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Dear Bossip,

Love the advice. I typically don’t usually have a good enough reason to email any problems to you, but I felt this was worth it!

So, long story short, I live with my boyfriend of almost two years. This man is my best friend, and we click extremely well. Hell, we’re at the point where we basically read each other’s minds!  But, there is one small problem: sex.

Our sex is pretty good. As this is my first non-black boyfriend I was initially skeptical, but obviously I liked the milk because the cow gets three meals a day and sleeps next to me! Now it’s good, not phenomenal. It’s the foreplay that is lacking.

Now, me and my boyfriend are both a little bi-sexual. We’ve had our experiences and we are actually open (Polysexual). Obviously I don’t have a problem with his bisexuality and vice-versa. But, when it comes time for foreplay that’s when I have an issue! He wants me to stick a finger in his ass.

Now, I know in this day and age that’s not unusual, even for a straight man. Intellectually, I know that it’s pleasurable for him, and that it’s not that damn hard. I know he pleases me and I want to do the same for him…But, I can’t do it!!!!!!

Somehow I can’t even get the nerve to do anything past slapping his ass! He could ask me to do anything else – Choke him, dominate him, role play, etc. But, the only thing he does ask for is ass play!

In the beginning I actually told him it wouldn’t be a big deal if he found a friend for anal play. Like I said, we are open. But, he doesn’t, and says it’s something he wants to share in our sex life. I agree. I just can’t get myself to do it!

So, basically that’s my problem. It’s such a problem now that I prefer to skip foreplay and just have sex! But, I don’t want to deprive him of something he enjoys. I love this man!  We’re probably going to get married down the road and I’m terrified our wedding night is going to be some sort of, “Dawn of the Ass.” Is there anything I can do to make myself more comfortable?

(At this point I should mention my job. I’m a wax specialist. LOL. I perform at least 5 Brazilians a day. I still do not like ass-holes. Actually, my job might make it worse. I’m not sure.

Hoping for advice and not shade (LOL). – Ms. No-Country-For-Old-Men’s-Asses

Dear Ms. No-Country-For-Old-Men’s-Asses,

How are you a wax specialist but don’t like ass-holes? Why commit to a job that you don’t like? And, now your work life has become a part of your bedroom, and unfortunately, it’s interfering in your sex life.

Well, I recommend that you be honest and upfront and tell your boyfriend your issue. You are not interested in sticking your fingers in his ass. It doesn’t turn you on, and you don’t find it intriguing or fascinating. However, I’m perplexed that you wouldn’t have had this conversation upfront in the beginning of your relationship. Why get involved with someone and you know that you can’t and you won’t help satisfy or bring them pleasure in the bedroom? Why not have this conversation from the beginning if you had an issue with it?

Yes, I understand that you and he are Polysexual, and you told him that if he wanted anal play then he could find someone else to pleasure him. But, he doesn’t want to do it with anyone else. He wants you to do it. He wants you to satisfy him and stick your finger inside him.

So, you have two options: 1.) Get yourself a finger cot and get over your anxiety. Find ways to make it pleasurable for you and he. And, make it fun and exciting. Do some role play, or make it a game. Get some flavored gels and make it memorable for him. Also, see if a sex toy would be pleasurable for him. Maybe instead of your finger you can improvise with a toy. Perhaps that will give him the same pleasure, and give him the satisfaction he needs.

2.)  Get out of the relationship. Yes, I know everything else is great, and you see yourself marrying him. But, if your sex life is not pleasurable and enjoyable, then either you or he, or both will cheat. You can’t even think about marriage until you resolve your bedroom life. Regardless if you are both Polysexual, and you enjoy sex with others. However, it will get to a point where your sex life will end because you are unwilling to give him pleasure, and he will feel rejected.

By the way, I don’t understand your statement, “me and my boyfriend are both a little bi-sexual.” What the hell is a ‘little bi-sexual’? That is the most asinine thing I have ever heard. Either you are or you’re not. There is no ‘little’ about it. That’s like someone saying, “I’m a little gay.” Huh? Or, “I’m a little lesbian.” That doesn’t even make any damn sense.

So, are you sure that you and he are bi-sexual? Are you sure that you and he are polysexual? Or, are you using these terms because they are the new hip and hot terms to toss around. You’re trying to say that you don’t feel inhibited by your sexual orientation or identity, and you can have sex with whomever you please. If that’s the case, then say that!

Now, talk with your boyfriend, and be clear with what you won’t do, and what you’re willing to do in the bedroom. Explain to him why you’re not comfortable doing it, and how it makes you feel. Give him the opportunity to say to you if it is a big deal, and if it is something that is a deal breaker for your relationship. If he feels it won’t work, and he really needs it, then you will have your answer. If he says he can work around it, and improvise with a toy, then good luck to you both. Whatever you decide, you have to be honest and upfront with your communication before you get married, or this marriage is doomed. – Terrance Dean

Photo source: Shuttershock

Hey Bossip Fam, what do you think? Share your opinions and thoughts below! Also, e-mail all your questions Terrance Dean:  loveandrelationships@bossip.com  Follow Terrance Dean on Twitter:  @terrancedean and “LIKE” Terrance Dean on Facebook, click HERE!

Make sure to order my books Mogul: A Novel (Atria Books – June 2011; $15); Hiding In Hip Hop (Atria Books – June 2008); 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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