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First time anal Stories

first time anal

I was a naughty college kid, well, a student nurse exactly, and found the coursework far too easy. I had too much time on my hands. Growing up in a small beach town, where I was bullied and teased for being gay, I pretty much did my own thing. Older, tall...

Babydoll's Sissy Virginity

An understanding friend offers more than just friendship

I'd just finished showering, running my fingers down my clean-shaven body, and enjoying the silky feel of soft skin on my smooth legs. I always felt incredibly feminine after a shower, pampering myself with creamy lotions and sweet-smelling perfumes. I'd...

Road Trip with a Sissy: Day Two

After discovering Kieron's sissy side, Jack uses it to act out his sexual fantasies

My alarm went off way too soon. Last night’s festivities had seriously cut into my sleep time and I was exhausted. Much as I wanted to sleep in, we still had a lot of miles to go today. I only had a couple quick stops I had to make before we hit the open...

Husband Loses His Anal Virginity

Sexy wife guides her hung friend to take her husbands anal virginity

I’m looking directly ahead, my arms outstretched in front of me. I’m naked, vulnerable. You’ve tied my wrists together and then attached them with two ropes to the solid wooden legs of the coffee table I’m bent over. I’m on bended knee. I’d gasped as you’...

Husband Loses His Anal Virginity

Sexy wife guides her hung friend to take her husbands anal virginity

I’m looking directly ahead. My arms outstretched in front of me, bound, my chest pushed up against the cold hard wood of the coffee table. A moment earlier I’d gasped as you’d gently pushed me down onto all fours over the table and the coldness had hit my...

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Blind Obedience, Chapter 8

I prepare to explore jewel's "final frontier" and take her anally.

The following weekend jewel came over looking visibly distraught. "Oh, Master I am so sorry! I was so looking forward to being with you today, but when I woke up this morning my once-a-month visitor had come to see me! I am sorry, but I had to wear pantie...

Meagan's New Toy Gets Its First Workout

Meagan never knew what she had been missing before her new toy arrived...

It has been another long day at the office.  Lawyers work long, long hours but after a while, you get accustomed to the grind.  Well, not really.  At the end of the day, you’re just simply tired and worn out and all you want to do is get home, relax, get...

The House Mother

I must pay the price so that my girlfriend and I can have a great college sex life.

I had to look down to confirm that it was, in fact, my girlfriend who had my cock in her mouth. As the embrace of her lips slowly moved up and down my shaft, her tongue waggled across the underside driving me toward the peak. “I’m gonna cum!” I cautioned....

She was only the Landlord's Daughter

All my best holidays and birthdays rolled into one

As we get older, birthdays seem less important and, in fact, are something to try and ignore. And presents are often embarrassing, particularly when it comes to saying thank-you. Not always. Last summer, my wife Trish and I set off for a week’s holiday to...

Mona Loses Her Anal Virginity On Christmas

Inspired by the true and raunchy story of the first time I had anal sex

It was Christmas Eve and Mona looked smoking hot. To appease her parents, she went to church with them around 6:00 pm-- but she was sure to dress to the nines in an outfit that made the entire congregation pray for her soul. To top it all off, her long da...

I Want You To Fuck My Ass

The night I lost my anal virginity, I said the same exact line.

I chose to wear the tight white mini-dress Thursday night for one main reason. It accentuated my curves in all of the right ways, especially my backside. Eric, my fuck buddy, the guy from the movie theater noticed as soon as he saw me.He took me out for a...