Four in a Penny

Notes: Thank you to kenjisato for the proofreading and editing of this story.

All characters in this work of fiction are eighteen years of age or older.

Saturday, August 21, 2021

It was a seasonably mild one hundred and two degrees in Las Vegas. The boys were enjoying what was left of their final summer before heading off in different directions. My son, Steven, and his long-time best friend, Craig, would be moving in a couple of weeks to start college. Each having earned a scholarship to play soccer at UC Berkeley. Their usually friendly competition led to them becoming the top two recruits in the state. Currently, their competitive natures were taking their toll on Mike and Ray, Steven's other two long-time neighborhood friends, in a spirited water volleyball match.

I was taking in the view from my usual chaise lounge at the far end of the pool in our backyard, beyond where the frequent splashes usually landed. I was sipping a skinny margarita, and occasionally glancing down at a book, not having turned a page in at least a half hour. I was painfully aware of the era that was coming to an end. Taking care of Steven, and the boys, had been my whole life, especially so, since my husband's unexpected passing five years prior.

Watching the boys, or, now men rather, since they had all turned eighteen during their senior year, with their tanned, muscled bodies, reminded me of just how much I needed to get laid. I had plans of scratching that itch, once Steven was away at school. That would be soon enough. For now, I would enjoy every minute of these last couple of weeks with my son.

"Hey, Penny." It was Craig, smiling playfully at me while retrieving the ball from an errant volley. Was it my imagination, or did they seem to hit the ball in my direction a little too often?

"That bikini looks really good on you."

"Thank you for noticing, Craig," I teased. Truth be told, I had worn my skimpier, white two-piece especially for him. It was no secret that he had been infatuated with me for years. The other boys would tease him mercilessly when he'd stammer awkwardly in my presence. That seemed so long ago. He was all muscle and dripping with confidence now. His lusty gaze had given me a little tingle. Okay, maybe a big tingle.

"Would you mind?" I asked, holding up the bottle of suntan lotion.

"Of course. Anytime, Penny," Craig replied.

"Thank you, baby," I rolled onto my stomach, giving Craig an eyeful of what I consider my best asset, and then, once settled, untied the strings of my bikini top. I knew men usually found me attractive. I have noticed the boys admiring my well-sculpted body over the years and I've heard their whispers. I've even caught Steven admiring the view on a few occasions. I knew this was only natural. And besides, they weren't the only ones enjoying the view.

Craig's big hands felt soft, and yet strong, on my back. I thought he could probably wrap them completely around my waist. I wished he would rub more of me, but he'd been respectful and kept to just my back and then quickly rejoined the match.

I watched the boys for another half hour and then headed back inside to shower and change. With the bedroom door locked, I started the shower, peeled off my bottoms, and grabbed my toys, the only action I'd had for the past year plus. Today, I grabbed my trusty vibe and my dildo. Sometimes I needed the actual penetration, to feel a big cock stretching and filling me. From the bulge in Craig's shorts earlier, I was pretty sure he could get the job done. It was this image, of Craig on top of me, giving me a good hard pounding, that sent me over the edge. I covered my face with my pillow to stifle a guttural groan as I convulsed and squirted my juices onto my sheets. That didn't take long. God, I fucking needed that.

*******

"Hey, Mom, I think we're going to stay in the guesthouse again tonight. We'll probably get some pizzas and chill, if that's cool?" The boys often stayed in the guesthouse behind the pool. They could stay up as late as they wanted, usually playing video games or whatever 18-year-old boys do. At least they were doing it here, where they were safe. I have always been the cool mom, which is why the boys were almost always at my house, which was just the way I wanted it.

"Sounds good, baby. Let me know if you need anything. Just put the pizzas on my card."

It looked like I was in for a quiet night, which was perfectly fine. A bubble bath, some light jazz, and a good book. Maybe I would actually read it tonight, thinking about the afternoon and how watching the boys had turned me into a puddle of lust. Would Steven ever forgive me if I gave in and let Craig fuck my brains out. Sadly, I knew I could never let that happen.

I wondered how long I'd been asleep, having dozed off after a big glass of red wine. It was one-thirty in the morning. The lights were still on in the guesthouse, which was no surprise. Wide awake now, I wandered around the pool, enjoying the warm summer night as I often do when I can't sleep. As I got closer to the guesthouse, I could see the shadows of movement in the living room and hear the rock music. It sounded more like a party than a group of boys playing video games. I didn't want to invade their privacy, but a quick peek seemed okay. I thought it was unlikely anyone would even notice me.

Stepping on the pavers, to avoid any noisy rock crunching, I crept to the window and looked in. Girls! My hand shot to my mouth as I gasped, audibly filling my lungs. Luckily, no one inside heard me thanks to the music and other sounds, mostly made by the two girls.

It was the twins. I recognized them immediately. Lisa and Sarah, a year older than the boys, had lived in the neighborhood for years. Mike was fucking Lisa doggie-style on the couch, his big, black cock making long strokes and his hips pounding against her creamy, youthful ass. A pair of massive tits swayed beneath her. They were at least D-cups. I knew it was Lisa because she'd always worn her crimson hair shorter, but the pair was otherwise indistinguishable.

As much fun as Lisa appeared to be having on the couch, Sarah was doing even better on the floor. She was on a blanket, on her back, with her legs spread wide, getting fucked vigorously by Ray. He didn't look to be as big as Mike, but he was well above average and Sarah seemed to enjoy it. Craig was filling her mouth with his extremely fat cock. I knew it. Craig has a great dick. I could feel the warmth in my mouth as I salivated, watching his shaft stretch Sarah's rosy, pouty lips.

I was unable to move, other than the hand moving involuntarily between my legs, putting pressure on my longing clit. I had never seen or done anything this adventurous in my life. Sarah's fair skin was silky smooth, her tits bouncing, her head bobbing on a fat cock with an assist from Craig's strong hand wrapped around her pony tail. My fingers started to move, rubbing my clit hard and slow, my hips rocking gently.

Ray grunted and arched his back, pulling out and spurting his seed onto Sarah's belly and her neatly trimmed, fiery triangle. I noticed Sarah had a piercing in her belly button that was now submerged in Ray's cum. As he stood and backed away, the surprises kept coming. Replacing him between Sarah's spread thighs was my son, Steven. His enormous erection waving above her. Fuck! He was bigger than the other boys. He was even bigger than his father had been. His father had practically ruined me for other men, with his powerful prick. My few attempts at dating since his passing had all ended in disappointment.

Sarah closed her knees playfully, acknowledging her rightful trepidation. I wondered if Sarah had taken Steven's cock before. The thought had me immediately gushing on my hand and biting my lower lip, stifling a groan.

Sarah allowed Steven to part her knees and she spread her legs wide for him while still bobbing back and forth on Craig's member. I could hear Sarah moaning as Steven slowly worked his cock into her, inch by inch. Sarah's moans, muffled by the fat cock in her mouth were so fucking sexy. My hands were now inside my shorts, with two fingers plunging through my soaking slit while the other hand rubbed my clit.

Craig was next, cumming in Sarah's mouth. She dutifully gulped his seed, losing only a few drops that ran down her cheek. Mike had pumped his load into Lisa long ago and the two were laying on the couch, watching intently.

Steven gripped Sarah's calves and placed her ankles on his shoulders, leaning over her. He started thrusting harder and faster, burying his cock with each long stroke. I could see Sarah's chest and face flushing as her orgasm swelled. When her moans and grunts stopped and her face scrunched adorably, I knew it was going to be the big one. She was about to cum on Steven's incredible cock. What a lucky girl.

Big doesn't begin to describe the sounds that came out of Sarah's mouth. Startled back to reality, I ripped my hands out of my shorts and began stumbling, retreating backwards. The fear of being caught was overwhelming. Once inside the house, I peeked back toward the guesthouse and watched for several minutes. The coast seemed to be clear. I sprinted into my room and locked the door.

Tuesday, August 24, 2021

"Hey, isn't that Sarah and Lisa?" I asked, as we drove past. "Do you ever hang out with them these days?"

"Yeah, we hang out with them every now and then," Steven replied casually.

Uh-huh, I wasn't going to let him off the hook so easily. "They are real cuties. What do you do when you hang out with them?"

"Oh, you know, just play video games and stuff."

"Ah, stuff. What kind of stuff do you do together?" I teased, unable to suppress the smile. "I bet that Sarah is more your speed, huh, baby?"

"Uh, what are you talking about, Mom?"

Pulling up in the driveway, I suggested, "Let's make some dinner. I'm starving. How about some lasagna?"

"That sounds great, Mom."

The conversation was light and cheery as we worked in the kitchen. Steven was interested in cooking and had even helped me improve some of our frequent dishes. I was nervously waiting to continue our conversation from earlier. "Dinner is in the oven. Come and sit with me."

"I have a confession to make," I started. "I saw you with the twins the other night in the guesthouse."

"Oh, yeah, they spent the night hanging out with us. It was a really wild night." Steven said sheepishly, "What did you see us doing?" He was obviously not sure how much to disclose.

"I only watched for a few mi--"

"You watched?" Steven interrupted, clearly shocked by the idea of his mom watching him have sex. "What did you see us doing?"

"It was only for a few minutes. I couldn't sleep and I was walking out back and heard some noises. Not loud, but sounded like young people having fun so I just wanted to check on you, without invading your privacy. I was so shocked that I think I just froze. At first, it was just the other three boys, Craig, Ray, and Mike having sex with the twins. Ray and Craig were both with Sarah on the floor and Mike was with Lisa on the couch."

"Where was I?" Steven asked.

"I don't know where you were. I didn't even think about it at the time. I was still in shock from what I was witnessing." There was no need for full disclosure of what I was actually doing. "Once Ray, uh, finished with Sarah, that's when I saw you for the first time. You took his place and started having sex with Sarah, while she was still giving Craig a blowjob. When you gave Sarah that near-window-shattering orgasm, it scared me back into reality. I panicked and ran back to the house."

Steven seemed at a loss for words and I couldn't really blame him. How do you respond to that? He was mortified.

I needed him to know it was okay. "I really am sorry for spying on you like that, baby. I know you are an adult now and deserve your privacy... I know it seems gross, a mom watching her son have sex. I have to tell you, baby, it didn't feel that way. Watching you, the man I love more than anyone else on Earth, give such pleasure to someone. I thought it was really beautiful."

"That's weird, Mom. I really don't want to talk about it."

"You want to know what else I thought?"

"Probably not."

"That Sarah is a very lucky girl. You take after your father in so many ways. You might even be bigger than he was." I gave him a wink.

"Mom!" Steven protested.

"And Craig is no slouch hi--"

"Enough! Stop it!" A smile appearing on his face for the first time, thankfully. Maybe we were okay.

Steven fixed our plates while I poured us each a glass of red wine. I had assumed that I saw most of the action, but apparently not.

"So, the twins stayed all night, huh. What happened after I left?"

"We're not talking about this. You're my mom."

"C'mon baby. You don't have to go into the graphic details, just give me the big picture. Give your lonely mom a treat. How'd you talk the twins into having group sex?"

"You've got it backwards. Those girls are wild. It was their idea. They just started taking off their clothes and then asked why we were still dressed."

"I can't imagine being that adventurous, especially at your age. Please, baby, fill me in," I begged, a little too desperately.

"Okay. I'll tell you one thing. They said they wanted to be DP'd and that we had the perfect numbers for it."

"DP? What's that?"

"Double penetration. One guy in the pu--, uh, vagina and the other guy in the, um, butt."

"Oh!" I got it. I think I was aware that people did that, but I was shocked that my son and his friends had DP'd the teenage girls I'd seen running around the neighborhood for years. I had to know more. "You had anal sex with them?"

"Yeah. We all did. It was the craziest night ever. Definitely a first."

I could envision the twins being impaled by my big, strong boys. "Thank you for helping with dinner, baby. I'm going to get cleaned up and change into something more comfortable." I gave Steven a kiss and a big hug. "Do you have any plans tonight, or am I lucky enough to have you all to myself?"

"No plans. Just you and me tonight, Mom."

"Perfect. Maybe you could find us a movie?"

"On it."

Once in the bedroom, I locked the door and started the shower. My vibrator was getting more action this week than it ever had. My memories of Steven and Craig double-teaming Sarah competed with the fantasy of Steven pounding Lisa's 19-year-old asshole. I sucked my middle finger and shoved it forcefully into my ass, quickly adding a second finger. I writhed on my sheets, working my clit with my vibrator and fingering my asshole until I exploded again.

Freshly showered, with dryish panties and back in my right mind, I sat down on the couch next to Steven and asked, "What did you find for us, baby?"

"A Quiet Place Part II. We saw the first one."

"Oh yes, I remember that one. You get the lights. I'll get the blanket and make sure the doors are locked."

It was a pretty suspenseful movie, but I had no idea what was happening. Twenty minutes in, I paused the movie and turned toward Steven.

"What is it, Mom?"

"Well, I can't stop thinking about what I saw last weekend. And, uh, I want to spend the night with you guys in the guesthouse," I just blurted. It had sounded better in my head.

"What!? What are you talking about?"

Well, in for a penny, "I want you boys to do to me what you did with the twins. Except, I'll have all of you to myself."

"Mom! Have you gone crazy? I'm your son. Why do I keep having to remind you of that?"

"Maybe a little, baby. It was just an idea. Let's just watch the movie and forget I ever said it."

Thursday, August 26, 2021

"Who's this handsome stranger, waiting at my front door?" I asked Craig. I was just getting home from a real estate appointment with one of my few clients. I kept my schedule mostly clear to spend as much time with Steven as possible. This client was an attractive younger man so I dressed a little sexier than I typically do. I didn't see anything wrong with sweetening the deal with a little eye candy. I wore a tight skirt, with a white, silk blouse that exposed a fair amount of cleavage, along with four-inch, black heels. Craig seemed to approve of my fashion choices as he looked me up and down.

"Hey, Penny. You look fantastic. I wish I could afford to buy a house," he said playfully. "I think I left my uniform in the guesthouse last weekend and I need to grab it, if that's okay."

"Sure. I think it's locked. I'll grab the key and meet you out back to let you in. Be right there."

Craig was waiting for me at the door again as I clicked down the cement path toward the guesthouse. He had no idea how lucky he was about to get.

"How good are you at keeping secrets?" I asked, closing the door behind us. I also turned down the thermostat. We don't keep it cooled when it's not in use. It would take a while to cool down, but that was perfectly okay. A hot, sweaty fuck was just what I needed.

"Uh, I'm great at it."

"Good answer." I leaned into Craig and kissed him. His tongue immediately responded to mine and we pressed our bodies tightly together, his big hands caressing my back. His touch felt electric through the silk blouse.

I pushed Craig back a couple of steps and he awkwardly plopped down on the sofa where I had watched Mike fuck Lisa the other night. I got on my knees between his legs and ran my hands up his thighs, squeezing his muscular quadriceps and then over the impressive bulge that was forming, giving it a big squeeze, as well.

"We won't be needing these anymore," I unbuttoned his shorts and slid them off, with Craig's eager assistance. "There's what I need," I kept eye contact with him as I took his mostly-erect member into my mouth for the first time. "Mmm. Delicious," I purred and began slowly bobbing up and down on his shaft.

I stroked his shaft as I licked and sucked his tightened sack and substantial balls. I was probably going to get an extra big load in my tummy soon, I thought. I had been so wet all day and I was feeling extra naughty. I moved farther south, licking the underside of his ball sack, finding the pungent, salty taste delightful. I wanted more. I pushed his legs back and worked my tongue down until I found his hairy asshole. Craig moaned as I forced my tongue as deep as I could into his anus, then licking it like a lollipop and then probing with the tip of my tongue again. I used to love giving my husband this pleasure.

Ready for the main treat, I moved back to the now-throbbing cock head swaying in front of my face. This time, I extended my tongue down the underside of his shaft as far as I could, making room in my mouth to get as much of his fat cock down my throat as I could. It really was like riding a bike. I had Craig balls deep in my mouth within a few bobs of my head.

"Whoa, Penny. If you don't stop, I'm gonna cum soon," Craig warned.

I sucked his cock harder and faster, my eyes never leaving his. He got the message and put his strong hand on the back of my head, pushing his cock deeper into my throat.

"Oh, fuck! I'm cumming!" Craig grunted, thrusted his hips, and pumped a hot, thick load into my mouth and throat, which I joyfully swallowed. I sucked as long as he would let me, milking out the last drops.

"That was so good. My turn, baby," I took Craig by the hand and led him into the bedroom.

I unbuttoned my blouse and let it fall to the floor. Craig helped me out of my skirt. Still wearing my soaked, white-laced panties and high heels, I scooted back onto the bed and Craig quickly followed.

Craig was the most muscular of the boys. Feeling his weight on my hips, while we made out, drove me wild with anticipation. I wanted those hips pounding into me hard. I put a hand on his head to urge him lower. He took his time, as instructed, gently squeezing my pillowy, full C-cups as he licked and sucked each of my nipples. He was very talented with his tongue. His fingers found the wet spot on my panties as he continued swirling his tongue around my puffy, erect nipples.