Maid To Serve My Wifes Friend 01

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Caught and made to serve as male escort and sissy maid.
3k words
4.26
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Part 1 of the 2 part series

Updated 08/01/2023
Created 06/19/2023
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I have always had a panty fetish. The feeling of the material against my nuts was sensational. I would shoot huge loads

This all subsided when I met my wife Christel in my last year of college. Christel went on to get a degree as a paralegal and works in a large firm. I flunked my finals and never finished college and am working as a stock clerk in a department store.

Early in our relationship my desires changed to fucking her and away from my panty fetish. My penis is somewhat small measuring about 3.5 inches when erect and about 3/4 inch when soft. Christel always calls it my little thing.

I had no sexual experiences with women before meeting my wife. I stand 5 feet 6 inches and am slender, my wife is 5 feet 7 inches and very curvy. We are both in our early 30's. She had many sexual partners before me.

After a year of marriage most of our sex involved me eating her to orgasms and then finishing with me masturbating her tits while she talked dirty. Intercourse was a rare treat. I usually only lasted a minute or two in her pussy.

The smell of her pussy always got me hard. One day after she had been at the gym, she came home showered and left for dinner with her best friend Cathy. I noticed her panties were hanging over the hamper and knew she would be gone for the evening, so I indulged my old kink.

The smell was intoxicating after her workout. Also, the crotch was quite moist. I came quickly and decided to keep them to wear later.

This was the beginning of my collection which now includes panties, bras, stockings and garters. I progressed to a full-blown crossdresser. I started watching online videos of transvestites with men and was always excited by them. I bought a but plug and an 8-inch dildo to suck while I watched the video.

I didn't consider myself attracted to men. I just get excited dressing up and love anal stimulation. I keep all my stuff secretly stashed away in the attic in an old suitcase. I only dressed when I knew my wife was going to be occupied away for more than 2 hours.

Last week Christel told me her friend Mary was having a girls' weekend at her house. Mary's husband had gone away for a week out of town. 6 to 8 women were coming over and it was going to be a blast.

Christel said she was going to have fun with the girls Friday night to Sunday afternoon. I told her I thought it was great.

My mind was racing at the possibilities of fun I could have when she was gone. Christel came home from work at 5 as usual. She showered and packed her bag and then kissed me goodbye.

"Don't have too much fun while I'm gone, Hun."

I had lots of time to play dress up and was leaking precum even before she left. I went to the attic and got my suitcase down. I took a long bath and shaved off all my body hair below my chin. I dressed in a black nighty my wife had thrown out last year and I fished out of the trash.

With that I put on black stockings and a garter and black panties. The silk on my skin gave me a charge. I got to my computer and started to watch shemale porn.

One of the actors was sucking off a shemale while another shemale was giving it to him from behind in a spit roast. I pulled out my but plug and slowly eased it in and out of my ass to the rhythm of the fucking on screen.

I grabbed by dildo and began sucking it. I was jerking off hard and came very hard shooting cum all over my panties. I heard rustling behind me.

"Paul how could you, you pervert". "How could you". "And you are sucking cock".

All the time I didn't notice Cathy was taking pictures and didn't know how long they had been there.

"Why are you back?" I asked, trying to hide everything around me.

"I forgot my phone charger."

Christel stormed out saying, "I want a divorce and I know just the lawyer at the firm".

Cathy looked at me and laughed. 'You do look cute but honey your penis is so small. I may be able to patch this up give me some time and do exactly as I say."

"Thank you Cathy I don't know what to do. Without her I'm sunk. I can't even afford an apartment on my wages."

"From now on you will call me mistress Cathy. This isn't going to be easy, and you are in deep. If you don't do exactly as I say, I will recommend a divorce to Christel. I have uploaded all the proof she needs to her secure drop box at the firm. Sucking like a slut and Cumming from excitement. Just wait for my text and I will tell you how to proceed".

She left after that, Cathy has always been a firm woman. She was being no nonsense. She is only about 5ft tall but is a real loud and opinionated woman. I am sure she wears the pants in her marriage. I got undressed after Cathy left laughing. I cleaned everything and put it back in the attic.

Late Friday night I got a text from her.

Move all your clothing and personal items downstairs and await further instructions. This includes all your toys and girly clothes.

Christel and I are living in a house with a walkout basement that we rent out as a VRBO. Her father gave the house to us as a wedding present, but it is in her name. She had me sign a prenup that put all her premarital assets out of my reach if we divorced.

I'm screwed if she divorces me because the cost of living in Seattle is so high, I don't stand a chance of finding a place to live.

Another text from Cathy.

Dress up in your girl clothes like before and I will be over at 12pm. I told the girls I must go home because my stomach was bothering me, and I would return in the morning.

Her husband Jim is a surgeon of some kind, and they are loaded. Cathy has never worked for a day of her life. What was she up to? I did as I was told and waited. She arrived shortly after 12 with a bag in her hand.

"Hello, sissy I'm going to save your marriage. First, as I told you call me mistress and any other woman you see use a respectful tone and greeting. I'm going to be frank with you, your stuff should be in the alley right now."

"So, Paul you enjoy women's clothes?"

"Yes"

Cathy slapped me hard across the face."yes what?"

"Yes Mistress Cathy"

She took out a pink nighty, pink panties and some pink 3inch pumps.

"Put these on"

I did as she instructed. I slipped the silk nighty over my head and then eased the panties up my leg. It took me a while to figure out the strap on the shoes, but I managed.

"All of the women at girl's weekend enjoyed your pictures and the video. They laughed and giggled but all agreed you need work. Sharon wanted to know how big the dildo was that you were sucking and how long you had a plug up your ass?"

Cathy took more videos of me dressed up and a few still poses.

"So, Paul, I have a few questions to ask you and you had better not lie."

"Yes, mistress Cathy."

She started her video. "How long have you been dressing in women's clothes?"

"Since I was 19."

"Whose clothes did you wear first?"

"My moms."

"You used your moms' lingerie?"

"Yes Mistress."

"Did you smell her panties."

"Yes mistress."

"I warn you if you get hard during these next questions you will be a permanent sissy for life. I want you to be quiet during the questions and let your penis do the answering. When you suck on that dildo of yours do you dream it's a real man? Watching your videos with that penis in your mouth thinking about it getting hard."

She took a finger and rubbed it on my lips. "Them making you their sissy to control. Telling all their gay friends about an obedient play toy? Leaking precum and you all dressed up sucking it."

I was stiff.

"Oh, look your hard. Although it's difficult to tell."

Cathy reached around and barely put a finger on my ass hole. I came all down the front of me. Cathy laughed very loudly.

"I plan on making your sissy dress up game a reality. Again, all of your actions are all on video all sent to your wife and her friends. I think we have a cock whore here and I know a way to earn money off you slut."

Next, she did dress me in the schoolgirl outfit and a French maid's outfit and took photos and video.

"How is Christel doing?" I asked.

"I think they were all headed to a cowboy bar and Christel had on a very short pair of daisy dukes. If she bends forward the whole bar is going to get a view of her sexy panties. And her top was a white corset that barley contained her tits. Isn't she a 40dd?"

"Yes."

"The corset made them stick out on display. I asked her if she was sure she wanted to go like that. She was sure to attract horny men.

She said Cathy, you saw what I have been dealing with for the last ten years. He is so small down there and I have been faithful for too long. So, I think I'm entitled to whatever I want, and I want a hung cowboy.

"I think I could use a cowboy too." Cathy whispered.

She lowered her jeans and commanded me to come over and smell her panties,

"Paul. Do I smell good? This has made me so hot."

She took her panties off and handed them to me.

"Have fun with them it's the last time your dick will see the light of day. I'm leaving now. I want you to shave off every hair below your chin before you go. And I mean every hair on your ass and pathetic clit.

Be at salon 7 on main street at 10am. Put the charges on your visa."

"Yes Mistress"

She left as quickly as she barged in. I googled the place it was a hair salon for women. Yikes, what is Cathy up to?

At eight I got a text from Cathy

Are you up?

Yes.

Yes what.

Yes Mistress.

I got up, showered, shaved everywhere, and put on jeans and a t shirt. I arrived at the salon on time. A woman named Debbie greeted me and said I would be there for a while. Cathy had given her instructions. I was taken back, and other women were giving me stares.

The smell of hairspray and women's cologne was heavy. I was set at a hair washing sink and my head was tipped back. Debbie took a razor and shaved my head. She then covered it with some adhesive and put a long black wig on me.

She Said, "this won't come off for a month with that adhesive.

She shaved my face clean and then for the next two hours used electrolysis to close every hair follicle on my face. She applied makeup, eye liner and lipstick. I was brought out to the front where I got more stares from the women.

Debbie yelled out, "Don't worry women his wife caught him in panties and now she is giving him what excites him." The women all howled.

I was put in a chair with a tub in front of it and a Vietnamese woman named Laurie worked on my toes in the end she put on pink nail polish and then I was taken to have my fingernails worked on. Fake 1-inch nails were glued on. She giggled and talked to the other Vietnamese nail tecks in Vietnamese.

I was sure they were talking about me. Asked them what they were talking about?

Laurie said, "You pretty, you gonna get fucked."

Everything was drying and I was led to a salon station where my wig was styled. I was told by Laurie to go to the back room and strip naked. I did as instructed and said thank you Laurie. You are so nice to me as are all of the women here. (Remerging what Cathy had said about being respectable to women.)

Debbie barged in and grabbed my jeans and t shirt and said, "These go"

"But what am I supposed to wear?"

She tossed me a bag. In it was a short skirt, a white blouse and some white panties. This is all we have in the shop. I gave your other clothes to Jan. She is the one who is staring at you. She is amused at your transformation. She said you are beautiful in drag.

Your clothes are on their way to goodwill. It was 2pm when I left, and I paid 1200 for everything. I got another text from Cathy.

Go to the mall and buy some black high heels!

Oh, crap how could I? One of my coworkers or someone might recognize me.

But I might be recognized Mistress.

Are you questioning me if so, Christel will file on Monday.

I will obey Mistress.

I went to the shoe store as I walked through the mall, I was getting stairs from both men and women. One of the men brazenly walked up slapped me on the ass as I walked by. I went into Nordstroms and looked around the Women's shoe store.

A salesman asked if he could help, and I said I was looking for some black high heels. What size heal and what shoe size. 3 inch heels and size 5. Mam, I think you are bigger than a seven let me measure you. He brought the women's measurements, and I was a seven.

Cathy Texted me

Are you at the shoe store?

Yes

Yes mistress!

You are going to Pay if you mess that up again.

Take a picture of every shoe and text it to me. I will forward it to all the women on the weekend.

I then proceeded to try on many. In the end I was told to buy Cathy the women voted, and it had to be the pattern leather ones.

Go to Claires and have each ear double pierced.

Pierced ears this was going too far but I had little choice Cathy is in the driver's seat now and must submit to everything. I walked up to the late teenage girl that was working there and told her I wanted my ears double pierced. She asked what studs I wanted, gold or silver for starters. I said silver and was led to the back of the store.

15 minutes later I was pierced with studs.

Go home and wait for me. Be dressed up in your pink nighty and fix your makeup.

Yes mistress.

I went home but my keys didn't work the front door. I went around back and got in. I noticed the door going upstairs has been replaced with a solid metal door with a mail slot. I noticed someone coming into the back alley around 5 and at 530 Cathy barged in. "don't you look nice sissy? I have plans for you. You must prove yourself to me. You are no longer allowed to go upstairs unless Christel requests.

She has new cameras everywhere upstairs. It's hers now and she plans on being very promiscuous up there. You might hear them upstairs. Or on a rare occasion she told me she would let you watch. Of course, dressed up as a total sissy and locked up. To give you some of the humiliation that you gave her. Watching her moan as a man with 3 times your size pushers past her underused pussy lips.

Stretching her vagina and bumped hard against her cervix. Making her scream in orgasm time after time. Yelling for him to fuck her. To take her. To be an animal and give her what her pathetic panty wearing small cocked sissy waste of a husband never could. Hearing her pant for him as he blasts a huge load.

Her words, "you will pay." Christel had a bag with her. She produced a metal cage and told me to stand still with my arms over my head. She went to the mini fridge and got some ice. She put it on my penis, and it got smaller to about 1/2 inch. She then fastened something tight around my nuts. After she put a lube on my penis and locked them together. "It's the smallest I could find. I hope it holds until we find a permeant solution.

From now on that useless clit will never get hard again." She slapped me in the nuts hard and I winced. She put a finger on my ass hole and rubbed it. "This is your pussy and I plan to make a fortune with it." I tried to get hard, but the cage stopped me." At 8 a man is coming over. He will pay for your service.

He answered the post I put I put on Seattle Eros Transvestites with all your pictures and likes. Goggle it after I leave if you like. Make sure you give him his money's worth." "I will" Smack, Smack, Smack! She hit me hard in the testicles. "Its mistress or mistress Cathy. If you fuck up again, I'm going to fuck your nuts up. You can stop now but you will be on the streets. I thought about being out in the cold rainy Seattle winter.'

"I will do as you asked mistress Cathy."

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6 Comments
Claudia69Claudia692 months ago

Shouldn't try to keep secrets from your wife. I liked the way the wife passed her husband over to her friend, Good Story..

AnonymousAnonymous4 months ago

Loved it want more Mistress

AnonymousAnonymous10 months ago

I personally dislike how a woman will treat her husband if he likes to dress up he doesn't have to be humiliated

robertw61robertw6110 months ago

I love it, I look forward to the next chapter!

AnonymousAnonymous10 months ago

This is dumb! He does all this stupid shit and hasn't even talked with his wife.

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