The BBC that Broke Me Ch. 01

This is a story I originally wrote and posted on another platform. Figured I'd share it here too!

I've written a few fictional stories (posted on Literotica, shameless plug) based on some of my sissy experiences, but this is the first true story I've ever written.

Truth be told, I'm kind of nervous about having this on the internet for random strangers because I'm very discrete with this side of my life and would very much like to keep it that way. For that reason, I'm going to keep some information vague.

I have told this story, privately, to a few people I've met online that are into the kink and was always super turned on writing it out. Something about having an internet stranger know about how I got dominated by another man really turns me on. I love the humiliation of letting others in on my slutty secret. I also really get turned on by emasculation, humiliation, degradation, and feminization so I think the daddy and sissy bedroom dynamic drew me in pretty naturally. I know it's not everyone's cup of tea, and I respect that, but for me it really gets my clitty in the bedroom (and only in the bedroom really).

With that being said, this is going to be a long story because I love to write. But once y'all get done reading it, I'd love to hear your comments on what you think of me and my experience.

I was already a couple of years into enjoying the sissy kink when this happened. It was way back when Craigslist was still a thing. One night, I had family from out of the country in, but they were really there for members of my family that they hadn't seen in years since I was just a toddler the last time they saw me. We didn't have any real relationship or connection and to be honest, I was pretty bored. Eventually, I found myself on my phone browsing the Transgender & Crossdressers section of my favourite dirty story site, Literotica. This, in hindsight, was a bad idea (some would say it was a good idea) because after reading for a bit, I got really horny. This lead me to search out something kinkier. Something dirtier.

At the time for me, that meant browsing Craigslist posts in my area. The things people would post on the site just felt more real than the stories people would write on Literotica. These were real people posting ads online. It sort of validated my own kinks knowing that others were searching for something similar.

Well, anyone who's had the pleasure of using Craigslist personals knows how this went. I found a handful of interesting ads and replied using my burner email. Full disclosure, my original intention was not to meet, but to find someone that I could possibly have a naughty chat with. I had to rule out a few right off the bat because all they knew were "wanna fuck?" or dick pic and those types of interactions did nothing for me based on what I was looking for. Eventually though, I did find myself having a couple of back and forth exchanges with two different gents.

One was about 20 minutes away from me and the other was in a nearby suburb just outside the city. One was 27 years old to my 21 and the other was 44. Age didn't really matter to me because as I said, I had no intention of meeting originally. The older gent was the one closer to me so I responded a bit quicker to him. The idea that we could possibly cross paths at random going about our regular day-to-day lives without even knowing it was a turn on. He lived alone and was feeling particularly horny that night because his girlfriend was away for the weekend. Oh yeah, this all happened on a Friday night, Saturday morning. He had a typical dad bod and was really hairy (not my thing really). I did my best to keep him interested with the prospect of having me but eventually he caught on to my game and stopped replying.

Thankfully, I still had the 27 year old to chat with. By this point, I was restlessly horny and was really trying to strike up a convo that could help me get myself off. This wasn't helped by the fact that my family was just one floor below me and they were getting really rowdy reminiscing on past stories. So, I hit up the younger guy and asked him what we'd get up to if I came over. I love reading what daddies want to do to me and was really hoping he was articulate. It didn't get off to a good start because he sent a dick pic *rolls eyes. Uhh, why do tops think this is a good way to start a convo? To be fair though, it was a gorgeous looking cock and it was the first pic of a black cock I was ever sent personally.

It's a good thing he followed up with "you'd be learning to take this" which was something that I could work with. I told him that he'd definitely have to teach me because I was a virgin and have never had anything other than my butt plug inside of me. This seemed to pique his interest. He told me about how he loved being the one to pop a boy's cherry and that he's only had the pleasure one other time. He told me about how he had met this twink at church and they really hit it off. He said his family did not approve when they saw the two of them being overtly friendly because of their religion, obviously, but he didn't care. He was determined to have that ass.

His sense of assertiveness was turning me on, so I asked him what he meant when he said he didn't care. He had said that for some reason he wanted to openly defy his parents and rebel against their disapproval of him taking interest in this church boy. So one night, when his parents were out for dinner, he invited the guy over and they eventually got down to it. He told me that he took charge and the guy didn't put up much resistance. He had the guy bobbing on his cock fairly quickly, but heard his parents come home shortly after. Instead of rushing to get covered up, he instead decided that it was the perfect time to introduce his cock to church boy's rosebud, and that's exactly what he did. Seeing as it was church boy's first time, he could not contain himself. He got loud with his moans of pain and pleasure. The whole house heard according to the guy telling me the story.

The whole time, I'm jerking myself furiously, but before I could climax, he stopped the story. Instead, he sent me an email with his phone number and said he'd like to take the convo to text because it was faster. I reluctantly agreed, but not before quickly setting up a number using a site called TextNow because I was way too paranoid to be giving out my actual number. I messaged him asking him to continue to the story.

He declined and said that writing it was getting him all kinds of horny again. He asked me for some pics of me instead. He said that he wanted some "motivation". Being the budding little sissy I was, I reluctantly got this hot pink thong I had out, and went to my bathroom to get a nice picture of my ass for him. I didn't know how he felt about sissies, so I wanted to make sure I set the tone by being in my thong for the pic, and personally, I thought (and still think) my ass looks great in a thong. Anyway, I snapped a few pics from different angles and sent him the one that made my ass look the best. I was desperate to hear the rest of his story.

He replied with a pic of his own. This time he was stroking himself. He said that my ass looked better than church boy's *blush and that he wanted a taste. It never even crossed my mind that guys would want to rim me before and I didn't know how I felt about that. I sent him another pic, followed by another request to hear what happened with his parents hearing him fuck church boy. He told me that when he was done destroying that ass, he walked the guy out of his house, right passed his parents who were sitting in the living room looking extra angry. When the guy was gone, he said he got into an argument with them and basically told them that nothing they say will change what he likes. Instead of hiding it, he wanted to force his family to just accept that he's bi. Over the years, he continued to bring guys over to fuck and that's how he knew he really liked anonymous hookups. He'd eventually bring both girls and guys over and his two brothers eventually just shrugged it off and no longer care about his sexuality. His parents still don't like it, but they're more annoyed by how loud he gets with his partners because he had a penchant for making them moan very loudly regardless of gender he humbly bragged.

I wasn't entirely sure when his story was going to end so in the middle of it, I had slowed my jerking to a slower pace because I was hooked and didn't want to cum and lose interest in the convo. I wanted to hear more about his hookups. Looking back on it, this is when I think he was catching on to my game. Unlike the other guy, the 44 year old, he didn't end the convo. Instead he pivoted back to his ad. He asked me where I was located and I told him that I wasn't exactly near him and had no car. I wanted to establish some excuses to help me out of the situation in case he actually tried to meet. He told me he'd come to me, but I told him about my family downstairs who were getting increasingly loud by this point. They were sort of killing my vibe. It's awkward to try and jerk off to bbc while listening to your uncle talk about the good ole days.

I then tried to pivot back to hearing more about his experiences and asked if all his experiences were strictly hookups, but all he would give me was that he had a girlfriend. He was more interesting in trying to lure me over to his place which was both frustrating and sexy at the same time. I just wanted to get off so not indulging my need for sexual conversation was annoying, but knowing that he really wanted to fuck me was so hot.

We continued to chat, but more casually for a bit before he asked me what I was hoping to get out of this convo because he was trying to get laid. I was too embarrassed and scared to just admit that I only wanted to jerk off to the chat but I was even more scared that he'd end the chat if I didn't tell him something that would keep his interest. So, I told him that I was looking to experiment and that I get turned on by the idea of having my sissy virginity forcefully taken by another man. He sent me this emoji as a response, 😏, and asked me to go on. Foolishly, I thought that I had just lured him in and taken control of the convo. I told him (and now you guys) that consensual non-consent is my favourite role play scenario to jerk off thinking about.

He asked me what that was, and I decided instead to just tell him my fantasy. I told him how I wanted to meet an alpha male type who viewed me as an inferior beta that didn't deserve to present as male in his presence. A man that demanded and forced me to dress in women's lingerie while we were together in private to symbolize my inferiority, not that women are inferior or anything, just that I find it embarrassing for a regular vanilla man to be dressed in it in front of his soon-to-be daddy. I also told him that I wanted said man to dominate me both physically and mentally. I wanted him to show me first-hand how a real man handles his business in the bedroom.

He replied by telling me that I was getting him real hard and that he really wanted me to come over. Once again, I thought that I had him. I figured I'd be able to hold his attention long enough to finally get off. Both he and my family had other ideas. My family was getting obnoxiously loud and it was becoming increasingly distracting. It was killing my boner (if you can even call it that).

He then messaged me his address. Just like that. I explained to him again that he was too far for me to travel to without a car. Public transit would be shutting down in a couple of hours and I'd have no way home and I had no plans of spending the night. His reply was coldly erotic to me. He said that he had no intention of having his booty call sleepover either. He just wanted to fuck and send me on my way as it's all I was good for. At the time, I didn't know it, but in retrospect, telling him my fantasy was probably hook, line, and sinker for him.

He told me that if I gave him an address, he'd have an Uber sent to pick me up.

My heart was racing after reading it. I was still hesitant and wanted time to think it over. I was telling myself this was crazy. Remember, I started the night having no intention of meeting. I had no experience with men before. All I owned were a few pairs of thongs and g-strings, a single butt plug, and the closest thing I had to stockings were a pair of knee high socks I wore for soccer.

The excuse I gave him was that I wasn't passable. This is a serious point of conflict for me. I actually like living my day-to-day life as a man. I don't have an excessive amount of hair on my body, but I also don't really want to shave it. What I do now is shave just enough so that I can cover the hair on my legs with a nice pair of thigh highs and wear a top to cover my pits. But at the time, I didn't have these items in my wardrobe. I don't have hair anywhere else on my body, but I told him this thinking it was going to back him off.

Throughout this mini panic attack, I didn't even notice I was still hard. I had even stopped jerking myself off to fully concentrate on getting him to back down. At the same time though, I felt a little bit guilty of leading him on. It was strange, I didn't feel this way about all the other guys I did this to in the past, but none of them actually got this far.

He reminded me that he had fucked plenty of non-sissy guys too and that how passable I was wasn't a factor. Uh oh. What now?

I told him that it was a factor for me. I said I wanted a man who would be able to put me in the role of the sissy and that being dressed played a big part in getting me in the right mindset. I told him that at the bare minimum I wanted my lower half to present as sissy. That meant stockings and possibly heels to go along with my panties. I honestly thought that this would be enough to back him down. I even insisted I wasn't meeting unless I could find the perfect scenario to live out my fantasy and that I really wanted my first time to be my fantasy instead of just a hookup. I thought that being demanding and overly needy was going to make him think I was asking for too much.

Apparently, it had the opposite effect.

He told me that my fantasy was incredibly sexy and that he had the means to set it up. All I had to do was send him an address to get picked up.

I did my best to ignore this request. Instead I scrolled up our conversation and tried to finish my jerk off session by re-reading his story with church boy, but I just couldn't bring myself to climax. I don't know if it was the volume of my family or that the story just wasn't novel anymore or a combination of both. Or maybe deep down, I secretly really wanted to have that dick inside me.

I made one last ditch effort to back him down and told him that I'm not into oral. I said I would not suck dick because at this point in time, I just couldn't bring myself to put another man in my mouth and look up at him as I bring him pleasure (although this is actually such a humiliating act in and of itself that it really turns me on).

This man was determined. He said my ass would suffice for the night. He just didn't want to jerk off. Unlike me, he had a strong need to fuck something.

He had me. I'll never be able to explain it, but I sent him my location. I didn't send my address, but instead the closest busy intersection where he could send the Uber. I pulled my thong up, covered up with a hoodie and sweats, and ran out of the house telling my family I was going to help a friend with something. I was out the door before they could ask any other questions. Once I was out of the house, I walked as quickly as I could to the intersection. It was now or never I told myself.

All I needed to do was get in the car and everything else would be out of my hands. I told myself that I wasn't exactly flush with cash so I wasn't willing to shell out whatever it cost to have an Uber take me back from this suburb to my place anyway. So as soon as I was in the car, I'd have to go through with this for him to get me my ride home. On top of that, I didn't realize just how far the suburb was. The ride was about an hour and a half, although it was a shared ride. There was only one other stop on the way, so it's not like it added much time to the ride.

When the car arrived, that's when I knew I was such a rookie. The driver rolled down the window and said "are you Jordan?" I was so confused like who the fuck is Jordan? Then I realized that Jordan was his name. I never even got his name over the last hour or so that we chatted. What was I getting myself into?

I hopped into the ride after confirming I was Jordan, not wanting to tell them the real situation lol. So there I was. In the backseat of this guy's car, on my way to my first ever hookup. There were two girls in the backseat with me who were together and asked me where I was headed. Another dumb mistake by me. I didn't even know where I was going. Not safe in hindsight.

I just told them that I was on my way to chill with some buddies. They bought it and left me alone the rest of the ride, but it did turn me on sitting there with the thong in my crack. I wondered if they also had thongs on, but to stop myself from getting an erection in the car, I pulled open my phone and sent a message to Jordan to try and distract myself. I made sure not to send him anything sexual and try and keep the convo as bland as possible to keep myself from getting horny. Sweats aren't the best in hiding things in my pants, another rookie mistake. I now know better and either wear pants that do a better job of hiding it or I just put on my cute little cage.

I told him that I was in the car and on my way. All he said was good and to send him a message when I was outside. After what felt like the longest car ride ever, I was finally there.

I got out of the car and sent him a message as I stood on the sidewalk. Still unsure of which house was his because I didn't bother to get his address beforehand like a dummy. It would be another minute or two before I saw a door open and a 6 foot 5 black man walked out onto a porch. He beckoned me over and introduced himself as Jordan. This was so awkward. I was so meek. I just sort of hung my head and said hey. He shook my hand for christ's sake, like "hello, nice to meet you, are you ready to get this black dick?" He didn't actually say that but that's what I imagined to myself. In reality, he lead me to the side of his house and into his backyard, told me to pull up a seat and relax for a bit. He then pulled out a joint and said he liked to smoke before a fuck. He offered me a puff, but I turned him down. By this point, I realized how many stupid and unsafe mistakes I had made and wanted to make sure I was sober to prevent any additional ones from happening.

As he smoked, I made sure to ask him if he had condoms and lube. That was one mistake I was not going to make. I told him that it was non-negotiable for me that we play safe and he agreed. He said he had a girlfriend and it wouldn't be right to put her at risk like that. This lead to us just chatting about his views on cheating and relationships in general. It was odd. He said he told his girlfriend that he really enjoyed anonymous hookups and wouldn't be willing to give it up just yet even if they dated and put a label on their relationship. At first, he said she was reluctant and they had some on and off issues about it, but like his parents, she eventually learned to live with it. I found that strange, but he smirked at me and told me it's because she loved his dick too much to give it up. I distinctly remember him holding the joint to the side of his mouth to inhale with one hand and had his other grab at his crotch when he said this. This lead my eyes down to his shorts. Even if the light on his back patio wasn't on, I'm sure I would've been able to see the outline of his cock.