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Anything Goes
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Straight Male / 45
Being Jacqueline
I’m a 45-year-old man whose work entails a lot of travel to various cities across the United States, but when that work is done, and I’m free to explore these unfamiliar places in full, I do so as a woman. I do so because I can. I can pretend to be someone else. I can actually become that someone else because no one there is any the wiser since none of them know who I am, and there’s something about the feeling of vulnerability that comes with both being a woman, and pretending to be someone you’re not. The threat of being found out is always present, and the fear of that begets a certain sense of exhilaration, but I’ve worked hard at successfully passing. I’ve learned to do my makeup, and to efficiently remove my body hair. I have also invested in wigs, fake nails, hip pads, and women’s clothing. I even have a silicone breast vest to wear under said clothing. It did not come cheap. I keep all of this in a storage locker, so my wife doesn’t find out, but this is not my confession.
Over the past year, I’ve grown more and more daring as a woman. First, I started allowing myself to be engaged in conversation by other men. Apparently, my voice is passing, too. I call myself Jacqueline, or Jackie for short (no, my real name is not Jack). One night, at a bar in Dallas, I let a guy buy me a drink, and he sat down at my table and introduced himself. He was probably less than half my age, but I let him keep buying me drinks as we talked, knowing what he hoped to accomplish in doing so. I let him get me falling-down drunk, and wound up splayed across the center console of his pickup truck with his dick in my mouth. I was still conscious, and aware of what was happening, but I pretended not to be as he worked my head up and down. I still remember the smell of his cock, and the taste that remained in my mouth until the morning after he blew his load down my throat. Once back at home, I was disgusted by the thought of it. I’m not attracted to men, so I don’t consider myself gay or even bi-sexual, but I’m not me when I’m away. I’m Jacqueline. Even so, I didn’t want to suck his dick, even as a woman. He did make me feel sexy. It felt good to be desired but, in hindsight, I had imagined that he was forcing me to do it, as it was happening, which wasn’t hard to do considering that it was true, at least from his perspective. From his perspective, it was a sexual assault, but I wasn’t forced to do anything. I let it happen, because part of me felt like I deserved it, for dressing up like that, and I wanted to be degraded for it. Another part of me felt exactly the opposite. As fucked up as it sounds, I didn’t feel that I was desirable enough, as a woman, for a man to want to take advantage of me, but I wanted to be. Subconsciously, I had been “asking for it,” and received a sort of sick validation out of what happened in the cab of that pickup. It made me feel more like a woman, and since then, I’ve been chasing both the validation and the degradation that I felt after that encounter. It has become a compulsion.
On my next trip, I dined at an expensive restaurant and purposely left my cash in the car (I avoid using my credit card as Jacqueline, for obvious reasons). After downing a $120 bottle of wine with my meal, I feigned distress when it came time to pay, rummaging through my purse for money that wasn’t there. My server called the bartender over, and told him to make sure I didn’t leave before he spoke to their manager. That’s when I made myself cry, begging him not to tell anyone else, and asking if there was some other way we could work it out. I sucked them both off in the men’s restroom. The bartender, an African American man, got rough, calling me a “dumb white bitch” as he slapped me and made me deepthroat his cock. I was terrified that he’d find out that I was a man and beat the shit out of me, or worse. That fear is always in the back of my mind now, with each new cock I accept into my mouth. I’m always more relieved than anything else, when they finish, but I keep doing it. I can’t stop. I’ve now sucked six dicks. One belonged to a cat-calling construction worker in Houston, who agreed to pay me $100 for it after I went out of my way to walk by the building he was scaffolding. I’ve even started trying to think of ways in which I could get bent over and fucked in the ass, without being found out, perhaps with a second cock in my mouth to prevent me from telling either one of them to stop, because I know I would want them to stop. That’s the idea. I don’t want to enjoy it. I want to feel like I’m being used against my will, and so I want to take my will out of the equation. I want to be made to take it up the ass, not until I’ve had enough, but until someone else has. I know I’ll make it happen, too, or at least try to, despite the increased risk. I just can’t help myself.
Over the past year, I’ve grown more and more daring as a woman. First, I started allowing myself to be engaged in conversation by other men. Apparently, my voice is passing, too. I call myself Jacqueline, or Jackie for short (no, my real name is not Jack). One night, at a bar in Dallas, I let a guy buy me a drink, and he sat down at my table and introduced himself. He was probably less than half my age, but I let him keep buying me drinks as we talked, knowing what he hoped to accomplish in doing so. I let him get me falling-down drunk, and wound up splayed across the center console of his pickup truck with his dick in my mouth. I was still conscious, and aware of what was happening, but I pretended not to be as he worked my head up and down. I still remember the smell of his cock, and the taste that remained in my mouth until the morning after he blew his load down my throat. Once back at home, I was disgusted by the thought of it. I’m not attracted to men, so I don’t consider myself gay or even bi-sexual, but I’m not me when I’m away. I’m Jacqueline. Even so, I didn’t want to suck his dick, even as a woman. He did make me feel sexy. It felt good to be desired but, in hindsight, I had imagined that he was forcing me to do it, as it was happening, which wasn’t hard to do considering that it was true, at least from his perspective. From his perspective, it was a sexual assault, but I wasn’t forced to do anything. I let it happen, because part of me felt like I deserved it, for dressing up like that, and I wanted to be degraded for it. Another part of me felt exactly the opposite. As fucked up as it sounds, I didn’t feel that I was desirable enough, as a woman, for a man to want to take advantage of me, but I wanted to be. Subconsciously, I had been “asking for it,” and received a sort of sick validation out of what happened in the cab of that pickup. It made me feel more like a woman, and since then, I’ve been chasing both the validation and the degradation that I felt after that encounter. It has become a compulsion.
On my next trip, I dined at an expensive restaurant and purposely left my cash in the car (I avoid using my credit card as Jacqueline, for obvious reasons). After downing a $120 bottle of wine with my meal, I feigned distress when it came time to pay, rummaging through my purse for money that wasn’t there. My server called the bartender over, and told him to make sure I didn’t leave before he spoke to their manager. That’s when I made myself cry, begging him not to tell anyone else, and asking if there was some other way we could work it out. I sucked them both off in the men’s restroom. The bartender, an African American man, got rough, calling me a “dumb white bitch” as he slapped me and made me deepthroat his cock. I was terrified that he’d find out that I was a man and beat the shit out of me, or worse. That fear is always in the back of my mind now, with each new cock I accept into my mouth. I’m always more relieved than anything else, when they finish, but I keep doing it. I can’t stop. I’ve now sucked six dicks. One belonged to a cat-calling construction worker in Houston, who agreed to pay me $100 for it after I went out of my way to walk by the building he was scaffolding. I’ve even started trying to think of ways in which I could get bent over and fucked in the ass, without being found out, perhaps with a second cock in my mouth to prevent me from telling either one of them to stop, because I know I would want them to stop. That’s the idea. I don’t want to enjoy it. I want to feel like I’m being used against my will, and so I want to take my will out of the equation. I want to be made to take it up the ass, not until I’ve had enough, but until someone else has. I know I’ll make it happen, too, or at least try to, despite the increased risk. I just can’t help myself.
