First Time Bottoming

This is a true story that happened almost a year ago. Little background before we get started, I’ll use only our first letters for privacy. Im R I was 28 at the time, and he is J and he was 36 at the time of this amazing encounter. 

So how we usually meet up is I wound message him and see if he was available during his lunch and if he was I would drive to his house and we would hook up together. Normally we would make out, suck and then usually I’d top him bc I would be too nervous to take his thick 6.5” cock in my tight ass. We always had the best encounters (in my opinion), but this particular day I was determined to not be a little wimp and let him pop my cherry. To prepare for this day I decided to use a dildo I have to least give my hole a little stretch so it would make his slide in easier.

I rode my dildo for a few mins and then got myself cleaned up and headed off to his house where he was already waiting. I walked into his house and we immediately embraced in a hot make out session. I could feel his cock get hard rubbing against my already hard cock. He let me lead him up the stairs to his room where he would grab my ass the whole time up the stairs. As we walk into his room we strip out of our clothes and back to making out feeling our naked hairy bodies against each other. He starts kissing down my neck, down to my nipples, giving them a kiss and suck. I let out a moan and he continues on down to my 6” cut cock. He takes it all into his mouth in one gulp, I let out a loud moan as I watch him start working my cock in and out of his mouth. As he’s sucking me I spread my legs out and he slides a finger under my balls and up to my hole. I start moaning more telling him how great it feels. J starts rubbing my hole with his finger slightly pushing in on my tight hairy hole. I let out a moan and tell him I need his cock in my mouth NOW! He pushes me back on the bed and then gets into the 69 position and I start sucking his huge thick cock. I take all of it into my mouth gaging on it. I’m too caught up in sucking him that I didn’t notice that he grabbed some lube and lubed up his finger and was sliding it into my hungry hole. I let out a muffled moan as his cock was filling my mouth.

I lay on my back and arch my butt up so he can get in there better. He starts fingering my ass and I just start moaning louder, grabbing the sheets and moving my hips to the motion of his hand. I moan out to J “I want you to fuck me with that big cock of yours” “bareback my tight hole” that’s all I had to say and before I knew it my legs were up on his shoulders, my hole completely exposed. He looked me in my eyes and said “look at this tight hairy hole” I told him “it’s all yours to fuck” he lubed up his cock and started pushing it in. He got the head in and I had to stop for a min, he was so much bigger than my dildo, he slides slow into me and then tells me he’s halfway in. He looks at me and asks if I’m okay and I said “mm yes I’m great!” He slides more into me, and then he starts to slowly fuck my tight ass. At first I was little uneasy with the pressure I was feeling down there but soon I lost all control of my body. I was in heaven! It was a feeling I never had before. The pressure turned to pleasure, he was making me feel so good! I was moaning so loud that I’m sure his neighbors could probably hear me ( they are like 50 yards away too) I grabbed his sheets and dug my heels into his back and said “don’t stopppp, ohhh fuck yes daddyyy don’t stop” he started thrusting harder and harder. I didn’t realize that he wasn’t touching my cock and I wasn’t either but I felt like I was about to bust. Then it occurred to me that he was pounding my prostate with every thrust, and that I was about to experience my first ever prostate stimulation orgasm. He started going harder and I just grabbed two fist full of sheets and screamed “ohhhh fuckkkk yessss!” I shot rope after rope of hot cum all over us. He continued pounding my hole as I was just in absolute heaven. I’m just a few more pumps J was pumping my hole full of cum! J said “ I’m going to breed this hole babe” I let out more moans telling him “make this hole yours daddy! Breed me” he pushed deep into me and let what felt like 6 huge ropes of cum into my ass!

We laid there and made out while he was still inside me, he slowly slipped out of my cum filled ass and now I felt empty inside since he wasn’t stuffing me. I lifted my legs so he could get a good look at my cum filled hole that he made. We made out and cuddled for a few mins till it was time for him to go back to work. We got dressed and he went back to work and I went home with his cum dripping out of my ass. After that day all I’ve wanted to do was be a bottom. And I think I may still top from time to time but I’m more into being a bottom boy.

Thanks for taking time to read!

-R