Just Like a Real Girl Pt. 01

When I first met Clint online, he seemed like most men I meet there; bi-curious, inexperienced, married (probably), with no intentions of ever meeting in person. In my experience, many men who go online looking to chat with other men (or men dressed as women) are there for just that; to chat, and fantasize, and possibly jerk themselves off while they fantasize about doing something considered somewhat taboo. Sometimes I allow men to indulge in such behavior out of indifference or boredom, behavior which invariably ends the moment they have an orgasm, after which they vanish into the ether, never to be heard from again. But once in a while, I meet a man who is tired of fantasizing, someone who wants to do more than chat, and I can often tell them by the depth of the questions they ask.

Clint asked such questions. Such as, "When was the first time you put on a pair of panties, and where did you get them?"

Most men, those who are online trolling for wank-fodder, would have asked instead, "What kind of panties are you wearing?"

Intrigued by the depth of his question, I decided to tell him, though the content of my answer was deeply personal and much too intimate to share with a stranger. "I was fourteen," I told him. "And they belonged to my stepsister."

Clint then surprised me with his insight with a statement, "You had a thing for her."

He was correct. "Yes, I was obsessed with her for quite a while."

"Tell me about the panties, what did they look like and how did they feel?"

Writing my response, I found myself shifting in my seat, "Well," I explained, "this was the early nineties, only hookers and strippers wore thongs, so they were little black satin bikini bottoms. Every other pair she had were just plain white cotton, these ones jumped right out at me when I saw them. At first, all I could think about was how hot she'd look wearing them, and nothing else. All of the sudden I got this urge to put them on, and even though I knew it was wrong and what was doing was a huge invasion of her privacy, I put them on anyway."

"This was your first time wearing women's clothes?"

"Yes," I replied. 'I'd never even thought of doing anything like that before. To this day I still don't know where it came from."

"How did it feel?"

It was a very good question, and one I found difficult to answer accurately. "It was like getting punched in the stomach. I took off all of my clothes right then and there in her bedroom, and stepped into them. They were tiny and tight, so the only way I could fit into them was to tuck my cock between my legs. And the moment I looked down and saw what I looked like, it was like an explosion in my brain. It was by far the most intensely erotic thing I'd ever experienced up until that point. About thirty seconds later I felt something hot trickling down my leg and I realized I was leaking cum all over the place. It was everywhere."

"What did you do?"

"I was freaking out,' I told him. "I took the panties off but they were soaked, I was dripping all over her carpet, so I ran to the bathroom and started cleaning myself up. I knew she'd be coming home soon, and I was terrified she'd catch me. I washed the panties in the bathroom sink and dried them with a hair-dryer, but I could still smell my cum in them. Then I used a wet towel to clean the place I'd been standing in her room, but the cord of the blow-dryer wasn't long enough to reach so I had to dry it with another towel."

"That all sounds terrifying," Clint observed, "were you successful?"

"Just barely. She came home about five minutes later, and I was sure she'd come out of her room screaming. Her father hated my guts as it wasn, so if she said I'd been in her room or that her panties had been tampered with, he'd have wrung my neck for sure."

"But she didn't notice?"

"No. Thankfully."

Then, as further proof that Clint was very much in tune with how my brain works, he asked, "How long before you wore them again?"

I laughed out loud. He hadn't asked IF I wore them again, because he knew I did. "About a week," I answered. "But it was tricky."

"How so?"

"Well, I never knew when she'd be wearing them, and I always had to make sure they were clean and back in her drawer when she came home in case she decided to wear them for her boyfriend. Sometimes she'd tell our parents she was going out with her girlfriends, but I could always tell when she was lying because she'd go out and the black panties would be gone. So at first I'd just wear them for a few minutes and then put them back, and I started slipping a wad of toilet paper down the front so I wouldn't get them wet."

"Did you jerk off wearing them?"

"Not at first. But putting them on was like taking a bottle of boner-pills before that was even a thing. Sometimes I was so hard I could barely get them on, so I'd jerk off to get rid of the hard on. Then I'd feel dirty and humiliated, so I'd stop for a few days, but then the urge would come back even stronger."

"What did you think about while you jerked off?"

Another good question.

"At first, I thought about her. I thought about fucking her, I thought about going into her room and find her wearing the panties, and I thought about her coming into my room and finding ME wearing them. It was all very confusing at the time."

"I imagine it was."

"At some point I started to fantasize that I WAS her, and I imagined how sexy she must feel to wear those panties for her boyfriend. Around that time I also happened to find a cheap pair of handcuffs with a furry liner on them, and that escalated things in a big way. I imagined her using the cuffs on her boyfriend, I imagined him using the cuffs on her, and eventually I imagined being her while he used them on me. At some point, it was like a switch got flipped inside my brain, and that became the only kind of sex I was interested in."

"Which part, having sex with a restrained woman or being restrained yourself?"

"Being the one restrained."

"What did you think about specifically?"

"Well, I imagined being handcuffed in bed wearing her panties, and having a man stand over me, jerking off while he looked down at me. Funny as it sounds, the idea of having a man shoot his load on me seemed like an impossible thing that could never happen to anyone. Then I imagined, what if instead of shooting his load on my body, what if some of it got into my mouth? And even worse than that, what if a man sat on my chest and actually put his cock into my mouth? Keep in mind, no internet back in those days, just a bit of VHS porn floating around, so I'd never seen anything like the things I was fantasizing about. It was all in my imagination."

"That's a pretty imaginative scenario to come up with when there's no frame of reference. Did you ever imagine being fucked by a man while restrained like that?"

Sitting at my laptop in my living-room, I felt myself blush as I admitted something deeply personal. "Yes, but only after I started tasting and swallowing my own cum."

His response made me smile, "WHOA. That's quite a leap, how in the hell did THAT happen?"

"By accident, at first," I replied. "I was just laying down and jerking off in the panties, but I came so hard that some of it actually landed on my lips and chin. I was disgusted at first and tried to wipe it off, but I got a little taste of it. It wasn't at all what I expected, in fact I HATED it, and I couldn't imagine how women could even stand it! I'd only seen a couple of porn movies and women seemed to really enjoy it, so I thought it must be one of the many differences between men and women that they actually liked it. But, from that point on, I started to taste it more and more every time I jerked off, which at that point was about five or six times a day. I wouldn't say I started liking it, but I definitely liked the idea of being made to do it. Eventually, that led to the thought of, what if after a man made me put it in my mouth, he put it in my ass and fucked me like a girl?"

His response made me grin and encouraged me to reveal more.

"Mmmmm."

"One night, just as an experiment, I took a new candle from the dining room, and decided to see what it felt like to put something in my ass. It was long and skinny, but I tried to put it in dry and it hurt like hell. Then I had a TERRIBLE idea, and I lubed it up with a little shampoo. I can't even tell you the amount of pain I was in. It was so bad I almost passed out and didn't try it again for weeks. The next time, I tried a little bit of cooking oil from the kitchen, and I was able to get it in without the pain."

"What was that like?"

"Weird, but good. The edges were kind of sharp and that made it rough, so I began looking for things around the house that I could fuck myself with that were rounded and smooth."

"For example?"

"Hmm...," I thought back, "... a carrot, a tampon, a waterproof case with a rounded top and a flat base that kind of looked like a dildo, but I had a scare when that one slipped all the way in and I thought I'd lost it up my ass. I realized I needed something longer that I could keep a good grip on, and then I was getting something out of the fridge and I saw a cucumber."

"Oh my," Clint remarked.

"Yeah. It was sealed in plastic already, but I stole one of my step-sister's condoms and put it over the cucumber, lubed it up with oil, and tried to fuck myself with it."

"Tried to?"

"It didn't go well... let's just say I had a lot to learn about 'prepping' for that sort of thing."

"Enough said."

"But I also started experimenting with putting my cum on the cucumber and then putting it in my mouth like a cock, and I started to like it more and more. I knew I was never going to be able to suck my own cock (I tried, believe me), so I knew if I was ever going to get the real thing, I had to find a man willing to give it to me. And that's when the walks began."

"The walks?" Clint asked. "What kind of walks?"

Taking a deep breath, I launched into the tale, my fingers pounding out my story in a frenzy.

"My step-sister was staying with her mother for a couple weeks, and she left the black panties at home. Then my mother and step-father went to Buffalo for a weekend so I was all alone in the house. I'd just turned sixteen the week before but I only had a learner's permit and my folks had taken the keys to my mother's car with them, so I was stranded in suburbia. The neighborhood we lived in was upper middle-class, and very new. After 10 pm it was pretty common not to see a single car or pedestrian out until dawn the next morning, so I would frequently walk out to this baseball diamond a few blocks outside of the completed houses, and just sit on the bleachers, enjoying the night air and looking at the stars. So, that weekend, I went there wearing the panties under my cut-off shorts and a tank top. Once I got there I took off the shorts and left them on the bleachers, and just sort of walked around in the dark for a little while. I started fantasizing about what might happen if a man 'caught' me out there, and what he might do to me in exchange for his discretion. It goes without saying, I imagined having to get on my knees and suck his cock, maybe even swallow his cum."

"Hot little scenario," he interjected.

"I thought so, still do, actually. So the first night I walked there in my shorts and stripped down once I got there, but the second night, around 2am, I looked out the window and saw nothing but fog that was so thick I could barely see the streetlights. It was hot that summer, so it was probably 75 outside even at night, so I decided to do one of the dumbest things I've ever done. I was about to walk to the park once again, but once I was in my backyard I imagined what it would be like if I left my shorts right there, and made the long walk in just the panties and tank top. Honestly, looking back on it I don't know what the fuck I was thinking..."

"Wow, so you did it?"

"I did. I left my shorts and walked the entire way in panties. I'd never felt so vulnerable or exposed, but I'd also never felt so sexy and powerful. When I got to the park I went and laid down on the bleachers and imagined being handcuffed like that, and having a man find me. I was having such a good time that I started to notice the occasional car drive by the park, so I knew it was time to leave. I was half-way out of the parking lot when a car started from behind me and their headlights came on. I started running like hell for the fence that separated the park from the houses rather than out to the sidewalk. I didn't know who it was and didn't care, but I found out about a minute later that it was a cop."

"No!!!" Clint exclaimed.

"I climbed the short fence, no easy task in sandals, and took them off once I was on grass so I could run faster. The park was a couple of blocks down from my street, but since most of these new houses didn't have fences surrounding their properties yet, I was able to cut straight across and made it home long before the cop came cruising with his searchlights on."

"Wow, close call. What do you think he would have done if he'd caught you?"

"Probably not what I was fantasizing about. More likely he would have arrested me and held me until my parents came back, and by then the parents of every kid I went to school with would have heard about it. My life would have been ruined. Or, who knows, maybe he would have beaten the shit out of me? People were still pretty homophobic back then, and this was kind of a small town just outside farm country, so there was a lot of bigotry and judgemental people. Gay people were getting beaten to death for holding hands in the cities, so it was a different time."

"But what an exciting experience to have had," he pointed out.

"Oh yeah, it sure was. Once I was home safe with the doors locked, I never tested my luck like that again, but over the years I'd make plans with men to meet in similar places. Construction sites... cemeteries... hell, I lost my anal virginity a few years later bent over a tombstone in that same small town."

"Really?!?"

"Yeah. I'd been going there at night on my bike and taking walks, mostly because it had so many entrances and foot paths to escape from. I answered an ad in the paper under 'alternative lifestyles' in the personals section, and began seeing a man from time to time. I told him about my fantasies and he agreed to try."

"And... how was it?"

"Awful," I replied, shaking my head as I remembered. "I hated every second of it, but I also realized that if a few details had have been different, it might have been the best sex of my life."

"Were you still a virgin with girls by that point?"

"No, I'd been with a few. I was kind of a fuck-boy, a permanent hard-on looking for a vagina to stick it in. But underneath all that, this other thing was still calling out to me. Plus, I was terrible at picking up women, but could already tell that I could easily pick up a man once he got a look at me in a tight pair of jeans, so even though I still considered myself straight I was dating five times as many men as I was women."

"How about now," he asked, "still consider yourself straight?"

Nodding in appreciation of his insight, I answered, "Honestly? Yes. I still prefer women, but women are so damned complicated and difficult sometimes. Plus, I had a couple of long term relationships and I'd gone through periods where I was having sex a few times a day, and somewhere along the line I'd always want to introduce the idea of my wearing her panties, or her using her dildo on me, and that would be the end of it."

"They weren't into it, huh?"

"A couple of them tried it, but they were never really into it and they didn't see me the same way after that. It was a real relationship killer. Meanwhile, I was going to parks where men went to cruise, and giving out blowjobs to total strangers. It was fun for a while, but it was so empty and meaningless that I eventually gave it up. Plus, most of those guys were just like me, they were there to give a blowjob, not to get one, and I didn't like having to let a guy blow me in exchange."

"Not your thing?"

"Nope, and it still isn't."

"Well you're in luck," he wrote. "I have absolutely no interest in putting a cock in my mouth. I'm a big believer that there are two kinds of men. Real men, like me, who get our cocks sucked, and then there's sissy faggots like you who do the sucking."

I had to read it three times before I was sure I wasn't misunderstanding the insult.

There are three insults that most self-proclaimed men would take as an invitation to physical violence... "fighting words", that obligated them to either throw down or walk away in shame.

Sissy... Faggot... and Pedophile. Call a man any of those things and you're asking for a broken jaw. Clint had just called me two of those things, and now I had to decide how to respond, and he'd gone quiet. He was waiting for it.

I struggled with my thoughts for a long time, walking to my kitchen for a tall glass of wine and returning to my laptop with it half empty before responding; "That's a pretty harsh thing to say," I wrote, immediately regretting my choice. I followed up with, "I can't tell if you meant it as an insult or not, but... " Unable to finish the thought, I sent the message as it stood.

"Oh no," he quickly replied, "don't get me wrong, I don't mean it in a negative way. Men who dress as females and let men fuck them in the mouth are sexy as hell. The amount of control and ego they're willing to sacrifice for another man's pleasure makes them extremely desirable to men like me. I mean, the fact that you get sexual pleasure from dressing like a slut and putting a man's hard cock in your mouth... Jesus I'm hard just thinking about it."

To prove this, he sent me a pic taken under the desk he was sitting at. He was wearing tight jeans and they were bulging to the point where if he had sneezed he might have busted the seams wide open. I was about to send the obligatory 'Mmmmmm' response to any such pic a man sends to me during a conversation, but Clint went on with his explanation as signalling that he needed no such reinforcement.

"As for the word faggot, I don't mean that in a derogatory way either. Only a person lacking enough brain cells to smash two of them together would put their cock into guy and call HIM a faggot. If that makes you a fag, then I'm a fag too for doing it to you. Just because I'm the top and something of a Dominant, it doesn't change what we are. I only meant that some people are the peg, and some people are the hole the peg goes into."

I chuckled to myself at the simplicity of the idea... he's a peg, I'm a hole. Two holes, actually.

"Thanks for clarifying," I answered dryly, hoping that the lack of more detail would be enough to discourage any further use of those types of words. Truthfully, once I got past the initial knee-jerk response to what could be perceived as an insult, I liked the primal aspect of his thinking.

I'm the man... you're the pair of holes I'm going to fuck. Very Tarzan/Jane, Predator/prey, or Batman/Robin.

He then surprised me with a joke, one which I'd never heard and made me smile as I read it, fully aware of what it was.

"Kay... so, Superman is flying around and he sees Wonder Woman laying naked on a beach with her legs spread wide open. She's moaning and rubbing her tits like she's horny as hell. Now, Superman has wanted to fuck her for a LONG time and he realizes that with his super speed he could fly down there, fuck her, and fly away before she even knew he was there. So, he does it. He flies down there at almost the speed of light, fucks her senseless and flies away before she can even open her eyes. 'What the FUCK just happened?' Wonder Woman cried. 'I don't know,' replied the Invisible Man, 'but my asshole is KILLING me!'"