My First Anal Sex Experience

My First Anal Sex Experience

I was just 17 and was about rounding up my secondary education. I was living with my mom and two sisters.

I was quite a close friend to this guy, a neighbor, in his mid-twenties. Let’s call him Daniel. I was always his “boy”, as I would call myself. My close relationship with some girls in our area helped our friendship since he would always send me to hit up on a girl he likes. I was literally the middleman in most of his relationships.

On this fateful Saturday, I dropped by his room to check up on him and probably take on a new assignment. He was initially doing his laundry outside before he joined me in the room. There was light, so I turned on his TV set and DVD player to see a movie while we talked. I was busy scanning his CD rack for a movie to watch when the DVD player started playing a CD that was already inside. I was startled and strangely excited when I stared at the TV screen to see that it was porn. Interracial porn! The sleek rippling muscles of the black men as they manhandled the simpering white female.

My attention was instantly arrested and I found myself smacking my lips. I was definitely settling for this. But Daniel was not having it. He attempted to remove the CD, asking me to see a Nigerian movie instead. I protested, wanting to know why he wouldn’t let me watch the porn. I was seventeen for chrissakes, hardly a child! His response wasn’t what I expected. He said he wasn’t comfortable watching porn if there wasn’t any promise of real-life gratification, no hope for pussy to relieve the stress on his hard-on.

I was adamant and struggled against his determination to take the CD out of the player. He finally gave up and simply sat down beside me.

OK! Let’s do this!

We were about ten minutes into the adult action, when I heard him sniffling. I turned to him and was surprised to see tears running down his face. He was crying!

Feeling slightly alarmed, I said, “Haba, Bros D, wetin dey do you, this one wey you dey cry like omormor so?”

He replied, “Shey I tell you before. I no dey fit watch this kind thing like that, unless me and babe dey together.”

I was at first amused, then I felt sorry for him. That is, until I noticed his bulge! He was clad in just his boxers, and I could see the outline of an angry erection straining toward the ceiling. Even without touching it, I could tell that shit was brick. I was already horny from watching the porn, and the feeling grew to its peak when I saw Daniel’s hard-on.

Cautioning myself, I reluctantly turned my gaze back to the TV.

But Daniel wasn’t done talking yet. “How we go come do this trouble wey you don put me now?”

“I no know o. That one na your problem,” I said sternly, acting like I really didn’t care.

“I wish say you be homo,” he said. “We for just run am sharp-sharp.”

In a morning that had been full of surprises, this one took the cake. Had Daniel just now talked about homo? As a teenager, I was already on my journey to discovering myself and my love for guys and penises. I wasn’t an adventurous person, but I’d had a lot of fantasies, some of them featuring Daniel. To hear him say what he’d just said filled me with surprise, elation and excitement in a rush.

Trying not to give away my excitement, I said as casually as I could manage, “You be homo?”

“Sometimes,” he said.

“What about those girls wey you dey send me dey go meet?” I asked.

“No reason that one. I dey go down with anybody.” He waited a beat, then asked, “What about you, you be homo?”

“I no know o,” I demurred at once, feeling the pull of caution. “I never know the one wey I be for now.”

“Make we try am na,” he said cajolingly. “Abi how you see am?”

My prayers were finally fully answered. Thank you, Master Jesus!

I reached out to his boxers and rubbed my hands against his bulge. The thing that lay beneath the boxers was the rock I’d imagined it was. I drew his boxers down to see a well-shaven pubic area, helmed by what was bigger than my enemy’s destiny.

Jisoxkraist of Nazareth!

It was a GBOLA!

It was massive!

It was girthy like that of Shane Diesel! Do you know about the porn star Shane Diesel? Google him and his erection and you will have an idea what Daniel’s preeq was like.

I’d seen a lot of porn movies at this age, and I knew just what to do next. I slid down to Daniel’s crotch and gave the GBOLA a kiss first. Then I put it in my mouth – or tried to – and began managing a passable effort at sucking him while massaging his balls with my fingers. I sucked and tried to deep-throat that dick. Big mistake. I gagged violently.

But it was heaven. Having this dick in my hands, in my mouth – it was the greatest thing. and I knew I was doing a good job when I heard him moan. Chai! His moans reignited my fire. I stretched an arm up to one of his nipples and let my fingers play with it. I continued my ministrations for few minutes, and then he stopped me.

“Make we do am,” he said in a low hoarse voice.

I knew what was now on the menu and my heart had started pounding really fast – whether from anticipation or fear, I had no idea.

I was still in my shorts. He stripped them off me, bent me over and smacked my ass.

“See as you carry big soft nyash like woman,” he said in a pleased growl.

I felt a rush of pleasure at his remark, despite the fact that I got that compliment a lot. At that age, I had a very feminine physique with an ass that was either envied or appreciated, depending on whose attention it had caught.

Daniel reached out to a rack by his bed and picked out a tub of cream, opened it, fingered a considerable amount of lotion, and dabbed it on my ass hole. The touch of his moist fingers on that very private part of me filled me with an instant frisson of tension. I stiffened. I mean, this would be my first time. I suddenly wasn’t sure I was ready. But I had to try at least.

He rubbed some more lotion on his cock before positioning himself behind me. As I felt his dick-head poking at my entrance, I gritted my teeth and prepared for the worst. He moved forward. His dick-head hadn’t even slipped through and a bolt a pain was shooting through my body, causing me to flinch away from him.

Chai! It was painful. I was gasping.

“No worry,” Daniel quickly said reassuringly. “I go take am easy… The head never even enter sef… I go put am small-small. No fear.”

I clenched my fists and positioned myself, ready to give it another try.

We die here!

Slowly, inch by excruciating inch, he managed to get his cock in. not all the way in though. He could only manage a quarter-length of that massive shaft and I was done taking in any more of him. So he stopped there and began pounding me. His hands on my hips, he gently thrust in and out. Flashes of pain ricocheted all over me, so much pain, but I didn’t want to spoil his fun.

That determination to not spoil his fun lasted only about a minute, and I was pushing away from him. Running from that cock. Eet haf do biko! I picked up my shorts and began pulling it on fast.

He looked startled and looked a question at me. “E dey pain you? Na only small I put na.”

“No o! E no pain me at all,” I denied. “Piss been dey catch me since. I no fit bear am again. I dey come now-now.”

“But I don almost do finish n,” he pleaded. “Just wait small.”

“If I wait another second, I go piss for body abeg. I dey come just now.”

I unbolted his door and ran out, off to my mother’s house straight. I wasn’t even able to walk well because of the pain. Thank God no one noticed. My mom wasn’t home and my siblings had gone out to play. We had this standing fan, which I turned on. Then I dropped my shorts, bent over and directed the fan to my burning asshole. I needed the breeze to cool things off down there.

After about an hour, I went back to Daniel’s apartment. He was still in the position I left him, but with his boxers back on. I could tell he’d been waiting for me.

“Bros, no vex,” I said. “My mama send person come call me before.”

“No problem.” His face had brightened some. “Oya come make we finish am.”

“No o, e go be another day. My mama send me message. I just come tell you, make you no vex.”

His face fell again. “OK na, another day.”

“No problem.” In my mind, I was like: No be me you go kill o! Go tell them say you no see me for house.

And I left feeling elated, like I had just overcome the devil.

Daniel and I would indeed get together “another day”. We eventually managed to have sex like twice. And it was painful every time. But I persevered because I felt like I owed it to him.

Written by Manuel

Previous A Story Of The Boys I’ve Loved
Next “The Accuser Never Said ‘Stop. I Don’t Give Consent.’” Kevin Spacey Pushes Back on Sex Assault Allegation in Court

About author

You might also like

Our Stories 80 Comments

I Was Warned To Leave Straight Boys Alone

I am in big trouble. Since I became aware of my sexuality, I have had my fair share of gay hook-ups, but my sheer love and attraction for straight guys

Our Stories 47 Comments


Previously on STRAIGHT BOY SPECIAL… * So, I woke up the sound of sex. Charles was fucking Vivica, his muscular ass contracting and expanding as he thrust into her. I

Our Stories 10 Comments


I matched with a guy on Tinder a few months ago. He was a very good looking guy, but when we started chatting, I was careful to not get flirty


  1. Sharp
    December 28, 07:04 Reply



    Let’s be honest, anal sex is painful!!!

    How do you so-called bottoms even do it.

    • Pink Panther
      December 28, 07:51 Reply

      Bottoms are not “so-called”. They just are. And if you wanna know how we do it, well, there’s a series on here called The Bottom Chronicles. You should check it out. 🙂

      • Delle
        December 28, 11:56 Reply

        *snaps fingers in the Zee, smacks lips and prances on*

    • Minxaspis
      June 21, 07:57 Reply

      No one is a so called bottom bro get you’re corrected

  2. Manuel
    December 28, 08:56 Reply

    Osheeeeyy! Thanks a lot Pink Panther for sharing this…Your editing skill is outta this world..So Apt! More to come..

    Thanks Again…

      • Manuel
        December 29, 18:26 Reply

        ?Correct…Proper Warri boy here!

        • Richie-Michie
          December 29, 20:07 Reply

          E nor dey hard to find una for new location. No worries, we go jam one day. I also stay in warri but currently out of town

  3. trystham
    December 28, 09:15 Reply

    It must be that I eat too much. I can never have sex at the drop of the hat

    • Solange
      January 01, 14:34 Reply

      There is this miracle called douching .

  4. that dark-fair guy
    December 28, 11:10 Reply

    See me laughing and I haven’t yet tried it o.Fear no go gree me.I don’t even allow the tip.

    This was a hilarious story.Enjoyed every bit of it.Well done Manuel!

    • Manuel
      December 29, 18:38 Reply

      There’s no harm in trying sha..Ur case may be different…

      Thanks anyways!?

  5. Brazyne
    December 28, 11:39 Reply

    Lol, I totally started smirking when I heard the ‘bigger than my enemy’s destiny’ part.
    Nice one manuel….u can still overcome it though

    • Manuel
      December 29, 18:40 Reply

      You shoulda seen it…?

      I did with time sha…

  6. gyrt
    December 28, 12:32 Reply

    I’ve always respected bottoms that do anal….

    e no easy……

  7. mike
    December 28, 13:13 Reply

    Lucky me, then.
    Lol yhur pigin lexicon sha, yhu try.

  8. Tristan
    December 28, 16:25 Reply

    The first time I got fucked, it was heaven. Why does it seem like I’m the only one who enjoyed it to the fullest? I can rmbr vividly how massive my partner’s schlong was.

    • Toba
      December 28, 17:59 Reply

      Mine wasn’t bad either, I was 15 then and I had looked forward to it all my life prior to that that.

    • Peskyme
      December 28, 22:24 Reply

      Please how did you prepare for it ,I’d like to know.and during the sex .was lube used..or what

    • Bobby
      January 03, 19:47 Reply

      Biko if anal sex is painful for you leave it ooo..send your men to us. Lets us help. I mean, what are friends for if not for inconveniences? …some of us like it. I like it. Inshort i love it. …especially when zaddy is hitting the right spot and my eyes roll back into my head.

  9. S.W.E
    December 28, 23:59 Reply

    Oh yes, I know Shane Diesel
    We have lots of “Night devotion” together.
    Also, taking D becomes easier as time goes on,you just need lots of lube & an experienced/patient Partner

  10. Half Naked
    December 29, 02:27 Reply

    Bottoming is sweet!

    And painless and… (insert whatever you like)

    Most bottoms end up hating anal sex once they have tried for the first time.

    We all know why.

    And I used to be one of those people until I discovered something most people are doing wrong.

    What was it?

    It’s all about the sex position!

    After I made this discovery, I began to enjoy sex like the porn stars.

    Here’s how I did it.

    I found out that whenever I insert something (READ – a butt plug) into my ass while LYING on my BACK (Note the capitalised words because those are the key points) , I feel tingling sweet sensations instead of pain which I felt when I tried anal sex for the first time with my partner.

    So, I did it more and more.

    Lying on my back and inserting a butt plug in my ass.

    NOTE: It’s important for you to lie on your back for you not to feel pain.

    I don’t know why this works but it sure does!

    When I finally used it with my boyfriend, we mutually enjoyed the sex.

    TL:DR – Always lie on your back for the first few sex that you will have as a bottom.
    After that, you can take on any sex position that you want.

  11. Delle
    December 29, 03:59 Reply

    My first time bottoming is one of my best so far (and I’ve had a number). I even went three rounds with my partner and it beats me how every other person seems to have it different.

    Oh well…

    • Colossus
      December 29, 11:02 Reply

      Wow! 3 times? No pain, just pleasure? How small was his dick?

      • Pink Panther
        December 29, 11:51 Reply

        Hahahahahahaa!!! You had to go there, eh Colossus?

    • keredim
      December 29, 11:47 Reply

      First time!! 3 times!! no pain!!!

      Please how relaxed is your sphincter muscle??

    • Delle
      December 29, 12:01 Reply

      Okay let’s all be calm ?. That my first time was great and all does not not mean I haven’t had trying (bottoming) times.

      I guess I was really ready for it that first time. Mentally prepared and all seeing as it was even me that called him over after finally wanting to get penetration done and over with.
      Being mentally prepared helped with relaxation which is key when bottoming.

      Then he, my partner then, was someone I was very much attracted to.
      Emotional connection helps as well as there’s a need to want to satisfy; the need that circumnavigates back to your satisfaction as well.

      Then his dick size.
      Pretty lengthy but quite slim. Just the type I’ll advise people to go for when wanting to get penetrated for the first time.

      Amazing, patient, thorough and self-sacrificing. For him, my pleasure was paramount (he knew beforehand it would be my first. Communication, indispensable ?).

      Of course there was enough lube use. The rest is history. The porn star in me couldn’t have hidden for long.

      But like I stated in my first paragraph, I’ve had sorry bottoming experiences. However, it would go down memory lane that I had an Amazing first time ?.

  12. law9
    December 30, 00:35 Reply

    hunmm nice talk but gay sex is sweeting only the man top wher bottom in painful

  13. Minxaspis
    June 21, 08:01 Reply

    Manuel baby the fan aspect almost killed me with laugh lol I’ve gone through it before as a lesbian my first time,my partner used a strap and shifted my precious womb but oluwa gat me lol

    • Manuel
      January 19, 02:00 Reply

      lol.. omo i totally gave up on anal sex since 2016. i’m currently married to Jesus, no be me and that pain abeg

Leave a Reply