Sissy Stories, Experiences and Memories

[pullupgurlie]

Hello everyone, I hope this sparks discussion about what helped shape our "Sissy" side. I know for me, this was a big tipping point. 

I wanted to make this thread to share specific memories or stories about your Sissy side.

I'll share some of mine, starting with the following. This is the most open I've ever been with any of my friends growing up about panties and sissy things.

When I was about a Sophomore in high school, i would stay the night at my friend Jim's house from time to time. We'd known each other since kindergarten and were really close. We both had younger sister's as well.

Well, one Saturday after midnight, he and I were sharing our favorite "adult" videos with each other on his computer. We'd been a little "worked up" and both went to the bathroom (separately) to finish the job.

Afterward, we were relaxing in his room and I half jokingly, asked "Have you ever wore Mel's (his sister) panties?"

He said "No dude, and i don't think i'd fit haha" "Have you tried Ashley's (my sister)?"

Nervously I said "Yes, sometimes when i'm home alone i "play" in them."

He was immediately curious "Wait, you fit?....how do they feel? Are they soft?"

We both wore generic store brand boxers at the time. His sister was almost the same age as us but on the "plus size". I knew she had a cute selection of panties from the many times I'd hung out at their house. She'd always bend over, showing her Hanes or Old Navy panties. Always with bright colors or cute sayings on them.

My sister was a few years younger and more petite. I had spent many hours (when home alone) modeling her panties in the mirror. She was more subtle with simple polka dots and stripes from Gymboree or Gap.

I told him "they barely fit, but they're so SOFT!!! and it feels amazing to 'finish' in them" "i know i could fit in Mel's just fine"

It was too late that night to do anything, but we began to plan. I told my friend he needed to try panties as soon as possible. He was apprehensive but agreed.

Just a few short days later, he sent me a text with a picture, "Dude i'm home alone which ones should i use" attached was a photo with 2 pairs of panties on his sister's bed. One was plain white with a very small pink bow on the front. The other was lime green with orange flowers.

I replied "use the green ones, ones with patterns are so much more fun" He replied roughly 10 mins later "Dude!!!! holy crap that felt so GOOD"

Later that week, i was home alone and sent him a similar message. The photo showed 2 pairs, one with rainbow polka dots and the others (and older smaller pair) with cinderella on it.

He replied instantly "o you have to use cinderella!!!! will you fit in them?"

I squeezed my butt into the cinderella pair and 'finished' almost instantly. I texted him back "i almost ripped them but it worked!!!!"

We would play this game for a few months, quickly learning our entire sister's panty drawers and which pairs fit and felt good.

Then one day he texted me and said "....would you ever want to wear Mels?"

Sheepishly i replied "....ya...they look so freaking cute....would you want a pair of Ashleys?"

"....ya.....if it's not weird..."

"...no dude it's cool...just our secret man...promise...?"

"ya of course man....totally.....when should we trade?"

we waited a few more weeks, then found the perfect excuse, we needed to study for finals.

He came over after school and my parents left us alone to study. We had the whole house to ourselves.

I asked "Do you still want to do this, we don't have too?"

"Ya man i;ve been thinking about it all day" Jim replied.

"what kinda panties do you want? I asked.

"The girlier the better dude"

I excused myself to my sister's room and selected the pair. It was all cotton. Red with white polka dots and 2 little white bows, one on each hip.

They were the largest size, so i hoped he would fit.

When i returned, he told me to close my eyes. I heard him unzip his backback and place some soft fabric in my hand. I opened them and my heart started racing. They were bright blue with tons of white and pink stars all over. The waistband was bright pink and the on the butt they said "outta this world"

I showed him the pair i selected and we both got tense. I told him to go first, if he wanted.

He walked into the bathroom and shut the door. I could hear his shorts hit the floor. Then him shuffle to slide into the panties.

"Wanna seee....just for fun hahaha" he asked. "Sure" i said. He slid the door open. He was barely contained by the small cotton panties that stretched around his waist.

"dang those look good on you hahaha"
"thanks man...these feel incredible...my sister doesnt have ones like these."

He closed the door and 'finished' in them. then i went in.

I couldn;t believe it. I was going to wear a real girl's panties!!! I practically jumped in them.

"wanna see?" i said after i had modeled them to myself in the mirror. They fit like a glove. better than any pair of boxers or tighty whiteies i had as a kid. I felt magical.

I opened the door and Jim said "whoa those fit you so well man!"

I blushed and said "thanks." I then closed the door and 'finished' in them.

We then realized we had 2 pairs of "dirty" panties that we didn't know what to do with. After a bit of deliberation, we decided to throw them in the dumpster behind my parents house.

We both really wanted to keep them but realized it would be impossible to explain if we got caught.

We never exchanged panties again but we would send pics and make each other choose which ones to "play with" throughout high school.
A couple times he even had his cousin visit who was a year older than us and how thongs and PINK brand panties.

We went to different colleges and soon only would reconnect on spring break or other holidays. We never spoke of the panties again.

Recently he moved out of my area and got married. we only reach out to say "happy birthday" or send christmas cards.
 

[Goodniteswearer89]

My first time wearing girls undies came when I was going thru puberty and lived at home. One day I was home alone and had just noticed a few days ago how my sister was starting puberty and getting boobs so I decided to sneak into her room and find some of her panties and bras and check them out. I found a pair of her underwear in the dirty clothes basket and took it along with one of her bras back to my room and put them on and liked how they felt. It wasn’t till a year or so later I was home alone again and decided to go to her room and take another pair of her dirty undies and bra only this time I didn’t plan on bringing them back. I eventually ended up taking one of her skirts too and wearing it. I have even gone as far as wearing one of her bras and stuffing it with socks to make it feel like I have boobs. Even now I will occasionally put on a pair of my girlfriends undies when I am home alone. 

[curiouswetter]

Those stories were really hot… here’s mine.

From a very young age I have been obsessed with panties. I would try and sneak a peek at them however I could, and growing up, on the playground, I had lots of opportunities to see up skirts, or down the back of shorts. Looking for frills on the waistband, a peek at the pattern or colour. It was always fascinating since all I ever wore were plain white briefs. I looked every chance I could and my heart always raced.

Eventually, this grew into stealing them. I remember the first time… my next door neighbours has a blue pair of Hanes bikini panties out on the line, and when I hoped nobody would see me, I snatched them. At this time I already had a solid wetting fetish, so I would squeeze into them, tuck my penis back, sit on the toilet and soak them. I loved feeling them get wet at the back, and see the crotch darken. Sometimes I’d look in the mirror and enjoy the look of my bulge in the front.

I never bought my own but stole them all the time as a teenager. Sneaking into my friend’s sister’s room while we were hanging out, snatching a dirty pair from the floor, or a clean pair from the hamper. Plain white cotton ones full of stains from his careless younger sister, or the properly-folded flowered bikini panties from his more uptight older sister. I’d wear them, wet them, or sometimes late at night, sneak them out of their hiding place and “enjoy them”.

Fast forward years later. I’m now in my late 30s, and have told my wife about my cuckolding fetish, and how I want to watch another man erupt inside her. She’s excited by it because I enjoy it, and I still have an intense panty fetish, buying her new ones regularly. She’s a fluffier girl and I definitely fit in hers, so she leaned into being dominant, making me wear them in bed, when we go out, sometimes with a plug. She wants to see me taken from behind by a man while wearing the panties she keeps aside for me…

Until that happens, I’ll still steal them and enjoy them any way I can, especially imagining their former owner in them as I enjoy them!