Sort by
Relevancy

Free Stories

100%
TO BE OR NOT TO BE – PART 6
TO BE OR NOT TO BE – PART 6 by Spanky de Bautumn Part 5. Sunny and Antonio got frisky at the bar, Sunny moved in with Mel and Shari, and opening night was a success The only other dress that I brought was one that I hoped I would get a chance to wear but didn't think I would. It was a black ... Read full Story
SpankydeBautumn 2021-02-26 2,459 Stockings Small Tits Crossdresser Cumshot Creampie Blowjob Big Cock Lingerie Guy Fucks Shemale cum in mouth
100%
TO BE OR NOT TO BE - PART 7
TO BE OR NOT TO BE - PART 7 by Spanky de Bautumn Part 6. Sunny, Mel, and Shari had a heart to heart and Mark took Sunny for a night on the town. I woke up next to Mark, he looked so peaceful sleeping. Was I dreaming? Did I fall asleep and dream that Mark said he was going to take me shopping... Read full Story
SpankydeBautumn 2021-03-01 2,616 Crossdresser Cumshot Bareback Blowjob Big Cock Lingerie Guy Fucks Shemale Interracial cum in mouth
94%
Sissy Slut: Gang Favored
I confess I am a nymphomaniac shemale slut who loves being the object of a man’s desires. That's why I was out here with these hookers trying to hook up with somebody to have sex. I'm either having sex or I'm thinking about having sex most of the time I like being a honey. I love having sex with men... Read full Story
Regina10 2021-03-02 7,507 Stockings Big Tits Cumshot Bareback Fetish Blowjob Big Cock Ladyboy gangbang Guy Fucks Shemale cum in mouth double anal
100%
Horny Writing A Strange Habit
I enjoy watching videos which I can Vicariously live. This is nothing more than my horny hobby, an amalgamation of various thoughts. My form of hands free edging. Spell checked only, "No I haven't proof read a first draft, not trying to publish masterful works here." Hope to hear from those w... Read full Story
Araina 2021-03-08 2,745 Crossdresser Amateur Big Tits Cumshot Bareback Fetish Blowjob Big Cock Guy Fucks Shemale Frottage Homemade Ass to Mouth cum in mouth
100%
Gemini Sluts and Gang
My good friend Renee and I had set up a double date gang bang for tonight now that she was finally out of the closet and ready. She has decided that life is too short to remain in the closet and miss out on all the fun. Renee and I have so much in common. Besides loving sex, we both have a fetish f... Read full Story
Regina10 2021-04-09 4,478 Group Sex Big Tits Cumshot Bareback Fetish Blowjob blonde gangbang Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
80%
Group Sex
Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... Read full Story
Jon Paul 2021-04-19 3,199 Group Sex Cumshot Bareback Creampie Shemale and Girl Guy Fucks Shemale cum in mouth
100%
Threesome goes clubbing
Ft. Lauderdale is probably the most LGBT friendly city on the east coast. So many nice restaurants and clubs that welcome all and have many LGBT employees as well. Lydia and I have been married several months, we had met Joanne an absolute amazing transgender girl during a weekend trip to the Baha... Read full Story
Jon Paul 2021-07-08 5,268 Big Tits Cumshot Bareback Creampie threesome Guy Fucks Shemale cum in mouth
100%
The four of us
Jan and I have been together now about 4 years but known each other since High School. We are both in our early fifties. We had met a transgendered girl (Gabby) about a year ago and we get together about once a month and enjoy each other’s company, going out playing and having intimacy together. Gab... Read full Story
Jon Paul 2021-08-02 4,207 Group Sex Big Tits Cumshot Bareback Creampie Blowjob Big Cock Guy Fucks Shemale Ass to Mouth
100%
Regina and Tommy
I was getting fucked hard and aggressively by a certified bad boy named Tommy. I've never been the kind of girl who liked bad boys until I met Tommy. Tommy like doing all kinds of wild crazy things to me and I was under a spell and couldn’t object. Tommy was like the asspussy whisperer and he gave m... Read full Story
Regina10 2022-03-02 2,981 Stockings Big Tits Cumshot Bareback Creampie Fetish Blowjob Big Cock Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
100%
Amy and the Straight Jocks PT1
Only a couple close friends knew for sure and most others knew it as just a rumor. Amy dressed and lived life as a girl like she had since the start of high school when she moved from a new town. The jocks would laugh and whisper to each other when she walked by debating if the rumors were true. Co... Read full Story
DADDY4sluts 2022-08-09 3,892 Teen (18+) Cumshot Bareback Creampie Blowjob Guy Fucks Shemale cum in mouth
100%
Couple and a Tranny
There is a saying that a single man looking for companionship and good fortune will seek someone for marriage. Lydia and I met several months ago on an online dating site. We agreed to meet at a bar restaurant for drinks and initial meeting. She was at the bar wearing a yellow sundress, white painte... Read full Story
Jon Paul 2022-09-20 5,329 Cumshot Outdoor Latina Bareback threesome Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth double anal
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 4,363 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale high heel boots
76%
She Male Sex Stories
I Lived Just Like Characters From She Male Sex StoriesWalking the streets as a true shemale lady is not always easy. People have prejudice although, at the same time, you can see that those same people would fuck you in a second if they knew that nobody would find out. Something similar happened w... Read full Story
shemale lover 2016-01-28 7,287 Cumshot sucking shemale
33%
Kimberly Wilder: An Assessment
Pull up a chair. Oh. That's right. If you're reading this article, you're most likely at your computer monitor, which means that you've already pulled up a chair. Okay, good. In this article, I'm going to review the splendid art of a magnificent (and very beautiful, too, by the way) transgende... Read full Story
shemale lover 2011-09-19 7,641 transsexual tgirl cock sucker
50%
A Night Out
I was at the bar one Friday night after a long, long week at work. It was one of these weeks where at the end you tell yourself you need a drink. I was still new to this town and haven't been out that much so I went to a bar near where I live in case I decided to drink myself into a stupor. I got th... Read full Story
shemale lover 2012-04-19 3,564 Cumshot Blowjob cum swallowing
100%
Shemale on wheels tour
Being a sexy naughty city girl like myself…I get allot of attention from the boys. I always enjoy getting the attention of the small town boys that are not used to seeing a sexy bitch like me roll though town. They jerk off to girls like me online all the time. But having me right in front of... Read full Story
shemale lover 2012-05-17 3,574 anal sex fingering domination oral sex facefucking
100%
Don't Avoid Daddy
It feels like I haven't been used in ages. I'm too much of a scared sissy. I find guys from all over, talk, email, text sometimes. But when it really comes down to it I get too scared. I've been with this guy before, his cock is soda can thick and he's really rough. The day after my first encounter ... Read full Story
shemale lover 2012-10-23 5,841 Cumshot oral sex deepthroating
100%
Lady and the Cop continued
The next night Regina got a visit from. Larry the cop who openly declared war on shemales and trannies. He was working a homicide where a trannie friend had been killed in her apartment. Larry was a known shemale hater and he never failed to express his opinions. Tonight he was in her apartment to ... Read full Story
Regina10 2018-03-06 4,679 Small Tits Big Cock Ebony Ladyboy Lingerie Guy Fucks Shemale Ass to Mouth
75%
My first night was making love to a man
First .... My name is Lely Bella Calistia, of course it's the name when I decided to become Shemale. My age is now 28th, I became a shemale when I was 24th, when I first chose to be a shemale because I was obsessed with my ex girlfriend, after parting ,, .. maybe because I really miss her an... Read full Story
Bella Calis 2018-03-13 9,386 Amateur Asian Guy Fucks Shemale
80%
How it started
What got me started off watching shemale porn was actually meeting a very beautiful shemale at a beach party. I already knew she was a guy but she was so beautiful. So at one point I asked her if she wanted to go for a walk and after a few minutes and let her know that I was down. Her response was ... Read full Story
PNPFUCKBOY 2019-02-12 11,891 Teen (18+) Small Tits Crossdresser Amateur Big Tits Outdoor Latina Bareback blonde Big Cock Ladyboy domination Guy Fucks Shemale Interracial Sex Toys Mature Homemade Ass to Mouth
85%
My Knight
I felt good as a looked around the club and watch the Queens on stage perform their acts. I felt like I belonged here among this faction of society. Drag queens and Trannies were my people and the only thing I regret is being in the closet and not having the courage to do it more openly. However i d... Read full Story
Regina10 2020-06-23 3,843 Bareback Guy Fucks Shemale Ass to Mouth shemale + shemale
100%
Sissy Slut Reunion
Rob had moved back to town and called me. He had just moved into his new place and he wanted me to come by and talk. I knew what he really wanted from the tone of his voice, because I wanted it too. He said he had been thinking and dreamed about me the whole time he was away. My spirits lifted and ... Read full Story
Regina10 2020-09-14 4,185 Crossdresser Big Tits Cumshot Bareback Creampie Fetish Big Cock Ebony Ladyboy Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Sissy Slut and Stepdads part 2
My mother kicked Frankie out and swore that he was the last loser she would ever date. She believed that we were still having sex, and she was right. Pure raw animal lust drove us, and It was even better when we sneaked and got. That nervous adrenaline mixed with my passion and made me super horny a... Read full Story
Regina10 2021-02-15 4,111 Teen (18+) Crossdresser Big Tits Cumshot Masturbation Fetish Blowjob Big Cock Lingerie Guy Fucks Shemale Homemade Ass to Mouth
100%
The 10 in Bay 10
On the USS Corinth, there were 10 bays - the first bay was for the captains and their personnel, the second bay for first class, the third bay for business, and so on. The back bays were reserved for the ship’s workers. All the way back in bay 10 was the engineering bay. Those in bay 10 rarely inter... Read full Story
sevon 2022-10-03 4,788 Cumshot Bareback Big Cock Futanari shemale + shemale
100%
Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
Chrissy Tunnell 2022-12-01 3,623 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
100%
Shopping plus extras!!!
Hi, so as you can probably imagine I buy a lot of underwear and have a few favourite places to shop. My favourite by far is Ann Summers. The range is great and the staff are so helpful . Anyway back to the story. So I decided to go get some new underwear to see in the new year, I got myself up and d... Read full Story
Samantha Jewels 2023-01-06 4,359 Crossdresser Amateur Cumshot Fetish threesome Blowjob Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Ass to Mouth cum in mouth
100%
A true first time.
I want to preface this reiterating that this is a real story about my first ever experience with a shemale. It's a memory I will hold forever as it was everything I could have hoped for and, as I may share in the future, lead to other experiences, too. A little history of before the first meet ac... Read full Story
Gtaaddict3 2023-11-21 8,584 first time cock suck Blowjob shemale Big Cock trans oral fantasy virgin escort big first time
100%
Seven Lessons Part 1
Bryan was king of the road warriors. Speeding around the country in his sleek, powerful Mercedes selling whatever his latest job demanded. He was damn good at it too, always raked in huge amounts of commission until some faggotty client bitched about a one-sided deal he had put together and then it ... Read full Story
shemale lover 2011-11-30 3,016 Cumshot shemale oral
81%
Husband and wife used by Mr. Big Black Cock
We had decided to take a trip to Vegas and spend some alone time together.. We started off with dinner, then went to hit the tables.. My husband was on a winning streak. He was up at least $1500. I whispered into his ear have fun I'll be in that cute little shop. ok? Then his luck ran out.. and befo... Read full Story
shemale lover 2011-12-18 7,946 shemales gay male interracial sex
100%
Amanda and Me
I walked in the door of my one bedroom apartment and headed straight for the computer. Lately it seemed like I had the same boring routine everyday: get up early, work all day at my stressful IT job, go straight to the computer when I get home to look at porn and masterbate, then eat dinner and go t... Read full Story
shemale lover 2012-10-21 7,338 Cumshot sucking shemale
100%
Leila My Hermaphrodite Lover
I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most. It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before. I'd stayed over at a friend's house and after a ni... Read full Story
shemale lover 2012-12-17 4,232 taboo Cumshot shemale Mature
93%
Miss Bernie
My name is Bernice McDonald and I am the very happy owner/ operator of a couple of children's day-care centers. I love my life and I love this work. I love children and since I have one of my own this helps satisfy my need to nurture. I have not always felt or recognized this need. I was born in... Read full Story
shemale lover 2013-02-22 14,096 hardcore sucking ass fucking Guy Fucks Shemale
86%
My TS experience in India, Pune
Im 6 ft tall fair with handsome looks and regular exercise keeps me fit and healthy. Im also blessed with quite big and thick cock with indian standards. Im total shemale fan and I watch shemale porn crazily every day. I was in search of TS or Shemale in pune since long then one day I was searchin... Read full Story
daynightfun7 2013-07-10 13,199 suck shemale fingering ass fucking Guy Fucks Shemale condom sex
63%
A Slice of Life - Ch. 1
Written by Nobody Home. All comments and feedback welcome! 1. It is dark out, night descending upon a wintery, snowcapped city backdrop. Cold against the windowpane, I feel my head shoved into it and my hand makes a streak against the glass. My would-be attacker tears my panties off of my slen... Read full Story
Nobody Home 2016-12-20 5,197 ass fucking cumming Guy Fucks Shemale cd sissy
91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,481 Big Tits Cumshot Masturbation Uniform Frottage
100%
Charisma Part 2
After fondling her breasts and her cock and balls for several more minutes while she probed Tiffany's mouth with her tongue, Charisma allowed her guest to get undressed while she removed her own clothes. The seamstress was a beautiful woman, for a genetic female, but, of course, she was nowhere n... Read full Story
shemale lover 2011-09-03 3,050 anal Big Tits Cumshot