Who here has a friend/submissive, visit their home to do housework chores, or is a male maid for a friend?
A lady I was once friends with once said she would love me as her maid and had previous male maids, but she bought a business and moved away.
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Have known this is something that’s out there in the world like naked cleaning services and the like. But have no personal experience of it. Although doing your own housework in the nude or subservient dress is an easier possibility.
I would not want a male maid , if i did i suspect I would get bored after about the second visit.
As a male maid / chef / servant / medical attendant / chauffeur / grounds keeper / pet groomer / accountant , I could see doing that for a little money and maybe even appreciation of my elderly body . If I had spare time I would rather be a nude or dressed as the lady might wish handyman . I love fixing things .
Plus would they even clean/maid the way you want the house cleaned.
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My wife often swaps me with her friend for her husband.We both dress full on sexy french maids complete with heels,wigs,make-up etc.We do light housework and prepare meals and sit together and share a bottle of wine afterwards.We usually spend about four hours together and although nothing happens sexually there is a lot of titillation and flashing.My wife’s friend gets ample views of my cock in see thru knickers and i sometimes accidentally slip out of them exposing myself fully.She in turn flashes her breasts often and also goes knickerless in a short skirt giving me lovely views of her shaven pussy.My wife does the same for her husband.We do this about six times a year and the sex we have when we arrive home and recount our day is always great.We have an older male friend who has joined us recently on a couple of occasions and he has expressed an interest in having us “Male Maids” visit him when he is dressed in similar fashion.Our wives say he is the epitome of a “dirty old man” which they find exciting and enjoy his company.However he did enjoy spanking us and caning all four of us recently and i suspect he may be hoping for a little bit more than flashing which our wives think is a lovely idea.I quite fancy the idea of watching him become aroused when i’m in Maid Mode and pretty sure i would allow him the odd feel.
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I used to have a male submissive maid, he left the lifestyle quite unexpectedly and came back to me some years later, said he couldn’t forget about me and that I was the only one who got him right. However, I noticed something very toxic in his behaviour - he kept trying to pick fights with me and “win over” on me, most likely because of some personal demons. No thank you, that’s not for me. I’m nobody’s punching bag.
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Depends if you would wear a sexy outfit for me while you clean my floors 
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That sounds like a lot if fun.
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Many years ago I lived in San Fran for a bit. It was when I was first cock-curious. I went on Craigslist to explore the personal ads, which was mind-blowingly new at the time.
I found one, as a live in housekeeper for 3 women and 2 men, to be freely used by any or all of them. I so wanted to apply, but a) got scared and b) was really enjoying my life as it was.
But I often wonder…
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That would have been quite interesting! I have so many questions I know you can’t answer them as you never applied, but I’m just thinking - Was it just free room and board; would they pay for the housekeeping portion of the work so you have a wage? Do you get a day off/holidays, dental or medical. How would you avoid prostitution charges.
So many thoughts.
It was live in and paid with a day off a week. Not a ton of money, but between 5 people it wouldn’t have cost them much each
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So,last thursday i actually became a “Male Maid” for an older male friend.It was a paid position for an afternoon and included “extras”.My wife has a friend whose husband is currently caged and in chastity once again same as myself.The three of them are experimenting with a cuckold situation and her friend has so far been well and truly taken by this friend on three occasions now whilst her husband sits and watches.We call him either “Headmistress Wright” or “Maid Wright” as he is also a cross dresser the same as us husbands.Recently “The Maid” expressed a desire to have me round to his home to do housework dressed as a maid.He wanted to add to the experience by paying me for my services.He also wanted me in my sexiest outfit complete with high heels,wig and full make-up.Plus,he wanted me uncaged and out of chastity for the day.This brought much giggling and merriment from the wives who said it sounded like he wanted a bit more than housework.After more giggling and discussion it was decided “extras” were on the menu as the idea of him paying for sex turned him on a great deal.My wifes friend also suggested how kinky and sexy it would be afterwards for the pair of us should anything occur as she would now be married to a prostitute and it would also further enhance my state of feminisation.This strangely excited me a great deal.Something which would have filled me with a degree of horror and dread in my younger years was now strangely very appealing.On the day my wife dropped me round to his house after telling me i did look really convincing and oh so sexy.I had to admit i did look quite stunning which gave me a hard on which was difficult to hide.It did not go unnoticed by my employer either and i was made to dust and polish on the higher shelves and display cabinets pretty much revealing all as i worked.After an hour he brought out a bottle of wine and told me to open it and pour whilst he went upstairs for a few minutes.When he came back down he too was dressed in a sexy maid costume but minus knickers.The rest of the afternoon i earned my money in a different way which included lots of stroking and rubbing.I came three times (which is something i have not done for a while) and he came twice during the afternoon. edited He told me he wanted to make sure my wife was satisfied i had indeed give him his moneys worth which would be obvious by the state of me.Before this afternoon i was thinking about how i would feel after indulging in not only sex such as this but the fact when i looked in a mirror from now on not only would it be the face of a cocksucker that looked back but also a prostitute of sorts and this could not be undone.I must admit it,i love it.I am also back in chastity and the wives will decide this thursday how much longer this will be for.I do wonder what is in store in the future but,as i am nearer to seventy than sixty i feel an ever growing need to explore this side of me further.My boobs continue to grow and we have now taken steps to enhance them as much as possible without surgery.I really am “one happy girl”.
That’s another one for my collection.
I want your lifestyle please.
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Enjoying life so much at the moment although it is in two halves.The caged chastity period both last time and now this time was and is fantastic.Being a Sissy,and being “forcibly” dressed in various what you could describe as ridiculous outfits ie:Ballet Tutu,Fairy costume etc etc is delicious.Couple that with the teasing,humiliation,degredation,punishment and total control given to both my Mistress and her friend is heady and intoxicating.Being hired out as a Sexy French Maid last week and told i must do as i was bid was awesome.Being turned into an oral prostitute for the afternoon as well to further enhance my paid servitude,nothing short of incredible.Wearing lingerie and high heels etc feels really sexy and naughty but at the same time it also feels right.Then,on the other side is also a state of life i equally love.I do not feel i am in the wrong body,i do not want to change sex and i do not want to date men.However,i love being a girl,wearing lingerie,make-up,perfume,wigs,high heels and dresses and skirts at home all the time when i’m not a caged Sissy.My breasts have grown and developed beautifully over the last few years and my nipples are big and sensitive.When out in the day i’m wearing more and more female items,blouses instead of shirts,womens jeans and i even have a pair of black Mary Jane blocky shoes which i can rock with the right black jeans whilst out and about.With the two sides of my persona in a sort of competition or tandem like state maybe i should find a chastity belt or something a lot more feminine to wear during my period of chastity so i look and feel more like a maiden of older times being kept chaste.I fully expect “Penelope” to be the side of me which becomes a permanent state but i am oh so loving this caged and controlled chastity at the moment and i can full understand why you spent years living this way,wonderful.
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