My Three Mistress's Ch. 05

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A crossdresser is controlled by his wife and her sisters.
1.4k words
3.97
11.3k
7

Part 5 of the 6 part series

Updated 06/16/2023
Created 02/16/2006
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The first four parts to this story were completed in what I thought was a couple of years ago, I then checked and realised the last part was over ten years ago! I have had the next episode in my head all that time. I revisited this story last year and it still turns me on. Apart from being married to one of these ladies I have kissed and cuddled two of the other women involved and had a brief affair with the fourth one.

As with part four of this story I continue to dress like a slut for these ladies and to serve them in any way they require. I especially love eating their pussy's and licking their bottoms, it is such an honour.

Life carried on as normal, Mistress Cheryl and Mistress Wife would sleep together with me laying at the foot of the bed, cuddling up to four stocking clad feet. Mistress Eileen and Mistress Kerry would sleep in the second bedroom together and I would serve them breakfast in bed. Mistress Eileen would always be ready for my knock on the door and would always try and shock me. I would knock on the door, wait to be told to enter then find the two of them locked together in a compromising position. I would act shocked, but I never was.

Mistress Eileen loved fucking Mistress Kerry with anything from a strap on dildo to fruit and vegetables to wine bottles. Whatever she fucked her with I would always have to watch and wait until she finished then, I would be instructed to clean the item with my mouth.

One day I was called into the living room and informed by Mistress Wife that Mistress Cheryl was leaving us. I was totally crestfallen and began to sob like a little girl. Mistress Wife told me to dry my tears and join her on the settee. I sat on the settee next to her and she undid her blouse and popped one of her titties out for me to suckle on. As I sucked on her titty, she told me of the reason for my favourite Mistress's departure.

Mistress Cheryl owed a restaurant in Egypt which was struggling and close to failing, she needed to go and try and turn the business around. As I suckle on my Mistress, she told me of the plan to save the business.

Mistress Cheryl undid her blouse and Mistress Wife told me to suckle on Mistress Cheryl's breast. I swapped titties and suck with renewed energy. Mistress Cheryl said in order to cut down on running costs at the restaurant myself and Mistress Kerry would be going to Egypt too, to work as unpaid waitresses for her. As I sucked her breast my Mistress had a wonderful orgasm.

The following week I kissed Mistress Cheryl goodbye as she left to save her business, she told me I would follow on in a few days.

The night before my departure Mistress Wife let me make love to her, I had to do this with Mistress Eileen and Mistress Kerry watching. Mistress Eileen was fucking Mistress Kerry with a vibrator, when Mistress Kerry orgasmed, she pulled the vibrator from Mistress Kerry's pussy and slid it up my bottom, I came inside Mistress Wife immediately. As soon as I orgasmed, I went down on my Wife and collected all my seed, when I came up Mistress Eileen kissed me passionately and we swapped my come, then Mistress Eileen kissed Mistress Kerry and swapped my come with her too.

After kissing Mistress Wife and Mistress Eileen goodbye, myself and Mistress Kerry were in a taxi to the airport. Mistress Kerry was dressed in a formal business suit with silk blouse and stockings. I was in male attire but with stockings and panties underneath. The journey was uneventful apart from when Mistress Kerry ordered me to follower into the toilet and pleasure orally, she raised her skirt and I put my head between those stocking clad legs and ate her to two orgasms.

When we arrived at the restaurant we were shown upstairs to our quarters, we were given a room with two single beds, issued our uniforms and told to get dressed. The uniform consisted of a white see through blouse, black bra, black hold up socking's and a very short tartan miniskirt and no panties.

As we were getting changed Mistress Cheryl came into our room, she was dressed in a white see through blouse, black bra and black nylons, but unlike us she had on a formal jacket and skirt. She kissed and cuddled us both, then said "You need to know exactly how things work around here" She slowly raised her skirt revealing her hold up stockings and naked pussy, placed one foot on the end of the bed and said "I want you two knelt down one in front and one behind me, one eating my pussy the other licking my bottom" we both knelt as instructed, I ate her pussy whilst Mistress Kerry licked her bottom. Mistress Cheryl then said, "Every time I request this double licking you will alternate between back and front, you are allowed to hold hands, but no more all your attention must be on me". When this gorgeous creature was satisfied, she made Mistress Kerry lick my face clean, then ordered us to kiss eat other clean.

We started working as waitresses, the work was fine but lots of customers had wondering hands. My thighs were groped on a regular basis and every now and the somebody would touch my cock; some were surprised but most were not bothered. I complained to Mistress Cheryl about the skirt being so short and worried about flashing my manhood. She grinned wickedly and said "Report to my office after work"

After work I went to Mistress Cheryl's office, she was not alone. In the office was a middle-aged fat woman. Mistress Cheryl said "Say hello to Mrs Aziz she is going to solve the problem of your cock showing under your short skirt" I was ordered to stand and raise my skirt, Mrs Aziz then wanked my cock with her fat hand, as I came, she caught my sperm in her other hand and ordered me to suck her fat fingers clean. She then fitted a pink chastity device to my soft cock, which she locked with a small padlock and gave the key to Mistress Cheryl.

Mistress Cheryl then said "I think it's time you showed your appreciation to Mrs Aziz" I looked over and saw Mrs Aziz unbuttoning her dress. This overweight middle-aged woman was wearing a black pantie corselette with an open bottom and tan stockings. She opened her legs, and I went to work eating her large pussy, the smell was strong but not unpleasant, when she orgasmed, she screamed and squirted everywear, I was covered in her juices. As I lifted my head Mrs Aziz just smiled and said "Again" So I went to work again on this overweight but still rather sexy lady. It took a lot longer to make her come the second time, but the scream was just as loud the squirting just as intense.

As Mrs Aziz regained her composure, I thanked her for allowing me to pleasure her and was told my Mistress Cheryl to run along and get cleaned up.

Once I was cleaned up myself and Mistress Kerry were told to report to Mistress Cheryl's office. Mistress Cheryl welcomed us then stood and raised her skirt and told us both to pleasure her. I knelt behind my lady and Mistress Kerry knelt in front as we went to work Mistress Cheryl said "Kerry can you feel how wet I am? That's because I have just watched this little slut satisfy one of my friends" I carried on licking her bottom and Mistress Kerry ate her pussy. As soon as Mistress Cheryl came, she moved away and told is to kiss each other. I licked all the juice off Mistress Kerry's face and shared it with her.

Mistress Kerry and I continued waitressing, at night we would share the one single bed, I told her all about my chastity device and all about Mrs Aziz. Mistress Kerry thought I looked cute with my pink chastity device fitted and as I pleasured her that night she said "Maybe I will have to get a copy of the key off Mistress Cheryl so you can fuck me now and again" as I licked her to another orgasm, I could not help thinking I was such a lucky girl.

I am only halfway through this part of the story.

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3 Comments
VincepetroneVincepetrone6 days ago

You never described Kerry.

AnonymousAnonymous4 months ago

To Anonymous

Don't make yourself sound more stupid then you are.

This is a story. If it took the writter 15 years to complete it. It doesn't mean that things that happends in the story took 15 years.

Real life and this story is not the same. And if you continue to read it after 15 years it actually tell's more about you then it does the writter.

The story is good, i gave chapter 1 3 stars but this one gets 4. The build up is good but the story still has some spelling errors.

AnonymousAnonymousabout 3 years ago

Not much of a series for 15 years of effort. If this is really happened then the last 15 years have been boring but your wife lived in a clean house.

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