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
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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
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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!!
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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
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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.”
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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…
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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.
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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!
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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?
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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+.
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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.
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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 …
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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. 😉
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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.
He reached down and guided his cock next to mine, putting it underneath mine as he held them together, pulling downwards. He was longer than me and it made me whimper boyishly as I felt the tip of him press into my sac. “Do you wanna take your meat, boy?” he asked, his voice low and dirty …
***
Tue, Mar 9 at 3:56 AM
I was so excited I was almost shaking, my stiff erection quivering and jerking in front of me as Theo peeled off my T shirt, and then I was completely naked in front of another man, with a raging hard on. He put his hands on my shoulders and started pressing me downwards, smiling wolfishly, and as my heart pounded loudly in my ears I let him push me down until I was sitting on the edge of his sofa, with his big hard cock right in my face. I’d never experienced anything like this before, although I’d sure daydreamed about it lately while I fucked Ava.
The porn he’d put on blared in the background, the actress now on her knees getting fucked by her muscular stud. I can still remember her moans, and the way her tits swung around and slapped together as she got fucked, while I sucked a cock for the very first time. She was brunette.
Theo started to run his fingers through my short hair, and with a soft moan I wrapped my hand around the base of his shaft, and took the tip of his cock into my hungry mouth. The head of him was big, and shaped very differently from mine, which surprised me a little for some reason. Where mine was kind of flared and and pointed, his was thicker and more blunt, and felt sort of rubbery in my mouth as I started to suck it. It turned me on so much I almost came right there, my hand squeezed tightly around the base of him, pressed into his dark pubic hair as I started to get into it, swirling my tongue over him, letting the tip press into the soft sides of my cheeks, the way I’d seen girls do in pornos, as my own aching cock twitched and bobbed warningly.
“Mmm, yeah … that’s it … suck that cock, boy,” he told me, his hands holding my head in place as he started to pump his hips a little. His cock was longer than mine, but thinner, and as I moaned around it he pushed it in far enough to make me gag. Hot spit drooled out of my mouth, and he pulled back a little bit, looking down, watching me intently … I managed to grin up at him a little, and then naughtily let his wet cock pop out of my mouth, and I started gently slapping it against my lips while I looked up at him.
“Yeah … yeah you like that cock … you like it, don’t you? Mmm…” Theo moaned at me, moving closer between my spread legs, and I nodded willingly, reaching down for his balls with my free hand, knowing how good it felt for me when Ava played with my nuts. Again, it surprised me to feel the shape of his anatomy, unattached to mine … as if somehow I was expecting to feel it more when I touched him. He grunted in approval, so I gingerly cupped his sac, being overly careful not to hurt him, feeling so new at all of this despite having the same body parts as him. As I started to fondle his balls, I lifted his shaft with my other hand, making it point straight up, and shivered a little as I pressed it against his body, and saw how the tip just barely reached up to his belly button. It excited me that he had such a big cock, and I knew from my own experience that my own wouldn’t quite reach as far as his did when I pulled it up against me like that. I held him right up against his body and started to lick him, pressing my tongue into his base, and then licking upwards along the thick vein in the center of his shaft, being naughty and flicking my tongue over the head as I reached the end of him. I wasn’t used to being with someone so hairy, and while I much preferred touching Ava’s silky smooth buttery skin, the roughness of Theo’s body reminded me that I was actually having this experience for real.
“Does your little girlfriend suck your cock like that?” Theo asked, leering down at me.
I nodded, squirming a little on the sofa, feeling excited bursts of energy shoot through my young body as I started to let myself imagine what it would be like to be a girl, pleasing a man like this, letting Theo imagine what little Ava would look like sucking my cock.
“Yeah, she’s good at it.” I let him pop out of my mouth, all sloppy now from my hot spit, feeling dirty and slutty and so sexy. I moaned into his shaft as I pressed his cock against my face, pursing my lips and pressing them into him, smiling to myself as I let him feel my big soft lips, the same big lips girls seemed to want to kiss, and other boys made fun of. I remembered everything Ava and my other girlfriends had ever done to me with their mouths, and started doing it to Theo, making him groan and arch his back as I tried to deep throat him and gagged again.
“You’ve got a really big cock,” I told him, experimentally, the words feeling strange coming out of my mouth like that. I’d never really gotten into dirty talk with my girlfriends, but I knew how much it turned me on when Ava said stuff like that during sex, so I wanted to try it, and in my drunken state I started slipping into these weird kind of thoughts about what it must be like to have a hot girl’s body that no man would be able to resist …
Theo’s cock throbbed forcefully in response to my words, and he didn’t say anything, just looked down adoringly at me.
“Mmm, you’re bigger than me,” I told him, looking up, slapping his cock against my lips again. It was a move Ava did particularly well, and I got a real thrill from performing one of her signature moves on another man.
She would fucking lose it if she knew what I was doing right now, I thought wickedly.
Theo groaned with pleasure, and I started concentrating on really sucking his cock, taking it in my mouth and then sliding my lips down around him, taking half of him, more, gagging a little and then starting all over, using my hands, the moans of the porn star loud in the background. If I glanced sideways I could see the TV and I watched it for a little bit, watching her get fucked while I sucked Theo’s big dick. His was more veiny than mine, and as I jerked him off with my hand I liked how hard and stiff he was. I squeezed his shaft a little harder, biting my lip as I looked up at him, knowing my hands were much stronger than any girl’s. Theo just moaned and didn’t say anything to make me stop, so I squeezed him a little harder, grinning as I saw how the tip got bigger, more red and angry looking, as I squeezed and squeezed and then finally took him in my mouth again.
“Ohh, fuck,” Theo groaned, and then abruptly stopped and pulled his cock away from me, taking a step back as he reached down and almost frantically squeezed the base of himself, doing what I know now to be a good technique to prevent yourself from cumming. “Fuuuuck…” he said again, his voice deep and growly. I giggled boyishly, feeling this strange and new sense of pride that I’d made him feel so good that he almost lost control and had to physically restrain himself. It felt so hot to be so desired, to see the abundant evidence of my own attractiveness in the visceral response of his body, in his big throbbing cock. I knew the girls I’d been with had wanted me, but the raw intensity of Theo’s erection was different, more thrillingly naughty somehow, and I loved that feeling.
The movie was coming to an end, and Theo walked over to put in another one, still holding his hard on tightly as he walked over, completely indifferent about his nakedness. Looking at his body like that didn’t do anything for me, I discovered, and I reassured myself that I much preferred a girl’s body to look at … but his cock was just … another story. I didn’t care about the rest of him, I just wanted to pleasure his cock, to play with it and do things to it that I knew felt so good for me, when girls did it.
I can do it better than any girl, I thought dirtily to myself, cuz I know what if feels like!
I reached over for my drink and grimaced a little as I drained it. It was mostly just Jack in that big glass now, and as my head spun, Theo started the movie and turned back to me, his cock free of his hands now, completely and fully erect, sticking almost straight up as he walked towards me, as I sat completely naked on the edge of the his sofa. “Lay back a little,” he told me, as he finished off his own drink…
***
Tue, Mar 9 at 7:43 AM
It’s an interesting literary choice, referring to a cock as “I” rather than “it”, as if their identity was tightly bound up in their dick. Perhaps that explains the otherwise inexplicable desire of guys to send unsolicited dick pics to women where even a modicum of knowledge of how women think would reveal that as a hard fail.
Sex with guys tends to be coarser, rougher, more raw and primal. Experiencing this on the receiving end can be very dirty and sexy and taboo, even if one greatly prefers women’s bodies over men’s.
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Tue, Mar 9 at 8:56 AM
I’m glad you like my story so far, it gets me hot writing it. It’s all true!
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Tue, Mar 9 at 9:09 AM
When you read my story, does it make you think about experiencing it as the younger me, or as the older guy? Or maybe you don’t insert yourself into the story at all? I like knowing what excites people and turns them on.
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Tue, Mar 9 at 5:05 PM
Mainly as the younger you, since that is the POV character, and most of my sexual interactions like this were on the giving end … occasionally I’ll flash to the older guy’s view …
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Tue, Mar 9 at 9:24 AM
What the hell am I doing?
My mind screamed that at me, unbidden, as I found myself laying back on Theo’s sofa, completely naked. Ignoring the thought, I smiled a little up at Theo, feeling strangely vulnerable and almost feminine in my desire to please this man with my body. I saw the way he stared at my cock, so I lifted it up for him, letting him watch as I held it by the base and made it stick straight up, wanting my cock to look as big as possible for him, wanting him to like it. Ava let me watch her playing with herself sometimes, which I liked, now I found the way Theo looked at me to be almost unbearably exciting, and I started touching myself a little, showing off, imagining that I was feeling the way Ava probably did when she showed off her body to me like that.
The weed and the bourbon was making it hard for me to see straight, but my cock felt like alive and harder than it’s ever been before, but and thick in my hand as I let Theo watch me. He got closer, and then lowered himself to his knees in front of me, pressed my knees apart, and moved up close between them, taking my throbbing cock in his hand. “You’ve got a nice cock, Sean,” he told me, grinning as he started molesting me … fondling my naturally smooth balls, shaking and waggling my erection.
Wails and moans of another porn star getting fucked filled the room, and Theo ran his palms up my body, from my pelvic region up to my chest, enjoying touching my soft skin. “You’re nice and smooth,” he said approvingly, reminding me of the way he might’ve talked about a sports car, letting his fingers play with my fine, light colored public hair. I’ve never had any significant body hair, to the point that my arms are still hairless, and Theo really seemed to like that…
***
Tue, Mar 9 at 10:14 AM
I don’t think there’s any way I would’ve lasted so long, if I hadn’t had been so messed up from the pot and booze. With my girlfriends, I’d discovered that if I wasn’t really careful, I’d cum too fast and then it would take a minute before I was ready to go again. This especially happened if the girl went down on me first, which tended to happen, and I’d come to rely on the ‘second round’ as my chance to satisfy and impress my lovers. Ava really liked making me cum with her mouth before she let me fuck her, and after she discovered that I could reliably rally for more fun after my first orgasm, she really had fun with it. I don’t think I’ve been with another girl since who acted like such a porn star, and she was just a teenager. I can still remember the jolt of excitement I felt the first time she made me cum in her mouth, and then opened her mouth wide to let me see my own cum all pooled up in her mouth before she swallowed it. She liked it when I came on her little perky tits, and sometimes she’d make me cum and then ride on top of me afterwards, with my semen still splattered all over her hot little body. She was a pale blonde white girl, and fuck it was hot when she’d rub my cum around on her pale pink nipples …
My mind snapped back into the present as Theo finally engulfed my cock completely, taking me by surprise and making me gasp as he easily took all of me, his lips sliding down to the very bottom of my base, taking me deeper and smoother than any girl ever had. He squeezed and tugged at my sac, less afraid of hurting me than I’d been, and he pulled his mouth off and kicked his lips hungrily, clearly enjoying himself immensely. I tried reaching down for him, wanting to touch his prick again, but he chuckled and didn’t let me reach him. “Don’t worry boy, you’ll get to feel it again in a minute,” he told me, watching my face as he worked his hand up and down my now wet shaft.
He only started calling me “boy” once I got naked, I thought abstractly to myself…
Theo stared at my face, watching me like some kind of predator as he slid a circle of his fingers down around my base and squeezed … doing the same squeeze technique to me that he’d done to himself earlier. He stopped playing with my cock as much, and started focusing on my balls, squeezing and fondling them, and finally lowering his mouth to lick and suck at them, getting them all wet with his spit, keeping my trembling cock pointed up out of the way.
“You’re gonna like this” he said, and then he started licking carefully underneath then. I gasped out loud and reflexively spread my legs apart, scrunching back on the sofa a little so I could lift my knees upwards a bit, towards my chest. “Mmm, yeah, that’s perfect,” he said softly, using the web between his thumb and forefinger of his left hand to encircle my sac, and lift it gently upwards towards my shaft. It almost reminded me of being at the doctor’s office, that strange sense of vulnerability that came with being exposed in that way, knowing that someone was looking right at my tight little asshole. Theo had purposefully used a lot of spit while he licked and sucked at my balls, and now little runners of it oozed down between my inner thighs, down under my sac as he kept it lifted up, pushing my knees further up towards my chest, staring intently at my tight little virgin opening …
***
Tue, Mar 9 at 1:42 PM
Until this moment in my life, I’d had zero experience with any kind of anal sex. None of the girls I’d been with were interested, none of my friends even talked about it, and it just wasn’t something that was on my radar. Being that this all happened before internet porn was a thing, I hadn’t even seen many dirty movies, mostly just snippets here and there, seen in stolen moments late at night at my friends’ houses. Most of what I knew about porn came from dirty magazines, like Playboy and Hustler.
As I lay back naked on Theo’s couch, my heart pounded away excitedly. I loved how dirty and incredibly sexy it felt to spread my legs apart for him, like a girl in Penthouse. He lowered his face and started licking me below my sac, carefully holding my cock and balls up out of the way, and I whimpered out loud when he started to lick my butthole. It was a completely new feeling, and I can remember it vividly, the way my cock jumped and throbbed uncontrollably as he ran his tongue around it, licking it, and as I now know, lubricating it.
“That feels good, doesn’t it boy?” he said, looking up at me as my cock twitched.
I nodded, almost unable to speak. “Yeah … yeah it feels good,” I whispered.
Theo didn’t need much more encouragement than that, and as he wrapped his manly hand around my eager young prick, he started gently pressing his middle finger against my tight little opening. “You like that, don’t you?” he asked me, teasing me, his grip around my cock almost painful as he probed me, teasing and testing…
“Yeah … so good…” I took a deep breath, letting my eyes move to the TV screen, watching a hot blonde getting spitroasted by two guys. “Do it. Do it,” I moaned to Theo, and he smiled evilly, and slowly pushed his middle finger inside of me, my hole all wet and slippery from his hot spit, and my entire body shuddered and flexed as he slid his finger in what felt like a huge amount, but which was probably only up to the second knuckle, I was so tight. “Ohh … oh fuck, ohh fuck!” I panted, gasping as he pulled his finger almost all the way back out, and then pushed it back in …
Theo knew what he was doing, and kept a tight grip around my cock as he started fingering me, knowing that I was dangerously close to cumming. I could tell he liked doing it, the same way I liked fingering girls, and the thought made me shudder all over again and I knew I wasn’t going to be able to take much more of this.
“I’ve never done this before,” I gasped out to Theo, and he seemed to like hearing that, because he grunted a little and started playing with my trembling cock again, gripping it tightly so he could feel it shuddering and starting to spasm.
Theo stared at my face again as he made my eyes pop wide open, my upper body lifting off the sofa as precum started streaming freely out of the tip of my cock, down over his hand. He made me take the entire length of his thick middle finger, making me cry out, my cock so stiff and leaking precum all over my belly as my body responded to his probing.
He lowered his face to me again and deepthroated my cock at the same time he pushed his finger in me all the way again, and it made me cry out again, boyishly I think, a sexy kind of sound that I’m not sure I’ve ever really made out loud again.
“Ohh fuckohfuckohhhfuuck,” I managed to moan out, trying to warn him, trying to lift his head off me but he wasn’t having it.
“I’m gonna cum!” I gasped out, thinking he’d want to move away, but he just sucked me even harder, putting his fist around my base and pumping it as he slid his wet finger in and out of me, sucking greedily at the top half of my cock until I cried out and started cumming.
My body jerked and spasmed as I felt the orgasm coming at me from the top of my head down to my toes.
Theo grunted hungrily as kept going, his finger pressed all the way inside me now, wriggling as he sucked me.
My cock exploded into spasms, cum erupting from deep in my balls and shooting deep down into his throat as he greedily milked me, knowing exactly what to do, timing his finger and his mouth and hand just right, so that just as I finished cumming, he let his finger slip all the way out, feeling my insides clench and clutch around him all the way out.
Theo swallowed every drop of my cum, never lifting his mouth off of me until I was completely done, and no girl had ever made me feel remotely like that before. My face and entire upper body were flushed red with excitement and now embarrassment, and I started lowering my legs as Theo stood up again in front of me.
“No, stay just like that,” he told me, and I stopped closing my legs, laying there halfway back on the couch, my cock slowly softening and twitching. He nodded and started jacking off, standing in front of me, looking down at my body. I spread my legs for him, thinking again of how hot I thought it was to look at pics of women posed that way, and he nodded, moving closer.
“I’m gonna cum all over you” he said dirtily, and my heart pounded all over again, my half soft cock twitching excitedly as he pointed his big swollen dick at me from above …
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.
***
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.
***
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.
***
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…
***
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. 😉
***
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…
***
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.
***
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…
***
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.
***
Sun, March 14 at 10:43 AM
Does your wife look like a mature version of the slim blonde girls you go for here?
***
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.
***
Sun, March 14 at 04:09 PM
Is there something you want to try with a guy, but the opportunity hasn’t presented itself?
***
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 …
***
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?
***
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.
***
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.
***
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.
***
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?
***
Mon, Mar 15 at 8:28 AM
I’ll tell ya the story if you want 😉 Theo did like giving me Jack Daniels …
***
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.
***
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?
***
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!
***
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 …
***
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 …
***
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?
***
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?
***
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!
***
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!
***
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 …
***
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 …
***
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!
Mon, Mar 15 at 7:09 PM
My personal view is you can’t have been raped if you’re OK with what they did, much less if remembering what they did still turns you on decades later. 😉
***
Tues, Mar 16 at 5:44 AM
He probably did assfuck me, didn’t he? Wow. My cock is bulging again just thinking about it. I guess from his point of view it must’ve been a dream come true.
***
Mon, Mar 15 at 8:29 PM
And it never occurred to me that he might’ve put something in my drinks. I never even thought of it, but I suppose it’s a possibility, isn’t it? I did get massively fucked up, more than usual even at that age … and I’ve always kind of wondered how I lasted so long before cumming, I remember being sooo turned on. And that feeling I think maybe I had just before I blacked out … Hmm
***
Tues, Mar 16 at 5:44 AM
I just can’t stop thinking about this. The idea that he assfucked me is driving me crazy. Even writing the word does strange things to me. You’re such a talented writer, maybe sometime you’ll write the story of my experience from Theo’s POV to help me understand what happened better
***
Tues, Mar 16 at 6:59 AM
At some point I’ll edit our conversation so far and turn it into the fourth chapter of my Cybersex series. I’d obviously need to clarify the teenager is 18+, and remove overly specific personal information about you and me. Is there anything else you’d want edited out because it would be too personal or identify you?
If you want to be credited as the coauthor in an author’s note prefacing the story, I need your Literotica handle.
I would probably need to know the full extent of your experiences with Theo to do the best job of writing from his POV, but my inclination is to go dark and have him roofie you and technically rape you without ever calling it that, and then juxtapose it with you getting turned on decades later remembering it, and wishing that he had fucked you while you were conscious and about to consent.
I do have several other stories in my writing queue I’d like to finish first before trying the Theo one, but the Cybersex one would be not particularly time consuming since it would just be copying and pasting and then some light editing. Though sometimes editing turns into massive rewriting as you tweak the story for maximum impact. 😮
***
Tues, Mar 16 at 7:29 AM
Oh damn, your “inclination to go dark” has me bulging in my jeans again. Honestly writing the beginnings story kinda brought up a lot of stuff but holy shit is it arousing! The more I think about it, the more likely I think the dark scenario with Theo probably was. It would’ve been hard for him to resist taking advantage of the situation. I was so young and naive.
And I love the idea of you publishing something I was involved with!! You can do whatever you want, I do t really care about credit or anything. Hot!!
***
Tues, Mar 16 at 8:52 AM
Cont. again… I wrote this part Mar 14…
I can easily remember how sexy it made me feel when he made me lay back on the couch with my legs spread apart like that, the way a girl spreads her legs when she wants get fucked, and how hungry for my cock he was, like he was doing it for his pleasure, not mine. He very obviously enjoyed fondling and sucking my young cock and hairless balls … it was an intense feeling, and it’s making me throb now thinking about it. He played with my balls and jerked me off in a way no one else has, not to mention the hungry, greedy way he sucked my cock, and I’m now realizing that part of what I was enjoying so much and found so thrillingly erotic, was the sensation of playing girlfriend.
—- break —-
Cont Mar 16…
When I think about the whole affair, which is quite often these days, it’s pretty clear that the consent issue was muddled at best. I had already let him penetrate me with his finger, the first time we fooled around, and I let him lick me all over down there too, and I liked it. Encouraged it, even, with my “do it…do it…” routine, which is still surprisingly vivid in my mind, when some of the rest of these things are kind of blurry. I wonder a lot now if I blacked out because he slid his cock up my ass … is that even a thing?
Anyway, after that first encounter, I went back a second time (and a third, and more), knowing that we were going to have some kind of sex, so that must muddle things too. On the other hand, I was underage for the booze, so in that regard, yes, he probably, technically at least, raped me. I honestly don’t remember everything that happened that second night, and even some of the first night is a little blurry, because of how much I drank. And now there’s the possibility that it was more than just booze.
I liked it when you asked me questions about this. If you want to ask more questions, for background research for your writing, or just because it’s sexy and it turns me on to answer honestly, fire away.
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Wed, Mar 17 at 6:14 AM
Read what you wrote about the first time you got fucked. Wow! That’s so hot. You’re starting to make me fantasize about assfucking a guy now …
On a related note, and forgive me for belaboring the point, but from your description of how it felt to get fucked, do you think it’s the kind of thing that could make someone black out?
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Wed, Mar 17 at 6:25 AM
An orgasm from just being fucked won’t make you black out. Make you sleepy as fuck, sure. Blacking out – not remembering how you got somewhere – my dad was an alcoholic, and he’d black out some nights, hours and hours missing according to him. So, drugs of some kind would be my guess.
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Wed, Mar 17 at 6:26 AM
Gotcha, it wasn’t the orgasm I was thinking of, as much as the prospect of having a cock going up my ass unexpectedly when I was drunk and disoriented ..
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Wed, Mar 17 at 6:35 AM
Can’t say for sure, since I’ve never blacked out. You have more experience than me there!
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Wed, Mar 17 at 6:44 AM
I definitely wasn’t planning on getting fucked. Honestly, after the first night I just mostly wanted to suck his cock again. I kept thinking about it, how it felt in my hands and mouth, how he reacted to my nakedness, and the way I pleasured his cock. I think I can see now how dressing up could make the fantasy more … immersive. It would’ve been pretty hot if he’d made me dress up in your schoolgirl costume. Maybe that could be an opportunity for some creative license. I’ll probably go jack off thinking about it soon.
What I’m starting to think, is that maybe I was on the edge of blacking or passing out, all drunk and high and possibly drugged, and when Theo decided to replace his finger with his big cock, it was so intense that I just kind of blacked out, and he had his way with me.
There’s also a chance he recorded it all on video, which I didn’t mention before. He had a VHS camera set up (on a tripod!) in the room, but it was never powered on while I was there.
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Wed, Mar 17 at 6:50 AM
A camera. On a tripod.
You’re wicked skilled at burying the lede.
Always assume a camera or a mic are hot (recording), even when you’re told it is off. First rule of TITAF (Teh Intertubes That Are Forever).
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Wed, Mar 17 at 6:57 AM
Yes, you’re absolutely correct. I know that, now. I did ask about it, though, and Theo showed me how it had a red light when it was on, and no light when off. I do remember glancing at it several times on both of those nights, suspicious of it, but again, I was a drunk and high teen, all naked with a big hard on, and didn’t have great judgement back then.
On my subsequent visits there was no camera in the room anymore.
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Wed, Mar 17 at 7:00 AM
I … fuck. Wow.