My Reluctant First Times

by MontanaBiGuy

25 Mar 2021 3586 readers Score 9.3 (65 votes) PDF Mobi ePub Txt


We started the day early again at 4:00 am. After a long hard days work I was worn out. Farm work was very demanding and steady, little or no breaks at all. As busy as I was a had a hell of a time forgetting what happened last night. God help me if anyone ever found out. The town I lived in did all but crucify gays. I would be ruined before my life even started. What had he done to me?

I worried myself into a frenzy till dinner. At dinner he was as nice as ever and put my days pay in the box he was holding for me till the end of summer. He assured me if I had needs he would make it happen out of his own pocket. He had such a warm and engaging personality it was hard to stay mad and worried. We had a roast and potatoes and carrots. The man was an excellent cook!  I ate my meal quietly and knew he was constantly looking at me. That made me feel even worse.

He then asked me if I was upset. I blurted out my worries and fears of anyone finding out. He took both my hands and assured me no one would ever know. He also said after this summer I could come back next year but only if I truly wanted to. He would not push and he would still help my family whether I came back or not. It did ease my worries a lot but the guilt was like a brick in my stomach.

We both showered and while I was in there he came in and washed my back and ass for me and left. I finished, dried off and put my pajamas on. We talked in the living room for a while and he told me I was one hell of a worker and he was glad for the help. After a while he went in for his shower. After he got out I did the few dishes and grabbed some jerky to snack on. We watched a bit of TV, I started to nod off and he declared it was bedtime. Oh no. What now?

We went back together and he got undressed again and told me to undress as well. I crawled in the bed and he did as well. Like the night before he pulled me to him and in a couple of minutes had my young cock in his hand again. I was still scared but secretly hoped he would suck it again. What was I turning into?  It was the most amazing feeling I’d ever had after all. His cock was throbbing against my ass again. It frightened me and turned me on at the same time.

He said quietly it was time to share the experience equally and he asked me to touch his cock. My hand shook as I reached back between us and felt his cock. It was much smaller than mine but it did feel good. His wasn’t as hard as mine but it was hard nonetheless. The head was spongy and felt good in my hand. He asked me if I liked him sucking my cock last night. I mumbled a yes. He said I love to be sucked too. Don’t you think it would be fair to suck mine a little too?

I hesitated for a while but he never said a word. I rolled over and slowly worked my head under the blankets and got within inches of his cock. I froze there for a moment and he gently eased my face closer to him. I reluctantly opened my mouth and slipped it over the spongy head. He groaned and said yes! That’s it my boy. Now make a sucking action like I did for you. I did as he asked. He said use your tongue on it son. Lick and suck it. That’s so good. This went on for several minutes. I enjoyed doing it a bit because how much he liked it but the taste would take me some time to get used to.

He was moaning and whispering things to me. Some I could hear some I couldn’t. What I could hear was pretty nasty! He was as nasty as those books in his bathroom. The  But unfortunately it was turning me on horribly. His cock was getting harder and he was throbbing every time I took him deeper in my mouth. He pulled me back up and held me to him. Tonite he whispered, your gonna be my little girl!  

He got up and went to the closet and pulled out a pink girls summer dress. Oh no I thought! Really?  He told me to stand up and he put the dress over my head and turned me around and zipped me up. He pulled me to him and squeezed me tight. He was grinding against my stomach and moaning loudly. He told me to slip on my shoes we were going somewhere. I thought no way am I going out in public like this. I would stab him first!  He slipped on his bathrobe and led me outside to the corral.

I was so glad we were miles from anyone in any direction, I would die if someone saw me. He had me crawl up and sit in the fence rails. He lifted my dress and took my cock in his hand. He bent over and sucked it again. Man did he know what he was doing! It felt so good I never wanted him to stop. He stood up and opened his bathrobe and said your turn, suck me son. I got down and started sucking his cock. He wasn’t near this hard before!  He moaned loudly as I slowly learned how to suck a mans cock.

He pulled me up and held me close. He whispered good girl. Now for the real fun! I want you to stand on the bottom rail and bend over the second rail. I did as he asked not sure what he was gonna do. I was very naive then after all. I heard the snap of the baby oil lid and next thing I know my dress was up and he was smearing it all over my ass. He massaged it into my skin and squeezed my ass a lot. He was really talking now. He said I knew how to be a man last night. Tonite I would be a girl. He started to rub my little hole with a oil covered finger. He teased my ass for a long time. I felt him move closer and his hand closed around my neck to hold me still and slipped his finger in my ass!

It did feel amazing! Scary, weird and amazing. He said this is how a girl feels and he started to finger fuck me. In no time I caught myself slowly pushing back against that invading finger. He slowly withdrew it and I felt his cock against my ass cheeks again. He ground against me even harder tonite than last night. Suddenly he pulled back and lined his cock up with my ass. Oh no! I can’t take that I thought. This was the worst predicament ever!  He pushed slightly and the head slid in to my tight ass. I tried to squirm away but he had me good and he gently reminded me of the picture.

He also whispered that he promised I would like this. It might be uncomfortable for a few minutes but in no time I would love it. He let go of my neck when I relaxed and he said that’s it. Relax and it will feel so much better. He grabbed my dress covered hips and started pushing further inside. I wasn’t totally relaxed yet but it did feel good. He told me he was all the way in, and he was going to fuck my little girl ass now. He pulled back and pushed back in slowly, developing a very easy rhythm. I can’t believe I was liking this! Except the damn dress part. The dirty talk had my cock throbbing. It was jerking like crazy as he slowly fucked me.

He was moaning louder and louder, and picking up speed. He begged me to ask him to fuck my ass. I couldn’t quite bring myself to say it. I did say don’t stop please!  That did the trick. He started fucking me hard and then he would stop with his balls up against me and his cock all the way inside. He leaned over me and said he was gonna cum soon. He picked me up, cock still buried in me and carried me to the house. He told me open the door. I did and he hurried to the bed. He laid down with me pinned underneath. With his weight on me, I wasn’t going anywhere. He started fucking me in earnest. His cock swelling and stretching me even more. It was tough to breathe but it was an amazing feeling.

Getting fucked like this was making me go crazy! My cock needed relief so bad. He let out a strange noise and buried his cock. It was jumping all over inside my ass. I wondered if my cock jerked like that when I came.  I could feel the warmth of his load in me as he squirted over and over. He slowly eased up from my back and said that was amazing and he thought I deserved something special. He rolled me over and took my cock in his mouth and started sucking like crazy! I felt that insane feeling in my gut and legs again and I exploded in his mouth again! I was squirming and thrashing bad enough he had to use both hands to hold me down. His mouth never let go of me though. He held me in his mouth till every last spasm was over.

He stood up and stood me up. He unzipped the dress pulled it over my head. He folded it and put it back in the closet. Go take a shower if you want he said. I did and was still shaking all over when I was done drying off. He sent me back to my room that night. He said the forecast was for rain so we could sleep in and take it easy tomorrow. Maybe even go into town for a movie if I wanted. I said sure. I hadn’t been to many movies and was looking forward to it. I went to my room naked and crawled in the sheets and was out immediately.

More to follow another night! Thanks for reading!

by MontanaBiGuy

Email: [email protected]

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