u/mrnawriter

This is a short story from a last weekend. I’m a guy that likes to crossdress and my wife sometimes lets me use her clothes.

She has this mini skirt that I love and when we went out the other day I asked if I could wear it. I wife agreed and I threw it on and loved how it looked. I then asked her if I could wear one of her crop tops and she let me wear that as well and I was ecstatic!

I looked amazing but as we were about to leave my wife looked me over and lifted up my (her?) skirt and saw my undies, a pair of men’s briefs.

She told me that if I wanted to wear her skirt then I would need to wear them with panties. So I had to go up and change out of my briefs and into a pair of bikini panties. As I was changing though she also said that if I wanted to wear her crop top then I would need to also wear a bra underneath so I had to slip on a bra as well.

We went out and had a great time in the city. But I was always reminded of what I had on underneath.

This is a story from a few years ago. I had gone to the mall and decided to get a little dressed up. I wore a black athletic skirt with a regular guys T-shirt and some sneakers.

I'm at a the mall I do some shopping but afterwards I go to one of those couch areas that you see every so often at malls and sat down. I made sure to sit with my legs crossed because I had cut the shorts out of my skirt.

I'm there minding my own business when a guy comes up to me and asks "you should sit like a man and let you balls breathe". I look up and see this guy whose maybe 19 or 20 and a few feet behind him are his friends that are all laughing to themselves.

I could tell the guy was trying to make me nervous and I wasn't about to give him the satisfaction. So I confidently and casually say: "I'm sorry I have to keep my legs crossed, I have panties on underneath". Both him and his friends seemed stunned that I would be open like that and walked away without saying another word.

So the other weekend a friend invited me to go see a World Cup game. I was absolutely pumped and immediately jumped on a flight to get out to him. But when I got there I realized the airline has lost my bag so I didn't have anything to wear besides the outfit I had on.

That night before the game we decided to go out for drink and while we were out, there was this really drunk girl at the bar that ended up puking all over me and my one good outfit.

The next morning when we woke up I had quite a problem on my hands. The game was in a couple of hours, my clothes were covered in puke and there were no stores open nearby to get a change of clothes. I would normally just borrow some clothes from my friend but he is a giant and when I tried on one of his T-shirts it was so long that it fit like a dress.

My friend knows that I like to cross-dress so he jokingly said that I should just wear his T-shirt like a dress to the game. At first I laughed but given my predicament, I didn't have many options so I tried on one of his T-shirts. To my surprise it fit pretty well and my friend said that I looked good in it.

Leading up to the game, we had a pre-game at his apartment with a few other friends. While we were talking he shared a story about how he always has girls over and they always leave their panties behind so he has a drawer full of women's underwear.

I don't know what came over me but after he said that I pulled him aside and asked if I could have a pair from the drawer. I was a bit surprised but then smiled a bit before showing me the drawer back in his room and told me to go wild. I looked in the drawer and it was all pink and other pastel colored panties, mostly thongs but a few bikini's and boy-shorts too. I picked up a pair of light pink bikini panties that were my size and went to put them on.

Back in the living room I was super nervous now, knowing that I just had my friends T-shirt on and a pair of panties underneath. Before long it was time to leave and we walked out of the apartment and to the metro station. My heart was pounding the entire time and I thought that on the train I would just stand but when we got on there was an open seat so I had to sit down. The T-shirt still made for a pretty short dress so I had to sit with my legs crossed.

As we rode the train the guys asked why I had my legs crossed and my friend started laughing. Everyone was curious and so I decided to just come out and say it: "I'm wearing panties". Everyone laughed but tried to keep things quiet because there were more people on the train now. They asked which one I picked out and I said it was the pair of light pink bikini panties. Then the guys started laughing even more and said "omg you're wearing Anna's panties!". It was embarrassing enough that they knew the girl whose panties I was wearing but to make matters worse they said "you know she's meeting us at the game today".

We get to the game and I'm starting to calm down a bit before seeing a girl approach us. All the guys go "what up Anna!" and my heart sinks a bit. We all talk in the metro for a bit, I introduce myself and Anna complements my outfit. We start walking towards the stadium and Anna asks my friend "do you still have those panties I left at your place?" to which my friend replies: "uhh I think so". My heart is pounding out of it's chest at this point because I know exactly where her panties are: on me!

We get to the stadium and I'm standing next to Anna. She leans over and whispers in my ear: "are you wearing panties?" to which I nervously nod. The game is amazing and I could tell Anna and my friend still have a thing as they are pretty kissy the entire match. Then I hear her ask my friend: "I want my panties back tonight" to which my friend smiles and laughs a bit before whispering something in her ear. Immediately afterwards she turns to me and goes "omg you're wearing my panties!!". Thankfully she finds this more amusing than anything else and then yanks on my arm and tells me were going to the bathroom together.

We walk to the bathrooms and she makes me go into the ladies room with her. Inside she lifts up the back of my T-shirt a bit and giggles before asking if I find her panties comfortable. We laugh a bit but then she reaches under her shirt and takes her bra off. She says that my friend loves it when she doesn't wear a bra and then proceeds to hand it to me, telling me that it's actually a matching set with the panties I have on and says that I should go put it on.

Walking back to our seats I'm even more turned on that before. I'm now not only wearing this girls panties but also her bra! We get back to our seats and my friends look at Anna and see her nipples and then look at me and see the outline of a bra. They all laugh because I have a "full set" on now and I get a little red but otherwise we watch the game and our team wins!

After the game we all head back to the apartment to post-game a bit and hit the sack. At the postgame I changed into another oversized T-shirt go to give the bra and panties back to Anna. She takes the bra but tells me to keep her panties.

The next morning the luggage arrives and I head back to the airport for my return flight home. But even though I had my clothes back with me, I decide to head back wearing just my friends T-shirt and Anna's panties.

So I have a bit of a confession to make. I bought myself a kilt a little while ago, but it was a ladies kilt. It was only 1-2 inches shorter than a mens kilt so it flies right under the radar and looks like a regular kilt while being just a bit shorter.

When the kilt first came in I wore it for the first time with a pair of panties underneath. I thought it wouldn't be that comfortable but I ended up getting addicted. They are super comfy and the idea turns me on whenever I remember I'm wearing panties.

I wear my kilt regularly but to this day I have never worn it commando and I've always worn it with panties and I intend on keeping it that way. Wearing my kilt as I type this out and I have a VS thong on underneath.