Best Mother-in-law

I have been married for about 22 years and my Mother-in-law has known that I loved dressing as a woman for about as long. She has always been very supportive and has even given me tips on how to be the perfect lady. She is one of those older generation women who are very feminine, very womanly. What I would call a very classy woman. A few years back I had an occassion to go and visit her while on a business trip. As we sat and chatted, our conversation turned to my dressing up. She asked me how I was getting on with it. I said fine, but was tried of dressing up alone. It was quiet for a long minute before she said, would you like to dress up with me? I was dumb founded. She just continuede and said, I think we are about the same size. What size bra do you normal wear? I told her that I was a 38C. When I told her this a smile came over her face and she said, the same as me! She took me into her bedroom and asked what would I like to wear of her's. All I could say was everything. She laughed and said, you get undressed while I pick a few things out. As I got undressed I could hear her going through her drawers picking things out. She finally called for me to come in to her dressing area. She looked me up and down and said, I'm glad you shave your body especially your legs. She had laid out her things for me to wear and started by handing me a pair of her panties. As I slipped them on I started to feel so feminine. It was a feeling I have never forgotten. Next she handed me her bra. It did fit perfect and I loved the fact that we wore the same size. She helped me to stuff my bra as I normally did and I soon had a perfect set of C's. She laughed and said, "We could be sisters!" Her wonderful sence of humor helped to ease the tension that I was feeling and helped me to really enjoy the experience. She had chosen a pair of slacks and a turtle neck sweater that I had seen her wear many time which made it even more special. After I was dressed I stepped into a pair of flats she had chosen for me. She said there, now that's better. She had me model for her walking back and forth a few times. Then she said, shall we do your make up? She spent a lot of time explaining to me what she was doing as she made me up. When she had finished we stood looking in the mirrow together and she asked me what I would like to do. I said go for a walk together around the neighborhood. This was something she wasn't expecting. I figured it was pretty safe as it was now night and there are very few street lights where she lives. She finally gave in and we put on our coats and walked out. I slipped my arm through hers like I had seen other women do and we walked out into the night. It was the most incredable feeling I had ever experienced. And I was amazed to think that it was my Mother-in-law who had made my dream of being out as one of the girls come true. When we got back to her house I gave her a big hug and a kiss and couldn't thank her enough. Now when ever we are able to get together she lets me go into her bedroom and get all dressed up in her things so we can have a girls night together.
silkstockings1 silkstockings1
56-60, M
9 Responses Mar 17, 2011

Lucky you

you lucky guy

i had a similar experience, except my MIL came home early and caught me wearing her clothes... see, i have always been deeply in love with my mother in law, i mean, head over heels, and i always loved going to her house during the day and dressing up in her dresses and skirts, i mean, i loved this woman so much, i wore her pantyhose, i would wear her panties i got out of the hamper, i loved the feeling of having her body fluids mixing with mine one way or another, i would put lotion in her soft leather shoe boots, and have the most intimate sex with her shoes, though i wore my own heels and boots... well one day, she came home and caught me wearing one of her dresses and pantyhose and my sexy black patent high heels, i felt so feminine, she literally caught me with my penis in her boot, while kissing and sucking her high heels, and of course she freaked, i convinced her not to call my wife, and i told her i was head over heels in love with her, how i loved her pretty shoes, and this was the only way i could get close to her.... then she says, David, why didnt u just tell me, we could have worked something out!!!!! she wont let me **** her, but now, after i mow her lawn or do something nice for her for her, she puts on my favourite high heels and skirts and lets me kiss and lick her shoes while ************, i come gallons when she wears her shiny high heels.... i love that woman so much, she is my love, she is my passion, i mean, ive actually given myself oral sex while playing with her pretty shoes!!!!!

I would never pass up a chance to visit

What a sweet mother in law, and to be able to spend some 'girl time' with her. She is really a special woman!

Silkstocking, Have she ever taken you out to dinner or to the mall for some shopping...just curious you are very lucky to have a mother-in-law like her!!!

What a wonderful mother in law! thanks for sharing.

wow - yeah , that is a great story. How cool is your Mothe in Law !!! Or any woman willing to be as comforting and sharing as she. Good times. Lately I too have been wanting to be in public and OUT. But , I'm not all the way out - no hair and make up or clothes/ dresses.... Typically, under garments and shoes ... Gotta have my shoes. I'm turning into a shoe ***** I can't afford to be... DARN it .... Trying to wear my shoes to the PO and gas station when the lack of patrons allow or I think they can't see my heels clearly. What a rush - good fun -makes me feel so much freer and would like to feel that way more often in my attire. SD

You are so lucky. Keep a good relationship with mother-in -law, also have somebody to spend some "quality" time. I think, just few of us, have same opportunity as you.