Pegging

A really big dream of mine is that a woman does me in a loving and passionate way.

My first pegging by wife came about during our sex play with me using a standard size vibrator on her vaginally then mounting her for missionary intercourse and suddenly without notice I felt my buttocks spread open and her vibrator entering me quickly and her laughingly exclaiming “time you felt and experienced what us girls endure and enjoy”. My ejaculation within her was massive . Have repeated this on occasion but the initial time was most definitely the best due to it's unsuspecting occurrence when it happened. Fretter

A few years ago my husband and I watched a live sex show in London involving a woman pegging eight or nine men in sequence one after the other. There was a wide variation in the response of the men, some remained limp, and others had a strong erection, a couple ejaculated just from the pegging stimulation but most needed additional manual help to orgasm. I have forgotten the stage name of the women it was a dominant female/submissive male show with a pegging end game with a lot of taunting and verbal abuse. We bought her “how to video”; I have no idea where it is now.

When we got back to the states, my husband bought pegging gear for me to use on him. The harness did not really fit right so it was uncomfortable and awkward for me to use. It took several tries to find a harness that is comfortable, and it holds the dildo firmly. The harness also allows me to wear a dildo in my vagina as well as the external dildo for my husband. My husband usually initiates the pegging activity a couple of times a month. It is all nonverbal, I know that he wants mt to peg him if he leaves the harness in the bathroom. He takes care of prepping himself with a couple of enemas, usually three. That helps avoid any mess. I bought him two peignoir sets, black and pink, to wear when he comes to bed for a pegging session. I usually put a hood withe a gag on him as well to further enhance my dominance.

Dita

@Dita - “When we got back to the states, my husband bought pegging gear for me to use on him. ……. My husband usually initiates the pegging activity a couple of times a month. It is all nonverbal, I know that he wants mt to peg him if he leaves the harness in the bathroom. He takes care of prepping himself with a couple of enemas, usually three. That helps avoid any mess. I bought him two peignoir sets, black and pink, to wear when he comes to bed for a pegging session.”

Good grief, Dita. What a lucky husband you have! And thank you for being such a loving wife - all good to both of you!!! I wish you many enjoyable nights.

I was only pegged once a number of years ago by a sweet gal that I was dating. I remember what a fantastic feeling it was! I would sure love to get pegged again, but finding a partner is very difficult.

Always wanted my wife to do that. When we were younger and crazier she used her fingers or a carrot on me a few times, but we never took it any further than that.

My late wife occasionally said she wished she had a cock to fuck me. Sadly, we never got around to trying it. I think you must be an amazing woman to be married to @Dita .

My girl friend lover really likes buggering me with a dildo. she likes to watch the dildo go in and out of my anus, she likes to hold my hips and sink suddenly and far into my posterior. she accompanies these movements with little cries. Maybe she's getting revenge for a lot of things she's suffered in her life? It's me who asks for mercy after a while because sometimes the feeling can be borderline painful. but I like that she likes and that it excites her. after we make love like crazy

I love love love pegging. I'm open to it every day. My wife is basically a sub, so it doesn't happen as often as I'd like

The only male partners who I've penetrated have been play doctor patients. I've put my finger (sometimes fingers!) deep in their bottoms, which I LOVE doing, but honestly the idea of wearing a strapon and dildo and fucking a guy doesn't appeal to me. Maybe with the right guy it will happen but there's no Right Guy at the moment.

As a gay total bottom, i don't even want a Man to wear a condom, i.e., i want skin on skin. If He is really into it, connected to what He is doing and using, toys are okay... but still not the ultimate, more foreplay.

Sex for me it about connection of need/desire and there are several things about a Mans needs/desires i am connecting too:

1) His need to penetrate connects to my need to be penetrated

2) His need to have an orgasm inside of another connects to my need for His orgasm inside of me

3). His need to plant a physical part of Himself, e.g. His seed, connects to my need to be His garden of sorts, the place where He plants, cultivates Himself inside of me.

i do wonder about pegging between a Woman and man... if She can get an orgasm by doing that, it would seem better to my psychological wiring, though i'd never want that being gay, but i'd want that for a Top either way.

It started with my girlfriend/wife fingering me. That led to butt plugs and prostate toys. A few years ago I finally convinced her to penetrate me with a dildo when we were on vacation. She has since pegged with a feeldoe but prefers to use a dildo manually. She is much shorter than me and it is hard for her to get the right angle. My favorite position is on my stomach lying flat. She starts by lubing me and slowly penetrating my ass with her fingers. Eventually she switches to a dildo and gradually increases the size. By the time we get to the biggest one, I'm on my knees with my ass in the air slamming back into her like a bitch in heat! The orgasm is intense!

My wife discovered I loved things in my ass! She was happy to massage it and stretch me. She even got vaginal stimulation when she put her fist in me! She never actually knew I also love to have men's cocks in me too! I'm sure she suspected be it never came to certainty.

My girl friend lover really likes buggering me with a dildo. she likes to watch the dildo go in and out of my anus, she likes to hold my hips and sink suddenly and far into my posterior. she accompanies these movements with little cries.

I'd say she's a keeper!

I too have had the pleasure of being spoiled by my wife in this way. She said I could feel what anal sex feels like. To her surprise, I immediately agreed. Since we don't have a strap-on, she held one of her other dildos in front of her vulva in the manner of an erect penis and slowly pushed it deep into my anus. I lay on my back with my legs raised and my knees pulled up to my chest. She wanted to stop soon because she was afraid of hurting me. But I begged her to continue and soon got a hard erection. So she continued to peg me until I squirted in a mega orgasm. She was surprised that I liked it so much, but since she also likes being taken anally, she finally accepted it.

My first attempt at getting pegged was at a CFNM event . It did not so well. I think of the problem then was I was not fingered first . This past weekend played with a female who loosened me up . Being my third attempt I was surprised that I took 3/4 of the average size dildo in my rectum.

Two words: Yes, Please!

I wish I could report that a loving or enthusiastic female partner had given me good pegging at some point in my life but sadly it hasn't happened. The best I've managed on this level has been women who were prepared to indulge me with a finger or vibrator. Good, but not good enough.

Therefore I have had to resort to professional sex workers who have varied from excellent to downright disappointing. One woman gave me a strapon fuck of sorts, & frankly, I couldn't decide if her mind was more on the clock or the cash register. A couple however were clearly ladies who took pride & pleasure in their work.

One memorable woman had me help her into her pair of latex 'triple penetrator' briefs which had an internal vaginal dildo & smaller anal one on the inside & a realistic looking rubber erection about 7" long & not too thick on the outside. Once pulled up tight with the internal dildos snug inside her it looked for all the world like she had sprouted a real erection out front. She gave me the most memorable fucking while at her request I masturbated my erection as she thrust into me. I ejaculated as she held my hips & kept the dildo pushed firmly in my rectum against my prostate as I came. Telling me all the time how I was her "anal fuck slave". Magic. Sadly she has now retired & all I can find online are a few old archive pictures.

The best I've managed on this level has been women who were prepared to indulge me with a finger or vibrator.

She gave me the most memorable fucking while at her request I masturbated my erection as she thrust into me.

i will not have sex with someone who is just "indulging" me, i'd rather go without. If they do not want it as much as i do, to me it's tantamount to masturbating. Actually, worse, because of the missed connection.

It reads like the sex worker was actually into it. Not a stretch to my way of thinking. i'm sure there are sex workers who do it just for the money. On the other hand, i know there are sex workers who love sex and just happen to make money doing something they love.

Personally, i've never been with a sex worker, and anyone asking for money for sex is a total turn off for me. i don't object to the profession, i just don't have sex with people who do not want to have sex with me... the money exchange gets in the way of that for me and reduces what for me is a profound intimate connection with another person to physical exercise with a piece of equipment, not a person. Not a universal judgement, just the way it makes me feel.

I'd have to be convinced the Top was really getting something out of it to be pegged by Him.

i will not have sex with someone who is just "indulging" me, i'd rather go without. If they do not want it as much as i do, to me it's tantamount to masturbating. Actually, worse, because of the missed connection.

The same here. It's a sort of 'pity sex', feeling sorry for the guy.

But as for paying for sex, obviously a sex worker will virtually never have a true desire to have sex with you. They are in it for the pay of course. But there is nothing wrong with that, just as there is nothing wrong with paying someone for a massage with or without a happy ending.

Both are payment transactions for some form of body contact.

i will not have sex with someone who is just "indulging" me, i'd rather go without. If they do not want it as much as i do, to me it's tantamount to masturbating. Actually, worse, because of the missed connection.

I agree and disagree with not having sex with someone who is just “indulging” me. (OK I’m conflicted!🤪) It’s different in a committed relationship versus casual sex. My wife and I often indulged each other because of our connection. We seldom declined the other. In the sexless marriage thread someone said at times the woman should just lay back and spread her legs, indulge your partner. My wife and I did, and usually, if not always, indulgement turned into enjoyment. Likewise, albeit more infrequent, I’ve ponied up when I was tired or preoccupied when my wife was up for it.

The difference is the commitment you have with your partner. Without it, I wouldn’t enjoy “masturbating “ inside a pussy that was just accommodating me.

That may or may not sense to everybody, it worked(s) for us.

After several sessions involving rectal and prostate massage, I asked 'Serena' — one of my two instructors in erotic massage — whether she would peg me.

During our sessions, Serena had masturbated me in many different ways, including (a) having me on my back, knees to chest, while she held my cock and massaged my prostate, to climax; and (b) having me on my hands and knees, and stroking my cock with her left hand, as the fingers of her oiled right hand slid in and out of my rectum.

The first time Serena (unexpectedly) performed (b) on me, it gave me one of the hottest, most intense orgasms I've ever had. (I remember my rectum spasming on her fingers, still inside me, while sending jets of hot cum all over her massage table. I don't think I'd ever had a rectal orgasm before, but that had just happened at the same time I came from my cock.)

Trying to let my breathing slow after all that, and still on my hands and knees, I heard myself say, "That's like being male and female at the same time." She patted me on my ass and said, "It is, isn't it?"

Which started me fantasizing...

One afternoon, after a prostate massage, and as Serena was wiping down my chest and abdomen with hot wet towels, I asked her, "If I buy a strap-on and bring it, will you fuck me?"

It wasn't just the thought of feeling her plundering me from behind, that was so arousing... I loved to imagine her, naked except for the strap-on, thrusting away, and was planning on asking her to let me make a video, if she said yes. (I'd seen every inch of Serena, of course, many times, but never with her hips thrusting.)

Serena paused in her scrubbing, and looked thoughtful. "No... I'm going to have to draw the line, there. Too close to breaking my promise to my husband." (She'd told me, early on, "No intercourse." But I was hoping that that applied only to my keeping *my* cock out of *her.*)

Serena did recommend a particular brand of vibrating prostate massager, and told me that if I wanted to, I could bring it to our sessions. She would masturbate me while it was inside me.

I did end up buying that massager — and I loved the very intense climaxes it produced — but I never brought it to my sessions with Serena. If she wasn't going to fuck me, I still preferred her fingers inside me, to the toy.

Being pegged by her remains a favorite fantasy, to this day.

@Parker Your story has some very hot details. Serena has a very interesting line drawn in her Go /NoGo list. Not the logic I would have used, but if it works for her I respect her honest answer and standing by her convictions. Glad you had such a good time with her. Thanks for sharing.

@Parker I think Serena sounds fucking hot! You were a lucky guy but imagine the treatment her husband must've got....

I agree and disagree with not having sex with someone who is just “indulging” me. (OK I’m conflicted!🤪) It’s different in a committed relationship versus casual sex. My wife and I often indulged each other because of our connection. That may or may not sense to everybody, it worked(s) for us.

That makes sense to me. my not wanting 'indulgence' sex is because of the missed connection, but if you already have that, it is already a part of the dynamic. Which is not to say i do not think a committed couple cannot have indulgent sex without the connection. i experienced that in my marriage, and it felt awful (to me) even though we both had orgasms and a sort of pleasure. Hello "conflicted." We were not a compatible couple though.

The experience burned into me the belief that commitment without that compatible connection, symbiosis, is not sustainable. Sort of like fast food sex, too much of it will give one atherosclerosis and a heart attack.

On the other hand, i have had connected sex with virtual strangers where the connection was so profound i had to bite my mattress to keep from declaring my undying love to the Man seeding me.

Life can be wonderfully complex, eh?

One can be in a “committed “ relationship for various reasons without the “connection” @tallslenderguy pointed out. Financial, security, children, status, fear of divorce and costs/stigma, religion, insecurity……. Lots of reasons to commit without connecting!

Fortunately we have both the commitment and the connection. Some say We “chose wisely”…I think we were incredibly lucky! Sexually, values, interests, physically, emotionally ….. we were the perfect storm.

@Parker I think Serena sounds fucking hot! You were a lucky guy but imagine the treatment her husband must've got....

@alan20cm Serena was fucking hot (and she still is, though our sessions together were some years ago, and as she got older, she moved on from teaching massage.) She really is one in a million... highly skilled herself, erotically; and someone who loved teaching erotic skills to male clients whom she trusted, and who was open to being pleasured, herself, during the training (within limits.)

And she is a beautiful person, both spiritually and physically. Dressed or nude, she always took my breath away.

Yes, I was lucky. I'll always be grateful to Serena for the new directions in my life that she made possible.

@Parker I was lucky enough to have someone in my life like that (sadly no longer) so I understand. Sometimes you have to accept what life throws your way & enjoy for the moment...I'm glad new horizons were opened for you