ACROSS THE STREET AND TWO DOORS DOWN
by
Spanky de Bautumn
Jamie knew he was different. He didn't fit in with the other boys, but
he didn't feel like he fit in with the girls either, he just knew he
was different. He wasn't into dolls or balls. He was the smallest boy
in his class and more than half the girls outweighed him. But the one
thing he had going for him was that he was smart. He wasn't in the
Mensa category smart, although he maintained a high GPA, he was more
street smart. He was a survivor. He was kind of like a chameleon, being
able to adapt to situations beyond his control. He figured out early
on that he could be an easy target of the bigger boys, which was just
about every one of them. He also observed that the way to get people to
like you is to make them laugh. He watched television, observed people,
and learned how to tell stories that made the human condition
laughable.
But, it was more than that, he had a natural talent and just polished
it with his observations. I know, because I've tried to retell his
stories almost verbatim and never get the same results. When he
finishes, people are laughing and talking about what they just heard.
When I finish, they just say that's nice and go about their business.
In fact, you'd probably find this story more entertaining if Jamie was
telling it, but, sorry, you're stuck with me. So, anyway, by the time
he entered middle school, Jamie was one of the most popular kids in his
class.
Tragedy hit the family when he was ten. The artery that supplied blood
to his father's brain ruptured and he died an untimely death. His
mother took it hard and started drinking to escape her suffering. She
was a substitute teacher at the local elementary schools and worked
about a week each month. She was smart enough not to let her drinking
interfere with her family responsibilities, but it also meant that
Jamie had to grow up fast in order to help her with her home life. With
her late husband's life insurance and her part-time job, they weren't
poor, but at the end of each month, they had to tighten their budget to
make ends meet.
As he got older, he found that he started to take an interest in
feminine attire. When the Sear's Catalog would come at Christmas time,
while other kids were checking out the toys, he was drawn to the
women's clothing. He found it interesting that women had so many
different types and styles of clothes to wear. He wondered if you could
get a read on a woman's personality just by the clothes she wears.
Women are more complex, maybe that's why they have so many choices.
Men, on the other hand, are basically stuck in one style, pants, shirt,
and a coat. Which makes sense because compared to women, men are
basically basic. That's not break through psychology, but kind of heavy
for a ten year old. He just chalked it up as part of being different.
In middle school, the class got larger, but he was still the smallest
boy and still kept them laughing. He got dates for some of the
important school dances, but in general, he wasn't sexually attracted
to either boys or girls. This was the time in most people's life where
they have that growth spurt. Jamie wasn't most people. One puzzling
thing about Jamie was that for being so popular in school, he didn't
have any close friends, so outside of school, he didn't have much of a
social life. If it wasn't for his humor, he would be a nerd.
In high school he started taking drama classes and, with his innate
ability, he took to it like a fish to water. He also started piano
lessons and became good enough to sit down anywhere and liven up a
crowd.
His mom did have some concern about her boy, she worried that his size
would be a real problem later in life and he didn't seem to have that
teenage healthy sex drive. He seemed to be indifferent about sex, he
had better things to do. Jamie's popularity gave him a lot of
confidence, the only thing that he had a problem with, and he figured
it was because of his overall size, is that he was also small where it
counted. He didn't lose any sleep over it, but it's something he kept
to himself.
***
The summer before his senior year, a new family moved into the
neighborhood. There were three kids, a girl, the same age as Jamie, a
son that was a year younger, and a younger daughter that turned eleven
the week after they moved in. It was a perfect opportunity for the
family to get to know the neighbors and vise versa.
Jamie had one sibling, a sister, Patty, she was ten. He was given the
responsibility of taking her to the party. Most big brothers would
rather eat buggers than take their little sister to a preteen girls
birthday party. But like I said, Jamie was different.
The family had moved to the city the year before. The father was in
management and was transferred from the main office to help start a
branch office here. The mother was a nice looking lady, you could see
where her daughter got her sense of style, was trying to get her own
beauty salon going. They weren't wealthy but they were well off and had
a lot of drive, which they passed on to their children. They had been
renting until they fell in love with the house across the street and
two doors down from Jamie's.
The oldest girl was Carrie, she was in the same grade as Jamie and
about his size, maybe an inch shorter. She was very stylish and kind
of had an air about her that rubbed some people the wrong way. The boy,
Matthew, was five foot ten and weighed a solid 165. He was a good
gymnast and an excellent diver. He was a good looking kid and a sharp
dresser and always seemed to be smiling like there was a joke and he
was the only one who knew the punch line. They called the birthday
girl, "Itsy", short for 'Itsy Bitsy', as she was short like her mom and
sister and on this day was a whirling dervish, in nonstop motion.
Jamie was his usual charming self and bonded with the two older
siblings right away. While the younger kids played outside, Jamie
entertained Carrie, Matt, and the other parents with his stories of
neighborhood mishaps. As a present, Jamie and Patty gave Itsy two
tickets to the local theme park. Patty said my brother is going to take
us and one of your other friends tomorrow. Itsy hadn't made any other
friends yet and asked Carrie to go. Carrie wasn't interested, it was
kids stuff, but Matt was glad to accept.
The following morning. Jamie's mom handed him the keys to her car and
told him she was putting her faith in him to be a good driver and watch
over his sister, don't let her eat too many sweets, and to be home in
time for dinner. Jamie asked her, "How do you expect us to have any
fun?"
She pinched his cheek and replied, "If you don't, it will be a long
time until you have any fun again."
"Okay."
"I hope you have some money for gas."
"I got it covered."
"Good, now you better get going. Your sister is chomping at the bit. Be
good and have fun, honey."
Jamie sat in the car waiting for Patty, who went to get Matt and Itsy.
The girls sat in the back and Matt hopped in front.
Matt said, "I haven't been to the park yet, I've wanted to go since we
moved here, just never got the chance. I've seen the adds on TV, that
Python Roller Coaster looks awesome. Have you been on it?"
"No, the last time I was there, they were just building it. That was
about five years ago. But, yeah, it looks insane. I can't wait."
"I'm not going on that thing," came Itsy's voice from the back seat.
"Oh, come on, Itsy. If you're scared, I'll hold your hand. It'll be
fun," Patty said.
"Maybe, we'll see," says Itsy.
"Girls," Jamie says turning to Matt, "you know what I mean?"
"Yeah, girls."
It was a half an hour ride to the park, the girls were all giddy in the
back seat, Jamie was concentrating on the traffic and humming along to
the Lady Gaga song on the radio. He looked in the passenger side mirror
to see if it was safe to change lanes when he caught Matt staring at
him. He changed lanes and looked at Matt who was looking straight
ahead. Maybe it was just my imagination, Jamie thought.
After a few more miles, Jamie glanced to his right and there it was
again, Matt just looking at him with that stupid grin on his face.
"What?" Jamie asked him. "You see something you like?" Jamie said with
a laugh.
"And what if I do?" Matt replied.
Jamie sat up and looked back to see if the girls had heard what he just
said. They were in their own adolescent world talking about what they
were going to do first thing.
Jamie turned to Matt, "What did you just say?"
"You heard me."
"Not in front of girls, we'll talk about this later."
Matt said, "Oh, alright," sounding disappointed but hopeful.
After finding a place to park, the boys had their hands full trying to
keep the girls from running amuck. They finally reigned them in and
while standing in line, Matt was thinking he might have blown it with
Jamie.
Matt had been into boys, especially feminine looking boys since he went
away to summer camp two years prior and got into a romantic
relationship with a boy named Frankie, who looked a lot like Jamie. Was
he mistaken, did he read Jamie wrong? He hadn't mentioned anything
about having a girlfriend. Maybe he hadn't been wrong and Jamie just
didn't know who he was yet. He made a decision to go ahead and take a
chance, what's the worst that could happen, he wasn't big enough to
beat him up.
Jamie was perplexed, he wasn't sure what he should do or what he should
say. This is the first to time anybody, male or female has ever made a
pass at him. What added to his confusion is that he had to admit he was
flattered that Matt appeared to be attracted to him. He was still a
virgin and a relationship was not at the top of his agenda, but he did
think Matt was cute, for a boy.
They got their sisters on the merry-go-round and stood there,
shuffling, neither one knowing how to start. Finally, Jamie said,
"Okay, Matt, what's going on?"
Matt looked around, waved at his sister, cleared his throat, and said,
"I don't want to get off on the wrong foot here, we just met yesterday
and I guess I made a mistake. I'm sorry."
"Mistake?"
"Yeah, well, I suppose you've figured out that I like boys."
"That would be my guess."
"When I met you yesterday, you were so funny and cute, and well to tell
you the truth the only reason I wanted to come is because of you, not
my sister, and I could give a shit about the Python. That's all I
thought about last night."
"Yeah, but..."
"When I saw you, I just assumed that you were gay. Are you?"
"I don't think so, I don't know to tell you the truth."
"How could you not know?"
"For one thing, I'm still a virgin and sex isn't the only thing on my
mind."
"A virgin!"
"Shh, you don't have to tell everybody."
Laughing, "Sorry, a virgin, that's a bummer. Have you ever kissed a
girl?"
"A couple. Oh, here come the girls."
As they joined the crowd on the way to the next ride, Jamie thought, so
that's why he's always got that smile on his face. He's living a double
life and no one knows, except me. They got the girls on the spinning
teacups and continued their conversation.
Jamie asked Matt, "Does your family know?"
"No, my dad would kill me."
"So why do you do it/"
"I don't know, why do you not do it?"
"Okay, fair enough. But, what am I supposed to do?"
"I know what I want to do."
"Easy, big boy, you're going to have to work to get this." Jamie half
turned and patted his ass, laughing. Matt laughed too and reached out
to grab Jamie's butt, but he jumped out of the way. Matt took a step
toward Jamie and he started to run the other way, just fast enough to
get caught. Matt reached around with both arms and pulled Jamie back to
him, "Gotcha, you can run, but you can't hide."
Jamie felt a flush in his cheeks and wiggled free, being in Matt's
strong embrace made him feel weak but somehow safe. This shook his
confidence, he was always the one in control, this was new to him. It
should have scared him, but it didn't.
Before either of them could say anything, the girls ran up to them.
"What are you guys doing, wrestling?"
Jamie gathered himself, "No, just playing around. You girls getting
hungry/"
"Yeah," they said in unison.
They all got hot dogs, except for Matt, he got a couple of corn dogs.
Jamie and Matt sat across from each other at a round table and the
girls sat together between them. The girls were all excited and could
not stop talking. Jamie and Matt were playing little games with their
eyes, making each other smile. When the girls went to refill their
cups, Matt took his second, uneaten corn dog and started giving it a
blow job while keeping his eyes on Jamie. Matt was trying to be sexy,
enticing, but Jamie threw a french fry at him because the girls were on
the way back. Matt stuck his tongue out at Jamie.
They did some souvenir shopping to let their food settle, then Patty
said, "Let's go on the Python now." Itsy was hesitant but Patty
promised she would hold her hand during the entire ride and she agreed.
The girls got in the front car and the boys in the back. As the car
started ratcheting to the top, Matt said, "Jamie, if I get scared will
you hold my hand too?"
Jamie chuckled and said. "Sure." He had barely got it out before Matt
grabbed his hand and held it tight. The young man doesn't give up,
Jamie thought. By the end of the ride, Matt's hand was gripping Jamie's
thigh for support on the bumps and curves.
After the Python, Matt became even more attentive, touching Jamie every
chance he got. At first, Jamie thought it was a bit too much, but
Matt's hands were soft and his touch was gentle and Jamie was starting
to like it.
When they rode the boat through the haunted tunnel, Matt put his arm
around him and Jamie surprised himself by scooting closer to Mark and
resting his head on his shoulder. Matt pulled him closer and laid his
head on top of Jamie's. Nothing was said, but neither can remember any
of the haunts, they had a moment and everything seemed to change. It
was a moment that would be remembered. Matt had been flirting and
treating him like a girl all day and Jamie wasn't resisting anymore. He
was used to getting a lot of attention, but this was a different kind
of attention. When he was telling stories he got the attention because
he was entertaining them, this was different. This was like being
spoiled kind of attention, having things done for him rather than him
doing for others and Jamie was finding it to his liking.
Having to turn their flirtations on and off depending on the nearness
of their sisters only added to the tension the two boys were feeling.
In the House of Mirrors, the boys got a little frisky. In the heat of
the late afternoon, Matt took his T-shirt off and was posing in front
of the mirrors. Jamie crept up behind him and started to tickle him in
the ribs. They ended up rolling on the floor with Matt sitting on top
of Jamie pinning his arms. Matt slowly started lowering his head, they
were looking eye to eye, he was inches away from sealing the deal with
a kiss when they heard the giggling of their sisters. "Oh man," groaned
Matt and they both sprang up and tried not to look frustrated and
embarrassed when the girls came around the corner.
It was nearing six, they had been there eight hours, Jamie's mom would
have dinner ready at seven, so they decided it was time to go. It was
kind of bittersweet for Jamie and Matt, they were really starting to
like each other and didn't want the magic to end.
The girls had worn themselves out and were asleep almost before they
were out of the parking lot. This gave Matt the opportunity to slide
over next to Jamie and put his hand on Jamie's thigh.
"I really wanted to kiss you back there, but I hesitated because I
didn't know what you would do."
Jamie looked at him, looked back to the road, then turned again and
kissed Matt on the cheek before he realized what he was doing. He
startled himself, but Matt took it as the green light and started to
paw Jamie. Keeping one hand on the wheel, Jamie slapped at Matt and
snapped, "Hey, I driving and the girls are right in the back seat."
"I know, I know, I'm sorry. It's just that you've been turning me on
all day and I just want to eat you up."
Jamie didn't know what to say, nobody had ever treated him this way.
?Well, at least keep your hands to yourself until we get home.?
?Okay, until we get home.?
Jamie always had a good feeling about himself, a positive attitude got
him through some hard times. But the way Matt was making him feel was,
was, well he just didn?t know, it was something he never felt before.
He reached over and put his hand on top of Matt?s. Matt looked back and
smiled.
A block before they got home Jamie woke the girls up and as soon as he
turned the car off, they ran across the street to show Itsy?s mom their
days take. Matt and Jamie sat silent for a minute, then Jamie said,
?This has been an interesting day, to say the least, Matthew.?
He liked it when he called him Matthew. ?I know, believe it or not, I?m
usually not this forward, you bring out the bad in me.?
?Oh, it?s my fault??
?Hell yes, I keep seeing you laying on a bed wearing nothing but a pair
of lacy panties or in a baby doll with some thigh high stockings.?
?Listen, I had a day that I will remember for a long time. You showed
me a side of myself I didn?t know I had, one I may have been hiding for
a long time, I don?t know. I do know you made me feel things I?ve never
felt, feelings about a boy and I think the best part is that you made
me feel like a girl.?
Matt still had that smile on his face, he really liked Jamie and was
glad to see he might have some feelings for him too.
?Do you know what would really make you feel like a girl?? Matt asked.
?What??
?If we finish that kiss we almost had earlier.?
?Mm, okay.?
Jamie couldn?t figure out what it was but this young stud seemed to be
able to talk him into anything. Or maybe he really wanted to do it and
just needed a little push.
They leaned into each other and pressed their lips together. When Jamie
felt Matt?s tongue try to part his lips, he pulled back. This is not
how he kissed the girls, there was never tongue involved.
?You really are a virgin, aren?t you??
?Told you.?
?Don?t worry, I?ll teach you all about it.?
?Who says I want to learn??
?If you?re going to be my girl...?
?Your girl??
?You know what I mean, my boo, my babe.?
?You?re awful sure of yourself.?
?Yes, yes I am.?
?What happened to that nice quiet boy I met yesterday at your house??
?Oh, that?s just an act, for the folks, you know??
Jamie took a good look at Matt, he was now seeing him in a new light.
Matt had a bit of a bad boy in him. Jamie found that a bit exciting.
His sister came running across the street, ?Hey, Matt, your mom says to
come home, it?s dinner time.?
?I better go, what are you doing tomorrow??
?Maybe mow the lawn.?
?You?ll be home??
?Uh-ha.?
?Can I come over??
?Okay.?
Matt took Jamie?s hand and said, ?Outstanding, I will see you
tomorrow,? hopped out of the car, clicked his heels, yelled, ?Oh,
yeah,? and bounded across the street.
Jamie laughed as he watched Matt?s antics, he was starting to have real
feelings for him.
***
At dinner, his mom noticed that Jamie wasn?t himself, normally after a
day like he had, at the theme park, he would be telling her funny
narratives about the day's activities. Tonight he was letting his
sister take the floor. Then as soon as he finished eating, he excused
himself and went to his room. His mom looked at Patty and she shrugged
her shoulders.
Jamie definitely had Matt and the day on his mind. This was all a new
experience and he had no idea how this game was supposed to be played.
He decided to try and not think or worry about it too much and see what
happens. This works okay when you are aware and have some control over
your thoughts, but not so good on your unconscious thoughts, as Jamie
found out later that night.
He was awakened in the middle of the night by a dream. In the dream.
Matt, Jamie and the two girls were back at the theme park. Jamie and
Matt were riding in the boat through the haunted tunnel just like it
happened. But when they got out of the boat, Jamie noticed that Matt
was wearing a tuxedo and looking sharp. Then the scene switched to the
House of Mirrors and Matt was posing in front of the mirror with his
shirt off. For a second, his thoughts were on how good of shape Matt
was in. When Jamie turned, he saw his own reflection and it shocked him
because he was wearing a wedding dress.
The shock woke him up, what the hell was that all about, he thought,
not trying to put too much meaning into a dream. He tossed and turned
for a while before falling back into slumberland.
He couldn?t get that dream out of his mind, sometimes it humored him
and sometimes it worried him. When he came down for breakfast his mom
asked if everything was okay, he seemed to be out of sorts last night.
He told her not to worry, he had a few things on his mind that he was
trying to figure out. She asked if she could help and Jamie shuddered
at the thought of telling his mom what was going on in his head.
He got up to put his dish in the sink and his mom asked, ?What are your
plans for the day??
?I was thinking about mowing the lawn, but it looks like it might rain,
so maybe I?ll wait until tomorrow.?
?It must be nice to be on vacation, I seem to remember something about
them, but that was a long time ago. I haven?t had a vacation since you
were born.?
?Thanks, mom, a little more guilt is all I need.?
?That?s what mothers do, son.? She laughed at her own joke. She had a
delightful laugh, it was infectious, and it made Jamie laugh too.
?I?m going to the market, do you need me to pick you up anything??
?Nothing I can think of.?
?Your sister went to the lake with the Peterson?s and I?ll be back in a
couple of hours, so you?re in charge, soldier.? She messed his hair up
as she said it.
?Aw, mom, cut it out.?
?A little touchy this morning are we??
?I just got a lot on my mind,? he said, going back to his bedroom.
***
An hour later, Jamie was making sweet music on his piano when the phone
rang.
?Hello.?
?Hey.? It was Matt. ?What are you doing??
?Playing the piano.?
?I didn?t know you played, you any good??
?Depends on who you ask. But, I think I rock.?
?Can I come over and listen? I promise I won?t bother you.?
?Sure, come on over. The door is open.?
?I?m there.?
Jamie returned to the second verse of ?Benny and the Jets?. A couple of
minutes later, Matt quietly opened the door and slipped into the den
where the music was coming from. Jamie didn?t notice Matt slip into the
room and when he applauded after his big finish, it surprised Jamie and
he got a little embarrassed. ?I didn?t hear you come in. How long have
you been here??
?Just a minute or so. You?re pretty good.?
?I like to play, it helps me unwind and stuff.?
?That?s how I feel about gymnastics. I get out there and there?s only
one thing on my mind, my routine. All the other bull shit gets tuned
out for a few minutes and my mind is just concentrating on one thing,
stick the next landing, you know??
?Exactly, the same with the piano, I?m only thinking about that next
chord.?
?Where is everybody??
?My mom?s shopping and Patty went to the lake with the neighbors.?
?When?s your mom going to be back??
?Bout half an hour.?
?I think it?s going to rain, not a good day to go to the lake.?
?Just what I was thinking.?
?Play another song.?
In the middle of his third song, his mom walked in carrying two bags of
groceries. Hearing Jamie playing made her smile. When a strange voice
started belting out the lyrics, she had to take a look and see what was
going on.
She set the bags down and peeked around the door jam to see Jamie
standing up and banging on the keys, while Matt was strutting around
like Mick Jagger with some rolled up sheet music for a microphone. Matt
knew most of the words and tried to make up the rest which only made
the whole scene that much sillier. When Jamie hit the last note, his
mom jumped into the room and started cheering like a teenage fangirl.
This embarrassed both boys to no end. She started laughing and said,
?You boys are lucky I didn?t have a camera. That was some kind of
entertainment. I?m just not sure what kind.? I think I?m beginning to
see where Jamie got his sense of humor. The boys didn?t think it was
that funny and went outside when she laughed all the way to the
kitchen.
***
?Your mom is funny,? Matt said, his smile returning to his face after
the embarrassment faded.
?She has her moments.?
?What do you want to do now??
?I don?t know, what about you??
?Nobodies home at my place.?
?How come??
?My parents are working and Carrie took Itsy back to the old
neighborhood.?
?What are they doing back there??
?Carrie went to see her boyfriend and a couple of Itsy?s friends wanted
to celebrate her birthday and they?re going to a pizza party, I think
that?s what they said. I really wasn?t listening.?
?Okay, let?s go.?
As they walked across the street, Matt looked around and seeing that
nobody was looking their way, reached down and took Jamie?s hand. It
startled Jamie and he looked around to see if anyone saw them, but he
didn?t let go.
They played video games for an hour, they were both competitive and it
made their play more intense. Because of his athletic ability, Matt
reactions were just a microsecond faster, giving him the advantage.
But, Jamie, the survivor, using his wits made it close until Matt
pulled it out at the end. Now that they were alone, Matt continued his
handy work from the night before and took every opportunity to place
his hands on Jamie. They were sitting next to each other on the couch,
the intensity of the game had them pressing their thighs against each
other, but Jamie didn?t realize it until the game was over. When he
did, he placed his hand on Matt?s thigh and asked him if he had
anything to drink and that he had to pee.
As he was closing the door, he heard Matt yell, ?You want some popcorn
too??
?Yeah, sounds good,? Jamie hollered back and closed the door.
***
Alone in the bathroom Jamie started thinking, he knew Matt was going to
try and get romantic, in fact, he was kind of surprised he hadn?t
already. He was really liking the time he was spending with Matt, in
just a couple of days he felt closer to Matt than any of his other
acquaintances. He decided to play it by ear and see what happens. If it
turns out not to be his thing, then that?s the way it is, but if you
don?t stop and smell the roses, you?ll never get a prick. I know,
that?s not how it goes, but you get the point, no pun intended.
Jamie returned to the living room and channel surfed until he found an
old Woody Allen movie that he had not seen before called ?The Curse of
the Jade Scorpion?. It was about an insurance scam and, oh never mind,
it has nothing to do with this story.
Matt brought in a bowl of popcorn and a couple of drinks, Jamie took a
sip his and jerked back, ?Eh, what?s in this?? For the most part, Jamie
didn?t think much of alcohol, he saw how it affected his mom and so he
wasn?t a proponent of drinking.
Matt looked at him innocently, ?What, oh, just a little vodka. Haven?t
you ever drank alcohol either??
?I?ve drank beer before, but never any hard stuff.?
?It?s basically the same thing, only you don?t have to drink as much to
feel good.?
?It tastes pretty strong.?
?Just sip it, it will be okay. What are you watching??
Matt sat down next to Jamie and thought, man, this guy is a virgin, he
doesn?t drink, his mom didn?t seem to be too strict, in fact, she was
kind of cool. He seems to have all the confidence in the world, I
wonder what?s wrong with him. Or maybe it was like he had thought and
somewhere in there is a different person that needs a little help to
get out. He remembered when he first met Frankie at summer camp and how
he was different too. The difference was Frankie, who was older than
Matt, had come to terms with his true self and it was a girl. Even
though he keeps it hidden from everyone else, he confessed his desires
to Matt and they played the role of boyfriend and girlfriend whenever
they could find some time alone. Matt came back from his reverie more
determined to find out if Jamie was hiding something.
Jamie started to feel a little buzz from the vodka, he wasn't
accustomed to the effect and it made him somewhat fuzzy. Out of the
blue, probably because of the booze, Jamie told Matt that he had a
dream about him. They both got a laugh at Jamie?s description, but Matt
stopped laughing when Jamie told him about the wedding dress. It only
reinforced his opinion of Jamie. He had an idea, got up, and said he
would be right back. He returned with a couple of magazines, handed
them to Jamie, and told him to take a look.
One was called, ?Transformation? and the other ?She-Males?. Jamie
started looking through the magazines and could not believe that the
girls on the cover were really men. Given his interest in women?s
fashion, when he saw the pictures of the girls in various stages of
dress inside, he wasn?t shocked, it only made him curious. Of course,
he had heard of transvestites, but what really surprised him was that,
after looking through the want ads, there were apparently a whole lot
more of them than he thought.
After giving the magazines a thorough look-see, he looked at Matt whose
normal grin was much more obvious, ?What do think of that?? He asked
Jamie.
?Is this what you want me to do??
?Well, I was thinking, ahem, you know, maybe.? As he said it he reached
over and squeezed Jamie?s shoulder.
The alcohol was making Jamie giddy, he teased Matt, ?You want me to
dress up like a little girl and then what? You going to be my daddy??
But he didn?t think his answer was so funny, ?Something like that.?
?Oh, I don?t know,? all serious now, ?what if somebody comes home?? It
was the best excuse he could come with on the spur of the moment.
?No one will be home before six,? Matt said, thinking that Jamie was
starting to not hate the idea. He noticed that his glass was empty,
another drink might be all it takes, he was thinking. It was only a
quarter to one, they had plenty of time to see where this would go.
?Another drink??
?Sure, only not so strong, okay??
?All right, you just think about it, my sister has a closet full of
sexy clothes. If you want to take a look, go ahead while I do this.?
Jamie was thinking about the models in the Sear?s Catalog and how much
he envied them for getting to wear all those stylish clothes. His
curiosity was getting the best of him and he wandered into Carrie?s
bedroom. The sliding door of the closet was open and it pulled at him
like a magnet.
Matt came back into the living room and saw that Jamie wasn?t there,
His smile got a little bigger, he sat the drinks on the coffee table,
and walked back to Carrie?s room. He stood at the doorway and watched
Jamie look through Carrie?s clothes. Jamie got the feeling he was being
watched and turned to see Matt smiling at him.
?See anything you like?? He asked.
Jamie?s cheeks turned red and started to walk away.
?I know you want to,? he continued. ?Why don?t you just admit it??
?That?s easy for you to say, you?re not the one being asked to change
their lifestyle.?
?I?m just trying to get you to open up and try something new, what
could it hurt??
?It just seems wrong.?
?I don?t think there is anything wrong with it and all those people in
those magazines don?t think it?s wrong. Pick out something and try it
on, what?s the problem??
?I?m afraid I might like it. Then what do I do??
?You won?t know unless you try, right??
This was only going around in circles, the only way to stop it would be
to do as he asks. Jamie reluctantly submitted. He picked out a short
summer dress that was red with a flowery print and held it up for
Matt?s approval. Matt said yes, then opened one of the dresser drawers
and pulled out a pair of pink panties. He handed them to Jamie. Jamie
was feeling self-conscience and asked him for some privacy. Matt closed
the door and went back to the living room.
***
Jamie laid the dress on the bed and stared at it while he sat down next
to it. He held up the panties and looked at them for a few seconds. It
was amazing how calm he seemed to be. His mind was completely blank.
Maybe it was the alcohol, maybe it was the calm before the storm. He
just sat there not moving.
There was a knock at the door. ?Come in,? he said.
Matt stuck his head in, ?You want your drink? Hey, want?s the matter,
you okay??
?I think so, maybe it?s the vodka, I feel kind of strange.?
Matt set the drink on the nightstand and pulled Jamie up off the bed
and hugged him, Jamie kind of melted into his arms and hugged him back.
He felt that same feeling as the day before when he was in Matt?s
embrace.
Matt said, ?If you're scared I?ll hold your hand.?
This cracked them both up.
?Just give me a few minutes to gather myself, I?ve never done this
before, you know??
?I?m excited to see how you look, I know you?ll be a knockout.?
?Then get out of here and let me do it, then see if you still want to
hold my hand.?
?Okay, I?ll be right out here, holler if you need any help,? Matt said
as he left the room and closed the door.
Jamie sat back down, he was thinking about being in Matt?s arms again.
Then he remembered the shemales in the magazines and how happy they
appeared to be. The alcohol was making him think about his life.
Although he was popular there was no one he was close to and it did
leave a hole that needed to be filled. He was thinking he was like the
clown that?s laughing on the outside to fill the empty space on the
inside. That internal dialogue went on for a few minutes and he finally
said, ?What the hell.?
He was only wearing shorts, a t-shirt, and flip flops and was naked in
a flash. He took a big drink and picked up the panties. As he slid them
up his legs, he knew something was different. The nylon material was so
soft and cool and when he stood to pull them on, his little dick
started to get hard. He had masturbated dozens of times, so having a
hard-on was nothing new, but the effect the panties had was something
new. He couldn?t explain it, but it was making him excited. He slipped
into the dress and looked in the mirror.
He liked the way the dress fit and how it moved when he did, but the
image in the mirror didn?t look very girly. He got an idea an went to
Carrie?s vanity, opened the top drawer and there was all of her make
up. Jamie had watched his mom put on hers and tried to copy what he
remembered.
He put some mascara on his lashes, they were already fairly long and
two coats made his green eyes look bigger. He put some reddish lipstick
on but had to wipe it off and do it over again. This time he got it
right and he was glad to see how that little bit gave him a more
feminine appearance. He had taken a few more sips from his drink and
was starting to get silly. When he sprayed on some of her perfume, he
got lost in the flowery mist and started to dance around the room
lightly. His acting classes kicked in and he started to take on the
character of a girl. He was about to go show Matt when he got another
idea. He went back to Carrie?s dresser and started opening drawers
until he found the one he was looking for. It had all her lingerie,
neatly folded. Jamie took out a couple of items, then found a pink
transparent chemise.
Matt yelled from the living room, ?Everything okay in there??
?Yeah, almost ready.? Now Jamie was getting excited about showing Matt
and about what might happen.
After a couple of more alterations, he stood in front of the mirror and
was a lot more pleased with the reflection. He had found a pair of
pantyhose, but her shoes were too small. Probably because of his size
he hadn?t grown much body hair, he had a little under his arms and in
the pubic area. The hair on his arms and legs was short, white, and
almost invisible, so in the chemise, he looked like a young teenage
girl. When he pulled the pantyhose up his legs, the feeling was
intense, like nothing he had felt before and his chubby got hard again.
He tucked it between his thighs and pulled the panties and pantyhose
tight to keep it in place. He combed his hair into something like a
pixie cut, finished the drink, took a deep breath, and opened the door.
***
As he walked down the hallway he could feel the nylon chemise rubbing
against his body and it was delicious. He more or less danced into the
living room. When Matt turned to look at him, Jamie said, ?Oh, Matthew,
darling, would you be a dear and pour me another drink??
It wasn?t that hot, but the clouds made it humid, and Matt had removed
his t-shirt. Seeing his muscular upper body reminded Jamie of the dream
and he felt a little twinge of desire and a stirring in his pink
panties.
Matt liked what he was hearing. Jamie was starting to get into the role
and seemed to be enjoying it. He sat down on the couch and crossed his
legs like he had seen his mother do. Matt was back in a flash with the
drink. Jamie said, ?Thank you,? smiled and batted his mascara
lengthened eyelashes.
?Wow, you put on some make-up too. You look really cute, I knew you
would.?
Matt had one more trick up his sleeve. He had brought out his laptop
and had it sitting on the coffee table. He was pretty sure of the
answer but asked Jamie anyhow, ?Do you ever watch porn??
?Nope? Do you have some?? Matt could tell by his voice that Jamie was
getting kind of drunk, his plan was proceeding as he intended.
?Right here on the internet,? and logged onto some porn site. Once he
got it going, he turned to Jamie and said, ?Stand up and let me get a
good look at you.?
He did as asked, threw in a couple of turns and a curtsy, then returned
to the couch.
?You look nice, that?s not what you were going to wear.?
?Nope, I thought this looked sexier and I wanted you to like the way I
looked.?
?I do, babe, I really do.? As he said it, he put his arm around his
shoulder and pulled him closer.
He called me babe, he said to himself with a sense of pride and scooted
over to make it easier for Matt. The movie started, surprise, it was a
shemale movie. Jamie smiled to himself, put his hands together in
prayer formation, laid them on Matt?s bare chest, then placed his cheek
on them, like a pillow. This will be interesting, he thought.
The touch of Jamie?s hands on his chest and feeling him curled up
against his side made Matt?s cock start to stiffen and he had to
rearrange his shorts.
Jamie was expecting Matt to make some kind of a move and when he hadn?t
about ten minutes into the movie, it got pushed to the back of his
thoughts. With that not on his mind, he started to get into the movie.
***
Matt had chosen just the right movie. It was about a teenage boy the
resembled Jamie in size and body type. He went to school by day as a
boy, but by night he would dress as a girl and go out searching for
men.
In the opening scene, the boy, a cute Latin teenager, comes home, lays
his books on the table and proceeds to transform into a cute young
girl. The scene is not rushed and shows how much pleasure the lad has
during the process. It?s actually sweet to see him start out as a sad,
lonely young man and change into a smiling, happy young lady on the
prowl.
Jamie started to understand why he liked the Sear?s Catalogs so much.
And maybe, just maybe, this was the cream filling he was looking for
to fill that emptiness he was feeling. He started to identify with our
hero and told himself that he was just as cute as the boy in the movie
and wondered if he would look that good with the right make-up and
everything else.
He wasn?t sure if that was it, but being curled up next to Matt, who
had his arm around him and drawing little circles on his bare shoulder,
with his head laying on Matt?s bare chest, the way he smelled, feeling
his heartbeat start to rise, and seeing that the bulge in Matt?s shorts
that was starting to get him excited, felt really good. It didn?t feel
weird or awkward. If the two boys were cats, you would be able to hear
them purr. If anybody walked in on them, they would have thought they
were an average teenage couple watching a movie.
***
The boy in the movie got picked up by an older guy, who took him to an
empty parking lot. He got out, opened the door for him, the shemale got
out and the guy kissed her before opening the backdoor, and they both
climbed into the back. In the backseat, the young shemale started
kissing the man and at the same time rubbed the bulge in his pants. The
man pulled back, unbuckled his belt, unzipped his pants and pulled them
down to his knees. The tranny grabbed his hardening cock, opened her
mouth, and engulfed it enthusiastically. As she bobbed her head up and
down, making all kinds of slurping sounds, Matt reached down and
started to massage his own hardening cock.
Jamie, too, was starting to feel the heat the movie was generating and
his little dick was hard and tenting his pink panties. He tried to hide
it, but Matt pushed his hand away and said, ?It?s okay, it?s natural,
don?t be embarrassed,? then he started playing with Jamie?s little
dick.
Jamie froze when Matt touched his dick. It was the first time, in his
memory that another person touched him there. Sensing his hesitation
Matt reached down with his free hand and lifted his face up to his lips
and kissed him. This time Jamie was ready and accepted his tongue when
it pushed past his lips.
The movie, the booze, the atmosphere, the chemise, the panties, and now
Matt?s kisses had Jamie in a fog of pent up sexual tension that he had
kept hidden in his subconscious for so long. Jamie let himself go and
his emotions flowed out of him like a dam busting. He started
returning Matt?s kisses with a passion he had never experienced before.
He hopped up on Matt?s lap and straddled him, throwing his arms around
Matt?s neck and kissed him hard, with feeling while running his hands
through Matt?s dark blonde hair. Matt was taken aback at first, he
thought, what have I unleashed. But that only lasted a few seconds and
he returned the kisses with equal passion.
He took Jamie?s hand and moved it down to his cock that was straining
to break free. Jamie squeezed the shaft and was surprised that it was
bigger than he thought. Taking a hint from the movie, Jamie stood up
and helped Matt pull his shorts off. His cock was twice the size of
Jamie?s and he was kind of mesmerized by the sight of it.
Matt said, ?Go on, it?s okay, touch it.?
Jamie put his fingers to his mouth, like he was thinking, and had a
real innocent look on his face. Matt nudged him, he looked at Matt,
smiled, then took his cock in hand. His cock felt warm to his touch,
the skin was soft and smooth, he liked the way it felt in his hand. He
started to stroke it up and down. Matt threw his head back and said,
?Yeah, Jamie, that?s what I?m talking about.?
Jamie laughed nervously, kind of lightheaded, happy that he was making
Matt feel good. He didn?t know why but he felt it important that he
satisfy Matt?s desire. It was like this muscular teenage stud had him
under a spell or something and his only thoughts were of how to please
Matt. It wasn?t how he normally thought or acted, but it didn?t feel
like it was something immoral, unnatural, or wicked. He was having
actually having a good time and by his reactions, so was Matt.
Matt stopped Jamie?s stroking and said, ?Spit on it, it works better if
there is some lubrication. Otherwise, you?ll pull all the skin off.?
Jamie tried to imagine Matt?s cock without any skin and said, ?Eew.?
?Yeah, so try to keep it moist.?
?Do you have any lube??
?Yeah, I do, but I don?t like to use it too much.?
?Why not??
?It doesn?t taste all that great.?
?Why would you taste it??
?When you put it in your mouth, it tastes like shit.?
?But, why would you eat it in the first place??
?No, you don?t get it. If you put it on my cock now, it would work well
with what you are doing. But, when you start putting it in your mouth,
you can?t help but taste it. Understand??
?Do I have to put it in my mouth??
?That?s step two, you are doing step one now.?
?Wait, there are rules??
?No, there are no rules. Well, but, I guess it?s more like one thing
leads to another. Didn?t you take sex ed in school??
?Yeah, but I never learned about the proper way to handle a cock, they
never said anything about steps. They just told us the basics, you
know, you stick your thing in her thing and you make babies.?
?Let me tell you, Jamie, there?s a whole lot more to it than that and
when you learn how it?s just about the most fun two people can have
together, it doesn?t matter what sex they are. You can take that as a
fact from me.?
?You?ve had a lot of experience??
?I?ve had my share and I ain?t no virgin.? He knew the minute it left
his lips that it was not the right thing to say.
?It?s not my fault, I can?t help who or what I am, can I? Besides, it
takes two to have sex and there doesn?t seem to be a girl in this city
that thinks of me in that way.? Jamie?s feelings were hurt and he
cursed his lot in life. He scooted over on the couch and turned away
from Matt.
?I?m so sorry, Jamie. I didn?t mean it that way. It?s just that you?re
the first person I?ve met in high school that hasn?t had sex. Really
I?m not all that experienced. Truth is, I?ve only been with one girl
and two guys. Two were just one night stands and the other was with a
boy, the one I told you about, he taught me everything I know. I?m sure
there?s a lot more I need to learn. Like keeping my big mouth shut
about things I don?t understand. Can you forgive me??
He reached out for Jamie and pulled him back his way. Jamie resisted,
he pulled again and said, ?Forgive me, babe, I swear I?ll try to be
more patient and understanding. I really like you and I think we could
have a good thing going on, give me another chance, please, Jamie??
This time when he pulled, Jamie fell back into his arms. Matt engulfed
him and started kissing the back of his neck which gave Jamie
goosebumps, but it felt so good, he didn?t want him to stop. If I had
known what I was missing, Jamie thought, I wouldn?t have been so
cavalier about sex.
Matt did a reach around and started playing with Jamie?s little dick
and made it hard. Jamie was leaning back into Matt, moaning how good it
felt. Matt kept kissing his neck, working his way to Jamie?s ear. While
pinching his little rosebud nipples, which made Jamie flinch, he
whispered about how good his body felt wrapped in lingerie.
Jamie raised his shoulder to his cheek, just like girls do when they
want you to stop doing something. He turned to Matt and said, ?I know
how we can solve our problem.?
?Problem??
?Me, the virgin, remember??
?Oh hey, don?t even worry...?
?Will you shut up and listen??
?Okay, okay.?
Jamie gets his smile on and says, ?It?s simple, pop my cherry, as they
say. Then I won?t be a virgin anymore. Easy, peasy, see,? then put his
arms around the teen's neck and gives him a quick kiss, keeps his arms
around Matt?s neck, and looks him in the eye to see his reaction.
Matt didn?t say anything for three minutes and twenty-two seconds, at
least that?s how long it seemed to Jamie. That smile started to get
even bigger, he turned and looked at the clock, it was only two thirty,
plenty of time.
?Let me see if I understand what you?re trying to tell me,? he said
feigning stupidity. ?If I do to you what that guy on the screen is
doing to that girl all our problems will be solved??
Jamie turned to the laptop and saw a guy with a huge cock hammering the
young shemale's ass like he would beat a mule. Jamie felt his ass hole
clinch up and said, ?Oh fuck, doesn?t that hurt? That?s got to hurt,
look at her face. Oh, my god. Maybe we need to rethink this idea.?
?It wasn?t my idea. Are you going to chicken out now, now that we?ve
gone this far?
Look at what you?re doing to me,? and grabs his semi-hard cock that was
leaking precum. ?And look at you,? and points to Jamie?s panties that
were spotted with his own precum and being brought to an apex.
They both stood there looking at each other, saying nothing, then they
both started laughing at the same time. Jamie put up both hands and
lightly hit Matt in the chest and they continued laughing as they both
fell onto the couch.
Their laughter died down and they grew quiet, their attention now on
the action which was hot and heavy. The shemale was now in a bar and
having sex with the bartender and one of the customers. They had her
laying over a bar stool with the guy in back fucking her bussy and the
other guy fucking her face. She sure looked like she was enjoying the
treatment she was getting, which is what got their attention.
Jamie was thinking, well, she doesn?t seem to be in any discomfort now.
In fact, she is even rocking back to meet his thrusts and how do you
suppose she can get that big ass cock that far down her throat. I
wonder if she is a circus performer on the side.
Matt was thinking, this is going to happen, this is going to happen,
this is going...
He was getting so excited, he had to pee. Jamie said that another drink
might help get things started and Matt agreed. This is going to happen.
When he returned with the drinks, Jamie was laying on the couch. He got
up, Matt sat down, and then he laid back down with his head in Matt?s
lap. Jamie was now watching two shemales giving each other a blow job
in the sixty-nine position. Matt asked him, ?You like that??
?Uh uh, can we do that??
?Anything you want, it?s up to you.?
?Okay, let?s see how this ends first.?
Jamie could see Matt?s cock getting hard and growing bigger. He placed
his hand over it and started to massage in gently. Matt reached down
and started teasing Jamie?s nipples through the chemise and with his
free hand, Jamie started stroking his own dick.
When both the shemales shot their loads on each other, Matt had Jamie
stand, he took off his shorts again and laid down on his back. Jamie
was watching his cock dance around as Matt arranged himself on the
couch. He couldn?t take his eyes off of Matt?s dripping erection. Matt
pulled Jamie?s panties off, said okay, and Jamie climbed on top of him.
Jamie used his finger to smear the sticky fluid around the crown of
Matt?s cock and
he groaned his pleasure. Jamie felt Matt?s lips wrap around his hard
dick and use his tongue to tease the tip. Following his lead, Jamie did
the same and tried his best to imitate what he saw the shemale in the
movie do. Matt?s cock was fat and Jamie could only get half of it his
mouth. The new drink had revived his alcohol buzz and he was
fantasizing that he was Matt?s steady and what that would be like. He
was thinking this ain?t so bad, I wonder if he would take me to the
prom.
The boys got into a rhythm, Matt had his hands on Jamie?s butt and
pounding it into his face, while Jamie was sucking on the half of
Matt?s cock in his mouth and stroking the bottom half with his hand.
Being his first experience, it wasn?t long before Jamie?s head started
spinning and all that built up tension exploded into Matt?s mouth and
he sucked and swallowed until Jamie went limp.
It took him a minute to recover and remember where he was, but when he
did he went after his job with new vigor. Now that he knew what the
reward was, he was determined to reward Matt too. When he started to
get close, Matt stood up, had Jamie kneel in front of him, and started
to beat his meat. Jamie watched with amusement as Matt made a variety
of faces before achieving his orgasm. Matt told him to open his mouth
and shot his load down Jamie?s throat. He gagged at first but managed
to swallow at least half of Matt?s cum. It didn?t have a distinct
taste, but he thought it made his tongue a little numb. He figured it
was all those wacky spermatozoa trying to fertilize it.
They laid there on the couch exhausted. Jamie was on cloud sixty-nine
and when they sat up and Matt told him how good of a lover he was he
didn?t think life could get any better. But he was still a virgin.
They sat on the couch, made some small talk, and finished their drinks.
Matt was still naked and Jamie was only wearing the chemise. It was
getting close to four and Matt was not yet through initiating Jamie. He
got up, picked Jamie up off the couch with hardly any effort. Being
held in Matt?s strong arms gave Jamie that feeling of being vulnerable
but safe right where he was again. Matt had turned from the somewhat
annoying pervert of yesterday into the cowboy in a white hat, riding
off into the sunset with Jamie in his arms.
He dropped Jamie on the bed, opened his bottom dresser drawer, moved
some things around and pulled out a bottle of KY Jelly and a box of
condoms. He turned and looked at Jamie with a shit eating grin that
caught him off guard and startled him, ?What?s that?? He asked him.
?Something to make your life a bit easier, you?ll see.?
?What do you want me to do? Should I get on my hands and knees like
that girl in the movie??
?Eventually.?
?What??
?Nothing, never mind. Lay on your back. I want to watch your face when
I take your cherry.?
Him saying it gave Jamie a little quiver of anticipation. He rolled
over on his back and started playing with his nipples like Matt had
done while he watched Matt put the condom on his newly recovered hard
on. He had never considered the male body as sensuous as the female
body, but watching naked Matt?s muscles ripple as he worked the condom
on and the cute dimples in his butt cheeks, was giving him a new
appreciation for them.
***
Matt lifted Jamie?s legs and placed them on his shoulders. He once
again flashed back to his summer romance with Frankie and was hoping
this summer would be just as sweet. He positioned himself and slowly
pushed the head of his cock into Jamie?s lubed up back door.
Jamie knew there was going to be some pain, Matt had walked him through
the experience. But, as his cock started to stretch the entrance, it
really hurt. Jamie looked up into Matt?s eyes and said, ?I?m scared,
Matt, will you hold my hand??
When he heard Jamie say that, it crushed him inside. It started out as
a joke but had now become their personal mantra and Jamie took a place
in Matt?s young heart. He looked into Jamie?s watering eyes and simply
said, ?Always,? and gently squeezed his extended hand. A few days ago,
when he first met Jamie, he thought he was cute, funny, and probably
gay. So he thought he would take a chance, maybe have a friend with
benefits in the neighborhood, that would be cool. But, Jamie was
turning out to be much more complex than the boys he was accustom to
hanging with. He couldn?t put his finger on it. Jamie gave the outward
appearance that, despite his size, he was full of confidence and in
control of his little world, but he was letting his guard down and Matt
was seeing that he was just as uncertain and apprehensive about life as
everybody else.
Once he was inside him, Matt paused to let Jamie?s expanded entrance
adjust to the invader. He started to rock back and forth slowly,
waiting to get some sign that the pain had changed to pleasure. The
lube helped a lot and after a couple of minutes Jamie was amazed over
how the pain changed to pleasure, it answered some of the questions he
had about the movie they had watched.
Jamie had his eyes closed, a little smile on his face, and was humping
back to meet Matt?s thrusts. Matt was watching Jamie?s face and saw a
look of total serenity. ?Do like this? Does it feel good?? He asked him
softly.
Jamie opened his eyes and saw Matt?s handsome face watching him. ?Oh,
yes, Matt. I had no idea it would feel this good,? he answered,
breathing heavy. Jamie stretched his arms out to Matt and he bent over
so he could put them around his neck. Jamie pulled Matt?s head down to
his lips and for the first time he pushed his tongue into Matt?s mouth
and did some exploring. He broke the kiss and said, ?You make me feel
amazing. I had no idea it could be like this,? he said still in rhythm
with Matt.
Matt?s thrusts got faster, his body tensed, and Jamie could feel his
cock twitch inside him. ?Ugh,? he groaned and collapsed. Jamie hugged
him and held him tight. He was wondering if this is how real girls felt
after they get fucked by their boyfriends. Boyfriends? Was he thinking
of Matt as a boyfriend? He said to himself, ?I could think of worse
things,? but doing this with Matt all summer was not one of them. Matt
rolled off of him and they laid quiet for a few minutes. The afterglow
and the feeling of guilty pleasure found them both at a loss for words.
Finally, Matt turned to him and asked, ?Do you feel any different??
?A little sore.?
?Is that all??
?How am I supposed to feel??
?I was just wondering if you feel any different, now that you?re not a
virgin anymore.?
?Oh, my god, you?re right. I forgot all about that. See what you do to
me.?
?Hey, babe, once you got going, you were like a wild animal. I was
worried I couldn?t keep up.?
?You?re just saying that.?
?No, seriously. If I didn?t know, I would swear this was not your first
time.?
?The movie helped a lot.?
?I hoped it would.?
Jamie was feeling like the Ying to Matt?s Yang and rolled over on top
of him. ?So, when can we do it again??
?Really? What have I created??
?Be careful what you wish for,? he said and gave him a long lingering
tender kiss.
All of Jamie?s fears and uncertainty about sex had been dashed that
afternoon and wearing Carrie?s lingerie was pretty exciting too. He was
still thinking of how he would look if he had all the accessories the
boy in the movie had.
?Matt,? Jamie said softly.
?What?? Matt responding like he suspected something was coming.
?Did the clothes make a difference??
Matt thought for a minute. ?I think so, you are a lot cuter in what you
are wearing than in what you were wearing.?
?Do you think I should dress like that more??
?I?d like it, but it?s up to you. Didn?t you like it? It seemed like
you liked it.?
?I did, I really did. But, I can?t wear Carrie?s stuff all the time,
can I??
?Probably not a good idea. Huh??
?My mom has a bag of clothes she going to give to Goodwill, I could go
through that.?
?Oh, you know what? You just reminded me, there?s a box of Carrie?s
things in the garage that she separated for the move. She doesn?t want
them anymore. We could look through that.?
Jamie found that idea exciting and couldn?t wait. The thought of
dressing like a fashionable young girl and being on Matt?s arm, walking
through the mall, and everybody stopping and watching the young couple
with smiles on their faces, just like a television commercial, thrilled
him.
?We should get things cleaned up. My sisters will be home pretty soon,?
Jamie was so comfortable cuddling with him and didn?t want it to end,
but he knew he was right. The worse thing that could happen would be to
get caught like this. The boys cleaned up their mess and were sitting
on the couch, playing a video game when the sisters got home. They
finished their game and Jamie said he better get going. Matt walked
with him to the sidewalk and said, ?I had a really good time with you
today. It?s funny, we just met a couple of days ago, but I feel like
I?ve known you all my life.?
?Yeah, I was kind of thinking the same thing. Kindred spirits, maybe.
You were an excellent teacher and took your time, never forcing me to
do anything I didn?t want to. That?s not how teenage boys are supposed
to act. They're supposed to be all hormones and grabby like you were
last night.?
Matt laughed, ?Hey, I told you I wasn?t usually like that. Today was
how I really am.?
?Well, I really like who you are and being with you today has been one
of the most memorable days I will probably ever have. I mean, how many
times can you lose your virginity??
?You?re so funny.?
?You make me happy.?
?So, babe, how are we going to work this out. I want to see a lot more
of you.?
?You saw me naked today, that?s all there is.?
Again he laughed, ?You know what I mean.?
?How should I know, I?ve never been in a relationship before.?
?We have a relationship? Are we going steady??
?Are you asking me??
?Ah, well, okay, yeah, do you want to go steady??
Jamie was just kidding and he wasn?t ready for Matt?s answer,
?Serious??
?Yes, of course. I don?t play about things like this. I want you to be
my girlfriend.?
?Oh, Matt, I?m really liking you, a lot, but going steady, your
girlfriend? This is all happening so fast. Would it be a problem if I
think about it, It?s not you, Matt, any girl would be proud to be your
girl. It?s my insecurities. The physical side of me is saying go for
it, but the logical side of me is saying slow down. Let me sleep on it
and I will tell you tomorrow, Is that okay with you??
?Only if you say yes. But, yeah, it?s about what you want too. In the
meantime, let?s get together and go through that box of Carrie?s things
in the morning.?
?Okay, that should be fun. I should get going, see if my mom needs
anything.? He smiled and said, ?If we weren?t in public I?d kiss you.?
?Come here,? Matt says and leads Jamie to a spot that couldn?t be seen
from the street. When they were standing, Jamie had to get on his
tiptoes so their lips could meet, but it was worth it and made him feel
small and girlish.
***
Jamie, who was starting to come down from the alcohol, but still had a
bit of a buzz, was feeling good. Matt was just what he needed at this
time. Matt brought out emotions and things he had never felt before and
he was liking it. He thought that it was nice to have somebody who
liked him for who he was and not for what he could do for them. He was
also thinking about looking through the box of Carrie?s clothes. Once
he got used to it, he felt quite at home in her lingerie and he loved
the way it felt when Matt would rub it against his skin.
He walked in and heard his sister complaining about her trip to the
lake. She said it was cloudy and windy all day, she had a terrible
time. At dinner his mom could see there was a difference in Jamie?s
demeanor, he was much more animated and teasing his sister about going
to the lake on a rainy day. It made her feel all warm and fuzzy inside,
the two glasses of wine before dinner might have helped too. She was
thinking that maybe a boy in the neighborhood his own age to hang
around with was just what he needed. She had no idea how right she was.
After dinner, he and his mom were in the living room watching
television. During one of the commercials, she asked him, ?So, what did
you and Mark do today? ?
?Matt, mom, his name is Matt.?
?Okay, what did you and Matt do today??
Jamie wondered what she would do if he told her the truth and just as
quickly put it out of his mind. ?Played video games and watched TV.?
Then he changed the subject. ?Their house is pretty nice, have you ever
been inside??
?Once, when your dad was alive, we went to a New Years Eve Party one
year, when the Sander?s lived there. That was before the Wilson?s moved
in. Hm, a long time ago.? Then she got quiet and Jamie could see she
was recalling a past memory. He loved his mom, if he could have one
wish in life it would be to have his father back, not so much for him,
although he did miss him terribly, it would be for his mom. He couldn?t
imagine how hard it has been on her, because she, like him, laughs to
hide the pain.
His sister came in and wanted to watch one of her shows. It didn?t take
him long to head upstairs to his room. He flopped down on his bed and
wondered what Matt was doing. He thought about calling him but changed
his mind. His butt was a bit sore and he couldn?t explain it, but he
got the itch to take a bubble bath.
***
Meanwhile, across the street and two doors down, this was taking place:
?Hey Matt, were you in my room today?? Carrie asked him.
?Hm, no, why?? He lied.
?Somethings seem out of place like someone was looking through my
drawers or something.?
?Did you ask Itsy??
?She was with me all day.?
?I don?t know what to tell you, it wasn?t me,? at least he didn?t lie
about going through her drawers. Damn it, he said to himself, Jamie?s
got to be more careful. If Carrie ever found out, the shit would hit
the fan.
Back in her room, Carrie was thinking, ?I know that little shit is
lying, he thinks he can fool me. I?ll show him.?
***
That night Jamie had another dream. He and Matt were huddled together
in the boat and once again floating through the haunted tunnel. Only
this time when the ride ended the boat changed into a car and they were
outside the school gym dressed in fancy clothes. Matt got out, wearing
a coat and tie, opened the door for him and said, ?You look beautiful
tonight.? Jamie got out of the car and when Matt closed the car door,
Jamie saw his reflection in the car window. He was wearing the light
blue mini dress that the boy in the movie had worn. He was in full
makeup, his hair was shoulder length, and he didn?t recognize himself
at first. When he did, that?s when he woke up.
***
Jamie woke up a couple of hours earlier than usual, the dream on his
mind. The thing about the dream was his reflection in the car window.
The face he saw was prettier than the boy in the movie and because of
his fair features and slim body, his overall impression was that he
looked far better as a girl than he ever had as a boy. Then again it
was a dream and more often than not images in dreams are distorted. So
it was kind of like eating one potato chip, he had to stick his hand
back in that bag and find out if he really looked that good when he was
awake. He wondered what Matt would say if he looked that good and made
up his mind to find out. He found that he was asking himself more and
more, ?I wonder what Matt would think if...?
***
His mom had to work and he was just pouring himself some cereal as she
was leaving. She grabbed her purse and said, ?I?ll be home around five,
keep an eye on your sister today, okay. Love you.?
?Huh, what, aw, mom...? But he was too late she was gone. He wasn?t
paying attention because he was thinking about the box of Carrie?s
clothes. When he realized what she had said, it was too late to try and
get out of it. Now, what was he going to do? He knew Matt was excited
too and he didn?t want to disappoint him. Little sisters, they mess up
everything.
***
Carrie was putting two and two together. She knew her clothes wouldn?t
fit Matt and she would have noticed if he was going through her stuff
before. He did say that the kid from across the street was here and
he?s just about the same size as she was. These facts did fit the case,
but they were circumstantial and she couldn?t say for sure. So she
devised a plan.
***
Jamie called Matt and told him the bad news, Matt took it in stride and
said, ?Don?t worry, babe, we got all summer.?
?But I?m starting to get excited about what?s in the box and I had
another dream that?s got me all confused and I need to get your input.?
?I gave you input yesterday, don?t tell me you?re horny again already.?
?No, silly. Not that kind of input. Besides, that was put in not
input.?
?It?s too early for this. I got to take a crap. I?ll call you later.?
?Hope everything comes out okay.?
?Oh, shut up.? Click.
Not a fan of humor in the mornings, I?ll have to remember that, he told
himself.
***
An hour later, Jamie was rocking out on the keyboard and Patty was
watching television in her room. The doorbell rang, it was Itsy. She
and Carrie were going to the mall to see a movie and they wanted Patty
to go. What a break, Jamie thought, the day is getting better.
He watched them get into Carrie?s car and as soon as they passed his
house, he picked up the bag with the bottle of wine he was sure his mom
wouldn?t miss, and he was out the door. He met Matt, who was thinking
the same thing, halfway. They didn?t say a word, just smiled at each
other and proceeded to the garage.
After his mom left for work, Jamie took a pair of his mom sexiest black
bikini panties and put them on under his shorts and they were doing
their best to keep him excited. As soon as they were in the garage,
with the door shut, Jamie showed Matt what he was wearing and told him
about the dream. Matt's eyes got big when he saw the panties. He was
kind of worried that Jamie wasn?t getting into the role, but the
panties and how stirred up he was about the box of clothes had him
rethinking that.
It was about eleven, the movies didn?t start until noon, so they
figured the girls would be back after two but before three, plenty of
time. Matt went to get some glasses and a corkscrew while Jamie started
looking through the box.
It was a large box, a good twenty-four inches deep and it contained a
treasure trove of feminine apparel. When Jamie opened it those youthful
days of perusing the Sear?s Catalog come flooding back, memories of
Christmas?s years ago, of Christmas?s with his father and it brought
tears to his eyes.
Is this what it was, was missing his father was the reason he had an
unfulfilled hole in his soul? Or was it the new person that he seemed
to have suppressed for so long and was only now coming up for air? Or
was it a combination of the two? He couldn?t do anything about his dad,
but he was on the verge of finding out about the second part.
When Matt returned, Jamie was separating the clothes by type. There
were stacks of dresses, tops, skirts, some leggings, a couple of bras,
and a pair of black, open-toed pumps with three-inch heels.
Jamie was beside himself in the midst of all the feminine attire. Matt
was happy to see him acting like this, it made him confident that he
had read Jamie the right way.
?See anything you like?? He asked Jamie.
?Yeah, I like it all, especially the shoes, they fit perfect.?
?Pick out something to put on, we don?t have all day, remember??
?Okay, what do like, this dress or a skirt and top??
?The dress.?
?What about a bra??
?Will it fit??
?I think so, but I?ll have to put something in them.?
?I?ve heard that some girls use tissue paper.?
?I?ve heard that too. We?ll see.?
?I?ve got the pantyhose you wore yesterday in my room.?
?Perfect,? said Jamie. He picked up the dress, the bra, the shoes, and
followed Matt to his room.
***
Matt sat on his bed and watched Jamie change. Jamie had forgotten about
being shy in front of him and was lost in his own little world as he
slid the pantyhose up his legs. He pulled the dress on over his head
and slipped on the shoes. It surprised him how easily they went on over
the pantyhose. When he stood to show Matt how he looked, the three-inch
heels come into play and he almost tripped, but Matt caught him before
he hit the floor.
?Whoa, easy, babe, you don?t want to break your leg.?
?They?re going to take some getting used to.?
Matt was enjoying Jamie?s discovering of the pitfalls that girls to go
through. Jamie took the shoes off, went to the bathroom and came out
with a nice pair of B cups pointing out beneath the dress. Remembering
his dream, Jamie wanted to put on makeup and find out if he really did
look as good as he did in the dream. He went to Carrie?s room and Matt
followed. Jamie did his best, but it was far from what he desired. He
did look more feminine, but in a drag queen way, with too much makeup.
It didn?t bother Matt, he knew it was a process and Jamie was still at
the crawling stage. He would get better in time.
They went back to Matt?s room and Jamie put the shoes back on and,
taking his time, stood up and did a spin for Matt. With a noticeable
difference, the shoes pushed his rear up and out, and the stuffed bra
giving him the appearance of a bosom, he looked more like a girl than
yesterday, and Matt?s little head started to get ideas.
The image in the mirror had Jamie hypnotized, he turned this way and
that trying to see himself from all angles. Matt left to refresh their
drinks and Jamie flopped down on the bed. He was getting excited about
the whole thing that was going on and about to happen. But he wished
his hair was longer and that he knew how to put on makeup better. It?s
all about practicing and that was his problem, when and where would he
be able to practice?
Matt returned and sat down next to Jamie?s prone body. He started
massaging Jamie?s shoulders and kissing the back of his neck. Jamie
could feel the excitement start to build in his black panties. He
rolled over on his back and put his arms around Matt, pulling him close
so he could kiss his young lover.
For all the time it took Jamie to get dressed, it only took a couple of
minutes to get him undressed. He lay on the bed in only his black
panties and admired Matt?s body as he stripped off his clothes.
He walked over to the edge of the bed and stood there. Jamie got the
hint and reached out for his cock. He took it in his hand and noticed
how small his hand looked wrapped around Matt?s hard manhood as he
guided it into his hot, wet, mouth. Matt threw his head back and
moaned, ?Oh, yeah,? with pleasure when Jamie?s lips took his cock.
He tried to get as much of Matt?s cock down his throat as he could, but
he ended up gagging and coughing up a mouth full of spittle which
lathered Matt?s cock. He sucked on Matt?s all-day sucker until he was
about to blow his wad. Jamie could tell it was about to happen and
worked harder to get his just reward. But Matt pulled his head off of
his cock and said, ?Not yet, you?re not getting off that easy.?
?What? I was trying to get you off.?
Matt laughed, ?Always with the comeback, funny girl.?
?It just comes natural, what can I say??
?I?m not complaining, it?s one of the things I like about you.?
?Good,? Jamie said and kissed him.
The two laid on the bed making small talk for a while. Matt started
teasing Jamie about something and he, in turn, started to tickle him.
This lead to the boys rolling around on the bed, wrestling, tickling,
laughing, having a good old time as young lovers do.
***
Carrie met Denise and her sister Danielle in the food court at eleven
thirty as planned. She had called her last night and arranged for her
to take the girls to the movies while she took care of some other
business. Her plan was to give the boys just enough time to hang
themselves. Then she would pop in and catch them with their pants down,
so to speak. She left the girls with Denise and walked around the mall
for half an hour, figuring she would be home by twelve thirty and see
what they were up to.
She parked across the street and two doors down and silently approached
her house. Before she left, she had used scotch tape on the bottom of
the blinds to create a small space so that she would be able to see
into any room from outside.
As she tiptoed up to the house, she saw the side door to the garage was
open. So carefully she looked around the corner and seeing her old
clothes spread around confirmed what she was thinking.
She looked in the living room and the kitchen but didn?t see them. This
only left the bedrooms and her imagination started drawing pictures of
what she was about to discover and it made her laugh. She was grateful
they were not in her room and that only left one more room. Matt?s
bedroom.
***
She peeked through the blinds and though it was what she thought, it
still surprised her. Jamie was wearing one of her old dresses and was
doing a slow spin in front of Matt, who was sitting on the bed. Jamie
was a little wobbly in those shoes. Hey, those are my shoes. She had to
put her hand over her mouth to keep from laughing out loud and possibly
getting caught when Jamie was posing in front of the mirror. This was
too good. She wished she had a camera. Humorous as it was, she thought
Jamie didn?t look too bad as a girl, minus that hideous makeup.
Matt left the room, had they heard her? She followed him through the
house to the kitchen and watched him pour some wine in the glasses.
Those little shits are drinking too, their toast.
Back at the window, Jamie was laying on the bed and Matt was sitting by
his side massaging his shoulders. Jamie turned over and they kissed.
They were kissing, she couldn?t believe it. Does this mean my brother
is a, is a, is a what, gay, bi, try. This was a bit more confusing than
she thought. And what?s up with this Jamie kid. Is this all his doing?
At Itsy party, I thought he was cute, a bit on the fem side, but he
didn?t act like it at all. You can?t tell a book by its cover, I guess.
In the room, things were getting hot and heavy. Matt had removed all of
Jamie?s clothes except for a pair of black panties. She didn?t
recognize them. When her brother stood and stripped, she was kind of
awed by his hard body and just as hard cock. If he wasn?t my brother,
she thought.
She watched Jamie?s look of hunger and desire as he put her brother?s
cock in his mouth and proceeded to polish it. As things heated up in
the room, Carrie felt a little heat flaring up between her legs. She
couldn?t help herself, there in the open, but fenced in, backyard, she
had her hand in her panties and working her clit as no man could.
She was worried they had heard her as she brought herself to an orgasm
that buckled her knees and had to grab the window sill to keep from
falling to the ground.
She gathered her wits and peeked back into the room. The lovers were
just lying there, cuddling and talking. It reminded her of the
afterglow times she has with her boyfriend. It was sweet, they appeared
to really like each other. They started wrestling and laughing just
like they did and she felt guilty for spying on them. She?s seen it
before, she?s lived it before, they were in love. And she was happy for
her little brother. This is a new world and we are finding out that
there are a lot of colors between black and white. Where do I get off?
I wouldn?t want anybody telling me who I can or cannot love. Damn, what
am I going to do?
***
They collapsed on the bed out of breath from their wrestling and
laughing. Jamie was snuggled up next to Matt, with his arm across
Matt?s chest. They were quiet, Jamie dragged his arm across Matt?s
chest and pinched his nipple. Matt jumped and said, ?Hey.?
Jamie started playing with Matt?s hair and said, ?Matt.?
?Uh-hu.?
?Yes.?
?Yes??
?Yes, I?ll be your girl. Let?s go steady.?
?You?re serious??
?Yes, I?ve been thinking about it and this is what I want, this makes
me happy.?
?And you make me happy.?
They started kissing and then froze. There was a sound. Someone was
home.
Matt jumped up and pulling up his shorts, said, ?Stay here and don?t
make a sound.?
Jamie looked like a deer caught in the headlights, holding the
bedspread up to his chin, covering his nakedness, just shook his head,
yes.
***
Matt peeked around the corner, no one in the living room. He peeked
around the next one and saw Carrie pouring herself a glass of wine. She
looked up, ?Hi, Matt.?
?I thought you were at the movies.?
?I was but I started to feel shitty, you know, girl problems, Denise
was there with her sister and the girls wanted to stay so I came home.?
She took a sip of wine and said, ?What are you up to?? As if she didn?t
know.
?Oh, nothing much, just hanging out, you know. Do you have to go back
and get them?? He asked hopefully.
?No, Denise is giving them a ride.? She loved seeing him squirm.
?Yum, good wine. Where did you get it??
Matt stuttered she had caught him off guard. ?I don?t know. It?s not
mine. Maybe dad left it out.?
?Oh, I was just wondering, I thought Jamie might have brought it over.?
Matt was looking at the floor and hearing this his eyes slowly started
to rise. When they met hers, she was smiling. ?He?s in your bedroom,
right??
It felt like all the air had been sucked out of the room, he couldn?t
breathe, he couldn?t talk, he just kept making a noise that sounded
like, ?Ayedintayenow.?
?It?s okay, Matt, your secret?s safe with me.?
?When, how do you know??
?I had my suspicions and I just watched the show you and Jamie put on.
Hey, that Jamie is pretty cute. Looks like he or should I say she gives
good head.?
That stupid smile of Matt?s was gone. He looked so ashamed and
embarrassed, she felt sorry for him. He didn?t know what to do, he
couldn?t think of anything to say, he just stood there with tears
running down his cheeks. Carrie wrapped her arms around him and
reassured him, ?It?s okay, Matt, there?s nothing wrong. Don?t be
ashamed. I should be the one ashamed for spying on you.?
?Yeah, you should,? he managed through sniffles.
?Why don?t you go get Jamie and let?s talk about it. Tell him or her,
what should I call him, him or her??
?We haven?t talked about it.?
?Tell her to wear that dress, it looked better on her than it ever did
on me.?
***
Back in Matt?s room, Jamie was freaking out. He tried listening at the
door and could hear people talking but couldn?t make out what was being
said. He couldn?t get to the bathroom to get the makeup off and worried
about what his mom would say when she found out. He was thinking about
using his t-shirt to clean off his face when Matt came back into the
room.
He told Jamie what took place and he had a hard time believing him. ?I
swear, Jamie, she doesn?t have a problem with it. I tell you, I was
seeing myself being shipped off the military school.?
?She?s really cool with it, with us??
?She said the only thing she?s pissed about is you going through her
drawers and me lying about it. So, come on, she wants to talk to us and
she said to wear the dress. She said you looked really cute in it?
?Really??
?Really.?
***
They stepped into the hall and Jamie said, ?Matt.?
?Yeah??
?I?m kind of scared.?
?You want me to hold your hand??
?Please.?
***
Jamie was literally shaking sitting on the couch next to Matt, who was
still holding his hand. Carrie just watched them for a minute, somewhat
enjoying their discomfort. She took a sip of her wine and said, ?Okay,
so what?s going on here? And don?t try to bull shit me. At this moment
I could be your worst nightmare or I can be your friend. Wow, I just
realized, I have all the power here, don?t I?? She looked at the couple
and they shook their heads. ?Now don?t get me wrong, I?m not a mean
person, Matt, you know that. You know, if you guys would have been a
little more careful you could still be in Matt?s room doing whatever.
But, you can?t put the lube back in the tube, can you??
Her little riddle broke the tension a little. She saw a flicker of
Matt?s trademark smile start to return. She continued, ?Look, at first
I was annoyed because you guys were going through my drawers, hup, no,
little me finish. Then I got curious and I put this plan in motion this
morning because I wanted to see what was going on. I must confess that
at first, I thought it was kind of funny watching you two, but when I
saw how you two were so happy together, I felt a little guilty and
embarrassed for spying.?
The young couple sat on the couch not knowing where this was going, all
kinds of troubling thoughts going through their heads.
?Now, I don?t want to get anybody in trouble, I think it?s okay for you
two to live your lives however you want, okay. I know a lot of kids our
age are experimenting with alternative lifestyles and I have no
problems with it. In fact, I was thinking, I?d like to help. As long as
you promise to stay out of my drawers.?
Matt and Jamie laughed nervously, they were having a hard time
processing what they just heard.
?What do you say, Matt? Jamie??
?What do you mean by help?? Matt asked.
?Well, the first thing is to get that makeup off of Jamie and see how
he really looks and go from there, okay??
Jamie felt his cheeks turn red but got excited at the prospect.
Carrie stood up, walked over to the couch, reached out her hand, and
said, ?Come on, Jamie. Matt, why don?t you go out and clean up that
mess in the garage while us girls have a moment.?
***
After removing all the makeup that he had applied, Jamie sat down in
front of Carrie, who went to work. She said she would show him how to
do this on his own later, right now she just wanted to show him what?s
possible. While she worked on him, he told her about the whirlwind the
past couple of days had been. Even though this was all still sinking
in, Jamie?s recollections had Carrie laughing. Carrie, who didn?t
really know Jamie very well, was starting to like what she did know.
Carrie put the cap back on the lipstick, sprayed a puff of perfume on
his neck, and said, ?There, you look so cute, I wish there was
something I could do about your hair. Oh, wait. Don?t move, I don?t
want you to see how you look until I get back. I?m not kidding, okay??
?Okay,? Jamie replied, but he was so excited it was hard for him to do.
A couple of minutes later, Carrie came back with a box. She opened the
box and pulled out a brown shoulder-length wig. Jamie?s eyes got big.
?This is one of my mom?s, from her beauty shop, let me put it on.?
?There, now let's take a look. Oh my, you are beautiful. The wig makes
all the difference. I think Matt will be pleased. Take a look.?
Jamie walked over to the full-length mirror. He couldn?t believe that
was the same person he saw in the mirror this morning. He did look
beautiful. He looked like the reflection in his dream last night and he
felt a stirring in panties.
?So, what do you think??
Jamie turned to her, his eyes all glassy, and simply said, ?Thank you.?
***
Carrie made Matt close his eyes, then motioned Jamie to come into the
room and had him stand in front of Matt. She told him to open his eyes
and the smile on his face brightened up the room.
?Wow,? he managed, ?you look amazing.?
?Yes, she does.?
He stepped forward and took Jamie in his arms, Jamie looked up into his
face and they tenderly kissed. Carrie watched and felt good about the
role she was playing, to help these kids.
?Okay, okay, that?s enough of that for now. There will be plenty of
time for that later. We still have some things to work out. Take a
seat.?
They returned to the couch, sat down, Jamie moved in close to Matt, who
put his arm around her, and they waited for her to continue.
?Besides trying to satisfy your teenage desires, have you given any
thought about what you?re going to do??
?About what?? Matt asked.
?Oh, let?s see, how about our parents? Jamie?s mom? What are you going
to tell them??
?I guess we didn?t think about it.?
?Well, maybe you should. I don?t think they are going to be thrilled
that their son is dating the boy from across the street. And what about
your mom, Jamie??
?I don?t know, I would hope that she would be understanding. But, I
don?t know.?
?Look, Jamie, I know this is different for you, you just lost your
virginity yesterday for Christ?s sake, I know how that feels, it?s
special and will be for all times. So, Matt here is your first
boyfriend, first love, maybe and it could be special. But it could also
be just a thing you?re going through and in a couple of months, you
won?t feel the same way. You need to be sure because there could be
some rough times ahead. The world is changing but there are still a lot
of ignorant people out there. Did you ever think of that??
They both shook their heads, no.
?I?m not trying to be the bad guy. I?m just trying to make you see the
reality here. It may seem like a fairy tale now, but they don?t always
have a happy ending. Understand??
?So, what are we supposed to do?? Asked Matt.
?If you keep on doing like your doing, somebody else is going to find
out. You have to know it would only be a matter of time.?
?Possibly.?
?No, probably. So, I?ve been thinking, you know Justin, right??
?Your boyfriend??
?Yeah, he lives about two miles from here and he is pretty cool. I
think I could talk him into letting you use his place a couple of times
a week. I?ll take that box of clothes and add a couple of more things I
think will look good on Jamie and leave them at his place. I?m sure
I?ll have to make some concessions, but I?m all about love and if
that?s how you feel, I?m here to support you. What do think, any
questions??
They both knew that she was right. They were so wrapped up in what was
going on between them, that they hadn?t considered the consequences.
?You should start to get changed, the girls will probably be back
pretty soon. You both have a lot to think about. So, talk it over and
let me know what you decide, okay??
They both agreed to do as she asked and returned to Matt?s room so
Jamie could clean up and get back into his boy mode. They agreed to get
together later that night and talk about what they were going to do.
***
Jamie was sitting in his room, when his mom knocked on the door and
stuck her head in, ?Everything okay, you?re kind of quiet.?
?Yeah, just got some things on my mind.?
Hm, I wondered what?s going on with him, she said to herself. ?Well, if
you need to talk about it, I?m always here.?
?I?ll be alright, just one of those things.?
?I worry when I see you like this.?
?Don?t worry, mom.?
?I?m your mother, it?s my job.? That brought a smile to his face. ?Wash
your hands, dinner?s almost ready.?
?I?ll be down in a minute.?
I wonder what she would say if I told her what was going on, he
thought. Would she understand? Could she understand? Was he really in
love with Matt like his mom loved his dad? Was Carrie right and there
would be rough times? Was Matt really serious or am I just a plaything?
And what?s in it for Carrie? All these questions and more were tumbling
around in his head.
***
Across the street and two doors down, Matt was making some hard
decisions. He had tried girls and other boys and he had no complaints,
but it was the small feminine looking boys, especially when dressed up
like a star, that really did it for him. Seeing Jamie after Carrie did
his makeup, changed everything for him. He had to admit that he liked
Jamie a lot, they meshed together well. That he pushed Jamie into this
just to see how far he would go and maybe get a little sex out of it
too. That Jamie looked okay in Carrie?s dress yet still just a boy in a
dress. But when he opened his eyes after Carrie?s work, it was a
completely different person standing in front of him. Jamie was like
Cinderella after her Fairy Godmother had done her magic. Just the
thought of it now made his heart soar. He was hooked. He couldn?t get
that vision out of his mind.
***
After dinner, Carrie drove over to Justin?s apartment. She was wearing
a pair of white short shorts and no panties that offered just a hint of
a camel toe, a navy tube top that was only about six inches wide, and a
pair dark blue sandals with four inches heels. She was showing a lot of
skin and hoped it would help in talking Justin into agreeing to her
plan for Matt and Jamie.
Justin was spread out on the sofa with a beer in one hand and a joint
in the other. He wasn?t aware that Carrie was coming over, when she
walked in, he about shit, he thought it was his landlord because he was
behind on the rent.
?Jesus, Carrie, you damn near gave me a heart attack, I thought you
were the landlord.?
?Why??
?I still owe this months rent and he?s been hounding me.?
A light bulb went on in Carrie?s mind. ?You having money problems??
He handed her the joint. ?Yeah, remember when I got that speeding
ticket a couple of months ago??
?I thought that was all settled.?
?I wish, you know what they do? When you go to court to pay for the
ticket, they tack on two-thirds of the fine as a court fee. So, the
three hundred dollar ticket cost me five hundred. And they don?t tell
you about it until you get there. It?s all fucked up. What a racket.
And that?s why I?m short this month. Hey, but you didn?t come over to
hear my problems, did you? Yeah, you?re getting the itch, huh??
?Oh stop. I need to talk to you about something.? She handed the joint
back to him.
?You didn?t come over to see ?Little J?, it looks like you?re dressed
for it.?
?Keep him in your pants for now. Got any more beer??
Carrie was seventeen going on twenty-five. Justin was twenty-one, her
folks think he?s eighteen and lives with his parents. She sat in
Justin?s lap and fed him the remaining french fries left from his take
out dinner. After which she would hold the clipped joint up to his
lips. All the while moving her hips, so his cock was right between her
legs, and getting aroused. She was fattening him up for the slaughter.
He pulled her tube top done and was sucking on her nipples and playing
with the camel toe in her shorts. She was rubbing his hard cock through
the baggy cotton shorts he was wearing and moaning. Attracted by
Carrie?s moaning, Justin?s lab, DeOhGe, came in from the bedroom,
looked around, and went back to the bedroom.
A few minutes later, Carrie was on her knees, between Justin?s legs,
with his cock in her mouth. She bobbed and slobbered, giving it
everything she had, wanting to get him to that point. She felt him
start to tense up and stopped.
?Oh, why did you stop? I was just about there.?
?I know, but first I have a favor to ask.?
In the condition, he was in and when she pointed out that he would be
able to make a few extra dollars subletting his place to the kids a
couple of days a week, he said okay before she had finished her
presentation. As a reward, she completed the blow job and let him cum
in her mouth. When she released a flaccid ?Little J? from between her
lips, she showed him the small pool on her tongue before she swallowed
it and licked her lips. She stood up, grabbed his head and planted a
kiss on his lips, sticking her tongue in his mouth so he could taste
the remaining bit of his own cum. Carrie was nasty. Justin was in love.
***
Matt rang the bell and Patty opened the door. ?Hi, Matt, you here to
see Jamie??
?No, I came to see you, cutie.?
?Oh, you're silly.?
?Is Jamie here??
?Yeah, he?s up in his room, Go on up. Hey Jamie, Matt?s here.?
He had never been to upstairs yet. ?Ah, which room??
?On the right.?
?Thanks, Patty.?
He knocked on the door and Jamie said, ?Come in.? Jamie was laying on
his bed staring at the ceiling.
?Hey. Whatcha doing?? Matt asked, sitting on the bed.
?Thinking.?
?Yeah, me too.?
?It?s just not fair.?
?No, it?s not.?
?What are we going to do??
?Well, I guess that depends on you.?
?What do you mean??
?Are we still going steady??
?Well, I guess that depends on you.?
Matt laughed, he knew something was coming. ?Why?
Jamie held his hand up, ?I don?t see a ring on my finger and you know
what Bey says.?
?You?re a nut.?
?Guess that makes you a squirrel, big boy.?
They both laughed at that, Jamie sat up and Matt pushed him back down
and kissed him. Jamie tells him to lock the door. They make out for a
while, but when Matt took Jamie?s hand and put it on his hard cock,
Jamie pulled back and told him not here, not now, not with my mom and
sister in the house. Matt said he was right, besides they had bigger
fish to fry.
***
?You?re right. It?s just not fair. This is supposed to be a free
country, right? What a joke, it?s only free if you do what they tell
you and isn?t that the very definition of not being free. It?s bull
shit. It?s all bull shit.? Matt was on a rant.
Jamie was quiet, letting him blow off some steam. They had been talking
for half an hour and still didn?t know what to do.
Matt sat down next to Jamie, turned, and said, ?You know, I have a
confession>?
?Okay.?
?When we went to the park the other day, I liked you, but I may have
come on a bit strong, and might have lead you on a little.?
?Go on.?
?But the more I?m with you, the more I miss you when you?re not there.
Does that make sense? Then today, when I opened my eyes and saw you, I
swear I almost shot my wad and I haven?t been able to think of anything
else since. This afternoon my sister was throwing the ?L? word around a
lot. I?m just a junior in high school and I don?t know what love is.
But what I?ve started to feel about you is the closest thing I?ve ever
felt to it. I guess what I?m trying to say is, I think I?m falling in
love with you. And right now I feel like I would do anything to be with
you. Whatever it takes.?
?Wow, that was beautiful and thank you for being honest.? Jamie could
feel the tears rolling down his cheeks. ?I don?t know what to say.?
?You don?t have anything to say? Call the media.?
?Haha, very funny.?
?Come here and give me a hug.? ?This is nice, hugging my little girl.?
Jamie agreed, from the first day, feeling safe in Matt?s strong arms
were some of his favorite times. ?Oh, Matt,? he sighed. Jamie wished
they could stay just like this for about three hundred and twenty-two
years, nobody lives forever.
They swayed to the background music in their heads. Matt said, ?So,
what are you thinking? You haven?t said much. I was joking about the
media thing.?
?It?s not that. I?ve got mixed feelings. No, not about you. About the
dressing part. But you?re right, when I saw myself in the mirror today,
I just about shot my wad too. But I also saw a future, a future that I
think I could fit in better than the one I have now. That girl had a
future. I could be that girl. And with you there to hold my hand when I
get scared. I can?t lose.?
?So what are you saying??
?I?m saying yes, let?s do it. If you think about it, it?s like the
perfect thing. We?ll have time alone, I?ll learn how to be a girl, and
we?ll eventually figure out if this is real or just another side street
on this journey we call life. Was that too deep? Sounded kind of heavy.
Whatever. I know we?ll have fun. We just met four days ago and I?ve had
more fun, and experience so many things, I lost my virginity.?
?I was there.?
?You were? I could have sworn it was the mailman.?
?Yeah, that?s right and he?s going to be delivering to your box again
in the near future.?
?Good one.?
?It?s getting late, I better be going.?
?Oh, okay, what are you going to do??
?I?m going to tell my sister that we are on board and I?ll tell you
what she says tomorrow.?
?Can you wait till tomorrow? I want to be there when you tell her,
okay??
?What if she asks??
?Just say we will tell her tomorrow, together.?
?Okay.?
They shared a kiss, unlocked the door, and Jamie walked him to the main
entrance.
?See you tomorrow.?
?Tomorrow,? Jamie said and closed the door.
***
That night, Jamie once again found himself floating through the haunted
tunnel, Matt?s arm around his shoulders, and his head resting on
Matt?s. Not a word between them. This time when the ride was over,
nothing changed. They got out of the boat and Matt was wearing the same
clothes. He got out and reached for his hand to help him out. When he
reached for Matt?s hand, he saw that he had long fingernails painted
bright red, some bangles for a bracelet, and a gold ring with a shiny
stone. He got out of the boat, looked down and saw that he was wearing
Carrie?s dress and shoes he had on earlier. And when he looked down his
long hair fell in front of his face. He looked up and Matt was smiling,
he said, ?Don?t worry, babe, you look great.? He put his arm out, Jamie
fell into his embrace, and peace broke out all over the world. He woke
up with a smile on his face. He knew he made the right decision. He was
at peace.
***
When they talked the next day, Carrie was just as excited as the young
couple. She told them that she would introduce them this afternoon, he
got off work at four. But before that, they needed to go to the mall
and get some things. She offered to lend Jamie some money to buy the
things he would need. But Matt stepped in and said he had it covered.
Jamie was impressed and rewarded him with a kiss, whispering in his ear
what he was going to do to him later and Matt laughed.
?You two behave now, we have things to do,? Carrie said. ?Matt get that
box out of the garage and put it in my car. Jamie, come with me.?
In her room there was a bag of things, she told Jamie to grab. Then she
went to her closet and pulled out the box with the wig. ?My mom won?t
miss this for a while, so I?m going to let you use it until you get one
or let your hair grow. So, can I trust you to take care of it??
?I promise, thank you. Can I ask you something??
?Anything.?
?I don?t want to sound ungrateful, but why are you doing this? Why are
you being so nice??
?I?m not sure. I was looking for something different to keep me busy
this summer. When I saw the sparks between you two yesterday, I
thought, now here?s a couple that could really use my help, especially
you, nothing personal.?
?No, you?re right, I need help?
?Plus, I love my brother, he?s annoying at times and hard-headed, but
he?s got a good heart. Can I trust you to take care of him too??
?I?ll do my best.?
?That?s all I can ask.?
She took the bag out of Jamie?s hands, set it on the bed, hugged him,
and said, ?Welcome to the family.?
They had a bonding moment.
?Now grab that bag and let?s go shopping.?
***
At the mall, Carrie embarrassed Jamie a couple of times, like at the
cosmetics counter trying to figure out if he was a summer or a winter,
or at the discount shoe store trying on women?s shoes, but the worst
was when she picked out two bras and had him try them on in the ladies
dressing room.
They had a late lunch and headed over to Justin?s. They got there at
three thirty, Carrie had a key and they unloaded the car. DeOhGe
greeted them at the door and sniffed his approval. She looked in the
frig and shook her head. She asked Matt to run over to the small market
a couple of blocks down the street and get some drinks and snacks.
Meanwhile, she took Jamie into the bathroom and started the process.
She had him Nair away what little hair he had. Then get dressed in the
new bra and panty set and one of her old dresses. Had him pay attention
while she did his makeup, Placed, combed, and sprayed the wig on his
head and stood back. Something was missing. She remembered the jewelry
set, with the clip on earrings. The last thing was to mist her with
perfume. Now he looked like a she.
When she lead him into the living room, Justin and Matt were sharing a
laugh. They both stopped, mid-chuckle, and their jaws dropped in sync.
They spent the next couple of hours nailing down how this affair was
going to work. Jamie had to change back but didn?t want to. ?Someday,?
he told himself. They said goodbye to Justin and DeOhGe and everybody
left happy.
***
The first couple of times they went to Justin?s, Carrie went along to
help Jamie. He was a fast learner and when he got to where he could do
it on his own, Carrie told them that she and Justin were going to take
them out to dinner Friday night. Of course, this caused Jamie all kinds
of anxiety, but Carrie and Matt kept telling him it was no big thing.
The night came, Jamie took extra care to make sure everything was
perfect. He walked, he was getting good in heels, into the living room.
The three others all complimented him. This was going to be his first
time in public and the butterflies in his stomach refused to calm down.
Justin opened the door, Carrie and he walked out. Jamie and Matt stood
at the threshold. Jamie said, ?Matt.?
?You scared??
?Yeah, will you hold my hand??
He looked down, smiled, took his hand, and said, ?Always.?
Together they stepped through the door, into a brand new world.
Which brings us to the end of this tale, or is it really just the
beginning?