Superb story site with lots of sissy stories. One sissy series in particular, I’m going to post the first part here. I’d love to get in contact with the author Joan Mitchel but I don’t have an email. So I cant really post the next 4 parts, you’ll just have to go read them on the site at the bottom of this post
Rob’s Sissy Boy – by Joan Mitchell – Part 1 of 5
Rob’s Sissy Boy 1
I am a secret panty wearer. I’ve always had a thing for satin and silky
things. After twenty-six years of marriage, I still love to watch my
wife put on her sexy under things. On occasions, I’ll wear my wife’s
panties to bed and have sex in them. If she goes down on me and finds
her panties on me, she’ll ask me why I am wearing them. Not in an upset
voice, but one that is unsure of my desire for her. She doesn’t
understand my fascination of women’s lingerie. I’ve tried explaining
how the silky, soft snug feel on my cock keeps me excited longer and
harder. I secretly keep a couple boxes of my panties, tap pants, bras,
slips, nylons, dildos and baby oil in my basement office.
My lust for sexy underwear started in my teens. I would find a pair of
my mother’s used nylon panties in the bathroom hamper. I would rub them
over my stiff cock until my warm cum shot over them.
I have three brothers, and we all are interested in girls. We would
check out skin magazines when we could find them. I also I would look
at Sunday newspaper ads of women’s bras, panties and girdles. I would
cut them out and hide them in my bedroom closet. Since, each of my
brothers and I had our own rooms, it was the safest place. When I felt
horny, I would pull them out and imagine I was dress in those shinny,
silky things and jack-off.
This love of lingerie was always with me. Especially when I went in a
department store, I would pass thru the women’s department as if I was
searching for my mother. But I was really in there to walk among the
satin and nylon under things, touching and rubbing them between my
fingers as I past the displays.
This love of lingerie got me my first sexual experience. Also, I should
mention first bi experience, at age 15.
As I lay asleep one night, I felt something press against my mouth.
Half awake and confused, I could feel a rubbery object slip across my
lips. I heard my brother Rob whispered, “I know your awake, keep
quiet”, as he pushed his cock past my lips. Rob is a year older and
very much interested in girls. I, on the other hand, liked girls but
was too shy to approach them. I knew being shy did not mean that I was
gay. But with Rob’s six inch cock sliding between my lips, I laid there
thinking I was dreaming, accepting his assault on my mouth. I should
have struggled against him, but I didn’t. We are about the same build
and size I could have stopped this. The only thing I could think of was
that Rob was horny and used me while he imagined I was his girlfriend
giving him head.
Rob whispered that he knew I would like his cock because he found a
pair of panties I had cummed on laying in the bathroom earlier that
day. I had left the bathroom in a hurry when he began to bang on the
door wanting to use it. I either
forgot to put them back in the hamper or dropped them and did not
Here I lay, wakened by a stiff cock forcing its way to the back of my
throat. Rob worked his hard smooth cock in and out slowly as he moaned
softly. I could not believe this was happening. I did not think of boys
sexually, I liked girls.
I lay quietly while Rob slid past my lips again and again. I was still
not fully awake but I felt my cock start to stir. I wanted to touch it
but I did not want to move and have Rob know I was totally conscious.
My teen cock was growing under the sheets but in the darkened room Rob
had not notice.
As he fucked my face I did something that I had no control over. I
began to lift my tongue up under Rob’s silky rod and let it rub his
cock as he pumped away. His cock had a taste of musk and sweat. I began
to lightly grip his dick with my lips. I could not believe I was
actually cooperating. My first taste of cock and it wasn’t unpleasant
Rob began to quicken his in and out motion and moaned louder . He
pulled out of my mouth, I felt him jerking him cock beside my head. I
could barely see thru the slits of my eyes as He let out an “ahhh” and
shot his load in to some of my clothes piled by my bed. I felt
disappointed, he used me then when I wanted more, it was gone.
Rob wiped and left without saying another word. I laid in the dark
trying to figure out what had just happened. I was confused and
During the next few days, I avoided Rob as best as I could. We did not
talk. I was ashamed and could not look him in the eyes.
The following weekend, our parents went away and took our younger
them. Both older brothers Phil and Rob went out Saturday night, leaving
me home alone. Phil usually is out until about two o’clock. As I sat
and watched TV, I heard someone come in the back door about nine
o’clock. It was Rob, he was home early. He went to the bathroom, I was
kind of nervous.
A few minutes later he came out, walked into the living room. He looked
at me with a lusty stare and said “Come with me”. He walked out towards
our parents room. I got up, my knees shaking, and followed like a
As I stepped into the room, Rob had our mom’s lingerie drawer open,
searching thru it. He pulled out a pair of panties, a bra and a half-
slip. He turned and tossed them at me. As I caught them, he said, “Put
them on”. I was completely surprised at this command, but didn’t
protest. As I fondled these silky things I did want to put them on. It
looked like my lingerie fantasy was going to come true, I but did not
know what else Rob had in mind.
I began to take off my clothes. As I did, I started to get hard and
knew I would soon not be able to hide it from Rob. I turned away from
Rob as he opened his zipper, taking off his pants then his shirt.
After all my clothes lay on the floor, I reached for the panties on the
bed. As I fumbled with them, I could see our reflection in the vanity
mirror in front of me. Rob was naked with a grin on his face, staring
at me from behind. I bent over, held the panties low to step into them.
I put one foot thru then as I lifted my other foot I began to sway off
balance from my nervousness. I caught myself and put the second foot
thru. As I started to pull the panties up my legs, I felt Rob’s hands
from the sides grab the waistband and help me pull them up to my stiff
cock. He took one hand, reached around, push my cock up and back
against my tummy. We pulled the panties the rest of the way to my hips.
Rob let go of my dick as the nylon material slid over forming a small
tent. I almost shot my load on his hand. For the first time someone
else had touched my cock. My knees were getting weaker.
Next I picked up the satin and lace bra, held it to me face and
inhaled. It had a sweet, sexy smell. I slipped my arms thru the straps
and reached for the hooks. I knew how it worked, but it was hard. As I
fumbled to stretch the ends, Rob took them from my hands and hooked
them together. I was getting as excited as on Christmas morning from
the sensations. Rob reached around and began to stuff
the cups with nylons to form breasts. I leaned back slightly for better
access. I could smell Rob as he put his arms around me to fill each
cup, brushing each nipple as he pushed inside. I was in heaven from the
attention he was giving me.
After the cups were full, I looked into the mirror and saw myself for
the first time in women’s lingerie. I loved the look and feel and knew
I would be doing this again.
I was brought back to the moment when from behind, I heard Rob say,
He was bent forward holding the slip waistband open. I stepped one leg
back in, then the other. My legs were made of rubber now. Whether Rob
knew of my desire for sexy lingerie or not, I was willing to do
anything he asked me to do now.
After the slip was pulled on to my waist, Rob had me turn around so he
could see my sissy look. He smiled with a knowing nod, stepped over to
the bed and sat on the edge. He motioned me to move in front of him.
With my head tilted down I was staring at his throbbing cock sticking
up between his legs. He said “kneel down”.
I knelt down almost before he finished. I knew what would come next.
I put my hands on he’s legs, and spread them wide, and leaned my mouth
towards his bobbing cock. I could see clear drips of precum at the hole
seeping out. I opened my lips, stuck out my tongue and flicked the top
of his cock head. I could taste his juices at the tip of his soft head.
I wanted more so I made an “o” with my lips, moved lower and felt the
head press into my mouth. I pushed down, the head passed thru and slid
along my tongue. I leaned down until my nose was buried in
his pubs. Rob let out a low moan, leaned back on the bed, stretched out
as he enjoyed my warm mouth and tongue.
I slid back up on his shaft until I hit the underside of his mushroom
head, stopped then slid back down. I was lost in the sensations of the
nylon and lace caressing on my body, and worshipping Rob’s stiff cock
with my lips and tongue. I felt like a girl, and I couldn’t get enough.
As I bobbed up and down I could hear Rob grunt and moan louder and
start to buck his hips off the bed. I sensed he was close to spraying
his cum down my throat, and I wanted him to.
But Rob quickly sat up and told me to slow down he didn’t want to shoot
yet. I didn’t want to stop, so I kept sucking and bobbing. Rob put a
hand on my head, held me down as he composed himself. After a few
seconds, as I licked his still wiggling cock in my mouth, he caught his
Rob told me to lay down on the bed. I did not have to be told twice. I
hopped on the bed lying on my back. I began to smooth out the slip, I
loved the touch of my silky covered legs. Rob turned and leaned forward
on his elbows with his face above my cock. He stared down at the tent
my stiff cock made under the slip and panties. He lowered his head
until I could feel his hot breath thru the layers on my penis. Rob
opened his mouth and moved down on to my aching cock. This was another
first, my dick receiving a pair of hot lips. I was ready to faint. Rob
teasingly rubbed his mouth over the tip of my twitching cock. My eyes
were closed and taking in all the oral sensations of Rob’s lips and
Rob stopped his tender attention as I felt him shift around and
straddle my legs.
He squatted down with his bare ass on my legs, just below the hem of
the slip. Rob reached under my knees, pulled and pushed my legs back,
so that they are bent up. As he did this , the slip slid down my legs
and bunched up on top of my standing cock. He opened my knees and
pushed them wide. Then moved up between my legs, where he was staring
down at my pantied covered ass. He slid the slip up above the panty’s
elastic top. He reached into the waistband and wrapped his fingers
around my throbbing cock. Rob slid and rubbed my cock and balls. I was
softly moaning and waving my legs from the anticipation. With his other
hand, he pulled the waist of the panties down, exposing my cock and
balls. He tucked the band under my ball sack, it felt very sexy. He had
complete access to me, and I was horny and waiting. He took my penis
and sucked me deep in his warm, wet mouth. Sucking and licking me like
a lollipop, it didn’t take long for me to feel my cum begin to boil in
my balls. I was bucking and moaning, expecting my release soon when Rob
slowed, then stopped his bobbing mouth on my aching dick. I was ready
Rob leaned back and told me to roll on my tummy. I was ready for
anything. I quickly flipped over. He placed his hands on my waist and
told me to raise my ass
up with my knees tucked under. As I brought my ass up, Rob flipped the
slip over my pantied ass and on to my back. Here I was wearing soft,
underwear, with my ass in the air like a slut. I could not wait for the
next step in to my sexual future. Rob pushed his belly up against my
ass, sliding his cock under me. His cock head rubbing under my hanging
balls and twitching cock. The panties waistband still stretched behind
my balls allowing him full access. He moved back and forth, at times
pulling out, laid his cock between my nylon covered ass cheeks and slid
it against my asshole. I felt like a sissy girl from head to toe,
completely at Rob’s command.
Then Rob stopped, backed off the bed and returned with a jar of cold
cream form our mothers vanity. He pulled down my panties, letting them
slid to my knees. I now felt completely exposed and horny. As he
scooped some cream, I clinched my asshole tight expecting the cold lub.
But instead, he softly kissed each cheek and lightly blew on to my
puckered hole as his mouth passed over.
As with this whole affair, Rob said little. But he did warned me, “this
is going to be cool”, as he placed his fingers on my tight hole. I
jerked a bit, then relaxed. He rubbed my asspussy with small circles,
then put a finger tip to the hole. His slick finger began to push in,
one knuckle then another. It hurt some, but I didn’t want him to stop.
His finger went all the way in, he stopped, then withdrew until the tip
was at my rose bud. Moving back in and out a few more times, it felt a
little better. Rob pulled out and added a second finger. Forcing their
way thru my slick, tight entrance, it began to hurt again. He stopped a
moment as I whimpered into the pillows I had buried my face in. His
fingers wiggled their way in to my bowels, as I adjusted to their
invasion. He worked them in and out until I was loose. Then he added a
third, until my asshole allowed little resistance. He worked them in
and out faster and faster until I began to push back to meet his
actions. He reamed me until I could take no more. I wished for him to
put his cock in my ass. He did not have to be told, he planned to fuck
me, whether I cooperated or not. He was ready too. Rob stop and pulled
his fingers out, scooped more cream, coated the tip of his cock and
moved it to my well stretched asshole. Placing one hand on my hip, and
the other hand guiding his hard cock in to my pussy. I thought with all
the fingers inside I was ready. But as the rubbery head slowly pushed
past my puckered hole, I felt a different sensation. It filled my ass
as it slid in, I wanted him to stop, it was hurting. Rob pushed until
he was in all the way. I cried and leaned forward feeling like I could
not take anymore. Rob held my hips to keep himself in. He stayed still
for a moment as he let out a groan. I could feel his pubs tickle my
cheeks as he wiggled his ass around a bit.
My asspussy held his shaft tight as I adjusted to his hard meat
invasion. I now felt comfortable with him in, so I slid forward feeling
his cock slip until it was almost out. Stopped, then slid back on his
pole. I was in command now, I thought, but Rob took over. Sensing I was
OK, He started a rocking motion, back out then in. My asshole no longer
attempting to stop him, I opened up and enjoyed his sliding and teasing
action. He began to squeeze my hip tighter and pickup the
speed of his attack. I was trying to keep up with him, but he started
to bang away
to fast. He was lost in his lust, slamming deep in me, then out harder
and faster. It felt like he had a piston in my ass. Rob was pulling me
back as he pushed forward, I was bouncing off his thighs. My balls were
smacking against his balls. I cried as I rode the waves of the senses I
was experiencing. I did not want him to stop, but I wanted the final
sensation of Rob shooting his cum deep in to me. I wanted it all.
I felt Rob reach under me, grab my throbbing cock and pump me as he
fucked me. That’s all it took for me to cry out, muffled by the
pillows, and release my hot sticky cum on to his hand and the slip that
hung below. Shot after shot blasted out from my cock, I was lost in the
joy of it all. I would never feel these feels again, my first fuck in
lingerie. As my sack emptied it’s load, I could feel Rob tense up, slam
hard in to me and let out a loud groan. He stopped, buried in my ass
and splashed his hot liquid seed against my walls. It felt like gallons
from the number of shots he let loose. He fingers dug into my hips as
he spent the last drops of his juice. He slid slowly as if he was going
to pull out, but stopped then back in again. He eased himself back and
forth milking the last bit of cum as my pussy gripped his shaft,
squeezing it dry. He stopped moving and he leaned on to my backside
forcing us both down. I lay there with my ass tilted upward with him
still inside. We laid still catching our breath.
Rob pulled out and rolled off on to his back, I was disappointed. But
then felt his warm cum run out my pussyhole. I needed to go to the
bathroom quickly. I got up, pulled the panties up and headed out the
room. Realized my legs were shaky, grabbed the door jamb and swayed
into the bathroom. I sat on the toilet trying to figure all my thoughts
out. Was I gay? Why I did I enjoy something that’s not natural? I was
confused and excited but I liked what had happened.
Still wearing the lingerie, I entered the bedroom thinking I would lay
down with Rob, relax and see what comes next. But Rob was up and
getting dressed. He said nothing until he was ready to leave. As he
walked towards the door he told me
to “clean mom’s things and put them back in the drawer before they get
back and straighten the bed”. He left, went in the bathroom then left
the house again.
I figured this was a one time experience. Over the next few days I
didn’t see much of Rob. We were never in the same room alone. I guess
we were avoiding each other.
About a month later, our parents and brother left to visit family over
the weekend. I hung around the house Friday night intentionally. About
eight-thirty Rob came in the front door. My heart started to pound with
excitement as he came in to the room. He looked at me and said, “Lets
go”, turned and headed in to mom’s bedroom. My heart went to my throat
as I got up to follow. My knees were weak as I approached the room. I
heard a drawer being slid open and knew what was coming. I could not
wait to see what I would be wearing tonight.
You can find the next 4 parts HERE