possibility that we might be hotel room watching porn together someday, while the chances of actually being with some hot little schoolgirl are zero. It's a lot of fun to fantasize about, though.

4. Fantasies involving me as a man in general: to be honest, most of the role playing I've done online involved me being a girl. I think it's because it's hard to find expressive, literate guys to play with, and playing a hot young girl is more likely to get results. I'd like to explore this area more. I'd like to be the one fucking the hot girl for a change, probably reliving the sex I had with Ava and my other girlfriends when I was a teen, but from my current perspective. I think visual aids would play a big role here too. My old girlfriend Ava looked a lot like an online model named Teen or Dream Kelly when we dated.

5. I can share more true stories from my past, and we could develop role play and/or story ideas from there. Beginnings wasn't the only time I went to Theo's house, for example, and there have been other experiences since, though none involve me as a teen with another man.

The list isn't finished, but I think it's probably enough food for thought for now...

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Sat, Mar 13 at 7:21 AM

Plots, cont.

6. A married man secretly meets up with another guy in a luxury hotel room, to watch movies and smoke some weed. They've exchanged a lot of emails, and know that they share similar taste in porn, among other things. As the married man walks in the door of the luxury suite, impressed, he sees that the big widescreen in the living room is connected to a laptop, so porn can easily be streamed on demand onto the big 4K screen. The door to the room is double locked and the curtains are all closed, making the room completely and totally private from the outside world, at least for the rest of the evening. A box of 32% THC joints sits on the coffee table, with an ashtray and a couple of lighters, along with a bottle of high potency Viagra, and a few bottles of water.

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Sun, March 14 at 10:43 AM

Does your wife look like a mature version of the slim blonde girls you go for here?

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Sun, March 14 at 1:00 PM

Lol no, she's a hot middle aged Latina actually. ;) The little blondes remind me of my teen aged girlfriends, that's all ...

She is much, much closer to the porn star Mercedes Carrera than the teens I've been showing you. Very similar body type and skin tone, etc.

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Sun, March 14 at 04:09 PM

Is there something you want to try with a guy, but the opportunity hasn't presented itself?

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Sun, Mar 14 at 6:21 PM

I'd like to help you fuck my wife, it's a fav fantasy of mine, not that there's a chance she'd go for it in real life. My ex wife, maybe ... but lots of fun to fantasize and pretend about.

I find myself wanting to do some serious cocksucking again, which is one of the things that got my attention about your stories, I love the idea of "playing girlfriend" for another man. It's what I wanted to do the few times I've been with another guy in adulthood, I just didn't know how to conceptualize it. I'm also increasingly turned on by the idea of letting another man play girlfriend on me, which could be a pretty convenient, reciprocal set of fantasies ...

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Mon, Mar 15 at 07:43 AM

So what other things have you done with men - got a blowjob? Got assfucked? Fucked his ass? Something else?

If you had a guy who wanted to play he was your girlfriend, what would you do?

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Mon, Mar 15 at 7:48 AM

I've had my cock sucked, I've been rimmed and fingered, and I've reciprocated.

If I was with a guy who wanted to play girlfriend, I guess we'd spend some time watching vids and looking at pics, picking out exactly the right girlfriend for him to "be" ... and then the girlfriend would start to play with my cock. I might be open to fucking the girlfriend but it's not something g I've done before. Definitely a lot of oral.

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Mon, Mar 15 at 7:49 AM

And ps - I do think I've gotten my ass fucked but I'm not completely sure. I guess maybe it's part of the next Theo story.

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Mon, Mar 15 at 8:10 AM

I'd also be open to role playing, and trading places during the fantasy. I think it'd be really hot. The last time I was with a man, I guess I did kinda play girlfriend for him, but I didn't know it at the time. One of the times he came over, Paul sent me mail earlier in the day, asking me to be wearing a robe, and nothing else, when I answered the door. He also asked me to shave myself bare, like a little boy, he said.

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Mon, Mar 15 at 8:21 AM

You * think * you've gotten your ass fucked? Talk about burying the lede.

Based on my experiences, you'd know if you had a cock push past your ring and go deeper - it's not a subtle thing, getting fucked, kinda painful and uncomfortably stuffed full and yet super hot, especially if he hits your prostate ... unless you had blacked out from all the alcohol?

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Mon, Mar 15 at 8:28 AM

I'll tell ya the story if you want ;) Theo did like giving me Jack Daniels ...

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Mon, Mar 15 at 8:29 AM

The playing girlfriend thing can be something just in your head, or in his, or it can be explicit and you or he uses the word "girlfriend". It's even more explicit if you or he crossdresses a little (or a lot) by wearing lingerie or panties or stockings or whatnot. I once wore my soon-to-be-ex-wife's black french maid's costume and fishnet stockings for a guy who came over for a blowjob.

I only crossdressed the one time ... it was kinda hot, but not as hot as it could have been, since he was a dick who roughly took what he wanted and then left.

I'm thinking my sexual number - the number of people I've had some sort of sex with - is in the low three figures. So, yes, fairly experienced.

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Mon, Mar 15 at 8:31 AM

The explicit version sounds like a lot of fun... I've never done anything like that before. I'd be willing to dress up I guess if it helped the fantasy. You've got much more experience than me in all of this :)

Did crossdressing help you mentally get into the role more?

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Mon, Mar 15 at 8:31 AM

I'd like to hear the story of the "I'm not sure if I got assfucked" thing!

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Mon, Mar 15 at 8:42 AM

After the first time, I couldn't stop thinking about what had happened. I found myself thinking about it when I was fucking Ava, I jerked off thinking about it a lot, and it just kinda stayed in my mind. I knew I was going to go back. I felt embarrassed about it, but didn't struggle with any of it too much, I knew that Theo wanting me was hot as fuck and I wanted more of it.

A couple weeks later I went back to his house, late at night when I'd already been out partying. He grinned when I knocked on the door and let me in. Porn was already on the TV, and another big bottle of Jack was sitting ready.

He poured me a couple shots and then said, "Get naked."

It felt different this time, I guess because I knew what was coming. I was hard as a rock before I even got my T shirt off, and by the time I was stiff and naked in his living room, I must've been as erect as I'd ever been.

Theo paid more attention to my body this time, fondling my balls a lot, commenting on how much he liked how smooth my body was. He kept telling me to take shots too, which I did ...

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Mon, Mar 15 at 8:54 AM

cont ...

After he satisfied himself fondling me and playing with my cock when I was standing up, he told me to sit on the couch. I remember being eager to do it, anticipating that he was going to make me suck his big cock again, but he didn't. He did a couple more shots with me, both of us naked, him almost obscenely edging himself, and then I remember being surprised when he pushed me back into the couch and got on his knees in front of me. He started sucking my cock really deep, easily taking all of it, and I remember gasping and kind of writhing on the couch, wriggling or something, as he went lower and started licking my ass.

"You like that huh?" He asked me dirtily.

I remember how it make my tummy feel all funny and excited. He watched my face as he stuck his finger up my ass and I remember how my cock went crazy, bobbing and twitching and jerking, and I think I came ... and then I blacked out.

I start remembering stuff again in my car, I was confused because Theo was driving, then it gets blurry again. I eventually decided that Theo must've driven me home in my car and then taken a cab home, and I must've managed to stumble into my room without waking anyone up.

I've never told anyone that story before, I don't have to mention it again if you don't want me to ...

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Mon, Mar 15 at 2:14 PM

Your story was sexy and exciting, though you implied you might have technically been raped, since you can't give consent after blacking out. Legally I imagine it's more muddled if you've given consent beforehand, or if he wasn't aware you'd blacked out. But, if no one is upset about what happened ...

I'd like to hear more, but if you'd rather not talk about it, then don't. I totally understand either way ...

Assuming you do want to talk:

Did you ever ask what happened after you blacked out? Do you think you might have been roofied? Was your ass sore enough that you think he might have fucked you? How did you feel about how that night turned out? Did you give or get blowjobs with him after that?

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Mon, Mar 15 at 2:33 PM

I'm glad it didn't scare you off. I do want to talk more about it. Is it too weird that even thinking about it makes my cock throb?

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Mon, Mar 15 at 2:35 PM

It doesn't seem weird to me ... I've been there too, incredibly horny just thinking about what a guy did to me ...

Tell me more!

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Mon, Mar 15 at 2:35 PM

God, I'm shaking a little bit and my cock is almost hard, just thinking about all of this. I guess he did kind of ... do that ... to me, but I think I wanted it. The first time, when he started teasing my with his finger, I moaned "do it...do it..." I remember that clearly, at least the first night, and then he started playing with my ass. I guess there's a good chance I might've said something like "do it" while I was laying back all drunk on the couch with my legs spread. What do you think Theo would've done?

I was a little sore, but it's also possible that it was just from him fingering me, right?

And... I did go back again ...

My head is just spinning thinking about the Theo stories. Never really thought about it like that somehow until I put the story in writing. Crazy!

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Mon, Mar 15 at 2:48 PM

Pretty sure he assfucked you ...

Watching this video on PronHub right now, titled "Anal Penetration!!! Face Expression Show how it Feels", which gives the POV of a woman getting anal fucked. I'm jacking to it, about to stick a lubed finger up my ass and remember how it felt getting fucked from behind like that ...

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Mon, Mar 15 at 2:53 PM

Can't watch anything right now but I will. Difficult enough to hide my hard on now. Do you think Tom raped me? I don't feel upset or fucked up about it. It's turning me on a lot which is weird but oh well?

Now I can't stop thinking about it. He had a pretty big cock, I'd guess more than 7 inches. I remember that it was kinda veiny, and really stiff, and I can remember how it felt in my mouth. I was a naughty age, completely buck ass naked, on my back with my knees pulled up and spread apart while a porn played in the background. He'd just sucked my cock like nothing I'd experienced, and had just started to lick my balls and my tight hole when I blacked out ...

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Mon, Mar 15 at 3:20 PM

I can remember how excitedly my cock was throbbing, even though I was really really drunk. Booze used to help me last longer with my girlfriends, but I must've been leaking precum like crazy, the way I do when I'm close. The first time I was with him he really seemed to like swallowing me when I came, I actually tried to pull away but he didn't let me. I honestly don't quite recall how or if I came that second drunk night, but I'm pretty sure I did. I remember my cock spasming like crazy in a new kind of way, like an explosion or something. And I do remember being all messy when I took a shower the next day and washed a bunch of dried cum off my torso.

I'm really wishing that I could somehow know what really happened now! I never asked him, though I did go back a few more times. Now that I think of it, I don't think he really tried to do anything like that to me again, it was more about him sucking my cock, and then letting him cum on me, than any more ass play.

Not sure what that means, if anything.

He really liked it when I was naked, that's a clear memory that keeps me hot about the whole thing. He desired me the way men desire women somehow, and it made me feel differently than when women have expressed their desire for me. it's interesting and sexy and fun even thinking about it all. Wow. Glad I found you!