Backdoor Battles

Five Very Rough Tales of First Anal Sex

Debbie Brownstone is the undisputed queen of first anal sex erotica. From her first bestseller BENT OVER ON A BLIND DATE to her remarkable semi-autobiographical JESSICA’S BACKDOOR; Brownstone has proven time and time again that nobody does anal sex better. And since it’s Debbie’s own preference, her stories aren’t often sweet but almost always tend to have intense and very rough anal sex. In this collection, you’ll be treated to five explicit anal sex XXXerotica stories, and Miss Brownstone is in fine, fine form.

1. MY FIRST ANAL SEX (Rough Backdoor Sex with a Stranger)

It was the latest in a string of one night stands for me, and I didn’t expect it to be any different from the others. I didn’t even know his name and it didn’t matter. I wouldn’t enjoy it but was driven by the desperate need to feel the emptiness in my heart. How could I have known that the man would bring me to heights of pleasure I’d never known and then to terrible pain and then back to pleasure again? It was a first anal experience I’ll never forget.

2. ME AND MY BOSS ON THE BALCONY (A First Anal Sex Office Humiliation Erotica Story with Rough First Anal Sex)

Hardworking and lonely 28-year-old Caroline has been eyeing a particular CFO position for some time. She's prepared to go to night school for her position, but she's about to surprise even herself with just how far she's willing to go for her career. She finds the perfect opportunity to really impress her boss. She's in for a long evening of promotions and her first anal sex experience!

3. BACKPACKING BABE BANGED (Rough First Anal Sex at an Orgy with Strangers)

During the summer before I went to college, I decided on an adventure and hitchhiked my way back and forth across the United States. It was on a highway in Iowa where Alex picked me up, and I was more than ready to have some fun with him. When he suggested we go to a party, I agreed. I had no idea the party was an all-out orgy. Before long, I was tangled up with everyone and taking on multiple people at the same time—both men and women. That wasn’t it, though. Right in the middle of it all, Alex decided to bend me over and give me my first anal sex experience, and boy was it rough!

4. ME, MY FRIEND, MY WIFE, AND ALL OF HER HOLES (A Wife Share Rough First Anal Sex Erotica Story)

When my husband told me his best friend was still inexperienced at thirty, I was surprised. When he told me he wanted me to sleep with Robert, I was even more surprised. When he told me he wanted me to do it as a threesome, I was surprised and turned on! I couldn’t believe what I was about to do, take on two men at once. My husband was going to share me with his innocent friend, and I was determined that no matter how much I wanted this double team sex experience and no matter how incredible it would be for me, I was going to make sure that Robert’s experience would be amazing! Of course, I had no idea that my husband would use the opportunity to give me a rough first anal sex experience at the same time!

5. MY FIRST DOUBLE TEAM (Rough First Anal Sex with My Husband and His Friend)

I’d shared some idle fantasies about having two men at once but I never thought my husband would take them seriously! I also never thought he’d take me so seriously when I told him I fantasized about it being kind of rough. Boy was I surprised when he surprised me and his best friend got involved. It was really intense, and it even included something very, very rough…my first anal sex! I couldn’t believe just how hard it all got, and I couldn’t believe how the two men turned me into some kind of a sex machine…a total slut wife!