Slowly Opening up on Vacation

We arrived at our resort with our bags and as we waited in line at the front desk a beautiful Latina woman in a short dress approached us with a tray of drinks and we each took one. Maddie knows I have a thing for Latina women and she gives me a little nudge as the woman is not out of earshot and leans in and whispers "did you see her ass? I may not be a lesbian but for her, all bets are off"

"Ha! Well now that you mention it, you're right." I replied.

"As if you didn't notice" she quickly shot back, still teasing me.

"I mean I did, but I didn't think I needed to point it out. Anyways, yours is just as nice," sliding my hand down her back and resting at the top of her ass.

"Listen mister, keep that up and we might not leave our room this whole trip." She said then pulled me in for a kiss with a bit of tongue. I noticed the welcome drink was fruity but very strong and I could taste it on her lips and sense it in her actions.

"Next" called the receptionist.

We got our key and they introduced us and another couple to the welcome party who was to give us a quick tour and drive us to our room in the golf cart. His name is Mateo and he was a local man around 50 years old with just a hint of an accent.

We got in the cart that showed us around the facilities like the various restaurants and bars and what they're known for as well as the several pools and the spa.

"Definitely looking forward to a massage this week," Maddie said.

"Excellent choice, if you like we can meet tomorrow morning to schedule all your excursions and services you want for your stay with us," Mateo suggested.

"That's a great idea," I said.

"Ok, I will meet you tomorrow at 9:30," Mateo added.

As we passed one of the pools it looked like they were setting up speakers and DJ equipment for some kind of party. "They are having a party this afternoon at the pool, you two should check it out if you like music and want to meet the other guest," Mateo said as we passed by.

Maddie and I like to get a solid buzz during vacations which helps me be a little more social and we try our best to keep it going the whole trip. We were dropped off at what was a nicer section of the resort for the higher paying guests. We really enjoy our time on these trips so we don't mind splurging every once in a while, even though we're not wealthy, we make a comfortable living. I gave Mateo a healthy tip as he was very helpful with our bags, even going so far as to carry Maddie's bag to our room.

As soon as the door closed Maddie turned to me and said "Time for your reward."

She immediately dropped to her knees, undid my belt and pulled down my shorts. My semi erect cock sprang free and she grasped it with one hand and kissed the head. She started sensually kissing all the way down the shaft and to the balls all while holding intense, lustful eye contact. She sucked one ball into her mouth, tickling it with her tongue and then repeated the treatment for the other. It took what seemed like seconds and I was fully erect. After she was done sucking my balls, she reached up with her other hand to cradle them and began tracing her tongue all the way up the underside of my shaft. She stopped just below the lip of the head to gently flick it with her tongue, then pursed her lips and ran them down and back up the shaft to the head. She parted her lips and took me into her mouth about halfway down my shaft then back up and down a few times before taking the rest into her throat slowly on the way down.(This was a rare treat for me as she didn't like to give blowjobs very often and usually saved them for special occasions.)

She repeated this taking my full cock into her throat and paused on the last time taking the time and looking me in the eye. Almost gagging, she lifted off my cock with a string of saliva connecting her lips to the head of my cock from inches away.

"You feel so good in my throat Jack, I'm going to suck your cock every night this trip."

With this she slurped the spit before placing the head in her mouth and began pumping and twisting her hands along my shaft. It felt so good and I knew if she kept this up, I wouldn't last long. About a minute later I couldn't hold out any longer and my balls tightened up along with my whole body and began to unleash all my cum. Looking down at her she had opened her mouth and left my cock resting on her tongue pointing into her open mouth allowing me to see the first couple jets of cum spray into her mouth before closing her lips around it and milking the rest out of me. With a couple gulps she had swallowed my load and I fell back onto the bed to catch my breath a bit. She came up to meet me there with a huge grin on her face and cuddled into me.

"Did you mean it? Every night on this trip?" I asked, half expecting a maybe.

"Yeah babe, I love you and I know I don't do it very often but for some reason I just have a craving for it, and I want more." She replied.

Feeling eternally grateful for hearing this I sit up, slide down the bed, lift up her dress and pull off her shorts and dive into her pussy. "She wasn't kidding, she is soaking wet already and I just began," making a mental note to myself. She was moaning in short order and before long she was shaking with a huge orgasm. This happened much quicker than it usually does so I gave her a minute to cool down before diving right back in and making her cum again.

Not wanting to waste a day in paradise we decide to head to the beach and relax (Maddie with a book and me likely with a nap). Maddie put on a red bikini which is one of her older, more conservative ones that covers most of her ass and tits and I throw on my trunks and we head out. On the way to the beach, we stopped at the drink hut that was at the entrance to the beach and got one of those fruity drinks with the little umbrellas. We then settled into a couple loungers in the sun to relax and enjoy our drinks. I pull out the sunscreen and apply it to all my exposed areas and ask Maddie if she wants any.

"No that's ok, I want to work on my tan" she replies.

"Suit yourself but if you feel yourself starting to burn let me know and I'll be more than happy to help you with that" I say with a wink.

"I know you would." Maddie says with a smile and opens her book.

I lay back and quickly fall asleep and awaken a few hours later. I hear music in the distance and look around to notice 3 empty glasses beside Maddie's chair and her sucking on the straw of a recently finished one in her hand.

"You started the party without me I see" I say to her.

She puts her book down and turns to me "I was hoping you'd wake up. I can hear the party at the pool if you wouldn't mind checking it out."

Feeling energized from my nap I agreed and we grabbed a couple of drinks on the way out of the beach area. On our way there I ask if Maddie is hungry.

"I'm sure there will be food there we can eat," she replied.

As we get to the pool, we discover what seemed like half the resort in attendance (close to 150 people). It was a nice mix of music that seemed to attract a variety of people to attend. There were young people in their early 20s mixing with older people who looked to be pushing 60. While we were in line Maddie struck up a conversation with a couple who, like us, were here from Canada. Jason and Amy, who are in their early 40s, told us that they come here this time every year and really enjoy the beach and the food at this resort. Jason and I also shared a favorite hockey team which was an easy topic for me to keep up with as I am sometimes awkward around new people. After collecting our drinks, they invited us to a table to sit down with them to keep talking.

Jason, who was lighter skinned like myself, was a bit heavier set, particularly in his round stomach that stuck out a good 5 inches. He was bald and had a goatee but certainly didn't lack confidence or charm which is probably how he landed a girl like Amy. Her appearance was quite the juxtaposition as she was a thin blonde with blue eyes and nice feminine features. She had C cup breasts that were just barely starting to sag and freckled from the sun as well as a tight looking ass that seems to have stood the test of time.

Maddie Asked Amy for recommended activities around the resort, "there's a lot to do here, there's always parties and activities to do on the resort itself. Definitely check out the steakhouse and the nightclub, that place gets pretty wild at night." Maddie had that look of intrigue with the mention of the nightclub getting wild but she let her continue. "There's nice hiking trails and a golf course pretty close by that we usually pay a visit to. If you guys are into golf, I think we'd make a good foursome." After a brief pause everyone shared a laugh. "But the beach is probably where we spend most of the time, I know it's shared with the resort next door but if you're willing to walk a bit there's a beautiful cove at the end that we go to sometimes and we think you guys might like."

Maddie turns to me looking really excited, "we should do all of those things! How about we go golfing on the 31st?"

"Count us in," Amy replied.

One of Maddie's favorite songs came on and when she drinks, she loves to get up and dance. She grabbed Amy's hand and dragged her out into the crowd near the DJ booth where everyone was dancing. I was still catching up so I went to grab a drink for Jason and I. While waiting for the drinks I turned to see Maddie and Amy dancing and seemingly they became fast friends. This is a trait that I've always admired in Maddie, I have always been a little slower to get to know people but she always seems to make friends. I make my way back to the table with a couple of rums and we continue to talk. I found out he's in sales in Vancouver and like me used to be athletic but kind of lost it somewhere along the line. We had another round before the girls returned. We all hung out and had some laughs before they left to make their dinner reservation. We exchanged numbers so we could set up the golf outing and we stuck around the party for a bit longer before picking a place to get dinner ourselves.

We picked a tequila bar that wasn't too far from our room that had amazing tacos and turned into a club later in the evening. It was already almost 7:30 when we arrived, and we were both pretty tipsy so I figured a nice meal would right the ship. It helped a bit but our server talked us into trying their house tequila (which was very smooth) and we ended up having several each and were right back where we started sobriety wise.

As the evening wore on, we hung out at the bar while we had some more drinks. Apparently at 11PM they dim the lights and play a little bit different music to get more people dancing. Maddie asked me if I wanted to dance with her but I told her I was still waiting for my dinner to settle and I could in a little bit. I guess she was talking pretty loud over the music and a guy sitting on a stool behind me heard and turned around. "Hey guys I'm Roger, my wife turned in early and we usually dance but I could warm her up for you in the meantime if the lady is interested."

He seemed friendly and harmless, wearing a fedora and a loose buttoned shirt and shorts offering his hand for Maddie to take to the dancefloor. She turned to me obviously wanting to say yes in her fairly drunken state (recall how she loves dancing when she drinks) so I pipe up. "Thanks man, I'll join you guys in a few minutes."

"First, a round of tequila for my new friends." He announces as he hands us both a shot which we down along with him.

They go off to the dance floor and this guy may have looked unassuming but he could absolutely tear up the dancefloor. He's clearly got a lot of experience with dancing as he is dipping her and spinning her in circles which I can tell she is pleasantly surprised with. This goes on for a while and I am just watching from the sidelines enjoying the show as it unfolds. I take a look around and I notice other couples are also dancing pretty similar but they seem to be getting progressively closer and dancing more intimate.

Maddie is wearing some shorts that are just long enough to cover the bottom of her cheeks and a coverup on top of her bikini so a lot less clothing than she normally wears when dancing. I notice that her nipples have become erect as sometimes happens on cool nights or if she gets a little excited. As I see him dip her, he dips his head with her body so that his face is mere inches away from her chest, undoubtably noticing her nipples, then brings her back up and holds her close. I feel a pang in my gut as I know the feeling of her perky breasts against my chest as there is now only a thin layer of fabric now separating them but not enough for him not to feel her pert nipples against his chest. Their hips, now attached, begin to sway together and his one hand now begins to drop from her middle back to her lower back, and now resting on the top of her ass. As it begins to drop, I find myself becoming jealous as Maddie probably doesn't realize this guy is about to cop a feel of her ass, right in front of me no less.

I stand up off my stool and instantly realize how drunk I am and given that she kept up with me, how drunk Maddie must also be. I walk over to them slowly as I'm trying to keep my balance, and by the time I get to them he has his hand fully on her ass. As I try to soak in the situation, I realize I'm wrestling with some internal feelings about Maddie because while I've realized I like when she shows off her body in a bikini and attracts attention, I hadn't considered how I would feel if someone was actually acting on that attraction. I sort of panicked and grabbed her by the waist and pulled her towards me releasing her from his grip and spinning her to face me. I looked past her at the man who had his hands on my wife's ass and said "Thanks Roger but I'll take it from here."

"Glad I could help, and thanks for the dance, Maddie." He replied giving her a smile that she returned before heading back towards the bar.

"I haven't danced like that in a long while," Maddie said, placing her arms behind my neck while we sway to the music as I close. "Someone's worked up."

After she said that I realized that I'm more than a little hard and she could probably feel it against her leg. She spins around and starts to grind her ass into my cock which is getting harder by the second. I let this go on for about a minute and at this point I'm almost at full mast and am hoping people don't notice the tent in my shorts. Maddie spins back around and I keep her a little further away because I would lose control and cum right there on the dancefloor if she kept it up. We danced for a few more songs while my cock went down to a less obvious state and we started sober up a bit from all the dancing. We went back to the bar for one last drink before heading out and I let Maddie order something she saw on the menu earlier that she wanted to try but didn't think it would go well with dinner. I don't know the name of it but it was bright green and strong as hell. We both had to nurse these as we joked around about the day's activities and shared our excitement for what the rest of the trip would hold.

I turned around and surveyed the bar noticing quite a few beautiful women on the dancefloor with their partners and then I noticed Roger was back out there dancing very close to another girl. She almost certainly wasn't his wife as she was easily 20 years younger than him and he wasn't just dancing with her but they appeared to be making out. He also had a hand in her blouse massaging her breast and she was feeling up the crotch of his pants with slow strokes up and down. Maddie turned to see what I was staring at and her mouth flew open in surprise. "I guess he found another dance partner," she said as she continued to stare.

"I'm not sure what they're doing is dancing," I added.

We both looked at each other and laughed as Maddie, for the first time, realized the guy probably had some ulterior motives when they were dancing. We watched the show for another minute before I announced that we should probably turn in as I was getting a bit tired from the long day of travel and fun. I started walking to the exit while Maddie trailed holding my hand and as we almost got to the door, I felt a tiny bit of resistance. This caused me to turn my head to see that Maddie was still watching Roger with that woman as we walked and I couldn't be sure but I could have sworn I was biting her lower lip which was a tell tale sign she was very aroused.

We took an unlit pathway back toward our room and were all over each other the whole way. We stopped about 100 feet from our ground level suite to lean against a tree as our making out escalated. I broke our kiss as my right hand found her ass and started kissing down her neck which usually drives her wild. It's getting pretty steamy and this is usually where she snaps out of it and tells me to take her to bed and continue it there but in the throes of our drunken passion, she must be too distracted. I decide to test my luck and start to kiss my way down to her collarbone and inch ever closer to those perfect breasts that are just begging for attention. I reach up and start to knead her left breast with my hand and still seems to be getting more and more into it.

"Fuck," she moans silently, starting to pant.

I push it even further as my kisses are now between her tits and I start to work my way toward her left breast. I Pull the fabric to the side to expose her breast to the warm air and trace my tongue around her firm nipple. Circling the edges before placing my whole mouth over top of it, sucking lightly and still swirling my tongue at the same time. Another moan escapes her mouth but this one a bit louder.

Her knees go weak as she starts to feel the beginnings of an orgasm approaching but as she catches herself, she opens her eyes for the first time since we got to the tree and sees that not only are one of the lights of the rooms of the top floor on but there's also a couple on the balcony.

"SHIT, someone's up there," she exclaims, recoiling and pulling her bikini back in rapid fashion.

We both freeze, burying her face in my chest as I turn around to check what she was looking at. I see the couple up there on their chairs having a seemingly normal conversation and looking at us at all.

"Don't worry they can't see us, they're on the 4th floor and it's way too dark out for them to see," I say trying to reassure her.

She lifts her head slowly to check to see if what I said was true and she realizes that they couldn't see us but also figures if she had moaned any louder, they might have.

We continue on to our room, me sporting a full erection and her a small wet spot that's soaked through her bikini and started to permeate through her shorts.

We made passionate love for hours that night despite initially being tired, the sexual energy was electric and she came like 3 or 4 times from oral and the pounding I gave her. I came on her twice and another time on her stomach (a new record for me).

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The next day at 11 AM we (or Maddie I should say) was awoken by a knock on the door. Still feeling a bit unsteady from last night, she sauntered over to the door and opened it to find Mateo standing there.

With a big grin across his face, he said "Good morning Maddy."

Wondering why he was so happy to see her, she looked down to see that she was wearing only an oversize t-shirt and her nipples were still hard which poked into the shirt. "Oh, sorry Mateo," she said as she covered them with her hands, being careful not to let the shirt ride up too much so as not to reveal what was underneath (more precisely what wasn't). "We're just waking up. Is there something I can help you with?"