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Tom was a nice guy. Sweet. Kind. Considerate. A great friend. But he wasn’t sexually exciting. Nothing. Not a turn-on.
He was totally in love with me. And, yes, I love back, just not in “that way”.
We were good friends. I could trust him. We even shared an apartment (separate rooms, of course).
And he was a great housemate. He did all of the household chores. The cleaning, the laundry, the vacuuming, even the cooking. And he was a hell of a good cook. It worked out great.
One day I came home early and discovered him in my clothes! He was frantically attempting to get out of my lingerie. He was standing there leaned over, pulling down a pair of my panties, with one of my brassières still attached around his chest and a pair of my stockings still held up by one of my garter belts. He froze, his face the brightest red I’ve ever seen.
I was furious. How could he violate my trust and our friendship by wearing my most intimate underthings?
And I became even more angry when I realized that was why my undergarments kept coming out of the laundry too big to wear. The jerk had been stretching them out.
After a flurry of rants, I finally told him to go ahead and pull the panties back on. He’d already ruined them and I really had no interest in seeing his tiny little cock. Cover himself up.
I made clear to him that he had to buy his own clothes. I didn’t care how he dressed in the privacy of his own room, but he couldn’t keep ruining my clothes.
He whined that he couldn’t afford women’s clothes, as he’d recently been laid off from his job and he wasn’t even sure if he could come up with his share of the next rent payment.
That’s when I got the idea of hiring him as a live-in sissy maid.
I was an up-and-coming professional with a clear path to success as a business executive. I could afford to keep him as my personal maid and servant. And I liked his company.
He agreed, excited as a puppy. His little penis was an erect tent in my panties. “That’s disgusting. I don’t want to see that. Go take care of yourself and then we’ll go shopping for your new clothes.”
I insisted that he shave his body completely. All of the hair was shaved off his legs, arms, back, chest, and underarms. All that was left was a neatly trimmed little pubic patch.
He was terribly embarassed shopping at the mall. We picked out a few dozen panties, bras, and other feminine undergarments to get him started.
The sales woman complimented Tom on actually shopping for lingerie for his girlfriend. Tom became especially embarassed when I explained to the sales woman, “the feminine undies are for him, not me. He’s useless to me as a man (too small a penis), so ’m outfitting him as mmy personal live-in sissy maid.”
As soon as we completed the purchase, paid with my credit card, I told him to go into the men’s dressing room and put on a pretty pink lace set of brassière, panties, and garter belt, along with black fishnet rear seam stockings.
When he came out, I burst into laughter. You could clearly see the pink outline of the bra under his t-shirt. And you could see the black fishnet stockings between his pants leg opening and his shoes. He wanted to rush back in and take it off, but I insisted that he either wear it or move out. He wore it.
People giggled and laughed and pointed at him as we walked in the mall.
At the next store, the sales woman didn’t even need to ask who the clothing was for. We picked out several ultra-short skirts and frilly, lacy tops. The sales woman and I had a lot of fun having poor Tom try on different outfits, while other customers snickered and giggled.
When we left the store, Tom was dressed in a very short black leather micro-mini skirt and a delicate see-through white lace blouse. His black fishnet stockings displayed his freshly shaven legs. The pink lace brassière wasn’t nearly as bright as his embarassed face.
By now we had gathered a small crowd of onlookers laughing and pointing and calling their friends and telling them to come check out the sight of a wimpy wuss being feminized and sissified.
Tom was so embarassed that I had to grab him by the waist and guide him to the next store.
And the miniskirt kept riding up his hips and revealing his pink lace panties. He struggled pulling the skirt back down over and over, juggling the growing collection of shopping bags filled with feminine clothes.
The next stop was a shoe store, where I purchased him several pairs of high heels. The sales woman and I laughed as Tom stumbled while trying on various high heeled shoes. We made him walk up and down the floor several times with each pair he tried on. He got better at it with repetition, but Tom was still shakey trying to walk in his new six inch white leather heels as we left the shoe store.
With the whole mall noticing his transformation, it was inevitable that some of Tom’s friends came up and asked what he was doing. I let him stammer out an abashed explanation that he was becoming my personal sissy maid before inviting all four of them to his coming out party. When it was clear that Tom and I weren’t dating, several of his friends openly hit on me right in front of his partially sissified ass. I flirted right back with Harry, one of his friends who was very masculine and tough-looking.
As soon as Tom’s friends went on their way, Tom immediately started trying to warn me what a bad guy Harry was. Tom described him as a self-absorbed, uncouth biker. It was so disappointing to see Tom’s jealousy flaring up. I thought I had made it clear to him that there was no way possible that he and I would get together sexually.
Tom was surprisingly grateful when we picked out a long curly blonde wig to cover up his short masculine hair. He almost looked like a woman. His features were naturally delicate. I could see the Tom was getting very excited about dressing up in public as a girl. As his transformation progressed, he became happier and more light-hearted, a better shopping companion.
Our final stop of the day was at a beauty parlor. In addition to having his wig styled in ultra-feminine little girlish curls, his fingernails and toenails were painted with very feminine bright pink nail polish and his face was made up with foundation, blush, eye liner, eye shadow, and lip stick.
Tom was absolutely glowing as we left the beauty parlor. Even though he was still unsteady on high heels, he was getting into a feminine swish and flow. He even tripped over himself trying to twirl like a little ballerina.
Upon returning home, I had him bundle up all of his masculine clothes and take them out to the trash, before he was allowed to put away his new feminine clothes.
In the morning Tom served me breakfast in bed and profusely thanked me for making him my sissy maid. He grovelled on his knees while I ate breakfast. For some reason I was hotter with him feminized than I’d ever been with him straight.
Although I am a straight woman, he brought out the dyke side of my nature. I knew I had to purchase a strap-on, tie him down, and take his cherry ass.
When I returned from work, I discovered him in his bedroom jerking off in his new women’s clothing. Ew! Yuck!
And his bed sheets were covered with cum stains. He’d been masturbating all day! Disgusting!
I insisted that he had to be cleaner than that in my place. The obvious solution was for him to masturbate with inflatable dolls. After he finished, he could carry the doll to the bathroom and clean up his mess without leaving behind disgusting stains.
We went to an adult book store to purchase a doll for him. He was terribly embarassed by the leering glances and comments of the rather shady clientele. A couple of them thought he was a she-male hooker and offered him money for sex!
He picked out the Alexa’s Essensual Elements Vibrating Love Doll, the Letha Weapons Doll, and the Chasey Lain Inflatable Fantasy Playmate. A blonde, brunette, and red head. Those were all expensive dolls. I picked out a couple of cheap dolls for him. The Island Babe Love Doll, the Nadia Russian Slut Doll, the Submissive Fantasy Doll, and the French Maid Love Doll.
Back home, I told him that the expensive dolls were special treats that he had to earn. He could hold onto the cheap dolls and use them anytime he got the urge to masturbate.
I locked up the expensive dolls and I would decide when he was to be rewarded. He worked really hard to please me so that I’d let him have a date with one of the deluxe dolls.
I custom ordered real French maid’s outfits, complete with lacy white sissy panties, white lace apron, and little white satin maid’s cap. It took more than a month to get them, but he looked fabulous in them. Well worth the money.
Of course, once Tom started dressing in maid’s uniforms, it didn’t make any sense to keep calling him by a masculine name. I started calling him “Fifi”. It took my live-in she-male sissy maid a while to adjust to her new name.
Things were progressing well. I got a promotion. Fifi took care of the household chores, freeing me up with time to date. Fifi would sometimes pout when I went out on a date, but whenever she did that, she was stuck using a cheap inflatable doll for masturbation. That straightened her out in a hurry.
After several men, I really hit it off with Harry. Harry was a great guy. Very masculine. A bit wild. And hung like a horse.
On our third date, I confided with Harry that I had a live-in sissy maid. At first Harry was horrified, but the twinkle in his eye revealed that he was more than a little curious.
We returned to my place and Fifi was decked out in skimpy black satin French maid’s outfit, white lace apron, black fishnet stockings, six inch white high heels, black satin sissy maid panties trimmed in rows of white lace, and full make up. She looked so incredibly cute.
Fifi was sullen, but she did serve Harry and I drinks and snacks. Harry kept calling for Fifi and sending her back and forth to the kitchen. Harry was turned on by embarassing the cute she-male maid, particularly enjoying watching Fifi’s sexy exaggerated feminine walk and watching Fifi bend over to pick things up.
Before retiring to my bedroom with Harry, I tied Fifi on her knees with her hands bound up over her head just like her cheap Submissive Fantasy Doll. I squirted some lube into his doll's asshole and positioned Fifi and the Submissive Fantasy Doll against the wall with Fifi’s tiny little sissy cock buried in a cheap plastic doll’s ass.
I lifted up the back of Fifi’s short feminine skirt, pulled down her panties and pointed out the base of the dildo buttplug up her ass. I slapped her sissy ass, jiggling the buttplug, while she started pumping her sissy dick in the cheap plastic doll. Harry laughed at Fifi for settling for a doll while he got the girl.
We retired to my bedroom, where Harry fucked me late into the night. Between orgasms, I heard Fifi weeping in his room. Sissy maids can be so emotional. But I also heard Fifi’s doll fucking all night long, long after Harry and I had fallen asleep.
Harry spent several more nights before Fifi finally adjusted to Harry’s presence and stopped her silly sulking. Her housework improved, and she performed all kinds of small romantic gestures that made my life more pleasant. I rewarded Fifi’s better attitude with permission to use her deluxe dolls.
Harry and Fifi actually got along pretty well, even watching sports on tv together. Of course, Fifi had to make all the runs to the kitchen for beer and snacks. And Harry loved seeing her sissy ass shake and jiggle as she ran off to the kitchen on any excuse for an errand.
Fifi referred to Harry as “Master Harold”, which was kind of funny, because not even his mom called him Harold.
One lazy afternoon, Harry asked if I would mind if Fifi gave him a blow job. I said that was Fifi’s decision, not mine, but I encouraged Fifi to do it because I really didn’t enjoy going down on a guy. How much easier it would be on me if Fifi would take over that womanly duty.
Fifi was very hesitant, at first refusing, but after a few days Fifi consented. Soon Fifi would miss some part of the games while she gave Harry multiple blow jobs. It so turned Harry on to order Fifi to curtsey and flash her tiny little penis.
Harry suggested that I have Fifi perform oral sex on me. Harry insisted that Fifi was great at it.
I was reluctant. Fifi didn’t turn me on and I’d never had sex with Fifi. Fifi had never even seen me naked.
Harry came up with the idea of blindfolding Fifi for the act. That way, I could try Fifi out for oral sex without the wimp actually seeing me naked.
Well, it turned out that Fifi was good at oral sex. Really good. I blindfolded Fifi several times a week for her pussy licking sessions. Fifi loved performing oral sex and was getting better all the time.
Soon Harry was demanding four or five, sometimes a dozen blow jobs a day from poor little Fifi. It became obvious that Harry was more into Fifi than he was into me, so I broke off the relationship.
Fifi seemed much happier not having to perform blow jobs all the time. She re-doubled her efforts at pampering me. And the mind-blowing cunnilingus helped tie me over until my next lover.
That was Ramone. A handsome, muscular Black man with his own business.
Ramone liked the idea of a dominant, successful woman with her own live-in sissy maid.
Ramone liked the easy access to blow jobs any time he wanted one, day or night. And Ramone was particularly turned on by blindfolding Fifi after Ramone and I had sex and watching poor little Fifi eat all of Ramone’s cum out of my cunt.
As much as Ramone enjoyed Fifi’s blow jobs, he wanted more. Ramone wanted to fuck her tight virgin sissy ass. It took a couple of weeks to talk Fifi into it, but eventually Ramone popped Fifi’s anal cherry.
Ramone and Fifi and I are very happy with our relationship, and soon Ramone and I will be getting married. Fifi is going to be my maid of honor and is taking care of all of the wedding arrangements.
I strongly recommend that all of you women out there turn your sweet, shy male friends into your own personal live-in sissy maid.
To be continued…
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Copyright © 2002, 2005 contact00@RealSissySchool.com
Last Updated: July 25, 2005
Created: September 23, 2002
Author of Live-in Sissy Maid page: contact00@RealSissySchool.com
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