First Anal Penetration – Steven Josephs Guest Blog

Like so many of my sexual adventures, my first anal penetration by anything other than a tentative finger, happened on the initiative of someone else.

Whilst enjoying my favourite post ejaculation recovery one day, being stroked gently by a woman half my age, she asked me if I fancied taking a strap-­on.

Yes, just like that.

She can be quite direct. I have learned that when a beautiful, intelligent woman suggests something, anything, there can be only one response. So she went out next day and bought herself a strap-on. Life is very simple really.

Next time we were together, we opened our ‘present’ and fixed the straps. I could not believe how sexy she looked in the strap-on, and that itself is a big turn on.

The girl is naturally submissive, which is lovely, most of the time. But I do enjoy her taking the initiative and becoming more dominant. I had been wondering how to encourage her to become that very thing, when she made the suggestion and then followed through by buying the strap-on.

Joys of First Anal Penetration

She ordered me to kneel, and pushed the hard rubbery ‘penis’ into my mouth. She held my head and began gently, but with growing force, to fuck my mouth. Not as pleasant as a cock (don’t ask?) but she needed to do it. And I needed to submit in that way for her. Withdrawing, she pointed to the bed.

Firstly, I went on all fours and she stood behind me. She lubricated my anus with her fingers, added lube to the dildo, then leaned forward and pushed against my opening.

The opening is tight, and there is an instinctive nervous resistance, but she eased gently into me, and I was conscious of being filled. She began to slide in and out and we continued for several minutes. Then she lay on top of me, a very gentle, loving experience.

I laid on my back, ‘missionary’, I guess, and had the experience of observing her determined face as she entered me again. The determination to control and set the pace was a delight to watch. This time she was harder. Soon, a thin film of perspiration covered her face and body, and her skin turned pink. As she took control of me, I had a feeling of overwhelming joy. I loved it. Honestly.

Then I made my masterstroke. I told her to ‘rape me.’ And that was truly dynamic. Her personality seemed to change. She placed her hands on my shoulders and, gripping me in place, rammed and rammed my aching anus until I pleaded with her to stop.

My first anal penetration was a delightful experience and I believe it would be for any man, particularly one who is endeavouring to encourage his lady to be more dominant, even aggressive. She is now threatening to buy a larger strap-on…..

Do you have an experience you would like to share? Write to me at chloe.thurlow@yahoo.co.uk

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