This story is about anal sex (A)
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Years ago, I never expected to write this story. But things change, and here I am, feeling like I can’t wait to relive my latest sexual experience with my wife. I will save details of the beginning of the evening for another story, but suffice it to say, in light of the quarantine living situation and her desire to not get too out of shape, my wife suggested the following.
“How ’bout on the nights we are planning to make love, I first put on one of my workout videos in the bedroom and work out while you watch, slowing taking off more of my outfit as I go?” Who could resist that offer? So that is how the night began, and once she finished her workout/show and took a quick shower, this is the story of how it culminated.
Now briefly, here is why I never expected to be writing this story. Years ago, at a time of self-evaluation of our sex life, my wife and I filled out a long questionnaire and had an excellent discussion about what we would or wouldn’t want to try. When the topic of anal sex came up, she said she was not really interested, and I said that was no problem since it really didn’t interest me either. I guess that changed somewhere along the line for each of us.
Just over the last few months, my wife has become more and more comfortable with me touching her anus. Quite often, when she is on top making love to me, I will reach my hand around her backside where I can lube up my finger with her pussy juice and then slide it up and into her back hole. The first time I did this, she told me it felt great and orgasmed shortly after. Since she often prefers to sit on top of me to cum, for a while, it was a sure way to help push her over the top. I think she eventually became used to it, so it didn’t always work the same wonders, but she continued to let me know that it felt good to her.
More recently, we had been at the beginning of an evening of sex, and I found myself lying behind her. She had her upper leg raised a bit and was super wet. I spent a long time pleasuring both her pussy and her anus and making her wet and slippery in both spots. I thought I would just tease a little with my cock at her back entrance to see her response. She just smiled and let me play. Unfortunately, it excited me so much to be that close to having my first anal experience that I couldn’t hold back an orgasm and just released my cum onto her butt cheeks.
She asked, “How was that?”
“I don’t think I actually went in at all,” I replied, “but it turned me on so much I couldn’t control myself.” That gave me the idea she wasn’t going to reject me if I tried again some time.
Fast forward to the evening of this story’s activity. I suggested my wife do some post-workout stretches on the bed for me, which she obliged; having been formerly a track and cross country runner, she knew all the various stretching positions. As I hoped and suspected, many of them required outstretched legs and an exposed pussy, and I took every opportunity to massage with my fingers or pleasure her with my tongue. Even before the added wetness from my tongue, she was super wet and excited. Eventually, she lay on her right side and twisted her torso, stretching her left leg over her body and all the way down to the bed. This arrangement exposed her vagina to me again.
I knelt below her, her right leg underneath me, and slid my hard cock into her. She relaxed in that spot as I stroked slowly in and out and reached down to massage her breasts—and at times elsewhere—to pull her tight to me, right hand on her left buttock and left hand on her left thigh, and to press in even deeper.
As I enjoyed stroking in and out of her and admiring her body underneath me, I had good access to her anus. I reached down to spread some of her juices over to her rosebud and inserted my finger while still filling “my” pussy with “her” cock. She seemed to relax and enjoy just watching me fulfill my pleasures, so I decided to push things a little further.
In the top drawer of my nearby nightstand, I had a container with a little coconut oil in it; I reached over to grab it while staying inside her. Now I could scoop out some oil with my thumb, use it to grease up her anus, and easily insert my thumb. I worked her with my thumb for about a minute, stretching her and spreading the slipperiness all around.
In hindsight, maybe I should have let her know what I was doing, but from the previous exploring around, I felt she was quite comfortable with what might come next. I pulled out my cock and moved it over to her back entrance. Not knowing for sure if I was at the right spot, I again first put my thumb in her back crack to make sure I had positioned appropriately, then slid it out and replaced it with the tip of my cock at her tightened opening, slowly pushing in. I easily and slowly slid in about 2 inches, our eyes locked on each other the whole time.
“Is it okay?” I asked.
“Yes, feels fine so far,” came the response.
Well, I wasn’t about to immediately ruin what she had given me approval to do by ramming her hard or causing any pain. I was very content just to enjoy the tightness of her anus around me. I then pulled out, replacing my condom with a new one, and moved back between her legs and into her pussy once again.
Now face to face, we talked briefly about what we had done. She asked me how it felt, and I told her what a new and wonderful sensation the tightness was. Then we ramped up our intensity towards orgasm. Maybe others have had this same experience when trying anal for the first time, but I was just overwhelming turned on—not by the physical difference in the feeling. I think, just the newness, the naughtiness of it, and her willingness to let me have this additional pleasure did it. I am certainly looking forward to exploring more in this area and interested in others’ stories on your first time with anal sex.
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