Dear Bossip: I’m A Divorcee Ready To Date & I Want To Explore My Freaky Side!

- By Bossip Staff Categories: Love and Relationships, News, Sex and Relationships

Dear Bossip,

I am a 36-year old divorced female, who enjoys sex very, very much.

But, I haven’t been active for a year and a half. I am at the point where I want my inner freak to come out! I enjoy sexual pain. It’s a turn on!!!!

My question is about anal intercourse. I tried it with a vibrator and I was petrified at what was on the other end when I pulled it out. Now I’m scared that once insertion with a penis takes place, with whomever I decide to get my freak on with, will this happen again? Would I need to do a cleaning, laxative, colon cleanse, or what?

How do you get around a boo-boo mess and is there a clean way for a freaky night? – Mizz Ready To Get My Freak On

Dear Mizz Ready To Get My Freak On,

Girl, girl, girl, girl, girl! Let me find out you are ready for some anal pain. And judging from some of the previous posts on this subject matter that I’ve answered, there are lots of men who wouldn’t mind pumping you.

I am glad you feel sexually liberated and ready to explore your freakish nature. Like Missy Elliott sang, “Get your freak on, get your freak on.”

You asked about the, uhm, unsightly discharge on the end of your vibrator as you attempted to pleasure yourself. Well, first and foremost before you do any anal intercourse, and since you are a single woman navigating the single scene please protect yourself and use a condom. Especially in anal pleasure, because if your mate is a “Rude Boy,” or he’s packing some serious meat, he will do some serious damage and do some tearing and ripping of your anal walls causing bleeding. That is not healthy or safe. GIRL, PLEASE USE A CONDOM and make sure to you use lubricants such as Wet, Astroglide, K-Y, or Eros. Do not use Vaseline, cooking oil, spit, or your own natural juices. You’re clutching your pearls, right? But, yeah, honey, you’ll be surprised at what some people improvise and use.

You are doing the right thing in preparing yourself with your special toy. You will need to get used to the penetration and insertion into your anal area. It’s something you can’t just jump into because, naturally, when you’re having anal intercourse your muscles will want to extract and push his penis out. This happens because the anus is technically a waste eliminator. Its purpose is to extract and push, and not receive. So, it will take lots of practice and lots of time for you to get comfortable in receiving. When you’re pleasuring yourself with your toy, practice taking deep breaths, relax your body, and insert a little at time. This is the exact same practice you will need when a man inserts himself inside you. Don’t let him thrust himself inside you. You guide him, taking little of him at a time, maintain your breathing, and relax. Take deep breaths as he inserts more of himself, and relax your muscles. You have to be in control and let your partner know if you are feeling pain. If you feel extreme pain and you don’t feel comfortable, let him know he needs to stop. You may need to change positions and gather yourself. Some of these positions may be on your back, or on your stomach, or doggy style. You will find the position you feel most comfortable and the least amount of pain.

Now, on to the answer of how to be prepare for anal intercourse. Honey, you don’t want to be a Picasso and paint all over your partner’s penis. On the streets and in the gay community it’s called a Picasso. You know, like the painter, thus the reference I used. Nor do you want to give him a sh****y deal. To avoid any of that happening here are a few things you need to do to get ready.

1.) Don’t eat a few hours before anal intercourse because you will find yourself having a bowel movement as he’s pumping in and out of you and it will not be cute. That means don’t go out to dinner, or have a big meal, and then when you get home you want to toot your behind in the air. Uhm, no sweetie, that night you will have to pass on the anal.

2.) I highly recommend an enema prior to intercourse. You can get a Fleet enema from your local pharmacy. The directions are on the box and it shows you how to use it. You can use an enema up to an hour prior to intercourse. It is a waste eliminator and flushes you. I don’t recommend a laxative because they give you the runs for the day. If you do a laxative, then do it two-to three days before you know you’re going to have anal intercourse. If you take a laxative on the day of, you will find yourself splattering all over him, and messing up your good sheets. That, Ms. Girl, is nasty!

3.) I also recommend thoroughly washing and cleaning your anus. Take a long bath, soak in some of your scented bath oils, and clean yourself before intercourse. There is nothing like an un-ghastly odor emanating from you when a man is ready to slay you. He will decline to enter you and retreat with a limp penis and his fingers pinching his nose.

So, Mizz Ready To Get My Freak On, prepare, prepare, prepare. You’re going to need to be ready for the man that YOU decide to let slay you anally. So, take it slow, don’t rush and try to take all his man meat at once. You will hurt yourself! And, please, USE A CONDOM and appropriate lubricants.

And, like the lyrics in Rhianna’s song, “Rude Boy” – Tonight I’ma let you be the captain, Tonight I’ma let you do your thing, yeah; Tonight I’ma let you be a rider, Giddy-up, giddy-up, giddy-up babe – Terrance Dean

Hey Bossip Fam, what do you think? Share your opinions and thoughts below!

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Make sure to order my books Mogul: A Novel (Atria Books – June 2011; $15), and Straight From Your Gay Best Friend – The Straight Up Truth About Relationships, Love, And Having A Fabulous Life (Agate/Bolden Books – November 2010; $15). They are available in bookstores everywhere, and on Amazon, click HERE!



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