A crossdresser opens up to his mom’s best friend

I’m a 28 year old single guy with a decent social life, condo, and friends. It was not my first choice to go with my mom for a week to visit one her childhood friends, but the woman, Mary, had this great lake house that I visited for many summers as a kid and I really loved it. I had plenty of vacation time, and the pandemic lockdown meant that driving vacations were better than flying vacations. So, I said yes.

My mom, Linda, is in her early 60s and is not what you would call a MILF. She dresses like a mom, has nice boobs and a modest belly bump with a wide, full butt. Nothing that would make a guy look twice, but not ugly at all. She does, however, wear what I think is the sexiest underwear, and I have developed quite an attraction to women’s underwear.

A few years ago, I was visiting her (my dad passed when I was in college), and she caught me “borrowing” a pair of her silky, white panties. She was surprised, but not furious or appalled as I would have expected. She started buying me women’s panties so I wouldn’t touch hers, and has referred to the moment as me “coming out” to her as a crossdresser. I love wearing panties, which I do daily, and she knows that I am straight though I like silky, feminine things as a turn on.

She makes sure to get me a few pairs of panties every holiday and birthday. I really appreciate her acceptance of my unique turn on, plus, she picks out great patterns and colors for me. She has bought me silky half slips and a few teddys over the years, and she knows I love getting a new treat when I visit her. I’m also pretty sure she knows that I go home and masturbate heavily with my new things.

When I arrived to pick her up for the late summer lake house trip, I was not surprised when she said she had a few vacation gifts for me.

“Here, I found these at the store and think they will look good on you,” she said as she handed me a small, handled shopping bag. My heart raced in anticipation.

I pulled out the first pair of panties, silky baby blue briefs with a white lace waistband. “Oh, mom, they look great, thank you,” I said. The next piece was a matching camisole – she didn’t often buy me tops – and this was a great looking set.

“I thought you might like some loungewear, dear. Panties and your old t-shirts don’t make the best look.” My mom was right, and I loved it.

“Mom, thanks, I look forward to wearing a matching set. I’m sure you’ll like it too” I said. I often modeled the gifts for her, and she seemed to like outfitting me. She knew by the bulge in my panties that I liked what she was doing.

The last thing I pulled from the shopping bag turned out to be a women’s one-piece bathing suit. It was a pretty simple black suit with a large Gucci “GG” logo on the front in white. I had never worn a woman’s bathing suit and surely never thought of wearing one to actually swim in.

“The back is a tanga cut so it’s a little skimpy on the butt, and I hope the front has enough material to hold everything in, but I saw it and just knew you would look good in it.” She knew that some pieces didn’t hold my package in place and was smart about picking out items with full front coverage.

I paused as I held it up to my torso. “Um, it looks great, mom, but I’m not sure I can wear this in front Aunt Mary.” Mary wasn’t really my aunt but she and my mom were such good friends that I grew up calling her Aunt Mary. Our families spent many vacations together so it made it more familial.

“Dan, it will be alright,” she said as she put a hand on my shoulder. “I tell Mary everything, and I mentioned your clothing preferences to her a few years ago. We talk about what you would look good in all the time. It’s time you came out to her too. You can think about it during the drive.” She hugged me and said, “Now, let’s get moving.”

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