{"id":53581,"date":"2024-02-10T19:52:57","date_gmt":"2024-02-11T01:52:57","guid":{"rendered":"http:\/\/idtryittwice.com\/?page_id=53581"},"modified":"2025-01-22T07:34:15","modified_gmt":"2025-01-22T13:34:15","slug":"maid-service","status":"publish","type":"page","link":"https:\/\/idtryittwice.com\/index.php\/maid-service\/","title":{"rendered":"Maid Service"},"content":{"rendered":"\n

Before Mary and I were married, we \u201cconfessed our sins\u201d, told each other about any secrets we thought the other person should know. Some of the confidences were trivial, and others not so much. For example, I told Mary I had shoplifted candy when I was a kid. I also told her when I was at camp as a teenager, I had a gay tentmate who had a crush on me. <\/p>\n\n\n\n

Mary\u2019s secret was a doozy. When she was in college working on a business degree, she was having trouble making ends meet. She was a barista at a local coffee shop, but the pay was dismal. She said she and two of her girlfriends created a business where they would clean peoples houses topless, wearing only panties. Older men would pay enormous amounts of money for the service. In fact, she seriously considered keeping the business after she graduated, but eventually the three women decided to get on with their careers.<\/p>\n\n\n\n

I naturally I wanted to know about her experiences. She told me she had three or four regulars, but also had dozens of one-time employers. I finally got around to the elephant in the room, was her employers allow to touch her. \u201cI allowed them to touch my breasts and my ass.\u201d It seemed Mary had been a sex worker. I finally asked her the obvious question; did she have sex with any of the guys. She said, \u201cA few.\u201d Although this had happened years earlier, it still made me jealous.<\/p>\n\n\n\n

Flash forward five years into our marriage. Our sex life was active and very kinky. Mary made three times my salary and consequently definitely wore the pants in the family. She also wore the pants in the bedroom and was effectively a dominatrix. She enjoyed facesitting and smothering, ballbusting and cbt, spanking and caning, and strap-on domination. She also liked to humiliate me by dressing me in woman\u2019s clothing, sometime before she pegged me. She never insisted in all out sissification, but she came close. We had also experimented with chastity, although I didn\u2019t wear a cock cage all the time, and I sometimes fucked Mary.<\/p>\n\n\n\n

One day after work, I returned home to find Mary was already there. Normally she\u2019d arrive home an hour or more after me. She said she had some disturbing news, her company was dissolving and its employees were going to be laid off. Knowing her paycheck was critical to the family\u2019s finances, she quickly pointed out that she\u2019d start looking for a new job in the morning. Two weeks later, she received her last paycheck and had not yet had any job leads. <\/p>\n\n\n\n

That evening we talked about our finances. Unless we came up with some new revenue streams, we would start draining our bank accounts. While brainstorming, Mary brought up the topic of the cleaning service. I told her I wasn\u2019t comfortable with her serving other men. Mary said, \u201cGood, because there is a morality clause in most contracts in my line of work, so I\u2019d be risking my career to do \u2018maid work\u2019 again.\u201d I asked her what she had in mind then, and she looked at me!<\/p>\n\n\n\n

\u201cYou want me to be a semi-nude butler for a bunch of housewives?\u201d, I asked half-joking. But like me, Mary had a problem with me serving the opposite sex. Motioning for me to follow her, she said she\u2019d show me what she had in mind. Leading me to bedroom, she told me strip. Complying, she handed me the pink cock cage. I put it on without asking any questions and handed her the key. She then took an outfit out of her closet. I had never seen it before, a kinky vinyl maid\u2019s outfit. It was black with white ruffles around the collar and cuffs. It also has a white hairband and a white apron. \u201cTry this on.\u201d, she said with a demanding tone. I did what she asked. While standing in front of the vanity mirror, Mary put on me a brown wig with the hair in a bun. She then applied makeup, including lipstick, eyeshadow, blush, and mascara. This was the first time she had put makeup on me. Mary handed me a pair of ankle-high lace socks and a pair of shiny black shoes. The sissification had never gone this far before.<\/p>\n\n\n\n

We returned to the living room and continued the conversation. Looking at my appearance, my cock cage was visible from the front and my bare ass showed from the back. I asked her, \u201cWho would possibly want to see me in this outfit?\u201d Mary\u2019s response gave me chills, \u201cCertain men.\u201d Mary wanted to whore me out to beer-bellied dudes who like trans and\/or sissies. I told her I wasn\u2019t keen about the idea, but she already had a plan. \u201cActually, dear, I have already made your first appointment for this evening.\u201d This was moving way too fast. With what I am sure was panic in my voice, I asked, \u201cWhat would be expected from me?\u201d<\/p>\n\n\n\n

Mary smiled and explained, \u201cYou will spend an hour with your client. He will ask you to serve him. The \u2018chores\u2019 are up to the client.\u201d I asked if the men would be allowed to touch me. Mary said mater-of-factly, \u201cYes.\u201d I asked how, and she repeated, \u201cThe \u2018chores\u2019 are up to the client.\u201d Then she explained the compensation would be $500 for a little more than an hour\u2019s work. Three sessions a week, and I would bring home $6000 a month, and there would be no taxes. I protested, but deep down I knew this was our only option. Without the income, the bank would foreclose on our mortgage.<\/p>\n\n\n\n

At 6:00 that evening, Mary handed me a raincoat to cover up, and she drove me to the appointment. She was going to wait in the car while I met with the client. I knocked on the door and a large man with a beard and dressed in a pair of slacks and button-down shirt opened the door. Without saying anything, he stepped aside, and I passed by him. Once inside, he pointed at my jacket, and I took it off and handed it to him. He threw the jacket on a chair and turned around to look at me. Sizing me up, he looked at my cock cage and smiled before signaling he wanted me to turn around. I assumed he was looking at my bare ass. \u201cTurn around. I am Bill. What is your name?\u201d Playing a character and not wanting him to know my real name, I said, \u201cI am Scarlet, Sir.\u201d When he left the room, I followed him.<\/p>\n\n\n\n

\"\"<\/figure>\n\n\n\n

Bill led me to the living room. He sat on the couch and motioned for me to join him. Unzipping his pants, he pulled out his semi-hard penis. There was no turning back now. While I had previously sucked Mary\u2019s strap-on, I had never had a man\u2019s dick in my mouth, but a moment later, I was on my knees and Bill\u2019s dick was in my mouth. Bill\u2019s penis swelled quickly as I sucked it. As it started to become ridged, Bill reached around and started fingering my ass. I kept telling myself this was no different than Mary getting me ready to be pegged, but deep down I knew it was. After sucking him ten or fifteen minutes, Bill pulled me onto the couch and put me in the doggy position. The only lube he used was his spit before he stuck his cock in my ass. It was the first time a real cock had penetrated my ass.<\/p>\n\n\n\n

After fucking me for about twenty minutes, sometimes slowing down and taking his dick out of me before starting up again, I could tell from the changing sounds of his grunts that he was nearing climax. Suddenly, Bill pulled out, turned my head around and he started jacking off. I held my tongue out and a moment later he ejaculated in my mouth. When the cum stopped flowing, he stuck is still-hard cock in my mouth. It was filthy, but I nonetheless sucked it until it was clean. When I was finished, he patted my cheek, dropped $500 cash in my lap, and then left the room. I got up, collected my coat, and went to Mary who was still waiting in the car.  When I got in, she asked how it went. I handed her the $500 and said, \u201cOne down and two more to go this week.\u201d<\/p>\n","protected":false},"excerpt":{"rendered":"

Before Mary and I were married, we \u201cconfessed our sins\u201d, told each other about any secrets we thought the other person should know. Some of the confidences were…<\/p>\n","protected":false},"author":1,"featured_media":53582,"parent":0,"menu_order":0,"comment_status":"closed","ping_status":"closed","template":"","meta":{"om_disable_all_campaigns":false,"rop_custom_images_group":[],"rop_custom_messages_group":[],"rop_publish_now":"initial","rop_publish_now_accounts":{"twitter_1636176473479581697_1636176473479581697":""},"rop_publish_now_history":[],"rop_publish_now_status":"pending","_exactmetrics_skip_tracking":false,"_exactmetrics_sitenote_active":false,"_exactmetrics_sitenote_note":"","_exactmetrics_sitenote_category":0,"footnotes":""},"categories":[324],"tags":[41,46,80],"class_list":["post-53581","page","type-page","status-publish","has-post-thumbnail","hentry","category-fiction","tag-feminization","tag-forcedbi","tag-serving"],"aioseo_notices":[],"jetpack_likes_enabled":true,"jetpack_sharing_enabled":true,"_links":{"self":[{"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/pages\/53581","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/pages"}],"about":[{"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/types\/page"}],"author":[{"embeddable":true,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/comments?post=53581"}],"version-history":[{"count":3,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/pages\/53581\/revisions"}],"predecessor-version":[{"id":56104,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/pages\/53581\/revisions\/56104"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/media\/53582"}],"wp:attachment":[{"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/media?parent=53581"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/categories?post=53581"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/tags?post=53581"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}