First Experience Bottoming for Two Guys

by Late Night Charlie

13 Apr 2023 4784 readers Score 9.2 (70 votes) PDF Mobi ePub Txt


When I was 21, I fantasized about bottoming and having another guy's dick buried in my ass. Just to some up this part which I will write about later. I met up with a guy a talked to for a while on craigslist. I'll say his false name is Kyle. He was 24, we were both stalky but in shape. I was 5'11", about 190 lbs, white and at this point bi-curious. Kyle was similar, white, chill, 5'10" about 200 lbs. And offered and chill, easy going, beer drinking, discrete experience to take my gay virginity. He was openly gay but respected my discretion and secrecy. Cutting to the chase, we met and I had a great experience being fucked by another guy. We wound up meeting up and having great sex multiple times at each others places. We stopped meeting after he moved for a different job. Over the years I kept getting urges to get fucked so continued meeting people, some were great and continuous, some were terrible and regretful. 

Often times I thought about Kyle taking my anal virginity and a lot of the times we met and he fucked me after. He wasn't the biggest I've over the years but he was still modest with a 6.5" thicker uncut dick and a lot of stamina and fast recovery. And easy to get along with and feel comfortable with. I'm 30 now, still the same build and weight. Closet Bi Bottom, still secret and discrete and only 2 people know I enjoy a dick up my booty. One day Kyle found me on social media out of the blue. I was surprised, nervous and somewhat excited thinking of what this could lead to.. Hopefully getting fucked by my first time guy and one of the better fucks I've had. I replied and we talked. He moved back close and bought a house with his partner/husband of 2 years. His husband we'll say Nick, was 34, about 6'2", 220, thick but fit. During conversation, we confirmed I still really enjoy bottoming which led to me admitting I've fantasized and being with 2 guys and being a bottom for both. I asked if Kyle and Nick might be open to a third guy in their mix for a first time casual 3 some experience. Turns out that's why Kyle reached out to me. They were a couple and flipped positions but neither loved being bottom. They've tried a 3 way twice before but they weren't great. Either not a good fit of person for them or they couldn't handle what Nick had to offer down below.. When they asked if I was interested in being a bottom for them, I was all in! I got pictures of Nick and vise versa to get to know him and seemed chill and easy to get along with just like Kyle. And of course I had to know what he was packing. He showed me a juicy fat 7.5" uncut thick dick. It made me extra horny and desperate to feel it. We decided to meet and I was gonna used and abused but both dicks. I was excited and nervous. It took a couple weeks for us all to be available and meet. One Sunday night it was finally happening.

After a not so Funday Sunday night of drinking at a friend's party. I was recovering and hydrating all day. Started to feel good, then horny. I had a long shower and wound up douching with plans of shoving a couple toys in my ass. I was prepped and cleaned just because. It was early evening, I went to my basement and ditched my clothes on the floor, put on some porn, laid back on the couch with my legs spread and feet on the coffee table and started to lubing and fingering my hole. As I shoved a vibrator up my ass, my phone went off. I ignored it as I slowly fucked my ass with my vibrator while watching gay porn on surround sound of guy's getting plowed in gangbangs. At this point I desperately wanted a dick inside me. I checked my phone and it was Kyle! Seeing what I was doing and if I was free to meet since both him and Nick were home and horny. "Absofuckinlutely!" I replied. I was so close to blowing my load but resisted, pulled the toy out and cleaned up one more time quickly, put on a jock, jeans, sweater. I got their address and hit the road. My heart and mind were racing, with excitement and nervousness, not knowing what to expect, or how a 3 some worked. 20 Minutes later I was at their house. They said come on in, Kyle was at the door. 

As I got out of my truck and walked up to the door, my legs were shaking, hands were cold and clammy, short breathes, and feet felt cold. My 6" cut average dick felt shrunk and pathetic in my jock but still felt pre cum from the nerves and excitement. Kyle opened the door and welcomed me in. I stepped in and scoped around their nice, cozy and freshly renovated home. My nerves started to settle as me and Kyle talked and caught up, felt just as easy to get along with as before. I followed to the kitchen and sat on a stool, he offered me a beer and we waited for Nick to finish showering. I just finished my beer and felt eager. Nick walked down the hall out of their room in a black tee and tight saxx underwear. We introduced each other and I didn't hide checking out his large bulge. We talked and had another beer to get familiar. He was very cool and easy to get along with. We were all masculin acting, Nick and Kyle were definitely open and gay and happy. We started talking sex. Kyle was already looking forward to it from knowing me and enjoying fucking me from the past. Nick admitted I was way better looking face and body wise than he expected, like wise. We all clicked. It was my first 3 way and their third. They were just as excited as me, the first two times weren't great they said. And they wanted a casual, clean, bottom to have multiple hook-ups. I was definitely interested if it went well, hoping it will so I didn't have to deal with flakes, no shows and shitty hook ups on grindr, etc. Fair to say we were all eager and horny after talking and finishing our beers. 

Here weee go, it was time! I followed Nick to the room and Kyle was behind me. Wearing a tee and sweats. Went into the room, cool sexy time lighting, smelt good and clean with a king bed. Kyle went around to the far side and peeled off his shirt and dropped his sweats showing his nice clean uncut cock that took my virginity. Watching it flop around as he laid on the bed got me revved up. If a man's ass could wet itself to get ready for a fucking like a woman's pussy. I would've been dripping haha. Nick grabbed my shoulder and turned me around. He kissed my neck and pulled up my sweater and tossed it. I pulled up his shirt and threw it down and got on my knees. I groped his bulge and felt his fat dick and full balls. I slipped my fingers in the band and pulled off his underwear. His half hard fat dick was dangling an inch from my face. I took a deep smell, grabbed his dick, lifted it up and sucked and licked his nuts then pulled back his hood slid my slips down his now rock solid dick as far as I could. I tried to take it all but I kept gagging and I'm not the best deep throater haha. But a damn good bottom. I stood up, laid on the bed and Nick pulled off my jeans, groped my cock through my jock and peeled off my jock saying they want to see my dick flopping around while they're fucking me. I was rock solid. I rolled over and started slobbering all over Kyle's cock. His dick tasted great and brought back memories. I could just barely choke down the whole cock. Nick pulled my hips up and pushed my legs apart and started jerking me and rubbing my ass from behind. It was great being between two confident guys that like being a bit dominant. Nick started fingering and eating my ass like it was his last meal. It was hard focusing on blowing Kyle while my ass was getting special treatment at the same time. Couldn't believe how awesome it felt and didn't think it could be better.. Definitely did!

Nick loved my ass, couldn't get enough. Nick and Kyle casually talked about who was fucking me first. Kyle decided to go first. I turned around on all 4s as Kyle repositioned on his knees behind me and started munching on my ass. He missed my ass. I was arched and ready, Nick tilted my head up and slid his cock in my mouth and slowly fucked my face. Kyle got up close behind me, lubed my hole and his cock. He rubbed his cock up and down my ass, I wanted it sooo bad! I felt his head pushing into my hole, he kept pushing in slowly until I felt his thighs pressed against my ass cheeks. I let out an accidental moan.. the feeling was ECSTACY! Kyle slowly started to give it to me as his husbands cock slowly fucked my mouth. Kyle began to pick up the pace, thrusting faster. I had to stop sucking Nick, I couldn't focus on anything but Kyle fucking my ass again and loving it. Him and Nick was talking about me, loving how well I take it and how hot I looked getting fucked. Kyle pounded me deep and hard in doggy for a while then got close. He pulled out and Nick grabbed my hips pulled me over and told me to give him my ass. I needed more! Kyle laid back again and positioned himself so his wet throbbing cock that was just pounding my cock hungry ass, was right below my chin. As nick fingered my freshly fucked hole, I took in the scent of Kyle's juicy cock that was just inside me and got a shiver of satisfaction! His cock smelt great! I pulled the tip of his cock down into my mouth with my tongue and started bobbing fast and as deep as possible. Kyle was getting close and moaning. I could feel Nick's lubed up thick dick pushing against my hole. His pressed his thick cock into my guts slowly and fairly easy. I was glad my cock pit was experienced. I felt his whole baby maker sliding inside me until his thighs were pressed against my cheeks. He was pumped how well I took his cock and kept saying how great of a bottom I was. He started slowly thrusting and sped up. Kyle was getting so close, he gripped my hair and fucked my face as his husband was fucking my ass at full speed. I was letting moans slip and wanted to stop sucking but wasn't allowed. Nick was fucking me like a porn star!! Kyle let out a groan as he pressed my head down until his throbbing cock was gone and shot his warm load into my throat! I gagged but made myself handle it, once he stopped shooting his load, I slurped and sucked tightly as I cleaned off his dick an swallowed his load. Kyle was out for the count as his cock started to soften. Nick never slowed at all still wrecking my ass hard and deep. I was semi hard and felt like I was gonna cum!

Nick pulled his cock out of my hole and told me to suck it for a bit. I turned around still on all 4s and obeyed and choked on his fat cock that was just fucking my ass. I loved it and they both couldn't get enough either! Kyle played with a dildo in my ass for a minute as he told Nick he was spent and just wanted to watch and that I was all his! Nick laid me back on the bed and pulled my legs up over his shoulders and stuffed his cock back in with speed. I was in heaven as he pounded my hole as hard as possible. We locked eyes knowing he was making me his bitch. He watched my semi hard dick bouncing around as he fucked my ass commenting how he loves bottoms that aren't totally hard when getting fucked. He pushed my legs back and said he was close, so was I. He started thrusting deep and hard then pull out, ripped his rubber off and blew his load on my hole then pushed some back in. Nick fell over beside me and I was between Nick and Kyle. They were pumped and want me to return. I definitely will. They asked if I like getting off as a bottom, and I told them after a session like that absolutely! They both leaned up and shared sucking and jerking my now rock hard cock. They pulled my knees up and each stuffed two fingers in my ass and finger fucked me right up while sucking me off. I couldn't believe how great it was being a fuck toy for two guy's! I blew my load all over my chest and belly as my hole clenched on their fingers with every pulse. 

The 3 of us laid there huffing and puffing. I loved knowing there was cum in both ends. Nick and Kyle groped my whole body and kissed me all over. Sent shivers everywhere. Eventually we got up and I got dressed. We talk and agreed that was fucking awesome and we all want more. They're happy as hell to have a bottom booty call when neither of them want to bottom. I'm pumped to have not one, but two safe, clean tops with great dicks that I can call up from now on!


Thanks for reading! This was a true story that recently happened. There was a lot of dialog the whole time, waaay to much to share. Going to write up a story of getting fucked for the first time soon!

by Late Night Charlie

Email: [email protected]

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