CHAPTER 1 - THE TRUE PART OF MY STORY
When I was 17, I still lived with my parents in a major midwestern city. I had gotten a pretty good job between high school and my first year at college. And I found myself temporarily without girlfriend since she'd already left early for college. My employer was located near downtown, which required a commute first by bus, then by commuter train. At that stage in my horny adolescence my hormones were raging, and I masturbated constantly while envisioning all sorts of sexual fantasies in my mind. I even had a pair of panties from my girlfriend, that she'd actually worn (they smelled wonderful). I jacked off with these quite often in her absence. She'd given them to me one night after we'd climbed into the back of my father's station wagon in a dark parking lot to make out. That night I talked her into giving me a handjob after I'd been finger-fucking her with her panties off. She wouldn't let me fuck her, but she agreed to jack me off, and I shot into her underpants. She presented me with the messy panties as a going-away gift.
During this period in my sexual development (I was still a virgin, much to my embarrassment), I found myself fantasizing more and more about what it would be like to have sex with other boys. Girl fantasies were becoming "old hat". I fantasized about things like.......jacking off one of my friends and watching him cum, getting fucked by my old little league coach, etc. Eventually, my thoughts became bolder, and I imagined being molested by our priest one evening after catechism. I was an alter boy, and I used to masturbate in the church men's room fantasizing that it was Father Carl's hand jacking me off. I had heard the stories about priests and young boys too. I also masturbated thinking about the times when all of the 11-15yo boy scouts used to line up just before summer camp and, one-at-a-time, we would stand in front of a doctor who would drop our pants and underpants, put his finger beneath our balls and ask us to cough, checking for hernia. I imagined our scoutmaster standing next to the doctor with a visible bulge in his pants, watching all the boy's penis', then taking me aside into the next bedroom, laying me on the bed, pulling my pants down and sucking me off until I came in his mouth. I also fantasized about my girlfriend's mother giving me a lecture on not going too far with her daughter, then demonstrating safe sex by masturbating me. I never lacked for imaginative fantasies with which to beat off. But this was only solitary fun, and I longed for more. Anyway, now that I've set the scene, back to the original point of the story. And it actually happened just the way I'm describing it.
One day I was standing at my appointed corner waiting for the bus, which was invariably late. It was maybe 5 degrees outside that day. I was stomping around trying to keep warm when a nice shiney white Pontiac convertible with a light blue top stopped at the light. There was a nice looking guy in his late 30's driving, dressed in a suit and tie. Anyone over 30 seemed old to me at the time. He looked over at me, rolled down his power window and said, "You look cold kid. Can I give you a lift. It's a lot warmer in here." (or words to that effect). I hesitated a bit, then decided to take him up his inviting offer. We introduced ourselves - his name was Gene (and I'll be damned if can remember his last name). He worked at one of the major banks downtown as a Loan VP. As it turned out, we also took the same commuter train, so we struck up an instant friendship on our way to work that day. He said that he drove by that bus stop every day about that same time, so why didn't I just ride with him and save the bus fare. It sounded like a good plan to me....plus I was really getting off on his neat car (as any 17 year-old boy would).
And the next morning....there was Gene in his shiney new Pontiac, just as he said he'd be. I don't think he ever let that car get dirty. That day we also arranged to take the same train home in the afternoon, so he gave me a ride both ways. After that, it became a regular routine every work day, and we became good commuting buddies.
At that age, it never occurred to me that Gene might have ulterior motives for the cute teenage boy he was now squiring to and from the train station in his fancy car. I was somewhat clueless back then, but I nevertheless I started including Gene in my masturbation fantasies (as I'm sure he did with me). I expect this could have been a bit of a turning point in my sexual orientation, but I didn't realize it at the time.
Commuting with Gene was very pleasant, and I started liking him more and more. It turns out that he was single, still living with his folks, but he also had a house in the trendy Old Town section near downtown that he owned with a "friend". His "friend" was Mark - a decorator for the major department store. They used to vacation in Provincetown on Cape Cod. Did I pick up on any of this, duh? Hell no. But the fact that I was jacking off a lot fantasizing about Gene probably gave me my first clue.
After a few weeks, Gene said he had to work late one evening, and asked if I would like to join him for dinner later at this really upscale restaurant that I'd heard of, but felt I could never afford....his treat. I was quite flattered. I thought about it for all of 2 seconds, and agreed. So, that afternoon instead of catching my train southbound, I took it the other way to downtown. And there was handsome Gene, waiting for me on the train platform in his black Vicuna topcoat and white silk scarf. I reached out to shake his hand, but he gave me a big hug instead - which seemed perfectly natural. He said that we maybe ought to stop by his Old Town place, so I could meet Mark, and change clothes for the evening.
We took a cab to Old Town. His house was charming...a little cottage tucked behind a picket fence, and beautifully maintained. Of course the interior was decorator perfect, as was Mark when I met him. He gave me a hug too, and said that he'd heard a lot about me from Gene....and now that he'd seen me he agreed that it was all true (young Will is still sort of clueless here but somewhat hopeful way down deep that something might come of this). Mark had prepared Mimosas (sp?), which is Champagne & Orange Juice, which he served in tall fluted stemware with a sprig of mint, on a beautiful silver tray. We sipped and talked for awhile. Then Gene said, "Okay, the two of us have to get going if we're going to make our dinner reservation.
He ushered me into his bedroom, and said, "Okay, you're about my size. Let's see what we can come up with for you to wear tonight. Here, take off your shirt and pants." I stripped down to my t-shirt and white cotton underpants. He asked my sizes, then held a pair of dark slax up to my waist. He said something like, "These look to be about the right length." As he did this, I was aware that his hand managed to graze, ever so slightly, across the front of my underpants. I recall that he patted me on the ass playfully as he said, "Okay, go try these on." During this whole exercise, I found myself getting a little aroused, which I think may have showed beneath my white briefs. I found myself a little embarrassed. He didn't say anything, but I'm sure he must have noticed the growing bluge. I dressed in his stuff, and it seemed to fit perfectly.
The two of us departed, and had a very memorable five-star dinner. The restaurant was everything I expected. We must have looked like father/son or uncle/nephew. Gene seemed to know the waiter, so he ordered me a cocktail, even tho I was underage. The waiter didn't seem to mind. After our delightful repast, we took a cab back to the cottage. Once inside, we took off our shoes and relaxed in front of a nice blazing hearth that Mark had prepared for us before he retired (conveniently). Johnny Mathis played on the stereo. Gene remarked, "Why don't you just spend the night rather than take the late train home at this hour?" Made sense to me, so I called my parents, and told them I'd be staying with a friend and wouldn't be home that night, and not to worry.
"Good, then let's get comfy before turning in" Gene suggested. He led me into the bedroom again, where he disrobed down to only his briefs, then put of a plush velvet bathrobe. I found myself staring at the bulge in the front of his underpants, and I think he was aware of this. I was now starting to get it, and the cocktails before and after dinner had put me in a very mellow mood. Gene watched as I undressed back down to my underpants, took his clothes and hung them up, then gave me a robe to wear. We adjourned back to the living room in front of the fire. We had more cocktails, and I found I was getting a little giddy. It had been a perfect evening so far.
I could feel an erection starting to rise in my underpants beneath my robe as I sat there in my armchair facing Gene. I think I was having the same lusty thoughts as I'm sure he was having at that moment. He and I had never even approached the topic of sex, or desires, etc. in all those weeks we'd gotten to know each other. For certain, I was much, much too shy and reticent to bring it up, even tho I felt I was ready to succumb to any advance he might make. As we talked, I thought about how it turned me on when girl's would inadvertantly sit in a way with their knees up and you could get a peek up their dress and see their underpants. I shifted the way I was sitting, and assumed a postion where I was hugging my knees, giving Gene a view of the crotch of my underpants up my robe. I wasn't sure whether he could see that I now had a hardon or not. He just kept on chatting, and I thought I noticed his gaze shift slightly. I'm sure that he was thinking - how nice it would be to have sex with this handsome young lad, but this could really be trouble if he freaked out at any advances I might make. And this kid was jail bait, for sure.
The conversation went on to all sorts of topics...nothing sensual at all. I was expecting him to broach the subject of sex, but he didn't. Now that I think back on it, I suspect that he must have been just as nervous and hesitant to make any indecent proposal, for fear that I would be offended, get turned off. I was definitely ready, but he didn't know that. And I was too nervous to bring it up myself. I was tempted to excuse myself, go into the bathroom, and masturbate. I did go to the bathroom briefly to take a leak, and I vividly remember that there was a round tilt-mirror sitting on the toilet tank, and it was angled perfectly so you had a perfect view of your penis as you stood there peeing. I thought that was pretty erotic. I jacked off a lot in front of mirrors then - still do.
Finally, Gene suggested that we retire. As we rose, it occurred to him that there was only one bedroom. He said, "Why don't I take the hide-a-bed here in the living room, and you can have my bed." I wasn't about to put him out of his bed and replied, "No, let me take the sofa." We wavered back and forth, then he suggested the idea of sleeping together in his bed.....if I didn't mind. I was delighted, and felt blood rush to my cock. I was trying to figure out how I was going to hide my embarrassing erection. That was solved when Gene turned out the lights (he may have known, and was being sensitive to my dilemma).
So there we were....the two of us, in just our underpants, in bed together. Nothing subtle about that scenario - even for my adolescent brain. I always sleep in my underwear on the left side of the bed, and that night was no exception. After we said our goodnights, I curled up with my back to Gene. Pretty soon I felt him cuddling up next to me, with his arm wrapped around my stomach, his face was nuzzled against my neck. My mind was racing with what would happen next. We stayed like that for quite awhile, with neither of us moving or talking. I pretended to doze off, but my mind was racing, and my rock-hard erection was still throbbing, just a few inches from Gene's hand resting on my stomach. I really wanted to get off.
IN REALITY...THAT'S HOW THE EVENING ENDED (WHAT A BUMMER FOR BOTH OF US), PROBABLY BECAUSE BOTH OF US WERE TOO FEARFUL OF REJECTION OR OF RUINING A RELATIONSHIP. WE BOTH JUST FELL ASLEEP, AND NOTHING EVER HAPPENED.
HOWEVER, THE THOUGHT OF WHAT COULD HAVE BEEN HAS BEEN THE SOURCE OF MANY OF MY MASTURBATION FANTASIES SINCE - LIKE THIS ONE.... See Chapter Two