Becoming my best friend’s crossdressing sissy girlfriend. CH 02 – Exploring

Jax did text me later. He told me about what his family had for dinner and we swapped a few memes. Neither of us said anything about our encounter or what happened. Was he avoiding talking about it? Was he even thinking about it? I went to bed that night with a million thoughts running through my head.

A few days later my sister was out of the house again. I used the opportunity to go through the box in the back of her closet again. I desperately wanted to wear that old pair of skinny jeans she had in there, but couldn’t get them past my squishy thighs. I could fit in the skirt she had though. It was khaki with heavy pleates at the bottom that stopped above the knee. The silk black blouse fit as well.

That weekend she had another tournament that my parents took her to. Jax text to see if he could come over. I told him to come around lunch, that gave me a little time to get ready.

I went to the bathroom and pulled out the clothes and makeup I had stashed away. This was it. There was no turning back now. If I did nothing, Jax and I could pretend it never happened and go on with our friendship and lives. But if I went through with this, it would forever change everything between us.

I looked long and hard at myself and got in the shower. In there my sister had one of those pink body razors. Luckily I wasn’t too hairy, but it did take some care not to cut myself. I started with my legs, then thighs, bottom, arms and armpits. The water on my shaved skin felt strange. My skin was so sensitive now.

I got out of the shower and blow-dried my hair to give it some volume. I put on a floral scented lotion to keep my skin soft and moist. I slid on the panties first. I had gotten more used to wearing them, so much that I didn’t get hard right away like before. There was still a buldge, but at least I could wear them comfortably.

The skirt was next and then I tried to do the makeup. I had watched a few videos for some tips. It wasn’t great, I needed more practice for sure. I think it looked ok though. The dark red lipstick just drove me wild every time I put it on though.

I snapped on the bra and used some socks to fill the void of the cups and my flat chest. Once the blouse was on, I had this muted hour glass type like figure. The socks helped with the top curves and the skirt sinched at the waist and made my hips poke out a little. At the last minute I found a set of stick on nails as well. Kind of a blush pink with a little glitter, nothing too bold or outrageous. One last spray with the floral body spray to match the lotion and I was ready.

Just then the doorbell rang. Jax text me and asked if he could come in. No turning back now. “Don’t chicken out” I told myself in the mirror.

I nervously walked down the stairs. I heard Jax come in and flop himself on the couch as he normally does. When I turned the corner of the hallway to the living room, the look of shock on his face traveled across the room. His jaw fell open and he covered his mouth with his hands.

“Oh my god” he said. “You…you ..” he stammered. “Yes?” I asked nervously, picking at my nails. “You look amazing.” The feeling of relief washed over me and I could breathe again. “Really?” I asked. “You think I look ok?” “I’m serious..I’m just at a loss for words here..”

My confidence went up a little and I got the courage to go stand closer to him. He was always taller than me, but I felt even shorter now. My eyes were at his lower jaw level and I kind of looked up at him. “Do you want to go upstairs?” I asked shyly.

“Yeah” he responded. As I lead him upstairs, I realized that with me a few steps ahead, his head level was right behind my bottom. Was he looking at me? Would he try to see up my skirt or grab me? Do these kinds of thoughts go through girls heads all the time? We got to my room and I sat on the edge of my bed. I had no idea what to do or what would happen, but I was here now and so was he.

He sat next to me, close enough that the sides of our legs touched. He leaned over to me and brushed my hair behind my ear again. He leaned in…and kissed me.

Softly he pressed his lips to mine. I would have been so terrified I would have been frozen if not for my body trembling with nerves. He leaned into the kiss a bit more and I felt the scruff of his face on my smooth skin. I started to lay back on the bed and he leaned over top of me.

I could almost feel the weight of his body on top of me. My hands found his thick hard arms and my nails gently caressed his muscles. His hand found my thigh and I felt it slip under the bottom of my skirt.

His hand found the bottom of my panties and his finger began to slip under and out of them. He made his way center and found my buldge through my panties. He squeezed it gently and I grew stiffer and winced at his grip.

He grabbed me by the hip and rolled me over. He flipped my skirt up and reached to slide down my panties. He pulled them down just past the bottom of my ass and then I felt his scruffy face press against my shaved smooth ass cheeks. He began to kiss and bite at my ass. Then his thick warm tongue slid between my cheeks to my center. I felt him lick at my hole and dribble salvia in and around it.

He pulled away and I heard him stand. I heard his belt come undone and his zipper fall down. I heard him take off his shirt and throw his pants and boxers aside. I felt him lay on top of me, his weight pinning me down on the mattress.

He leaned over and kissed my face and neck. I grabbed handfuls of blanket and tried to control my breathing. I felt his warm stiff cock begin to slide and poke at my ass cheeks. He then let the head begin to press against my hole. My pulse raced and my body clenched. He pressed the tip a bit more firmly again and I tried to press my hips into it. Slowly the head began to slip inside me and I moaned in pain. He paused and allowed me time to try and relax.

I felt his hand grab my hips and hold me down. He slid his cock a little further in and I winced and cried again. Being penetrated is the most helpless of feelings. Even if I wanted to leave, it was almost as if I was paralyzed and my legs couldn’t move. Any shift or movement on my part sent pain shooting up from my bottom through my back and abdomen. I was completely at his will.

I breathed and relaxed my body again. I guess he could feel the tension leave and he pushed further one more time. With this final gradual thrust, he was fully inside me. I felt his pelvis and legs pressed against the back if my ass and thighs. His weight drove his cock the last inch inside me and we both laid motionless for a moment.

My body and ass twitched and a few tears ran down from my eyes. His hips raised and he began a slow humping on top of me. His cock didn’t move much, but his humping had the effect of thrusting while still inside me. I began to match his rhythm and meet his thrusts with my ass.

Then he slid his cock out of me slightly and back in again. His saliva aided the motion and his thrusts flowed more easily. My hole was much more relaxed and though each thrust in sent screaming levels of pain through my body, I wanted more of it. I found pleasure in this pain.

His thrusts didn’t increase in speed, but they did get more forceful and harder. I felt his body tense and he began to grunt. His hard thrusts went deeper and deeper and until he could go no more and then he stopped. He clenched his body around mine and dug his fingers into my soft flesh. I felt this exploding warmth inside me that spread in my center. He grunted more and his grip tightened. I tried not to move and just receive Jax’s cum inside me.

Then his grip loosed, his body relaxed and his breathing began to slow and deepen. Mine as well and the fistfuls of blanket I had were released.

We laid there for a moment. Silent and unmoving. His heavy body pressing mine down. He shifted and slowly slid himself out of me. He stood up and slowly walked to the bathroom. I laid there, processing what had happened and what I had gotten myself into. I rolled over and the shooting pain from before returned. I felt his cum leak out of me and drip down the back of my thigh.

When Jax returned he got dressed and said he needed to go. I think we both needed time to reflect and think about this experience. He did lean in to kiss me on the side of the face again and then he was off.

I tried to walk to the bathroom. Each step felt like burning fire in my butt. My legs shaked with each step and I had to hold myself against the wall just to make it the 5 feet to the bathroom. I showered and put everything away. The shower did help, but I still felt like I got hit by a truck.

I made it back to bed just in time to hear my parents and sister come home. My mom came upstairs to check on me. I told her Jax and I had worked out in his garage gym and I was super tired and sore. I was probably just going to nap for a bit and she left me to it.

Source: reddit.com/r/Erotica/comments/u2504r/becoming_my_best_friends_crossdressing_sissy