Sissy Dating Porn Videos Free Videos Short videos Premium Videos Photos Did you mean sissy dancing? Best Videos 04:05 Another straight boy turned by Elizabeth Stewart Elizabeth Stewart 3M views 10:46 First date with a pretty French trans girl, she sucks me and swallows in the kitchen. Kern Ostrova 582.9K views 06:06 I turned my straight roommate into my wife CutePinkUnicorn 2M views 17:26 German anal tranny date outdoor on holiday in Mallorca EroCom 423.6K views 28:49 Sissy cum dump compilation 2.6M views 07:37 I FUCK ON THE FIRST DATE Third sex XXX 2.3M views 16:14 shemale dresses sissy to fuck 2M views 08:12 Date Night with Mature Crossdresser Pure Ts 199.6K views 16:00 Male to female gender transformation smoking whore 674.4K views 06:16 TS TRAP SISSY DATE HIKE 1.3M views 04:52 Guy loses bet turns into sissy CD giving blowjob 1.2M views 07:07 Watch Transgirl Ria Bentley Fuck Her 9" Bull on Their First Date Ria_Bentley 562.4K views 16:46 My stepmom is a tranny Combat zone transsexual barebacking 1M views 21:12 Ria Bentley Gets Impregnated by Her 10" Bull Date Ria_Bentley 199.8K views 08:12 Loser Boyfriend Gets Feminized and Fucked Pure Ts 271.7K views 08:13 Intense Passionate Kissing & Makeout Foreplay on Date Night with this GORGEOUS Black Trans Girl Eros Orisha K KirkRyner 158.2K views 08:12 Never Expecting to Be a Sexy Girl Pure Ts 448.8K views 01:12:51 Tgirl Riley anally used and pleasured on a first date Tgirl Riley 123.7K views 11:13 My wife told me to play this 946.8K views 05:00 Our First Date Cassandra Lovit 8.1K views Relevant Short videos Ria Bentley Gets Impregnated by Her 10" Bull Date Ria_Bentley 5.9K views Sissy cuckold Delilah humping pillows while her wife is dating Delilah Quint 11K views Cum after Date Katha Vika 2.4K views Must-see moment from "German anal tranny date outdoor on holiday in Mallorca" EroCom 1.7K views Emotional moment from "Tgirl Riley anally used and pleasured on a first date" Tgirl Riley 1K views Iconic moment from "Tgirl Riley anally used and pleasured on a first date" Tgirl Riley 1.1K views 08:12 How to Train Your Sissy Boyfriend Brat Perversions 91.5K views 14:11 Humiliating Date Story by a Pathetic Piggy JessicaLynn15 14.8K views 05:11 Dads Bestmate Bangs Femboy mothplayboy 706.7K views 07:00 Sissy Doll Fucking in a Pegging Date Brat Perversions 11.1K views 05:20 I turned my straight roommate intro trans wife CutePinkUnicorn 450.5K views 01:02:22 Sexy Tgirl shoots a lot of cum while getting fucked bare on date #5 Tgirl Riley 146.4K views 05:59 dominant stepmom helps out her sissy slave Pure Ts 342.5K views 55:16 Tgirl Riley getting fucked bare in Date #6 PartII Tgirl Riley 160.9K views 43:09 Sissyfication 1M views 12:18 German amateur homemade anal creampie sex date with teen shemale EroCom 823.7K views 08:12 Dating a mature crossdresser Pure Ts 199.7K views 58:36 Mtf Big Tit Asian Redhead Impregnablelexa and Wolfdaddy901 Clean Their Pipes for Their Big Date with New Hottie DaddyandLexa 22.2K views 08:25 Sissy CD sucks and is fucked 1.4M views 11:35 A slutty college girl wearing date outfits and black pantyhose moans loudly while trying deep anal fingering for the first time Harinni 12.1K views 03:20 Feminization Positivity Trainer 703.3K views 03:12 Face-to-panties: an Intimate Close up with My Bulge Medi Voi 4.1K views 07:22 Girl forgot to tell her Tinder date that she’s Trans JsseMontz 609K views 09:40 Gina ́s New Year's Date Strapsex 109.7K views 23:32 A guide to sissication: Beginner - Am I a sissy? 729.1K views 11:25 When you feel horny, try dating a crossdresser like me. WanidaCrossdresser 36.4K views 08:12 Daddy's Good Girl! Pure Ts 883.3K views 01:20 POV Taking Cute Sissy's Virginity on the First Date - full vid on LayneLovee Manyvids Layne Love 43.4K views 15:35 Sissy #2: Becoming A Cock Slut 850.6K views 02:50 Dating a Guy, I'm the Only One in the Camera. Taiwancdgirl 15.8K views 13:00 Crossdresser shop owner gets fucked by a man in the shop WanidaCrossdresser 330.7K views 12:54 German amateur teen shemale get anal fuck in bathroom homemade Transen-von-Nebenan 697.5K views 18:34 I was about to have a happy married life, but I got Fuck by a stranger before marriage. WanidaCrossdresser 289.9K views Back 1 2 3 4 5 6 ... 80 Next Searches Related to Sissy Dating Crossdresser Seducing a Straight Guy Beautiful Femboy Sissy CD Fucked Sexy Femboys Secret Sissyboy Sissies in the Hood Whore Training Traps to Love Caught Crossdressing and Fucked Trap With Boyfriend Crossdressers Hardcore Very Faminin Turned Country Girls Fucking Sissy Caught Make up Traps Femboys and Sissys Beautiful CD Cute Couple Sissy Teens Hot Couples Straight search results Gay search results