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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.
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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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Real talk from straight and straight-ish guys.
And as a heads up, some of these stories get kinda graphic and NSFW.
"A guy once gave me his number out of the blue at a restaurant. A few weeks later I was bored and horny (and a little stoned) so I called him. He invited me over to his place to watch porn with him and his roommate. It wasn't long before we were all in bed having a threesome. I'm happily married to a woman now, but I'm glad I did that back then. It was fun and it felt good.
"You don't have to be gay to enjoy playing with a dick at some point!"
"I was in a weird place after a messy breakup with a long-term girlfriend when I was about 24. I don't really know how or why I started, but I began watching and getting off to gay porn. The thing is, outside of watching porn, I don't find men attractive at all. I have never checked out or noticed another man in a real-life situation, but I can completely fantasize about it if I'm watching gay porn.
"So after a few months of regularly getting off to gay porn I decided to seek out an opportunity to experiment and met with a guy in a parking lot of a local store. We went for a short drive and talked for a few minutes and I started backing out so he took me back to my car. We pulled up beside my car and he gave a last shot at keeping things going and asked if I just wanted to try holding his dick, and I agreed. He took it out and I started giving him a hand job, which lasted about a minute before I just went for it and started blowing him. I blew him for a few minutes in his car and then we decided I'd jump in my car and follow him back to his place just a few minutes away. We got to his house and I got back to sucking his dick on his couch, and he got my shorts off and rubbed my dick some while I blew him.
"After a few minutes he wanted to switch and go down on me, that's when everything sort of hit. He was really excited to blow me, but I wasn't the least bit hard and nothing he was doing was making it happen. I was just over it at this point — told him I was sorry but I needed to go, and bailed quickly. I felt bad ditching the guy. He seemed nice enough, but I had my moment of experimentation and realized it wasn't what I was into."
"I met a friend of a friend who was somehow into me. I was single and 23 at the time and selfishly thought, 'Welp, somebody thinks you're funny and attractive, you'd totally do Chris Hemsworth, why not give it a go?' He was a super great guy, we had a lot in common and enjoyed each other's company, and we unofficially dated for about a month or two.
"Fooling around with him was fun, but when it came down to actual *sex* sex (I'd top and he'd bottom), I wasn't as nearly attracted to it as I am with women. I distanced myself without officially breaking up, and I never heard from him again."
"I was at a typical high school party in sophomore year and my best friend Matt and I were egging on some girls to make out. They told us that we have to first if we want them to, so being close bros and all, we started to make out. More girls started looking and were actually getting quite turned on so we started getting more into it because we knew if we give it our all we'll get something better after. The reward afterwards was totally worth it!
"We're still the best of friends, and I'm still straight but he's bi (not sure if it's something he realized after this event and I don't want to ask). We just laugh it off as a good story now."
"My first hookup with a guy was a few years ago with a guy I met on Whisper. I'd been curious for a while before this happened. He identifies as gay. We drank some whiskey and one thing led to another and we ended up sucking each other's dicks and making out for a while."
"I considered myself totally hetero at the time. I was hanging out with my BFF since fourth grade, who's gay. We were probably both 19 or so. On two occasions, we put on some porn, starting masturbating, then gave each other (very excellent) hand jobs. I enjoyed the hell out of it until he came, and was freaked out/grossed out by encountering another dude's semen. I never even considered getting involved with another guy for years after, and am happily married to a woman. But as I've gotten older and shed some cultural baggage, I've allowed myself to be attracted to men, and would totally date/sleep with the right guy.
"It was a very positive experience; I learned a lot about myself and LGBT issues, and the guy is still my BFF."
—32/Cismale/Somewhere between straight and queer
"I had been curious about my sexual preference for a while, but I was a FratBro so there was no way I was gonna do it for fear of someone finding out. So once I went to grad school in another state, it seemed like the perfect time. I downloaded Grindr and had quite a few hookups. I eventually realized that I was doing all these anonymous hookups out of physical attractions and mostly boredom. Hooking up with guys is a lot easier than girls. Now I consider myself straight and looking for the right girl with the occasional guy hookup when I'm bored."
"When I was in middle school, a friend and I used to 'experiment' when one of us would spend the night. Nothing ever went too far, typically just masturbating together and occasionally jerking each other off. He was the one who initiated it; it came about as a truth or dare game. I was hesitant at first but eventually came around. It was fun but nothing that I would do anymore."
"I was 18 and just lost my virginity to a girl. I had always wondered if I was actually gay, so I started looking at both genders on Tinder. I matched with a 22-year-old guy and we ended up having sex in the woods near his house. He was actually really strange and I didn't feel comfortable about it at all. I've hooked up and had sex with other guys since then, but always in a period of severe loneliness. I'm not really sure I'm gay, but I'm probably not entirely straight either. Looking back on it, I don't regret all of my male sexual experiences, but the first one has always left me feeling a bit disgusted with myself."
"During my second semester in college, I ended up moving out of the dorms and into the apartment of a friend I had from a fraternity I was in. I kind of sensed that he was attracted to me, but I never paid any mind to it. Everyone was pretty sure he was gay, but none of that mattered. I myself was known for sleeping around, and I was in an on-and-off relationship, but never considered myself gay.
"One night, we had a small party at our place, with people coming and going all night. Things got wild, and I ended up trashed. Everyone did.
"Everyone ended up leaving, and I went to my room to wind down. My roommate ended up stumbling into my room and landed on my bed. I just laid there and blew it off. He started getting handsy, and I immediately knew where this was going. He told me to relax, and I was pretty horny anyways. He ended up giving me a blowjob, and it was completely mind-blowing. We ended up doing things the rest of the time I lived with him. I eventually reciprocated, but we never did anything aside from oral or masturbation.
"Looking back, I have no regrets about any of it. I don't think it defined my sexuality, because I still identify as straight. It was a good experience, and I wouldn't change anything."
"When I was 13, one of my best friends told me he was bi. Later that night at his house, we were watching a movie and he started playing with my crotch with his feet, and ended up unzipping my pants. He asked if he could give me a blowjob and I said sure. He did, but I couldn't give one to him because it was too weird for me at the time. That was my first sexual experience in general, let alone man-on-man experience. I didn't end up having sex with a girl until I was 18, five years after that gay experience."
"One of my high school best friends is gay. One time I gave him a ride home and he jokingly said, 'I'd offer to blow you but my tits are in the shop.' I was 18 and probably just hearing 'tits' was enough to get me hard. So I unzipped my pants and took my dick out kind of joking, kind of not. He started sucking and I kept driving until we got close to his house and he told me to pull over and I blew my load in his mouth and then he said he was going to eat my ass. He got out of the car, walked around to the driver's side and opened my door. I got out and leaned onto my car and he ate my ass for a long time. This was on a suburban cul-de-sac (he loves puns so maybe that was part of his plan). Anyway it was unreal. It felt so good my legs were shaking. I kinda came again but there wasn't much and he said, 'You don't have any more for me?' And I thought that was so hot that someone wanted my cum that much.
"I finished driving him home and stayed up all night kind of grossed out, but not? Also I'm embarrassed to admit I worried about AIDS. I was so nervous to see him at school. But he claimed not to remember anything ’cause he was drunk. He wasn't that drunk though. Nothing like that has happ
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