A Question for the Gentlemen

So...you lovely fellows who have discovered your love of Pegging...

Just how did that happen?

What changed in your world so that you found yourself dreaming about being on the receiving end of a strap-on?

Smooth transition? Rough transition?

Tell us your story...I can guarantee the Ladies are all ears.

*relaxes in an overstuffed chair with a margarita*

Ruby Ryder

8 Responses

  1. Well if you ask me what got me into it I would tell you a long while back I found a porno under my brother’s mattress, can’t remember the name China Girls or something like that, well while watching there was a scene where a guy picks up a girl at a bar takes her home and while fucking “accidentally” penetrates the wrong hole, any way a couple scenes later this woman’s sister sees this man in the same bar, picks him up and brings him home she is giving him oral and binds his hands then tells him about her sister as she brings out a vibrator, lubes his ass and pushes it in. I didn’t know why, but I became so excited by this I came almost instantly while watching (dick in hand of course). I decided to see what it felt like and after a few tries I got it right and it felt better than what I expected. I have been wishing and wanting for it ever since, I do myself but it just isn’t the same.

  2. What caused me to know that being penetrated was incredibly pleasurable was something that happened when I was 14. I was being examined by a number of doctors because my doctor was having a difficult time figuring out what was wrong with me. As part of this one doctor was mid to late 30s, brunette, glasses and uber hot. She totally got my motor going just looking at her. She decided that she need to give me a full exam. As part of it she asked me to drop my trousers and underwear. I was not sure what was coming but I was half way hard just from being near her. When she slipped her well lubed finder inside me and massage my prostate I went from half hard to wildly shooting my load more than ten feet across the exam room in seconds. I was mortified and expected some sort of trouble from this (not that I cared that much at the time), but she kindly cleaned me up, sat me down and assured me that everything was fine and that this was an intense but fairly normal reaction. I have been into the thought of ass play ever since. It took me many years to find a lover that enjoys it like I do but that is another story.

  3. ezduzit – what an amazing thing for you to experience at 14…wow. Thanks for sharing your story.

    I’ve always wondered about men’s prostate exams. There is enough porn out there with the nurse doing the exam/enema/pegging that it’s obviously a thrill for some. That well-lubed finger might be the only exposure some men ever have to anal pleasure. Glad to hear you took that experience and ran with it…eventually!

  4. From a reader…
    My wife and I occasionally get away for the weekend without the kids. I noticed that she was intrigued with the gay porn movies in the hotels. We always seemed to be watching them. I didn’t mind because it made her incredibly horny. We talked about about it a few times and she played with my back door in the shower. It was an incredible orgasm! I finally got the courage to ask her to do me with her dildo. It was amazing! I might have enjoyed it too much, as I think it may have scared her a bit.

  5. Sometimes the intensity of orgasms with anal stimulation are a bit wild. I hope she sees it for what it was – passion with a capital P. Ask her for it again and offer to please her sexually in whatever way she desires as an exchange…maybe that will get her to put the strap-on where you want it!

  6. My introduction to anal stimulation occurred nearly 40 years ago, when I was 13. I had some major abdominal pain and my parents took me to the local hospital’s emergency room. I had some major blockage, relieved by a hospital enema. Upon discharge, the doctor recommended that I have a weekly enema and recommended that my parents order an enema kit through the hospital’s supplier. He explained it was top grade, better than drugstore quality and was available at cost e.g. no mark-up. My Mom agreed and my Dad pulled out his chequebook.

    My Mom had never given an enema before, so she called her Mom [my grandmother]. Leave it to me, Dear, was her response. Fortunately, my grandmother lived a couple neighbourhoods over. Granny was an early riser and directed that I drop by her house early Saturday morning. If that worked out OK, then early Saturday morning would become a weekly routine.

    Granny was very adept at giving a gentle enema and putting me at ease. She was extremely impressed with the enema kit obtained through the hospital, ordered one for herself as well, and highly recommended that Mom and Dad get their own too.

    The kit had a rather large, bulbous retention nozzle. Getting that in required a lot of Vaseline and prep, but she did it gently and soon that rather large nozzle was nuzzled in my rectum, secure, with the widest part of the bulge pressing against what I later learned was my prostate gland.

    I won’t go into any more detail, but if there is enough interest, maybe I’ll write some stories about my past experiences.

    1. Ahhh! An enema introduction. That’s a new one – you are the first man I have met who found out about prostate pleasure through enemas. I’m quite sure you are not alone – they just have not written me. 🙂

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 »