Date: Mon, 11 Aug 2014 09:58:32 -0700
From: J R <pluckyd29@yahoo.com>
Subject: Rest Stop Bathroom part 3 (tg_teen)

Rest stop bathroom 3

I had sucked two dicks since our trip started.  I was recounting my sexual
encounters while we entered Montana.  I definitely did not plan on this
trip turning out this way, but pleasing those men the way I did, and
hearing their moans and feeling their cum shoot into my mouth was becoming
the only thing I thought about.  Feeling my femininity start to take hold
of me and my desires.  There was no going back, but there was much to look
forward to: getting fucked by a man.

I still had my panties on under my clothes, and wasn't planning on ever
going back to boy underwear.  It just felt so right to have on cute
panties.

By the time we got to Helena, it was close to midnight.  We found a small
motel not far from my sister's new school, and unloaded the car. After a
long drive I was looking forward to sleeping in a bed.  We got one room to
share between the three of us, which meant I got to sleep on the air
mattress, which I didn't mind.

The motel was filled with seemingly two types of guests: families of new
students like us, and permanent residents/drifters.  It was run by a
conservative elderly Christian couple and their family, so it didn't seem
bad at all, regardless of how some of the people seemed.  Oddly enough, I
was too preoccupied with my own fantasies to care about the condition of
the motel.  Every dad I saw, I imagined what his naked body looked like,
and if he would fuck me, and what way he would fuck me.  Also looked at the
"permanent residents" and shuddered at the way they'd handle me.  Finally I
found a dad that was to my liking.  He wasn't a big man, just slightly
taller than my sister (maybe 5'7"), slight build, with a little bit of a
belly.  Looked to be about late forties, clean shaven, and kind of a nerdy
look to him, with a full head of salt and pepper hair combed loosely to the
side.  I thought about how gentle he'd be with me.  I looked, but couldn't
find a wife around.  Maybe he's not married.  I didn't know, but it made me
think that I had a shot.  I just had no clue how to go about it.  How on
Earth does a 12 year old boy get a clearly straight man like this
interested?

I loitered around outside until I saw what room was his: room 127.  I had a
feeling that I would have my chance during the five days we were spending
at that motel.  That night was when I made first contact.  I figured during
these last few summer days, the ice machine was going to get some traffic.
If I timed it right, perhaps a chance encounter could be had.  I was
wearing gym shorts that were a little snug around the hips (mostly due to
my bubble butt), a yellow tank top, and flip-flops.  Oh, and my new yellow
lace panties, making sure that just a little bit of lace shown at the
waistband.  I didn't have a set plan, but definitely an idea of how it
would go.  Finally from our window, I saw him emerge from his room with ice
bucket in hand.  I quickly got ours and told my mom I was getting ice,
leaving before she finished saying okay.

Walking towards the ice machine, I felt like the butterflies were going to
carry me away.  I came up behind him and he looked back at me and gave a
smile.

"Hello" he said.

"Hi..." I said.

"Nice night, huh?"

"Yeah...it's not too hot."

"Yeah, I love the weather up here..."

"My name's Jamie..." I blurted out.

"I'm Brian, it's nice to meet you Jamie."

"Nice to meet you Brian." I said as he picked up his ice bucket to leave.

"Nice to meet you young miss." He said as he walked away.

I was stunned.  Sure I've been mistaken for a girl before, but this time it
felt different. This time, it felt like a compliment.

I had met him, now I needed to somehow get him alone either in my room or
his.  The next few nights, I was able to recreate our chance meetings at
the ice machine.  I learned that he was 56, he was married, and had 3
children, with his youngest daughter now entering her second year at
college, meaning he wouldn't be staying as long as I was.  I also decided
to tell him that I was a boy, to which he apologized.  I reassured him that
it happened all the time and that it was no big deal, I didn't mind.
During one such encounter I discovered that Brian was a history professor
at a community college in his hometown in northern California, about three
hours north of my hometown.  I would be able to use this fact to set up our
alone time.  I knew that the students had activities set up for them, and
knew that my mom would be busy with my sister; I also assumed (correctly)
that Brian would be in the motel while his older daughter participated.  My
plan was simple: fake some sort of summer school assignment and ask for his
help, the rest would take care of itself.  On one of our ice machine
visits, I asked him for help on my "assignment" to which he agreed,
although a bit hesitantly.  Now to get ready.

I decided I was going to go for broke.  I pulled out my new white thigh
high stockings, white camisole, and yellow lace panties.  Tomorrow would be
it.  He suggested we study in his room, which I took as a good sign that he
might be interested in some extracurricular activity, with maybe a bit of
persuasion.

 On the day of, I put on my thigh highs, put on my lace panties, put on my
cami and looked in the mirror.  I decided to take a few provocative photos.
Taking the pictures made me feel sexy and got my all hot and bothered.
Even my neck length hair felt softer and looked shinier.  I would want to
fuck me.

Seeing as how I could just walk out like I was (although the thought
crossed my mind) I put on my running shorts that showed a bit of leg, and
in a bit of brilliance, I put on sweats and a long sleeve shirt before
grabbing my back pack and heading out the room.  Nerves began to creep into
my tummy as I approached the door to his room, knowing what I had on
underneath my long clothes.  I took a deep breath and knocked.  He answered
almost immediately, with a smile on his face that eased my tummy a little
bit.

"Good morning Jamie"

"Morning Brian, or should I call you Mr. Swanson? You know, because you're
kinda my teacher now..." I said, and we both chuckled slightly.

"Either is fine.  Come on in, and tell me about your paper." He said.

I entered his room and laid my bag down. It was getting hot outside, so
inside his room was a little warm.  He was wearing a short sleeve button
down, and some cargo shorts.  He closed the door after I walked in, and I
had noticed that the curtains were already closed.  I started to get
excited.  I sat down on one of the beds with my bag at my feet.

"Would you like a soda or something?" He said.

"Sure..."

"So what's the topic of your paper?" He said while handing me a soda.

"The Vietnam war..."

"Oh that's a real interesting topic, what specifically about the war?"

"I'm not sure, that's the problem." I said, trying to seem as stressed as I
should have been.

"Well there's a few ways you could go..." He began to say, but then paused
and looked at me.  "It's kinda warm, do you have a shirt under your
sweater?  You could take it off you know, might feel better."

Jackpot.  The plan had effectively worked.  Now I could innocently expose
my secret under garments and test my desirability as a girl.  I'd have to
tread lightly though, and not let my excitement get the better of me.
Vulnerability would be key.

"I would," I said coyly "but...my luggage was lost on the way here, so I
had to wear hand me downs from my sister.  I am a little warm, but it's a
little embarrassing.  I don't want you to think I'm weird."

I could see the sympathy building in his eyes.  His reaction was very much
what I had hoped.

"Oh that's ok, there's no one here but us, and my daughter's not coming
back to the room tonight, so there's no need to fear.  I would like for you
to feel comfortable, both physically and mentally.  I won't judge."

With that said I proceeded to stand, looking him in the eyes as I slowly
pulled my long sleeve shirt off exposing my girly camisole tank top that
exposed the bottom part of my smooth flat belly.  I watched his eyes as he
processed what was in front of him.  I watched as desire began to creep
into his mind and he tried to hide his unexpected excitement.

"You were right, it does feel much better, thank you for being so sweet
about it." I said

"That's quite alright, like I said, no one will judge you in here." I could
see him struggling a bit; I wondered what he was thinking.

"I'm also wearing shorts under these sweat pants, but..." I started hoping
for him to probe for more.

"But what?"

"Well...I'm wearing my sister's old running shorts, and since I didn't have
any socks clean, I had to borrow the closest thing to socks she had..."

"I don't think that's too bad, like I said I just want you to feel
comfortable, you could be wearing a dress and I wouldn't judge you." He
said.

I couldn't help but smile.  I felt like he secretly wanted to see me in a
dress, so I was confident in my next couple of steps.  I got up once again,
looked him in the eye and gave a shy smile.  I turned slightly so I could
bend over (and also so he could see my ass a bit) as I peeled my sweat
pants off.  I was finally exposed in my rather feminine attire.  I awaited
his reaction.

"Wow...you have very nice legs...I'll bet a lot of girls would be jealous
of your legs." He said.  He seemed to get a bit nervous after he said it.

"Thanks, I'm a little worried that I don't have any hair on my legs yet." I
said with a slight giggle.

"I wouldn't worry, hair is over rated...besides, I think you look just fine
without it.  Plus your legs probably feel a lot softer hairless."

"Yeah, that's true.  Thank you for being so nice, I honestly don't know
anyone who would be this nice to me...can I be honest with you?"

"I would certainly hope so..."

"I actually don't mind wearing my sister's clothes...I kinda like them
actually..." I admitted.

After a brief pause, I felt my gambles beginning to pay off.  He smiled at
me, but kindness was beginning to give way to what I hoped was lust.

"Lemme grab my laptop so we can find some sources for your paper." He said.
As he got up I noticed a slight bulge in his crotch.  Maybe he thought I
wouldn't notice.  Maybe he wanted me to notice.  Either way, it was time to
pounce.

"You know," he said as he sat down with his laptop "a lot of boys like
wearing girls clothing." He said.

"Really?!" I said, encouragingly enough to hopefully keep him going.

"Oh yes, and some boys even let their hair grow long and wear makeup.  Hear
lemme show you."

He opened his laptop and typed some words up.  A second later he changed
seats to sit next to me to show me pictures of what looked like young
girls, only they had penises.  I was very familiar with this sort of porn,
but acted as if I was seeing it for the first time.  His enthusiasm was
infectious.  He was like a kid in a candy store.

"These boys look just as pretty as any young girl.  Is that something you
think you'd wanna be?  A girl? It's ok if you do, nowadays it's fairly
normal..." He said.

"I don't know if I could be as pretty as them, though..."

"Nonsense, I think you're very pretty." He said, his smile said a little
bit more.  "Would you like to keep looking?  Maybe you'll see some outfits
you like..."

I nodded my head, returning a smile.  We spent about ten minutes looking at
pictures, commenting on each one.  Then I found my moment when we came
across a picture of a boy in yellow panties.

"Hey I have panties like those!" I said in my most excited innocent voice.

"You do?  Well maybe someday you'd like to model them for me?  I bet you
look really cute in them."

Without saying a word I got up, and excitedly pulled my shorts down just a
little to expose the yellow lace.

"See?  I'm wearing them now."

"Oh my goodness!" He said with wide eyes and a small excited chuckle.

"Yup." I said with a big silly smile.  I raised my hands as if to say
'tah-dah' and allowed my shorts to fall to the floor.

"Very nice...very very nice." He said as his eyes studied my young body
very hard.  "Can you do a little spin? Let me look at you."

With the big smile still in place, I nodded.  I walked toward the door and
stopped. I span around and started to walk across the room as if I were on
a catwalk.  I then did a slow twirl, and giggled.  His eyes had already
started to fuck me.  I did my best 'little girl' act, and walked back
towards him.

"This is fun!  Whattaya think?" I said placing my hands on my hips.

"Would you mind if I touched you?" He said barely containing his lust,
raging hard-on now very visible through his clothing.

"Nope." I said moving closer to him.

Still sitting, his eyes studied my tight petite body as he brought his
hands up to take my waist.  He then caressed my tight belly, letting his
hands drop to feel my smooth legs.  He then turned me 90 degrees to see my
profile.  My butt stood out quite a bit; he reached and cupped it in his
hand while his other hand lightly grazed the front of my panties, and my
already hard 21/2 inch boner.  He then turned me completely around and used
both hands to rub, squeeze and tickle my butt.  Then he kissed it.  I could
the heat of his face hovering near my butt as he gave it another kiss on my
other cheek.  Then he inhaled as if he smelled freshly baked cookies.

"Mmm...You smell so good."

"Thank you..." I said and then giggled.

After a few minute of him playing with my backside, he turned me to face
him, and gave the same treatment to my front.  As he leaned in to give my
penis a light kiss, he deeply sniffed it.  I looked at his encased penis,
just dying to get out of its cotton confinement.

"Can I try?" I said motioning towards his crotch.  Without saying a word,
he leaned back.  I knelt down between his legs, and rested my head on one
of his thighs as I reached out to feel the bulge in his cargo shorts.  I
leaned forward and gave the head a kiss through the fabric.

"Would you like to see it?"

I smiled and nodded.  He sat up and motioned me to sit next to him.  Once I
sat down, he undid his fly, and pulled his shorts down and off, revealing
his boxers.  He quickly pulled them off leaving him in just a shirt.  I
leaned in to study his wonderful cock.  It was about 6 inches long, average
size I guess, his balls were still tight, but fairly good sized.  Even
though his cock wasn't the biggest I'd seen, it was by far my favorite, it
was just very pleasing to my eye.  I lay prone on the bed and just placed
my head on his lap and stared at his beautiful cock for a while.  He
stroked my hair, and caressed my bottom.  His hand would on occasion slip
under my panties and give my smooth booty a gentle squeeze before slipping
back to stroking my hair and face.  After a couple of minutes I looked at
him and smiled.

"Would you like to kiss it?" He asked.

I smiled and nodded.  I inched closer and kissed the head of his cock,
looking at him and smiling afterwards like a puppy looking for praise.  He
smiled back and stroked my hair.

"Go ahead..." He said.

I took the advice and proceeded to kiss and lick the entirety of his penis.
He kept stroking my hair and face as he whispered to me.

"Good girl...goooood girl..."

After about ten minutes of kissing and licking, he finally wanted more.

"Mmm...Now put it in your mouth pretty girl."

I looked at him and smiled.  I took the base of his cock in my hand and
slowly lowered my mouth over the head.  I could taste his sweet precum as I
swirled my tongue around.  I then slowly tried to fit as much into my mouth
as I could.  I nearly got the whole thing in my mouth, and then gently
sucked as I pulled away.  I closed my eyes to savor the flavor.

"Mmm...Oh my god!...look at me sweetie...let me see your beautiful eyes."

I repositioned myself back to the floor between his legs and we locked
eyes.  I couldn't help but giggle a little, with his cock still in my
mouth. He chuckled a little too.  As I gently sucked his cock he put both
hands on my head as it bobbed up and down in a steady rhythm.  With our
eyes still locked, he smiled slightly as he just sat and enjoyed the view
and feel of being in a young girly boy's mouth.

"You're so beautiful." He said.

I just smiled with my mouth full of penis.

"Do you know what semen is?"

I nodded, mouth still full.

"Do you mind if I finish in your mouth?"

I paused very briefly as if to think about it.  Then shook my head and
mumbled 'nope' and continued to suckle on his cock as he stared into my
eyes.  After about half an hour of sucking his cock, he started to fidget
and squirm a little, and gently moaning.

"Ooohn god you're so precious...oh I'm going to cum in your mouth...are you
going to swallow it, sweetie?"

I nodded.

"Good girl...such a good girl..." He said, now breathing heavier.
"Ooooooooh!" He let out a final moan as his penis swelled in my mouth and
he shot glob after glob of hot salty cum, filling my mouth to the brim.  I
swallowed as fast as I could, but some dribbled out my mouth.  He collapsed
back onto the bed, and I continued to clean his dick of any cum, until he
finally shrank down to flaccid.  When I got up from my knees, he surprised
me by sitting up to kiss me on the mouth, his tongue playing with mine. He
pulled back and stared at my face.

"You're perfect." He said

"Really?" I said

"Really..."

He pulled me down to the bed, and held me in his arms as we kissed.  After
some time he started to fall asleep.  I got up out of bed and started to
gather my clothes.

"What are you doing?" He asked.

"Getting dressed..."

"Do you absolutely have to leave?  I'd like to have you stay if you
want. Of course you could stay in your underwear, no ones gonna bother us
tonight."

I smiled at the thought of staying the night.  I dropped my clothes and
scurried back to the bed and laid into him.  We spooned, me being the
little spoon, as we drifted to sleep.  I've never felt so good.

I woke up some time later, with him kissing my ear, and poking at my butt.
He turned me into him and we kissed passionately.  He then kissed my neck,
and slowly moved down, kissing around my collar bone.  I sat up and took
off my cami, and he immediately found my nipple with his mouth, gently
licking and kissing both of them. He then proceeded down my belly, french
kissing my belly button on his way to my panty covered penis.  He kissed my
panties before pulling them off.  He then went straight for my penis,
easily taking the whole thing in.  It was a sensation like no other.  I
squirmed as he sucked on my penis like a lollipop for nearly twenty
minutes, then came up to kiss me.

"I could stay here forever." I said.

"So could I."

I pushed him to his back as I crawled down to his cock.  I found his balls
and licked and sucked on them like they were covered in frosting.  After a
few minutes I looked up at him, met his eyes, and swallowed his hard cock
whole.  He stiffened and gasped.  Then I felt both hands come down on my
head as he held me there for a few seconds.  His eyes closed for the first
time, biting both lips.  I sucked him for about ten minutes, before coming
up to make my request.

"What's wrong sweetie?"

"Would you like to have sex with me? Like real sex?"

His face was stunned, and I could feel his heart racing through his chest.

"Are you sure?"

"I think so..." I said to him with a coy smile.

"I don't want to hurt you"

"I know...but I like you, and I know you'll be gentle...I've been wanting
to ever since I first met you..."

"Ok my sweet girl."

With that he got up, and went to his bag, bringing back a small bottle of
lotion.  He looked nervous and excited at the same time.

"Are you sure about this?"

"Very much."

"Ok, but I don't have any condoms, is that ok?"

"I don't see why not." I said with a grin.

He kissed me again.  After some more kissing, and groping, I turned around
flat on my tummy.  He immediately buried his face in my butt and took a
deep sniff.  He laid there sniffing my butt and kissing my cheeks for about
ten minutes before plunging his tongue deep into my little butt hole.  It
took me by surprise, as I let out a very loud gasp.  The pleasure was
amazing, and I wanted more than ever to have him deep inside me.  He worked
my butt with his tongue for about five minutes, and then took me by
surprise once again by sticking in a finger.  It was a bit uncomfortable at
first, but he took it slow, and after some time I was beginning to get used
to it.  He alternated his finger and tongue, and after a while I started to
want more.  Eventually I felt more, as he stuck another finger deep inside.
I took a deep breath as he his fingers slipped out and then back in
rhythmically.

"Do you like it?  Am I hurting you?" He asked.

"I love it, it feels amazing...I don't ever want it to stop." I cooed back
to him.

"Are you ready for the real thing sweetheart?"

"Uh-huh..." I whispered.  I wasn't sure how ready my butt was, but my lust
filled brain was more than ready.

"Ok my dear..." He said as he gave my butt a deep passionate kiss, and then
moved up my back, kissing along my spine.  He kisses my ear and whispered
to me:

"Turn over baby, I wanna see your face as we make love."

I obliged, and our eyes meet.  He gave me a passionate kiss, and I could
taste my butt on his tongue still.  He reached for the lotion, and squirted
a glob on his hand and coated his throbbing cock, wiping the remainder all
over my saliva coated hole.  He positioned himself between my legs, and
lifted them over his shoulder.  I could feel his hardness rub against the
back of my thighs as he positioned our bodies, the he guided the tip of his
cock to the entrance of my boy hole.

"Here we go, ready?" He smiled.

"Do it." I said quietly, returning his smile.

With that last consent, he pushed forward, putting pressure on my opening,
and I took a deep breath.  I let out a loud cry as the head popped into my
body.

"Are you ok?" He said.

After a few seconds, I caressed his biceps, and nodded.

"I'm ok, I'm ok...just go slow..." I smiled at him, although my discomfort
was fairly clear on my face.  He lowered my legs to his side, to lower
himself to kiss me.  I responded by wrapping them around his body.

After a nearly ten minutes of me just getting used to the head, he began to
inch his way in deeper, which wasn't as bad as the initial entry.  Soon he
was completely inside me, and our kisses became strong and lust filled.  As
he pulled out, he gazed into my eyes, and then pushed back into me.  He
began to get a steady rhythm, and soon he was fucking my hole to his
heart's content.  After about fifteen minutes of slow fucking, I went from
discomfort to extreme pleasure.  I wanted him to always be inside my butt,
fucking me with that stern expression on his face, vein in his forehead
popping out.  His body pressed against my hard penis and just added to the
pleasure.

"Oh fuck me...Brian give it to me!" I loudly moaned.

"Oh sweet girl, you're so tight and warm!"

"Fuck me harder, daddy!"

With that the intensity grew, and he sat up and put my legs back on his
shoulders and took hold of my hips, and then began to fuck me with long,
deep strokes.  For twenty minutes, he fucked me with those long strokes,
and then he began to speed up, using short, hard strokes.  He was pounding
me like a jack hammer, grunting in rhythm.  I whimpered with the extreme
pleasure as I bounced around on the bed.  His grip tightened and for the
first time I felt how strong he truly was, as he was now fucking me even
harder.  Each time he thrusted, he used his full strength.  The impact of
his body and my ass was almost painful, if it wasn't so pleasurable.  His
breathing was getting shallow, his thrust longer.  He was about to cum.

"Oh my god!  Here I cum...Here I cum baby...look at me...tell me you want
me to cum!"

"Cum daddy, cum inside me!"

"Where do you want me to cum baby?!"

"Cum in my ass daddy!  Give to me...oh daddy please cum deep inside my
tight warm ass daddy! Oooh!"

"Aggghhh!"

With on final hard, deep thrust, his cock swelled inside of me and
exploded.  I could feel his hot semen shoot out into me, filling me to
capacity.  Two, three, four, five, six spurts of cum shot into the deepest
reaches of my butt.  He stared intently into my eyes, as we both watched
the expressions of euphoria on each other's face.  He released my legs and
collapsed on top of me.  The only sound was our heavy breathing.  He kissed
my neck lightly, and then kissed my lips. His erection subsided, and he
slipped out of me releasing a flood of cum out of my used ass.  We laid
there side by side in silence for a few minutes.

"That was amazing..." I managed to say between breaths.

"It most certainly was..." He smiled.

"My ass is all squishy." I giggled.

"Well give me some time and we can go again." He said as he leaned over to
kiss me.

"Ok"

He turned on the TV and we watched it for a while.  We talked and joked
around, we ordered a pizza, and Brian dared me to answer the door dressed
as a girl, which I did, completely fooling the pizza guy.  It was a great
evening; we fucked three more times throughout the night, trying different
positions.  He was completely obsessed with my butt, as he was touching it,
kissing it, sniffing it whenever he could.  That night started something
amazing that I never wanted to end.  I slept in Brian's arms that night,
and he woke me up the way a daddy should wake up his girl, with a poke in
the butt.