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I published this story and took it back, but I'm republishing again. If you enjoy it please do let me know so I feel confident enough to do the same with the following parts.
This is a fictional story that I have combined with some of my own personal experiences. Everyone is over 20.
A rainy day in the winter we were heading to my friend David's house to work on a project for college. We have known each other for a year and a half and had shared a lot of good bonding moments together and become really close to each other.
On this particular day we had to work on a project for a class and wanted to finish as soon as possible to go back to college life, but since it was a big assignment we knew we had a long time ahead of ourselves.
We arrived at his house and noticed there was no one else aside from us.
"Everything feels so empty," I quietly said.
David remarked that his parents and older sister were out of town for a family gathering.
I smiled back at him and we walked to his room. We spread our stuff around and began working as fast as we could, but no matter what we did we could not focus so we ordered a pizza and just chatted.
After a few hours of unremarkable time eating pizza and watching tv David stood up from where we sat and said he had to go to the convenience store to pick up some beers since there were none at the house at the moment, I on my part was completely exhausted so asked if I could stay. He smiled at me and left right away.
Once he had left I stood up as well and walked all the way down the hall where the bathroom was and I couldn't help but notice that his sister's room was open, my eyes opened wide and stood in front of the door.
For a while I had been crossdressing by "borrowing" some of my older cousins stuff whenever I could. The feeling of panties against my skin, the soft pressing of a bra on my chest made me overwhelmingly excited. However, I haven't had a chance to cross dress in long time. In between college and my lack of access to clothes I had become obsessed with the idea of feeling feminine again.
That's when I saw that door open and an idea rushed into my mind. David's older sister had kind of a similar build to mine. She was thin and small breasted and around my same height, in that moment I took one look to the left and right then entered the room as quietly as I could.
I didn't turn on the light so I wouldn't let David see whenever he came back home. I rushed to the closet and opened the doors, it was a heavenly view. Dresses lined up the tall racks and a few drawers were in plain sight.
Reaching for the first drawer my hand shook and trembled in anticipation. Once I finished opening it I saw a whole drawer of panties.
I reached into it and started browsing until I fished out a few. One was a lace black thong, another was a pink bikini pair with a small bow in front, and finally the one my eyes were drawn to, a pair of white lace cheeky panties with floral patterns.
I quickly tossed that white pair to the side while rearranging the drawer as it was before I found it. Suddenly, I found myself opening the second drawer where her bras were stored, giving me a rush of adrenaline once more.
There in front of me were more bras that I had ever seen before. Too many choices, too little time.
I decided I would grab the first pair I could find. Reaching down the drawer my heart pounded harder and harder, my cock hard as a rock as I felt it pressing against my pants. It felt like ages but it was probably a couple seconds before I took a dark blue sports bra.
It wasn't my first choice but I figured I wouldn't have any more time to keep browsing.
Once I had my "attire" complete I figured I would quickly rushed to the bathroom to try it on and masturbate. However, as I started to walk I found myself thinking it wouldn't enough time, so I stopped and started undressing right on the spot.
Then, I slowly pulled up the panties until they covered my hard cock. I could see a drop of too of pre cum coming through the fabric. It felt like a perfect fit.
I twirled a little bit as I admire my figure in the mirror, after which I decided to try the sports bra.
Once everything had been set I checked once more, I couldn't fathom how feminine I looked. It was amazing and exciting.
I slowly began rubbing the palm of my hand against the panties. I couldn't have enough of the feeling so I kept rubbing over the soft fabric, taking me close to cumming.
In that moment I heard a small creak on the floor and horrified turned my head up. There, in front of the bedroom door was my friend David just looking at me, holding a bag.
"I can explain," I said almost in a begging tone.
He gave me a look and turned around, just mentioning that we didn't have to talk about it.
"Just put on your clothes and pretend I didn't see you dressed up like that," he droned.
I just nodded and dressed back up in my male clothes. The rest of the evening we just worked in silence, drinking one by one all the beers he had bought before.
Then, he quietly reached for a small bottle of tequila he had in the corner of his room, asking me if I'd like to join him. Quietly I nodded and got closer to him, already feeling shy enough for having tried his older sister's underwear.
He handed me a shot glass with tequila and I just finished it one gulp, he did the same afterwards. The evening kept going like that until we were pretty drunk.
"I don't think we're in the mood of more homework," he chuckled.
I smiled back at him.
We sat on his bed, both of us tipsy from all the beer and booze we've had before. Time seemed to go by so slowly as we watched whatever was on the TV.
After what felt like the longest awkward silence ever I jumped slightly as I felt a his hand reaching my lower back. Turning around I could see David with a rather cute smirk.
"You looked quite cute," he said so quietly it almost felt like he was whispering.
I was in shock, didn't know how to react to a comment like that. It had been the first time someone had seen me in a more feminine outfit, let alone remarked on it. I quickly took another sip of the drink I had in my hand muttering a thank you along the way.
For a second everything felt tense, until David turned around and looked at me with a small grin on his face. He asked if I could dress up for him right in that moment.
A huge moment of doubt came at hit me like a wave. On one side I felt extremely embarrassed because of what had happened before. However, I was craving more.
My mind just desired to feel feminine again. To dress and just embrace that side.
"Please, I promise it's not to make fun of you," he said.
I stood up and just nodded at him, a few seconds later we were walking down the hallway to his sister's room.
The hallway seemed to go on forever. My heart bumped so hard I could almost feel as if was coming out of my chest. Finally we got to his sister's room and opened the closet together.
"Go ahead, try on whatever you like," David said with a genuinely sweet smile.
I grabbed the pair of panties I was wearing before, however I looked around and found a nice bralette to complement it. It was white as well with soft lace and a cross strapped back.
Then, a bit nervous but excited, I checked the next drawer and found a pair of black tights. Afterwards I kept perusing the closet, after all David had given me the liberty to take whatever I liked.
I found a skampy green summer dress. Gathering my whole outfit I ran into the bathroom ready to get changed.
I removed my clothes and my underwear and as I did I noticed how much precum was leaking already. I couldn't believe I was going to be modelling in full femme for someone.
Quickly I started moving the panties up my thighs until I could feel that snug embrace of the fabric against my cock.
I put on the bralette and the tights, finally, I put on the dress. As I was about to leave the bathroom I spotted some sparkly lipgloss on top of the sink. I applied it fast as I heard David reaching from the room.
I was trembling as I opened the door, almost feeling like I was about to cum just from him seeing me in femme.
Slowly I made my way out of the bathroom and I could see David sitting in bed, his face almost completely red and eyes fully open.
"Is, this okay," I asked.
"You look incredible," he managed to reply.
"If you're going to mock me then I'll just leave," I stated in the bravest tone I could muster.
"No no! I mean it, you look incredibly sexy," he yelled.
I had already noticed how drunk and aroused he was.
My ears perked up, I had never heard someone saying that about me. I always thought I looked completely unappealing in masculine mode so to hear someone saying I looked cute in femme made me really happy. And even hornier than I was at that point.
I came closer to him so he could see me better. David just continue to look at me, mesmerised about that way my hips (the very little I had) moved in the dress.
As soon as I got close enough to him I saw a smile on his face.
"I guess someone is excited," he smirked.
Looking down I saw how my boner was visible over the dress. Quickly I put my hands on top of it as I felt David's eyes scanning me up and down.
I smiled back at him.
Before I could think about what to do next I felt his hand grazing my leg over the tights.
"Can you come closer," he asked.
I stepped one foot forward. He asked twice more to go closer to him.
I was right in front of him feeling his knees touching my legs. Then I felt his hands touching my thighs, grabbing them. He made all the way to my ass and pulled me over him so fast I couldn't react.
We were both face to face, close enough we could smell the tequila we had just drank before. All of the sudden he reached and kissed me, it was one second but it felt like forever. He recoiled right after and as I moved away from him I could feel his boner against me, it was too much, I haven't felt so exposed ever.
I was so horny, so excited and such ecstasy that I couldn't contain myself anymore and felt a wet sensation running down my thigh, I had cum without even touching myself.
My face went blank as I tried to pull away from David, wanting to rush out of the room, but then I felt a hand grabbing my wrist. It was David, an incredibly vulnerable moment occurred.
He leaned in and kissed me once more, as he undressed me. He moved the straps of my dress first and felt it fall down exposing my body and the underwear.
He then removed the straps of the bra and admired my chest.
"Fuck you're sexy," he said.
All of the sudden he was all over my nipples, sucking and biting them.
I was melting down from all that was happening.
David came even closer and lifted me up as he removed the tights (now soaked in my cum) revealing the panties and my still hard cock.
"I want you," he huffed.
He grabbed my ass in a way that almost made me melt.
"Fuck me, now! Here," I screamed.
He hesitated, after all we were at his sister's room. Then with all his force he grabbed me and carried me out to the hallway.
The idea was for us to go all the way to his room but we both knew there would not be time for that.
We collapsed on the hallway floor and David removed my panties. I was completely exposed to him.
He removed his clothes as fast as he possibly could showing me a body so closely similar to mine that I was almost certain he would look great in a dress too.
But before I couldn't think any longer I felt the tip of David's cock close to my hole. I didn't have time to tell him I haven't been fucked like that.
However, before I could say anything I felt the penetrating sensation of his cock in my ass pussy.
It burned, hurt and made me horny in a way I could have never imagined before. In an instant David started pounding thrusting in and out.
Over and over I felt the force of his pelvis against my ass.
"I'm cumming," he moaned.
"No! Not yet," I begged.
My arousal was just starting once more, I wanted more, I wanted to cum.
He didn't listen though, instead he started moving even faster. That sensation fullness, of that raw encounter we were having just made my mind go wild, I lost any sense of direction direction and became just his cum dump.
After what felt forever the thrusting suddenly stopped and I felt the pulsating sensation of David cumming inside of me.
Then, he started rubbing my cock until I came. Both of us collapsed after that and silence filled the whole house once more.
We spent what felt like hours just there on the floor, until David pulled his cock out and I felt his cum dripping down, after that we both fell asleep right then and there.
I woke up to the sound of stuff being moved and as I opened my eyes I saw David already dressed coming close to me.
"Good morning," he said.
He was making some breakfast and smiled at me. That smile alone made me feel warm inside, I felt almost blushing.
I took a shower and slowly cleaned myself from all the cum that had dried in my body.
Returning to the kitchen I saw David once more. We had both returned to our "usual" looks. We exchanged a few words but everything felt awkward.
After a long time of cleaning the hallway and washing his sister's clothes we returned to his room and sat quietly in bed. I was checking my phone trying to figure out something to do when I heard David speak.
"Can we dress up together next time," he asked.
His smile was sweet and his hand reached my thigh.
My heart skipped a bit, not only we had enjoyed each other but he also wanted to dress up with me.
"Of course," I replied.
He put his hand on top of mine and we both smiled.
This would mark the first of a few more experiences we would share together.
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