First Time Topping A Man

[tripppleP]

There are a lot of threads on guys having their first experience bottoming for the first time with another man.

I wanted to hear about your first time topping another man. I have only been with women and prefer to be in relationships with women but watch a lot of gay porn. I have been wanting to try hooking up with a guy to see what its like but specifically would want to be the top for my first experience. I have been messaging people on Doublelist trying to find the right person but am not in a rush.

So tell me what your thoughts were when you topped another guy for the first time.

 

[tripppleP]

So no one recalls their first time banging a dude after exclusively banging women their whole life?

 

[WilliamG]

Someone once told me there are more bottoms than tops.

 

[halcyondays]

My first time topping was with a cute guy who invited me to his room after hours at the hotel where I worked in college. I was 22 he 20. He was flaming gay rocking a nice bulge in spray on designer jeans. He was maybe 5'7 and 135 with a hot slim runner's body and a cute tight butt. He flirted with me many times over a few days before inviting me to his room.

He started undressing as soon as the door closed. Blew me but was in a hurry to fuck. I had condoms he had lube. He put me on my back and got on in his own time. I'm big so it took a while for him to relax, open and take all of me getting on and off me many times before he was comfortable with all of me inside him. He rode me till he came all over my chest and belly. I fucked him all over the bed, room and bath late into the night filling 3-4 condoms. He was an experienced bottom.

My first thoughts were "I don't know what I'm doing so I'll let him lead and do what he needs to do as a bottom." After he came the first time I fucked him pretty much any way I wanted but like all sex there was plenty of communication about what we both wanted.

He asked if I had been with a guy before. When I said no he smiled and said don't worry I'll show you what to do.

Funny. The first woman I was with said the same thing.

 

[Iggles_yunker]

So embarrassing to look back on. We started talking on Craigslist he was 19 and I was 25. We met in his car and exchanged oral the first time we met. The second time I was in no way prepared. Only used spit as lube and tried to start with him bent over. He said it was too big to do it that way and laid on his back and I had no idea guys fucked in missionary position. We fucked in his back seat and it was a lot more fun experience than I anticipated.

 

[latinluva]

Like most of my other experiences, in an adult video arcade. I was about 20 years old, looking to get fucked in the ass. Another young guy, about my age, cute and medium build. We make eye contact, I think he wants to fuck me in the ass, we go into a both, start sucking each other off, I start pulling my pants off all the way and offer my ass to him. He starts to giggle. I ask why he's laughing? He said that he doesn't top. I looked confused and he said he was hoping I would fuck him. So I said sure, I fucked him and loved it, but not as much as getting fucked.

 

[CaptainRugby]

It was someone I had messed around with for a while, a friend. We had said to each other that it was okay to suck and stuff, but “fucking is gay”. However, it was clear that he loved my big dick and was the more passive of us. One night after a few beers at his house we started playing and, unusually, we did a lot of kissing. He was getting really hot and horny and he stopped and asked if I would fuck him, and he pulled out one of my condoms he’d taken from my room at some point.

He’d prepped (thankfully) and without saying a word I yanked off his clothes and got to work on his arse. I had fucked a couple of girls in there’s before and knew that because of my girth I needed to prepare. I rimmed him and fingered his hole whilst he moaned (literal pillow biter). Then he lubed up and slowly started working my way in. There was pain and tears in his eyes, but we kept going and I was able to get most of my length in. He was super tight so it was pretty quick for me. And it turned out he was very anally sensitive and jizzed hands free.

One of the best fucks I’ve had. Turned out later he’d always wanted me to fuck him and take his anal virginity, but didn’t have the courage to ask. So he’d been practising with dildos borrowed from his sister.

 

[curtdude]

my first top was with Michael we were in his room naked fooling around both of us hard as a rock he was on his back legs in the air was on top looking into his eyes as the head of my cock found and pushed in his hole it was right and as my head popped in I stared into his eyes a grimis on his face as I pushed in further until, my balls were on his ass I pumped in and out until I unloaded deep inside him my sperm was now inside him part of me was in him
it felt fantastic

 

[dickthrobbing]

So no one recalls their first time banging a dude after exclusively banging women their whole life?

The tightness of his hole and the warmth totally different to pussy

 

[Sunman_Universe]

I was fooling around with a beautiful boy. We blew one another and he sat on my cock until I came. It was totally different from pussy but very nice.

 

[pnwboy]

My man had only been with women before we started. He was also my first sexual experience. I have always naturally been his bottom and when we first started, I asked him if he liked being with me or women better. He told me after the first time he made love to me that it was different but that I felt so much better than any woman he'd ever had sex with. I don't think he was just saying it either, because neither of us could get enough of each other after that. lol He didn't date any other women for several years.

 

[beginner63]

My first time was 6 years ago. I had only bottomed once and was ready for more . I had talked to a guy online for a while and he agreed to do me if I did him too. I wasn’t really into it but was horny and agreed. I had assfucked a few girls years ago and had a little experience. I did like seeing his ass in the air while I entered him from behind. I also did cum while fucking him. I do prefer to bottom

 

[tripppleP]

Anyone else? Seem like the bottoms out number the tops here.

 

[1373263]

My first time topping was with a FB who had helped cement my interest in M2M sex. He very gently seduced me into bottoming for him, and I was a willing student because I found that I not only liked his cock in me, but I liked the sensation of lying on my back and letting him pleasure my ring with his tongue before slipping inside and pleasuring my insides.
One morning he firmly told me he needed to be filled up, it was my turn, and he had wanted me to fuck him for some time. I was apprehensive but evidently had learnt well because I repeated on him what he had done to me, in the same way and shortly received a great reaction as I gently opened him up. I'm not massive huge but clearly mine was more cock than he expected from the very beginning. I was surprised at how hot and tight his ass was initially, and how it relaxed with prolonged fucking- totally different to any pussy I had experienced.
I liked the intimacy of facing him and seeing his facial reactions to each thrust. He eventually closed his eyes and I filled the condom with a substantial load.
"Feed it to me" he moaned... and I did

 

[lighthero33]

Mine was with a guy I had been speaking with on Grindr for a long time but he was hesitant on meeting up. Finally we did, and initially he was just going to suck me off. Once I got to his house and on the couch, he started blowing me and eventually asked me to fuck him. I agreed and we moved to the kitchen because he didn’t have lube but had some vegetable oil (I know, but I was young and horny). He wanted me to sit on a chair while he rode me, but the angle wasn’t right to do it, so he got on all fours and I fucked him doggy. Felt amazing, nice and tight. Didn’t take long for me to cum and for him to do the same.

 

[bijockfl]

My first time was in college with an agent showing me rental apartments. I was ignorant that he was flirting with me. A week later he calls to check in and we grab a drink end up at his place. I spit on his hole slipped in and pounded out two nuts. He didn't come out of the bathroom so I left..he explained later that the cum wouldn't stop dripping out that is why he stayed in the bathroom

 

[LOVE_MMFs]

Thankfully, the first time I topped a guy, it was was an experienced bottom. I basically let him take the lead. I remember thinking the initial penetration was more difficult than I expected it to be but then I slipped past his first ring and was inside. I let him control the pace. I was pretty nervous because up to that point I’d only done oral with guys.

 

[theplayerking]

It was an online hookup right after college. He was older and I wasn’t particularly attracted to him. I was just horny and wanted to be naked with a man. We were making out in bed and he asked me what I wanted to do. I told him I wanted to fuck. I put a condom on, slid in his ass and came in 30 seconds. I then flipped over and asked him to fuck me. Not a memorable experience.

 

[justatadhorny]

Mine was 5 or 6 years ago. We'd been chatting on Grindr and to be honest, I thought he was catfishing me because he was model-worthy gorgeous with an 8 pack! He wanted to meet, but I said I was going to see a movie. He asked if he could tag along. I said sure, worst comes to worst if he's catfishing me at least I'm in public. Good news...he wasn't!

I picked him up on the way to the cinema and literally said, "oh my god, you're gorgeous!" as he got in the car. He laughed and looked bewildered and said, "but you already saw my pics on the app?"

On the drive there, he placed his hand on my crotch and started massaging and I was rock hard straight away. No girl had ever been this forward. I did the same to him and found through his loose fitting fitness shorts that he was freeballing. During the movie, I more than once put my hand down his shorts and fondled his dick and balls. The precum tasted great.

Got back to his place and literally as we walked in his room, the clothes were off and we were 69ing. I was terrible at oral as I'd only done it drunkenly once in my teens, but he was great. Soon he was sitting and grinding on my cock (but not inside). I was beyond horny after this huge build-up. "Condom?" I asked him several times (we'd only discussed oral on Grindr and in the car). "Yep" he replied AS HE SLID DOWN ON MY DICK BAREBACK. I was shocked...but horny and figured it was too late now, so I fucked him like a rabbit until I unloaded inside him. Felt sooooooo good. When he hopped off, he said sorry and that he was super horny and said it was ok to fuck raw because he was on prep. I was cranky because it was unexpected and really, I was taking his word for it. But by the same token, I couldn't be too angry, because I hadn't stopped him grinding his hole on my dick before I entered him.

We laid there for 10 mins chatting while he kind of played with my dick. I started to get hard and he grinned and said "round 2?" before starting to suck me. I was a bit shocked because it had just been in his butt and we weren't in a porn movie, but he assured me he knew he clean. Horniness took over and I flipped him over and starting eating him out. Was a weird sensation because I knew my cum was there, but it was also super hot. After a couple of mins, I started fucking him doggy style for a while until I came inside him again. Felt almost as good as the first time.

And after that very long story, I went home and had a wank to this super hot memory.

 

[deleted5199391]

My first time was fine, since I already had a lot of anal sex with girls, and he was a gay guy.
No pain and the fuck was amazing.