‘shemale on male’ stories

Active tags
Active tags
shemale on male 

Category

Shemale Step-Sister

Teen boy spies on his shemale step-sister and gets a treat.

H
4.54
713.7k
1k
57
1.4k

Family Issues Ch. 01

A futa girl forces an innocent young man to share her bed.

H
4.58
409.4k
639
48
1k

Shemale Sister

Victor's sister has secrets, now he finds out.

3.84
264.8k
160
15
231
0

Jeremy's School Bully: The Ending

Jeremy finds a way to deal with his bully.

H
4.76
238.4k
510
67
571

Shemale Step-Sister Ch. 02

Ethan and Morgan fuck some more.

H
4.56
226.4k
404
53
528

The Bet

Hung girl wagers that Billy will love her cock in his ass.

H
4.76
197.4k
598
46
959
0

A Shemale Surprise, and No Choice

She has a surprise, and isn't letting him go...

4.24
180.5k
102
6
169
0

Stolen Away

T-Girl meets a guy in a relationship and has to have him.

H
4.66
168.9k
232
27
281
0

A Futa Mom's punishment

A futa Mother is pushed too far. Naughty boys get punished.

H
4.62
168.8k
398
27
691

His Futa Auntie

Muscled Futa Auntie wants to widen his sweet asshole.

H
4.51
158.7k
317
17
575

How I Met Alyssa

A young guy finally meets his shemale girlfriend.

H
4.64
157.3k
189
18
251
0

A Debt to be Paid

Chris comes up short on the rent.

H
4.61
157.1k
240
37
305
0

Late Ch. 02

Freddie gets anally massaged by his shemale coach.

H
4.79
151.1k
330
30
421

The Roommates Ch. 02

Brad copes with big-titted Daphne's girlhood.

H
4.73
149.3k
176
24
207

Family Issues Ch. 04

A futa girl forces an innocent young man to share her bed.

H
4.88
136.3k
161
81
192

Futanari Birthday

Jess grows a dick for her birthday wish.

4.35
131.8k
117
8
152

Meat

A man takes home the waitress from his favorite steak house.

H
4.59
126.3k
162
12
217
0

Family Issues Ch. 02

A futa girl forces an innocent young man to share her bed.

H
4.65
116.3k
161
31
194

Finding Aimi

His dream girl is hung, and wants to fill him with love.

H
4.66
116.2k
269
29
456
0

Family Issues Ch. 06

A futa girl forces an innocent young man to share her bed.

H
4.87
112.3k
142
75
163

The Panty-Chasing T-Mom MILF Ch. 02

Luke and Alina get closer while plotting against his mother.

H
4.61
109.3k
144
36
172

Shemale Orgy

Ladyboy Mistress shares submissive with other shemale Doms.

H
4.59
108.5k
169
6
244
0

Mai and I

A man and his dominant & romantic transsexual girlfriend.

H
4.65
107.5k
156
8
207
0

Becoming Her Bitch Ch. 03

I finally become the ultimate male slave whore.

4.33
104.9k
33
8
44

No Self Esteem

Colin just can't tell Shelia no.

H
4.72
100.7k
234
30
307
0

Family Issues Ch. 05

A futa girl forces an innocent young man to share her bed.

H
4.86
100.4k
131
84
154

A Good Fucking Examination

Tyler receives a very special treatment from Doctor Kendra.

H
4.77
94.3k
270
51
441
0

My Wife's Big Dick

Date night might never be the same for Laura and Matt.

H
4.81
90.3k
158
15
277
0

Family Issues Ch. 03

A futa girl forces an innocent young man to share her bed.

H
4.79
89.2k
145
94
171

Fucked Ch. 02: The First Date

Jessica ploughed his ass and now she's back for more.

H
4.55
84.6k
120
19
177

Changing Rooms

Adversity leads to hot showers in the men's room.

H
4.69
81.7k
106
1
174

My Mom's Shemale Lover Ch. 01

My Mom's Shemale wife forced me to be her sissy.

4.23
79.2k
105
4
182

Alabama Nan: On the Road

Transsexual & sister's adventures on road home.

4.41
76.8k
27
0
38

Craigslist Encounters Ch. 01: Craigslist Cumslut

Jake searches Craigslist and finds a ladyboy Mistress.

H
4.69
73.6k
102
11
149
0

Family Issues Ch. 07

A futa girl forces an innocent young man to share her bed.

H
4.76
73k
95
58
115

The Package

She's delivering her biggest package between his legs.

H
4.68
71.8k
134
10
270

Bully Ch. 01

The road to hell is paved, but I used to take the school bus.

H
4.75
69.9k
143
83
256
0

Craigslist Bottom Bitch

Jake and Candy get ready and experience their next encounter.

H
4.72
67.5k
61
3
99
0

The Tower

A Tower that gives women cocks and changed men into sluts.

4.17
67.2k
85
6
149
0

Samantha Ch. 01-03

Artist makes a discovery about his model, and he likes it.

H
4.68
59.9k
24
1
38
0

Nadia Ch. 02

Nadia teaches me a lesson in control.

H
4.67
59.1k
67
3
79

After Hours at Self Checkout Ch. 01

Darrel's normal self checkout shift takes a kinky turn!

H
4.52
58.8k
81
14
133

Call in the Professional

He misses his flight and had to find a way to fill his time.

H
4.55
58k
67
5
91
0

The Quickie

Horny transgirl takes a coffee shop worker into a restroom.

H
4.77
57.1k
169
19
265
0

Your Best Damn Girlfriend Ever - Final

Mandy is going to help Thomas get over Angel.

4.44
56.8k
97
25
135

Oliver's Corruption Pt. 01

A beautiful boy is wanted by everyone around him.

4.39
55.6k
143
20
246
0

Her Property Ch. 01

Tony's new life is honey on a razorblade...

H
4.61
55k
101
9
159
0

Anywhere Anytime

A Thai ladyboy and man have one week before their wedding.

H
4.65
52k
87
6
131
0

If You Scratch My Back, I'll...

A man visits a masseuse and receives more than he bargained.

H
4.53
51.2k
77
8
142
0

The Beast in the Basement

Jill is the beast in the basement, or is she?

4.11
49.8k
49
29
82
0

Shemale in a Bar Pt. 01

First day on a trip to the US ends promising.

H
4.63
49k
94
7
153

Double Cheeked Up Pt. 01

Having a phat ass might not be so good.

4.4
49k
77
13
142
0

A Futa Mom's Punishment Pt. 02

A futa Mother is pushed too far. Naughty boys get punished.

H
4.77
45.7k
135
30
216

Our New Babysitter Ch. 02

My wife is sober this time with the babysitter.

H
4.82
41.5k
71
14
107

Dark Forest Ch. 01

Eric learns solo backpacking makes him very easy prey.

H
4.6
40k
105
8
199

Festival of Seasons

A boy meets a lascivious futa tanuki inn mistress.

H
4.77
40k
119
10
227

What's Wrong Sis'?

Quinn has pissed her off for the last time...

3.95
38.8k
49
8
80
0

The Fifty-Cal Gal

Traci heads into the Red Light district and meets its queen.

H
4.59
38.1k
78
5
130

Changing Rooms Ch. 02

Sexual chemistry reacts and a physical relationship ignites.

H
4.82
37.9k
48
1
60

Goth IHOP

Chubby homie meets his female goth friend from Discord IRL.

H
4.72
37.5k
137
7
195
0

His Futa Auntie Pt. 02

Muscled Futa Auntie wants to widen his sweet asshole.

H
4.66
35.5k
75
4
121

Lance's Seven Sins 01: Envy

Lance encounters someone "bigger" than him.

H
4.52
34.4k
44
1
77

Fucked Ch. 03: Night Cap

Jaz and Dom learn what two horny futas can do to young men.

H
4.77
33.9k
81
10
120

Loyce

Tim meets his foil in an "unfortunate" living situation...

4.13
31.9k
34
8
49
0

Lexi's New Life

Lexi loses weight, but gains a penis.

H
4.53
31.3k
78
15
109
0

Our New Babysitter Ch. 04

My wife goes on a business trip, leaving me home alone.

H
4.76
31.2k
52
11
78

Festival of Seasons Ch. 02

Bell's new life at the inn begins.

H
4.88
29.5k
60
22
95

Changing Rooms Ch. 03

Romance blossoms and leads to sex for the first time.

H
4.8
28.6k
38
3
48

Shemale in a Bar Pt. 02

1st half of the 2nd day on the trip to the US.

H
4.71
26.6k
47
2
66

Changing Rooms Ch. 04

Boyfriend and girlfriend, life half a year later.

H
4.76
26.1k
43
6
55

Our New Babysitter Ch. 03

Things continue in the bedroom for the night.

H
4.81
25.7k
44
7
67

Tuxedo Rental

Renting a tuxedo turned into something more.

4.43
23.7k
31
10
58
0

Late Ch. 05

Jane tries to win Freddie back, but gets carried away...

H
4.62
23.4k
80
24
109

After Hours at Self Checkout Ch. 02

Darrel has decides to go home with Tammy and things happen.

H
4.76
22.7k
56
7
76

His Futa Auntie Pt. 04

Muscled Futa Auntie pursues her quarry...

H
4.6
22.3k
41
9
62

Fucked Ch. 04: Housemates Pt. 01

Twink vloggers vs a gym full of horny futas. Carnage ensues.

H
4.84
21.7k
48
17
80

A Mother's Duty Ch. 01

An Empire, and a new boyslut in charge. What could go wrong?

H
4.57
21.7k
42
0
72

Kinky Anniversary Ch. 04

Will Jim be able to take Sheera's monster cock?

H
4.85
21.4k
48
17
72

Dark Forest Ch. 02

Eric think's he's safe with Clara, but he's really not...

H
4.7
19.2k
52
16
86

The Fifty-Cal Gal Ch. 02

Lashona guides Traci on his first day of the job.

H
4.64
18.9k
43
6
62

His Futa Auntie Pt. 03

Muscled Futa Auntie wants to widen his sweet asshole.

H
4.58
17.4k
38
3
60

Mortal Cumbat

Brother and Sister take on a Futa demoness and a Warlord.

H
4.56
17.2k
65
4
122
0

Our New Babysitter Ch. 07

Wife has me locked in a cage, and surprises with a new guest.

4.42
16.8k
27
13
48

Brewery Magic

Abby and Russ have a hook-up that turns into more.

H
4.82
16.4k
54
14
94
0

Deep Space Lust Ch. 01

Girly-looked cadet receives training from an shemale alien.

4.43
15.2k
37
5
70
0

Late Ch. 07

Jane and Freddie rekindle their desires...

H
4.84
12.1k
54
19
77

Wrestling Match Went… Wrong?

A foreign beauty with a secret recently moved into town.

H
4.51
11.9k
43
17
68
0
12
Active tags
Active tags
shemale on male
Separate tags with commas. More info in the FAQ