Billys Introduction to a Sex filled Weekend
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Billy's Many Adventures I free porn video
Billy's Many Adventures I
Billy is an average young man at the age of 21 has had his share of women that he
has met at the clubs. Billy has one secret is that he is a crossdresser. Billy
has been one since before he can remember. He enjoyed wearing women's clothing,
starting with going through his mother's drawers and finding her panties, and
finding enjoyment in wearing them for brief periods of time.
As a child Billy did like most young cross dressers wore his mother's underwear
underneath his clothing. To school he would wear them, and even around the house
he would wear them, getting pure excitement in wearing silk underwear that is
forbidden by young boys to wear. Again Billy like most found that wearing
underwear soon was not enough, he started to get into his mothers panty hose
drawer, and tried on some lingerie.
This was the best time for Billy because he was so excited about wearing silk
lingerie that he would masturbate on a regular basis with his mother's lingerie
on. The time Billy was going through this was the time of the Internet, so Billy
was very lucky to have support groups and Internet friends that eased him through
his dressing, unlike many who did not have help in years past, who had no help at
all. So Billy was very comfortable in his dressing and knowing that he was not
"weird".
Billy had just graduated high school at the age of 18, and for a graduation
present for himself he bought a cheerleader outfit through the Internet that he
had been eying up forever. The package came just in time, his mom and brother
were going to visit friends for the weekend and Billy had the house all to
himself. As soon as they left Billy ran upstairs and threw off his boxers and
into the cheerleading outfit. Staring in the mirror at how well it fit, and how
he really felt like a cheerleader. Billy figured if I am going to look like a
cheerleader he may as well look up some cheerleader routines so he could
practice. So on the Internet he went looking for a good routine. Billy forgot
that he had left the door opened downstairs, and he could hear noice coming from
downstairs, his mothers boyfriend Mark.
He shouted "Hey Billy, the door was open I just wanted to bring back your sports
illustrated I borrowed."
Mark was a good guy, he was 45 years old, had a good job, and he treated Billy's
mom right. He had been dating her for about a year. Billy and he really got along
as well as they like to go sporting events together. But what would Mark think
about Billy being dressed as a cheerleader????
As Billy heard Mark coming upstairs he had no time to get into other clothing as
he was in his mom's room where the computer was and no clothing to change into.
Mark came into the room and really at first just stared at Billy for a few
seconds, and finally after a dead stare said "Uh... Billy what are you doing
there?"
Billy after a few "uh's" said, "Well to be honest I like wearing women's
clothing."
He could not have been more honest than that as he had total respect for Mark,
and besides there really was not anything else he could say.
"Please don't tell anyone about this please!!!!" he bellowed.
Mark looked at him and said, "You know I am pretty modern, and I understand, can
you tell me more about it though??"
Billy said, "Okay why don't we go downstairs and talk, but let me change first."
Mark very quickly said, "No, you don't have to change on my account, just come on
downstairs with me and talk about it."
Billy did not put up a fuss and went downstairs in the kitchen with mark.
The two sat down to a beer, and Billy spilled his guts on everything, telling of
his crossdressing since he was young, and the many adventures he had with his
mother's clothing. Mark listened and gave empathy to Billy and gave Billy this
advice.
"Don't try to be anyone you don't want to be, if you enjoy cross-dressing then do
it, you only live once in this lifetime and if you want to crossdress then I
respect you no differently."
Billy was very happy with what he had heard as mark was the first person he ever
told his real feelings to, and he believed in Mark. Mark also assured him that
his secret was safe with him, and that he would not tell his mother about it.
After this conversation the two decided to make a day of watching sports on TV,
racing was coming on, and there would be a football game on after that.
Billy went to change, but mark stopped him and said, "Hey be yourself today, I
already know about it. so be who you want to be, and enjoy what you are wearing,
and besides..." as he chuckled. "You look cute."
The two got a laugh out of that comment and Billy decided to not change his
clothes, he would stay in the cheerleader outfit for the day.
As racing came on, Mark and Billy started to get very involved with the usual guy
talk and drinking beers, and eating pretzels. They talked about his mom, and that
Mark may soon be popping the question, this made Billy very happy, as he always
wanted the best for his mother, and Mark should be the best thing that has
happened to her. After the racing was over the football game came on, and the two
teams were the Bears and the Vikings, Mark loved the Vikings and Billy loved the
Bears, so this got some competition going between the two of them as they each
cheered for their team. By half time, they had put away almost a case of beer,
and were starting to slur their words a bit. But having fun was exactly what they
were doing.
In the third quarter they started arguing a call as guys do, and Mark said that's
it its wrestling time. And the two jumped on the floor and were wrestling as they
had done in the past. Both were very weak and sloppy when wrestling after so many
beers, Mark, the stronger of the two, got Billy head down first into the rug, and
grabbed Billy by the knees. Mark had won the match, but Mark also noticed
something that he could not take his eyes off of.
As he had Billy by the knees, he could see Billy's red panties through the skirt
of the cheerleader outfit, and that Billy was hard as a rock!!!! Mark stared for
a few seconds and feelings that he had never felt before started to arise, he
really liked what he saw in Billy's growth in the panties. As his drunken
instinct took over he placed the tips of his fingers on Billy's panties and
rubbed for a second.
Billy flinched and tried to pull away, and Mark, the stronger of the two, held
onto his knees and said to Billy, "Relax for a second."
Billy with no strength left. could not pull himself out of this. Mark rubbed
Billy's penis through the red silk underwear and flipped the side panel to unveil
Billy's erect penis. Mark, who at this point had no control over his new found
feelings, took his mouth and tasted the tip of Billy. Billy felt he should not
let this happen, but for some reason he liked it, and did not resist. Mark took
his mouth all the way over Billy's manhood and began to give him the blowjob of a
lifetime. It only took a few seconds for Billy to erupt very massively. Mark took
all of the juices Billy had spread out and tasted for the first time in his life
another man, and he liked it.
After taking Billy's juices, he could see that Billy had a feel of relief that he
had let his load out, but Billy also had a guilty look to him.
The two stood up, and Mark said, "Billy I am so sorry, but I have never felt
those feelings before, I did not mean to break your trust, I just could not
control it."
Billy just wanted to ensure that nobody would find out about it, and that it
would not get in the way of his mother marrying Mark. Both men agreed that they
really did enjoy their first feeling, but maybe it was the beers talking.
Billy said "Well now that you have had me I think it only fair that I have you,
but not dressed as a man, I want to dress you up as well, it's only fair."
Mark tried to play the macho card, but deep inside really liked the idea, so he
agreed to Billy that he would dress as well. So now Billy had some work to do,
what to dress Mark in????
As he took Mark by the hand he went into his mom's room and pulled out a pink
bras and panties set, and said, "Here you go, put these on while I look for
more."
Mark pulled himself into the panties with a struggle and took a few seconds to
figure out how to put the bras on, but mastered it very well.
As Billy came back in the room with clothes in hand he said, "My how lovely you
look in that."
He handed Mark a white silk blouse, black thigh highs and black leather mini.
Mark put on the panty hose, got a few runs in them, and put on the rest of his
outfit, Mark started to get very erect.
Mark looked at himself in the mirror, and very pleased with what he saw and said,
"Okay, now what to do?"
Billy turned to him and said, "Just do what comes natural."
Billy came close to Mark and kissed his new friend, it was pretty bad kiss, kind
of like he was kissing his grandmother, he really was afraid. Mark, the more
experienced of the two in kissing, opened his mouth and let out his tongue, and
pushed into Billy's mouth, finding Billy's tongue. The two started to French
kiss, like they were kissing women, it was so exciting for both men. Billy
commented about how well Mark looked as a girl and opened his blouse and started
rubbing his manly breasts through the bra he had on. Soon he started to kiss his
new friends chest.
The smell of another man was pleasantly exciting to both men. Billy took control
of the situation, and said, "I am gonna take you down." as he pushed his friend
to the edge of the bed he pulled down the leather skirt, and saw exactly what
Mark had found earlier in the evening, a very erect penis in very sexy silk
underwear.
He rubbed his mouth over the panties and the shape of Marks manhood, Mark let out
a yell of excitement and screamed, "Take me in."
Billy pulled off the panties and deep throated Mark and had the best taste he had
ever had in his life, he continued to enjoy what he was taking in and decided
that he would take his right hand and rub the bottom of his friend, slowly and
sensually.
Mark then yelled, "Oh my God I am gonna cum!"
Billy felt the penis getting very hot and as Mark started to cum, Billy took
every juice his friend had to offer, and as a good little slut swallowed every
bit of it. After the rumble the two sat next to each other and kissed for a
moment.
As guilt had now set in on Mark (after he came that is), he said, "What do we do
now???"
Billy said, "I really enjoyed what we did today and I would really like to do it
again, you have made me feel so good, if we could keep it a secret and every now
and then have fun."
Mark agreed that he would be disappointed if he never did this again. The two
made a pact that night that if they were both alone and the opportunity was there
that they would continue having fun, and it would be their little secret.
The two have continued for the last three years even after Billy's mom had
married Mark. They enjoy each other's company about once a month on a continuous
basis, and have not looked back since. ---
Louise
- 24.09.2022
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