I got this wonderful true story from a sweet caller, Prissy Sissy! She wanted EVERYONE to know her story. She went down the rabbit hole into sissyhood, and wants to know what is next. Her story is amazing!
I have been happily married for almost 10 years. The past 2 years I decided to open up to my wife Jess and a few mistresses at LDW, and explore becoming a sissy. I started wearing panties, Jess started calling me Prissy, and when we would have sex she would begin taking control.
After wearing panties for a while and doing humiliation tasks like checking the mail in nothing but panties I was given a task by an LDW mistress. It was to wear a but plug and panties during my 45min drive to and from work. We then started exploring strap on play.At this stage I was now wearing panties every day, I was plugged to and from work. I would be told to pull over on the side of the road heading to work and call an LDW mistress and suck a pink dildo stuck to my steering wheel. I would dress up in a pink sissy maids outfit and do all the housework.
Then came chastity play.
When I started playing with chastity my cock was around 8 inches hard. I started with a cage that was too big and only used it on the weekends.
Then I got a smaller cage when I realized that it is to house my flaccid cock, not an erection. Then I started sleeping with it on.
Jess allowed me a key and I would wear it to and from work (my job made it difficult, if not dangerous to wear at work). I then started wearing it from Friday afternoon all the way to Monday morning. Then we went even smaller. Settling for the vice chastity cage and the vice mini when Jess wanted to really test how small we could go.
At this point orgasms were few and far between and regular marital sex was out of the question.
The next step was cuckolding.
To be honest when I think about it Jess found someone way to quick, and they had such a connection almost like they had known each other for a while. Maybe she had been cuckolding me longer then I realised, I have never been brave enough to ask.
The next big step was David (the boyfriend) coming over to the house to fuck Jess. Then he started staying the night…I would cook them dinner and serve them drinks. Sometimes they would leave and go out on dates. But they would always end up in the bedroom and I would hear Jess absolutely loving being fucked by a real man.
I started sleeping in the spare room and David actually moved in after a few months.
Listening through the bedroom door sometimes changed to sitting in the corner and being allowed to watch. Then I started giving David a hand job to get him hard so he could fuck my wife. Then one day he pushed my head down… Sucking cock turned to sucking cock while Jess fucked me with a strapon.
One night David was still horny and Jess was exhausted so i got to my knees ready to do my job as a good sissy cuckold. But David wanted more…he asked me to take off my panties and lay on the bed. I placed my head in Jess’s lap and I noticed she grabbed some lube from the drawer. I liked how gentle he was…easing his way in. I didn’t know where to look, should I look into his eyes, should I look up at my wife who was running her fingers through my hair and grinding her pussy on the back of my head, should I look down at my caged clitty and watch a real man’s cock sliding in and out of my sissy pussy.
The next big step came at work where I received a promotion and changed sections at work…I now worked in an office setting. This allowed me to wear chastity at work. Around the same time I found a blog online about being pussy free for life, complete with a 12 step program.I was now at the stage were at home I was only ever called Prissy. My male name was all but forgotten. I no longer even owned male underwear. I couldn’t remember the last time I had sex with Jess in a way that wasn’t fitting for our new found relationship…in short I already was Pussy free I just needed to say it out loud.
After exploring this 3 way relationship and as we grew as a throuple we started going on dates. David not only encouraged the 3 of us to go on dates but sometimes Jess and I by ourselves. I even went on a few dates with David as his girlfriend. Our relationship was perfect.
At this point you should all realise I love tattoos, and my tattooist is one of my closest friends. I tell her literally everything. After a few drinks at home with some friends lexi (the tattooist) brought up the fact that I hadn’t had any work done in a while, and Jess who was already talking about me being pussy free merged the two conversations together and the idea for pussy free being tattooed on my pubic bone was born…it didn’t really take that much convincing on my part once Lexi burst out in laughter and said she would do that one for free the next time I was in to get work done.
After getting my tattoo, I wanted to push my chastity even further so I bought a 1 inch birdlock from mature metal. When talking to an LDW mistress about my new tattoo and the new cage she said that i might as well just throw away that key.
That line just went round and round in my mind.
So i set myself the goal of not taking my cage off for the next 100 days. If i could do that and i didnt have any issues with hair removal and general hygeine i would have a party with some friends and we would go down to the Jetty and throw that key into the ocean. So now I’m pussy free for life, in permanent chastity and I still wear that but plug to and from work.
Fast forward into the new year 2020.
My wife begins talking about her relationship with David and how they are madly in love.
In order for them to really have there relationship flourish she wanted for me to move out into the 1 bedroom (tiny) apartment that we bought together as an investment property.
Jess explained to me that thinking of me all alone in my tiny apartment while she is with David was insanely arousing….So I agreed. I would still return home on occasion to do the housework and cook them a nice meal, but mainly just to see them.
Then came Feburary and the divorce papers.
Jess explained to me that she just no longer saw me as the person she married and although she loved having me as her little sissy bitch, having me as her sissy husband just wasn’t something she felt she needed anymore.
So we went to see a lawyer together. Now usually during a divorce you would first have a 12 months separation. Jess was able show that we had already had this separation explaining to the lawyer how i have been activly cuckolded, that we no longer have sex, that we havnt even been sleeping in the same room for well over 12 months and how I recently moved out entirely. The lawyer then set up another appointment.
At the next appointment, we discussed who should get what assets. Jess mentioned that she wanted the house that I received in an inheritance before we ever met. The lawyer mentioned that this would be difficult to do in this format, but that I could sign the house over to her separately.
Jess spoke with me about this for a long time explaining how she wanted me to sign the house over and pretty much give her everything so she could be happy and she mentioned how much she enjoyed me being all alone and that without her i would have nothing.
She told me that if I do this that life can keep going along how it has been these last few weeks since I moved out….I’ll be allowed over from time to time…and I will remain her little sissy bitch.
She said that if I don’t sign the house over and sign the divorce papers then she really will leave me and really will have nothing.
So now I’m pussy free for life, in permanent chastity, divorced and live all alone in a tiny one bedroom apartment.
I still get to be a sissy maid and look after Jess’s house. I still from time to time get fucked by jess and her strapon. But that throuple from 6 months ago is gone. Jess has moved on, expressing our relationship as a dom and sissy…I am more her property or her toy than anything else, and that’s ok.
I didn’t see myself being here 2 years ago when I started wearing panties. I just kept going down that rabbit hole. The further I went the harder it was for to go back. I funny thing is, I begged for this.
So I will continue down this rabbit hole, guided by Jess and the mistresses at LDW.
Tell me ladies what is next?
Oh my goodness. Thank you so much Mistress D. For publishing my story.
A few things have changed even since writing this for you Mistress.
I just love when I read this and think to myself, how did i ever pretend that i was a man.
Oh, prissy sissy!
What has changed? You will have to tell me everything soon. I can not wait to hear what is going on!!!
Ms. Delia
Wow, just wow! Good for you Jess and thank you Ms Delia for sharing her story!
Rabbit hole, indeed! Just so Delicious!
It does seem inevitable in these situations where the wife at the end of the day wants to be married to a Man not a Sissy. Sure it might be fun for a while for a Wife to have a Sissy Cuckold but after a while She just needs a Man to take care of her and her needs.
I feel bad for Prissy Sissy but it’s for the best. Maybe one day she’ll find her own Man to take care of her needs.
That’s hot how you did this to him Ms Delia!!! Seeing how guys look better as girls I’ve decided to let my married friend/the ldw mistresses do this to me. Especially how my friend played with my breast forms and wig telling me I have perfect curves/build and look better dressed up as a girl. Now she’s training me to sit like a girl and walk in heels. 3 dresses she picked out for me are in and said after coronavirus is over she wants me to try them on for her all madeup/lipstick/bra/breast forms/wig/nylons and heels. She said this is who I am and become as well best and needed for me.
Prissy sissy is amazing, Ms. Erika!!
Today she called and tried to say masculine phrases like, “I am a stud with a big cock!” and a good laugh was had by all!!!
Ms. Delia
I think you are right! I hope one day Prissy Sissy will have her own man!!
We can wish hard for this 🙂
Ms. Delia
Oh Paulina!!!
Such a perfect comment. And you know, this IS who you are!!!
Ms. Delia
Thank you for this story Mistress Delia! I feel like this is me in the future… I am also married and I just started wearing a chastity cage… married for 15 years and I’m just not sure how to get my wife to move forward… it’s obvious my clitty is too small to please her… I doubt she even feels it… I’ve gotten to the point where she only orgasms when I go down on her. I can’t remember the last time she actually touched my clit… can you help me reach my potential?
Sissy Ava Black
OMG! Prissy, your living the dream!
Wow every t gurl.hss a different life hut i found out when you srr with women who haveanother man involved you can be fucked on more wsys tham one
Oh my goodness.
Is this my Prissy?
Yes Prissy how did you ever think you were a man… no need to pretend anymore sweetie.
Next for you I’m hoping is a happily ever after with me.
Please be my cute little sissy girlfriend?
You are very welcome, sissy!
I would LOVE to help you reach your potential…and find ways to help you with your wife too! I love to do that.
Ms. Delia
Oh sarina!
YES! Prissy is indeed living the dream. Such a sissy!
Ms. Delia
A sissy fucked more ways than one…Hmm!!
Sounds delicious.
Ms. Delia
Ohhh Miss Lexi, that sounds like a sissy proposal!!
SQUEEEEE!!!!!!! Oh wow! And here on my blog. 🙂 Awwww!
Congrats, I hope!
Ms. Delia
Of course Miss Lexi I will be your sissy girlfriend, and I promise no more pretending.
Thank you so much Ms D for everything this year it has been a bit of a rollercoaster… I love the little “squee” comment aswell.
Sorry to all those hoping I would get a boyfriend… it turns out what i was after all along was a women who likes me for Prissy (the real me).
Here is hoping this is the beginning of a happily ever after
Awww love this!!!!
Prissy sissy really traveling down the Rabbit Hole to the extreme. Every tim e i give up the sissy world & crossdressing. When i come back to this life i come back even with more desire. Was totally just internet for a while now on sissy pills & hair removal to the max & searching net for local misstress 4 pegging