tagTranssexuals & CrossdressersMy Three Mistress's

My Three Mistress's


This is my first attempt at fiction of any kind, not just the erotic. This has been a favourite fantasy of mine for some time now, it always makes me come. I have kissed and cuddled the two women involved but that's all. Wish it could be more!

I have been a cross dresser since I was about 10 years old, I started off wearing my mothers rather plain, underwear. When I found myself home alone I would indulge in my secret pastime of dressing as a girl. I will never forget one time when I searched her lingerie drawer and found a set of stockings, suspenders and crotch less knickers what a thrill, they were my first ever stockings, up until then it had only ever been pantyhose.

When I first left school I took some time out, this meant I could fully dress up most days and indulge in some solo fun. I would wander around the house loving the freedom and remaining turned on as my skirt swished against my nylon clad legs.

This usually ended in me reliving my excitement whilst fully dressed.

I followed the usual life path and met a young girl, we dated a few times then when I told her of my love of dressing, she arrived with two sets of lingerie including stockings. We made passionate love together whilst both dressed. The experience left a lasting impression on me, especially as I was already madly in love with her.

Sometime later we were married and life was good, she allowed me to dress once in a while and whenever I was alone I would indulge myself for some solo fun.

Then one day it all changed, she arrived home unexpectedly and I was caught in full female attire. I was wearing hold up stockings, bra, panties, miniskirt and a blouse. Her immediate reaction was "what the fuck" then she calmed down and told me to lift my skirt up so she could see everything. She then proceeded to rub my stiff cock through my nylon panties; I came in no time at all, filling my panties with goo. She lifted her hand to my mouth and ordered me to lick her fingers clean. In that short moment our relationship changed forever. From that day on I was dressed most of the time, and whenever we made love she would climb on my face and force me to clean he freshly fucked pussy. She would use this time to bring herself off at least two more times. I was forced to eat pussy whenever she felt the urge and regardless of how clean she was. I was hooked on eating that pussy.

The dressing continued into a Mistress/Maid scenario, I was a loyal Maid and did all of the cooking and cleaning. As I was cleaning the house she would sit on the couch, drinking coffee and she would constantly tease me, she would call me over and rub her hands up and down my nylon clad legs. Around this time I was given a Butt Plug which I had to wear whenever I was dressed, she would torment me by putting her had up my skirt and giving the plug a little wiggle.

One day she called me into the bathroom, the scene before me shocked me and filled me with dread. My Mistress was sat on the side of the bath wearing a pair of black stockings, protruding from between her legs was a huge black dildo. I was instructed to bend over, pull my panties to one side, removed my Plug and impale myself on her false cock. I slowly slid down on her cock and started to ride it. She made me bounce up and down, I loved it, and I was a complete slut riding this big cock as fast as I could. What a rush, I came and exploded all over the place, I stood up on wobbly legs and re- inserted my Plug. She made me lick all my come up, then after removing her cock she put one leg over my shoulder so I could satisfy her with my tongue. Her pussy was soaking wet, but I did my duty and ate her to two orgasms.

Life continued in much the same way for many months, and then one day just before my fortieth birthday she informed me she was going to "lend" me to her sister. I was shocked and confused and started to cry, she held me close and told me everything would be ok and that she did love me. I was temped to ask which sister as she has two sisters, one younger and one older. She knew I fancied them both! I discovered it was to be the younger sister I would be loaned to. The sister in question was at 36, two years younger than my wife, she was married, but there were problems in the marriage and her and her man where not having sex. Everything was organised for the following Saturday night. As the husband would be away at work that night.

I spent Saturday morning carrying out my maids duties and then in the afternoon my preparations for my loan period started. I was ordered to bathe; I shaved my whole body from the neck down. My wife produced brand new lingerie for me. I had a matching bra and pants set with black hold up stockings. I put on my highest heals, and my maids dress followed by a blonde wig. My wife attended to my make up and attached false nails to my fingers. She made me stand up and do a twirl for her. When she was satisfied she bent me over and fitted my Butt plug.

I was now ready to go to my new mistress's house, but before I went, my wife told me I was to carry out all his sisters wishes, but I was not allowed under any circumstances to put my cock in her pussy. So with that we walked out to the car for the short drive to her house. On arriving at my new mistress's house my wife kissed me on the cheek and left me stood in the middle of her living room. After a few moments the younger sister came downstairs, and sat on the couch. She was dressed in a see-through blouse, black bra and a leather miniskirt. I could see her stocking tops and when she crossed her legs I could see she was not wearing any panties and had a completely smooth pussy.

I said "hello mistress Eileen, how can I be of service to you". She told me to pour her a drink and to kneel at her feet. Kneeling as I was, I could see up her short skirt. She told me to kiss her ankles, as I kissed the first she proceeded to rub her other foot up and down the bulge in the front of my skirt.

I kissed both her ankles, and then worked my way up her gorgeous legs. When I reached the top of her thighs I could smell he scent, I was so turned on.

She ordered me to eat her sex starved pussy, as I did she moaned and told me this was the first sexual contact she had experienced in over a year. I ate her to at least four orgasms, and then she told me she wanted me to fuck her. I reminded her that I was not allowed in her pussy; she just smiled and said "you can have my arse then"

Mistress Eileen ordered me to stand and raise my skirt; her hands went straight to my cock she rubbed my cock through my nylon panties making sure I was nice and hard. She knelt on the couch and leaned over the back of it, I was instructed to raise her skirt and start kissing her arse, and I work my tongue up and down her arse crack then proceeded to tongue fuck her sacred hole.

I then put a finger in her and started to rhythmically finger fuck her arse, she then said "come on bitch put your cock in me" I did as I was told and proceeded to fuck her arse. She was insatiable, she kept orgasiming and telling me to fuck her hard, and I kept going until I filled her with a huge amount of come, she orgasm once again.

Next she laid me on the floor and sat on my face, I ate her pussy as she proceeded to rub herself all over my face; she smothered me until she had another orgasm.

Finally she was satisfied and it was time for to leave this divine creature, my wife arrived to take me home, I had to thank Mistress Eileen for using me so well, I kissed both her feet and said farewell.

I arrived home and went for a bath, my Mistress wife came in to see me and I had to tell her all about my evening, in full graphic detail. I omitted the part about fucking her arse. Then came my next surprise, I was to entertain her older sister. Now her older sister is 48 years old and she is what you would call buxom, she has been in my fantasies for years. There was a twist this time though, Mistress Cheryl was coming to our house and I would have to entertain her in front of my wife. I awoke the next day and carried my maid's duties, and then it was time for me to prepare myself to serve two Mistresses. When Mistress Cheryl arrived I was ordered to carry on with my chores whilst both Mistresses went to prepare themselves.

About four hours later the two ladies made there entrance, both were dressed in full dome apparel and both looked incredibly sexy. I was terrified and turned on at the same time.

Mistress wife was wearing a black leather skirt, black stockings, black high heeled shoes, black bra and a low cut black blouse. Mistress Cheryl was wearing a black Basque, black skirt, black stockings and knee length high-heeled boots. Both had there hair tied back and had on the brightest red lipstick.

I was ordered to serve them drinks, then I had to lift up my skirt and show Mistress Cheryl my panties, my cock was rock hard, she rubbed my cock through my panties, I almost came there and then. I was ordered to kneel at there feet and kiss Mistress Cheryl's ankles. She remarked to my wife "how lovely it must be to have such an adoring husband" and my wife replied "Yes I am lucky, and he is so attentive"

I then found myself staring straight at Mistress Cheryl's pussy, I could smell her sex, and this was a place I had dreamed of being for years. I have had many a good masturbation session thinking about this women s=and what I would like to do to her.

I never dreamed I would one day end up crossdressed in front of her.

Then I leaned forward and started to lick her pussy, she was obviously turned on as her pussy was dripping wet.

My Mistress wife then left the room; I continued to eat Mistress Cheryl's pussy.

When my Mistress Wife returned she had another surprise for me, as with was Mistress Eileen and a young lad who I new was called John, I new him because he worked with my wife and it was common knowledge he was bi-sexual. I was a little embarrecedd that he was seeing me dressed like this, but continued eating Mistress Cheryl's pussy.

Then Mistress Wife announced it was time to continue this upstairs. Once in the bedroom, Mistress Eileen laid down on the bed and John started to eat her pussy. At the same time Mistress Cheryl laid down on the bed and I ate her pussy, as I was eating her pussy Mistress Wife started to finger fuck my arse, then I felt the tip of her strap-on dildo slowly start to invade my arse. I could see John was now fucking Mistress Eileen and by the sounds coming from her she was really enjoying herself. I then started to moan too as my Mistress Wife began to really fuck me.

Mistress Eileen then got on all fours so John could fuck her doggie style, my Mistress Wife stopped fucking me and ordered me to lie with my head underneath Mistress Eileen, I could now lick her pussy and his cock as he was fucking her. The bastard even began to pull completely out of her and briefly put his cock in my mouth. As I was attending to Mistress Eileen and John, Mistress Cheryl started to suck my cock.

John then pulled out of Mistress Eileen and put his cock in my mouth I started sucking him and he came almost immediately, as he filled my mouth with come I started to come in Mistress Cheryl's mouth. I drank all John had to offer, and then Mistress Cheryl kissed me and emptied all my come from her mouth to mine.

As I looked over to my Mistress Wife I could see she was smiling broadly and she mouthed "I love you to me" I don't think I could have been any happier.

I was then ordered to suck John's cock to get him hard again so he could fuck me, but that will be in the next chapter, I this part gains a far reaction!

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