A Story of Tighty Whiteys

February 18, 2020

In 1999, I was an 18 year old high school senior. My greatest frustration in life was that I was still a virgin. Attractiveness wasn't the issue. I had light blue eyes and a mop of skater-style blond hair crowning a face of delicate, almost feminine, features. I had a thin, slightly athletic build. I wasn't athletic in the sense of having developed muscles from lifting weights, but I was athletic in the sense of being very physically fit from all the outdoor activities I enjoyed. Altogether, I looked young for my age.

The 1990s marked the early days of the Internet, and I began spending more and more time online. One day I was particularly horny and was browsing some ads from a now-defunct personals site. Someone had posted an ad about watching porno movies. The guy who posted claimed to have a huge library and was offering to allow guys to come over and watch them. Strangely, the ad was clear about not wanting "old dudes." I browsed the partial list of movies that he owned, and his tastes seemed similar to my own. The movies were all straight porn, which I found reassuring at the time.

On a lark, I sent him a message asking if he was serious and if there were any catches. He emailed me back responding that he didn't mind other guys watching porn with him, and he was hoping that he might even make some friends in the process. He reassured me that there were no catches and introduced himself as Jack.

I thought about it for a minute and recalled that I had been both horny and a bit lonely over the last couple of weeks. I decided that he was probably another young guy just like me facing the same kinds of teenage issues I was confronting. I emailed him back telling him that I was interested. He got back to me quickly, and I was briefly taken aback by part of his response.

"Just so you know man, I can't watch porn and not jerk off. That takes all the fun out of it. I just don't want you to be surprised. You can jerk off too; I don't mind," his response stated.

I paused for a second as I had never masturbated with anyone else before. I had heard of circle jerks, and I knew there had to be guys my age who jerked off together, but it was slightly out of my comfort zone. I struggled with this for a few minutes and considered that he was a perfect stranger who didn't know anything about me, my family or my friends. I began to feel that these facts made the encounter safer. If I got uncomfortable, I could just leave. If I didn't enjoy it, I would just change my email address and cut off contact with him.

"Yeah, no problem. Send me your address," I responded.

We made arrangements for me to go over to his house after I got out of school at around 3 PM. I was nervous that whole day in school. More specifically, the feeling was nervousness coupled with anticipation. When school got out, I got on the bus that took me to the general neighborhood that he lived in. I followed the house numbers on the street until I reached the address he had given me. It was a well-kept, one story house in a working class neighborhood.

I paused briefly as I was overtaken by anxiety. I wasn't sure if I really wanted to do this. I wasn't sure what I was getting myself into. I forced myself to overcome these insecurities and knocked on the door. The door opened, and I was stunned to see a tall, well-built man in his mid-fifties standing in front of me.

"Um, is your son around?" I stammered after a pause.

The man gave a bemused laugh and said, "It's me. I'm jack. You're here about the movies, right?"

For a moment, I was actually scared. Everything about our interaction online had suggested that he was around my age, and here I was confronted with a man three times my age. I could have easily been his son. I started to consider the possibility that he had lured me here under false pretenses to cause me harm. I briefly considered running away.

"Were you expecting someone younger? Sorry about that. I just don't get along well with older guys. They're too boring," he responded as he sensed my fear.

"I understand if you are uncomfortable. No problem. If you want to take off, my feelings won't be hurt. On the other hand, I've got some good weed and some hot porn if you want to hang," he offered as he gestured into his house.

I forced a smile and stepped forward through his door and into his home. As I did so, Jack seemed slightly surprised and genuinely excited. As an adult, I obviously question the wisdom of my choice in retrospect. However, I had the feelings of invincibility that often accompany youth. What seems like an unacceptable risk today seemed like an adventure back then.

As we walked through his house, he turned to me and asked, "What's your name kid?"

"Adam," I replied quietly.

"Nice to meet you Adam. We're going to have fun, but first we need to get you loosened up a little bit. You look tense," he said with a tone of concern.

Jack retrieved a pipe and stuffed the bowl with a bud covered in THC crystals. I could tell it was going to be good stuff and potent too. He handed the pipe to me along with a lighter. I lit the bud and inhaled deeply.

"Good boy," he said slowly and approvingly as I exhaled a large plume of smoke.

Whatever he had was really powerful stuff. It might have even been laced with something. I immediately felt light headed, disoriented, and a little euphoric. I started to hand the pipe and lighter back to him, but he held out his hand in refusal.

"I want you to finish the bowl," he insisted.

I took hit after hit of that stuff and was starting to get really fucked up. Jack began to notice this as well, and then he performed a little test to satisfy himself that I was relaxed. He ran his fingers slowly through my hair. I offered no protest or resistance. In fact, I believe I even smiled as I enjoyed the feeling of his thick fingers playing with my hair. Jack took the pipe from me and set it down on the counter. He then put his hand on my back and walked me over to the couch in the living room where I sat down.

I checked out Jack as he put the porn DVD into the machine. He was ruggedly handsome. He stood around 6'1" tall and had a powerful chest and arms. Overall, he had the weathered and conditioned look of a construction worker. Jack turned around and walked back to the couch where he sat down very close to me.

The porn video was in full swing now, and the screen showed a blond bimbo getting double penetrated by two hung guys. Jack unbuttoned his pants, unzipped his fly, and pulled his pants down around his ankles. He then pulled his boxer shorts down to join his pants. I was briefly confused by this in my intoxicated state, but I quickly remembered that he told me in advance that he was going to jerk off while he watched the movie.

My eyes traveled over Jack's cock and balls as he began to stroke himself. His cock was a little longer than mine and considerably thicker. I was amazed by the size of his balls and the scrotum that covered them. His balls had to be twice the size of mine. He was definitely a man's man. Jack stared at the TV, not me. This made me comfortable enough to disrobe as well. I pulled off my shorts and then paused briefly before pulling off my tighty-whitey briefs.

I couldn't believe what was happening. I was sitting there naked from the waist down on another man's couch while he jerked himself off next to me. I was confused and disoriented from the weed, but also a little turned on from the raw sexuality of what was happening. I slowly began to stroke my cock as I watched the movie.

After a few moments of watching the movie, I turned to look at Jack again. To my surprise, he was intently watching me jerk off and completely ignoring the movie. I enjoyed this attention and reciprocated by watching him as I jerked. After a few moments, we were both rock hard.

"It feels better if someone else does it," he said looking into my eyes while continuing to stroke his cock.

He reached his free hand over and grasped my cock. I immediately released it and let him take over. He was right. His hands felt amazing. He had this way of jerking me off that was simultaneously gentle and deeply pleasurable despite his large, rough fingers. I hesitated about returning the favor as I still had hangups about physical contact between men. I eventually capitulated and took his cock in my hand feeling pressure from the norm of reciprocity.

Jack and I sat there jerking each other off while looking at one another, not the movie on the TV. I realized that I was receiving sexual pleasure from a man and I was giving a man sexual pleasure. It may sound strange, but this had never occurred to me as a viable option. I had never even fantasized about it before, and here I was giving a handjob to a much older man and receiving one in return.

"Kiss my cock Adam," Jack said out of nowhere.

"Uh, that's okay. I'm good like this," I hesitated.

"You don't have to suck it. Just kiss it with a closed mouth. You are already touching it. Nothing is going to happen," he urged.

Jack was continuing to stroke me while we had this discussion. By that point, I was very sexually aroused and decided to play along until things got too uncomfortable.

I tentatively leaned over and kissed his mushroom head with my lips. He was right. It wasn't bad, so I decided to make a good faith effort. I held his cock with my hand as I slowly kissed up and down his shaft and tip with closed lips.

After a few minutes of this, Jack said, "Now I want you to lick it."

"I think that's too much," I said with all the confidence I could muster.

"Really? How did you feel before you came over here?" Jack queried.

"Lonely and horny," I replied honestly.

"Right. Now how do you feel?" He asked as he continued to stroke me.

"I'm really enjoying myself," I assured him.

"Right. You are enjoying yourself because you have done what I told you and have followed my lead. Keep doing what is working. Stick out your tongue and lick my cock," he urged.

I gave in to Jack and lowered my head to his cock. I stuck out my tongue and ran it over his cock from base to tip repeatedly. Jack leaned back and let his eyes close as he surrendered to the experience. I watched the expression of pleasure on his face as I licked him. I felt powerful in the sense that I could give another man this kind of pleasure and vulnerable in the sense that Jack had basically ordered me to do something that I wasn't ready for. I found this particular mix of feelings intoxicating. Jack slid his hand under my chin and lifted my tongue off his cock.

"Suck my cock Adam," Jack said with complete confidence.

I looked down at Jack's cock. It was hard as a rock with protruding veins along the shaft. A small bead of clear precum had formed at the tip of his deep purple mushroom head. I didn't need to debate this with Jack this time. I didn't need to be convinced. I wanted this stranger's cock in my mouth. I found it amusing that I planned to come over here to watch straight porn and ended up sucking a dick. Life can be funny, I thought, as I lowered my open mouth over Jack's tip.

I closed my mouth around him and began to run my tongue over his tip licking up his precum. Slowly, I began to take more and more of him into my mouth. I felt Jack's big hand gently grasp the back of my head and begin to guide my mouth up and down on his cock. I liked that Jack was taking control of the situation as I wanted to please him the best I could.

A number of things surprised me about sucking cock for the first time. The first thing was how soft it felt in my mouth compared to how hard it felt in my hand. The second was the intense musk that I could taste. It was like Jack's cock was coated in his pheromones and it was starting to drive me crazy with lust.

"Yeah, that's right. Suck daddy's dick Adam," Jack groaned as he guided my head up and down his cock with increasing fervor.

I liked that he was talking dirty to me. It made me feel slutty. I was also beginning to get turned on by the inappropriateness of our age difference. The realization that I was blowing a much older man caused precum to roll from the tip of my dick down my shaft. I began licking and sucking him with even greater intensity until I felt his cock pulsate violently for the first time.

Immediately, I felt something hit the back of my throat and provoke the urge to cough. While my natural instinct was to pull off of him, Jack held my head on his cock and continued to work it up and down. I felt his seed flood my mouth.

Never having done this before, I assumed that guys collect the cum in their mouths and spit it out afterwards. I was having difficulty with this approach as he was shooting what seemed to me to be enormous quantities of cum. By the time he was finished, I couldn't contain it all in my mouth and it was beginning to leak from the corners of my lips and run down my chin.

Jack kept his cock in my mouth for a few more moments before he began to pull it out. I tilted my head up to keep the cum from spilling out of my mouth. Jack could sense what I was trying to do.

"Open your mouth so I can look inside," he said.

I obeyed, holding my head at an upward angle and opening my mouth as wide as I could without causing his cum to spill out.

"Swallow it little boy," he ordered.

I hesitated for a second before I closed my mouth, looked him in the eyes, and swallowed his whole load. I felt it slide down my throat, and I wondered why I didn't swallow it in the first place. It was slightly salty and had a little bit of a bleach aftertaste, but it wasn't unpleasant. In fact, having a much older and more powerful man force me to swallow his cum turned me on.

I opened my now empty mouth to show Jack that I had done as he had asked.

"Good boy. Now lean back and let daddy take care of you," he said in a compassionate tone.

Jack spread my legs and put his face between them. I felt his tongue begin to flick against my asshole. That was followed by deep licks. Finally, he brought his tongue to a point and pushed it inside my asshole like a small cock. I was overwhelmed by the feeling. Having another man eat my ass was unlike anything I had imagined. Jack withdrew his tongue and put the tip of his meaty index finger up against my asshole and pushed in halfway. I felt a surge of pain.

"Push out like you're taking a shit," he advised.

I did as he instructed, and it felt a little better while the rest of his finger entered me. He left it there for a moment before working it in and out.

"Goddamn, you're tight. We're going to have to work on that," he said.

He withdrew his index finger and placed both his index finger and middle finger against my asshole. My asshole stretched to accommodate him as he pushed both fingers inside. While he was working two fingers in and out of me, Jack lowered his mouth to my cock and began to suck me. Jack was a master at sucking cock. He ran his tongue underneath and over my shaft as he went up and down. The combination of being fingered and sucked at the same time was amazing. The greatest satisfaction came when my asshole finally adjusted to his fingers and the pain was replaced by pleasure.

"Oh, daddy. Suck your boy's dick," I moaned with pleasure as Jack's head bobbed up and down between my legs.

I quickly reached orgasm and shot my load into Jack's mouth as my asshole spasmed around his fingers. Jack kept his mouth on my cock, swallowing continuously, until I had shot my load in its entirety. Jack pulled his fingers from my ass and brought them to my mouth. To Jack's approval, I opened my mouth and sucked them clean.

I happened to gaze over to the time on the DVD player and noticed that it was 7:00 PM.

"Holy shit!" I yelled.

"I have to go. My parents are expecting me for dinner. They will wonder where I am," I explained.

Jack seemed disappointed but nodded in understanding. We continued to check each other out as we got dressed. He walked me to the door where I turned and kissed him. Our tongues rolled over one another and we held each other tightly. It was more magical than kissing any girl. I had found my daddy and he had found his boy.

I whispered into his ear, "I want you to fuck me daddy. I want you to stretch me out, and I want you to send me back home with your seed leaking out of my ass."

"Hell yeah. After school tomorrow?" He queried.

I nodded, turned, and walked out the door heading off to dinner with my parents.