Sort by
Relevancy

Free Stories

100%
Mein erster Kunde
Mein erster Kunde (Kurzes Intro für die, die meine Sissy Geschichte nicht kennen) Es ist jetzt ca 3 Jahre her das ich meinen ersten Kunden (freier) hatte und es ist noch wie heute in meinem Kopf eingebrannt. Ich war zu diesem Zeitpunkt 21 Jahre jung und habe in meiner Single Wohnung gelebt u... Read full Story
SissyAngelina 2021-09-08 1,840 Crossdresser trans slut sissy femboy Deutsch german hure
100%
Meine ersten Kunden
Mein erster Kunde (Kurzes Intro für die, die meine Sissy Geschichte nicht kennen) Es ist jetzt ca 3 Jahre her das ich meinen ersten Kunden (freier) hatte und es ist noch wie heute in meinem Kopf eingebrannt. Ich war zu diesem Zeitpunkt 21 Jahre jung und habe in meiner Single Wohnung gelebt u... Read full Story
SissyAngelina 2021-09-10 1,975 Crossdresser sissy german
77%
im a cd slut
i started dressing about four years ago and i love it. it turns me on to see the guys watching me. to know that they are thinking about fucking me. i loved it. so i called a friend that i knew was gay and we couldnt wait to get together. it was on. i was invited to his house for drinks and a dip i... Read full Story
jenny green 2022-06-17 7,633 Crossdresser Bareback Lingerie Guy Fucks Shemale Mature
50%
女装マゾひとみ
ひとみは、１８５ｃｍ、７３ｋｇ、４６歳女装マゾ。 この関連の掲示板で50才以上のソフトSの女装女王玲子様と知り合った。 ゴメオ（フォクシー）と2C-I（ケミカル系合ドラ）を使ってのプレイを 紹介します。 知合った玲子女王様は根っからと言う訳じゃ無いがSっ気のあるタチ。 何度か電話やメールでやり取りしてあう事に決めた。 場所は玲子女王様の住むマンション。 近くの駅まで車で迎えに来てもらう。 駅に着いて、持っていたゴメオをカプセルでアナルに挿入しておく。 迎えに来てもらった玲子女王様に「仕込んだの？」と聞かれたのでうなずく。 ヒーターのきいている車の中でゴメオが効いてくる。 ... Read full Story
YukiAoyama 2021-09-22 870 Crossdresser Amateur Asian
100%
Camming down the rabbit hole Ch5
I was jolted out of my sleep by the phone on my bedside table vibrating, bleary eyed I picked it up and saw a message from the couriers that a package would be delivered today around 4pm. The realisation that this was the package I had been waiting for and I could finally wear something else in my s... Read full Story
Dani_does_Dallas 2021-09-29 4,773 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade cum in mouth webcams
50%
Story of me
I have SOMETIMES been a cross dresser and enjoyed it.
 Maybe it was too much at times. I some how let the fantasies
go too far with me., but i love the feeling of another beauty of me, especially with my lovely beautiful masks. I loved the feel of the silk under-wares
on my body, and my long lo... Read full Story
Siziko Asia - Asian Beauty 2021-10-07 1,559 Stockings Teen (18+) Crossdresser Asian Lingerie
100%
Meine erste Erfahrung
Ich schildere hier meine Erfahrungen und wie aus mir die wurde, die ich jetzt bin. Es ist 1993, Ich bin zu diesem Zeitpunkt 8 Jahre jung und lebte in einer normalen Familie. Meine Eltern sind an einem Freitag Abend zum Essen gegangen mit anschließendem Kino Besuch. An diesem Abend sollte meine Cou... Read full Story
beginnertranny 2021-10-07 2,736 Stockings Crossdresser Amateur Cumshot Blowjob cum in mouth
100%
Sub to a Tranny story
One night as I was leaving a bar, I was approached by a beautiful woman who asked for my help. Not having plan I agreed. I followed her to her car and helped her take some stuff inside her apartment. After a couple minutes, I was about to leave when she offered me a cooked dinner. Well I am not ... Read full Story
77James 2021-10-07 4,995 Crossdresser Shemale Fucks Guy cum in mouth
100%
Camming down the rabbit hole Ch6
In the morning I decided to give the running a miss and do a long session with the DVD, my legs had become a little sore and tight so some extra stretches and yoga would really help. I once again surprised myself with how much more flexible I had become, the plug still in my ass giving me occasional... Read full Story
Dani_does_Dallas 2021-10-11 4,616 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade pov cum in mouth webcams
100%
Γιά τα βυζιά μου. Μέρος 1ο
Είμαι μιά ώριμη κροσς και λειτουργώ σαν πουτάνα. Γαμιέμαι πολλές φορές μέσα στην μέρα από πολλούς και πάντα δημόσια. [για τις εικόνες που αναφέρονται σε παρένθεση, βλ. την συλλογή Lara : sissy boobies part 1 & 2] Έφαγα τον πρώτο πούτσο το 1991. Και τον διάλεξα μεγάλο. Για όσα χρόνια ήμουνα st... Read full Story
hotmatureLara 2021-10-13 802 Crossdresser nipple play sissy boobs public fuck nipple suck
100%
When I was caught the first time.
I haven been dressing up for a long time, on/off as life and relationships would have it. But these last few years I really begun to take control of my desires and persuing this part of my life fully. So with the increase in frequency and openness of my dressing I was bound get noticed would co... Read full Story
love2crossdress 2021-10-13 2,513 Crossdresser Amateur Big Cock Lingerie
50%
How I became a Straight Crossdressing Guy
I'm a Straight Guy obviously with a CD Fetish that started 20+yrs ago when a Woman I was with asked me to dress up in her Roomates Lingerie as that was Her Kink. At first I was like Hell No!! Well she was very Sexy so I ended up doing so and to my Surprise it was Extremely Hot and Sexy in the Bedroo... Read full Story
Str8CD 2021-10-13 2,203 Crossdresser guy Straight
100%
Γιά τα βυζιά μου. Μέρος 2ο
..... συνεχίζεται από το part 1 ..... Σύντομη σύνδεση με το 1ο μέρος. Είχα περιγράψει το τί μ’ ενεργοποίησε κι άρχισα ν’ ασχολούμαι με τα βυζιά μου. Έκλεισα με την περιγραφή της αυτοσχέδιας ρογορουφήχτρας, λέγοντας «Έμενε να παίξω.» Πάτησα το κουμπάκι της αντλίας και πλησίασα τα κουπάκια στ... Read full Story
hotmatureLara 2021-10-14 941 Crossdresser sissy whore nipple play sissy boobs public fuck nipple suck
100%
Paula Herts UK and girlfriend in the woods
Paula and Girlfriend in the woods My ex gf used to have me dress up, go for a drive in the car, maybe to a truck stop or to the local woods. The 1st time she did it she had me dress up in sexy red lingerie, parked up near a local woods where people go to walk their dogs etc. She had me get out... Read full Story
PaulaXD56 2021-10-19 2,452 Stockings Crossdresser panties wanking uk
100%
Camming Down the Rabbit Hole Ch. 07
Opening my eyes I struggled a little as the residual cum on my face from last night’s show hadn’t been fully wiped off, I felt the dry and crusty leftovers crinkle on my skin, but couldn’t help but smile to myself as I remembered how it had got there. The intensity of that orgasm had been on another... Read full Story
Dani_does_Dallas 2021-10-22 6,073 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Lingerie Sex Toys Homemade self sucking pov cum in mouth
50%
My sissy, his first rime
My fella has always been happy to dress and be a slut for me, suck my dick and take a small dildo in his pussy. Until now I hadn't fucked him properly as he was to nervous. Recently we had been following the exploits of a CD friend through his blog and I knew they really excited my husband. When the... Read full Story
Aplane1 2021-11-01 1,910 Crossdresser virgin sissy
100%
My Sissy, his first time
My fella has always been happy to dress and be a slut for me, suck my dick and take a small dildo in his pussy. Until now I hadn't fucked him properly as he was to nervous. Recently we had been following the exploits of a CD friend through his blog and I knew they really excited my husband. When the... Read full Story
Aplane1 2021-11-01 3,384 Stockings Crossdresser Amateur Cumshot Lingerie Sex Toys
100%
Ein geiler Zwischenhalt im xxx-Kino
Meine erste Geschichte, auch so erlebt. Sie kommt hoffentlich gut an. Erlebt habe ich das in München, da gab es in der Schillerstraße noch ein rustikales Kino im Keller. Zu dem Zeitpunkt war ich Wochenendpendler und meist bin ich sonntags, bevor ich mich mit der Bahn auf die lange Strecke nach ... Read full Story
CD_Lisa_69 2021-11-02 1,721 Crossdresser Cumshot Bareback Blowjob gangbang Lingerie domination cum in mouth Kino
50%
Ashemaletube here we go…..
Today at 31 I finally got my own profile on ashemale and I’m so happy I can’t wait to post my pics and videos and hope everyone loves them and wants more to come. This is gonna be fun…... Read full Story
Serenity$$ 2021-11-11 1,757 Crossdresser
100%
Признание себя. Возбуждение от чисел.
Это - Часть 2. Я, согласно выбранному нику - "Скрытый Транс". И это именно так. Скрытый. Застенчивый. Стесняющийся самого себя, или части себя, своей части желаемого эротического сознания, той Сучки внутри себя. Той, которая испытывает возбуждение от женской части себя. Возбуждается от надевания се... Read full Story
Latent TS 2021-11-12 1,698 Stockings Small Tits Crossdresser solo Lingerie Sex Toys cum in mouth webcams
87%
My best night at a gloryhole and theater.
Hello, this is an account of what I consider my best night of my life; I was living in Baltimore, MD, Essex area at the time. A little background on me is that I am married now and at the time of this night but not that happy at the time. I was married for about 8 years and my wife and I decide to f... Read full Story
jenniferboobs 2021-11-12 5,041 Crossdresser Cumshot gangbang Compilation cum in mouth gloryholes theater
100%
Lope
Je suis une salope C’est un des fantasmes récurrents de la majorité des hommes qui aiment se travestir. Et j’avoue que l’idée m’a souvent excitée. Alors que j’étais avec ma femme dans une boutique de lingerie à Pigalle , des dessous très sexy entre les mains, un homme d'un certain âge a surpri... Read full Story
osvp75 2021-11-12 1,233 Stockings Crossdresser Cumshot Outdoor Masturbation Fetish Ladyboy Lingerie domination Premium HD
100%
Die Schwanz Insel
Es heißt eigentlich Huntington Island. Und es ist schon lange her und die meisten von uns in der Gegend wussten nicht viel darüber, außer dass die Gäste mit ihren Sachen mit dem Wasserflugzeug kammen und auch Essen und andere Lieferungen . Ich meine, es war ein Mysterium und nicht in der Stadt... Read full Story
jimyblue 2021-11-15 1,729 Crossdresser Fetish gangbang domination
90%
Camming Down the Rabbit Hole Ch. 08
A familiar sensation greeted me as my eyes opened and a yawn escaped my mouth, that oh so delicious feeling of my morning wood straining against my silk night ware. It was becoming an ever occurring pattern that no matter how large the orgasm the night before I would wake with the hardest of cocks, ... Read full Story
Dani_does_Dallas 2021-11-15 3,653 Stockings Small Tits Crossdresser Amateur Cumshot Masturbation Fetish Uniform Lingerie Homemade self sucking pov cum in mouth
100%
A Perfect Pandemic: A Transsexual Transition in a Troubled Time
A Perfect Pandemic A Transsexual Transition in a Troubled Time A Novelette by Alexandra Rios Text Copyright Reserved © August, 2021 Dedication Transgender Day of Remembrance is a solemn occasion. I am offering “A Perfect Pandemic” for free as an antidote to the fear, phobia, discrimination, d... Read full Story
the greatest liar 2021-11-16 4,783 Teen (18+) Crossdresser Group Sex Big Tits Bareback Creampie Big Cock gangbang domination Guy Fucks Shemale Interracial double anal webcams
100%
Hello!
Hello, I am posting this as a story because I couldn't couldn't  say everything I wanted to in me profile. I have just joined AShemale, I am a mature chap who had been on XHamster for nearly two years,  I love crossdressing and gurls, I have been dressing regularly for many years and before that... Read full Story
LanaLouissa 2021-11-22 2,402 Crossdresser
100%
Die Geburt von Isabella -Teil 1
Schon so lange ich mich erinnern kann, finde ich Damenbekleidung interessant. Ich war fasziniert von Frauen die adrett gekleidet durch die Fußgängerzone stöckelten oder schöne Kleider trugen. Mit dem Einsetzen der Pubertät entdeckte ich allerdings eine ganz neue Neigung. Ich begann die Wäsche un... Read full Story
Isabella93 2021-12-02 2,080 Teen (18+) Crossdresser Masturbation Fetish blonde Shemale and Girl
100%
The Fabulous Alessia Travestita
Alessia is a real transexual. Several of her porn videos are on this site. She collaborated with me in this story. Alessia is a natural blonde haired, brown eyed, mature fifty -five year old Transsexual woman from England. She is tall, very fit, stands 5'11," 36B-26-30 and a slender 133... Read full Story
darrell 2021-12-14 4,075 Crossdresser Blowjob blonde Big Cock domination Mature cum in mouth
87%
Maria's Fifteen Loads
I had always wanted to try Gokkun, all that cum seeing it in video's being drank down in big gulps always got me so horny and hard. As you see this girl likes her cum mmmm. So on a site that shall remain nameless those of you who have met me here and that other site will know shhh. I arranged wi... Read full Story
Sissy Fag Maria Clayton 2021-12-16 3,506 Crossdresser Blowjob Big Cock Lingerie cum in mouth drinking cum Swallowing Cum
100%
Cinema
Un día que andaba Excitada y con ganas de conocer chicos me fui a un cine q había donde había de todo chicos trans gay papis q iban a q se las chupara y pues ese día nu fue la excepción. Me vestí algo simple una camisa apretadita obvio mis pantys muy sexis y un pantalón de vestir obvio de niña. Y ... Read full Story
🫦💋💋🫦Maryfer 🫦💋 2022-01-03 1,397 Crossdresser Amateur Masturbation
100%
Klassenfahrt nach Köln
Diese Geschichte habe ich tatsächlich so erlebt. Es war mein erstes sexuelles Erlebnis überhaupt und es hat mich nachhaltig geprägt. Ich besuchte die 10. Klasse eines Gymnasiums einer norddeutschen Kleinstadt. Ich hatte zwar Interesse an Mädchen, hatte aber keinerlei Erfahrungen mit ihnen machen ... Read full Story
KatjaNDS 2022-01-03 3,288 Crossdresser Amateur Frottage cum in mouth
100%
First time doing that!!
So I love to dress like a girl and have done since I was about 15, but being married and all it’s a bit hard to do it very often,. I’m a local tradesman so am out all day in my van and have a good knowledge of the area I live in, or so I thought. About 2 miles from my house is a crushing site tha... Read full Story
Samantha Jewels 2022-01-03 2,370 Crossdresser Outdoor Creampie Blowjob Big Cock Mature Ass to Mouth cum in mouth
100%
Ein Sommertag
Nachdem ich während einer Klassenfahrt nach Köln meine ersten sexuellen Erfahrungen als Crossdresser gesammelt hatte, hatte ich mehr und mehr den Wunsch, die Zeiten, in denen ich mich als Frau fühlen konnte, weiter auszubauen. Ich genoss dabei insbesondere Zeiten, in denen ich allein zu Hause war un... Read full Story
KatjaNDS 2022-01-03 1,931 Amateur Bareback Blowjob Lingerie
91%
Aby my trans daughter
I am 50 and great shemale fan. I met Aby through PlanetRomio during covid lockdown. I was alone at home that time and i was searching for some good trans or shemale. So Aby so my profile and sent me message. I immediately replied. we exchanged our contacts and then shifted our chat to Whatsapp. ... Read full Story
Stud4Shemale 2022-01-03 4,018 Crossdresser Cumshot Bareback Shemale Fucks Guy Blowjob Big Cock Asian Guy Fucks Shemale cum in mouth
100%
Noche loca
Hola chicas y chicos que nos leen. Bueno les platico q otra de mis aventuras fue un día salir en el carro a recorrer la ciudad vestida toda de mujer, situación que me excita mucho y me encanta ver como te buscan los hombres. Pues andaba por la ciudad y que se me ocurre pasar por un motel de medio p... Read full Story
🫦💋💋🫦Maryfer 🫦💋 2022-01-03 1,596 Crossdresser Amateur Cumshot Masturbation threesome blonde cum in mouth
50%
Turned into A Feminized Slut by FeminizedBBCslut
Bound and Turned into Feminized Slut by FeminizedBBCslut Chapter 1 - How I ended up meeting John I am an asian TV on hormones for 3 years and as a result have developed a pair of budding breasts that fill out my A cup bra. I have always been fantasizing about being turned from a shy conservative asi... Read full Story
8thick_ 2022-01-03 3,542 Crossdresser
100%
think about cock all the time
i find myself looking at chicks with dicks all the time. i love them. they turn me on so much. i cant stop thinking about being with one and im going to be with one very soon. i cant wait to swallow all of her shaft. every inch of it. and when she starts to cum i will suck it in deeper. fuck that tu... Read full Story
jenny green 2022-01-05 2,395 Crossdresser Cumshot Bareback Blowjob Big Cock Mature cum in mouth shemale + shemale
100%
Sissy gets her Prezzie
Justina woke up on Monday morning and was already tired, she had been dogging till 3 and her little ass was a little bit sore. She made her way to the bathroom and had a pee, brushed her teeth then headed for the kitchen to make coffee. As she was walking her phone went off, she had a text from ... Read full Story
Samantha Jewels 2022-01-06 2,968 Stockings Crossdresser Cumshot Bareback Blowjob Big Cock gangbang domination Mature Homemade Ass to Mouth
50%
La trasformazione di una sissy parte 1
Ricordo ancora come se fosse oggi la prima volta che conobbi Franco, non so nemmeno io come ma quella sera in cui mia moglie si trovava di turno notturno mi sentivo particolarmente eccitato. La lettura di un libro particolarmente coinvolgente si era impossessata di me. Molte volte mi chiesi se davve... Read full Story
pinkslip 2022-01-06 1,271 Crossdresser Amateur Blowjob Lingerie domination Sex Toys humiliation sissystart
50%
Lacey gets dominated
thx, get rid of some work, but the pensum will rise again, meetings awaiting ... business as usual. But never mind, I will find some time to play with my sissy slave... thats me lacey Seeing you standing there like this ... I got a new idea. It might bring you up a bit to be ordered to go d... Read full Story
goodgurl34 2022-01-12 1,535 Stockings Crossdresser Blowjob Lingerie domination Guy Fucks Shemale Sex Toys Homemade
50%
Not your usual birthday present
So here we go again “Happy Birthday” to me, at 51 it’s not that great really it’s just a reminder your getting older!! Anyway here I am 51 having an absolute ball and fulfilling my wildest dreams, Justina likes being out of the closest and loooooves cock.. So for her birthday she hopes someone has ... Read full Story
Samantha Jewels 2022-01-12 2,603 Stockings Crossdresser Amateur Blowjob Big Cock gangbang Lingerie domination Sex Toys Mature cum in mouth
100%
Caught Dressed
Caught Dressed by Jordan Skythe Chapter One He turned in fright as the bedroom door opened, and frantically pulled his comforter off the bed as Bradley entered. “That was locked!” Brad straightened and smiled. “Woah! Hi!” “What the hell!” Brad motioned to the door frame. “You do know there’s... Read full Story
AuthorJordanSkythe 2022-01-20 3,373 Stockings Crossdresser Bareback Blowjob Uniform Lingerie
100%
New Game by Jordan Skythe
New Game Alan tossed his game controller, then reclined on the bed and sighed. “I’m bored.” He nodded in agreement. “So am I.” He wasn’t, but wanted to see where the declaration could lead. “We need to do something new.” He felt his breathing increase, wondering if this was the moment he could... Read full Story
AuthorJordanSkythe 2022-01-24 1,902 first time Stockings Crossdresser Bareback Uniform seduction Lap dance
100%
How I Became Chrissy the Caged Sissy
I am a sissy, or femboy, or tgurl, or shemale? Well either way I like wearing female clothes and being treated like a girl, especially in the bedroom, and now I also like being locked up in a chastity cage that I wear 24/7 now. This is the story of how I became a caged sissy: "Put it on and ... Read full Story
Chrissy Tunnell 2022-01-27 3,871 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
100%
Making Love Vs. Fucking
We all know the difference between making love and fucking, but for those that may not here is my take on the subject. When my partner makes love to me it is slow, gentle, sensual....he does it not only to make himself feel good, but to satisfy me as well. Making love is selfless and sacrificia... Read full Story
Chrissy Tunnell 2022-01-28 2,338 Crossdresser Amateur Masturbation Bareback Creampie Fetish Blowjob domination Guy Fucks Shemale Homemade
100%
He Could Have R*ped Me!
This guy was so big, taller than me and I'm 6 feet, and bigger, not fat, just right for his big size, and I am so skinny, except for my tummy, that he could have pinned me down and forced himself onto and into me against my will, and no matter how much I'd struggle with him and fight back, he could ... Read full Story
Chrissy Tunnell 2022-02-02 2,566 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
100%
das erste mal im pornokino
Meine erste Erfahrung als Damenwäscheträger in einem Pornokino. Vor einigen Jahren hatte ich mal einen bekannten, den ich am Telefon kennen gelernt hatte. Er war sehr dominant und ich musste ihm am Telefon mit „Meister“ ansprechen. Vor den verabredeten Anrufen habe ich mir immer einen dicken Jo... Read full Story
ritadwt 2022-02-01 1,571 Crossdresser
50%
municipal worker
We met him on Twitter for a long time, we chatted on the phone and on Twitter for a long time, then he invited me to his house and I went and he fucked me but it wasn't good, he ejaculated inside me and I went to the room and masturbated in front of the large mirror it was a different experience... Read full Story
Beyza_Trans_Girl 2022-02-01 1,592 Stockings Crossdresser Amateur Masturbation Creampie Fetish Lingerie Guy Fucks Shemale Mature Homemade
100%
K*dnapped & R*ped
"You're nothing but a tease, a flirt, you just like to play around and lead guys on," someone messaged me on the swinger site I'm on called AdultFriendFinder. "No," I replied, "I have actually hooked up with guys I met here, I am just very busy." And that is the truth. I work a full-time job and ... Read full Story
Chrissy Tunnell 2022-02-02 3,273 Crossdresser Amateur Outdoor Bareback Fetish Ladyboy domination Guy Fucks Shemale Homemade
100%
Sissy Femboy Chrissy in Drag at the Club
"Can you wear a dress tonight?" "I can't crossdress in public, I'm not 'out' and don't want to be seen that way." "That's okay. We're going to a gay-only club that has a drag queen show tonight, so you'd fit right in." "Cool, but I'll have to change when we get there." "Awesome! See you tonight!... Read full Story
Chrissy Tunnell 2022-02-03 4,695 Crossdresser Amateur Bareback Shemale Fucks Guy Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature Homemade cum in mouth
100%
Для сисси-девочки. (сисси-мотивация)
Подойди к зеркалу и посмотри... Что ты видишь? Ты ничего не видишь. В зеркале ничего не отражается, потому что тебя нет. Ты пустое место. Ты сейчас – лишь возможность стать чем-то... По сути - ты каркас, из которого можно что-то делать. Сбрей на теле лишние волосы. Особенно на груди, ногах, под мыш... Read full Story
ALLA_off 2022-02-04 1,307 Crossdresser solo sissy slut
50%
Need A New Keyholder/Daddy
I get an erotic thrill off of the thought of another man "owning" my body and having control over my sexual pleasure. I enjoy having my boyclitty, my cock, locked up in a chastity cage; it represses my erections, hides my cock so I rarely see it, and denies me any of that little sexual pleasure of t... Read full Story
Chrissy Tunnell 2022-02-14 2,071 Crossdresser solo Amateur Fetish Ladyboy Lingerie domination Guy Fucks Shemale Frottage
50%
About Rachel Bottoms
What turns me on sexually is being with a dominant male, female or couple that is confident. The thought of submission and the offering of my body and mind for your pleasure is what I am after. Knowing you like what you see and feel or that you are turned excites me. I want intense encounters. S... Read full Story
Rachelbottoms 2022-02-14 1,603 ass Crossdresser Lingerie sissy bottom
100%
The Opening of Villa Olivia
All Stories are 100% true. Names and Locations might be altered to protect the privacy of myself and others. In my last blog post I have given you an overview of what happend in the past months. In the beginning of January we have finished the works on my new "working environment". We call it "Vi... Read full Story
TV_Whore_Olivia 2022-02-21 2,341 Crossdresser Amateur Group Sex gangbang Guy Fucks Shemale Homemade escort sissy prostitute hooker slaves owned Hooker cd
100%
First Week of Work
All Stories are 100% true. Names and Locations might be altered to protect the privacy of myself and others. On the day after the opening I felt very exhausted. Since I haven't had any similar events lately, my body just isn't used to this stress. In order for me to be ready for monday, J let me ... Read full Story
TV_Whore_Olivia 2022-02-21 3,249 Crossdresser Amateur escort sissy prostitute hooker slaves owned Hooker cd
100%
How I Became His Office Fucktoy
Until this job ended last year, every day at my lunch break I would service one of my many Daddies in his office in the building where I worked. He'd always slip me a few bucks, a $20 or even $50 afterwards, not as a payment for sex, but as a "tip" "for all the hard work you do here," he says. I wor... Read full Story
Chrissy Tunnell 2022-02-18 3,515 Crossdresser Amateur Fetish Blowjob Ladyboy domination Guy Fucks Shemale Mature cum in mouth
100%
An Orgasmic Uber Ride
"Chris?" the Uber driver asked me after driving up and rolling down his window. "Yes," I replied and then I got into the passenger seat next to him. I usually ride upfront in Uber rides because I get car sick easily in the back. After fastening my seat belt we were off. The guy was older, maybe ... Read full Story
Chrissy Tunnell 2022-02-18 3,260 Crossdresser Amateur Outdoor Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
100%
Как стала девочкой!
В детстве примерно лет в 5-6 я любила ходить с родителями к родственникам на всякие вечеринки типа свадьба или рождение ребенка. У этих родственников в доме был туалет совмещенный с ванной комнатой и для ребенка он казался довольно большой и свободной комнатой. Дети частенько использовали свободно... Read full Story
MarryCro 2022-02-21 3,954 Crossdresser Masturbation domination Guy Fucks Shemale Homemade e
100%
CD/TS Shemale Chrissy Fucked On the Ranch
I met John on the swinger site AdultFriendFinder. He was everything I was looking for: old, in his late 60s, and not rich, but financially stable and independent, owning a ranch that has been in his family for generations. Maybe he could become the Sugar Daddy I am looking for? I am a shaved-smooth ... Read full Story
Chrissy Tunnell 2022-03-04 3,406 Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
75%
Mein gestrenger Meister - Sie war bei dir
wie unglücklich du mich machst, weißt du gar nicht. Seit du meine Frau gesehen hast, als sie uns beiden einen Kaffee reingebracht hatte, als du in mir stecktest. Diese Begegnung hätte nie stattfinden dürfen... Wie sehr du mich doch schon kennst. Du weißt, dass ich nicht von dir los komme, obwohl du... Read full Story
L-u-c-y 2022-03-11 1,919 Stockings Crossdresser threesome blonde domination
50%
Why Do Guys do this?
Why do guys on the porn, dating sites and social media sites I'm on want to chat live on video all the time? And if I don't agree they unfriend and even block me. Why? Aren't my videos and pixies good enough? They are of me...they ae real, and not photoshopped (except for sharpness and clarity.) I h... Read full Story
Chrissy Tunnell 2022-03-14 2,408 Crossdresser solo Amateur Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Frottage Homemade pov Compilation
100%
Closet sissy takes 5 strangers cocks in one afternoon
Wife went away on holiday so it was time to change into my alter ego Kirsty. I put an Ad on Fabguys and within minutes I was getting guys wanting to come and fuck me. This was the second time this year I had been on Fabguys looking for stranger sex and so far I have been fucked 31 times within a t... Read full Story
Sissykirsty 2022-03-14 2,327 anal Crossdresser sissy
100%
In the village
In my 20s i moved to a small village, I live on a very quite road with about 10 houses on it a two pubs in the main village. One of the older men that lived on that road every time i walked pasted his house he'd say hello seemed a nice bloke, i never dressed as a girl near my house so he'd got no i... Read full Story
Kelly Abbey Anderson 2022-03-14 3,039 Crossdresser Bareback Creampie Mature
100%
Big cock
I've had a lot of black men I still have a few around here two black men from Nottingham invite me over every now and then. But the biggest was when I was about 25, he was white, in his late 60s but when he unzipped I could not believe what I saw! it was like a trunk 12inch + and about 3inch thick h... Read full Story
Kelly Abbey Anderson 2022-03-14 2,891 Crossdresser Creampie Big Cock
100%
Dominated sissy goodgurl34
Mmmm ty Sir Deitrich --I'm standing in your open doorway wearing black latex stockings and garter and some hott red lace panties over top -I have a black corset on and a very sheer dress on ,wig and gurl mask ---my wrists are cuffed to a circle hook one on each side of the doorway door jam about 6... Read full Story
goodgurl34 2022-03-15 2,141 Crossdresser threesome redhead domination Guy Fucks Shemale Sex Toys Homemade shemale + shemale
100%
Camming Down the Rabbit Hole Ch. 09
As per my previous mornings recently, I stirred and rubbed the sleep from my eyes, that delicious feeling of my silk night ware stretching over my taught nipples and my morning wood throbbing in its lace enclosure. The urge to touch myself was palpable, it seemed no matter how hard I came the night ... Read full Story
Dani_does_Dallas 2022-03-22 3,151 Stockings Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking pov cum in mouth webcams
100%
Sono una cagnolina in calore per Paola
Oggi al lavoro è stata una giornata lunga ed impegnativa, arrivo a casa, una doccia e via corro da Paola. purtroppo arrivo con mezz'ora di ritardo al nostro appuntamento. Lei è bellissima, è seminuda, indossa un reggiseno composto solamente da due triangoli di perle che circondano i suoi seni, i ... Read full Story
Sissy Mari 2022-03-22 1,722 Amateur Fetish Lingerie domination Sex Toys Homemade sissy shemale + shemale sissy slut sissygasm sissy crossdresser
100%
2nd date with Latina Sissy Destiny
So this was my second time with Destiny, a really cool Latina CD/Sissy who had just turned 22. You might want to read my first goaround with her title, “Deflowering Latina Sissy Destiny” as it will give background and context here. After our first encounter, she signaled that she was definitely... Read full Story
AllenB 2022-04-05 3,847 Crossdresser Cumshot Latina Creampie Shemale Fucks Guy Blowjob Interracial cd Homemade sissy cum in mouth cum swallow amatuer cd
100%
My Sugar Daddy Fucked My Girlfriend...And I Joined In
I am a shaved-smooth, boyish bisexual male slut. At 43, I still look and feel young, and I enjoy the feel of and attention from older men, the older the better, 55 and up, with gray hair, wrinkles, and very hairy chests and bods. My Daddy, a 70-year-old White man that fits this description, "owns" m... Read full Story
Chrissy Tunnell 2022-04-12 2,475 Crossdresser Amateur Shemale Fucks Guy Fetish Blowjob Ladyboy Shemale and Girl Guy Fucks Shemale Mature cum in mouth double anal
100%
My Sugar Daddy Spanked Me & My Girlfriend (I screwed up again)
In my last fantasy article I explained how my Sugar Daddy allows me to date girls since I am bisexual and attracted to them too, but they, and in fact anyone, are not allowed to touch me intimately without explicit permission from my Daddy. Anytime a girl wants to touch me: kiss, hold hands, put her... Read full Story
Chrissy Tunnell 2022-04-12 2,053 Crossdresser Amateur Big Tits Shemale Fucks Guy Fetish threesome Blowjob Big Cock Ladyboy Shemale and Girl Guy Fucks Shemale cum in mouth
100%
Camming Down the Rabbit Hole Ch. 10
As the sun beamed in through a gap in the curtains my now familiar morning wood strained at the silk of my nightwear. How was it that no matter how hard I came the night before it would wake up eager and ready to go. As had become customary my mind would be filled with the events of the previous nig... Read full Story
Dani_does_Dallas 2022-04-12 3,193 Crossdresser solo Amateur Cumshot Masturbation Lingerie Sex Toys Homemade self sucking cum in mouth webcams
87%
Fuck me like a girl❣️🫦👸🏻🙏
I’d like meth 💉🧘🏼‍♀️ and get fucked, be completely used like a girl👩🏻‍🎓💄🫦 👙👗💍👛👠👠💅🏼👸🏻👰🏻‍♀️ by you❣️🫵🏻 I will be absolutely happy, if you treat me like your little girl, you give me a kiss and we start cuddling together, then I’ll reach into your pants and get your cock out of them🫦👅 I’ll start ... Read full Story
ViktoriaCD 2022-04-12 3,190 Crossdresser sissy trap
100%
Expérience étudiante
Lors de mes études, je me trouvais dans un logement étudiant. Chaque semaine le propriétaire des lieux passais voir chaque résident afin de recevoir son loyer, et comme chaque vendredi soir il frappa à ma porte. Cette semaine la, je n'avais pas reçu l'argent de mes parents, je lui explique donc que ... Read full Story
Sara Tissy 2022-04-20 350 Stockings Teen (18+) Crossdresser Blowjob Lingerie
100%
First Time Buying Lingerie
As a youngster, I couldn't help but notice the carousels of hosiery on display in various shops that my mother would visit. Displays of stockings and tights (pantyhose) for the discerning housewife. Brands like Pretty Polly, images of nylon clad legs on the glossy cardboard and a see through window... Read full Story
Daddybear71 2023-09-13 6,221 Stockings Crossdresser Amateur Masturbation Lingerie teen (18+)
100%
Camming Down the Rabbit Hole Ch. 11
I sat there for some time, my phone still in hand. I couldn’t fully comprehend the situation and where I was. All this started when I was put on furlough and thought I would be losing my job, an idea born out of boredom, hornieness and desperation. What started as a regular cam show with a guy hopin... Read full Story
Dani_does_Dallas 2022-04-25 3,927 Crossdresser Amateur Cumshot Masturbation Blowjob Uniform Lingerie Shemale and Girl Sex Toys Homemade self sucking pov cum in mouth
100%
PK Moosburg 26.04.22
Hallo ihr Lieben, heute war ich mal wieder seit langer Zeit im Pornokino in Moosburg. Coronaregeln sind aufgehoben, man(n) kann sich also wieder frei bewegen. Bin von der Arbeit aus direkt hingefahren, war so 15 Uhr. Auf der Arbeit habe ich meist meine Halterlosen und ein Spitzenhöschen an, das Ge... Read full Story
CD_Lisa_69 2022-04-27 2,010 Crossdresser Amateur Outdoor Bareback Blowjob cum in mouth
83%
My first crossdresser experience
Hi. I am a bisexual(passiv), i was born in muslim county and being bi is like crime. Thats why i never had any sex with a guy. I was just mastrubating and fingering my ass, sometimes was using cucumber . Finaly i had a opportunity to go Europe and study at the age of 29. When i arrive to France, fir... Read full Story
Private_love 2022-05-06 3,596 bisexual crosdresser passive
100%
Camming Down the Rabbit Hole Ch. 12
We woke up many hours later, still intertwined, my morning wood throbbing as Ellie slid inside my panties and wrapped her hand around it. This was a much better way to wake up than usual, and we proceeded to have a really relaxed slow fuck. She reached a much more low key orgasm but I knew I wouldn’... Read full Story
Dani_does_Dallas 2022-05-09 4,981 Crossdresser solo Amateur Cumshot Outdoor Masturbation Blowjob Shemale and Girl Sex Toys self sucking pov cum in mouth webcams
100%
Gangbanged at the beach
My BBC friend took me to the beach, where people make sex. We arrived in his van. I was in the back of the van, chained blind folded, with my mouth wide open and a huge horse dildo in my sissy pussy. Suddenly I hear the van door opening. I hear many voices of other men. My BBC friend was telling oth... Read full Story
brunasissyslavedolrj 2022-05-09 4,234 Crossdresser Group Sex Outdoor Fetish Big Cock Lingerie domination Guy Fucks Shemale Interracial Sex Toys Ass to Mouth cum in mouth
80%
intimate Cousins
My favorite cousin and first lover, Billy, was just released from prison and I was anxious to see him. I am ecstatic that he is out, and I am thinking about all the past fun we had as I prepare to revisit those good times. Tommy knows all about my relationship with Billy and he understands my need t... Read full Story
Regina10 2022-05-13 5,748 Stockings Crossdresser Cumshot Masturbation Bareback Blowjob Big Cock Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth double anal