Date: Tue, 2 Sep 2008 13:30:45 EDT
From: JamiebiTV@aol.com
Subject: My First Nylon and Girdle Experience (Part # 3)

Synopsis: I as a young boy (me) lived in the conservative  Midwest starts on
his life long journey of the joy of cross dressing and his  deep desire and
lust for silky sexy nylons. Soon he starts to learn with much  encouragement
what it's like to be a girl from his Mom's best friend!

My First Nylon & Girdle Experience
By Jamie  R.

Written & Published Exclusively for Sheer Delight  (trannycafe.com) Copy
write 1998-2008 by Jamie R. of T. H. Ent. ALL Rights  reserved and property is
absolutely not to be posted, printed, or used in ANY  way other then by readers
for own their personal use.

My TRUE STORY! I as a young boy (me) lived in a conservative Midwest town
starts on his life long journey of the joy of cross dressing and his deep
desire and lust for silky sexy sheer shiny nylons! While this part of the
story is complete. I am writing the continued journey he makes after the
first time!  More of my true and fantasy stories about cross dressing,
nylon stockings, pantyhose and smoking fetish are available on my T-girl
fetish web site, TrannyCafe.com. Opening fall 2008 Kisses! Jamie

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Part III (Becoming a real girl and not just a cross  dresser)

Well, the next big event happened when I went over  to play with the boys
(more like see sexy Sally to remind her of our weekend if  she saw me) and found
them not home. Sally's current steady boyfriend was home  and told me to come
on in but the boys went with their Mom to the beach. I was  about to leave
when he asked me if I wanted something to drink and watch some TV  with him. I
said sure and went to the living room and sat on the couch. I was  not paying
much attention but as Bob (not his real name) came in, he handed me  the drink
and I thanked him as he sat down next to me. We watched the show and  than
after a few minutes, he asked if I could do him a huge favor. I did not  know what
he had in mind but said sure. He said he had heard of my little  adventure in
the bathroom from Sally and thought it was cute. My mouth dropped  to the
floor and the blood went right to my face! I could not believe Sally had  told
him but I quickly remembered she told me she would not tell my Mom. She  never
mentioned not telling anyone else. I was speechless but Bob saw the
embarrassment I was dealing with and he quickly told me that he did not think it  was a
bad thing. What? Did I really hear him say that? Wow. This made me feel a
TINY bit better but I was still pretty blown away. The next thing he told me
almost knocked me right over! Bob said he wished he was there that day and could
have seen me and in fact he would give me some money if I went in the
bathroom  and changed into what I was wearing that day and "model" for him. Pay me?
Wow! I  was at this point so much in a state of shock that I did not know what
to say or  do but I knew that he said he was ok with me dressing that way and
that he  offered me $$$ and finally, I have been dying to try it on again
since that day!  I let out a meek ok. He said ok, well Sally and the boys would
be gone all day  so get started and we can have a little fun. I got up with my
numb body barely  responding and went back into the "den of lust" of my
desires (the bathroom) and  behold there were all of Sally's finest again! My heart
skipped a beat or two  and I quickly stripped my clothes off to be totally
naked and than went to her  hamper to see if she left me any fragrant item to
hold up those yummy nylons.  She of course did not disappoint me again! I found
a very sexy garter belt and  it was very femm and lacy. I also found a very
nice slip with lace around the  bust to match my garter belt. I then chose a
pair of her coffee colored  stockings off the rod. I sat down to roll up the
nylons on my young hairless  legs and melted with the feeling of them on my skin
again! I was soooo hooked to  enjoy doing this forever! Next I put on a
matching pair of panties and the  garter belt and than threaded the straps through
the panties in case I had to  take them off to go potty. I attached the clips to
the nylons and than smoothed  those yummy items on my legs loving the
feeling! I than put on Sally's silky  short slip that just barely covered the tops of
my stockings. I felt so sexy and  hot! I also was sooo afraid to open the
door and go back in with Bob. I than  worked up my nerve and after all he told me
her would give me money.
Bob was sitting on the couch very relaxed watching  the TV when he looked up
and saw me standing there in my pretty attire. His  mouth went open and than
he sat up and said WOW! It made me feel wonderful that  he clearly like it. I
was lightly shaking and was embarrassed beyond imagination  but the funny thing
is I also felt very very good and feminine! So as I started  to relax by his
obvious approval and him telling me I looked GREAT! I started  the agreed "
fashion show" and did what I have seen on so many pageants on TV. I  made like
there was a run way and modeled walking away from him and back and  even tried
to move girlie. This was so much fun and the nylons were making their  sexy
swishing whispers. It really was becoming so very nice and I felt more and  more
relaxed dressed this way. Bob kept encouraging me and telling me what a  great
model I made. He told me that I had great legs and my outfit made my butt
look very feminine and nice. I just got more into the part and was on a cloud as
 I wiggled my body more like a girlie girl. As I made my way for about the
forth  time away from Bob on the couch I turned and my whole fantasy girlie
bubble  burst! Bob was still sitting on the couch but had his pants open and this
big  penis in his hands. He was looking at me with total lust in his eyes like
I was  a steak on a plate in front of a hungry man just out of the desert
island for 6  months living on only coconuts! I stopped in my tracks and my mouth
fell open.  The fear rushed back into my body and I felt the blood in my face
again. I did  not know what to do. I never saw a penis that big. It had to be
three times  bigger than mine. Bob told me he was sorry but I looked so nice
and don't be  scared. He was just very turned on by my modeling and my legs in
the sheer shiny  coffee nylons. I just stood there not saying anything or
moving. Bob said it's  ok and to come sit on the couch next to him as he patted
the seat with his free  hand. I did not respond so he tried again to reassure
me and once again invited  me to come by him. I stated to slowly move closer
and could see more of his huge  semi hard penis in his hand that he continued to
slowly stroke. I gingerly sat  next to him and my eyes were locked on his
meat. It looked unreal and something  in me would not let me take my eyes off it.
He asked me if I thought it was  nice. I shook my head lightly yes. He than
asked if I wanted to help him. I was  scared but excited inside beyond
explanation! I surprised myself and again shook  my head yes. Bob wasted no time by
taking my little hand in his as he said he  would pay me more if I can help him
feel better. I still said nothing. Bob told  me that I was soooo sexy and
looked sooo good in my lingerie and silky nylons  that he was never so turned on.
He told me that I was a the perfect model and I  should dress more often cause
I was a natural. All his words came to me and  registered but I was still
locked in my gaze on his COCK! I watched my hand get  closer and than I felt my
first cock other than my own. Oh my! It was hard but  soft and so smooth. Bob
wrapped my hand around it and got me started to stroke  him and than removed
his hand. I was watching his head of his cock pop in and  out as I skinned back
the foreskin. That was amazing as I was circumcised and  never saw a cock that
looked like that. It looked so incredible. I started to  relax and Bob just
kept telling me how good that felt. I was hypnotized and was  enjoying touching
it. I also noticed some cloudy liquid forming at the tip as it  became harder
and harder in my hand. It no longer had extra skin and it was  longer and
very defined. It was 8.75" long (as I found out later) and it was  fairly thick
but not too much and it tapered to a point at the head. It was  unreal and I
just kept pumping him looking at this incredible monster in my  delicate hand!
Bob said I was doing so well and asked me if I wanted to make  even more money.
I did not look at him but quietly asked how? He said if I  kissed it and put
it in my mouth he would pay me more money. I quickly shook my  head no. Bob
asked if I did not like his cock and I said yes. He said he would  give me
twenty dollars if I would kiss just the top and for the modeling. I did  not
respond. He again encouraged me and told me he knew I wanted to and it was  ok. He
than took his hand and placed it around my head and slowly pulled my head  down
to his cock. It was right in front of my tender lips and the goo was so
tempting. I slightly opened my lips and moved in to kiss the tip. As I did the
liquid spread across my lips and I got my first taste of precum. I liked it even
 if it was a tiny bit salty and Bob just moaned with delight. I wanted more
so I  again kissed it and tried to taste more of him and he again took his hand
on my  head and gently pushed me into his cock so more of the head slid
across my lips  and into my mouth. I could feel my own cock was very hard in my
panties now and  I did not want to stop! I willingly took more of him in my mouth
and while I was  still scared, I was excited beyond words. He kept telling
how sexy and pretty I  was and he started to buck his hips to move his cock in
and out of my mouth. He  asked me if I wanted to be his special girl. I just
shook my head yes as I  continued to give him my first blowjob. I got more and
more into the role and  REALLY enjoyed sucking him. He kept moaning so I knew I
was doing a great job. I  wanted so much to please him! Bob told me to lick
around the shaft and take my  hand and play with his balls as I sucked him. I
did and they felt equally as  nice and foreign. He told me something that made
me turn a corner in my life  forever! Bob told me that I not only looked great
in my sexy girlie clothes but  that I was a wonderful cock sucker! I loved
that! I wanted to be that! I wanted  to do this forever! I continued to suck his
cock like I was on a mission. Then  it happened. I felt Bob tense up and move
his hips up as he told me that I was  going to make him cum and to be a good
girl and not let any liquid fall on the  couch! I than felt his cock swell in
my young mouth and than a flood of cum  filled my mouth and some went down my
throat! I did not know what to do and  backed off as the last of his sperm hit
me in the face. I was like a deer in the  head lights but I knew I did
something right! Bob moaned loudly and than took  his hand to finishing milking the
last of his cum to the tip of his beautiful  cock. He asked me to lick it off
so not to waste it and I eagerly did so as I  really loved the taste. Bob told
me I was a very good girl and than he took his  finger and wiped off his cum
still on my face and said open baby to feed it to  me. Bob asked if it tasted
good and I quickly shook my head yes with a light  smile on my face. He said
good cause he would love to give me more in the  future. I just said ok.
Bob pulled me next to him and wrapped his strong  arms around me as we sat
side by side for him to recover. I felt like his  girlfriend and it was really
nice, safe and warm there. He kept telling me how  sexy I looked and that was
sooo wonderful what I did for him. He asked me if I  enjoyed being a sexy
little cock sucking girl. I said my first words other than  yes, I told him I would
love to do it more. Bob just smiled and told me he was  very happy to teach
me everything I need to know to be the best and hottest  girl. I said ok, that
would be wonderful. Bob got up to get a drink and I just  watched him as he
dropped his pants and took off all his clothes. He walked to  the kitchen and
his semi hard cock just bounced wildly as he did. I knew I would  be getting
more of that beautiful cock again soon! I watched TV as I sat like  his little
girlfriend on the couch waiting for him to return. I gently rubbed my  own still
hard cock thinking how lucky I was and how much I enjoyed what just  happened
to me and be a girl! I forgot all about the money!
Bob returned with a drink and one for me. He  noticed that I had a stiffy in
my lingerie and told me that it's ok if I want to  play with my self cause I
earned it for being a very good girl. I smiled and  pulled out my little cock
and started to stroke it in front of Bob as he drank  and just smiled at me
with loving eyes. He said he hoped I had fun being a girl  cause he really loved
having me as his special girlfriend. It would be our  little secret and he
said if I ever wanted to suck his cock again all I had to  do is ask. He had NO
idea how happy that offer made me or how much I would take  him up on that! The
thought of it and all that happened was getting me ready to  cum too. I was
building to probably a huge orgasm but just than Bob told me to  wait. I
snapped out it at the height of my lust to see he was again stroking his  beautiful
cock. I looked at him as to ask him why he stopped me and he asked if  I
wanted to make it an even $25 and learn something REALLY good. I said ok as my
trust was now very high with him and I wanted to please him and $25! Wow! He
knew I was sooo turned on at this point that I was ready to take on the football
team if he asked. He told me to first come over and kiss his cock again which
I  quickly and hungrily did for him because I loved it! He than said as I
sucked  him, he wants me to stand up and stand between his legs. I sadly let lose
of his  cock with my mouth and did as my man asked. He smiled and ran his
hands all over  my waist and than down to my silky nylon covered legs. I felt
electricity as he  touched them through the thin nylon. I LOVED this feeling. I
was becoming more  and more sure that I wanted to dress like a girl forever! I
also knew I wanted  to be Bob's girlfriend too! He could do anything with me
and I would dress  however he was pleased. He than told me to turn around and
than he ran his hands  across the soft slip covering my butt and that also felt
wonderful. He said I  should get ride of the panties witch I did. As I bent
over to take them off my  feet I felt his hands go under my slip and rub my
naked butt and it was  wonderful. He told me to stay bent over for a bit and told
me I have the  sweetest little ass. Anything I can do to please him was all I
wanted. I moaned  as he lightly rubbed it and grabbed it now and than. He
than said to wait a  second as he reach for something on the lower self of the
night stand next to  the couch. As he sat back up he told me to stay like I was
and that this was  going to be a little wet and cool but don't move. I said OK
with a "I will do  ANYTHING you want" tone in my voice! He than took his
finger with something wet,  cool and slippery on it and he started to enter my
butt. I was sooo confused but  I trusted him as he worked his long adult finger
in me deeper and than I felt  him add another finger. He slowing moved his
fingers back and forth and it  started to feel wonderful so I moaned lightly and
pushed my butt against his  hand. I wanted him to keep doing this and wanted
him to know I liked it. He sure  did and than asked me if I was ready to become
a real girl. I did not know what  he meant but being I had not cum yet and I
was at the height of my excitement  and lust I said I did. He told me to turn
around as he slowly drew his fingers  out of my ass even if I did not want him
too. I did as I was told and he told me  to kneel on the couch with my legs
lightly spread. I did as he got up off the  couch and got behind me. He told me
to bend over again as he used his hand on my  back to guide me. I was than
with my butt in the air and he told me to just  relax and trust him. He told me
that this would hurt a little for a little bit  but would soon feel really
good and be worth it. I was again scared but as  before, I trusted him and did as
I was told. He told me to push out like I was  taking a poop when I feel him
against me. I thought he was going to stick his  fingers back in but I than
felt his beautiful cock at my rosebud. He very slowly  started to push into me
and made little stops. He kept asking if I was ok and I  shock my head yes.
Hurt a little? OUCH! It was hurting a lot and was about to  tell him to stop when
I felt a pop and than he glided much deeper in my tender  little butt. I
still hurt but it was not as bad and I felt like I had to take a  poop. I let my
man do as he wished with my ass and soon I felt his body right  next to my ass.
He had that huge cock all the way in me but was not moving. Bob  told me he
wanted me to again relax and get used to it in there. He then started  to pull
out and then in and again out and back in. His hips started to move in  rhythm
more and more fast and the pain was going away fast! In fact, I was  moving
my ass to meet him. I started to feel as he promised! It started to feel  soooo
good! I wanted it more and he was now thrusting in me and out full speed.  He
told me what a sexy girlfriend he had and I loved every word as I loved this
man's cock. He kept fucking me and I kept telling him yes! I told him I
wanted  more! He told me I was his special girlfriend and that he was going to do
this  and have me suck his cock often while dressed sexy for him. I told him I
wanted  that sooo much! What felt like hours (actually about 10 minutes) I
felt Bob's  body tense up again and he told me he was coming in me! I told him
yes, please!  I wanted to feel him explode in me! He wasted no time to my
request. I felt his  body jerk and than a wonderful warm flood of his delicious
cream fill me deep  inside! Than something I did not know could happen, I cam in
an explosive orgasm  all over the couch and I NEVER even touched my own cock!
We both collapsed and  he reached for some tissues to wipe my cum off of the
couch. I was soooo  satisfied and felt soooo wonderful and relaxed. I was very
happy how my life was  turning more and more interesting and exciting. I just
loved being a girl and I  loved this man who was helping me become one. He was
a great lover. Even at that  age, I knew this to be so! I wanted to be his
girl whenever he wanted me! He  made me feel so wonderful inside when he told me
that was some of the hottest  sex he has ever had. He also told me that some
girls and even some "special  girls" like me were made to be a "man pleaser".
He said I was a natural and born  to suck cock and born to get fucked. I was
soooo happy!
Bob told me I had better get changed back and run  along to my house so I don'
t get in any trouble and reminded me that what  happened MUST be between me
and him! I said, I understood and went to change.  When I was back in boy mode,
I went to my new lover and kissed and hugged him to  thank him for a
wonderful experience. He than also reached in his pocket and  handed me $25 dollars. I
had forgotten all about that and it was very nice to  make for a perfect
time! I guess it was the start of my future as a "kept" girl.  After the time of
my life and feeling wonderful with Bob's cum slipping from my  ass, I floated
home on a cloud and wondered if I would be able to do that again,  SOON! As it
turned out, Bob left the next day for his business and I did not see  him
again for a few weeks. I missed him so much! I wanted his cock in my mouth  and
ass again! I wanted to taste his wonderful sperm  again!

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

I hope you enjoyed this third part of my  autobiography on how I started my
journey into the erotic and wonderful world of  being a T-girl and how I fell
in love with yummy, silky, sheer, & shiny  nylons and how I became a Virginia
Slims girl! Your feedback is very much  appreciated and I would like to know if
I should post more chapters of this on  going part of my life that was the
best years of my life! Kisses Jamie  (_Jamiebitv@aol.com_
(mailto:Jamiebitv@aol.com) )