What Was Your First Time Like? 15 Guys Share Their First Gay Hookup Stories

There’s really nothing like that very first time, when awkward fumbling and nervous excitement begets either ecstatic pleasure or embarrassing failure. Luckily, most of us get lots of chances to try, try again.

For better or for worse, everyone remembers their first time.

Here to take you back to those formative years are fifteen Whisper about that first time hooking up with a guy.

Enjoy. And perhaps tell us about your first time in the comments section. 🙂w1w2w3w4w5w7w6w8w9w10w11w12w13w14w15

The one about the black stereotype tho… LOL

71 thoughts on “What Was Your First Time Like? 15 Guys Share Their First Gay Hookup Stories

  1. My first time was in an all boys boarding school….you know…senior friend calling out his junior aside and whipping out his dick in the dark……was so ooo …dunno!!!

  2. My first time was in a movie cinema while the movie “Rio 2” was playing and boy, it was the most heady feeling ever.
    Exactly a hundred and fifty eight days from today.

  3. Mine was 5th of December last year, and the only thing I still clearly remember is that I was more concerned that something might go wrong so much that I barely gave in to the moment. Simply put, no amount of videos or information whatsoever, can fully prepare you for that 1st front row experience.

  4. Everytime is like a first time to me because it takes forever before hooking up with someone else so each time feels like u am starting over again. Did that sound corny?

  5. Oh, my first time was with 3 guys when I was Five. Lawd knows how hard I’ve tried blocking those memories. Yes, Molested and No, its no cliche!

  6. My first real penetrative sex was so painful, couldn’t sit for days…cried all week, thought my bum was damaged beyond repair and I was going to become incontinent, vowed never to do it again. I was 15 . lol.

  7. My fiRst time was exciting, painful, crazy and really scary especially when I saw blood on his big dick, won’t trade dat grt sweet painful experience for anything though cus It made me to understand and accept me.. Btw I was just 14yrs old #wink

    • 14 years?? @ 14 I was thinking about playing the latest PS2 games.. And ppl were already getting royally plunged… Hmmmm. Nice name though.. It has one ring to it.. IVANKO..

  8. Masked man ,no be only you waka come ooo…My sheets are still clean too.

    You know,I am so apprehensive about penetrative sex in whatsoever way.

    Maybe my first time,the person in question will get me alcohol so that I can just dozz off ……,I wonder how alcoholic drinks taste sef…..or he gets me a sleeping pills….so I will not be aware of what is going on…
    Maka chukwu,I can’t be awake and see one *amu uwa* dey enter *my temple of the most high oooo….

    Nah,not for me…..

  9. Mine was with an admirer, saw me at my sister’s wedding, walked up to me, introduce himself and got me talking, shared a lot of laughs and he made me feel so special. He never made his intentions known that day tho. We exchanged numbers and got talking for sometime. I was 16 then and he was about 10yrs older at that time.. So over the phone, he told me he liked me and wanted us to be very good friends. I liked the idea cos I liked him. Took me out couple of times, but one night, to have dinner, not far from his place, while eating he kept staring at me lustfully then he said he really likes me and wanted me to be his boyfriend, I laughed so hard that I almost choked. When we finished he offered for us to go get some drinks at his place, we got there, got the drinks and saw drinking while he still stared at me. He then made his first move, my first gay kiss! 😍😍😍 I was so thrilled that I was kissing this guy who made me feel so special, like I was some chick😂😂😂… One thing let to the other and we got naked, he gave me the best bj I ever got In my entire ermmm…..
    He rimmed me, then fingered me, then ploughed me for the first time. BTW, he made me sniff something tho(poppers) that made the ploughing easy and pleasure/fun filled all the way. This was how my first time went down. This is my first time ever to post here, forgive the Typo errors and my lack of writing skills.

    • Hun, ur 1st time was pretty gud :), I mean he took u on a couple dates, got 2 know u b4 making a move, dats sweet.oh & I don’t c any typos + ur writing is solid.

      1st tym commenting??? welcome 😀

  10. lol… I think I gave up after 10 seconds of trying to “get it in”.. We both went up disappointed.. I was sooo scared 😀

  11. My first time was with my inlaw in a hotel room (trust me you don’t want the details). I just finished WAEC then and I didn’t even know what happened for over a week. Was that naive.

  12. @Jace….yes oooo….Its a therapy for being disvirgined….so says alot of girls and my wonderful sisters…lol.
    At least you will be rest assured that you will not be aware of what is going on until everything don finish,

    I say the pain for a first time na die oooo
    Its better not to know what happens on your first time….,you can enjoy it subsequently as they say.

    Better still,just take sleeping pills….the best they say

    • Eew. That’s risky, having sex without your wits about you. You’re exposing yourself to rape, condom-sabotage etc. If anal sex is too uncomfortable then you should probably stop trying to have it. It’s not a big deal.

  13. after a few years of “groping in the dark”, blowjobs and pawing frantically at a string of guys, i finally had my first attempt at penetrative sex when i was 15, we were in dormitory bathroom. I can still remember how he walked up to me with his intense, sparkling eyes, and with a towel slung over his shoulders and very little else, said “its very hot, lets go and shower” … how could i resist being in the shower with this hunk who carried between his legs something i loved to play with and to suck at every opportunity i got? We got to the bathroom and lathered up, and he moved behind me and “commanded” me to lean forward … dizzy with youthful exuberance and anticipation, i quickly complied, i had then never heard of lubricants, my knowledge of condoms was only limited to the gold circle condom adverts i saw on tv … so, with no lubricant or condom, he PLUNGED into me!!! what can i say? i never in my wildest dreams knew that such pain existed, it hurt like a bitch who was chained and being burned at the stake … i felt like my insides had been ripped and torn asunder, i could feel the pure unadulterated PAIN, as the pain impulse traveled from my behind up along my spinal column and finally registered repeatedly and with shocking intensity in my brain … It hurt so bad, i didnt know whether to clutch at my ravaged behind or to clutch at my head where i could feel the pain washing over me in excruciating waves … i hurriedly pushed him away, he profusely apologised and when the agony subsided, he presented himself asking me to “enter” him … surprisingly, he felt no pain and his entry was smooth as a whistle … After that horrible experience, it would be about ten years before i would even contemplate allowing anything larger than a medium sized finger get anywhere near my hole … the memory of that painfilled night lingered for about a decade and in the meantime, i left a string of frustrated angry men who’s dreams of plundering my booty were always cut short … That’s what my first time was like …

  14. My first time was in skl.. With a course mate.. Used the good ole spit…😳😳 😖😖.. Its so embarrassing thinking about it now.. I was a damn novice..

  15. At first I thought being gay was about kissing and vaseline in between thighs. First time someone tried to penetrate me I was 14 and couldn’t bear it so I made it stop. A year plus later an older classmate of mine made me penetrate and fuck him, I was in high heavens. And so did I become top, living the black stereotype, as like yesterday. I can still hear the white twink screaming “it is so fucking big, I can’t take it.” Yet he was clutching to my body like his very existence depended on it.

  16. Had my first time with another male back in the early nineties when I was about 8….and it was with my eldest brother who was 13 then…. I gave him a head and he used my laps. Thank God there was no penetration. #OkBye

  17. My first time was with my handsome corper maths teacher…enjoyed every bit on it was about 15 then and in ss3….got A in maths that term too

  18. Winsh, this ya ass was a good student ooo. To get the perfect A in the most dreaded subject maths. Any way mine was @ 7 with a chad neighbour of mine like 170% of my age
    Usually done in hide and seek method any where in the building as far as say nobody smell that area in the year 2000

  19. Late. My first time was with my neighbours sales boy. He was always groping my cock whenever no one was watching us and I was very excited and looked forward seeing him. One day he asked me to come to the tailoring shop where he worked and he picked a Sunday. All through that day in church I couldn’t concerntrate…I couldn’t find an excuse to leave my house under the surveillance of my strict religious “thou shall not” parents. Well,once I got home I braced up and sneaked out of the house damning all consequences. I got to the shop and he was waiting. He got a fanta and buscuit for me and before I could touch the refreshment he descended on me. He has just had his bath and was oiling his body in front of me and came to me. Pulling me up he started slowly touching me and asked me to turn. I thought at first we would do our usual cock rubbing and that was all but how wrong I was. He brought a huge dressing mirror and positioned in front of a big table. He told me lean on the table which In my state of confusion,I obeyed. I felt him rub Vaseline on my ass and then WHAM!!!! I went biserk like a terrified chicken but his strong hands gripped my hips very tight and dragged me back to his throbbing cock. ‘Its painful’ I whimpered in agony….still thrusting and moaning he said ‘na lie…e dey sweet you…stay well’…..I was in pain…my legs where shivering while I bit my hands in agony. I could see us in front of the mirror and my neighbors sales boy was flexing his muscles and doing fine boy faces to himself while fucking me. After what seemed like eternity he started talking some rubbish and began to rock his body back and forth while moving his head from side to side. I felt something rush into my stomach and dripping down my thighs. My neighbours sales boy (Obinna by name) staggered out of me and stumbled to hold a chair while moaning. Thick white cum was oozing from his cock..the floor was covered with sperm and we both where sweating like criminals caught red handed.
    I have never seen sperm in all my life. I was just 10 and he was about 17.

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