Reader Question

Hi, I'm **** and I'm from Spain. I have a stable relationship with my girlfriend. I met her more than 5 years ago.

Since 2 or 3 years, I receive anal pleasure from her, first with fingers and after have talked with her, we incorporated a little dildo in our games.

I love to being fucked by it, and also I've told her that I want to try it in different positions.

Now, I want to incorporate a strap-on.  It is one of my biggest fantasies, but I don`t know if it's early for this, because, as I say before, we have the dildo since a month.

The other problem is I'm afraid about her feelings, if I tell her that I want to be pegged. I love her, and we're waiting for a baby, and I don`t want to hurt her feelings, maybe, she can think that I'm interested in men.

Thanks to hear me, or read me, and I will wait for a possible response from you.

Kind regards, and sorry if my English is not very correct.


Hello Dear Reader from Spain!

Your English is just fine - very understandable.

I am very happy for you that you and your girlfriend already enjoy anal play. If she is already using her fingers and a small dildo to give you pleasure, you are more than half of the way to pegging. She is okay with anal play. She is aware of how much pleasure you receive from anal stimulation. And she is okay with using a dildo to give you that pleasure. These are all very positive signs.


I can think of two reasons she might have difficulty accepting the idea of using a strap-on harness to peg you. The first is that some women have an emotional block when thinking about actually strapping on a dildo. They fear a loss of femininity and attractiveness. They also might have issues with the role reversal involved. I'm not talking about you dressing up as a woman or her pretending to be a man. I'm simply referring to the thought of being the one who penetrates and does the fucking instead of what a woman is used to, which is being penetrated and receiving.


The second is the fear that you might be gay. Since you two are already using a dildo and she has not expressed that fear - hopefully she is not affected by it. But sometimes the act of strapping the dildo on can bring it up.


I suggest you be honest with her and tell her. First tell her that you are really enjoying your sexual relationship and she makes you very happy. Then tell her that of the most arousing things you can imagine - one that thrills you just thinking about it is her wearing a strap-on dildo and you both continuing to explore anal play in that manner. She is obviously interested in giving you pleasure so she will probably take your request seriously. Present it as something fun and exciting to explore, without shame or embarrassment. Be sure to tell her how intensely the thought of her wearing a strap-on turns you on and you can't wait to see her wearing one. This will likely ease her fears of looking awkward or unfeminine, which some women have. Using a position in the beginning that does not require a lot of skill on her part is a good idea when you get to that point. If she lays on her back and you ride her, it will be easiest for her.


As far as her fearing that you might like men, I wouldn't bring it up unless she does. If she says anything about it,  be sure to stay calm when responding. Don't get angry or defensive. Just tell her that's not the case. Here are some possible ways to respond - choose the one that works best for you.

  • Don’t be silly. 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 my ass is you.
  • Nope, I definitely prefer breasts with my strap-on. Would never let a guy near my ass. You have nothing to worry about, Sweetheart.
  • 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 are all I need.


If she worries that pegging you will turn you gay, try this one:

  • “That’s doesn't make sense, Honey. If fucking a guy in the ass with a dildo will turn him gay…then fucking a lesbian with a strap-on will turn her straight!”


One last thing. You mention you are "waiting for a baby" and I'm thinking this means she is pregnant? If she is pregnant be very careful because pregnancy can make women feel unattractive. it can be a delicate time to introduce a new toy when she might be feeling unattractive with the extra weight. When a woman is pregnant it is so important to tell her how beautiful and sexy she looks. The hormone changes in pregnancy can also make her more emotionally reactive. Since you are enjoying sex with anal play, it should be okay to talk with her about it, but if she is not interested or reacts badly be prepared to put it on the shelf until after the baby is born and she returns to her normal sexual self - which could be a while.


Good luck to you and let us know how it goes!

♥Ruby Ryder♥


Leave a Reply

Your Source For All Things Pegging

Information and resources for anal sex, bdsm, strap-ons, intimacy, and female domination. Let Ruby know what you think! Leave a comment, register for erotica, or catch a webinar.

More Articles

Anal training cone pops right up

Podcast #303 Pops Right Up!

Pegging Paradise Podcast #303 Just when you wondered if you’d lost me… Another podcast pops right up! Information/Articles Equipment I hope you enjoy this podcast.

Read More »
Ruby Ryder shares stainless steel chastity cage with lock for chastity play

It’s Good to be Clean

Masturbation Month 2024 #29 (Link to Part One) Cleaning day! What the actual fuck, thought Frank. Sure, he could see the point behind it, and honestly

Read More »
Sportsheets Thigh Harness offers the best kind of railing

The Best Kind of Railing

Masturbation Month 2024 #27 (Link to Part One) Times past when Frank had wanted to be fucked hard and powerfully, and Cynthia hadn’t been able to

Read More »