from Jenson

Dear Auntie Helga,

My wife and I have been interested in role reversal type relationships for a long time and have tried many things. We have always done this on weekends then gone back to our regular lives during the week. Over the last year we have talked about settling into something on a more permanent basis. My wife is leaning toward a Mistress and sissymaid relationship. To prepare us both for a life changing relationship since I will be the sissymaid my wife introduced a few things for us to try. First off I started to wear a few feminine things at home like panties, bras, girdle and nightgowns to bed. We both agreed to try anything each other asked so I kept my word by wearing the feminine items while my wife worked at putting pressure on me to do so.

Fran saw a milking machine a few months ago so she bought it after watching some videos. We have a bed in the basement where we played games with bondage from time to time. Last night Fran tied me to the bed in the nude then hooked up her milking machine to my penis. Some penis milking machines slide up and down the penis but the one Fran bought was used to milk a cow so it sucks my penis all the way in then releases for a second and the sucks hard again. Fran got creative last night by putting a vibrator wand on my testicles which caused me to ejaculate a couple of times while the milker kept sucking my penis so hard I thought it was going to come off. Fran turned off the vibrator and massaged my testicles hard while the milker kept sucking my penis. I was getting sore which caused me to be vocal so Fran stuffed a gag into my mouth then left the room to go pee. The machine kept sucking on my penis until Fran returned to shut it off. She took the gag out of my mouth with a big smile then asked how was it. Fran took the teat cup off my penis which was all red and covered in cum.

Tonight Fran wanted to go play again so we went to the basement where she took my clothes off and kissed me all over. Fran bent me over the wooden horse then tied down my wrists and ankles with the leather straps on the horse. I was about to ask what she was up to when she gagged me so I couldn't talk. Fran brought the milker over to the horse and lubed up my penis then put the teat cup on my penis again. The milker did its thing again sucking my penis very hard then released then sucked hard again. I think Fran made an adjustment to the milker so it would suck so hard. I then felt Fran behind me playing with my ass then she shoved her strapon into me. Fran was fucking me and the milker was sucking me. Fran was fucking me harder while the milker sucked the cum out of me. There was no pleasure to the milker because it didn't slide up and down my penis. It just sucked me dry. I could feel the suction all the way through my penis as though it was actually emptying my testicles. Fran fucked me harder than the last few times as though she was working on my prostrate to feed the milker. When Fran was done she turned off the milker to check how much it sucked out of me. Fran told me more than last night which she attributed to fucking me at the same time. Fran cleaned me up the released me. I put my panties and nightie on that she brought down. Fran asked me if I wanted a blow job but my penis was sore and red. She pointed out how happy she was for buying the machine.

I'm sorry to tell you so much about our basement equipment but though it would help you know more about us. Auntie Helga I'm not sure if other Mistresses like bondage and machines to be used on their sissymaids but Fran wants to include it. Fran doesn't want me to have intercourse with her anymore but instead as her sissymaid when I become one she will be fucking me. Fran will not give me anymore blow jobs since she bought the milker to do the sucking.

Do you agree with Fran's approach so far Auntie Helga? It might be a few weeks yet before I am her fulltime sissymaid and she my fulltime Mistress. We are still testing everything right now to determine what each other wants out of a role reversing lifestyle. Fran has it in her mind I will be getting boobs but I am not so sure I agree with her on that one. Her logic is I should look more feminine and boobs will help. Fran also wants me to agree for her to take my testicles but leave my penis. For some reason Fran said more Mistresses today insist on castration for all sissymaids. Auntie Helga can you comment on that topic please?

It's getting late and Fran is already in bed so I better go too. If you would be so kind to let me know your thoughts next week I would appreciate it.


How nice to hear from you and thank you for writing about the changes in your marriage. I do appreciate the information on the milking machine, it does sound very efficient, I am familiar with them, though never have I used one, I have seen them in action. Obviously Fran has a vivid imagination and that should make for some very interesting times ahead.

Mistresses enjoy all sorts of activities, from bondage and discipline to S&M. There is no one right way to do this, just as in life, there is variety and whatever she enjoys is a normal approach. Usually however the sissymaid is feminine, many with breast implants, others castrated or their little penis removed. Its becoming more common for Mistresses to prefer a modified or as we call it, a corrected body.

I suggest you relax and enjoy this new life, devote yourself to the woman you love and make her happiness your reason to live.

Auntie Helga

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