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After listening to the Raw Attraction Magazine podcast about strap ons, 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.

At this time in my life I am currently single and so I looked up a kink practitioner in my local town.

She didn’t show her face on her website but there was a section of her site where she was dressed up in a leather kink outfit and she was wearing a strap on.

I decided to write her. I wasn’t brave enough to ask to be fucked in the ass with a strap on the first time we met. I wanted to feel what she was like as a person before we got to that. I booked an hour massage with her.

I had never done anything like this before, meeting a woman for a massage in her apartment with no idea of what she looked like. I traveled 40 minutes across town and then up fourteen floors to the top of this new tower block and entered her apartment.

tower block

14 Floors Up To My Destiny

The door was open and she greeted me. She was super cute and you would have absolutely never had guessed she was doing this type of work. If you saw her in a supermarket, it would probably be the last thing you thought she did. She looked more like a teacher of kindergarten kids or something.

We spoke a little but not much and started the massage. It was great, we had a super connection and I told her what I wanted next time.

attractive woman

Innocence (not Diana but she looked similar)

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 nail the fuck out of me beforehand.

Narcissistically, I bought a cock that was almost exactly the same size as my own masterpiece. He looked familiar and for someone reason I was weirdly attracted to the cock. I just wanted to know what it was like for a woman to be penetrated with a cock the same size as my own. I figured it would give me more compassion.

I got to know my new cock a little before I met with Diana again but I nearly broke my own asshole. I was hoping that it wouldn’t be the case when I met my strap on destiny later in the week.

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

So, I began the travel across the city again; this time armed with my cock. I arrived at Diana’s with a smile and passed her my money in a sealed envelope as well as my new cock. She smiled and told me to go shower, which I did.

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

Massaging is critically important to relax the body and mind before anal penetration. I HIGHLY RECOMMEND IT. Diana was super great at massaging me. She relaxed my whole body for at least 30 minutes before she put on some gloves and started massaging the anus (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 (silicone) cock and put it on, and then gently put it inside me.

Complete surrender is what I had to find.

Deep compassion entered me. 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, perhaps though, (it is not such a struggle and it is obviously more natural to penetrate vaginally) but I really felt like my inner feminine was being fucked.

She fucked me for about 10 minutes and then went back to using her fingers on my p-spot (which must feel like a g-spot). Diana 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.

how to do sacred spot

I would highly recommend this experience. Either using a kink sex worker, or asking 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 deep surrender and it’s not something I want to do every sexual session but with the amount of deep compassion it opens up, I know it makes me a better lover every time I penetrate a woman from this moment forward.

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Raw Attraction is the leading magazine for men and women about love and sexuality. Founded in 2012, we aim to bring you life changing articles, podcasts, and videos about love and sex.

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