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Bet with Roommate Leads to Cuckold

Bet with college roommate goes wrong and I end up cucked.

by voyeurman27 in Interracial Love 12/10/2010
4.25
2M
2.1k
0
2.7k
0

Home Run

Friend preys on hot mom.

by sa2222 in Mature 07/18/2007
4.26
1.65M
1.4k
187
1.9k
0

The Bet

Son bets a friend that he can't score with his mom.

by TheStinger in Mature 10/07/2009
4.47
856.9k
1k
31
1.3k
0

Anything I Want?

A poker bet puts Jackie's tight ass in the pot.

by LexxRuthless in Anal 10/30/2018
H
4.73
592.2k
850
45
1.2k
0

Daddy Wants to Poker

Daughter's boyfriend plays poker with Daddy for her pussy.

by VanillaExtract in Incest/Taboo 03/16/2018
H
4.67
284.4k
544
34
818
0

The Bet

My girlfriend puts her ass on the line.

by Mostdefinitely in Anal 12/15/2021
H
4.79
494.8k
464
46
749
0

Hypnotism Doesn't Work

Bet he can't hypnotise his busty stepsister.

by GeorgeTasker in Mind Control 08/24/2009
4.49
443.8k
460
51
607
0

Two Moms, Two Laps: United

Don't you love it when a family comes together?

by Tx Tall Tales in Incest/Taboo 08/16/2013
H
4.75
333.4k
459
199
570

BunkBed

Lost bet lets roomate fuck girlfriend on the bunk above.

by quale in Exhibitionist & Voyeur 11/23/2009
4.3
267.1k
450
18
616
0

Straight Musician Turned Gay Whore

He see's a jock turn out his emo bandmate over video games.

by GGandG in Gay Male 03/28/2012
4.44
247.9k
410
26
522
0

Put It Where Your Mouth Is

A sibling wager leads to a dream come true (his version).

by ItchyTasty in Incest/Taboo 08/04/2014
H
4.62
445.5k
398
42
552
0

New Shemale Stepmom

Stepmom teaches her new son a valuable life lesson.

by silkstockingslover in Transgender & Crossdressers 09/24/2021
H
4.7
179.6k
376
53
649
0

Football Bet FTW!

A costume reveals a new woman, and the bet is on!

by Tx Tall Tales in Erotic Couplings 10/11/2010
HW
4.77
373k
341
78
457
0

Teacher Poker

Teacher's poker lesson backfires.

by quale in NonConsent/Reluctance 08/05/2012
4.42
322.8k
301
22
435
0

Mom Sits on My Lap in the Car

A son shares a car seat with his mother.

by SisterWife in Incest/Taboo 11/10/2022
H
4.56
244k
294
26
530
0

The Bet

GF bets her BF is bigger... and loses.

by Luv4hotwives in Fetish 10/19/2020
4.38
163.2k
292
14
505
0

My Wife's Big Mouth

Hockey mom loses wager and pays in pussy.

by Jordan45 in Loving Wives 05/12/2022
3.8
139.2k
285
68
478
0

Shy Wife's Forced Black Hand Job

She lost a bet and has to pay a price, while hubby watches.

by dr13bone in Interracial Love 06/01/2010
4.29
466.5k
282
20
364
0

The New Neighbors

Neighbors move in and take possession of couple next door.

by watchdwag in Erotic Couplings 02/03/2010
4.46
259.6k
281
22
396
0

Straight to the Bottom Pt. 01

I (straight) bet on a blowjob and swallow more than pride.

by Megahomingberry in Gay Male 01/17/2020
H
4.56
119.8k
237
15
363

Getting Even

It all started with a lap dance.

by msound1 in Incest/Taboo 12/03/2008
H
4.52
340k
236
24
388
0

Lost a Bet

He lost the bet, but I have to pay the debt.

by kgardner in Group Sex 11/20/2010
H
4.52
275.8k
235
16
333
0

Poke Her Poker

A Mom must pay off a poker bet.

by Thecsm in NonConsent/Reluctance 12/18/2012
4.35
326.4k
231
0
330

Brother's Incestuous Bet Ch. 01

A brother and sister make an incestuous bet!

by mypenname3000 in Incest/Taboo 03/22/2022
H
4.54
197.4k
224
11
663

Worlds Best Diet Plan - Jingle Bell

Wife agrees to 2 days sexual slavery if he loses weight.

by Thors_Fist in BDSM 12/22/2016
H
4.71
112.9k
201
54
311
0

Side Business Ch. 01

My wife and I need help starting a small business.

by monkeytail10103 in Loving Wives 06/04/2017
4.38
124.8k
201
51
273

A Rape Game

A bet with the girlfriend goes wrong.

by Ashson in NonConsent/Reluctance 02/25/2017
4.4
240.8k
189
21
314
0

Katie's Lost Bet

A young wife loses a bet and fulfills a fantasy.

by Captain_Ron in Exhibitionist & Voyeur 09/24/2015
H
4.5
252.2k
186
11
340
0

The Bet

4 MILF Teachers make bet and get blackmail.

by Thecsm in NonConsent/Reluctance 03/03/2021
H
4.56
120.7k
180
0
366

Julie's Piss Bukkake Forfeit

College bet leads to a night of humiliation as a urinal.

by TheDarkCloud in Fetish 01/01/2017
4.39
95.4k
180
11
249
0

TCCS Pt. 01 Ch. 03: Two Hot Blondes Bet on BBC

Mom and daughter bet on BBC.

by Stormbringer in Interracial Love 10/15/2017
H
4.68
127.1k
174
9
241

A Neighborly Bet

A neighbor bets that his wife will sleep with me.

by cuninglinguist61 in Loving Wives 07/12/2010
H
4.57
260k
170
26
275

Car Trouble!

Jenny makes a bet with her uncle to fix her car.

by sethp in Incest/Taboo 06/21/2008
4.12
258.5k
163
19
229
0

Two Friends Make a Bet

First to bed four women, but one must be their mother!

by chris99999 in Incest/Taboo 06/23/2020
H
4.62
100.2k
162
18
281

Wife Becomes Fuck Slave

A bet leads wife to become a fuck slave and be used.

by SweetVibes in Loving Wives 05/10/2013
4.41
270.7k
157
10
239
0

The Wager

He bet her in a poker game and lost.

by m-o-t-o in Loving Wives 08/30/2009
4.24
187.4k
156
0
246
0

A Day's Wait

Never Make Sucker Bets.

by dtiverson in Loving Wives 06/10/2016
4.48
182.4k
156
85
223
0

Erica's Tiny Bikini Bet

Erica is made to wear not just a tiny bikini to the beach.

by Jappio in Exhibitionist & Voyeur 03/01/2014
4.4
227.4k
153
16
256
0

A Winning Wager

A wager over a football game gets out of hand.

by swingerjoe in Loving Wives 01/02/2014
4.04
224.2k
151
48
237
0

The Bet and the Gangbang

Heather's next adventure - sequel to Seduced by the Game.

by FatjackFallstaff in Loving Wives 08/23/2013
4.31
161k
147
23
215
0

A Game of HORSE Pt. 01

Brady loses a bet and becomes Brandi.

by emelle78 in Transgender & Crossdressers 05/06/2021
H
4.7
77.2k
143
16
227

I Bet More than I Should Have

Teasing husband in a poker game with his bosses.

by Willowifey in Group Sex 07/30/2019
H
4.65
111.3k
142
22
253
0

Dear Prudence

Another dangerous wager on fidelity.

by Harddaysknight in Loving Wives 01/12/2007
H
4.57
315k
141
145
249
0

Transformation Ch. 01

Jessup loses a bet.

by stillconfused in Transgender & Crossdressers 09/30/2006
H
4.66
312.7k
139
23
196

The Bet

A bet gets out of hand

by youbadboy in Incest/Taboo 11/12/2013
4.45
351.4k
138
19
276
0

BabySitter Bet

Babysitter is used to settle a friendly wager.

by Ashson in NonConsent/Reluctance 03/26/2014
4.13
256.6k
137
9
170

The Bet Ch. 02: The Challenge

More teasing, she ends up on display at an art gallery.

by storm_usmc in Exhibitionist & Voyeur 03/30/2016
H
4.82
198.9k
137
21
175

Babysitter Abandoned

Arriving home and finding the sitter half undressed

by Ashson in NonConsent/Reluctance 09/12/2016
4.43
277.7k
137
7
210

My Boss is a Bastard

A bet goes wrong, or right.

by JessieSmith in NonConsent/Reluctance 08/27/2016
4.43
133.3k
135
17
186
0

A Challenge

How many times can a gay man make a straight man nut?

by drmweaver705 in Gay Male 12/31/2019
H
4.62
76.9k
134
17
203

Another Really Stupid Bet

Can she beat the machine and win ten thousand dollars?

by staciliv in Exhibitionist & Voyeur 01/20/2008
H
4.53
152.2k
132
14
194
0

The Hunting Lodge

Indian wife is shared amongst friends on a hunting trip.

by spankedboy in Loving Wives 01/06/2022
4.44
115k
129
66
237
0

Pool Party: A Bad Bet

A game of pool has lifelong consequences.

by DonorArbalest in NonConsent/Reluctance 11/01/2022
4.31
72k
127
19
269
0

Double or Nothing

Idle bet turns enemies into passionate lovers.

by SPEN STERLING in First Time 06/28/2010
H
4.68
140.2k
126
18
174
0

The Bet

Wife loses a bet and has to play with hubby and his friends.

by arturos68 in Group Sex 12/06/2007
H
4.52
203.6k
126
23
194
0

Wife Wager: Episode 01

Participants wager their wife on TV for a cool million.

by quale in NonConsent/Reluctance 11/23/2009
4.21
194.4k
125
11
228
0

Dick Size Bet

A guy ends up being a sissy maid for his friend.

by alexmuntz109 in Transgender & Crossdressers 04/23/2020
4.35
74.7k
125
7
185
0

A Bet's a Bet

Two straight friends make a bet.

by RaulBloodworth in Gay Male 11/01/2022
H
4.7
62.9k
124
9
210

Hockey Bet

Jenny hates when the Devils lose.

by WhiskeyIsGood in Transgender & Crossdressers 03/21/2013
H
4.56
137.1k
123
13
148
0

Sandy Strips For My Friend

Girlfriend shows her exhibitionist side.

by writemarksmith in Exhibitionist & Voyeur 06/09/2014
4.46
156.9k
121
16
192
0

Poker Night

A wife plays hostess.

by bluebaloo in Loving Wives 08/21/2005
4.39
375.1k
121
0
187
0

Never Bet with your Heart Ch. 01

A friendly bet leads to an exposed wife.

by monkeytail10103 in Loving Wives 06/23/2013
4.1
190k
120
50
202

Texas Hold Em

Wife loses at poker, so they take turns to poke her.

by Woody Woodwood in Loving Wives 05/12/2008
4.21
305.9k
119
27
214
0

My Roommate

In which my sexy roommate and I make a bet...

by ElspethMoans in Erotic Couplings 06/18/2017
H
4.65
98.6k
118
10
166
0

Centerpiece

She loses a bet an has to bare all.

by Daniellekitten in Group Sex 02/16/2008
H
4.64
177.2k
118
28
176
0

Under the Influence

I'll bet someone was betting they could get me drunk.

by laptopwriter in Loving Wives 06/16/2017
4.29
158.6k
118
123
182
0

Camping with my Futa Bully Ch. 01-05

A young man's very confusing vacation...

by Serca45 in BDSM 06/19/2022
H
4.7
40.7k
114
14
229

Erin Goes Anal

Erin goes anal, in a big way.

by Mike Franklin in Anal 10/10/2005
H
4.54
394.5k
111
2
162
0

Winner Takes All: Round 01

Frank enters a high-stakes tournament.

by CoreyStreber in NonConsent/Reluctance 04/30/2016
H
4.61
84.8k
111
3
173

Playing to Win

Lauren finally breaks Josh's winning streak.

by __Lisa__ in Erotic Couplings 02/01/2014
H
4.73
60.4k
111
11
159
0

Harry and the Stupid Bet

To win, he has to fuck his mother-in-law.

by chris99999 in Incest/Taboo 07/24/2021
4.49
90.7k
110
13
210
0

Hubby Losses a Bet

Husband losses a bet and wife becomes a date for another man.

by Sexybeast8899 in First Time 09/30/2020
4.43
84.9k
110
32
231
0

A Sure Bet

Girl is taken by the men she trusted most.

by abnormal_libido in NonConsent/Reluctance 03/29/2008
4.15
241.9k
110
4
164

Lesbian Co-worker

Straight girl makes a bet with a butch lesbian and loses.

by Hotelroom in Lesbian Sex 10/14/2021
H
4.6
74.3k
109
45
191

A BF's Bet Goes Wrong

Ellen's boyfriend makes a bad bet with her ex.

by lockerman138 in NonConsent/Reluctance 08/29/2021
4.43
73.9k
107
5
267
0

I Lost the Poker Game

Strip Poker did not go the way he hoped.

by belted and teased in BDSM 08/31/2007
4.37
217.9k
107
16
191

I Don't Want to Spoil the Party

A dangerous wager between friends at a party.

by Harddaysknight in Loving Wives 03/03/2006
4.35
455.1k
107
103
185
0

March Madness Ch. 02

Man loses bet to buddy as he slips further into domination.

by watchdwag in Gay Male 07/10/2009
H
4.53
211.3k
104
11
130

That Ass, Though

A redhead loses a bet to a friend with a big secret.

by solitarycafe in Fetish 11/21/2017
H
4.61
71.4k
104
6
157
0

Heavy is the Head

Max makes a bet with his ex's little sister and wins.

by EnvywithJadee in First Time 03/17/2016
H
4.67
95.7k
102
14
148
0

Teachers Bet

An angry bet with huge implications.

by TheDarkCloud in NonConsent/Reluctance 01/09/2015
4.14
168.2k
101
16
157

Airtight

Filling all three holes to win a bet.

by rthnck in Group Sex 01/05/2006
H
4.51
208.7k
99
12
163
0

Patriots v Giants - Superbowl Bet

She loses the bet and loses again.

by tantric_explosion in Loving Wives 04/03/2008
4.43
193.9k
92
24
129
0

A Week

She hates his guts!

by May_I in Interracial Love 12/23/2014
4.49
66k
91
17
112

Poke Her Poker Ch. 02

A Mom continues to pay off a poker bet.

by Thecsm in NonConsent/Reluctance 03/05/2013
4.45
172.6k
91
0
126

Becoming Her Bitch

A simple bet changes everything.

by Mistress Drusilla in BDSM 04/26/2007
4.33
250.3k
91
17
125
0

Alex & Maggie: The Bet

Brother & sister make a bet, but sister wants friend to pay.

by JustAKSGuy in Incest/Taboo 02/15/2014
4.23
165.3k
90
9
137

The Football Bet Pt. 01

Easy Money, Never Comes Easy.

by Shadowforce1 in Interracial Love 02/11/2016
4.43
65.9k
90
4
137

Dominating the Lax Bros Pt. 01

Shorter younger guys dominate cocky lacrosse studs.

by somebody123 in Gay Male 12/31/2021
H
4.8
41k
89
9
151

Gentelman's Bet

Always be careful how you word a bet.

by HosieryExpert in Loving Wives 05/05/2008
3.74
208.7k
89
31
145
0

Baseball, Billiards, and More

Mom and Aunt have fun, son watches.

by Thecsm in Incest/Taboo 04/03/2013
3.89
181.3k
87
0
141
0

Straight Chris Makes a Bet

Straight and gay best friends make an interesting bet.

by dunnohowtosex in Gay Male 09/02/2015
H
4.51
124.3k
86
14
135
0

The Asshole

The Asshole does me a solid!

by imhapless in Loving Wives 12/13/2019
H
4.52
73.3k
85
35
135
0

Gal Gadot: One Hot Blowjob

Losing a bet, Wonder Woman pays up.

by MeanBlackjack in Celebrities & Fan Fiction 06/11/2017
4.42
86.1k
84
2
132
0

My Wife and the Cross-Country Team

Coach's joke offer leads to unexpected encounter with team.

by ScottGreen in Group Sex 07/13/2023
H
4.65
39.2k
84
10
171
0

A Lost Bet Ch. 01

A lost bet with dad makes her have to do whatever he wants.

by sexyinaf in Incest/Taboo 11/07/2008
4.14
231.2k
83
12
124
0

The Big Bet

A summer long affair that started with a bet.

by Fostery in Incest/Taboo 07/18/2020
4.3
77.3k
82
13
132
0

Sportswriter's Dilemma

If her team loses, will she pose in the nude?

by rd75000 in Exhibitionist & Voyeur 01/30/2016
H
4.63
69.2k
82
12
147
0

Sister Wins a Bet with Me Pt. 01

Brother hates to lose, how does she fix him?

by BigMadStork in Incest/Taboo 11/10/2020
4.07
58.6k
81
18
174

A Bet with My Wife

Wife takes bet too far, I retaliate.

by Treated2 in Loving Wives 12/17/2022
0
60k
80
41
182
0
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