Falling for an older man

Fun with Jason after church leads to my first anal experience

Being a 12 year old boy suddenly infatuated with girls fashion and infatuated with sex was torture. The day after my first sexual experience with Jaaon, I waa at church as usual. I found myself checking our what the girls and women were wearing to church, wishing that I could dress like them wishing that I could have breasts like them. On this morning I did have to things in common with the girls and women, I liked men like they do and I was wearing panties like they do.

When church ended, I grew excited knowing that I was heading to see Jason. I had been thinking about him and his cock since I left the day before. Mom told me to be home by five for dinner as i got out of the car. I entered the mall, not busy as usual. I saw Jason sitting on a bench in front of his store. He smiled and stood as I approached. He looked so good in his jeans and tshirt. I wanted to hug ans kiss him as soon as I saw him.

Jason lifted the gate high enough for us to get in ans then closed it. He turned the lights on and said I could pick out my work outfit for the day. It was so hard to choose. I finally came to a rack that had what looked like a woman’s shirt, but it had snaps at the bottom.. Jason explained that it was a body suit and snapped closed at the crotch. I waa curious so I took a red one in my size. I kept looking until i found a rack of skirts. I chose a black mini skirt and took them to the fitting rooms in back ans changed. I instantly loved how the tank top style body suit felt when I snapped it closed at my crotch. The skirt fit tight and looked so good on me.

Jason gave me a smile of approval and walked to me, pulling me to him and.kissing me. I had missed his embrace and his kiss. I told him i had to leave at 4:30 to get home for dinner. He said we should get to work. I set about unpacking boxes and sorting things put by size before hanging them up. I loved working dressed as a girl.

It waa about 3:30, I was working at a rack when I felt Jason’s arms wrap around me from behind and pulled me against him. His hand moved over my chest and down toward my skirt

“I think we have worked enough for today” he said

His hand moved to the bottom of the skirt and up the inside of my thigh to my crotch. He could feel that I now had an erection. His hand rubbed it and I turned to face him. I was shorter than him by a lot, so I raised onto my toes to kiss him. I could feel the bulge of his boner against me. The kiss was slow and loving, his hands on my ass

“We should go somewhere more comfortable” he said ans I nodded as I smiled.

He took my hand and.led me to the back and into an office. There was no desk yet but there was a mattress on the floor. Jason said he slept at the store when he needed to work or if he had an argument with his wife. He led me to the mattress and we got onto it and onto our knees facing each other. We embraced and kissed, our tongues rubbing together slowly. Jason slid his hand back under my skirt and when he reached my crotch, he unsnapped the body suit and took my cock in his hand. I undid his jeans and lowered them off of his ass. My young hand held his cock.

We kissed and stroked each other, his free hand pulled my skirt up and he placed his cock against mine, rubbing them together. He started to kiss me faster, we were both getting hornier by the second. Jason broke from the kiss ans was looking in my eyes

“I want to make love to you” he said “can I put it in you baby?”

My mind raced, would it hurt? Would I like it? I could truly feel like a girl if I did it. My brain was screaming for me to say no, but my heart knew what it wanted and.i nodded. I laid back on the mattress and watched as Jason opened a box by the mattress and took out a bottle of astroglide. At the time, I didn’t know what that was. He smiled as he pulled the skirt off of me and lifted the body suit to.my chest.

He waa between my legs, his opened the bottle and put the liquid on his cock and stroked to coat his cock. He leaned over me, laying down on me. As we kissed, I felt his fingers move between my ass cheeks, his fingers coated with the liquid. His fingers circled my hole and he slid a finger into me gently. The feeling was new and a little uncomfortable but it didn’t hurt. He moved his finger back and forth slowly. He pulled his finger out and i felt the head of his cock against my hole

“Just relax baby, I’ll be gentle” he said lovingly.

Jason pushed against me, I could feel his cock wanting to enter me. He pushed again, when he kissed me, he pushed a third time and I felt my ass start to open up a tiny bit for him. The head of his cock entered me, a man’s cock was entering me I thought as he kissed me. There was some pain, not a lot, more uncomfortable than anything. Jason took his time pushing deeper, allowing my ass to adjust to his cock. I moaned into out kiss, Jason pushed deeper, and I loved having a man’s cock inside me. I felt truly like a girl in this moment. I felt his hips touch my skin, Jason was all the way inside of me

He stayed still inside ot me, we kissed lovingly, my hands caressed his back. Jason broke from the kiss ans held himself up on his hands, he looked down at me as he started to slowly move his hips back and forth. I could feel his cock moving inside of me. I began to moan, my voice hadn’t changed from puberty yet so my moans sounded feminine. Jason smiled at me and asked if I was okay, I smiled and nodded as I moaned, my eyes closed, I wanted to savor his thrusts that were going a little faster now. He raised to his knees and as he made move to me, he held my cock and stroked it. He took my hand and moved it to my cock. I started to stroke myself as he started to fuck me taster. My moans grew louder, my hand moved faster. Being fucked while I masturbated felt amazing,

My orgasm built fast, when I came on my belly my tightened on his cock Jason was moaning louder as he gave long hard thrusts, then I felt him pull put of me, he pointed his cock at my belly and came on my belly. His cum mixing with mine. He smiled at me as i smiled at him. Jason leaned down and cleaned up our cum with his mouth and tongue. He leaned over me and we kissed, I tasted our cum on his tongue and lips. Jason moved onto the mattress and I laid on my side facing him. I was so happy being there with him. We had a few minutes to cuddle.

When it was almost time to go, I snapped the body suit closed and put on the clothes i had worn in. I tucked my panties into my pants pocket and the skirt rolled up in a tight roll fit perfectly in the inside pocket of my jacket. Jason gave me another $100 bill.

As I walked home in the body suit under my clothes, I felt feminine, my ass still felt like he was inside me. I loved how it felt after being fucked. With school the next day, I knew I wouldn’t see Jason until next weekend, which made me sad. Jason had understood and said he would be waiting for me. I felt a little jealous of his wife, she got to feel his cock anytime she wanted. She got to go to bed and wake up with him.

I knew I still smelled like sex when I got home, so I hurried to my bedroom and gathered things to take a shower. If mom and sis only knew what I had been doing that afternoon, would they disown me? As I showered, I smiled proudly. I was in love

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