Date: Tue, 17 Dec 2013 11:11:48 -0500
From: Charles Anderson <CharlesAnderson1980@mail.com>
Subject: Sissie Bo Alex and David.

This story is a story of fiction, based on my real life, names, places and
events have been changed in order to protect the willing actors, the story
is about a 11 year sissy boy and a 53 year old man. If that idea does not
turn you on, or if it is illegal in your area, then you do not need to read
further.  If you are under 18 please leave the site.  I hope you enjoy the
stories.

Characters:

Alex(is), Little Marissa:  11 year old sissy boy (me)

Marissa: Alex's Brazilian mother, divorce and supportive of Alex sexual
orientation.

Christina: Marissa's best friend and mutual friend of David, also encourage
Alex to seduce men, a Sissy boy needs a mature cock.

David: 53 year old man who has a boy fetish, and is Marissa's landlord and
next door neighbor, friends of Christina.

Mr. Parker: Math teacher at Alex school, Friend of David and also one of
his lovers.

Barry: Online Chart friend – 58 years old has a boy fetish.


Part 5.


It was 5:30 in the morning when Mom woke me up; I had over slept half an
hour.  I was in the shower when Mom knocked my door.  "Babe you have phone
call from David, when can he call you back?" she said, I asked her to tell
him to call me in 10 min, I was so happy to hear back from David after one
day of silence.  After 10 min David called back, I was sitting next to the
phone waiting his call like a good sissy boy waiting for his man to call.
"Hello David, how are you? Oh I am fine, You missed me? Good to hear! I
missed you too, I have to be at the bus stop at right at 6:15 so I am not
sure I can go to see you now, Oh you can drop me off at school, ok, let me
tell Mom and I will be there in 15 min.

I cleared with Mom that it was ok for David to drop me at school, I
finished dressing in school uniform, blue shorts, white short-sleeve shirt,
blue tie, blue sucks to the knee, I took my book bag and ran to see David.
He asked me in and as soon as closed the door he grabbed by the waist and
brought me close to him and gave me a very passionate kiss, we must have
kissed for a few minutes, his tongue playing with mine, his lips sucking my
lips, his hands grabbing my bubble butt, his fingers caressing my butt
crack, I was already hard, and I could feel his dick getting bigger and
bigger I brought his zipper down and I put my hand inside without saying a
word, and I grabbed his delicious cock.  I pulled it out and he pushed my
head down, so I knelt in front of him and I opened my mouth and started to
suck his dick slowly.  He was enjoying it, "mmm, Alex I missed your wet
warm mouth, mmm how good you are sucking cock, oh yes baby suck it, swallow
my cock" as I did what he asked me, he said "I heard Mr. Parker asked you
if you want to meet other men?"  I took his cock off my mouth and said "Yes
David he asked me" and he pushed his cock back inside my mouth.  "Ok, I am
ok with that, but you have to be careful who you meet, and you will need
precautions, not every Daddy out there is good for you baby, and I promised
Christina I will take care of you" he said.

"MmmmJJJJMmmm, I said still with his cock in my mouth, he just grabbed my
face and said "but you are first My boy, and will always take care of my
needs first" I took his cock out of my mouth and said "yes David I am your
boy first", it did not take long when he said "ready for my load baby?
Drink it all..." I opened wide, and he let me have a delicious white creamy
thick load of cum.

After that he took me to the office as he gathered his papers for whatever
business deal he had that day, and then we got on his SUV and we drove to
school.  "So, David" I said " How do I know who to go with? Do I need to
get your approval for seeing another man?"  He laughed and said "no, just
be careful, get to know him first, if Mr. Parker introduces to one, or if I
do that it should be ok, but do not go with the first man who wants to fuck
that gorgeous ass of yours."  I was glad to hear that, I wanted to make
sure I understood our arrangement.

He dropped me in front of the school, before leaving his SUV he asked me to
give him another Blow Job, so we parked a block away, he unzipped his pants
and I put his massive cock in my mouth taking my time to tickle his cock
with my tongue, and sucking on the head, I pulled his foreskin all the way
back and sucked on the head tasting his pre-cum and enjoying the wonderful
smell of cock. I must have sucked him for a good 20 min because we heard
the bell ringing from the school just when I was swallowing the last bit of
cum.  MMmm delicious, so cleaned me up, gave me a kiss in the mouth and
sent me to class.

During first period, Mr. Parker asked me to come to his desk as the others
worked on a math problem, he told me he had discussed with David and I had
the green light to meet other men. He said he would arrange for me to meet
them at his place, right after school.  The rest of the day was uneventful,
played with other kids, and was anxious to go home so I could get online
and talk to Barry.  Just the thought of seeing him cum so much made me
horny.  I wanted Barry.

I got home around 2:15 like I always did, when I got home I found a note
from Christina "Honey, I heard about the wonderful weekend you had with
David, I thought I give you a gift to celebrate your new Sex life, I know
you will look sexy in those, let me know if the size is right, and remember
LUBE is the key to good anal sex, I hope you use it and enjoy it...remember
what I always told you, your ass baby can drive any man crazy use it
well...sissy boys need man cock, and you will always get your way, love
Christina!"

I ran upstairs and on my bed I box with a pink bow, I opened it, it there
was a see through black baby doll, black stockings, a pair of crotch-less
panties, garters, and fishnets thigh highs, and a pair of 6 inch heels,
with it a little make up case with blush, red lipstick, and other
make-up. I was thrilled. I loved to feel all sexy wearing those. Then I
noticed there was another bag. In it there were 2 small hipster mini shorts
and a couple of t-shirts that showed my belly button, a bottle of shimmery
oil, and more lip-gloss.

Wow Christina had gone shopping and she had bought me some nice things to
wear.  I looked at the clock and it was almost 2:30, I had agreed to see
Barry online around 2:30 so I took my clothes off, ran into the shower and
cleaned myself well, and put baby oil all over my hairless body, my butt
looked very delicious, I went to mom's room and took one of her panties.
It was red with white dots, small thong style, with wide lace and satin in
the front, wide enough to cover my fully erected 3 inch cock. The band came
high to my hips and then arched back into my butt crack showing my butt
cheeks nicely.  I put on a small t-shirts, combed my hair towards my left
side, put some lip gloss and turned on my laptop, I placed the laptop on my
desk made sure I showed full body if I got up from the chair.

I logged into the site, my heart was pounding, then a bunch of alerts
showed up on my screen, I had closed to 100 messages from different men, I
guess my profile was being viewed by many horny daddies, I also found,
requests to connect, I was really exploring the site, I was about to open
my some of the notes I had received when I got a message from Barry; "Hello
baby", "My cock has been missing that gorgeous body of yours, I cannot wait
to see you on cam baby" with that I received a Webcam request, which I
accepted immediately.

I fixed my hair and prepared to see Barry.  "Hello Doll" he said when he
saw me..."Hello Sir" I said ...Barry responded "Sir? Please, call me Barry
or Daddy, do you want to call me Daddy? My beautiful boy!"  I must have
blushed there was something about Barry's voice that made me very horny, he
could fuck me anytime, I melted every time I heard his voice.  I responded
"I like the idea of calling you Daddy, you know I don't have a Daddy, and
you make me feel so warm inside, I would like that".

Barry came on camera, he was totally naked seating on a sofa, the camera
showing him full body.  He had his massive mushroom head in full view, his
cock was so thick and yummy. I liked his looks he was a Daddy type for
sure.  You could tell he did not work out on regular basis, he had at least
a 40-42 inch waist, thick calves, and thighs, nice bubble ass, and broad
shoulders, he was tall but I could not gauge exactly his height so I asked
" Daddy how tall are you?" He quickly responded" I am 6 feet 3 inches tall,
I am 260 pounds, 41 inch waist, and my dick is 8 inches cut baby, do you
like Daddy?" with that he got up and walked towards the camera, showing me
his cock up close.

I was still sitting down at my desk with the camera on my face, I realized
my mouth was opened, and I was day dreaming of sucking that cock.  Barry
said " Baby get up and show me that lovely body of yours, I have been
dreaming of that gorgeous body specially your delicious ASS baby, and that
cute mouth, I can see you wrapping my cock with your full lips and tasting
my cock"

I quickly Got up and made sure he could see me and said "Oh Daddy, I would
love to suck your cock, and I want to be in your bed, feel your body next
to mine, I want you Daddy, since I saw you yesterday I have not stopped
thinking of your cock spraying so much cum on your lap and the floor, I
want to be with you... when Daddy...when?"  Barry was stroking his
cock... "Oh baby you are such a beautiful boy, take your shirt off baby, I
want to see you just with that sexy panty, take it off now!" Barry was a
bit dominant...  I loved that..." take it off baby now" So I did, as I took
it off he was stroking hard and fast, his purple cock head was expanding
even more.  "Oh baby...I love your body I want to fuck you so badly, when
you ask...if it was for me I would fuck you today baby...but you are at
home and I am here, do you think you trust me enough to tell me where you
are, I could pick you up and bring you here, we could play, I will respect
your wishes if you want me to stop I will, and when we are done I will take
you back home, but it is up to you I do not want you to get in trouble with
your mom" Barry said.

"Oh Daddy I want you so much I do want to go with you, let me call mom and
let her know I will be going out and also call a friend to ask her
something, and I will give you my address...you can pick me up " I said.
Barry interrupted me and said "Give me your address now, so I can tell you
in how long I can pick you up" With that said I gave him my address, and we
agreed he was going to pick me up in 20 min.

We disconnected, and I ran to call Christina... she answered the phone, and
I explained to her that I had met a man online, and I wanted to meet him, I
explained he has said he would respect my boundaries, and he had also said
we would not do anything I did not want to do.  She asked me where he
lived, and I told her.  She said that he must be rich, because that is a
very affluent side, then she asked me what I wanted to do.  I said I wanted
to go, so she said "Call Marisa, tell her you are going to play outside, I
will cover for you, I will take Marisa for some drinks after work, just
make sure you get back home before 8 pm.  Hey wear something sexy for this
Man, and remember LUBE is the secret to good Man-Boy sex, take good care of
yourself Alex."

I got ready put one of the short t-shirts and mini shorts that Christina
had given me, I put on a pair of gold sandals, fixed my hair to one side,
and looked myself in the mirror, I looked very sexy, m shorts were very
sexy and you could see the bottom half of my butt cheeks and you could see
where my thong panties buried inside my butt crack. I looked very sexy, I
wanted to be as sexy as I could be for Daddy Barry.  I looked at the clock
and it was 18 min since I had talked to Barry, so I called mom.  "Hi Mom, I
wanted to let you know I will go out and play in the neighborhood" Marisa
responded; "Ok honey, have fun, I will be home late, Christina has invited
me out after work, so eat something, don't wait for me, not sure what time
I will be home, go see David, I am sure you will like that, make yourself
pretty and pay him a visit, I won't come looking for you so if you want to
spend the night, just let me know, bye".

I put the phone down when I heard a car pull up the drive way... to the
door and signal him to wait.  He stayed inside the car I picked my keys,
and closed the door behind me.  Barry was driving a late model Mercedes
Benz S Class very nice car with dark Windows.  I went to the passenger side
and opened the car door.  Barry was wearing a t-shit, shorts, and
loafers. "Hello beautiful boy "he said... "Hello Daddy" I said... he was
checking me out from my toes to my head.  "Wow, you are more gorgeous in
person than in camera, I must be the luckiest man in the world" "Are we
ready?" he said.

I said "Yes Daddy I am ready, but I would love a kiss from you before we
go" He leaned towards me and was going to give me a kiss on the cheek when
I moved my face and opened my mouth inviting him to French kiss me" we
kissed for a few minutes, he was a very good kisser, soft tongue and lots
of tongue action. When we stopped he said "Mmmmmm, Alex you are a dream of
a boy" with that we left my house and drove about 6 min and we were at his
home.  We lived about 6 streets away from each other.

We drove into his drive way, Barry had a large estate, very nice home, he
opened the garaged and went in to the house, it was great very discrete.
When we went inside his home, Barry took me by the hand and we walked to
the second floor. We went into a very large bedroom.  His bed was the
largest bed I had ever seen; the room had a large sofa, the computer desk
to one side. I recognized the sofa from our web cam sessions.  His computer
was connected to the Webcam site. His house was very large, and nicely
decorated.  " Do you live all alone in this big house Daddy?" I asked "Yes,
my dear boy I do, do you like Daddy's place?" he said.  I responded by
nodding my head. He then proceeded to take me to the sofa, he said "seat my
boy, are you comfortable?, what do you want Daddy to do?"  I sat motionless
seating in front of him, his pant's zipper at my eye level, I reached with
my hand and lowered his zipper and opened his belt, his pants fell on the
floor, he cleared them out of the way, I could see through his briefs a
very fat bulge, he asked me " Do you want to suck my cock baby?" and he
caressed my face and put his thumb on my lips, which I caressed with my
tongue and sucked he pull my face up from my chin, and said "Look at me"
his was so commanding I shivered in heat.

I loved his dominance. I looked up, and he lowered his face and French
kissed me, then he said " Lower my briefs and take my cock and suck It
slowly baby, take your time, show me how good a cock sucker you are" As he
said that I lowered his brief caressing his thighs and calves as I lowered
the underwear, when I looked up I saw the massive pink mushroom head ready
for me to suck... I dropped on my knees to have a better angle, My had was
a bit lowered than his balls... I opened wide and with my tongue I started
to caress his shaft and suck on the shaft, going from the outside in,
making it wet, and he was guiding my head making sure I was making all of
his shaft wet..."mmmm Alex baby that feels so good, are you ready to suck
my balls?" as he said that I grabbed his balls and started sucking on them
they felt so big inside my mouth I could put only one at the time... he was
moaning, "SUCK MY DICK, baby show me what you can do" he commanded, I
opened wide and took his massive pink head slowly inside my mouth,
caressing it with my tongue, swirling my tongue all over his head, and
grabbing the shaft with both hands , I tilted my head backwards like David
had taught me, and I slowly allowed his cock to enter my throat, I started
to gag and I pulled out a little and sucked on his head to taste his
pre-cum and use it as throat lube and again I tilted my head backwards and
I pushed in allowing his cock to pass beyond my palate without gagging and
his head was tickling the back of my throat..Barry moaned " Ooooohhhh baby
this is amazing your throat is so warm, I want to fuck you forever..." as
he said that I started to pull and push my head deep in his cock my throat
expanding with every push, he was in a frenzy, he grabbed my head deep
inside and pushed his dick as deep as he could, I had his balls on my chin,
he started to pull out and push in slowly then faster, I needed to breath,
he realized that and pulled out, I took a big gulp of air and followed his
cock and put it back in this time not as deep, I grabbed his cock with both
hands and started sucking going in half way and jerking his cock with my
hands, he was spewing pre-cum, it was dripping from my chin, at that moment
he pulled his cock and said.. "spit that pre-cum in your and baby" so I
obeyed... He took his shirt off and he stood naked in front of me. He said
"time to fuck you my boy... come let me seat in the sofa, and I want you to
get naked for me...do not wipe that pre-cum from your hand we will use it
as lube for that gorgeous ass baby".


I started by taking my shirt off, then I started to pull my shorts down. He
stopped me and he said he wanted to do it.  He began by caressing my legs,
then turned me around and sucked on the half of my ass cheeks that were
coming out of my shorts.  His tongue was all over my ass.  He pulled the
shorts off and buried his face on my ass caressing my rosebud with his
tongue, and then he ordered me to spread his pre-cum on my rosebud.  I was
in heat, I wanted Barry more than ever, I turned around to face him he was
totally naked seating on the edge of the sofa, I was standing in front of
him only wearing mom's panties.  He had a look that said I want to fuck you
now... I pushed him softly so he would lay on the back of the sofa I climb
on top of him with my knees on the sofa around his waist, my ass sitting on
top of his erected penis, his hard cock parting my crack, my face in front
of his face, and I started French kissing him, caressing his shoulder and
chest, kissing his neck, going back to French kiss him, he was parting my
butt chicks with his hands and placing that massive head right at my
sphincter, if he had pushed down on my shoulder his massive head would have
entered me easily.  But I wanted to eat more cock so I slowly went down on
him kissing his check, belly until I drop myself to the floor, and knelt in
front of his cock and started to suck him slowly taking most of his cock
in...Barry was in only moaning "oh baby you are the best fuck I ever had,
never stop baby suck me until I cum" I wanted to taste his cum...but I also
wanted for him to fuck me , I wanted Daddy's dick inside me.  I must have
sucked that delicious daddy cock for a good 20 minutes I really took my
time savoring his pre-cum, taking his cock all the way down my throat,
socking on his big mushroom head like a lollypop.. he was so relaxed as I
sucked his cock. Edging him to almost climax and then climbing on him and
letting him taste his cock by French kissing him.

But he was ready to fuck me: "Stop" he said "On your knees facing away from
me... part your ass with your and rest your head on the carpet, spread
those butt chicks as wide as you can I am going to eat your ass and then
fuck you boy..."  I obeyed..turned around facing the computer and my ass
facing him, I got on my knees, rested my head on the carpet, both shoulders
touching the carpet, and with both hands I parted my butt cheeks...My
rosebud, my fuck hole, my boy's pussy pulsating inviting Barry to fuck it.
He got behind me also on his knees , he bended and buried his face in my
ass crack, his tongue swirling wildly, spitting on my sweet ass, probing
with his finger making me beg for his cock... "Oh Daddy, I love how you eat
my ass, and finger me, put more fingers in Daddy, I want you to open me
well, so I can take your cock deep in me..." I said.

Barry was really enjoying my ass, he would put his tongue in as deep as he
could, and the spit in my ass.  He would push my back down and he would eat
my ass ensuring it was wet and ready for his cock. He then asked me to turn
around facing up...he pushed my legs back towards my chest, my knees
hitting my chest, he placed a pillow from the sofa on the floor, and placed
me at the edge of the pillow.  He then pushed my legs backward again he was
kneeling in front of me.  He had his cock in his hand ready to plow it
inside me... but first he lubed and greased me well.  Then he lubed his
thick man's cock, he pulled me from my thighs closer and pushed my legs
back and said " I am going to put my cock in your baby, I will go slow let
me know if you need me to stop"

With that said I felt my sphincter expanding and big mushroom head went
inside me.. I was in terrible pain but at the same time I wanted his cock
so badly.  " do you like it baby?" he said, I moaned..."mmmmm, YES daddy I
can feel your cock inside me, fuck me daddy, fuck me deep, make me your
little boy, fuck me all afternoon, fuck me all night if you want to, make
me your little girl, your lover" with that he pushed his dick more inside
as he pulled on my tits... he pulled me a little closer and I felt his cock
get past my second sphincter, it hurt for a little while but the sensation
of having his cock in was what I wanted So I started moving up and down he
got with the motion and soon he was fully pumping my ass getting his cock
as deep as I could take it I could feel his ball crashing on my ass as he
pound me.

He spread my legs held my ankles and fucked me deep..then he pulled out and
with one swift move he picked me up and took me to the bed.  He dropped me
in the middle of the bed which he climbed and put me on all four legs and
started fucking me doggie style, the deeper he got his dick in, the more I
wanted him " Oh Barry Daddy fuck me, fuck me hard" I said.  He was not
talking just pumping my as he was dominating me keeping me on a submissive
position head on the bed, shoulder on the bed, ass in the air, he was on
top, so he could stick his cock all the way in.  He was really enjoying it
when he finally cried out " I am coming" at the moment he buried his cock
inside me I could feel his cock pulsating feeling my ass with his cum, " I
want some in my mouth" I yelled... pulled out still spewing sperm out of
his pulsating cock and put his cock right inside my mouth, I had cum
dripping from my chin, my nose and I was drowning in cum.. "swallow" he
said ...I obeyed him and took a big gulp of cum down my throat, he pulled
his cock out of my mouth and put it back inside my ass.. It went in easily
my ass was gaping wanting more cock, he continued pomping me and pulling
his cock out and putting it back in my mouth and spewing a little more cum
every time he did that.  He must have gone back and forth about 3 times
before his cum stopped. I was drenched in cum, my ass was dripping cum, my
mouth was dripping cum, my back had cum, my sides had cum, I turned to him
and sat on the bed, took his cock and started cleaning his cock, eating
every drop of cum Daddy was giving me.

After a few minutes his dick started to go limp.  We lay in bed, kissing,
and caressing each other.  He was a very caring man; he kissed me all over
my body, and took my little cock in his mouth and sucked it, I was really
enjoying him sucking me, when I looked at the clock and said Oh God it is 7
pm, we had started arrived at his house at 3 pm, and now it was 7 pm.  He
took me to the bathroom and we bathe, he cleaned me all over making sure to
clean my ass well, was we were showering I sucked his cock one more time,
he was in heaven, he kept calling me the best fuck he ever had. After we
showered I told him I was not in a hurry to get home, that Mom was not
expecting me in until late, he said he rather take me home so My mom would
not be upset with me.  I agreed.

We kissed in the car in front of the house, and I pulled his zipper down
and had a little taste of his cock, I sucked him to completion I drank all
his cum, and headed to bed.  Barry pinged me on the site the moment he got
home.  "you are the best fuck I ever had Alex, when can I see you
again"... I told him I would let him know, but I did want to see him again.
I was just turning the computer off when the doorbell rang.  I ran
downstairs, my surprise, It was David.

Hello beautiful I said... want to come in?  He looked at me and said...
"Come to my house and service me before I go to bed. I need a good
cocksucker".  I could not believe it, It was going to be a long night...