The latest (f) who gave (m)e her anal cherry | 2016

Lets call her Jane. She lived downtown in a small southwestern city. She was stressed with her job, and ready for love.

The first time I have sex with a woman, I give her nonverbal hints about my anal fetish. When she's riding me I'll lube up her asshole with her pussy juices and touch her rear hole lightly and if her reaction is good or neutral I rub my middle finger on her pucker without penetrating while fucking her. If I'm fucking her doggy style, I'll wet a thumb. Some women push right back against it. If she's one of these, I'll get my thumb soaked with vagina mucous and put it in her ass while I'm fucking her from behind.

By the fourth time I fucked Jane, she knew I was a dom. I knew she was a sub. She was in her early thirties and despite a few flings she'd had, she'd never had a steady boyfriend. She was ready and willing for me to corrupt her as I wished. Corrupt her I did, as you'll see below.

She liked it when I bit her nipples and squeezed them hard. She liked it when I slapped her ass and pulled her hair during sex. Plus, we were becoming great friends too, so we had easy conversations about everything. Including anal sex. I told her the story about my initiation into anal sex when I was 22. I liked having these conversations with her while cupping her pussy in my hand, so I could tell how she reacted.

When I told her about the time I fisted my former literature professor, her pussy gushed. I kept talking about my experiences fucking women's asses and how much they loved it, and finally Jane just said "Do it. Get it over with."

"Do what?"

"Do it to me?"

"Do you have any lube?"

"Yes" She reached into a top drawer and pulled out a small bottle.

"Turn over."

She did.

"Let me massage your ass for a while."

I made sure all the muscles in her ass were relaxed, had her put her ass in the air and her head down in the pillows, then reaching down with my right hand put my thumb in her cunt hole, and started massaging her asshole with my left thumb. She was soaking wet but I'd added some lube anyway. Before long I had another thumb all the way in her ass. "How does that feel?" I asked.

"Gooooood."

"Do you like it when I do this?" I pulled the thumb out about a quarter of an inch and put it back in.

"MMMMMMmmmmm"

It wasn't long before I'd stretched her out enough with another finger and she was ready to take the cock. Indulging in ass play with a young woman gets me hard as a rock, and the next thing I knew the head of my cock has popped through her virgin backdoor hole. I love the sound a woman makes the first time she has a cock up her ass.

Jane was the latest in a long string of women I've introduced to anal sex, but the thrill was still there. This conquering action, this planting of my flag in virgin territory, this first opening up of woman's most intimate place, the knowledge that she is surrendering completely to my will, my desire, my throbbing dick-there's no other feeling like it. That rush of colored light and heat runs through every cell in my body in waves.

I slide it in little by little. Its like a vice. It was the size of a pinhole when I'd begun and now my bursting hard cock all the way up inside the forbidden, dark tunnel. Time for the kiss. Always kiss a woman the first time you fuck her ass. Lean down to where her mouth is and make out with her while she adjusts to the new sensation. Touch tongues. Mix saliva. Suck on her lips. Moan into her ear. Prayers laced with profanity. Let her know how much you appreciate being in her ass for the first time (whether its her first time getting assfucked or not its good to kiss her the first time you fuck her ass - but especially if it is her first time, if you're taking her anal cherry, take the time to kiss her mouth and her ear flesh, beg the ass gods for mercy, thank them for another opportunity to visit these heavenly spheres, another shot at ecstasy.)

Once she was used to it, that first time, I brought it to a quick conclusion. Its important to make a woman's first time as enjoyable as possible. Sometimes, if she's not a natural born anal slut, that means making it quick. The first time I fuck a woman's ass, especially if she is a virgin back there, I try to keep it down to a few minutes. Sure, the entrance is slow. Long and drawn out. But once she's open enough, and the in and out has begun, I'll try to shoot my load before she gets too sore. You want her to be able to feel it the next day, but she should remember it with a smile, not a grimace every time she sits down or goes to the bathroom.

Over the years that followed I spent many hours with my dick up Jane's rear end. If you add up all the ass fucking we've done, at six inches per stroke, and thousands upon thousands of strokes, I've travelled miles in and out of her ass. And that's one of the the best part of these relationships, when it comes to the sex. The intimacy of turning a woman into an anal cumslut. Jane likes me to stay in her ass afterwards, which is rare. She likes to stick her fingers in her ass when I'm fucking her pussy. She's even sucked my cock straight out of her ass, another rarity. She hasn't done it much, but several times I've had the privilege of watching her suck my cock when it is still wet from being inside her exceptionally clean ass.

She has also became adept at deepthroating. A dedicated student of cockworship. In the 69 position she takes me all the way in her throat and I've felt my come shoot out of her nostrils onto my upper thighs. I love the idea of coating every interior surface in her body with my slippery sperm, her esophagus, her intestines, her vagina (though its less than 1 percent of the time I come in her vagina, for reasons of birth control) her sinuses. She'll fuck her throat on my cock until tears stream from her eyes. Her nose runs until it drips. One of the last times she did this, it was a morning BJ! The idea of her going down that hardcore first thing in the morning, hard to fathom. I'd marry her if I could.

But the fact is that I was already married until just a few days ago. And as soon as I finalized my divorce with my ex, within a few days, Jane said she wanted to take a break. She'd been the other woman all along; as soon as a real commitment became possible, she wasn't able to do it. I don't know if Jane knew that even though I was separated from my wife these last four years, on rare occasions I would fuck my wife's ass in the morning and Jane's in the afternoon. (One day, I had to gently kick my wife out of the house, telling her that my girlfriend is on her way over.)

Some of my fondest memories of Jane are all those a monday mornings that started with me plowing her ass until I come. It was a great way to start the week. Later I started a business, and she worked for me for a few months in the office, so there was the added thrill of fucking my secretary in the ass before work in the morning, or fucking her throat until it was sore, and then having her answer the phone all day, remembering what my cock did to her with every word she spoke.

When she used to come and visit from out of town, sometimes I would have texted her instructions to enter my room naked with a bottle of olive oil in her hand. I'll be in bed waiting for her, naked. She isn't to touch any part of me before my cock is in her mouth. Then in her throat. I love to play with her ass while she sucks me, oil it up, get it ready. If I have a thumb up her ass and she gags on my cock, I can feel the contraction in her ass. Then, without even touching her pussy, I'll welcome her to my house with a load of semen up her thoroughly fucked ass.

I'm looking forward to this last trip we'll take together.