Maui Mischief 2020

Thumb deep in Cindy, I say, "this is so fucking sexy, mom!" Gasping between every word, Cindy says, "don't call me 'mom' while your thumb is stuffed up my snatch and your fingers are polishing my pearl!"

Gulping for air, Cindy arched her head down on her folded arms pushing her pussy harder on my thumb.

The girls both writhe as my thumbs manipulate deeper into their pussies. Jen just giggled and squirmed against my hand. Flicking my thumb in the warmth of two slick pussies while simultaneously teasing two slick clits, I looked up to see Pigtails and Sugar Daddy watching us. Whispering, "we have an audience, girls."

Still gyrating on my thumb, Cindy looked up from her pleasure and, breathlessly asked, "well, 'Chicago', you just gonna' watch or are you and your girlfriend going to do something?" What happened next was enough to push the three of us over the edge.

Pigtails stood up and stripped off her bikini bottoms displaying her bald snatch, bent down and manhandled Sugar Daddy's erection out of the top of his swimsuit. "Daddy, it's time to show those good people what you have been saving for me." Sugar Daddy lay back on his elbows while Pigtails slipped off his suit. This guy had an enormous hard-on. It was not particularly long or big, but I am certain his arousal was due to our actions and the unexpected actions of the Asian girl with him. She was impressed, she teased, "is that all for me, daddy? I don't know if I can take it all into my tiny little girl twat!" She straddled his thighs facing him.

Cindy and Jenn were squirming against my increasing massaging of their snatches. "I gotta' see this," Cindy whispered to us both. "She's too small to take a real man's cock."

Pigtails and Sugar Daddy had an audience of discreet couples sitting on their own blankets. My threesome was the closest to observe and I noted that a few couples were diddling and stroking as they watched the three of us and Pigtails. Pigtails stretched up on her knees and challenged sweetly, "you ready for the ride of your life, daddy? I don't do this for just anyone." Holding Sugar Daddy's cock in her right hand and hovering above it, Pigtails lowered her tiny little pussy. She stroked his pre-cum coated cock front to back past her lubricated vagina to her tiny little clit.

I swear Jen was ready to burst with her orgasm when Pigtails pushed her over the top. Pigtails lowered her tight little pussy over the all-too-big cock head. Pigtails bit her lower lip as she struggled to take it all in. She whimpered as she got the head just inside her tight little snatch. Stretching further, she hovered there for just a moment. Sugar Daddy moved his nervous hands from squeezing Pigtails' nipples to her hips. "You can take it sweetie, just take your time." With a snarl, Pigtails took a deep breath and took another two inches into her twat. "Oh god, daddy, I want it all so bad." That put Jen over the top as she humped my thumb and hand as hard as she could. "Oooooooo, shit! Fuck, fuck, fuck, fuck I can't stop," and then Jen collapsed, exhausted.

Pigtails whimpered and plunged the final three inches into her immature pussy. Sighs of appreciation from the observers nearly ruined the moment, but Pigtails was too far gone to care. She rocked that cock like a bucking bronco as she came. She is a howler by the way. Sugar Daddy kept pulling her hips trying to get even deeper into the little Asian girl. I wondered if she was a local or a hooker or something. Anyway, the thought of this guy fucking his would-be daughter was fantasy enough.

My Cindy was bucking against my hand gasping, "faster, deeper, oh fuck!" Like Jen, she came buckets on my hand just having witnessed Pigtails' struggle to mount her boyfriend's cock. Pigtails collapsed on her 'daddy', panting rapidly, kissing him passionately on the neck. Pigtails was spent. Jen rolled off my hand and teetered off to wash off in the surf. Cindy cooed, "stay in me while I come down. Stroke me. Softly, Cam. I haven't cum like that in years." I whispered, "how about this?" I moved my thumb to the entrance of Cindy's butt hole. Still lubed I pushed gently against the entrance. "Do you do that to Jen? She never talked about that kind of sex. Give it a try and be gentle."

My cock was beginning to ache. I gently pushed my thumb into Cindy's butt hole up to the first knuckle. Her sigh told me she liked it. I pushed deeper and reassigned my index and middle fingers into Cindy's still lubricated hoo hoo. "Oooooo, that's incredible, sweetie. Careful, you might make me cum again."

I could feel my fingers and thumb meeting inside. Cindy reached her left hand out to my cock. "Oh, Honey, I thought you'd cum already. Please forgive me."

Jen was staggering back from washing off in the surf, she grinned at Sugar Daddy who was still root deep in Pigtails' tight little snatch. Looking at me and Cindy, Jen observed my erection, "you should probably take care of that 'throbber', Cindy." Cindy responded, "you're absolutely right, sweetie, and I will. Cam, lay back." I did as told, but not knowing quite what to expect. Cindy squeezed a dribble of oil on my stiffy and straddled me to sit on my belly. Jen kneeled facing her 'sister'.

Jen took hold of my lubricated cock that was oozing pre-cum in abundance. She used her left hand to cup my balls and squeezed gently. Grinning with mischief, Jen looked Cindy in the eyes, "you gonna' take care of that or am I?" Cindy responded by raising up on her knees, "you'd better help since he is your husband." Jen simply maneuvered my cock closer to Cindy's waiting pussy.

Cindy's pussy was dripping sex juices. Jen whispered, "move toward me, Cindy." Cindy scooted just above my aching erection. Jen held my cock just below Cindy, "come down just a little, I need to lube you two together." Oh shit, this is really going to happen; and my wife is encouraging Cindy. Cindy used both of her hands to open her lips. I watched my cock less than an inch from Cindy's inviting snatch. Jen stroked Cindy's pussy with the tip of my cock. "Cindy, this is the hottest thing I have ever seen in my life, I think I'm gonna' cum myself," urged Jen.

Looking toward Pigtails and Sugar Daddy, Cindy challenged, "watch this little girl." Oh fuck, Cindy drove my cock deep into her pussy in one swift move. Deep. All the way. Cindy caught her breath and let out a squeal; then a sigh of contentment. Damn, she was tight. Jenn had one hand on her own clit while massaging Cindy's clit at the same time.

I reached around with both hands to cup Cindy's tits and pinch her nipples. She has terrific tits. This was surreal. Cindy came quick. More rapidly and enthusiastically than the first time. She kept gyrating. "Honey, pay attention to my ass hole." I did and inserted my thumb as far as I could. Cindy gyrated even harder. Rocking reverse cowboy with the help of my wife was enough to wear her out. She collapsed into my wife's arms resting her head on Jen's shoulder. "Oh wow, you two made my year." Then Cindy kissed Jen on the lips maintaining a hug with my cock buried deep in her womanhood and my thumb in her ass. Cindy's vagina was squeezing my cock for all it was worth.

When she finally dismounted me, our observers along with Pigtails and Sugar Daddy quietly applauded with appreciation. We three took a bow and headed to play in the surf. We weren't that long, but long enough. I had my hands full, literally, with the girls. Jen asked me to do to her what I did to Cindy. With Cindy's help, we made a sandwich of Jen with my engorged cock balls deep in her pussy. Jen wrapped her legs around my waist while Cindy cupped her tits. "Jen, I want Cindy to do your ass with her fingers."

Cindy nodded to me and asked. "you okay with this Jen?" Jen nodded and gasped in pleasure as Cindy inserted one finger then two fingers into her butt hole. I could feel Cindy's fingers with my cock. "Oh god, I'm gonna' cum." With that statement escaping her lips, Jen bucked back and forth between me and Cindy until she collapsed her head against my shoulder. Cindy grinned and I let loose my cum deep in my wife. Wham, great!

Pigtails and Sugar Daddy were gone by the time we got back to our blanket. I patted dry my ladies. Life is great and I want to repeat this tomorrow. We could always just stay in the condo and play. Just a thought.

Chapter Three

Back at the condo we relaxed waiting for Rob to get home. Cindy threw the chain on the door and turned to me, "I don't want Rob to disturb anything without warning. Jennie, honey, do you mind if I use your husband again before mine gets home?" "Go for it!"

Cindy opened her beach robe to reveal she had nothing on underneath. She walked to me and dropped my speedo to the floor. "Come over here, Cam. I have some oil I want to try." Cindy poured a lot of baby oil onto her hands and was rubbing it on my cock and balls. There he goes again, hard as a rock. "This is just so wrong, Cindy," I started to say, but was interrupted. "I want this, Cam, and you're going to give me what I want. I cleared this with your wife. So, you may as well do as we say."

Cindy took me over to the kitchen island, turned away from me and said, "eat me from behind and, Jen, you watch to make sure he does it right." I knelt with Cindy's ass at nose level. Gahd, she has a nice looking, bald, snatch. My tongue was drawn to her ass first, then to her pussy. My right hand explored her pearl. Wow, Jen was milking my cock and applying baby oil at the same time. "Slow down or I'm going to cum too soon," I said as I stuck my tongue deeper into Cindy's delicate ass. Two fingers in Cindy, my wife milking my cock; what could be better. Boom, and then it was better. Jen retreated to the sofa and lay face up. Patting her own mound, "Cindy, you better come eat this while Cam fucks you." "Okay," Cindy gasped as she pushed me away.

Cindy grabbed my hand and took me over to Jen. Cindy looked me in the eyes, kissed me deep. Tongue dancing with my tongue, "you do me while I do Jen." At that, Cindy bent at the waist and buried her tongue in my wife's vagina, licking like there was no tomorrow. Me? I drew up behind Cindy's fabulous, glistening butt and stroked ass to pussy with my rigid manhood. "You gonna' do anything with that weapon, Cam, or do I need to do it myself?"

My cock stopped at Cindy's ass. I gently pushed the head past her ass muscle. "Oh, good work, Cam, keep it up." Cindy spread her legs wider, stuck her thumb into my wife's ass and uttered to us both. "Will you please get it on!" I pushed my length into Cindy's ass moving in slowly. Holding her hip with one hand and my thumb in her pussy. I braced for deeper penetration. "Oh god, that feels divine. Why did we never do this before?" Jen gasped, "oh yeah, we should have done this years ago." Jen bucked her hips cumming on Cindy's tongue. I painted the inside of Cindy's ass with cum and Cindy spasmed with another orgasm. "Cum together, like wow!" I hated to pull out, but someone put the key in the door lock. All three of us raced to throw on suits before Cindy unlocked the chain. "Hi, honey, how was the conference?"

Chapter Four

The next day was a bit more tame in that we stayed in the condo except for a trip to the beach at the end of the street. Jen and Cindy frolicked in the water again. I played with them a bit and caught some sun. Spreading sun block on both of my girls wasn't quite the same, but still a pleasure.

Toward afternoon, Cindy announced "we should shower and dress for dinner. Rob wants to introduce Dr. O'Brien to us at dinner. Rob says it's about time we met his partner." We showered, in that I mean, we all were in the oversize shower together. I had the pleasure of soaping both of my beauties as they soaped me. Cindy took the liberty of soaping my cock and balls while Jen soaped her tits and scrubbed my back with them. Glorious for me. Cindy bit my ear lobe and whispered to me so Jen could hear, "turnabout is fair play." With that, Cindy eased her finger into my ass hole. Never had that before. "My turn," whispered Jen. Cindy removed her finger and I felt Jenn go knuckle deep in my rectum with two fingers. Holy cow, we are definitely going to do this again when we get home. Cindy lowered her head and took my hard cock in her mouth. Soap and all, she sucked on me as I had never been sucked. "I'm going to cum," I grunted. "Give it all to me, baby," mumbled Cindy with my cock halfway to her throat.

Jen kept her fingers in my rectum and her left hand squeezing my balls as I let loose in Cindy. She gulped down all of it. "We are going to have to do this again," is all I was able to gasp.

We left the condo around 5:30 heading to the restaurant. Rob and Dr. O'Brien hadn't arrived yet from their conference. We sat at a table for seven and ordered cocktails. What happened next is not to be believed, but this is what happened.

Rob walks into the restaurant and sits down with us. "Dr. O'Brien should be here soon. She's bringing her husband and daughter to join us." In walks a stunning, tall, willowy Asian woman and Dr. Rob stands up to greet her. "Cindy, this is my partner, Dr. Sue Lin O'Brien." Trailing her is a man and girl, "and this is her husband, Michael, and their daughter, Cho Lin. Remember I told you Cho Lin is a junior at UC Berkley."

Holy crap! They're Sugar Daddy and Pigtails. Sugar Daddy's mouth is wide open. Pigtails grins and trills "hi, handsome!" Gotta' love a free spirit. Rob introduces us, "Sue Lin, this is my wife Cindy, our son Camden and Cam's wife, Jennie."

The only sound was my mother laughing the greeting, "how you doin' Chicago? Nice to finally meet you!"