Going Off Script

Story Info
A crossdresser invites a man to pretend to take advantage.
16k words
4.7
14.3k
18
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Author's note: This one is a period piece, and a bit "harder" than my recently published stories. Readers who are fans of "Found Out" will likely be happy.

Disclaimer: The following is a piece of fiction. Fiction (in case you don't know) means it's made up, not real, a bunch of lies. The characters in the story are all fictional too, meaning they don't exist. While non-existent, if they existed and had an age they would be over 18.

Furthermore, since the characters aren't real they can't possibly be harmed by the stuff they do or that happens to them in the story. This would not be true in reality, meaning you should not think you can do the same things safely, legally, or ethically in real life. Just because bullets bounce off Superman (he's fictional) that doesn't mean they're going to bounce off you, got it? If you believe that the things fictional characters do in a pornographic story are a valid guide to behavior in the real world, then you have much bigger psychological problems than a story could ever cause and you should stop reading this and seek medical help immediately.

Ben lay tied to his own bed wearing a corset with attached garters and thigh-high stockings and a dog collar, another man's cum in his stomach and rectum. "How on Earth did it get to this?" he wondered.

But of course he knew. It was all due to that deck of cards.

[]

Much, much earlier. Ben is in the attic of his house, trying to pick the lock on an old steamer trunk. The trunk had once been owned by Ben's grandfather but now ostensibly belongs to his Uncle Tim. Ostensibly because Tim had left it with his sister saying only, "Hey, hold on to this for me till I get back," before going off to South America to "seek his fortune" seven years ago.

Uncle Tim was never one to hold down a steady job, and his letters to the family got more infrequent over time. At this point in time no one has heard from him in over two years. The family isn't sure if Tim is alive, and in any case everyone has forgotten about the trunk except Ben, who's found it behind a bunch of other old stuff.

The trunk is the kind with its own lock, to which Uncle Tim presumably has the key. Ben meanwhile doesn't know any more about lock-picking then he could learn from watching gangster movies and reading pulp novels. He's mostly just messing around, but the lock is old and cheap and by sheer chance he gets lucky.

Ben is surprised when the lock makes a loud clunk and the lid to the trunk cracks open. He lifts it and the first thing he sees is Uncle Tim's old Army uniform, smelling strongly of mothballs. The discovery gets Ben excited as it reminds him that Tim had done his Army service in Germany in the early 1960s. Maybe he brought back something cool, like a machine gun, or at least a Nazi dagger!

Sadly the majority of the contents of the trunk are old clothes, old photos (a young Uncle Tim posing with a bunch of other guys in uniform, lifting steins of beer), and old documents. In other words, nothing interesting to Ben. But tucked away down in the bottom of the trunk is a cloth bag. Inside the cloth bag is a small metal box. Inside the metal box is a deck of playing cards. And on the playing cards are naked ladies.

Which is to say each card in the various suits has a different photo on it of a nude woman in a studio, doing something innocent like reading a book, pretending to serve a tennis ball, or holding a fishing pole next to a clearly fake tree with no water in sight. You can see the naked ladies' tits, and on quite a few you can see their hairy pubic areas. This latter aspect made the cards outrageously obscene from the standpoint of 1960s American standards, which was probably why Uncle Tim had acquired them somewhere in Europe and then hidden them away in the trunk.

As erotica the photos aren't quite as unusual when Ben finds them as they had been when his uncle bought them, but during the pre-Internet era they are pretty much the only erotica Ben has ever seen aside from copies of Playboy passed around among his pals. Naturally he immediately confiscates the cards for his own purposes.

[]

Now if the naked ladies were all there was to it, Ben wouldn't have ended up the way he did. But aside from the four suits there were also two jokers in the deck. The jokers had neither photos nor women on them. Instead they had drawings.

One drawing was of a man in a big-nosed mask (later Ben would find out it was a traditional Harlequin mask) who was otherwise naked. He had a knowing leer on his face and was standing at a little angle to the card face, the better to display both the cat-o-nine-tails whip he was holding in one hand and his grotesquely large erection (even bigger than the nose on the mask) that filled other.

The other drawing, clearly by the same artist, was also an almost-naked man but in this case his sole garment was a pair of high stiletto heels. This man was standing doubled over grabbing his ankles, with his butt toward the viewer. Like in the other drawing this man's dick was visible, though it was hanging straight down and not nearly as large as that on the other joker. A little inked star indicated his butthole, and he was looking at the viewer upside down from between his knees, a silly grin on his face.

Now, it was simply a fact that you could look at the naked ladies on the suit cards but not one of them would look back at you. Which is to say their gazes were all focused in any other possible direction than toward the camera, giving the impression that they were either pretending no one was there or else deliberately ignoring the onlooker. In either case that must mean the naked ladies didn't consider your gaze of any importance or significance whatsoever. You meant nothing to them. The only two cards where someone did look back and acknowledge you were the jokers.

Also, all the naked ladies were busily doing things that, if you ignored the fact they were naked while they did them, were completely unrelated to sex. The two jokers on the other hand very obviously (and urgently) wanted sex. And since the photos gave you the feeling that none of the ladies were interested, that left each joker with only one choice for satisfying his blatantly obvious needs. Namely, the other joker.

The other male.

[]

Growing up in a small American town in the early 1970s there were several things of which Ben was absolutely certain, and one of those was that "homosexual" was a synonym for "hopelessly depraved" as well as "disgusting" and "evil." Since Ben was none of those things, he clearly could not be a homosexual.

It didn't help that in the town where Ben lived there were no gay people (or at least none that weren't completely closeted, meaning Ben never heard about them). Also Ben liked looking at girls, and gay men didn't, did they? (Ben had never heard of a bisexual, and wouldn't until he went to college.) So again, he couldn't be gay.

So Ben dated girls, kissed girls, made out with girls. He lost his virginity with his date for the senior prom, though they split up after he went away to college. Where he continued to pursue girls.

Ben sometimes thought about sex with men. Or to be more accurate, he fantasized about it. In his fantasies he was always the submissive partner, possibly because somewhere along the way he began to identify more with the bent-over joker rather than the whip-and-dick joker. Maybe it was because whip-and-dick too obviously had to be one of those aggressive, deviant seducers of unwary males that homosexuals were rumored to be. Meanwhile the other joker was probably just his innocent victim, which somehow seemed less shameful and damning.

Whether this was the explanation or not, it was definitely the case that when Ben fantasized about another male he was always the passive partner, never the active one. In these fantasies he would be forced to submit sexually to another man, and the coercion was a vital part of the excitement. For one thing it neatly dodged his socially-conditioned aversion to being considered queer. After all, if he were to be forced to do things like suck cock or take it in the ass, he wouldn't have to admit he wanted to do them.

College was also the first time he ever put on women's clothing, in this case a pair of his current girlfriend's panties while she wasn't around. He was surprised at how much the simple act excited him. After that he couldn't seem to stop stealing panties (from girlfriends, their roommates, the coin-op washing machines) and wearing them in secret, to help with his submissive fantasies.

But everyone knows that fantasy is one thing, reality something totally different. Ben didn't even consider trying to have sex with another man. When he was in college alternative lifestyles were more openly talked about than in his hometown, but even in this bigger and somewhat less conservative town the gays kept a very low profile (out of self-defense, as being homophobic was still considered acceptable if perhaps gauché in this era). Ben had no idea how to approach another male and was scared to try. Instead he kept on dating girls, and if he had any complaints about heterosexuality at the time then the only one he'd admit to was that there was never enough of the "sexual" part of it for his liking.

After college Ben got a job and moved to a bigger city, but by this time it felt like it was too late to change the patterns he'd ended up in. He dated women, less often than in college because there were fewer opportunities for him to meet women who wanted to date him. The Eighties were in full swing, the disco scene and the casual hookups he used to find at those clubs long gone. As for newer music scenes, Ben didn't enjoy New Wave and girls who were into punk just plain scared him.

So Ben ended up with a good job, hobbies, some friends from work though he didn't hang out with them all that much, and his own condo (one with its own garage and front walkway, what they were calling a townhouse). Despite this he was masturbating about as much as he had when he was a lonely teenager. He hadn't had a date that ended in having sex for almost two years.

[]

Ben's grandma had always told him that an idle mind is the Devil's workshop, and Ben suspected there was some truth to that. Certainly now that he had free time, his own place, disposable income, and a lot of backed-up cum, he got more deeply involved in some old habits. Namely the ones involving wearing women's clothing while fantasizing about being made to submit to another man.

Living in a "real"city in the 1980s meant Ben finally had unfettered access to adult book stores, which despite the name contained a far wider variety of merchandise than just books and magazines. In particular they stocked both "naughty" lingerie and what at the time were still often called "marital aids," things like dildos and vibrators. It took Ben a couple years, mostly because he was far too embarrassed about it to buy more than a few items at a time, but eventually he collected a whole suitcase full of kinky stuff to enhance his masturbatory sessions. Negligees, crotchless panties, garter belts, dildos, butt-plugs, handcuffs, gags, a riding crop (this proved to be a mistake, Ben discovered it's very difficult to whip your own butt with a crop), and so on. All for use by him on himself.

(At this point it's worth mentioning that Ben was never interested in having a woman dominate him. You might think this would be a solution to his quandary about wanting to be forced into submissive sex while not wanting to think of himself as queer, but for one thing he didn't encounter the very idea of Femdom until late, and for another his ideal of a dominant partner had been set years ago by the whip-and-dick joker. So even when he became aware that this option was available it didn't appeal to him.)

As Ben's collection of kinky items grew, his fantasies became ever more involved and complex. It was still basically the same notion of forced sex with another male, but now his dress-up play got more involved and more firmly linked to the submissive part. He would make up scenarios to play out in which he dressed up in female lingerie only to be caught doing so by some man (a neighbor, the meter-reader, a fireman responding to a false alarm) and as a result end up forcibly used to satisfy his discoverer's rampant lust. In other words, he was now acting out fantasies about him acting out fantasies which then became reality.

Ben found this sort of roleplay would temporarily satisfy his needs, but it kept becoming increasingly elaborate as time went on. It was no longer enough to merely put on panties or pantyhose, he started wearing more complete female outfits. To go along with the clothing and make him look even more feminine he started using cosmetics. He did this in a very small way at first (a little hastily-applied lipstick), but once he found out how painless it was to purchase both makeup and glamour magazines (for tips on how to apply it) at the drugstore, where everyone assumed they were for his wife or girlfriend, he rapidly got more thorough and skillful doing his face. He practiced speaking in a femme voice and acting in what he thought of as a "girly" way too, to complete the illusion.

Ben convinced himself that appearing to be female made his fantasies less and not more homosexual. After all, if he was attracting a straight male and they forced him into doing things with them because they initially thought he was female, that wasn't gay sex, right? (Ben knew that on some level this didn't make any sense, but was able to ignore it.)

Over time playing out his fantasies in this way made them seem more important, more urgent. It was no longer a matter of bringing out his toys and women's clothing once in a while for some fun, he was doing it at least once a week. He also felt horny almost all the time and started daydreaming about the fantasies during other activities, even while at work. It got to the point where he couldn't seem to masturbate enough to relieve the desire he felt.

Ben knew he was missing something in his life, and that this something seemed to be man-shaped. He had finally come to the realization that maybe what he really needed was to get together with a male who could satisfy his specific desires. Even if it did seem kind of "homo" and he (as Ben was still convinced) wasn't.

But as mentioned earlier, this was during the 1980s. Ben had heard the horror stories about the mysterious disease called AIDS, which pretty much took any notion he'd had about finally visiting a gay bar and carpet-bombed it into a huge smoking crater.

But there was a special wrinkle to this, or so Ben thought. At the time the things he heard about AIDS made it seem to be a disease peculiar only to certain groups; Haitians, hemophiliacs, heroin users, and his own concern, homosexuals. Thinking about this, Ben came up with the concept (which he believed, anyway) that the solution to his problem would be to find a non-homosexual male who would dominate and have sex with him.

Ben "solving" his AIDS dilemma in this way had a major effect on him. For some reason it took the matter out of the realm of fantasy, "it would be nice if," and "well, maybe some day," and moved it into the section of his brain headed "I need to plan this carefully, then I can do it." The many other problems and issues and dangers involved in actually carrying out his fantasy in real life, which had previously always prevented him from seriously considering doing anything about it, got quietly shuffled into a dark corner of his mind and conveniently forgotten.

In short, Ben was now convinced he was going to do this thing.

[]

Long before you "swiped right," even before Craigslist and other Internet pickup methods, there was a way to arrange a hookup with someone you had limited information about before you met them in person. Any fair-sized city had at least one and often several "adult" tabloid newspapers, usually given away free from vending machines. What you did was pick out a pseudonym and pay the newspaper to run a classified ad about what you were looking for. People who thought your ad sounded interesting then wrote to the paper, who would forward you the letter. Then you could answer them in the same way by writing back to them and so forth and so on, exchanging whatever information you wanted (including photos) until you finally agreed to set up an actual meeting somewhere. It sounds awfully cumbersome now, but back then it was your best hope of remaining anonymous while trying to find someone who matched your kink.

Ben put an ad in a tabloid of this sort, calling himself "Betty" (without specifying gender) who was into light bondage, anal, and oral, and looking for a "clean" man between the age of 21 to 30 (Ben was thirty-one at the time himself), please include photo in reply. The ad got him a large number of responses, most of which were easy for him to reject out of hand.

The approximately two dozen he had left got a letter back in which "Betty" admitted "she" was a passable crossdresser (Ben had only his own opinion on the "passable" part but was pretty confident it was true), including in each a Polaroid of his face with cosmetics on and asking if they were still interested. This weeded out many of the remaining respondents, but there were still a half-dozen left. Of these the one who really caught Ben's eye was Rocky.

The photo alone Rocky sent made him the cream of the crop. Clean-shaven, muscular but not overly so, a little sneer that looked oh so sexy. Rocky said he was straight but not turned off by the fact Ben was a crossdresser. Nor was he unwilling to accommodate Ben's instructions about how their encounter should go.

Which brings us to the Script. Once Ben decided he wanted to realize his fantasy, he started writing down things he wanted to happen (for instance light bondage, maybe a little manhandling) and also the things he didn't want (any real pain). Ben spent a lot of effort on this while waiting for responses to his ad, and it got quite detailed and specific. So much so that after he mailed the single-spaced several page document it to Rocky, Rocky's response letter referred to it as "the Script" and the name stuck.

Some parts of "the Script" were:

Rocky had to come over freshly showered (he'd let slip that he worked in an auto repair shop, which sounded wonderfully masculine but also kind of dirty, and not in a sexual sense).

He was to "discover" Betty dressed up and "capture" him, but there was to be nothing too rough. Definitely no hits to the face.

He could call Betty "slut," "bitch,""whore," "cunt," or other degrading terms so long as they were feminine, in fact Ben wanted him to use such words. "Faggot," "sissy," "queer" and so on however were out.

Betty's clothes were not to be torn, ripped or otherwise damaged (lingerie can be so expensive!).

Betty wanted his ass to be spanked, but there was to be no use of anything other than hands in the process. No spatulas, whips, etc.

If Betty used the word "infinite" they would take a break. If Betty said "synonym" the date was over.

Betty would suck cock and take it up the ass, but only in that order. Rocky was not to put his dick back in the mouth after it had been in the butt.

Definitely no deep throat, and no fisting.

Rocky could come in Betty's mouth or on her face if he liked, but Betty wanted a load in the ass at some point.

And so on and so forth. It turned into quite a list, the Script.

But as mentioned, Rocky seemed to be okay with it. In fact in the last letter he sent he joked that if he forgot a step, "Betty" should please remind him.

[]

Having done his best to determine that Rocky was a good choice, Ben wrote him setting up a "date" for the Friday after next at Ben's townhouse.