Roliing in the Deep: My Adventures in Anal Sex

Published under The Comedy Series.

Last Saturday night I finally hooked up with this girl that I had been after for the past nine months. Just when I was beginning to doubt if we’d ever get together; as luck would have it– and after weeks of back and forth messages on Facebook, she finally agreed to meet me out for drinks. It was my lucky day (and so I thought).

After several rounds of vodka gimlets we were both well on our way to being smashed. So naturally I ordered a few more rounds for good measure. Although things in my opinion were going pretty well, my first clue that something was off should’ve been all of the “casual” prison references she kept dropping all throughout the night. At one point she even commented that her favorite TV series of all time was OZ because of all the love scenes. Now although in my mind I was thinking, “Okay…I don’t particularly remember that program being known for its touching love scenarios.” I figured “Hell…maybe I just missed an episode or two.”

Now fast forward to a couple hours later and the two of us getting hot and heavy on my new Ikea sofa. It’s amazing what $60 bucks and a good relationship with your local bartender can get you these days. Finally she muttered those words every guy longs to hear in that situation, “We’d probably be more comfortable in your room.” I’ll tell you; those damn vampires from True Blood could not have zipped to my bed any faster.

Twenty minutes later in the midst of making out, to my surprise she asked “Hey…how do you feel about anal sex?” I thought “Huh?” Talk about being thrown for a loop. So of course not wanting to sound like a square, I replied “I guess I’m okay with it.” With a huge smile she replied “Great!”, and then before I knew it she had reached into her purse and whipped out the biggest rubber dildo I’d ever seen. Now in my mind I’m thinking “Although I certainly appreciate a woman coming prepared just like the next guy. I kind of already have a built in version that I’m particularly partial to.” So her pulling out hers was kind of like bringing your own ground beef to McDonalds. And that was when it sunk in; “Holy shit Brett! She obviously wants some double insertion action.” Although I’d seen it done countless times in some of my midget porn movies; never in my wildest dreams did I think I’d ever find a girl freaky enough to give it a go. I was so ecstatic it took everything I had not to immediately grab my phone and check in on Facebook: “Hey guys– guess what I’m about to do?”

As we tore through our clothes still in the heat of passion, she whispered “Papi…you have any lube?” Remembering that one really old bottle somewhere in the back of my closet that came along with that DVD I bought titled Backdoor Midgets 64; I quickly scrambled through the dark until I spotted the long blue tube near my shoe box. I snagged it up, and we were ready to go. But just as I was preparing to grease up; to my astonishment she began strapping on the dildo and then exclaimed “Okay, now I’m going to try my best to be gentle on you in the beginning.” I literally heard a record scratch, as I did my Scooby Doo double take “On me?! WTF?” I replied, “Wait…you were talking about doing me?” And with a slight attitude she commented, “Well…turnabout is fair play. So…if you want to hit it from the front, you’re gonna have to let me get it from the back.”

I couldn’t believe my ears. “What kind of a f*cked up ultimatum was that?!”  I felt like I had just been masterfully set up, and I had the right mind to ask for my damn $60 back. I was beyond perplexed. My dream date had somehow just turned into a horrible episode of Deal or No Deal. I thought “okay, at this point do I just walk away with all my earnings? Or instead do I stay and go for it all?” And as horny as I was from all of the night’s foreplay, she knew she had me exactly where she wanted me. My natural instinct was to call the whole thing off. But then I looked down at my penis looking all excited, like a little retarded kid on Christmas morning, and suddenly I just didn’t have the heart to disappoint him. Yep; he had been a great friend to me over the years, and I reckoned if ever I had to “take one for the team”, it would damn sure be for him. So…I did what any man would do in that situation. I replied “Okay, but only two pumps.” I then turned over and gripped the bed posts, as I took a deep breath and prayed “Jesus please be with me?”

Next it was the craziest thing. She tried and tried, but for some reason she just wasn’t able to past go. I remember her saying several times, “This sure is some dry ass lube. Do you have anything else?” But I just figured with it being years old and all, who knows…perhaps it had just went bad? I suggested that maybe she just needed to try doubling up on the recipe. However as much lube as she would spray on, nothing seemed to work. Apparently my ass had a mind of its own that night. After several attempts she finally decided to give up, which I was more than okay with.

Early that next morning I got up to go take my morning leak. As I walked back into my room, suddenly I noticed there in the window seal above my bed, a big ass blue can of Lamisil Foot Spray. Still hung over, I thought “Huh…that’s strange? Had that can been there the entire night?” I suddenly shrieked with embarrassment thinking “Dammit Brett! What a stupid place to leave your damn foot fungus spray– especially with date. Now there’s no telling what she must be thinking now? And that was when it hit me. I thought “Oh no!” and immediately ran to the closet. I could not believe my eyes. There next to the shoe box sat a long blue bottle of lube. I was mortified. In all the darkness I must’ve accidentally grabbed my foot fungus spray. It suddenly made all the sense in the world. Specially all her remarks about how dry the lube was. It was that exact moment that I realized that God must’ve obviously heard my prayer. I then of course spent the next three hours trying to scrub Lamisil out my ass. We’ve all heard of the condition Hoof in Mouth; but leave it to me to become the first person on the planet to ever contract Foot in Ass disease.

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Tue, 09 Aug
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35 Comments to Roliing in the Deep: My Adventures in Anal Sex

  1. Tasha Smith,

    Hahahahaha!!!!!!!! Boy you seriously have my mascara running!! Thank you for your sick and twisted life.

  2. June,

    Okay, I heard a coworker literally crying at her desk so I had to check it out for myself. I spit coffee out all over my monitor and my new trousers. You are hilarious!!!

  3. Beverly Wilson,

    Lol!!!!!! You poor guy. I am in tears now. Tears I say!!!! I can not wait to see the series!! You are my new Curb Your Emthusiasm! You are actually a Black Lary David. (but much cuter I might add)

  4. admin,

    Tasha: Thanks so much for your continued support!
    June: PLease don’t get fired on my account. I have enough pending law suits. LOL
    Beverly: Thanks for taking time out to check me out.

  5. Meg Scott,

    Okay, so my dad a retired judge who only calls me in at work for emergencies just called my office and said “there’s a new Brett and the City up. You may want to check it out”. Lmao!!!!!!! You are now the topic of many family discussions and we don’t even know you.

    Keep up the great work and were all waiting for the series.

  6. admin,

    LOL!!! Thanks so much Meg. And please save me a side of bbq at the next family function. :-)

  7. Sab,

    You’re a mess! I can’t take it. I am in tears. I see the golden rule actually applied here, do unto others as you would have them do unto you. Hilarious, “two pumps” is that so..just freaking creative!

  8. admin,

    SAB: LOL!!! Yes, the golden rule most certainly applied. But thank god he was on MY side. LOL Thanks for the continued support.

  9. Dave M.,

    All I have to say is Brilliant! And man where on earth are you meeting all of these girls? Between the Down Syndrome lady, the religious freak, and the girl with the handicapped boyfriend, man you’ve had some bad luck.

    Great work!!!

  10. admin,

    Dave: Thanks man for keeping up so closely with all of my dating catastrophes! LOL

  11. Rita,

    Boy I’m gone hurt you! Bahahaaaa! Your poor mama what she must go through. A mess!!!!!

  12. Jason Buckley,

    I have never laughed so hard in my life before my morning coffee. Thanks for the much needed kick start. My favorite line “ok but just 2 pumps”. Lol! I hope this wil be an episode in your web series.

  13. admin,

    Rita: Yes, but I’m afraid she’s used to it by now. Theere’s actually 2 of us.
    Jason: Thanks man, and we will certainly try to add this to the first season.

  14. janice jackson,

    OMG!!!!Tooo Funny

  15. Kat,

    1 question….since she didn’t get it….did U still “get it”? LOL This was
    hilarious. I’m glad U mixed up those cans…

  16. Shawn Osband,

    Is Backdoor Midgets 64 better than 63? I thought the series was starting to lose its luster. Can’t wait to see the show, although I don’t look forward to a graphic version of this episode. Funny stuff as always

  17. admin,

    J. Jackson: Thanks babes. And you are the sunshine of my life. :-)
    Kat: LOL!! You better believe I did. Specially after what I had to endure. LOL Thanks!
    Shawn: What’s up dude?? And to answer your question 64 was wayyyy better.. due to the all the new arial shots! LOL Thanks man!!

  18. Mia,

    Brett,

    You have a seriously twisted sense of humor and I guess I do as well. This story is friggin hilarious! My favorite line is “This sure is some dry ass lube” lol

  19. admin,

    Mia: Thanks soooooooo much. Yes, I think that’s my favorite line too. Specially since it was repeated several times. :-)

  20. Nixxom,

    Young man I have followed your career for a while now, and I must say your are a brilliantly gifted comedic writer. I grew up with the likes of Richard Pryor and Dick Gregory and your work takes me right back.

    Please keep entertaining us with your gift. Something tells me the whole world will know your name some day. I eagerly await this web series you’ve been mentioning. I can hardly wait to see if you are equally as gifted in front of the camera. Something tells me you won’t let me down.

  21. Sabir,

    Brett, I have to work at not reading your page while in the office. Too many outbursts. Keep it going partner. I love it.

  22. SheSan,

    Brett, After seeing the title, I had to go and get a cup of tea and make myself comfortable in preparation for being shocked… my mind was way down in the gutter. Well, having finished reading the article over 5 minutes ago, I am still laughing. You have an extremely warped sense of humour but I guess we love it! (ES)

  23. admin,

    Sabir; Hey man!!! Yes, I have been banned from certain offices for that exact reason. Had a HR director write in and say she felt bad because she put her employees on to my site.. then had to ban them from reading it at work because of all of the laughing.
    SheSan: Thank you so much. Love the pre Brett and the City preparation ritual of calming tea. LOL!!!!!! Thanks again.

  24. Mel,

    See, I kind of believe in turnaround too…but “if you want to hit it from the front you have to let me hit it from the back?!” That’s ridiculous. My idea of reciprocity is “if you’re gonna hit it from the back, you gotta let me hit it from the back first, so you can give me an idea of how much it’s gonna hurt!”

    Thank GOD you grabbed the Lamisil! Too funny, you’ve got me snorting over here.

  25. admin,

    Mel: LMAO!!!!!!!!!!!!!!!!!!! Now that was funny. Thanks for the love! And good luck with the snorting thing.

  26. Mel,

    Brett, I just noticed that you are from Grand Rapids…and that you consider Grand Rapids a small town. Love the west side! I’m originally from southeast Michigan….great to find a fellow Michigander (or Michigoose, as I prefer to call myself!) out in the blogosphere

  27. Gayle,

    The GOOD news–you won’t fungus in your ass.

  28. admin,

    Mel: Yessireebob!! Howdy my fellow Michigander.

  29. admin,

    Gayle: Thanks now can I hold you to that. Because if I do you are the first one I’m looking for. LOL

  30. DOC,

    LOVE IT LOVE IT MAN!! LOL Good to see you still have good comedy rolling in hahaha keep it up Brett!

  31. admin,

    Thanks Doc! :-) I appreciate all the support.

  32. Biany,

    Hilarious!! Thank you for sharing this story.

  33. admin,

    Thanks Biany. Glad you were able to get a good laugh :-)

  34. LaTonya,

    Oh Dear Sweet Baby Jesus! I have never seen your blog before today but I promise another day will not pass in my life that will not have at least 10 minutes devoted to your blog!

    This is some of the funniest stuff I’ve read in a long time! Thank you so much for making me laugh up a lung!

  35. admin,

    Thank you so much LaTonya!! It’s an honor to have you visit the site!

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