1. Adventures in Babysitting. A True Story.

    I used to babysit for this couple that were friends with my folks. The husband, Jim, was a tall, stocky man who was rumored to be “connected” with organized crime. The thought of this gorgeous man and his connectedness and power were always intoxicating to me. I constantly fantasized about him and thought that I could never let him know of my secret attraction. Every time I’d babysit, and once the kids went to bed, I would find a pair of his worn underwear, bury my face in the crotch area and jack off while fantasizing about what it would be like to have the real thing.

    On one occasion, there was a neighborhood party for the adults and I was asked to babysit for the evening. As always, I was eager to get a chance to see my man-crush and grab me another pair of his worn undies to rub my face into.

    Well, the party was running late and it was getting close to my own curfew. He came back to the house - alone - to take me home. He had obviously been drinking. He smelled of booze and his shirt was unbuttoned, exposing a mountain of hair on his stocky frame. I could feel my face getting flush from the excitement of this sexy man standing before me. I’d never seen him like this before and I liked the fact that he was being so friendly and jovial. I asked where his wife was and he said that the party was still going on and now that his kids were asleep for the night, that he’d come back to take me home and then return to the party.

    "Before we go, I need to take a piss," he told me. Trying to veil the fact that I couldn’t keep my eyes off of his hairy chest and belly, I awkwardly said something like "I’ll get my stuff and meet you out at the car."

    "Good boy," he said as he grinned and playfully tousled my hair with his big, strong hands. All of this adulation was making me a bit weak in the knees. With that, he proceeded to unzip and turned to walk into the bathroom which was in the short hallway between the kitchen and the front room. As I went to gather my things, I realized that he had left the bathroom door open and that I could hear his strong stream of piss hitting the water in the bowl. I stood there frozen. Could this be my chance to get a look at Big Jim’s cock?

    I had completely forgotten about collecting my things and started up the hallway to see if I could get a good look. My heart was racing as I strolled by the bathroom door and tried to glance at his manhood without him noticing. It was beautiful. Bigger and more beautiful than I had ever imagined. I was so engrossed by his cock, that I hadn’t noticed that in that quick couple of seconds, he had turned his head and caught me looking. I kept moving, as if I was headed toward the front door when he called my name to come back. I was terrified. He caught me. Was he mad? Would he tell my folks? Would he hurt me? This guy was as straight and masculine as they come - well respected, powerful, had a beautiful wife and 5 kids.

    I slowly walked back to the bathroom door. All sorts of bad thoughts raced through my young, inexperienced mind. As I crested the doorway, he was still standing over the toilet with his dick out. I tried to look him straight in the eyes without diverting my glance to his cock or his open shirt that exposed his hairy torso.

    "You forgot to get your stuff in the kitchen!" he said as he started to wag the last drips of piss off of his cock. I couldn’t help but look down at it. It seemed to be a bit larger than what I had seen on my first pass and he didn’t seem to be going to any trouble to hide it from view. "Go get your things and I’ll meet you in the car," he said as he stuffed his semi-hard dick back into his pants and turned to the sink to wash his hands. "Yes, sir," I muttered with embarrassment.

    I went to gather my things, when he came back into the kitchen to grab something out the top of one of the cabinets. As he reached up, his shirt rose up and exposed his hairy belly. He glanced over at me as he grabbed a bag full of what looked like dried weeds and handmade cigarettes and put it in his pocket. “Busted again,” I thought. Not for seeing what I later figured out was his pot stash, but for being queer. I figured that I’d never be babysitting for him again. I was scared that now everyone would know my secret. “Go get in the car,” he said, “I’ll be out in a minute.”

    His was the only house on a newly added dead-end street in the neighborhood. Big Jim’s family owned the construction company that built the house. There were no street lights yet, so it was very dark and the rumors of his connections to organized crime only added to my nervous state. I went outside and got into Big Jim’s Cadillac. The engine was still running and the Carpenter’s “Goodbye To Love” was playing on the 8-track stereo. I didn’t have to wait for him long, but it felt like an eternity as wild thoughts of the repercussions of my secret sexuality being exposed ran through my head. “It’s going to be goodbye to me, if he thinks I’m queer,” I thought. But having seen this gorgeous man’s cock hanging out of his pants, I couldn’t keep from getting rock hard. It was thrilling and terrifying at the same time.

    The car door swung open and Big Jim plunked himself down in the driver’s seat. “What did you see in there?” he asked somewhat sternly. “Nothing!” I said, “What do you mean?” I thought for sure he was angry that I was looking at his cock.

    "That stuff I took from the cabinet. I know you saw what it was," he said.

    I didn’t know what to say. “You mean those cigarettes? I don’t care if you smoke, Mr. D.”

    He seemed relieved that innocently assumed they were cigarettes. “Yeah, I roll them myself,” he said. “Don’t tell anyone - and I mean anyone. I’d be very upset with you if you did.”

    I said, “I won’t say a word, I promise. I know how to keep a secret, Mr. D.”

    I noticed that his left hand reached down to his lap to adjust himself. Through the dim light of the dashboard I could see the shape of his cock down the inseam of his pants.

    He turned to me, gave me a smile and said, “Great. You’re a good kid, Mike. I really like you.”

    "I really like you, too, Mr. D," I said with a nervousness in my voice.

    With that, he reached over with his right hand and grabbed my still rock-hard cock and said, “Yeah, I noticed that!”

    Feeling his strong, masculine hand on my cock was almost too much for me to take. My heart jumped into my mouth and I couldn’t think of what to say.

    "Relax, Mike, I know you were checking me out in the house. Have you ever fooled around with an older man?"

    I couldn’t believe what I was hearing. Could this really be happening? Unable to utter any sort of intelligible words, I felt him let go of my cock. He pulled me closer to him, took my hand and brought it over to his lap, placing it on his now fully engorged cock. He groaned a bit as I began to feel his manhood through his pants.

    "We can’t do this here, buddy," he said. "Let’s go somewhere a little more private. I don’t want my kids waking up and finding their Dad out in the driveway with his dick in the babysitters mouth—umm, if that’s what you want—I don’t want to do anything unless you want to." It was then I was finally able to speak up, perhaps saying a bit too much… "Oh, yes! I’d like that very much, Mr. D. Ever since I can remember, I’ve thought about what it would be like to see you naked and touch you down there." He looked a bit surprised by my comment. He chuckled endearingly, pulled me even closer to him and said, "Oh, reeeeeally?!! I didn’t realize until tonight that you thought about me that way."

    I continued, “I hope you don’t tell anyone, Mr. D. My friends wouldn’t like me if they thought I was a queer.”

    "Don’t worry," he interrupted, "I know how to keep a secret, too, buddy. But don’t think there’s something wrong with you. Lots of guys keep secrets, if you know what I mean."

    "Yes, sir," I said as he put the car in gear and pulled my head into the garden of chest hair bursting out of his open shirt. "Let’s take a ride," he said, "I’d like to show you the new houses we’re building up the street."

    I didn’t say a word as we left the driveway. I unfastened the last few buttons of his shirt that weren’t already unbuttoned and began exploring his stocky torso with my right hand and rubbing his thick, hard cock through his dress pants, eventually reaching for his belt buckle. “Go ahead,” he said as he gently kissed the top of my head. “It’s all yours, buddy. Enjoy yourself.”

    I got his pants open and reached in, feeling the heat of his cock. It was too difficult getting it out of his pants while we were driving. It was so big and was wedged down the left leg of his pants. “Hang on, buddy,” he said, “We’re here at the site.”

    Big Jim stopped the car and lifted himself off the seat a bit so I could finally free his fat cock from his pants. It was like a dream. His hard dick slapped against the steering wheel of the car as it sprung from its restraint. I couldn’t believe what was happening. My first look at Mr. D’s fully engorged cock. It was like nothing I’d ever seen. Even bigger than what I had seen in the bathroom. He turned toward me on the big bench seat of his Caddy and lowered my mouth onto him. This beautiful bear of a man’s cock was in my mouth! I couldn’t believe this was actually happening! I could hear Big Jim groan with approval.

    "You’re a natural," he said as he grabbed my head firmly with his strong hands, regulating the speed at which I was eagerly devouring his manhood. "Slow down, buddy, it’s not a race."

    Big Jim seemed gentle and loving. Quite the opposite of his rumored reputation. He really seemed to care for me. He stopped me several times, edging himself with my mouth, finally asking me if I’d like to taste his cum. I’d never tasted a man’s cum before, so I was a bit nervous, but agreed.

    "Okay," he said, "You’re doing great, buddy. Just keep doing what you’re doing—your mouth feels sooo good—I’ll let you know when I’m ready."

    Mr. D was a big, masculine man and I had no idea what to expect. I could tell he was getting closer as he grabbed my head, holding it still, controlling the rhythm as his cock slid up and down in my mouth. His moans turned into words of encouragement. “Mmmmmm…oooh, yeah…that’s it. Mmmmmm…suck it boy. That’s right…Mmmmmm. You ready, buddy? Unffff… You ready, buddy?”

    With my mouth full of his cock, all I could manage was, “MmmmHmmm! MmmmHmmm!” In my head, I thought, “Oh yes, sir, please give it to me, I am so ready for you.” All of my nervousness was gone. I wanted more than anything to please this man, eagerly gagging on his huge dick as he plunged it deeper into my mouth.

    His rhythm got faster and faster… “Mmmnff… Awww… Fuck, yeah… Here it comes, buddy… Here it comes… Aaaaawwwww… Unfff… Fuuuuuuuuuuuuuuuuuuuuuck……”

    Suddenly I felt a huge blast of warmth explode against the back of my throat as his entire body shook. There was so much cum that I choked and blew most of it back out of my mouth before I could swallow anything. “Good boy… good boy,” he assured me as he backed out of my mouth. I found myself looking down the barrel of his cock as he spewed rope after rope of cum into my mouth and onto my face.

    The amount of cum was overwhelming, but I wanted nothing more than to please him. His spunk tasted sweet but musty at the same time. I was unsure if I liked it or not, but I wanted it badly enough that I didn’t care—I wanted it all. When he stopped cumming, I continued to clean the shaft of his cock with my tongue, burying my face into his hairy belly and thick bush, eager to get every last drop of spooge that Mr. D had to offer. Each time I put my mouth on his cock, I could feel his body shutter. “Easy. Easy. Easy,” he said, “Wheeeeeew! That was fan-fucking-tastic! We’ve got to get you cleaned up and back home.”

    He pulled some napkins out of the glove box and proceeded to clean his cum from my face and dropped them on the floor of the car. “Damn, little buddy. I really made a mess, didn’t I?”

    "It’s okay, sir," I said, "I don’t mind. I’d be happy to do that for you anytime."

    "Let’s get you home. I’ve got to get back to that party. This has got to remain our secret, Mike. You can’t tell anyone. I’ll tell your folks that I brought you to see the new construction over on Drover Lane before bringing you home. That should explain why I’ve been gone so long. Technically it’s not a lie, and you’re a good boy, so they’ll think nothing of it."

    When we got to my house, I reached down and grabbed all the cum-soaked napkins from the floor and told Mr. D that I’d get rid of them for him. He surprised me with a passionate kiss and said, “Now that we know we can both keep a secret, I hope we can do that more often. I’d like to get a taste of you, too!” 

    "I’d like that more than anything," I said, and with that he backed out of the drive and headed back to the neighborhood party.

    I stood there watching his car until he was out of site. I was so excited and couldn’t wait to get up to my bedroom with those napkins covered with Big Jim’s DNA. I kept running the entire experience over and over again in my mind, sniffing and sucking on those napkins while I jacked myself off to sleep.

    Mr D and I continued to keep our secret for another few years until I moved away. I continued to babysit for his family and we always had a good time on the ride home. We were always discrete around others, keeping our secret between the two of us. Nobody ever had a clue that I was this well-respected, powerful man’s personal cock sucker. I think he still lives in that house—he’s got to be about 70 now. Maybe some day I’ll stop by and say hello.


  1. huskycub1988 reblogged this from psyckogreg and added:
    Fucking hot story. I kept thinking of the sopranos.
  2. psyckogreg reblogged this from bigmenarebest
  3. thisbearishot reblogged this from masterlovechop and added:
    So fucking good!
  4. masterlovechop reblogged this from bigmenarebest
  5. markni766 reblogged this from lilbong
  6. lilbong reblogged this from bigmenarebest
  7. huskyfun reblogged this from huskyfun
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  13. ebox3 reblogged this from bigmenarebest and added:
    very hot
  14. nightofthechubs reblogged this from bigmenarebest