Below is a true story. The names have been changed, to protect the innocent...except Brandy, who isn't so innocent. ;)
Words are powerful things.
Sitting in a college lecture, bored and tired, a female friend, Amanda, passed me a sheaf of papers. A quick glance revealed that the papers were a wall of unformatted text. Looking back at Amanda, I noted she had a gleam in her eye and a wry smirk on her face. Glancing around at some other friends in the same lecture who were looking back at me conspiratorially, I could see that I wasn't the first one with a chance to peruse whatever was contained on these pages. With a shrug, I started reading.
The words that leapt from those pages embedded themselves in my brain and planted a seed that has never died to this day, even if it has been neglected for long intervals.
The papers contained a story, downloaded and printed from the (at the time) fledgling World Wide Web. The story involved a man 'forced' to transform into a crossdresser, complete with sexy panties, bra, makeup, wig, garter belt, stockings, and high heels. The man in the story got to have sex with the hot woman who dressed him this way, so long as he also serviced her male partner. As I read, my body responded, cock stiffening in my pants. By the time I'd finished reading the story, precum was leaking into my boxer shorts as I ached with desire. I passed the pages back.
Amanda and another woman, Jian, exchanged a few words and jotted something down on a scrap of paper. Then a note was passed to me. It read:
"So, Brandon... Hot or Not?"
There were little check boxes next to the words "Hot" and "Not".
Without hesitation, I checked the box next to "Hot" and passed the note back. The women read it, exchanging looks and giggles. Being entirely heterosexual to that point, I didn't know why I'd checked "Hot" - though I assumed it had something to do with the searing iron rod in my pants.
Over the next couple of years of college, I had a number of wild sexual encounters including an MMF threesome with my girlfriend and best friend and some involving Amanda (alone and with others, including Jian), but we never revisited the scenario described in the story.
Yet the seed had been planted.
Fast forward. I was 27 years old, living in a bachelor pad in New York City. I was 5' 10" and 180 lbs of mostly muscle developed through years of playing sports and hitting the gym at varying degrees of frequency and intensity. Good looking, with short hair the colour of dark chocolate contrasting nicely with my pale skin, I'd had no trouble attracting the ladies. In fact, by this time, I'd already been with more than 50 women. On the evening in question, I was also in the "off" cycle of an off-and-on relationship.
In reality, I was bored of the bar pickup scene and, truth be told, perhaps getting a little lazy. I started calling escort agencies searching for something new and exciting. I was with wonderful women of every colour of the cultural rainbow: African American, Asian, Hispanic, Italian, Eastern European, Indian - you name it. I had a preference for thin ladies and even preferred small breasts; in truth I was more of a "pussy man". I even tried a couple of times to have a threesome with two women, but there always seemed to be an issue with the women who were sent over not really wanting to be with one another. Understandable, but an expensive and not particularly satisfying experience.
One Saturday night, I was looking at the website for an agency that had previously sent over a particularly attractive and fun Eastern European woman. I reviewed their "Services" page. One item on the list of services offered was "Light BDSM". Now, I knew what BDSM stood for but hadn't really explored this path before. I pictured a skinny, severe Asian woman in black patent leather tying my hands and smacking me with a paddle. Dubious as to whether this was my jam but simultaneously curious as to what might happen, I rang up the agency and told them I wanted someone interested in "Light BDSM".
"Zat ees noh pobblem," the woman on the phone responded in a thick Eastern European accent. "You wan Ber-jeet." I quickly pulled up the photo of "Brigitte" on my computer; she wasn't one of the ladies that I'd been particularly drawn to previously. But, what the hell? I thought. I wanted to try something different.
"Sounds good," I responded.
After hanging up, my nerves began to get the better of me and I downed three rum and cokes during the 30 minutes that I waited for Brigitte to arrive. Suddenly, there was a rap on my apartment door. Opening the door, I was confronted by a tall woman, maybe 5' 11" or so. She had caramel skin, and slightly exotic looks - maybe a Filipina and African American mix. It was hard to tell. She had long auburn hair - obviously dyed. Her face was not gorgeous but not bad either. She wore bright red lipstick on full lips that really stood out. But what truly caught my attention was her voluptuous frame: Very large breasts - perhaps an E cup (or bigger?) - skinny little waist, wide hips and thick thighs with a full butt. She was not my usual type.
The woman in my door frame scanned by being, from head to feet and then back up again, before saying, simply, "I'm Brigitte."
I invited her in, shutting and locking the door behind us, and escorted her into the living room. Brigitte untied her black wrap dress, as though freeing herself from bondage, and sat on the couch, making herself at home. Underneath she wore a black satin overbust corset, black satin thong panties, black thigh-high stockings with garters, and 4" black stiletto pumps. My cock stirred in my pants. If nothing else, I was right about the black outfit. That's when I noticed that she had a bag with her - not a purse, but a duffel bag that appeared to be full - which she dropped on the floor with meaning. She had a commanding presence. And she was still studying me.
"What's your kink?" It sounded more like an accusation than a question.
"Honestly, I don't know," I responded submissively. The nerves were still there and I suddenly worried this might not go anywhere.
But without hesitation, Brigitte unzipped the duffel bag, rummaged for a brief moment, and then threw something at me. "Take off your clothes and put those on," she commanded. I collected the items and saw that it was a pair of white mesh thong panties and a crop top with a leopard print. As I looked up at her, she had also produced a pair of white strappy sandals with thick 2" heels. "These too," she added.
Now, this was a critical life moment, one in which a person should take pause and carefully consider their next course of action. Me? I didn't think at all. I just pulled my t-shirt over my head and tossed it onto my bed in the next room (New York railroad apartments aren't that big). I then popped the button on my shorts and pulled them down to the floor along with my boxers, my semi-hard cock springing free. They quickly arced through the air as they chased my shirt onto the bed.
What was I doing? I didn't know, but this definitely seemed like a new path to explore. I pulled on the crop top which stimulated my right nipple (a.k.a. my "on" switch), causing it to become erect. I then stepped into the panties and slid them up my legs until they enveloped my balls and the strap of the thong slid up between my ass cheeks and tickled my hole. I got goosebumps and the hairs on my arms and legs stood on end. Shivers ran through me. My whole body felt electrified. I'd never felt anything quite so sensual. Is there anything that feels as good as women's panties caressing your balls and asshole?
Bending over, I strapped on the heels and then stood up straight and looked back at Brigitte. I felt silly but also incredibly horny. My cock was growing as the rush of desire began to overtake me. There was a gleam in Brigitte's eye, despite the outwardly commanding demeanour.
"Now walk, bitch," she ordered.
I tried walking from one end of the narrow but long living room to the other. I stumbled frequently and I'm sure I nearly broke an ankle. It wasn't pretty. She made me do it a few times. I thanked whatever sick god might revel in this sort of behaviour that the heels weren't stiletto. The sound of the heels on the hardwood floor of my apartment could certainly be heard by the landlord and his wife living in the apartment below. But that click-clack sound, made by me as I walked, added a rhythm to the building symphony of my sexual arousal.
Suddenly, I became aware that the drinks I'd downed before Brigitte's arrival had worked their way through my system. I told Brigitte that I needed to pee, but that to get to the bathroom, I'd need to walk through the kitchen - there were no curtains on the window in the kitchen. What I wanted was to be able to change out of this outfit or cover up, but that wasn't what Brigitte wanted. "Do it," she demanded. "Keep those clothes on and do it." The thought that people in neighbouring apartments might see made me feel sick...but the potential humiliation was also strangely exciting. This was certainly turning out to be an interesting experiment.
As I returned to the living room, still stumbling in my heels, Brigitte laughed, and said "you'll get better with time, sissy." She then stood up, slid her panties down, and reclined back into the couch, spreading her legs. "Now come here, bitch, and eat my pussy."
If there's one thing you need to know about me, it's that I absolutely love eating pussy. Say what you will about macho, athletic, jock-types, but honestly there is nothing better in his world than eating a beautiful pussy. I dived into this task with absolute gusto. I must have licked her pussy for a good 15 minutes.
As things worked toward a crescendo, Brigitte stood up, placed her hand on the back of my head and pressed me harder into her dripping cunt. It wasn't necessary as I was completely committed to eating her to orgasm. But she held the next surprise.
Spinning around, Brigitte reached back and spread her ass cheeks. "Eat my ass, you slut."
I almost came in my panties.
As Brigitte spread her ass cheeks, I stared at her large brown rosebud. Desire almost completely overwhelmed me and I buried my face in her ass and my tongue deep in her asshole. It tasted bitter at first, but I pushed that out of my mind and lunged into the role of ass licker with wanton abandon. I pistoned my tongue in and out of her asshole like it was a pussy being fucked. I pulled out, swirled it around her anus, and then dived back in. Brigitte reached back and grasped the back of my head, forcing me deeper into her and fucking herself with my head.
"Oh, you're a nasty fucking whore, aren't you?" she said. "I knew I had you pegged."
Pushing me back, Brigitte spun around and lay back on the couch. "Alright, slut. You've earned a little reward. Come over here and fuck me!"
Suddenly, I needed to be a man again. It was jarring. I pulled the panties down below my balls. Getting hard wasn't a problem - I'd been hard as a steel pole since I'd slid the panties on. And I still loved pussy. So I moved up between Birgitte's legs and slid my cock up into her dripping cunt. As I slid in, I pulled her bustier down and freed her massive tits. Licking and sucking her nipples and areolae while pumping into her, I got lost in the moment for a minute or two. But I also realised that I probably wasn't going to cum. I didn't know why. Then I had an idea...
"Can I fuck your ass?" I asked Brigitte.
The force of the blow caught me by total surprise as my mistress struck me across the face. "Never!" she screamed in momentary fury. I saw stars.
Pushing me off of her, she told me to lie back on the couch. "I know what you need, faggot."
Reaching into her magic bag of tricks, Brigitte produced a jar of lube. She dipped her left hand in and then began expertly stroking my rigid cock. She dipped her other hand into the lube, and then shimmied my legs wider apart. While stroking my cock with one hand, Brigitte began circling a lubed finger around my exposed hole. Ooh, that felt good. She then slipped her finger into my well-lubed ass. At first, she just played at the entrance, going about one knuckle deep. All the while stroking my cock. Then Brigitte pushed her digit in two knuckles deep. This was more than I'd ever had in my ass. But it felt good, and something possessed me: I rotated my hips and pushed down on her finger, engulfing it all the way to the hilt. That felt amazing!
The move didn't go unnoticed.
"Ooh, you like it deep in your ass, don't you? I should have known you little fucking sissy slut."
Brigitte began pumping her finger all the way into the hilt and then back out again. Then she slid two fingers in while stroking my cock, massaging the underside of the tip with her thumb. "Take it in your hungry pussy, you fucking sissy whore." With two fingers sliding in and out of my ass pussy, legs in the air with heels on, I really was a sissy whore. But it felt so good - I was in sissy heaven. Applying a little more lube, Brigitte slid a third finger deep into my hole and pumped my cock faster. I felt full, and somehow, whole. Suddenly, I felt an overwhelming sensation deep inside me, and my orgasm flooded over me like a tsunami. Cum exploded from my cock high up into the air, landing on Brigitte's hand and arm as she continued to pump. Usually a 'quiet cummer', I roared out a guttural orgasm as Brigitte fucked my pussy and pumped my cock. Jet after jet of hot cum erupted from me until there was nothing left.
Brigitte slowed her stroking of my cock and slid her fingers out of my hole, leaving me with a strange empty feeling. The stroking stopped, and Brigitte went to the bathroom to wash up. When she returned, Brigitte had a smile on her face and a gleam in her eye. I was still lying on the couch in my crop top, panties, and heels.
"I'll need those clothes back," Brigitte said. "But now that I know who you are we're going to have some fun."
Who you are.
Powerful words that sunk deep into me. An hour ago, I was a normal guy, a "womaniser" even. Now, I was some kind of crossdressing sissy slut. My cock tingled at the thought.
"What's your sissy name, bitch?" I stared at her blankly. "I can't call you by your 'man' name, now can I?" she continued. "What's your sissy name?"
"Brandy," I blurted. Where the hell did that come from? Was that growing deep in my subconscious all this time? I guess it wasn't a big stretch from Brandon.
Brigitte smiled. "Brandy. Well, Brandy," she said, emphasising the name, "here's my direct number. Fuck the agency. We've got work to do if we're going to turn you into a sissy cocksucker."
That should have set off alarm bells. Instead, my cock started to swell.
Brigitte, now fully dressed, packed up her bag and moved to the door. "Until next time, Brandy." She left and I closed and locked the door behind her.
With those words, Brandy the sissy slut was born.
Let me know if you'd like to hear more adventures. Kisses, Brandy.