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Bestselling author Debbie Brownstone brings us a very personal erotic story, continuing the chronicles of Jessica, the woman who helped Debbie explore her own erotic anal sex ambitions. In this story, Jessica introduces a friend to the joys of anal sex. That friend's name? Debbie! Jessica not only introduces her friend to her first anal sex experience, but decides to go all out and give Debbie her first lesbian sex experience at the same time.

Cynthia would do anything to get a chance to speak with her superstar husband Ty, but after six years she's losing hope. When she finally gets in touch with one of his agents, the man shows up with a group of friends. Cynthia can get an appointment with Ty, and all it will cost is her virgin asshole! Cynthia is willing to do whatever it takes to get to see Ty, and when she agrees, she even agrees to first anal sex. The rough gangbang that ensues is painful with deep throat, anal sex, spanking, hitting, and slapping!

When a woman marries a man ten years her senior, she has to be prepared for a difference in sexual drive and ability. This bride understands that, but she doesn't mind. She's in love and she's willing to spend her life without any hardcore sex if that's what it takes for them to be better. Her fiance Andrew minds, though; and if he can't satisfy her, he's going to make sure someone else can. In this case, it means her first lesbian experience with a hot Asian girl and a scorching MFF threesome complete with her first anal sex experience-and she has it in her wedding gown!

Ainsley can't believe her car has given out, but she's pleasantly surprised to find the tow truck driver is Chris, the football player she had a crush on back in high school. She does her best to show off her perfect little heart-shaped ass, but he doesn't seem to pay any attention to it at all. She keeps it up but nothing's going anywhere. Worse, when Chris tells her he has news about her car, she can tell things are going to be bad. Chris is going to teach Ainsley exactly what happens when a girl walks around with her luscious ass on display.

Tara is unhappy with her little dog. The damned thing wants to go for a walk at five-thirty in the morning, and Tara hasn't had a lot of sleep! Reluctantly, she takes him out to do his business, but she has no idea what's in store for her! On this walk, she'll meet a man who wants her body, and in her half-awake weakened state she's willing. Of course, this man wants more than what's she's ever given before. This man will take her tight virgin asshole, and he's not interested in the word, "No." Right in the park!

Tiffany isn't sure why her doctor would order x-rays for what is certain to be a case of Montezuma's Revenge, but she obediently heads to the hospital to get it done. There, the sexy technician hurries her through the process, but he doesn't stop when the pictures are taken. Instead, Tiffany has her very first anal sex, in a rough and reluctant doctor/patient sex encounter complete with rough deepthroat and semen swallowing!

It's Charlotte's final day with her airline before changing jobs to work on a corporate jet, and she's stuck on a transpacific flight handling the first class cabin. All nine of the passengers are from the same internet startup company, and all of them are difficult customers. Still, it's Charlotte's job to please them, and she isn't going to let them deplane dissatisfied. Of course, she didn't know that all nine of them want to join the mile high club, and they've decided that she's the perfect one to initiate them…all.

A mistaken perception about a business trip leaves morale low, and Katie wants to help the five disgruntled employees feel better. She was thinking it might make sense to buy them lunch, but they have a different idea altogether. Katie is going to take them all on at once in an office sex gangbang that will include semen swallowing, first anal sex, and double penetration!

After the last explosive episode, Casey's been dreaming of another threesome. When Jim asks for a repeat with another client, she readily agrees. She's even happier when she sees Jim at the bar with the most beautiful redheaded woman she could ever imagine. From there it's to the hotel room, and a shocking surprise!

Constance finally got up the guts to admit to her fiancé that she wasn't really a virgin, and she did it a week before the wedding. Jamey takes it in stride, though, after a little bit of anger. Of course, Constance didn't realize he was going to have a virgin on his wedding night no matter what, even if that meant his new bride would be giving up my virgin ass and bent over for a very rough and reluctant first anal sex experience!

Clarissa is getting tired of hearing her friend Sally constantly describe her sexual conquests. There's no way her friend is anywhere near as sex-crazed as she claims…is there? Surprised to discover that she's getting a little self-conscious about it and even a bit sex-crazed herself, Clarissa decides to throw caution to the wind and visit The Circle Club, a black tie nightclub that, if the rumors are true, never stays formal for long. She's ready to let her hair down and really show that she can shine as brightly as Sally, but has she gotten herself in too deep?

Korrine and Max are back, and Korrine is worried that she and her husband have become too busy with work to keep us their new adventures fulfilling the fantasies Korrine obsessed over and Max discovered. Her fears are put to rest when he brings home a sexy coworker to f--- his wife, and suddenly Korrine has two cocks, and before the night is through she'll have every hole filled in her fist mmf threesome complete with more deep throat, more anal sex, and her first ever double penetration!

Best friends Kiara and Diane share everything, and when Kiara gets engaged, Diane's a little worried that their relationship will change. There's nothing for her to worry about, though, because Kiara is more than willing to share EVERYTHING! That includes her fiance, Eric, and that means that Diane and Kiara are in for their first ever anal sex threesome, that is if Diane is able to fit Eric's massive, thick penis into her tiny, virgin ass!

Millie is a bit of a rebel, and this barely legal eighteen year old is about to learn that you don't break into neighbors' homes! When she's caught, she thinks she's in for a trip to the police station, but instead she ends up tied to a bed, and the angry neighbor teaches her all about rough sex and humiliation while his wife watches, but even the man's rough treatment doesn't prepare her for what comes next, a hard and painful first anal sex experience!

I just didn't want to wait for the next bus, and I was tired of waiting altogether. What kind of a vacation is it when all the time is spent waiting. I got my way, though, and my friends and I scrambled onto the crowded bus. We didn't get to sit together, but that's no big deal. Unless...unless the person sitting next to me decides he wants to touch me and take my mouth right on the bus!

I couldn't believe how sexy it felt to have a young man like Toby want me, and it was especially wonderful to be reminded just how much an 18 or 19 year old boy can accomplish. We'd already had a blistering hot time, and five minutes later he was ready again! It was another incredible session, but then he did something I didn't expect. He focused his attention on my tiny virgin ass!

Evan and Tricia have planned a night of intimacy for a while, but just when things heat up, Tricia's friend Shelly calls. She needs to talk with Tricia all about her recent breakup. Of course Evan's angry! Just like Shelly to call like that, and now the evening is ruined…Or is it? After all, even if Tricia is on the phone, Evan still has access to her legs, her pussy, and her tiny, tight virgin asshole for some first anal sex.

Jill and her friends decide on a popular nightclub for their girls night out. They're disappointed when it looks like they'll never get past the velvet ropes, but they're overjoyed when they're given an opportunity to join a wealthy patron in a private club room. Of course, the patron has a number of other guests, and Jill is about to be initiated into the world of anal sex, by six or seven guys! Will this be her First Anal Sex experience and her first gangbang too?