Lipstick Kiss Stories

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Learning to Crossdress Pt. 03

by crossdressme70 on Sep 15, 2017
Transsexuals & Crossdressers

I had just had the most amazing first time sexual experience, with the most beautiful erotic lady, I could have ever have imagined, who would introduce me to silk, satin, nylons, and then cover me in lipstick and lip gloss and have me cover her breasts in more and more lipstick kisses before losing my virginity. We had been "relaxing" together for about an...

The Toy Ch. 04

by kmarkk on Jul 14, 2020
Erotic Couplings

"Baby!" She called out to him softly from the dresser as he stepped into the room after his shower. His body was nothing spectacular. Yes, he had that lean build she liked, but his lower abs were buried under a small pouch of a belly. His arms showed tone, but only when he moved them and they flexed. It was a good starting point, and he'd get better with tim...

Burgundy Lips Ch. 02

by qdata on Sep 15, 2017
Fetish

Author's preamble: After a long time, I return to the story related in Burgundy Lips. The story tells of consensual heterosexual sex between a youth and an elderly widow, and contains an element of fetish. I urge you to read the original story to get the full context of this chapter but a brief synopsis is that a young man is seduced by an elderly spinster...

A Little Diddling

by organic_bologna on Sep 14, 2017
Erotic Couplings

I am waiting for you downstairs while you get ready. As usual, you are not on time but I have learned to expect that. Finally, I hear you coming down the bare wood stairs. I can often tell what shoes you are wearing by your steps, very quick childlike steps when barefoot or wearing sneakers, kinda of a slap when wearing sandals and slower when in heels. The...

Make Up

by ElWapo on Sep 16, 2017
Interracial Love

Hi, let me tell you about myself before I start my story. At the time of this story I was about 44 years old. In my entire married life, I think my wife dressed up with makeup and lipstick maybe once or twice. I think my wife look good enough that she didn’t need any of that stuff. I came from a blue-collar family and I don’t remember my mother ever wearing...

Learning to Crossdress Pt. 02

by crossdressme70 on Sep 15, 2017
First Time

Since relating my "First Experience" to you, I have been re-playing it over and over, in my head, and realise how fortunate I was to meet a lady who wanted to indulge her fetishes with me, and established my desire to crossdress. As I left off, she had me wearing her silk panties, with her kneeling across me, my hands sliding up and down under her half slip...

Hot Sex Instead of Dancing Ch. 08

by SusanJillParker on Sep 12, 2017
BDSM

Please give me the support of your vote. * Bound to the bed and blindfolded, instead of taking her dancing, Walter gives his wife, Linda, what she really wants, hot sex. With her on her back naked and helpless, Walter imagined his wife, Linda, tied to the bedposts at her wrists and ankles. In the way she was staring at him was the same way he imagined him...

Deep Cherry Lipstick

by MalDufleurs on Sep 11, 2017
Anal

More adventures with Penny and Mr H, first featured in Nice Substitute... ************ When Penny came in, announced she had dumped her boyfriend, then stripped down to her new lingerie and said she was going to be my "breakfast" I wish I could tell you that I made love to her slowly and gently for hours. The truth is that in five seconds my cock was out...

March Madness Ch. 04

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Suspected Affair - Confirmed

by 69Jance on Jun 1, 2020
Transgender & Crossdressers

Second Part of Suspected Affair After confirming my suspicions, I was looking forward to seeing what was next with a hot wife and a pair of handsome twins. Actually though, from what Maxwell said, they all were looking forward to bringing me out of the proverbial closet and see what is next for their new sissy. Maxwell had said "We should go meet Heather a...