Lost Bet Gay Stories

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Orientation
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Girls Club Ch. 01

by ValerieMay on Mar 7, 2018
Transsexuals & Crossdressers

I stood by the bedroom window, letting the morning sun shine bright lines across my face. I closed my eyes and inhaled deep through my nose as the hazelnut flavored steam from my coffee reminded me of when everything was so ordinary. Ken was still in the shower and I wondered how he would like seeing me in my new XL knit sweater without any pants or underwea...

Sports Medicine Ch. 03

by Leezy on Sep 12, 2017
Anal

So Julie and I are now bonded stronger than ever. We have had every intimate experience together that I can think of, except we haven't licked each other's assholes. Maybe that is next. After my assistance in helping her to take all of John's cock up her ass, she became more open to letting me watch another woman in a special session. My mind was spinning a...

The Shoot

by TheLoafer on Sep 13, 2017
Erotic Couplings

He was twenty minutes late. Keith was never 5 minutes late, let alone twenty. Nicky twitched the curtains in the bay window but she couldn't make anything out of the ordinary on this bright summer morning. She'd done 5 shoots with him already... the only shoots she'd ever done outside personal pics for partners and playmates. Butterflys batted around her tu...

Dream Cum True, Sort of

by WhiteBoisWetDream on Sep 19, 2017
Transsexuals & Crossdressers

God damn it, she's here again. Cameron Williams. She's my sisters' best friend and for the past few years she's been my chief sexual fantasy. Dream on dream of hot nasty sex of all kinds. Filling her mouth and pussy with cum, and eventually even her ass. God what I would do to have a cha- "Hey Nick what are you up to", she said in that sweet sing-song voic...

Lovely Jade Ch. 02

by LuckyBob on Sep 13, 2017
Transsexuals & Crossdressers

Jade and I stumbled into our respective beds, and I slept like a dead man. In the morning, I woke to the smell of eggs, bacon, and coffee. Jade and Little Jim were in the kitchen making breakfast. I took a quick shower and joined them. Jade greeted me with a big smile, a kiss on the cheek, and a cup of coffee. Little Jim was grinning too. I guess Jade had ma...

My First Bi Experience

by biisgreat on Aug 18, 2017
Fetish

That first night with my wife, Sue, and her best friend, Clare, had been totally unexpected but incredibly hot. Clare started staying over on a regular basis and each time the girls were both so turned on by my feminisation that the sex was incredible. I had discovered Sue's bisexuality and it was so sexy watching her make love to her friend. ****** It ma...

Caught by My Bully and Exgf Ch. 01

by CindyTightass on Sep 15, 2017
Transsexuals & Crossdressers

Dear readers, this my first erotic story, all of protagonists here are fictional consenting adults, I hope you enjoy reading it! ***** I was 21 year old student with part-time job, living in a small flat in big city when this all happened. I broke up with my girlfriend Michelle, after seven month long relationship with her, because I received a video from...

Humiliated Sissy Husband

by rik581 on Sep 12, 2017
Transsexuals & Crossdressers

Content Warning: To Literotica readers. This is a story of degradation and demeaning of the male sexuality as retribution for an extra marital affair. It consist of a strong female character and a wimpy willing male character. The sexual hypocrisy built in the story is intentional an meant to be part of the demeaning aspect. There is "NO" gay scenes in the s...

Taking What I Can't Give Back

by EuropeJenn on Sep 12, 2017
First Time

This is a true story; in classic form names are changed, except mine. I also glossed over some of the more mundane details. I had always wanted to take someone's virginity but I didn't think that I would ever get the chance. Actually that isn't quite true, when I was 15 I lost my own virginity to my then boyfriend who was a virgin himself. It was a disappo...

Timmy Gets a Girl

by Bakeboss on Sep 14, 2017
Transsexuals & Crossdressers

The day my life changed was a day of infamy and one I shall never forget. Although it happened years ago, every detail was fresh in my memory as though it happened yesterday. Almost daily, it replayed in my head as if my mind enjoyed torturing me. Freshman year of high school and although I'd discovered girls I was far too shy to do anything about it but dr...