My First Time Bottoming

BlueBearCub

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Back in my college days roughly 2009 was the first time I experienced anal sex as the receptive partner. I was still deep in the closet, so my only gay experiences have been with hookups on the popular gay "dating" apps like Adam4Adam and the personal sections of Craigslist. (Yeah I know really dangerous) I have topped once or twice, but really wanted to try bottoming. I had a previous experience where I tried bottoming for a guy, but could just not relax for the guy and he eventually gave up. Wanting to redeem myself from that moment, I decided my next hookup I would finally lose by bottom cherry.

Fast forward weeks later and I am in my room and of course horny as fuck. I decide to make a post on the personal section of craigslist detailing that I am a virgin looking to bottom for the first time. This type of ad always led to my inbox flooding with messages from lots of guys. Finding someone who actually looked attractive and also sounded normal was the hard part. This was not my first time doing this, but I never gave up hope finding the right person.

As I waited for the ad to become public and the responses to start arriving, I wondered what would I do if I actually found someone worth meeting. I still was very nervous to bottoming, but my horniness was overriding by anxiety and fears.

Once my ad posted and became public I started getting responses within minutes from a wide arrange of men; old, young, skinny, fat, etc. I find myself a very open guy and open to various ages and body types, but something about it being my first time I was looking for someone who I found to be very attractive in my eyes.

I probably talked with about 10-20 guys, but either they would be really sketchy, not share enough pictures to get a good feel of what they looked like, or would just not be my type.

I was starting to lose hope and started contemplating if I should just jerk off and go to bed. It was already getting late around 10-11pm and the chances of getting someone still wanting to meet up this late was getting slim. As I was just about to give up I receive a response to my ad from this guy. He sends me his stats, 6ft 4 210lbs black muscular/athletic build 8in cut. I am stunned by these stats and assume they are exaggerated. I ask him of course to send pics to prove some of this. He quickly sends back pics and I was surprised to see how accurate they were. My first thought was, how is this stud of a man interested in me? No way he could want to actually meet and hookup with me.

We quickly share a few messages back and forth and he seems truly interested and also open to the fact it would be my first time and that we would need to take it slow. Before I even had a chance to think, he sent me his address and said to come over now. I was like oh shit this is actually going to happen and the ball is in my court. Being a 19 year old horny guy I immediately jump in shower and get in the car to start heading to this guys place.

The whole ride to his place, I am shaking with nerves. Was I really about to give up my virginity to this guy I only said maybe 5-10 sentences to? What if I was being catfished or what if something else?

My nerves did not let up and I was almost visibly shaking as I got to his door. With me throwing all fear to the side I message him that I am at his place. Within moments the door opens and I am surprised to look up at exactly the same muscular athletic tall from the pictures. He was wearing basketball shorts and a t-shirt. He quickly greets me and pulls me inside. He tells me his roommate is asleep and that we have to stay in his room and not be to loud.

He pulls me into his dimly lit room and closes the door. I was so nervous I didn't really know what to do. Sensing my nervousness he comes up to me and pulls me toward him and starts to passionately kiss me. I am stunned by the quickness, but that quickly fades because I am so turned on. I was making out with one of the most attractive men I have ever seen. I couldn't believe how lucky I was. We started shedding our clothes and seeing him shirtless just turned me on more. His muscular build was stunning and I could not get enough exploring it with my hands while we made out passionately.

We quickly moved to his bed and nothing could have felt better to have this stud on top of me. Feeling his muscular body on top of mine was amazing and I could not get enough of his arms. As our bodies rubbed together, we both were getting rock hard. I could feel his large dick rubbing against mine and I wanted to see more. Before I could even ask, he straddles my chest and I am face first with his amazingly large rod. Without any hesitation I open my mouth and start to suck his thick cock enjoying every second. Not wanting that to end he quickly pulls his cock out of my mouth and moves down to mine. He immediately takes me in his mouth and I am in heaven. I am so turned on that I cant even comprehend how good everything was feeling.

Before I knew it he is lifting my legs up exposing my hole. Not sure what he is about to do, he goes face first and starts to rim my whole deeply. This was the first time ever having a man eat my whole and I was experiencing a world wind of ecstasy. He had me moaning so much I couldn't handle it. He rimmed me for what felt like forever, but was most likely a few mins.

He pulled his tongue out of me and I knew he was ready for more. This was the moment I was wanting for soo long, but I was still nervous. Would I be able to relax, would he fit, would it hurt? He grabbed a condom and some lube and started to get himself ready to to fuck me. He lubed himself up and then my hole and started to slowly tease my whole with his cock. AS he teased he started to slowly insert into my virgin hole slowly opening me up. He may have been about an inch or so in when I started to get nervous and started to hold his hips back a little. He told me to relax and that he would go slow but I was still nervous and kept my hand on his hip. He started to kiss me and as he kissed me he took my hands and held them above my head. I was still nervous and said please go slow and he kept slowly pushing deeper inside me. I was scared it was going to start hurting especially since he was so large, but all of a sudden i feel his hips touch my ass. He was fully inside me all 8 inches of his thick cock. I was surprised and never felt anything like it before. The feeling of fullness and that tingle feeling of your prostate being hit.

He slowly started to thrust in and out and with each thrust he started to go a little faster and faster. Every thrust I was sent a shock of sheer pleasure throughout my body and I was in absolute Ecstasy. This man was fucking me and I could not get enough. What made it even better was he was fucking me and jerking me off at the same time which is a feeling like no other. Before I knew it I was blowing my load all over us and then he was shooting his load into his condom inside me.

We cleaned up and chatted briefly and then I was walked out. Such an intense first experience I had with such a stud of a man.
 

BlueBearCub

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It didn't even hurt one bit?
I was so turned on and loosened up from him rimming me that surprisingly it barely hurt at all. It was my first time bottoming for a guy but ive played with my ass a bunch way before ever thinking about getting fucked: fingering and some toys so that helped. My first time bottoming really got me craving to do it more and was way better experience than topping pleasure wise.
 

BlueBearCub

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Here is picture of what the guy kind of looked like:


sensual-picture-id93274602
 

dojoman

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I still can’t believe it didn’t hurt at all . But props on taking it! Did you know about douching and all that before u met him? I think most first time bottoms think you can just jump into it but like, nope .

Did y’all meet again afterwards?
 

BlueBearCub

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I still can’t believe it didn’t hurt at all . But props on taking it! Did you know about douching and all that before u met him? I think most first time bottoms think you can just jump into it but like, nope .

Did y’all meet again afterwards?
I cleaned in shower but everything was good. It was a one time thing unfortunately
 

BlueBearCub

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Idk why but I’ve always been worried about bottoming. Like I have done it twice. First time didn’t end well and second time, he only got a bit more after his head in. Maybe it’s cause I’m nervous or something
I can understand man. There was a time before this experience where i attempted to bottom but got nowhere fast. I don’t count that as my first time bottoming since there was very minimal to no penetration. Surprisingly that guy was not as big in size but it goes to show how much of it is mental and how turned on you are. Keep trying and find someone who really turns you on and it will be a much smoother experience.
 

nhguy78

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Tops that have no bottoming experience tend to assume that bottoms magically feel only pleasure and come pre-lubed and pre-gaping.

I'm glad this was a good experience for you. I've been taking an interest in bottoming but not much I've read here gives me any hope. So, thank you
 

BlueBearCub

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Tops that have no bottoming experience tend to assume that bottoms magically feel only pleasure and come pre-lubed and pre-gaping.

I'm glad this was a good experience for you. I've been taking an interest in bottoming but not much I've read here gives me any hope. So, thank you
Yeah you need someone who is patient and understands what it feels like. The best tops are ones who have bottomed before.
 
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