The Price of Silence

I'm not going to lie: The best part of being friends with Jim was being around his mom. She was, quite literally, the definition of a MILF, and we all reminded Jim of that constantly. April was a curvy 40-something redhead with green eyes, pale skin, an ass kept firm from spin classes and Pilates, and heaving DD cups that somehow still defied gravity. It was safe to say that I wasn't the only one of Jim's friends who jerked off to her on a regular basis. I think, in a way, she knew how we all lusted after her because she was often flirty which, again, not going to lie, may have made me cum in my pants on more than one occasion.

It was a beautiful August day and I was spending the afternoon at their pool. My sunglasses were dark enough that they completely hid my eyes, so I could stare at April all afternoon. Whenever my thoughts drifted too far towards the carnal side I would take a dip in the pool to make my cock soft again.

The patio door opened and April came out, ready for a swim. She was wearing a white one-piece suit that dipped low in the front and rode up her ass in the back. She dove into the pool and swam a few laps before she climbed out and headed over to a lounge chair to. I didn't have to work too hard to undress her with my eyes because the suit had no lining. It had turned practically see-through, her nipples and small patch of bush on full display. I looked over at Jim, who was reading his phone, and his dad Tom, who was reading a book.

"Damn, they are missing out," I thought as I watched April lay down on the chaise across from me, her legs playfully open. I felt my cock come alive and I knew cold water wasn't going to do the job this time. I told Jim I was going to hit the head and then hurried into the house before my boner became too obvious.

***

The plan was simple: go up to Jim's room, jerk off on his bed, then head back to the pool with none the wiser. Instead, I paused at the top of the stairs and stared into his parents' room. I looked behind me, confirmed I was alone in the house, and ventured in.

I tip-toed to the dresser, which seemed silly considering I was the only one inside, and quietly opened one of the top drawers.

Bingo.

It was April's underwear drawer. I rifled through her collection of lace bras, the cups so large they looked like hats, and then moved over to her panties. As I rummaged through her pile of panties I quickly discovered that April was a thong girl. It was literally all she owned. I pulled out a tiny white lace thong and thought that Jim and Tom were lucky bastards. I listened quietly for a moment and, satisfied no one entered the house, I pulled off my board shorts and wrapped her panties around my stiff shaft. I drooled some spit onto it and started stroking, her thong firmly held between my hand and throbbing dick. Years of watching porn had me picturing a scenario where I blew my load all over her thong and placed it back in her drawer a cummy mess. Of course, she would find her thong while they're still soaked with cum, would figure it was my gift to her, and she'd rush over to fuck my brains out.

The reality was quite a bit different. I was jerking quickly, knowing I needed to cum before anyone noticed how long I was gone. I was right on the edge of shooting my load when a voice snapped me out of the moment.

"What the actual fuck do you think you're doing?" I turned around, absolutely pale, and stared at Tom. I stood there like a deer in headlights, my hand still holding her thong around my cock. He looked down at my dick, and her thong, and closed the door behind him.

I was scared shitless.

"Give me one good reason why I shouldn't tell your fucking parents what you're doing," he threatened as he walked closer to me. My heart was practically beating out of my chest. Telling my parents would be an absolute disaster. They were ultra-conservative; sex was something you subjected yourself for the sole purpose of having a baby. The thought that their 18-year-old son was using his friend's mom's thong to jerk off with while thinking about pounding her pussy? That would literally be a "tossed out of the house on your ass" moment.

"Please, please, please don't tell them," I said, fumbling with the thong, trying to unwrap it from my shaft. "They'd kill me."

Tom moved closer and laughed at my attempts to free my dick. I finally unraveled it and was about to put it back in the drawer.

"What do you think you're doing with that?" he asked, nodding at the thong.

"I was putting it back in..."

"Shut the fuck up. I wasn't looking for an answer, you dumb ass. You like her thong?" he asked me. I furrowed my brow, wondering if this was a trick question.

"I said, do you like her thong?" he repeated, becoming impatient. I sheepishly nodded my head.

"Tell me," he answered.

"Yes, I like her thong," I whispered.

"Louder!" his voice boomed.

"Yes I like her thong," I answered, so quickly that it almost came out as a single word.

"Then put it on." I hesitated. "Put it the fuck on, or I'm texting your dad."

I almost tripped myself as I tried to put my feet through the leg openings. I pulled it all the way up, the thong sliding deep into my ass crack, my balls flopping out either side of the fabric, the head of my dick poking out of the low-cut top. Tom looked at my package straining inside the panties.

"Show me your ass," he said. I turned slowly until my back faced him. I looked briefly over my shoulder as he moved closer. I felt his strong hand slap my ass and squeeze it firmly. His thumb slid under the thong, lifting it out of my crack. He pushed his thumb down, the tip of it finding my hole, and he pressed firmly. I squirmed a bit at the sensation of his thumb just barely entering my hole. He kept his thumb pressure on as he squeezed my ass with his other hand.

"Your ass looks good in a woman's thong. Tonight, you're going to go to the store and replace all of your underwear with thongs, you got it?" he asked, slapping my ass again.

"Yes, sir," I answered. Hell, if this was all it took to buy his silence, I was game. I had to admit, I liked the way they felt, so win-win!

"Turn around and kneel," Tom commanded, removing his thumb from my hole. I turned around and knelt before him, his crotch inches from my face.

"Do you want to see my cock? Will that make your little dick in those thongs grow?" I stared at his board shorts and was able to see the subtle outline of his package. This wasn't my first time being this close to a man, and it wouldn't be the first time I'd see a man's cock. My roommate and I experimented quite a bit in my dorm room, having started out as porn jerk buddies, and progressing to us sucking and jerking each other off pretty regularly. Besides, I was curious to see what kind of cock was needed to land a piece of ass like April.

"Yes, sir, can I please see your cock?" I asked, looking up at him, my own cock straining inside April's thong. He nodded and I reached up and pulled the string tying the waist taught. I bit my lower lip and slowly lowered his trunks to the floor. My eyes practically popped out of my head from the sight before me.

For the record, as much fun as I've had with my roommate, his cock was pretty average... somewhere between four and five inches. Tom was an absolute fucking monster. With shaven balls that looked like tennis balls, he had a ridiculously thick foot long dick with prominent veining and a bulbous head.

"Holy fuck," I said before I could stop myself. Tom smiled and grabbed his dick by the base and slapped the head against my face.

"Yeah, you like this fucking dick?" he asked, his cock head bouncing off my forehead, off my cheeks, off my lips. "You ever see a dick this fucking big before? No? This is the kind of dick you need if you're going to get a woman like April." He lifted his cock up, pointing it to the ceiling, giving me a perfect view of his heavy balls.

"Get your mouth in there," he commanded. He didn't have to ask twice. I moved my head between his legs and bathed his massive balls with my tongue. They were perfectly smooth and my tongue swirled effortlessly around them. He let go of his dick, letting its full mass rest on my forehead as I started to suck his balls. I was able to suck both of my roommate's balls in my mouth at the same time, but that wasn't happening here. Tom's were far too big. I alternated ball to ball, sucking and licking one for a while before switching back to the other. Back and forth, sucking and slobbering his massive nut sacks.

"God, I love these fucking balls," I whispered as I slurped and licked them.

"That's a good girl," he groaned. "Now you need to suck my fucking cock." I moved my head away, his dong sliding off my head and dangling seductively in front of me. I grabbed the base and lifted it up, his mushroom head pointed at my mouth. I licked up his salty precum before opening my mouth wide for him. I could barely fit much of him in my mouth, so I resorted to strong suction and my tongue dancing all over the head. I wrapped both hands around his pole and started stroking as I sucked. I could tell that he needed lubrication, so I removed his cock from my mouth with a pop and bathed every veiny inch of his rod with my tongue.

"That's it, Little April, get that dick nice and wet," he coached as I made his dick slick with my slobber. My own dick was slick with its constant flow of precum. I wanted to reach down and stroke, but I needed two hands to handle his monster. I slipped as much of his cock into my mouth as I could and swirled my tongue all over his head. My hands pulled and twisted on his shaft, slowly at first, then faster and faster.

"That's it, Little April, make me cum... make.... me.... cummmmmm!" My roommate's orgasms didn't prepare me for the copious amount of cum that was about to erupt from Tom's cock, his balls pumping what felt like a gallon of cum in my mouth, thick and salty and heavenly. I swallowed as fast as I could, but it was like drinking from a garden hose. I couldn't keep up and some of the jizz spilled out of my mouth and onto the floor. His orgasm subsided and he pulled his dick out, slapping my face with it, splattering cum on my cheeks and forehead. I made a move to stand up, assuming I paid the price for keeping my secret.

"Where do you think you're going?" he demanded. "Lay down." He took me by the shoulders and laid me on the floor, positioning me so that the back of my head was in his pool of cum, the warm wetness absorbing into my hair.. I turned my head and could see him take something out of a nightstand. He walked back over to me and knelt below me, his knees by my ass.

"Lift your legs," he instructed. I didn't know what he meant, so he grabbed my legs and lifted them, eventually getting me into a position where my back was arched, my ass was pointing to the ceiling, and my feet were on either side of my head.

"Now, jerk off. Jerk off until you fucking cum." My balls were aching from needing to cum so badly that I didn't hesitate. I grabbed my small-by-comparison dick and jerked as fast and as hard as I could, my purple helmet pointed at my face. Tom popped open the bottle of lube he had taken from the nightstand. Pulling April's thong to the side, he poured a large amount of lube in my hole.

"Oh, fuck, he's not going to..." I thought, concerned that he was going to try to shove that foot long monster in my tight ass. As if sensing my thoughts, Tom assured me that would not be the case.

"You can't handle my dick... yet..." he said before sliding a finger inside of my well-lubed hole. He slid it slowly in and out, all the way in with each thrust, as my hand worked my dick furiously. His finger tip found my prostate and massaged it as I jerked faster. My hole clamped tightly against his finger as my whole body stiffened. I let out a loud scream and my cock pulsed almost uncontrollably in my hand, shooting thick, salty cum all over my face and in mouth. I slumped back onto the floor, my face looking like a glazed donut, utterly exhausted.

"That will keep our secret a secret," Tom said as he stood up and put on his board shorts.

"For today."