My First Anal Sex

Ed: This is totally a work of fiction, and I’m trying to work out whether the feelings this brings up inside me are real, and whether I would find some of the scenes written in this story turn me on or not.

One weekend while M was busy doing overtime for work to help make paying off our new mortgage easier each month, I decided to do some online shopping at some of our favourite online adult toy stores.

While browsing through the pages, my cock aroused when I got to the strap on cocks. I had previously explored with anal play in the past with a review butt plug from an online store, and I really enjoy wearing the butt plug out and about, as well as at home. I thought that I would surprise M by purchasing one of these, and letting her use it on me. I wanted to know how being ass fucked felt since I was hoping to M to let me ass fuck her as well. I was hoping that by letting her do it to me, that she would be more open to it as well.

The strapon arrived on the Wednesday, and there was a little something else in there as well. I had purchased a new butt plug for myself, and some handcuffs for the bed. I hid them from M until the weekend, and over those few days, I wore my old butt plug everyday without revealing anything to M at all.

Each night when M and I climbed into bed, we made sweet passionate love in all kinds of positions, from missionary, to cowgirl, and doggy as well. Each time I made M cum before I let myself orgasm. I had her squirming on the bed, before squirting all over the bedsheets and my chest.

When we woke up on Saturday morning, I pulled the new toys our from the hiding spot, and lay them out on the bed in front of M, before waking her up by kissing her from head to toe, and dragging my fingers over and nipples and pussy slit, getting her pussy wet. As she woke up, I was getting more horny each and every minute, and was hoping to have M slide the strapon harness on and fuck my ass.

As M woke, she slid her hands down to my cock and slowly stroked it. I took her hand and guided it towards the new toys and their boxes, in particular the harness.

She grabbed the harness dildo, and slid it along her sweet pussy lips, coating it in her pussy juices. I told her that she could fuck me with it, but first she had to plug me with my new toy.

M graciously obliged as I got myself into position, she grabbed the lube from the bedside table, and squirted lube on my anus and all over the butt plug. M had never done this for me before, so it was new for her to insert the butt plug into me. I told her how I usually did it, push, wait, and then pull it out, push, wait, and pull it out. Each push being slightly further than the last until the toy is fully inserted and my ass grabs onto it and doesn’t want to let it out.

Once M had the toy fully inside me, and I could feel it, I had M lay on the bed, and I grabbed the hand cuffs and cuffed her to the bed posts before going down on her. I loved going down on M and her pussy, I loved parting her pussy lips and licking her juices up and covering my face in them. So I brought M to an orgasm, with a small squirt of pussy juices.

I was ready to be fucked, and wanted M to do the honours. I helped M slip into the harness while she was still handcuffed, and pretended to masturbate the dildo like M does to my cock. I even sucked on it for a bit, I wanted to know what sucking a cock felt like.

I helped M out of the handcuffs, and got back on my hands and knees so that M could ass fuck me. She removed the butt plug from within me, and lubed my ass up again. She also lubed up the harness dildo. I told her to do the same thing as inserting the butt plug. Push, wait, and pull.

M worked that dildo inside me until it was right up to the hilt. Boy could I feel that toy inside me. I felt so full, so much fuller than the butt plug has ever made me. I now wanted to be fucked like a little whore. Being ass fucked by M had brought the submissive out of me, and I really loved it.

M slowly slid the dildo in and out of my ass making sure not to fully remove it. It felt so great having it slide in and out of me. M slowly got faster and faster. We always had a safe word when it came to sex so that we knew if we were hurting the other. I was expecting to have to use that word at some time during my ass fucking, but I never did. I actually really enjoyed it.

Knowing that I could take the entire dildo inside my ass, I now wanted to fuck M like she does in cowgirl. I wanted to ride M like she rides me. M pulled the dildo out of me, and she lay on the bed with the dildo standing to attention, I straddled her, and squated over the dildo. I spread my ass cheeks and guided the dildo inside me ass.

I bobbed up and down on the dildo fucking it and really enjoying it. Now that my cock was exposed, M grabbed it and started wanking me as I ass fucked the dildo in the harness.

M’s face lit up and it looked as though she was enjoying this, even though she wasn’t getting any stimulation from me, I think it must have been the fact that she was ass fucking me. M wanked me real good, almost to the point of an orgasm.

M wanted to have my cum all over her breasts, so I let her finish wanking my cock while I sat there with the dildo deep in my ass. I was so fucking horny by then that I exploded instantly all over M’s breasts. There was more cum than normal, and I wonder if it had anything to do with my prostate being massaged by M as she fucked my ass.

I climbed off M, and we cleaned up slightly, removed the harness, and I went to town fucking M every way possible. After pleasuring M, she deserved the return fucking I gave her. I made sure that she cum, and orgasm.

Following our sexual adventures, we headed off to cleanup, where some more frivolity occurred before returning to bed a happy couple.