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.