Interesting Reversal

[Saikotsu]

Good day everyone,
Have you ever inspired your SO to try out your clothes after they saw you crossdressing?

My girlfriend decided she was curious about it and asked if she could sleep in a pair of clean boxers the other night and if it would bother me. I told her she could go right ahead. She's been uber supportive of me over the years, letting me sleep with bra and forms and night gowns and stuff, so I figured I could hardly say no to her sleeping in boxers.

Has this happened to any of you? We're kinda curious.

[IamWren]

I'm not out to my wife but she does know and like for me to wear boyshorts undies and she thinks girls' skinny jeans fit and look better than baggy ol' guy jeans. Even seeing me with that little bit of girl clothing she hasn't been inclined to ask to wear any of my guy clothing.

Out of curiosity, what did your girlfriend think of the boxers?

[Saikotsu]

She has mixed feelings. She thinks they feel a lot looser and provide more freedom of motion, but they're a bit too breezy for her liking.

[Jennifer0874]

My wife usually sleeps in my boxers. I have little use for them anyway.

[Kate Simmons]

Not really but my alter ego Ericka likes to wear tighty whities sometimes.

[pamela7]

no, she prefers to be naked in bed and our sizes don't match. We dress tho for the occasion/function, so gardening clothes might as well be male - even if i'm in a skirt+leggings, that's a reversal of sorts.

[ReineD]

I'm in my 50s now, but when I was younger it was a sort of honor badge to wear my boyfriends' jackets or shirts. Doing this meant that we were intimate enough to be a couple and I was "his" girl. Also, whenever I did this I perceived that my bfs thought it was cute because their clothes were really too big for me. It made them feel more masculine. If any of them had ever perceived that my wanting to wear their clothes meant a role reversal, I would not have even considered wearing those clothes. A role reversal was the furthest thing from my mind.

When I was older and had teenage sons, I sometimes would wear the shirts or sweaters they had outgrown (and that were looser on me due to the masculine cut) as work clothes - they were less restrictive things I could wear while doing messy stuff around the house, when I didn't want to ruin my own clothes. My husband at the time was much bigger than me and his old clothes would have been way too big.

Your girlfriend might be wanting to wear your things for intimacy reasons, or she may like the shorts because they are looser and more comfortable. But I would ask her if she is wanting to experiment in gender role reversal before making that assumption.

[Dana44]

My girlfriend wears many of my T-shirts. I asked her if she wanted to wear my boxers. Maybe

[sometimes_miss]

Good day everyone,
Have you ever inspired your SO to try out your clothes after they saw you crossdressing?

My ex wore mens' clothes all the time; jackets, work jeans, flannel shirts, work shoes, problem is, it's perfectly acceptable for women to do that. When she asked how I would feel if she occasionally wanted to put her hair up, put on a fake mustache, and act like a man I said sure, but you're preaching to the choir. She couldn't accept what she perceived as a girly guy as a husband.

[OCCarly]

My wife has been stealing my men's logo T shirts for years. Her latest score was a really nice Aeropostale oversize men's T shirt I bought to wear as a bikini cover up around the pool.

Since I came out to her she has been stealing some of my better women's clothing as well. She cadged two of my best fitting sports bras in the recent past. Oh, well...

[Alice_2014_B]

I let my wife wear some of my heels, some are off-limits.
Though we have the same shoe size, we do not share the same size in clothes.

[Tracii G]

My first wife forgot to do laundry one Sunday and I didn't have any clean uniforms so I wore a T shirt of hers and a pair of her jeans to work.
I was nervous but no one noticed I guess.

[AllieSF]

Not yet, but it is interesting when you think about it a little more. A woman wants to try on some typical male clothes like a baggy tee shirt, loose fitting jeans (AKA boyfriend jeans) and boxer shorts. I wonder how they feel knowing that they probably have already tried them on before and actually worn one or more of those items at the same time as they went about a casual dress day. Just look at some of the women styles. Except for the boxer shorts (as far as I know) most of these male styles are already available in the women's and girl's section of the clothing store. My daughter and her girlfriends went through that wear male boxer shorts, sometimes wearing them out during the day like regular shorts. You could readily tell they were male by the way they stuck out in the back and sometimes in then front.

I do congratulate you for having such a wonderful girlfriend. Think twice before moving on for that greener grass next door. You might get there and find out that it is all crab grass!

[alwayshave]

When I gave up wearing boxer briefs years ago, my fiancee grabbed them before I could through them out. She has been wearing them on and off since.

[Saikotsu]

Your girlfriend might be wanting to wear your things for intimacy reasons, or she may like the shorts because they are looser and more comfortable. But I would ask her if she is wanting to experiment in gender role reversal before making that assumption.

Actually, I very much doubt she wants to engage in role reversal. She's very much a genetic girl and quite happy where she's at. I titled this post as an interesting reversal because up till now I've always been the one who wore clothes of the other gender. I got to see things from her perspective in a way. I think you're right about it being more about intimacy, though I think it was also curiosity. Plus, you're right, I definitely think my oversized clothes are cute on her.

That said, perhaps I'll ask, like you suggested. Might be interesting to explore. However, I don't really see this going that far.

By the way, my mom was the same way with my clothes I had outgrown. For a while there we would trade clothes. When I was younger she'd give me some of her jeans that I was growing into and then when I outgrew them she would take them back.

[deebra]

True Story. Years ago I was in Walmart in the men's department and there was this round rack with colorful silk men's boxer shorts on it. Just to be sure I asked the SA were these men's boxers, she said yes and women buy a lot more of them than men and wear them for outer shorts. And CD's are timid about going public ?????, chalk one up for the ladies. They probially didn't know it but they might have contributed to gender neutrality in clothing but that said women wear both sex clothes and men are afraid to.

[Krisi]

Nope, never happened. My wife has a couple of things from the men's side of the store but they have nothing to do with crossdressing.

[Saikotsu]

Lots of interesting replies. Thanks for taking the time everyone.

@AllieSF
I'm not sure what you mean by moving on to greener grass. I can't imagine there being a better person to be with than my girlfriend. I know I'm super fortunate to have her.

[ReineD]

Actually, I very much doubt she wants to engage in role reversal. She's very much a genetic girl and quite happy where she's at.

Oops, sorry I misunderstood your thread title.

[debstar]

Probably jalousie guys have real pockets you can put things in

[AllieSF]

Lots of interesting replies. Thanks for taking the time everyone.

@AllieSF
I'm not sure what you mean by moving on to greener grass. I can't imagine there being a better person to be with than my girlfriend. I know I'm super fortunate to have her.

Sorry for any confusion. My point (trying to be funny) was that you have a gem so don't do something foolish and lose her. I know you know that, but people like her are rare when people like us are involved. Thanks for sharing.

[Cheryl T]

My wife enjoys my style and she has upped her wardrobe a bit in the last few years.
Mostly though she uses very little makeup and when we go somewhere "dressy" she asks for advice and loves having me do her brows for her.

[Saikotsu]

No worries, Reine, I appreciate the feedback.
Same to you, AllieSF, I can be a bit literal at times. Especially online since text lacks many of the tonal and non verbal context cues that regular communication provides.

[Lexi_83]

I had a GF who liked to crossdress sometimes. But it was a "pre-existing condition," lol. She was 5'10 but it was still hard to get things to fit: the opposite problem we have, of course, shoulders too narrow and hips too wide.

[Nolacdflorida]

The only problem I have since coming out to my SO is that she has fallen in love with my skirts and tops and at least two items now reside in her closet instead of mine. Its all very good though.