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3 reasons men are choosing the transgender side chick








By
Mo Barnes




Aug 02, 2017



8:20 am



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Men going to transgender escorts is nothing new and in countries like Brazil, it is common practice. The recent scandal involving R&B singer Bobby V has drawn attention to men who choose to have sex with transgenders. Bobby V has stated that he did not know escort Reima Houston was a man and ran from the apartment when he realized this was the case. Some are disputing Bobby V’s claim that he did not know the person he was with was transgender. The debate as to what actually happened continues. Still, the incident has presented a topic of discussion many avoid. It appears that many men are choosing to have a transgender side chick. Whether for exploration or living a taboo alternative lifestyle, there are a variety of reasons men are choosing this option.
1. Looks. According to porn star TS Madison during an interview with rolling out, looks do play a part. She stated, “I do not consider any heterosexual man that has an attraction to a transgender woman a homosexual. A transgender personifies a genetic woman, some say we over-exaggerate a woman because we go to the extreme of larger breasts, hips, and buttocks but at the end of the day we still look like women. We are the ones who put in the time to look like a woman. So, when a man is attracted to a transgender woman, he does not say, ‘Oh my God look at the good-looking guy.’ He’s looking and saying this is a beautiful woman. When you tell him you have male genitalia, it makes people label you gay. There are some men who will go through their relationship with transgender women and have nothing to do with the penis. But yet they want it to be there because it is taboo.”
2. Taboo sex: Some male customers enjoy the aspect of power and sexual domination that they may not receive from a female lover. In 2015, pro boxer Yusaf Mack , came out as gay and announced that he was looking forward to having a transgender relationship and exploring his sexual identity.
3. Pleasure : For some men , anal penetration is pleasurable and stimulates the prostate, known as the male G-spot. Last year, Amber Rose sent out a tweet about former lover Kanye West that read:
Even among heterosexual partners, some couples engage in what is known as “pegging“ where the man is anally penetrated by his female partner with a strap-on dildo or other sex toy. The whole purpose of this is to reach the male equivalent of the “G-spot” and has nothing to do with being homosexual. There are some men who are frustrated that they can not engage in this practice with their female partner and choose a transgender escort. Being able to engage in this behavior without emotional attachment through prostitution is an outlet for some men.
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3 reasons men are choosing the transgender side chick








By
Mo Barnes




Aug 02, 2017



8:20 am



Copyright 2022 © Rolling Out. All rights Reserved.
This website uses cookies to improve your experience while you navigate through the website. Out of these, the cookies that are categorized as necessary are stored on your browser as they are essential for the working of basic functionalities of the ...

Functional cookies help to perform certain functionalities like sharing the content of the website on social media platforms, collect feedbacks, and other third-party features.


Performance cookies are used to understand and analyze the key performance indexes of the website which helps in delivering a better user experience for the visitors.


Analytical cookies are used to understand how visitors interact with the website. These cookies help provide information on metrics the number of visitors, bounce rate, traffic source, etc.


Advertisement cookies are used to provide visitors with relevant ads and marketing campaigns. These cookies track visitors across websites and collect information to provide customized ads.


Other uncategorized cookies are those that are being analyzed and have not been classified into a category as yet.


Change Location
Find awesome listings near you!

Men going to transgender escorts is nothing new and in countries like Brazil, it is common practice. The recent scandal involving R&B singer Bobby V has drawn attention to men who choose to have sex with transgenders. Bobby V has stated that he did not know escort Reima Houston was a man and ran from the apartment when he realized this was the case. Some are disputing Bobby V’s claim that he did not know the person he was with was transgender. The debate as to what actually happened continues. Still, the incident has presented a topic of discussion many avoid. It appears that many men are choosing to have a transgender side chick. Whether for exploration or living a taboo alternative lifestyle, there are a variety of reasons men are choosing this option.
1. Looks. According to porn star TS Madison during an interview with rolling out, looks do play a part. She stated, “I do not consider any heterosexual man that has an attraction to a transgender woman a homosexual. A transgender personifies a genetic woman, some say we over-exaggerate a woman because we go to the extreme of larger breasts, hips, and buttocks but at the end of the day we still look like women. We are the ones who put in the time to look like a woman. So, when a man is attracted to a transgender woman, he does not say, ‘Oh my God look at the good-looking guy.’ He’s looking and saying this is a beautiful woman. When you tell him you have male genitalia, it makes people label you gay. There are some men who will go through their relationship with transgender women and have nothing to do with the penis. But yet they want it to be there because it is taboo.”
2. Taboo sex: Some male customers enjoy the aspect of power and sexual domination that they may not receive from a female lover. In 2015, pro boxer Yusaf Mack , came out as gay and announced that he was looking forward to having a transgender relationship and exploring his sexual identity.
3. Pleasure : For some men , anal penetration is pleasurable and stimulates the prostate, known as the male G-spot. Last year, Amber Rose sent out a tweet about former lover Kanye West that read:
Even among heterosexual partners, some couples engage in what is known as “pegging“ where the man is anally penetrated by his female partner with a strap-on dildo or other sex toy. The whole purpose of this is to reach the male equivalent of the “G-spot” and has nothing to do with being homosexual. There are some men who are frustrated that they can not engage in this practice with their female partner and choose a transgender escort. Being able to engage in this behavior without emotional attachment through prostitution is an outlet for some men.
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Also: What do you call a committed three-way relationship?



by
jmartinache
January 11th, 2013 May 14th, 2021
"I live in D.C. and want local news."
"Y'all are doing real local D.C. journalism."
" Washington City Paper has made me feel like I am part of the D.C. community."

I’m a straight male, 21 years old. I love women, I’ve always loved women, I’ve always loved having sex with women. However, in the last year, here and there, I’ve jerked off to transsexual porn. One night, after drinking with a friend and smoking some hash, I arranged a date with a trans sex worker. She was totally womanly, nothing manly about her, except for, you know. She licked my butt, gave me head, and fingered me. I’ve been on the receiving end of anal play before from girls, so nothing new. But somewhere during this encounter, I became the receiving partner during anal sex. At the time, I was too fucked up to care. But the next day, I started to feel REALLY bad. She was very safe and used condoms for everything. I just can’t get past the fact that I did the gayest thing a guy can do. I feel really depressed about this traumatic situation. I can’t seem to enjoy my life anymore. I’ve even felt somewhat suicidal. (I would never kill myself—I wouldn’t do that to my family and friends.) I still want to date women and have sex with women. I don’t regret being with a trans woman because I wanted to experiment. I’ve been tested since the encounter to make sure I didn’t catch anything. What I regret is her sticking her thing in my butt. Can a single act like this make me gay? Please help. —Wrong Side Of Wild Side


Yes, yes: You did the gayest thing a guy can do—you allowed someone to put a dick in your manbutt—but now you’re doing the second-gayest thing a guy can do. You’re being a huge drama queen about the whole thing. Stop acting so cray, as the kids say, and repeat after me: One dick in the ass does not a gay man make. Look at it this way: The difference between having a woman’s finger in your ass and having a woman’s dick in your ass is a matter of degree. If the woman’s finger was fine—to say nothing of the woman’s tongue—why freak out about the woman’s dick? Remember: You don’t sleep with men, you’re not attracted to men. You made an exception for this woman’s dick because her dick is exceptional: It’s attached to a woman.


So maybe you took a longer walk on the wild side than you might have if you’d gone on that walk sober, WSOWS, but thankfully, your sex worker was conscientious and responsible and used condoms. So you didn’t emerge from this encounter with anything more devastating than a touch of gay panic. Be a man about this—be a straight man about this—and walk it off, as the football coaches say.


Maybe this will help: Like a lot of gay men, I had sex with a woman before I came out. I did the straightest thing a guy can do—I put my dick in a vag—and it didn’t make me straight. You did the gayest thing a guy can do—you let someone put a dick in your ass—but that didn’t make you gay. Because you’re not gay, WSOWS, and one ride on a trans escort’s dick can’t change that.


If nothing I’ve said has made you feel better, WSOWS, maybe this will: Gay men don’t hire trans women sex workers. Wanting to be with a woman who has a dick is an almost exclusively straight male kink/obsession/wild side. Gay men are into dick, of course, but what we’re really into is dudes. There are gay men out there who date and fuck and shack up with trans men—men with pussies—so not all gay men are after dick. What we’re all after is dude.


If our gayness can’t be defined solely by dick, WSOWS, then surely your straightness can’t be undone entirely by dick.


I’m a married straight man. I recently spent a lovely day snorkeling with my wife in Mexico. We were grouped with three men who were obviously in a committed three-person relationship. I lacked the cojones to ask directly, but they had an extensive travel history together and lived together, everything was “we” this or that, and there were various PDA pairings during the day. They were lovely people. I wish we all lived in the same city, as it’s hard to meet cool people who aren’t exactly like you when you’re married with kids. Several questions: (1) What do gay people call such a union? (2) Does the gay community think it’s odd? Unremarkable? Sensible? (3) How does a union like that form? A couple adds a third? (4) Do these relationships last? Lots of pros and cons, just curious how it plays out.


—Three-way Relationship Intrigues Oblivious Straights


I recently used the term “saddlebacking” to indicate the position where a man rubs his penis between his partner’s ass cheeks as either foreplay or nonintercourse sex. My girlfriend, a regular reader of your column, insists that I used the term incorrectly. Did I? —Rubbed The Wrong Way


You did, RTWW. “Saddlebacking,” as defined by Savage Love readers (the Académie Française of sexual neologisms), is when two straight teenagers, endeavoring to preserve an evangelical girl’s virginity, engage in anal intercourse. This is a thing that really happens. Since anal sex isn’t really sex, according to the abstinence educators evangelical teens are exposed to, many good Christian teenagers rationalize that getting fucked in the ass doesn’t really count against a girl’s virginity.


The act to which you refer—rubbing your penis between someone’s ass cheeks as foreplay or as a substitute for intercourse—is known variously as frottage, outercourse, the Princeton Rub, or “the pearl tramp stamp.” But in Chicago, it’s known as “the Cardinal George.”


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