We'd met on Craigslist in the Casual Encounters section. I can’t even remember what I was advertising for. Probably some form of sexual fantasy fulfillment/role play. He was one of many guys who responded to my ad and at the time we couldn't really decide on a time and place that would work for both of us, so I'd met up with someone else that particular weekend. I'd been intrigued by the tone of the emails he'd sent me and I’d liked his photos. One of them was him in the nude, sitting with his arm resting in a way that partially blocked the view of his cock. From what was visible of it, it looked very large and thick, a true BBC. I could only wonder if I would be able to take it all. I saved his emails and photos in the hopes that we would find the time to meet in the future. In fact, in the email I'd sent him telling him that we couldn't meet at that time, but could possibly meet later, I'd given him my cell phone number as a gesture of good faith. That's not something that I typically do and it would turn out that I wouldn't regret it, either.
Some months later, I was at work when I got his first text message. He simply asked if I was available and when we could meet. Again, I wasn't available and I texted back to him saying so. He messaged back saying that he really liked my photos and that he's looking forward to finally meeting me and then followed that with "I'ma tear that ass up." Wow! That got my attention. I completely stopped what I was doing and read his message a few times, taking it in and realizing how incredibly turned on I suddenly was. I texted him back "Wow! I like the sound of that." Moments later he responded. "Yeah, every time I look at your pics, that's how it makes me feel and I know I can fuck you good and make you my private bitch on the side." followed shortly by "completely bitch you out". My mind was blown. He was pressing my buttons in exactly the right way. I was at work, I'd been doing my job and in a few short sentences sent via text, he'd totally taken me someplace else psychologically. I felt like a femme slut, his bitch, and what's more, I totally loved it. My cock was as hard as a rock and I found myself wishing I was dressed up in drag and at his sexual service right at that moment. The unfortunate reality was that I couldn't do that and wouldn't be available to meet him anytime soon. I texted him back saying as much and he replied "Alright, Ho... get back to me... get them panties and that asshole ready... I want you wearin' white panties and be a straight up bitch..." followed by "I want you swishin' that ass hard and teasin' me to tear that bitch ass up... shake that ass like a bitch." then he finished with "Have them heels clompin' when you walk." My sexually piqued mind was racing and I couldn’t think of anything else but sucking his big black cock, bending over for him and feeling his thickness stretching my ass as he made me his bitch. Throughout the rest of the day, my mind drifted over and over again to fantasies of sexual submission to him and what it might be like to have him verbally humiliating me in person as he used me for his sexual gratification. He had made me so horny that I had to masturbate on my break.
It wasn't until a couple of months later that I heard from him again. Like before, I was at work when he texted to ask if I was available and my response was the same as before. I was unavailable. He wrote back "I want you to be my bitch... u make a hell of a bitch." He'd done it again. In the space of two short text messages he'd feminized me and totally turned me on. I texted back "I like the way you talk to me. I’ve asked guys to talk to me that way and they never get it right." He wrote back "I'm real... I naturally just know how to treat a bitch... I don't have to fake it, it comes natural... You want to be my bitch on the side?"
I didn't know what to say, so I simply replied "I like it. Turns me on." and moments later he responded "I don't think you've ever been turned out the way I want to turn you out." followed by "U gon' know that u are definitely a bitch." and then "bitch legs, bitch voice, bitch attitude, and a bitch mind." My mind was spinning and my cock was rock hard. I wanted so badly to meet him and feel his dominance in person, but I couldn't think of when I might be able to do so. We exchanged a few more messages about staying in touch and whatnot and then I had to go and relieve my desire by masturbating again.
I saved his text messages and in the months that followed, I would occasionally read them just for the sexual thrill they gave me. Those messages from him were the fuel for many sexual fantasies and just as many masturbatory orgasms.
A few months later we were back in touch. This time it was I who emailed him. I was actually available. I told him that I was going to be dressing up and asked if he was still interested in meeting me. He was. In our initial emails, he'd suggested a date at the movies. We'd never gotten into the details, but I always imagined we'd go to a movie nearing the end of its run so that there wouldn't be many people in the theater. We'd sit at the back and when the lights went down he'd start feeling me up, stroking my legs, and making me rub his big cock through his pants. I imagined that he’d tell me to unzip them and I’d do as he told me, pulling his thick, hard cock through his fly and stroking his naked cock while he watched the movie. Eventually, he’d just push my head down into his lap and make me suck him. To orgasm? I'd wondered. Or maybe he'd just make me suck his cock and lick his balls all through the whole movie. Or, at least until he couldn't wait any longer and just had to fuck me, and then he'd take me by the hand, lead me out of the theater, back to his car and into the back seat where he'd make me his bitch for real by fucking me deep with his huge black cock. Until now it had all been just a fantasy, but now it seemed a real possibility that it could happen. He was down for the movie and said he would come to San Francisco to pick me up. We'd settled on a time and a neutral location. We'd meet at the Safeway grocery store between Mission St. and San Jose Ave. and then go from there. He’d really liked the miniskirt that I was wearing in one of the photos he'd seen of me. It was black, pin-striped, tight and very short and he told me to wear it and some white panties. It really turns me on to have a guy tell me what to wear and so I was extra excited while I was getting dressed. Unfortunately, I'm notorious for taking way longer to get ready than I allow time for and so I had to message him that I was running late. He was very understanding and patient and told me that he'd be waiting at our meeting point. When I finally arrived at the Safeway parking lot it was pretty late and for discretion's sake, I parked behind the grocery store on San Jose Ave. I didn't see the black SUV he'd told me that he would be driving, so I texted him. He texted me back that he was in the parking lot on the side of the store, so I got out of my car and started walking in that direction. The clicking of my 5" stiletto heels against the sidewalk seemed loud to me as I carefully minced along. Although it was dark and the sidewalk was empty except for me, the distance I had to walk was about half a city block and I knew that my clothes made me look like a whore to anyone who might see me. I must admit, though, that nervous, exposed feeling is a real rush and I kind of like it. When I finally reached the parking lot I immediately saw his vehicle and him inside of it. I added more of a strut and wiggle to my walk as I approached him and made an effort to give him as good a look at me as possible as I walked around to the passenger side and climbed in. We exchanged pleasantries and he complimented me on my looks. He reached out and started rubbing my bare thighs and then pushed my skirt up to see that I was wearing white panties as he'd instructed. Deciding that we were too exposed under the lights in the parking lot, he drove out to the street behind the store and parked there. He instructed me to get into the back, so I got out of the car and re-entered in the back seat. He joined me moments later.
As is usual with these hook up blind dates, there were a few awkward moments as we tried to transition from saying hello for the first time to me on my knees with his cock in my mouth. Also as is usual, it didn't take too long for him to finally just whip out his cock and let me get my hands on it. It was big. It was barely starting to get hard and was already much longer and thicker than mine is when it's fully erect. I stroked his cock with my hands until it was nice and hard. I was about to get down and start sucking when he pulled a condom out and started putting it on. I appreciate that he wanted to be safe, but I always find it disappointing that I'll be sucking cock but not tasting it. Not to mention the desensitizing effect that a condom has. I knew I'd have to really work some magic to make him cum with a condom on. When he was ready, I bent down and took his cock head between my lips and started swirling my tongue around it. Once it was wet enough, I started bobbing up and down, sucking hard as I took more and more of his thick cock into my mouth. A few minutes into it, I realized that I needed a more comfortable position to work from, so I kicked off my heels and got onto my knees on the floor of his car and resumed servicing his cock. My head was bobbing up and down, my lips gliding over his thick shaft. I was sucking his cock for all I was worth, working hard to make it feel good for him through the condom when something happened that caught me by surprise. He started talking dirty. I love dirty talk, the filthier the better. But what he said wasn’t anything I’d ever imagined I’d hear.
It wasn't until a couple of months later that I heard from him again. Like before, I was at work when he texted to ask if I was available and my response was the same as before. I was unavailable. He wrote back "I want you to be my bitch... u make a hell of a bitch." He'd done it again. In the space of two short text messages he'd feminized me and totally turned me on. I texted back "I like the way you talk to me. I’ve asked guys to talk to me that way and they never get it right." He wrote back "I'm real... I naturally just know how to treat a bitch... I don't have to fake it, it comes natural... You want to be my bitch on the side?"
I didn't know what to say, so I simply replied "I like it. Turns me on." and moments later he responded "I don't think you've ever been turned out the way I want to turn you out." followed by "U gon' know that u are definitely a bitch." and then "bitch legs, bitch voice, bitch attitude, and a bitch mind." My mind was spinning and my cock was rock hard. I wanted so badly to meet him and feel his dominance in person, but I couldn't think of when I might be able to do so. We exchanged a few more messages about staying in touch and whatnot and then I had to go and relieve my desire by masturbating again.
I saved his text messages and in the months that followed, I would occasionally read them just for the sexual thrill they gave me. Those messages from him were the fuel for many sexual fantasies and just as many masturbatory orgasms.
A few months later we were back in touch. This time it was I who emailed him. I was actually available. I told him that I was going to be dressing up and asked if he was still interested in meeting me. He was. In our initial emails, he'd suggested a date at the movies. We'd never gotten into the details, but I always imagined we'd go to a movie nearing the end of its run so that there wouldn't be many people in the theater. We'd sit at the back and when the lights went down he'd start feeling me up, stroking my legs, and making me rub his big cock through his pants. I imagined that he’d tell me to unzip them and I’d do as he told me, pulling his thick, hard cock through his fly and stroking his naked cock while he watched the movie. Eventually, he’d just push my head down into his lap and make me suck him. To orgasm? I'd wondered. Or maybe he'd just make me suck his cock and lick his balls all through the whole movie. Or, at least until he couldn't wait any longer and just had to fuck me, and then he'd take me by the hand, lead me out of the theater, back to his car and into the back seat where he'd make me his bitch for real by fucking me deep with his huge black cock. Until now it had all been just a fantasy, but now it seemed a real possibility that it could happen. He was down for the movie and said he would come to San Francisco to pick me up. We'd settled on a time and a neutral location. We'd meet at the Safeway grocery store between Mission St. and San Jose Ave. and then go from there. He’d really liked the miniskirt that I was wearing in one of the photos he'd seen of me. It was black, pin-striped, tight and very short and he told me to wear it and some white panties. It really turns me on to have a guy tell me what to wear and so I was extra excited while I was getting dressed. Unfortunately, I'm notorious for taking way longer to get ready than I allow time for and so I had to message him that I was running late. He was very understanding and patient and told me that he'd be waiting at our meeting point. When I finally arrived at the Safeway parking lot it was pretty late and for discretion's sake, I parked behind the grocery store on San Jose Ave. I didn't see the black SUV he'd told me that he would be driving, so I texted him. He texted me back that he was in the parking lot on the side of the store, so I got out of my car and started walking in that direction. The clicking of my 5" stiletto heels against the sidewalk seemed loud to me as I carefully minced along. Although it was dark and the sidewalk was empty except for me, the distance I had to walk was about half a city block and I knew that my clothes made me look like a whore to anyone who might see me. I must admit, though, that nervous, exposed feeling is a real rush and I kind of like it. When I finally reached the parking lot I immediately saw his vehicle and him inside of it. I added more of a strut and wiggle to my walk as I approached him and made an effort to give him as good a look at me as possible as I walked around to the passenger side and climbed in. We exchanged pleasantries and he complimented me on my looks. He reached out and started rubbing my bare thighs and then pushed my skirt up to see that I was wearing white panties as he'd instructed. Deciding that we were too exposed under the lights in the parking lot, he drove out to the street behind the store and parked there. He instructed me to get into the back, so I got out of the car and re-entered in the back seat. He joined me moments later.
As is usual with these hook up blind dates, there were a few awkward moments as we tried to transition from saying hello for the first time to me on my knees with his cock in my mouth. Also as is usual, it didn't take too long for him to finally just whip out his cock and let me get my hands on it. It was big. It was barely starting to get hard and was already much longer and thicker than mine is when it's fully erect. I stroked his cock with my hands until it was nice and hard. I was about to get down and start sucking when he pulled a condom out and started putting it on. I appreciate that he wanted to be safe, but I always find it disappointing that I'll be sucking cock but not tasting it. Not to mention the desensitizing effect that a condom has. I knew I'd have to really work some magic to make him cum with a condom on. When he was ready, I bent down and took his cock head between my lips and started swirling my tongue around it. Once it was wet enough, I started bobbing up and down, sucking hard as I took more and more of his thick cock into my mouth. A few minutes into it, I realized that I needed a more comfortable position to work from, so I kicked off my heels and got onto my knees on the floor of his car and resumed servicing his cock. My head was bobbing up and down, my lips gliding over his thick shaft. I was sucking his cock for all I was worth, working hard to make it feel good for him through the condom when something happened that caught me by surprise. He started talking dirty. I love dirty talk, the filthier the better. But what he said wasn’t anything I’d ever imagined I’d hear.
“Suck my dick, Faggot. Suck it, you fag.”
Believe it or not, I'd never been called a faggot before. When I dress up as a woman, I like to consider myself female. Yes, I am male under all the feminine clothes and makeup, but generally, in these situations everyone simply accepts that I am female and treats me as such. By calling me a faggot he had changed the dynamics of our relationship. I was no longer a 'gurl' sucking a man's cock. I was now a feminized guy in drag being emasculated, dominated and sissified by a another guy, a REAL man. In my many sexual encounters with men, none of them had ever suggested that I was gay, never mind any of them calling me a faggot. I was a little bit taken aback. Should I be offended? I certainly wasn't. As I wrestled with my feelings about what he'd said, I kept bobbing up and down on his thick cock without missing a beat. He kept calling me a faggot and I kept right on sucking his cock like a faggot. "Suck my dick, faggot. Suck it like a bitch, you fag." For him, I think it wasn't enough that I sexually submit to him as a 'gurl'. He seemed to get off on acknowledging my maleness while simultaneously emasculating and humiliating me, as well. For me, I was starting to realize that I liked it. There was no denying that the more he called me a fag, the more my cock strained against my panties which held it firmly tucked between my legs. Sucking cock is always a turn on for me, but this was different. Being called a faggot, being called the name that describes exactly what I was in that moment as I sexually serviced his cock, was thrilling and even liberating. I wanted to be what he was calling me. I wanted to be his cocksucking faggot bitch and I tried to show him that by sucking his cock as well as I could. "Suck it, fag. Suck my dick, fag." This went on for quite a while. It was like a mantra that he never stopped repeating, drumming it into my head, into my psyche. And I embraced it, owned it, and used it to fuel my desire to pleasure his cock with my mouth until, finally, he was climaxing, his cock filling the condom with his hot seed. I was elated to have made him cum, but it was a bit anticlimactic to not be able to taste it.
When he was done, he carefully removed the condom and fastened up his pants while I straightened my clothes and put my heels back on. I gathered my purse and glanced around to make sure I wasn't forgetting anything and by then he was already stepping out of the car to return to the driver's seat. We said our goodbyes and I walked back down the block to my car. I like to think that he enjoyed the view of my ass wiggling in my obscenely short skirt as I walked away. Once back in my car I found myself filled with regret, not for the things I had done with him, but for what I hadn't. I regretted not thinking to ask him to pour his cum from the condom into my mouth so I could drink it down, or onto my face for a nice facial. I'd like to think that he would've enjoyed seeing me savor his cum. I know I would've loved it. "Next time..." I thought as I drove away.
When he was done, he carefully removed the condom and fastened up his pants while I straightened my clothes and put my heels back on. I gathered my purse and glanced around to make sure I wasn't forgetting anything and by then he was already stepping out of the car to return to the driver's seat. We said our goodbyes and I walked back down the block to my car. I like to think that he enjoyed the view of my ass wiggling in my obscenely short skirt as I walked away. Once back in my car I found myself filled with regret, not for the things I had done with him, but for what I hadn't. I regretted not thinking to ask him to pour his cum from the condom into my mouth so I could drink it down, or onto my face for a nice facial. I'd like to think that he would've enjoyed seeing me savor his cum. I know I would've loved it. "Next time..." I thought as I drove away.
