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‘anal cherry’ stories

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My First Time - Anal Sex

Finally take the plunge loosing my anal cherry.

by LitXDesires in Gay Male 01/03/2024
4.4
18.8k
7
5
15
0

Warmer, Sultrier, Kisses Pt. 09

On morning of her wedding, Brandi learns truth about Jameer.

by Differentendeavours in Loving Wives 09/21/2022
3.06
4.6k
5
3
8

My New Boss Pt. 14

Suky returns home and catches Lisa and I in the act.

by RegularGuy2020 in Fetish 12/30/2020
3.97
5.1k
2
0
3

My Best Friend Regrets It Pt. 02

Adrian purchases Jaime's anal cherry.

by RegularGuy2020 in NonConsent/Reluctance 11/18/2020
4.19
16.7k
8
1
15

My Best Friend Regrets It Pt. 01

Sara sees the sex tape, cancels her wedding.

by RegularGuy2020 in NonConsent/Reluctance 11/16/2020
4.22
25k
19
2
56

Mothers' Day Weekend Ch. 07

Fielding Marshall: Penny's ruse brings welcome reprisal.

by highshine808 in Incest/Taboo 09/24/2018
4.43
11.9k
15
1
28

Only the Landlord's Daughter

All my best holidays and birthdays rolled into one.

by literot in Group Sex 08/21/2018
H
4.58
45.2k
28
1
46
0

The Two Cherries

A short story about taking my girlfriend's anal cherry.

by re808 in Anal 06/30/2018
4.13
45.1k
17
1
22
0

Humiliated Wife Turns to Her Son Ch. 05

Sandy and Steven explore new horizons.

by OG4U in Incest/Taboo 11/16/2017
H
4.71
80.3k
142
10
173

Few Real Hours with My Online Wife

Online couple meets and has a nice time.

by sunnyboyz in Erotic Couplings 07/28/2017
4.09
6.8k
3
5
3
0

His Sweet Girl Ch. 04

Boss takes young secretary's ass publicly.

by naughtysexmouse in Erotic Couplings 07/02/2016
4.49
63.4k
34
3
38

Wait... What?

A rebuttal.

by HaydenDLinder in Anal 06/29/2016
4.06
46.3k
12
28
13
0

Anal Awakening Ch. 02

The other wives are invited to join the fun.

by SarahsHooters in Anal 11/03/2015
H
4.51
84.6k
38
3
50

"Ask Anna Anything" Ch. 02

Anna is used by six forum members in a hotel room.

by Anna_Exposed in Group Sex 10/27/2015
4.43
209.8k
108
3
120

Sarah's Story Ch. 01: First Gangbang

She shares her fantasy but gets more than she bargained for.

by SarahsHooters in Group Sex 08/20/2015
4.36
93.6k
71
10
96

The Perry Brothers

Adult brothers, same sex incest.

by XXNoraJeanXX in Incest/Taboo 02/17/2015
4.4
100k
117
14
144
0

Popping The Wife's Anal Cherry

As I take my hot wife's anal cherry, I set up a threesome.

by HungLikeAMonkey in Anal 11/22/2013
3.81
76.3k
21
5
25
0

I Have a Proposition For You

A saga of a hot wife.

by maninconn in Loving Wives 09/09/2013
3.74
182.7k
83
0
132
0

My First Gay Encounter

Gay Male Adventure

by bigskyben in Gay Male 08/26/2013
4.35
55.7k
24
10
25
0

Surrogate Husband Ch. 07

He gets his mother's anal cherry.

by pennylesspauper in Incest/Taboo 03/08/2012
H
4.66
114.2k
65
7
78

Teacher's Pest Ch. 02

Teacher and female student have anal "first time" for both.

by AverageBear in Anal 02/03/2012
H
4.51
105.8k
39
4
45

Becky Ch. 05

Becky seduces two friends into taking her ass cherry.

by Many Feathers in Anal 08/06/2011
4.44
86k
16
0
19

Taking You

She takes you, her bi-curious lovers anal cherry.

by JustifyablyGrown in Anal 06/22/2011
4.03
75.4k
23
6
34

Mid-Life Oasis Ch. 02

Jill reveals her deepest fantasy and loses her anal cherry.

by meddlesome in Anal 06/20/2011
H
4.65
91.7k
24
2
37

Educating Shannon

A chance to get even with his first love.

by Rehnquist in NonConsent/Reluctance 12/22/2008
H
4.7
580k
542
179
655
0

Andy as Mandy Lose His 'Virginity'

Andy finally loses his anal cherry to a strap-on.

by LucyCanyon in Transgender & Crossdressers 12/18/2008
H
4.55
77.4k
32
0
51
0

What Men Want Ch. 02

Young Mary-Jane takes an advanced course in hard sex.

by Jaymal in NonConsent/Reluctance 07/18/2008
H
4.64
184.1k
115
21
143

Honey I Was Just Wondering...

An anal cherry proposition.

by jjblue in Anal 04/25/2008
3.96
52.8k
6
1
9
0

Angela's Punishment

A tease gets what she deserves.

by Jizaz_Jester in NonConsent/Reluctance 03/19/2008
3.73
116.4k
26
2
51

To Honor and Obey

A TG bride's wedding night adventures.

by slutty_jannelle in Transgender & Crossdressers 07/28/2007
4.14
76.7k
30
8
36
0

Not Gay, Butt... Ch. 02

Couple's sex life is reawakened.

by Sacanaz in Anal 01/04/2006
H
4.61
110.2k
20
4
23

Cuckolded by Boss

Wife is in love with her husband's much older supervisor.

by vyasya in Loving Wives 03/08/2005
3.7
338k
66
42
102
0

Anal Virgin

Daddy takes coed daughter's anal cherry.

by Jim McKay in Incest/Taboo 07/21/2004
3.86
200.4k
32
2
40
0

Semantics

She visually defines the term "slut"

by Barnaby in Group Sex 08/20/2003
4.27
61.1k
4
1
8
0

Pushing Her To The Edge

He spanks her then takes her anal cherry.

by hollyh in BDSM 06/05/2003
4.32
155k
29
0
33
0

Leasa Ch. 04

Leasa goes home for boost from Daddy.

by LeasaJ in Incest/Taboo 08/28/2002
4.36
160k
44
0
50

Karina Writes

Friends tricked into wife swap form bond.

by Tallus in Loving Wives 02/15/2002
4.12
188.4k
12
0
19
0
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