The Challenges Begin

Challenge 1: Show and Tell

John didn't waste any time getting me to play his game. The very next day he came to my classroom after school and gave me my first challenge:

"Let another man see your penis."

Well, that doesn't seem too hard, I thought. I grinned, checked the door, and started to unbuckle my belt.

"Nice try," he said. "It has to be someone else. Also, once they see it, you can't try to hide it. Leave it out in plain view until they've had a chance to get a good long look."

Still, I wasn't too worried about this one. We had a decent gym in the staff housing with a locker room and communal showers, so many of the teachers would use them after working out. Those of us who lived on campus used them regularly. I particularly liked using them because they were spacious and more luxurious than the cubicle shower in my tiny apartment bathroom.

I kept an eye on the gym area for the next few days waiting for someone who I wouldn't mind seeing me naked. I was happy to see Russ O'Connell entering one Tuesday, which was a pretty quiet day for the showers. It would make it easier if we had the place to ourselves. And as an added benefit, Russ was one of the large, bearish men on staff that I was intrigued by. Along with letting him see my penis, I would get a chance to see him naked too.

I got changed in my room and scooted over to the gym to find Russ walking on the treadmill. I did a circuit of weights, spent some time stretching, then headed over to the elliptical next to him. Russ was reading a magazine, so we exchanged brief greetings and carried on. Russ finished fifteen minutes later and wished me a good work out. I waited a few minutes, then followed him in myself. I undressed quickly, not wanting to miss my first view of Russ naked.

I wasn't disappointed.

The showers had no stalls, it was just a square tiled room with four shower heads, two on one wall and two opposite. There was a line of hooks outside the room for towels. When I came in Russ was adjusting the water temperature. He was facing away from me, standing to the side of the spray and testing it with his hand. Russ had strawberry blond hair that was very wavy, but not long enough to curl. The hair covering his broad back was blond and curly, covering the expanse of his shoulders and down his arms. His flanks and buttocks were less thickly covered, and his legs mirrored his arms. The skin underneath was pink, probably flushed from his workout.

When I turned on my shower, he turned around to see, and I got the first full on naked view of another one of my bear fantasies. Ever since I came on staff I had wanted to see more of Russ' body. All I had to go on till now was the tuft of tantalizing chest fur that always escaped the collars of his dress shirts. I had ogled his golden arm fur plenty, as well the hair covering his thick legs when he wore shorts, but had always been careful not to let anyone see me staring.

"Have a nice work out?" he asked me, stretching his hand back into the water. The temperature must have been good, because he stepped into the stream and let the water spray on his back. He rolled his head around under it, getting his hair wet, and running his hands through his hair to let it soak in.

I must have stammered something, reaching over to turn on my shower head opposite his, not wanting to take my eyes off the scene in front of me. The water was hitting his head and back, so the fur on his chest and large belly was still curled thick and dry. It was a beautiful blond, with a lot of snowy white highlights -- he must have been older than I had imagined. I had assumed he wasn't too much older than me, since his kids were pretty young. His face was always ruddy and clean shaven, and cherubic in a manly sort of way. The only sign of age there was the beginnings of laugh lines at the corners of his eyes. But the amount of white in his fur put him probably closer to John's age or older. His pubic hair was almost completely white, and thick enough that his testicles were mostly hidden. The base of his thick penis was hidden in the snow, but what was hanging out was dark pink with a matching glans. It hung supported by the balls underneath it, not quite long enough to point straight downward.

The water spraying on his head and back was splashing enough to slowly soak his chest fur, which was starting to lay flat now. I looked forward to a better view of his genitals once his pubic hair was soaked through, but figured I'd better get into my own shower stream before I was caught staring, and before I got a hard-on from the sight.

Remembering that I was supposed to be the one on display, I stepped into the shower and let the water run over my body. I decided to wash my hair first, facing him, to make sure he got a chance to check things out. I soaped up my hair and beard together, keeping my eyes closed and arms up scrubbing so he could get a good look without the risk of being seen. I leaned my head back into the stream of water, letting all the shampoo run down my body in rivulets. If he hadn't gotten a look at my penis by then, he never would. When I finally opened my eyes, he was still facing me, and looking straight at my genitals. I looked away quickly to avoid eye contact, then I turned around, slightly embarrassed now that I may have been too obviously voyeuristic.

I finished washing quickly, turning a few times as necessary, but Russ seemed to be taking his time now, soaking in the hot water, his hands up against the wall and letting it run down his back. I rinsed and soaked with the water on my back and shoulders, enjoying the warmth, and the view. Russ' whole body was big, but not in an obese sense. He was clearly strong, with a thick neck, broad shoulders, and barrel like torso. A good layer of fat covered it all, but it was compact, not bulging over anywhere. His buttocks and legs were thick, but well proportioned.

Keeping his hands pushed against the wall, Russ moved one foot back and bent the other leg, stretching. "My calves always tighten up on the treadmill," he explained, not looking back. The calves were thick, probably the place where his muscle showed through the most. They were carrying a lot of weight around. After a minute he switched to the other calf. Finally, he bent over briefly, his arms hanging loosely as he stretched his back. The hair on his back continued down between his buttocks, which opened slightly as he bent over, but not enough to see the pucker of his anus, disappointingly. It was a thrill to see the water run down to stream through his crack and then disappear below him, I imagined it flowing down to the underside of his scrotum to waterfall down to the floor.

When he stood I turned back away quickly, not wanting him to think I was staring at his butt. We turned off our showers together, and Russ chatted amiably as we dried and dressed ourselves. I didn't get a sense that he had been put off by my display, or that he even thought it was a display.

I proudly reported the next day that Mr. O'Connell had gotten a good look at my penis in the showers. I admitted I had taken a good long look at his too, while he was getting wet.

John responded immediately with his next challenge:

"Now let him see your penis again, only this time, let him see it fully erect. The same rules apply: once it's seen, you can't try to hide it."

Challenge 2: Hard Show and Tell

This challenge, of course, caused me much more angst, and it took me a few times seeing Russ in the gym again to work up the nerve for it. You would think after my experiences with John, being seen naked - or erect - would be no big deal for me. But I was still very shy, and worried that others might find out about my attraction to men. This was a conservative school, in a conservative time, and I honestly didn't know any other openly gay men.

Also, I liked the company of masculine men. I didn't know back then that you could be masculine and gay at the same time. I figured anyone I was attracted to would by definition be disgusted at my attraction to them. That's why John's acceptance of my obvious attraction to him was such a surprise and relief. That kind of thing couldn't happen twice, right?

Finally, I got up the courage to join Russ in the showers again. A few minutes after he left the work out area, I followed him to the locker room. Just the thought of having him see me erect got me hard the minute I started getting undressed. I had to hide it from him as I entered the showers because I didn't want it to be too obvious. This time I took a shower head next to his instead of opposite, so we were side by side. I stayed facing the wall while getting myself wet, then turned around to make sure I was in full view to fulfill the challenge.

Russ turned to face me while he was soaping himself up, talking about summer plans and end of year wrap up activities. I wondered what his reaction would be when he finally realized I had an erection. I turned my head back and forth to let the water get all of my hair and run down my front, and saw Russ glance down at what was poking out under my belly. I was in full profile to him, so it was quite obvious, pointing very slightly upward. Realizing how obvious it must have been I panicked and turned back toward the wall, hunching over to draw it back from view and letting the water flow over my back. But Russ kept talking without missing a beat, and kept facing my way.

I remembered I was not to try to hide it, once seen, so I turned reluctantly back away from the wall and soaped myself up. There was no risk of the erection deflating with how turned on I was getting. I noticed him glancing down a few more times and getting a view of my member. I soaped up my hair and angled myself a little obliquely to him, closing my eyes and letting the soap run down so that he could get a good look while not risking being seen spying on me. I slitted my eyes open just a bit while I had my arms up scrubbing my hair, and saw that he was totally staring at my hard-on with an amused smile, and peeking to see if I was looking.

We continued our small talk and I turned toward him while washing up. I was breathing hard from the excitement of being seen in a state of arousal, and it was a bit hard concentrating on what we were talking about. I asked about his kids, and what the family was planning for vacation. While he outlined their plans, I risked a look down at his private area. He was at the moment washing his chest and belly with a soapy facecloth, and his balls were swinging under his penis like a little double pendulum. His white pubic hair was hard to distinguish from the white soap suds partially covering his genitals. I don't think he saw me staring, but he stayed facing me throughout his washing routine, only turning occasionally to get his whole body wet or to rinse.

We finished up together, and I thought to myself that Russ may have spent a little longer than normal with this particular shower. He followed me back to the lockers and my erection stayed full and hard the whole time I was drying off. Russ kept glancing at it surreptitiously, I noticed, until I had pulled on my underwear.

Russ put a foot up on the bench one at a time to dry each leg off, and thoroughly dried his pubic hair and perineum each time, his thick penis and testicles wobbling around as he dried. I couldn't help thinking he was purposefully letting me get a good look in return, but he didn't do anything overt to make me sure. He never got erect himself, but it seemed he had enjoyed the show, based on how long he had stuck around talking. And maybe he enjoyed giving me a good view of his nakedness in return. I certainly fantasized that this was the case. My story seemed to please John when I reported back to him, and he ribbed me for a few weeks about how I obviously enjoyed having guys see me naked.

The next few challenges were more private, and harkened back to my first exposure to John when he found my roll of pictures. He gave me several photo assignments, just dropped a note in my mailbox with one line on it, like:

"Five prints of you tied up in your underwear."

"Ten print series of your penis from flaccid to fully erect."

"One print of you outside and completely naked."

He told me to put them in a manila envelope in his mailbox, which made me sweat, worrying about someone else grabbing the wrong envelope. Although, now that I had spent some time naked with Russ, I wouldn't have minded too much if he had been the one to accidentally see them. After the last picture challenge, we went a while without another one, and I thought maybe he was letting me off the hook. I was wrong.

Challenge 3: The Working Underwear Work Group

Several months went by without any new challenges from John. I was fully enjoying our new camaraderie. I had never had someone to speak so frankly to, and I loved that John was married, and we could hang out and do masculine things without feeling at all awkward. He had me over to their house for dinner frequently, we went fishing, we hung with the other guys.

Then one day, out of the blue, John handed me a cardboard box that had come in the mail. "I signed you up for something. Open it when you get back to your room."

It had been so long since we had talked about the challenges that when I opened the box it took me a minute to realize he had set me up again. In the box were four separately packed pairs of underwear from Duluth Trading Company, and a letter thanking me for my willingness to participate in this Working Underwear Work Group.

Now I've always loved Duluth's products, especially their advertising. Their Buck-Naked Underwear icon with the sexy bear and the "Censored" bar is like my alter ego. John had picked a real winner of a challenge here. The letter asked that I spend the next two weeks wearing the underwear for various activities, and it had some questionnaires based on different activities. Then there was an in-person meeting where I would meet with some of the designers and share my thoughts in a work group setting.

There were two pairs of boxer briefs and two pairs of regular briefs. I knew I wouldn't like the boxer briefs as much, but I would try them out and take notes as requested. My chief complaint about anything other than briefs is that my scrotum tends to stick to my thighs throughout the day. I like the fabric to tuck all the way up between my legs, cupping my balls the way a scrotum does. With boxers and boxer briefs, I'm constantly tucking the fabric up to either side of my scrotum, but as soon as I walk a few steps the fabric settles back down and they start sticking to my legs again.

I wrote all this in the notes on the different pairs of underwear, and enjoyed using frank and descriptive anatomical language. I even mentioned how each pair felt when getting an erection. I imagined a secretary getting flustered as she typed up the notes, imagined a big executive smiling and getting just a little aroused at my descriptions of myself. When I had finished the survey, I gave it to John with the return envelope, as he had asked to read what I had to say before I sent it in. I figured he would enjoy the read.

When I arrived at the office building two weeks later, I couldn't help getting a boner thinking of the upcoming conversations, and hoping it would be exclusively with men. I would feel awkward talking about this with a woman around, and I wanted the freedom to discuss things openly. I was wearing the pair of underwear I liked the most -- the briefs.

When I arrived upstairs the receptionist brought me back to a very plush board room, and announced me to the three men waiting there. There were two older men, likely in their 60s, and one guy that looked to be my age, maybe a little younger. One of the older men got up and welcomed me in, grasping my hand in both of his with a firm, warm grip. He introduced himself as Charles, and led me over to the others with a hand around my shoulder, like we were old friends already. He introduced his fellow designer Doug, who also stood and shook hands with me.

Doug turned to the younger man and introduced him as his son, Doug Junior. "We call him D.J. here, to avoid confusion. He's interning with Duluth this year, and starts grad school for design next year in L.A."

All three of them wore dress pants, well cut shirts, and ties. Junior had a nice black suit coat as well. I felt very under-dressed in my jeans and polo shirt.

Charles led me through to the other side of the room, which was more of a lounge area, with potted plants, plush chairs, and farther in the corner an area with a tailor's platform next to a set of full-length mirrors. The others followed us over, D.J. bringing some note pads and a pen. Charles handed me a white bathrobe that had been hanging on a coat tree. Next to it hung two jackets and a pair of jeans with a belt still in the loops.

"There's a dressing room through there" he said, pointing out an oak door with fancy brass hardware. "If you wouldn't mind coming out with just your underwear and the bathrobe on, we can get started."

He walked me over and held the door open for me.

The changing room was large and well furnished, with thick carpet, upholstered armchairs and a foot stool. No sterile plastic department store benches here. I felt like I was in a very expensive gym or salon. Around a half corner was what looked to be a sauna, and beyond that a large walk-in shower. On one side of the changing area was a sink with a good compliment of shaving equipment, powders, creams, and colognes, combs and brushes, a hair dryer tucked in a little cubby. On the opposite side was a full floor to ceiling mirror with a guilt frame.

I undressed down to my underwear, hanging my clothes on hangers in a narrow cubby next to the mirror. Then I put on the soft terry cloth robe. It was big enough to tie around my waist comfortably, but it was not very long, only reaching halfway down my thighs. My chest hair was also clearly on display in the deep V below my neck. Before walking out I took a look in the mirror. Out of curiosity, I sat in the chair facing the mirror.

Looking down I seemed fully covered by the robe. But looking in the mirror, with my legs open they way I normally sat, I could clearly see the white underwear, and the contours of the private parts held inside it. Sitting also made the V open up, revealing my large hairy chest and the top half of my ample belly. Where my pecs and at the top of my belly met there was a deep valley of brown fur. I figured I'd better make my way out before I turned myself on by staring at what the bathrobe revealed.

When I walked back out, Charles was still waiting by the door ready to receive me. I wondered if he had stood there the whole time. He had a habit of reaching up to stroke his full beard with his left hand when he wasn't talking. It was auburn, matching his hair, which had highlights of almost white blond. The sideburns had started to turn as much white as blond. Doug was sitting in one of the plush leather armchairs over by the tailor's platform, and D.J. was fussing with some tailoring equipment on a low table nearby.

Charles smiled warmly and walked with me over to where Doug was sitting. "I just wanted to thank you for agreeing to meet with us, and for filling out the survey so candidly. Also, thanks for offering to go along with the extra fitting session."

He motioned to the love seat across from the two armchairs. I sat, wondering what he was talking about -- what fitting session? John must have added something with my survey response when he sent it in.

"It's not part of the normal survey process, but it will give Doug Jr. some extra experience for design school, and round out his internship here with some more practical experience. Now, while he's finishing puttering around, why don't we go over some of your feelings on the underwear. I see you're wearing your preferred pair of briefs right now."