tagTranssexuals & CrossdressersPayback Ch. 01: Entrapment Begins

Payback Ch. 01: Entrapment Begins


The phone started ringing at 9:44 pm. That seemed awful late for a non-emergent call, but I let it ring anyway. "Call from San Diego, Kaw," it said, and again, "Call from San Diego, Kaw. I guess the telephone voice machine didn't know that CA stood for California not "Kaw." I get so many crap robo calls that I only answer calls that my system identifies by source using my google contact list. This wasn't one of them, so I let it ring knowing that robo callers don't leave messages. I figured if it was important the person calling would.

I went back to watching the news, but a few seconds later my phone system beeped, indicating that I had a phone message. I was surprised . . . . none of these solicitors ever left messages. I entered my access code and heard a sweet feminine voice say, "Hello, Mr. Andrews. This is Julie Jordan calling and I have something important to discuss with you. Please call me back as soon as possible."

I knew my system had saved the number this person had called from, but, since she didn't leave a call back number, I figured I could ignore her request. What these solicitors wouldn't try, I thought.

At 10:12 pm the phone rang again. Again the synthesized phone voice said "Call from San Diego, Kaw." I didn't answer. I now had lost interest in the news and waited to see if there was another message beep . . . . there was.

"Hello again, Mr. Andrews, please do call me immediately . . . . I have possession of your key."

"Oh God," I thought as a tingle of fear vibrated through my body. I even forgot to breathe for several seconds. This couldn't be happening. I know that Chris threatened to do this, but I never thought she actually would. Recently she had had me fitted with a very tight, and very secure, padlocked male chastity device. This cock cage was supposed to guarantee my faithfulness to her while she went off on a round-the-world cruise with her band. Now I was wondering if I could really get the thing off without injuring myself. Then the phone rang again.

I couldn't answer it. I needed time to think. "How does she know I'm even home to get these calls," I wondered.

A few seconds later the message beep went off again. I didn't listen to it. I couldn't . . . I had to get my wits together.

I decided I was panicking for no reason. I didn't even know this woman wanted. I mean, it might be extortion or profiteering, but maybe, just maybe, she wanted to sell the key back to me.

I pushed the play button.

"Listen, asshole, enough games, call me now. I also have your laptop and it's fully loaded." The female voice now had a sharp, demanding edge.

I couldn't believe it. My heart was racing and I broke out in a cold sweat. Now I had to call . . . my whole life was in jeopardy. I pushed the call-back button.

"Hello, Ray, I'm so happy you decided to call. I was starting to get concerned about losing my investment," said the now friendly voice.

"Who are you?" I asked.

"I told you, Ray, I'm Julie Jordon."

"What do you want?" I queried.

"I want you, Mr. Andrews," she said.

"I don't know what you mean. What are you talking about?"

"Chris Arnold has sold your care and control to me while she's off cruising the world. She has named me as the "delegate" on your slavery contract. I have the key to your chastity device, your laptop loaded with kiddie porn and a written agreement making me your Mistress."

"Why would you do that?"

"Because you owe me, Mr. Andrews. You owe me big time . . . and I'm going to collect that debt. As part of that repayment you are going to do anything and everything I tell you to do." The voice had turned nasty and cold.

"What are you talking about? How do I owe you? I don't even know you." I stammered.

"Oh, but you do, Mr. Andrews. I wasn't always Julie Jordan. Eight years ago I was Jack Jordan and I was in your class at Marshall Continuation High. Or, at least I was until you had me expelled."

'Jack Jordan,' I thought. Yes, I remembered him. He was an uninterested student who paid little attention when he rarely attended classes. He was slightly built, a little effeminate and thought to be gay. It was rumored that he was selling blow jobs in the school parking lot for five dollars. I had warned him several times about his attendance and study habits, but he had always pleaded with me to give him another chance. One day I caught him selling marijuana to another student and a later search of his locker turned up salable quantities of other drugs. His case went to the school superintendent and, when consulted, I recommended that he be expelled. On his last day at school, we crossed paths in the parking lot and he grabbed my sleeve.

"I hate you, Mr. Andrews," he said. "You could have gone to bat for me and got me another chance, but you didn't. Now I've got no place to go. I can't stay home and I can't go anyplace. I hope you're satisfied with yourself, but you've ruined my life and I'll never forget it."

I never saw Jack again.

I found out later, from another student, that his mother was a local tramp who was well known to the local police. His father was in state prison for molesting a neighbor boy. The student also claimed that Jack told him that his drunken father had forcibly sodomized him many times starting when he was eleven years old.

"Yes, I remember you, Jack," I admitted.

"Good, Ray, I'm happy to hear that. That way you'll understand the rationale for what's going to happen to you."

"And what's that, Jack?"

"Don't ever call me Jack again," the voice almost shouted. "I haven't been Jack for years and quite probably never was. I believe I've always been a female even when I was forced to be a boy. I think I've always been a girl who just happened to be born with a dick instead of a vagina. I think like a girl, I act like a girl, and for the last several years I've lived completely as a girl."

"I apologize. I can understand how you feel. As far as your expulsion goes, I really had no choice. I had already given you several chances and the dope thing was the last straw." I offered.

"Fuck you, Mr. Andrews, you never cared. You never tried to talk to me. You never knew what I was going through. You could have helped me, but you didn't. If you would have checked you would have found out that I was sucking dicks and selling dope to have money to live. My miserable father was in prison and my alcoholic mother would spend every dime of her unemployment check on booze and cigarettes. There was never food in the house. I ate almost every meal at fast food joints bought with the money I made on the streets," he ranted.

"I'm sorry. I really didn't know any of that," I said. I really did feel bad for him . . . her, but there was no way that I could have gotten involved in a student's personal affairs. I had errored and done that once before in my career and couldn't let it happen again.

"I know they had counselors at the school that were supposed to handle stuff like that. Didn't they do anything?" I asked.

He laughed, "Yeah, right . . . when I told them what was going on in my life, they called the probation department and had me sent to juvenile hall. That was a really big help. There I had to suck cock for free just to survive. When I was finally released a gang of midgets on mopeds could have ridden in and out of my asshole."

"Look Jack . . . sorry, Julie, I'm very sorry about what went on in High School, but that was a long time ago. Right now I'd like to get the key and my laptop back. How much do you want for them?" I asked.

"Is that what you think teacher, that I bought them to make a little money blackmailing you? How wrong can you be for a smart guy? I bought them to get revenge. I plan on making your life as miserable as mine was because of you." she hissed.

"Julie, again, I'm sorry for what happened to you, but we've both moved on in our lives. Those items are valuable to me and have no value to you. I'd be willing to give you . . . ah, a couple of thousand dollars for them."

"Wrong again, Teach, they're worth a lot to me. All those little naked kiddies on your laptop guarantee me your loyalty and obedience for the rest of your teaching career."

"Listen, Julie, please. I'm begging you just take my money and let me have my stuff back. I absolutely meant you no harm." I pleaded.

"Listen up, Ray! If it wasn't for you I wouldn't be what I am today. After you expelled me I damn near starved. I had to move out of my Mom's house 'cause every drunken asshole she brought home would try and put the make on me. I was staying with a high school friend when one of my blowjob clients told me I was very cute and could make a lot more money giving head if I did it as a girl. I thought about that for a couple of days and then went over to the local thrift store and bought some girl's clothes. That night, I looked more like a boy in a girls dress than a real female, but I still had more "dates" and made more money. The next day, I drove across town to a beauty shop that specialized in "transitional" makeup and spent most of it. That night I made even more and I never went back to being a boy."

"I'm sorry, I'm sorry, I'm sorry. I'll do anything I can to help you. I'll pay for some psychological counseling and we'll get you back on the right track." I offered.

"Right track? You cretin . . . finally, I'll be on the "Right Track" you think? I've wanted to be a girl ever since I can remember and now I am one. You're so stupid; this is exactly what I've always wanted."

"So what do you want with me?" I tried.

"You're going to work for me."

"I already have a job."

"This will be a part time job and besides, you're on summer vacation right now." She said.

"What's your business?" I inquired.

"I think of myself as an agent although others might call me a facilitator or expediter. I represent clients who are seeking certain types of specialty employment and I match them up with employers who desire the services they offer."

"That sounds like interesting work, but I don't need a part time job. I'm really not interested," I told her.

"Listen up, dipshit. You don't have a choice in this," she snarled. "I looked over your laptop and Chris' computer guy did a wonderful job. He intermingling the kiddie porn with actual photos of your students and even family pictures. If I turn it over to the school district, you will not only never work as a teacher again, you'll probably be sent to prison on felony charges. You know what they do to child molesters in jail."

"Please, please, Julie, you can't do that." I pleaded because I knew that with my prior incident she was almost certainly right about the outcome.

"Meet me for lunch tomorrow at Lyon's and we'll talk about your new position," Julie said and the line went dead.

* * * * *

I met Chris on a cruise. I was working as a bartender and she was a singer with the band. Chris was one of most beautiful women I have ever met. She looked to be in her early thirties and was tall, attractive and statuesque. She had a narrow face with high cheekbones, large deep set green eyes, and full natural lips. Her hair was an auburn color and flowed in waves around her face to her shoulders. She had a smattering of freckles across her cheekbones and a dimpled chin. She had full "C" cup breasts and a narrow waist above wide hips. Conversations in a room stopped when she would walk through. Frequently she wore skin tight yoga pants and a cut off top that left her midriff bare. I was absolutely enchanted.

Off duty, we both pretty much had the run of the ship and since we both worked nights, we would see each other frequently to nod and say "Hi." She was so gorgeous that I was thoroughly intimidated and never went beyond our occasional greeting.

One afternoon I was reading by the pool, cooling down after a run around the deck, when she walked by, stopped, came over to me and stuck out her hand.

"Hi, I'm Chris. Mind if I join you?" she asked.

I was so surprised that I could barely speak, "Yes . . . . I mean, no . . . . sure, please do," and fumbling with my book, finally stuck out my hand.

"And you are?"

"Oh, sorry, I'm Ray," I stammered.

Chris started to sit on the bottom of my chaise lounge and I had to quickly move my legs to accommodate her.

"Glad to meet you, Ray," she smiled with her beautiful white teeth. "I never see you with anyone, are you on the cruise by yourself?"

"Yes, I am. I'm not a passenger, I'm a teacher on summer break and I'm working as a bartender."

"Wow, how nice for you. I don't see a ring, are you married, Ray?"

"No!" I laughed, "Never found the right one."

"Well that's too bad, you're certainly a nice enough looking fellow," she complimented as she lay her hand on my bare knee.

"Are you gay?" she smiled.

'Oh, boy,' I thought. She doesn't mess around with small talk.

"No, just haven't found the right girl," I repeated.

"Well, well for me. While we're cruising around, how would you like to keep each other company?"

I couldn't believe what I was hearing "keep company" with the most gorgeous girl on the whole ship. "Yeah, sure, I'd . . . I'd, uh . . . really like that."

"Good, good, I need someone straight to spend some time with. The two guys in the band are swishy gay lovers and the other girl, LeeAnn, is a transsexual like me, but a real bitch. She keeps trying to put the make on me and when I turn her down she just becomes a giant cunt. I keep telling her I don't swing that way, but she just can't seem to get it through her head." Chris confided.

I couldn't believe what I was hearing. I was stunned. Did I mishear? Did she just say she was a tranny? I automatically glanced down at her crotch to see if I could tell. She caught me looking.

"Oh," she said, "you can't tell by appearance. I'm not that huge and I use medical tape to keep it back between my legs. Sometimes that hurts a little or I get a rash, but usually, it's fine. I'll show you how I do it sometime if you like."

She swung her legs around on the chaise and spread them a little. "Can hardly tell can you?" she questioned as I looked her over.

"Uh, no, no . . . . it looks just fine," I mumbled. I was so shocked and confused that I could hardly think, let alone combine words together. Was I going to wake up in a minute?

"You're probably a little surprised, but I've found over the years that it's best to get my sexuality out in the open right away. There's too much time spent messing around otherwise. You date a guy for a while before you tell 'em and they get offended or pissed or even nasty. If I tell them right off the bat they either take it or leave it. Makes everything a lot simpler don't you think?"

"Uh, uh . . . yeah, I guess so."

"So where are you, Ray. Do you take it or leave it?"

'Wow, what do I do?' I thought. 'She looks like a girl, she acts like a girl, and she's as pretty as any girl I've ever seen . . . . but, jeez, she's got a dick.'

"It might help, Ray, if you just think of me as a real girl with something extra."

'She's right,' I reasoned. 'She's certainly not anywhere close to being a man in any other way. And it's not her fault she was born with a penis.'

"I think I'm okay with that," I said softly.

"Great, that's a relief because I think we could really hit it off." She gave me a big smile and slid her hand down my leg to my crotch and rubbed her hand over my dick."

"There are a couple of other things we ought to talk about though," she confided.

"What's that?" I hesitantly inquired.

"I like kinky sex," Chris proclaimed. "I mean sex with a tranny like me is already going to be different, but I like to take it somewhat further on the wild side. Don't get me wrong, I'm not into real serious stuff and it would all be with mutual consent and safewords."

'Jesus,' I thought. 'I can hardly believe what I'm hearing. I met this gal a few minutes ago without even a date and she's talking about kinky sex acts.' I had a rock hard boner and my brain was swimming. A previous relationship had been with an older widowed neighbor who wanted to try just about any sex act imaginable. Carlotta would browse the internet for new and different stuff. Although reluctant at first, I found myself as excited as she was about new sexual adventures. She almost always took a dominant role, but that was fine with me. She sometimes called me "Bitch Boy" and I found that to be kind of endearing. Being ordered about always made me more accepting of some of the weird things she had me do. I guess I figured that being ordered to do those things by my "Mistress" made them okay. It was kind of like I just did these strange things to keep her happy and satisfied and not that I actually enjoyed them . . . . but I did. I loved our relationship. I would still be seeing Carlotta if she hadn't married another neighbor a couple of years ago.

All this flooded through my mind as I was trying to organize my thoughts to give Chris a response.

"I think I'm okay with that," I said. As the words came out of my mouth I wondered, 'what if this is really sick stuff, so I added, "What kinds of things are you considering?"

"Oh, well, like I said, nothing real heavy . . . no scat, no blood, nothing real painful. Some spanking, a little S&M, some bondage, D&S for sure . . . you know, stuff like that."

She must have noticed the hard-on in my shorts because she used her hand resting on my bare thigh to slip up the leg gap in my shorts. She grabbed my penis and gave it a painful squeeze. "And maybe a little cock and ball torture if you like that." She said with a mischievous grin.

"You know, I've done a little of that stuff before and I think I'm alright with that." I said, thinking those were exactly the things I liked.

"All right, this is going well. I think we're in agreement and are going to have a great time together," Chris said, "But, there is one last important thing."

'Oh crap,' I thought, 'I hope this isn't a deal breaker.' This whole thing was perfect. I had really missed the fun I had had with Carlotta, my neighbor, and had always hoped I could find someone else like her.

"I like to be in charge," she announced.

'Oh, my God,' went through my mind. 'This is perfect. Just that kind of thing I've been hoping for . . . . If only she didn't have a dick.'

"If that makes you happy, I think that's all right with me," I agreed with a sincere smile.

"Yay," she screamed and jumped on top of me. "We've got a deal."

Her weight on top of me misbalanced the lounge chair and it went over backward with our feet ending up higher than our heads. Chris wrapped her arms around my neck and held my head firmly in place while she gave me the most sensual lengthy French kiss I've ever had.

Other passengers were walking by and staring at us, but Chris made no attempt to move. After the kiss, she still held my head in place. Then she whispered in my ear, "We're already four days into this cruise, but I'm going to use and abuse you as much as possible in the remaining ten days. Do you have a roommate?"

"Yeah," I replied, "another bartender."

"That's okay, we can use my room. My roomie, LeeAnn, has hooked up with a housekeeping supervisor and they've taken up residence in an empty passenger cabin. My room is very private; it's got a stairway on one side and a storage room on the other . . . . nobody will hear you scream," she laughed as she bit my ear . . . hard!

We disentangled ourselves from the lounge chair while I tried to conceal my erection.

"My room number is 311. Be there as soon as your shift ends tonight," Chris said in a tone that made it sound like an order.

"I'll be there," I replied as she turned and let me admire her great ass as she sashayed away. Half a dozen steps later she turned, gave her crotch a yank and thrust like Michael Jackson. Then she followed with an exaggerated wink and turned away.

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