New Age Lifestyle

Hello all

I have been reading the posts on this website for a long time. My girlfriend has read a few as well. We talked about testing out this kind of lifestyle a few times. The way it was left last time we talked about it was if I wanted to do it then I would have to purchase what I wanted to wear myself. Jackie felt if I was serious enough then I would buy the clothing and if I wasn't then it wouldn't happen. I called a few women's stores but none took me serious. Then I thought ok try thr bra and lingerie shops. The first few said no men thank you but one said sure I could come in after hours. So I went there to meet the owner named Mary. She was very nice as she asked me a few questions. I told her I wanted to see if being sissymaid for my girlfriend was something that would work for us. Mary thought it was cool I wanted to do that for my girlffriend. Mary had me try on a few bras with different cup sizes until she picked one out that fit my body type. Then we looked at breast forms. Mary asked if I wanted to wear panties so she showed me ones that would work best for me. Then we looked at garters and stockings as Mary felt they would be better than pantyhose. Mary then asked if I wanted to wear a dress, French maid or commercial maid uniform for my girlfriend. I wasn't sure so Mary showed me a French maid uniform that was a return. I went to the change room to try everything on including the French maid dress. Mary looked me over to tell me that everything looked good except I needed a larger cup bra since the French maid dress was designed for larger breasts. She got me the larger cup bra with larger breast forms then I tried the French maid dress again. Mary told me that looked much better so I took it all off and got back in my jeans. Mary told me where to buy shoes in larger sizes and maid uniforms since I would need a few of them. I thanked Mary as we wished me luck.

I waited for the weekend before I let my girlfriend know I had done the shopping myself. She was quite suprised that I had done the shopping so she knew I was serious. Jackie said ok go ahead go get ready. I was more nervous with Jackie than with Mary. I took my time getting ready since I wanted it too look perfect. I had only worn the high heels once before so I was a bit wobbly. I slowly walked down the hall into the living room where Jackie was ready to see me. Her eyes popped out of her head as I walk in the room. All I heard was OMG you actually did it. Jackie looked me over while she kept saying OMG. Then she said you now what you me. Jackie said she was sorry she doubted me and that she was so proud of me for taking that huge step. I told her about the stores I went to and the ones that said no way. I also told her about Mary's help. Jackie gave me a big hug and kiss. She told me I looked really cute and that I had nice legs. I showed Jackie my other maid uniforms, bras and panties.

That was the beginning of my feminization as Jackie got more involved helping look more feminine. She did my hair and nails and peirced my ears. For the first few weekends Jackie helped me with cleaning, laundry and cooking. She told me it was all mine in a few weeks and was I ready. It was something Jackie asked a few times. Was I ready and was I sure I wanted to be her sissymaid. Each time I said yes so Jackie replied that is good to hear. One night Jackie bought me a gift. She pulled my panties down then put a pink chastity device on me. She didn't say much when she locked it in place then pulled my panties up again. Later that night when I changed into my nightie Jackie told me she had another surprise for me. Jackie took my panties down then pushed me face down on the bed. The next thing I felt was something going in my butt. I tried to get up but Jackie had me pinned while she gently pushed a dildo in my butt.  I kept asking what was she doing while the dildo went deeper in my butt. Jackie said to me remember when she asked if I was sure I wanted to be her sissymaid. I replied yes so Jackie said well as her sissymaid it was her duty to get my butt used to being filled by her dildo. The next day I walked funny with Jackie getting a good chuckle. As the days went by Jackie used the dildo on me a few more times and bought another for me to learn to suck on. 

I know it was all my idea to be Jackie's sissymaid but I had no idea she would learn to love it. Things have been great as Jackie and I both learn our new roles in life. Our love life couldn't be better as Jackie shows her appreciation for my submission to her. We have kept most of or home life private however Jackie's twin sister and mother know about us. They have both seen me and love what Jackie has done with me.

Sissy life might not be for everyone but it is working out well for us.

Love this life

Louise    

Congratulations Louise, may you both be happy and in continued live with one another as you go down this path!
Miss ATT

Wow Louise, sounds like a dream come true for many potential sissy maids and I’m sure some will feel jealous. It is wonderful to have something work out so well. I hope it lasts as long as you and Jackie desire and that you become totally proficient in your new role.

Loved the letter of your new lifestyle!  It looks like your GF is your new Mistress too.  My, but she took your domination and sissification like a duck to water.   She literally has you by your balls now!!  Since her twin sister and her mother (know and approve) of your sissyhood, you might as well marry your new Mistress.  While your at it, make sure to invite Mary to the wedding.

This is so exciting to read. It gives me some hope for the future.

My wife of almost 50 years is not into the feminization but loves that I do all the chores unless she wants to help. She has the final say on decisions but asks my opinion too.

She refuses to spank me and considered the idea of pegging once but decided no.

I so much wish she would take charge the way Jackie has with you.

On the other hand, we’ve been evolving in the whole FLR scene and come further than I ever imagined possible over about the past 9 years when I ‘came out’ to her.

One aspect of your story I find particularly exciting is her twin and Mom knowing and accepting this decision you have both made together.

You have a wonderful wife and lifestyle I would love to get there someday with my sweet wife.

Sissy Maid Stephanie.

Hello Sissy Maid Stephanie

It sounds like you have done well even though your wife is not 100% into it. As long as you show her the advantages of being her sissy maid I would hope she will come around in time. Remember not to try to force the issue as most women do not like that at all. How about chastity? Have you tried it and would your wife like control of you noodle?

Keep up the good work and hopefully you will get what you want. I know I am fortunate to have Jackie take this life on and enforce it at times too. Just don't give up and enjoy what you have already.

Take care,

Louise

Hi to Louise22 and Sissyswife

We have played with chastity. Over the weekend mostly. I even got her to wear the key in a necklace I bought just for that purpose. Also an ankle chain. Both quality pieces.

She was playing along as a gift to me though and not really into it or the powerful feelings I had hoped she would feel.

My imagination creates so much more in terms of desire but I stay the course. Work on her confidence. Tell her when she does something I like…it is a long uphill journey. There are times we backslide, but we are making progress.

I agree!  Show your eagerness to please and serve!  Always putting her wants and needs first and never expecting anything in return …