Todds Goodbye Fuck
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Todd's Story free porn video
Todd's Story
by Todd
In the beginning, and I am not certain that this has anything to do
with the rest of the story but you never know, my sister used to love to
dress me in her doll clothes when I was very little. I do not know how
long this took place or how often. But my parents have confirmed that it
did take place.
Later in life, in junior high, I shared a bathroom with my older
sister and our dirty clothes were gathered in a common hamper. One day
curiosity got the better of me and I put on her pantyhose. The feeling was
incredible and I was rock hard and had to jerk off immediately. I pulled
the pantyhose down to my knees and jerked off right there in the
bathroom. When I was done I was very embarrassed and confused. I did
not do anything else for several months then, my horniness got the better
of me and I tried it again only this time I wore them a bit longer and
walked around my room in them enjoying the feel on my legs and the hug
around my penis and ass. I could not get over the feeling when I ran my
hands over my legs and ass. I did this a few more times each time getting
a little bolder and even tried some of my sisters panties, they were a bit
small but were an instant hard on when I put them on. Once I tried on one
ov my sister's skirts with the panties and hose, but as soon as I got into
them I heard someone come home and had to quickly return everything. I
did not attempt that again, and eventually my sister went off to college and
that source was gone.
In high school I really tried nothing, but discovered Variations
magazine which often would have a story or two about crossdressing.
Then in College I was able to maintain a relationship with a girl for a year
or so, and lost my virginity to her. She was very exciting and energetic, I
was so excited about actually having sex with a girl that wearing woman's
clothes did not really draw me. Although I still got excited upon reading
any story that involved any level of crossdressing. I dated this girl for
over ayear and she introduced me to some light bondage and she liked to
be in control. We broke up before my senior year of college and I did not
find another steady girlfriend in college.
After college I ended up in Germany with the Army. Ok
Crossdressing was not in the forefront of my mind, but I did do some
experimentation on my own. I shaved my pubic hair and played with that
for a while. It was a thrill to perform the shaving and the feeling of the
hairless skin was exciting and a turn on but it did not last, and the re-
growth period was very uncomfortable. The fear of having to explain the
missing hair was a major deterrent in the army.
After a tour with Uncle Sam, I found myself working in Chicago.
Over time work settled down and my horniness grew and I was again
reading Variations each month. I my thoughts started to drift back to the
idea of wearing panties again. Then on a spur of the moment I bought a
pair of panties and some pantyhose. Once home I put them on and
immediately jerked off , just like before with my sisters. This time I was
hooked. And then the next night I started a ritual of putting the panties and
hose on after work. Then I would wear them and read Variations. One day
while in downtown Chicago I noticed and adult book store and I ventured
in. Inside I saw all sorts of sex toys and magazines and such. I left the
store and went home stripped downs and jerked off just thinking about all
the stuff I saw.
As time went on I began to pay more attention to the other stories
in Variations, and I cam across a story about a woman who used a dildo
on her boyfriend and this got me hard, and I found myself jerking off to
the story. The idea was planted in my head. I read the story again and
started the jerk off and then I reached down and played with my asshole.
Then I put some lotion on my fingers and slid a finger in my ass and
continued to jerk off with the other. The orgasm was earth shattering. It
was a few months later that I ventured back to that adult store and bought
a very small dildo (about 6") and brought it home. That night I found
myself sliding that dildo into my ass and jerking off.
In the spring of what would be my last year in Chicago my interest
had again turned to the panties and I spent several weekends in various
outlying malls/department stores shopping for a gift for my
girlfriend/sister, but not ever having the courage to buy anything. Then
one day on my way home, I stopped in at a small store and was greeted by
a young female sales clerk who asked me what I was looking for. I
blurted something about having to replace a skirt of my girlfriend that I
had ruined or something to that effect. She pointed me to the skirts and I
bought a simple black pleated skirt and made a hasty retreat. Once home I
could not get undressed fast enough. I slipped on the panties and the hose
and slid on the skirt and loved it. The next day I had the courage to buy a
matching panty and bra set and a simple light blouse. That night I spent
the evening dressed in my completed outfit and cleaned my entire
apartment and then jerked off with the skirt pulled up and my panties
pulled down. I continued with this one outfit until I moved to New Jersey.
Before the move I purged, and threw out everything.
In Jersey, as in Chicago, work was a 18hr day event and I spent
most of the weekends getting oriented to my new surroundings and doing
some more work. But as the pattern continues, as the work became
manageable I began to dream of the dressing. I replaced the panties first at
a little store that was just opening. The panties were these little white lace
things that looked great but did not feel great. About a month later I
bought a couple pairs of panties and a bra that matched one pair of the red
satin panties. I also picked up( at a different store) a couple pairs of
pantyhose, one black and one nude.
I had taken several business trips to California and each time I
would visit several adult bookstores. On most trips I never bought
anything, but on one trip I saw a small butt plug and the spur of the
moment got the better of me and I bought it. It was small no, more than 3"
long, and I did not use it until I returned to Jersey. When I did, it was
always a short usage just long enough to jerk off. Then one weekend,
when I was particularly bored I decided to push my limits a bit and I
stripped down and put on my red panties and my black pantyhose I
slipped on the bra and cleaned my apartment. Then I wanted to see if the
new Variations had come out so I slipped on a pair of jeans and a bulky
sweatshirt, pulled on some socks over the hose and stepped out of my
apartment for the first time wearing women's underwear. I drove to the
convenience mart that I usually bought variations and was disappointed
that the new one was not out yet, but I had to buy something so I bought a
diet soda and a copy of Penthouse Letters. I then drove home, nervous
and very excited. Once home I stripped off the boy clothes and jerked off
to the first story I read.
A couple of weeks later I was in the mood to try it again only this
time I added a new twist, I slipped in the butt plug before I left the house.
I then drove to a store farther away. I was trembling as I drove and damn
near uncontrollably shaking when I entered the store. I was the only
customer and I just eased down the isles. At one point I squatted to look at
something on the bottom shelf and almost fell over as the plug shifted a
bit. Again it was a nervous drive home and the same end result.
About three weeks later came my boldest adventure yet, I put on
my white satin panties and the nude pantyhose and then dressed normal
and headed out for a Mall about 45 min away. Once in one of the major
department stores I went to the Men's section and selected a couple of
pants that would fit me, and then casually strolled across to the women's
section and picked out a skirt. I slipped the skirt between the pants and
walked back to the men's section to browse some more. Then I headed for
the dressing room and locked myself into one of the rooms. I was slowed
down a bit when I noticed that the bottom of the door was about 18" off
the ground. Anyone could see my feet, my stocking covered feet! I
slipped out of my shoes and my pants and then quickly slipped on the
skirt. It was a bit small but I was able to zip it up. I stood there and spun
around in front of the mirror and froze when I heard the voice of a woman
approaching the dressing rooms. I stood dead still as a mother ushered her
son into one of the other room and then stood outside of mine waiting for
her son to emerge in his new pants. He must have tried on a dozen pairs
of pants. When she finally did leave I changed back into my clothes and
left the dressing rooms quickly without trying to attract any attention to my
self. I then went for a walk in the mall for about 20 min to calm down
before returning to the woman's section of the department store. I then
went back to the display of the skirt I had just tried on and picked up the
next size up and a blouse that I thought would fit. I then proceeded to the
sales counter and asked if they could gift wrap them, which they did and I
paid for them and was on my way. As I left the mall I saw a little lingerie
boutique and mustered up the courage to go in. As I was standing there
looking at all the panties and bras to choose from, a mother and her
daughter entered and soon the daughter was in the dressing room of this
store trying on several different bras. I found myself jealous that she could
try on the bras and I had to guess which one would even come close to
fitting. I bought a new matching bra and panty set and was then
homeward bound. Once home I had to try out the first complete outfit
since Chicago and spent the rest of the evening dressed.
I did not buy any more clothes in Jersey, however I did start to
spend more time online in the chat rooms of AOL. I hung out in lots of
different room. I hung out occasionally in the crossdressing rooms but did
not enjoy the conversations much. Then I found some fun the Truth or
Dare rooms. These rooms were great as you could interact with other
people and tell them the truth, stuff that you could never tell anyone in
person. I would play and I loved both the truths and the dares. The truths
were a kind of therapy as I could tell someone what I had done or what I
was wearing and they would usually be very understanding. The dares
would offer a new sexual excitement as someone you barely knew was
telling you to do something and then you would do it. The shear
amazement of some people when they dare you to do something and you
actually do it, their disbelief is fun. One woman told me to stick my finger
up my ass and I said ok and did it and she was so shocked that I did not
flinch that she pressed me to be sure that I actually did it. I then told her
that I had a butt plug I could use if she would prefer. That was it we spent
the next hour just chatting about what we had and had not done, what we
were curious about and she promised to do any dare that she accepted.
She had lower limits than I did but we still had fun. We hooked up on line
several more times and then we lost touch.
Over the course of the next few months I started to hang out in the
"submissive males" chat rooms and had some fun encounters with some
female Doms. Some of them wanted just cyber stuff, with a lot of Yes
ma'am over the internet, others wanted me to come to their dungeons in
real life and pay them hundreds of dollars. I did not want either of those, a
couple of the doms liked to tell me to do stuff right then and there and
trusted that when I said I did it that I really did. They would have me get
dressed or insert something in my ass. Sometimes I would be told to dress
a certain way and go outside or walk by an open window. These late night
sessions would continue till I moved to Maryland.
After a little more than a year in NJ I took a new job with another
company in Maryland. Once again I purged my collection of toys and
clothes before the move. When I moved to MD, I had the chance to save
some money a share a condo with an old friend from high school. For the
first few months it was a typical situation of two guys living together.
Then I started to spend hours online again, surfing the chat rooms. One
night I came across a fantasy room and I jumped into a fantasy that
someone else had started. The scene started with someone tied up on a
hotel bed, I stepped in and said it was me, then as people asked questions
about what I was wearing and such, one woman took over. The two of us
went back and forth in the room describing the action and it became a
version of cyber sex but with a large audience. In the scene I was tied up
and wearing panties, bra, garter belt and hose. I was blind folded and had
my feet tied together and my hands handcuffed behind me. She entered the
room with a key that I had left at the front desk under a code name. I could
hear someone enter but I could not see a thing. Then she approached the
bed and she proceeded to fuck my mouth with a strap on dildo and then
she rolled me over and fucked my ass. The scene took a while to develop
but was very erotic. She was so excited and happy with how I had played
along that she asked if we could meet online again later. I of course
agreed.
When we met again, we chatted for hours about our history and
likes/dislikes. As I told her my story, she asked if she could be my new
Mistress. I agreed on the spot. She then had me take one of those 1500
question purity tests only instead of yes I have done it, she wanted yes I
would try it. That was her first command of me. Over the next couple of
months she had me going to stores buying new panties and bras, but she
was telling me specifics, as to what stores, and colors, and even cup
sizes. Then she insisted that I wear some combination for the next
session. This was difficult due to the roommate. I would put on what she
requested and have sweatpants and a sweatshirt handy in case my
roommate came home or knocked on my door.
Eventually Cynthia (my Cyber Mistress) had me go out and buy 2
dildos. She also had me buy a corset like bustier with attached garters and
some hose. The shopping lists occurred about once a week and she would
send me to buy one or two things. She had me buy some makeup, lipstick
and eye shadow, mascara and such, but she never had me put any makeup
on. She would have me wear panties or panties and hose under my clothes
to run errands. One day she told me to wear panties under my suit to
work. I go no work done that day! A week later she had me wear panties
to work again only this time she told me to go into the men's room and
jerk off in the stall! I did, but I was a nervous wreck the whole day. She
had me wear panties to work a few more times but not many.
Then one night we got online and she asked if she could call me. I
agreed and the next Saturday afternoon, my roommate was out of town.
Cynthia called me and we had a phone session. She had me get dressed up
in the new clothes and then after parading around the condo, she had me
sit down and take out one of the dildos. She then told me to suck on the
dildo. Soon she had me giving that rubber cock head. After a bit she had
me take out the second dildo and grease it up. The next thing I new my
panties were around my ankles and I was inserting the dildo up my ass.
Once it was all the way in, she had me kneel with a paperback book under
my ass to keep pressure up on the dildo in my ass. Then she had me start
sucking on the other dildo again. Then as I was sucking, she had me lift
my ass so the dildo would slide a bit out of my ass and then sit back down
on it. Soon I was riding the dildo and sucking the other for all I was
worth, all the while wearing a pretty emerald green panty and bra set and a
bustier/garter and black hose. What a sight I must have been. Then all of a
sudden she told me to grab my cock and make sure I caught all the cum.
Well I came as soon as I touched my cock and my cum filled my hand.
The she had me remove the dildo from my mouth and lick my cum filled
hand clean. After I was spent she had me clean up and get dressed in some
fresh panties. We spoke for a while and then agreed to meet back online
later that night.
Cynthia and I continued meeting online for another month and then
I stopped seeing her online and it was over. I did not find another online
mistress. Though I did keep the clothes and toys she had me buy. I
dressed a few more times but it was not the same. Eventually I did another
purge of all the stuff and that was it. Over a year later I met a woman at
work and we started dating. Over time we shared most of our sexual
history. I told her that I had experienced anal sex, but I lied about the
circumstances I told her that it was an old girlfriend who initiated it. I also
said that it was that same old girlfriend that had me wear panties. I
eventually married this girlfriend from work. Perhaps I will tell her
someday the whole truth, or perhaps she will find this story on my PC. I
am not certain what I want of this, but I know there is a certain sexual
high when I am involved in it. The mere purchasing of the clothes gets me
very excited. I have never dressed for anyone in person and I do not know
how I would handle that. Perhaps some day I will know.
(fin)
Myra
- 19.05.2021
- 26
- 0
