Gentlemen

First of all…

You are not alone.

Certainly not alone in the sense of enjoying anal stimulation, and not alone in the sense of scared to tell your significant other. It can be a super scary thing, for a lot of reasons.

Telling your partner requires 3 things.

  • Communication
  • Information
  • Patience/Persistence

Communication:
Do you two talk in bed?? Do you talk about sex? Do you tell each other what turns you on and how things feel and what you fantasize about? If you don’t, start right now. If you are not used to it, at first it will be hard to open your mouth and get the words out. Communicating about sex opens doors and brings you much closer together, beside adding a bit of titillation factor to both of your sex lives!
Information:
Does your wife know that prostate massage has been proven to help with a healthy prostate?
Here’s the study
Does she know that the prostate is capable of giving intense levels of pleasure, just like her G-Spot?
Does she know that pegging doesn’t have to be like pegging porn?
Does she know that you enjoying anal stimulation says nothing about your sexual orientation?
I created a podcast just for the women, to address all of their fears and concerns. I recommend you listen to it first, because only you can decide whether it’s right for your partner. Many men have had great success with it!

Patience/Persistence
When you tell her about it, don’t present it all self-conscious like you have leukemia. Tell her you discovered something way cool – that you have another erogenous zone and you want nothing more to explore it with her. Be excited! Give her the information and then be patient for a few days. Ask again, no resentment, no impatience, just eagerness and curiosity whether she looked at the information or listened to the podcast. Be patient, but persistent. And above all, calm.

Of course you have fears! Among them…

  • She will think you are gay
  • She will think pegging will turn you gay
  • She won’t respect you in the morning
  • She will tell her/your friends

The podcast will help a lot with all of these.

Because here’s the thing…
Do you want to live the rest of your life never asking her? If she is down to try it, you could be enjoying pegging right now. And if she isn’t, then you at least asked. So many men wish they had not waited so long to ask their partners. Pegging is a very intimate act, so wouldn’t it be awesome to be doing it with the person you are the closest to in the whole world?

Now, if your partner is sexually inhibited, sexually conservative, sexually close-minded, and you only do it missionary position, no oral or anal, then perhaps it would not be a good idea to blow her out of the water with pegging. Only you can decide!

Good luck!
Ruby

newryder7

Podcast: For the Ladies

I have been recording podcasts for some time, but this last one might be of particular interest to you.

For a while now I’ve been working on a book, a short and read-in-one-sitting book, in my voice, that was specifically intended for men to give to their partners to introduce them to the concept of pegging. I’d pretty much finished it, but I changed my mind.

I made it a free podcast instead. I decided that I wanted it to be available to anyone that wanted/needed it instead of being something they had to pay for on Amazon (my original plan). Because, basically my goal is to facilitate as many couples understanding and enjoying pegging as possible. Especially the women!

And I think this might help.

Men could introduce the basic concept to their partners and then direct them to the podcast and say “listen to this”.

I address the common misconceptions and fears, hold space for those who decide it’s just not their thing as well as those who decide to embrace it, and through it all, emphasize over and over again that it took a ton of courage for you guys to approach them, and it is truly a gift of intimacy. Because you are allowing them to know a deeper part of you, no matter how they decide to respond. I encourage communication over and over, because good communication about sex is indeed the sexiest thing out there!

For those who are interested – could you give it a listen and let me know what you think? Feedback? Did I miss anything important? Criticisms?

Podcast is 50 minutes in length and you can stream it directly from my other website. Click the link under the photo above.

 

 

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 man who wants to approach your woman about pegging this article is for you.

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

 

http://isissandosiriss.tumblr.com/image/28677070563

http://isissandosiriss.tumblr.com/image/28677070563

Podcast #112 – For the Ladies

Update: I recorded the above podcast specifically for the circumstances where you have just introduced your partner to the concept of pegging. The podcast is in my voice, talking to her. I offer accurate information, dispel myths and misconceptions, and emphasize the health of the relationship above all. I don’t try to persuade, I inform, and verbally hold space for those who decide it’s not their thing. Please listen to it first before sharing it with your partner, because only you can decide whether it’s appropriate for her!

I Don’t Want Her to Think I’m a Freak

For you gentlemen who have an established relationship and you want more than anything to convince your partner to peg you…what is the best way to do this? How can you approach your lady…and let her know that pegging is what you fantasize about, dream about…that you’d like nothing more than to have her slide a smooth silicone cock slowly up your ass? And how can you get this idea across without her thinking…you are a freak/gay/twisted/weird? I will do my very best to try and help you here…but please realize there are many contributing factors. While some of you may be able to just casually mention your interest and quickly find yourselves shopping for the right dildo, others will find that despite their best efforts, their partner won’t consider pegging…at all, period, end of discussion, case closed. But let us remain hopeful…


Communication and GGG

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, she is not going to magically intuit that you want to get fucked up the ass with a dildo. If you demand instead of ask…that’s not likely to meet with any success, either. 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.'” If you just want to find one more way to please yourself and you don’t really give a flying fuck about her pleasure, don’t bother asking for anything until you get your act together…seriously. We are not just talking about your lady’s willingness to peg you…we are also talking about the state of your relationship with her…Think about it. Make sure you take into consideration her state of mind and whether she is stressed out with time demands, work, children, etc. Do your best to alleviate her stress and make sure you contribute equally to the relationship.

If you are indeed GGG and think you have a partner who is so open to new things while remaining unaffected by misconceptions and stereotypes that you can just tell her straight away that you would like to try pegging, by all means go for it. Some men actually have success this way! But be forewarned that you may also put her off the idea for good. Big risk. If you even get a hint that any part of her will be reticent about the idea for whatever reason she may have, I’d advise using a different, more gradual approach. Keep reading.

 

Important – Do Not Ask For Strap-on Play Right Off!

Patience is the key here. Many women when asked for strap-on play right off the bat have refused because they have no idea what pleasure the prostate can bring. Also, they have nothing to counter the usual misconceptions connected with pegging. If those same men would have asked just for fingers to start with it’s likely that some of the women who refused would have indulged their men in an attempt to bring him pleasure and then discovered just how amazing it could be for their man. So remember, have patience and ask for fingers first. Bide your time.

Next, let’s divide your women into two general categories: those who accept anal stimulation themselves and those who don’t.

 

She’s Into Anal

If your lady has already shown a willingness to engage in anal play, you have a foot in the door. If she is willing to let you put a finger or toy or your cock in her ass, there is a much better chance she will consent to exploring yours. Tell her you can see she is enjoying it and you want to see what it feels like. Or…you read an article about prostate orgasms and want to experiment. Or you heard from a friend/read on the internet that men can have insanely powerful orgasms with a lot of come and you’d like to try it out just to see what happens!

 

She’s Not Into Anal

This is a more difficult category, guys. Maybe you have a woman who has always refused anything anal; you touch her anus and she flinches or pulls away. There can be a lot of reasons for this. Perhaps she was told as a child her anus is dirty and should never be touched. Perhaps she thinks that only sluts have anal sex. Perhaps she is a bit of a germaphobe. Maybe she’s just totally grossed out by anything to do with excrement. Or maybe it’s just as simple as she has not yet been able to open up and own her sexuality without being concerned about what other people think. Sometimes that comes with age. Any or all of these could be true. Or…it could also be true that no one has ever played with her ass before (including you) and she just doesn’t know how pleasurable it can be.

Be aware that there are women out there that just don’t like receiving any kind of anal – yet that does not preclude their interest in fucking you! So even if your partner is not into anal at all – she could still be an enthusiastic pegger. Receiving anal herself is not a requirement. So if your partner gladly slips a finger up your ass during a blow job but steadfastly refuses to let anything near her ass, this is still good news. Just skip down to Offer Another Trade.

 

For the woman who is not into anal, consider the following approaches and ideas:

Explore Her Ass First

Two ways to do this…only you know your partner well enough to know which one might work best.

1) Get her incredibly horny (oral, kissing, nipple play, etc.) and ask if you can please, please, please play with her ass. Put your pride aside and fucking beg, if that’s what it takes. Promise her that you will only use your lips, tongue (if you are into rimming) and one finger or a small toy; your cock is not going to come anywhere near her ass. Because that is the fear of many women – the ignorant and savage thrust of a cock up an ass as if it were a pussy has put many women off anal sex….forever. So you need to go at this ultra-slow. And no matter how tempting it is for you to slide your cock into her ass…don’t do it unless she asks for it! And even if she asks for it, continue to tease and play and open her up for a while until she’s begging for it and you can easily put 2 – 3 fingers inside her. If she doesn’t ask for it…do some ass play as foreplay and then fuck her vaginally. Afterward, wax poetic about how totally hot that was to play with her ass and you absolutely loved it. The idea here is to get her used to ass play in general before asking her to peg you…and to wake her ass up to the pleasure potential there. Important: while you are playing with her ass keep the communication lines open and keep asking her if she likes what you are doing as you try different things.

2) Discuss your desire to play with her ass when you are not in bed, when you are having some close together time. Ask her if she would be willing to let you play with her there…that you promise it won’t hurt and just the thought of it really gets you excited (and you swear you will absolutely not put your cock up her ass). Reassure her, if it seems necessary, that you will love and respect her no matter what you two do in bed, and you will attend to cleanliness issues in whatever way helps her to feel comfortable. If you are not into rimming or the thought of it grosses her out, fingers and small toys are fine…even a small toy that vibrates! If she agrees, proceed as described above. If she becomes receptive to anal play, consider anal beads and experiment with pulling the beads out at the moment of orgasm trick. Find out what she likes best – ask questions!

 

Offer a Trade

If she is reticent – offer a trade. Tell her that if she will let you play with her ass one night, you will do whatever she wants the next night. And be ready to fulfill any reasonable request of hers. This is all about mutual pleasure. If you can get her to enjoy anal play…it is much easier to introduce the concept of her exploring your ass. (If she refuses – see below “Show her How Good it Feels For You”.)

Once you have played with her ass several times very successfully (not necessarily even fucked it) you can try talking with her about how you would really like to know how ass play feels. You can see how much she is enjoying it, and you read/heard that orgasms for men can be insanely powerful with anal play. Don’t mention the strap-on yet. If she goes for it – excellent! If she is still reticent…

 

Offer Another Trade

Tell her you will trade her one night of pleasing her in whatever way she likes best (it’s all about her) for a night where she indulges you in some ass play (it’s all about you). Suggest that if there is something she’s wanted to try but hasn’t asked for yet, this would be a fine time to put it on the table, as you are very interested in pleasing her sexually in the way she wants to be pleased. And you’d like to explore your interests as well. Just be ready to put on the lace panties or paint her nails or whatever it is she wants. As long as it is not a hard limit – it would behoove you to indulge her…just as you are asking her to indulge you.

 

Resistant? Start Off Slow

Do not go straight to asking her to fuck you in the ass with a dildo! Too much, too fast. Tell her again that you have discovered/read/heard that ass play feels really good for men and you want to explore it with her. Have her try fingers first (gloves if she wants them), giving her nothing but positive feedback if she’s game. Pick out a plug together and ask her to put it in you to wear while you are fucking her or when she is giving you a blow job or hand job. (Invite her to wear it while you are fucking her, too!) Exclaim how amazing your orgasms are with the plug in and suggest you try other toys. Maybe at that point talk with her about strap-ons. Tell her, while looking into her eyes with the best smoking-hot look you can muster, that just the thought of her…wearing a strap-on and doing you…about sends you over the edge. Just the thought.


Choose Your Timing

Do not start a conversation like this when you are in the middle of having sex. Talk with your partner about this out of the bedroom. Otherwise she will feel pressured and believe me – you stand a really good chance of killing the mood…and killing your chances. Choose a time when she is relaxed, receptive and maybe even had a glass or two of wine. An incredibly important point here is that you need to be a partner who is responsive to her needs if you are asking her to be responsive to yours. Read that again and think about it…and if you are not that kind of partner, make those changes before you ask for pegging. Your woman needs to feel that you take very good care of her needs and desires in the bedroom. If she feels that way, she will be much more likely to give you what you are asking for.

 

Confidence

A friend of mine offered another very important point to keep in mind when you ask for what you want. Her words say it best.

“Women are like dogs in that we can smell fear….if, when you ask us to play with your ass, you are worried or nervous, we will sense it and think you’re asking for something weird. If you project confidence that you’re asking for something totally normal, we’re more likely to agree.” Strap-on Jo

 

You’re Gay?!…This Will Turn You Gay!!

Undoubtedly, some of you will encounter the “gay” reaction from your partner. So…

I am going to give you a few choices of what to say if she accuses you of being gay or worries that if she pegs you it will “turn” you gay.

  • “That’s silly, Honey. If fucking a guy in the ass with a dildo makes him gay…then fucking a lesbian with a strap-on will turn her straight!”

Okay, maybe you don’t talk this way…maybe you are at a fine restaurant and trying to have this conversation clandestinely. Here is a toned-down version:

  • “Don’t be silly, Darling. The area of my body that I enjoy having stimulated has no bearing whatsoever on the gender I prefer. I am completely, 100% straight, period. The only person I want playing with me…there…is you.”

Other options:

  • “Nope, I definitely prefer breasts with my strap-on. Would never let a guy near my ass. You got nothin’ to worry about, Babe.”
  • I am just interested in exploring whatever brings us pleasure, Honey…I haven’t switched camps!!”
  • Your pussy is the only thing I want to sink my cock into, and your strap-on is the only thing I am interested in having sunk into me.”

You can also show her or read to her “No, He’s Not Gay” where I go into this in more detail.

 

She’s Freaked Out by Wearing a Cock

I didn’t know this was an issue, because I never had any back off strapping on a dildo. Some women, however, have a real reaction to it. She may think it means she wants a cock and it freaks her out (tell her you know she doesn’t want a cock for real – this is just about using toys to play)…or it feels too much like role reversal and she is really not into that idea (tell her you have no interest in reversing roles…but you are interested in playing with toys)…or it’s just too awkward and she feels foolish (tell her trying something new often feels awkward and that’s okay – you will both figure it out). If your lady has played with your ass and is okay with that, leave the harness aside and let her use the dildo with her hand. Once she tries it she may warm up to the idea of strapping it on. She may not, but one can hope.

 

It’s Dirty

If she’s resistant because of the “dirty” idea, tell her you will prepare by giving yourself an enema and she can use gloves. You will do everything you can to be as clean as possible. This means not eating a lot of crap or drinking alcohol a few days before, too, because that will make your feces stink more than usual. Read “Keeping Things Clean” and take the advised steps to ensure a positive experience for both of you.

 

Do NOT Show Her the Porn

Whatever you do, do NOT show her your favorite porn clip of pegging! I say this because the vast majority of “professional” pegging porn includes aspects of humiliation, feminization and abuse. If you play that way – more power to you, but I suspect if you are here reading this article you have a partner that might be a little more vanilla. The very last thing you want is for her to see that porn showing a guy dressed up as a woman and being beaten while she taunts him and fucks him. Again – this is not a judgment about what turns you or your partner on. I am just saying be aware of what you are exposing her to and how she might react to it. Spend some time looking for a few hot amateur porn clips that are loving and gentle and the man is moaning in ecstasy. They are out there!

 

Show Her How Good it Feels For You

If she is completely unwilling to give or receive anal pleasure and you are not willing to live without it, go ahead and carefully lay your cards on the table that you are very interested in ass play yourself, even if she does not want her ass explored. Consider asking her if you can just put in a butt plug while you fuck her, just to see what it feels like. She won’t have to do anything; you put it in yourself (moan a little). When she sees/hears the intensity of your orgasm, she might be more curious and interested in checking out your ass. This works for women who are sincerely interested in giving their men pleasure. If she doesn’t give a hoot about your pleasure…I don’t have any magic words for you. Maybe call Dan Savage (sex advice columnist) to explore your options.

 

Warning! Read This Before You Act!

Men who would love to experience pegging have fears of expressing their desires, understandably. There are some men who never confess their fantasies much less try to turn them into reality because they are so afraid of or even certain of rejection. Indeed, with the taboo factor and society’s puerile judgment that if a man likes anything anal he must be gay, men’s fears are legitimate. I’m telling you this because you need to make sure your partner is trustworthy before you divulge your innermost sexual desires to them. Only you can make that judgment call. And I so wish I had a magic wand for you. On one hand I would love to see you guys let go of your fears and express your desires to your partner.

I have heard amazing stories of men who did just that and their women, after initial surprise, agreed to try it and ended up loving the feeling of fucking their husbands. I have heard stories of how it totally renewed the sexual spark in a relationship of many years. Yet I have also heard sad stories of women who called their husband gay and never fucked them again. Honestly, I just want to slap those women for being so sexually fucked up and for being so cruel to their husbands. So again…we come back to the point that your relationship needs to be solid, intimate, sexual, trusting, open and communicative. If divulging a yearning for pegging might destroy your relationship, you need to decide whether you can go the rest of your life not having your sexual needs met, whether you need to leave the relationship and find someone more sexually compatible or whether you can come to an agreement that you can get your needs met elsewhere. Tough questions.

 

A Request From Ruby

For those of you who have success with your ladies, do me a HUGE favor and ask her what it was exactly that convinced her to try it? Then write me an email and tell me! I want to know what persuades an initially reluctant woman to strap one on and learn to love fucking her man. And then I will do my very best to bring many more women around to the idea….because I know how much you all want it.

 

Gentlemen…I will keep your wanting and willing asses in my thoughts (that’s easy) and hope you all find yourselves enjoying a thorough pegging very soon.

 

Ruby Ryder

 

 

 

 


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.

Thanks to my friend D for allowing me to post this piece. There are so many men out there who want it, need it and crave it. Here is one man’s suggestion on how to find a woman to peg you.

This is for all those guys who are begging for some random lady to bend you over. Here is how I did it.

I met a regular young vanilla girl on a very vanilla dating site. We went out on a date or two before we had sex. We talked about sex more and I made some comment about how young girls are prudes. She asked how? I said that they are not adventurous. So we talked about anal sex and eventually on date 4 or 5 we have anal sex and she loves it.

A few dates later I took her to a sex shop that just happened to be in the same parking lot as the restaurant we are ate dinner at (nod nod, wink wink). After dinner and a few drinks we walked around looking at all the lingerie, toys and videos. In the toy section I casually pointed out a strap-on and asked her if she would do a girl with it. She said no way, she is not into women. Later we have more regular sex.

Then we texted a lot about all sorts of sexual topics including blow jobs and prostate massage. She said she was unsure about fingers in the ass as her nails might scratch. At some point she put two and two together and asked what I thought of strap-ons. I played dumb and said I’d like to try it with her.

I sent her to www.take-it-like-a-man.com and she did some reading. We sent more texts about it to each other. I sent her to www.peggingparadise.com/blog and she read more. Along the way she had some reservations… like – is this the only sex I want? How often do I want to do this? Etc…. She said she wanted to try it but only because we were now in a relationship. We had been dating for a few months.

She was concerned that she may not like it and didn’t want to invest in the equipment. Lucky for her I already had my own equipment. She was ok with that…and the obvious fact that I had done it before. I assured her that everything was sterilized and clean. Our first time is using a regular strap-on dildo and she is very awkward at it. I get off and keep reassuring her how great it was. She wasn’t that into it the first time.

Then I let her borrow my Realdoe. It’s a double ended dildo and she likes the flesh color. She just happens to like watching porn so I sent her to www.xhamster.com and told her to search for strap-on scenes. She got to masturbate with the Realdoe for a few days before we saw each other again. It was important that she felt comfortable with the dildo and knew how to get pleasure from it.

The second time we were together for pegging,  she was much better at fucking me because she had warmed up to the idea and knew how much I liked it. Of course I was still pleasing her first sexually before she pegged me.

So that’s it, guys. You are not going to just find some random chick off the internet and say hey baby bend me over. Find a real woman to date or get your significant other to do it.

I have done this in my past 2 relationships and it blows the girls away to do something different and unique. It’s all in the delivery and it takes time and effort but it is so worth it.

Happy Pegging!

Sort of like the cart before the horse…

For the Gentlemen…

Since diving dildo-first into exploring the world of pegging…one thing has really jumped out at me.

It is this…There are many, many of you men out there who are interested in being pegged, whether you are new to the experience or you have your own equipment in your dresser drawer. You dream of feeling that dildo slide into you, teasing you, filling you up, thrilling you. You want to be used, fucked, lovingly pegged or hammered. You crave it. You want it. You need it. You beg for it! And you frequent any websites where there might be women who are interested in it. Wow.

I guess what I am saying is I get that you guys who love pegging really love it. I mean really.

Now…I have witnessed how profoundly my guy is affected by pegging. He swoons with pleasure and gets pretty damn loud with passion. In fact he recently described his ass as “wanting and willing”  (that man so knows how to sweet talk me). So, guys, I can understand  your desire to regularly experience that intense degree of sexual bliss.  Once you’ve had it…you want more. Like your first blow job. You might even obsess about it. I get it. The strength of your desire for pegging is intense. Not to mention that men are pretty single-minded about sex in general.

Which brings me to…the methodology behind your approach of potential pegging partners.

First, I offer you an example of the worst approach I have ever personally experienced via email.

“your cock would look good in my hole”

I swear to God, just like that. No capitalization, no punctuation, nada. This approach is definitely not recommended if you are interested in finding a woman to peg you anytime in the next century.

From the woman’s point of view, here’s a hint, guys.  Don’t pursue the toy with greater enthusiasm than you pursue the woman. We women who peg, yes, it’s nice to know how much you guys enjoy it…but it is also nice to feel like you are interested in us as people first and wearers of dildos second. Get to know us…meet us for coffee or dinner…have some conversations with us. To be pursued as primarily the wearer of a strap-on is quite off-putting; like being used to satisfy your fantasy. (If you truly only want to get pegged and are not interested in the woman doing the pegging, just go find a professional.)

Please remember…There is a woman at the end of that strap-on!

An alternative method of finding a woman who pegs is to find a woman…..and turn her into a pegger. Here is a story from a friend of mine who did just that: “Vanilla to Pegger – One Man’s Story.”

 

Happy Pegging,

Ruby Ryder

Pegging…this thing we love and indulge in with such passion and excitement…requires equipment. Indeed, much has been discussed here at Pegging Paradise about the necessary equipment; lube, harnesses and dildos. Let’s back up a step, though. Let’s talk about the step between “Approaching Her About Pegging”  and the act of pegging itself.

 

She needs to actually strap on a cock

This is not as easy for a woman as you may think. I am going to address this article to you men who want more than anything for your woman to fuck you with a strap-on. Let’s say you have already broached the subject – she’s interested and is considering it….

  • Assuming she understands that the male prostate can provide intense pleasure and she really wants to give her partner pleasure
  • Assuming that she has gotten past the misconception or fear that her partner is gay
  • Assuming that she is open enough to not be freaked out by sex toys in general

Even assuming all the above, actually strapping on a cock may be a huge step for a woman. If you sense some reticence, consider the following…

She is being asked to do something that messes with strict social gender roles. Though one can say it’s just a toy and it doesn’t mean anything other than that you like to use toys…that’s not the reality of it in that moment when the buckles are fastened and she has…a cock. Having a cock, penetrating and thrusting are quite male-associated things. The whole idea that she could take on the active, penetrative role might take a while for her to adjust to.

Some women have fears that they will look ridiculous. Partly because they have never had a cock hanging between their legs and it looks quite strange from their perspective. What most women do not realize is that if their guy is interested in strap-on sex, actually seeing her put on a harness and dildo is so hot they can barely stand it! (And she thought she would look ridiculous…)

There are women who cannot reconcile wearing a cock with their femininity…they want to be feminine and see strapping on a cock as acting like a man. Though it is far from that cut and dried, there is no denying that the role of strapping on a cock and fucking her man requires a woman to be active instead of passive, giving as opposed to receiving, penetrating instead of penetrated.

Indeed, there are a fair amount of emotional factors that can interfere with…strapping on the cock.

So take it slow. Let her hold the dildo in her hand without the harness and fuck you with it first for a few times so she can see how intensely it turns your crank. The first time you use the harness…try to have it fairly well adjusted from a previous try-on so she can just step into it and you don’t have to struggle with getting it just right. Otherwise all the straps can be a lot to figure out. Once on – tell her how unbelievably beautiful and hot she looks…because you know she will.

 

Remember, she’s never used a cock before

Another concern women have when strapping one on for the first time is that they have no idea how to use it. They are completely unfamiliar with the body motions required to fuck their guy.The lovely hip roll and thrusting instinct that men have is a learned skill for a woman. At first it feels quite awkward and it is common to feel a little ridiculous. For the first time she does you…suggest that she lie on her back and you can ride her. That eliminates the skill factor on her end – and gives her a great view! Plus access to your cock, which in pegging play is always a good thing. (Do make sure you tell her that it is common and normal for men to lose their erections or for them to come and go and it still feels incredible.) Tell her this so she won’t worry whether you are having a good time or not. And keep telling her how good it feels while you are riding her. Make sure she has no doubt that you love it.

Above all…have fun! Don’t get too serious about it all. Laugh and play and talk and experiment together…that’s the stuff good sexual relationships are made of.

Ruby Ryder