Teen Male Gets Caught
By: Date: 2022.10.30. Categories: Sex Stories Tags: , , , ,

Ever since I was a teenager and tried on a pair of my mother’s
silk panties when I was home alone there has been an exciting
mystique about women’s lingerie. I am not hung up on it but
I still like the feel and smell of panties (worn ones) when I
masturbate. I have never worn womens panties during the day
but I can see how they have an appeal. I guess the most involved
that I ever got in lingerie was to make it with a teen age guy
who I caught dressed up in my girls panties and bra while he was
looking at himself in the mirror and masturbating. I “played”
the dominent male and treated him like a girl. It was very
exciting and satisifying for us both.

At the time I was working in Wisconson and living with a gal.
She also worked. One day in the summer I returned to the house in
the middle of the afternoon and let myself in by the front door.

As I stood in the lower hall I heard noises from upstairs. I had
seen the car of the kid who cut the lawn outside, so he seemed to
be the only one who could be in the house – but what was he doing
upstairs? As I started up the stairs the sounds definately sounded
sexual. Did he have his girl friend up on one of the beds and
was he fucking her? I started to get excited (I have always liked
watching others have sex) and went into a “stealth” mode as I
got closer to the sounds. They were coming from our bedroon.

The door was partway shut and as I peaked in I saw this nice looking
16 year old guy standing in front of the big mirror jerking off.

He was dressed in my friend’s panties white swet sox and his moccasins
his hard prick and his bag of balls hanging out of one leg band. He
was also wearing a bra. He had filled the cups with something and had
added string to the back so that it would fasten around his chest. As
he watched his right hand stroke his cock his left caressed his body
and fondled his “breasts”. I was excited and took my own cock out and
began to play. He was talking to himself as he milked his dick and
those were the sounds that I had heard. He was pretending that
he was with a guy who was trying to secuce “her”. He kind of
whimpered things like, “Oh please mister, don’t do that. Oh God,
no one has ever touched me there. I’m scared but I like it, mister.”

That play acting of his gave me my idea. Figuring that the kid was
wrong for being in the bedroom and for dressing up in lingerie and
for jerking off (everybody feels guilty about that) I decided to
strip and come on to him. Regardless of what happened it would be
exciting, if he gave in it would be doubly so. If he didn’t the
whole thing would be an exciting event which never came off. I
stripped and left my clothes in the bathroom in the hall. Then
I slowly pushed open the door to the bedroom and stepped inside.

He was faced away from the door and couldn’t see the reflection in the
mirror. My own prick was hard and bobbed in front of me as I walked
up to where he could see me in the mirror. He was still stroking his
prick with one hand and caressing himself with the other. Then I
realized that his eyes were closed in his fantasy. That was just
the opportunity I wanted.

I quickly moved up behind him and took him in my arms and held him
so that he couldn’t get away. He struggled but I was stronger. At first
he was terrified. I immediately started kissing his neck and shoulders
and started talking to him like he was my little girl. “Oh, you darling
sweetheart. What a nice baby. You feel so soft and warm, darling. My
beautiful little baby girl has made my cock so hard. Your breasts are
sooo nice”. He stiffened up as soon as my arms encircled him and started
to struggle. I could tell that he was really scared. But after starting
to struggle to get away, he just kind or melted and kept whispering, “Oh
God, please don’t” and then whimpering, “Oh God, please don’t do this to me”.

At first his cock softened but soon it grew hard again. He could feel
the hardness of my prick rubbing against in the crack of his ass. His
name was Tom, but as I held him in my arms kissing his neck and licking
his ear I called him “Tommi darling”. I moved from being directly behind
him and took his hand and put it on my cock as I said, “Here Tommi you
sweet baby, feel what you have done to me” and I closed his fingers

around the hardness of my quivering prick. He seized it like a lost toy
and stroked it as though he had played with a hundred, but this was the
first except for his own, and the first big hairy man’s cock he had ever
touched. As I carressed him and kissed him and felt
the excitement of his hand on my cock I told him what a pretty girl he
was and how much I wanted him to take my cock in his mouth and to milk
it with his lips and roll my balls around with his fingers until I could
feed him the warm salty cream of my seminal fluid. He whimpered, “Oh
yes. God I would love it.” Then I told him that I also wanted to
slide my cock up inside of him and fuck his warm tight ass until I filled
his body with my cum. Again, this brought an excited “yes, yes” from his
lips. As I caressed him I let my hands slowly move down to the panties
that he was wearing. Suddenly I “found” his cock and acted surprised.

“Whats this?” I said. Then “Don’t tell me that my little girl is really
a boy? Tommi baby, are you really a boy instead of a girl?” He was
confused and didn’t know how to respond. I guess he didn’t know enough
to be sure whether I really didn’t know that he was a boy to begin with.
To settle him down I said, “Oh, this is exciting. My darling little
girl is really a boy-girl. She has a nice hard cock and a tight boy-pussy.
How nice”. Then I reached down, “Oh, the sweetheart also has a beautiful
pair of little boy testicles.”

Then my fingers tightened around his testicles, just enough to
get his attention. As I circled his warm sack of goodies
with my thumb and forefinger I tightened still more and his gonads were
forced to the bottom of the bloated pink sack. “Hey waaa….” he
started to say, but I interrupted with a growl. “You little prick.

What do you mean sneeking in here to play with my girls panties and
bra? You want to want to be a girl do you? Well I’ll treat you like
a girl, you little bastard.” I kinda made myself sound tough. Then
I picked him up in my arms and dumped him on the bed. Now he was scared
and it excited me. “You little bastard. You want to be a girl? I’ll
show you how to be a girl. I held him down with my weight and turned
his head to kiss him. He struggled but I forced his head to turn and
and my lips came down on his. When he didn’t want to open his mouth
I again reached for his balls. I grabbed then and squeezed. “Oh God”
he cried and I slipped my tongue into his mouth and relaxed the pressure
on his nuts. Our kiss grew passionate and he finally gave me his own
tongue. I sucked it eagerly and rubbed my hard cock against his soft
body. When the kiss ended I grew gruff again. “Now my little boy/girl
is going to find out what it is like to be fucked.” He struggled again
and begged me not to do that to him. He said that he couldn’t take anything
the size of my cock. I knew differently, and while I held his struggling
nude body down with mine I reached over to the bedside table for the
vasoline which I used when I fucked my girl’s ass. Taking a gob on my fingers
I smeared it around and into his ass hole. As my firse finger and then
a second slipped into that tight secret entrance to his body he cried out
and struggled again. Then when he felt the sensations he was overcome
with another feeling and he squirmed down on my fingers. The little
bastard liked it. I spread the remaining vasoline on the head of my
cock and wiped my fingers. Then I spread both of his legs and held
them apart and raised them over him as I kneeled with my glistening cock-head
just inches from his pockered rosebud. I put his legs over my shoulders
as I moved until by dick touched his ass. He tried to struggle. He
even begged me, “Please mister I’ll do anything. Please, please don’t
do this to me.” He was crying, the tears running down his cheeks. “Don’t
fuck me. Please, don’t fuck me. I’m scared that you are gonna hurt me
mister”. I looked down at his boy penis. It was violently hard. He
was very excited. Then I positioned my cock-head against his tight ass
and pressed toward him. His scared voice said, “No”, but his eyes
said “yes”. I pressed more feeling his ass start to open. He gasped.

I looked down and I could see my cock-head starting in. My big hairy
bag of balls was swinging between my legs. Now the head was almost in
to the rim. He whimpered and cried, “Oh, God it hurts”. I growled
back, “Thats what you get for jerking off in my girl’s panties.” One
more shove and my cock-head popped in. One high pitched cry from him
and he bit his lip. I was in. The head of my dick was inside of that
nice warm tight little boy asshole. I left it there and let him get used
to it. Then I leaned forward and kissed him gently. As I slid my
tongue into his mouth by hard cock slid deeper and deeper into his
body. He trembled in my arms and sighed. I hugged him and he hugged
back. I told him I loved him and in a quiet whisper he said, “I love
you too mister. I’m scared but I love you.”

When I was buried to the base in his tight ass my hairy balls hung
down between his legs and tickled him. Gently I started fucking
and I talked to him like a lover. I also let him know that I was
the lord and master and that he would do anything I said and that I
would strap him and force him to if he refused. I pulled back till
my cock-head almost came out then slide down deep into him. I moved
back so I could look down to see where we were joined and watch my
dark stiff man’s cock slide in an out of his pink boy hole. While
I fucked him I also reached down for his cock and masturbated him.

Suddenly I realized that I was close to cumming. I started fucking
faster and deeper. He could tell that I was close to an orgasm. “Oh,
do it mister. Cum in my ass. Please fuck me and cum in my ass”.

Suddenly I felt like being rough and I fucked harder. I started
calling him a little bastard, and a little shit, I told him he was
only good to be my little fuck boy and then I felt it start. I
rammed my prick up his ass, and my sperm started to gush out. I
grabbed his body and pulled him to me – as tight as we could get.
Gush after gush of creamy hot sperm squirted into his bowels.

As suddenly as it started my feirceness turned to love and I started
talking sweetly to him. He was my lover. He had accepted my sexual
organ into his body and his insides were bathed with my liquid love.

I held him and rocked him in my arms and told him that I loved him.
We hugged and kissed and I felt my cock start to grow soft inside
of him. I moved and we slipped apart and then I realized that he had
cum between us while I was shooting in his ass.

I got a towell from the bathroom and cleaned him up. I wiped him gently
and turned him over on his tummy while I spread his cheeks and wiped
off the sperm that was oozing out of him. We fell asleep in each others
arms.

When he woke up he started playing cute and I then forced him to give
me a blow job, but that is another story.

After some weeks I finally told my girl friend about him and she first
watched us together and then finally joined us. That was his chance to
fuck his first girl and I took his hard cock in my hand and guided it
into her pussy. I loved being dominant over him and he loved it too.
I loved to fuck his tight ass while he was fucking my girlfriend. Also
my girlfriend got turned on punishing him. She spanked him and she
also spanked his bag of balls as they hung between his legs. Once she
brought two girlfriends over and they took turns using him, making
him jerk off for them while they took pictures of him and forcing him to
suck my cock and later to take my prick in his ass, and to eat their
pussys. Sometimes when he fucked a girl I would slip my hard cock
into either his ass or into the girl’s ass. While it was a turn on to
act rough with him I also found it exciting to be very gentle and
tender with him. He never seemed to get enough of my cock, always
wanting to suck it and drink my sperm. I loved to feed it to him. I
sometimes called him my baby boy when I was cuming in his mouth. Some
times he called me dad.

If you have fantasized about same sex, whether a guy or girl, email me.
Also if U are young and would like older, email too.

(Visited 451 times, 1 visits today)