Below is another installment of my “Resort Tales” collection.   These are one-off tales of seduction and boy love from my frequent trips to various resorts around the Caribbean (usually Mexico, but not always).  These are each individual stories – no chapters.   Just a reminder - I probably embellished just a bit to make a better story….. if it helps your enjoyment to assume what I have written is 100% true, then go ahead and think as such.

This particular tale is as much as about seduction and friendship as it is sex (there’s still some of that too, don’t worry).  I hope you enjoy it.

I love to hear comments & feedback.  My email is craigpnifty@protonmail.com

 

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Resort Tales 3 – Jesse’s VD

I had been at the resort for several days and so far there had been very little in the way of cute boys to chat up.  The 11 year old Brazilian boy Phillippe was sure hot to look at in his tight Speedos, but the language barrier between us prevented any real conversation.  Though - I did have way of giving him a teasing look or smile during pool volleyball games that would send him into fits of laughter.  But I digress, this story is not about Phillippe.

I was especially bummed about not meeting much in the way of cute boys this trip, for this time I was flying solo.    The kids were away at school and my wife had to cancel at the last minute because of a work emergency.   I had a whole room to myself and was hoping to get some play in while I could freely host.  While I was of course hoping for a cute teen or boy, I would have settled for a hook up with a decent looking man.  But so far, other than hanging nude in my room and having a nice wank thinking about the cute bump in Phillippe’s bright blue Speedos, I had done little to take advantage of my private accommodations.

And then Jesse fell into my lap.

They had just finished some silly pool game and we were going back to play pool volleyball when he swam up.   He was a dark skinned, dark haired very Hispanic looking boy.   My first thought was that he was probably another foreign boy that I would struggle being able to talk to.    (The resort was full of Mexican families this time of year.)   So, I was quite surprised when he looked at me and asked, “Is it ok if I play too?”

He settled into the game quickly on the other team.  I didn’t find him especially attractive so didn’t really pay much attention to him.   (I had Phillippe on my team and his tight Speedo-clad ass to look at after all).   At some point I did hear someone ask him his name and where he was from.    I learned that his name was Jesse and he was from Chicago.

As I observed him, my boy love meter never really went off.   He was behaving in slightly obnoxious ways, grabbing at the ball and little things like that.   I didn’t even put him on my mental list of kids to try to approach.

Things changed however when the game moved onto water polo.   I was tired so I volunteered to play goalie – less moving around required.   Jesse took up a defensive position near me and he gave me a few smiles whenever I would outlet the ball to him.   I didn’t especially think much of him at that point, but I always do my best to make sure all the kids that are playing aren’t left out.  Watching kids have fun makes me smile.

After a few minutes, he told me he was tired.  He could easily keep his head above water, but to do so, he had to continually bounce just a little bit.   “Here, have a seat,” I said as I lifted my leg up and mad a bench out of it by pushing my foot against the pool wall.    I pulled him up and put him onto my thigh so he could sit.

“Thanks,” he said a bit sheepishly.   “That’s better.”

I let him sit for a few seconds until the ball came back to our end and we had to resume playing.   Once we fought off the attack and sent the ball back down to the other end of the pool, he begged for me to let him sit again.   The feel of his butt on my legs wasn’t a bad thing, so I of course let him.  

“Ah yes, my throne,” he joked as he eventually climbed up the third time.  I laughed.

After 5 minutes or so of this interaction, his mom came up beside us with Jesse’s little sister.    The mom was young and very Caucasian.  She looked a little rough: stringy hair, poor complexion.  The sister – who appeared to be 3, maybe 4 obviously had a black father – her hair was very kinky.  The two kids clearly had different fathers.   “Interesting mix,” I thought to myself.  I didn’t see any dad around.

As we played, the daughter desperately wanted to join the game, but could neither touch nor swim.   As the mom struggled to keep her occupied but also try to let her play somehow, the girl was all over the place.    “Take her away mom,” Jesse said, “she’s gonna drown.”  I couldn’t tell if he was genuinely concerned about his sister or if he didn’t want anyone cutting into his attention from me.  I surmised it was probably a bit of both. He was being very adamant with his mom – almost having a ‘man of the house’ kind of voice.

The mom moved the girl up onto the side of the pool and sat with her and watched the game.   Jesse climbed onto my leg again – resuming the position on his ‘throne’.   What he said next shocked me.   “Wow, if you were my dad my life would be so awesome,” he exclaimed out of nowhere.   I was shocked.  At that point I’d been paying a LITTLE bit of attention to this boy for maybe 10 minutes.    Other than asking him where in Chicago he was from (a semi-rough part by the way) and his age (he was 10), I hadn’t really said much to him.  The game was busy enough to keep us occupied.  Now, I have had boys latch onto me and follow me around like a puppy dog before, but I’d never had it happen this fast!

I wasn’t sure if his mom heard him and I tried hard not to overreact to what he had said. “Well that’s a very nice thing to say Jesse,” I told him.    “Is your dad here with you?” I asked quietly so his mom – now 10’ away couldn’t hear.

He turned to me and looked me in the eye.  “No!  My dad’s in prison,” he said sharply.   It all became crystal clear to me at that point.   The boy was absolutely starved for positive attention from a man.   He had latched onto what little interest I was showing in him, even though it was not even very much.

I struggled for a minute with what to say.   “Oh man, that’s horrible,” I said.   “That makes me sad Jesse,” I whispered to him as I gave him a bear hug from behind.    “I can be your water polo dad, how’s that?”

He turned and looked at me with a huge smile on his face.   “You can be my vacation dad the whole time!” he said excitedly…..   And that was how I became Jesse’s VD (Vacation Dad).

^^^^^^^^^^

I was a bit worried about how his mom would take this proclamation from her son.  But she never said anything and I tried my best to interact some with his little sister too.  I made small talk with mom too but she was very reserved.  Frankly, it was all a bit awkward.

When the game broke up mom left with Jesse and his sister to go find food.  I didn’t see him the rest of the day.  The next day I hung out in the same pool again, hoping to see him but he wasn’t around.   I figured he’d try to be there for water polo that afternoon but he was absent.  I was starting to worry his mom was intentionally keeping him away from me.  (Which considering how much I’d been thinking about running my hands over her son’s naked body – would actually have been prudent.)

I headed back down to the beach area to see what was happening there, hoping to find a volleyball game or something.   I was getting thirsty though so my first action was to hop into the pool there and swim up to the pool bar.   And there on a cement stool, I found my young friend from Chicago sporting a red mustache from the overly-dyed strawberry daiquiris they served.

“Hey Jesse, you missed water polo today.  We needed your help.”  

After yesterday, I was expecting him to be super excited to see me.   But he was almost a little cold.   “Really, oh.   We’ve just been down here by the beach today.”  I was worried his mom had had a talk with him.   But when I took my beer and headed away from the bar, he followed me.  I soon saw his little sister and mom near the pool edge so I went that way.  Little sister soon was desperately trying to get my attention.

I played with the little girl, who was basically climbing all over me while I tried talking to the mom.   Carrie was a single mom (which I had already guessed) and had an ok job at some sort of supply company.   She told me that her parents paid for their trip to Mexico so she could get away for a few days.  I didn’t ask anything about Jesse or his sister’s fathers.  I didn’t want her to know what Jesse had told me about his dad being in prison.

After several minutes I could tell she was at ease with me and probably wasn’t ever really worried.  I told her about my own kids and how my wife couldn’t come at the last minute, but that I still came because we had a few friends at the resort.  She didn’t seem suspicious of me at all.

About that time a man came around selling tickets to a special party being thrown that night at the local Senor Frogs.    They were having a bikini contest and as usual per any Senor Frogs, it was basically going to be a drunk fest.   The guy didn’t even ask me – I was too old to be cool enough for that I guess, but invited Carrie.

“I’d love to,” she told the man.  “But it’s hard when you’re here alone with two little ones.”

Then another woman who I hadn’t really noticed before came up to Carrie.  “Girl!  You should totally go.  I’m making my sister go and have a fun night for once.  I bought her the ticket and I’m watching the twins.   I can watch your two as well.”

While the two women spoke quietly, I took a few minutes for assess the situation.   There were twin girls now playing with Jesse’s little sister – her name is Mia by the way.  They appeared to be a year or two older.   The twin’s mom looked just like to woman talking to Carrie.

“OK, what the hell, I’m in,” I heard Carrie finally say.   “I need a night to let go and get f’d up.”

“That’s the spirit girl.   You single moms have to bust out when you can,” answered the woman.

“Mia will be excited to hang out with the twins.  I don’t know how Jesse will be though,” Carrie stated, before calling to Jesse who had swam back to the pool bar to refill his strawberry daiquiri.

A few feet away, I leaned against the side of the pool taking in the exchange.   My mind leapt immediately to the possibility of watching Jesse so he wouldn’t have to be stuck with three little girls.  But I also knew it would be better not to be the one to come up with the idea.

As Carrie started to explain the deal to Jesse, a look of disgust came over his face.  “But mom, those three will drive me crazy.  I don’t wanna.”

“Well, I need a night out Jess, so you gonna have to just deal!” his mom answered.

“It’s not fair!” he barked back.   Then he looked over and saw me.  “Why can’t you get HIM to watch me instead?”   Before his mom could even answer he had ducked under the water and swam to me.  “Would you vacation dad?  Would you watch me?”

I pretended to be ignorant of what he was asking about.  “Watch you do what Jesse?”

Soon his mom was over with us.  “I’m so sorry, he doesn’t know manners sometimes,” she said grabbing his arm and pulling.

“What’s this all about?” I asked.

“Well, another single mom and I are wanting to hit up this Senor Frog thing and cut loose.   Her sister is going to watch her twins and offered to watch mine, but SOMEBODY isn’t down with the plan,” she said, staring at Jesse.

“Ohhhh, so when he said watch him, he meant like babysit him.  I thought he wanted me to watch him do a flip in the pool or something.”

She chuckled.  “No.  I’m very sorry he’s been bothering you so much.”

“He’s fine Carrie, really.   And to be honest, I have nothing going on tonight.  All the people I knew here left this morning.  I was going to maybe go into town and get some cheap tacos.   I’d actually love to have some company, that is if you don’t think it would be too weird or anything.”

She thought for a moment.  “You’d really wouldn’t mind?  I mean we might be out pretty late.”

“Oh I know,” I answered.  “I may look a bit old but I have been to the Frog a few times.  The party there can go on quite late.   He can just crash in my room, there’s plenty of space.   That is if it’s ok with him.”

Jesse jumped in immediately.   “Please mom, can I?  Pleaseeeeeeeee!” he added, using the sad puppy dog face.

“Are you sure you won’t be a bother to Mister Craig?” she asked, glaring at him.

“Promise mom, promise!”

“He’ll be fine Carrie, really.  I’ll take good care of him,” I told her.   Little did she know that taking good care of him might include touching him all over and showing him how to suck daddy cock.

“Ok then.” She finally gave in.  I gave her my cell number and room number and she gave me her spare key so we could stop and get clothes later for Jesse.  Then she took off with the other single mom to get ready for her night out.  I could tell in her swagger as she left that she was excited about being granted a night out to let her hair down.   Part of me was actually judging her a bit harshly – ironic I know - given I had plans to do dirty things with her son.   But part of me understood what it was like being tied down as a single mom.

Jesse and I played in the pool for a while.  I flipped him over my back and we goofed around, taking frequent breaks to refill our drinks.   While we played, I took every chance to run my hands over his smooth back and legs and to occasionally grip his meaty ass cheeks.   I even managed to run a forearm over his crotch a few times to assess what he might be packing.   Though he was probably too young to penetrate, it didn’t stop me from thinking about sliding my thick perv cock up his pert ass.   My cock was soon half hard.    It was hard to believe his mom just granted permission for this boy to spend a night in my bed.  

I asked Jesse if he had been snorkeling yet.   There was some decent snorkeling just off shore at this resort.  He didn’t even know what it even meant exactly.   “Oy” I thought to myself and set off to grab him a set of snorkel gear from the sports hut.   I had him try the gear on in the pool for a few minutes and he was comfortable with it quickly so we headed to the ocean.  As we first peeked our heading in the water, which was just a couple feet deep in the protected cove, he immediately stood up.  “Holy crap, there’s fish everywhere.”   There were always a bunch of common plain looking but larger fish that hung out at this spot regularly waiting to be fed by the hotel guests.

I laughed at his naivety.   “Just wait, those aren’t even the cool fish,” I told him.   I took him by the hand and drug him out just past the sea entrance where the water was noticeably cooler.   As I took him along the shore I pointed out lots of various creatures:  wrasses, sergeant majors, some urchins, a huge angel fish.   Each time he came up he was more excited than the last.   He was amazed that so many colorful fish were right there, just off shore.   When swam out a little deeper and got super lucky.  Not only did we swim past 3 medium size Barracudas, but when we got out to the deeper area there was a small sea turtle!

When we finally got back into shore, he was tired, but also so excited.  “Dude, you must be a good luck charm,” I told him.  “I’ve never seen that much stuff on one trip out here before.   And that’s the first turtle I’ve EVER seen here.”   This made him smile really big.    We were still sitting on the sand at that point and he threw his arms around my neck and gave me a tight squeeze.

“This is like the best day in my life!” he said.   As he hugged me tight I thought I could almost hear him sniffling a bit.

I pushed him away from me so I could see if he was crying.   He was, but I know they were tears of joy.  “Aww, Jesse, buddy,” I said as I wiped his cheeks.   “We’re just getting started too.   We have lots of time left and all day tomorrow before you have to leave.   It makes me happy that you’re having so much fun.  C’mon, let’s get this gear turned in so we can go get ready for dinner.  I’m going to take you to my favorite taco place.  You do like taco’s right?”

^^^^^^^^^^

We dropped off the gear and grabbed our stuff and headed back to the hotel rooms.   Jesse’s room was on the first floor (a crappy location they only stick people when the place is full or those with the cheapest of deals) so we went there first.  

It had been almost two hours since his mom had gone back to get ready to go out, so I fully expected her to be long gone.   I wanted Jesse to take a shower, and I was hoping he would be ok just grabbing some clothes and showering in my room.  Ideally WITH me, but step one was getting him to skip taking a shower in his own room.

When we slid the keycard into the slot and pushed the door I think we were both surprised when the door only opened a few inches and caught on the night lock.    Suddenly we heard a cacophony of voices from inside.

“Oh shit,” I heard a man’s voice say.

Followed by a “shhhhhhhhh” from a lady.

Then, “Jesse, that you hon?” from his mom.     “Just a second baby.”

She closed the door to release the lock and then opened it, but only slightly more, clearly not wanting him to come in.  “I forgot you were coming by still,” she said.  I could tell she was half crocked already and there was a faint smell of weed in the room as well.  I hoped that Jesse didn’t notice either of those things.   “Kim is trying on different bikinis for the contest, so you can’t come in.”

“No worries,” I tried to reassure her.  “The kid just needs some dry clothes to wear to dinner.”

“Just a sec,” she answered, closing the door.   She reopened it a few seconds later and shoved a wad of clothing to Jesse.  “Give me a hug little man,” she said trying to give her son a hug.   His response was half-hearted, almost trying to get away.   He was clearly annoyed with her.

We walked down the hall to the elevators, neither of us saying a word.   Once we got on the elevator, I put my hand on his shoulder.  “You ok amigo?”

“Yeah,” he sighed.   “I just hate when she gets jacked up.”   I didn’t know if he was referring to her being drunk or stoned, but I didn’t want to point out the weed if he wasn’t aware.

I gave his shoulder a squeeze and ruffled his hair.  “Well, let’s forget about that and have some fun,” I said as the elevator opened.   

“Which rooms yours Craig?” he asked as we headed down the fall.

“The last one at the end,” I said.    “Race you,” I said as I started running.

He took off after me and quickly passed me.  In flip flops I was slow and he was holding his slides with his clothes.   He was laughing as I pulled up to my room door several seconds behind him and out of breath.   I was glad to see him smiling again.   A little game (which I would have lost intentionally) was just the thing to cheer him up.

I let him inside and he walked in and dropped his clothes.  “Whoooooooaa,” he said with his jaw dropped.  “This room is awesome.”   I had a deluxe room which was much grander than his with a jacuzzi in the corner.   He was soon jumping up and down on my bed and laughing.  “This is gonna be so fun.  I love you vacation dad,” he said as he plopped down onto the bed.

“Okay! Okay! Chill.   First thing we need to do is get those wet trunks off before you get the bed all wet.   Stay here,” I instructed.  I pulled one of the hotel robes from the closet and draped it around him.   “Now, give me those trunks so I can put them out on the patio to dry.”

He stood up and pushed them down and kicked them towards me, laughing.   He used the robe to dry his butt and crotch a bit before sitting down on the bed.   The thought that my new young friend was now sitting naked under that robe had me a bit excited.   I peeled off my swim shirt and pushed down my trunks, standing there in my Calvin Klein athletic trunks which were starting to fill with my expanding cock.

 “Why are you wearing underwear vacation dad?

“Well, that netting stuff always rubs against my legs.  I hate that,” I answered as I pulled on the other robe and pushed the trunks off me.   I went out to the patio and laid all of our wet clothes on the chairs to dry before returning.

“Now,” I said.

“Yes, what now?” Jesse asked.

“Well, if you’re going to be my vacation son, I thought maybe we could do some things regular dads and sons do.”

“Like what?”

“Well, dads and sons often take showers together,” I said smiling.

A look of concern came over his face.  “That means you’ll see my dick though.”

“Yes, and?” I answered.  “Do you think dads and sons get shy around each other being naked?”

“No,” he said thinking.  “But I’m afraid you will make fun of me.  My friends all say I have a little bald turtle dick.”

“Oh they do huh?” I replied.   “Well, Jesse, I hope you know by now I’d never make fun of you.  I am sure your penis is perfectly normal.   I’m guessing you got skin on the end that some of your friends don’t have?”

“Uh uh,” he confirmed. 

“Well, they were all born that way too you know.  And you’re 10. So you’re not supposed to be big or hairy yet.  Trust me.  That will all come fast enough.  Besides, I’M afraid too!  I’m afraid you’re going to laugh at how fat my belly is?”

“I won’t!” he protested, actually thinking I was serious.

“OK, then we have a deal.  No making fun of MY belly or YOUR dick?”   He nodded.   “I’m gonna go start the shower,” I said and rubbed his bare thigh.

After I started the water in the shower, I slipped out of the robe before I came back around the corner into the bedroom.   As I came around the corner I was patting my slightly chubby belly and making drum sounds with my voice.  “Bud-da-da-da,” I said on repeat.

After a moment of hesitation, he immediately burst into laughter.  “HEY!  I thought we agreed no laughing,” I teased him.

He tried to stop laughing and speak but his laughter took back over.  Finally he was able to stop and speak.   “I’m not laughing at your belly.  You’re just so silly.  It’s funny!” he said.

“I know,” I said as I reached for his hand and pulled him to his feet on the bed.    “Okay then,” I said as I untied the belt of his robe and slipped it from his shoulders.  It fell on the bed and there Jesse stood, naked before me for the first time.    I intentionally didn’t look right for his crotch, despite how desperate I was to see his best parts.  I didn’t want him to worry.   Instead I pull him towards me and kissed him on his forehead.    “Come on son,” I said as I slid my arm under his smooth ass and lifted him until his legs wrapped around my waist and his hands slid around my neck.   I loved staring into his brown eyes as I took us into the shower.

I sat him on the bench and ran the soap all over my body and quickly washed my hair as he watched.  As I did so, I finally took a peek at his undeveloped crotch.   His brown uncut cock was about 2” soft and rested on a taut ball sack.  Extremely average for a boy his age.   He was of course completely hairless.   As I washed, I noticed he seemed to spend a lot of time looking at my cock.   “Whatcha looking at little man?”

“Uh, nothing,” he said looking down in embarrassment. 

“It’s ok Jesse.   You can look at your vacation daddy’s dick if you want.   Does it seem really big to you?”

He nodded.   “Did you have skin too before?  Where did it go?”

I rinsed the last of the suds from my hair and sat beside him on the bench.   I explained the concept of circumcision to him and told him my foreskin was cut off when I was a baby.  I showed him the dark scar band that circled the midsection of my cock.  With that out of the way, it was his turn to get cleaned up.   I told him to stand up and loaded up a washcloth and began washing him.

“I can wash myself you know, right?” he said.

“Oh I KNOW you CAN, Jesse.   But I WANT to do it for you if you don’t mind.   Did you real dad ever wash you when you were little?”

“No, he wasn’t really around much.”

“Well then I think you need to experience it from a dad then.   Mom’s aren’t the only ones who can be all loving and cuddly.”  I washed him from head to toe, taking time to run my hands over his soapy ass, gently sliding a finger into his crack.  It felt warm and inviting.   I hadn’t done much to wash his penis yet other than to run the soap over it.   “I’m gonna need your help with this part I think,” I said pointing to his penis.

He looked at me confused.   “Can you pull the skin back so we can wash up underneath.    If you don’t keep it clean under there it can get kind of smelly and gross.   You might not care now, but someday your wife or girlfriend might when you’re older.   You might as well start practicing good hygiene now.”

“Ok,” he shrugged.   He gripped the skin of his dick with fingers from both hands and pushed back until his pinkish head finally poked free from its sheath.

“So this is your little turtle,” I said as my soaped fingers gently rubbed around his tiny dick head.   He drew back in a flinch from the tickle.   “Tickles don’t it.   It’s almost clean.  There was a little buildup that I didn’t quite get off.  You don’t mind me touching you there - do you? son?”  It was really clean as it could be (he’d been in the pool and ocean all day), but I wanted an excuse to fondle him some more.

“No, it’s cool.  It just tickled a lot,” he said as he skinned his dick again.  I could tell it was just a bit fuller than before.   I rubbed his smooth head some more, tickling his perfectly centered piss hole just a bit before removing my hand.   I had him turn around so he wouldn’t see my now half stiff cock sticking straight out from my body.   I gave my member a few tugs before washing his hair and rinsing it clean.   “Stay here,” I told him as I slid out the shower door and quickly dried myself.

I grabbed a large dry towel and opened the door and turned off the shower.   I knelt down and motioned for Jesse to come to me.  I gently dried his hair with the thick towel before wrapping it around him and patting the rest of him dry.   He smiled as I gave him this royal treatment.   I scooped him up, towel and all, and carried him back to the bed and laid him, chest down, onto a pillow.

“What are we going to do now?” Jesse asked, turning his head to look at me.

“I’m going to make you feel really good.  Then we’re going to go eat,” I whispered as I kissed his cheek and began rubbing his back under the towel.  I rubbed his shoulders and scratched his back, working the towel off of him as I went.  “You’re so cute, I could kiss you all over,” I whispered as I kissed his neck and back as my hands went lower.  I traced over his firm butt, gently kneading each cheek before running my hands down his legs.   I kissed onto his lower back, stopping just above the crack of his ass as he gasped.   I moved down and rubbed my thumb into each of his smooth feet, admiring the lighter colored skin on the pads of his feet.   Guttural moans of approval slipped from his lips.

As I had worked him over, my eyes were drawn into the cleft of his round ass.   I couldn’t help but to think of the treasure that was hidden inside.   My cock hardened as I imagined what it would be like to take Jesse virginity, sliding my thick cock into what had to be a super tight boy pussy. 

Finished with his feet, I scooted back up beside him and told him to roll over.   “I can’t,” he responded. 

“Why not buddy,” I asked softly.

He buried his head into the pillow.  “Because I got a boner,” he said giggling. 

I gripped his hand nearest me and guided it to my own erection, which he felt with a bit of hesitation.   “Me too mijo,” I said.

Jesse pulled his head up off the pillow and looked at my engorged daddy cock.  “It’s so big!” he exclaimed.  “Why do we have boners?”

“Well, I think it means we really like each other and like being near each other and cuddling like this,” I answered as I reached my hand under him and turned him over.

“Yeah, I think so too,” he agreed as he stared into my eyes and reached for his boner, gripping it and pulling it. 

“I’m going to make you feel so good Jesse,” I whispered just before my lips met his and I kissed him softly.   I took his lower lip gently between mine and pulled.  Then I kissed down his neck, leaving warm breathy kisses all over him.   He said nothing and did nothing to stop my advance.   I reached down and pushed his hand away from his cock.  I replaced his hand with mine and gently stroked the stiff 3” nail.   I kissed down his chest, licking each nipple as I continued manipulating his little cock.

He was beginning to breathe faster.  I could feel his heart beating faster beneath my cheek.   “You like this,” I stated.

“Yeessssss,” he moaned.

“It’s going to get better even,” I told him, staring up into his face.  His eyes were closed and his mouth was slightly open, breathing quickly.  I gently tugged the skin of his dick, freeing the smooth pink head.  I swooped down on it and licked it all over, eliciting gasps from him.

I took all 3” of him into my mouth and sucked gently as my tongue swirled the sensitive tip.    The thing that always amazes me about a boy getting blown for his first time is how instinctual it is for him to start humping.    It was just a few seconds of his cock in my mouth before his hands were on my head and his hips were thrusting.  I let him take over, knowing his inevitable dry orgasm wouldn’t be far off.

He thrust a few more times before he began to moan loudly and steadily.   “Let it come Jesse, let it come,” I said the best I could with his little prick in my mouth.

He started thrusting faster and faster.  I knew he was about to explode.  Finally he gave out one last yelp and pushed down on my head.  I felt his balls draw up even tight and his cock twitch.   Then he pushed me off him.   I looked at him and smiled.  “How was that?”

“Oh god, that was amazing.”  I slid next to him and kissed him on the cheek.  His entire face was warm and sweaty.   

“You’re gonna need another shower,” I joked. 

“Nah, I’m starving.   Can we go eat?”  The mind of a 10 year old boys moves fast apparently.

“I was joking,” I told him.  I got up and tossed him his clothes.    He quickly pulled up his blue Hanes boxer briefs and had his athletic shorts and plain t-shirt on before I even had my underwear and socks on.  When I was finally dressed and had tied my shoes, I gave him a big hug which he returned.   “Still the best day of your life Jesse,” I asked.

“For sure,” he answered.   “The best.”

“Good,” I said as I took his hand and led him out the door to dinner.

As we walked down the hall he asked me a question.  “Vacation dad, can you do that to me again when we get back.  You know when you sucked  –“

I jerked his hand and cut him off. “Shhhhhhhh,” I told him.   “Let’s not tell the whole world,” I whispered as we rounded a corner and I made sure the hallway was empty.   “But you bet we can do that again.  Maybe even twice,” I said with a grin.   He smiled back at me and giggled.

^^^^^^^^

Our trip to town was a blast.  We had the taxi drop us off at my favorite taco joint, well away from the main tourist areas.   I exposed him to REAL tacos with a variety of meats, though like most, he liked the al pastor the best.    I also showed him what it looked like in the areas where the locals lived.   He said it kind of reminded him of parts of Chicago.

Instead of hailing a cab, we walked all the way back to the waterfront, winding our way through the narrow streets with damaged sidewalks.  While I was anxious to get back to my room and further defile the cute young boy, I managed to push that thought of my mind and devote extra time in town.  I wanted to him to remember everything about this day and night and not just the sex.  Hopefully in the context of all that we did that day the dirtier parts could never be warped into something bad inside his mind should someone find out or should he grow older and the mores of society began to weigh on him.

 Jesse held my hand most of the way.  It was a little dark down some streets and in those areas he squeezed a little tighter.   I kept trying to reassure him that the backstreets of Mexico were nothing like a rough section of Chicago, despite the fact they might look similar.  By the time we got back to the main plaza, we’d both walked off enough of our dinner that ice cream sounded good.   We each got an ice cream bar from a local vendor that was selling ice cream and steamed corn dessert (with mayo) from a cart.

The cutest thing about the whole night was how many times someone referred to Jesse as my son.   First the cab driver, then the waiter at the taco stand, followed by people in the square, and finally the ice cream man.   Several complimented me for having such a handsome son.  I didn’t disagree and we didn’t bother to correct any of them.   Jesse would just give me a huge grin each time someone called him my son.

We sat on a bench in the square and ate our ice cream then we walked around.  We watched a spray paint artist do a couple of quick paintings and then headed off to catch a cab.   “What time is it?  I’m getting tired.”

I checked my phone.   “Damn, almost 11,” I answered.   “Later than I thought.   You still going to want to do that sucking thing again?”  Of course I leaned over and whispered the last part of to make sure nobody heard me.

“I’m not THAT tired,” he answered sharply.   “You could wake me up if you’re going to do that.  I wouldn’t mind.”

“Hmmm.  Maybe that’s how I WILL wake you up tomorrow,” I said tousling his hair.

^^^^^^^^^^

The prospect of getting another blow job must have had Jesse a bit excited because he was a chatterbox on the way home in the cab and all the way through the hotel lobby and on to my room.  I was worried he might crash in the cab, but he showed no signs of being tired.

When we got to my room, he went straight for the fridge and got himself a coke and sat down on the bed and started peeling off his shirt.   “Well, I guess someone’s a bit anxious for something… hmmm… I wonder what it could be?” I teased him.

He didn’t get my sarcasm.  “You said we could do it again Craig!”

I sat beside him and reached for his crotch.   It was clear that his cock was already hard.  “Oh, were going to do it again,” I said before I pulled him towards me and brought his lips to mine, kissing him a bit more forcefully than I had before.   I even poked my tongue into his mouth before pulling away.  “But someplace different this time you little horndog.  I can’t believe you’re already hard.”

“Sorry about that,” he said.  “But I was thinking about it all the way back in the taxi.”

“Don’t be sorry son.  I love that you want it as much as I do,” I said as I got up and went to the Jacuzzi tub and started the water.    “This time were going to do it in here,” I told him.    I motioned for him to come towards me.   When he arrived I aggressively pushed his shorts and underwear off and threw them back towards the bed.    His rock hard erection sprung free, gently pressing free from his supple foreskin.   “Now you take my pants off Jesse,” I instructed him as a tossed off my shirt.

He fumbled with the button on my khaki shorts for just a few seconds before finally solving it.   As he unzipped my shorts they fell to my ankles.   My semi-erect cock was poking towards my left hip in my tight athletic trunks.    “Go on Jesse, go on.”

He pulled the waistband of my trunks down until my cock sprung forward.   He reached with both hands and worked the red trunks down my thighs.  I was just sweaty enough that they stuck a bit so I pushed them off for him.   I stood before him, naked.  “Ok, Jesse boy, did you have an awesome day or what?”

“You know I did vacation dad!”

“Ok, good.  Then I want you to do something for me my vacation son.   Kiss my dick, just like I did to you.   Then lick it.  Ok.”

He looked at me.  “Do I have to?”

“No, you don’t have to.  But I’d really like it.   Just give it a quick try and if you don’t like it it’s fine.  I will still do it back to you no matter what.”  I raised my hand into the air.  “Promise.”

He leaned forward and stuck his tongue out just a bit until the tip of his tongue touched the head of my cock.   Then he pulled away. He must have decided it wasn’t too bad, because he leaned in again and kissed it and gave it a lick.

“Well done Jesse!  How was it?”

“It tasted kinda sweet!  It wasn’t really gross like I thought it would be”

“Yeah, that’s because it’s dripping some precum and that tastes sweet.”

“Pre what?” he asked, clearly puzzled.

“I’ll explain later,” I answered.  “Let’s get into the tub.”  I led him over and helped him step in and climbed in behind him.  I sat against the reclining back of the tub and pulled him onto my lap.   His smooth butt rubbed against my throbbing cock as I wrapped my arms around him and began kissing his neck.  As I kissed him all over from behind one hand began to rub his hard cock while the other groped his chest.

“Oh wow that feels so good.  Don’t stop dad, don’t stop!”

I didn’t stop.  I kept working him until I could tell he was worked into a frenzy and then I pulled him to his feet and spun him around.  I leaned in and took his hard nail into my mouth and sucked the sensitive head.   He almost immediately began thrusting into my warm mouth.   I grabbed his butt cheeks as he grabbed my head and together we managed the rapid thrusts that quickly brought him to his second dry cum of the day.   He didn’t yell out this time, or if he did I couldn’t hear it over the sound of the Jacuzzi jets.

I released my grip around his waist and let him slide back into the water.  I turned off the jets so we could hear each other.   “Was it as good as the first time my man?”

“Even better!” he answered.

I pulled myself up until I was sitting on the edge of the tub.  “You think you could do it a little bit more to me now?”

Jesse nodded and leaned forward.  He surprised me by not only licking the head but taking the first 2” of my cock into his mouth.  I began to guide him on what to do.   I told him to use his tongue and to watch his teeth and not to take too much at once.   He tried hard but he was too new at it to provide me much pleasure, but still the sight of this dark haired beauty with my cock in his mouth was certainly enough to please me.   Finally without warning he tried to take more into his mouth and immediately gagged and pulled off.

“Ok buddy, that’s enough.   Good job, it felt really nice.”  I decided he was done.  I was still going to blow my load, but I wasn’t going to push him too far.  I pulled the plug on the tub and as it drained we say on the edge.  I dried both of us off and helped him over to the bed where we both laid down.

“Do you masturbate Jesse?  You know - play with your dick?”

“Yeah,” he answered.  “A friend showed me.  But it wasn’t as awesome as when you did it with your mouth.”

“Cool.  I’m going to play with mine now until I cum.  I want you to watch ok?”

“What cum?”

It was time to explain a few things.   I gave Jesse a sex talk.   Of course mine came with lots of demonstrations.  I explained orgasms and cumming which he obviously already had experienced, but hadn’t known the terminology.   I explained pre-cum to him.   In fact I showed him by pushing a large bead of precum from my slit and swabbing it with my finger.   I had him taste it, showing him it was the sweet stuff he had before.   Then, while I stroked my cock, I told him about sperm.   It wasn’t long until I was showing him jizz.   It was quite a show.  Having been horny all day thinking about him, the pressure had been building up and when it released it was spectacular.   I usually dribble but this time I exploded and cum flew all over my chest, face and even over my head onto the wall.

“Holy shit!” he said.  “That was awesome!”

“Yeah well it doesn’t usually do that.   It only exploded like that because being with you has had me excited all day.”

“Really?  Me?”

“Yes, you,” I answered as I smiled at him and poked him on the nose.

I wiped the cum from my chest and face and from the wall the best I could and then we both got ready for bed.  He didn’t have a toothbrush but I gave him the one from the hotel that I hadn’t opened and we stood naked side by side as we brushed.  It was a nice image in the mirror that I won’t forget.   We both took a leak and then climbed back into bed, where he cuddled up beside me.

I had one more thing I needed to talk to him about.  As I rubbed his back gently I spoke.  “Jesse, you know some of the stuff we’ve done, the sex stuff like sucking and stuff… You know you can’t tell anyone about that right.”

“I know,” he said and then paused a bit.  “Did we do the bad touch stuff they warn us about in school all the time?”

“Yes, sorta.  Depending on who does it to you and how it can be a very bad thing.  Did it feel like a bad thing to you at all when we did it?”

“No way!”

“Does it feel wrong or bad now?”

“No.”

“Good.  Then I don’t think what we did is bad.   I want you to think about how you feel about it.  How you feel about it right now.  And never forget how you feel.   Don’t let anything or anyone ever change your mind about how you felt ok?  The people that teach about the bad touch and all that just don’t realize that sometimes a man and boy, like us, or a dad and son, can have fun like we did and both enjoy it and not get hurt by it.   They think it’s always a bad thing and that’s why it’s illegal.”

“Illegal.  You mean we could go to jail or something?”

“Not you buddy, just me.  But since were in Mexico that’s not even very likely.  But still, you need to keep this a secret.  That means you tell nobody. NO-BODY got it?  Not mom.  Not your best friend.  Nobody.  Understand?”

“Yes, daddy.”

“Good boy, good boy.”  I pulled him into me.   Conversation ended, we both drifted into a restful sleep.

^^^^^^^^^^^

I awoke the next morning with a raging hard-on.   I was in the middle of an erotic dream when the maid cart clanked into the wall in the hall and stirred me.    In the dream I had bent Jesse over the bed and was I thrusting my cock deep into his bum.   I gave my cock some strokes as I turned over to locate him.   He had rolled over away from me while he slept and was now on his stomach, facing away from me with his hands both up under his pillow.

The towel I had used the night before was still on the floor next to the bed.  I grabbed it and put it on the bed between us as I scooted over closer to him.  Under the cool sheet, I ran my hand over and found the warm cleft of Jesse’s ass.   I delicately ran my fingers into it as my other hand slowly stroked my aching cock.  I closed my eyes and tried to take myself back into the dream that was so rudely interrupted.  I was soon back to the scene in the dream where I was giving Jesse a hard fuck with him bent over the bed and my hand holding him down.   It was a much more aggressive scene than anything I would ever do to a boy Jesse’s age, but as a fantasy it was incredibly arousing to me.

In my now self-directed fantasy, he was taking each thrust of my cock with a loud grunt.   I could hear it in my mind along with the sound and feel his ass slapping against my body as I gave him all I could.   And I could feel the tight grip of his virgin hole squeezing my cock each time I impaled it deep into him.  My hand naturally squeezed tighter.  As I played the hot scene out in my head and played gently with Jesse’s ass, my orgasm came rushing forward from deep within me.  I stifled my moans as I squirted another load into the white towel.

All through my self-pleasuring Jesse had not stirred.  He was apparently a deep sleeper.   I quietly slipped from bed and crept to the bathroom and relieved myself.   I came back and dumped a bottle of water into the coffee pot and hit the start button.    As I waited for it to brew, I began to think about how to best handle this situation going forward.   My affection for Jesse was genuine, and I was sure that his attachment to me was too.

Today was his last full day at the resort.   He had a late morning departure the following day.   I knew he would be stuck to me like glue all day, which I wouldn’t mind of course - but I wasn’t sure how his mom might react.   I decided it might be best to include his mom and sister in as many activities as possible.   I figured it might be a good plan to treat them all for dinner at a nicer place in town and do a little sucking up to mom.   The bigger question was what to do when Jesse invariably started asking about keeping in contact with me longer term.   I knew from his deep connection, this would be inevitable.  I’d had one other boy bond with me like him and he begged and begged to be able to talk to me.   That one was less complicated though, as I hadn’t managed to get into his pants.

As I sat naked in the chair and sipped my coffee, I watched my boy sleep.   He was facing me with his longer hairs on the top of his head draped over his forehead.   He was really cute when he slept.  I grabbed my phone and took a few pics of his adorable face.   After a bit he rolled onto his side and I carefully slipped my phone under the sheet and snapped a few pics of his butt and dick.   They were poor pictures but at least I had some

While he slept I went ahead and got dressed.   I was actually quite hungry and as soon as he got up, I wanted to go eat breakfast.   Had I not jerked off when I woke up, I probably would have wanted another play session with Jesse first, but alas, I was satisfied for the moment.

Jesse finally stirred about 45 minutes later.   Once I knew he was starting to wake up, I helped the process along a bit with some kisses and tickling.   Once he realized where he was, his arms were wrapped firmly around my neck with his head resting on my chest.  “You’re chest is really fuzzy dad,” he told me.

“Yeah, sorry,” I told him.

“It’s ok, I like it,” he said.   “Dad,” he said looking up at me.   “Thank you.”

“For what buddy?”

“You know yesterday.  All the cool stuff we did.  I love you and I don’t ever want to leave.”

“I know, I know.  Me too.   I’m going to be really sad tomorrow.  But we get to have another day of fun first.  Go take a piss so we can get breakfast and start having fun.”

“Okay,” he said.  As he climbed up he kissed me on the cheek before darting naked into the bathroom.

^^^^^^^

We were in the breakfast buffet when I ran into Kim, the aunt of the twins and the lady who watched Jesse’s little sister Mia.   I was making a bowl of oatmeal when she came up behind me.   “Geez, I sure as fuck hope your night was better than mine,” she said, startling me at first.   “That girl is a lot of work.”

“Oh, sorry to hear that.   Jesse was a piece of cake.   No problem at all.”

“Yeah, well lucky you,” she responded sarcastically.  “Don’t expect to see his mom too soon.   They stumbled in wasted about 4 a.m”

“No worries.   I can keep tabs on the boy.   We’ll be down at the beach pool after breakfast if you’d like some help keeping an eye on Mia,” I offered.

^^^^^^^

The day was rather uneventful.   I did hang out with Kim and the three little girls for a while and managed to tolerate playing with Mia for a bit before Jesse and I went snorkeling again.   After that we went back to the main pool and swam around and played with a couple of Mexican boys who were tossing a ball around.

It was almost 2pm before his mom finally made an appearance.   She was haggard and clearly hung over.   After forcing Jesse to give her an awkward hug, she went to get lunch.  She wanted him to come with her, but we had just eaten a little before that.   “I’ll just stay with Mr. Craig,” Jesse told her.

“Fine,” she huffed.

“I need to run up to my room for a minute to get something.  Come with me?” I said to him.

When we got to the room and closed the door, he asked me what I came to get.   I stared at him. “You baby boy.   I came to get you.”  I picked him up and brought his lips to mine and kissed him madly.   “I want to make you feel good again Jesse.”  

I carried him around the corner and tossed him atop the freshly made bed.   I untied his trunks and ripped them off and took his soft dick into my mouth.    His cock reacted immediately and was soon stiff as a nail and poking free of its prepuce.   I teased his bared head and licked his piss slit and soon Jesse was moaning and thrusting his cock into my warm mouth.   As usual, he didn’t last very long.

When he came this time, I kept teasing his cock until he couldn’t take it anymore and practically yelled for me to stop.   “Wow,” he said as he was catching his breath.  “That ….was….awesome… did you really just …. come….up here just…to do….that?”  He had a huge smile on his face.

“Of course I did.  I love making you squirm and scream and I didn’t figure I’d get another chance now that your mom’s up.”

“Oh,” he answered looking a little dejected.  I don’t think he’d realized our alone time had probably about come to an end.   I could tell he was getting sad again.   “I wish we didn’t go home so soon.  This sucks,” he said, smacking his hand down on the bed.

I sat beside him and pulled the naked boy into my arms.   I talked to him about feeling sad…..  about how being sad means you had made some fantastic memories.   I told him that if he wasn’t sad about leaving, then it meant he hadn’t really done anything all that great.   I asked him if he’d rather not had all the fun we’d had the past few days.  He shook his head.   “Good, me either.  I’m going to be super sad tomorrow too when I say goodbye.  But I wouldn’t trade the past couple days for anything Jesse.”

He was quiet for a few moments.   “Can I like call you after we get home sometimes, just to talk and stuff?”

“We’ll talk to your mom about it, but I don’t see why not.”

Inside I wondered if committing to that was a huge mistake.   Considering how often his cock had been in my mouth, and mine in his, I knew it was probably safer to just say goodbye for good tomorrow.   But… alas…I just couldn’t do that to Jesse.

^^^^^^^^^^^^^

By the time we went out to dinner, Jesse’s mom had erased enough of her hangover to be pleasant.  I took them to a nice authentic Mexican restaurant that was built in an outdoor oasis of tropical plants decorated with Christmas lights.   It wasn’t the best place for kids, but they put us in a corner away from people so at least we didn’t feel self-conscious about being a bit noisy.

We were discussing what time they had to leave the next morning (11am) when Jesse blurted out an unanticipated question.   “Mom, can I crash in Mr. Craig’s room again tonight.   That way Mia can have her own bed and we won’t be fighting.”

“Jesse!” she answered sharply, admonishing him.  “I do think we’ve intruded enough on Mr. Craig.  You can’t just invite yourself like that.  That’s rude.”

He shrunk into his chair and frowned.  I hadn’t considered the possibility of having Jesse in my room again that night, but with him asking I saw an opening.   “Really, I do have a plenty of room if it would make your life easier.   They gave me this large suite for some reason this time.   I know how kids can be trying to sleep together, believe me.  When our two were younger, we would each sleep with one just to make it bearable.”

“Are you sure you wouldn’t mind Craig?   I mean it’s a lot to ask.  I feel like you’ve been taking care of him more on this trip than I have.”

“Truly it’s fine.  I don’t mind.  In case you haven’t noticed, spending time with him makes me happy to.  He seems to be in need of some time with a good male role model.”

“More than you’d even know,” she answered.  She was still unaware that Jesse had told me about his birth dad being in jail but I assumed that was what she was alluding to.   “So you’ll have him again then?”

“Yeah, sure,” I replied, trying to sound as nonchalant as possible.  However, my mind was already starting to consider some things I might do besides just sucking him off again.

Jesse jumped up and hugged his mom.  “Thanks mom, you’re the best.”

Our conversation was interrupted by Mia.  “I gotta go pee,” the girl said, squeezing her legs together.    The mom asked Jesse to take her to the bathroom, which wasn’t far away.

While the kids were away, I took advantage of a few minutes alone with mom.   “Listen, Jesse’s been bothering me about something else I wanted to ask you about.   Would it be ok if he called me every once in a while once we all get back in the states?  I won’t mind and I figure in a few weeks he’ll lose interest, but I’d be willing to talk to him for a while if you wouldn’t mind letting him.”

“Yeah that’s fine, whatever,” she answered.   Her casualness made me wonder how much she even really cared about Jesse.

^^^^^^^^^^

When we got back to the hotel, I sent Jesse with his mom and told him to get all of his stuff packed so she wouldn’t have to do it AND so that he wouldn’t have to scramble in the morning.   I told him to just bring a change of clothes and to come back to the lobby bar and get me when he was done.

I had barely gotten my margarita and sat down when he came running up with a small bag in his hands.  “Ready,” he said beaming from ear to ear.  I noticed he had changed clothes as well.

“That was fast.  You really got everything packed.   What did you change clothes for?” I asked him as we walked away.

“These are my PJs,” he said and then he whispered up to me.  “Mom doesn’t know we don’t need them at your room.”

“Well good of you to play along with that one Jesse.  Good job.”

In no time we were back in the cool confines of my room and out of the humidity.  My whole shirt was soaked just from the trip into town and back.   “I need a shower I think,” I told Jesse as kicked off my shoes.

“Me too!” he answered and immediately began to disrobe.  I guess he took it for granted that he could shower with me.   He learns quickly.

We stood under the shower and washed ourselves this time for the most part.  I did wash Jesse’s hair for him before standing him up on the bench in the shower and kissing him.  I looked into his eyes as my hands reached around and grabbed his wet butt cheeks and pulled him into me.  The bench was just the right height that our cocks pressed together – his soft hairless uncut cock against my hairy cut daddy cock.

As I ground my hips into his, I could feel his pecker begin to stiffen.  “You like this buddy?”

He nodded and responded with an airy “Yeaaaaah.”

I shut off the shower and patted us both dry with a towel.  We were both still wet in places as I carried Jesse back to the bed and lay him on his back.   I was determined that this time he was going to make me cum.

I draped myself over him, kissing him.   I pushed my tongue into his mouth and then withdrew waiting for him to reciprocate, which he did for the first time.   I sucked his tongue into  my mouth and toyed with it as my hand roamed up and down his leg until I settled it onto his throbbing little boy dick.   I rubbed it up and down until he was moaning as our tongues danced.

“I think this time I get to cum first.   That ok with you Jesse?  You want to make your vacation daddy feel good?  You do don’t you?”  I was putting words into his mouth.  But I knew they were words he wouldn’t say no to.   I planned to walk him through a lot of new things before we succumbed to sleep.

“O-O-Okay,” he mumbled hesitantly.

“I won’t hurt you baby, you’ll be fine.  Trust me, okay,” I said before I pulled him higher onto the pillow so that his head leaned forward at an angle.    I swung my leg over his chest and straddled him, sitting gently on his chest.   “Open that cute little mouth and taste daddy’s dick my boy,” I instructed as I pointed my boner towards his mouth.

He did as instructed and when his mouth opened I pushed my entire plump cock head inside.    “Now, lick it all over,” I commanded.

As his tongue bathed by sensitive crown, I gave him lots of encouragement.  “Oh man that feels amazing Jesse.  You are so good at that,” I told him.  “Now suck just a little bit.”

When the suction greeted my cock I pushed in just a bit, pushing a bit more of my 6” into his warm mouth.  It felt amazing.   “There, there keep sucking and licking.  Push your tongue into my hole…yeah that’s it….as far as you can…..”  He was doing a great job working the end of my cock and I very slowly began a slight pumping motion, edging the top two inches of my dick in and out of his cute latino mouth.

I pulled my cock out and moved up a little higher so my balls were dangling just about his mouth.  “Now my boy, can you lick and suck on my balls.”   I was surprised he wasn’t balking at my instructions but he kept doing what I said.   As his warm mouth tickled my shaved balls, I slowly stroked my cock with one hand and reaching around, his with the other.

I would have loved trying to fuck his virgin ass but I knew he wasn’t ready at his young age to be penetrated.   So I decided to at least feel the warmth of his ass around my cock.   I moved off of him and rolled him over.   I scooted down the bed, kissing his back until I got to his crack and then I left a large glob of spit in it.   I rubbed the head of my dick up and down his crack.   He leaned up alarmed and turned to me.   “You’re not gonna try to put it IN there are you?” he asked.

“No baby, no.  You’re not ready for that.  I just want to feel the warmth of your tight ass surrounding my big daddy cock,” I answered, reassuring him.  I leaned over and pressed my cheek to his as I pumped my cock between his warm mounds.  He rolled back over and relaxed as I pressed my body to his, being careful to not put too much weight onto him.   I continued sliding my thick cock up and down his crack.

It felt amazing, but I needed something tighter.  I pulled myself back off of him and gently rolled him over onto his back.  I grabbed a tube of lube from the night stand and coated my cock with it as Jesse watched perplexed as to what I was up to.   “I’m gonna pump my dick between your legs until I blow,” I told him.  I lifted both his feet straight in the air.   There was a slight opening between his thighs – very slight.  I squirted some more lube into my hand and smeared it around the small opening and then I knelt forward and pressed my hard cock into the opening.   I looked down over his outstretched legs until I saw my cock finally poke free on the other side.  “See, like that, won’t hurt a bit,” I told him as I began thrusting.

I couldn’t believe how delightful his thighs felt wrapped around my cock.  I held his feet together which force his thighs tight around my cock.   I pumped and pumped, slowly feeling the heat build from the friction.   I closed my eyes and imagined I was actually plundering his tight boy pussy, stealing his virginity, as my cock repeatedly pressed into and through the gap between his soft smooth thighs.

I opened my eyes and was surprised to see that Jesse had begun rubbing his own cock as he watched mine slide between his legs.   “Oh shit,” I said, realizing the site of my vacation son pleasuring himself as I used his body to get off was going to send me over the edge.   “Look out,” I yelled just in time as the first jet of cum erupted from lube coated cock head.  It splattered across his chest and neck.  He closed his eyes once he saw the first jet coming which was good because the second one landed across his brown nose and strung across his closed eye onto his forehead.

I quickly grabbed my shirt and wiped his face clean of my goo.  “Sorry about that Jesse, you ok?”

“Yeah, that was weird.  I didn’t realize it was so warm,” he replied.  I wiped the rest of my load from his chest and then wiped my cock off as well.

“Well, damn that was really awesome Jesse, thanks,” I said before kissing him on his forehead.  “I suppose it’s your turn now little buddy,” I added as I groped his still hard dick.

“Wait!” he said sharply, somewhat startling me.  “I wanna do the same thing you did to me this time.”  I wasn’t sure which part he meant – the rubbing of my cock in his crack?  the leg fuck? 

“So, what should I do then buddy?” I asked, seeking clarification.

He patted the bed.    “Lay here, on your back,” he instructed.

No sooner had I rolled over and propped myself onto a pillow, Jesse was sitting naked upon my chest, his smooth ass pushing into my hairy chest and his partially covered erection bobbing in my face.  “Now open your mouth and taste my dick dad,” he commanded.   I gladly obliged and took the top half of his 3” boner into my mouth and teased it with my tongue.  “Now lick it all over daddy,” he then told me.   I was already licking it but made more slurping sounds to make sure he knew I was doing as he asked. 

This continued for a few moments when he spoke again.  “Now push your tongue into my pee hole,” he said in a bossy way.   It dawned on me then that he was parroting all the things I had said to him when I pushed my cock into his mouth a few minutes prior.   Realizing this I grinned and went back to work on his dick.  I pushed his skin back with my tongue and lips and poked the tip of my tongue into his tiny hole, pushing as hard as I could.  

Remembering the sequence of things I had him do, I was pretty sure I knew what was going to come next.   And I was right.  “Now lick my balls,” was his next instruction.   Inside I was laughing, but I was also secretly loving it.  I tend to be submissive with other adult men, so having a cute boy tell me what to do was striking all the submissive chords in my body.  

I licked and sucked on his balls, though his drawn up taut ball sack made it somewhat difficult.  As I worked them, I loved the feel of his steely little boner rubbing my face and nose.  I couldn’t get enough of his little rod.  

“OK, now roll over,” he said.  I knew he was just going through the sucking parts quickly in order to get the part where he put his cock between my ass.  

“Here,” I said handing him the lube.  “Put some of that on your dick and squirt some into my crack.  It will feel amazing, promise.”

As he lubed up his dick, I found myself wishing he was just an inch or two longer.   At 4” he could have managed to push inside me a little bit and then he would have been the youngest lad to fuck me.  (The current youngest was a rather hung barely 12 year old.)  But at just 3”, it wasn’t likely to be physically possible to actually get his dick inside my ass.   I felt bad that he probably couldn’t experience the warmth of a tight sphincter squeezing his dick.    

When he had squirted some lube into my crack, he flopped on top of me and I felt his thin boner fill the tight space between my cheeks.  I squeezed them together the best I could to make it as warm as possible.  “Oh WOW!” he exclaimed.  I guess he thought it felt nice.

He immediately started thrusting his hips and pumping his cock in and out.   “Scoot down a bit,” I told him, hoping to at least feel the tip of his cock tease my hole.    That did the trick and with each thrust forward, the edges of my hole tickled from his cock pressing into it.   It wasn’t going in but this still fell nice and I knew it felt great for him.  

As he pumped away a, my mind slipped way back in time to when I was just about Jesse’s age.   Back then, Adam - a cousin of mine - and I would play every time we spent the night together which was fairly often.   We always fondled and sucked each other and that we understood and quickly became proficient at.  We both knew there was something about butt fucking but neither of us was clueful enough to understand the need for some sort of lubrication.  But it didn’t stop us from pushing our dicks against each other’s buttholes and into each other’s crack.   Feeling Jesses dick (which was about the same size Adam’s at the time) pressed into the cleft of my ass immediately took me back to Adam’s basement, where most of our playtime went down.   Suddenly I could feel Adam on top of me again.  In my mind I could smell his unique musky scent along with the smell of the musty bed in the basement.   My cock was rock hard from these memories.

My trance into the distant past was broken with a yelp from Jesse and then a scream, as apparently he was reaching his peak.   As he moaned and kicked and his body shuddered, I could feel his fingers digging into my shoulders.   It was amazingly erotic.  

When he was done, he rolled over and flopped next to me with a huge grin on his face.   I rolled over too and immediately started stroking my cock which was hard as a rock again.  “Oh man that was so hot you made me all hard again,” I told him.  “Now I gotta shoot one more time.”   He sat up on his elbow and watched as I quickly jerked myself into yet another orgasm.   The tiny load dribbled this time instead of exploding.  I wiped it off with my shirt and threw the cum rag onto the floor.

I leaned over and kissed Jesse on the chin.   “Thanks.  You’re the best vacation son I’ve ever had Jesse.”

He kissed me back.  “You’re the best dad I’ve ever had.   Ever.”

I pulled him tight and clicked off the lights.  We drifted to sleep, no more words said.

Epilogue

For all the expected fan-fare, the goodbyes the next morning were rather anti-climactic.   Jesse was clearly struggling with how to deal with his sadness, so the result was him being oddly aloof.  We still hugged our byes in the hotel lobby – much less drama filled than I expected – and he climbed into the cab.  

I’m sad to say I have not had any contact with Jesse since I waved bye to him as his taxi drove off.   I figured I’d get a text from him (via his mom) or something but after almost two weeks I finally sent her a quick one.    I told her to say hi to Jesse and that I hoped they were all doing well.  I never got a response.

Jesse still crosses my thoughts often.  I hope wherever he is that he is well.  Te amo mijo!

 

My other story on nifty: https://www.nifty.org/nifty/gay/incest/los-gallos-resort/