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How would I go about finding a lady to help me dress up?

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Question - (15 March 2020) 3 Answers - (Newest, 19 March 2020)
A male United Kingdom age , anonymous writes:

as a boy I was fond of silky dresses my mother wore. when I was 6 I dressed up in them and also my two sisters clothing.i loved the feel of smooth fabrics. I wore my sisters school knickers and the feelings as I pulled them up.as an elderly man I have thought about paying some nice lady to help me dress up. masturbation would be my goal but I feel guilty. I was brought up in a religious family. what can I do? my erections are very poor and marital sex is nil for years.

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A female reader, Honeypie United States + , writes (19 March 2020):

Honeypie agony auntYou know you can buy silk/satin boxers for men these days, right?

So it doesn't HAVE to be women's clothing. Unless it's more the fact that it IS women's clothing rather than the actual fabric that turns you on.

If it IS the latter, there are plenty of online stores where you can discreetly buy more or less any kind of clothing you wish.

I do think, however, it's something to talk over with your wife, regardless of the none-existent sex life. I think SHE rather you do this in private by yourself or with her help rather than ask a total stranger for help. It's RARELY a good idea to add more people to a marriage. Especially if this is a longer marriage and you wish to stay married.

If what you are REALLY looking to try is cross-dressing I don't think there is an "easy" way to do this without hurting your marriage and your wife.

Also, I think like FA pointed out, it looks like you are looking to replace you none existent sex life with something that really CAN'T replace it, outside of your fantasies.

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A male reader, Fatherly Advice United States + , writes (18 March 2020):

Fatherly Advice agony auntWell if you have money to throw around. A urologist and a family law lawyer would be the logical first steps. I'm really more understanding than I'm coming off.

If marital sex is nil because of erection insufficiency, then the implant is the way to go.

If marital sex is nil regardless of erection ability, then the solution is to dissolve the marriage and find a compatible partner.

If Marital sex is nil because of the dressing then . . . Well a long term compatible partner would be better than a temporary hire.

I'm just thinking that you want to replace a hum drum marital sex life with a poor substitution (fetish and self care).

Then there is the issue of guilt. What path is going to leave you feeling least guilt?

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A female reader, Andie's Thoughts United Kingdom +, writes (17 March 2020):

Andie's Thoughts agony auntI’m sorry, but I’m not sure there is a way through this, while staying in your marriage. It’s not an uncommon fantasy, but it’s not spoken about often due to stigma. Perhaps find men’s silk clothes and masturbate by yourself. That may be the closest you’ll get while still married, without cheating or lying.

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