Tag Archives: cross-dressers

Dear Bossip , I love reading your responds to everyone relationship problems. Here is my problem: I have been married twice and have two grown daughters. I am currently divorced, and I have been dating my girlfriend for 2 years now. My problem is that I enjoy sleeping with Transsexuals and Cross-dressers from time to time. I am not attracted to regular guys, only the ones with breasts and who look like a female. I also enjoy being on the bottom sometimes. I guess you can say I had one that turned me out and showed me that I can enjoy being on the bottom because normally I would never do that. So, my question is am I gay or what? I don’t like regular guys. I think that it’s gross to sleep with a regular guy. I love eating a woman out a lot. The feeling of p***y is 200 times better than the feeling of ass. So, I love women. But am I gay? – Questioning My Sexuality Dear Mr. Questioning My Sexuality , First, and foremost, lawdy, lawdy, lawdy I pray that you are being upfront and honest with your girlfriend about your desires. Have you communicated honestly with her that you enjoy bottoming, and engaging in sexual relations with Transsexuals and Cross-dressers? And, I hope you are using protection while engaging in these sexual acts. Wrap it up, and keep it safe. Don’t get caught out there letting someone run up in you raw! I don’t care who they are, what they may look like, and how sexually turned on you are by them. DO NOT ENGAGE IN UNSAFE SEX WITH ANYONE! Now, look here, sir, I know you better tell your girlfriend what you’re into, and don’t lie to her. Be upfront, and honest. She deserves to know the truth, and what your sexual desires are. She needs to protect herself, and more importantly, you can’t leave her in the dark and make decisions for her on what you think or how you feel she may respond. Let her be able to decide for herself if she wants to be with a man who is sleeping with other men. And, however, you try to justify it with all this bull-ish about how you are not into regular men and that you like men with breasts, or men who look like females. At the end of the day, they all have a d**k, and they are banging you out! So, to answer your question if you are gay. Well, my first inclination is to say, uhm, sir, YES YOU ARE GAY! You are engaging in sexual acts with men. Regardless if they are Transsexuals, Cross-dressers, or effeminate men who can pass as women, they are still men because they still have the equipment of a man. You are engaging in gay sex however you try to define it. But, let’s take a deep breath, and take a step back. I’ll introduce you to what may possibly describe you and your sexuality. There are three categories, and the first is called, “polysexual.” It is the attraction to multiple genders and/or sexes. A polysexual person is one “encompassing or characterized by many different kinds of sexuality.” People who refer to themselves as polysexual may be attracted to transgender people, third gender people, two-spirit people, genderqueer people, plus people who are intersex. The next is, “pansexual.” This is a sexual attraction, sexual desire, romantic love, or emotional attraction toward people of all gender identities and biological sexes. Self-identified pansexuals may consider pansexuality a sexual orientation and refer to themselves as gender-blind, asserting that gender and sex are insignificant or irrelevant in determining whether they will be sexually attracted to others. Finally, there is, “bisexuality.” This is a romantic attraction, sexual attraction or sexual behavior toward both males and females. The term is mainly used in the context of human attraction to denote romantic or sexual feelings toward both men and women. I strongly urge that you get into counseling, or seek out an LGBT center and speak with a specialist who work and deal with men such as yourself. There are many men like you who do not consider themselves gay because you don’t like or feel you have an attraction for “regular” men. You don’t engage in sexual acts with “regular” men, but will engage in sexual acts with men who appear as female, or have both sexual parts as men and women. However, one thing is for certain, and that is you have to come clean with yourself, and be honest with yourself of why you have this attraction. Be honest and tell yourself the truth of who you are. Yeah, it may be difficult to come to grips with your sexuality, but, chile, being honest will set you free! You won’t be dodging, hiding, and being deceptive with the women you are involved with. You have to be upfront. And, particularly, you need to be honest and truthful with your girlfriend, or any woman you are romantically involved with. Do not deceive or manipulate women into believing they are in monogamous relationships with a heterosexual man. You are not! And, sir, how the hell can you sit up here and say having sex with a “regular” man is gross, but you are letting a Transsexual and Cross-dresser bang you out? HUH? Really? Chile, some Transsexual has truly banged you good and made you hit your head on the damn headboard. And, I am not throwing shade to the Transsexuals and Cross-dressers, but, sir, you are a man still letting another man hit you doggy style. Another man is still bottoming you, regardless if he has breasts, or is dressed like a woman. You are still taking d**k! So, what’s gross about a “regular” man? Look, you need to answer some serious questions. Ask yourself how long this has been going on? What triggered this attraction to Transsexuals and Cross-dressers? Have you been suppressing your desires during both of your marriages, or were you engaging in these practices while you were married? Are you truly gay but afraid to allow yourself to be in a relationship with another man? You said you wouldn’t consider bottoming until you got turned out by a Transsexual. Why would you bottom for a Transsexual but not a regular gay man? Read the definitions of the three categories I provided. See where you fit in, and which one you feel bests describes you. Do your research. And, definitely get into counseling, and speak with a specialist who can help you assess your sexual attraction, desires, and needs. It’s time to start being real with yourself, your loved ones, and definitely your girlfriend. Don’t you dare continue deceiving her and manipulating her into believing she’s in a relationship with a heterosexual man. Stop the bull-ish today, and lay it on the table. – Terrance Dean 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 “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!             Continue reading →