Special thanks to Ed Miller for creating Jackie in his classic "Addicted." This story always screamed MORE to me. It took me thirty years and my entire family fortune ... and here it is.
I took a long, slow deep breath and pushed the button. The five or six seconds that I waited for a response felt like two or three million years. "Yes?"
"Hi, is Jackie there?" I said through the speaker.
"Um, who is this?"
"My name is Chase."
"Ok, Chase is it? Who are you and what do you want with Jackie at this hour?"
"Well, um ... could I... ," my voice cracked, "talk with her face to face, it's kind of private."
"Listen Chase, I'm not in the habit of letting men I don't know in to speak with ... Jackie at... 1:30 in the morning."
I felt the tears and the emotion beginning to surface. I tried to hold it back, but it was no use.
"Please, I HAVE to speak with her," I cried. "I've spent the better part of the last two years looking for her. Please."
"Two years? What are you talking about?"
"If you let me in, I'll explain everything ... and everything in the briefcase is yours." I saw the camera globe above the door and propped the aluminum Zero Halliburton briefcase on my knee. I snapped open the case.
"How much is in there?"
"Five figures. Please."
She took a long moment before answering.
"Just so you know, I'm a 4th degree black belt in karate, and highly skilled in Krav Maga -- no funny business. Am I clear?"
"I'm in suite --"
The buzzer sounded, the door clicked and my heart almost leapt out of my chest. I opened the gate and entered the courtyard. The courtyard was small and the whole building only had twelve apartments so number six was easy to find. I rang the bell. I was petrified and excited beyond experience.
The door opened to reveal a dark interior.
"I'm Chase. May I come in?"
"Remember what I said."
I opened the screen door and walked inside. The screen door shut behind me and presumably the voice's owner closed the heavier door. A light flicked on.
The woman before me was quite beautiful, with deep brown eyes and nearly as tall as my six feet, with lush dirty blonde hair past her shoulders. From all of my experience, she was showing off as if she had perky D-cups, but that might easily be false advertising courtesy of a push-up bra. Or it could all be her. I didn't know how it worked and I wasn't sure she could affect herself.
"Are you Jackie?" I asked the woman.
"Give me the briefcase and start talking. Wait, what's on your back?"
I handed her the briefcase and told her there were clothes for me in my backpack. I explained that if she could do what I thought she could do, the contents of he briefcase were hers. For the briefest of moments, I swear I saw a twinkle in her eye.
"Well?" she said as she sat on her couch.
"Like I said, I'm Chase. But I would prefer ... um, what I mean is that I..."
I stopped and took a big deep breath.
"You mean, what? Now sit." she asked, clearly reveling in my discomfort.
"I'd prefer to be Barbie," I answered her as I sat next to her.
"I see," she said with a large grin, "What makes you think Jackie can help?"
"You are Jackie, yes?"
She looked at me for a few moments like a lepidopterist looks at a butterfly, and then smiled. "Yes, I'm Jackie. What makes you think I can help you?"
"A lot of research I've done over the past two years. It seems you have some type of power. There have been so-called fictional stories written about you and this power ... I spent a lot of time and money trying to figure if it -- and you -- are real."
"I'm real, that's for damn sure, but a 'power'?" she gestured in my direction, "Didn't you check this out with Snopes.com and the other urban legend sites?"
"That's what is so interesting -- " My vision blurred and I felt like someone just made solid contact with my head during a nasty pillow fight, yet it disappeared as quickly as it arrived.
"You ok?" she asked.
"Yeah. What was I saying? Um?"
"You looked at urban legend sites..."
"Right. There's not a mention of you or this power at all. I took that to be a very good sign."
"Interesting. The fact that you couldn't find anything about me aside from some fictional stories proved to you that I existed?"
"Using negative proof isn't easy, but if you really had a power of this kind and it existed, it wouldn't be talked about anywhere. You'd be buried so deep in some lab somewhere, you'd probably never see sunlight again."
"That's not really a pleasant thought."
"Exactly. So ... do you have a 'power?'"
"What would this 'power' do?" she asked, clearly playing with me.
"I believe it could transform a man into a woman, possibly more."
"That could have its uses," she said as she waved her hand in my direction.
My vision momentarily blurred as my head went all cottony again. And it was once again gone as fast as it came; yet this time I noticed heaviness on my chest and looked down. My brain couldn't process what appeared to be two large mounds under my shirt. "What ... but ... I... ?"
"Isn't that what you wanted?"
"But ... I ... How --" and my eyes rolled back in my head and I promptly passed out onto the couch next to Jackie.
Jackie smiled. "Aw, Chase, too much of exactly what you wanted? This is going to be the most to be the most fun I've had in quite awhile."
I woke up on the couch next to Jackie and immediately put my hands to my chest. Nothing out of the ordinary at all.
"Hey there sleepyhead. You alright, or are you going to pass out again?"
"You did something to me. I swear that I had tits for a minute."
"Why would I do that?"
"Because you can."
"I can? Cool," she crowed as her big brown eyes sparkled and got larger to emphasize her words.
"Did I imagine it?"
"You tell me," Jackie said with a chuckle as she scooted up next to me on the couch. "Do you find me attractive Chase?"
"Um, well, yeah, you're beautiful."
Her eyes bored into me as she said, "Thank you, Chase." Jackie scooted even closer forcing me to move in the opposite direction -- a direction that had the arm of the couch in the way. "Did you know you're making me wet?"
"I am?" I gulped.
"Yes. Very. My nipples are quite hard as well, but you can see that through my shirt."
I glanced down to her chest and clearly saw her seemingly rock hard nipples practically calling to me. I couldn't find my voice.
"Aw Chase, cat got your tongue?" She reached up and gently stroked the back of my head.
"I'm fine, " I said unsteadily. "Why are you telling me this?"
"Well, wouldn't you like to feel what that's like? To get wet. To feel your nipples get hard. To want to be filled. To feel these," she hefted her tits, "resting softly in your bra ... Among many other things?"
The only answer I could give was one where my eyes got wider than dinner plates and my world started to swim.
"No answer, ok. I guess you don't --"
"N, no. I do. Really."
"Really? Is that why you're all flush? Or maybe it's just a fever. Lemme feel your head."
Jackie leaned over, pushing her right breast into me and wiping her hand across my forehead. Now I felt hot, faint and cotton-headed. And intensely horny.
"You do seem warm to me."
"It does feel warm in here."
"Why don't I distract you from the heat?"
"Why don't you distract me from the heat."
In one motion, Jackie leaned over me and straddled me while pulling her shirt off to display her bra-clad D cups. "Is that better?"
I'd never been so hungry and turned on ... and scared in my life. "Are you going to change me?"
Jackie began grinding her hips into me, up and down and back and forth. "Change? I was planning on fucking you, you're pretty damn cute and I haven't been laid in awhile. What kind of change are you talking about?"
"To make me a girl."
"Don't you want to fuck me?" as she leaned her tits into my chest. I couldn't respond because for an eternal instant, I felt her tits as if they were my tits.
"Can't talk? How 'bout a kiss?"
Jackie leaned into and kissed me. It was a kiss that was so deep and so complete, combined with the feelings of her chest and mine, short circuited my head and ... I was gone.
Jackie pulled away from the kiss and straightened my hair. She was flush all over her chest. Her nipples were visible through her bra and looked as hard as drill bits. She ground into me one last time and then moved off of the unconscious me. "So easy," she said with another glint in eyes.
"Can I help you?"
"Are you Jackie?"
"Yes. Are you Chase?"
"Please come in, quickly." Jackie looked good enough to eat and I would have loved to, except I wanted to be her more than I wanted to do her.
"You have luggage?"
"If you can help me, the briefcase and its contents are for you. The bag is for me."
"I understand you can turn men into women."
"I can do what?" Jackie asked with an amused look on her face.
"I believe you can turn men into women. Is it true?"
"You can?!? I searched you out for years, but I didn't really believe it was possible."
Jackie looked me up and down and back up again. She let the grin face from her face.
"Oh it's possible ... it's just that I'm not sure I want to do it."
"I have a lot of money in the briefcase," I said as I was overcome with a strong feeling of déjà vu.
"Are you ok, Chase?" Jackie asked.
I hesitated and locked onto her eyes. "Have I been here before?"
Jackie laughed. "Not that I know of. Now you were saying something about the briefcase?"
"There is nearly $25,000 in that briefcase for you if you can help me."
Jackie's eyes lit up as she tried to hold her excitement in. "That's a lot of money."
"Jackie, please, tell me what I need to do to convince you."
Jackie looked at Chase, like she was thinking something through and pulled her shirt over her head. She was clad in a beautiful pink bra.
"Put your hands on my tits."
"Chase, most men wouldn't question that command."
"But, um ... this seems familiar."
"Does that mean you don't want to touch me? Do it. Now."
My hands went directly to Jackie's tits. They felt as wonderful as they looked. Jackie sighed a pleasurable sigh.
"Go on, squeeze 'em," she said with a glint in her eye.
I overcame my embarrassment and began to gently knead them. A few seconds into this instant trip to second base, I felt a brief tingle shoot through my entire body. Jackie's eyes bored into mine. I continued touching her tits and a wave of disorientation came over me. I felt like I was touching my own chest. I squeezed them and I couldn't form words or thoughts. It felt like I was perpetually passing out.
"Do you like that?" Jackie cooed. She looked at me like a predator who just caught her prey.
I couldn't say a word. Jackie laughed. "I guess you do from the look on your face. But, too bad."
I managed to make an unintelligible noise.
Jackie smiled at me hungrily and said, "Nighty night." I saw her wave her hand out of the corner of my eye. The feeling of her tits as my tits swallowed me up and I was, once again gone.
I woke up on the couch, feeling very disoriented. Jackie was right next to me and I had a cold compress for my forehead.
"Not telling," she grinned. "I like you, I like how shy you are about what you want, I like how you've been respectful of me -- well other than ringing my doorbell at 1:30 in the morning, but I can understand." She took a few moments. "And you're kinda cute," she paused. "Barbie."
It took me a moment to realize what she called me.
"I've decided I'll help you. I'm a bit bored anyway."
I sat up, a dump of adreneline poured into my system. My breathing got short, my cock gained iron bar status and my vision got swimmy. "Really?! What do I need to do?"
Jackie laughed softly. "My, we're anxious."
"I'm sorry, I guess I am."
"Aren't you embarrassed? I mean, most guys who want to be women don't exactly blurt it out."
"I'm insanely embarrassed, but I'm way past that. And it's not like you're someone I hired to pretend that I'm a woman where I'll feel shame; You're actually going to do it to me. For me."
She tossed me my backpack.
"Go ahead and get dressed."
"Where should I go?"
"Just change right here ... I mean, you're going to change right here anyway."
I dumped the contents of my bag onto the couch. Jackie looked over my girl clothes.
"I see you like Spandex."
I was feeling a little faint; like that kid on Christmas morning who wanted a particular gift but never thought in a million years he'd actually get it. I'm pretty sure I'd never had so much adrenaline in my system.
"Yeah," as my eyes became transfixed on Jackie.
As I was fumbling with my girl clothes, Jackie slid her jeans off to reveal a perfect set of legs and a sexy pair of satin panties. She placed her right hand at the left bottom of her shirt and the same with her left hand on the right side. In one motion, she pulled her shirt over her head to reveal an absolutely killer body, that featured a satin bra that held picture-perfect D cups (which matched her panties) and a flatter-than-flat, perfectly toned tummy. I was nearly at a loss for breath.
"You're absolutely gorgeous Jackie."
"Thank you. Your turn to do the opposite."
I took no measures to insure my clothing wouldn't stretch and showed no pretense whatsoever. I pulled off my clothes as fast as I could. I was naked and excited beyond words. In a moment, I would crossdress in order to become a woman in front of this gorgeous woman and I was about as hard as I'd ever been in my life.
"Damn, you're a healthy boy. You really want to give that up? We could have a good time..."
I couldn't meet her eyes, but drank in her body. I closed my eyes, shook my head lightly and softly said, "I'd love to, but I have to ... I need to..."
My voice died out right there.
"Chase, look at me," she said very softly.
I did sheepishly, and saw a kindness in her eyes.
"It's ok. Really," she gently touched my cheek. "Now get dressed."
I took a deep breath and sat on the couch. I went to pull on a pair of purple satin panties, but had a problem. My cock was harder than diamonds with no sign of retreating.
I looked at Jackie. "Um?"
"What's the problem?" she looked down. "Oh whoa. I see. Seriously, you don't want to... ?"
I pled with her with only my eyes. She gently nodded and looked right at me. Jackie gestured with her hand in the direction of my crotch. Immediately, I felt a charge run through my cock, somewhat like moment just before orgasm but it was gone as fast as it arrived. With it leaving, I felt my cock deflate and my arousal amp up even more. "There you go."
Now that that issue was taken care of, I pulled on that pair of panties and tucked everything away to create the illusion of a female crotch.
"That's a good look for you, but I bet I can make it better. A lot better."
I really couldn't respond to her anymore. I still felt a kindness from her, but coupled with my somewhat buried embarassment, I knew she knew what this experience was doing to me and I'm quite sure she was getting off on it.
I pulled out a near-black satin 40DD bra and strapped it on my chest by reaching behind me and securing the hooks into their eyelets. I reached for my breast forms.
"That was some impressive bra work. I know a lot of women who can't clip their bra when it's behind them. Leave the forms, you won't be needing them." I simply nodded. I needed to focus on dressing and breathing.
I pulled on my beautiful shiny lilac spandex catsuit, which covered me completely from the tips of my toes to my neck. I went to reach around to pull the back zipper up. "Turn around, I'll do it," Jackie said.
I stood and set my back to Jackie. She zipped me up. "I kind of like the slutty 'look-at-my-bra-under-my-shirt' look. It's a good one for you, but the head really doesn't go with the it."
Jackie held her arm out, in a kind of a wave and I once again felt a small tingle run through my body.
"Omigod," I squawked as I felt like the world was going to swallow me.
Jackie tapped me firmly on the forehead and said, "Enough. You will not pass out."
Jackie's hands began to gently caress me starting at my shoulders and roaming all the way down my body. I started feeling a ripple in my midsection as Jackie just smiled at me, still looking amazing in her bra and panties. The ripple extended down to my hips, cock, my thighs, legs, calves and feet. It settled in my feet and I felt them getting smaller. There was no pain; it was like a very strong invisible massage.
"Tell me what you want."
"I already told you."
"I know, but say it again. I want to hear it."
"I want you to make me a girl."
"What kind of girl?"
"Like Barbie. Big heavy tits, wide eyes and a tiny waist."
"Is that all?"
"A pussy. A pretty face. Long hair. Sensitive," as I lowered my eyes and my voice trailed off.
Jackie took her hand under my chin and raised it up so our eyes met. "And?"