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‘craigslist’ stories

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Rye's Encounters Pt. 03

Rye discovers the true path on her journey towards sissydom.

by sissyrye in Gay Male 03/26/2024
H
4.7
2.4k
3
3
7

Older For Younger: First Gape

My first online hookup in a motel, he was 40+ years my age.

by loveofstory in Gay Male 08/10/2023
H
4.6
15.7k
16
8
30
0

That Ginger Guy at 1am

Craigslist hook up at 1am with a Ginger guy.

by RRNB in Exhibitionist & Voyeur 02/02/2023
H
4.6
3.3k
3
1
6
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Broke Straight Boy Forced Gay Pt. 01

A straight student gets caught up with a Craigslist dom.

by NotSoStraightSlave in NonConsent/Reluctance 08/18/2022
H
4.58
69.3k
93
9
175

Giving it up on Craigslist

Sex starved husband ends up pleasing man from Craigslist.

by ginaxx in Anal 04/25/2021
4.14
29.1k
12
3
20
0

He Wanted Me to Meet Her

I took control of his game and his woman.

by ShowTime8 in Loving Wives 02/19/2021
4.14
30.9k
41
11
70
0

Exploring My Feminine Side Ch. 01

My journey through bicurious sex.

by Lindseyxoxo in Gay Male 11/05/2020
4.15
25.7k
10
3
22

Craigslist Pt. 03: Fucking the Innkeeper

Hot anonymous pleasure on a cold January day.

by Ken Nitsua in Gay Male 04/15/2020
4.28
7.1k
6
1
11

Jessica, Anal Bitch

Late 20s SWF hooks up w/ daddy-type, gets anally fucked good.

by ifry in Anal 03/29/2020
4.2
69.8k
81
2
138

Jailed

A low self-esteem woman becomes a dynamo.

by amyyum in Loving Wives 08/21/2019
4.24
23.9k
23
13
35
0

While the Wife Sleeps

Fantasy Craigslist man for a neglected married bisexual.

by EveWillSin in Erotic Couplings 07/10/2019
4.06
7.3k
4
1
8
0

First Time with Sam in the Car

First time hookup with my FTM lover in my car during the day.

by maxsmithdfw13 in Transgender & Crossdressers 10/23/2018
H
4.55
24.4k
15
8
26
0

A Couple's First Online Ad

Jim and Diana post an online ad to find another couple.

by TexAF in Exhibitionist & Voyeur 07/03/2018
3.99
18.5k
9
5
16
0

Craigslist Surprise

Story of some interesting and surprising CL encounters.

by hornyyoungguy69 in Exhibitionist & Voyeur 04/17/2018
3.8
13.9k
2
2
6
0

Craigslist Chronicles Ch. 07: Steven

21st birthday fun with a missed connection...

by Profanity89 in Gay Male 04/17/2018
H
4.74
8.2k
5
0
5

Craigslist Chronicles Ch. 05: SUV

Evan has some fun with Mr. G, then a hung black guy.

by Profanity89 in Gay Male 03/10/2018
4.3
14.8k
8
2
10

Natalie Ch. 01

Natalie gives a blowjob.

by the_proletariat in Romance 03/03/2018
3.68
19k
5
3
10
0

Chocolate on Aisle 10

Clandestine fun at the store...

by mrpeachesva in Exhibitionist & Voyeur 12/12/2017
3.86
7.8k
2
0
3
0

In Between Girlfriends

Weary, a straight guy experiments with Craigslist.

by Paperpiece in Gay Male 11/22/2017
4.48
46.5k
60
6
92
0

8 in a Box

3 friends discuss their fantasies, causing ones to come true.

by RandyXXX in Group Sex 11/17/2017
4.4
33.1k
12
1
25
0

Please Fuck My Wife Ch. 01

Man's wife discovers his chastity and cuckolding fetish.

by CuckedByJenn in Loving Wives 11/08/2017
4.38
84.5k
145
21
194
0

Coffee Table for Melissa

Big-tittied girl desperately needed a coffee table.

by away443 in Erotic Couplings 09/15/2017
4.1
30k
12
1
23
0

No Strings Attached

A classified ad leads to a fantasy fulfilled.

by eternal_student in Erotic Couplings 08/25/2017
4.44
14.8k
7
1
11
0

My Twins and My Man Ch. 02

Kalie is at it again with a few changes in mind.

by Ganistaniro in Incest/Taboo 08/18/2017
4.26
15.8k
11
1
15

A Slut Awakening - Blow and Go

I suck a stranger off in his car.

by Silkess in Erotic Couplings 08/12/2017
H
4.57
47.6k
48
10
82
0

My Twins and My Man

A man's fantasy turned reality; the beginning of a series.

by Ganistaniro in Incest/Taboo 08/11/2017
4.14
36.4k
42
2
59

Make Me Your Plaything

A man and woman meet and explore role-reversal.

by dlcalguy in Toys & Masturbation 07/24/2017
H
4.62
48k
64
4
87
0

Curious Teen Sucks Craigslist Cock

My first experience sucking cock when I was 18 on Craigslist.

by hotlatino18 in Gay Male 05/20/2017
4
58.1k
21
7
29
0

Craigslist Adventure

Dylan meets a girl from craigslist.

by Leszoccer13 in Erotic Couplings 01/24/2017
3.79
13.4k
6
1
9
0

My First Crossdresser

My First Encounter with a Hot, Sexy Crossdresser.

by IrishJamesHot in Transgender & Crossdressers 10/20/2016
4.17
40.6k
22
10
25
0

Please Fuck My Ass

Many encounters failed but the tranny...

by atitagain991 in Gay Male 10/14/2016
4.07
66.5k
27
12
43
0

Adventure in the Ghetto Pt. 01

An office worker takes a different kind of vacation.

by cinnabutt in Gay Male 07/01/2016
4.31
26.2k
14
1
23

The Introduction

A guy loses his inhibitions.

by Hiddeninplainsight in Gay Male 04/30/2016
H
4.67
26.9k
16
13
20
0

The One that Changed Everything

A man takes a cue from his ex-girlfriends and tries BBC.

by pervertedstoryteller in Gay Male 03/03/2016
4.25
42.3k
29
6
39
0

Alone with a Sissy

Frustrated man indulges in his women's underwear fetish.

by JRussell in Fetish 11/17/2015
3.83
27.1k
5
1
7
0

Peter Meets Mr. Johnson

A fantastic journey of sexual exploration.

by 1mbibry in Gay Male 10/20/2015
4.27
35.1k
7
5
12
0

Another Craigslist Adventure

The third person I met with from craigslist for some fun.

by hornyyoungguy69 in Gay Male 04/01/2015
3.96
24.1k
5
0
8
0

First Time Ch. 01

My first time fucking a man I met on Craigslist.

by ScottyValentine in Gay Male 03/31/2015
4.44
41.7k
16
8
20
0

Craigslist Adventures Don Ch. 03: Rob

I now head over to my new friend Rob's house for play time.

by hornyyoungguy69 in Gay Male 03/24/2015
3.72
10.8k
2
1
2

Craigslist Descent

Married man takes a turn for the worse on craigslist.

by cinnabutt in Gay Male 02/24/2015
4.14
43.5k
22
6
26
0

Craigslist Adventures Don Ch. 02

Our final time meeting up, a new guy joins us.

by hornyyoungguy69 in Gay Male 01/28/2015
3.74
12.9k
3
1
4

Craigslist Adventures Don Ch. 01

I made a new friend named Don.

by hornyyoungguy69 in Gay Male 01/27/2015
3.96
13.9k
5
0
6

A Craigslist Experience

A quick Craigslist hookup in the woods.

by hornyyoungguy69 in Gay Male 01/16/2015
3.93
44.5k
7
5
9
0

Mind of Straight Married Cocksucker

The 10-part philosophy of a straight cocksucker.

by silkstockingslover in Gay Male 01/15/2015
H
4.54
118.3k
121
58
163
0

Hotel Stranger Sex

Horny business woman looking for anonymous hotel sex.

by Erinteresting in Erotic Couplings 12/28/2014
4.08
71.7k
23
7
37
0

Over the Phone Cuckold Pt. 01

Wife accidentally calls husband while getting fucked.

by UsedPantiesStore in Loving Wives 11/30/2014
3.94
196.9k
89
56
122

London Slut

Tales from London.

by samlibertine in Erotic Couplings 12/22/2013
3.84
24.2k
7
0
12
0

The Dare

She dared me to write a little something about her.

by that_other_other_guy in Erotic Couplings 07/31/2013
3.62
11.1k
00
2
0

Cullen Ch. 05

Cullen answers a craigslist ad, again.

by rckplsky in Gay Male 05/02/2013
4.09
13.8k
3
1
3

Fucked by a Stranger

A hookup for just a blowjob turns steamy.

by married_but_curious in Gay Male 04/09/2013
4.45
106.9k
63
18
86

Pissing on Craigs List Ch. 02

Gay and bisexual threesome with pissplay.

by westvme in Fetish 01/31/2013
4.26
53.6k
19
4
20

Young Chrissy Dresses and Sucks

I dress as a girl and meet a guy from Craigslist.

by CrossdressingChrissy in Transgender & Crossdressers 12/28/2012
4.19
100.2k
18
12
25
0

Craigslist Dream

Sexually deprived single braves a new adventure.

by vblizz in Erotic Couplings 12/16/2012
4.25
16.4k
5
0
7
0

Missed Connection Ch. 02

A response...

by Bizzy_Bish in Interracial Love 06/05/2012
H
4.62
29.9k
28
18
33

Missed Connection

I try to find my mystery lover.

by StoryTimeBeth in Group Sex 05/09/2012
4.24
14.1k
2
3
7
0

Allie's Encounter on Craigslist

Allie loses her virginity.

by allycd in Transgender & Crossdressers 03/20/2012
4.2
66.7k
14
10
19
0

Comic Book Sex

The author poses for an erotic comic book.

by Johnevie in Group Sex 02/07/2012
4.44
27.6k
13
2
28
0

First Encounter

Sometimes I use ads to solicit photos of women.

by jack_be_not in Exhibitionist & Voyeur 10/20/2011
4.39
13.3k
5
2
8
0

Night in Montreal

My first time of being with another man.

by ishyone in Loving Wives 10/13/2011
3.94
70.6k
17
17
22
0

Litost

Best friend's sexual frustration transforms Alex.

by rex_gladiorum in Transgender & Crossdressers 08/22/2011
4.25
60k
11
0
14
0

Casual Encounters of Transition

Experiences leading to huge sexual reveals.

by rex_gladiorum in Gay Male 08/10/2011
3.8
20.2k
1
2
3
0

Nineteen - Looking for Older Man

A random encounter sought by a lonely guy.

by timmywells in Gay Male 07/15/2010
4.49
82.5k
21
3
28
0

Helping a Stranger

Her husband cant get her pregant, so she turns to the Internet.

by tmartin96007 in Erotic Couplings 04/04/2010
3.8
40.9k
12
3
17
0

Craigslist Casual Encounters, Vol. 01

You meet in person.

by mstarling in Erotic Couplings 02/02/2009
4.43
20.3k
5
1
7
0

He Brought Me Panties

A description of a crossdressing liason.

by Cute Little Thing in Transgender & Crossdressers 05/04/2008
4.22
128.6k
27
14
39
0
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