He turned his attention to me, leaving the porn on in the background. “Wow, that pill really looks good on you Harry! Turn around for me.” I spun, letting him take in the look. “Have a seat.”
I settled onto the ancient couch in his backroom office, the only other piece of furniture other than his desk and chair. “Thanks for giving me the hook-up. I’ve also decided to go by Jane as my ‘real’ name and Eve as my stage name.”
“Lovely names. You know the deal; I’ll buy the pills for when you work. But your dancewear is on you. And if you decide to take them recreationally, those are on you. You run out on a work night because you wanted to be Jane for a date…you know where to get the replacements. Understood?”
“Yes, Terry.”
“Good. Now some girls decide that they want to become permanent women. Those pills cost about the same as three months of pills for my part-time girls. But it’s a one-time cost for me so I’ll cover it. You just gotta sign a contract agreeing to dance for me for four months. Sound good?”
“Sounds fair.” I said with a smile.
“Good.” Terry turned to his monitor. “You know, it’s a shame guys can’t be free to be so free with one another.” I looked and the women were just kissing. Stripped down to their panties, naked breasts pressing into one another. Lips exploring and tongues tasting one another. Hands gently caressing. I found myself entranced by the images…and Terry’s idle thought.
We snapped out of it at about the same time. “Anyway, Jane. Let’s get you out of those street clothes and onto a pole.”
“Okay, where’s the dressing room?”
“You wearing a bra and panties along with those nylons?” I nodded yes. “Well then no need for a dressing room. Off with ‘em.”
I was shocked by the brazen direction. “Here? In front of you?”
“Listen, not trying to be an ass. The door is open and I’m not going to try any funny business. I want to see how comfortable you are taking off your clothes with one person watching in a private setting. Because if you’re gonna wilt in here, you’re gonna shrivel up out there.”
It made sense. So, I stood, took my top off and tossed it onto the couch. It caught me that I wasn’t doing this with any kind of seduction, and in fact probably took the shirt off as if I were presenting as a man. So, I sat on the edge of the couch, sliding one foot back and extending the other one. I looked at him with a smile on my face. I raised that foot off the ground and slid off the heel. Then repeated with the other foot.
I stood and began unbuttoning my pants, slowly unzipping them. Then pushing them down, just a little, over my now wider hips. I tried one of my soft giggles and turned around to push my pants down around my ankles. This way I gave him a chance to appreciate my heart-shaped ass.
I arched my back as I stood and reached up with both hands to let my hair down and fluff it as I turned towards him. A big smile had spread across his face. “I think you’ve got it, Eve.” He stood and came out from his desk. “Now put those heels back on and let’s get you on the pole.”
∞∞∞
A few minutes later and I was on the main stage. Terry, Jefferson (the bouncer), and “Chastity” were sitting watching me dance. Chastity is a real MILF-y dancer. Gorgeous in her late thirties, she’d been working for Terry for the last fifteen years. I was told she managed, mentored, and trained the talent. While Terry made the final hiring decision, it was obvious he rarely went against her recommendation.
I was dancing to a playlist on Chastity’s phone. I had discarded my bra and had a few bills tucked in my panties and garter. They said it was part of the audition and I could keep it at the end. Terry and Jefferson alternated between varying degrees of appropriate commentary on my body and ignoring me completely.
“Don’t show your frustration. Never stop smiling, you’re creating an illusion. You’re selling an illusion.” Chastity said. “Sometimes business and the allure of money will distract men from the allure of pussy.”
The mental chips fell into place. They were testing me. Seeing if I could smile and pretend to be interested in guys absorbed in whatever business they had going on. And Chastity was testing to see how well I took direction. I smiled and danced for them. When I got bored, I crawled over to Chastity and began rubbing on her.
“You can do more with women, push my shirt up and play with my breasts.” She whispered and I complied. They were magnificent, a little droop but they were still perky which made me think they were implants. (Spoiler alert: a few weeks later she confirmed they were.) “Now kiss me.”
I pressed my lips against hers and enjoyed kissing a woman as a woman for the first time. This drew the attention of the manager and bouncer back to me. She broke the kiss to whisper. “If the men around you aren’t responding and a woman is close by, a patron, waitress, or another dancer…flirt with them. If you kiss and play with them, you’ll get the attention of plenty of men.”
A few moments later, Chastity’s playlist stops, and Terry ends the rehearsal. “Wanna step back in my office?” I follow him, struggling to put the bra on as we walk. “You’ll learn soon enough. Most girls just walk back with their tits out.” It made sense to me, so I stopped trying to put them in boob jail.
∞∞∞
We get to his office and he shuts the door behind me. I stand there and put on my bra, then my shirt. He takes a seat behind the desk. His computer paused on the two lesbians kissing in the porn he was watching earlier. He sighed. “I wonder why men can’t be so free.”
I take a seat to put on my jeans, but something about his question makes me pause. “How so?”
“Well, you’d never see two men kissing like this in a porn. Much less real life. But I come in here and see women being so free with one another.” He looked at me, then back at the screen. “I mean, hell if I saw you on the street, you’d rev my engine. But knowing you used to be a guy? It’s weird.”
I blush at his admitted attraction.
“What about you?” He pressed on. “You ever had attraction to a guy?”
I looked down at my thigh highs. Alabaster thighs. Black panties. The names and faces of several guys from my past came to mind. “Yes.” My voice trembled just a little. It was the first time I ever admitted this to anyone out loud. “But I’ve never acted on it.”
“Do you want to?” He pushed away from his desk, making room on his lap in silent invitation.
I stood and stepped over to him, softly lowering myself into his lap. I wrapped my arms around his neck and looked him in the eyes. After a moment he pressed his lips against mine. I could taste beer and the cigar he had earlier. But I didn’t mind, it was the first time I kissed a man. Period. And I liked it.
His hand slid under my shirt, pushing my bra up and squeezing my breast making me squirm. His fingers rolling the nipple. I could feel his bulge against my thigh. I pulled away from his kiss. “Terry, there’s something I’ve always wanted to do…”
At that moment a realization hit me like a ton of bricks: that the rules were different for me know. That if I spoke my desire, he’d think me a slut. A nympho.
“What?” He rubbed my back. “It’s okay.”
I blushed. “I’ve always wondered what it was like to suck a dick.” I don’t know why, but at that moment I didn’t want this man who made his living off sex work to view me as a slut.
He kissed me tenderly. “Well if you’d like to try.” He spread his legs causing me to slide down a little. I went with it and found myself on my knees looking up at him, knowing what to do next but too timid to do it. “Here, let me help you.” He lifted off my shirt and then my bra. “Don’t want to get my cum on your street clothes, Jane. Now, go ahead and take it out for me.”
He spread his legs a little wider. My hands trembled as I reached for his belt.
“Are you okay? Do you want to stop?”
I smiled. “No…I mean yes…I’m okay…I don’t want to stop…I just don’t know what I’m doing.”
He ga
ve me a grin as he unbuckled, unbuttoned and unzipped his jeans. He even fished his cock out for me.
At that point, maybe it was his surprisingly gentle nature. Or seeing another man’s cock and feeling free to play for the first time, my nerves went away. I took it in my hands and started stroking it. Looking at it. I sniffed it, making him laugh a little. “It’s okay, put it in your mouth.” His tone was as soft as it was commanding. I leaned forward and took him in my mouth.
It tasted…bland. There was a spice to it and a musky scent. But I was shocked at just how little of a taste there was. Yet, it was amazing too. Having another man’s penis in my mouth. Giving him pleasure. I started sliding back and forth on his cock. Trying to do what came naturally and thinking what I liked.
The bottom of my shaft is the most sensitive, so I made sure to lick along the bottom of his root. I had a girlfriend once who would tease my balls with the tips of her fingernails, so I did that to Terry. I licked the bulbous head. I even stopped sucking enough to say, in what I think was a sexy voice, “I love your cock.”
“Do you want my cum, baby?”
“Yes.” I tried to sound like every porn star I had ever heard. “I want your cum in my mouth.” I leaned forward again and started sucking. I think I was doing a good job. He was just leaning back and moaning.
My feet were getting cramped in the heels, so I reached back at slipped them off. He reached down and started playing with my breasts. All the time his cock is getting larger in my mouth. I can taste precum. I moan along his cock, he responded by running his fingers through my hair and pushing me down on his cock. Holding me there.
Soon both hands were on the back of my head. My hands gripping his roller chair’s armrests for support. He started driving in and out of my mouth. Fucking my face. I could feel his balls smacking on my chin. I knew what he was doing, I’d seen it done in porn a lot. In fact, I thought back to the first time I got a BJ from a date. He was lost in lust and fucking my face. I just went along for the ride and soon he fired his load in my mouth.
Most of it went straight down my throat--but the last weak rope or two landed on my tongue. It wasn’t a horrible taste, but it wasn’t pleasant either. I pulled off, leaving a mess of slobber and cum on my lips, chin, and dribbling onto my chest. “Stay there, I’ll be right back with something to clean you up.”
He left me there on my knees, not knowing any better I stayed there. He returned with paper towels from the Men’s room. Some wetted, most dry. I cleaned myself up as best I could before getting dressed. “So, do I have the job?”
He leaned back in his chair and appraised me. “You still want it? I’m not going to demand them, but now that we’ve crossed that line…I’m going to want some more head from you. Are you okay with your boss asking for favors?”
I smiled, thinking how I could use head to my financial advantage. “I don’t mind.”
A grin spread across his face.
And that dear reader is how I got my job as a stripper.
Love,
Jane/Eve
Cover-Girl Confession: Andi the Plus One
Dear XChange Confessions,
This is something crazy that happened last June. I’m a good looking 28-year-old IT professional working for a conservative financial institution. I had to move to a new state in the Midwest and to a small city in the middle of the state. It’s one of those cities that grew because it’s a prime vacation spot for people in that state. So, it’s a blend of local yokel and Midwest “big” city.
Anyway, my story begins with a proposition from the son of the financial institution. “Andy,” not my real name, “what do you say?” Eric, not his real name either, looked at me intently over beers.
“Is this because I’m from San Francisco?” They assume I’m at least bi because of where I’m from.
“No.” He couldn’t look me in the eye. “Okay, maybe a little. But really its because you’re not going to be missed.”
I shook my head. “You really know how to make a guy feel important.”
He sighed. “Why do you have to make things so difficult?”
I smirked. I like to troll. I’ve always been that guy who fades into the background. When I’ve got someone like Eric asking me for a favor, I tend to savor it. What favor was he asking for? His little sister was getting married and Eric needed a date to the wedding. A year earlier he broke up with his fiance that everyone expected him to marry. He came home early from a business trip and caught her and some summer intern in the house they shared.
He was 32 and, like I mentioned it’s a conservative area and his family expected him to find a proper woman and settle down to start a family. After all, he was being groomed to take over the bank and an expectation was he needed to produce an heir.
“C’mon, please?” He said as he shook the bottle of pink pills, the label had a gorgeous redhead on it.
“$500, you buy all my clothes and pay all my expenses for the weekend?”
He nodded yes and I took the pills from him.
∞∞∞
Since my name (real and alias) is gender neutral, we decided to just change the -y to an -i. That way it would be one less thing to trip me up on. I two weeks to learn as much as I could about being a woman. Walking in heels and applying make-up where the most difficult but with a little perseverance I taught myself the finer art of these things.
The Thursday afternoon before we were supposed to leave for the four-day weekend I took the 96-hour pill. The transformation was not the best part of the weekend. I don’t know what was worse: the sensation of my body changing from male to female or the anxiety over whether or not it would go back as advertised. Maybe it was not knowing what I would look like; if the results were horrible, we were going to call the whole thing off.
But when I looked at the mirror a gorgeous redhead stared back at me. The only thing that looked the same were my green eyes, but they were different. I could see better out of them and didn’t need my glasses. I had beautiful, D-Cup breasts and a tight slit between my legs. I had to resist reaching between them, I only had a couple of hours to get some shopping done. The town had only one upscale boutique and it closed at 8pm.
∞∞∞
I don’t want to bore with the details of my first-time shopping as a woman. It was fun and I got noticed by a lot of guys. This aroused me, which surprised me since I never really thought of myself as even bisexual. Nor will I bore you with all the small talk on the ride to the venue a couple hours away at a vineyard. And yes, it shocked me that they have those in the Midwest! What shocked me more was the wine was actually really good!
What you want to know is what happened after the rehearsal dinner.
We got back to our hotel suite. The plan being I got the bed and he would sleep on the fold-out. We got a little tipsy at dinner. His family loved me, and I got along with his sister, which is amazing because we don’t get along at work. (Did I mention she was head of the bank’s IT and Cybersecurity department? Genetics played more of a role in her getting the job than her ability.)
I had slipped out my heels on the way back up the room. Eric was making me giggle the entire way up. But once we got to the room, I dropped the act. Not that I wasn’t enjoying it—it was fun to be the girl. It was a different kind of pressure than being the guy—but it was nice because I wasn’t sweating any of it. (Dating always made me nervous as hell.)
“Glad that’s over. Goodnight!” I stepped towards the bedroom.
“What? No goodnight kiss?” He asked playfully.
“Good night, Eric.” I paused at the door before passing through it and closing it behind me.
I had worn a Navy-blue dress that showed my curves and ended above my knees. It looked good on me, but I was glad to get it off. I don’t like tight clothing, with one exception: I really liked the feel of my nylons. I had bought a couple pairs of thigh highs on a lark. These were nude colored with a back seam and reinforced heel, sole, and toe. The sales lady said it would gi
ve my legs a classic look.
She had been right.
I’m standing there in nothing, but a navy bra & panty set complete with garter belt and thigh highs. There was a knock at the door. “Hey Andi…I’m curious…can I see.”
“Good night, Eric.”
“C’mon…please?”
I must admit that I understood his curiosity.
“Listen,” he persisted, “the fold-out is broken. I’m going to sleep out here anyway. Like the gentleman I am. Perhaps a little peek would make it worthwhile.”
I opened the door and did a turn for him. “Happy?” I said with a wink.
“Very, thank you.” He grabbed the doorknob and closed the door.
XChange Confessions 2 Page 2
