from Linda

Dear Helga,

I have always been a somewhat frisky woman. I enjoy sex and am somewhat demanding about my pleasure, his skill and his stamina. He has been somewhat disappointing in those important areas. But with that said he is a good provider, will have a nice retirement pension, he had a home at the beach, nice cars, needless to say he was a catch. We have been married for eleven years. It is a somewhat late in life marriage and a second marriage for both of us. One of his quirks is a love of feminine lingerie and women's shoes. I have capitalized on that and have a brilliant shoe and underwear collection . He is an eager if not skilled lover and to his credit willing to go down on me. That is something I demand in a man.

The aging process has taken its toll and his ability to become erect and to maintain an erection has gone by the wayside. Many wives would try to reassure their husbands with platitudes like "Don't worry dear it happens to all men" "Oh sweetie it just a temporary thing" "its nothing I enjoyed it anyway." But I am not like that.

The morning after his failure I had to tell him that he would be going into chastity for the foreseeable future and in an effort to stimulate him he would be wearing the lingerie, stockings and shoes he so dearly loves. I also had to inform him that if he could keep me happy and satisfied with his oral service I would try to remain faithful but if his tongue failed the way his penis did fidelity is not guaranteed.

That morning he went into panties and a bra, I ordered a chastity device online and he and I went shoe shopping. We both love shoe shopping but my husband would have a bit of a tough time today. You see I was serious about him wearing women's shoes. He would have to find shoes he could wear every day. I told him he would need loafers, oxfords, ankle boots, athletic shoes, sandals as well as flats and pumps for at home or when we went out. He was going to have to learn to keep a low profile with his bras and shoes.

We visited a large department store noted for their extensive shoe department. I signaled a young female shoe clerk and gave her a idea of what the blushing sissy would need. I could see the dollar signs go off in her eyes. I told her to call him Phoebe. She sat him in a chair, removed his shoes and I heard her say "oh good your wearing stockings". I told Phoebe he would need a few handbags to go with his shoes. Poor Phoebe was busy trying to hide under the chair .

The shoe shopping ordeal now over and Phoebe now outfitted in proper footwear and underwear we could get on with life. Well Helga my healthy sex drive overcame my promise of fidelity and soon I was making friends with real men. I had to have a long talk with Phoebe about my needs as a woman. Phoebe of course tried to explain he had needs as a man. It is very difficult for a man to put his foot down when it is shod in delicate footwear and his small penis is locked in a soft pink plastic chastity device. And it was decided I would have occasional dates.

My dating remained rather innocent, just drinks, dinner and sometimes dancing until I met Mr. Evans. My life with Phoebe had settled into me receiving oral sex, foot service and cuddling. Phoebe wanted more but with her in chastity and by now mostly in frocks at home there would be no attempts at sex.

Mr. Evans was now a frequent dinner guest at my home and he had of course met Phoebe. By now Phoebe often served as my maid and was properly attired in a rather smart uniform and mid heeled pumps. Phoebe served a nice supper she had cooked, offered Mr. Evans drinks and preformed a proper curtsy. I told Mr. Evans about Phoebe's various problems with sex, size, softness and quickness and now the chastity.

Mr. Evans became very interested in Phoebe and her situation. He asked her all sorts of questions about chastity, humiliation and the eventual sex between him and I. Phoebe was very upset at the idea of me sleeping with Mr. Evans and what would happen in the marital bed.

On the night it happened Phoebe was sent to the guest bedroom and Mr. Evans and I retired to the master bedroom. In the morning Mr. Evans and I sat at the breakfast nook and shared intimate moments while Phoebe fixed breakfast for us. Phoebe was still in her night gown, robe and pink slides. She appeared quite embarrassed to be the cross dressed cuckold that she was. Mr. Evans noticed the embarrassment and offered comfort to the poor anguished sissy.

When Mr. Evans left for the day the sissy and I had a long talk. I told her that Mr. Evans would be staying over on a regular basis and as a cuckolded sissy Phoebe would be obligated to offer him foot rubs, and shoe shines. As a cuckold she would shop for condoms, personal lube and the things a sexually active couple may need in their private space. On the nights my guest would be staying over Phoebe would lay three condoms out on the night stand along with personal lube. She would offer to shine his shoes and would leave them outside the door in the night. In the morning she would dispose of any used condoms, make up the bed and change the sheets if necessary.

Needless to say an argument followed up this conversation. I had to tell the sissy that I didn't think it was too much to ask for a cuckold to assist his wife in having a satisfying sex life as the said cuckold was unable to provide it.

I will put the question to you and your readers; Is this too much to ask? BTW I could tell from the sissies reaction he was enjoying the idea.

Linda in California

Thank you for your letter Linda. A proper response when he failed to perform, after all he loves dressing as a sissy so he should not have a problem doing what's required, no its not too much to ask. Readers will note that I have started to include letters that feature extra marital sex, it will be limited to those situations I feel are stable, comfortable and pleasurable, it also seems that some sissies actually enjoy the idea.


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Letter 6