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FirstTimes

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- Gay Stories -
Bi-Sexual Male / 29

Second Night In A Row Bottoming

I posted earlier about my first time bottoming in a while. I wish I had gone into greater detail. I don't see an option to edit after you've posted. So here's part 2.

So like I said, I only had bottomed once before when I was much younger. Then I met a guy, we hit it off, and last night we went to his place and he fucked my ass for an hour straight. All day I could still feel him. It left me wanting more.

We made arrangements for me to come back over, so tonight he messaged me he was getting home late and I could meet him at his house. I went over and after exchanging hellos we stripped and I laid on the couch. He put me on my back and began sucking me, licking my inner thighs, and eventually giving me rim job. The way he eagerly stuck his tongue in my hole was exhilarating.

Before he could continue I sat him on the couch and sucked him for a while. Oral is not my specialty, but sometimes I love it, other times not so much. But knowing what that big dick was going to do to my insides I licked and sucked his cock, tasting his precum, till I couldn't wait anymore.

He got his lube got me on my back on the couch again and started working his fingers into my ass until I was nice and stretched and lubed. He then worked his dick into my hole and wow... The best word to describe it at first is relief. I felt relieved his dick was fucking me for the second time. As he picked up the pace I felt a wash of pleasure. I know I involuntary threw my head back and moaned, tongue out, as he began thrusting. He got my ankles up on his shoulders and he pounded me like that for a good while.

After we switched to doggy style. He plunged right back in. I made sure to crouch real low and arch my back so my hole was at just the right height for his fucking. While he thrusted I was grunting in pleasure on each thrust, making sure to push back and grind my hips against his invading cock.

Yesterday when he was fucking me doggy style there was a point where if he thrusted too hard I would let out a little surprised yelp as I felt my insides rearrange. Not today. Each thrust was sending waves of pleasure as I licked my lips pushed back.

That's when he suggested we try me on top, which we didn't do yesterday. I've never rode a dick like that before but I was excited to try..so I climbed on him, facing him, and slipped him in. I COULD NOT GET ENOUGH. I was grinding down on that dick, gyrating my hips as I bounced up and down. The whole time he was looking up at me smiling.

Then we switched to side-by-side. He spooned me from behind and I arched my back waiting for him. He thrust it in and began fucking as I begged for more. Eventually I flipped into my stomach while he just smashed my ass in the prone position. There is nothing like feeling a guy on top of you totally buried in your ass.

So I'm moaning as he thrusts harder into me as I reach behind me and grab him. I was wrapping my legs around his forcing him in deeper. Finally he exploded raw in my ass.

I just got home and I can feel the absence of cock in me. I was still feel his cum leaking out a little as I type this. For my third time bottoming, boy did things get better. Today was raw, primal, rough fucking I've never had before. I used to think I was mostly a top, but after today, I think I'm mostly a bottom...

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# 72264 - by FirstTimes / July 6, 2024
- Gay Stories -
Bi-Sexual Male / 29

My Second Time Every Bottoming

So, I had bottomed once before. It wasn't bad but awkward. It was when I was younger. Sure it was a lot of fun, but I knew one day I'd try it again. In the meantime I got a bunch of experience topping.

So yesterday I meet this guy on Grindr. So many people flake out but we hit it off and chatted all day and agreed to meet up that night. I had told him I only bottomed once before and he said he was fine with it. Well, I went over and we got into it pretty quickly. Before I knew it we were naked and he was twisting me up like a pretzel licking and rubbing himself on me. I told him I wanted him to fuck me. He was so gentle. He took his time getting me ready and gently stretching me. By the time he put his dick in I was more than ready. It seemed like no time but he fucked me for over an hour. He fucked me bent over on the couch, with my legs over his shoulders on my back, doggystyle on the floor, spooning side by side on the floor (new favorite.) All I can remember is going wild. I was thrusting my ass back onto him and grinding my hips on him.

So I went from bottoming once and thinking it was okay to getting one of the best sexual experiences I've ever had.

4
# 72254 - by FirstTimes / July 6, 2024

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- Gay Stories -
Bi-Sexual Male / 39

Discovered I'm Mostly Gay, But There's A Problem Pt. 3

I told him I was 29 years old when we talked on Grindr. I definitely look 29, maybe even younger. Usually I tell people 29 because if I told them my real age they wouldn't believe me. Anyway, I told him I'm really about 10 years older, married (to a woman), and have kids. He took it very well and didn't get upset with me. Like everyone he was shocked by my age, but also by everything else. Of course he had a million questions. How many kids do I have, how long have I been married... I told him the truth about everything.

I told him how I had been in a sexless marriage for over 10 years. We didn't even have sex on our wedding night, and not for lack of me trying. Long story short, she just really doesn't like sex that much. I can literally count on one hand the number of times we had sex over the last 5+ years. She doesn't know about my urges toward men and can't know. I thought I was just letting off some steam by getting something my wife can't or won't give me. I didn't realize how much I'd love it. I told him about how my marriage is super platonic.

I don't remember all I said, other than I was truthful... For the first time I told someone everything. Now he knew all my secrets. He asked a lot of questions and was concerned about every aspect of what I was going through and what it could mean going forward. I remember he stood up and asked me to stand up... When he said that I know I stammered a little bit because I wasn't sure what he was going to say or do... I managed to croak out "you're not going to hit me are you?" He laughed and told me to stand up again. When I did he gave me a big hug and told me he was going to have to think about whether he wanted to continue a relationship and that he was sorry I was so lonely and had no one to talk to. I stressed to him that the reason I told him is because I did really like him and if there was ever a chance at us really being friends with benefits I had to tell him. He said it might take a while to process and we said our goodbyes.

I spent the next few days verbally kicking myself... Thinking things like "obviously he's going to say no. I'm like 15 years older than him and married. He's hot and could probably get any number of guys. Why would he want to hook up with me?" So basically I spent the next few days convincing myself I would never hear from him again. I remember one night I finally put my phone down on the nightstand ready to let it go, ready to accept that I'll probably never have sex again... I had told him as much. I was tired to looking around, living a sexless life and wanted to find one guy to connect with, but if this wasn't it, I was going to give up.

The next morning I woke up to a text from him. It said "hey, sorry it took a few days to process, but I think I want to keep meeting."

It's been about a week since and we hook up whenever we can. He's training me to deepthroat him. Today we met in a parking lot and I sucked him off in his car. He's been sending me messages telling me how good I make him feel and I've been giving him similar compliments. Since I told him the truth it feels more like we're actually dating on the DL rather than just hooking up. I can't wait to see what else our relationship brings, but he made me realize I'm mostly gay, and mostly a bottom...

6
# 72778 - by AnonDL / August 7, 2024
- Gay Stories -
Bi-Sexual Male / 39

Discovered I'm Mostly Gay, But There's A Problem Pt. 2

We had agreed that we were both looking for something more regular and had made plans to hook up again, but do it bareback next time. I also wanted to try sucking him because I never had really done it before.

So we met up the next night and it was a repeat of the previous night. Except I sucked him and swallowed to start things off. I had gone from never sucking a guy really to deepthroating him until he completed down my throat. After that he gave me a massage. Finally it came time for him to top me bareback. He lasted a lot longer this second time.

I was kind of on my side laying on the bed but he stood beside it. In that position I could look back at his smiling face while he absolutely wrecked my ass. It made me feel like I never had before. I went from only having bottomed once and not having strong feelings either way to absolutely loving this guy pummeling my ass. I was making all kinds of noises and high pitched squeaks as he pounded away. I know at one point I got so lost in it I'm laying there moaning with my tongue hanging out looking back at him just absolutely dominating my rear. Finally he came in me. I had come so close to coming and I hadn't even touched my own dick. I remember loving the feeling of my stretched hole and the slick feeling between my ass cheeks popof his cum leaking out a little as I walked back to my car. I made sure to leave his seed in me that whole night.

We immediately messaged each other after I left and exchanged phone numbers. We had agreed to meet up the following morning because we had such a great time. For the third day in a row I sucked him and swallowed and then he dominated my ass...

This is where the problem comes in. He made me realize that what I really always wanted was to be a bottom. He was looking for a friends with benefits type situation. When we first started hooking up I let him know that I was DL. He was fine with me not being out, as I didn't need to be out to be friends with benefits. I knew if we were ever going to connect on the "friends" part I had to come clean.

I messaged him the next day and asked if he had a few minutes to talk. Immediately he got worried and I told him I just wanted to come over to work on the friends part of "friends with benefits." He agreed and I went over to his place.

When I got there he asked me what was up and I laid it all out on him...

1
# 72777 - by AnonDL / August 7, 2024
- Gay Stories -
Bi-Sexual Male / 39

Discovered I'm Mostly Gay, But There's A Problem Pt. 1

So I've always considered myself bisexual. However, I had never hooked up with a guy for most of my life. I had lots of girlfriends in highschool, fewer in college, and never had any problems getting it up, but it was always so hard to cum.

When I watch porn it's almost exclusively gay porn. There was just something about it that got me so turned on, but I still never tried it. I convinced myself the reason it was hard to cum was because I wanted to fuck girls in the ass and most wouldn't let me. I come from a religious background and coming out would mean being shunned from my family... But after being stuck in a sexless relationship I decided it was time to give it a go with a guy.

I downloaded Grindr and hooked up with a bottom. We met up for a while and it was definitely fun, more fun than most of the girls I had been with. Personality wifdtTVFse though we just weren't a match (he left glitter all over the inside of my car like he was the gay fairy of glitter) and we stopped hooking up... I was inexperienced with guys and the poppers thing really turned me off. The smell might as well have been a custom made boner killing fume device.

I tried out bottoming one time but it just was awkward because it was in the back of a car. After a lot of work getting it into me he basically gave a couple pumps and said he was done. I didn't hate it, but I wasn't in a rush to try it again. So for a while I just stopped actively trying to hookup.

One day I got a message from a guy wanting to top me. He was hot and young and tall. I'm tall myself, but he was even taller. I wasn't against trying it again and something about the way he approached me and the things he was saying convinced me to give it a try. When I went over he had the bedroom lit with mood lights and essential oil diffusers around the room as well as light music playing. Already this was a far cry from my first time bottoming. He slowly undressed me and gave me a whole body massage. I had never really been into foot stuff, but he rubbed my feet and sucked my toes which was a turn on in a way I didn't think it would turn me on.

After, he laid me on my stomach and made sure I had plenty of pillows and blankets. Then he ate my ass for what seemed like an hour, until eventually he was sliding fingers into me. I was over the moon with feelings I had never felt before. That's when he leaned over me whispered in my ear "are you ready for me to take care of you?" I gently moaned my approval. I heard him open a bottle of lube and he spread it on his dick and worked some into my ass. His dick was about average length, but thick. I laid there on my stomach my heart pounding. Then I felt the head of his dick approach my ass cheeks. As soon as I felt it approaching my back door I instantly got the hardest I've ever been in my life. He slid it in me and immediately I could tell something in me changed.

Suddenly, everything made sense. It suddenly made sense why I never really liked going down on girls. It suddenly made sense why I tricked myself into thinking I wanted was to have anal with girls. It made sense why a girl could suck me for hours and I would never reach orgasm. It also made more sense to me now why topping a guy didn't quite do it for me.

He didn't last long but I can remember while under him I was making noises that surprised even myself. I laid in the prone position while he pumped me into the bed. I reached back and grabbed at his legs and body, lost in the throws of pleasure he was sending through me. After he came we lay there together panting with me trying to process what had just happened.

1
# 72775 - by AnonDL / August 7, 2024
- Gay Stories -
Bi-Sexual Male / 39

Learning About Lifes Ways

As a teenager I absolutely hated school. I was constantly bullied and often punched by those who took pleasure in making my life a living hell.
As such I often stayed away from school as 'grassing' only gotten you more bullied.
During one of my truanting days, I ended up in the woods about two miles from where I lived.
I'd only just entered when I was grabbed by a big guy who I guessed to be in his forties or early fifties.
He told me immediately I shouldn't be in his woods, nor should I be missing school (uniform).
He mentioned telling the school, my parents and the police that I was 'wagging it'.

So when he took his cock out, and it was big, fearing the bullies more than him, I didn't try to stop the man when he pushed me down and forced his cock into my mouth.
I'd not even kissed a girl by then, so I didn't have a clue what he wanted me to do, but over the next however long it was, he taught me how he liked his cock sucked.
He wasn't gentle about how he fucked my mouth, but he wasn't overly mean either. And in that respect as I think back now, I kind of accepted my need to pleasure him.
I had wanked many times by then, and sometimes in the woods I was now sucking on a grown man's cock.
But he wanted more and had me totally strip naked.

I knew by then he was going to fuck me, yet I didn't try to run. He'd have easily caught me I and didn't want to anger him.
As soon as my undies were off, he grabbed me and had me lean up against a tree. That's when I felt his hot breath on my arsehole.
He spent the an absolute age tonguing my rear hole, telling me all the time how beautiful my arsehole was and how he was going to take my virginity.

When he did stand up and slowly slide his cock up my saliva coated hole, it was like trying to fit a train through a man hole opening.
It hurt and that's when I did struggle, but he was far too powerful as he held me fast.
Not once did he stop talking to me as his cock eventually bottomed out up my arsehole. That's when he brought my head back, turned it and kissed my mouth.
He was fucking me and kissing me at the same time and strangely the feeling up my backside changed. Like flicking a light switch, the pain stopped and was replaced by an overwhelming feeling of pure joy throughout my entire body.
It was so powerful, my knees buckled which made me push back onto his cock.
He took that as encouragement and fucked me harder. Which only made those feelings more intense.
And before I knew it, I was cumming all over the tree in front of me.
My arsehole tightened around his cock then, and I felt his cock explode up my rear passage.

He still held me and began kissing my neck telling me I was a good boy over and over.
Releasing me, he had me get dressed and he lead me deeper into the woods. We talked as we walked and I explained why I wasn't in school. It was the first time I'd told anyone why and it angered him.
He'd built a small fire and that's where his back pack was. Offering me a drink and part of his sandwich, we talked for some time before he said I should go.

Before I left he said if I wanted to enjoy myself again, he usually walked from ****** **** to the woods most days.
For the rest of that school term when I didn't go in, and through most the summer break I visited those woods and each time he fucked me, or had me suck his dick to completion.
One day he didn't show up and I found out later on he'd been killed in a car accident.

Throughout those months however we talked a lot about the people who bullied me.
Once I returned to school after the summer break, those who bullied me found out I'd found my fighting mojo. I didn't win every fight, but no one bullied me again.

What's bizarre, is one of those who bullied me is someone who I recently fucked at a cruising spot, and the reason I'm here confessing my story.
He obviously didn't remember me from school, but he'll sure remember me destroying his arsehole as others watched me fuck him. One of those wanking and cumming over his face and hair.

This is a 100% true confession. And I've left some parts out. I didn't want to overstate anything, but what I will say is, be careful who you tread on, on the way up. You never know who you'll meet on the way back down.

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# 72265 - by John / July 7, 2024
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