Bi-Sexual Male / 19
The Maid Caught Me
I have a pretty good job for my age. I am a waiter in an upscale restaurant and I get more than $200 a night in tips alone and another $50 in wages so working six nights a week that gets me $1500 a week. I've been waiting tables since I turned 16. I'm pretty good. I am fast so that means less time doing nothing and more time earning money. The management has even expanded my section to take pressure off the other wait staff letting me earn more.
So this means I get to indulge in a couple of expensive hobbies. One is cross dressing. The other is hiring the occasional lady of the evening. I also live at home rent free with my indulging parents. If you are able, choose parents with lots of money who don't require you to pay rent despite working. It's probably because their home is owned by a family trust set up by my great grandfather in the 1950's and all their bills are paid for by the trust including taxes and utilities. So basics, healthcare, food, shelter they pay for, my hobbies I have to pay for. So I wait tables.
So I spend a few thousand dollars a year in frilly slutty wardrobe. Being slender and having a sort of baby face and long hair pulling off a feminine look is easy for me. In fact even when not cross dressing and not wearing make-up I have had on more than one occasion walked into a men's restroom and told by men in there I was in the wrong restroom. My mom always said I should have been born a girl. I look in the mirror when all dressed and made up with my blond hair in pigtails and jerk off imaging women watching me and making fun of me. I do wish my cock was smaller and I had boobs to complete my embarrassing appearance but I suppose one can't have everything.
So I go to cheap hotels and rent a room then I go on the internet and look for hookers to come to my room and all I ask is they critique my appearance as viciously and brutally as then can while I jerk off in front of them. This usually costs me about $500.
So last week I did this only the hooker canceled at the last minute and I could find nobody else. So I gave up and started to surf for porn but it wasn't the same so I just went to sleep with my hair in pigtails, wearing red fishnets with ruffled lace trim, a matching garter belt, a bra with cutouts for my pumped up nipples to poke through, red six inch pumps and fishnet fingerless gloves with ruffled trim at both ends all red. I had just gotten my nails done also in red, nice and long, hoop earrings and I had gone to the one public place I dare go to a department store that does free make-up if you buy a kit which I had just done and was in my car. I looked positively slutty and feminine and was all dressed up with no place to go. I had paid for two nights and hoped the second night would be more successful.
I should also point out at this point that due to the noise level in such motels I always sleep with ear plugs in. So I had given up around three in the morning when I drifted off to sleep.
I was woken up by a scream. I sat up straight and saw at the foot of my bed a maid holding a vacuum and wearing earphones listening to music. She had accessed my room and had made it to the foot of my bed before noticing me sitting there in all my cross-dressed feminine unglory. Seems she had knocked and when nobody answered assumed the room was vacant and I had forgotten to put out the do-not-disturb sign. She was a woman in her forties, Hispanic, more or less average with long hair in a bun and a little heavy set but not morbidly obese. I was still in my slutty red lace and fishnet lingerie with my nipples and erect tiny cock fully exposed having been sleeping on top of the sheets. She looked at me and I looked at her and she ran for the door. Only she didn't run out the door. She closed and locked it. Then she put down the vacuum and proceeded to scold me. I tried to cover my crotch up with my hands but she came around to the side of the bed and slapped my hands away and called me a puta repeatedly. She swatted at my balls and asked me why I was dressed like a puta and I told her I liked to jerk off dressed this way in front of women who I hire (this motel was known as a place hookers go to meet clients) to laugh at and ridicule me and that I was into it and I don't know what made me say all that to a stranger but she did ask. So she looked absolutely disgusted with me and then said what I did not expect. "So jerk off already you filthy puta!" So I did. I jerked off for about twenty minutes using up all her time she was allowed to clean the room. She berated me and ridiculed me better than any hooker ever did. I then stood up and just three feet in front her her masturbated insanely while confessing to everything she accused me of and came harder than ever in my life. I tipped her the $500 intended for the hooker who canceled. We do this monthly now.
So this means I get to indulge in a couple of expensive hobbies. One is cross dressing. The other is hiring the occasional lady of the evening. I also live at home rent free with my indulging parents. If you are able, choose parents with lots of money who don't require you to pay rent despite working. It's probably because their home is owned by a family trust set up by my great grandfather in the 1950's and all their bills are paid for by the trust including taxes and utilities. So basics, healthcare, food, shelter they pay for, my hobbies I have to pay for. So I wait tables.
So I spend a few thousand dollars a year in frilly slutty wardrobe. Being slender and having a sort of baby face and long hair pulling off a feminine look is easy for me. In fact even when not cross dressing and not wearing make-up I have had on more than one occasion walked into a men's restroom and told by men in there I was in the wrong restroom. My mom always said I should have been born a girl. I look in the mirror when all dressed and made up with my blond hair in pigtails and jerk off imaging women watching me and making fun of me. I do wish my cock was smaller and I had boobs to complete my embarrassing appearance but I suppose one can't have everything.
So I go to cheap hotels and rent a room then I go on the internet and look for hookers to come to my room and all I ask is they critique my appearance as viciously and brutally as then can while I jerk off in front of them. This usually costs me about $500.
So last week I did this only the hooker canceled at the last minute and I could find nobody else. So I gave up and started to surf for porn but it wasn't the same so I just went to sleep with my hair in pigtails, wearing red fishnets with ruffled lace trim, a matching garter belt, a bra with cutouts for my pumped up nipples to poke through, red six inch pumps and fishnet fingerless gloves with ruffled trim at both ends all red. I had just gotten my nails done also in red, nice and long, hoop earrings and I had gone to the one public place I dare go to a department store that does free make-up if you buy a kit which I had just done and was in my car. I looked positively slutty and feminine and was all dressed up with no place to go. I had paid for two nights and hoped the second night would be more successful.
I should also point out at this point that due to the noise level in such motels I always sleep with ear plugs in. So I had given up around three in the morning when I drifted off to sleep.
I was woken up by a scream. I sat up straight and saw at the foot of my bed a maid holding a vacuum and wearing earphones listening to music. She had accessed my room and had made it to the foot of my bed before noticing me sitting there in all my cross-dressed feminine unglory. Seems she had knocked and when nobody answered assumed the room was vacant and I had forgotten to put out the do-not-disturb sign. She was a woman in her forties, Hispanic, more or less average with long hair in a bun and a little heavy set but not morbidly obese. I was still in my slutty red lace and fishnet lingerie with my nipples and erect tiny cock fully exposed having been sleeping on top of the sheets. She looked at me and I looked at her and she ran for the door. Only she didn't run out the door. She closed and locked it. Then she put down the vacuum and proceeded to scold me. I tried to cover my crotch up with my hands but she came around to the side of the bed and slapped my hands away and called me a puta repeatedly. She swatted at my balls and asked me why I was dressed like a puta and I told her I liked to jerk off dressed this way in front of women who I hire (this motel was known as a place hookers go to meet clients) to laugh at and ridicule me and that I was into it and I don't know what made me say all that to a stranger but she did ask. So she looked absolutely disgusted with me and then said what I did not expect. "So jerk off already you filthy puta!" So I did. I jerked off for about twenty minutes using up all her time she was allowed to clean the room. She berated me and ridiculed me better than any hooker ever did. I then stood up and just three feet in front her her masturbated insanely while confessing to everything she accused me of and came harder than ever in my life. I tipped her the $500 intended for the hooker who canceled. We do this monthly now.
