What’s your first gay experience?

[Jay toscano]

Hey, I just want to know about your first gay experience. Details are optional but would be interesting to include, all experiences must be involved with legal age experiences, no underage

 

[Torontoguy411]

Here's my first experience having sex with a guy...most mind blowing experience of my life.

A few years ago I finalized my divorce (54 now), and up until that point had considered myself str8. Sure, I was confident enough in my masculinity to notice a good looking guy on the street, or admire a nice body and cock in the locker room, but I had never had the feelings of "I want to suck that man's dick". The most I had ever done was compare with a couple buddies, and while drunk let a guy blow me in university on a dare.

I went through a pretty nasty divorce with a bitter woman who could never take responsiblity for her role in breaking down the marriage. I had a couple close buddies who were amazing supports during my separation and moving into my own place. One of those guys was my best friend, a married dad, my age, and I've known him for 20 years. We did a lot of things together including travel going to the gym, going to sporting events, hanging out in each other's back yards, etc. His wife wasn't the nicest person, and I knew their relationship was pretty much roommates after their two sons moved out. He often made jokes about not getting sex at home at all, but that was almost a standard line from most married guys

One night at my new condo, we were hitting the vodka pretty hard, and my buddy kept bringing up the topic of sex and masturbation, and making comments about how much I must be jacking off now that I have my own place, and hanging out naked and enjoying being single. He kept asking about what porn I was watching and how often I was jacking off. Then he just blurted out "so how big is your dick?" He went on about how we've travelled together and gone to the gym but we've only seen each other soft. He said from what he's seen he assumed I'm longer and thicker than him. I said I hadn't measured in years, and wasn't sure, so he challenged me to compare with him.

I had been into the vodka enough to have my guard down, so I agreed, and we stripped, and jacked ourselves hard, and he put our dicks together and compared. Feeling my buddy's hand on my cock like that was electric - like super charged energy going through my cock while he compared them. Then he was visibly turned on even more when he discovered I was longer and thicker than him. By now both our precum was leaking all over his hand, and he kept looking up at my smiling and feeling us both up. He then pulled back a bit but didn't let go of my cock, and just kept stroking me. I couldn't resist any longer, and reached for his cock and stroked him as well. I could hardly believe I was doing this but moreso I couldn't believe how hard and turned on I was to be jacking my best friend's cock. I suggested we go to my bedroom, and we ended up on my bed stroking each other, and then I felt that almost forgotten feeling of a mouth on my cock, and I looked down and saw him sucking me. I was losing my mind, and eventually he pulled off, and I went right to his cock and put a penis in my mouth for the first time. It was amazing - I just did to his cock what I like having done to my own. He was moaning like a whore and holding my head as I blew him.

That night we blew each other, showered together, and he crashed at my place in my bed and we slept together naked. In the morning we woke up and blew each other again. I didn't feel any remorse at all and didn't regret anything that we did. He went back home later that morning, and we started texting and sending pics of our dicks back and forth.

We jacked and sucked often after that, and a couple months later I took his ass cherry and mounted that hot beefy dad ass of his. It was the tightest thing I have ever fucked.

We talked about what happened a couple days after the first time we did this, and confided to each other it was our first time ever being with a guy and how great it felt. We did this for 3 years including going away on "just us guys" weekends together and stayed naked the entire time at a cottage and fucked like rabbits.

Unfortunately his job took him to the UK last November, and that was the last time I got to suck his cock and fuck his amazing ass. We still text dick pics back and forth, but I miss that experience with him. I probably would never have tried it with a guy if I didn't trust him like that.

So, I wondered if any other guys had their first experience with guy sex in adulthood, and it was with a married buddy similar to my experience. Would really like to hear about how others made the leap to explore guy fun together.

The pic is my married buddy blowing me in a hotel room on a weekend away. Seeing his ass always makes me hard knowing I took his ass cherry and mine has been the only cock ever in there.

 

[Malany_hill85]

My first experience was with my first boyfriend... though I had alteady had sex with women before when I "was" straight.

We were just "friends" but we both highly suspected that the other one was gay, so the sex tension had been building up between us for quite some time then. One day, I went to sleep over his house so we could study for a test. Obviously we did not study at all.

We were watching some movies and we started cuddling. My dick got instantly hard, and I tried to hide it. I guess he must have noticed bc he said he was going to sleep and asked if I wanted to go, too (we were sharing his room).

We went to the bed and soon enough started kissing and touching. The mouth kissing rapidly went to cock kissing. He sucked me and it was so good - my fisrt time having a man swallow me. I am pretty big but he swallowed me to the root. I got to his hard dick and sucked it as well, lincking the head like a lollipop. Then, I put the condom on me (obviously I took a condom for the sleepover) and penetrated his tight, juicy ass. Turns out he was a power bottom and he danced on my cock while riding me like a cowboy. We had to keep it quiet bc we were on his parents place, which is hard since I am very loud. I cummed so hard that day...

We eventually broke up after almost two years. It happened almost 15 years from now, but I remember this episode to this day...

 

[sac1066]

My close friend from school. We camped out in his backyard. We had just graduated and were both 18. I was leaving for the military in about a week and decided to camp. He had a tent and pads to sleep on. He had a very narrow but long back yard so were some ways away from the house. It was very hot even at night. We took our shirts and shoes off and were laying there talking about girls and getting horny. There was whiskey involved but i dont remember where it came from. he said he was hot and was going to take the rest of his clothes off and i followed his lead.
As we talked about girls, i could tell he was rubbing his crotch so i played with my cock. I said i would give anything to get a blowjob and he said no kidding. Then he made the offer. No one had to know and we could suck each other. I thought for a while and said sure! He reached over and touched my hard cock. He played with the head and then he moved over and kissed the tip. WOW!!! I asked him to do that again and then he licked it...wonderful. He bobbed up and down on it for about a minute and i came in his mouth. What a great feeling. I then returned the action.
He tasted like sweat and his was a little bigger than mine. I licked the head like a lollipop, not really knowing what to do. He loved it and moaned. I put the head i my mouth and sucked on it. He thought it was great. I wound up getting about 3 inches in my mouth and went up and down like he did. I rubbed his balls and bobbed. He shot in my mouth and i wound up swallowing it not knowing what else to do. After a few minutes he said we should have been doing that for years. i chuckled and said we should do it again. I was hard from sucking him. He didnt say anything after a few minutes he leaned over and started sucking me again. This time he rubbed my balls and my butt cheeks. I didnt last very long that time either and it felt really good. I sucked him off again until he shot in my mouth.
We fell asleep, woke up in the morning, put our shorts back on. we never really spoke of it and didnt do it again. i left for basic training and we lost touch. I never forgot and it gave me a curiosity about cocks and having them in my mouth. Man, that was great!

 

[deleted20046451]

The year 2000 I was 24, I had been wondering about guys for a while just never did anything about it. I posted an add on some "dating" site and explained i was a virgin with guys etc. After sorting through the replies I messaged back one guy in particular. We messaged on and off a month.

On Friday night he messaged asking how I was and how was my week etc. Told him I was horny and really wanted to try it with a guy that night. So eventually that night I'm round at his. And we kissing and touching each other. He blew me first and then I blew him. He gave such good instructions.

The he asked If i wanted to fuck him. well yeah I'm game. Well i failed and was not very good at it. He then asked If I wanted fucked instead. OMG it was fab and I loved it. Oh I was so green i never asked him to wear a condom so my first guy fucked me bare and filled me with his cum.

 

[halcyondays]

I was 22 he 20. College boys. He invited me to his room after hours at the hotel where I worked. Me 6'2 190 he 5'7 maybe 135 slim runner's body killah runner's ass cute face slim nose eyeglasses tousled brown hair blue eyes perfect smile. He flirted with me at reception where I worked. Stereotypical effeminate gay affectation--voice especially. He wore spray on designer jeans to show off his package and ass. Skin tight shirts highlighted his slim but athletic form.

(tbh I thought he looked better relaxing in a pair of roomier Levi's and a size-too-large t-shirt,)

Cock crazy boy his clothes came off as soon as I was in the room. He went down on me immediately. Had to see what I was packing in my slacks and have it on his lips. Gave great head. I had condoms he had lube. We went at it deep into the night. I filled three condoms and started a fourth. Insatiable hungry little bottom.

His full bulge consisted of average cock but big balls which shot copious amounts of come.

"Have you ever been with a guy before?" he said.

"You're the first," I said.

"That's okay," he smiled. "I'll show you what to do."

I had to smile. The first woman I was with had said the same thing.

 

[deleted2780451]

::redacted:: lmao

 

[sissyjanine]

So far its just been phone sex with men while my wife is away.

 

[Linkguy13]

I college at the dorms the blowjob was great, the anal sex not for me. Yeah it hurt I had no pleasure. Exit only.

 

[mrbigdoc]

Mine first time was a man much older than me. 45 years older than me. It was a great time and I sure learned a lot. We enjoyed time together for about a year.

 

[Jacksbiguncutcock]

Back in the days that defined my sexuality, I was over at the house of an older guy, Gary, that lived down the street. I considered myself straight at the time but had several jerk buddies that were impressed with my big uncut cock and thick creamy cumshots. They had told Gary about it. He asked me if I’d ever seen a big hard cut cock. I told him no, that my buddies and I were uncut. He pulled it out and got it hard. He asked me if I wanted to feel it, and I was excited and eager to do so. I jerked his cock a little and he asked me how it felt. I told him that his skin felt soft but his cock was very hard when I squeezed it. His huge erection was dripping precum, and Gary used his finger to collect it and then he sucked the precum off his finger. He told me that my friend had told him that my cock the biggest he had ever seen and asked if I thought his was as large. I asked if I could measure it. Gary got a ruler and I measured him as almost 8” long. I could barely get my hand around it. I told him we were comparable in size (mine longer but maybe not quite as thick).

Gary asked if I wanted to see him cum. I didn’t answer, I just started fondling his balls with one hand while steadily jerking his shaft with my other hand. After a couple minutes Gary pulled away and shot his load into his hand. He then licked it all up and swallowed it. Had never seen that before.

Gary’s mother got home from work right afterwards, so we couldn’t do more. But I saw him many times after that first meeting. He invited me over often, sometimes with a friend. It turns out that what Gary enjoyed most was eating cum, his or better yet someone else’s. He became obsessed with my big meaty uncut cock and huge mushroom head. I could deliver load after load of thick creamy cum that Gary loved to eat. I do not eat my cum but love to feed it to anyone that likes to eat it,

Hope you guys enjoy my true story and please check out my cock - I have many photos and vids in my galleries. Would love your comments!