Sissy Male Stories

Sissy Male Stories
You have found my stimulating collection of sissy stories! All have been submitted by real people wanting to share their stories with the lovely people who read my blog. So whether you’re a sissy yourself, curious about the fetish, or you want to try being a sissy out these stories will not just give you a great idea about what goes on behind these sissies closed doors but also they will turn you on like never before.
A man with a BBC wants to choose one of his favorite sissies and cum deep inside of her and try and get her ‘pregnant’. In this submission you can read all about how and who he chooses and what their alluring meeting is like and let me just tell you this, it’s seriously hot.
A wife and her husband are training him up to become the ultimate sissy. He has a long way to go but in this story, we get to learn all about how he is getting used to male cum and what he and his wife do to get him prepared for taking his first-ever real load.
An eager anal virgin sissy wants our protagonist to be her first. We get to feast our eyes upon their first meeting and the first time she gets her ass penetrated. It’s exciting to read and a real thrill between the legs.
A husband and wife duo decides it’s time for her husband to be transformed into the sissy he has always wanted to be. You can read through their transformation, the sexual journey they took, and maybe even get some tips for yourself.
Love BBC stories? Well, this one has a bit of a twist. We get to ride along with this well-endowed hunk as he takes us on a journey of breaking his sissy partners in with his large member. It makes you crave being a fly on the wall at one of his meetings.

GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressed and made into girls and sissification listed by date.
14 Jun 2022 2219 Readers 10 comments 16 Min Read
I finally found someone that could help me fulfill my desires.
Topics : Crossdressing, First Time, Sissy
29 Jun 2022 2576 Readers comments 2 Min Read
How I became a sissy slut addicted to big black cock
Topics : Crossdressing, Humiliation, Slut, Interracial, Sissy, BBC
10 Jul 2022 New Story comments 6 Min Read
Dad's looking for a submissive wife
Topics : Black Men, Big Dick, Incest, Cum, Sissy, Dad & Son
9 Jul 2022 308 Readers comments 5 Min Read
My name is Sissie it used to be Matt, but that name doesn’t fit. I just put up a sissy pride flag in my window. Mine has pink and white stripes with a modified phallus symbol that looks like a heart with a limp arrow jutting out of it.
1 Jul 2022 705 Readers comments 12 Min Read
The Rest Stop Digest . This is one of many stories I have written through out the years.
Most of these stories are real experiences. Some of these stories are
about different people, but they are based on real event and told as close to a
Accurate as possible. This is a true story but the names have been changed ..
Topics : Crossdressing, Cruising, Cum, Sissy, Oral & Blowjobs, True Story, Stranger
2 Jul 2022 377 Readers comments 11 Min Read
Although this is ch 4 , it is the 2nd part of the Jill Jordan story.
Topics : Crossdressing, Cruising, Sissy, Breeding, Anonymous, Submission, Stranger
13 Jun 2022 3575 Readers 2 comments 4 Min Read
White boy thinks he's gonna get lucky with hot black woman.
Topics : Black Men, Transgender, Interracial, Drugs, Sissy, BBC
19 Feb 2020 12580 Readers 1 comment 118 Min Read
Abused, rejected little boys journey to a manipulative, desirable and successful woman
Topics : Black Men, Anal Sex, Crossdressing, Dildo, Big Dick, Group Sex, Transgender, Sissy, Oral & Blowjobs
15 Sep 2021 31528 Readers 2 comments 17 Min Read
Interracial rape story. A young sissy boy meets a cruel mature black man and dresses as a schoolgirl for him, he gets spanked and raped. The cruel man treats the little sissy rough, tearing off his clothes and ripping apart his favourite little white cotton school panties. He forcefully spanks him hard then rapes him. The theme and story line runs parallel to "Sissy Boy Loses Panties To Perverts"
Topics : Black Men, Crossdressing, Rough Sex, Spanking, Daddy, Interracial, Sissy, BBC, Rape
7 Jul 2020 18762 Readers 1 comment 13 Min Read
Cat-sitting for your neighbors becomes alot more exciting when you stumble upon their wardrobe collection.
Topics : Crossdressing, Bondage, Sissy, Face Fuck, Master & Slave, Domination
21 Dec 2019 24298 Readers 3 comments 28 Min Read
2 blonde bimbos help a little sissy faggot become the girl he always wanted to be and Introduce him to a man who knows just what to do with a special girl like this!
Topics : Anal Sex, Crossdressing, Dildo, Big Dick, Gloryhole, Sissy, Oral & Blowjobs, Small Cock, Blond
7 May 2018 23195 Readers 7 comments 3 Min Read
After fighting with a drunk girlfriend, a boy is fed up with women. He decides to finally live out a fantasy he's had for years.
Topics : Black Men, Crossdressing, Sissy, Drunk
9 May 2018 17925 Readers 2 comments 2 Min Read
After fighting with a drunk girlfriend, a boy is fed up with women. He decides to finally live out a fantasy he's had for years.
Topics : Crossdressing, Sissy, Drunk
12 Jun 2021 6085 Readers 1 comment 4 Min Read
The neighbor boy finds neighbor Daddy
25 Jul 2016 47061 Readers 3 comments 15 Min Read
Sissy boy loses the game, now he's going to lose his anal virginity.
Topics : Black Men, Crossdressing, First Time, Sissy, Sportsmen, Virgin
16 Sep 2021 7501 Readers 1 comment 4 Min Read
My first visit to a bathhouse, where I learn about poppers and BBC
Topics : Black Men, Anal Sex, Poppers, Interracial, Sissy, Bathhouse & Saunas, Gangbang
17 Apr 2022 4058 Readers 5 comments 36 Min Read
Continues the journeys of two brothers months after the events of Part One. Darren and Randy both find themselves beginning a new chapter of their lives with new and old friends.
Topics : Anal Sex, Dildo, Brothers, Rimming, Sissy, Master & Slave, Raunchy, Control
16 Mar 2021 12674 Readers 2 comments 3 Min Read
The guy who brought out my submissive side and made me his sub sissy wife.
Topics : Anal Sex, Bondage, Sissy, Submission
1 Mar 2010 54157 Readers 15 comments 5 Min Read
I try pantyhose for the first time, enjoy it, get my buddy Corey to enjoy it too and we become sissy buddies.
Topics : Crossdressing, Sissy, Pantyhose
11 Feb 2021 10942 Readers 1 comment 10 Min Read
I go to an adult bookstore for my first time while dressed as a Gurl and get my first sex with men, lots of men. sissy, first time, spanked, DP.d, oral, anal, domination, sexy, slut
Topics : Anal Sex, Crossdressing, DP, Spanking, First Time, Slut, Sissy, Oral & Blowjobs, Domination
31 Oct 2021 3996 Readers comments 23 Min Read
While well over the legal age of sexual consent, my looks represented a much different picture. Broght up by a single parent overbearing mother, my being raised was far from the normal channels of a lone single male son.With mom making dresses and me the perfect slender size to model her creations, I guess you could say that the soft silk and lace never failed to stimulate me in a secret sexy way
Topics : Crossdressing, Voyeurism, Sissy, Oral & Blowjobs
9 Oct 2021 3823 Readers comments 11 Min Read
Being used like a queer is a turn on, but being treated like a girl is too!
Topics : Anal Sex, Neighbour, Outdoor, Sissy, Oral & Blowjobs
15 May 2020 9186 Readers 3 comments 2 Min Read
Topics : Black Men, First Time, Sissy, BBC
9 Jan 2022 4457 Readers comments 20 Min Read
Topics : Black Men, Slut, Interracial, Drugs, Sissy
28 Dec 2019 7827 Readers comments 10 Min Read
A gay sissy bottom receives a surprise birthday gift
Topics : Anal Sex, Crossdressing, Hairy men, Sissy
24 Sep 2021 6375 Readers comments 4 Min Read
I was blackmailed to be a sissy faggot for old men
Topics : Group Sex, Daddy, Sissy, Blackmail
13 Jan 2022 2922 Readers comments 4 Min Read
My gay lover left me but not before he turned me over to a gay Dom Master. I guess I should have been more careful of what I asked for.
Topics : Bondage, Sissy, Cash Master
4 Mar 2022 5092 Readers 1 comment 5 Min Read
One of several kinky bondage games the boys like to play.
Topics : Bondage, Forced, Slut, Sissy, Seduction, Gangbang
8 Jun 2018 20936 Readers 4 comments 7 Min Read
Adam MacDonald secret life of crossdressing has always been both the escape and high of his life. A mysterious package with no sender address arrives one day, and inside it contains: a dress and more!
29 Nov 2018 23732 Readers 4 comments 22 Min Read
Charles has battled against his feminine features all his life. It takes a single experience with a dominant, alpha high school jock in the locker room to make him know his place in the world. ! ARCS Needed !
Topics : Anal Sex, Crossdressing, Public Sex, Locker Room, Transgender, Sissy, High School, Twinks, Oral & Blowjobs
© 1999-2022. GayDemon ™ This site is labeled with RTA.

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Kate had a dark side to which his slave was not aware till now as. As kate reveals her other side to her slave as he begs for mercy
Ben didn't know what he was in for when he first applied... he soon found out the hard way.
Dave Newant comes home to find his wife at the feet of a black man. You are furious but soon he turns you into a cute little plaything along with your wife.
When John tells his mother that he wants to be a sissy baby, how will she react?
Ryan has been left off at a daycare for all ages but Ryan finds a magical device granting his every wish.
Sean goes shopping with his best friend Josh and is humiliated.
WARNINGS: NON-CON, IMPRISONMENT, ENSLAVEMENT, BODY MODIFICATION, FORCED TRANSITION, ABUSE (LIMITED), OBJECTIFICATION, GORE, YOU GET THE JIST. YOU'VE BEEN WARNED.
one-sho...
David's wife make him live life as baby.
Sissy gets her first man, ready or not.
A husband and wife have lost the flame of passion in their marriage, but a new neighbor offers new perspectives that may change their lives forever.
Chris is abusive and drunk most of the time he is awake. Finally, his wife has enough, she finds an ageplay site, and things only go downhill from there. Chris must say...
Ryan, an eighteen year old college student, has recently heard that his old school had shut down, and Ryan decides to sneak into the school that is definitely not haunte...
This story follows Casey as his girlfriend subtly introduces new changes into his life.
A teen boy can't resist the sudden urge to wet his bed and pants. He doesn't understand why he has these unusual urges to wet in spite of his dismay and discomfort at be...
a bunch of random, free hand one shots of gay men. any suggestions are welcome.
Steven and Connie fuse a bit to often and some strange side effects occur to them.
Justin is a 14 year old boy who wet his bed sometimes, he is small for his age, he lives with his mother and he is happy, but one day after school, everything changes, h...
𝐈𝐍 𝐖𝐇𝐈𝐂𝐇, astrid and her friends make a content house, not expecting lots of hate and drama.
john is confronted by two girls he used to harrass in highschool. no it his turn to become the victim, to feel what its like to be a helpless diapered sissy.
This story...
Sophie is desperate to win the barista championship but doesn't feel she is up to the challange. Tom, her work mate, is extremely good at being a barista. This gives her...

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How many of you sissies enjoy slathering on that smooth, creamy, lipstick. For some of you that is your absolute FAVORITE part of getting all femmed up.
While so many girls and sissy girls clamor over the 50 shades of grey…THIS sissy falls over 50 shades of RED. This is what she had to say about her red lipstick:
I really love putting on and wearing women’s lipstick. It feels so smooth and sexy on my lips. The way is glides across them creating a slippery, shiny coating. It can never be a light shade, it always has to be a dark slutty color. The kind that stains my lips when I’m wearing it so I might not be able to hide it the next day.
To be a man wearing tons of bright red lipstick is embarrassing and exhilarating. But the feeling of it on my lips, the smell, the taste. Makes my heart pound in my chest.
The latest one, a color called “Tempt” is long-lasting, but also has some lip plumper in it. It makes my lips tingle as they become more pouty and the color sets into my skin.
Mistress Lillith loves making me put on tons and tons of it, making me ask repeatedly for more and more until I can not take it anymore. Then she makes me add more still.
I love that she is turning me into a helpless sissy lipstick addict for her amusement. I can’t resist the feeling when she tells me to “put on LOTS more” .
I fear my future as a lipstick slut, but I also can’t help but love the idea of having constantly red and shiny lips for everyone to see what a naughty little lipstick slut I have become for Mistress Lillith.
That was a lot of femininity to absorb and that shot in the arm toward the end helped me recover a little.
There’s of course another possibility–one that is deeply erotically humiliating–but I still suspect my gut instinct interpretation was correct.
My legs and chest feel different. Actually super weird is more apt.
It’s the strangest sensation but I swear I feel like my legs are wet all the time, like I’ve just gotten out of a pool. Does hair soak up moisture or something? Actually I think what’s happening is in the past when dry, the hairs protruded a bit and on contact with something they would trigger the nerve. Previously when getting out of water the hair would be weighed down by the weight of water and pressed flat against the skin, and wind or something else would trigger the nerve. Now without hair, any brush against the skin is triggering a sensation has historically been associated with wet hair and my mind is confusing the two. At least I think that’s the explanation but I’m not sure. I keep reaching down to brush water off my legs but they are dry and smooth. WHAT IS HAPPENING!?
The strangest, most surprising thing I still quite can’t get over though is my stomach. It’s like I don’t even recognize it. I look down but I’m still not quite convinced it’s my stomach and my belly button. I can hardly keep my hands off of it, feeling the smooth foreign skin over and over again.
For the first 18 hours a red bump appeared in place of every single hair that was ripped out.
Jessica assured me those would recede and they did.
I have smooth hairless skin from my neck down (okay, my arms still have some fine hair and i didn’t have my armpits waxed or my bikini line).
While my shoulders are a little broad, I don’t quite have the physique of a masculine male… Not many muscles anyway.
I’m acting and behaving girlier too : getting waxed, chatting about skin care with a pink haired girly girl, shopping for girly skin care products.
Something that’s kind of turning me on too is that the mantras feel different now. They feel … more effective and more real. Something about looking girly and doing girly things and having it repeated in my head is powerful.
It’s been a deep, er
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