Sissy Story Sex
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Sissy stories that will make you horny for sissy mouth and delicious hole. Here are quick teasers, I quickly fell on my knees and took the large head of the dildo in my mouth and began to suck… I felt Ramon gently bend me over, apply a sticky goo to my ass and very gently enter me… She scooped up her own precum from her erect sissy cockette and fed that to her lover…
Aunty gives me Surprise Present (Sissy Stories)
It has been 3 weeks since my last weekend with my 70 yrs old aunty and I am going to stay bathers again as my wife has gone to Cornwall again...
Late Night Surprise (Sissy Stories)
My wife is out of town for this week. This morning I had nothing on my calendar. So last night I went and shower around 9pm, used my wife's electric razor...
I Told my Mother the Truth (Sissy Stories)
Last night I went out as I normally do on non-working nights, I take some of my mother's clothes with me, she doesn't know I do this. I get dressed up...
Aunty Uses me as Her Mannequin (Sissy Stories)
My old aunt ex seamstress uses me as her mannequin as we are the same size, it started a few months ago as we discovered she loves sex after living in...
Mom is Demented and I like it That Way (Sissy Stories)
Mom has been diagnosed with early onset dementia and is oversexed. Dad left and i have power of attorney over mom's estate. This provides me with...
Mom's Little Sissy Mother Fucker (Sissy Stories)
Mother dresses me up in frilly lingerie for the experience of having incest both dressed like hot lesbians. Long ago I told mom i enjoyed wearing her...
Caught, The Wife Story (Sissy Stories)
One day, just like any other day, I woke up in the mood. I was feeling sexy and in need to feel my legs covered in black nylons while wearing sexy panties...
Father's Choice (Sissy Stories)
My 60 yr old father (Jack) and I (John) had not gotten along since my mother passed away. He always thought I was too feminine and a mother's boy...
Me and My Sexy Old Grandma (Sissy Stories)
I was at my old grandmas doing some decorating for her she had gone to the mall shopping for the day and I needed some more...
True Story my First Time with an Older Woman with a Difference (Sissy Stories)
Having finally left school I was in my first year as an apprentice and I had an accident at work and was sick for a while luckily it was summer...
Submit Like a Girl (Sissy Stories)
One nice summer day, my BFF and I were sitting around the house when he asked me if I would wanted to get dressed up? It would be fun...
First Time With Another Crossdresser (Sissy Stories)
I have been dressing since I was 14 but never indulged with another guy. One day I was looking at transliving and I came across an ad with a fairly inexperienced...
I was Introduced to Crossdressing (Sissy Stories)
I was at college and need some spare cash and I got chatting to a guy I knew from the pub I said I need a weekend job to earn some money to make life easier...
True Story my 70 yr old Aunty Discovers Sex for the First Time (Sissy Stories)
My dear very smart lean and very fit 70 yrs aunty always to me and in the summer she would be in her garden in the skimpy shorts and her blouse tied up...
Aunty Helped me to Crossdress (Sissy Stories)
It all started when I was 50 and my aunt who is 70 yrs very smart and very fit came to stay a few months after her husband died. My wife was working...
Mom Showed Me How (Sissy Stories)
My girlfriend was very pretty and undeniably not a virgin like me. I hadn't been with a girl before and all I knew was I very much had a naughty fetish...
Sissy Suck (Sissy Stories)
My wife and I live in a nice house in a rural area. We are in our late 40's. I am Mike a small skinny man and always felt lucky to have found Karen...
I am a Sissy Faggot (Sissy Stories)
I used to dress up like a slut and my girlfriend would lift up my skirt and pull my panties to the side. And fuck me with a strap on dildo all night...
I wish I was a Girl (Sissy Stories)
I met the girl of my dreams and told her that I loved dressing up with full make up and fuck me boots. She was delighted and arranged a hotel room...
I Need Cock (Sissy Stories)
Hi my name's Jeremy. Ever since I was a teen Ive had thoughts of cock. It wasn't until I met my wife that I finally accepted I was at least bi...Continue reading
Downgraded (Sissy Stories)
My sister and her husband were killed in an aircraft accident returning from a vacation. She was 38 and I her brother am 40 years old. My name is Henry...Continue reading
Sissy Pantie Boy (Sissy Stories)
This is a true story, though I would share. I was going to live with my father in Houston. I was 19 very much into porn and smoking weed...Continue reading
Played Out (Sissy Stories)
I had married into money. My wife was beautiful and we lived in a large house in the country. I had never met her parents and they were against our marriage...Continue reading
Best to Just Submit (Sissy Stories)
When younger (in college) my best friend and I lived at opposite ends of our street. We would get into his father’s girly magazines and enjoy reading...Continue reading
Overtaken (Sissy Stories)
My brother in law and his wife had been trying to get their hands on my money for some time. This time their scheme worked. They all knew of my...Continue reading
She Was Soft Spoken (Sissy Stories)
I have been chatting with her for about a year now. She was about 145lbs with short black soft hair. Her breasts are a B cup and she is about...Continue reading
Grandmother's Sissy (Sissy Stories)
I am a life long sissy crossdresser. I had a Grandmother that I loved to visit every chance I got the opportunity. I began crossdressing at the age of...Continue reading
Outcast (Sissy Stories)
Debbie and I had been dating for several months. We were both in our 20's and from upper middle-class families. Debbie's mother had passed away...Continue reading
Secrets of a Closet CD (Sissy Stories)
I had not dressed for many years, not since we had got married. I had wondered if I had actually grown out of it, but the desires had crept back in...Continue reading
Sissyfag at the Motel (Sissy Stories)
I checked into the motel put some gay shemale porn on the TV and then striped out of my clothes and put my lingerie on. A black push up bra with matching...Continue reading
Dressing With An Old Friend (Sissy Stories)
It was 1970s I was 18 and a bit of a loner. I had tried without success to find a girlfriend but always felt inhibited and awkward around girls...Continue reading
Made Me Do "CRISTAL" Then Turned Me Into A Girly Sissy Slut (Sissy Stories)
I was driving alone one day, and seen this car with its hood up..So I stopped to help...It was over heated...I told the guy if he wanted a ride somewhere...Continue reading
My New Employers (Sissy Stories)
Tired of our boring marriage my wife had started becoming interested in other men. I was short at 5' 7" and only 155 pounds. I was actually a bit smaller...Continue reading
Forced To Be A Girly Slut (Sissy Stories)
I answered an ad for work, this guy was looking for a hand packing his house..So we talked I went and met him the next day.. He was tall African American...Continue reading
Showing My Son About Being A True Mama's Girl (Sissy Stories)
At the start of high school my transitioning from Male to Female started in earnest. My psychiatrist started me on feminine hormones and I began dressing...Continue reading
Caught By My Wife While Sucking Cock And Dressed As A Slut (Sissy Stories)
I had been a life-long crossdresser and had finally given in to the desire to be with other men. I had never been attracted unless I was dressing as a...Continue reading
Maid For Good (Sissy Stories)
My girlfriend Joan has always known of my crossdressing and somewhat lets me dress on occassions. Her girlfriend Darlene also knows I dress but has never...Continue reading
Sordid Affair (Sissy Stories)
My wife was away for the week so I was free to indulge in my secret life. I brought the old suitcase down from the loft and laid out my female clothes...Part 1, Part 2
Taking Her Place (Sissy Stories)
It all started when my best friend Bruce caught me crossdressing. He was married to Tina and we all knew each other. I knew Bruce had a touch of bisexuality...Continue reading
Hot For Teacher (Sissy Stories)
School was a special education. Mommy taught us well. Covid-19 was a blessing in disguise. Home schooling became necessary as the corona virus pandemic...Continue reading
The Power Of Cross Dressing (Sissy Stories)
I started being interested in women's clothes at a very young age, like most cross dressers, I started out slowly with just pantyhose, over time this progressed...Continue reading
Derailed By Mother In Law (Sissy Stories)
I am on the short side for a 40 year old man. 5'5" and barely 135#. I was always made fun of and people told my wife I looked more like her son...Continue reading
A Sissies Story (Sissy Stories)
So for this story I'll jump right in after posting a few thing I would enjoy doing on a few adsites I finally got a responds from somebody that didn't...Part 1, Part 2, Part 3, Part 4, Part 5
My Best Friends Mom (Sissy Stories)
My best friend lived across the street and we spent the night at each other’s houses. His mom was always wearing a tight one piece swimsuit, they had...Continue reading
Trained Servant (Sissy Stories)
My wife and I were both retired. She still had a nice body and very outgoing. I was slim and actually smaller than my wife. I had always crossdressed...Continue reading
Carol Crossdresser (Sissy Stories)
I am a closet crossdresser. Whenever I get the chance I love shedding my boring male clothes and slipping into panties and bras. Occasionally my wife...Part 1, Part 2
Boy-Girl For A Summer (Sissy Stories)
It was summer and that morning Ron’s mother was sitting out on the back patio in the shade painting her toenails. Ron walked out in his t-shirt and shorts...Continue reading
From Tight Ass King Of His Castle To His Servant (Sissy Stories)
Up until about six months ago I would say I was pretty average really good looking sexy average height 5 960 lb closet crossdresser my most proudest and...Continue reading
The Summer Girls (Sissy Stories)
Barry was very nervous. Just the thought of going out in public dressed as a girl was extraordinary. Dylan seemed much more confident about it...Continue reading
Luscious Lingerie From Mom (Sissy Stories)
Mmmm. Luscious lingerie from mom. Mother knows exactly the effect smooth silky lingerie has on her sweet boy, her damp panties and pantyhose feft so...Continue reading
Incest Novels (Sissy Stories)
Mother supplied us with lots of hot incest novels to better entice us into a "let's get mommy" scenario. Her wet panties conveniently strewn about...Continue reading
Girdle Fetish And Nylons (Sissy Stories)
Mother has a nice selection of luscious lingerie, her little plan is to buy me sexy expensive girdles, nylons and associated silky smooth articles that...Continue reading
Fun Being A Slut At A Card Game (Sissy Stories)
I have been dressing for many years. One day after work i was horny as hell and had decided to dress up and have some fun. I put my red garter on...Continue reading
Bill Mom's Waiting (Sissy Stories)
Dear Bill, Mother is dressed to please! She’s wearing your favorite outfit along with those "fuck me" high heels. Her vagina is nice and wet...Continue reading
Sissy Loves Mommy (Sissy Stories)
Darlings are inevitably mother's pride and joy. They need their mom's luscious breasts. Mom's need their babies lips. The instinct never...Continue reading
Miss Alice's Lingerie Shop (Sissy Stories)
It's difficult to know where my story really begins. It was back in the mid 1960's when I became aware of my, shall we say, penchant for ladies underwear...Part 1
My Summer As A Girl (Sissy Stories)
It was the beginning of summer and already I was feeling bored. That was usual and to be expected, of course. My mom had already left for work and I...Continue reading
Mother Made Me Do It! (Sissy Stories)
Caught red handed wearing my mom's nylons and openly sniffing her womanhood from her pretty pink lace panties (good and wet) my mom intentionally barged...Continue reading
Jennifer's Dream (Sissy Stories)
I was 18 when mother caught me wearing her girdle. I just loved the firm all around feel and how smooth the front panel and butt was. I didn't know mom...Continue reading
Mom's Best Intention (Sissy Stories)
Poor mom. Her well intended ideas of being my tutor and showing her son the "errors of his ways" was her intent. She obviously was concerned about my curious...Continue reading
Straight Husband Road To Sissy (Sissy Stories)
Our story starts some 25 years ago. A couple of years after my wife and I married, she expressed regret that she did not have more sexual experiences prior...Continue reading
Delicious Dainty Drawers (Sissy Stories)
Mom got tired of her son's deliberate outright theft of her expensive undies. Knowing full well it wasn't about to stop anytime soon she simply devised...Continue reading
All In The Family (Sissy Stories)
I had no idea my wife was so upset about my crossdressing. My wife is 12 years older than me but has very good looks. She had seen me dressed many times...Continue reading
Mom's Drawer Of Seductive Undies (Sissy Stories)
All boys started with their mommy's panties and pantyhose, the mom's learning quickly would allow this behavior knowing full well it would lead to a nice...Continue reading
Mom Knew Her Son Was Now Hers (Sissy Stories)
Convincingly my mom continued to tease me after finding me wearing her expensive lingerie. Son, these are your mom's best imported European undies...Continue reading
Mommy Wanted A Little Girl (Sissy Stories)
Mommy, (she prefers this immature nickname) long ago told me she had always wanted a pretty girl instead of the little boy she had. I remember as a toddler...Continue reading
Moms Cum (Sissy Stories)
Mom quickly found out about my curiosity for her pretty things. Her drawer began to expand extensively. Soon colorful silky nylon panties replaced cotton...Continue reading
Looks Like I'm Mommy's Boy (Sissy Stories)
Mom was intentionally seductive, her needs were insatiable and unrelenting, mom's pretty attire was so attractive, her legs long in luxurious pantyhose...Continue reading
My Sister Helped Me Become A Gurl (Sissy Stories)
Even while we both lived at home my older sister had caught me multiple times dressed up in her panties and bras or come into our only Bathroom catching...Pt 1, Pt 2, Pt 3
My Dream Of Being Pegged Finally Came True (Sissy Stories)
I have been reading online Husband Pegging Sex Stories from multiple porn sites until I realized one day the only way to get this to happen to me, was...Continue reading
Pretty Panties And Pussy (Sissy Stories)
My 'lil brother was caught by mom wearing her nylons and sniffing her panties while masturbating. She told me about it and to have a "talk" with him...Continue reading
New Job Physical Exam (Sissy Stories)
I just turned 26 and very happy to be able to finally go to work after completing eight year service in the US Army. I knew applying for this new job...Pt 1, Pt 2, Pt 3
Give Anything To Be My Mother In Law's Daughter (Sissy Stories)
I met my wife at college, as time went on and holidays were approaching she took me to her family's home. I met her family and grandparents, my wife's...Continue reading
Mothers Little Helper (Sissy Stories)
Mom seemed to protect me from any adversity or perceived harm or unhappiness. Always coddling me, even at age 4 I was seemingly cuddling and mom's kisses...Continue reading
Nosey Boy (Sissy Stories)
When I was 18 years old I was living with my aunt and she was gay and I got suspended from school and I was looking through my aunts VHS tapes and I saw...Continue reading
Submissive Husband Turned Sissy Boi (Sissy Stories)
I 66 years old new and my wife has been the strong one in our marriage our entire time together! She is the real bread winner as she does software development...Continue reading
Heaven Found In Moms Top Drawer (Sissy Stories)
I was 19 and always horny. I started noticing the clothes mom wore, short skirts, stockings (this was 1960 ) girdle with garters to hold up the stockings...Continue reading
Sissy Incest With Brother (Sissy Stories)
Since I was wearing mom's panties and nightgown (my little brother was also wearing some of mom's nylons) my brother a little sissy himself...Continue reading
Lil Mother Fucker's Club (Sissy Stories)
My Jr high buddies all had a club that turned into something extra special. We would get together for sleep overs at each other's homes. One friend Dennis...Continue reading
High Heels, Hosiery, "Family Time" (Sissy Stories)
Mom runs a chic Boutique. She carries sizes for tall women. Mom is herself tall as am I. Mom's 6 ft 2 inches and I'm over 6 ft 7 inches. Occasionally...Continue reading
The Appointment (Sissy Stories)
I woke up early, it was Saturday and I was going to be alone in the house when he called to keep secret arrangement. It had been going on for a few months...Continue reading
Dressing For My Neighbor's Wife (Sissy Stories)
An interesting development in my ongoing sex only relationship with my neighbors wife occurred last week. For a year we’ve had about a dozen “quickies”...Continue reading
House Clearing And The Benefits (Sissy Stories)
I love it when University splits for the summer holidays. My friend and I were hired by a local Landlord to clear out various of his properties vacated...Continue reading
Dressed For Glory Holes (Sissy Stories)
Im a latin male smooth body and love to dress in womans clothes. I dress alone take photos and post on line i always loved to sit back and read comments...Continue reading
First Time In A Long Time (Sissy Stories)
I had never fantasized about sex with another guy before it happened, it just happened. We were both very young. Starting innocently as watching each other...Continue reading
Mommy's Sissy (Sissy Stories)
MOTHER was very domineering and insisted upon strict adherence to her specific instructions. All males at birth were began upon a regimen of feminization...Continue reading
Begging For Mommy's Attention (Sissy Stories)
Mommy started out seducing us as adolescents. The Mr. Bubbles bath time was always our favorite time (except bedtime) Mommy always took time to carefully...Continue reading
Revenge On Ex-Girlfriend Goes South: A Spiral Down A World Of Hypnosis (Sissy Stories)
So where to begin? A couple weeks ago the girl I fell in love with broke up with me by filming herself sucking another man and having her virginity...Continue reading
My Love (Sissy Stories)
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Sissy Story Sex
