tagTransgender & CrossdressersCraigslist Encounters Ch. 01: Craigslist Cumslut

Craigslist Encounters Ch. 01: Craigslist Cumslut


The following story includes transgender characters, Domination/submission, and denigrating terms used to humiliate. If this offends you please do not read any further.

Feedback on my stories is always appreciated. There maybe additional chapters to this story depending on how this is one is received. If you would like to see a second chapter let me know by leaving comments, rating this story, and/or sending me a message.


Jake stared at the screen on his phone. He had opened up a page on its browser to an ad he found on Craigslist. It said,

Looking for my own personal cum slut - t4m

I am a slim Dominant Asian ladyboy looking for an extremely submissive bitch to use on a regular basis. I am cute, feminine, 25, 5'4" tall, have small breasts, tight abs, a small firm ass, and a 4" long uncut cock when it is soft. The right slut will find out how big it is when it gets hard.

You should be in decent shape, but I don't necessarily need you to have a perfect hard body. What I really need is for you to submit to what I say, when I say it. I find any disobedience a turn off.

You should be able to cum multiple times and be prepared to swallow as all good faggots do. You will submit to my big cock for hours at a time.

I am drug and disease free and you must be also, as you will be getting fucked bareback up the ass on a regular basis.

Convince me to meet you by honestly telling me why I should let you worship me in your reply to this ad. Include a picture of yourself naked.

Below the text was a picture of a thin body from the neck down to just above the knees wearing only what looked like an A cup size white bra. There was no fat on the perfectly tanned torso. There was almost a hint of a six pack in the abs. As Jake's eyes continued down the body he came to a small but thick patch of black hair above the junction of the legs. Protruding out of this hair was a very thick uncut cock which arced smoothly down between a pair of slim perfectly toned legs.

At twenty-two years old Jake had been with a few women in his time. None of the relationships, however, lasted more than a few weeks at the most. Which meant there was a great deal of time when he had nobody to sleep with.

Although very few people talk about it in polite company, outside of computers, the business sector that probably benefited the most from the Internet is the Porn industry. Transforming itself from dirty magazines and VHS tapes purchased by underage boys and old "perverts," to images and videos that are easily and regularly accessed by fathers, sons, mothers, and daughters in rural, urban, and suburban homes connected to the Net around the world.

Just as millions upon millions of others do, Jake spent a lot of time jerking off to online porn when he was between girlfriends.

Over time most of the porn he watched involved bigger and bigger cocks. While ogling these hung studs fucking women, Jake liked to think of himself as a grower not a shower. That was mostly fooling himself, although there was some truth to this description. When flaccid his cock was only two inches long. As for growing, when hard it was thin and almost five inches. That does qualify as growing, but not anything like the thick eight inch, nine inch, or bigger monster cocks he found himself spellbound by during his stroke sessions.

Eventually in the last two or three weeks he had started admitting the truth to himself. That he was not cumming from watching the tits and pussies, but from watching the cocks. Questions had started to occur to him. What would a cock feel like in his mouth? In his ass? What did cum taste like? Was he gay? He didn't know. But if he was, he would also have to accept another truth - he was a size queen.

This probably helped explain why none of Jake's relationships had lasted. How long could a woman put up with a guy who deep down wanted to swallow a megacock rather than fuck her. Even if he didn't yet realize it. Maybe especially if he didn't yet realize it.

In the relationship that he had enjoyed the most and which had lasted the longest, his girlfriend Bella was a strong, unbelievably sexy women. She had a Spanish pedigree which showed in her deep olive skin, her black tresses which she liked to keep in a long braid down her back, and her hour glass figure which included large thirty eight inch DD soft breasts, wide thirty six inch Latina hips, and a soft plump booty.

Outside of the bed she tended to make the decisions about where they would go and what they would do. In the bed the first couple of times they had sex Jake had cum quickly, but it wasn't earth shattering for him by any means. Bella had moaned a lot as he fucked her hairy cunt. Sometimes riding him, sometimes on her back with her thick legs spread wide apart. She never came while he fucked her so she would masturbate after Jake quickly blew his load.

Although Bella enjoyed spending time with Jake, sexually she didn't think his little cock would ever get her off. When they would walk together at the mall, however, she did take pleasure in the way he would squeeze her big J-Lo booty. She could tell he was obsessed with her ass.

So the next time they were in bed with her voluptuous tear drop shaped tits in his mouth, she pushed him on his back, firmly sat on his face and demanded, "Eat my fucking ass." Pulling each of the big globes in front of his face apart, and only hesitating for a second, Jake pushed his tongue forward seeking out her hole. Even though his face was covered with her ass, he immediately knew when he reached it. His tongue found the smooth feel of her asshole incredibly sexy, circling it over and over. He had found heaven, and it was the tight pucker in between this woman's fat ass cheeks.

Jake started to reach for his cock to jerk off while he licked Bella. She wouldn't have any of it though. Slapping his hand and balls hard.

"You do that, and you'll come in five seconds and be fucking useless to me won't you? Focus on my pleasure not your little cock. Eat that hole you fucking ass licker."

He couldn't believe how much at that moment things became so clear for him. He became obsessed with doing anything she wanted. For the first time the submissive man in him was defined and released. The incredibly compliant act of licking her ass, along with her profanity laced verbal bombardment, and attacking his masculinity by referring to his cock as small made the submissive buried deep inside him feel more excited than he ever had before.

Just as this was the first time Jake had ever eaten ass, so it was also the first rimjob Bella had ever experienced. The pulses shooting through her from his tongue were nearly orgasmic by themselves. In addition to this pleasure as she rubbed her ass harder on his face, Bella was also circling her huge clit with her hand through her thick dark bush. Her body was on the verge of a massive orgasm.

She then dropped her pussy where her ass had been, her engorged lips spread open like petals from a flower dripping with dew. Jake's passion continued, now licking her cunt. He lapped up her nectar as it streamed out of her when his tongue tracked up and down her pussy lips. He eventually started focusing exclusively on her clit. It was standing straight out having escaped the protection of its hood and was almost as big as the tip of her little finger. He started sucking on it and Bella lost all control. Juice squirted all over his face like a shower.

When things finally subsided Bella rolled out of bed, walked to the foot of it, and sat in a chair facing Jake. She placed her feet up on the bed, her legs spread wide apart. Panting to get her breath, her face dripping with sweat, her tits rising and falling with each large breath she took, her bush her cunt and her legs literally dripping wet; at that moment she was sex personified.

Looking at Jake through barely opened eyes she said, "Jerk off. I want to see that little cock squirt."

He was basically already only seconds away from cumming. Within three strokes he was shooting cum over his head and onto the pillow. They both started laughing once it was over.

It had been the best sex either of them had ever had, even though Jake's cock had never touched her pussy, and never would again. There were a few more sessions like it which they both enjoyed. In the end, however, Bella was still a strong sensual straight woman and she wanted cock. In fact she wanted big cock. As it turned out so did Jake. He just hadn't yet faced that fact. So like all Jake's other relationships it eventually came to an end.

Once Jake was willing to tell himself that what he really wanted was cock, he had to find a way to get it. He certainly wasn't prepared to come out and tell people yet. Hell he wasn't sure he was prepared to actually do anything about it.

He started looking for a place where he could take his time if he wanted to pursue his increasing fixation on big cocks. That left out a gay bar. In the bar scene people don't take time to consider their decision. They act on impulse and instinct. Plus nobody really knows someone else is hung until it is all on display. And Jake wanted his first cock to be BIG.

So he went to the same place where his obsession started. The same place so many go these days when looking for love. The Internet. He thought of a dating site but he figured that was more for people looking for a relationship. At this point he was looking for lust, not for love. Then a want ad occurred to him. And off to the personals on Craigslist it was.

Realizing that his cock was hard from staring at the picture in this ad, it occurred to Jake this may be the perfect sex partner for him. He absolutely loved looking at beautiful women. He also loved the power which a strong woman exudes when he was in her presence. Just the opposite of what society indoctrinates people to believe is the natural order of things. His growing cock obsession didn't change any of his lust for a strong beautiful women. The "woman," in this ad offered him the opportunity of potentially more complete satisfaction than he had ever yet experienced. He decided he was going to reply.

After having once again reviewed the ad he opened up his email and wrote,

Re: Can I be your cocksucker


My name is Jake. I read your ad and needed to respond. I will be up front with you. Not only have I never responded to an ad like this before, I have never had any experience with cock before. I have only recently come to realize that I want to be a cocksucker. Reading your ad and seeing your picture just now made me realize it's more than that. I want to suck ladyboy cock. REALLY BIG ladyboy cock.

I tend to let the women I know take charge. So I welcome you making me your bitch. I love to give rimjobs and hope you will let me stick my tongue up your ass.

I have never tasted cum but I want to and will drink every drop you tell me to.

I have also never had anything in my ass. I was thinking of buying a dildo but I want the first time I am fucked to be with a real cock. I love huge cocks and want to give my ass up to your impressive piece of meat.

I have attached a picture. I am 22 years old, white, 6 feet tall, 200 lbs. As you can see in the picture I am a grower. Soft, like I am in the picture, my cock is 3 inches long. When hard I am 5 inches.

Please let me know if I can be your bitch.


He attached a selfie he took standing naked in front of the mirror. With his short cut dirty blonde hair, a reasonably fit hairless chest, and a two inch cut cock barely long enough to hang as low as his tight balls

After writing the email Jake hit send and waited. He immediately felt nervous about having done it. He wasn't sure if he wanted a response or not. He felt scared, and he felt anticipation, that he might finally get to suck cock. About an hour later his phone beeped informing him that he had received an email.

Re: You would have made me a such good slut


I loved reading your email. When I placed the ad it never occurred to me that I would be interested in a reply from a cock virgin. At first I didn't think a virgin would make a good match to be my slut, but I was impressed by how much of a cock whore you appear to be. And a completely virgin ass is every hung tranny Mistress' dream. That is why I am so disappointed to have to tell you that I won't be able to make you my cocksucking bottom faggot.

As I said in the ad, disobedience is a major turn off for me. I told you to be honest in your response and I can see that you lied to me. You say in your email that your cock is 3" long. Yet I can see in the picture that your pathetic excuse for a cock isn't that big.

If you are already lying to me about this, what else are you lying to me about. Too bad as I could have turned you into, and used you as such a good bitch.


Immediately Jake slammed his palm into his head saying, "You fucking idiot!" How could he be so stupid.

Now there was no doubt in his mind, he did want a reply. Just not this one. How could he fix this? Whatever he did would have to be fast before she found herself another guy.

He had to reply to her. What did he have to lose. All she could do was say no again. Hitting the reply button he started typing.

Re: I am sorry Mistress

Mistress Candy

I am sorry for what I said in the email. I did lie, but not with intent to deceive you. Rather because I was embarrassed at how small my dick is. Especially when I compare it to your big beautiful cock. Hard I am probably only a little longer than you are soft, and not as thick.

My little cock is only 2 inches long. I am less than 5 inches when I get as hard as possible. As I am right now from looking at your sexy body.

This is the only thing I wrote that is not true. I do want to be your cocksucker. I am a complete ass whore and would eat your ass for hours at a time. I will willingly give you my virgin faggot ass to fuck as hard and as long as you want.

Please don't hold my embarrassment about the fact I am a little bitch stop me from being your submissive slut.

Your personal whore,


Attached to the email he sent two pictures of a measuring tape next to his cock. One when it was soft (two inches exactly) and one when it was hard (four and seven eighths).

He shaved all his pubic hair all the time. Using the traditional logic that it would make his cock look bigger. But when your cock was as small as Jake's, all it does is bring attention to just how, as Candy had said, "pathetic" his little cock was.

A second after he had pushed send, on the other side of town in a house at the end of a cul de sac in a quiet neighborhood, a phone beeped.

A sweet looking small Asian woman picked it up. She had slightly longer than shoulder length black hair framing her pretty face. She had a small mouth below an adorable nose, and dark eyes enhanced by misty grey eyeshadow. If you looked closely, the left eye would open slightly less than the right. Perfection is boring and this trait actually enhanced her looks.

Candy smiled as she read Jake's response. She had always planned on meeting him. Her reply had just been the first step in her dominance by making him beg for her cock. The next step was to make him so appreciative that if there was any resistance left it would all fade away.

Re: I will give you a chance faggot

Alright my bitch I will give you ONE chance to prove your words with your body. You will be at Strumpet Road at 7 pm Saturday night. I guarantee a night you will always remember.

Until then you can't touch your cock.

Mistress Candy

Jake was instantly hard upon reading the email. With so much anticipation how was he going to keep from touching his cock for two days? Yet after she had found out about his lying to her as to the size of his cock, there was no way he was going to disobey her about this or anything else - ever.

On Saturday he left an hour earlier than his phone's map app told him it would take to get to Candy's house. But he wanted to make sure he found it on time and that he didn't get caught in traffic. He arrived at the house about seventy minutes earlier than he was supposed to be there. So he drove over to a coffee shop while he waited.

This hour long wait was the first time it really hit him what was going on. He was going over to a stranger's house to suck a cock and get ass fucked by a person who looked like a woman. Put in those harsh terms it sounded like a horrible idea. But then he thought about how much he wanted to suck cock. How sexy the "woman" was. How Dominant she was. This wasn't strange it was exactly what he wanted. He was determined this would be the last doubt he would have, at least until this night with Candy finished.

Dressed in jeans and a T-shirt he walked up the driveway and knocked on the door. Candy opened it, with Jake towering over her petite body. Until now he hadn't appreciated from the picture just how tiny Candy was.

She was dressed in scarlet red stockings and a garter belt along with a matching tight thong, and small A cup bra. The panties barely hid anything. Her balls spilled out both sides of the crotch. Above this the underwear bulged out and down between her legs. She was in no way trying to hide anything. In fact the lingerie actually accentuated her cock by failing to cover her balls and by displaying her swollen panties. This wasn't a mistake. Candy could have tucked things away better. It was a physical display of her supremacy over him and his little cock. She wanted him to know right from the start how hung she was and that she was in command.

Candy and Jake's former lover Bella were opposite sides of the same coin. Where Bella had a full figured soft body, Candy had a lithe hard body. Bella was five foot nine. Candy was five foot four. Bella had large DD breasts. Candy had small A cup tits. Bella had a soft plump booty. Candy had firm trim ass. And of course Bella had a juicy tight pussy and Candy had a large thick cock. Despite such obvious differences, the common thing about both of these powerful women was an intense lust by Jake for both of their bodies.

Anyone would have described her as cute. But she had a smirk on her face as she watched him become entranced while looking between her legs. This gave her a mischievous and ever so slightly evil look to her.

"Take your cloths off and leave them on the chair there. You won't need them until you leave."

He stripped quickly and revealed his hard-on to her when he removed his briefs. She lightly ran her fingers across his hairless chest while telling him, "I like it." Then she reached down and squeezed his cock and balls. "It really is small isn't it? Jerk off!"

While continuing to stare at her, Jake grabbed his cock and slowly moved his hand up and down. Candy reached behind her back and her bra fell to the floor. She had small breasts with noticeably large warm ochre colored areolas, capped by hard eraser shaped nipples. They were so sexy on her tiny frame. Seeing them Jake started sliding his hand faster up and down his cock. It didn't get any bigger, but it did get harder.

Next she turned her back to him. Most people don't ever notice other people's backs. But for Jake a firm toned back is like a work of art. And Candy's flawless light caramel colored skin stretching tight across her back was like experiencing the Venus de Milo come to life.

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