Young Greg Ch. 01: A Boy's Curiosity

All this started a couple of years ago when I was in college. I was hanging out in my buddy Steve's dorm room one Sunday afternoon. Steve had a corner single, which made it a cool place to hang out. He also had a pretty large TV, which doubled as a computer monitor. We were just sitting around, shooting the breeze, when he asked, "You wanna put on a porno?"

"Sure," I answered, not wanting to be uncool. Steve went to a porn website and downloaded one of the longer videos, and soon we were being treated to a widescreen color performance full of tits, cunts, big dicks and assholes (the little round kind), in every possible position and combination. After about twenty minutes, my cock was straining inside my jeans, and Steve said, "Damn, I'm horny. I haven't gotten laid in a month. How about you?"

"Me, too," I replied. "It's been a long time." In fact, it had been a long time, a bit over a year, since I had had sex with a woman. Cathy Winnstrom and I had gone out for a couple of months, and had had sex exactly six times in the three nights we had slept together during my sophomore year. I had been a virgin. She was a little more experienced. Living in the dorms, it was difficult to find privacy, but roommates do occasionally go home for a weekend, and we made use of the opportunities. Since then, Cathy had moved on to other fellows, and I was left to masturbate nearly every night, imagining her sweet breasts, her round bottom and her wet pussy.

Steve started unbuckling his belt. "I gotta jack off," he announced. "Want to do it too?"

I did, desperately, but wasn't sure where this was going. "What are we talking about?"

"Nothing queer," he responded. "I'm gonna jerk my cock, and you can, too, if you want." Steve was naked by now, his hard penis in his hand, and I started to strip. We sat back, next to each other, on the old couch, and started to play with ourselves as the porno vid continued. Steve had a big erection, and all of the hair around his dick and nuts had been shaved smooth. My own stiff cock was considerably smaller, and was surrounded by my big blond bush, of which I was rather proud. The dorm showers being open bays, with six shower heads each, we all saw each other naked, which was no big deal. I guess about two-thirds of the guys shaved all their pubes off, most of the rest, like me, sported full bushes on their crotches, and a very few eclectic individuals cultivated landing strips, tiny patches, and other offbeat stylings of their pubic hair.

After about fifteen minutes or so of masturbating, stopping to rest, letting our dicks go soft, massaging them back to full erections, and repeating the process, I fired a big wad onto my chest and belly, followed by several smaller ones. Watching me shoot my load, Steve started coming on himself as well, and soon we were sitting naked, with limp cocks, just relaxing. Looking at my sticky jungle, Steve remarked, "Man, you should shave that bush off. Who's gonna want to blow you with all that hair?"

Actually, Cathy had sucked my cock every time we were together, though as foreplay and not to make me come in her mouth. But I knew the cool guys mostly shaved their pubes, and, from what I had heard and the little I had seen, virtually all of the girls did as well. Not really wanting to lose my bush, but, again, wanting to fit in, I asked Steve how best to do the shaving. He told me, "If you really want to do it, I'll help. First, we'll lay out a towel on the floor, you stand on it, and I'll trim the hair off with electric clippers. Then we'll go in the shower and I'll help you shave everything smooth. You can do me at the same time, 'cause I'm about due, too. Not likely anyone else will be in the showers at this hour, so we'll have some privacy.

So, he trimmed me up, and we went in the shower. Handling me very gently, he, soaped up my stubbly pubic area and my nutsack. Then, with a new razor, he very carefully went over my skin, shaving it smooth like a small boy's. Stretching my scrotum tight, he shaved off all the hairs around my balls. When he finished, I rinsed off down there, soaped up his groin, took the razor and shaved him smooth as well. We both became erect again during this, but did not try to play with each other. That would have been just a little too gay. Steve rinsed himself off, we got out of the showers and dried ourselves, dressed and went back to his room to chill for the rest of the day.

After that day, we would get together in Steve's room occasionally to watch a porn video. Inevitably, the penises would come out and we would rub one out together. Never did it go any farther than that, although I would have liked it to, to hold his boner in my fist and feel it pulsate as he came in my hand. I wondered if he felt the same way, but neither of us ever worked up the nerve to ask the other to go forward.

Graduation eventually arrived, and I moved to a new city to take a job in an office. I had no friends or family there, so it was a clean start for me. In particular, I was not meeting many available girls, and the hornies were setting in. The closest thing I was getting to a sexual encounter of any kind was Linda Levy. Linda was a well put-together woman of around fifty, who had worked at the company for many years. After being introduced, she had taken up the habit of laying her hand on my forearm when we would chat in the break room or in the hallway. Having sat through the sensitivity training videos, I immediately recognized this as technically being sexual harassment by a senior employee of a subordinate. However, being new, I did not want to be "that guy," the candy-assed new hire who could not handle a very minor come-on without running to HR to lodge a complaint. At the same time, I did not want Linda to take ownership of me as her bitch, either. I needed to address this from a posture of equality. What to do?

I eventually decided on a two-pronged approach that would preserve my work relationship with Linda unless she decided to get nasty. First, whenever she would place her hand on my arm during an otherwise innocent chat, I would reach back and stroke her forearm with my fingers. This would send the message that I welcomed, even enjoyed, her little attentions, and that I felt sufficiently empowered to return the gesture, and not helplessly forced to submit as her toy whether I liked it or not.

Second, I described, in a detailed writing, everything that had occurred between us during these incidents, as minor as they were, including the names of any witnesses present. When completed, I sealed it in an envelope and mailed it to Stan, my best friend in the office. Whenever another little encounter would occur, I would write up a description, seal it up and mail it off to Stan. My instructions to him were only to date stamp every envelope he received from me, to keep them in a private drawer that only he had access to, and to never, ever open any of them. I did not tell Stan what these letters contained or who was involved. I only told him that I was documenting some questionable conduct that may affect me in the future. My plan was that, if Linda should ever make trouble for me, I could then go to HR and file a complaint for sexual harassment. When, inevitably, she would call me a liar, I would ask Stan to produce the letters, and HR could read for itself my account of events as they transpired, taken from sealed, dated envelopes clearly sent well before any of the trouble began. Stan did not need to back up my story, thereby harming his own relationships with co-workers. All he had to do was hand over sealed envelopes to Human Resources. Unless the shit ever hit the fan, he would never even know that Linda had any involvement with me at all. It might not be ironclad evidence of my case, but it just might be enough to save my ass.

It didn't take long. After a couple of months of touchy-feely, Linda had a little too much to drink at the office Christmas party. She got quite flirtatious with me when no one was looking. Other than the usual arm touching, she didn't get physical, but freely made some off-color comments and double entendres, and very plainly let me know that she would welcome an intimate encounter with me. I wasn't prepared. I honestly didn't think she would be this blatant and, frankly, I hadn't thought about an affair with a much older woman. I was way too interested in scouting out cute young girls around my own age. I gave Linda a noncommittal response and walked off to another part of the party.

A week or so later, Linda encountered me back in the filing area with no one else around. She started to chat, placing her hand on my arm as usual. I responded in my accustomed way. Then, suddenly, she leaned in and kissed me full on the mouth. Her tongue was down my throat, and her hand was clamped over my penis, which automatically started to swell. After about four long seconds of shocked paralysis, I pulled away. As nicely as I could manage, I said, "Linda, I like you. I think you're a nice lady. Let's just pretend this never happened."

She glared at me, and through clenched teeth, muttered, "Of course." Upon later reflection, it occurred to me that an encounter with an attractive fiftyish cougar might be enjoyable after all, but this was work and I didn't need to create problems for myself. Linda, however, didn't give up. A couple of days later, she cornered me alone in the break room, and asked me flat out, "Greg, what the hell is wrong with you? Most men would give their left nut to get me in bed," probably true; she was a hottie, "and you just blow me off like I was the cleaning lady! You'd better get it together and start slipping me some of that boycock, or things might not go so well for you around here. I know everybody, and I could make your job hell, or even get you fired. Don't think I can't!"

I was stunned. I never thought anyone would take harassment to this level in the current day and age. I responded as calmly as I could. "Linda, I'm not going to be your boy toy. Yes, you're attractive, but this is work and I'm not going to mess up my reputation or be the guy who sleeps his way to the top. We can forget all this and go on as normal, or I can complain to HR. It does nobody any good to be accused of sexual harassment, but I will go there if you force me."

"You wouldn't dare," she hissed. "I'll make you look like a liar and a pervert, and you'll be out of here on your ass before you know what happened! You have no proof, none."

"Maybe not, but here's what I do have," I shot back. "I have postmarked, sealed, dated envelopes containing full descriptions of every little innuendo you have made, every time you rubbed my arm in the hall, your drunk performance at the Christmas party, word for word," hoping she might not remember everything she said, "and last week's physical assault on me, because that's what it was. If I have to go to HR, I'll just hand over the stack, tell them this is my story, and let them open and read the narratives for themselves. It's clear that the stuff was all written and mailed before you started strong-arming me this morning. I'm telling you now, because all I want is for this to go away. I could have just taken the stuff to Human Resources and let them decide what to do with you, but I didn't want to do that. I don't want trouble for me or for you. Let's just let it go."

Linda thought hard about it for a long thirty seconds. Finally, she caved. "OK, you win. Back to normal." I started searching for a new job that afternoon, it didn't take long to find one, at a higher salary than I was making.

In the meantime, I started thinking about what if I had taken Linda up on her advances. What I really wanted, I knew, was a real girlfriend, a contemporary, to go out with and do all the fun stuff my friends back home were doing with their girlfriends and boyfriends. But I wasn't finding much yet, even though I was going to the local bars and clubs and trying hard to meet people, and the cry of my penis was growing louder in my head day by day. Linda was, after all, a pretty lady, and we could have fucked and sucked each other into oblivion if I had let it go there. But where would it end when and if I ever found The One? Would she let me go? Or would she blackmail me into staying on as her sidepiece? Because, by then, she would own me.

Then I thought about Steve, his big cock, and our times masturbating together in the dorm. Had we taken things farther, I think I would have liked it. We could have jacked and sucked each other off, and stayed happy and sane while we chased girls. Maybe what I needed was a boyfriend to fill the space between girlfriends. A bi buddy wouldn't get in the way of women, especially if he was chasing women, too. Maybe I needed to explore bisexuality. Maybe I was bi.

Time to consider this seriously. I started reviewing the various and different personals ads online. There were so many possibilities. Gay guys, bi guys, bi-curious guys. Bi guys seeking bi-curious guys. Guys who dressed like women. Guys who wanted to be women, some of whom had had some of the surgery to get them there. It seemed there were a lot of women with penises running around the city. Could be fun . . .

I knew what I wasn't. I wasn't gay. I did not want a permanent boyfriend, a male lover, or to be in love with a man. What I wanted was more recreational than that. A buddy to have fun with. To share sex with, with no strings attached, for as long or as short as it might work. I realized I was curious, and I might as well start there.

At six on a Thursday evening, as arranged, I rang the bell at Roger's house. I had answered his personals ad, in which Roger had described himself as fifty-five, divorced and free, seeking bi-curious men, and who could host in his home, discreetly and privately. We didn't exchange any pictures, but did trade some emails. From what I could tell, Roger seemed to me to be a solid, considerate guy and, in thinking about it, it occurred to me that an older, more experienced man might be a good way to start out. When I would wonder about what Roger might look like, I felt my dick twitch between my legs. Surely that was a good sign.

The door opened, and I saw Roger for the first time. Handsome, a few inches shorter than me, with dark brown hair, a touch of gray, and a bit on the stocky side. All in all, very pleasant looking. He smiled as his gaze took in my appearance, tall and slender, blond hair and, I've been told, gentle looking, slightly effeminate even. Roger invited me in and led me to the family room, a masculine space with leather furniture and dark wooden tables. He had me sit on the sofa. "So," he began, "you're exploring your bi side. Ever done anything sexual with a man before?"

" Just jacking off together with a buddy in college," I replied. "But we never touched each other. Except he shaved my pubes off the first time."

"I see," Roger went on. "What are you expecting here? Because, if you're thinking a blow and go, this isn't it. I've helped lots of boys like you explore their bisexuality. If we go forward, we will be together many times, over a long period of time. We won't be a couple. This won't interfere with your straight sex life. But we will have a relationship. We will care, we will be intimate, we will do it all, all in good time. You don't have to do anything you don't want, and I won't ask you for anything I won't give in return. I'm not your daddy, I'm not your Dom, I'm your friend. How does that sound?"

"It sounds good," I said. "It sounds just like what I'm looking for."

"Excellent. If you like, then, let's start by getting undressed."

With that, we started shedding clothes, removing shirts, shoes and socks, pants, eventually standing in only our briefs. Roger had a broad, hairy chest and just a bit of a belly. I'm nearly hairless, with just a few blond wisps around my nipples, and small tufts under my arms. He smiled as he saw me, then put his thumbs in the waistband of his briefs, grinned, and pulled them down, revealing the most massively hung cock I have ever seen. His nuts hung down low behind, in a big hairy sack, and a thick, dark furry bush all around, reminding me of my now lost blond one.

"Now you," he directed. Trying to act nonchalant, I pulled down my underwear and exposed my much smaller dick and balls to him, all shaved baby-smooth as they had been since that day, long ago, in Steve's dorm. Roger smiled. "Cute," he said, taking his big, fat penis in his hand. I held mine as well, and we moved closer together. I became erect immediately, but Roger's cock remained limp, hanging down, although it did start to grow a bit longer and thicker as I watched. Noticing my stare, he grinned. "At my age, boy, it takes a bit longer to come to attention. Don't worry it'll stand up soon."

We approached each other and Roger put his hands on my chest, letting them slide down until he was tickling my bare pubis with his fingers. I ran my fingers through his dense crotch hair, remembering the feel of a bush, and then grasped his penis, which continued to grow and stiffen in my hand. When Roger achieved a full erection, I was simply in awe. I had never seen anything so big before. My little prick twitched in anticipation. We pressed our naked bodies together, cock against cock, and he drew me in for a gentle kiss on the mouth. I didn't resist, and he followed with a long, deep French kiss. Our tongues danced together, and Roger took our two hard dicks in his big hand, squeezing them firmly together.

"First things first," he said. "Let's get to know our bodies. Go ahead, touch me all over. Everywhere. Get comfortable with my feel. I'll share it all with you." I reached out, starting with his furry chest and his nipples, ran my hands all over his torso, briefly held and examined that remarkable cock, then walked around and put my hands on his asscheeks. Roger spread his feet apart, and I reached under and hefted his heavy nuts in my hand. Taking a chance, I spread his cheeks and ran a finger deep inside his crack. Finding his puckered asshole, I fingered it gently. Roger never flinched. I slid my hands up to his shoulders and nuzzled him from behind. His hand reached down behind himself and caressed my erection as I again teased his nipples and then his hard cock.

Roger then turned to face me and, slowly, ran his hands down from my face to my scrotum, stopping at all the good spots along the way. After gently fondling my penis and balls for a long time, he turned me about and bent me over at the waist. Wetting a finger in his mouth, he spread my ass open, found my little hole with his finger and slid it inside. Surprised, I started, but it felt good and I relaxed and let him probe me.

When he finished, he sat down on the couch and pulled me down next to him. "That was nice," he said. "A good start, don't you think?" I nodded in agreement. "Let's talk about man sex a bit," he went on, as he cuddled me. "Remember, who you sleep with isn't anybody's business but yours. You don't have to label yourself one thing or another, whatever the LGBTQ activists tell you. When you walk out of here, you won't have 'FAG' written on your forehead. Nobody will know, and they shouldn't. Once you get comfortable with that, it all gets a lot easier.

"The truth is, sex is basically sex. It's all about making yourself vulnerable and exposed to another person. You're a man, you have a dick, and it needs to be relieved sometimes. When you figure out who you're attracted to, it all falls into place. You can suck a lady's smooth titty," he said, pinching my nipple, "or you can lay your face on a hairy chest," taking my hand and resting it on his fur. "You can do both. Once you get past who you're with, licking balls is pretty much the same as licking vagina lips. It may sound odd, but sucking cock is not so different from licking and sucking a clit. Fucking an ass is fucking an ass, and getting a blowjob is getting a blowjob.