strapons.tumblr.com

Podcast #175 is going to be comprised solely of stories and offerings from the giving side of the pegging equation.

Most of my readership and listeners are the Receivers. For this podcast…

I want to hear from the Givers!

Tell us all the things you love about pegging…
Tell us the story of your favorite pegging encounter…
Tell us about your first time…
Tell us about your last time…
Tell us about a funny time, or an embarrassing time…
Tell us about your favorite pegging fantasy…

One sentence, a paragraph, several pages – I want it all!

Spill it, Peggers!

You need to get your stories in by Saturday, November 11th to have them included in this podcast.

You can write me at ruby@peggingparadise.com
Or send me an MP3 of your recorded story
Or record your story on my call line (805) 500-6544

We are going to blow the Peggees/Receivers away with podcast #175!

Love,
Ruby

This piece is included in the Kinky Sex Tips Blogfest 2017 !!

Click here to see the links to all the other kinky bloggers who have participated, there is sure to be some great writing, great sex tips and all around sexiness.

Also – don’t miss this part, there are PRIZES. Yes, I said PRIZES. Click the link!

#KinkySexTips

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Women (or Givers) – are you new to pegging? This article is for you!

Definition: Pegging is when a woman straps on a dildo and penetrates a man’s ass (like in Broad City and Deadpool).

Why are so many people talking about it? Why would anyone want to do it? What’s the big deal?

Let’s start with corrections of misconceptions about this amazing sexual experience, because there are many. You might be surprised to discover the truth behind some of the fears and assumptions.

Pegging Fears and Misconceptions

  • If a man enjoys anal stimulation, he must be gay.

First, think about it…A sexual act that involves a man and a woman is by definition not gay. Now let’s personalize it. If your partner has been happily fucking you and giving you oral sex for years, he is certainly not gay. (Gay men don’t eat pussy.)

Here is another way to look at it. The area of your body that you enjoy having stimulated has absolutely no bearing on the gender you prefer to do the stimulating. Read that twice if you need to.

There is an unfortunate assumption that men who enjoy anal stimulation or penetration must, by default, want sex with their own gender. Studies say only about 40% of gay men even have anal sex. And while there are indeed some men who are bisexual and enjoy sex with men as well as woman, there are also many, many men who are totally straight and love receiving ass play.

  • If you fuck a man with a strap-on, it will turn him gay.

Many women have a fear that if they peg their man, he will leave them and run off in search of real cock. Here’s the deal: There is no magic switch inside a man’s ass, that when tripped by a strap-on, all of a sudden causes him to crave hairy muscular bodies. If he is bi-curious, he might be a little more curious after you peg him, but straight men don’t change their gender preference simply because of anal penetration.

If this were true, then a lesbian woman who fucks her lover with a strap-on would turn her straight, right? Ridiculous. See how the logic breaks down?

The more likely result of fucking your man with a strap-on, is that you will send him to the moon with pleasure, and deepen the intimacy that you share with him.

  • Pegging is painful.

Anal penetration never has to involve pain. If it hurts, you are doing something wrong, like going too fast, or using too big of a toy, or not using enough lube (the most common mistakes).

Not only is pegging not painful, it has the capacity to bring amazing amounts of pleasure to your partner! His prostate is much like your G-spot. Combined prostate and penile stimulation often result in an orgasm that men describe as ten times more powerful than a regular orgasm!

  • Pegging is…messy.

There is no getting around the reality that pegging takes place in the same area of the body that handles waste elimination, to put it delicately. To depart from delicacy, every once in a while shit happens. If the thought of a small mess freaks you out, pegging may not be for you.  If the thought of that small mess doesn’t freak you out, rest assured there are tried and true methods of cleaning out before pegging that usually completely eliminate messes. The occasional messes that do occur are typically very minimal.

  • Pegging is just not ‘natural’.

I encourage you to let go of your ideas regarding what is ‘natural’, and instead think about what interests you and your partner. Are you interested in giving and receiving more sexual pleasure? Then pegging would be a great thing to try.

For some people, all sex toys are not natural. For others, they would never bring whipped cream and chocolate sauce into the bedroom to add to their sexual experience. Some couples have ventured into the 50 Shades territory while others would never consider it even close to ‘natural’.

You and your partner are adults, and the cool thing about being an adult is that no matter what others might think, what you decide to consensually do in the privacy of your own bedroom is no one’s business but yours. If you try pegging and love it, you will be so glad you tried it! If you try pegging and decide you don’t like it, at least you tried it and now know it is not for you.

I’m thinking that since you are here at the Blogfest, you are curious about different sexual activities that can bring you more pleasure. (If someone told me there was a way I could have orgasms 10 times more powerful than any orgasm I have ever had, I would find it difficult to pass that up.)

  • Pegging means I have to tie him up, dress him like a woman and beat him.

If you have watched pegging porn, I can see how you would assume this. While it is true that some couples who enjoy pegging also enjoy one or more of these activities, they are by no means a requirement for the experience. Pegging can simply be one more way to make sweet, intimate love with your partner.

  • If I strap on a fake cock it will destroy my femininity.

There is no rule that says when you strap on a fake cock, you are no longer feminine. It’s just a sex toy! You can be as feminine or not feminine as you like while pegging.

Some women might be happy to know that there are ultra-feminine harnesses available, some of which have sexy garters attached. There are buttery soft leather harnesses in colors of Prince Purple and Nicki Minaj Pink. There are non-realistic dildos that don’t resemble a penis in the least!

There is nothing in pegging that says you must do it a certain way. You (and your partner) get to choose what feels right to you.

 

With the fears calmed and the misconceptions corrected, now let’s look at why couples decide they want to explore pegging…

Pegging Facts

  • Pegging is pleasurable for men.

Why would men want to experience this? Because it gives them a lot of pleasure! Men have a prostate gland, which is responsible for manufacturing fluid that helps carry the sperm out of the body. Stimulation of the prostate gland is indeed quite pleasurable for most men. The prostate gland is most easily accessed through the anus.

  • Prostate massage is healthy for the prostate.

Besides the pleasure aspect, pegging can be good for the prostate. Stimulation of the prostate gland, from anal play or pegging, helps keep the prostate healthy. Regular prostate massage can help avoid swollen prostate. It can also help relieve and sometimes eliminate the symptoms of swollen prostate (BPH).

  • Men can orgasm from pegging.

We are not talking about just a little bit of pleasure, here. Again, most men who have experienced an orgasm resulting from a combination of prostate and penile stimulation describe it as roughly 10 times more powerful than a normal orgasm.

In addition, some men can orgasm from prostate stimulation alone, with no penile stimulation. As if that weren’t enough, prostate stimulation can offer some men multiple orgasms, which, in heterosexual couples has typically been something only women enjoy. Has your partner ever been jealous of your multiple orgasms? Try pegging and perhaps he can enjoy them, too!

  • Pegging is pleasurable for women.

Women enjoy pegging for a variety of reasons. The taboo aspect can be very hot. Some enjoy the experience of switching roles and running the show; they relish the power and control. Some enjoy giving their partner remarkable levels of pleasure, making them squirm and moan. And that’s not all…

  • Women can orgasm from pegging.

Harnesses and dildos offer a wide variety of clitoral stimulation and G-spot stimulation to help women attain orgasm while fucking their partner. Some women orgasm easily from pegging because the very idea of it excites them so much.

  • Pegging allows you to experience sex from the opposite side of the bed.

Think about it – do you really know what your partner experiences when you have sex? You will when you try pegging! And so will your partner.

You can discover how fucking a partner requires strength, endurance, grace, balance and multi-tasking. Your partner can experience how important foreplay is, how every night is perhaps not a penetration night and the vulnerability required when allowing penetration.

One of the most amazing things about pegging (besides all the pleasure) is that you both gain more understanding and compassion for each other’s usual role in sex, which deepens the intimacy that you share.

  • Pegging offers one more thing for your sexual treasure chest of choices.

Pegging involves role reversal, heightened intimacy, and the thrill of breaking taboos. Pegging can be the totally hot go-to that you enjoy on rare occasions, or the meat and potatoes of your sex life! It’s up to you.

 

©Ruby Ryder 2017

Pegging101.com, your source for pegging information without the kink.

badwomaninside.tumblr.com

badwomaninside.tumblr.com

One thing I have been hearing about over and over lately is couples who rush through the period of time between getting excited about trying out pegging, and the first time the actually do it.

There is so much to learn and so much to enjoy during that space of time! Not only will you really miss out if you rush through it, your initial experience with pegging might be more awkward and difficult as a result. So many ‘firsts’ happen, too! You don’t want to miss a one.

I’m big on anticipation. If I could give lovers a timeline to follow from when they share that first exciting moment of embracing the concept of pegging, feeling all that eagerness to explore, to the actual moment of insertion, it would look something like this…

  • For the next 5 or more times you have sex, explore his ass as a part of your foreplay. If you want to try rimming for foreplay, but aren’t sure about sticking your tongue in his ass, try a dental dam – they are sheer and ultra-thin – he won’t be able to tell the difference. Use fingers and plenty of lube. Gloves are optional. Take it really slow, make it a sensual experience. Stay in communication and have fun. Giggle and laugh if you feel like it. Sometimes exploring new territory is funny and it’s okay to feel nervous or self-conscious. Go so slow that he is arching his ass back to meet her fingers.
  • Around the 3rd or fourth time, once he can easily take a couple of fingers, use the beginner dildo that you bought for pegging. She can hold it in her hand and discover what angle, depth, and speed sends him to the moon. This is what she will be trying to duplicate when she straps it on.
  • Spend one evening staying in. She wears the harness while you both cook/eat dinner, watch TV, or clean the kitchen. This gets her used to putting it on and how it feels to have a cock! It also teases the fuck out of him to watch her walk around with it. Heh heh.
  • Finally – this is the night. He cleans out. He has no fear whether he can take the toy or not – he’s already had it inside him. She knows what she is aiming for after playing with the toy and her fingers. She’s used to wearing the harness and cock and knows how to put it on. The blanket is on the bed, because you’ve done this before. The lube is handy, along with a towel, and you are ready to begin pegging…

Enjoy.

  • Write and tell me how it went and I will play the music for you on my next podcast!

 

 

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Okay Ladies…

Let’s explore what makes you orgasm while pegging. Inquiring minds want to know, including your partners, beginners, other women who peg, and their partners!

Engaging in pegging gets me so hot that I’m dripping, but I am typically more about the orgasm that I give my partner than about me getting off. That’s the way I am built sexually. I love to give pleasure. We are all special snowflakes when it comes to our sexuality. Some women (like me) focus on giving pleasure. Others enjoy pegging men for their own pleasure, not caring about his. Some women are adept at the multi-tasking that men usually perform during PIV, and they can get themselves and their partner off. Some women come easily while pegging. Others never will. All of this depends on responsiveness of the participants, toys, technique, positions, and many other things.

Responsiveness plays a huge role in women’s orgasms during pegging, almost equal to the mental factor! Some women can get off just from the pressure of the base of the dildo against their clitoris. Of course this requires a good fitting harness that will securely hold the dildo low enough to cover the vulva and stimulate the clit. Some women get off easily because the thought of what they are doing is just so fucking hot. Some women need a Magic Wand level of clitoral stimulation to get off, and struggle to orgasm while pegging. So what are some of the factors that provide her pleasure?

Dildo Options for Her Pleasure

Doubles

Every woman’s vagina is different! The various sizes and shapes of bulbs (the end that goes in her) will vary in comfort for each woman. There is no one size fits all. Here’s an article that compares doubles.

Double ended dildos can offer excellent G-spot stimulation. Although there is not a lot of in and out thrusting motion from the bulb end that fits inside her, there is definitely some movement as well as excellent pressure when fucking him. When that pressure hits the G-Spot just right, it feels amazing! For women who orgasm more easily from clitoral stimulation (or a combination of both clitoral and G-Spot) the best double with a vibe option is the Fuze Tango, with the We-Vibe Tango Mini Vibe. Rumbly and not buzzy, this mini vibe is the strongest, rechargeable, and waterproof. It has 8 different vibe choices (three speeds and 5 patterns). Though it doesn’t insert flush into the vibe pocket space, it will never get in the way, and makes it easier to remove for cleaning.

Keep in mind that Doubles require harnesses for 95%+ women who use them, despite the ‘strapless’ claim of many manufacturers. Read more about that here: The Truth About Strapless Strap-ons. Also, many women find that using a double to begin with is difficult, because they need to learn how to fuck first. The learning curve can feel pretty steep for beginners. Of course practicing and getting good at it is quite fun!

Single Dildos

The best clitoral vibe option for a single flare-base dildo is also made by Fuze (what can I say, those Canadians have it down). Their entire line of Fuze Singles, the Velvet, Harmony, Alpha and Wilde all have well placed vibe pockets to hold the We-Vibe Tango.

There are many other dildos made with a hole in the base to insert a vibe as well. Women who need medium to strong clitoral stimulation report that the vibration is insufficient with these models, but some women love them. The We-Vibe Tango may not fit in the dildos with a hole in the base, requiring a shorter bullet vibe instead.

When choosing a dildo with the idea of her clitoral stimulation in mind, think about what she enjoys. If she likes to get off with a motion of pressing against him to increase the vibe on her clit, be sure to choose a dildo that isn’t too long so that she can be in to the hilt (when the best vibe pressure can be obtained) and it is not too deep for him. Nothing worse than needing to push hard against him to get off but not being able to do so because the dildo is uncomfortable when it is in that deep.

The dildo vibe option is great for women who like to fuck with enthusiasm, because there is a cushioning layer of silicone between her clit and the hardness of the vibe. Vigorous thrusting is still comfortable!

Harness Options For Her Pleasure

Vibe Pockets

There are a variety of harnesses with pockets to hold bullet vibes. Spare Parts Harnesses (the Joque, Sasha, Bella and Tomboi) all have two pockets for bullet vibes, above and below the O-ring on the back face of the front harness piece. Using the We-Vibe Tango (which I firmly believe is the best mini vibe in the world) will not work because it’s too long. Regular bullet vibes will work, and you can decide which pocket gives you the most stimulation, or consider using both!

The Sportsheets Plus Size Harness has a vertical pocket for the bullet, which works better, allowing the vibe to nestle in between your vaginal lips, in which case the We-Vibe Tango will work great!

Using the vibe pockets with bullets may reduce the amount of vigorous thrusting you can do, because you basically have a hard metal or plastic vibe between you and the base of the dildo. But some women don’t need as much pressure, and are more sensual peggers, so the pockets work great.

Other Harness Options

If you are a woman loves something in her ass, and you have a two strap harness like the Jaguar or the Minx, the Aslan Leather Double Up Cuff allows you to use a nice butt plug, like the Tantus Ryder or the vibrating Je Joue Nuo, which is an amazing toy all by itself (remote and long distance phone app controlled vibrations). You can enjoy the feeling of your ass being filled while you fuck your partner! You could even give him the remote to the Nuo if you wanted to….

The Double Up Cuff can be purchased as an extra for the Jaguar, but already comes with the Minx. It should work with any 2 strap harness that you own, provided you can detach the straps.

Positions

The positions women prefer vary widely, and seem to have a large mental/visual component. One of my favorite positions for my own stimulation is laying down full length on top of my face down partner and slowly thrusting into his ass (even better if he’s got a Liberator Ramp under his ass). I do have a dominant streak, so that plays into my fantasies, like I am holding him down and he has no choice. Other women find that it’s the most exciting laying on their backs while their partner rides them, simply because the visual is so fucking hot. Doggie style can feel like the ultimate power trip and be extra stimulating mentally, too. Or consider this, if you are a woman who literally gets off because he gets off, you will want the position that produces an orgasm for him, which can trigger yours.

Foreplay Before You Start Pegging

Another consideration to help you achieve orgasm during pegging relates to what you do before you start! Engage in extended foreplay, kissing, and nipple stimulation. Have your partner give you oral sex, fingering or intercourse before you start. But he can’t come if he fucks you! He will lose interest in getting pegged…. 🙁

Other ‘before you start’ options include watching porn together, abstinence for a few days prior to pegging, and even edging for a few days before, too. All those can help!

Men Love to Feel a Woman Orgasm from Pegging Them

Many men talk about how hot it feels when a woman lets go and moves for her own pleasure instead of his. Many also say that the hottest thing ever is when a woman comes from pegging them. So this isn’t only about your orgasm, your partner will enjoy you getting off, too. That’s worth working towards. Practicing is such fun!

 

 

mysextagram.tumblr.com

mysextagram.tumblr.com

So…

Over at PeggingParadise.com I’m planning a special podcast.

Podcast #115 is going to be comprised solely of women’s stories and offerings.
Most of my readership and listeners are men. For this podcast…

I want to hear from the women.

Tell us all the things you love about pegging…
Tell us the story of your favorite pegging encounter…
Tell us about your first time…
Tell us about your last time…
Tell us about a funny time, or an embarrassing time…
Tell us about your favorite pegging fantasy…

One sentence, a paragraph, several pages – I want it all!

Spill it, Ladies!

You can write me at ruby@peggingparadise.com
Or send me an MP3 of your recorded story
Or record your story on my call line (805) 500-6544

We are going to blow the men away with podcast #115!

Love,
Ruby

So, dear readers, it’s that time again. Periodically, I write a post about how pegging is not gay.

Why? Because the assumption is so very prevalent that monthly reminders are necessary for all the newcomers to my blog.

A reminder is also necessary for those of you who are considering trying it out but you have concerns. You guys lurking and reading and trying to decide if you really want to do this wild thing called “pegging” or not? Yeah. This post is for you. Here’s my message for you today:

 

Don’t listen to the little voice.

You know, the one that says…

 

He must be gay if he likes ass play.

If I peg him, he’ll leave me and go get a real cock.

If I like ass play I must be gay.

If she pegs me it’s will be like a gateway drug and I’ll want men!


That little voice is not your friend. That little voice is lying to you, misleading you and scaring you. Conclusion: that little voice is not nice. Ignore it.

 

The only thing that determines your sexual orientation is which gender you are attracted to – not what they do to you!

 

♥ If you are sexually attracted only to the opposite gender, you are heterosexual.
♥ If you are attracted only to the same gender, you are gay.
♥ If you are sexually attracted to both genders, you are bisexual.

 

In this age of marvelous and hi-tech sex toys, we can do so many things we were unable to do without them, no matter what gender we are. One of these things is pegging.  Pegging is just a heterosexual couple playing with sex toys! And believe you me, a strap-on is one fun toy to play with.

Take a look around the website and see what the men say about it, how insanely pleasurable it is.

Read why I like pegging.

Read what another woman says.

And ignore the little voice!

 

I hear from the women all too rarely. I think it is important to hear our point of view in order to understand what motivates us to lovingly fuck your delicious asses. Men often ask – why would a woman want to use a strap-on? What does she get out of it? There are many answers to that question, but sometimes it’s helpful to hear a personal story. The rest of you women out there…we would love to hear your stories, too…

Ruby,

Six months ago my fiancée, then boyfriend of two and a half years, told me he had tried anal play during masturbation and was interested in exploring this together. At first I was mildly upset/offended. Hadn’t I been a good enough lover? Was he bi-because he certainly isn’t gay. Most importantly we had been fucking for two years and he never mentioned it, although he had mentioned an interest in giving anal pleasure. I began to feel ill-equipped to please him, compared to a toned man with a raging hard cock.

Since then he has shared all of his sexual experiences with me, and I have learned that no, my future husband is not gay. Rather he is a heterosexual male who really enjoys having his ass fucked by a woman, and a prostate massage in tandem with being blown.

The best part is…I LOVE it. Seeing my glistening purple Share dildo right before I penetrate him gets me so hot, and I love hearing him moan as he gives me his ass and totally submits all thought.

There is something so erotic about being fucked and submitting as I am being penetrated. To simply feel, and not think. I am so happy to bring that same pleasure I experience to the best lover I have ever known and get to spend a lifetime in the sack with. Since we have started pegging, it has become a normal aspect to our sex life.

I am still coming to terms with accepting that I like to fuck and make sweet love to his ass, but I am coming to accept it. I enjoy taking his ass, and desire to be inside him almost as much as I long for his tongue on my clit when he is at work.

I love anal sex, and what is has done for my sex life.

-Happy Fiancée-

If you are a woman who wants to approach your man about pegging, this article is for you.

(If you are a man who wants to approach your woman about pegging click here.)

Plumisms 1

Communication

First, communication is the key. You need to be able to ask for what you want. If you can’t open your mouth and talk with your partner about sex, he is not going to magically intuit that you want to fuck him up the ass with a dildo. Take a good long look at your relationship first. Do your very best to practice Dan Savage‘s GGG – Good, Giving and Game.  “Think ‘good in bed,’ ‘giving equal time and equal pleasure,’ and ‘game for anything—within reason.'” We are not just talking about your man’s willingness to explore pegging with you…we are also talking about the state of your relationship with him…think about it. And before you blurt it out there that you want to pay his lovely ass some special attention, please read the rest of this article!

Trust

Okay, ladies – Trust. Is. Huge.

I am talking about your man’s ability to trust you not to out him. This is a bigger factor than you could ever imagine! For younger men whose generation is more open to and accepting of different types of sexual play, this may not be as big of a deal. But for men, say 30 and up, it can be the single largest factor holding them back from exploring pegging. Why? Because societal repercussions can be severe for men who enjoy pegging.

And even if they have a loving, intimate relationship with the woman of their dreams…what might happen if things don’t work out and they part? Will she tell? Will their circle of friends find out that he likes to get fucked? Will his friends or coworkers judge him? All those people likely have the same silly misconceptions about pegging that most people do and they might not look at it as just another passionate way to have sex with your partner.

Some men decide this is too big of a risk to take; getting outed. Perhaps because of their career, their religion or perhaps they live in a very conservative community. So the challenge is for you women to swear on whatever you hold sacred that you will never, ever out your guy. And keep that promise no matter what.

You know how men supposedly brag about the sex they are having? Well I’m sure there are some men who do…but the majority actually don’t. Ask around if you don’t believe me. They might make crude comments about the waitress or the woman that just walked by, but they do not talk about the details of the sex they are having with their significant other.

You know how women supposedly talk about….everything? That is actually true. Women do talk about the details. And men know that. So here is my advice around pegging. Just simply don’t ever tell. Make pegging a secret thing between you and your partner that you will never tell anyone, even your best girlfriend, even if you’ve had too much to drink. Make it a sacred thing between you and your guy so he can relax and really enjoy it without worrying about what will happen if anyone finds out…because he knows no one ever will.

So how can you reassure him that you won’t tell even if you don’t stay together? You make a big deal out of it. You tell him sincerely, to his face, making sure the timing is right (special dinner, just after sex, romantic moment, no one else around), swearing to him that it will be just between you two…forever. Another idea…consider giving him some compromising pictures of you naked that he can put up on the internet if you out him. That way you are both operating on trust.

There is also the kind of trust he needs to allow you to play with such a sensitive part of his body. Anal play is quite intimate. You are asking him to open up and be vulnerable, completely vulnerable. If you have received anal sex before you know how important technique is and taking thinks slow and easy. If you have not received anal sex before – please read up on it because ass play is best done after educating yourself! Here is a basic educational article for women who are beginners at male anal play.

Pegging is Not Gay

The biggest hurdle you will likely have to get beyond is the “No – that’s gay” hurdle. It’s like a knee-jerk reaction in many men that no one is coming anywhere near their ass…because that’s just…gay. There is a sad and rather unfortunately automatic connection between male anal play and homosexuality in so many people’s minds. Very common misconception that is 100% incorrect. The part of a man’s body that he enjoys having stimulated has absolutely no bearing on the gender he prefers to do the stimulating. (And actually there are a fair number of gay men who never have anal sex.)

Even if pegging does not threaten their sense of sexual orientation in any way…what stops most men is the thought that other people will think that they are gay or somehow less-than in terms of masculinity because they enjoy something up their ass.  For men…the blow back can be harsh. It leaves them vulnerable to ridicule, rumor and ridiculous assumptions from a largely homophobic society. Plus they certainly do not want their lovely partner to ever think that they are anything less than manly because they like ass play.

The Magic Thing to Say

Most men are pretty intensely sexual beings…if you tell them that pegging along with cock stimulation can produce orgasms 10 times more powerful than anything they have ever experienced with tons more come, most men will want to try it. I mean really, if you were a normal horny guy after hearing that could you really live the rest of your life not exploring pegging? No, I didn’t think so. Few men can.

Yet as with everything…there are all different types of men. Some will be quite ready to play at the merest suggestion. Some may require a little convincing but warm up quickly to the idea. And there are indeed those men who want nothing to do with anal play…ever, period…it’s “exit only” territory. Only you women out there have a sense which category your man falls into.

Vulnerability

Remember that men are not used to receiving and being penetrated. There is a vulnerability and openness inherent in penetration that is completely new to men. Women are quite familiar with the feeling of being penetrated during sex. For men it’s a whole new deal. And that level of vulnerability can be pretty scary, surprising, and amazing all at once. Often that vulnerability is part of the turn-on for men, but that doesn’t necessarily mean it is easy for a man to go to that space or that it is comfortable for him to be seen there. Being able to trust that the woman understands this role reversal and will not suddenly judge him when he softens and receives helps him to more fully relax and allow that vulnerability to happen. Promise him that you will handle his ass with care!

Semi-Guerrilla Ass Play

Many guys get interested in anal because a creative woman slid a well-lubed finger up their ass during a blow job with quite good results. This does present a way to introduce your guy to anal play…even if it’s a little sneaky. I don’t prescribe to the sneak-it-in-there theory…but I have heard many a man say that this is exactly how they discovered that something up their ass really turns their crank. The part of this idea that really works is that prostate stimulation generally feels best when a man is already really turned on. But… instead of sticking your finger where you do not yet have permission to go, wait until he’s very close to coming and just circle your finger around the opening of his anus and see what kind of a reaction you get. The more turned on he is by your blow job the more likely you will get a good response. If he’s not giving you any signals and you’re not sure whether he likes it, ask him!

Testimonials

If your guy is on the fence, considering it but not sure…here are some testimonials from men who love it.

Best of luck encouraging your man to let you explore his sweet, handsome ass….

Ruby Ryder

(Many thanks to my friend fliedermaus for his help with this article. His willingness to be so open about the male viewpoint was invaluable to me.)

What does an orgasm feels like with combined prostate stimulation or pegging and cock stimulation?

Is an orgasm like that really 10x more powerful than a “normal” orgasm?

♥ It’s 100% more intense than a normal orgasm due to the fact that a normal pegging means a fair amount of prostate stimulation before hand, and so long as she doesn’t stop while he’s cumming it can feel like the world has gone dark and time has slowed.

♥ Like my penis no longer matters.

Joking aside 99% of any orgasm I’ve ever had with prostate stimulation is better than any orgasm with out. The difference in feeling at least for me is that a cock orgasm is centered around the gathering pressure in the cock that feels like it tightens until you finally get release. That release is brief and short lived but amazing none the less. A prostate orgasm ignored the build up of tension and is more a build up of waves that start at the point of pressure and slowly ripple out over the rest of my body. Each subsequent wave slowly building, rolling through my body, and crashing against the seams of reality bringing me to an ever higher and longer lasting state of release from tension I didn’t even know I had. Either way orgasms are great and we should all try and have them as often as we can. If having something in your butt may make that orgasm better why not at least try it?

♥ Prostate stimulation enhances orgasm by different degrees for different guys.

For me, I’ll admit that at first it feels rather odd (probably because it doesn’t happen very often) and it can be uncomfortable if there’s too much stimulation to either location. It turns me into a moaner (I very rarely make involuntary noise), and makes my orgasm incredibly intense, it also increases the amount of my ejaculate.

♥ I like a vibrator against my prostate while I masturbate. My body just goes limp when I cum. Complete loss of all control and a blinding orgasm.
It’s even better if you can get a partner to do it for you, though. If you can get a blowjob while they work the vibrator, it’ll change your life 🙂 Or a handjob while getting strap-on fucked is pretty awesome too. I came on my own neck while flat on my back once from that.

♥ Pegging and cock stimulation give a fantastic orgasm. If you can cum at the right moment, double orgasm, it is indescribable. Its full body and brain. When it happens to me I am out of this world for some time. I am very experienced with anal orgasms. To cum at the right moment (double orgasm) takes a lot of exercise and skill from the person pegging.

♥10x…I guess I’ve never attempted to quantify the power of my orgasms. I can tell you the following characteristics.

  1. I, also, shoot my load much further and harder from orgasms that correlate with anal penetrations. I can feel my come moving along the entire length of my shaft. I often edge quite a bit before I come during anal penetration because my body and mind go numb with pleasure after these intense orgasms.
  2. I stay harder longer after getting off with anal penetration than I do without. I also get harder more quickly afterwards. Starting with anal penetrating orgasms (APOs) has led to the longest, wildest, and most satisfying sexual romps of my life.
  3. While normally not a talker, I cuss, moan, pant and go crazy with a strap-on stretching me. My heart races just thinking about the energy it feels me with.
  4. Pegging and self play is all I’ve ever engaged in. I’m always a switch but I prefer the more submissive orgasm to the dominant one because of the intense out of nature experience I have. I’m a corporate leader type, captain of sports team type, by day and most nights, but the right woman can find a deep wild lust that’s animalistic.

So, I reckon that means its a 12x better orgasm. Hell, maybe even a bakers dozen.

♥ Pegging gives the most fantastic Orgasm. If done right in combination with stimulating the cock, it will blow your brains out. If hands free it will last and last, you will keep cumming. My friend gives me the most fantastic prostate massage, no cock stimulation, which can last for hours and you keep cumming and cumming. Better than pegging.

♥ It’s both a mental and physical orgasm. Like, I can feel it throughout the body whereas a regular, strictly handjob, orgasm has like a two-eight second feel. It’s one of those weird times where the body takes over and the brain takes a hike 🙂

♥I’ve never been pegged, despite my very intense desire to be, however when I purchased one of those Rude Boy prostate/perenium massagers, I got a taste.

For me, it’s the first time I’ve ever been breathless during and because of an orgasm. The pressure and the alien sensations at first were mindblowing enough, but when I got used to it, I find myself wanting to just grind there constantly. I’ve not quite had a handsfree orgasm from it yet, but I’ve had a good 10-15 minutes of constant dribbling until I get so pent up I need to bring myself to a full climax. What I’m saying here, is that I can’t wait for the real thing.

♥ I can’t say for full blown pegging since my girl and I haven’t tried it, but I was trying to describe the orgasm I got from her fingering my ass while she blew me to a friend, and the only thing I could think of was: It’s like the ghostbusters threw one of their traps near me, and my cum was the ghost getting sucked inside. It was mind-blowing.

♥ My response to this might be strange because I discovered at a very young age (13 I think?) that I could have prostate orgasms… and I used to have sessions where I had those because they are so amazing and different from the norm. But, as I have gotten older, I usually end the session with a combination of prostate and edging into a… I guess the analogy would be a blended orgasm?

Ten times more powerful would be accurate, but not in all cases. I would say the average prostate+cock orgasm is 10 times more powerful than the average masturbation session. But I have had some incredible regular orgasms with women before, that rival my prostate orgasms. It just comes down to how different they feel.

As others have said, any orgasm involving the prostate feels so deep inside. A regular orgasm does have an internal component, but it gets so overshadowed because of the strong contractions and pure pressure in the base and length of the cock. A regular orgasm feels so right, like I’m totally in control and working toward this pleasurable goal and release. With prostate stimulation the orgasm always comes outta nowhere; I’m working toward it but each one seems different in some way, and I always worry that this time, I won’t get there. And when it does come, I feel totally out of control, like my body is almost doing something wrong. The tension/release and waves of pleasure are almost unbearable.

Of course, my description might differ from those simply getting prostate stimulation while they come… those are usually pretty intense but nothing like the ‘blended’ orgasm. I have never been pegged either 😛 Prostate play has always been my personal thing I do. Luckily I have a partner that wants to get into it, so we’ll be doing that soon. Can’t wait!

♥ Most of the time my man doesn’t squirt that far when he does come but lately, since we have started pegging, he is now shooting it hard and far. One cum shot flew past my face while he was riding me and landed a few feet back. He was also thrusting uncontrollably to the point I was a bit concerned. ( I have NEVER seen him like this in the 5 years that we have been together. ) He has become a moaner, which he never does.

Intimacy is often a necessary ingredient in pegging, and cannot be created with the buckle of a strap-on harness.

The fantasy of meeting someone, going home with them and pulling out the strap-on makes for great erotica fodder, yet it rarely happens in real life. For most people, a certain level of intimacy is necessary to consider indulging in pegging. Intimacy is created through trust, affection, understanding and sharing of confidences, among other things. Why does pegging often involve intimacy? Let’s take a look.

 

Trust, Trust and Trust

Anal sex requires trust. Just as most women would not consider receiving anal sex during a casual one night stand, men can feel even more strongly about needing to establish trust before allowing a woman to peg them. Basically there is a lot of room for error. The anus is a delicate area of the body and needs to be treated with care and respect. Just as it is possible for a man to give bad anal sex to a woman because he is not knowledgeable about the act and has never received anal sex himself, the same can be true for a woman pegging a man. She needs to know what she is doing and he needs to know that she knows what she is doing.

Education is extremely important. Learning about the best ways to make it enjoyable and even more importantly the mistakes to avoid can literally mean the difference between pleasure and pain. Before you try pegging, whether you are the pegger or the peggee, doing your research first will help you enjoy a better first experience.

 

Vulnerability

Men are not used to receiving and being penetrated. There is a vulnerability and openness inherent in penetration that is completely new to men. Women are quite familiar with the feeling of being penetrated during sex. For men it’s a whole new deal. And that level of vulnerability can be pretty scary, surprising, and amazing all at once. Often that vulnerability is part of the turn-on for men, but that doesn’t necessarily mean it is easy for a man to go to that space or that it is comfortable for him to be seen there. Being able to trust that the woman understands this role reversal and will not suddenly judge him when he softens and receives helps him to more fully relax and allow that vulnerability to happen.

 

I Don’t Know What I’m Doing

Women are not used to taking the reins and running the fuck. They have never had a cock, they don’t know how to use it and often have fears that they look as awkward as they initially feel. To be sure, wearing a strap-on and using it takes some getting used to. That initial period of awkwardness can be alleviated by being with an understanding partner whom you have a comfortable and close connection with. She needs to trust that he loves everything about her fucking him with a strap-on and that any learning curve will be accepted gracefully.

 

Emotional Responses

Just as the female G-Spot can trigger emotional responses in women, prostate stimulation can trigger emotional responses in men. Tears are possible. Yes, tears! Not many men will talk about it, but it does happen. Both G-Spot and prostate stimulation can touch a very deep, emotional part of some people. Those responses are not uncommon and are most often described as “good tears” or “letting emotions out that needed to come out”. (First time a man stimulated my G-Spot I was in tears.) It’s all good, but it may be surprising to experience and/or witness. Trusting his partner to be understanding and accepting of emotions or tears that might surface is so important for a man to fully open to the experience of pegging. This one is huge. Those deep emotional reactions can feel quite out of place during a casual hookup.

 

Her Reaction…to His

Men can have valid concerns about how their partner will react to their experience of being pegged. Aside from the potential emotional response, prostate stimulation can be so all-consuming for some men that it puts them in a bit of an altered state and the resulting orgasm can be full-bodied and very intense to experience and witness. The sight of a man deeply opened up, exposed, vulnerable and completely sensorially overwhelmed…is a rare and beautiful sight to behold. But more than one woman has gotten a little freaked out by seeing her man like that. Again, trusting his partner to accept what happens and not freak out is very important.

 

Peg and Tell

Social taboos seem to inflict more severe repercussions on men who enjoy pegging than on women who do. Many men will not want anyone other than their partner to know about their enjoyment of strap-on sex. Trusting their partner to keep that confidence is essential. That trust has not been established with a casual hookup. (The younger generation seems to be less concerned with this, which is quite encouraging. Slowly but surely, attitudes about pegging are relaxing.)

 

I Need a Woman to Peg Me!

I suspect all of this contributes to the difficulty men experience in finding partners to peg them.  There are few enough women who are interested in pegging to begin with. With the likelihood that a man will need trust and intimacy to feel comfortable exploring pegging, that takes it out of the realm of casual sexual exploration. So while thoughts of pegging may dominate a man’s fantasies, the reality often requires…a connection more akin to a relationship.

A man can pay a professional and trust her to be knowledgeable, keep confidences and not judge whatever reaction he has. I have recommended this to men who are intensely craving a pegging experience and I believe it is a valid option. Sex workers appreciate a clean, respectful client with specific needs. For men who crave it so much they tend to approach the strap-on before the woman, this can help to take the edge off.

 

Because of all these factors, it is more often an established couple who will engage in pegging instead of a casual hookup. The intimacy of pegging can be very powerful for all the reasons mentioned. It is good for both genders to be aware of these factors when considering pegging play, lest they be caught unawares at different turns.

This information certainly does not apply to everyone. There are people who can practice pegging with a casual hookup, and may even prefer to. Perhaps there are some parallels here to regular PIV (penis in vagina) sex, which can be engaged in either in a more casual, for fun type of manner, or can be deeply emotional and intimate – depending on the connection of the couple involved. But because pegging takes normal penetrative sexual experiences and reverses them, many unexpected things can happen, taking either gender by surprise.