Recovering from our first time together was slow and painful. In the days after, my ass was sore and I had to walk slowly. I hadn’t anticipated how tight I would be nor the burning sensation that accompanied him fucking me like that. Still, I caught myself daydreaming about the feeling of his hot stiff cock in my ass and longed for it again.
This weekend, both of our families were at home. The opportunity to spend our time together seemed hopeless. Jax text me on Saturday and asked if I wanted to go for a ride. “To where?” I asked. “Just around.” He said. I knew what that meant. In our younger years, Jax and I used to smoke a lot of weed. To avoid stinking up the house or garage, we would go for these long drives around some rural roads, away from people and the town. Some of these roads would go for dozens of miles in all directions and never more than an house or two on each.
I threw my things in a bag again. I was slowly building a respectable wardrobe. For instance, I had managed to buy a pair of black thigh high stockings in a shop on the other side of town. I was paranoid someone might see me, so I rushed in and out. The girl at the counter kind of gave me a smile when she saw what I was going to purchase. Part of me thinks she probably sees a guy like me buy stuff like this for the exact same reason from time to time.
Once Jax arrived I tossed the bag in the back and got in. Once we were out of town a little I told him I was going to hop in the back. Getting undressed, redressed, and putting on make up in the back of a ten year old 4 door sedan is not that easy. It took me a good 30 minutes. I wondered if Jax was getting annoyed or tired of waiting as he just drove around and around and listened to the radio. I was forward thinking enough to go ahead and wear my panties and stockings under my boy clothes, so that saved a little time.
By the time I squeezed myself back up front, we were well away from town. “How’s that?” I asked. ” Gorgeous, as always.” He said with a smile. That made me feel good and I smiled, bit my lip a little and tucked my hair behind my ear. My hair was getting quite long now and the more I brushed it and styled it, the more naturally feminine it looked.
Jax reached over and put his arm around my shoulder as he drove. I rested my head against his shoulder and in this moment, it felt so intimate to be dressed like this and be snuggled up against the man who has kissed me, fucked me, and whose cock I have had in my mouth. With these thoughts, my heart fluttered and my pulse quickened.
Jax pulled me tighter and I leaned my face next to his neck. My lipstick covered lips kissed his neck gently and then his lower ear. I licked his ear softly and let my hand rest on his lap. An old familiar buldge began to grow under my hand and I gently squeezed it to encourage its growth some more. I kissed his ear and neck some more and I could hear him breathing deeper and his heart racing. His hand that was on my shoulder then found the back of my head and I felt it pressing it down toward his lap.
I leaned over the center console of his car and began to unbutton his pants. I slid them down then undid the fly on his boxers. The musky fleshy smell of his cock was glorious and I reached in to pull it out. I immediately took him into my mouth and slid my hand between his legs to cup his balls. I sucked on his cock and fondled his hairy testicles. I sucked down his head and shaft and pressed my tongue under his cock firmly. Every bob of my head took him deeper and my hole ached for him again.
His hand trailed down my head and back until it found my skirt. It lifted up the bottom of my skirt and flung it over my back. His hand continued further south and came to rest on my satin pantied ass. He then drifted further and found the soft exposed part of my thigh between the bottom of my panties and the top of my stockings. He ran his fingers inside the stockings and between my legs. As he fondled me, my sucking intensified and I pulled on his cock with my lips and mouth.
His hand found my own balls, tucked neatly in my panties. He caressed them at first and then began to squeeze them. That hurt and the pain made me moan. My moans muffled by his fleshy cock in my mouth. He squeezed them harder and then slapped them. My moans grew louder and I whimpered a little, never releasing him from my warm wet mouth.
He squeezed them harder again and my whimper grew loud. I forced my head down on his cock further and swallowed his shaft as far I could take it. His grip on my balls tightened, I cried tears down my face, then the warm saltly explosion filled my throat. I swallowed and swallowed more. Drinking him down as his hand loosened and his body went soft.
I licked up the saliva and cum that had dripped down his shaft and wiped my mouth. I buttoned his pants back up and then sat back in the passenger seat again.
His eyes were relaxed and he had this perpetual grin on his face. I blushed and smiled, knowing it was me that made him feel that way. We made our way back to town and as we started seeing more cars, I began to feel nervous. What’s if someone could tell I was just a boy in make up and skirt? Would they laugh at me? Call me names? I felt very insecure. Just then, as if he could read my mind, or just my body language, Jax reached his hand over to my soft thigh and in his deep calming voice said “Don’t worry. You look great. No one can tell.” I felt comforted, if not still a little nervous.
We parked at the mall. A big crowded parking lot where our car just blended in with everyone else. We sat there for a moment and then Jax began to speak. He told me how he wasn’t sure what he was feeling lately, but he knew he couldn’t wait to see me each weekend. He said sometimes he laid awake at night replaying our encounters over in his head. And at least once or twice, he has jerked off to the memories of me sucking him off or him fucking my ass. He says my shy face, hidden under my hair and softened with makeup, is there every time he closes his eyes.
I was weak.
I suddenly didn’t care what the world thought. I wanted this man and I wanted him to take me however he wanted.
We started to drive back home. I had just enought time to throw my boy clothes on and baby wipe most of the makeup off before we got to my house. I tried to avoid contact with my family as much as possible and sprinted upstairs without them getting a good look at my face. I closed the door to my room and collapsed on my bed.
After a moment, I heard a knock coming from the bathroom door. The bathroom was a jack and jill style. It had two doors leading into it, one from my bedroom and one from my sisters. If I was hearing a knock on it from within my room, that meant my sister was in the bathroom and wanted to come into my room.
“What?” I called out to her. “Hey, it’s me” she replied. “Yeah I know it’s you. What do you want?”
“Well your finally home..” she said
“Yeah, what’s your point” I asked curtly
“Well I was wondering if you were ever going to give me my makeup back? I am going out tonight.”
I froze. My worst fears were realized. Someone knew.
Source: reddit.com/r/Erotica/comments/u6dhuw/becoming_my_best_friends_crossdressing_sissy
✨Wet pussy💦🐱like suck on video🍌👅👉 [**Hot Girl**](https://www.321.ge/lO1rC)