My First Time


So thanks to you – best readers ever – I topped what I did last year and am nominated for four Black Weblog Awards! You guys fucking rock. Now you know what to do right? Head over here to get instructions and whatnot and help me bring it home this year.

First off,  my sincere apologies to you guys for not giving you something nasty on Friday. Blame it on the combination of being fresh out of dirty ideas and a nap that went horribly wrong. But to make it up to you today I’m telling you  a story a lot of you have been asking me about for a long time – the first time I had sex.

So I was 18 and newly attractive; having only recently learned the value of contact lenses and gotten my weight, hair, and eyebrows under control. And one Friday night my sister and I set out to see a show. As is our custom, we got there early and secured our position at the very front of the stage – we don’t like being at concerts when you can’t see well. Pretty much everyone we knew in life was at the show too, so we talked and drank and cut up with our friends until the show started.

Not too long before this day I’d seen this person (let’s call him Doc) perform and met him and some of his entourage. So when, throughout the show he was grinning and winking at me, I really didn’t think much of it. Like I said I was newly attractive and not yet able to see the meaning behind that particular gleam in a man’s eye.

Anyway, two twos the show was over. We’re milling around, talking, laughing and making plans about what to do next when a burly man who had been on the stage came over and said Doc would like to speak to me. Let me just say this now in my defense – I was 18 and very very stupid – so I went. Doc and I chatted, he probably flirted with me and I probably didn’t realize that’s what he was doing. He asked where I was going next and I told him and he asked if he could roll with us. I said sure and he told me to meet him at his van out front and I could ride with him and show him where the place was.

So I tell my sister the plan and we head outside. A little time passes, he comes out and he and I get in the van. My sister…I don’t know what happened to her. I pretty much stopped thinking about her the minute burly dude said Doc wants to talk to you.

So yeah I’m in the van and we’re talking; I don’t remember much of the conversation. After I wrote that sentence I sat here for a minute with my head turned up; searching the recesses of my brain for just one thing we talked about. I can’t remember a thing. Anyway, a little time passes and next thing you know his dick is out.

Now I’m 18 and I’m a virgin but I’m not completely inexperienced. I’ve seen dicks before but this? This was – gargantuan. This was less a cock and more a…third arm. I’d never seen anything like it in my life. And as I marveled at it in a combination of horror and fascination it struck me that that THING was supposed to go inside me.

I said something to that effect and he reassured me that it would be fine. That yes – we would be able to get that thing in there. Don’t worry, just relax and leave it up to me, he said.  I was laughing in that hysterical nervous way I do when I know I’m about to get hurt and to calm me down he suggested I suck it a little.

Um….you want me to do what?

Colour me stupid but before that moment I didn’t know people did that. I truly didn’t. Even though I was 18 and even though I’d gone to school with pervy Catholic school boys my whole life, I still didn’t really know that that went on. My classmates used to joke about giving head and I used to laugh along but I never really knew what it meant. I thought I did but I was always like….but there’s no way anyone could do that. Well guess what?

Charming devil that he was, Doc convinced me that yes people do this and yes people like it. Let me show you. So I lowered my head, he put his hands in my hair and slid his dick in my mouth. And the sky opened. I didn’t really know what I was doing, but I liked it. I liked everything about it. I liked the smooth hardness of his dick, liked the noises he was making. I liked the gentle tug on my hair and the pulsing in my pussy that all of this was causing. I was ready for what came next.

He undressed me and laid me gently down.  He got on top of me, put a condom on. With his dick hovering just outside the path to glory, he began to tell me stories. He rocked gently against me; lightly hitting my pussy with his cock as he told me a story of something funny one of his dancers had said on the way there, then told me a story of the time they all got in a huge fight after a show in Saskatchewan. He told me story after story of his adventures while he gently eased that anaconda into me.

And then he stopped talking. And I was filled with him. As he stroked me he told me what to do – wrap your legs around me, arch your back, tilt your pussy up (at that one I was like  – huh?!?) he contorted me into whatever position he wanted me and he coached me and encouraged me the whole time.

And then, when he was close, he put me back down on the floor. Got on top of me and pounded me, hitting that spot years before I even knew there was a spot to hit. Sounds I had never made before began to come out of me and I clutched him and tried to draw him deeper into me. He began to moan louder and louder until he collapsed on top of me.

We were both quiet for a minute or two and then he looked at me and said “Holy shit! Are you sure you never did that before?”

After that we chatted for a bit, laid there idly stroking each other as he asked me if I was okay, how I felt, if I liked it. Then people began to knock on the door of the van and we had to organize ourselves and head over to meet up with everyone. When we got there, he asked me for my number and I gave it to him; knowing even at that age that he would never call me.

Surprisingly enough, he did call the next day. Just quickly to let me know he was heading back home and to let me know he’d had a good time. Shocking right? But get this – the next time I saw him, which was probably about 7 years later and after another show of his, he apologized to me. He said he’d been thinking about me and he realized that he’d taken advantage of me and that I was a nice girl who deserved a better first time than that.  Weird, right?

Anyway – that’s the story of my first time. Are you guys gonna tell me yours?

And please don’t forget to vote for me to win a Black Weblog Award or four. If you don’t want me to be the Susan Lucci of black blogging, do me a favour and click here

bag lady. digital nerd. beauty junkie. shoe whore. i'm a sucker for big words and box-fresh kicks. know a little bit about a lot of things and have something to say about everything.

Comments 36

  1. Malik says:

    Wow, that actually seemed like a pretty great first time.

  2. Alana says:

    I agree with Malik. That was a great first time. He definitely seemed considerate, concerned with you both accomplishing the goal. Unlike some of our frist time, just a horrible experience when I think back and compare.

  3. LaLaBakir says:

    c/s Malik and Alana…seems like a half way decent 1st time if you ask me.

    1. max says:

      It was a great first time; I have no complaints. And Doc’s position as one of the nicest guys I know is forever solidified for the way he handled it. I’ve had men I know a lot better treat me a lot worse so hats off to him.

  4. RedLady821 says:

    yeah…it was pretty good Max. I would have taken that over MY first time. Total wackness.

  5. Malik says:

    I’ll tell a little about my first time. It was with an older woman, though not cougar older, but old enough to have been out of college for a couple of years and already starting a career. Like the majority of the dubious events in my life in the last few years, I met her online at a certain rapper’s message board. She grew smitten with me, first phone conversation I had her play with herself (one of the top 10 moments), we talked for a couple months. When I finally went off to school she decided to visit me in DC for a weekend.

    Met her at the subway, it was awkward for the first few minutes because she was buying something from a street vendor. We strolled back to the hotel she was staying at and she immediately decided that we should have sex. She went into the bathroom to change into some lingerie, I laid naked in the bed. She came out, I admired for about 5 seconds before tearing them off. Apparently this upset her because she put a lot of effort into picking out the set, so after coaxing her and kissing her for awhile she calmed down.

    Then after running the gambit of the rest of the zones (lips, neck, nips, etc.) I went down on her. I gave like 12 seconds of a terrible effort before she told me to stop. I was not using any of the tips given over the past few months. I collected myself after asking for a second chance and tried to apply everything that I learned (granted it was far from perfect, but it wasn’t exactly something you would turn down either!). I rolled my tongue around her clit and gave ‘candyland’ (as she calls it) a kiss every so often. Ran my tongue around every centimeter of candyland and then attempted to do this thing her Asian ex-girlfriend did to her. I place her clit between my teeth (I made note to the bite down but to simply hold it in place) and started sucking on it to various degrees while moving tongue around, across, and pressing on it. Her thighs almost crushed my skull. I lost track of time and later she had to pull me by my hair.

    I now finally had a chance to go in and dear lord she was tighter than a vice grip. I suspect it didn’t help at all that I have a curve (upwards and to the right in case you’re wondering). I dug in regardless, trying to go as deep and hit as many spots as I could. In hindsight, I was probably too aggressive. I didn’t really care though because it was my first time and certain animalistic urges told ‘ricky’ to attack candyland like a wolverine attacks anything. I was in their for a surprisingly long time trying to contort her into as many positions. Towards the end I finally settled on doggystyle. I was still acting an ass, so my immediate reaction to how great it felt was to grab her hair and force her face into the pillow. I kept it like that until I just switched to me entire right arm. Then I came I think like 3 or 4 times. Woo no condoms!

    Finally I slid out. She went to the bathroom to clean up. About 10 minutes later, I asked her if we could do it again. And that’s pretty much it for what we did for the rest of our weekend with occasionally stopping for food, movies, or sleep. I did constantly wake her up by eating candyland though. That’s pretty much all I did for the second half of the 2nd day and almost the entire 3rd day.

    1. max says:

      Now that was a good story!

      1. Malik says:

        I sent my interpretation of the events to her. She said she would like a rebuttal, so if she gets back to me today I’ll copy and paste what were her feelings and what she remembered about it.

    2. GirlSixx is ChloeRayne516 says:

      *Blink Blink*

      All of this went down –being it was your 1st time??…

      1. GirlSixx is ChloeRayne516 says:

        Well Damn between your and Max’s story I don’t know which one has me *swooning* the most..

      2. Malik says:

        Yes. I think I had a clear understanding of what she wanted prior to the act. From there on out I just went on instinct.

    3. Malik says:

      Here’s her response. One quibble aside, I like her interpretation better.

      “When I saw him, I didn’t know what I was doing. Who I decided to become and exactly what was happening within us both, but I loved him. And that I knew and was fond in learning him.

      His eyes were silent, lost in mine most of the time. He was coy like a handsome school boy with all the arguments of a scholar of course with a kitty mentality around a woman. Indeed I was very much a woman, his at that. I did what I know how to do best; I l talked. I asked all the questions spiked from my nervousness of the whole situation.

      We reached my hotel. I made sure we could be comfortable and cozy in a capital house hotel room. And I got double beds just in case I flipped and cried for the next 48 hours -I’m an emotional head case. I didn’t wait for the commencement of searching in each other’s eyes. I had already made up my mind to agree with my hormones and set the direction I was headed for intimacy. He, a young man was a hung virgin who never touched wet panties let alone entered walls of a water slide like mine.

      I went into the bathroom to change and came out in playful blue and black 2 piece lingerie set I found at Vickie’s. And like any primitive animalized ram, he did just what he was supposed to in seeing me in this. He opened him mouth and clung his hands to my body. Ripping the cloth off me, I angled my body gyrating in motions that would lead his baby face down the trail of my candyland…

      The first effort, mouth on my entire nappy dug out lasted 12 seconds straight. He took all he asked and spoke in a new language! I gently sat up pulling my coochie out his face. “part my lips, position my clit in your mouth with your teeth and suck….”

      My legs struggled to stay up at first. Slowly, surely, he found his rhythm in his Panamanian cumbia soul. I couldn’t help it. My legs grew strong… tight and I squeezed the cum from my womanhood into his mouth and running down his chin.

      His mankind saluted with full attention. Surprised by how much of it he enjoyed, pleasing me became the vice to his cumming. He slid him. I hesitated because I was tight and he was curved with girth.

      Slowly his grunt pushed through passing through my pleasant walls. And I did not mind. I invited him, his love, and could see us quietly in love and I an army wife with a man who could name my babies.

      Welcoming him in, open I stayed and when he came… I swear I prayed.

      I took his virginity, he took my dreams- fair enough.”

      1. max says:

        Well damn. Looks like you two are a match made in heaven.

    4. Obsidian says:

      This is a very interesting series of comments – a true Field Report! May I use it at the O-Files? I think the fellas will learn a heck of a lot from it. Please lemme know. Thanks!


  6. MsEsquire77 says:

    1) I know who Maxie’s first is and he’s FAHN!! *swoons & faints*

    2) My first time was with my first love. It was the week of my 18th birthday and I’d snuck him in my dorm room. It was supposed to be ON my 18th birthday but Hurrican Opal caused my campus to be evacuated and we spend the next few days at my great-aunt’s house. Anyway, it was lovely…and we screwed like rabbits until we broke up 6 months later 🙂

  7. SmartFoxGirl says:

    *fans self* This was HOT!!! Nicely written too. I envisioned all of this. *fans self again* I hear some people (read men) say that big d*ck men don’t always know how to work it but I refuse to believe it. Women talk and one thing I’ve heard is the masters of big D are EXCELLENT with their tool. I have yet to hear a bad story and the way your friend worked you deserves some time of an award. That was really smooth.

    So what you lost it to a friend, actually that probably was the best thing for you. What if he would have stuck around and made you his woman? Your life could have been filled with drama, disappointment and MAJOR heartache. It’s probably better he left…especially since he was clearly a master D slanger. I wish I would have lost mine to a stranger. Good post.

    1. max says:

      The only useful thing my older sister ever told me was to make sure I did not lose my virginity to someone I loved. She said he would own me for the rest of my life. She said pick someone you like who is cool and it will be a pleasant experience. I didn’t exactly do my due diligence with this guy but I got lucky and he ended up being cool as shit. I’m always happy to see him when I run into him but he doesn’t own me in any way shape or form.

      Now that man who turned me out ( though, that’s a different story. I can’t shake that one for the life of me!

      1. O_D says:

        Men strongly advise to this same idea also. Of course it’s more judgmental in that “oh you can’t really aim too high for your first piece”.. but it’s the same theory.

        BTW since everyone is over sharing, I’m still waiting for your story SFG!

  8. GirlSixx is ChloeRayne516 says:

    That was HAWT!!!!

    My 1st time was romantic, sweet and just NORMAL nothing to write home about except that Momma Sixx found out the next day — a friend of hers caught us leaving the telly, took a pic and everything, mind you said friend was a sista in the church and married to a deacon o__o.

  9. my first time.

    october, 2001. a woman who was one of my close friends. i had a crush on her the minute ii met her. she had a boyfriend so she curbed any advances i made toward her. 2 years later she broke up with her boyfriend and all of a sudden she was being extra nice to me.

    i will say that even today i have a hard time determining when a woman likes me. so me being a naïve virgin back then i was completely oblivious.

    one night after a sigma probate we were chatting and she asked if i could come back to my room. even though it was after 2 in the morning i still had no idea what was about to go down. all of a sudden i’m naked in a bed with this woman.

    my first time was cool. lasted longer than i thought it was going to last (15 minutes). the next day we had sex again and we went 3 rounds. lol she introduced me to almost every kinky, perverted thing i love to do today. needless to say she became my first girlfriend and we were together for 2 years.

  10. Cheekie says:

    LAWD, that was hot. Looking forward to telling mine, which I may have to do as a guest post at Max’s spot. LOL

    1. O_D says:

      I second that, without the guest post of course lol. Def can’t wait for that one cheekie!

      Really enjoyed it max, great write up and really solid comments also, lovely post.

  11. BP says:

    I loved your first time story. Mine was not that memorable…but yours? WHOA! I even *blushed* at “a third arm”….

  12. LaLaBakir says:

    Welp, looks like I’ll bring some wack juice to this party.

    I was 17 years old. The boyfriend and I were messing around as usual. It was summer time, school was out and everybody in our “crew” would pretty much take turns having company at their house before going to the Boys and Girls Club.

    Anywho, D and I were doing our usual which mostly consisted of him giving me oral and some fingering. Today, was different as he attempted to get it in. Literally. I’m chilling, watchin Married With Children while he’s doing his thing. I figured I would know when he got it in.

    Things wrap up, and we go about our day. Later that evening he calls me and is like “Did you write it in your diary?” and I’m like “Write what?” D: “That you lost your virginity.” Me: o_O oh, ummm…yeah.

    Clearly I lied as I didn’t have sh*t to write down. I don’t think he “took” my virginity. He wasn’t big in that department by any means, but I think I’d feel something penetrating my body. Needless to say I didn’t try again (or have sex again if he really did take it) until 2 years later.

    This story just depressed the sh*t out of me,lol

    1. GirlSixx is ChloeRayne516 says:

      “Did you write it in your diary?” and I’m like “Write what?” D: “That you lost your virginity.” Me: o_O oh, ummm…yeah.

      Okay. I’m Done!!!!!


      That’s horrible Ms. Bakir

    2. BGirl says:

      Im sorry to laugh at this horrible tragedy, but this was hilarious. Didn’t interrupt your show though so its not too bad. lmao

  13. Starita34 says:

    YAY!! We finally hear the virginity story!! He was incredibly sweet with it.

    So, you said that you didn’t know it was going down until it did. Had you already decided that you’d go with your older sister’s advice or was it a lucky accident? I don’t wanna agree with that advice, but it’s so true…and I inadvertently followed it as well. And much like your guy that turned you out, I was still unable to escape being “branded” by the one that I shared intimacy with that I loved, first or not.

    Also, WHY does the “whip it out” continue to be so effective!??! LOL Proof that we want it just as bad…we’ve got all sorts of excuses and rationale’s and “we should waits” until we see it, lol

    Thanks for sharing! All ya’ll that shared! I love hearing about first times for some reason…

  14. Mrs.Brightside says:

    I always wished my first time was more exciting. I was 15 and it was the summer. Back in those days I was a pimp/ playa. I had all the guys checking for me and only wanted one asshole that out of spite I slept with his best friend. Sad but true.
    One of our mutual friends had keys to his mom’s house that no longer had power. We decided it would be fun to play hide and go(get it) seek in the dark house with our crew of 8-12 people. Me and the best friend decided to hide in the bathroom and started kissing and touching. He fingered me and then pulled out his dick and a condom. I was like well hell why not. This was a small bathroom so he sat on the toilet and I got on top and did what I thought I was supposed to do. At some point someone came and knocked on the door and then the whole crew was outside the door. Being the G that I am/was I kept going with all the taunting and banging outside the door until he came. By then only my ex and the guy whose house it was were left. They walked me home and that was the end of my night. It was nothing like I imagined. 2 guys later I met the man who should have been my first and will possibly be my last minus the swinging we will likely do.

  15. Sam Sharpe says:

    I almost spilled gin and tonic all over my laptop. Twice. Thanks for sharing the story. And the comments were just as good…..

    Oh and I’m all for sharing. But you won’t have me talking about my first time….

    1. BGirl says:

      aw come on!

  16. candice says:

    Yeah, malik was most certainly one of the greatest lovers I’ve ever had. I still love him

  17. Max, that’s a great way to lose your virginity. Good story.

    When I was a teenager, I imagined losing my virginity in a similar fashion to Tupac. See, the plan was for me to attend a Tupac concert, get backstage, smoke a little, drink a little, and let it go from there. Thug passion all night long, somebody rockin’ knockin’ the boots. lol.

    Needless to say, my first time, several years later, wasn’t nearly as exciting. But it was sufficient. lol.

  18. emti says:

    me: is it in?
    him: yes
    me: oh so we’re doing it now?
    him: yes


    1. Keisha says:


  19. bumblebee_c says:

    Aww that story had a great ending…well in hindsight that is. I have pictures from the night of my entrance to (whoredom) womanhood. They are g rated. It was pretty fancy, I was lucky. But great post!!!

  20. keisha brown says:

    funny that Doc could call the next day, but some random dude who works for CIBC can’t because of some wack-a$$ theory that it makes em look weak.
    WACK!! lol.
    i like Doc, but even more because of this story! 😉

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