Straight Mans Smart Mouth Gets Him First Time Gay Anal Literotica Stories

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It Hurts

by wanderinjoekidd on Sep 16, 2017
Anal

It hurt, it hurt a lot, she had never had anal sex before, not until about 5 minutes ago. How did this happen? Today should have been another average day in the in average life of an average 32 year old single woman living in an average sized town in an average Midwest state. Instead, today was anything but average. She was laying face-down on her bed with h...

A Fantasy Gone Too Far

by prev on Sep 1, 2017
Group Sex

"What's your address?" The words were written across my computer screen. "Serious?" "Yea, what's your address? You've got me so turned on that I need to see you right now, I'm very rich." We had been making up erotic story ideas for a while, so I thought she was kidding, I gave her my address and said," what are you going to do jump on a plane and fly ov...

AliExpress and Sissy Downfall Pt. 02

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

Charlie had really done it this time, deciding on his first big self bondage session in his hotel room after picking up all his kinky goodies he bought on AliExpress. Then his wife had surprised him by joining him for the weekend and found him, fully dressed as a Sissy slut, make up, wigs, high heels the lot. Locked in bondage at his own hands. Now she was a...

Cuckolding Manual Ch. 01

by erotictim69 on Sep 12, 2017
How To

A guide for a dominant woman and her submissive husband. Installment 1 At the urging of my wife I have decided to write a sort of "manual" about our cuckolding sex life. This is based on the real (not fantasy) experiences of my wife and I, as well as the many people we have corresponded with who also enjoy this sexual scene. We decided I should write this...

Fantasy Come True

by RAPIDROY on Sep 12, 2017
Group Sex

I've always known that I enjoyed anal play and that ever since I started masturbating that I would sometimes use men in my fantasy. I'd even tried going to gay hangouts and answering classified ad's but always either backed out or ran like hell. So even though I wanted to try man to man sex it looked like I wasn't going to ever find someone I was comfortable...

Ellen Starts a New Life

by c7racer on Sep 2, 2017
Loving Wives

She was glad he kept in touch. As her first ever lover, despite the passing of a decade and a half since they split up, there was always a place for him in her life. They had always stayed friends, had occasionally screwed in the first few years after they broke up. He had attended her wedding, by then recognised by the friends and family of Ellen as an ol...

A Cum Filled Condom Ch. 01

by curiously_curious on Jul 31, 2019
First Time

The ad went out... My urges written down with unsure trepidation. Did I really just post an ad to the world about my deepest darkest secret fantasy?! But I'm straight...I'm not gay?!...am I?! oh what have I done. *PING* With surprise, only 10 minutes later, my computer sprung to life with a waiting email. 'Tomorrow is the day your life changes! call in...

I Pay For A Pie

by DiggerDave on Sep 17, 2017
Fetish

I have been married for fourteen years now, and have never been unfaithful to my wife. I love my wife dearly, however when it comes to sexual matters in our relationship she is quite a prude. We do make love with each other, and she tries hard to please me. However because of her strict religious upbringing she will not participate in anything that she consi...

Just Another Day at the Office Ch. 06

by LeStrange on Aug 31, 2020
Fetish

Danial awoke amidst the bodies of three of his female staff, enjoying the soft warmth of the female flesh, especially the slim brunette who he still had his cock in as he spooned her. Sandra was her name he recalled and the slut had feinted from a huge orgasm as Danial fucked her. Danial had cum about six times the evening before and he realised he must hav...

Clean Up Fantasy Becomes Reality

by Mister8ball on Nov 4, 2019
Fetish

The beginning So I've met the love of my life recently. She's everything I've ever prayed for. She's smart, she's funny, she's loving, and caring. And my oh my she's quiet the hottie. She's a little above average height for a woman and is carrying some extra weight, but she carries it well! She's got the prettiest eyes and a smile to die for. And did I ment...