Man to Woman

by Jane Futa

  I looked down and brushed off my shirt. I’d chosen a button-down shirt the color of slate, along with some comfortable but faded denim jeans. I didn’t need impress or anything – the ad had certainly made that clear. In fact, my only job was to stand around and flaunt my size; something I could easily do for five-hundred bucks.

  I wasn’t exactly making in the Bay Area. Rent prices were through the fucking roof. Add that to the list of expenses when I signed up for a few community college courses to get back on the right track, and I was poorer than I ever wanted to admit. So I traded out the football team for a few bouncer and bodyguard gigs. As we rounded the last corner and came to a pink door, I couldn’t decide if I was in over my head yet, or not.

  “Here ya’ go,” the man said. He knocked and after a moment heard an older woman ask, “Who the hell is that?”

  “It’s C,” the man said in his low, hulking tone.

  After a short pause, the door cracked open. A woman, about as I imagined – maybe mid-forties with a tight scowl across her lips and a haircut way too young for her – looked us over.

  “Security?” She asked.

  “What do you think?” The man laughed and looked at himself before turning to me. The woman didn’t share his sense of humor. “You were supposed to be here fifteen fucking minutes ago.”

  “Martha, please,” we heard a sweet and high-pitched tone calling from somewhere deeper in the bright, pink room.

  Suddenly the door swung open, and I was met with the cutest, most fuckable little tart I had ever seen in my life. The girl had a short pink wig on and was covered in glittery eye-shadow, which made her blue eyes pop. Her lithe frame curved like a bell at her hips, only rivaled by the unexpectedly large breasts hanging in her rainbow leotard, which was donned with some sort of tutu around her waist. “Shit,” I whispered beneath my breath and hoped for dear life that nobody could hear. The girl smiled and said, “I’m sorry. Um, right in here.”

  She moved to the side and did a little playful courtesy. The larger man motioned toward me and said, “She’s all yours. Whatever she wants for the next few hours, you give it to her – no questions asked, got it?”

  I only nodded and smirked with confidence. What’s the worst that could happen? I thought to myself.

  The older woman was all but pushed out of the room by the girl and suddenly I was standing in a dizzyingly colorful dressing room with just me and the pop-star only known to me as “Ash.”

  “Um, you can have a seat if you want,” she said with a mousy laugh as she sat back in her chair and pulled her lithe legs up, tucking them and setting her chin upon her knees as she scrolled through her phone.

  I sat on a giant lime-colored bean-bag chair and sighed. Shaking my head, I started to wonder if I’d made a huge mistake. What the hell was I doing? She didn’t need me; she had a million assistants.

  I looked around the room and saw a small plate of food, likely brought in from the catering table but hardly touched by Ashley. As I scanned the room, I couldn’t help but see the girl continually stealing glances at me. Her blue eyes were wide and curious; she had that look that girls sometimes get when they definitely want something, but because it makes them look like little sluts, they keep it sneaky. Of course, I didn’t exactly connect these dots in the moment. Sure, I’d bedded plenty of girls when I bounced the clubs, but I wasn’t about to assume that some national pop-star was eye-fucking me the moment I entered the room.

  “Um, are you Ashley?” I asked, before laughing. “Fuck – of course you are, right?”

  The girl laughed and nodded. “You don’t get out much, huh?”

  “To tell you the truth,” I started, laughing and shrugging.

  The girl stepped from her chair and came over, sitting on the floor next to the bean bag chair. She looked me up and down and seemed particularly slow to move her eyes from my crotch as I sat splayed in the giant bag.

  “So, you’re security for the night?” She asked.

  “I guess neither of us knows what we’re doing,” I noted. She laughed and shook her head. “I didn’t know if you were maybe one of the backup dancers. Sometimes I hang out with them.”

  “You thought I was some prissy backup dancer?” I asked, taken a back and slightly insulted. “Come on.”

  “Sorry, I don’t know,” she said. She shifted her eyes playfully and added, “So you’re cuter than I would expect a bodyguard to be, is all.”

  I shook my head and simply sighed, “Whatever.”

  “Seriously though; whatever you need tonight – I’m your man. The uh, the big guy back there mentioned that I would be escorting you to the stage and be in section A8 for the concert, and then we’d come back around…” I explained, before Ash immediately interrupted me.

  “What? Um, no, no. Your job is to stay here, in this room,” she said with wild and wide eyes. She bit a pink-painted nail nervously for a moment. “I need you in here the whole concert, and then after.”

  “Really? I mean, it makes no difference to me, I just wanted to make sure…” I continued.

  “Yes. You’ll stay right here, and then I’ll see you after the show. C is going to be my escort to the stage, which should be any minute.”

  “Sounds fine with me,” I said, leaning back. “Whatever you need while I’m in here, then, I’m your guy.”

  “Oh yeah?” She said with a curious tone.

  “Yep,” I said, innocent as a freshman.

  She looked over and bit her lip, before jumping up. “Tell me what you think of this, then.” Ashley stood up and did a small dance about the room. Her outfit sparkled and her pink wig tasseled from side to side as she started to sing beneath her breath, what I could only imagine was one of her hit singles.

  “Did you want commentary on the dancing or the outfit?” I asked.

  “Why? What’s wrong with the outfit? You can’t see anything can you?” She asked, bending over and lifting up her tutu playfully. The sudden image of her perky little ass sitting in her bright red stockings, made me harder than I wanted to admit. This spry eighteen year-old pop-star was either oblivious as fuck, or a dirty little slut in secret.

  She stood back up and turned around. “Um, everything looks good,” I said.

  “I need you to zip up the back part here really quick before C takes me to the stage,” she said, pointing to just between her shoulder blades. I hopped up and obeyed, though I certainly wasn’t expecting this sort of work when I signed up for the job. Ashley stood still for a moment as I approached behind her and grabbed the zipper. I focused and pulled it up as she suddenly backed her ass right into my crotch.

  “Whoa,” I said, jumping back as if a snake had jumped out of the water and headed right for my dick. “What um… what was that? You okay?” I asked.

  Ashley only laughed hysterically and turned to face me. “You’re fun,” she said in-between her laughter.

  “I think I’m going to need some clarification here. I’m started to wonder just what my job here tonight, is,” I admitted, rubbing the back of my neck.

  “What do you mean?” Ashley said, staring me down and stepping closer toward me. She was a bi-polar piece of work if I had ever seen one. She seemed all over the place, and in my line of work, that wasn’t good. But then, I was starting to wonder just what my line of work entailed in that moment.

  “Well, I took this job because I thought I was going to be your bodyguard for the night,” I explained stepping back.

  “Right,” she nodded.

  “So… when am I supposed to, you know, guard your body,” I said with a tense huff of laughter. I might have carefully planned that double entendre as well.

  “You were hired to do whatever I need,” Ashley said, pursing her red lips together and smiling. “Right now, you’re entertaining me before I go on stage. Sometimes I get a little adrenaline rush before the show and I kind of go spastic. So your job is to entertain me, silly.”

  Ashley finished her lecture with a small kiss on my che
ek before she pulled back. She continued to eye me as she walked back to the vanity mirror before her chair. Within moments, the large man from earlier popped his head in the door and motioned for Ashley.

  “Let’s do this,” he said, eyeing the ceiling as we all heard the audience growing wilder by the second.

  Ashley looked at me as she made her way out of the room and disappeared for the next few hours.

  I looked around, and when it became evident that she wasn’t coming back, I started to scroll through my phone. Eventually, even this became too dull to take, and I started to get curious. It didn’t hurt that I could hear that pink-haired little tart singing her lungs out just up above my room, that I felt more relaxed in poking around her dressing room.

  Though admittedly, I knew what I was doing was probably going to get me fired if anybody were to walk in. The evening had been so strange as it was, I almost didn’t mind either way. Hell, I figured maybe I would find something I could take with me and auction off; maybe an authentic Ashley wig or something.

  I rustled through a few of the shopping bags next to Ashley’s chair, and didn’t find much. After looking through the tiny makeup bottles on her dresser, this novelty ran its course as well.

  Why would she have anything of interest? What the hell is wrong with you, creeping like this? I thought to myself in a moment of guilt.

  I started to walk back to the beanbag chair and endure the next hour or so of complete nothingness, when I noticed another bag out of the corner of my eye. This one had seemed hidden, tucked just behind a speaker. The small, purple reflective bag was eye-catching, when you actually noticed it. I walked over and, after looking towards the door once more, peeked inside.

  “Holy shit,” I gasped, sinking my hand in the bag. I wrapped my fingers around the rubbery girth of a massive, lifelike dildo.

  “No way,” I laughed, looking at the monster cock as I shook my head. “There is no way this is hers, is there?”

  Just as I’d been holding the giant cock in my palm, the dressing room door swung open and Ashley came rushing in, her face sheened with sweat as she stormed towards me. For a moment, she seemed completely focused – her eyes were direct, as if she knew she needed to do something immediately, so much so that the guy holding the giant dong in the corner of her room hadn’t so much as caught her attention.

  I tried to pull the dildo behind my back, and watched as Ashley turned. Her pink wig tasseled to the side and she squinted her eyes. “What are you doing?” She asked, pulling a few strands from her sweaty forehead. She looked hot as fuck in that moment; the only thing I could think about, was how much I’d have loved to be the one to make her sweat, rather than a list of stale pop songs.

  “Uh… what? Nothing – I wasn’t doing anything,” I said, shaking my head with a nervous smile.

  Ashley rushed around to my side and saw me holding the dildo. Her giant eyes glared towards me. In the moment, I was too busy trying to figure out how I was going to explain all of this to her. I didn’t for a moment believe that it was her dildo, and so I was trying to think of how I would explain to her that her bodyguard had somehow snuck a giant fake dick into her dressing room.

  “Who said you could go through my stuff?” She cried.

  “Whoa, whoa, this is all a huge misunderstanding,” I explained, tossing the dildo back into the bag and listening as the tissue paper crinkled beneath it.

  “Why were you holding that?” She asked, still trying to catch her breath.

  “I uh… I found it,” I said, laughing and hoping to lighten the mood.

  Ashley stepped toward me and her cheeks flushed red. “That’s not yours,” she said.

  “Sorry; I really am. I wasn’t expecting anything uh… like that,” I explained. “I should probably just go.”

  “Um, what?” Ashley said, jumping in front of me.

  “I obviously fucked up and so I’ll just see myself out,” I said. I felt like a total idiot. I had one chance at five hundred easy dollars, and I fucked it up by getting too nosy.

  “Um, you’re not going anywhere,” she said. She stepped back and locked the door behind her small body, before stepping back toward me.

  “What?” I laughed and shook my head as I looked down. “You’re not going to try and stop me, are you?”

  “I don’t have to try and stop you. I’ve got photo evidence of you holding a giant dildo,” Ashley said as she pointed to a small security camera sitting on her desk.

  “Uh,” I started, rubbing the back of my neck.

  “You’re my assistant for the night. We already went over this – whatever I want, you deliver,” Ashley said. “And now you’ve really indebted yourself.”

  Ashley looked up and batted her eyelashes toward me, as if to feign some sort of innocence.

  “Um, aren’t you in the middle of a concert or something?” I asked.

  “It’s an intermission. Sure, I’m supposed to be back out in ten minutes tops. But I’m the star; the show will continue when I say so,” Ashley said, tossing her head to the side and smiling defiantly.

  “Right now, you’ve got to give me one good reason why I shouldn’t post this picture on my online account and broadcast it to my millions of followers,” Ashley said with a mischievous grin.

  “Ok, listen. I’m seriously sorry. You seriously don’t have to do anything like that,” I said. The girl I’d originally pegged as bat-shit crazy was proving to be just that. She stepped toward me again and grabbed at my shirt, pulling the black cotton out.

  Ashley pulled me toward her and stepped up, bringing her lips dangerously close to my own, as she whispered, “You’re going to make it up to me, then?”

  “Yeah, definitely. Whatever you want,” I said, clearing my throat.

  “Excellent,” she smiled. Her lips curled devilishly and her eyes widened with excitement. She brought her lips in and pressed them against mine. At once I could taste her sweet, vanilla tongue on my own as I brought my hand around the back of her tiny, tight frame and pulled her in.

  “Fuck,” I whispered as I pulled back and sighed.

  That’s it? She wants me to fuck her? All I have to do is fuck this smoking-hot babe and I’m off the hook? I wondered to myself. I thought to pinch myself – I must’ve been dreaming.

  “What do you think of me, honestly?” Ashley asked, whispering toward my ear.

  “I think you’re pretty damn hot,” I admitted. “But you probably have millions of guys masturbating to your photos online somewhere, so I doubt that means much to you.”

  I cringed at my observation, but I couldn’t deny that it was probably more accurate than not. Ashley laughed wildly at this. It was a sort of laughter that seemed to hide something – seemed to convey that she’d pulled something over on everybody. And as we touched further, I realized that she most definitely had.

  I pulled her in and pressed my lips against hers again, before making my way down the curve of her neck, biting and caressing with my tongue as the pink-wigged pop-star moaned and signed with release. I ran my hands over her giant, perfect breasts, and she gasped as I grazed over each hard, sensitive nipple.

  “Fuck,” I growled. I wanted her right then and there. I was going to split her pussy open and the only downside would be that none of my buddies would ever believe that I’d banged such a famous girl.

  Ashley pulled back and looked up into my eyes. “You’re willing to make it up to me, then?” She asked again. I nodded, a bit impatient. After all, how could I have made it any clearer that I had no problems making it up to her.

  “On your knees, then,” she insisted. She seemed to enjoy giving demands like this, and her jubilant expression confirmed as much.

  I laughed and shook my head as she fell back into the beanbag chair before me. Her little body sank into the center and she kicked off her red slippers, before reaching under her tutu and grabbing her stockings.

  “Fuck,” I growled, as my cock swelled beyond belief. I grew painfully hard simply watc
hing the fabric roll down those gorgeous, smooth legs and off her feet. I reached down and gave each of her feet small kisses, watching as she sighed and giggled.

  “I’m going to ask you one more time,” she said, with a serious expression returned. “You will do anything I ask to make it up to me?”

  I nodded and said, “Oh yeah.”

  “Good,” Ashley said, before grabbing my hand and pulling it under the red tutu. As my fingers grazed the inside of her thigh, I couldn’t bear to wait any longer. I was going to push her farther back into the beanbag chair, pull her legs out, and eat her pussy until she was screaming for me to stop.

  But as my hand reached beneath the small fabric tutu, I felt something totally unexpected.

  “Holy shit,” I gasped as my fingers wrapped around a giant, stiff cock that was throbbing and warm. Ashley laughed wildly as I lifted up the tutu and saw her massive cock, jutting right into the air, atop two big balls and a tight little asshole.

  “What the…” I said, squinting. “Holy fuck,” I said, unable to believe my eyes.

  “So, I’m a pop-star princess with a little extra,” she laughed. “You’ve got some work to do.”

  “I don’t know,” I said, pulling my hand back for a moment.

  “You said you would do anything,” Ashley noted with a look of frustration. “The other guys…”

  “The other guys?” I said, interrupting her. Suddenly, my mind raced with a million thoughts. “Wait a second,” I started, pointing toward her. “You put that dildo there, and you put that camera there, trying to set me up.”

  Ashley laughed and kicked her feet, before grabbing her cock and stroking it. She sighed and nodded with a smile. “Obviously, I’d have a hard time maintaining my little secret if I didn’t have my bodyguard’s total assurance that he wouldn’t tell.”

  “I hope you’re not too upset,” she squeaked.

  “Mad? Are you kidding?” I said. I crawled up and over her body, grabbing Ashley’s jaw and staring right into her eyes. “Nobody makes a fool out of me. You might think you’re just having a bit of fun, but I’m about to put you in your place.”