Cybersex

Author's note: This story was cowritten with Literotica author SeanSteyvens. Names and identifying details have been changed to protect the culpable.

***

Friday, March 5 at 1:06 AM

Subject: Literotica: Feedback for married_but_curious

I love your stories. I've had similar fantasies for many years, being a middle aged married but curious guy myself. I've had some real life experiences I might want to share with you, some of which happened when I was a lot younger than I am now.

If you think you might want to start corresponding, hit me back!

Sean

***

Mon, Mar 8 at 6:56 AM

Hi, thanks for writing back!

Sure, I'd like to hear about the most vivid or memorable things you did when younger. You've already got a massive trove of my experiences, albeit edited using artistic license.

Married But Curious

***

Mon, Mar 8 at 12:29 PM

Thanks for getting back to me! It gives me excited feelings even writing to you about this stuff. So hot!

I guess I could start by telling you a few stories about my experiences... which do you think would be more fun to hear about: some things that happened when I was eighteen, with an older guy in his forties or so; or, some of the fantasies I've roleplayed online over the years? If I'm being honest, a lot of the latter includes me pretending to be a girl, which makes me blush to even admit...

So cool that you answered!!

***

Mon, Mar 8 at 12:31 PM

PS - I probably should've described myself a little. I'm in my mid-40s, 6'2, lean and smooth skinned. Shortish dirty blond hair, hazel eyes, tattoos on the arms...

Sean

***

Mon, Mar 8 at 1:52 PM

We have similar stats, 'cept I don't have any ink - we could almost be brothers. "We few, we happy few, we band of perverts."

***

Mon, Mar 8 at 12:56 PM

Beginnings

I was 19, and was loving life. I had a new (used) car, and was enjoying all the freedoms it afforded me, not the least of which included fucking my hot blonde girlfriend whenever I wanted to. I kept my hair cut crew cut short, and was a skater and soccer player, so I've always been in pretty good shape. When I was in my teens I was always a little self conscious about being thin, and used to work out a lot to gain muscle but my metabolism was so high that it never worked.

Anyway, during that time in my life I was partying with my friends, drinking and smoking pot a lot. I'd always had pretty good luck with girls, and lost my virginity to a cute art student with vastly more experience than me. My current girlfriend was a hot little petite blonde, who sucked my cock the first night I met her, and let me fuck her the first time I got her alone in a room. It was awesome and I still think about her a lot. We're friends on Facebook now. Even though I was getting very high quality regular pussy, I was still curious about other things, and kept finding myself fixated on my girlfriend sucking my cock...the way she licked it and played with it...the way she drooled when she tried to take all of it.... watching her suck me was almost better than fucking her, and I kept finding myself imaging what it would be like to suck a cock like that...

As we were under 21, we were always looking for ways to get alcohol. One of my buddies knew a super cool older dude named Theo, who lived alone just outside of town, and who would sometimes have some pot for sale. He would also go to the liquor store to buy booze for us if we paid him to, and sometimes he'd encourage us to hang out. He had a huge TV for the time, and a big collection of movies, and over the course of a couple weekends I ended up hanging out there late at night. He was always really cool to me and had no problems hooking me up, letting me drink a lot of his booze and smoke his weed. About the third time I went over to party at his place, no one else was there but us. Instead of the light beer he usually shared with us, he had a big bottle of Jack Daniels and several two liters of Coke...

***

Mon, Mar 8 at 1:58 PM

Hey!

Glanced at your most recent email, which looks like it's about you when you were 19 and with a 40ish guy.

Perhaps we could roleplay / cyber about the stuff that makes you blush, being a girl / gurl (unclear from the context which option turns you on the most)? I don't feel shame about my sexuality - why pretend to have someone else's desires instead of what you actually want?

Gonna read your Beginnings email now, see what it's about.

***

Mon, Mar 8 at 1:52 PM

Back then, when I drank with my friends, we would all pretty much keep going till the booze ran out, or until we all passed out. I'd developed a taste for Jack and Coke, and liked how quickly I got fucked up when I drank a lot of it. My inhibitions went out the window, and I had fun getting hammered and then fooling around with my girlfriend. The things little blonde 18 y/o Ava encouraged me do to her probably deserve their own set of stories, as she was a dirty girl, and because of her I had some experience with drunken naughty sex. She liked making me cum and the first time I fucked her, she stopped me before I got close and told me she liked the way cum felt on her skin. This pushed me over the edge and I erupted all over her smooth flawless young skin, as she moaned and writhed around, eagerly jacking me off and then rubbing my hot jism into her skin like it was lotion.

I'd brought Ava to Theo's a couple times, and he was cool to her but a little aloof, I think trying not to make me feel jealous or anything. Looking back I'm pretty sure his dirty mind must've been racing, imagining the teenaged sex we were obviously having, but at the time it seemed like he was playing it very cool. This time, when it was just the two of us, he mentioned her a few times, telling me how luck I was to have a little hottie like that. I liked the way it made me feel when he talked about her like that, and I'm sure he noticed.

"So...you wanna watch a movie?" Theo asked me, handing me a big pint sized glass of Jack and Coke and ice.

I grinned as I took a big slug of it, icy cold and sweet but burning as it hit my belly. "Yeah... let's watch something with some tits!" I felt buzzed from the first few sips of my drink ... butterflies twirling excitedly in my tummy.

Theo looked at me quizzically, then slowly grinned, not so subtly glancing down at the way my jeans fit me. "What's the matter, no Ava tonight?" he asked, raising an eyebrow suggestively.

"Naw, not tonight. I'm not pussy whipped or anything." I grinned, feeling macho talking about her like that, liking the way it felt ... downing more of my drink.

"Well, if you wanna see some tits... I've got plenty of that," he said, "but I gotta tell you, I'm not shy." He had this knowing smirk when he said that.

My tummy did somersaults then and it still does now, thinking about those words.

Theo dug out a movie, one of those juvenile 80's T&A movies, plenty of hot girls running around topless. He kept the drinks flowing and lit a joint, commenting about the girls on the screen.

Theo was in his forties, probably around the age I am now. He was medium height, dark hair and eyes, with a little beer belly. He usually dressed pretty casually, jeans and polo shirts, but when he got up to make us our third big rounds of drinks, it took him a little longer, and he came back in wearing sweatpants and a white t shirt. It was pretty obvious that he was getting a hard on, if he wasn't completely erect already, and he didn't try to hide it as he walked back in and handed me my drink. "I told you I wasn't shy," he said, winking at me as he reached down and tugged on himself thru his sweats.

My heart skipped a beat or two and started to pound ... it was the first time I'd ever seen a man touch himself like that. His grey sweats showed a big bulge, and as he sat a little closer to me on the couch he took a big sip of his drink, looking at me sideways over the brim of his red plastic pint glass, as he reached down with his other hand and very obviously rubbed his cock ...

***

Mon, Mar 8 at 2:03 PM

Hi,

I'd say you're about a quarter of the way into a publishable story for Literotica ... I'd like to see how it turns out!

***

Mon, Mar 8 at 2:04 PM

You're a talented writer, BTW. Do you have any published stories on Literotica I can check out?

***

Mon, Mar 8 at 2:41 PM

Thanks! I've never posted any stories, or even ever really tried to write them, so you're my first reader! I used to role play online often, but that's the only real experience I've got with writing, besides a lifetime of reading. I did go to college for liberal arts...

One aspect of your stories that really got to me, was the idea of playing girlfriend for another man. I've had so many resolved fantasies in that direction, which have until now I've only been able to give life to by playing a girl online ... which is a lot of fun and very hot but this is ... real ...

***

Mon, Mar 8 at 2:55 PM

I didn't know what to say, so I took a big long sip of my drink, trying not to stare as he kept finding reasons to touch himself thru his sweats as he sat next to me.

"Wanna see something hotter?" he asked, grinning lewdly.

I nodded, grinning back, loving the growing tension and the taboo-ness of having a hard on in front of another man ... and being able to see that he was hard too. The idea that he was turned on by me made my whole body tingle and feel electrified. It's kinda the same feeling I'm having now, writing about it, all these years later ... reliving it ... confessing it ...

Theo got up and put in a different movie ... lighting another joint and handing it to me.

By then I'd had three big glasses of mostly Jack with ice and a splash of Coke ... and nineteen year old me was really feeling it. The movie started and predictably enough, it was hard core porn.

Theo took the joint back from me and sat down next to me on the big sofa, close enough that our legs were touching. "I warned you that I'm not shy."

The tone of his voice was somehow making me feel submissive and feminine.

He put his drink down, and then slowly reached down to the waistband of his sweats, and pulled them down, letting his big cock spring out.

It made my heart pound in my chest to see his cock so close ... the first time I'd ever done anything like this. It was long, longer than mine but a good deal thinner, I thought as I stared at it, fascinated.

He must've been completely hard already, because as he grinned and reached down to play with it, it was springy, and slapped powerfully up against his abdomen when he pulled on it and let it go. He had dense dark pubic hair, and as I watched he tugged his sweats lower, pulling his big balls out, letting me see his entire package, throbbing so hard and so close to me ...

***

Mon, Mar 8 at 3:06 PM

Theo was watching me watch him, I discovered, as I finally looked up at his face again. I could feel myself blush bright red, the excitement and embarrassment mixing with the Jack, making me feel incredibly aroused ...

"It's no big deal" he said casually ... slowly sliding his hand up and down his shaft ...

I looked back down, that crazy fascinated feeling taking over me, watching as he played with himself. I felt nervous as hell, but I took a last big hit off the joint, set it down, and started unbuttoning my jeans. The handfuls of girls I'd had experience with at that point had all been very complimentary and flattering about my manhood, but being young and naive and self conscious, I never really knew if they were telling me the truth or just being nice.

The way Theo stared down at my crotch as I undid the first couple buttons turned me on. It made me feel like a woman must feel when a man lusts after her. I remembered how Ava would give me this sexy come hither stare as she undressed for me, and how it turned me on to see that. So I gave him a similar look, took a deep breath, working up my courage, and then let the tip of my penis peek out over the top of my boxers...

***

Mon, Mar 8 at 3:55 PM

Hi Sean,

I get how good it can feel to embrace your feminine side. I've roleplayed being a girl several times in real life, and fantasized it quietly (or not so quietly) while having sex with girlfriends or my wife. My story documenting my first time doing anal (The First Time I Got Fucked), which I wrote a few days after the event, involved roleplaying being a schoolgirl. It was extremely hot.

That first time I got fucked, I met the guy on Craigslist. I kind of nervously went over to his place, having only sucked my first cock a few days before. Didn't really know what to expect. We talked a bit at his house, making sure I was comfortable and felt safe. He had this schoolgirl fantasy - even had an outfit his ex-wife had worn. So at his urging I shyly got dressed up as a slutty Halloween version of a schoolgirl while he watched me with this lustful stare. Then he coaxed me onto my knees, and I sucked his cock until he was super hard. He then wanted to fuck me bareback, but I insisted on a condom, because I'm not a reckless idiot.

So he got a condom, and I did this thing, "Oh, I'm a virgin, please don't fuck me."

He got this evil grin. "I'm gonna fuck your tight virgin pussy."

"Please. No. Fuck my ass instead, so I can stay a virgin."

"Stand up. Bend over the bed. Spread your legs. Wider, slut. I'm gonna fuck your ass now."

I reached behind me and made sure he'd put on the condom, then guided it towards my arsehole. He pulled to the side the pink panties he'd given me to wear, lubed up my ass, slide a finger in, and when I start thrusting back he started pushing his cock against my tight hole. It felt like he was aiming too high, like he missed the hole completely and was shoving against my skin. Then he popped my cherry. It fucking hurt, and I made this startled squeaky cry, like you hear in those Asian porn videos. He pulled his cock out, and I thought he'd changed his mind because he'd hurt me, but he was just slopping a lot more lube on his cockhead. Then he grabbed my hair and my neck, roughly bent me over more so I felt even more submissive, and started fucking me hard, balls deep after a couple of strokes. It still hurt and felt incredibly full, but by then he'd started hitting my prostate and it was both hot and painful and super sexy, and oh so good every time he nailed my prostate. I started fucking back at him, trying to make him cum, and soon he grunted and pulled up my plaid pink schoolgirl skirt and spanked my ass while he shot his cum while inside me.

Then I laid on the bed and stroked his cock after he'd removed the condom and cleaned his dick, and at his urging gently kneaded his balls, and he got hard again and climbed up so he was sitting on my chest. He facefucked me, his balls hitting my chin with each thrust into my face until he shot hot sticky cum in my mouth, and told me to swallow. So I swallowed like a good girl, kept on sucking all the remaining cum out of him.

He was still straddling my chest, I wanted to just lay there a bit, savoring the moment, my mouth still salty and a bit coppery tasting from his cum, wanting to feel some intimacy, but then he said his roommate would be home soon and I had to go now.

***

Mon, Mar 8 at 3:59 PM

P.S. This is an amazingly good story, especially if it is a first draft. If you choose to submit it for publication, I'd have to change some details, so the editors at Literotica don't send it back for revision. In particular, if you mention anyone being a teenager, you can't just leave it at that. For obvious legal reasons they'll require you to specify that they're 18+.

***

Mon, Mar 8 at 4:01 PM

Thanks! It is absolutely a first draft, I'm writing it now as I'm thinking about it.

***

Mon, Mar 8 at 4:05 PM

And of course I totally get it about the age thing. I'm just telling the story as it happened, and honestly, the age thing makes it even more taboo. Totally as it happened though. I think age play is hot too, you're not the only one who's gotten off playing a naughty schoolgirl...

I'm glad we connected! I have to be super careful, I have a wife who uses my phone sometimes, to look at photos and videos. In the past, I chatted via an online service like yahoo messenger (which doesn't exist anymore) or certain chat sites online. I'm leery of the chat services now, I don't want to get malware or anything. Maybe there's a discreet messenger I could use for role play ...

***

Tue, Mar 9 at 7:37 AM

I'm not sure why you feel you have to be so careful - it's not like talking to someone is wrong. Is your wife homophobic? My ex was, and it was a real pain to keep stuff hidden from her because she couldn't accept me as I am. Until I got divorced and found a wife who accepts me and my highly checkered past. ;)

***

Mon, Mar 8 at 4:53 PM

"Fuck yeah" Theo growled, staring down at me.

My cock throbbed excitedly, the tip swollen and big as I let it peek out, loving the way he reacted.

"If you get naked, I'll suck that thing dry" he said dirtily, eagerly peeling off his sweatpants, making his cock bob around almost menacingly. He was old enough to be my father, and his body was much more hairy than mine, coarse dark hairs over his chest, running down to his crotch, such a contrast to my mostly hairless skin. In soccer in high school other kids made fun of me in the showers sometimes, because I had hardly any hair on my body. He had this gleam in his eyes which kind of sent alarm signals to me, but I was very drunk and high by then, and extremely turned on and horny.

As Theo stood there watching me, he started masturbating, his strong hand sliding up and down his long stiff shaft while he leered at me. I couldn't believe what was happening. I felt really drunk and fucked up, but it was just so damn hot ... I was almost convincing myself it was a dream already ...

I took a breath and stood up, kicking my sneakers off, and peeled down my tight fitting jeans. I wore old school cotton boxers back then, and I can even remember that it was a red plaid pair, something that might've come from LL Bean one Christmas. I glanced at the TV and had to stifle a moan. There was a hot, slutty looking chick naked on her knees, passionately sucking off a well built, studly guy as he stood in front of her, her big tits bouncing, her spit all over him. My cock was throbbing and I felt dizzy as I tugged my boxers down, until I was standing there in front of Theo in just a T shirt, nude in front of a man for the first time in a context that wasn't a gym or locker room kind of thing.

Theo grunted and moved closer to me, making me feel dizzy and nervous, in a way I can still remember clearly. It was hot and exciting and a little scary, and I loved it. He reached down and made me gasp by cupping my bare balls. I wasn't expecting it and as he squeezed a little my knees buckled and I couldn't help moaning out loud as he started to fondle me, exploring my young teen body. His hand moved to my young stiff cock and I remember gasping out loud, completely involuntarily, the first time I'd ever had such a strong reaction.

I'm about 7 inches long and cut, and pretty thick around. Every person I've been with has commented on my cock being "nice" or "big," or something cool and flattering like that, and I've always been a little proud of it. I think when it's hard it's a pretty damn nice cock.

Theo must've thought so too, because he put his other hand on it and started jerking me off, his other hand still fondling my parks smooth balls. It almost felt like he was molesting me ... and I liked it ...

"You like that, don't you, boy" he said gruffly, and my knees felt weak. I was drunk and it felt like maybe I wasn't completely in control of what was going to happen next. I reached out for his cock, wanting to see what it felt like, and not wanting to wait anymore. He grinned as he felt me tentatively put my hand around him. It felt so strange in my hand, not like my own at all. I squeezed it experimentally and he grunted with approval.