Hello everybody, just wanted to give some background on the story as it is a long story with many parts but I promise it's worth it. This is a story about a first cuckolding experience that takes place on vacation. There are elements of SPH, interracial cuckolding, threesome, cream- pie clean up, cum kissing, and more. If any of these things make you feel uncomfortable this might not be the read for you. Otherwise this is going to be the best cuckold story you have ever read. Please check my profile for all the parts.
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Chapter 1-Day 1: Megan and Her Desires
My girlfriend Megan and I had planned a vacation and were very excited to go spend some time and enjoy a couples vacation. It was our first vacation in a long time and we couldn’t wait to finally get away from the cold. Megan and I met in college and have been dating for over 7 years. She is the love of my life and is the most stunning girl you’ll ever put your eyes upon.
We met during our freshman year of college as we lived in the same dorm room together. We hit it off right away and within the first few weeks of each other we hooked up for the first time and started dating shortly after. We were both our first, as we both went to college being virgins, and it was a magical moment we’ll both never forget.
I was just a young college freshman and so was Megan, but I always thought she was beautiful. Although she has changed and grown up over the years, she is still a very sexy woman who guys can’t get their eyes off of. Megan is 5’3” and definitely on the slim and petite side. She has smaller but perky boobs with perfect nipples that fit her body so well. She has a perfect plump ass and skinny, but toned legs. She has beautiful blonde hair and big brown eyes with a great smile that can seduce any guy she looks at. I always catch guys staring at her and although I should be getting jealous, I’m happy to say that she’s mine and I get to go home to her every night.
Myself on the other hand, I’m not too bad looking. I’m 6 '2 ", about 200lbs, and I'm in pretty good shape. I don’t have a crazy six pack or anything but I’m in the gym almost every day and have a good physique. I have short brown hair and blue eyes and I wouldn't say I’m a 10 like Megan, but definitely above average. Girls check me out too, but none of them could come close to Megan so I never bother looking back.
We arrived on a Sunday and immediately got to our hotel and checked in. We were staying at a beautiful all-inclusive resort with a swim-up bar, multiple pools, and multiple beautiful white sandy beaches. We were lucky enough to get a hotel room on the top floor and our view was incredible. We had one bed, a small living room, and a beautiful balcony to step out on. It really was paradise on Earth.
“Wow! This is incredible!” Megan said,
"I can't believe we're here for a full week! " I said,
“We’re going to have so much fun!" said Megan,
We both started to unpack our clothes and get settled in the room and then laid on the bed as we were tired from our long day of travel.
Megan then climbed on top of me and straddled my waist. I immediately got hard and she looked me right in the eyes.
“This is going to be such a fun trip.” She said in a sexy voice.
I grabbed her and we started kissing on the bed. She quickly started taking off her clothes and pulled down my pants and started sucking my dick. Megan has always given good blow jobs but throughout the year she's gotten better and better. Her eye contact always gets me going and I get so hard looking at her pretty eyes. She quickly got up and started riding my dick and we ended up having some great sex.
"Wow, what got you so horny? " I said.
"I’m not sure, I’m just really excited to be on vacation and I love the warm weather." She said in return.
"Well that was amazing and I certainly am excited to see you in a bikini this whole trip. " I said smiling,
"Yeah, you and all the other guys here," she said, teasing me.
We changed shortly after into our bathing suits and decided to head down to the pool. It was the late afternoon and we knew we wanted to get some drinks before heading out for the night. We decided to go to the swim-up bar pool area. We put our stuff down on some pool chairs and we noticed the crowd was a lot of younger people, which we thought was nice. I was checking out some of the girls and I could tell that Megan was doing the same to some of the guys.
“You better not be looking at any of these girls," She said, teasing me again,"Trust me once you take off that cover and you’re in your bikini, all eyes are going to turn to you." I said.
"Damn right," She said, "Everyone’s going to love looking at my big ass."
"I know I certainly will." I said.
"Try not to give the guys too much attention, I know they’re going to be getting boners looking at you." I said unexpectedly,
"Haha, that sure would be funny to see." She said,
We finally got into the pool and swam up to the bar together and ordered some drinks. We were chatting with each other for a while and then more people started coming over and we sparked some conversations. I was talking with a younger couple that was there on vacation but had a big group of friends with them as well. The guy’s name was Jake, and he was a financial advisor who seemed to be pretty successful. His girlfriend was Amber and she was an absolute smoke show. I was surprised they were together but I could tell the guy was really nice so it made sense. Amber was about 5’8”, with tan skin, dark hair and perfect D cup breasts.
We were really kicking it off and they invited me to come up to their room with Megan to pregame before going out later. I turned to Megan to see if she would be down, not realizing I haven’t spoken with her for about 20 minutes.
I turned around and noticed that Megan was talking to a large man. The guy was probably 6’5” and towered over her. He had a very impressive body, not too muscular but definitely had an impressive six pack, and dark and smooth skin. He noticed me turn around and stuck out his hand.
"Hey you must be Joe." He said, as he shook my hand with a very firm grip.
"Uh, yeah I am." I said with a slight stutter,
"Hi, I’m Jason."
"He's friends with Jake and Amber." Megan said,
I looked at her confused, wondering how she knew Jake and Amber.
"I was talking with Jason and he was explaining the situation because you didn’t want to introduce me to your new friends." She said, looking at me.
"I’m sorry babe." I said,
"Jake and Amber, this is my girlfriend Megan. Megan, Jake and Amber."
They introduced themselves and we chatted for a little longer at the bar before heading back to our room to get ready for the night.
"They all seem nice." I said to Megan,
"Yeah, I'm excited to pregame with them and go out." Megan said.
"What were you and Jason talking about?" I said.
"Oohhh, is someone jealous?" Megan said, teasing me.
"Haha, maybe a little, a big guy was checking out my sexy ass girlfriend, just want to know what you guys were saying."
"Oh not much." She said
"What? Were you too busy checking each other out?"
"Oh stop it." Megan said.
"We were just talking about the trip and what we had planned. He’s staying by himself and wanted to be looped in on what the plans were for later, which I didn’t know because you didn’t want to introduce me to Jake and Amber."
"I'm sorry again about that. " I said.
"It's okay, I’m just teasing." She said,
"Wait, did Jason tell you he was single?" I said.
"What do you mean?" She said,
"You just said he was staying by himself, How do you know that?"
"When he first came up he introduced himself, I think he was probably trying to get my number but I said I was here with my boyfriend, then we started talking more and he said he was with Jake and Amber and the big group they have but was staying by himself." She said
"Oh, okay." I said.
"Did you think he was going to invite me up to his room or something?" She said, smirking at me.
"What, did you want to go? I bet he would have loved that." I said.
"Babe stop it, of course not. " She said.
"I saw the way he was looking at you, I wouldn’t have been surprised if he asked you that. I wouldn’t blame him." I said.
" I wouldn’t have blamed him either, look at this sexy body." She said as she slowly undid the top to her bathing suit.
She took off her bathing suit and went into the bathroom to shower. We both were getting ready and I finished before her so I sat on the couch in the living room and sipped a beer.
"Okay, I'm ready!" Megan said enthusiastically.
I turned around and saw the hottest woman you could ever imagine. She was wearing a short black dress that hugged her flat stomach tight. She did a 360 and I could see her perfect ass stretching the dress out. She started walking towards me and gave me a passionate kiss on the mouth.
"Are you not wearing a bra?" I said.
"Hey baby, you look amazing, wow I’m so lucky." She said sarcastically,
"Babe, you look fucking incredible don’t get me wrong I just saw your nipples were poking through that sexy dress." I said,
"Yeah, it looked weird so I ditched it." She said,
"What about those little nipple covers?"
"Oh come on, what’s the big deal? It’s just my nipples, we're on vacation babe, remember?" She said,
"Yeah, I guess you’re right. You look so sexy, baby." I said.
"Oh, I know, let’s go." She said,
She got up and started walking to the door and the dress slid up a little bit so I could see the bottom of her ass, and the red panties she had on underneath.
"I can see your underwear." I said,
She grabbed her dress and attempted to pull it down but it didn’t do much, just covering her underwear for a brief moment.
"Oh stop babe, it’s fine I just had to pull it down." she said,
"I’m not complaining." I replied,
We started walking towards the elevator and once again her dress was rising up but I didn’t say anything. Her ass was looking incredible. We got to Jake and Amber’s room and there were about 10 people in it, Jason included, all drinking and chatting.
"Everyone this is Joe and his girlfriend Megan, Joe and Megan this is everyone." Jake announced,
We introduced ourselves to everyone slowly and after about an hour we all headed out to the club located in the resort.
The club was a short walk and when we got in we noticed lots of young people dancing. Jake got us A VIP table that we all stayed at. We danced at the table throughout the night and chatted with our new friends we made. At one point Megan suggested we all go on the dance floor.
"Babe are you coming?" Meg asked me,
"Of course!" I said.
"Jason?" She said,
"I'm in!" He said with excitement,
We all got on the main dance floor and we’re having a good time. I could tell all of the guys were checking her out and I don’t blame them cause she looked sexy as hell. I made sure to keep her close, and we danced together for a while. Megan was grinding on me which wasn’t anything out of the ordinary, but she seemed really into it. I don’t know if she was drunk or super horny but either way I loved it. At one point her skirt was almost all the way lifted up and her bare ass was rubbing on my hard dick through my pants.
"What got into you tonight?" I said,
"What do you mean?" she said, confused.
"You seem really horny I’ve never seen you lift up your dress and grind on me like that." I said,
"Did you like it?"
"Of course I did"
"Well then what's the problem?"
"Nothing! Just don't want other guys seeing your perfect ass."
"Well then you shouldn’t have let me leave the hotel with this little dress on. Guys have been staring at my ass all night!” She said,
I had a surprise look on my face and she quickly said
"I'm just teasing." she replied,
"So guys have been checking you out?" I said teasing her,
" Oh I'm sure they have but you're the only one that's getting lucky tonight.”
"I can't wait"
We continued dancing and I let my eye off Megan for a bit after what she said. It made me realize that I have nothing to be jealous about and I’m the only one that's going to be sleeping with her for a full week. We continued dancing with the group and at one point Amber got close to me and I got a chance to check her out. She was wearing a red dress with lots of cleavage but a bit more humble than Megan's dress.
"Are you having fun?" Amber said to me,
I was completely checked out, looking at her beautiful D cups in the revealing dress and I paused before looking up at her eyes.
"Oh yeah, tons of fun." I said embarrassingly, knowing she just caught me checking her out.
She gave me a quick seductive smile before turning away and continuing to dance again. I saw Jake look at me and start laughing.
"What?" I said,
“I see you like Amber’s dress." Jake said.
"What do you mean? I said,
"I don't blame you for looking man, I’m just messing with you."
"Oh, haha, sorry bro."
"Don’t say sorry she has them out for a reason, she likes the attention, seriously I’m messing with you, don’t worry about it. She knows guys are going to look at her, I don’t blame you, everyone else is doing the same thing."
"Yeah she's cute, you're a lucky guy." I said,
"I know I'm a lucky guy, but you're the luckiest guy. Megan is a smoke show and every guy in here is checking her out. I won’t lie, I’ve gotten caught staring once or twice."
"Haha it's all good man, I don’t blame you either."
I kept dancing with Jake and Amber for a while stealing some glances at Amber’s tits again. After a while I noticed I hadn’t seen Megan in a little bit so I started to look for her. I pushed through the crowd and found her dancing with Jason and some of the rest of the friend group. Before I went up to her I wanted to see if guys really were checking her out and it was true. There were plenty of young guys, some single, some with girlfriends, all taking glances at Megan at one point or another.
She was dancing with the group like everybody else but the guys seem to like getting teased by her in her short little dress. They were checking out her titties poking through her dress and trying to catch glances at her ass when the dress got pulled up. I didn’t mind, I would have been doing the same thing.
I kept watching for a little longer to see her sexy ass dance from a distance. At one point Jason came over to say hi to her. He put his arm around her shoulder to greet her. Megan looked at him and smiled before dancing closer to him. She started to dance really close and it looked like her ass was rubbing against his leg near his hip. He noticed and started checking her out and seemed to shift his waist towards her ass to try to get her to twerk on him. She didn’t quite twerk on him, but I could tell they were getting pretty close and she kept rubbing her ass against his leg and he grabbed her waist a few times. I came over and started to dance with the group and Megan finally saw me.
She looked at me with her “horny eyes", as I like to call them. It’s a super seductive look she gives me when I know she wants to fuck. Most guys would probably cum in their pants if she looked at them like this.
"Hey babe," she said in a seductive tone,
"Hey, are you having fun?" I said,
"Yeah, lots of fun, let’s get out of here though,"
She winked at me, before grabbing my hand and pulling me through the crowd. I looked down and almost half her ass was out and it looked so sexy. A few guys were watching us walk out and looked at her before looking at me. Some of them were looking at her ass while others looked extremely jealous but gave me a smile that read "congrats bro."
We walked back to the hotel quickly and walked towards the elevator. I smacked her bare ass and said
"You know your ass was hanging out all night, all the guys were looking at it."
She lifted her dress up to her belly button as we waited for the elevator and bounced up and down so her ass bounced and jiggled.
"Does it look nice?" She said,
"Yeah, it looks amazing. I love those red panties."
"Oh do you?" She said and gave me the horny eyes look again,
"Yeah of course I do." I said.
She started grinding on me with her dress still pulled up. Eventually, she pulled me in and started making out with me. She then pushed me away after not too long and said,
"You have to wait a little longer, horny boy."
I looked at her with lust and love but obliged to her commands and quickly pressed the elevator button to get up to our floor. The elevator finally came and the ride up seemed like an eternity. She got into the corner of the elevator and spread her legs so I could see her panties. I went to grab her and make out with her but she pushed me back with her foot and said
“You’re going to have to wait.”
I continued to stare at her and she continued to tease me. She put her fingers in her mouth and acted like she was sucking a cock and then grabbed her panties and pulled them to the side and started rubbing her clit and fingering herself while moaning. I sat and watched and rubbed my hard dick. She stopped and moved my hand away from my pants and said
“Not yet.”
She then stared straight ahead, and we waited for the rest of the ride up. I was super horny. I closed my eyes and waited for the elevator to go up. We started to slow down and were almost at the top when she hit her hand on my chest in a fist. I looked at her and she said
"Here's a present, I heard you like these."
I looked down and she opened up her fist and her panties were on my chest. I looked back in shock as she started to walk out of the elevator with her dress pulled up to her belly button again and her full bare ass out. I stood in the elevator for a couple of seconds, shocked, before following her out and walking down the hallway. She looked back at me and put her hand down to her bare and freshly shaved pussy.
She gave me another wink before doing a cat walk down the hall and I watched as her ass jiggled. We were almost in our room when I heard the stairs door open and a group of Jake and Megan's friends entered the hallway. Megan was opening the door to her room but a couple of guys saw her, and her bare ass and said,
"Damnnnn, nice ass."
They looked at me before one of them said
"Oh shit, Joe’s getting some pussy tonight."
She looked at all of us and smiled, giving me the horny eyes again, before entering our room. I was surprised that she didn’t feel uncomfortable with the guys looking at her, but I felt proud knowing I was about to go in there and sleep with the most beautiful girl in the world.
I got into the room and noticed that Meg was in the bathroom. I got onto the bed and laid down waiting for her to come out. A few minutes later I had the surprise of a lifetime.
Meg was wearing a sexy lingerie set I’ve only seen her wear a few times, on special occasions. It was a red one piece that wasn’t exactly see-through, but left little to the imagination.
She walked over to me and said
"Are you ready to fuck my little pussy."
"Fuck ya babe." I said,
She climbed on top of me and was straddling my dick through my pants.
"I’ve been a bad girl, are you going to punish me?"
My mind was racing and I was rock hard.
"Fuckk." was all I managed to say.
She layed down and whispered in my ear
"I think a proper punishment would be stretching my little pussy out till I can’t take it anymore,"
As she ran a finger down my stomach and touched my cock.
"What do you think?"
"I think I can do that," I said.
We started to make out and she slowly backed down and started kissing my stomach before taking my pants off. My 7-inch rock hard cock sprung out and slapped against my stomach.
“I think this should do." She said looking at me,
She licked up and down my shaft and sucked on my balls before getting up to sit on it.
"I need a really big dick to destroy my pussy, are you going to be able to do that?" She said, rubbing my dick against her pussy lips.
"Fuckk" I moaned again,
She finally sat down on it and she was super wet and it slipped right in. I was surprised as usually it’s a little bit of a struggle to get my dick in right away. Normally, I would eat her out or finger her to stretch her out before putting my dick in because she has the tightest little pussy.
I was shocked but in the moment it felt so good I didn’t even care. She was soaking wet and started moaning right away and bouncing up and down very quickly. She was never this aggressive but I loved every second of it. She started grinding really fast on my cock I was trying to get every inch inside of her.
"Oh my God baby you’re so sexy." I said,
"Yeah, you like fucking this little pussy?”
"Yes baby, it feels so good."
She kept grinding on me quickly. I had to grab her hips to slow her down.
"Oh is somebody about to cum already?" She said,
"Oh fuck baby, I don’t want to cum too quickly."
I never have a problem cumming too fast but I was so turned on and she was riding me like never before. I threw her off with me onto her back and stuck my dick in her in missionary. I started pounding her hard right away and she had her legs behind her head and I had every single inch of my dick inside of her. I was shocked as normally she isn't able to take my whole dick, but here she was with her legs behind her head wanting every inch of it.
It seemed like she wasn’t in any pain either. She was looking at me smiling and would moan when I went deep inside of her. I slowed down and had my entire dick in her moving around slowly, trying to stretch her out. She aggressively grabbed my ass cheeks and pulled me in so I was as deep as possible, which caught me off guard. She had never done that before.
"Oh fuck baby, give me more I want all of that dick." She said,
I was already balls deep in her so there wasn’t much more to give but I started pounding her hard and deep and she started to moan.
"I’m going to come baby, please fuck me from behind."
I pulled my dick out of her and she flipped around and bent over in doggystyle and stuck her ass high in the air. Her ass was perfect, and just looking at it almost made me cum. I had never seen her so eager and aggressive to have sex and she arched her ass higher than I'd ever seen before. Once again I stuck my dick in her quickly and she had no problem taking it. I pounded her hard for about 15 seconds before she said she was about to cum. She moaned incredibly loud and started shaking as I pulled out. I flipped her over and was about to come all over her stomach and perfect perky titties.
"I’ve been a naughty girl, cum all over my face."
She stuck her tongue out and looked at me while stroking my cock. I was absolutely shocked as she normally says no to facials but I wasn’t going to question it. I came all over her face and it dripped down her chin, onto her tits.
She licked her lips and grabbed the extra cum with her finger and put it in her mouth, sucking her whole entire finger. She kissed me with a little bit of cum on her lips, which I found a bit uncomfortable but I didn’t care cuz I was so horny. She grabbed my head and pushed it down to her pussy and I began to eat her out. She was super wet and after about a minute I stuck two fingers in easily and started fingering her. She seemed pretty loose so I stuck in a third and she moaned and slowly stuck in a fourth before putting almost my entire hand in her, to really stretch her out.
"OMG BABY, THAT FEELS AMAZING!" She screamed,
Her pussy was completely stretched out and I could feel her orgasm coming.
"YOUR GONNA MAKE ME CUM!"
I now had basically my whole hand in her, fingering her aggressively before pulling them out. A huge stream squirted out of her pussy. I was shocked about how fast it came out. She started rubbing her clit super fast and before I knew it there were another few streams that shot out.
"OH MY FUCKING GOD!"
She screamed nearly at the top of her lungs in pleasure before closing her legs and shaking. She laid on the bed breathing heavily for about 30 seconds before turning on her side to fall asleep. I had never seen her squirt like this and thought it was super hot. I layed next to her, still surprised by how the night went. We then both slowly drifted away into a deep sleep.