My name is Tim, mid 50s from the mid states. Came across this site and decided to log on. My story isn't wildly unorthodox but my latest relationship has me a bit bemused.
First a cursory background. Twice divorced, the 1st was a "marriage of honor" in my 20s, it lasted about 9 years and gave us 3 great kids. But eventually we both realized the marriage wasn't good for either of us and we both moved on. Fast forward 10+ years, the 2nd was a marriage based on a little fantasy on both ends. I grew up small town country, she grew up very city. I was blue jeans and boots, she was always dressed to the nines. Turned out we had some good times together but by the 5th year we were on the decline and by the 6th i moved out.
Fast forward a few more years & i meet a gal >10 years my junior. She chased until i caught up. We've been together for about 3 years. We do have a lot of mutual interests, are compatible in background and lifestyle. It has a been a great relationship.
We both have always been very up front about our past so there are no surprises. She admitted to a couple of lesbian liaisons back in the college days. About a year or so ago the evening was lubricated with red wine, minimal clothing and more than the usual sexual electricity (which has always been abundant). She brings out a hi-cut, black lace panty and with promises of wonderful things to 'come' convinces me to put them. Which of course after some reluctance on my part and more detailed promises from her, i did. The activities were fantastic! A few weeks later a repeat and i was a little more willing to oblige her inclination. This scenario became more frequent. One evening i decided i wasn't going to play along without further explanation. She admitted that although she had her 'flings' she wasn't attracted to females enough to have a long term relationship but she did like the way lingerie looks on a body. She said she liked the way i looked in the panties and it did heighten her sexual excitement as well as her sexual enjoyment. I caved after a while and put on a new pair of red french cut lace paneled panties.
Since then things have progressed. At first it was "wear this panty on our date tonight." Then "wear this one to work for our early evening rendezvous." Eventually she asked me to try on a matching camisole, stroll around the house before our 'encounter' and like always the result was fantastic.
Over the months she's added an assortment of nighties, negligees, chemises and other lingerie items to my side of the closet and my dresser drawers. She has convinced me to wear camisoles, chemises and even bras almost everyday (she lays out what she'd like me to wear, but it's always my option to decline). She has reassured me she'll never want me in anything more than lingerie. but ...
She has not gone through menopause yet & a couple months she asked if i'd be willing to wear a 'pad' during 'those' days. I respectful declined but she has been pressing me to try it.
my concern is: Will it go further? What happens if someday i decide i am uncomfortable with all the lingerie expectations from her? Will our sexual relationship become more dependent on my wearing lingerie more often? How will our total relationship fair in the future especially if my willingness to 'cross-dress' declines?
I broached these subjects with her & she has given me countless reassurances that it will go no further then lingerie, but I still wonder.