I didn’t expect much for graduating from college, but the best present I ever received for that expensive piece of paper was from my mom’s friends.
The day started with waking up at dad’s condo and having lunch at our favorite Cuban food spot.
He gave me a card, some money, and after finishing my shredded beef, he drove me across town to mom’s and stepfather’s lush south side mansion. Two years after the divorce and you could still see the hurt on dad’s face when he pulled up in front of that white stucco mansion with palm trees and a flat roof. Chaz, my stepfather, had a flair for throwing big cookout celebrations. He also used it to flaunt his money and wealth, not to mention parade my forty-plus-year-old mother around like she was some prized big-breasted trophy wife. Beauty’s in the eye of the beholder, but it still stung dad knowing it was Chaz who wooed mom away. In the end, my stepfather was someone dad could never keep up with.
After a solemn handshake (and pretending to not see him hold back tears) I left dad’s beamer and went on to join the festive celebration.
The backyard cookout and pool party was in full swing as I walked up the wide driveway and around the side through a heavy oak fence gate. It paid to be the CEO of one of the most successful yacht and speedboat companies in Venuz Beach, Florida. My stepfather’s work colleagues and customers wealthy enough to live a life of luxury littered the backyard, getting drunk on sangria, as Jimmy Buffet-esque “Gulf & Western” music belted from the white patio stereo system. Chaz stood behind the grill in his goofy chef’s hat and smock, giving me an exuberant wave and clicking his tongs. He didn’t even bother to show me where I would be staying for the night, and he went back to cooking.
I stood there holding a suitcase and my backpack like an idiot. Like most parties, I was the oddball out in the crowd of mid-life crises yuppies and bitchy spoiled housewives. The only tolerable two were mom’s longtime friend’s Nancy Halo and Tricia Bermudez, who lounged out by the pool in their swimming suits.
Nancy and Tricia were like surrogate sisters to mom. They were all friends since the eighties, taking part in both high school soccer and varsity cheerleading. The years since then have been alright with them. They honestly weren’t bad for being in their early forties. Nancy and Tricia weren’t necessarily chubby, but there was a “soccer mom bod” thickness to their thighs, stomach, and hips that came naturally with age and having kids. But even with their rolls and vague cellulite, they still possessed the athletic frames for their youth — just with more to grab.
Their most defining feature between them both was their tits, which spoke nothing but volume and mass from under their bathing suits.
Nancy was the alpha of the two. She was thick, domineering, and two inches taller than me. Nancy also was the one who fully ignored her age, wearing a pink and yellow spaghetti string two top. The outline of her heavy cleavage pressed up against each other in her tiny bikini and her long curly dark blond came down over her left shoulder. Tricia was shorter, with small feet, wide hips, and longer tits that were held up her navy-blue one-piece. Her mocha skin made the white pearls she wore stand out; the golden hoop earrings gleamed under from her wavy raven hair. And where Nancy’s domineering personality flourished, it still was no match for that Puerto Rican allure that Tricia had when she smiled at you.
It was obvious they were dressed to impress. Tricia and Nancy, according to overhearing mom’s past conversations, could be quite assertive and insatiable when they wanted to be. I didn’t know how much truth there was to that, but their husbands, even their kids, were nowhere in sight. However, the attention they were trying to attract went ignored by the ambitious and successful older men there. Whether it was too much money or even that youthful gold digger pussy that clogged their brains, but a bubble seemed to form around mom’s two friends. Those who knew about the bubble beforehand stayed clear of it. Then there were guys like me, recent college graduates, who nothing to show for it except working the same landscaping, pool, and handyman job I’ve had for five years. Guys who had no fear, let alone an idea that there even was this bubble, to begin with, and would naively cross over. But once you crossed into their bubble, you were at their whim.
Not really. But then again, maybe I just had respect for the classic, instead of the new. Dad said it best: never take a sleek, eco-friendly sedan for a cruise, in you can still burn rubber on a ’76 Camaro. I’ve never been big on dad’s allegories or quasi-wisdom, but I always did like that one.
It didn’t take much for mom to spot my arrival, and she greeted me in her typical long sundress, bug-eyed sunglasses, and long flowing bleached blonde hair. After giving me a big hug and congratulating me, she then began to lead me around the party and introduce me to my stepdad’s business partners, loyal customers, and co-workers. Many of them were vapid, ego-driven men, insecure about their middle age, and could only hold a conversation about money. Some even-sized me up (the 20-something young buck) as competition, holding their trophy wives at bay.
I don’t blame them. Not to break the fourth wall or anything, but I am pretty much the living caricature of the “Latin Lover”. I’m half-Cuban, half-Sicilian; my body is lanky yet muscular; and from past girlfriends, my penis can only be described as “long and girthy”. (How’s that for tooting your own horn?) That’s probably why most of those “SWASP” (Southern White Anglo-Saxon Protestant) assholes saw me (a Cuban-Sicilian, 2nd gen-born American guy) as a threat. All the money in the world couldn’t stop their girlfriends or second and third wives from desiring a good romp, even if it were for just a quickie — all it took was a look, but not from me, but them.
No, I swear, I’m not bragging. It’s been both a gift and sometimes even a minor problem for me since my lawnmower business ended at eighteen.
As I was paraded around by mom, where I shook hands with about twenty or so guests, I was finally led to Nancy and Tricia. I’ve been acquainted with these two since I was a kid, but even behind their sunglasses, I could see they were eyeing me up with lustful intentions. It was initially a little awkward, to be honest. I’m usually the one checking the women out. But to have it done to me, by two obvious MILFs and cougars, the shock of the postured role-reversal fizzled, and excitement came over me. Especially when I saw Tricia staring right through my flowery shorts as if my cock were hanging out.
Mom, who despite all her complicated personality features, was naive at first to all the eye-fucking that went on.
“I’m sure you both remember who this handsome fellow is,” she said.
Her two friends laughed. I tittered with them feeling like we were all in on a dirty inside joke at the behest mom.
“Yep!” Tricia said with excitement.
“We sure do,” Nancy added.
I smiled, reluctantly giving in to my childhood shyness, and waved. The two then laughed again, this time with a mom like I was out of the loop.
“So, Mike, a little birdy told me you just graduated from our very own local Augustana University,” Tricia said.
I cringed in the way that hot mature Boricua worded it. It was common vocabulary among the “new money rich” that infested Venuz Beach’s upper-class southside. Everything was deemed theirs, even universities they never attended, but it was a part of “their bubble”.
“I did. With honors,” I played along.
Mom’s friends lit up like I just announced my cure of cancer.
“Really? Congratulations!” Nancy said. “What did you graduate in?”
“Business marketing.”
Mom’s friends looked at each other and nodded in approval. It was an acceptable degree on the southside. It would fit and further their bubble for the next generation.
“He’s going to be staying with us too for the summer,” Mom added.
It was an exaggeration. Ever since Mom and Dad divorced, Mom has been trying to make up for whatever perceived mental and self-esteem trauma that may have occurred within me because of it. When, the only thing it did was make was deal with Chaz’s persistent badgering on giving me a job at his boat sales place.
“Well, the southside certainly better, and safer, than what I’ve been hearing on the northside. Can you believe there were four shootings last night in Mayport?” Tricia said.
“He’s from the West Side.”
Ah, yes, the boring, middle-class, suburban wasteland of the west side. At least the northside bore some danger to it, a hardness that was attractive to most girls in their early-20s who liked bad boys and have convinced themselves they know better. But the mere mention of the west side, the middle-class average joe side, seemed to entice the older ladies. Nancy even wiggled those soft, wide hips deeper into the chair and softly moaned.
“Well, welcome to the better side,” Nancy added. “You’re more desired down here.”
I opened my mouth to speak, but the way she worded her remark caught me off guard. Nancy was hitting on me, I felt. Even worse, she had the guts to do it in front of Mom. From the corner of my eye, I watched mom’s narrow in suspicion. You could tell she didn’t like what her friend said, but before mom could say anything, Chaz called her over. After patting me on the shoulder and giving me a look as if to say, “watch yourself”, Mom left me her best friends.
The steel drums and twangy guitar continued to play through the speakers; the ambiance of chatter surrounded me as I stood there alone. I even held onto my Nancy and Tricia sipped from their daiquiris. Nancy then slipped her hands behind her tits. They vanished under the large, sagging breasts and pressed them together to scratch deeper.
“So,” Nancy began, scratching the underside, “you graduated with a girlfriend?”
“No, not really.”
Nancy grinned, rolling the tits together to show how large and soft they were.
“Seriously?” Tricia said. “Cute college grad like you? I find that hard to believe.”
I shrugged my shoulders, pretending to not notice the flirt. But when I returned to Tricia, she didn’t look me in the eye. She continued to stare into my lap region, looking to spot my growing bulge behind the fabric.
“Guess I like to keep my options open, y’know.”
Pausing, I wondered if that could be perceived as flirting or a joke. Nancy and Tricia proceeded to smile with lustful intention at that one.
“Well, maybe you’ll find one or two here,” Nancy added, “just keep your eyes open.”
Putting my mouth into a smiling, crooked grin, I nodded and said sure.
The feeling of sex was imminent. It was the gut feeling that grew from having so many one-night stands and unforeseen romps at college. Reminding myself that these two were mom’s best friends, I told them to enjoy the party and left the scene quickly. I was stuck here until Monday morning when dad picked me up again, so I did my best to privately celebrate on my own.
After putting my suitcases in my regulated bedroom: the white stucco and oak pool house that stood semi-isolated at the far-end of the backyard. I then skipped right through the party and went to my stepdad’s study. He was still trying to get on my good side, which constantly put himself in “yes man” mode when it came to me. I raided out the good stuff from the hidden compartment under his desk: a small bottle of hundred-proof Cuban rum (illegal in the states) and a couple of nugs of some good and frosted purple kush. I then took the stuff back outside and made my way toward the pool house I used as my bedroom.
Following the edge of the pool and avoiding any more eye contact with yuppies and their female prized possessions, I looked back over my shoulder in the direction of Mom’s two best friends. Nancy and Tricia continued to eye me down from afar. My sex experience all up until that time was one of the mostly young adult women, no higher than twenty-five. Anyone older was all but foreign to me, but I was FAR from being uninterested.
As the muffled sounds of Caribbean and country music pressed against the tinted windows, I alternated between the bite of the rum and the spark of bud, playing video games until I passed out. Anything was better than having to socialize with those people. Except for maybe Nancy and Tricia. I hated to admit it, but the first word that came to mind describing my encounter with them was a couple of “cougars”.
***
I woke up early, really early with a slight headache from the rum and the wavy after-effects of the weed. Oddly, my cock was semi-hard, and I didn’t even have to piss.
In my dazed state, I was unsure how that was even possible until I felt a pair of hands under my tank top, caressing my flat, washboard stomach.
I was half-awake but came to when another pair of soft hands pushed themselves up through the pant legs of my shorts and grabbed a double-handed grip on my cock. Opening my eyes, I sat up to find that it was still nighttime but somewhere in the wee hours of the morning. The festivities outside were done. The pool house carried a low red neon light from the ceiling: enough to illuminate the small room, but not enough to bleed through the tinted window or doors.
Blinking the sleep from my eyes, I saw that it was two older but curvaceous females who were touching me.
“Oh shit,” I said, laughing nervously. “What the hell is this?”
The two laughed and I recognized the voices. Tricia and Nancy nuzzled a little closer over me in response. A rush of excitement ran through me as Nancy’s cold hands traced the lines in my pecks and abs, but I cut it off. I was still figuring out what exactly happened between my arrival and then. If I didn’t know better, I thought my stepdad’s stash would be a little “weaker”.
Everything was starting to come back to me.
I had passed out with my legs dangling off the foot of the bed. Tricia had kneeled between them, her arms shoved deep up into my trunk pant legs. The roving fabric of my shorts described the motion of her tugging on my hardening cock. The mattress then sunk to my left, and I looked over to find Nancy kneeling next to me, putting both arms around my shoulders. My cock stiffened as Tricia’s grip tightened around the skin.
“Whoa, whoa, wa–”
Nancy silenced me by clasping a hand over my mouth, using the other to caress my stomach and chest.
“Shhhhhhh,” she said. “We want to give you something.”
I shook my head, still seeing the look mom gave me earlier.
When Nancy pulled her hand away, I said, “I-I don’t know about this.”
“Relax, Mike,” Tricia said, her hands stroking my hard cock. “We’ve always thought you were a cutie. Mary is lucky to have such a good son like you.”
“Yeah, but if she finds out about this–”
Nancy leaned in closer into me. Her plump tits mashed up against the side of my face. She smelled of mango body lotion and her bulging tits were so soft that the temptation became overwhelming.
“Think of this as your graduation present, Mike,” she said.
Nancy’s free hand slid down from my chest to breaking just under the elastic and massaged my cockhead with her fingertips. Tricia cupped my balls and slowly caressed the underside. It was too much; I became erect within seconds. The wave of excitement began to burn the more I fought against the temptation.
“Let’s just have some fun. From us to you.”
I gave Nancy my answer by wrapping my left arm around her waist. Exhaling deeply, I pulled her body closer and shoved my face deep between her tits. The burning inside me subsided — shit was gonna go down. Nancy welcomed it by holding the back of my head there with her hands. My mouth frantically kissed and sucked the outer edges of her thick cleavage. I brought my hands up and scooped both tits from the bikini top. Her mature tits slumped out in front of me, a little saggy with large areolas.
Pressing them back together, I pursed my lips and continued to suck and kiss them.
I held nothing back at that point because, well, this would be my first threesome.
Tricia eventually let go of my cock. Grabbing my swim trucks, she yanked them down to my ankles and left them there. Grasping the bottom shaft of my cock, she squeezed hard enough for my entire penis to throb and slid her thick lips over it. She sucked my penis tightly, pressing my cockhead against the inside of her wet and silky cheek. I sucked in a short breath from the sensation, pulling my mouth from Nancy’s left tit. She responded by angling my head up to her mouth and kissed me hard. We exchange tongues, making out intensely for lord knows how long, all while Tricia sucked and slurped on my cock.
The ecstasy at that moment was so overwhelming I experienced brief moments of light-headedness. I have always had an attraction to older women, but Tricia and Nancy being firm and assertive in their passion made me want to fuck them till the sun came up.
To show them I meant business, I pushed a hand between Nancy’s legs. The thickness of her inner thighs pressed against both sides of my hand as I wiggled my middle and ring finger up around her bikini bottom and through her fat pussy lips. Curling them inside, I felt Nancy gasp in a sharp breath and lean into me so I could feel her body weight.
We fell back onto the bed as Tricia’s head bobbed up and down on my cock, our lips continuing to suck on each other’s tongues.
“I want to ride the shit of that young cock,” she whispered through our kissing and me squeezing down two handfuls of titty fat.
I happily played her game. “You do that and I’m going to fuck the living shit out of you more than your husband ever could.”
Briefly, we connected eyes in the red dimness, and I watched her mouth make the words: do it.
Tricia pulled her mouth off my cock with a sharp pop and Nancy sat back to straddle me. Tricia hopped on the bed next to me and took Nancy’s position. She shoved her mouth onto mine, her lips a little firmer and thicker than Nancy’s. As we kissed, Nancy held my penis in place and lowered her wide hips down onto my cock. My dick penetrated slowly through her fat lips; her pussy was a little loose, but the girth of my cock filled her up.
As Nancy gave me a couple of slow, warm-up bounces, Tricia pulled her mouth from mine and threw a leg up over my face. I pulled aside the one-piece bikini bottom and shoved my tongue deep into her pussy. Her shaved lips pressed tightly against my mouth, and she moaned softly as I began to suck and lick on her clit. Tricia’s body trembled as she moaned, and I ran my hand up her cellulite thighs to hold her in place.
Our moans and breathing quickly filled the quiet room, arising in synonymous groans and heavy exhales that grew in intensity. Soon, Nancy bounced up and down my cock like a wild banshee, alternating between that and rolling her torso like a wave. Tricia did the same over my face, leaning into her friend and kissing her firmly. I moved my hands from Tricia’s thighs to Nancy’s, wrapping around her hips, and cupping the outer edges of her basket seat butt.
“You like this milf pussy?” she asked, panting heavily.
I gripped Nancy’s ass with one hand and slapped it with the other. She laughed and moaned, going back to twerking her ass up and down on my cock. To compliment her bouncing squats, I thrust frantically upwards over and over, lost in the darkness and the passion of the moment. Nancy bounced with my cock until her body suddenly froze.
“Oh fuck!” Nancy yelled, pressing her hands against my chest and holding her trembling body upwards.
Her body shook intensely and finally became dead weight atop me.
“Is it good?” Tricia asked her.
“Oh…fuck…I just cummed. He’s great!”
“My turn, Nancy. Let me give him some,” Tricia finally said.
Nancy pulled my cock from her pussy without question. As both bodies slid off the top of me, I went to a kneeling position, hoping to give my penis a few strokes before going at it again. The two women threw themselves at me on both sides, drowning my face in their heavy tits, and stroking my cock for me. We three-way kissed, swapping tongues once more; their hands pulled my already hard cock and I squeezed down on their ass cheeks.
Finally, Tricia fell onto her hands and knees, shifting that jiggly plump ass of her’s toward my penis. Nancy meanwhile shifted her body behind me and pulled my tank top up over my broad shoulders. Naked and slightly sweaty, I pressed my hips forward and pushed my cock into Tricia. Her pussy was tighter than Nancy’s, and the sensations rippled a little bit more as my crotch popped against her chunky butt cheeks.
Her moaning grew louder with each thrust of my hips, eventually, she spoke only in Spanish and demanded me to give it to her harder. Nancy’s tits pressed up right up against my back, as she ran her hands up and down my chest and abs. Licking my neck and nibbling on my earlobe, she began to talk dirty.
“I want to jerk that cock. I want you to see that cum, baby.”
“Yeah, how bad you want it?” I asked her, thrusting my cock into Tricia.
“Bad. I saw you walk in today, and I knew I wanted it. I don’t even care that your mom is my friend, I knew I was going to have it.”
We continued to talk dirty to each other, resulting in me thrusting faster and deeper into Tricia. Eventually, I was so aroused that I hit that pussy as hard fast, and hard as I could, pumping my cock until Tricia gasped and lowered her upper body down into the mattress. My senses rose to see that I had made her orgasm, and instead of stopping, I only continued. Raising a leg and hooking it up over her waist, I continued my heavy pounding.
“Yeeeeaaaah, that’s soooo hot! So fucking hot!” Nancy said, gently turning her fingernails into my skin.
“Oooooooooo, I love…I love this young cock!” Tricia yelled.
“Way better than that husband of yours. How long has he been limp for?” Nancy added.
The two laughed. I continued to thrust until I grew winded in the lungs and slowed.
Neither responded at first. I looked back over to Nancy, who moved to the side of me again. Her eyes were wide and glossy with ecstasy as she looked at me. Without saying anything, I leaned over and firmly began to kiss her. She did the same and I ended it with nibbling away at her bottom lip.
“You want this cock?” I asked her again, running my hands under her pussy once more.
She just breathed heavily, wrapping her arms around me, and shoved her tongue down my throat. Tricia screamed out in orgasm a second time, and through her moaning, I heard Nancy finally say yes. Tricia then pulled her ass from my cock and spun back around to face me.
Standing there naked and so fully erect that it ached, Tricia quickly pushed me back down onto the bed. I fell right to my back with the two forty-year-olds pressing their doughy bodies between my stretched-out legs.
“Suck that cock, give us that cum!” Nancy told Tricia, grasping the bottom of my shaft and squeezing tightly.
Tricia, still reeling from her double orgasm, moaned and panted, and wrapped her mouth on my cock. The sucking was intense, and the sensations grew quick as I leaned my head back. She only continued this until I finally burst.
Nancy and Tricia’s moans reached their peak just as cum erupted from my cock. Nancy gripped my shaft even tighter in the climax. They pushed their faces into my penis, fighting to lick and suck away the cum. It eventually went to Nancy, who pressed the exploding tip against her inner cheek and gently rotated her head. I orgasmed so hard that my legs tightened, and my toes curled. And even after my dick grew limp, Nancy continued to suck and then swallow. The feeling felt so good it was paralyzing.
When it was over both sat back on the edge of the bed. Nancy rubbed away at her mouth and Tricia panted. Their un-toned hourglass bodies came out in the red neon sweaty and plump.
After Nancy finished wiping away her mouth, she rocked forward and patted me on the stomach.
“Don’t say we never gave you anything for graduation.”
“Oh, fuck…oh, fuck…. oh, fuck….,” I whispered.
Eventually, I could move again but barely did, rolling to my back. I laid my arms across the pillows, allowing the two moms to nuzzle up next to me on either side. The feeling of their soft bodies against mine, where they did prop their legs over each of my thighs (that’s hot as hell when women do that by the way), felt almost as good as my orgasm. But as the effects of my cumming fizzled out and the drowsiness swooped over me once more, I felt Nancy and Tricia’s bodies become dead weight into mine. It was then that I realized they were going nowhere for the night.
The silence fell between us for some time. I kept my eyes closed; the comfort I was in was astounding. Nancy’s head adjusted and then lifted off my chest; Tricia had already fallen asleep cause I could hear her soft snoring. Nancy’s finger then tapped me on the tip of the nose and ran down over my lips. I opened my eyes to the darkness of the pool house again and Nancy’s voice came through the void.
“Are you staying with your mom the whole weekend or just the night?”
“The whole weekend,” I said.
Her warm cheek pressed against my right peck. She rubbed her wet pussy against my leg, getting comfortable once more, and circled her hand around my stomach. You could tell Nancy liked the fact I had a six-pack.
“Good,” was the last thing either of them said. “So are we.”
TO BE CONTINUED
Author’s note: An earlier draft of this story was originally published on here back in 2018. Still, constructive criticism is always welcomed.