When and who's lingerie did you first wear?

I can't fit in my petite wife's lingerie or dresses but she does help me with lipstick etc
 
Ive only wore panties once. Met up with a guy and he had some. Wore panties and thigh high stockings as he gave me a blow job. Was so hot, really wish i could do again. Love the feel of the stockings and panties.
 
It was a full corset

One of those kinds you see old ladies wear long ago. Spent weekends at dad's girlfriends house and middle drawer had a full white bra and full white corset. I slept in the corset so many times. Dad's girl friend had big jugs too. Humped in between the mattresses between two wadded towels wearing too. Those were the days!
 
Ex-girlfriend...

I was in my mid-20's. She had a sexy silky red teddy. We were playing around and after I told her how much I liked it she asked me to wear it. I did and secretly loved it, I never told her how much. Something just clicked. I've wanted to re-capture that feeling with another partner ever since...
 
Early in high school I had a paper route. One of my customers asked me to feed their pet's while they were on vacation. Of course I went through her drawers and hamper and dressed in her underwear, pantyhose, shoes and dresses. None of it
Was sexy, but I felt sexy.
 
My older sister's.
I was eleven and she was 16. I heard her leaving the house as I was heading to the bathroom for a pee. I saw her knickers on the laundry basket. To this day I cannot understand why I did it but I reached out grabbed the knickers and put them on. My little cock immediately stood to attention and i loved the feeling. I was hooked. nearly 60 years later I still adore slipping on panties, lingerie, dresses and of course my đź‘ 
 
I started when I was 12 trying on my Mom's nightgowns, bras and panties. My sister caught me some time later and made me dress up for her. She tried to get me to suck her boyfriend but I wouldn't do it. I got angry with myself for not going through with it. But I found out later all bout cocks and men.
 
I was 19. I had been over at a friend's house the day before to do some shooting and had accidentally left a boresighting laser at his house, so I texted him to see if I could pick it up. He told me I could, that his little brother (14) should be home.

I went, got the boresight, and agreed to let his little brother shoot the .22 I still had in my car while I went inside to use the bathroom. As I stepped out of the bathroom, I noticed his little little sister had left her door open right across the hall.

I'd had a crush on this 16yo for a couple years now. She was gorgeous, with straight blond hair, magnificent tits, and a hypnotically perfect ass. I always fantasized about her wrapping those thick volleyball-player thighs around me and slamming that ass against my hips as I fucked her.

Still hearing the shooting outside, I stepped into her room. It was a wreck. Clothes were scattered everywhere, including a pair of faded cotten panties with a used but spotless panty liner still attached. I went to her clothes hamper in the corner and near the top found a pair of volleyball shorts with a wad of cotten panties rolled up inside where she had peeled them off after practice. I pulled them out, held them to my nose, and inhaled the scent of her dirty pussy.

I put them in my pocket and left. Saying good bye to little brother, I went home and jerked off furiously to the scent of my crush's sex for months. When her scent had finally faded, I began to wonder what they felt like. I tried them on and was immediately in love. They couldn't contain my cock, but the material was so soft I couldn't wear them long without pitching a tent.
 
I was in my mid-20's. She had a sexy silky red teddy. We were playing around and after I told her how much I liked it she asked me to wear it. I did and secretly loved it, I never told her how much. Something just clicked. I've wanted to re-capture that feeling with another partner ever since...

I had the same experience. Except it was a little pair of boy shorts.
 
Similar experiences...

I had the same experience. Except it was a little pair of boy shorts.

If I had only felt more comfortable with myself and had been mature enough to deal with my feelings and explore it could have been an incredible situation...
 
Not my first time but, I'll be going to the gym wearing my wife's right now as I've been asked to by my online dom. Hope to take a pic.
 
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