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

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

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68 Comments

  1. Lord II
    December 20, 04:23 Reply

    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. Anonymous
    December 20, 05:08 Reply

    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.

    • shuga chocolata
      December 20, 05:39 Reply

      WTH!!! @ the cinema???? Meh the thirst is real. My first time was so embarrassing that I had to go bck to make it EVEN. *sips iced tea*

      • pinkpanthertb
        December 20, 05:40 Reply

        All you people that are having grown-up first times… Hmm, those of us that had first times as teenagers nko? *facepalm*

      • supercharged69
        December 20, 05:59 Reply

        @Pinky trust me on this one, when it comes to “sex-matters” it’s best to be an early comer than to be that one last uninformed latecomer! But your own case be like sey e waka come alone sha, poor rotten child. *sprinkles preservatives on you**

      • u.k
        December 20, 08:17 Reply

        those of us that b4 teenage nko?

    • Peak
      December 20, 09:23 Reply

      @supercharged69 guy u no lie oooooooo
      I have been wishing I started early enough.
      My 1st time wasn’t that bad cos I had watched enough porn to hold a Phd over the year (thanks to living in denial). But its just embarrassing to be trying things that ppl are over and done with and having guys lose interest or look at u as a clueless dummy all cos u don’t ve a body count that dates back to the victorian era

      • Max
        December 20, 10:59 Reply

        Hahahaha hahahahaha… Skl days… I left quite a few body trail.. But thankfully I can still recall all of them… @ least I haven’t fallen off the wagon..

      • Airdeecan
        December 20, 17:11 Reply

        Yeah me too….. I was six my first time was six with my best friend J behind the couch in NY living room.

    • Airdeecan
      December 20, 17:01 Reply

      I know you,I walked with you once upon a dream……

    • Airdeecan
      December 20, 18:10 Reply

      @anonymous..Awwwwww, you remembered…..

      • Anonymous
        December 20, 20:15 Reply

        Yea baby … Remember I keep a journal.

  3. supercharged69
    December 20, 05:47 Reply

    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.

      • supercharged69
        December 20, 06:04 Reply

        You’re probably a natural, for some of us it takes an overtime skill acquisition to sync with the rythm.

        • pinkpanthertb
          December 20, 06:08 Reply

          It wasn’t me at all. I was green, trust me. and very fearful. It was all Him. The other guy. He was the one with mad skills on bedroom antics.

      • Max
        December 20, 11:00 Reply

        @Pinky, is it someone we both know!?? Looks @u with odu Anya..

  4. Ace
    December 20, 05:49 Reply

    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?

    • A-non
      December 20, 07:41 Reply

      @Ace,same here as well…

      • B.A.D
        December 20, 14:06 Reply

        lol, thank u 4 dis. Wayyy too corny

      • Ace
        December 20, 15:18 Reply

        Lol! Well it is true nah. Right now only two people i hooked up with are etched in my memory and that’s because the romance and foreplay (which i am majorly only into) was breathtaking. The others are just like leaves blown like the wind in my head. I cannot remember them and it is most like because the time we shared was boring or not good enough to be remembered. Did this sound less corny now?

  5. Vhar.
    December 20, 05:54 Reply

    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. daniel
    December 20, 06:40 Reply

    I don’t remember my first time, am I that weird?

  7. FKA Chizzie
    December 20, 06:43 Reply

    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.

  8. IVANKO
    December 20, 08:02 Reply

    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

    • Max
      December 20, 11:02 Reply

      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..

  9. Handsomely Inclined
    December 20, 08:04 Reply

    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…..

  10. Absalom
    December 20, 08:20 Reply

    My first time was awkward and uncomfortable. But the foreplay and afterplay was great. Lasted the entire night.

  11. tobby
    December 20, 08:41 Reply

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

    • pinkpanthertb
      December 20, 08:53 Reply

      Lmao. That ‘get it in’ sef… It can be very terrifying for virgins

      • Jace
        December 20, 09:53 Reply

        It is very terrifying. I’ve tried a couple of times but still can’t go through.

        @Handsomely inclined, does getting drunk help?

    • Max
      December 20, 11:06 Reply

      That’s the most boring part of it all…ndi virgin… So annoying… They’ll keep whimpering like you’re about to kill em….hahahahahahaha.. That’s why most times I just skip that part.

  12. DeadlyDarius
    December 20, 08:49 Reply

    My first time was not as bad as I thought it would be. Late-bloomer here…I wasn’t a teen

  13. enigmous
    December 20, 10:00 Reply

    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.

    • Khaleesi
      December 20, 10:25 Reply

      ***jumping up and down and flinging hands widely in the air**** i want details, pleaaassseeeee, i wanttttt …

  14. Handsomely Inclined
    December 20, 10:22 Reply

    @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

    • Absalom
      December 20, 10:31 Reply

      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.

  15. Khaleesi
    December 20, 10:24 Reply

    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 …

    • A-non
      December 20, 10:40 Reply

      Lol @ frustrated angry men whose dreams of plundering my booty were always cut short.

  16. trystham
    December 20, 11:46 Reply

    All I remember from my 1st gay hook up is me screaming “ouch ouch ouch!!! Take it OUT”. I can’t remember his face sef

  17. Dom
    December 20, 13:43 Reply

    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.

  18. B.A.D
    December 20, 14:00 Reply

    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 😀

  19. Adrian
    December 20, 15:47 Reply

    My first time was with my neighbour in school…it hurt tho…the guy was abnormally big…buh I wanted more later on…

  20. KingBey
    December 20, 19:43 Reply

    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

    • Khaleesi
      December 21, 07:52 Reply

      ***breaks out in cold sweat*** oh God! Sweet Lord! …. i hope you and your brother have been able to move past that and find normalcy in your relationship ….

  21. Emii
    December 21, 13:39 Reply

    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

  22. Promise4all
    December 25, 00:21 Reply

    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

  23. Frank enStein
    December 26, 00:45 Reply

    My first time was in my first week of university with a guy I met the same week

  24. courtsofdomasiobo
    December 28, 15:04 Reply

    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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