by Miss Andrea
I am a very high rank officer of a very successful organization in the midwest. I love to take control in the business and my professional dealings. I am in full control of my business operation and my personal life until this happened one day.
I met Trish the day she first came to the United States. Our feelings for each other grew over the three years that I have known her and recently we decided that we want to start a more intimate relationship.
First, let me describe Trish. Trish is about 5 feet and 3 inches, with long silky black hair, a gorgeous butt and have a pair of small firm tits. She is very independent and like me, love to take control.
Our relationship was going really well until this one day. Trish normally has a group of her girlfriends over our place on every Tuesday at about 8:30 p.m. to play some cards, watch some videos, gossips and etc. So I usually comes back early on Tuesday to help her clean up the place before the girls come over. But lately, I have been busy at work so I have not being able to get off early on Tuesday to help her clean the place. I thought it would be all right since Trish is not currently working. Not knowing, Trish was thinking that I am having affairs with the girls at the office and was getting upset with me coming home late.
It has been at least four Tuesdays that I have not being able to help Trish clean up the place and she is not very happy about it, as I can tell when we get into bed. She was normally very enthusiastic about sex but this has changed lately.
This is what happened on the fifth Tuesday that I thought I could not make it home to help her clean up the place.
Although I am have a very manly appearance to the outside world, I have this fetish of cross dressing. I develop this fetish while I was a little boy, trying out my mom and sister's panties, bras, skirts, and etc. I first thought that this would go away as I grow older, but it never seemed to be true. I told Trish when we first started our relationship and she was not too keen about this fetish of mine. I also have mentioned to Trish that I like a little domination game with her in bed (me in charge).
On this fifth Tuesday, I called Trish at about 2:30 in the afternoon that I could not help her again to clean the house. She sounded very upset and she told me over the phone that if she do not see me at 5:15 at the front of the door, I am going to be in big trouble. I have no idea of what she was going to do with me. Unfortunately, I could not leave on time as I have to get certain things done for the next business day. I got home at about 7:00 in the evening. As I walk in to door, Trish was standing at the doorway with this outrageous outfit. She had on a four inch spike with a jet black thigh high stocking, suspended by a black garter, a skimpy black leather g-string and a matching bra. She looked really pissed that I am back so late! As I shut the door behind me and about to ask what going on, she told me in a very commanding tone to get naked! Not knowing what else to do, I striped off my business suit and took everything off. I was getting a hard on right there and then. Again I ask her what's going on and she to me that I had disappointed her for the past month and I need some punishment. I tried to bring up the point that her friends are coming over later and she said not to worry about them
She first led me into the bath room to get me all shaven (I mean all - legs, public area, arm-pit, chest and my stubby face) I guess this is a reversal, as I normally shave her, especially her pubic area (she didn't like the idea too much). She then led me into the living room where on the table I saw some lingerie. She told me to put them on. There is this size 55D black bra, a matching T-back panty, a garter belt and a pair of Leggs stockings. As I hesitantly put on those lingerie, she brought me this silicon breast to fill up my 55D bra (I like big breasted women). After putting on the lingerie and the silicon breast, she commanded me to sit down and she started making up my face. After about 20 minutes, I was beginning to look like a whore. After the make-up, she make me put on this short skin-tight dress that I bought her last Christmas (she never wore it because she said she will look too slutty).
After putting it on, she put on a wig on my head and brought out this six inch heels. Seems like she has been shopping for these just for me.
As I slip my size 10 feet into the six inch heels, she started calling me sluts and whores. I tried to speak up and out of nowhere came a whip.
She told me to address her as Mistress Trish and I am only to do what she commands from this day forward. Although I felt like a slut, dressing up as a girl really turns me on. My dick is getting really hard and I was hoping that Mistress Trish would let me fuck her there and then. Mistress Trish then tease me a little by rubbing my dick through the fabric of my dress and I can see a drop of pre-cum on the material. She scolded me for messing up the dress. This is then a little after 8:00 p.m. She then command me that I am to clean up the place, which then was still a little mess. I started to vacuum the place and clean up some dishes. As I was cleaning up the place, the door bell rang. Trish opens the door and there was Shannon, Mindy and Teri. I tried hiding myself behind the oven but was in vain.
Mistress Trish then called out my name (then changed to Angel). I tried not to answer her, but I heard the crack of the whip. I slowly came out of the kitchen and I can see the excitement in the faces of the visitors. Mistress Trish must have this all planned out before - I am here to serve her guests all night long, obeying any commands of the girls. Before we can head our way to the living room, the door bell rang again, and this time at the door was Jamie and Sara.
Let me introduce these girls to you. Shannon is about 5'8", well built (she does aerobics 3 times a week), nice pair of firm breast and a tight butt. Mindy is shorter, about 5'4", have a nice set of tits (38C), and a round ass. Teri is a Japanese exchange student, short, 5' 2", small set of breast and short black hair. Jamie is a model. She is a six footer, slender body, a nice firm breast and long sexy legs. Sara is this southern girl, well built, with a good size breast (42DD).
To start-off the evening, Mistress Trish commands me to serves them some wine coolers (I guess it is to get them loosen up). Then, she commands me to make some of my special spaghetti. After serving them, I was humiliated by my mistress, being made to eat like a dog off a plate on the floor. They cuff my hands to my back and enjoy seeing my trying to eat the noodles. My butt was sticking up, exposing my butt. One of the girls start spanking on my butts and I almost fall flat on my face. The other girls follow suit and after a while my white t-back covered butt was fiery red. I was hurting then, but I was getting excited at the same time. My dick was getting hard and the girls notice it but they were restraining themselves for doing anything -- I guess that was the plan.
Each of the girls have brought a bag with them to our place and I was wondering what was in it. They led me into the living room and as I walked in, the girls started emptying their bags. My jaw almost dropped off. They were here all ready for a all night orgy. There were dildos of all sizes and colors, vibrators, chains, whips, cuffs, nipple clips and other sort of toys that I am not familiar with. Sara then took out a video recorder. I almost died there. They were going to film to whole evening.
Shannon then came up to me and ask me to bend over at the couch. She then pull my t-back down to my knees, exposing my big hard on. She came over my back and started stroking my hard on. As I tensed up and getting ready to shoot my load, she stopped. About 15 seconds later, I felt something hard at the opening of my anus. I felt my anus widening and this greased dildo was slowly entering up my butt hole. It was a good seven inch dildo. Although it was then I lost my "back virginity", I was able to take all seven inches of it. They then asked me to turn over and to start jacking myself off. Sara was having this all on video. Without much choice, I was stroking myself off, feeling a little uncomfortable with a dildo sticking up my butt and 12 pairs of eyes looking on. I guess my action was getting the girls hot then. I see Shannon start moving her hands to her crotch and started rubbing herself.
In a moment, she had her short dress all the way to her waist and I was shock to not see any underwear. She had nothing under that skimpy dress.
She started moaning and groaning and I can tell that she's really hot by the moisture around her pussy. Mindy was pulling her dress over her head, exposing her uncovered 38C breast and her neatly shaven pussy. She started rubbing her 38Cs and another two fingers up her snatch. Teri was at the la-z-boy with one of her legs on the arm of the chair and sticking an 11 inch dildo into her cunt. She is in a world of herself. She had her eyes closed and she keep on licking her lips. In less than a few minutes, she started to shake and she let out this low moan. Guess she's not loud in bed. Jamie and Mistress Trish was doing a 69 at the corner. Both were tonguing each other and really seemed to enjoy each other sweet tasting pussy. Jamie was moaning loudly while Mistress Trish has this quiet groan. I don't know how Sara is holding herself back, trying to catch all this in the video.
I was getting close to shooting out my wad, so I motion Sara over to get a closer shot. As she came closer, I shot a big load and it hit her on her face and also at the video camera. She was really upset then. She told the rest of the girls of what happened, and I guess I just got myself into deeper trouble. They decided to chain me up, not letting me touch my already hard again penis. The girls then got in front of me and start teasing me. Shannon did a slow strip tease and gosh, I am not surprise if she does this professionally. My hard dick was starting to ache. Sara started rubbing her titties on me, brushing over my purple head penis once a while. Sara would also jack me a little here and then, just to get me even closer to orgasm. But she always knows precisely when to stop. She was also having two fingers sticking up her own love pot. Shannon started necking me from the back while Jamie was sticking her dripping cunt so close to my face, but not close enough that I can lick it. The smell was just killing me. Jamie was sucking on Mistress Trish and her sticky cunt juice was dripping on my face. Teri was down between my thigh, rubbing and kissing my inner thigh, and moving closer to my prick, but she would not touch it. Mindy was sticking up a dildo in Shannon twat while Teri was sticking three fingers up Mindy. They were doing this for at least 30 minutes before the girls were all drowning in orgasms. Moans and groans were drowning the soft background music. I am sure the neighbors can hear all the loud noises. After they all calm down, my prick was so hard that I thought it would burst. The girls were having so much fun, seeing me so desperately trying to get off, that they started teasing me again by talking dirty to me and among one another. I was getting so hot then that I just blew my wad without any one touching it. My load trickle down my dick and thigh and dripped down on our carpet. Mistress Trish was upset with the mess that she commanded my to lick up all the sperm off the carpet. After that humiliation act, the girls demanded that I lick them off one by one.
Mistress Trish, Shannon, and Jamie was all seated on the couch and I was to lick them one at a time. I started with Jamie and it didn't take her too long before she started to groan loudly. Then there comes a gush of cum and I almost drown in it. Then I moved on to Shannon. She must have just douche her cunt as I can tell it is the sweetest cunt I have ever tasted. It took Shannon a little longer that Jamie to cum. I had also to use my fingers to get Shannon off. Mistress Trish then signaled me over. Over the time we spent together, it has always been difficult for me to get Mistress Trish off. I know this is going to be a long night. After about 15 minutes, my tongue was getting sore and tired. I asked her if I can used some of the toys that the girls brought and I guess she was too hot then to not get off. She moaned softly as I started to slowly insert 12 inch dildo into her cunt. After some time she started to breath heavier and started to talk dirty. She told me to stick another one up her butt. I grab hold of a metallic vibrator, stuck it up her butt. She let out a loud streaking sound as a turn on the vibrator. She was shaking so violently that I thought she was going into a seizure. I started pulling the dildo out and she grab hold of my hands, not wanting me to pull it out. She was experiencing an major orgasm and it lasted for a few minutes. I turned around and Sara, Teri and Mindy was fucking each other. Mindy had on a strap-on 8 inch dick and was pumping it in and out of Teri's pussy. Teri looks like she was experiencing a orgasm that she would never had in Japan. Sara was holding a vibrator and was sticking up Mindy's butt. Mindy must be having a time of her life, fucking Teri and getting fucked by Sara. I moved over to Sara and started sticking my prick up Sara's tight cunt. She doesn't mind at also and we were in a nice daisy wheel. After a few stroke, I felt a hand started to massage my balls. I turned over and it was Jamie. She has so soft hand and with her expert caress, I know I am not going to last long.
Before I can cum into Sara, Shannon pull me off and I shot all over her face and tits. She enjoyed it well and started to rub all my cum over her body. She said it's good for her skin.
Mistress Trish immediately came over and was licking my cum off Shannon's firm tits. After finishing licking it off, she came over to me and started stroking my penis again. I was kinda tired and limp then, which made my mistress very upset. Since she cannot get me hard, she decided to give me a good fuck. I was commanded by her to beg her to fuck my ass. She put on this hardness with a 7 inch black dick hanging out. She rub some KY jelly on her tool and started ramming me from the back, while I was crying out for her to fuck me harder. She was also getting excited fucking me from the back as she started to change her breathing pattern.
After a good five minutes fuck, I was getting hard myself. She then commanded me to fuck her. She was so excited that she tore off the hardness and also my t-back. She sat on my hard-on and started bucking like she was riding on a bronco. Since I have came a few times that night, I was able to hold my load. She had a great time riding me as she was experiencing some small climaxes. After about fifteen minutes of riding me, my cum was starting to boil.
Then Mistress Trish let out a loud moan and her whole body shook. At the same time, I release a big load into her cunt. She continue riding me, milking me dry and until my penis was soft. After this orgasm, I looked up and saw that the rest of the girls was having their own fun. They were all in a daisy wheel, sucking and licking each other off. I was so drained then that my limp penis was so purple. After the girls had their fair share of orgasm, they all got dressed and thanked me for such a wonderful service. They told me that this is what they expect every Tuesday night from then on. After all the guess had left, I was left with one more load to fuck my Mistress.
She made me sit on the la-z-boy and again she stranded herself a top me and was pleasuring herself. We fuck for another thirty minutes before she orgasm and flood our lovely la-z-boy with her juice, mixed with my cum.
The next morning, as I was getting dressed for work, I could not find any of my brief or socks. All I find in my closets were panties and stockings. My mistress then told me that as of last night, I am to be only dressed in panties and stockings. Sometimes I even have to wear brassiere to work. I am also to be dressed as female at home, with everything from make-ups, wigs, brassiere and pads, dress (usually tight and short) and heels. I am also expected to do all the "female" chores.
I guess my mistress gets the kick out from not having to do all the vacuuming, cleaning and etc. From that day onwards, I was also being taught by my mistress to walk and sit and talk like a female. I guess she is fulfilling my fantasies of cross dressing and also submission. Since then, we have great fuck session each night, me serving my nymphomaniac mistress to her fullest satisfaction, only then I can cum. I guess this turn out to be a win-win situation!