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A Vacation to Remember

By John

Views: 6,820 | Likes: +30

A few years ago, my wife and I decided to go to an all-inclusive in Mexico.  Because of the global climate, resorts were capped at 30 percent capacity, and prices were low.

It wasn’t our first time going to a resort.  We’d been to one in Jamaica a couple times, another in the Bahamas, and a couple in Cancun.

My wife Sam’s confidence was at an all-time high.  She had been working out hard, especially her lower body, and had recently dieted down in weight for a powerlifting competition.  Her waist was tight, her stomach was flat and toned, her legs were thick and strong, and her ass was unbelievable in size and shape.

Of course, I wanted to show Sam off.  I went online and ordered some of the tiniest swimsuits I could find.  Tops with tiny triangles that would barely cover her areola, g-string thongs with a tiny strip of material in front, a slingshot thong, and some other slightly more appropriate items, just in case.

It had been nearly 6 months since her last haircut, and I asked if she planned on cutting her hair for the trip.  It was currently grazing her shoulders, not far off the longest it had been since we’d met.

Sam was no stranger to short hair.  In our 8 years together, it had ranged from below shoulder length at its longest, to a #1 buzz all over at its shortest. We went back and forth over pictures of undercuts, pixies, and even some bowl cuts and buzzcuts, but she came home the day before vacation with a sleek and sexy chin length bob.  I wasn’t upset, but I was hoping for a bit more, and I think she knew that.

 

Day 1

 

Our direct flight landed us at 9am on Saturday, and we were checked in and in our room before 11. Immediately, I stripped Sam naked, and fucked her at the railing of the rooftop ocean view balcony, admiring the view of her back, ass, neck, and blonde bob.  While she cleaned up the creampie I left her, I took out the bag of tiny swimsuits and laid them out on the back of the couch for her to pick from.

She picked a white thong with not much material in front, and a white top that we both suspected might be just slightly see-thru when wet.  “Glad I waxed before this trip.” Sam said as she adjusted the bottoms to cover her pussy.  She looked incredible with her little blonde bob and completely hairless body.  Her ass and legs looked phenomenal in the tiny thong.

I packed light on clothes for this trip.  A small heathered gray speedo was all I had for swimwear, but I didn’t care.  I was in great shape from years of working out and eating well.  It was fairly revealing itself.  I’d shaved my cock and balls, and trimmed everything else, including my chest, pits, arms and legs, to a quarter inch.  My head was smooth shaved and beard was sandpaper stubble from the clippers.

We ventured down to grab a light lunch, then to the pool to test the waters. I grabbed us some drinks from the swim up bar, then Sam grabbed my arm and nodded toward the walkway.  A couple had just checked in, and was being toured around the main pool area on the way to their room.

The man was fairly everyday casual looking, wearing a baseball cap and sunglasses, a plain gray t shirt, and cargo shorts.  The woman was wearing jean shorts that didn’t cover the bottom of her ass, and a sports bra, revealing full sleeve tattoos on her arms and legs, and a mostly tattooed torso.  Her dark brown hair was in a sizeable bun on top of her head, and the sides and back of her head were buzzed to about a quarter inch in length.

“Did you see her hair?” Sam asked. “I know you like that kind of thing.  They’re kind of hot, too, especially her.”  I had to admit that they looked pretty fit, and the woman’s hair was hot as hell.

It wasn’t an hour later, when the same couple came down to the pool from their room.  The man was wearing board shorts, revealing a fair number of tattoos.  The woman was wearing a black slingshot thong, showing off her DD fake tits and pale bottom, some of the only places on her tight, slim body without at least some ink.  She’d let the bun down in a long braid that reached most of the way down her back.

With a smirking glance and without a word to me, Sam went over and introduced herself.  I followed, and met Chris and his fiance, Kate.  They got drinks, and we chatted for a bit.  Chris was an electrician, and Kate was a tattoo artist.  Chris and I went on a side chat about working out and hiking, when I heard the ladies getting friendly.

“I love your hair!” Sam said, clearly trying to lead the conversation that direction and get me a little excited. “Do you usually keep it that short underneath?”

“Oh thank you!” Kate replied.  “I usually keep it pretty short. I can’t believe how hot it’s going to be this week.  I wish I’d shaved the sides and back before we came, but now it’s too long to shave with the razor Chris uses for his head.”

Sam was really going for it now. “I’m sure my husband here brought something you could use, didn’t you babe?”

I had, in fact, brought a few disposable razors, along with clippers and a few of the shortest guards, in case I wanted to re-buzz my beard or touch up my body… or in case Sam decided she wanted to do something adventurous with her hair.

“I did, actually.  I have a set of clippers you could borrow if you want.”  I said.

Kate was happy to hear that, and the conversation and all-inclisive drinks continued.

A few hours later, I had kind of put the hair thing out of my head, when suddenly, Chris was gone.

“Yeah, so Chris had to go to the room.  He wasn’t feeling so great.  I think the shots and jetlag hit him a little too hard.”  Kate seemed slightly embarassed.  “I do want to take care of my hair before dinner, though.  Do you think I could come to your room and you or your husband could clean me up?” She asked Sam.

Sam was beaming with delight.  We were almost immediately out of the pool, toweled dry, and on our way to our building.  Sam pulled me to the side, and whispered in my ear. “Kate wants you, honey, and I wouldn’t mind sharing.  She’s hot.”  My heart was pounding as I followed a bit behind, the two ladies chatting closely and quietly all the way up to the room.

I pulled out my clippers from my bag, and Kate decided to stand in the shower, her braid now in a loose bun on top of her head.  “Wait a second.” She said, and she slipped her sling swimsuit off and set it in a heap on the bathroom counter.  “It’ll be easier to just shower the hair off after, and not have to get it off my suit.”

Sam chimed in.  “Babe, why don’t you do the same?  Then you can just rinse her hair off you after.”

I looked down at the erection that was not fully being contained in the narrow waistband of my speedo.  The head and some shaft were out in plain sight.

“You probably should.” Kate said, eyeing my package.  “They’re not hiding much anyway.” I slid them off and tossed them onto the counter next to Kate’s swimsuit.

Kate and I stepped into the shower, and I started up the clippers.  She tilted her head down, and I put one hand on her neck to control my movement before starting at her nape and buzzing her hair to a short stubble.  Kate shivered and let out a tiny squeak of a moan.  I glanced down to see that she had one hand moving down over her pussy.  I worked from one side to the other, and Kate was breathing heavily.  My cock was hard and throbbing.

“Do you think you could razor shave it too?” Kate asked, her voice shaking just a tiny bit.

I set the clippers back on the counter, and looked up to see Sam standing there, completely nude, smiling back from the bathroom doorway. “Shave her, but don’t fuck her.” she said in a sultry tone with a grin.  I brought a razor and shaving cream back to the oversized shower.

I got the hot water running, and started applying shaving cream to Kate’s stubbly sides and nape.  I wetted the razor, and went from bottom to top, against the grain, from temple to temple, taking care over and above her occipital, revealing clean, white, high shaved skin.  Kate was clearly loving this, one hand still down at her crotch, the other lightly massaging a nipple.  She and I rinsed the rest of her hair off, and exited the shower.

Kate thanked me, slipped back into her slingshot thong swimsuit, and left to get ready for dinner.

Sam had been watching closely the whole time, with a big grin. “You have quite a bit of self control.”

“Me?” I laughed, appreciating her strong, beautiful, naked body. “Usually it’s you who would be all over her by this point.  I don’t know whether to be impressed or disappointed that you didn’t get in the shower with us.” I said.

“I just wanted to leave some excitement for later in the trip.” Sam walked over and jumped up into my arms.  “Fuck me right now.” She said.  I carried her into the steaming hot shower, sat on the tile bench, and let Sam wrap her smooth legs around me as I grabbed hold of her firm ass and entered her.

 

Day 2

 

We didn’t see Chris and Kate the following morning.  Instead, we ordered breakfast to our room and enjoyed our rooftop plunge pool while sipping coffee and aggressively playing with each other in the nude.

“I want to shave you like I did Kate last night.” I said to Sam.  “I feel like this bob haircut was a tease.”

“It was a tease.”  Sam replied with a smirk.  “I wanted to leave you something to play with on this trip.”

I gulped, and my heart raced.  Holy cow, was Sam really, finally going to let me have my way with her hair? “How about right now?” I asked.  “Don’t you want to be able to put your hair up?”

“Not yet babe.” Sam replied.

Eventually, we got dressed, and headed to lunch and the beach.

Laying in the sun, my speedo bunched up to let my butt tan, I watched Sam come out of the ocean, the dental floss straps holding tiny triangles of nearly sheer fabric over her nipples, her whole perky natural C cup breats showing, and a thin strip of fabric that her pussy lips were barely bridged by.

Then I heard a familiar voice.

“Nice to see you guys again.” Kate said, walking up the nearly empty beach in just a tiny black thong bikini, the shaved majority of her head glistening in the sun.  Chris was lagging a few steps behind, clearly a little slow today from a hangover.

Kate and Chris pulled up beach chairs next to us, and ordered some drinks.  Sam greeted Kate with a warm hug. “Dinner tonight?” Sam asked.  “We want to try the beach grill.”

Kate agreed, and she and Sam removed their bikini tops before lying down and chit chatting.  Chris seemed tired, and laid back under the umbrella to shut his eyes.  I was trying to pick out words from the ladies, but it seemed fairly vanilla, so I got up to go for a little walk down the beach in the direction where there were no resorts or people.

On the way back up the beach, a topless Kate intercepted me, while I could see Sam lying back in her chair off in the distance.

“I appreciate what you did last night.”  She said.  “I’d like it if Chris and I could repay the favor.”

Knowing Sam wanted to swing with Kate and Chris, I was open to the idea.  “Sure thing.”  I said, trying to maintain eye contact and not oggle her bare tits.  “Our room after dinner?”

Kate gave a nod and a grin, and jogged off back to the beach chairs.  I admired her fit, slim, inked body and perky ass in her high waisted thong as she ran away.

Sam wore a white, form fitting mini dress that ended at the bottom of her butt, to dinner, with dark blue heels I hadn’t seen before.  She was a total knockout with it showing off her legs, ass and body.  I wore a stretch-fitted hawiaan shirt buttoned 2/3 of the way up and 3″ inseam khaki shorts with canvas boat shoes.

We ran in to Chris and Kate poolside.  Chris had on a baggy polo and cargo shorts, looking a bit dumpy standing next to Kate. She wore a 2 piece outfit, with a small bra-type top that wrapped around her shoulders, and a sheer black mini skirt, on top of black heels that made her at least a few inches taller than Chris..  Black was clearly her color.  Her long dark hair was in a braid hanging over her breast toward her waist.

Dinner was full of light conversation, until Sam decided to dive straight in.

“So, how big are you?”  Sam asked, looking directly at Chris.  “Not that it matters,” turning to Kate,  “since you said he’s a cuck and only watches.”

Chris blushed a bit, before Kate replied. “Not very, but he’s never been inside of me.  I peg him when he deserves it, but he’s only allowed to use his hands and mouth on me.  He likes it that way, though.  When we’re with another couple, he only watches, and I usually play by their rules.”

I could see Chris withdrawing into a clearly submissive role, while Kate’s body language and tone expressed total dominance over him.

We skipped dessert, and Sam and I led the way to our room.  She squeezed my hand, and whispered in my ear.  “Remember what you asked to do to me this morning?”

We got back to the room, and I popped a blue pill first thing.  I didn’t need it to start things off, but it had been a long day, and I was expecting it to be a long night.

Chris took a chair from the table and moved it over to the corner.  Kate gave him a look that could cut stone, and he quietly sat with straight posture, hands on his legs.

Sam took my clippers from the charger, and Kate helped her section a 3 inch wide portion of hair on top of her head into a little top knot, leaving most of her blonde bob hanging down.

I didn’t think Sam would want to start off bald, so I put the #2 guard on the clippers and peeled the tight dress off of her, while Kate started to undress herself.  Neither of them had worn bras or panties underneath.  I was hard as a rock, and as I started to buzz the side of Sam’s head, Kate undressed me, before kneeling down and taking my cock in her hand and my balls in her mouth, one at a time.

I groaned and tried to keep some focus while Kate worked her magic down there.  Sam was working her own clit furiously and panting.  I kept a firm hand on Kate’s neck and head as I sheared her sides and back to a quarter inch.

I finished with the clippers, and set them down.  Kate released my package, before turning around and kneeling down on the couch, angling her hips back and pushing her pussy out toward me.  Sam almost always got the first go with me in a threesome, but she told me to go ahead.

I grabbed Kate’s long braid, gave her pale ass a hard smack, then ran 2 fingers from her back, over her pink asshole, and into her pussy, turning then down to hook on to her.

“How do you like it?”  I asked.

“However you like, Daddy.” Kate replied.

I was a little surprised by Kate’s seamless switch from dom over Chris to this more subservient demeanor.  Apparently that was also a cue for Chris to undress, his little member standing erect as he started to masturbate.

I forgot about him and focused on Kate.  I removed my fingers from her pussy, then smeared them under her nose and put them in her mouth for her to suck for a moment, before slowly sliding my raw cock into her.

Kate moaned loudly as my girth stretched her.  I started moving slow and smooth for a minute before picking up speed, keeping a hold on her braid and admiring her mostly shaved head.  Sam sat on the couch next to Kate, legs splayed, looking at me and masturbating with a vibrator on her clit.

Kate was wet and hot.  She took the pounding with loud moans and squeals.  I pulled out as I was about to cum and shot my load directly on the back of her head.  Kate immediately took what she could of it in her hand and put it in her mouth.  I rubbed the remainder into her head, before Sam put her mouth on Kate’s and they started playing.

I took a minute to grab a sip of water and watch as Sam started working Kate with a dildo, and Kate grabbed the vibrator Sam had been using to add to it.  They were making out aggressively, when Kate had another orgasm, squirting and squirming as she moaned loudly.  Sam kept up with the dildo, and I took over the dropped vibrator as we kept the pressure on Kate until she nearly passed out from pleasure.

Basically incapacitated, whimpering from pleasure, Kate laid down on the couch, a hand slowly and gently rubbing her sex.  Sam bent over to grab her head and give her a wet kiss with tongue, before turning to me with a naughty look in her eyes.

I went to my bag on the table and pulled out some straps.  I grabbed Kate by the fuzzy nape of her neck and led her to the table, making her sit on it before laying her back and strapping her wrists and ankles to the table legs.

Grabbing the vibrator and dildo from the couch, I gave an admiring look at Kate’s sprawled figure and head, and turned my attention fully on Sam.

I took the vibrator and dildo in one hand, and started working Sam’s sex aggressively.  She arched her back and clenched her jaw as she held her breath and tried not to scream as I wrenched her nipple hard with the other hand.  She was nearly hyperventilating as I kept on the pressure for minutes, pushing her into an orgasm that had her fingernails threatening the laquer on the wooden table top.

I released Sam’s legs from the straps, and pulled her hips to the edge of the table, where my recovered cock was waiting.  It slid directly in to her pussy, and she nearly screamed as she adjusted to the difference from the average male sized dildo.

Desensitized a bit from the recent pounding of Kate, it took a solid 20 minutes to cum deep inside Sam.  By that point, she was shaking and whimpering, but the pill I’d popped earlier had taken full effect.

I released Sam’s wrists and pulled her off the table, guiding her by her beautifully buzzed nape to the bed, where my enhanced cock entered her again from behind as I forcefully massaged her buzzed head and pulled on the little ponytail left on top.

“Do you want to get rid of this thing?” I said roughly, pulling on her remaining longer hair.

“Please daddy.  Please shave me.  Please shave my fucking head bald.” Sam said back, in a mix of words and gasps.

I kept fucking Sam and admiring the haircut I’d given her as she periodically begged me to remove the rest of her hair.  Her pleas for a shearing turned ne on even more. Eventually I was able to cum again, and unloaded my third load of the night inside Sam, before laying down next to her, exhausted.

Kate came over and laid down with us, and I put a hand on each of their napes, rubbing and admiring, as they lightly played with and kissed my package and touched my stomach, arms, and chest.

After a few minutes, I heard an all but forgotten Chris stand up and start getting dressed.  A glance at the clock said it was just ticking over to midnight. He walked wordlessly to the door, eyes downcast, and waited for Kate, who slipped her heels back on and grabbed her clothes before making a sultry walk to the door, nude, showing off for everyone.

Sam kissed me deeply before nuzzling into my shoulder and chest, and falling asleep.

 

Day 3

 

The Monday morning sun peeked through the open blinds, and woke Sam and I from a tangled up slumber.

Sam still had some bits of hair on her shoulders and chest, and we both had dried cum and feminine juices on us from the night before’s activities, but the first thing Sam did was go down on my cock before throwing a strong leg over me and purring as she slipped her sex over my shaft.  I took her big ass in my hands as she leaned over for a deep kiss.

We did room service for breakfast again, and caught a 30 minute taxi to a tourist trap for the day.  Sam wore her little remaining blonde hair in a loose bun on top of her head.  It was too long for an undercut pixie look, and there wasn’t enough of it to wear down as a bob.  A wide brimmed hat covered most of the rest, so only her quarter inch buzzed nape was visble.

We got back to the resort in the early afternoon, and it was HOT, so we changed into swimsuits and headed down to the pool.  This time, Sam was feeling bold.  The resort couldn’t be at 10% capacity, and we were barely seeing anyone during the day.  She donned the tiny g string thong from the day before, and left the top behind, but wore her big hat.

Kate and Chris were at the main pool bar when we got down there.  Kate was back in her slingshot thong, Chris in his board shorts.  Chris acted like last night’s events never happened, and rolled right in to pleasant conversation.

There was a clear theme for the afternoon, with a bubble machine setup pool side and deep bass beats pumping from the speakers.  After a few drinks, Kate and Sam were danging in the waist deep water.  After a couple more rounds, they were making out, constantly giving Chris and I mischievous looks.  It got the message across.

“You know, this shave you gave me is growing out fast.  I might need a touch up, if you don’t mind.” Kate said to Sam.

“I was thinking of changing things up myself, actually.” Sam replied.  “I was begging for something last night, but never got it.

My heart almost lodged itself in my throat.  Sam was suggesting I shave the rest of her head.  She’d had a buzzcut before, but it was just one time, and it was so long ago.  Althpugh we both liked it, she’d grown it out almost immediately after, stopping at a high undercut pixie phase for a couple years before growing it back to a bob.

We ended up grabbing a quick pizza dinner by the pool, before Sam and Kate led us up to our room.  I noticed Kate playing with her hair under the scrunchie she always kept at the base of her braid.

Back in the room, the ladies stripped out of their swimsuits almost immediately.  Awkwardly, Chris shuffled out of the way, watching.  I figured tonight would be at least as exciting as the night before, so I washed down another blue pill with a few gulps of water.

I took Kate into the oversized open shower with the shaving cream and razor.  We were less shy with each other than the first night.  Kate had my cock in her right hand and her pussy under her left as I scraped the stubble from her scalp, leaving her just a tiny bit tanned, shiny, and smooth, besides the patch of long hair on top.

We got out of the shower and dried off, when something unexpected happened.

“Get those clippers out and buzz the top, like you did  to Sam’s sides last night.”  Kate said.  “This braid is fake.  You’ll only be taking a few inches of my real hair.”

I didn’t hesitate much.   I glanced at Chris, who looked a bit pained, before taking the clippers with a #2 guard to Kate’s forehead. It only took a few passes before the ponytail was free in my hand and dropped to the floor.  A dozen more passes, and she had a nice, even pelt of quarter inch dark brown hair on the top of her head, surrounded by glistening bald skin.

Before we could step into the shower to clean Kate off, Sam was in my ear.

“I asked you last night babe.  Please shave me bald.”  Sam whispered.

I looked her in the eye and maintained contact, while I flicked the guard off the clippers with my thumb and clicked them on.

Sam was squirming as I peeled the sides and back of her head to blonde sandpaper stubble.  Then I took the hair tie out and let the top of her hair down.  I looked her in the eyes to make sure this was what she wanted.  She grinned and nodded, then looked down to see that Kate was sucking on my balls.  Sam began stroking my cock with one hand and pleasuring herself with the other as I sheared the rest of her head to the shortest it had ever been.

The three of us stepped into the large shower.  Kate began rinsing the hair off herself, but Sam grabbed the shaving cream and spread it all over her own scalp.

“Please shave me, daddy.” Sam asked as she lowered herself to her knees and took my cock in her mouth.  There wasn’t much hair to take from her at this point, so there was no hesitation, and I began shaving her head clean with the razor.  Kate knelt behind Sam and reached a hand under her ass to touch her sex.

I touched and caressed Sam’s beautiful, pale, glass-smooth scalp as she did her best not to gag on my shaft. Her bald head was the hottest thing I’d ever seen. I came on her glossy head as Kate continued working on Sam’s privates.

I touched up my shaved cock and Kate’s pussy with the razor, cleaned us all up in the shower, and we exited.  Chris retreated to the same chair as last night.

Sam and Kate had clearly been talking today.  They both walked over to the couch, knelt on the floor facing me, and bowed their heads.  It seemed they were wanting to submit to me entirely tonight, and who was I to say no to two beautiful, bald subs?

I went to my bag and spread the full contents of the toys I’d brought onto the table.

I had two brand new butt plugs.  Both purple silicone with a little jewel on the flat end.  One was a size Sam had just started using occasionally, the other a size smaller.  I spread some lube on the plugs and walked over to the ladies.

“You’ve been such good girls tonight.  You deserve some jewelry.  Bend over and show me your assholes.” I said sternly.

“Yes Daddy.” Both Sam and Kate said, almost in unison.

I squirted a little lube straight from the bottle onto Kate’s asshole, then worked the smaller plug in.  She let out a little yelp and shuddered.  Then I stepped over to Sam, doing the same with her.  She had a similar response, but moaned just a little after I pulled away, and let out a soft “thank you, Daddy.”

I only had one collar, Sam’s good black and green leather one. I put it around Sam’s neck and clipped the chromed chain leash to the ring at the front.  It looked incredible on her nude, curvy figure with her bald head.

The whole picture was amazing.  Sam’s strong, curvy, clean body and shining head, in her collar, next to Kate’s slender, inked body with big bolt ons and that incredible buzzed and shaved head, both kneeling in front of me, was a sight to behold.

“Ladies, I want you both to fuck me, and pleasure each other too.” I said.  “You can act freely tonight,  since you’ve been so good.”

“Yes Daddy” Kate said.

“Thank you Daddy.” Sam followed.

Quickly, Sam was on me, kissing me, pushing me back onto the bed. I found her smooth waxed pussy and started working her clit with my fingers. Realizing she was soaking wet, I moved to put my index and middle finger inside her, hooking and rubbing the front wall of her from the inside, while massaging her clit with my thumb. My other hand was on the back of her head, feeling her slick shaved scalp, then grabbing the back of her neck to control her.

The next thing I knew, Kate grabbed my dick and ran her tongue from my balls to the tip of it, before putting her mouth on it and gagging as she took as much as she could.  She took as much of my cock in her mouth as she could, sucking and working her tongue around it, while grabbing the rest in her hand and jerking up and down.

I put a hand on Kate’s slick nape to guide her for minute before I pulled out from her mouth. Sam mounted me, gasping and squirming as she lowered herself onto me, and started sliding forward and back.

Kate knelt beside me and began making out with Sam and fingering her clit. Sam was moaning loudly when I grabbed Kate and pulled her slender leg over me, positioning her hips right over my mouth.

I devoured Kate’s tight pussy as she moaned and kissed Sam, who was now making higher pitched gasps and seething through gritted teeth as she was pleasured inside and out.

Sam came, shaking and moaning “yes Daddy, oh Daddy” repeatedly, still moving forward and back on me in a more jerky motion as she trembled. Finally, she pulled herself off of me, and started furiously fucking my cock with her mouth and hand. I almost immediately came, caressing her beautiful bald head, as she swallowed my load and sucked me dry.

Kate fell onto her back on the bed during all of this, pleasuring herself, and after cumming down Sam’s throat, I rolled over and finished her off with my mouth and fingers while Sam sucked on my balls and still rock hard, blue pill dick. Kate came with a whimpering, shaking orgasm and squirted profusely.

Things didn’t really slow down from there. I stood up next to the bed, and Sam knelt in front of me and started sucking my dick and jerking it off.  The sight of her bald head working was glorious. Running my fingers and hands over her scalp was incredible.  Kate stood on the edge of the bed before stepping off into my arms.  Her hundred pound frame felt like nothing. I had her sitting in my hands and making out with me while Sam worked down below.

Sam told Kate it was her turn, and pulled back to grab a bottle from the table.  She slathered my cock and Kate’s pussy with completely unneeded lube. I lowered Kate down and my veiny cock entered her smooth sex a little too fast. She yelped like she had yesterday as her lips stretched around the girth.

I spun her around onto the bed and started absolutely jackhammering her from behind, reveling in the sight of her shining scalp and hot inked body, leading down to the jeweled plug in her ass. Sam stood behind me, feeling my chest, abs, and butt as she furiously masturbated with way too much lube. Kate was starting to shake and whimper again as she had in her last orgasm, before totally locking up and squeezing my rod tight. I continued hammering her through the squeezed pussy, with her moaning and breathing erratically. Being only a few minutes out from my prior ejaculation made it almost impossible to cum, and I continued railing Kate through at least 20 minutes of her orgasming, squirting, and moaning “yes Daddy, please Daddy, I’m your bald little girl Daddy,” when I finally came deep inside her tight sex.

Kate collapsed onto the bed muttering how good she felt and that she could barely feel her legs. I was getting tired, but Sam was wanting more. We left Kate to sleep on the bed and headed for the shower.

Sam washed my dick and balls while I massaged her nipples and washed her gorgeous slick head. It didn’t take long for me to get hard again, and she turned around, putting a foot up on a low shelf and leaning forward to grab a bar mounted to the shower wall. I lifted her big strong ass up and slowly entered her, admiring her hourglass shape, glistening wet scalp, and beautiful neck and shoulders.

Sam reached a hand back and aggressively rubbed her clit while I fucked her from behind. She came three times before turning around and kneeling down to take it in her mouth again. I massaged her bald head and grabbed her neck as I came down her throat.

Kate slipped into the shower a minute later, and we spent a good half hour washing each other, fondling each other, and making out. It was amazing going back and forth between such beautiful bodies and bald heads, when Kate made one last request.  I obliged, and shaved the top of her head with the razor to match the rest.  She would surely need to tan the top of her head tomorrow.

Chris was standing outside the bathroom watching, as we exited the shower.  He started putting his clothes on, expecting Kate to do the same.  Instead, Kate walked over, put Chris’s hand on her bald head and told him to leave, and to think about her riding my cock and me cumming on her head when he got back to their room.

I was a bit shocked by this, but I guess they were really, really into the cuck role for him.  He didn’t seem upset.  He watched as Kate walked back over to me, and the last thing he saw before walking out the door was Kate’s hand on my semi hard cock.

We walked to the king size bed, nude, clean, and strikingly bald.  I couldn’t believe my situation, with two beautiful, smooth bald women in bed with me as I lay on my back and Kate’s mouth headed toward my waist.

 

Day 4

 

I woke up Tuesday morning to quite the rise, literally.  Guess that second pill I took before passing out was still working.  I was laying in bed, dick standing erect, sun shining through the window, as Sam took her mouth off my now very wet cock for Kate to lower her sex down onto it.

I admired the morning sun shining off of their bald heads, as Kate rode flat footed on my shaft, her slim tattooed body moving gracefully as Sam began kissing me.  I moved a hand onto Sam’s glorious scalp and took in the moment.

We switched positions, and I ended up behind Kate, with Sam lying on her back, legs spread, Kate’s face in her waxed, smooth sex.  I fucked Kate until I was about to cum.  When I pulled out, Kate immediately brought her head around for me to land my load on top of.

Kate rubbed my seed all over her scalp, before donning her tiny swimsuit from the day before, and heading back to her room, no doubt for Chris to witness my load on her head.

I turned back to Sam, her pussy still swollen from Kate’s mouth, and pleasured her with my own mouth and fingers until she came.

We made coffee, skipped breakfast, fucked at the porch railing, re-shaved Sam’s head, donned our swimsuits sans Sam’s top, and headed to the beach.

Much to our surprise, Kate and Chris were stepping out of the water.  Chris was wearing his same gray board shorts, Kate in just the bottoms of the tiny two piece thong from a couple days prior, no hat, her bald scalp shining in the morning sun.

“I need to talk to you.”  Chris said to me.  I had a slight feeling of dread, and hoped he wasn’t too upset about me stealing his fiance for a night of fucking and shaving her bald.

“This is probably the best vacation I’ve ever had.”  Chris said to me.  “I just want you to know, you can use Kate however you want the next couple of days, as long as she’s okay with it.  I… uh… you know, it’s my thing.”

I didn’t really know what to say.  Sam and I had done threesomes with hotwives who had cuck husbands before, back near home and on some prior trips, but this had quickly turned into nearly total control of someone else’s spouse for most of the week.  I figured I’d lean into it a bit. Best case, he gets a turn on out of it. Worst case, no more banging his fiance.

“Kate’s been a good girl.”  I continued.  “I like it when she calls me daddy.”

“Me too.” Chris whispered under his breath.

A few hours later, in town, Kate stepped out the door of a small tattoo parlor where we were all waiting outside.  We stopped at a bar on the beach before heading back to the resort.  Chris sweating and nervous, but he was smiling.

We hit the beach instead of the pool, Kate not wanting to get her dressing wet quite yet, and enjoyed some pina coladas and tequila shots before dinner.

It was almost routine now in action, but the vibe was different.  Chris took his seat in the same chair.  I brought the ladies to the shower for a clean up and fresh head shave, and then they knelt down by the couch.  Tonight, we were celebrating a bit, so Sam wanted Kate to wear the collar.

I walked up and admired Kate’s slim, tattood figure and round tits.  My right hand took the collar,  leading her by the leash to the bed.

“Suck it,” I said.

“Yes Daddy.  Anything for you Daddy.” Kate replied.

She knelt down and slid her lips over my cock.  I took a hand and caressed her neck, sliding it upward and over her head, placing my palm down over her forehead for a moment.

I looked over at Sam, a big grin on her face, then moved my hand off Kate’s smooth, bald, beautiful head.  Above her forehead, just behind the hairline, it read “Daddy’s Girl,” in perfect black script.

2 responses to “A Vacation to Remember”

  1. What next,Sam getting a matching tattoo?

    I’m a little confused by your swimsuit terminology…as I understand it a “thong” can be a one- or two-piece (it’s defined by how much the butt is exposed),but a “bikini” MUST be a two-piece (one over crotch,the other over breasts) and a “slingshot” MUST be a one-piece (strings directly linking cloth at crotch to cloth on breasts and then going over shoulders to unite with behind)…yet you refer to a “slingshot bikini”.

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