Tranny Pegged

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Tranny Pegged
Home » I pegged my boyfriend and now he wants to be ‘the girl’

Kinky sex can be wonderful, but it won’t fix your relationship.



by
Dan Savage
February 11, 2020 August 18, 2021

Chicago’s alternative nonprofit newsroom

Q: My boyfriend and I were having relationship issues until we tried something new: pegging. He wanted to try it, but he was afraid and sometimes said the idea disgusted him. Then we tried it, and it was better than normal vanilla or even kinky bondage sex. It was the most emotionally connected sex we’ve ever had. I actually pegged him three times in 24 hours. He says now he wants to be “the girl” in our relationship. He doesn’t want to transition to become a girl, but to be more “the girl” sexually and emotionally. I see this as sexy and loving. I’ve always taken care of him in a nurturing way, but this adds so much more. I feel bad about sending this long story just to ask a simple question, but . . . how do I be more “the guy” for my boyfriend who wants to be more “the girl”? Not just sexually, but in everyday life? — The Boyfriend Experience


A: “It’s amazing these two found each other,” said Key Barrett, a trained anthropologist. “They communicate and obviously create spaces to be vulnerable together and explore.”


Barrett has studied female-led relationships (FLR) and written books—fiction and nonfiction—about them, TBE, and his first concern was your boyfriend succumbing to “sub-frenzy,” or a burning desire to realize all his fantasies at once. You guys aren’t new to kink—you mention bondage—but you’ve found something that taps into some deep-seated desires, and you don’t want to move too fast. “Pegging opened up a huge box of shiny new emotions and feelings,” said Barrett. “That’s great, but they should take it slow, especially if they want this dynamic to be a part of the day-to-day relationship.”


You also need to bear in mind that pegging, while wonderful, won’t solve your underlying “relationship issues.” Unless, of course, the issue was your boyfriend feeling anxious about asking you to peg him. If he was worried about walking back his previous comments, or worried you would judge, shame, or dump him over this, that could have been the cause of your conflict, and the pegging—by some miracle—was the solution.


But, hey, you didn’t ask about those other issues, so let’s focus on your actual question: you being “the guy” and your boyfriend being “the girl.”


“The boyfriend wants TBE to be ‘the guy’ in the relationship to reinforce his desire to be ‘the girl,'” said Barrett, “and she seems okay with this, although she does acknowledge that this would require more than the nurturing and caretaking she’s already showed toward him. That’s a valid concern. His desire to take the kink out of the bedroom and merge it with the day-to-day risks turning her into a kink dispenser. There’s also the aspect of the boyfriend’s gender stereotyping. Being dominant isn’t unique to men, and being submissive isn’t a ‘feminine’ trait. There are a lot of alpha men in FLRs who shine in support roles for the women they trust. Female-led relationships don’t rely on stereotypes. Indeed, they often flout them by relying not on stereotypical behaviors but on what is a natural dynamic for the couple. In that sense, each FLR is unique.”


While it’s possible that “I want to be the girl” are the only words your boyfriend has to describe the dynamic that turns him on, for some men, sacrificing their “male” power and privilege is an intrinsic part of the eroticism of submitting to a dominant woman. And that’s okay, too.


“If he legitimately wants to take on a role of supporting her and being her adoring submissive partner while thinking of that role as ‘feminine,’ it could work for them,” said Barrett. “He might really enjoy supporting her decisions and being more of a domestic partner. She might enjoy the support and validation that comes from having a partner who revels in her successes and strength. This could fulfill the ‘caring for him as if I were the boyfriend’ portion (what a loving a statement!) while still feeling natural for TBE.”


So how can you get started as “the guy” in this relationship?


“They should, again, start small,” said Barrett. “Maybe delegate a few tasks that were ‘hers’ to him, and she can tell him how she wants them done,” whatever it is (dishes? laundry? cocksucking?), “as this will help ensure the outcome they both want. I would also recommend they both read about what FLRs are and aren’t. FLRs are often kink-friendly, but kink is not required. And they need to remember the key word in ‘female-led relationship’ is ‘relationship.'”


Q: I’m a woman, and I was contacted on an app by someone claiming to be a “guydyke.” Based on their profile pictures, I was basically looking at a white, cis, masc-presenting man who’s said he is queer but only attracted to women. And by masc-presenting, I mean I could not pick him out of a lineup of the most average of average-looking straight dudes: drab clothes, a week’s stubble, bad haircut. Granted, nobody is obliged to announce their gender identity through clothing or grooming choices, but how is this guy not straight? — Perplexed


A: “I happen to be one of those ‘old-school’ lesbians, despite not actually being what most consider to be old,” said Arielle Scarcella, a popular lesbian YouTuber with more than 600,000 subscribers. “Back when I was coming out in 2005, if a male person who lived as a man—a male who lived in such a way that he was always perceived to be a man—claimed he was a lesbian or a dyke, we’d shut them down. But in 2020, it’s only acceptable to accept everyone for what they say they are. I disagree. Part of being a lesbian, being a woman, is also cultural and societal. It’s not simply an identity. Living in the world as a woman matters . A biological male who presents as a man and has sex only with women will never know what it’s like to be treated as a woman or a lesbian. He can identify however he likes, of course, but he will be perceived as a straight man who’s fetishizing queer women.”


Q: I’m in my late 20s and genderfluid. I have a male physique, but at times I feel more feminine. I suddenly can’t shake the desire to have more feminine breasts. I’ve been looking at women with C or D cups and wishing I had boobs that big. I’ve spent time looking into breast enhancement, but I live in the midwest. It’s not as bad as the south, but there are still plenty of people who believe violating gender norms is a sin. I guess I don’t know what I’m trying to ask other than whether this is normal. —Bro Obsessed Over Bust Size


a: It’s not normal—in the literal, non-pejorative sense—for an “assigned male at birth” person who presents as male to want to slap large boobs on his otherwise male-presenting physique. But so what? If you’re worried about how your boobs will be received there in the midwest, perhaps you could get yourself a pair of what drag queens call “chicken cutlets,” i.e., silicone breasts enhancers that tuck into a bra, and try wearing them out. For the record, kids, I’m not equating being genderfluid with drag, even though many drag queens (but not all) identify as genderfluid and many genderfluid people (but not all) do drag. (I never get tired of tap-dancing my way through this minefield.) But back when I was doing drag, BOOBS, a pair of chicken cutlets artfully placed under my pecs created a pretty realistic looking set of big ol’ titties. Think of chicken cutlets as a temporary, nonsurgical breast-enhancement option—to test the locals as well as your desire to have breasts.  v


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It's time for your partner to strap on that strap-on.
So you want to get pegged. Makes sense! Pegging is when your partner wears a strap-on and enters you from behind. Yes, it's super hot, but it also stimulates your prostate, which is packed with nerve endings—hello, best orgasm ever. (Don't believe us? Here are six guys on what it's like to get pegged during sex .)
Whether you're a seasoned peg-ee or new to the sport, you might be on the lookout for pegging positions to try. The good news is, you have plenty of options, each allowing for different sensations and very sexy views.
"Any position that you can imagine people having penetrative sex in, you can probably make it work with a strap-on as well," says Dr. Zhana Vrangalova , LELO sexpert and NYU professor of human sexuality. You can try it standing; you can try bending over a piece of furniture and having your partner enter from behind... You should feel free to experiment with whatever feels best for the both of you.
With so many booty-ful options, you might need a little guidance, so we asked Vrangalova which pegging positions she recommends the most—from rear entry-level to the more advanced.
Great for beginners, this is one of the most common pegging positions. On the bed, couch, or hey, even on the floor, you get on your hands and knees and have your partner enter you from behind. This is a sturdy position—if it's your first time experiencing anal penetration, you might appreciate not having to balance in some complicated configuration.
This common pegging position is also ideal for newbies. "It's comfortable for everyone involved, and it's kind of an easy position to penetrate someone in," Vrangalova says. "It gives [your partner] a nice view as well, which is great."
Lie on your back and bring your knees toward your chest; then, have your partner enter you. You could be lying at the edge of the bed with your partner standing between your legs, or have both of you on the bed together, with your partner kneeling.
Either way, it "really gives you a great view and provides eye contact between you and your partner," Vrangalova says. It also gives your partner easy access to your penis, so they can give you some manual stimulation at the same time.
In this position, your partner lies on their back with the dildo sticking up in the air; you kneel or squat over them, riding in a sort of cowboy-style. Once again, you and your partner will have eye contact, and they'll also have access to your penis.



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Savage Love

Mar 26, 2019 at 2:06 pm




She Used to Enjoy Pegging Her Hot Husband — Should She Tell Him What's Wrong?



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The trouble is, the more time goes on, the more our pegging sex—which plays a significant role in our sex life (maybe 30-40%?)—is feeling... well, more and more gay and I'm not sure I'm enjoying it anymore. For a long while, I regarded his affinity for pegging, and his appreciation for sex with dudes, as the separate things they are. For example I knew he watched both pegging porn and gay porn and I was totally cool with both. He would discuss how much it turned him on to watch a woman in latex fucking a bound dude, (which I was happy to reenact!), or show me a hot gay sex scene he had just enjoyed.
However, over the last year or so, the pegging has stopped feeling like what it is (a hot lady fucking her hot husband) and more like... a hot husband is trying to reenact his gay fantasies with his wife. For example, our pegging play has turned into a lot of him sucking the strap-on and wanting me to role-play and dirty talk about him being a cum slut for hot man cock. The first few times it was fine because it was new and different and he was enjoying himself. Now that this is how our normal pegging experiences are going, I'm feeling increasingly disengaged and even turned off by this sex, which makes me feel all sorts of things—sad, uncomfortable, ashamed. The last time I fucked him, he asked if I'd be open to binding my tits and not wearing my sexy strap-on sesh lingerie. I said yes, but after, I realized I had reached a point where I felt like a sub-par stand-in sex-prop, and felt turned off and embarrassed afterwards. Nothing about it makes me feel sexy, or like I'm "part of it'- anymore, if that makes sense. I feel left-out and inadequate.
My feelings about this are leading me down one of two paths (perhaps both wrongly), which is why I'm writing you. Because I'm feeling disengaged and even turned off, I feel guilty, and like I'd be bi-shaming him to bring it up. Why would this be different than any other role-play? On one hand this makes me feel disgusted with myself—but on the other hand, I don't have fucking nerve endings in this cock, and I'm not a dude, so watching him suck it and pretend like I'm a dude is just not working for me, and is that so wrong? So option one was to gently tell him it isn't working for me. But the idea of accidentally shaming him, or it resulting in him closeting this fantasy outlet (since we're monogamous) also feels shitty.
So maybe my other option is opening the relationship up so he can get his gay sex on, if that's what he's really after? We had discussed this potential in the past, many years ago, and never got anywhere. I was potentially open to the idea of being poly (separately, I'm not interested in sharing our intimacy). He was not interested in being poly because he was anticipated an imbalance in the extra-marital relationships (that I'd get laid a bunch more, and he rarely would; which is maybe true since we live in a mid-sized, conservative town, and he can be shy). Instead of being poly, he was more interesting in bring extra people into our bedroom. I hate this idea for all of the stereotypical reasons monogamous folk often do, I fear my reaction, being left-out, what it would do to our intimacy to see him get rock hard for someone else, etc. Because of our conflicting interests on this, we axed both possibilities and have just stayed (I think) happily monogamous.
What do I do, Dan? I don't want to keep having regular sex that turns me off and makes me feel like a stand-in for the gay sex I imagine he wants to be having. Am I reading too much into this and projecting? Is this more about my feelings of inadequacy than my partner?
P.S. To be fair to him (which I want to be) our hetero-ish sex and/or other kinky sex is still awesome and he seems to enjoy it just as much and we have it just as frequently.
To recap: your husband is asking you to do something that makes you feel sad, uncomfortable, and ashamed (bind your breasts, pretend to be a dude, role-play dude-on-dude sex)... and you've hesitated to say something because doing so might make him feel shamed. Oh, and this kind of sex—you pegging him—constitutes roughly a third or more of your total sexual activity. So if you don't say something and these role-play trends continue on their current course... you're gonna have a lot of sex over the next three or four decade that makes you feel terrible.
Sometime like this: "It's always turned me on to be this hot woman in l
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