Sort by
Relevancy

Free Stories

81%
Forced Entry
Danny sat at the bar of the Holiday Inn nursing his fourth double scotch, espousing to the man beside him the reasons why his company was the best designer and distributor of accounting software in the world. Danny was a large man in his forties and was running to fat. He was dressed in a travel-... Read full Story
shemale lover 2012-11-16 15,974 Big Cock oral transvestite forced sex
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 17,577 Crossdresser sucking Big Cock ass licking big boobs
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 5,298 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
96%
Family Frolic
FRIDAY My sister and her husband wanted to take a few weeks off in the sun and asked me to look after their kids for a while. I'd move out of my tiny apartment and into their house for the duration. As I was still living off my severance and they had a nice spread with an indoor pool and a h... Read full Story
shemale lover 2012-01-14 31,318 strapon porn
50%
HOSPITALITÉ DU SUD
Ash regarda sa mère, incrédule quant à ce qu'elle venait de dire. Il comprenait la prémisse de base de ce qui s'était passé, mais le raisonnement qu'elle avait dû le déconcerter. "Pourquoi ?! Pourquoi ferais-tu ça ?!" Il a plaidé, la voix légère et désespérée. Elle haussa l... Read full Story
Femboy 2021 2023-02-05 1,328 Stockings Crossdresser Shemale Fucks Guy Big Cock Lingerie Guy Fucks Shemale
100%
Mes débuts
Travesti depuis longtemps maintenant j'ai toujours aimé les tenues de serveuse la jupe et le chemisier sont pour moi la féminité absolue, ados je me suis mis à la couture je chapardait les vêtements de ma grande soeur les gaines et combinaisons de ma mère, un jour j'ai même fait des photos de moi as... Read full Story
bernadette trav 2023-07-26 974 anal Stockings Crossdresser solo Big Tits Cumshot Fetish Uniform Lingerie Sex Toys Mature Homemade
72%
The Weekend
The weekend A story inspired by the very sweet and sexy samantha satine and my beautiful wife Part 1 - The preparation samantha packed her suitcase with her usual attention to detail, makeup, lingerie, wigs, but no dresses. Her head was confused by this, Master D had given her instructions... Read full Story
MasterofSissies1 2018-12-04 9,019 anal tranny Stockings Crossdresser Group Sex gangbang oral domination Guy Fucks Shemale transvestite schoolgirl School uniform maid uniform
100%
2.ΜΕ ΕΝΑ ΦΙΛΟ ΓΙΑ ΤΣΟΝΤΑ ΣΕ ΚΙΝΗΜΑΤΟΓΡΑΦΟ Μια φορα με πηρε ενας
2.ΜΕ ΕΝΑ ΦΙΛΟ ΓΙΑ ΤΣΟΝΤΑ ΣΕ ΚΙΝΗΜΑΤΟΓΡΑΦΟ Μια φορα με πηρε ενας φιλος μου να παμε να δουμε κινηματογραφο τσοντα.Δεν ηξερε τιποτα για εμενα οτι ειμαι crossdress.Εγω τις περισσοτερες φορες μεσα απο το τζιν φοραω καλτσες η καλσον ανοικτα απο κατω, σουτιεν η μπουστακι και φυσικα στρινγκ.Η αισθηση του ν... Read full Story
crossofia 2023-10-01 4,825 anal Stockings Crossdresser Amateur Group Sex Cumshot Masturbation Lingerie Sex Toys Mature big ass sissy cum in mouth
89%
The Magic of my first Blac Coc
Wow! This was my first real experience with Black Cock. it was right after my divorce. I was in my late twenties. I ran my ads as a crossdresser on a few dating sites and on Craigslist. I received a message on my AFF site from a member whose profile name was BBCRicky. My interest was immediately... Read full Story
Tvtrinity 2021-04-07 21,976 Stockings Amateur Bareback Lingerie Interracial transgender sissy bbc сrossdresser tvtrinity
100%
Porn Cinemas and GinaG
I really like porn cinemas, there is a certain seediness and sleaziness about them that makes them alluring to me. My problem is that living as I do in the south of the UK, there are no porn cinemas anywhere near me. Fortunately, I travel in my job quite a bit and so can get to cinemas in Birmingham... Read full Story
GinaG 2019-01-08 3,627 Stockings Crossdresser Amateur Cumshot Masturbation Blowjob Lingerie Mature cum in mouth shemale + shemale
100%
FÉMINISÉE PAR BBC MALE ⚧️
Après avoir abandonné l'université, je n'avais évidemment plus le droit de vivre dans les dortoirs. Mes parents ne me reprendraient pas. Je n'avais qu'un seul endroit où aller : l'appartement de mon ami Jack. Nous nous sommes rencontrés au collège en première année. Il a toujours été bon avec moi. ... Read full Story
Femboy 2021 2023-02-16 1,306 Stockings Crossdresser Fetish Blowjob Big Cock Lingerie domination Guy Fucks Shemale Interracial cum in mouth
100%
Beryl's birthday suit
I tried on my sister's panties when I was 12. They looked so cute, so sexy.. I couldn't help myself. I tucked my dick between my legs and pulled them over my hips, delicately positioning them just like a girl. They felt yummy! When I saw the shiny, lacy pink briefs in the mirror - snug, flat pu... Read full Story
Beryl 2023-12-12 7,599 first time Stockings Crossdresser Bareback Blowjob Big Cock Lingerie redhead sissy cum in mouth
100%
Danielle's First Meeting
Daniel stood on the front porch and waited for his date to arrive. Well, Daniel at this particular time was actually Danielle. You see, Daniel was a crossdresser. Danielle was his female alter ego. He was 37 years old, medium build, average you might say and stood 5-feet-10-inches tall, weighing in ... Read full Story
shemale lover 2012-06-18 4,453 Stockings Crossdresser Cumshot shemale oral sex
100%
A Wife Comes Around Chapter 2
I caught my breath after my wonderful experience, as we were all around the table now commenting on my orgasm. I sipped my drink and exclaimed that was the best orgasm I've ever had. It was getting late now and I had to get going. I put the sopping panty in my bag and thanked everyone. About a mo... Read full Story
shemale lover 2012-07-25 4,315 Group Sex Cumshot oral
100%
Junior's Department
Junior’s Department The long-haired young male browsing alone in the ladies’ junior’s department caught his eye and he stopped walking to the store exit. He stepped behind a display rack across the aisle, then watched him approach a mirror and scan the area before holding the skirt and blouse up ... Read full Story
AuthorJordanSkythe 2022-01-20 2,903 first time Stockings Crossdresser romance femboi
33%
Old Folks Chapter 1
I had been cross-dressing for some years, but I had never been with another man. I had been talking on a gay chat site for some months when I found someone who I got on with well. We exchanged photos I was happy with his and he was happy with mine. Deciding to get together, we arranged a date and ti... Read full Story
shemale lover 2012-12-21 4,418 Stockings Crossdresser Lingerie Mature cd
14%
Young CD wants to be used
My biggest desire is to have my make up done by a professional. And then be tied up in a room where all of a sudden at least 10 Big Badass guys enter the room. They use and abuse me and put cum all over and all inside me and they leave me there tied...... Read full Story
ASlaveToYourCocks 2018-03-02 3,120 Stockings Lingerie domination Interracial Sex Toys cum in mouth double anal
85%
Becoming Zoe
My soon to be wife Annie had taken a job out of town and I only saw her every two weeks or so. I was so missing her. She and I had become long distance lovers. She was scheduled for a flight home on Friday night. I was going to pick up her son Zakk from his dorm and the two of us were going to p... Read full Story
Zöe from Kingston 2018-08-09 9,418 Stockings Teen (18+) Crossdresser Cumshot Bareback Blowjob blonde Big Cock Lingerie Mature cum in mouth
100%
Vanessa gets more than she bargained for!
Vanessa had it all planned out meticulously. She had taken the day off and planned on doing a bit of last minute shopping before checking into the hotel in the early afternoon. She eventually decided on buying a massive dildo to get her ready for the party. This would give her plenty of time to take... Read full Story
Vanessa Luv 2020-05-15 8,023 Stockings Crossdresser Group Sex Big Cock gangbang Lingerie Interracial cum in mouth double anal
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 2,690 Crossdresser
50%
L'INVESTISSEMENT SISSY ⚧️ ⚧️
La fin d'une autre longue journée. Près de 19h00 et Colin Spencer travaillait toujours dans son box, presque terminé avec le dernier des papiers que l'un des associés principaux de la société d'investissement dans laquelle il avait effectué un stage depuis près d'un an maintenant l&#... Read full Story
Femboy 2021 2023-03-21 1,065 Stockings Lingerie domination Guy Fucks Shemale Interracial Sex Toys cum in mouth
0%
Latex succubus
The lights of the city obscured the supposedly brilliant starlight in the night sky, leaving only dim and scattered scattered stars adorning the gloomy night sky half-covered by dark clouds, and the crescent-like crescent moon guarding it in the distance makes the night seem less empty Lonely. Mayb... Read full Story
Alicexiao 2023-01-06 4,646 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
100%
The Story of Stephanie (Chapter 2)
So there I was. Kind of at a crossroads. I didn't know what to do with myself. The months previous, anytime I had free time on my own, I was crossdressing and going on cam getting a thrill out of men watching me. Men! That was just strange. But I didn't know what to do with myself. I really did get ... Read full Story
Stephanie Wild 2024-07-10 3,108 Crossdresser Amateur
86%
Hotel Heaven or Nightmare
You've enjoyed a relaxing bubble bath, you're smooth skinned and perfumed. You dress with your new purchases, Gio seamed stockings, leather mini skirt and Carvela heels with sexy peep toes. You take time to apply your make up while you contemplate what the evening will hold for you. There's nothing ... Read full Story
shemale lover 2013-03-12 6,136 sex toy Crossdresser Cumshot Big Cock Lingerie
100%
CONTINUO AD INCONTRARMI CON PAOLA, LA MIA MISTRESS
E' trascorsa anche questa settimana, è stata lunga, molto lunga, non vedevo l'ora di vedere Paola, di succhiare il suo cazzo, e di farmi scopare. Finalmente arrivo a casa sua, è pronta e mi sta aspettando. E' splendida, anche questa sera indossa gli stivaloni alti di lacca rossa, un piccolo tang... Read full Story
Sissy Mari 2021-10-07 1,210 Stockings Crossdresser Amateur Lingerie Sex Toys Homemade sissy shemale + shemale sissy slut sissygasm sissy crossdresser
85%
Признание. Часть 1
Никогда не думал, что здесь буду писать о своих, скажем так мыслях. Не думал, не гадал, но женское эротическое бельё меня всегда возбуждало. Пишу рассказ с телефона, поэтому буду краток. Покупая красивое эротическое бельё жене, я возбуждался уже только при его выборе, до покупки. Моя Возлюбленная не... Read full Story
Latent TS 2020-06-26 3,297 Stockings Small Tits Crossdresser solo Masturbation Lingerie Sex Toys Homemade КроссНачало
75%
Honeymoon Suite 2
Jason is on the phone with room service, while I am about to change out of my wedding gown. I had just got married, and I was now the blushing bride. Yes I got married. I was nervous now and my pussy was burning, because of the crazy bet we had made about not having sex a week before the wedding. We... Read full Story
Regina10 2021-02-22 3,840 Stockings Crossdresser Big Tits Cumshot Bareback Creampie Blowjob blonde Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
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 2,099 Stockings Small Tits Crossdresser solo Lingerie Sex Toys cum in mouth webcams
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 1,907 Stockings Crossdresser Blowjob Lingerie domination Guy Fucks Shemale Sex Toys Homemade
50%
Ma femme et maintenant elle va me transformer en Sissy
Karen et moi sommes mariés depuis 28 ans. Nous avons eu nos hauts et nos bas, mais nous sommes restés fidèles et avons produit deux excellents sexe en conséquence. J'ai toujours été secrètement bi. J'ai été pris au piège de quelques accessions, mais j'ai résisté aux tempêtes et j'ai visité des relat... Read full Story
Femboy 2021 2023-01-24 1,160 Stockings Crossdresser Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys
50%
Ado est forcé à poule mouillée
Ma première fois avec un autre homme était quand j'avais 18 ans à la fin des années 80. Ma copine était vierge et le plus loin nous sommes allés baiser et frotter avec nos vêtements. J'emmènerais mes magazines sales là où nous habitions dans les bois et enlèverais tous mes vêtements et me mastur... Read full Story
Femboy 2021 2023-01-27 855 Stockings Teen (18+) Crossdresser Fetish Blowjob Lingerie Shemale and Girl domination Sex Toys cum in mouth
50%
DE QUOI UN HOMME A-T-IL BESOIN ? ⚧️
"Tu es marié, n'est-ce pas ?" L'employé a demandé alors qu'elle prenait mon argent. "Pourquoi tu demanderais ça ?" "Évitant la question, oui marié et depuis un bon bout de temps." Elle l'a dit avec un tel sourire que je n'ai pas pu m'empêcher de répondre. "Oui, en fait je le suis." Bon je s... Read full Story
Femboy 2021 2023-02-17 861 Stockings Crossdresser Fetish Big Cock Lingerie Guy Fucks Shemale Sex Toys
50%
💘 SES CADEAUX ⚧️ ⚧️ ⚧️
Elle lui réservait plusieurs surprises... Nous venions de rentrer du mariage d'un ami. Ils ont organisé une belle cérémonie sur un terrain de golf sous des arbres, puis une fête à l'intérieur du club house. C'était un bar ouvert et ils avaient engagé un groupe. Nous avons passé la majeure partie ... Read full Story
Femboy 2021 2023-02-21 753 Stockings Crossdresser Cumshot Creampie Fetish Lingerie Shemale and Girl Sex Toys
100%
Caught In Your Wife's Panties
DRESSED IN YOUR WIFE'S PANTIES I called on a girlfriend of mine the other day and you'll never guess what. I'd gone upstairs to use the bathroom, and I noticed her bedroom door was ajar and, me being a nosy fucking bitch, glanced in. What did I see? I saw her kinky husband pulling on a pair ... Read full Story
shemale lover 2013-01-17 8,525 Crossdresser Cumshot sucking Big Cock Lingerie
100%
Becoming a Cock Worshipper
I first realized I was bi the summer after high school. Up until then I had only been really interested in girls. Like any high school guy I watched a lot of porn and soon realized that I really liked really nasty deep throat blow job scenes. I especially enjoyed watching a girl choke and gag and... Read full Story
shemale lover 2012-02-29 4,047 Fetish crossdressing
100%
Anastasia's Life So Far
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barbi... Read full Story
shemale lover 2012-11-27 11,203 Fetish crossdressing feminization
75%
Sissify Your Boyfriend Manual - transation
original= manual-sissificar-a-tu-novio-4979 Used google translate, found some pronoun/object/context issues, and I believe ladybug = ladyboy Sissify Your Boyfriend Manual MANUAL FOR WIFE/GIRLFRIEND TO SISSIFY YOUR MAN, DISCOVER HIS SUBMISSIVE SIDE AND TURN HIM INTO ?HORNAND? AN... Read full Story
shelli_k18 2021-04-20 8,913 femdom sissyboy sissification sissy training FLR hotwife guidelines Modern Marriage Power exchange
100%
With an 'E'
This story could come under a range of headings, Mature, Couplings, or Transgender. But, I guess, Transgender is best, as I have enjoyed the luxury of satin against my body for some time now. Having Lived alone for the last few years, soft, swirly clothing and satin panties keep me constantly ... Read full Story
shemale lover 2012-10-10 2,949 anal cum oral
100%
Anastasia's Life
Chapter 1: Humbling Beginnings My story starts where most every crossdresser's story starts. It starts somewhere around the time I was an infant. I can remember, not to mention being told several thousand times that my choice of toys as a child was dolls, strollers, dress up and tea parties, Barb... Read full Story
shemale lover 2012-11-26 7,413 Fetish cock sucking crossdressing
100%
Threesome fun
We had invited friend over who has big cock --he arrived and we sat around for awhile talking about sexual encounters of the past --I'm a bi part time shemale cross dresser who is very kinky --anyway it got around to looking around the house and as it happened we stopped in the bedroom , and all o... Read full Story
goodgurl34 2019-01-08 4,664 Stockings Crossdresser Amateur Big Tits threesome Blowjob Big Cock Lingerie domination Guy Fucks Shemale Mature Homemade threesome sex