Cumming While Pegged

Cumming While 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.”

Did you know? The Reader is nonprofit. The Reader is member supported. You can help keep the Reader free for everyone—and get exclusive rewards—when you become a member . The Reader Revolution membership program is a sustainable way for you to support local, independent media.

“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

Download the Savage Lovecast Tuesday at savagelovecast.com .
Get our free daily newsletter delivered straight to your inbox Monday through Friday. Dive into our most recent stories and exclusive insights from our editors and staff.

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.”

Did you know? The Reader is nonprofit. The Reader is member supported. You can help keep the Reader free for everyone—and get exclusive rewards—when you become a member . The Reader Revolution membership program is a sustainable way for you to support local, independent media.

“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

Download the Savage Lovecast Tuesday at savagelovecast.com .
Get our free daily newsletter delivered straight to your inbox Monday through Friday. Dive into our most recent stories and exclusive insights from our editors and staff.

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Here's the honest truth: I had no idea what pegging actually is until pretty recently; what's worse, I thought I knew what it was, but I was sorely mistaken (pun not intended). To really give you a sense of how far off base I was on this particular sexual act, the following is based on an actual conversation:
Friend: Have you ever pegged?Me: Sure, haven’t you?Friend: Um, no. Wait, have you really?Me: Of course I have. And what do you mean you haven’t?Friend: Do you even know what pegging is?Me: It’s just sex, right?Friend: [Uncontrollable laughter]
Bottom line: I thought pegging was just your run-of-the-mill penis in vagina sex. Call me naive, but hey, it sounds like it, doesn’t it?
I could not have been more wrong, obviously. And after this very real, very mind-blowing conversation about what pegging actually is, I began to research more about it, including of course how to actually do it . What I uncovered is that this sexual practice is not only very much on the rise in popularity (yep, a lot of people are giving this a go !), but that there are many, many myths that surround it. Not just myths about sex, but specifically about pegging. Because remember, pegging is not just sex. (I'm just reminding myself.)
Here are the five biggest myths about it that exist.
When it comes to actually going through with said pegging, this is the biggest deterrent. It's pretty understandable, especially this is your first time. Don't let the jitters run too rampant, according to several subjects, and much like most things in life, the pain is far worse in your mind. Think about when you lost your virginity (gals, I'm talking to you here): Sure, it wasn't, well, ideal at first but you go slow and eventually get over that hump in a big way (pun not intended). Speaking of which, the secret to minimizing discomfort as much as possible is likely the same thing you relied on then: lube, lube,, and more lube. Especially since the natural lubricants are lacking in this particularly orifice.
You know how role playing can be a huge turn on ? It shouldn't be any different here. For both parties involved, pegging can be pretty hot: the woman gets to dominate, and the guy is at her mercy. Not to mention, the gal will likely also receive a good amount of physical stimulation from the strap on itself — there is a harness involved, after all.
And then there are the taboos around pegging that stem from homophobia. Sure, historically a woman putting on a strap-on could often elude to sexual intercourse with another woman — and that's still true. But that doesn't mean it's the only truth. Like I mentioned, pegging is on the rise in popular culture, even Broad City incorporated into an episode . A wo
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Cumming While Pegged

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