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664 votes, 45 comments. 541K subscribers in the Pegging community. A subreddit solely for the purposes of pegging. All submissions must show pegging!…
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Forewarned is fore-armed, as they say. In my experience I have met thousands of people now, and below are the most common questions I have been asked over the past 20-odd years of going out dressed, from people who may want to know more about you as a Cross-Dresser. So it may be worth asking […]
Pegging is a way that we express our love together and we both enjoy the incredible connection that it affords. If you are female and apprehensively thinking of "trying pegging out" because one of your friends suggested it, you read a blog in Cosmo about it, or your boyfriend begged you for it; whatever the reason.
Pegging is usually referred to a cis woman penetrating a cis man with a strap-on dildo. You've come to the right place; here's how to have strap-on sex as a straight couple.
Want to incorporate strap-on play into your sex life but not sure how? Five queer women share their tips.
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.
Pegging also requires immense trust; being penetrated anally with a strap-on dildo by a pro-domme or dominant partner allows cishet men to not only receive anal pleasure but become vulnerable and ...
This step-by-step guide to pegging for beginners takes you all the way from bringing it up with your partner to tips for aftercare.
Started crossdressing at an early age. I have a sister that is older, but we were similar in size that I could wear her clothes. She had dressed me up in her skirts, dresses, and school uniforms several times. My mother had seen us playing several times and commented that I looked cute as a girl. Then one day, my sister didn't want to play dress up any longer. I still liked dressing up, so ...
As orgasmic as pegging can feel, it isn't for everyone. If you don't want to sport a strap-or take it anally, there are plenty of ways to get pleasure.
Pegging is a way that we express our love together and we both enjoy the incredible connection that it affords. If you are female and apprehensively thinking of "trying pegging out" because one of your friends suggested it, you read a blog in Cosmo about it, or your boyfriend begged you for it; whatever the reason.
Sep 2, 2024
Mom really did all the talking, obviously she was a talker. Over the next couple of days we "bonded" well. She is really a very nice lady, I found. She had no idea I was a man. Bob was happy, I was happy. This "game" was working and I was having lots of fun. Later in the week she asked me out for a "girls' shopping spree" .
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Discover the heartwarming story of a mother and son as they explore identity, confidence, and transformation in this compelling MTF crossdressing journey.See...
Couples interested in pegging may want to expand other creative ways to experience pleasure, she continued, or struggle to feel pleasure on other body parts. Also, if one partner doesn't want to be or can't be penetrated, pegging can be another way to connect. Preparing to peg Anal sex is different from vaginal sex.
This video is about a forced crossdressing story. A man is abducted and made to dress up like a woman against his will. He struggles to cope with the situati...
At first I celebrated how open and accepting I was—but my positive response was short-lived.
What does pegging feel like and why do men love it? We asked some guys who've tried it for their experiences and tips for those considering it.
This is a wonderful thread, Rachel. I love happy endings. I do not know how I missed it up until now. I hope more people contribute their positive "caught" stories. I wish I had a story to share, but I have never been "caught." I can only say that the few people to whom I have presented intentionally have either been supportive or have not cared. Only one person laughed when I ...
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Every time a couple steps into the pegging world, they're giving a big middle finger to stereotypes and proving that intimacy isn't one-size-fits-all. Choosing pegging means you're saying, "I make my own rules, thank you very much." And nothing screams confidence louder than living authentically—even if it's with a strap-on involved.
There are plenty of stories of women who suddenly found out about their partner's crossdressing after years of marriage and were horrified. There are also those who found out, or were told early on in the relationship, and were more able to be accepting, but still did not feel quite the same as I do.
Jul 7, 2025
Feb 10, 2025
Pegging is one of those topics that's been slowly shifting from hushed whispers to bold, empowering discussions—and rightfully so. At its core, pegging is about loving dominance, flipping the script, embracing role reversal, and most importantly, creating a bond of trust and pleasure that feels both vulnerable and empowering.
My boyfriend is a crossdresser?! You're likely feeling a bit shocked - after all, this is unlikely to be something you expected when you entered the relationship.
Pegging is when a woman uses a strap-on dildo to have sex with their partner. Women share why they like pegging men, and how they first got into pegging.
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