A gay story: 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.”
I leaned forward, remembering how I was on display the way I was sitting. I leaned on my knees with my hands together, partly obscuring the view, which I guess was silly seeing as my underwear was the reason we were all here. Charles leaned forward on his knees in the same pose, making my movement feel more natural. I wondered if it was intentional. Charles seemed to be a natural at putting me at ease — they all did in fact. Doug was reclining with one foot up on his knee. He looked as if he could easily be smoking a cigar in a lounge.
I cleared my throat, and decided what the heck, I had written all those details for this exact purpose, so why act shy now.
“Yes, I almost always wear briefs. I don’t mind boxer briefs sometimes, like for lounging in the evening, or if I’m somewhere communal where I might be walking around in my underwear. They feel more like shorts and I feel weird having people see me in briefs.”
“Well, I hope you feel comfortable here. This is our business, after all, and I don’t want you to feel at all shy about our conversation. That’s why we appreciated your survey responses so much.” As he spoke, he straightened a little, separating his hands and relaxing them on his knees — a slightly more open pose, allowing a better view of what was between his legs. His tie reached down to his belt buckle, which was hidden by his good-sized belly that overshadowed his lap. But below I could see the pouch where his balls lay heavy and pushing against the fabric of his pants.
I pulled my gaze forcibly back up to his face, and he was smiling warmly at me, his eyes twinkling and kind as if to say it was perfectly normal to be looking at someone else’s package. Which in his line of work I suppose it was. I forced my hands to relax and come back to my knees like his had.
Doug spoke up for the first time. Where Charles had a deep earthy growl of a voice, Doug had a more musical baritone. “You mentioned in your notes that it is an annoyance having your scrotum sticking to your thighs. Is that why you prefer the briefs?”
I nodded.
“Have you ever tried body powder in that area?”
I shook my head. “Not for every day use, no.”
“When do you use it then?”
I realized I had stepped in it then, and blushed. I occasionally used gold bond cooling foot powder on my perineum and bottom when masturbating, which made the bare skin feel more exposed in the cold air, but I couldn’t tell them that. I stuttered, trying to think of a reason, but failing. I must have looked like a deer in the headlights.
Charles stepped in to rescue me, “Please, don’t feel like you have to discuss anything you’re uncomfortable with.”
Then he sat back and waited, lacing his fingers together and resting them on his belly. This had the dual effect of soothing me, and at the same time pushing me to fill the silence which he let hang there. I sat back, again mirroring Charles’ posture.
“Well, when I play with myself, I sometimes put cooling powder on my underside…” I paused, remembering my intent to use correct anatomical language like in my survey. “…on my perineum, and between my buttocks. It kind of… increases the sensation there.”
Doug smiled widely, “I guess it would.” He glanced at Charles and winked, then addressed D. J. behind him. “How about you, Dougie, have you ever tried putting cooling powder on your bum-bum?”
Charles rolled his eyes at the banter, it seemed this may have been a running joke for Doug, flustering D. J. with these kinds of comments. Doug Jr. spluttered that no, Dad, he hadn’t. Doug carried on, “I’m just saying, it sounds exotic.” He turned back to me. “But the reason I ask is that I feel the same way — about my balls sticking to my legs. But briefs always feel too confining, so I use body powder and wear regular boxers.”
“What kind do you use?” I asked, enjoying the talk about Doug’s privates. He was not as large as Charles, but was cutely chubby, just like his son. They were both clean shaven, and where D.J. had firm chubby cheeks, his father had the faint beginnings of jowls. His receding hair was clipped short, and it was a dark grey fuzz that made me want to rub my hands on his head. My palms could almost feel the sensation as I imagined it.
“I usually use Gold Bond, but the original, not the cooling powder. We have several kinds of powder in the dressing room. I like to freshen up with a handful in the afternoon, especially when it’s a hot day. Feel free to try some when you try on the boxer briefs later.”
D.J. had come over to sit on the love seat next to me while his dad was talking. He had a cloth tape draped around his neck, which reminded me of how John wore his stethoscope around his neck all the time while he was working. Charles leaned forward, “Are we all set then?”
D.J. nodded and got up. Charles and I stood too. I was a little nervous, not knowing what came next. Charles gestured to the platform next to the mirrors, and I stepped up onto it. I felt awkward, up on display like that. It seemed that D.J. was feeling awkward too, probably shy about getting measurements on someone wearing only a bathrobe, also probably shy about having his dad and boss watching him do so. It was cute. I determined to be as laid back and confident as possible to help put him at his ease.
Doug was still in his armchair, which he had shifted to face the platform while we were moving around. He had resumed his laid-back stance with one foot up on the other knee. His tie was draped over slightly to one side, showing the row of buttons leading down to his pants. The stomach was well rounded, but not hanging down, I could see the simple silver buckle of his belt.
Charles put out a hand and said “I can take the bathrobe, now.”
I guess I should have been expecting that, but my hands fumbled a little with the tie, and when I handed Charles the robe I kept my eyes shyly on the floor. I had expected to be chilly, but there was a tall space heater a few feet away beside the potted tree, which hadn’t been visible from the rest of the room. Once I took the robe off, I noticed the warm air moving around me. It was a delicious feeling.
When Charles came back from the coat tree, I risked a glance up at his face. He was smiling at me warmly and he nodded. It warmed me through, like he was proud of me.
“Like we put in the letter,” Charles said, “D.J. just needs some practice with the full tailoring measurements, so he’s going to do the full works, even though we don’t strictly need it for our purposes. I’ll scribe for you if you’d like, D.J.”
D.J. handed him the clip board and pencil he had been holding, then stepped up onto the platform. He was still avoiding my eyes at all costs.
Doug piped up from his chair, “You’re going to have to look at him at some point, D.J., otherwise you’ll end up poking him somewhere he might not like.”
D.J. blushed deeply, but put on a brave face and looked me in the eyes. I smiled warmly and imitated the encouraging nod Charles had given me. “Don’t worry, I’m not shy. And I’m sure this isn’t anything your dad hasn’t seen before.”
That got a chuckle out of him. “Thanks,” he said, and I sensed him shifting into a more comfortable role as he lifted his tape from around his neck and started the measurements. “Lift your arms up for me?”
I had been measured by a tailor once before, but that had been fully clothed. It had also been one on one in a private area of a store, with no one watching. Two big differences from what was happening now.
As D.J. worked he walked around me, gently moving my limbs and head where he wanted. After the first direction to lift my arms, he just moved them around himself like I was a mannequin. As he took each measurement, he called it out to Charles, who marked it on the clip board.
D.J. had the gentlest touch I had experienced, his fingers barely touching my skin as he held the tape to different parts of me. It was like having a butterfly flutter over and land on different parts of my body. After a while it was making my skin extra sensitive as I had to focus to feel where he was touching me, and when he did touch me it made me shiver and get goose bumps. My stomach lurched a little when he put the tape around my widest point under my belly button.
“Sorry,” he apologized, “you’re a bit ticklish, I guess.”
I nodded in agreement, though it wasn’t tickling, as much as the feathery touches causing a heightened sensation. “Not a problem,” I assured him.
“Could you put your hands behind your head for a moment?” he asked. I did so, which lifted the slight overhang of my belly out of the way of the waist band of my underwear.
“I just want a waist measurement with the waist band out of the way.”
Reaching around my waist with both arms he slid his thumbs under the waist band of my underwear and lowered it half way down my bum, just revealing the top of my crack. Then he tucked his index fingers into the band and slid them forward to my front, causing the whole band to lower to my hips. He deftly slid them out again once he reached my crotch, managing with his gentle touch to completely avoid touching my privates. The waist band in front was now just over the base of my penis. I imagined a slim band of pubic hair showing.
He wrapped the tape deftly around me, and held it at my waist briefly reading the measurement, then reached around again and reversed the process with thumbs and forefingers sliding the band back up to its original place. The whole move took only about ten seconds, so there was a delay in the response of my penis to this most intimate of clothing adjustments. But as soon as the underwear was back in place, I felt the beginnings of arousal taking shape.
Ever since Charles had led me out of the changing room, my nerves at being in an unusual situation had filled my consciousness, not leaving any room for erotic thoughts. But the sensation of D.J.’s fingers moving my waist band had started a movement that was not likely to stop. I had time now to think about the view of my normally private skin Doug and Charles had gotten while my underwear was lowered. And now I couldn’t stop thinking about getting an erection and how obvious it would be to the men watching me get measured. Trying not to get an erection never works, it just makes it happen more slowly (if I’m lucky) and usually makes the end result even stronger.
When D.J. brought the tape around the back of me for the next measurement, I could feel the blood flowing in to fill the soft tissue of my penis. At the moment, the head of it was pointing straight forward above my testicles, gently pushing forward the loose fabric of the underwear. From the front you would see my testicles cupped by the underwear where they were pushed forward by my closed legs, and a small bump representing the head of my penis couched in the middle right above them, but not pushing out any further than they were. With the inflow of blood, the head was starting to edge forward subtly over the curve of the testicles.
The measurement he was taking now was around the widest part of my hips, and the tape measure came across the front of my underwear just at the top half of my glans. D.J. matter-of-factly pushed the head downward with one finger to let the tape slide behind it, getting a more accurate reading. Once the tape was gone the head slid back noticeably into position, now with some pressure building up to begin the stiffening process. Because of the position of my penis pointing straight ahead as it grew, it had to push out against the stretch of the fabric, which slowed the process. The only noticeable difference to the onlookers would have been a slight growth of the size of the head and a little more stretch forward than was present before.
“Can you spread your legs out for me?” D.J. asked.
I shifted my feet apart one at a time, until there I could feel that there was a gap between my thighs. This freed up some pressure from the fabric, allowing my testicles to drop a little in the scrotum, and my erection tent to stick out a little farther. I kept my hands by my sides, but it took a conscious effort not to readjust my lengthening member to point upwards to keep it from tenting my underwear so obviously. D.J. slid the tape up into the gap I had created and wrapped it around each thigh in turn, again so deftly that I barely felt his fingers, and he somehow did it without brushing the bottom of my underwear where the testicles were cupped under my now fully grown erection. The pressure of the underwear pulling against the head of my penis was pulling the glans upward slightly. It wasn’t terribly comfortable, but I thought maybe that would make it go away again more quickly.
“Sorry, guys,” I said, just to break the silence and the embarrassment I was feeling.
“Sorry for what?” Charles asked.
I looked down at the tent pole pitching my underwear straight forward. D.J. looked up from where he was measuring my calves, smiled, and rolled his eyes at the question. Like the others, he was great at deflecting awkwardness.
Doug spoke up from the chair for the first time. “I think he means the parasympathetic reflex of arousal caused by D.J.’s tactile stimulation of his erogenous zones, leading to the inflow of blood to engorge the spongy bodies, enlarging and stiffening his penis into its erect state, allowing it to become an organ of penetration.”
I was redder than ever, and D.J. looked up and smiled again.
“Yes Dad, I’m sure that’s exactly what he means. His boner,” he rolled his eyes again for my benefit.
“Yeah, well, I didn’t mean to get an erection,” I admitted.
“Most of us don’t,” Charles chuckled. “But what I meant was, its nothing to apologize about. It’s the natural response of a man’s body when it’s touched in that area. And you’re only in your underwear, with three men watching you. I’d certainly be in the same boat if I were you.”
“I’m sure D.J. doesn’t mind, he probably has one himself by now,” Doug added.
“DAD!” D.J. protested, and now he was looking down again. I could see his ears getting red, along with the back of his neck. He had finished the leg measurements, and was currently down on one knee. I was curious if his dad was right, but I was not at the right angle to see.
“One more measurement,” he said. He took the end of the tape with one hand and brought it up to rest right under my crotch. He pushed the tape lightly against the inside of my thigh, pushing up my right testicle so that it rested on the back of his hand. He brought the other hand over to my right foot to measure the length of my inseam. His palm laid against my thigh felt very warm, and when he removed it my scrotum settled back down to its original spot, sending a tingle through my loins and causing my penis to tense involuntarily, lifting slightly for a second before dropping again to point straight ahead.
“You can put your legs together again,” he said, standing back up next to the platform. His face was still a little pink, but not as bright as his ears had been. I avoided looking at his crotch, but it was hard not to.
“Don’t you want to get the rest of the underwear measurements?” Charles prompted him.
“Well, I thought I’d give him a minute to, you know…” he faded off.
“Soften up?” Charles queried.
I felt my face reddening again as he mentioned my state of arousal. Charles reached out a hand and put it on D.J.’s shoulder, giving it a gentle squeeze.
“You’ve got to get comfortable with working on clients when they have reactions like this. You can’t exactly skip measurements, and waiting for someone with an erection to soften up again isn’t always practical. Arthur here has demonstrated in his survey and since being here that he’s not shy, so he’s a good one to get comfortable working with.”
He took his hand off D.J.’s shoulder and addressed me. “Are you OK with going on?”
I nodded.
Charles addressed D.J. “Go ahead and pretend this happened during a normal fitting. I would generally ask someone if they needed a minute, or if they wanted to continue. The more you talk with people about awkward subjects, the easier it becomes. In all honesty, even if you wait until someone’s penis is flaccid, it grows right hard again once you go back to measuring. Sometimes its best to help the client work right through it.”
“You could always try to trigger a refractory period,” Doug piped in helpfully.
Charles sighed and closed his eyes in mock patience, “Yes Doug, not always the most professional of techniques, though.”
D.J. gave an extended eye roll, took a deep breath and grinned at me. “So, do you need a minute, or do you want to go on?”
“I’m fine,” I said.
Doug chimed in from his seat, “Look at them blushing, Charles. Aren’t they cute?”
Charles chuckled, but D.J. ignored them — all business now.
“I’d like to measure the underwear lines around your legs, would you mind stepping out of your briefs for a minute?”
“Sure,” I said. This was not what I had been expecting, but I had said we could go on. I bent over, lowering my briefs down around my ankles. I stood back up, and Charles offered me a hand for balance as I stepped out of them. Then he bent down, picked my underwear up off the floor, and folded them, holding them in one hand.
D.J. got back down on one knee. “Spread your legs apart again for me?” he requested. “A little bit wider.”
I shuffled my feet apart, until I felt my scrotum pulling away from my thighs, leaving a little gap. My erect penis was pointing straight ahead, its usually slight upward angle held down by the weight of my testicles hanging freely under it. D.J. passed the tape around behind my right leg, half way up the thigh, then slid it up into the crevice between my scrotum and my thigh. He slid it back and forth once to seat it along the line where my underwear would normally lie, along the bottom of my right buttock and back around to the front. The sensation of the tape rubbing somewhere so seldom touched sent another jolt to my loins and my penis tensed upward again for a few seconds, then relaxed back to pointing straight at D.J.’s bent head.
He called out the measurement, and Charles tucked my underwear up under his arm to write on the clipboard. It made me feel more completely naked having Charles holding my underwear, like I didn’t have any clothes to get back into.
Keeping the inside part of the tape where it was, D.J. reached with his left arm around behind and drew the tape up, so that it traveled straight from the bottom to the top of my crack. He seated it again sliding it back and forth once, then drew the back of the tape up around my hip and to the front. The tape joined for the measurement right in my pubic hair. I was glad I had showered that morning as his fingers pressed into the soft, freshly conditioned curls.
He lowered the tape to pass below my scrotum and moved it over to my left leg, following the same procedure. On the first side, D.J. had been blocking Charles’ view and giving a good view of my erection to Doug. But now he shifted to my left, giving Charles a clear view. I had been watching D.J. this whole time, with his red ears and neck. I looked up to see what Charles was doing. He looked up from where he had been watching my genitals, smiled warmly at me, and then looked back at my penis, not at all shy about what he was looking at.
The gentle brushing of the tape against my legs and scrotum was sending waves of heat through my genitals, and the arousal was getting so strong I was a little worried about having an orgasm. My breathing was getting deep and fast, and I had to keep my mouth open to keep it from being too obvious. When D.J. moved the tape back between my butt crack the second time his hand brushed the side of my scrotum, and I had to tense my butt and squeeze my pelvic muscles to keep from spurting right there. D.J. paused there as I panted for a few seconds.
“Sorry,” I apologized again.
“No worries,” D.J. assured me. “I’m actually impressed you’ve lasted this long.”
It was an odd thing to say, and I looked up at Charles, confused. He had a twinkle in his eyes. I looked over at Doug and noticed he had leaned forward for a better view. They were all smiling big smiles. D.J. looked up at me, still a little pink in the face.
I stood there, legs spread, my fully erect penis dipping and bouncing with my racing heart beat, with a bead of pre-ejaculate forming on the tip of my penis. I flexed my penis again and the drop slid down to hang from the bottom of my glans, but didn’t fall.
Charles was the first one to speak. “Well, to be honest, it seems that we have a mutual acquaintance – I believe you know John?”
I could barely think, “You mean, this was a set up?”
“Well, not completely,” Charles replied. “The survey you turned in was real enough, but this was all added as a bit of an extra bonus. John was actually a respondent to the same survey almost a year ago. D.J. had just started interning here, and the two of us had a similar experience with him to what we’re having now.
“He was very candid, maybe even a bit graphic, in his survey answers, which intrigued me. So I decided to have D.J. do a full measurement work up on him. I may have had D.J. get a few measurements not strictly necessary, and the measurements had much the same effect on him as they have had on you.
“When he took off his underwear for the final measurements, he had already made quite a wet spot on the front with pre-cum. And when D.J. slid the tape measure up next to his scrotum the first time it was more than John could take. Without any warning he shot a volley of semen right into D.J.’s face! It caught John off guard, and he almost stumbled off the pedestal before I caught him. He was still squirting semen over and over as I lowered him to the ground.
“I had never seen someone cum so much. He just lay in my lap, gasping until the last of his orgasm ended, oozing out onto his own leg. D.J. was caught off guard too, and got a few squirts on his face and chest before he could move. John must have apologized twenty times before D.J. could convince him it was all right. I think he had been fantasizing about something like this happening when he filled out his survey. Based on his physical reaction, he had probably fantasized about something like this for a long time, but when the real thing came along it floored him. Literally.
“Anyway, we’ve been in touch a few times since then, met for drinks a few times, nothing more, but I think he likes talking about his experience here, even though he seems embarrassed by it at the same time. About a month ago he called up and asked if we were still doing the underwear work groups. I said we weren’t, but asked why he was interested. He said he had someone he thought would get a kick out of the measurements, the same way he had, and he was wondering if we wanted to run a re-play. He thought you would have a similar reaction to what he had. And it looks like he was right.”
He was looking down at my fully stiff member. Hearing his description of John’s equivalent experience had only served to stoke my arousal, stimulating more pre-cum production. My penis was dripping a long pearl of it down to the floor as he spoke. “So what do you think, do you have it in you for one more measurement?”
D.J. didn’t even wait for an answer, but spread the measuring tape out wide and pressed it against my waist, passing the ends around behind me with both hands. He crossed them over at the back, and then let both ends dangle behind me, holding them there with one hand while he reached down between my legs with the other to pull the two ends forward. He pulled these ends snugly, which pulled them forward right between my butt cheeks, sliding all the way into the crack from top to bottom, where it pressed lightly on my anus. I now had the tape wrapped around my waste and then down my crack like a thong, coming out the front along my perineum.
He had done this swiftly in a well practiced manner. At the same time Charles had stepped behind me and started to kneel, and Doug had walked over to stand next to D.J., watching intently what his son was doing.
D.J. smoothly wrapped one end of the tape around the base of my scrotum, wrapping it like a purse string, trapping my testicles away from my penis and pulling them downward. At the same time he was wrapping the other half of the tape around both the scrotum and the base of my penis, a full loop and a half so the end was pulling up along my stomach. This was all happening so fast that my body didn’t have time to react with an orgasm, though it was fully primed and all this contact was sending me quickly to the edge.
He handed the top end of the tape to Doug, who held it up snugly against my belly. He handed the other end, the one wrapped only around my scrotum, back between my legs to Charles. Charles pulled his end gently but firmly back up through my open butt crack, causing more pressure against my anus, and pulling my scrotum down and backwards. Doug’s firm but gentle pressure in the other direction kept my penis from being pulled downward, so it stood pointed straight forward, the skin stretched taught, precum continuing to bead up and drip in thin strings to the floor.
Charles lightly brushed the open space between my butt cheeks with the fingers of his free hand, stimulating the hair and skin there. Doug used the fingers of his free hand to brush through the hair on my chest until he reached the nipple nearest him, which he brushed with each finger. I felt the shift from control to reflex as I passed the point of no return, the sympathetic nervous system taking over control of my loins. I knew that nothing could stop the ejaculation that was building there. At this point if everyone had backed off and left me there, it would still have happened, just a ruined orgasm where the semen would flow out like lava, but without the propulsion from the rest of my pelvic muscle involvement.
But they did not stop touching me. As the dam was about to burst, D.J. fondled my testicles, then reached the tip of his index finger up and gently brushed the underside of my penis, from the base of the scrotum all the way up to the most sensitive part of my body, just behind the head. Reflexively all my pelvic muscles clenched in preparation for my impending orgasm and I came up on my toes. Sensing what was happening D.J. wrapped his hand around my penis, but feather light like the rest of his touches, and pumped it back and forth as I ejaculated.
I have always found my ejaculations to be most powerful when the skin of my penis is pulled tight, so when masturbating during my climax I grasp the base of my penis with thumb and middle finger and pull down into my pubic area. The tape Charles was holding, pulling my scrotum backwards towards my perineum, was doing essentially the same thing, so my first shot sent a rope of semen right over D.J.’s head. The next two shots went straight into his face, and then they started losing height and two more ropes squirted onto his chest and stomach.
My calf muscles wobbled and my heels came down to the floor unsteadily. I don’t think I had ever cum while standing up before. The pull Charles was holding on my testicles threw me off balance and I stepped back with one foot to stabilize myself. But Charles was squatting there, and I tumbled backward into him. He must have been half expecting it, because he dropped the tape, caught me with one arm and leaned back himself, guiding me down and back so that I landed on my butt with him sitting right behind me, holding me reclining in his lap.
My orgasm hadn’t finished before I stumbled, and as Charles was guiding me down my penis kept shooting smaller and smaller ropes of semen across the floor. As I lay back gasping in his lap, I continued to squirt a few more puddles out over my right thigh. Charles reached around and brushed his fingers over both of my nipples while my penis was oozing out its last reserves of semen onto my leg, and the continued stimulation caused it to jerk reflexively, and my stomach convulsed as a few gasps escaped me. I was completely spent and had little control over my body’s reactions at that point. I just lay there catching my breath and looking down at my naked body. My legs were straight out and spread, and I was angled over to my right, as my left side had come to rest propped against Charles left leg. My penis was starting to soften, and was bending over to the right.
Doug reached down and picked up the end of the tape that he had dropped and proceeded to unwrap it. D.J. reached out and lifted my penis and scrotum out of the way as his dad unwrapped it. My loins tensed again when D.J. touched my genitals, and a three more gentle flows of semen pooled out into his hand, a mini-orgasm. He looked over at me and smiled. Watching father and son move my softened manly parts around was like an out of body experience in my post orgasmic state of contentment, like I was watching it all happen to someone else.
Doug moved my left leg up and bent my knee, placing my left foot flat on the floor. “Could you lift your bum for a second?”
I lifted it, then lowered it again after he had fished Charles’ end of the tape from under me. I moved half in a trance as he continued to unwrap me. When they lifted the tape away it trailed threads of semen with it. My penis was fully flaccid now, and rested over to the right of my scrotum. Some of the semen that had pooled on my groin sent a small drip down toward my right hip. It was cold, and tickled. My eyes were half closed, and I was taking slow, deep breaths.
Charles held me gently back against his chest, and let his hands explore my chest and upper belly from behind, brushing through my chest fur with his fingers. While I lay recovering, they talked amongst themselves, comparing my reaction with what had happened to John. I half closed my eyes and visualized their meeting with John as Charles told the rest of the story, his hands wandering over my upper body. D.J. and his father started to do the same down below, Doug focusing on my lower legs while D.J. got to play around with everything in between. For the first few minutes I was still in my refractory stage, so my penis remained completely soft. D.J. enjoyed waving it back and forth, or in circles, massaging the head with his fingers, pulling it taught and brushing his fingers along the sensitive length of it.
Charles told about how they had played in a similar way with John after he had collapsed and finished his long orgasm. He had almost shrieked when D.J. had grabbed the head of his flaccid penis right after he had finished, it was so sensitive. This had intrigued D.J. more than he could control, and he had driven John half mad playing with it while Charles gently held him from behind.
“Are you as sensitive as John after cumming?” asked Charles.
“I don’t know,” I lied, hoping their curiosity would lead them to find out on their own.
Doug moved up between my legs, saying “You got to play with John last time D.J., I think I should get to try this out on Artie.”
D.J. obediently moved to let his dad set himself up between my legs, while Charles shifted behind me, opening his legs to either side of me, and gently lifting me under my arms so that I was reclining against his chest. I could feel his boner against my back through his suit pants.
Doug lifted my legs and bent my knees, wrapping his arms around my thighs and back up to the sides of my stomach, while my feet rested on the ground to either side of him. My testicles hung down in my scrotum and my flaccid penis hung loose between them, only a few inches long in its natural state.
I had expected Doug to jerk me off or rub the head of my soft penis the way John had when he had me tied up, so it was a shock when he put his head down and
took my soft penis into his mouth. His shaved chin was rough with half a day’s stubble as it rubbed downwards against my scrotum. He adjusted his lips and pulled my penis further into his mouth, lifting the head with the tip of his tongue, then sucking in and creating a vacuum that drew my penis to its full soft length inside him.
It was a completely different sensation from John’s post-orgasm torture, but as he sucked on it, the roughness of his tongue had much the same effect, causing me to gasp and squirm with the overpowering stimulation. Doug pulled his head up and let my penis pop out, smiling up at me wickedly.
“Looks like we have another sensitive one, eh?”
Immediately he bent down and sucked it back in again, now bobbing up and down pulling the soft penis around like a worm being pulled out of the earth, and I started squirming again. I didn’t really want to get away, but the torment on the soft head made me try to escape instinctively. I tried lifting my hips, but his arms were wrapped around my thighs and it just lifted his upper body up with them, his head securely latched onto my fleshy manhood. He was as intent as a piglet on its mother’s teat, and as aggressive. I squealed myself, as it became clear he was not going to let up.
D.J. laughed watching his dad ride around on me as I squirmed, and Charles kept his arms firm around me, fingering my nipples occasionally. This was the first time I had someone’s mouth on my penis, my first blow job. It was the first time anyone other than John had done anything sexual with me, and all completely unexpected. I was completely naked, being played with by three men in suits and ties. A true gift set up by John.
My penis seemed to have been pulled erect again by Doug’s ministrations, and it didn’t take long for the over-sensitivity to give way to a second orgasm. Doug kept sucking through it, swallowing each squirt of semen as it came. And he kept it in his mouth, suckling gently as it softened again. He kept suction as he pulled off it with a pop, letting it fall wetly back over to the right side of my scrotum, completely flaccid again.
I stayed reclining back against Charles, still recovering from the shock of this whole scenario. Doug pulled himself back and stood, wiping his lips with the back of his sleeve.
“D.J., why don’t you take Artie back to the shower and help him get cleaned up. You’ll need a change of clothes, it looks like, so you might as well join him in the shower. Charles and I will clean up here. Then maybe we can try out some more measurement techniques with the boxers. Make sure you help him out with some of the powders, too.”
D.J. smiled, “I’ll get in with him and make sure he doesn’t have to lift a finger.”
Charles took a phone out of his pocket and looked at the screen. Then he looked up at me with a mischievous grin.
“John says he’s on his way. He’ll probably be here when you come out with the boxers. I’m sure he’ll want to help with the measurements too.”