As companies cut back on employee benefits, you have to find your perks where you can. My perk was having a desk across from the photocopier. When I wasn’t focused on my computer screen, I was watching women’s butts as they bent over to load paper in the copier. I never caught a glimpse of panties, but I kept hoping to see stocking tops and garters someday. That was my Holy Grail, and I prayed that short skirts would remain in fashion.
I surprised myself one morning as I realized I was looking at Greg’s butt. Greg was an analyst in a neighboring department, and we got along pretty well. I’d even gone to his wedding the year before, taking a woman we worked with as my date. I noticed Greg’s butt as he leaned over the copier because it looked like he was wearing a jock strap. Greg’s beige slacks showed distinct bands running under his butt cheeks and up the sides of his hips.
Did guys still wear jocks? I know I’ve seen close-ups of football players with visible jock strap lines, and I suppose baseball and hockey players need the cups for protection. But I thought basketball players and cyclists and most everyone else had switched to compression shorts. And why would Greg wear one to work? Maybe he hadn’t done laundry, but I just go commando when that happens.
It distracted me all morning wondering why Greg was wearing a jock. I saw him head to the break room for coffee and I jumped up to follow. I was too wound up to even start with small talk.
“Greg,” I spoke softly, “are you wearing a jock strap?”
He immediately looked down at himself and said, “Why, is it showing?”
I took that as confirmation and assured him it wasn’t visible right then. I felt compelled to explain why I’d noticed, and I made a point of saying it was women’s butts I watched. His just stood out because of the jock.
“I like ’em,” Greg said without apology. “I wear one a lot. I’ll have to remember not to wear one under these slacks, though,” he added, grinning.
It became a game for me, trying to decide each day whether Greg was wearing a jock. I almost asked him how many he owned; and did he have them in colors? I knew I’d gone off the deep end when I wondered how often he washed it/them. I had flashbacks to junior high school when I took my gym clothes home to be washed only every other week or so.
We were alone in the break room again, and I couldn’t resist brushing my fingers across Greg’s butt, checking to see if he wore a jock strap. He was, and he blushed at my touch. I grinned at him. If I’d been a nine-year-old kid I’d probably be singing, “I know what you’re wearing, I know what you’re wearing!”
And if only Greg hadn’t blushed. It gave me power over him, at least in my own mind. I’d learned how to push one of Greg’s buttons, and like a kid I didn’t let up. I touched his butt nearly every day to see whether he wore a jock. Most of the time, he did.
After the third or fourth time touching Greg’s butt and him not slugging me or calling me a pervert, I started trying to snap the leg band against his skin. It didn’t take me long to realize he did have multiple jock straps. The leg bands were different sizes. One jock in particular must have been new — the elastic was still strong enough that I could elicit a small ‘ouch’ when I snapped it against him.
I was obsessed. When Greg told me his jock that day was red, I insisted he show me. We went to the men’s restroom and Greg dropped his slacks and pulled his shirt up. I could see the trail of hair leading down from his navel and the dark, curly pubes peeking out each side of the jock’s pouch. He gave me only a quick look because we were afraid someone would come in and see us. Greg turned his back to me as he pulled up his slacks and my brain captured an image of his hairy butt just before it disappeared.
We tried to pass off what we’d just done as idle curiosity. I asked Greg how his wife liked his jock straps. I thought mentioning her would revive our heterosexuality, and hide that I’d just been checking out his ass.
“She likes to slide her fingers inside along the bands,” Greg told me. “The jock is all I wear around the house sometimes, like when we’re watching television.”
The image of Greg’s butt haunted me, and it popped into my head at the oddest times, like during staff meetings. I found myself daydreaming about Greg’s butt.
I probably had a normal boyhood, including the camaraderie of sleepovers, camp outs, and group showers in gym. We’d go skinny-dipping and play grab-ass games, but I never considered myself gay or bisexual. On the other hand, I’d not dated any particular girl for very long. I told myself I needed to establish my career before settling down.
Thinking about sex with men didn’t automatically disgust me. Sex was sex, and I could see benefits to getting off with another man. We wouldn’t have relationship issues and feelings and ‘that time of the month’ to deal with. But in this age of AIDS, promiscuous partners were dangerous. I couldn’t justify the risk, but I wasn’t finding energy for a heterosexual relationship, either.
The next time I saw Greg bent over the copier, I went over and grabbed his ass with both hands.
“What are you doing?” Greg hissed as he quickly stood up.
“It’s like waving a red cape in front of a bull,” I told him. “If you shake your bootie at me, you have to expect a reaction.”
We both laughed like it was another childish game, but now there was a tension in our friendship. I couldn’t keep my eyes, or my hands, off Greg’s butt. Twice, I came close to being caught by others with my hands on Greg’s ass. Fortunately, no one suspected the two of us might have something sexual going. And it was sexual — my dick started getting hard whenever I followed Greg around the building.
I wondered if Greg was getting hard, too. The next time we were alone in the break room I felt his ass, sliding my fingers along the side strap of his jock. Then I moved my hand around his front and felt for his dick, squeezing it. It wasn’t hard at first, but I could feel it rapidly growing in my hand.
“Jeez, Mike,” Greg whispered, “not here!”
“Where, then?” I responded, louder than I wanted.
I hadn’t thought things through. I guess I was expecting something quick in the men’s room, or maybe a broom closet. Instead, Greg suggested my apartment, after work on Friday.
“I can tell my wife our company is having an after-work cocktail party. She hates those things.”
That was on Wednesday, and I bet if I’d taken my temperature I would have found it elevated for the next two days. Maybe I was gay — I spent Wednesday and Thursday nights cleaning my apartment, even going so far as to buy new guest towels for the bathroom. And lube. And condoms.
I didn’t know what to expect on Friday, but I kept telling myself, “He’s safe, he’s married.” I could barely function at work as I tried to imagine what sex with another man would be like. Greg followed me home from work, and my hands shook as I unlocked my front door.
“Relax, will you,” Greg said. “This is supposed to be fun.”
“You’ve done this before?” I asked. The question had been on my mind all day.
“Nope, but we both figured out how to have sex with women. Men have to be a lot less complicated.”
I laughed, but it probably sounded forced. I didn’t know what to do next. Did we go straight to the bedroom? Did we undress each other? I never worried this much with a woman. I just did what felt good. I asked Greg if he wanted a drink.
“No, not unless you need one to relax. I can’t stay all night so let’s just get to it.”
Greg’s eagerness threw me. I’d been the one after him. On the other hand, if Greg hadn’t suggested coming to my apartment, I’d probably still be patting his ass at work and totally frustrated. I was no longer sure who seduced whom, but I was positive I wanted Greg’s ass. I led him back to the bedroom.
We each stripped. I’d tried on three pairs of underwear that morning before deciding on black silk boxers. I removed everything but my boxers and Greg stripped down to a black jock strap.
“At least we’re color coordinated,” I joked.
I waved at the bed, indicating for Greg to climb on first. Seeing his ass as he crawled up the bed lit a fire in my belly. I quickly followed and placed my hands on his butt. Greg sank down on the bed and rolled onto his back. I was disappointed at losing my connection with his firm, beautiful ass, but there were plenty of other parts to explore, and at the same time Greg was checking me out. We actually got in each other’s way. Greg pushed me back on the bed and told me to let him go first.
Greg seemed fascinated by the hair on my chest and he ran his fingers through it. He pinched both nipples, and then moved his fingers down to my navel. As he poked a fingertip in my navel, I realized my dick was already hard and throbbing, making a tent of my boxers. Greg noticed, too, and placed his hand over my erection, rubbing the silk up and down on it.
I gasped, thinking it was too soon to come, and fortunately Greg moved down to fondle my silk-covered testicles. I was still boiling but the danger of an eruption was past — for the moment. Greg then stroked my hairy thighs, and worked his hand inside one leg of my boxers, brushing across my hip and finally twisting in my pubes.
“You are a healthy boy,” Greg said as he traced a finger over the length of my erection.
I was so turned on that I wanted to jump up and take his ass right then, but Greg continued to tease me as his fingers roamed my crotch. Finally, he took hold of the waistband on my boxers and slowly pulled them off me. I said prayers of thanksgiving when he kissed the head of my dick.
When Greg moved lower to kiss my testicles, I moaned. And when he took one of my balls in his mouth, I was ready to do anything for him. He owned me then. I loved having my balls played with, and Greg did it aggressively. He tugged so hard on my balls with his mouth that I cringed, but my dick got harder than ever.
It was almost a relief when Greg moved back up to my dick, but the relief was short-lived. He licked it all over like a lollypop and then in one quick plunge shoved the whole thing in his mouth. That was it for me — I immediately started shooting come down his throat. There’s no way I could have warned him first; it happened too fast. And I was embarrassed, of course.
“Taste’s great!” Greg said brightly.
I mumbled an apology for coming so soon.
“Relax, dude. The evening is young. I expect you’ll be good for another load or two.”
I was grateful that Greg was understanding and not disappointed. The gratitude dissipated when he crawled up the bed and sat on my chest. Greg pushed his jock right in my face and said, “How do you like this one?”
Greg didn’t wait for an answer. His knees pressed on my shoulders and prevented me from moving much. Greg rose up on his knees and began to brush his jock-covered crotch back and forth against my chin.
“You need another pillow.”
Greg pulled the other pillow over and placed it under my head so that now my nose pressed right up against his jock. He had a day’s worth of sweat and odor built up and I sniffed at it. No deodorant or cologne there — he smelled like a natural man. I remember thinking I should be turned off by him pushing his crotch in my face, but I wasn’t. I opened my mouth and made a playful bite at his jock.
“You dog,” Greg shouted. “Bite this!”
Greg pulled the pouch of his jock strap to the side and started slapping my face with his erection. This was the first time I’d gotten to see his dick and it looked huge up close. And it was really hard — I definitely felt it when he hit me.
Greg rose up and pressed his balls against my lips. I wondered if his were as sensitive as mine, and I opened my mouth to lick one. With his knees on my shoulders, I didn’t have much use of my hands, so I used my tongue to guide one testicle into my mouth. I couldn’t fit both of them in at once, but Greg didn’t seem to mind. Once he thought I’d sufficiently laved the first one, he pulled it out and shoved the other testicle in my mouth.
I tried not to think about what was coming next. Greg was getting so vocal that I thought maybe I could get Greg off just from sucking his balls. No dice. Greg pulled back a little, grabbed hold of his dick, and pushed the first couple inches into my mouth.
Fortunately, Greg didn’t immediately try to shove his whole length down my throat. He took his time and gave me a chance to get used to his size, and to learn what to do. If I started choking, Greg quickly pulled out and said, “Sorry.” But then he’d push right back in. I figured this was payback for all the times I got aggressive when a girlfriend gave me a blowjob.
Unfortunately, Greg didn’t have a hair trigger like me, and it took awhile to get him off. I realized he was intent on shoving his whole dick down my throat, and the sooner I learned to take it the sooner he’d come and then pull out. My throat felt raw — the angle was bad and the head of his dick hit the back of my throat each time Greg thrust in.
I didn’t understand why Greg stopped, until I felt his dick pulse in my mouth and his warm come spray into me. I smiled, although Greg probably couldn’t tell, since my lips were still wrapped around his dick. But I was happy I’d succeeded in getting him off, and in surviving my first blowjob. Giving my first blowjob, that is. I did wonder if he’d permanently altered the shape of my throat. Even after Greg pulled out I could taste and feel him in there.
Greg flopped down on the bed beside me and unceremoniously pulled the second pillow out from under my head for his use. He laced his fingers behind his head and his eyes closed. I studied the dark hair in his armpit, eventually moving on to look at his belly, still rising and falling as he caught his breath, and my eyes followed the treasure trail down to his now softened dick.
The jock strap was still pulled aside, exposing his dick and balls. Over the course of that evening, Greg never did remove his jock. We either pulled it to the side, or reached in from the top, but we left the elastic bands in place. A jock strap is a remarkable design in that it doesn’t hide the one place I really wanted to get to.
I rolled onto my side and place my hand on Greg’s belly, trying to show ownership.
“Am I going to get to fuck you?” I asked.
“It’s why I’m here, stud,” Greg responded. “That’s the one thing my wife can’t do for me. I want to try this. Once, anyhow. See if I can take it. But don’t you think you ought to romance me a little first? You don’t get to just slam it in there!”
With that, Greg pulled me over on top of him and pulled my lips down against his. I hadn’t planned on this part. In my wildest dreams I figured suck, fuck, say something about the ball game that weekend, and call it a night. I didn’t think we’d kiss. After all, this was just sex — we weren’t lovers. And we were guys. Greg had a fucking mustache and chin whiskers!
Which felt pretty damned good. Probably better than my five o’clock shadow. And Greg had a talented tongue. But I was on top and he let me lead. Without thinking much about what I was doing, I moved over to nibble on Greg’s ear. He seemed to love it when I licked inside his ear and then sucked on his earlobe.
As I kissed down the side of Greg’s neck, he warned me not to leave any marks. I treated him like my girlfriends except he had hairy armpits, flat tits, and a baseball bat growing from his crotch! I couldn’t believe he recovered so quickly. Of course, I was hard, too, and I rubbed our crotches together.
I couldn’t wait any longer. I stretched out to get the lube from the nightstand, and then I pushed Greg onto his side with me lying behind him. I greased my fingers and then tickled his ass hole. I wiggled my index finger, adding just enough pressure to dent the skin a little. Greg shimmied, which allowed my finger to slip in a bit further. As long as he wasn’t complaining, I continued to press on, sliding my finger all the way into his ass.
I leaned over and kissed his shoulder. As I finger fucked Greg, I tried to compare it to fingering pussy, but Greg’s broad shoulders and musky smell told me he wasn’t a woman. I had the sudden urge to bite his shoulder and I really had to fight it. I wanted so much to leave tooth marks showing that I’d been on his back. His ass was mine.
I slipped a second finger in. Greg wiggled some more, and I asked him if it felt okay.
“See if you can find my prostate,” he told me.
I didn’t know what it was supposed to feel like, but I figured Greg would let me know when I hit it. He started panting and he hissed, “Keep doing that!”
I did, but only for half a minute longer. Then I pulled Greg up on his hands and knees and crawled up behind him. Greg’s hairy ass, outlined by the black jockstrap, was beautiful. Beauty is in the eye of the beholder, and I was the one holding his ass as I lined my dick up with his pucker. This was something special — a man’s ass just waiting for me to mount it.
And Greg took it like a man. He didn’t cry out when I pushed in. I was the one who had to stop after getting just the head of my dick in his hole. It was so tight and I was so turned on that I had to stop and regroup for a moment. Both of us were breathing hard.
“You all right there?” I asked.
“Yea, just take it slow, will you?” Greg replied.
I pushed on in, slowly as requested, but without stopping until I was completely buried inside Greg’s ass. I could feel his ass muscles clinching around my dick and it was wonderful. And warm. I had my hands on Greg’s hips, holding him tight against my crotch. He wasn’t going to get away from me — I’d found the perfect home for my cock.
“Okay, you can start moving now,” Greg said.
Fortunately Greg couldn’t see my face. He thought I’d been waiting for his ass to get used to me. However, I’d just been savoring the moment. It was a reminder that there were two of us involved. I started to slowly withdraw and then inch back in, and I asked Greg how that felt.
“Well, it’s not a walk in the park, but I can deal.”
After another minute, Greg told me to speed up a little. His hips started swaying in rhythm to my thrusts, and I started pounding just a bit harder. And harder. I quit worrying about how Greg felt and began plowing his ass the way I wanted.
“Go for it, stud!” Greg yelled.
Boy, did I! I grabbed hold of Greg’s jockstrap and held it like the reins on a horse. I rode that stallion until my nuts exploded, and I tried to bury my dick even deeper in Greg’s ass as my come started squirting into him. I collapsed on top of Greg, pushing him flat on the bed. I could have fallen asleep right there in the saddle, with my dick still in Greg’s ass.
But Greg wouldn’t stop wiggling — his ass, especially. Eventually, he managed to flip over so we were face to face. Alas, my dick lost its warm shelter.
“You look like you enjoyed it,” Greg snickered.
“It was fantastic. Thank you.”
My girlfriends nearly always wanted to talk or to cuddle after sex, kind of a cooling down time. I hugged Greg, trying to convey my sincere appreciation for a wonderful evening. Greg squirmed out of my embrace, and, actually, I was fine with that. It seemed like a more ‘manly’ reaction than cuddling.
Greg, however, only wanted out from under me so he could be on top. He kissed me, forcing his tongue down my throat, while grinding his jockstrap-covered crotch into mine. I had just come, but Greg hadn’t, and he seemed intent on evening the score. When I felt his finger trying to breach my asshole, I finally realized he truly wanted equal access.
“No, I can’t,” I started to say.
“Yes, you can,” Greg murmured. “You’ve just had the best sex of your life, and you want to make sure it’s going to happen again. Besides, you’re curious. Aren’t you?”
By then, his finger had made it inside and was starting to explore. I lost track of what Greg was saying as I concentrated on the internal massage I was receiving. Every few seconds my body would twitch from the sensations his finger was causing. My ass would rise, and then come back down on his finger. I felt like I was being impaled, and I wasn’t sure I wanted something bigger than Greg’s finger in there. It didn’t ease my mind any when Greg wedged a second finger inside me.
I was on my back watching as Greg pulled his jockstrap aside and started lubing his dick. When he lifted my legs onto his shoulders, my asshole clinched in anticipation — or more correctly — in fear. I tried to will it to relax as Greg pressed forward. I know I gasped as the head of Greg’s dick finally poked through my asshole. I wanted to scream, but I knew Greg hadn’t when I entered him, and I tried to match his stoicism.
Despite Greg’s instructions to me about taking it slow, he seemed to think it was better to get it over with. Greg sank his shaft into me, and he was just too big for me to take without a sound.
“Shh, shh. It’s okay,” Greg told me. “The worst is over.”
He leaned forward and kissed me on the lips, which I suppose was one way of quieting me. It didn’t do much for my mind, though. I was on my back, sharply folded in two with my knees by my ears, my butt in the air and with a man’s dick speared through it. All the kiss did was reinforce how little control I had and how much in the ‘driver’s seat’ Greg was. I guess his tongue did provide a little distraction, though. I’m not sure when I realized Greg had begun the tiniest little jackrabbit thrusts into my ass.
I can’t tell you when I changed from wishing it would end to hoping it wouldn’t. I’m sure my prostate was involved, although there wasn’t any Eureka moment where I screamed, “That’s it — you’ve hit it.” I do know I started anticipating Greg’s thrusts and rocking my butt up to meet him and I clinched my ass around his dick as he withdrew — like I didn’t want to let go. We built up quite a rhythm, and again Greg had me beat in the stamina department. I’m sure I didn’t screw him for nearly as long.
It was a shock when my dick started squirting come on my belly. I don’t know for sure that I was even hard. I thought this was about Greg getting off, not me. Who knew having your gut massaged from the inside could cause an orgasm!
Greg swore later that he knew it could happen, and he was waiting for me to come before he started drilling my ass in earnest. He said the best part was knowing I was a man, and therefore not fragile. He didn’t have to worry about leaving bruises. Greg spent his energy beating my ass into submission.
It was a long time afterward before either of us had the energy to get dressed. Greg felt perfectly comfortable wearing only his jockstrap around the apartment as he went to the bathroom to clean up and then joined me in the kitchen for a post-coital drink.
Still acting like a kid, I had to point out that I’d come three times and Greg had only come twice.
“I’d better save one for my wife just in case she’s feeling frisky when I get home,” Greg joked. Then he added, “Otherwise, I’ll just take it out of your hide the next time we get together. You want to shoot for next Friday again?”