Vanilla to Pegger – One Man’s Story

Thanks to my friend 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 and she did some reading. We sent more texts about it to each other. I sent her to 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 have 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 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 like 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!

7 Responses

  1. Few years ago, I was involved in a heterosexual relationship. For the first year we engaged in straight forward sexual behaviors. She used to call me MY KING, and we were so in love w/each other. Later on, one evening while we where making out on the sofa, she asked me if she could finger me while giving me a blow job, and I agreed. From that moment on, she loved fingering me often, till one afternoon she told me that she wanted to penetrate me with a dildo. Because I was so in love w/her I decided to go along w/it. At first was uncomfortable because she got a kind of a big one for me. To make a long story short, I got used to getting pegged by her, and I got so involved/in love/infatuated/lost for her/insane. But…And because this is life, she stopped loving me and I lost her. I wanted to die, I lost weight and for two years my sex drive went null. Although I haven’t forgot her, life is still beautiful, but I haven’t been able to find another loving pegging female partner and I need it so much. I’ll never be the same man I was before I meet her, but life goes on and I want to be happily in love again.

    1. doug – Ahhh. What an amazing story with a very sad ending. I send you virtual ((hugs)). Losing someone is hard, especially when you are the one who was left. I know how it feels.

      You will find someone new someday. And she will thrill you just as much as your previous partner, in a slightly different way. Join me in keeping your chin up and remembering, as you said, life is still beautiful.

  2. Thank you for answering me, I wish you could take me further in my quest.
    Ruby Red you’re the only other person to know me better. Is not easy to want to be somebody’s sweetheart without thinking if she’s going to be able to handle it and panic. I wish I could meet women like you who knows how to make of us better sex partners and male companions

    1. I wish I had a magic wand that I could use to create a bunch of women who love pegging for all you men who crave it. I feel for you, truly! Best of luck in your search.
      All the Best,

  3. Hi Ruby,

    I have a similar story. I am 29, married for about 6 years now. When I was in high school I dated a woman who was very experimental sexually and one day put her finger in my ass while giving me a blowjob. It felt great, and I recall an older guy who I worked with that I respected saying I should let a girl try this sometime. This girl and I broke up, but I dated another girl a few years later who seemed to pickup on the fact that when she rubbed her hand around my ass when playing with my balls during a handjob that I seemed to enjoy it and eventually bought a small vibrator to use on my ass when we had sex.

    At this point, I never heard of pegging. I actually got somewhat confused on my sexuality. I got teased a lot in high school with people think I was gay mostly because I wore tight fitting jeans, and as I found out later after discussions with my wife it seemed to be a jealousy issue with other guys because I was frequently dating women but was never bragging about any sexual exploits. I actually tried meeting up with guys a couple of times, but could never get past making out with them or fooling around sexually for a couple of minutes because I was simply not into at all.

    I have been into TS pornography for years. At some point I came across amateur pegging pornography. I got hooked on the idea after that. Previously, and as mentioned in some of your articles, a lot of professional pegging likes to focus on crossdressing, humiliation, and other kinks like latex, etc. Stuff I am not interested in. The amateur pegging porn made sense.

    My wife is pretty good at picking up on what I want sexually. She always knew about the TS pornography, and she was actually totally fine with it because her older brother got caught with a TS porn mag back in his high school years. She is also into watching lesbian pornography, as she’s not interested in the hardcore aspect of professional porn. When we were first dating, she realized after a few months that I was always interested in playing with her tits during foreplay and during sex that she started giving me handjobs on her tits and titjobs. It took about 2 years of dating to admit to the TS porn and was comforting to know that she didn’t find it odd or questionable.

    I was working a boring job at a grocery store and we were talking on the phone via text messages on my break. She was horny, and it was easier to talk about sexual stuff over text than face-to-face. I am pretty shy sexually, socially I am not… Probably from the catholic school upbringing I had as a child :D. In any case, I mentioned pegging during this conversation and she said she would do it for me, but it would take her a while to get used it as she wasn’t interested in “being the man”. I tried to reassure her that it’s not about feminization for me. She already understood about the prostate gland and how it could potentially feel good. She did have some concerns, particularly that she couldn’t understand how good it feels as she has never good anal experiences. We have tried anal sex before but she’s just legitimately not into it. She doesn’t even enjoy fingers her ass. That’s OK. Everyone likes different things.

    It took a long time, but every now and again I’d get very horny during a handjob or something and ask her to put fingers in my ass. It was very difficult to ask; I felt embarrassed at first. It’s hard to do these things in real life, especially when you have had a fantasy brewing in your head for years. But, occasionally I got her to do it. She even would ask sometimes if that’s what I want. She wasn’t disgusted by it.

    A couple of years go by, and I brought up pegging sometimes to her and she was still wary about trying it. She was nervous, still didn’t quite understand it. She said she would do this for me, but that she wasn’t ready to try it yet. I didn’t push the issue.

    A month ago, I got home early from work. I was at home masturbating and she came in. She didn’t catch me, but I just mentioned to her that I was in the middle of jerking off and got interrupted. We went upstairs and she was jerking me off but could tell I wanted more. She asked me what I wanted, and I told her I don’t think she’s ready to do what I want her to do yet. She told me she’ll do whatever I want, but I just need to be more confident. She said it sounds hot if I tell her that I NEED it. I told her I NEEDED her to fuck me. She smiled and said that’s better. I have a strap on I have been practicing with for a couple of years, which she already knew about it and was fine with this. I went downstairs and got it, she got dressed up and it was an amazing experience.

    It feels great when you masturbate yourself this way, but to have someone else bend you over and jerk you off at the same time makes you come so much faster and harder. Afterwards, she was much more open to it and was like wow that wasn’t so bad. We talked about it more afterwards positively. We haven’t done it again, but plan to soon. We actually just had more sexual discussions the other night and talked about our sexual confidences (she has some insecurities herself with being eating out and she gets insecure if I try to play with her clit with a vibrator) and she reaffirmed me telling her about what I need. I told her I may need something again in the future ;).

    So, my story is similar to the one mentioned above. You really must take time with it, you cannot just go to the bar and take a girl home the first night and ask her to fuck your ass. I think part of the appeal of pegging is the level of trust you share with your partner. It’s actually helped her to be more open about what she wants during sex as she realized how incredibly difficult it was for me to ask for something I wanted sexually… especially something that’s considered taboo.

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