Back when i was 18 i was young and did stupid shit. I remember i was horny and didn't have a girlfriend at the time. I was tired of masturbating all the time, so i decided to go on the local craigslist m4m page and make a post about wanting someone to fuck me. Not 5 minutes later i had 10 replies. After weeding out the bots and tweakers i had one email left. It read: 47 Bi male, Daddy. After carefully exchanging a few more emails we decided that he would host at his house. But he had one condition. I had to wear women's clothes.
I snuck out of my house and skated to his house. When i knocked on the door i was greeted by the same face i had seen in my emails. He was talking on the phone with someone. After a few moments he said "I gotta go, a friend just showed up." I waited until the phone call was over then said "Hello, i'm the guy from Craigslist." He smiled and said hello. We talked as he closed the door and led me into the living room. As we reached the sofa we had finished exchanging pleasantries. He took the break to change topics. "You know why you're here, right?" I said I did. He informed me "That i was to call him Daddy the rest of the night, and he would call me son." I agreed and started calling him daddy. He told me that i was to go take as shower as i had gotten all sweaty on the ride. "There will be clothes on the sofa when you finish showering." he added, "Meet me in my room, when you get dressed." I raced to the shower and striped off my clothes. I hopped in the shower, and found a butt plug and a note saying 'Put it in.' I showered and slid the warm glass plug in my ass. I emerged from the shower and dried off. I walked out of the bathroom and was greeted by a set of shining white lingerie. Another note read 'Put it on -Love, Daddy.' I slid on the white stockings and pulled up my new panties. I slid on my garter belt and clipped my bra. And finally I put on the sheer robe that had been laid out. I walked calmly across the house, thinking about what daddy was going to do to me. As i opened the door to his room, I saw him buttoning his shirt up. He looked up and said "Son, you know what i said would happen if you were caught wearing your Mom's clothes." I spoke back playing along, "I know Daddy, but i just think i look like a pretty girl." He sighed and looked me up and down and then undid his belt. He roughly spoke "Take off your moms robe and bend over the bed." I did as he said. As i bent over i felt the stinging pain of the belt across my plugged ass. He sacked my ass twice more and said "i'm sorry for punishing you, i'll make it up to you." Slid his pants to the ground. I looked up at him and ran my tongue around his cock. Then again, and again until it was completely wet. I then licked the head a few times before taking it as deep as I could. I kept sucking, sometimes switching to his balls. Finally after a few minutes he came on my face. He then told me, i had done such a good job that he was going go reward me. As he told me this he slowly rubbed my erection through my panties. He told me to get on all fours. I did as he said. He slid my panties off and began to lick my ass, and balls. He was very good, but I fought against cumming, i was almost beating it until he lightly traced my cock. I came hard and fast. He looked at me and told me to clean up my mess. I began licking up my mess, and by the time I had fully cleaned up, he stood behind be with lube and a condom on. He grabbed my hips and eased me back onto his cock. He slid into me and began to slowly fuck my ass. After a few moments getting used to it he began to speed up. Harder he fucked my ass, slowing down occasionally, until finally he pulled out of my ass, slid the condom off and came in my mouth. After he had cum he told me i could leave the clothes on and slide the plug back in. I left and returned a few more times.
Source: reddit.com/r/gonewildstories/comments/3ikow5/my_first_time_with_a_man
Great story!
Thank you!
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Thank you!