First time sex as a CD

by Jester4fun

21 Apr 2023 5035 readers Score 9.3 (96 votes) PDF Mobi ePub Txt


We were older teenagers Charlie and I. He was a very best friend and we were inseparable. Charlie would stay the weekend with me and vice versa. So ever since I was a young man I had weird feelings. I became very curious and started looking at naked pics of guys. I came to learn that it turned me on my bad!! I began to wonder what it would feel like to be with a guy sexually. The Weeknd was coming up and Charlie was planning to stay the weekend at my house. All day at school Friday I couldn’t think straight, excited and nervous I was gonna plan my move. What the hell am I doing I thought. I was tall, slender, smooth all over and tanned. The night came that Charlie drove over and we hung out in my room listening to music, playing video games and talking about girls. I knew what I wanted to do but didn’t know how to approach this at all. Charlie began playing video games and was glued to the Tv when I asked him if I could ask a serious question. Charlie replied”sure Jess ask me”. I said”have you ever thought of being with a guy?”. Charlie laughed and said no, have you? I said “well yes it’s crossed my mind before”. He continued to laugh and asked what guy did I want to be with. I lied and replied “I don’t have anyone in mind”. He continued to giggle as I went to the bathroom. While in the restroom I put on a very tight black shirt and tight booty shorts. I looked in the mirror and thought to myself “oh fuck I’m about to make my move”. Heart pounding and shaking I wanted to experience sex with a guy, with Charlie. Charlie was a fighter and most guys our age was scared of him including me. I exited the bathroom and walked back into the room. I immediately got under the covers while Charlie continued to play video games. I began to slowly rubbed myself until I was so turned on. I asked Charlie again “so hey really have you never ever thought what it would be like to be with a guy maybe just one time!”. He said “I have but never put a whole lot of thought into it”. I was so damn nervous I said I’m going to get some water and asked Charlie if he wanted any. He said yes. I got up and Charlie saw what I was wearing. I noticed him looking at me differently and staring at my ass and long legs. He watched me till I got out of sight. I retrieved some water from the kitchen heart still racing. I just knew I was gonna get Charlie’s dick tonight. I returned to the room and Charlie was still sitting in the same position on the corner of the bed not playing the game anymore. I walked straight to him and straddled him wrapping my long smooth legs around his waste and placing my arms around his neck. I figured he was either gonna whip my ass and tell everyone I was gay or we were gonna fuck. I didn’t care I had to find out. Much to my desire we began to kiss. I could feel my heart race high and my cock getting harder than it’s ever been. We kissed it seemed like for ever as our tongues met. I thought OMG I can’t believe this is happening. Anyone could have walked in and I wouldn’t have even noticed. Charlie at once lifted me up and placed me on my back and slid his pants off and I noticed he had a huge boner. I grabbed his boxers and he said “you want this don’t ya”. I head nodded yeah as he pulled his dick out, I thought oh my God we are really doing this aren’t we! On all fours with him standing by my bed, I cuffed his balls with my hand and began to lick his hard shaft up and down while massaging his balls. I was thinking to myself fuck I’m gay and I loved it. I then began to suck his cock as it started hitting the back of my throat. Charlie started to moan slightly saying fuck yes fuck yes. I continued to suck his dick until I felt him tense up. I knew he was about to explode before he announced the words that blew my mind away. He said “I’m about to cum baby where do you want it”. I continued to suck and suck until I felt him shoot his load down my throat and all over my face. I was moaning and sucking his dick till he couldn’t cum anymore. I then laid on my back as Charlie began jacking me off with his cum as lube. He didn’t feel comfortable sucking me so I just enjoyed a awesome hand job as I climaxed busting my load everywhere moaning and squirming. I laid panting and smiling on the bed as Charlie cleaned up. 
  
     Months went by before our secret happened again. The next time was something I’ll never forget. Charlie and I went to Nashville for a football game and we decided to drive up Friday evening and stay the night. On the way we were manly and never really spoke of our dirty little secret but I knew without a doubt I was gonna have his dick for the second time that night. Once at the hotel we settled in and I went to the restroom. Applied my eye shadow and makeup flawlessly, I then put on a pink garter belt that connected to black thigh high stockings. Tight black shirt and placed a chocker around my neck. I’d already let my hair grow so it was medium length blondish and I had my belly button pierced. I walked out of the bathroom and he said “oh my fucking God baby”! Lips immediately locked while he squeezed my ass so hard I thought it would bruise. He slammed me on the bed and started eating my ass, I was lost in ecstasy as I told him I was his and that he could do whatever he wanted to. After eating my ass for several minutes I couldn’t take it anymore. I told him to please fuck me, he flipped me around and put me on all fours. He lubed his dick up and slowly started fucking me from behind. I was pushing my ass against his cock matching his rhythm. He began to speed up the pace grabbing my hair and kissing me on my neck while fucking me like the whore I am. I’ll never forget his moan, me cumin so hard just by him fucking me. I cum so hard I blacked out!  I had his cum running out of my ass as he laid on his back exhausted and resting. I climbed on him and laid my head on his chest. We were soaked in cum and sweat, I was so horny and comfortable I kissed his lips and said without knowing wtf I was saying “I fuckn love you baby and I wanna do this everyday”. Well it didn’t happen everyday but that was 15 years ago. As life took us to different avenues in life we had sex maybe 10 more times give or take. I haven’t seen him and years but every now and again I think about that night and get so horny for him.

by Jester4fun

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