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Sissy playlist
Curated by: Kyliecage | updated: 9 months
![A Perfect New Life Episode 3 A Perfect New Life Episode 3](https://tbi.sb-cd.com/t/13565977/1/3/w:800/t6-enh/a-perfect-new-life-episode-3.jpg)
8,356
76%
1 year
![A Perfect New Life Episode 2 A Perfect New Life Episode 2](https://tbi.sb-cd.com/t/13558726/1/3/w:800/t6-enh/a-perfect-new-life-episode-2.jpg)
12,936
78%
1 year
![X-change Xmas X-change Xmas](https://tbi.sb-cd.com/t/13646589/1/3/w:800/t6-enh/x-change-xmas.jpg)
9,721
88%
1 year
![Total Recollection Total Recollection](https://tbi.sb-cd.com/t/9601368/9/6/w:800/t9-enh/total-recollection.jpg)
13,148
73%
3 years
![Hypno Hypno](https://tbi.sb-cd.com/t/7029805/7/0/w:800/t6-enh/hypno.jpg)
20,383
86%
4 years
![Perverted Meditations - First Trip to the Gloryhole Perverted Meditations - First Trip to the Gloryhole](https://tbi.sb-cd.com/t/9892970/9/8/w:800/t6-enh/perverted-meditations-first.jpg)
9,266
87%
3 years
![Sissy caption story Sissy caption story](https://tbi.sb-cd.com/t/9588689/9/5/w:800/t6-enh/sissy-caption-story.jpg)
44,097
83%
3 years
![EAT YOUR CUM SISSY BITCH!! EAT YOUR CUM SISSY BITCH!!](https://tbi.sb-cd.com/t/12652322/1/2/w:800/t6-enh/eat-your-cum-sissy-bitch.jpg)
21,528
83%
1 year
![bukkake trainer bukkake trainer](https://tbi.sb-cd.com/t/5263245/5/2/w:800/t3-enh/bukkake-trainer.jpg)
36,378
90%
5 years
![Becoming Dora Becoming Dora](https://tbi.sb-cd.com/t/3467558/3/4/w:800/t6-enh/becoming-dora.jpg)
22,924
94%
6 years
![Femme sissy hypno Femme sissy hypno](https://tbi.sb-cd.com/t/9808619/9/8/w:800/t6-enh/femme-sissy-hypno.jpg)
8,805
88%
3 years
![teen bbc orgy teen bbc orgy](https://tbi.sb-cd.com/t/4568441/4/5/w:800/t6-enh/teen-bbc-orgy.jpg)
76,399
97%
5 years
![real deal 2 real deal 2](https://tbi.sb-cd.com/t/7349778/7/3/w:800/t6-enh/real-deal-2.jpg)
5,661
83%
4 years
![Stare Deep Into Her Eyes Stare Deep Into Her Eyes](https://tbi.sb-cd.com/t/3883270/3/8/w:800/t6-enh/stare-deep-into-her-eyes.jpg)
103,458
93%
6 years
![Glory Hole Dick Suck Training Glory Hole Dick Suck Training](https://tbi.sb-cd.com/t/9873267/9/8/w:800/t6-enh/glory-hole-dick-suck-training.jpg)
16,830
90%
3 years
![Perverted Meditations - Anonymous Perverted Meditations - Anonymous](https://tbi.sb-cd.com/t/10317596/1/0/w:800/t6-enh/perverted-meditations-anonym.jpg)
6,669
87%
2 years
![Gloryhole sissy Gloryhole sissy](https://tbi.sb-cd.com/t/12659614/1/2/w:800/t6-enh/gloryhole-sissy.jpg)
6,986
90%
1 year
![Sissy gloryhole pmv Sissy gloryhole pmv](https://tbi.sb-cd.com/t/7969501/7/9/w:800/t6-enh/sissy-gloryhole-pmv.jpg)
12,878
92%
3 years
![Perverted Meditations - Anonymous 3 Perverted Meditations - Anonymous 3](https://tbi.sb-cd.com/t/10317500/1/0/w:800/t6-enh/perverted-meditations-anonym.jpg)
5,857
81%
2 years
![Part Time Sissy Part Time Sissy](https://tbi.sb-cd.com/t/12310159/1/2/w:800/t7-enh/part-time-sissy.jpg)
4,157
81%
1 year
![TEEN VS BBC GANGBANG TEEN VS BBC GANGBANG](https://tbi.sb-cd.com/t/10074121/1/0/w:800/t5-enh/teen-vs-bbc-gangbang.jpg)
32,818
96%
3 years
![A friend in need is a friend indeed - Sissy Caption Story A friend in need is a friend indeed - Sissy Caption Story](https://tbi.sb-cd.com/t/13337782/1/3/w:800/t6-enh/a-friend-in-need-is-a-friend-i.jpg)
36,451
95%
1 year
![Filthy sissy slut Filthy sissy slut](https://tbi.sb-cd.com/t/12391790/1/2/w:800/t6-enh/filthy-sissy-slut.jpg)
14,791
98%
1 year
![Amber Blank Bi Cuck Sissy Amber Blank Bi Cuck Sissy](https://tbi.sb-cd.com/t/9546478/9/5/w:800/t6-enh/amber-blank-bi-cuck-sissy.jpg)
100,479
97%
3 years
![IR Blowbang IR Blowbang](https://tbi.sb-cd.com/t/13292722/1/3/w:800/t10-enh/ir-blowbang.jpg)
5,647
93%
1 year
![Cum Quickly Cum Quickly](https://tbi.sb-cd.com/t/12755168/1/2/w:800/t2-enh/cum-quickly.jpg)
3,163
90%
1 year
![the mirror sissy caption story the mirror sissy caption story](https://tbi.sb-cd.com/t/13295556/1/3/w:800/t6-enh/the-mirror-sissy-caption-story.jpg)
20,569
92%
1 year
![Gangbang Girl 14 - 01 (AI Upscaled) Gangbang Girl 14 - 01 (AI Upscaled)](https://tbi.sb-cd.com/t/10507240/1/0/w:800/t10-enh/gangbang-girl-14-01-ai-upsc.jpg)
129,221
98%
2 years
![brownie mcghee brownie mcghee](https://tbi.sb-cd.com/t/9860813/9/8/w:800/t9-enh/brownie-mcghee.jpg)
29,059
97%
3 years
![f. shy grl bob f. shy grl bob](https://tbi.sb-cd.com/t/10648628/1/0/w:800/t1-enh/f-shy-grl-bob.jpg)
65,079
98%
2 years
![fkcotymfinz fkcotymfinz](https://tbi.sb-cd.com/t/10572486/1/0/w:800/t6-enh/fkcotymfinz.jpg)
17,446
84%
2 years
![CEI Super Cum Party 2 - The Great Night CEI Super Cum Party 2 - The Great Night](https://tbi.sb-cd.com/t/8118564/8/1/w:800/t8-enh/cei-super-cum-party-2-the-gr.jpg)
66,785
96%
3 years
![gratfuhrrdnr5 gratfuhrrdnr5](https://tbi.sb-cd.com/t/10550275/1/0/w:800/t6-enh/gratfuhrrdnr5.jpg)
10,253
81%
2 years
![sisygngncv sisygngncv](https://tbi.sb-cd.com/t/10572179/1/0/w:800/t6-enh/sisygngncv.jpg)
10,738
81%
2 years
![Magic Potion Magic Potion](https://tbi.sb-cd.com/t/7443831/7/4/w:800/t6-enh/magic-potion.jpg)
18,567
86%
4 years
![BBC Slut DP BBC Slut DP](https://tbi.sb-cd.com/t/11709433/1/1/w:800/t8-enh/bbc-slut-dp.jpg)
13,405
98%
2 years
![big tits threesome cuckold big tits threesome cuckold](https://tbi.sb-cd.com/t/6269103/6/2/w:800/t5-enh/big-tits-threesome-cuckold.jpg)
77,645
98%
4 years
![Tease Tease](https://tbi.sb-cd.com/t/12920060/1/2/w:800/t2-enh/tease.jpg)
9,887
93%
1 year
![Sissy Story - Mo' Money (Ebony Sissy vs BWC) Sissy Story - Mo' Money (Ebony Sissy vs BWC)](https://tbi.sb-cd.com/t/6703703/6/7/w:800/t6-enh/sissy-story-mo-money-ebony.jpg)
20,718
93%
4 years
![First Ones Free First Ones Free](https://tbi.sb-cd.com/t/12755135/1/2/w:800/t2-enh/first-ones-free.jpg)
10,686
86%
1 year
![Sissy Titties Sissy Titties](https://tbi.sb-cd.com/t/12920179/1/2/w:800/t1-enh/sissy-titties.jpg)
2,275
97%
1 year
![Spa Day Spa Day](https://tbi.sb-cd.com/t/12920176/1/2/w:800/t1-enh/spa-day.jpg)
8,804
83%
1 year
![Debt payment Debt payment](https://tbi.sb-cd.com/t/12927172/1/2/w:800/t6-enh/debt-payment.jpg)
882
94%
1 year
![Need A Ride Need A Ride](https://tbi.sb-cd.com/t/12927330/1/2/w:800/t6-enh/need-a-ride.jpg)
6,048
92%
1 year
![You Came In Me? You Came In Me?](https://tbi.sb-cd.com/t/12927388/1/2/w:800/t2-enh/you-came-in-me.jpg)
9,903
89%
1 year
![Reverse Curse Reverse Curse](https://tbi.sb-cd.com/t/12927362/1/2/w:800/t1-enh/reverse-curse.jpg)
11,686
95%
1 year
![Favor for Friend 2 Favor for Friend 2](https://tbi.sb-cd.com/t/12927395/1/2/w:800/t4-enh/favor-for-friend-2.jpg)
12,404
91%
1 year
![Sissy Pet Sissy Pet](https://tbi.sb-cd.com/t/12927397/1/2/w:800/t10-enh/sissy-pet.jpg)
4,536
86%
1 year
![Magic Mirror Magic Mirror](https://tbi.sb-cd.com/t/12927410/1/2/w:800/t3-enh/magic-mirror.jpg)
3,643
90%
1 year
![Racketeering - TG Creation Racketeering - TG Creation](https://tbi.sb-cd.com/t/4817615/4/8/w:800/t6-enh/racketeering-tg-creation.jpg)
9,995
96%
5 years
![Fitness Training - Sissy Caption Story Porn Fitness Training - Sissy Caption Story Porn](https://tbi.sb-cd.com/t/12843852/1/2/w:800/t6-enh/fitness-training-sissy-capti.jpg)
14,467
89%
1 year
![ijdahiwehwiehweioahewaoehwieo uypkload tax ijdahiwehwiehweioahewaoehwieo uypkload tax](https://tbi.sb-cd.com/t/12834549/1/2/w:800/t6-enh/ijdahiwehwiehweioahewaoehwieo.jpg)
8,032
94%
1 year
![Blowjob contest (captions TG story) Blowjob contest (captions TG story)](https://tbi.sb-cd.com/t/6046513/6/0/w:800/t8-enh/blowjob-contest-captions-tg-s.jpg)
12,189
85%
4 years
![Costume Party: Part 2 - TG Creation Costume Party: Part 2 - TG Creation](https://tbi.sb-cd.com/t/4817079/4/8/w:800/t6-enh/costume-party-part-2-tg-cre.jpg)
46,690
97%
5 years
![Costume Party: Part 1 - TG Creation Costume Party: Part 1 - TG Creation](https://tbi.sb-cd.com/t/4817068/4/8/w:800/t3-enh/costume-party-part-1-tg-cre.jpg)
19,178
100%
5 years
![My First BBC Contact 2 - A Sissy Caption Story My First BBC Contact 2 - A Sissy Caption Story](https://tbi.sb-cd.com/t/12847070/1/2/w:800/t8-enh/my-first-bbc-contact-2-a-sis.jpg)
12,860
79%
1 year
![My First BBC Contact 1 - A Sissy Caption Story My First BBC Contact 1 - A Sissy Caption Story](https://tbi.sb-cd.com/t/12836222/1/2/w:800/t6-enh/my-first-bbc-contact-1-a-sis.jpg)
16,823
87%
1 year
![Well Paid Experiment Part 1 - A Sissy Caption Story - SissyFan Well Paid Experiment Part 1 - A Sissy Caption Story - SissyFan](https://tbi.sb-cd.com/t/12709479/1/2/w:800/t1-enh/well-paid-experiment-part-1.jpg)
31,615
94%
1 year
![Well Paid Experiment Part 2 - A Sissy Caption Story - SissyFan Well Paid Experiment Part 2 - A Sissy Caption Story - SissyFan](https://tbi.sb-cd.com/t/12803190/1/2/w:800/t7-enh/well-paid-experiment-part-2.jpg)
25,305
97%
1 year
![Jennifer Stone x Jennifer Stone x](https://tbi.sb-cd.com/t/10420751/1/0/w:800/t9-enh/jennifer-stone-x.jpg)
2,665
98%
2 years
![Interracial Blowbang Interracial Blowbang](https://tbi.sb-cd.com/t/9166718/9/1/w:800/t6-enh/interracial-blowbang.jpg)
12,777
95%
3 years
![MEMENTOMARLY & BBC MEMENTOMARLY & BBC](https://tbi.sb-cd.com/t/12423048/1/2/w:800/t6-enh/mementomarly-bbc.jpg)
42,811
90%
1 year
![Addicted to cum Addicted to cum](https://tbi.sb-cd.com/t/10097271/1/0/w:800/t6-enh/addicted-to-cum.jpg)
32,614
98%
3 years
![what it feels like what it feels like](https://tbi.sb-cd.com/t/10976911/1/0/w:800/t6-enh/what-it-feels-like.jpg)
15,404
87%
2 years
![~BBC~Cuckold~Session~ ~BBC~Cuckold~Session~](https://tbi.sb-cd.com/t/12605240/1/2/w:800/t9-enh/bbc-cuckold-session.jpg)
7,315
98%
1 year
![Blondelashes19 Blondelashes19](https://tbi.sb-cd.com/t/12098879/1/2/w:800/t6-enh/blondelashes19.jpg)
6,543
96%
2 years
![Vault share 1 Vault share 1](https://tbi.sb-cd.com/t/12006987/1/2/w:800/t6-enh/vault-share-1.jpg)
7,091
94%
2 years
![Bible Study Bible Study](https://tbi.sb-cd.com/t/11970624/1/1/w:800/t2-enh/bible-study.jpg)
15,029
92%
2 years
![Pale ass turns red from bbc Pale ass turns red from bbc](https://tbi.sb-cd.com/t/12549909/1/2/w:800/t6-enh/pale-ass-turns-red-from-bbc.jpg)
13,845
98%
1 year
![Feeling Herself Feeling Herself](https://tbi.sb-cd.com/t/11961297/1/1/w:800/t7-enh/feeling-herself.jpg)
8,307
91%
2 years
![gendertransformation gendertransformation](https://tbi.sb-cd.com/t/5063732/5/0/w:800/t6-enh/gendertransformation.jpg)
8,622
92%
5 years
![BBC Surprise 3some - 60fps (P4PI 33) BBC Surprise 3some - 60fps (P4PI 33)](https://tbi.sb-cd.com/t/9371424/9/3/w:800/t6-enh/bbc-surprise-3some-60fps-p4.jpg)
75,647
98%
3 years
![story time 2nd story time 2nd](https://tbi.sb-cd.com/t/9289158/9/2/w:800/t4-enh/story-time-2nd.jpg)
68,443
92%
3 years
![Becum our girlfriend Becum our girlfriend](https://tbi.sb-cd.com/t/11429947/1/1/w:800/t2-enh/becum-our-girlfriend.jpg)
18,076
91%
2 years
![Dick Energy - By Drogon Dick Energy - By Drogon](https://tbi.sb-cd.com/t/11429960/1/1/w:800/t10-enh/dick-energy-by-drogon.jpg)
18,466
72%
2 years
![Drogon - STOP Drogon - STOP](https://tbi.sb-cd.com/t/11603896/1/1/w:800/t6-enh/drogon-stop.jpg)
9,247
73%
2 years
![CEI Super Cum Party 1 - The Preparation CEI Super Cum Party 1 - The Preparation](https://tbi.sb-cd.com/t/8101492/8/1/w:800/t9-enh/cei-super-cum-party-1-the-pr.jpg)
91,077
96%
3 years
![Sissy Cumslut Demise Sissy Cumslut Demise](https://tbi.sb-cd.com/t/3263302/3/2/w:800/t6-enh/sissy-cumslut-demise.jpg)
98,779
94%
6 years
![Your new life sissy Your new life sissy](https://tbi.sb-cd.com/t/9804918/9/8/w:800/t6-enh/your-new-life-sissy.jpg)
21,466
83%
3 years
![Beautiful transformation just the perfect size Beautiful transformation just the perfect size](https://tbi.sb-cd.com/t/12500859/1/2/w:800/t6-enh/beautiful-transformation-just.jpg)
12,967
92%
1 year
![asdsacsccsac asdsacsccsac](https://tbi.sb-cd.com/t/10438422/1/0/w:800/t6-enh/asdsacsccsac.jpg)
5,224
78%
2 years
![TikTok Hypno Challenge TikTok Hypno Challenge](https://tbi.sb-cd.com/t/11998626/1/1/w:800/t6-enh/tiktok-hypno-challenge.jpg)
8,555
77%
2 years
![Give in Give in](https://tbi.sb-cd.com/t/10993169/1/0/w:800/t3-enh/give-in.jpg)
96,062
96%
2 years
![Best Full Sissy Feminization Hypno Training Best Full Sissy Feminization Hypno Training](https://tbi.sb-cd.com/t/10450036/1/0/w:800/t2-enh/best-full-sissy-feminization-h.jpg)
226,658
94%
2 years
![crossdresser step son crossdresser step son](https://tbi.sb-cd.com/t/7413372/7/4/w:800/t6-enh/crossdresser-step-son.jpg)
21,560
97%
4 years
![ckcskchbby2 ckcskchbby2](https://tbi.sb-cd.com/t/10550292/1/0/w:800/t6-enh/ckcskchbby2.jpg)
33,471
92%
2 years
![Saphire @ Black Dick Gloryhole Saphire @ Black Dick Gloryhole](https://tbi.sb-cd.com/t/11402741/1/1/w:800/t3-enh/saphire-black-dick-gloryhole.jpg)
4,654
97%
2 years
![BBC Hypno Trainer BBC Hypno Trainer](https://tbi.sb-cd.com/t/12064195/1/2/w:800/t7-enh/bbc-hypno-trainer.jpg)
37,392
79%
2 years
![sissy pmv sissy pmv](https://tbi.sb-cd.com/t/11525919/1/1/w:800/t6-enh/sissy-pmv.jpg)
13,457
95%
2 years
![bdddydhduh bdddydhduh](https://tbi.sb-cd.com/t/10572312/1/0/w:800/t6-enh/bdddydhduh.jpg)
10,767
81%
2 years
![Sissy Fuck doll hypno Sissy Fuck doll hypno](https://tbi.sb-cd.com/t/9804733/9/8/w:800/t6-enh/sissy-fuck-doll-hypno.jpg)
6,984
86%
3 years
![Sissy Desires Sissy Desires](https://tbi.sb-cd.com/t/9011982/9/0/w:800/t6-enh/sissy-desires.jpg)
25,048
79%
3 years
![Broken by Cum Broken by Cum](https://tbi.sb-cd.com/t/6992684/6/9/w:800/t1-enh/broken-by-cum.jpg)
34,251
98%
4 years
![Broken By Cum 2 Broken By Cum 2](https://tbi.sb-cd.com/t/11121063/1/1/w:800/t5-enh/broken-by-cum-2.jpg)
17,307
93%
2 years
![sissy fuck machine hypno sissy fuck machine hypno](https://tbi.sb-cd.com/t/9811225/9/8/w:800/t6-enh/sissy-fuck-machine-hypno.jpg)
6,812
73%
3 years
![The Incentive: Caption Story by Kaori Kaps The Incentive: Caption Story by Kaori Kaps](https://tbi.sb-cd.com/t/11341164/1/1/w:800/t9-enh/the-incentive-caption-story-b.jpg)
43,836
94%
2 years
![The Fill In: A Sissy caption story The Fill In: A Sissy caption story](https://tbi.sb-cd.com/t/8682621/8/6/w:800/t4-enh/the-fill-in-a-sissy-caption-s.jpg)
175,988
97%
3 years
![Temporary Change Part 2 - A Sissy Caption Story - SissyFan Temporary Change Part 2 - A Sissy Caption Story - SissyFan](https://tbi.sb-cd.com/t/12462457/1/2/w:800/t7-enh/temporary-change-part-2-a-si.jpg)
19,042
95%
1 year
![Temporary Change Part 1 - A Sissy Caption Story - SissyFan Temporary Change Part 1 - A Sissy Caption Story - SissyFan](https://tbi.sb-cd.com/t/12455182/1/2/w:800/t6-enh/temporary-change-part-1-a-si.jpg)
44,054
86%
1 year
![I Was Just Curious Part 2 - A Sissy Caption Story - SissyFan I Was Just Curious Part 2 - A Sissy Caption Story - SissyFan](https://tbi.sb-cd.com/t/12454994/1/2/w:800/t1-enh/i-was-just-curious-part-2-a.jpg)
30,148
93%
1 year