Date: Sat, 12 Nov 2011 09:53:25 -0800
From: Dave <outinwest@gmail.com>
Subject: The Society Boys Part 9

The Society Boys
By Connor Matthews


Chapter 9 - Adventure Day

We received a text early Friday to check our email.  The message was to
show up at the address provided by 9am on Saturday.  We were to arrive
wearing a dress and either briefs or no underwear at all, along with
whatever shoes we wanted, but nothing else.  We were also told to walk,
bike or take a bus only. No driving, cars or taxis. Neither Alex nor I have
sisters, so we elected to go to the thrift store to buy a dress.  We had a
ton of fun trying them on, and the girl in the store was totally helping us
out as she kept finding stuff in our sizes.  We had our underwear on, but I
think she was enjoying watching us change and probably got a kick out of
how much goofing around we were doing.  After picking two dresses that we
were told looked good with our hair and eyes, we headed home to get ready.
Alex decided to be the daring one, yet again, and went without underwear.
I chose to be a little more cautious, even though he tried to convince me
otherwise.  I wore my blue briefs.  This could be the Halloween drag thing
that Alex wanted to try.  With me being so much smaller framed, I looked
like the better girl.  I suppose with a wig and make up and some sort of
stuffed bra, I might actually pass as a chick. As for today, I looked like
a boy in a dress.

We rode the bikes to get there quickly and avoided the main roads to
minimize contact with the public, but as we found out quickly, it was a
moot point. As we arrived at our destination a guy came up to us and handed
us a sealed envelope and walked away without saying anything

We opened the envelope and inside were tickets, $200 and instructions.
`Enjoy the day at Playland.  Q'

This was our local amusement park.  As we made our way there, I was betting
Alex wished he'd worn underwear.  We walked around the park getting a few
wolf whistles from guys, and laughs from people wherever we went. It was a
blast enjoying all the rides, food and games, but it would have been much
more fun without the dresses. We did meet the other 4 guys in the
park. Sometimes hooking up with them to ride a ride, and other times we
were on our own.  A few hours later, a guy came up and handed us another
envelope.  We opened it and the instructions said `take the car waiting for
you at the corner of Geronimo and 12th. It will drive you to your next
adventure.'  There were two generic `admit one' tickets in it as well. We
left Playland and found the car easily enough, as the driver was holding a
card with the axe symbol on it.  He drove us a short distance to a bungee
jumping area.  I laughed.

"Guess you better hold your dress down or they're gonna see everything" I
laughed.

"So you go first and I'll wait until you get back up. Then just give me
yours."  He said simply enough.

We ran up to the platform which overlooked a ravine a few hundred feet
below, dropping into a large pool at the corner of the river.  I watched as
a few guys jumped. The bungee was long enough that as thy slowed down, they
went face first into the water. For Alex, this was no big deal as he was
used to diving from heights into water, but for me, this was terrifying.  I
had never bungee jumped before as I hate heights, but I could do it, as
long as I took a few deep breaths.

"Oh" I pouted "My pretty dress is going to get all wet and my mascara will
run" I said batting my eyelashes at Alex, who just laughed and slapped me
on my back.  I handed my ticket to the guy at the entrance to go and be
tied in.

"Where's your partner?" he asked.  I pointed to Alex.  "You two are to jump
as a pair" he announced signalling Alex forward.

"So much for wearing your underwear" he said quietly as we were strapped
into the harness. "Guess I'll just have to hold my legs closed or put my
hands on my crotch or something."  He said as we made our way to the
edge. "You ready?" he asked. I shook my head wishing it was over already.
"Three, two, one, jump" he yelled and we dove off the edge.  The fall was
unreal.  A feeling of flying and one of `oh my god, I'm going to die'.  I
had my eyes closed so tight that I thought they might be fused shut.  I
felt the bungee pull tight and we slowed until our hair hit the water.
Fortunately we didn't go in very far, before we bounced back up. We did
several more bounces, and I was acutely aware that my dress was flapping
all over the place. Note to self.  Don't bungee jump in a dress again.
They slowly lowered us into a boat that came up.  We were lucky as the only
part of us that got wet was our heads.  It was actually a total rush, but I
need a major pee when we got to land.  Another envelope was handed to us. I
was beginning to think we were in the Amazing Race.  I was waiting for Phil
to come out and tell us that a detour was a choice between two tasks, or
that a road block was a task that only one of us could perform.  This time
the envelope said `return to the car. Once there, switch ALL clothes you
are wearing with your partner (except shoes) before you get to your next
adventure.  Alex laughed. "I guess I get your underwear after all."

As we rode to our next destination, we switched clothes as told. It felt
really weird having no underwear on under the dress.  I felt more than a
little vulnerable. It was bad enough with underwear.  The car pulled up at
a sports field where we were to join a rugby game.  Alex was on one team
and I was on the other. I was slightly pissed as he at least had underwear
on.  My underwear.  We had to play until each team scored. I had no idea
how to play, but I certainly was grabbed a lot and tackled quite a few
times. Of course the guys all made smart ass comments about us being in
dresses and each time they saw me naked or Alex's underwear, the cat calls
went out and they laughed.  After both teams scored, we were given another
envelope and sent to the change room to get cleaned up. Fortunately the
field was just dusty, so the dresses were still ok and only needed brushing
off. Towels had been left for us to shower, which we did quickly. I
suggested that we keep the clothes in sight, so that no one could steal
them and make us head home in just towels.  We needn't have worried as we
were left alone in the change room. After we dressed, we opened the
envelope `leave any underwear you have in the change room, and head back to
the car.'

Next it was dinner time at a fancy restaurant.  Everyone just stared at us
and made small talk under their breath. No doubt they just assumed it was a
frat prank, which was okay by me as long as I didn't have to do cartwheels
all the way to the table. The other four guys were already there and as we
talked we found out that they had done the same things, either in a
different order or time. It was a lot more comfortable in a group than just
by ourselves.  The dinner was enjoyable and I almost groaned when another
envelope was given to each of the three pairs. Looking at ours, it said
`You will begin your evening with relaxation, followed by a few drinks and
some music. We hope you are enjoying your day.'  "Thank God" I said was
beginning to feel the effects of the Rugby.

Our stop was the Serenity Spa. Yet another thing I had never done. A nice
massage would feel good right about now. We began with a sparkling water as
our feet were soaked in a warm bubbling foot thing. The music was soothing
and I could have fallen asleep right there. Our hands were put into warm
slippery water.  I looked at Alex and said "It's so gentle, I'm soaking in
it" I giggled trying to remember the actual lines from the dish soap
commercial. I was talking quietly to Alex when a few ladies came up and
began to work on our feet and hands. Now, the worst thing you can have
happen when you are ticklish is to have someone play with your feet. I was
no longer relaxed and almost kicked her across the room. I apologized and
calmed down in preparation for her to touch me again.  They gave us
pedicures and manicures. God, how do girls do that? Those things actually
hurt as they push skin back to expose cuticles. Who needs their cuticles
exposed? It was bad enough having my boy bits exposed. They finished and
let us sit there for a few minutes before taking us to a room with two
massage tables. We were instructed to get undressed and lay face down on
the table with a towel across our buttocks. After stripping off the dresses
and lying face down, I talked to Alex "You ever had a massage before?", my
face resting in the hole at the top of the table as I looked at the floor.

"Nope. Have you?" he replied

"No, but I definitely could use one." I said trying to sound like I knew
what it was all about.

"Yeah, me too."  He agreed.

I looked up as two guys walked in wearing white shirts and pants. I don't
know if I was relieved or sad that we were going to be massaged by guys. I
had heard that a lot of guys got hard when being massaged, so I was trying
to process which would have been better. A guy or a girl. They introduced
themselves and asked what type of massage we wanted. I said I didn't know
while Alex replied `a sports massage?' with a question at the end of it.
The massage began with oil being poured all over my body and started at the
neck and shoulders. It felt good, and the guys had pretty powerful hands. I
was pretty sure he could snap my neck if he wanted to. I could feel him
working every knot and muscle. At times it hurt and I jumped, but tried to
sack up and accept it.  As he moved down my back, I turned my head to look
over at my best friend. He was getting the same treatment as me.  "Howz it
going over there?" I asked.

"Great, I should do this every week." He replied turning to look back at
me. "I may have found a new favorite thing."  I agreed, and we made more
small talk before placing our faces back in the head rest. The massage
moved to my arms and fingers, before proceeding to my legs. Each one was
raised and stretched back as the calves and thighs were rubbed hard. I was
beginning to feel like Jell-O, although acutely aware that each time my leg
was raised he could probably see the crack of my ass or even my balls. I
ignored it and just felt the tension being squeezed and beaten out of me by
his hands and elbows.  This guy was certainly powerful and at times
painful. I was wondering if maybe a girl would have been gentler. Hands
moved up my legs and as he passed my thigh, I felt his hand touch the
bottom of my glutes.  He worked there for a while and even opened my legs a
bit to get his hands around my thigh more. His fingers touched the bottom
of my testicles a couple of times.  Notice how I'm using the technical
terms glutes and testicles instead of ass and balls? After all, this was a
professional massage, not a sex orgy, so I'm trying to fit in.  After
working this area for a while, I felt the towel being lifted up and folded
over half my ass, umm, buttocks. The crack was covered as he applied more
oiled and worked on the cheek. Is it one glute and two glutes, and does the
crack have an official name?  Who cares...he was rubbing my ass, and as he
applied pressure, he was pulling the cheeks apart slightly. I could feel
the cool air getting to my hole and although I was still partially covered
by the towel, it felt like I was naked.  He covered me completely again
before moving to the other side to work on the other cheek. Once that was
done, I expected the towel to cover me again. Instead it was removed
completely and I was sprayed down from head to toe with more oil. His hands
worked from my neck all the way to my toes in one continuous movement. His
fingers even went slightly into my crack and I thought I felt it brush
against my hole. I turned to look at Alex who was already staring at me. He
mouthed `Oh my God!' and had a worried look on his face. I glanced down his
body and his masseuse was on the opposite side with his hands working on
Alex's ass. It almost looked as if the guy hand his thumbs in his hole. I
smiled knowing that the worried look was probably because he was enjoying
it a little too much and had reacted.

My guy was working on my toes one at a time, and I was trying my best not
to giggle like a little girl. It was taking every ounce of my energy not to
yank my feet out of his hands and kick him in the face.  As he put my feet
down, he placed my legs slightly wider apart before he moved back up to my
ass. I felt his fingers go into my crack and down to my balls. There was no
mistaking that this was a deliberate part of the massage. He pressed at my
hole, but didn't go in, thankfully. He pushed down along the crack and
worked a couple of fingers at the base of my balls. Now I don't care
whether you're straight or gay, or being massaged by guy or girl, when
someone plays with your ass and balls like this, you're going to get
hard. Some faster than others, but all will get hard.  So I was getting a
little uncomfortable as my dick stretched to full length. I wanted to reach
under myself to pull it up instead of letting it push down between my
legs. I was sure the guy could see all of it by now. How embarrassing. He
must have noticed because the massage stopped and the towel placed back
over my ass. I let out a big breath that I didn't even know I was holding.
"Okay, turn over." He said. I grabbed the towel and turned away from him to
lie on my back, trying to adjust my dick as I did. Looking over at Alex, he
was already on his back getting his chest massaged. He had his eyes
closed. Probably trying to will his dick to go down. The process began on
my front too, but not as forcefully as it had been on my back. He worked my
chest, arms, abs, legs and ankles before. Then moved the towel to one side
as he worked on my upper thigh, or whatever the area is called between my
thigh and abs. Hips?  He pressed almost right against my hard cock, umm
penis and a few times actually pushed it to the side using the towel.  He
repeated the process on the other side.  The towel was returned to
completely cover my groin until he raised the bottom half of it up and
folded it to meet the top half. I felt the oil being sprayed on my thigh
and balls. He gently pulled on my balls and rolled them around in his
fingers, gently applying pressure to each one. I was getting a testicle
massage. I didn't even know that was part of it. But I guess to a masseuse
this was just another body part. Then the towel was removed entirely and
put aside. I took a deep breath as I realized that he was now staring at my
8 ½ inch boner. I wondered if every guy got this hard. I peeked out of one
eye just enough to see if my dick was leaking precum, which would be a
total humiliation. I didn't see anything, thankfully. I closed my eyes
again and tried to think of anything disgusting that I could, in hopes that
my dick would go down, or at least behave itself. I felt him spray it with
oil and the penis massage began. He rubbed it carefully, lifting and
rolling it between his fingers. I made a note to pay attention to his
technique as it actually felt pretty good. More oil was poured onto it as
he began to jerk me off. Now I may not have had a massage before, but I've
jerked off enough to know that if this was a massage, then I'd had tons of
dick massages since I realized I had a penis. He was obviously going for
the happy ending that I'd heard about. Turning to look at Alex, he was
gripping his table as his guy was furiously jacking his cock too. That's
about all it took for me as I watched my boy being played with. My brain
immediately told my penis that we liked being jerked off.  I couldn't hold
back any longer, and all the tension that had built up in my cock, flew out
in massive jets onto my chest. The masseuse kept going even as I subsided
and the last bit dribbled out of me. He squeezed and rubbed my cock gently
as he placed it onto my stomach. I was breathing rapidly and just lay there
horrified. I watched as Alex raised his hips and unloaded his juice all
over himself, just as I had done. He was staring at me without blinking. I
figured seeing me shoot had no doubt sent him over the edge. We were both
wiped down and told to go to the shower at the end of the room. The guys
left and we headed to clean up. We had to do it one at a time as it was one
of those little metal stalls barely big enough for one person.

"I'm coming back tomorrow!" announced Alex grinning like he'd won the
lottery.

"I'm sure you are."  I laughed as I punched him in the arm. We got back
into our dresses and headed to the reception area to meet the
driver. Fortunately both us had gone soft again.  What I hoped was our last
destination, was going to prove to be the most difficult.  Since neither of
us had underwear now, and were simply in a dress and runners, going into a
country bar was not my idea of a fun filled night. First, it was a COUNTRY
bar, and second it was a COUNTRY bar. Not to mention we were probably going
to be killed.

A couple of total redneck looking guys came up to us "Well, lookie here
boys. Got us a couple of pretty girls needing a real man."

"Ha ha. Very funny" said Alex trying to look tough in his dress. "It's just
a dare."

"Oh, they're doing dares boys. Okay, I got one for you. I dare you to dance
with your girlfriend out there on the floor." I tried to ignore them, but
they were kind of herding us toward the dance floor. Fortunately a couple
of girls came to our rescue.

"Leave them alone Scott. Fuck, you're such an asshole sometimes." The girls
grabbed us and took us to their table. They asked questions about what we
were doing, so we stuck with the story that we were just doing dares. The
girls were pretty friendly and even bought us a few drinks. I don't mean
just one drink; I'm talking a few beers, several shots and an appletini,
which I thought tasted way better than beer.  Looking at Alex, he looked
about as drunk as I felt.  Somehow the girls managed to get us onto the
floor to dance with us. I vaguely remember our dresses being flipped up and
comments being made about how we weren't wearing `panties'.  The more we
danced, the more attention we are attracting and the more gropes we seemed
to be getting. I decide to sit down as I needed some water. I made the
mistake of grabbing Alex by the hand and pulling him along with me.

"Awww, ain't that cute.  Dorothy is taking Daisy to make out. Maybe we
gonna get to see some girl on girl action." He cackled.

I sat down trying to ignore them.  "So are you a friend of Dorothy?" the
huge cowboy looking dude asked Alex.

Now at the time I had no idea how funny that was, but looking back, it was
actually pretty good. Alex replied in his drunken state "Yep, Dorothy is my
best friend."  He leaned forward and put his head on my shoulder. More like
his head fell on my shoulder as he was obviously so pissed.  I really
needed to get him home to sleep.

"I'm sure she is" said the guy. "Maybe we should tap those asses before you
go home tonight." He grinned licking his lips.  I was now a little
scared. This guy could obviously do that if he wanted to. Not only was I
too drunk to fight, but there was a hell of a lot more of them than us. I
put Alex's head on the table and stood up to face the guy.  Well, okay I
stood up to face the guy's chest. "I'm sure you could, but then wouldn't it
be you who was gay, and not us?"  I said trembling.  "I mean if you really
want this, this I probably couldn't stop you." I lifted my dress and waved
my cock around in front of him. "Does that turn you on so much that you
really want sex with me? Or are you just jealous that I have a bigger
dick?"  I looked at him, and hoped I hadn't just signed my death
certificate.  I didn't have to wait long as the girls interjected
again. "Jesus, Scott, if you and your dumb horny buddies ever want to get
laid again by a real girl, leave these guys alone.  Perhaps you'd prefer
them to these." She said as she cupped her breasts and lifted them up. "I
don't think these boys have boobs for you to put your face in. Make a
choice asshole."

Scott obviously decided that he didn't want to lose his chance to get the
girls. "Whatever! We were just having fun with the little bitches. Teach
them not to put on dresses and act like chicks." He turned and headed back
to the bar.

"You guys should probably get out of here." She suggested. I agreed and
lifted Alex up to help him to the door. As we got outside, a final guy came
up and gave us another envelope. I was almost too drunk to read it, but
managed to get it open as I held Alex up. `The day is over. You're bikes
are tied to the post across the street. The combination for the lock is
2354, or you can use the $50 in the envelope to catch a cab home. I decided
that we were in no shape to ride home, so I kept the paper with the
combination on it and hailed a cab. We went back to my place.

I helped my boyfriend up the stairs to my room and closed the door after I
sat him on the bed. I undressed him and pulled the covers down as I lay him
on the bed. I grabbed a couple of glasses of water for the night table
before undressing and getting into bed with him. He cuddled up against me
and said in a slurred voice "I love you Dorothy" He kissed me sloppily on
the cheek.

"I love you too Daisy" I giggled and kissed him on the forehead, before we
passed out.

I awoke to a killer headache and a blow job well under way beneath the
covers.

"Oh yeah buddy, I love waking up to great head. I gotta get you drunk more
often if you suck like that afterwards." I reached down to rub his head and
realized the head I was rubbing was definitely not Alex.  I threw the
covers back and Randy was looking up at me; his lips around my cock and his
hand around Alex's, who was still sleeping. "What the fuck, Randy?" I
whispered "What the hell are you doing here? How did you even get in?"

"Jason let us in last night because it was too late to go back to my place
and Austin's house was locked." He whispered back.  "I just thought I'd
give you a nice thank you for letting us crash."  He grinned, as he went
back to suck my cock.  I heard him say `us', so I looked over the edge of
my bed and saw Austin lying on my floor sandwiched between a blanket and a
comforter. Randy was naked as I expected, and as I looked at Austin, and
around the room, I saw his dress too. So now there were four naked guys in
my room. Three in my bed alone.  If Jason walked in with his camera, there
would be no way to explain this. Come to think of it, having two guys show
up in dresses in the middle of the night might be just as hard to explain.
I lay back and let Randy finish. After all, why stop a great blowjob. It
didn't take long for him to reach his goal and swallow my entire load. He
moved over to do Alex, who didn't even wake up. I wondered if he was still
drunk.  Randy must have taken his load too, as Alex's dick was dripping
slightly as he pulled it out of his mouth and licked the tip. He slid out
of bed and put the covers back over us. He then went under the covers with
Austin.  I moved slightly closer to the edge so I could see what was
happening. I heard Austin wake up and I quickly closed my eyes almost all
the way, leaving them open just enough so I could see.

"Stop dude" he whispered quietly obviously not aware that he was actually
third this morning "what if they wake up and see us."

"Then I guess they'll be jealous" he whispered back, as he ducked back
under the covers. I saw Austin look up at the bed and I froze hoping he
didn't see me looking through my eye slits. I watched as Randy inched the
covers off Austin to expose him, probably knowing that I would be watching,
or perhaps he was just getting too warm under there.

"Wait, I don't want to cum yet" whispered Austin, pushing Randy off his
cock.  "Let me fuck you" Randy lay face down beside him, and I watched as
Austin leaned over and dribbled a lot of spit onto Randy's ass before
slicking up his own dick. He pressed his dick against his target and lay on
top of Randy. He began to move his hips up and down as he fucked slowly and
quietly. It wasn't long before I noticed the telltale signs that he was
cumming. He stopped and was breathing rapidly and quietly. I've never seen
such a quiet fuck before. Obviously they had done that before.  Austin
pulled out and wiped it dry on Randy's ass before lying down to go back to
sleep. Randy was left to jerk off, which he did as he stared directly at
me. I opened my eyes to let him know I was watching. He smiled and began to
jerk more furiously. Yep, that boy had the total hots for me. I licked my
lips to tease him and he shot his load onto his chest. When he finished, he
quietly got up and went to the bathroom. I heard him piss before he came
back.  We all woke up a few hours later as if nothing had happened at all.

I loaned Austin and Randy some of my clothes so they wouldn't have to walk
home in the dresses, as long as they promised to get them back to me.
After they left, I went and got us some coffee and water to help our
headaches.  We went to retrieve our bikes and hung out at Alex's to
recover.

We received an email after dinner and when we opened it, there was a link
to a site and a password. When we logged in we were shocked to see a
webpage with all the pictures of our day in the dress.  It had everything
and showed everything. From riding rides, to the incident at the bar and
everything in between. I had no idea how they got a lot of the pictures,
but our junk was visible in a lot of them. There were even shots of us in
places like the car where we got changed.  In the shower, and pretty much
everywhere else.  We selected them all and saved them into Alex's computer
so that we had a copy. He then duplicated them onto a jump drive so I could
have them too. I kinda wanted to see the pictures of the other pairs as
well. I knew if I traded with Randy, he would give me his and Austin's. I
figured Darren might share his and Brandon's too.  Damn I look cute in a
dress!  I'd date me.




I know, that chapter was a drag. OMG, I'm funny! Either that or I took
extra meds today.  More to come next chapter as the boys undergo another
test.  Feel free to read more adventures on my site at
www.pridecanadabc.com and I thank you for all your comments and suggestions
and even pictures to include with the website version of the story. I'm
trying to include as much as I can. Feel free to keep it all coming at
outinwest@gmail.com.