Pegging

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Porn star Dani Daniels says here at 7:42, that she's fucked a man in the ass, but I've never found the video of it... if it were filmed at all! Would be hot!

 
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Porn star Dani Daniels says here at 7:42, that she's fucked a man in the ass, but I've never found the video of it... if it were filmed at all! Would be hot!

Couldn’t find it either.
Holly Randall is pretty cute herself. Anyone know if she’s done any porn?
 
Long time lurker. I've posted the following on one of the Reddit subs recently. Here's my real-life pegging-only marriage story, 100% true.

TLDR; Wife converted me to pegging-only via pegging marathon session over the course of a month, with me eventually cumming hands-free and not looking back since.

45 year old, here. I've had crossdressing tendencies since I was a child and my wife knew about them before getting married. Our sex life for the past 10+ years incorporated all sorts of kinks (including once a month pegging, with me dressed in lingerie), but mixed in missionary, under the sheets, with the lights off type vanilla sex. It was a varied mix - my wife didn't care as long as she got off. The normal routine would be for me to be moving inside her while she got off on clitoral stimulation with a vibrator. Afterward, I would get off with me still inside her. We were the typical once-a-week sex type couple and maybe twice on a weekend. During the beginning of our marriage, we both got laser hair removal and have been hairless from our eyebrows down. She encouraged it because of her dislike of pubic hair and when that was removed, she thought it was odd to have hair on other parts, so the torso was next and then the legs. She liked it because of the feeling of rubbing our smooth bodies together.

After she hit her early 40s (with one child under her belt), I noticed that she was becoming physically uncomfortable with any further penetration after she had already gotten off, especially if it was two days in a row (like on a weekend romp). I would be gentle with her, but constantly having to think about her comfort put a damper on the mental component during sex and I would start going soft after she had gotten off and it was difficult for me to finish after that. It was easier when I was crossdressed with a butt plug for extra stimulation, but I would still overthink her comfort level and would inevitably not be able to finish because I didn't want to be too rough, which is how I always was used to doing it. This resulted in me starting to take care of my own needs with me starting to hump the pillow next to her while she was getting off again. I would be crossdressed, usually in pantyhose and a slip and while she was getting off and I was humping, she would start saying things like "You can't even please your wife", "You're so pathetic", "A real man would cum inside his wife and not his pantyhose." I know she didn't mean those things - it was just a bedroom thing, she assured me. We then progressed to me just staying inside her, motionless, while she would stimulate herself. Then it went to me just orally pleasing her while she was saying more things like "all you're good for is using your tongue to please me", "you're such a good sissy." I knew that her verbalizing things like this was helping her get off since it certainly wasn't for my benefit when I was between her thighs. During this "transition" period, I would let her know that I miss penetration.

After "whining" enough (her words), she said "You want penetration, fine, you're going to get penetration." Out of the blue, in the middle of a day (99.9% of the time we have sex at night) she forcefully told me to get dressed in my usual outfit and get on the bed. She put on her strap-on and started fucking me. I wasn't even in the mood for sex because it was so unexpected. I started humping the pillow with her pounding me and I came. Nothing different from the other times we pegged, except for the whole new take on it as I would soon find out. She then proceeded to get herself off, again commenting on what a sissy I was. The next day, she pegged me again. Same thing the day after that. And the day after that one. I liked that I was able to come, but asked her what the deal was. She said she's giving me what I always wanted. I told her that was not true and that I wanted a mix of everything. She said that I wanted penetration, but due to me going soft, that she's giving me penetration that I can't otherwise have. I said that it's because I worry about her and don't want her to be uncomfortable. She said that I should know that she doesn't need penetration and how we're doing things is fine with her. She then proceeded to peg me for almost three weeks in a row. Then in the third week something happened that I've never experienced before. The pressure was building up with a warm feeling and then there was release without an orgasm - just a flow of my juices. I completely froze and said "What just happened? I just came without any orgasm." I then started whimpering due to the emotional aspect of what happened - here I was dressed up, being taken anally, certainly not cumming like a man, and without orgasm. My wife, still inside me, whispered, "Looks like I finally milked you." She pulled out and I was still horny, which was odd. I then researched everything about what happened and found out that hands-free prostate orgasms, based on angle, can result in either milking without orgasms or they can result in powerful orgasms. The next couple of times we did it, I realized that I could orgasm from further pegging even after being milked just minutes prior. My wife then smiled saying that she's trained me. I said that it's not my fault that this happened and she said that it's OK and she's just brought my true self out. She told me that she sees how pegging and taking the submissive role in bed has made me a calmer person (which she is correct about).

Fast-forward to the present. We're at the point where the moment before being penetrated, I go immediately soft, which my wife says is an indicator that my body knows that my penis is worthless because my body knows that anal penetration is the only form of sex for me. I have not been inside my wife since the pegging marathon session that occurred two years ago. Since then, sex is exclusively me orally pleasing her, then her penetrating me (sometimes when I release without orgasm, she will pull out and tell me that "sissies don't get pleasure, they just get used/milked."). I will then have to finish off by humping the pillow while she pleases herself next to me. While pleasuring her, I will be wearing some sort of lingerie, but usually pantyhose and a slip, and a butt plug, usually inflatable. While I stimulate her, she will then pump up the plug as her pleasure increases and say things like "Don't stop! Make me cum, you worthless sissy slut!"

Over the past two years, my nipple sensitivity has grown and I feel like a connection is made between penetration and nipple play. I've been using using nipple aspirators prior to sex so that after I please my wife my nipples will be engorged and she will play with them as she takes me from behind. Regular manual masturbation is impossible for me, which results in either humping the pillow with a toy pushing against my prostate, which is underwhelming. I prefer to use my Njoy 2.0 to achieve a hands-free prostate orgasm in under 5 minutes. My wife knows that this is the way I please myself due to my mind having been rewired.

So what prompted me to write all of this was what happened last weekend. After two years, my wife told me that I should try to enter her - I was taken aback and said I don't know if I can and if she's sure. She said, "just give it the old college try" with a sly grin. I said, OK, and proceeded to pound away. Five minutes later and still nothing. I then refocused on imagining myself being pounded by my wife and the movement of my penis being the movement of me taking it instead. It was one of the weakest orgasms I had ever experienced. I told my wife about what I had to think about to cum and she said - "I know. It was a test to confirm who the penetrator is in this marriage."

So for those trying to have hands-free orgasms, know that it takes a while because brain rewiring is required. Try to abstain from traditional sex and explore your prostate on your own, so that when you get penetrated you will adjust to the right angle. Ridged dildos (turned the correct way is key for rubbing the prostate). For me, feminization is key, because then I can focus on cumming not like a real man (e.g., a traditional man who cums from penile friction doesn't wear lingerie and take it in the ass). Not judging here on gender stereotypes and roles, just sharing how it all came together for us. And in case anyone is wondering, no, my wife is not a closet-lesbian and she is not interested in cuckolding and neither am I.

I feel better writing this and wonder if anyone else's relationship mirrors parts of mine.
 
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We haven’t had quite that experience, but some of it reminds me of my wife and me. Our sex is infrequent so I’ve turned to Lit and masturbation for most of my pleasure. (My ultimate pleasure is making my wife cum, it is a powerful high I can’t get any other way. But opportunities are limited.). I play a lot with anal toys and nipple clamps, both of which quickly have my core contracting to the point I can achieve a dry orgasm…I suppose that’s the opposite of being milked! If I need extra stimulation I’ll also suck and deepthroat a dildo and that gets me off great.

But this is a pegging thread isn’t it? So when we do have sex, I can’t maintain an erection enough for vaginal penetration without a blue pill, and the side effects for me are irritating and last 24 hours, so I usually skip that. I’ll get my wife off with tongue, fingers and toys and it can take an hour or more. If she’s rolling she will get at least three strong orgasms before she’s done. Afterwards she wants to help me get off. She’s pegged me several times but it’s a lot of work for her after up to 2 hours of sex already. So she skips the harness and penetrates my ass with one of our vibrating dildos using her hands. She’s noticed how I stimulate my nipples and like to suck on a dildo, so she keeps up a steady stream of dirty talk about how much I like getting my ass fucked and how she’s going to get me fucked by a real cock. That combined with my filled ass and vibration pushes me over the edge to a really strong climax. Whimpering is often involved.

I’d like her to peg me more though I’m not complaining about what I get now. I have had success riding her dildo while she’s on her back, maybe I’ll try for that again soon.
Sounds like progress to me! When you allow an opportunity to cum about, it opens up more chances to explore.
Have you tried in a different environment or a 69 position so that you both climax at the same time? I'm excited to hear your next move in this sexual adventure of yours.
Happy Holidays ♡
 
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