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The Benefits of Pegging

 

After researching about pegging, I decided to bite the bullet. I had kind of been interested in doing this for a while and thought about asking ex-girlfriends to fuck me with a strap on but I always thought that they would judge my manhood if I did.

I am currently single and so I decided to look up a kink practitioner in my local town. I found one which intrigued me but she didn’t show her face in the photos. Most of the photos on her site were her showing off her collection of strap-ons.

I wasn’t brave enough to ask to be fucked in the ass on our first meeting. I wanted to feel what she was like as a person before we got to that, so I booked an hour massage with her.

I travelled 40 minutes across town and then up fourteen floors to the top of this new tower block and entered her apartment. The door was open and she greeted me. She was super cute and you would have never had guessed she was doing this type of work. If you saw her in a supermarket, you would have thought she was a kindergarten teacher.

The massage was great, we had a great connection and I told her what I wanted next time.

A week later I arrived again into her apartment but this time I came armed with my own strap on dildo. I felt that I should get to know the cock that was going to penetrate me.

Narcissistically, I bought a dildo that was almost exactly the same size as my own member. For someone reason, I was weirdly attracted to the dildo. I wanted to know what it was like for a woman to be penetrated with something the same size as my own. I figured it would make a more compassionate lover.

I got to know my new dildo before my next appointment but I nearly broke my own asshole. 

Note: If you are going to try this... please know how to clean your ass before anal sex.

The next week, I began the travel across the city again; this time armed with my dildo. I arrived at Diana’s with a smile and passed her my dildo. She smiled and told me to go shower.

I came back to the bedroom and laid down. She then went for a quick shower and then she was ready to massage me.

Massaging is critically important to relax the body and mind before anal penetration. I HIGHLY RECOMMEND IT! She was super great at massaging me. She relaxed my whole body for at least thirty minutes before she put on some gloves and started massaging my anus.

Everything felt great. She used one finger, then two fingers. This was everything that I needed to be fucked in the ass just right. After time went by, my ass was literally begging for more. She got my dildo and put it on, and then gently put it inside me.

I had to find a complete surrender.

I suddenly felt like what it was to be a woman to be penetrated so deeply. I imagine there are similar sensations to being vaginally penetrated, and I really felt like my inner feminine was being fucked.

She made love to me for about ten minutes and then went back to using her fingers on my p-spot (which must feel like a g-spot). She was jabbing hard and fast at it, I asked for more and had such a deep orgasm that it was just crazy. It was nothing like I had ever felt before.

I would highly recommend this experience. Either using a kink sex worker or ask your partner to do it for you.

It’s not something I am going to do every week or even every month. Maybe I’ll do it two or three times a year - it requires a deep surrender and that's not something I want every day. I know it makes me a better lover every time I penetrate a woman from this moment forward. It also makes me understand that it needs specific energy to want to be penetrated.

Written by a member of ULS