"Never did this before," I said, as my new friend Jesse pulled my shirt up over my head, exposing my pale, hairless chest which was in stark contrast to the one of the man who was undressing me.
"I know," Jesse said quietly. "You told me that already. Relax, Tim. No reason to be afraid."
Not only was Jesse in his middle 20's, making me about 20 years his senior, but the young man was in superb shape, his upper torso like that of a weightlifter with the bulging muscles in his shoulders and chest visible even through the thick black hair that covered him from his neck down, front and back.
My fear was clearly evident, not only given away through my trembling hands but from the sweat that had my skin glistening despite the coolness of the motel room we were in, and it was only the fact that Jesse was being so nice and understanding that kept me from bolting out of the room and into the night.
Jesse's hand were on my belt, undoing it and then coaxing my slacks down off of my legs, leaving me with only my baggy boxers protecting me from being totally naked.
We had been taking turns in taking each other's clothes off, and now it was time for me to take Jesse's jeans off. He stood up in front of me, looking even taller than the 6'2" he claimed to be, and as I leaned closer to the edge of the bed my butt was perched on, my hands struggled with the button that secured his snug jeans.
"I have trouble with that too," Jesse said about the button, which was probably a lie designed to make me feel less pathetic than I was, and mercifully it opened up.
Jesse's zipper made a roaring sound as I pulled it down, or at least that's what it sounded like to me, and as I tugged the pants down I could smell the manly aroma of him that was released.
My face was directly in front of Jesse's crotch, scant inches away from the black boxer briefs, and I was unable to contain the gasp that escaped my lips as I stared at the outline of Jesse's cock which was very evident through the snug cotton.
I managed to stop gawking at the massive bulge long enough to get the jeans off of Jesse's profusely furry legs, but as I straightened back up my eyes went right back there.
"It's okay," Jesse said. "Here."
Jesse reached down and took my hand, bringing it up and placing it right on the bulge that ran down the inside of his right thigh. I felt the heat that oozed from the penis on the other side of that cotton; a penis that was still soft, I discovered as I let Jesse guide my trembling hand down the length of his organ.
"Unbelievable," I managed to say in a breathless voice as Jesse let my hand go when he found I was able to move it on my own.
"Told you I was kinda big," Jesse said as he looked down as my awkward massaging of his cock.
Indeed Jesse had done just that when he answered my ad that brought us together. It had been a very simple ad that I had placed in an alternative weekly paper, expecting to get maybe one or two responses.
"Middle aged man," the ad had read. "Very shy and nervous. Small build. Always curious but never willing to try before. Seeking patient guy to help me experience being with another man for the first time."
It was completely honest in every way. I had been curious all of my life, but kept my desires hidden under the charade of my marriage. With that gone, and me not getting any younger, I thought that the time had come.
The nondescript ad, hidden in the back of this free rag that I assumed nobody read, got 24 responses in the first few days. So many that I stopped the ad before it ran again. Jesse's was one of the nicer responses, and when I wrote him back I made sure to explain that when I said in my ad that I was small, I meant that I was small all over.
"That's good," Jesse had replied. "I like men built like that. I'm big - all over."
His hands on his hips, he exuded confidence but not arrogance as he seemed to enjoy my awe of him. I guess it was an example of how naive I was, but I had no idea a man could be so well endowed. Oh sure, I remembered in my youth taking showers in gym class and seeing the wide variety of sizes of their genitals, but seeing it was one thing and having the evidence right in one's face was something else altogether.
"Can we turn the light off?" I asked - pleaded.
Jesse smiled and went over to the light switch and turned the dial so that the lamp was dimmed but not off. It was still too bright for me but it was better than it was before, and as I watched Jesse's muscular body walk back over to the bed I knew that the moment was at hand.
How I dreaded this moment. In a matter of seconds my boxer shorts would be coming down, and my shortcomings would be revealed to Jesse. While he was being so nice that I pretty sure he wouldn't laugh, this was still terrifying to me.
Jesse eased down and sat next to me on the bed, the coarse hair of his thigh tickling my bare skin, and as he leaned toward me his hand came onto my bony knee, gently squeezing it in his meaty paw.
"Relax," Jesse said, leaning over and kissing me.
Our lips met as I experienced my first kiss from a man, and if I didn't know better except for the roughness of his five o'clock shadow I wouldn't have been able to tell the difference. When he felt me responding, Jesse turned up the passion, parting my lips with his tongue in search of mine.
Jesse's hand left my thigh and moved over to my boxer shorts, and unlike me, when Jesse probed around my underwear he had a bit of trouble finding my dick, which made me even more nervous.
"Ah! There you are," Jesse sighed when his fingers finally got hold of my little toadstool, which was trying to retract into my intestines from fear, and after rubbing it for a few seconds I felt the clasp of my boxers come open, giving Jesse a bit more room.
I saw Jesse glance down at what he was holding, but while he smiled he didn't laugh, and instead kept massaging my dick while leaning over and nibbling my neck. To my surprise, Jesse's comforting touch began to make me relax, and soon I felt myself responding to his touch.
"Tim," Jesse whispered in my ear as his fingers slid up and down the shaft of my stiffening dick. "You're not that small. You've got a beautiful cock."
That was a lie, because I knew I was small. My wife had called it my "little Dickie" for years. In the beginning she said it affectionately, but later used it derisively, blaming my small penis for our inability to have children as well as most of the other problems of the world.
As it turned out, it wasn't my fault that we couldn't conceive, but hers, but by then it didn't matter and it was probably just as well we didn't have kids. In the end, as the private detective discovered, my wife had sought satisfaction with a man better equipped to serve her needs, and that brought our marriage to a merciful end.
That was then, and this was now. There was nothing negative coming from Jesse, who seemed quite happy with what he was holding no matter how little it was, and when he eased me back onto the bed I felt his mouth envelop me. His moist lips slid right down until they were nestled in the tuft of pubic hair that I had trimmed in a futile effort to make me look bigger.
Our eyes met as he looked up at me, and he kept looking at me as my dick throbbed in his mouth. His lips slid up to the gumdrop sized head of my member, his tongue toying with the sensitive tip, before his lips slid down again.
My wife had given me oral sex from time to time, but what Jesse was doing went far beyond anything I had ever experienced. Jesse sucked on my balls tenderly, rolling my nuts around in his mouth and making me groan with pleasure before going back to my dick.
