Adjusting My Attitude Pt. 08

(WARNING! This story is a FANTASY; in real life, human beings are never property or sex objects and informed consent is always MANDATORY. This story is set in a world where legalized enslavement for crimes, for indebtedness, or by self-surrender is common.)

(Dan Martinson's experience)

If you haven't read the previous sections of this odd tale, you will undoubtedly be confused. If you HAVE read the previous sections, you've probably decided long since that I was an idiot and a total wimp. At the time, I would have agreed with you, but please remember that people do the dumbest things for love.

In brief: I had a superb education and a successful career for the first 36 years of my life. The only failure I ever encountered was my inability to convince Laura Simmons, a beautiful and brilliant attorney, to marry me. Having made her own way in life, she objected (with considerable justification) that I was too spoiled, too entitled to live with, even though we were otherwise very close and compatible. I came up with a crazy solution to her critique: I would strip myself of all my advantages by putting my wealth in a blind trust, sending my staff on a paid vacation, and voluntarily making myself her slave for one year. That way, I argued, she would be free to retrain me to value and support others, putting their needs before mine as a slave is always expected to do. Laura warned me that she would have to be harsh with me, but finally went along with my plan.

She insisted that I go through all the public humiliations and slave market processing that other slaves had to endure. Then she turned me into a domestic servant, having me do all the household chores not only for her but also (one day a week) in the home of my best friend Jim and his wife Terri, who had reluctantly promised to support whatever Laura wanted to do with me. Oh, yeah—I forgot to mention that Laura applied a special form of control typically used for male slaves, installing a chastity cage that caused severe cramping every time my cock tried to grow. And she seemed to delight in encouraging such growth by walking around the house half-naked. Only rarely—4 times in the first 3 months of servitude, when she thought I deserved a reward—did Laura chain me down, remove the cage, and ride my cock in a more-or-less conventional form of love-making. The rest of the time, both Laura and Terri were free to use my tongue to bring them to a climax. Laura went even farther and began pegging me, although to be fair when she did this she always removed the cage so that I, too, might climax from the odd role-reversal of having the woman I love invade my rectum with a strap-on!

As part of my re-training, my Mistress had insisted that I learn to dress, walk, act, and speak as a female. She also encouraged me to think like a female, to "get in touch with my feminine side" so that I would care more about others. I doubt that I convinced very many people that I was a genetic, cis- (or whatever you want to call her) female. Eventually, however, I did become passable as some form of trans-woman (with apologies to all trans-women, who have to overcome great adversity to achieve their true gender identity, and do not deserve comparison to involuntary sissies like me.) I rebelled in the process because she seemed to be humiliating me meaninglessly when she had no respect for or interest in me. By the time I was passable, my relationship with my lover/owner was so disturbed that Laura had to bring in slave psychiatrist Nikki Sheldon to straighten us out. Nikki got us most of the way back together, to the point where I acted less like an outraged shemale and more like an eager-to-please submissive, to which Laura responded with more love and intimacy.

At Nikki's urging, Laura then proceeded to phase 3 of her retraining plan, which involved farming me out to experience various servant roles associated with women. I had succeeded as both a childcare worker in a nursery and an evening-and-weekend fill-in for Laura's paralegal, Jenny, who got to stay home with her two small children while I tried to support our mutual boss. Laura brought that part-time job to a halt not because I failed in my duties but because the managing partner of the firm, who saw me as another transsexual office slave, had me suck him off one Saturday in the office after I crawled under his desk to fix his computer. He actually tried to buy me, so Laura decided I should disappear from the office to avoid further confrontations (and further cocks).

I forgot to mention that I got through that unpleasant episode only because Laura had previously exposed me to a far greater trauma, having me chained on my knees in a commercial glory hole where I had to fellate about 30 cocks in a single evening. Yeech.

The next female service position that Laura planned was actually the first one I had performed—doing household chores as a transgender or at least transvestite French maid. I had already done this for both my owner and my friends Terri and Jim. Now, however, Laura proposed to rent me out to a visiting maid service.

Understandably, the slave maid company first wanted a reference, someone other than my owner who had used my services for household chores. The obvious candidate was Terri, but when asked, she started to joke about the idea:

"Well, I know Danielle [my female persona] is a whiz at cleaning and pretty good with her tongue. But, you keep telling me what a great piece of ass she is—if I'm a reference for her service, I want a sample. And before you ask, yes, my husband has agreed that I can do this. Before he left on a business trip this week, his exact words were 'I don't want to know what you put into Dan, so long as only his tongue goes into you.' So, how about it?" What a friend Jim was, I thought with a wry smile—I foresee some very uncomfortable conversations once this year is over!

Laura's impish sense of humor took over, teasing me. "That sounds reasonable, but I'll have to go home and get my strap-on."

I think Terri was surprised at how fast the conversation was moving but she recovered promptly. "No need, girlfriend! I've got my own cock and lube. I've been wanting to try it out on Jim for years, but he's too much of a chicken to let me. Let me go get them." She hurried off to her bedroom, leaving Laura and I staring at each other.

Raising one eyebrow, she asked, "Are you up for this, Danielle?"

I had mixed emotions, of course—as a guy, I still found the idea of being penetrated disturbing. On the other hand, I wanted to keep Laura happy, and Terri had been my only friend for some time. They could just order me to take it, so I appreciated Laura consulting me. Perhaps she was testing my willingness to serve. Besides, in one corner of my mind there was the sneaking admission that I had come to like being pegged by a woman I cared about, because of the intimacy as well as the chance to get off myself. I decided to give her a slave's answer.

"Whatever you wish, Mistress."

"OK, then, off with your dress, petticoat, and panties, then bend over the back of that padded chair behind you." Once I complied, she hooked my wrists together in front of me, then used my leash to tie the cuffs to one of the front legs of the chair. I suppose I might have escaped if I really tried, but I was effectively immobilized by the time Terri returned. Laura also extracted the remote-control vibrating plug from my butt (after a hiatus of several weeks she had surprised me by insisting on it this morning, an indicator that the two women had already discussed pegging me.) My traitorous cock stiffened painfully against its cage, but externally, I looked like a woman with a somewhat narrow butt, wearing only a bra and restraints, ready to be used sexually.

"Actually," Laura remarked to Terri in a humorous tone, "I think Danielle's been a bit slow to obey today, so let's warm up her bottom a little before you mount her." Suiting actions to words, she began to spank me, but so softly that it was more a teasing caress than a punishment. I felt a second soft hand join her as they both commented about what a nice pink color my butt was turning. I might have felt humiliated by being spanked in such a position, but in fact I was glad to share any form of intimacy with these two lovely ladies. After about a dozen slaps on each cheek, Terri walked around the chair into my field of vision. I had expected that she would wear a strap-on, and was relieved that it didn't appear very large, but I WAS a little surprised that she had removed her slacks and panties to strap the dildo directly onto her crotch. Having serviced her orally on many occasions, I was familiar with every inch of her labia and vagina, but it surprised me that she would expose herself to Laura. I guess she really wanted to get off, rather than simply dominate me.

As she brought the intruder close to my face, Terri used a gentle voice to tell me to "Open wide, Danielle." A second later, she became the third woman to insert a pseudo-prick into my mouth, as I reflected again how much less repulsive this was than sucking a real cock. Fortunately for my breathing, she pumped very slowly in and out and didn't try to shove the entire thing down my throat. Meanwhile, my Mistress continued putting love taps on my exposed butt cheeks while encouraging me with wry comments such as "Good girl, Danielle," and "Bill [her managing partner] was right, you are a GREAT cocksucker." Her tone wasn't cruel or jeering, but actually approving of my performance. Despite these distractions I remembered to set my teeth into the sides of the dildo and move my head back and forth, shifting the butt end of the toy so that it rubbed Terri's clit. My trick was rewarded by a quiet gasp. For a minute, Terri seemed to be enjoying this so much that she had forgotten what the main goal was, but eventually she came to her senses and withdrew from my mouth, moving back around to my rear again. The main event was about to begin.

I am not an advocate for pegging or for any form of anal sex—having been on the receiving end of numerous role-reversal butt-fucks, I've had to admit that, as a man, I had been far too callous about pressuring a woman to let me invade her rectum that way. I don't intend to apologize to Laura, because she has more than paid me back for anything I may have done to HER ass, but I probably did need to look up the other two women who had let me screw them that way. Fortunately, both Laura and I had been gentle and careful when it was our turn to invade the other, and I think we had enjoyed both combinations. Still, I can only imagine how damaging and painful it would be to have someone FORCE a penis or strap-on into your rear end. Even though I trusted the two women standing behind me, my body involuntarily tightened in fear at the impending intrusion.

That said, I have to admit that I had come to enjoy Laura pegging me, because it was a form of love-making and intimacy that brought our bodies together and gave both of us pleasure. Once I adjusted to Terri's initial, very careful insertion into my body, I was able to relax and appreciate the sensations of her beautiful breasts pressing into my back while her soft thighs pumped steadily into me and the head of her lifelike dildo stimulated my prostrate. Laura pegging me was a form of love-making, while Terri pegging me was primarily sex!

Terri quickly vocalized her delight to my owner and me. "Oh, my god! This is so great! Now I understand why Jim enjoys doing me doggie style—it feels fantastic to be in charge, to have the GUY bent over while I fuck HIM rather than let him fuck ME. Oooh, this is such a rush, sinking that rod into you." After that, her speech rapidly deteriorated, to the point where she was mindlessly repeating phrases such as "Oh, yeah! Right THERE! Wham! FUCK you! How's it feel to be fucked, Babe? You love it, don't you?" with each phrase punctuated by another thrust of her plastic penis.

I wasn't much more articulate, to be honest. I didn't realize that Laura had released my cage until I felt her hand guiding Terri's down to fondle my "wedding tackle." That enabled me to enjoy almost as much pleasure as did Terri. I certainly came long before she did, after which I just accepted the steady pounding she continued until a final series of shudders indicated that she had climaxed. She and I lay together, bent over and still joined by her strap-on, until she caught her breath, lifted her body off my back, and slowly pulled out. This was a final role reversal, with the woman choosing to end our intimacy by extracting HER "dick" from MY body rather than the traditional situation where the guy withdrew from the woman.

A few minutes later, I felt a warm, wet cloth wiping me thoroughly back there, after which Laura released first the leash and then my cuffs. After re-installing my cage, she gestured for me to get dressed again, although I sensed that my makeup and hairdo needed repair.

Terri was gushing with excitement. "That was even better than I imagined. Thank you, thank you, Laura, for letting me do this! And thank YOU for being my sex toy." She said, winking and kissing me on the cheek to take the sting out of her words. "I mean, I knew you were good with your tongue, but now I know you're the finest fuck a girl could ever want."

"You'd better not let Jim hear you say that," Laura replied, lightly.

"Mistresses," I said, being careful to preface a wise-ass remark with the correct title, "Why does this feel like one of those stories when an older guy helps a younger one reach adulthood by hiring a hooker, and I'm the hooker?"

Laura grinned. "That's because you ARE the hooker, sweetie. But don't worry, you're MY hooker." She hugged me briefly and kissed my other cheek. "Besides, I am NOT older than Terri! Anyway," she continued, "I'm sure Danielle would be happy to have you peg her again, Terri, but let's not risk it except when Jim is out of town. Your husband may have agreed to this in theory, but I'd hate to think how he would have reacted if he walked in a few minutes ago and saw his wife bending his best friend over to penetrate him."

(Terri did find several more opportunities to peg me during my remaining indenture. She assured me that she never told Jim what she had done with me, but I still dreaded future conversations with my friend. I would definitely have to stay sober around him for the next few years so I didn't let anything slip. Come to think of it, drinking with Jim was where I got the dumb idea to enslave myself to begin with. That thought was enough to make me join AA.)

*****

After such a lurid, detailed introduction, the reader may be expecting similar tales of debauchery in the suburbs when I worked as a slave maid for hire. Would that it were so. In fact, the next several months were mostly drudgery. Several days each week, Laura and I would rise very early so that she could drop me off at Collared Maids LLC, from which I put in long, humdrum days cleaning houses while wearing a very drab but practical maid outfit. (Who would ever have thought I would criticize a maid's uniform for being drab?) By this time, the combination of practice, diet, exercise, and clothing had given me the appearance of a true female. Not only was the work boring, but Collared Maids followed all the conventions of slavery. Along with a group of other slave maids, I rode in a minivan with my hands and feet cuffed and tethered to the floor. My handler, Mistress Carolyn, always used leashes to tow the cuffed maid or maids up to the door, unlocked the building if the owner weren't at home, and then released the maid(s) to work, leaving him/her/they with bottles of water and sandwiches for lunch. When she returned to pick me/us up, she would inspect to ensure everything was done properly.

Sometimes, if more than one of us shared a larger job, we maids were able to talk with each other, relieving the tedium. When the female owner of a home—often a trophy wife—was present, she frequently was so bored and lonely that she was glad to have a conversation with me. Of course, this sometimes degenerated into me servicing her orally, which bothered me only because I might fall behind on the assigned work. One day after I had worked for Collared Maids for two months, the husband came home unexpectedly and took offense at finding a shemale slave licking his wife to orgasm. (Personally, I think he should have been grateful that he didn't have to do that for her, which he apparently avoided, but he didn't look at it that way.) Fortunately for me, since I wasn't allowed to defend myself, he decided not to beat me but to use my mouth as well, becoming the 33rd or 34th (I'd lost count) cock I had to suck that year. Yeech again.

The owners said nothing about this to Mistress Carolyn when she returned to pick me up, but I needed to cover my bases against later complaints, so when we got back to the office I politely approached her.

"Mistress, something happened today that I believe you should know about. I'm not complaining, of course, but the owner of the house made me suck him off."

She was unfazed. "Humm, I'll have to charge him for the blowjob. Did you lick the mistress as well?"

"Yes, Mistress, she's had me do that for the last three visits."

Fortunately for my peace of mind, these two people apparently objected to being billed for my oral services, because they cancelled the cleaning contract!

*****

Soon after that incident, Laura decided it was too much bother for her to drive me to and from Collared Maids, so she sent me back to the childcare center. I was overjoyed to be back in a more sociable and permissive environment, and Mistress Helen was glad to have my help. (All this time, I still spent one day a week at Terri's and frequently serviced her orally on the side. Jim still pretended not to know about the side service, but usually managed to be absent on the days I cleaned his house.)

Laura had interviewed me after each of these occupations—childcare worker, secretary, and maid—and appeared satisfied that I had re-oriented into a service mindset. I began to hope that she would let me finish my indenture working for Mistress Helen and (maybe) even love me thereafter. Unfortunately for my peace of mind, she had one more experience to expose me to.

On a Saturday, she took me out for one of our infrequent "girls shopping trips" and lunch. This was always fun for me and, I think, for her. I was selfish enough to be glad that, after that one Friday night hookup with a junior lawyer, she had not dated again, but she worked so hard at her career that she did very little socializing. She was much more affectionate to me than she had been during the first few months of my slavery, and made regular use of me for licking, pegging, and female-superior coupling, but she wasn't getting enough interaction with others.

At lunch, she told me of what proved to be my final challenge. She had found an LGBT-friendly restaurant and bar that would "employ" me as a waitress on Friday and Saturday nights, when it was busiest. I use quotation marks around the word "employ" because, being a slave, I didn't get paid—they paid my owner the minimum hourly wage for my service. In practice, I did get a few tips, but I felt obligated to turn that money over to my owner because I knew she was spending more on me than my blind trust paid for my upkeep. It sounds funny for a guy worth $200 million to be worrying about a few bucks in tips, but I didn't want to put Laura to any expense. After all, this whole situation was my idea, not hers, even if she got some value out of my slavery. (That one sentence, by the way, summarizes my mantra for still loving her despite all she had put me through.)

After lunch that Saturday, she took me to a uniform supply store and bought two simple waitress outfits—bellow-the-knee black skirts and white blouses. Then she drove me to the restaurant/bar and introduced me to the manager, Master Chuck. She also gave me a bus pass and showed me the schedule at the nearest bus stop, about two blocks away from the restaurant. She left me so that Chuck could give me a brief orientation and then put me to work that evening.