First Time With The D

First Time With The D

The plan was that he’d come over first thing in the morning and we’d do it quickly before he went to work. Work resumed at eight; we agreed on seven. How silly that seems now, puerile. What does ‘quickly’ even mean?

It is exactly two-fifty-four in the morning. I’m naked, sitting on my bed with the laptop on my lap. There’s no light, a bead of sweat is rolling down the left side of my face. Outside, I can hear the night watchman blowing his whistle. There are crickets too, and night birds. I’m trying to find the right voice to tell this story in. I think I might be traumatized. No, I’m not trying to blow it all up more than necessary – after all, I did have a good laugh afterwards telling it to my friends  – and I do agree that ‘traumatized’ is a strong word, not to be thrown around carelessly. Still, how else do I describe it? I keep getting flashes of memory that make me grimace and clench my butt tightly, that keep me from sleeping. My butt is still sore.

He’d said: “It’s because it’s your first time, you have to endure it, you have to endure discomfort.” Or something close to that, I can’t be entirely sure. His eyes were pleading; there was sheer need in them.

You have to endure it, you have to endure discomfort.

A bit of context: I’m twenty years old. Bisexual. You could call me greenhorn: I’ve only been with two men. Both times, I topped. (I don’t like those words we use to describe sex between men, ‘top’ and ‘bottom’, or between women, ‘dominant’ and ‘subordinate’, as though one were better than the other.) On Grindr, my profile reads Top. The night I met him – let’s call him Ben – I’d switched that up to “I’m a top who wants to bottom for the first time. If you have a small dick, HMU.” I’d read something recently on Twitter about how bisexual men who top don’t really know what they want, but this was not what I was thinking when I made that change to my profile; in fact, it’s only now, writing this, that that tweet comes to mind. Of course, I think it’s a piece of drivel, the tweet, but I’d always been fascinated by the thought of having someone inside me. I dreamt about it, longed for it. I knew it was only a matter of time. I read articles on the internet about how to prepare, like how to douche, and how to find a comfortable position, and how what kind of lube to use: water-based, not oil-based. It’s going to hurt, the articles said, the first time always does. So I had prepared my mind. But I couldn’t have guessed just how much pain I was bargaining for.

I woke up late that morning. Maybe I should have taken this as a sign. It was about twenty past seven and Ben had been waiting for so long at the bus stop. I received him on the street, led him up to my flat. He was my age, tall, slender, dark-skinned. He typed fairly badly on Grindr, but in person, he spoke well, or well enough. It was awkward: in those first few minutes, I don’t recall either of us smiling. We didn’t waste any time. He brought out the condoms, I pulled him to me and kissed him and his hands flew to my chest and pinched my nipples through my shirt. He kissed badly, pulled my lips with such force that they hurt – and with such urgency too. He was hungry, I could tell, and perhaps there was something in this that made feel good: he was hungry for me.

I found his dick quickly. Oh, how much I love dicks! I tell myself that I simply find the human penis fascinating, sounding to myself like an anatomist, which makes me laugh. I love butts too, perhaps just as much as I love dicks, but I can never quite intellectualize it in the same way. Every time I’m with a man, the first thing I grab is his penis, then his butt. With women, it’s the butt first, then the breasts. But anyway, I found his dick (it was about the same size as mine, which should have worried me) and he found mine, and in a minute, we were both naked. At some point, I went and played a movie on my laptop so that the audio would drown out our moans. He waited impatiently, looking at me. When I returned, he put me on my back, raised my legs high apart in the air and put his face between my butt cheeks. And that was perhaps the best moment of that morning for me.

Let me say here that I’d never gotten a rim job before. With the two guys I had been with prior, I always forgot to ask for it, but the night I met Ben on Grindr, I had asked, “Do you eat ass?”

And he had replied, “Yes, I love that. Wash it up.”

His tongue was warm. Thinking now about the sensation it filled me with, I find that I’m getting hard. No one had ever touched me there before, I realise now. It was the most intimate part of my body, and to be touched there so warmly was the best thing in the world. I threw my head back and moaned and nothing mattered more than what he was doing to me at that moment with his tongue. It lasted about five minutes, then he took my balls in his mouth and sucked on them, a little too hard, just like with the kiss and, later, with my dick.

And then it was time.

“Fuck me,” I told him.

He started to turn me over.

“Where’s the lube?” I said.

He stopped. “Ohhhhh!” he said. He had forgotten to bring it.

Perhaps I should have taken this too as a sign. Use a lot of lube, the articles had said. The first time, you’d probably have to use the entire thing to make sure it is as slick as possible. I should have taken this as a sign and stopped right there, but I was already too far gone. So when he suggested using my lotion, I sighed and went over to get it. You fool, I’m thinking to myself now. You foolish, foolish boy!

This is not a sad story. I fear my voice is too grave, making it seem for all the world as though this were a rape account. It is not. When it was all over and I told my friends about it, we had a good laugh. Even now, I’m trying to put some humour in it. I fear also that I’ve not been generous with Ben in how I’ve portrayed him in these pages. After all, he was considerate enough, and stopped precisely when I asked him to, even though he was so hungry for me, I could see it in his eyes.

We made do with my lotion. He had brought three sachets of condom. The first we were careless with and ended up tearing. The second was better. He squirted the lotion on my opening and, rubbed it down the length of his penis, and then proceeded to stick a finger in me. I had taken the doggy position, my head flat on the bed, my butt high up in the air. I asked him to be careful; he understood that it was my first time.

I remember the first touch of his penis.  My eyes were closed, my mind empty.

I remember him trying to find my opening. I had drawn the curtains earlier and it was dark.

Fuck me, I was thinking. Fuck me!

I remember him finding my opening.

I remember him nudging. And then there was a sharp pain.

When I told this to my friend later, I said laughing, “The funny thing is, he did not even enter, he was still at the tip, and I felt like I was going to die.”

For the purpose of this account, I tried to find ways to describe the pain and came up with a few similes: like I was being stabbed with rusted sword; like a bullet had ripped through me;               like nothing I had ever felt before.

I recoiled and tried to endure the first flash of pain.

“Easy,” I breathed out. I pulled away to relax my muscles. “It hurts. Be careful.”

“Lie down,” he instructed.

I did.

When the second flash of pain came, more intense than the first, I knew I couldn’t do this.

“Oh God!” I gasped. “Stop! Stop!”

He had only pried me apart with the tip of his penis, not even an inch in. He stopped, but remained on me, his weight crushing me, and for a moment I had the sickening thought that he would hold me down and force himself into me. He didn’t. He rolled over and lay on his back, looked me in the eye.

“I’m sorry,” I said. “I can’t do this. It hurts too much.”

And that was when he said what he did about my having to endure discomfort.

“Have you ever bottomed?” I asked.

“Yes,” he said.

“How was the first time?”

“It was hell. But after that, it was better. But I had to stop because I had tears in my anus.”

“Hmmm,” I said. “I can’t do this. I’m sorry.”

He was quiet for some time, then he said, “It’s fine.”

“We can do lap sex,” I said, straddling him. My butt was sore, but I had to compensate him one way or the other.

After we both came, I lay beside him on the bed and tried to catch my breath. The pain in my butt had gotten worse, and would worsen still when, an hour later, I’d be sitting on the toilet trying to take a shit, thinking, What have I done to myself, fighting back tears.

I still get flashes of pain and it makes my heart race. I still can’t take a shit in peace. I still smell him on me sometimes.

A friend of mine said, “I think it was a lube thing. Maybe you should have stacked up lube first, and maybe done some fingering first. I wish I could give you practical advice, but like you, my hymen is still intact. But I’ll be sure to keep my ass as oily as a bottle of ororo.”

Another said, laughing, “Lotion dries up faster.”

To both of them, I replied, “I have sha learnt my lesson.”

After Ben left that morning, he sent me a message on WhatsApp: ‘Many thanks for today.’

I wasn’t sure how to reply, so I didn’t.

Yesterday, I went to a pharmacist and asked for the price of lube.

Will I be trying this again? Yes, most certainly. In about five months.

Written by Ijapa

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  1. Chris
    April 21, 05:58 Reply

    I have a feeling you’ll be fine. And you’ll know what to do next time.

  2. James
    April 21, 06:40 Reply

    Brother. Don’t go out there to bottom again if you haven’t done a little work on your self.

    We both have same story. I dated this guy for 3 years and as top in the relationship he was very loyal and submissive but we were both alpha males sort of and he even looks rugged than I am and even more masculine but he went down for me for 3 years. One weekend when we went on picnic and lodged in a hotel in badagry Lagos, he suggested that he should top so I feel what it takes to be bottom. We were really in love so saying no feels like betrayal so stupidly said yes. Now before now I haven’t thought about it or dreamt my self in it before. So i said ok lets do it. To cut this short i visited the clinic more than 10 times to treat the tear i suffered from. I couldn’t walk properly on the first day cuz I was bleeding so bad.
    We used water based lubricant and flex condom which I like much but no lubricant on earth could help the evil pain that almost killed me.

    SOLUTION: after 12 weeks I realised I got healed completely and my then bf was so afraid thinking he had destroyed my internal organ cuz of the bleeding. I said to my self that this pain would not just be for nothing that I must learn this thing and become fully versatile if i wanna survive in the Nigerian gay community .

    A doctor friend ( queer ofcourse) , advised me to start with self pleasure with a lot of lube. He said when ever I wanna wank I should try to stick my one finger in there and enjoy the doubke feeling . I took his advice and tried it out and it felt strange but gradually I started doing it often and will imagine my finger is a cock . He also told me never to try any Dick thicker than my two fingers . At this time when walking he told me to try two fingers. It hurt badly but I was determine to take the discomfort and not be on a situation where I will have to visit the clinic again.

    After taking my two fingers in for about a month of wanking … I felt I should try the doctors advice . I then decided to cheat on my bf just to shop a smaller Dick cuz his Dick was really huge few inches Niger than mine but too huge for a starter.

    I met this guy from church who obviously wanted more than just church brothers .
    He told me he was versatile and hey that was a relieve cuz I know I will have to fuck him first. After fucking I tried not to cum and told him yo come and try me too. I checked with my double finger and it seems almost the thickness and was a relatively smaller Dick compared to my bf.
    We consummated and it hurt from the beginning but all of a sudden I felt this pleasure I have never felt before .. I didn’t know God created men and put their G-spots in there . Little wonder my bf will moan so passionately , even though I couldn’t relate , I will just flow with the rhythm. Man it was something else , this guy knew how to stroke slowly and gradually … I couldn’t feel my legs .it was one of the best feelings I had.
    So I decided to double date . I had the church guy who we will flip flop sex and my bf whom I top only. I didn’t want to let go the church guy cuz his Dick was the exact specimen I needed in the laboratory in testing my ability to bottom. Well he didn’t know cuz he was all over my Dick as he liked my Dick more than him fucking me.

    So when I started feeling comfortable, I had to let him go and stopped double dating . But unfortunately for me my bf was also into another guy who was bottoming for him. I quickly cut ties with them both and went my way.
    I had become versatile already and prepared for the Nigerian gay community . It’s only a pity that my bf wasn’t patient with me enough to have the side if me he yearned for. We are just friends now and he is on his 13th relationship. I wish him luck . Hahahah.

    So man if you need a change , change it your self.

    Thanks for reading !

    • Facade
      April 21, 08:15 Reply

      You broke up with your boyfriend for doing exactly the same thing you did?

      • James
        April 21, 09:19 Reply

        I left him because he was already into another person who could bottom for him properly . And we were and are still friends so his happiness was paramount.

        • razup
          April 21, 20:04 Reply

          Wow! That is my story beside am still in double relationship. Am verse but i don’t like to Top my guy i prefer to Top another bottom or Verse.

    • Starrise
      April 21, 09:39 Reply

      So pathetic, you the wicked guy here, you first cheated on him so why did you abandon him for what you knew he was yawning for. Go get the nigga back biko. I love the way you narrated your relationship with him. I’m feeling for him now…. Wow 13th? Lol

      • James
        April 22, 14:18 Reply

        Hahahaha bro. This story is not cwntwrwd around me ooo. They asked us all to comment and help the original poster , so I had to karate my own story , I am not trying to steal attention from the original complainant ooo… Pls advice him and leave my own story there ooo . Lol

  3. B
    April 21, 08:24 Reply

    Virgin as I am, and 17, I still find time every other weekend to open up the hole a bit more. I’m very comfortable with 2 fingers now (and gosh, it feels so ecstatic already that I wonder what I’d feel with abs, strong arms and the LOML behind me), and will soon start off with 3 (yes, I want to be a “power bottom” ?). I think I can handle an average-sized D now, so I’ll suggest you practice a lot before you next time.

    • Nna
      April 24, 07:51 Reply

      That’s nice. You want no stories?

  4. B
    April 21, 08:25 Reply

    Virgin as I am, and 17, I still find time every other weekend to open up the hole a bit more. I’m very comfortable with 2 fingers now (and gosh, it feels so ecstatic already that I wonder what I’d feel with abs, strong arms and the LOML behind me), and will soon start off with 3. I think I can handle an average-sized D now, so I’ll suggest you practice a lot before you next time.

  5. Boniface
    April 21, 09:48 Reply

    bottoming is quiet a painful experience especially the first day l bottomed the guy has a huge dick but well experience in the sex he knows when to thrust and when to stop though after the sex l had no tear since then we’ve been dating

  6. PinkJaguar
    April 21, 11:32 Reply

    If Bottoming hurts then you are doing more than two things wrongly.

    From your write up multiple things went wrong hence the pain.

    I personal hate water based lubes, they dry up really fast and its so much work to do the re-applying thing. Use Silicone based instead. Use a river of silicone based lube and your first time would be orgasmic.

    The lotion thing made you nervous, so next time put on a good song that makes you happy. The foreplay should end with you smiling if not taking dick is gon hurt. Just generally be in a sexy happy mood.

    Entry; Lay on your side??????. Not missionary. Not doggy. On your side. Believe me it’s the most comfortable and when you start getting the hang of it you can do all the positions you like like a crazy ex pornster. But for the entry, on your side.

    Also Tops, when someone says its his first time, try to go as slowly as possible for the first few seconds. Slowly. Its tiring but its worth it (speaking from experience).

    And first time bottoming shouldn’t be a rushed activity. No No. its should be enjoyed.

    My first time didn’t hurt at all, I started feeling discomfort on subsequent occasions because I was rushed, not enough lube, wrong position, and if I was in a not so great mood.

    I hope this helps.

  7. Bee
    April 21, 13:50 Reply

    Virgin as I am, and 17, I still find time every other weekend to open up the hole a bit more. I’m very comfortable with 2 fingers now (and gosh, it feels so ecstatic already that I wonder what I’d feel with abs, strong arms and the LOML behind me), and will soon start off with 3. I think I can handle an average-sized D now, so I’ll suggest you practice a lot before you next time.

  8. Orobo Hunter
    April 21, 14:03 Reply

    Hey Ijapa. This explains a lot. lol

    Oh well, I’ve waited this long, I guess I can wait for five months… Xoxo

    • Ijapa
      April 21, 16:22 Reply

      You haf find me reach here again. God save me!

  9. George
    April 22, 08:12 Reply

    Suprisingly, i barely experienced any pain during my first time. Just a little discomfort

  10. Dennis Macaulay
    April 24, 06:29 Reply

    I always say listen to your body, you have no point to prove. If it hurts too much, then maybe it isn’t for you.

  11. xoxo
    April 24, 15:45 Reply

    Personally, I don’t think it’s something u have to be overly prepared for… too much preparing makes u too anxious and thus, spoiling all the fun, Just go with the flow.. if u know he is an amateur at topping, don’t even try it, u gonna regret it… I feel many pipo have wanted to try bottoming but their first experience ruined it for them, thus they get scared and say it’s not for them… just be comfortable, there is no rush, u are just 20, u still have like a lifetime

  12. xoxo
    April 24, 15:49 Reply

    Plus u are bottoming for the first time and u pick some random dude on Grindr who u have no feeling for watsoever to do it with and u are wondering what u did wrong, I dunno know about other pipo but when u meet someone u really like, it kinda makes it easier…. plus y’all had to do it in a space of less than an 1hr. And u tried doggy style first.. osheeeee baddest, what happened to simple missionary style for first timers.. honey this is just me, but u didn’t do anything right…

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