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Embarrassing Confessions

A messy date

I’d been flirting with a girl in our extended group of friends for a few weeks and things were looking promising. One Saturday evening we’d been out with the others, but we ducked out early and I took her back to my house. My parents were away until the following day, so I knew we would have the place to ourselves, and she was as keen as I was... (more)

4

Boys can be confused also.

I learned how to “beat my meat” at about twelve. I quickly became an expert.
Then I learned how women got pregnant. This white stuff (cum) was deposited inside a woman. But the confusing thing to me was; I insert my dick into the girl but then what? What makes my cum shoot out?
The only conclusion that made sense to me was, I jack-off... (more)

1

Catfishing

My older sister is in beauty school. Several times I let her practice on me. I'd become comfortable doing it. Once she put hair extensions in and styled my hair. Then she did my make up. I admit I looked cute. I tried on several outfits of hers and posed for pictures. My dad wasn't impressed but Didnt make us stop. mom laughed about it and... (more)

1

First Pussy Sighting

What was your first pussy sighting?
I’ll tell you of my first and second. During the seventh grade we discovered a peep hole to the girls’ dressing room. When the lunch bell rang we scurried as quickly as possible to the gym in hopes of catching the high school girls. When my turn to peep came my eye locked on a blonde senior. Her large... (more)

6

Red handed

I really thought my wife had left the house, and like any normal husband of 12 years, I decided to check out some porn, and rub one out with no distractions. I had the tv on, and my phone on some good ol fashioned gangbang porn, and well, got to business. I was pretty much taking it slow, enjoying myself and for whatever reason i happened to look... (more)

Called

I really want to be called a faggot by a woman.

3

Things you do for money

Hi im angie,54,divorced recently lost my job and really struggling to make ends meet,id applied for every job you could think of but nothing,I had no help from the system,so there was only one thing I could think of,sell myself! I knew of the brothel in the city so I swallowed my pride and jumped on the bus and headed there,the girl on the desk... (more)

1

I'm a man and I got knocked out by a younger woman

I'm a man and I've been boxing for several years to stay fit and learn to defend myself
A young woman joined the boxing gym a month ago. She came from a powerlifting background so she was very strong
When we started sparring, I quickly realized that her punching power was too much for me to handle. She stunned me pretty badly the first time... (more)

2

Shamed

Hi I'm a 16 year old crossdressser but I do feel so guilty that I have told my mum I dress in her clothes and that she would spank me while dressed but have family and friends over to watch I deserve the shame and humiliation I'm waiting to see what mummy says

1

She used her perfect ass to sissify me...

My girlfriends perfect ass and dominating dirty looks turned me into her sissy bitch boi.
Janice tricked Chris Using Forced Feminization, and Forced Sissification.
The Evil bitch slayed my soul with her absolutely perfect ass, destroying my manhood a little more with each sexual encounter. CFNM was our thing. She would never let me fuck... (more)

2

Need to break my wife's bad habitI

My wife dresses like a skank, in fact several times when out dancing and drinking some guys think she is a hooker.
It's always deep cleavage, or tops a bit too large so she can let her boobs peek out, short skirts without panties or if they are there they might as well be plastic wrap.
In public, at parties, we have been in a few scuffles as... (more)

4

Wife's first married date

After being married for nearly five years my wife, Ginny, told me that a guy at her work had been flirting with her and had asked her out on a date. Ginny asked me if she could go out with him. She told me that two of her married girlfriends dated other men and that their husbands knew about it and actually encouraged them to date.
I told her... (more)

4

My Freshman year

I was bad when I was younger.
My mom ran off when I was 5 leaving my dad to raise me and my 8 month brother.
I went to public school till 8th grade but I kept sneaking off with guys so dad enrolled me in a strict private high school.
Early my freshman year, I was invited to a pool party. At first my dad was reluctant but after some... (more)

2

Dirty wife

I'm a contractor so I get to travel a bit around the country,met some crazy friends along the years,all sorts! Fighters,ladies men,drinkers you name it,one of the lads Jordan came into work Monday telling stories about the weekend,he'd met some milf on fabswingers that was gagging for it,Jordan is in his twenties,well there's a few of them on the... (more)

9

After prom with the assistant principal

This is my first post. I had previously read someone’s prom confession and I had a similar experience......26yrs ago….
After some thought, I decided to post my confession.

Long story but my at my senior prom, my boyfriend/date, the only guy I'd been with, got in a fight and the cops came. They took my boyfriend and other’s involved home... (more)

Dr visit

So I had to make a appt to see the Dr I felt my plumbing was not working properly was not getting hard as often or spontaneous like before. I have a primary Dr I see I tell her everything when it comes to my health she Indian not to good looking. So I go to my appt the nurse calls me in tells me my Doctor is out today will I be find seeing doctor... (more)

2

Mom's Grateful Sissy.

Mom wanted a daughter and she got me instead.
I saw little of my Dad who was in the military. I met him when I was five years old and then again at seven. Then when I was ten he came home "to stay" which ended up being a very traumatic three months. The entire time he berated me referring to me as a "filthy little sissy faggot" constantly... (more)

1

Little show off on the subway

I work in a dentist's office in the city centre
The doctor had already left and I was taking care of our last patient. He a gentleman about my age, very handsome and I suspect he had a little crush on me. He was always trying to catch my look, stare into my blue eyes and smile. I stayed cool and finished my work professionally and when he was... (more)

2

Little show off on the subway

I work in a dentist's office in the city centre
The doctor had already left and I was taking care of our last patient. He a gentleman about my age, very handsome and I suspect he had a little crush on me. He was always trying to catch my look, stare into my blue eyes and smile. I stayed cool and finished my work professionally and when he was... (more)

1

Revenge for the Jock

When I was in high school, my Dad got a job and we had to move from what was a large city to a much smaller community, It was just before my junior year. I was about 5'9" at the time and around 150 pounds.
There was this one guy, a senior, easy 50 pounds bigger, who liked to pick on me, not much I could do about it. He was the captain of the... (more)

3

I made my wife perform oral sex on a friend

My wife and I had only been married about 6 months. I was a really kinky husband. She was 18 and I was 21 . I loved hearing her tell me about past relationships. I got off on listening to my sexy young wife recounting her exploits before me. Including her giving head to a couple guys she went out with a couple times. So I decided that I wanted my... (more)

6

Naughty mouth and talking back

Looking for a female nurse to spank me over her knee for my own good sometimes I walk around with an Erection and I think I need some punishment done to me to teach me a lesson before my birthday this November thanks my name is Kevin m Smith and I live in ACTON Mass

Groped

I got seduced by a !esbian couple. I didn't want to do it, but they got me so horny licking my breasts and figering me, I let myself go. Ended up getting my pussy sucked with her lover rubbing hers on my face and climaxing several times. Don't know how I let it happen but I loved it.

1

Gym showers

I was the youngest boy in our class at school, and after gym class we all showered together in this big locker room. I used to get erections quickly when I used the washcloth on the genitals, so I always tried to be quick.
Some of the other kids would notice and laugh, make fun of me. It was pretty bad, I was only 14 and just getting hair down... (more)

5

My mother married a queer WTF!

So my father died about 10 years ago and mom stayed pretty much alone. That was until a year ago. She meets this man. As soon as I met the guy and shook his limp sissy hand shake I knew he was light in the loafers. I tried talking to mom but she didn't want to hear it. I asked her what she was going to do on her honeymoon night watch him have sex... (more)

4

Male massage?

The place I go to has female "therapists", first thing I noticed was they all wore shorts and halter tops.
It took awhile until I became a regular, then some fun began, a happy ending from most of them, tops off, about it, NBD and sort of normal at many places.
I was going in once a week, way cheaper than dating.
No appointment needed although... (more)

1

Tired of being made fun of.

I am so tired of being made fun of by both men and women. My penis is only 4 inches long and 3.75 in circumference. Yes I know I'm small. I don't need you to remind me. I stay home and jerk off when feel the urge . I went to get a blow job one time and the girl said wow I should only charge you half cause that's like half a normal sized cock. If... (more)

6

Weakness for tights

For as long as i can remember I've loved the thought of a woman sitting on my face in a well worn pair of panties and tights. Ever since my ex boss used to do it to assert her dominance on me. It's an embarrassing thing to ask a woman to do, just wish I could find like minded women near me to do it, i'm in the north east of England. Not interested... (more)

1

A stranger fondled and exposed my tit in public

I was taking the bus home from work and as usual it was super crowded. I had a heavy bag over my right shoulder and a pile of books in my right arm so I found my spot, balanced as best I could and took hold of the handhold above me to keep from tipping over. Most people don't get off until a lot further down the line so I knew I was in for a... (more)

3

Wife fucking with another man humiliating her husband

My dominant wife, is the head of our household. My wife thoroughly enjoys her superior status over me and had a large collection of whips and paddles to keep me subdued. She gave me permission to write about my submission to her and her newly rejuvenated sex life.
When she learned of my secret desire to be totally dominated, she was more than... (more)

2

Drag brunch

My mother owned a bar and grill and to pick up extra money started a drag brunch. I'd help in the kitchen. The "girls" who were the waitresses for the brunch would tease me about being shy and cute, about having a girlfriend... Before opening they'd tell me I'd look good as a server etc... We had 4 girls as waitresses and three that were the... (more)

Naughty girl friend

I thought I was in for bit fun when girl friend said let's go bed and you get undressed then she tie me to 4 corners left room and come back with the cat and some food to she started rubbing over my cock and sh8the cat left room and hear her leavening home she returned about hour later and came see how was going car meow so she covered my cock... (more)

2

Penis pills

Yesterday was a long day on the farm working with our fish tanks, chicken coops, and vegetable crops. I came in before dinner with a bad headache. I asked my dad for some Tylenol. My mom said we don’t have any but there is a pack of headache pills in the kitchen drawer. I went in and the only pills I found were red ones so I grabbed them and... (more)

6

MM4M “Big Nigga Dick Spitroast”

Wife was out of town and I was craving dick bad, so I went on Doublelist to look at ads. One ad, “Big Nigga Dick Spitroast” sounded amazing! The ad said “two hard dick niggas looking to spitroast white sissy”. I am not a sissy, but I do love a big nigger dick now and then, so I responded to the ad and met them at a picnic table just off a hiking... (more)

5

Jacking off in the barracks

I was 19 and in the Army, on my bed in the barracks in just a tee shirt and socks, boxers on the floor across the room in front of my wall locker. My door was locked, so I felt comfortable I wouldn't be walked in on, I had my own room at the time. I was taking my time and really getting into it. Wiggling my little ass, moving my hips, caressing my... (more)

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