I've always hesitate sharing this story, because its gets pretty outlandish.....but I like to re-live these good times by writing them out, so I guess you're along for the ride. Kinda long, so I broke into pieces.
CHAPTER 1
Maybe 2-3 years after graduating college a bunch of the guys were sitting around telling stories about the wild spring break stuff we did, and decided, fuck it, we should go on spring break again.....who cares that we're 24-25 and that sounds a tic pathetic!?! Since we all had jobs and money, we booked an amazing penthouse suite with a jacuzzi, pool table, the whole nine yards, for a long 4-day weekend in Cabo and did it up right.
Now just in case it needs to be said, the pretext here was find the 'college party girls', our own Girls Gone Wild live and in person, again fully admitting how dumb that sounds in hindsight -- which is important to note, because thats not how things went at all. We headed out the first night for Cabo Wabo, which at the time was supposed to be the hot place in Cabo, and I wouldn't say the place was dead, but it also wasn't spring break packed either. Quickly I started to wonder if anyone had actually looked to see if any of the west coast schools were on spring break....and looking at my collection of meathead jock buddies, I was pretty certain no one had. Still, we had a good crew, the dance floor was packed enough, and the bartender with the whistle and the tequila poppers shots was making his rounds through the club, so it was a good time.
At some point, a big bachelorette group showed up of older 30-40 something ladies and gravitated towards our group on the dance floor, and lucky for them, a couple of my meathead buddies were at the right point of drunkeness to jump right in on that mix. Next thing I know, two of my friends are full on making out with a couple of these ladies, and another is dragging me over to the bar to be his wingman. As I get over to the bar, my buddy's lady is on the older side of the group, easily mid-40s, wearing a halter top and jeans, showing off some large fake tits and giving him a look like hungry lion. It was probably a bit much for me, so I was a little nervous about my wingman assignment before getting introduced to Cindy, a short blonde milf with short spunky hair, probably mid-30's with large fake breasts herself, tight white button-down shirt tied off to show her middrift and a sparkly diamond wedding ring. We got a round of drinks, talked a bit and went out on the dance floor again, where Cindy quickly went to grinding on me and encouraging me to explore her body with my hands. I'm not the type to grab a tit on the dance floor, but this woman was fully grabbing my hands and guiding them there!!
I couldn't help but ask "Is your husband alright with this?"
"He's not here, is he?" She chirped, grabbing my hands and putting them firmly on her tits again.
So that's that....
As the club closed, I was ready to go home, but my buddy, Scott, was holding hands with his lady, Sandra, and it did not seem like our night was ending. As we walked out, he gave me a hard stare and said "We're going to share a taxi with the ladies back to their place", even though we weren't staying anywhere near them, and ushered me into a white taxi van. As soon as we got in the van, Scott and his lady start full on making out....like not even attempting to be coy. He's got his on hands up her shirt, I hear his pants unzip, like its on, so it wasn't real surprising when we pull up to the hotel that he motions to get out "We'll walk them to their room".
Even walking up to the room, we could hear ladies laughing and screaming, so Cindy confessed they had crammed 8 of them in a two bedroom suite -- we weren't heading towards any privacy. I was ready to call it a night, but Scott and Sandra weren't ready to end things, and I could see them looking around spinning on what options were on the table. Suddenly Sandra sparked up, "Let's go skinny dipping!!" and started off for the beach. Scott followed eagerly, but Cindy didn't budge....until Sandra spun around and grabbed her, dragging her with reluctantly.
Sandra was naked instantly and forcibly stripped the hesitant Cindy, before the two ran hand in hand in the ocean stark naked, white asses glistening in the moonlight, cackling wildly. For late 30's/early 40's both were in pretty good shape, and the fake boobs gave them each the true hour glass figure. I stopped by a cabana to snag some towels, and by the time I got down to the water, Scott was already in and he and Sandra were getting down to business post haste. After dancing and sweating all night, the water felt so good when I ran and dove in, just a little cool yet refreshing. When I came back up, I was a bit shocked to see Cindy right in front of me coming to put her arms around me. Now without a tight bra holding them back and pressed against my chest, her fake tits seemed much larger than I noticed before and I couldn't help but get aroused feeling her hard nipples rubbing against my chest. I wasn't sure where this was going, but she went right in for a kiss. She pulled away after 30 seconds or so, and I thought she'd maybe thought better of things....until I felt her hand wrapped around my now fully hard cock.
"Of course you have a big dick" she laughed "....ahhhh, I can't do this..." she muttered, still not removing her hand from my dick.
"It kinda feels like you already are..." I pushed.
Apparently that wasn't the right thing to say, because she peeled off me and started in for the beach. I followed behind her but when I got in she already had a towel wrapped around her and sat down on the beach chairs. So I grabbed a towel and started drying off now.
"Do you have to do that so sexy?" she quipped
"I'm just drying off", now playing it up for the attention. Rubbing by chest, abs and cock with the towel.
I could tell she was biting her lip watching me and clearly enjoying the show.
"Do you like watching me touch myself?" I asked.
She smiled and nodded eagerly. I grabbed my cock and gave it a long slow stroke. I could see her melt a little.
"How about you now?" I pushed
"Nah-uh" she protested turning away.
So I wrapped my towel around my waist and sat down on the other end of the lounge chair.
Facing each other now on the lounge chair, naked but for our towels, she pleaded again.
"Do I have to beg for it?"
"That would help, but I need some, uh,...motivation too"
She undid the knot on her towel, revealed her huge round fake tits, and leaned back on her hands to put them on display for me. "How about these?" she said with a smile
"That's a start..."
"So then, show me" she pushed.
Sitting back against the seatback, I undid my towel, dropped my legs off the sides of the lounge chair and showed her my still hard cock.
Her eyes lit up "Do what you did before"
"I thought you said you were gonna beg?"
"Please"
"Please what?"
"Please show me how you play with your cock"
As I started, she scooted closer to me, now sitting on her knees between my legs, eagerly watching me stroke.
"Is that how you do it when you're alone?" she asked
"It helps to have some kind of lube....maybe your mouth could help with that??" dying to have her lips around my cock
"Not happening.....I just can't"
"We're pretty far along for 'I just can't aren't we?"
"You have no idea how bad I want to....but I just can't. If you could feel how wet I am..."
" I mean, I can..." I offered leaning forward
"No!" she snapped
I started stroking again to tempt her more, and I could see her start to melt a little.
Then all of the sudden she dropped her towel, completely naked now, sat up on her knees and spread her legs apart, reached her hand down, and buried her ring and middle finger deep in her pussy. She pulled them out, rubbed her clit for a few strokes, her eyes rolling back in her head now, before thrusting her fingers in. I could hear the wetness now as she started going faster and locked eyes with me, her other hand reaching up for her breast now, rubbing her left nipple. Then she shot me a sly smile, before reaching out with her wet hand, grabbing my cocking and covering it up and down with her wet juices and adding 2-3 extra strokes for good measure.
"How's that for lube?" she winked, leaning back again.
Honestly, stark naked, her knees spread, her nipples hard, her wetness fresh on my cock, I could practically feel my cock inside of her. It was torturous, and worse yet when she stopped stroking.
"You're going to give me blue balls" I begged
"You can finish any time you want" she retorted.
"That's what you want?
"Uh huh" she nodded, reaching her fingers for her wet pussy again.
"No chance you'll help?"
"Nope" she said firmly "but you can finish anywhere you want" she add with a wink.
Testing her invitation I stood up, surveyed the empty dark beach to make sure we were alone, and then started stroking in earnest, her face less than a foot from my cock. She buried her hand in her pussy again, rubbing her clit eagerly and looking up at me with a thirsty smile. I kept thinking she was going to give in any second and wrap her mouth around by cock, but she never did. Still, the thought of it made it hotter and hotter. As her moaning got louder, and I could tell she was getting off on this, I gave up and started stroking for the finish line, before losing control and bursting rope after rope of hot cum on her face and tits. I was expecting some reaction or shock, but she was lost in ecstasy herself, until she shuddered once then again as she came fast and hard to those eager fingers.
As she carefully opened her eyes, she wiped the cum off her cheek, she put her fingers in her mouth, locked eyes with me with a smirk and sucked them clean. Then to my surprise, she grabbed my cock, leaned forward and licked the tip, before grabbing her towel and running off. A little bewildered, I got dressed and headed off for my hotel.
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CHAPTER 2
The next day I finally rolled out of bed at noon and headed down to the pool to see the bros, but during the normal post-party story time I wasn't sure what to say. Did I get some? Or did I just beat off in public? It was hot and weird all at the same time. Scott apparently didn't get laid, and was acting weirdly shy about his night, so I figured that was the end of that chapter of our trip.
We went about day drinking at the hotel pool and enjoying the sun, when, sometime around margarita #4 or so, I got a tap on my shoulder.....from Cindy, followed by a coy "Hey stranger". Already in the pool, she gave me a big hug that lasted a little too long, before insisting I introduce her to the boys. Apparently, Scott had gotten Sandra's hotel and room number and called to invite her over....to which Cindy had to join.
Now in the daylight, Cindy was shorter and curvier than I remembered, but she definitely pulled off the crochet triangle bikini she was rocking and I couldn't help but wonder where this was going. Again, like last night, she had her hands all over me, rubbing my chest, my arms and practically insisting I do the same. And now with a healthy day-drinking buzz, I wasn't being shy myself, my hand reaching under her bikini bottoms to fondle her ass cheeks under the water or around for some side boob; the more I did the more she pushed the limit in response, until finally at the swim-up pool bar she reached her hand in to my shorts and grabbed a handful of cock again.
At this point, we did have the privacy option -- our suite was just up the elevator -- so I leaned down and whispered in her ear, "Maybe we take this back to my room?", and without missing a beat, she whispered in my ear "It would be hotter if we did it here". Then she pushed me on to the stool in the swim up bar, and sat on my lap. Not one to give into a tease, and with the cover of the bar somewhat shielding us, I reached around slid my hand in between her legs and slipped a finger inside of her. Even in the warm pool, I could feel she was wet. She tensed up and immediately sat up straight, arching her back and sticking out her chest. She was clearly caught off guard, but didn't want to lose our little game of chicken. She tried to act cool and started to order another drink, but as I slid in another finger and started to move them in and out, I heard her mutter "Ffffuck!" under her breath and let out a loud exhale. Now putting both hands on the bar to brace herself, she stopped..."OK, ok.....you win" she panted "where is your room?" nuzzling into my chest.
I told her to meet at the towel cabana, as I had to figure out how to get out of the pool without showing the world the massive erection I was sporting. I snuck out the side of the pool, closest to my towel and quickly slinked to my chair to dry off sitting down. But when I finally looked up I saw Scott and Sandra talking to Cindy, motioning me over. I buttoned up my shirt, held my towel in front of me to hide my erection and headed over to see what fresh cock block was awaiting me.
"We're taking the ladies back to their hotel to clean up" Scott announced. And off we went in another white taxi van, except this time it was Cindy and I practically having sex in the back of the taxi, with her hand down my pants and vice versa the whole ride back.
When we got back to their suite is where things get a bit outlandish..... I was hoping for an empty suite when we got their room, but had no such luck -- it was 5 or so and a few of their friends were back from the pool and starting to clean up for the night. Still Scott and Sandra bolted for one of the rooms and Cindy pulled me into the other. Now finally alone and secluded, we started kissing frantically, tearing at each others clothes. I yanked off her bikini bottoms and thrust my fingers inside her as I pinned her against the wall, kissing the side of her neck and up to her ear. She pulled down my shorts and started grabbing my cock. I wrapped her arms around my shoulders and lifted her up, her legs wrapping around, just about to slide inside of her, when all of the sudden the door burst open and two of her friends came in dragged her out.
"Oh no big boy, she is off limits" they cackled, dragging her away.
Now call it a mix of alcohol, confidence in my naked body, and pure horniness after an entire afternoon of foreplay, but after taking a beat to process what had just happened.....I just walked out into the suite stark naked and followed them. They'd gone to a bathroom down the short hall, and I could hear the shower turning on. I went to follow them, but the door pushed closed on me and I heard "She'll be out of the shower in a minute big boy". Again, I took a beat before trying the handle and finding it unlocked. I walked in to see the three women naked in the walk-in shower together behind a fogged up glass door, laughing and screaming loudly as the saw me following them in. Fully pot-committed, I walked straight into the shower with them and locked eyes with Cindy, and her with me.
I don't know that I'd really thought through how this was going to play out when I walked in the shower, but I wasn't expecting what happened next. While was focused on Cindy, one of the ladies started rubbing my chest and the other grabbed my cock, fully treating my like a piece of meat.
"Damn, he does have big cock!" I heard
"He's definitely hot enough to cheat for" the other heckled.
"Why didn't you let me then???" Cindy howled, now turned away and washing up with a loofa.
"You're taken. Leave the good dick for the rest of us!"
"Help yourself, whore!" Cindy barbed.
Then the one to my right got on her knees and started going down on me.
"You SLUT!!!" Cindy howled again
"Oh, I'm doing you a favor girl" before going back to town on my cock.
I was too shocked to do anything, but at 24 I'd never been with a partner 10+ years my elder, and was a little shook at how good this woman was at giving head. I can hardly even picture what either of the two women looked like, what with wet hair and faces, so its hard to give a great picture, but their wet bodies remain clear in my mind, no doubt. The blowjob ninja was the older of two, maybe 40+, but in excellent shape. Her ass was rock hard like she was clearly a gym rat, she had visible abs despite a pretty thick build, and sported some awkward looking fake tits and light brown hair. The other one was younger, maybe early 30's, or at least looked that way, tall and lean with tiny perky tits, fair skin, and maybe reddish-blonde hair. She probably wasn't the type I'd notice out or be into, but naked in front of me, her thin frame was calling me.
I locked eyes with Cindy now -- she was clearly enjoying the show, but jealous at the same time. She leaned into me;
"Have fun you big stud.....I'd just give you blue balls again" she whispered and then walked out of the shower. Leaving me behind with her two friends.
Seeing her friend abandon her stake on me, the one on her knees looked up at me, "Can I feel it inside me?" she asked with a big smile.
She spun around eagerly, I slid my cock inside her with a moan. After so much teasing it felt soooo fucking good even if it wasn't the pussy I thought I'd be fucking.
Once I made it past the first couple strokes without cumming, and managed to gain my composure, I noticed we weren't alone in the shower and the tall skinny redhead had stayed to watch. Catching her gaze and recognizing a twinkle of desire in her piercing green eyes, I pulled her closer and started kissing her while I fucked her friend from behind. The friend kept demanding "harder, harder", but I was barely holding on as it was and knew if I let myself go unrestrained, I'd blow immediately. I held on for a little longer, but as I grabbed a handful of the redhead's ass now pulling her closer as we made out, it all become too much and had to pull out and slap my cock to on that tight ass to scare away my orgasm. Then getting a little bold, I grabbed the redhead by the waist, pushed her up against the wall, lifted her legs to wrap them around me, and positioned my cock to slide inside her before looking her in the eye and giving her beat to consent....to which she bit her lip and nodded before I thrust my hips forward. She was way tighter than her friend, and by the squeak she let out, less experienced, clearly struggling with my size with her lithe frame. She begged "go slow" in my ear as she wrapped her arms tightly around my neck desperately trying to maintain some shred of control. Still, holding her up, legs wet and slippery around me as the shower beat down on us, I couldn't help but go all the way in, as gravity forced her down on my cock before my thrusts popped her back up again. I could feel her arms tense around me each stroke, clearly struggling to hang on to edge of pleasure and in what felt like no time, her head dropped on my shoulder and I could feel her legs start to shake. It was all the signal I needed to start pumping harder, my legs burning now to hold her up, her arms nearly choking me as she tried to survive the body-shaking orgasm. Finally, with my orgasm now past the point of no return, I couldn't take any more, pulling out hurriedly and setting her down, all on one awkward motion. As she slumped to the floor of the shower, I came for what felt like 30 seconds, jacking off to finish, until my knees went weak and I was nearly falling over.
As caught my breath and re-established by bearings, the friend wasn't happy -- "Did you cum already?" she pushed, as if navigating a threesome without blowing your load was an easy feat and I'd failed her.
"I'm still hard" I retorted, grabbing her arm, spinning her around again, and slapping her ass hard before thrusting my cock in again.
Whether a blessing or a curse, I've aways had zero refractory period....I stay hard even after I finish, for 5-10 minutes plus, and can easily go again if I wanted to....and given the situation, I definitely wanted to. Where I was struggling to keep from cumming the first time, the second time I knew I could control it more, so I started pounding away vigorously, smacking her ass hard again and again. I wouldn't say I'm much of an ass slap guy, but her ass was so firm, it felt oddly satisfying to lay into it and based on her reaction, that was most certainly her thing so I really went for it! This time there were no more calls for "harder" and she was the one struggling to hold on. I pounded and pounded and pounded until my legs were literally ready to give out, until finally she reached back with a hand to stop me and caved down to the shower floor panting. Between the alcohol, the sun and sex, I fell back into the shower wall and slid down to the floor myself to catch my breath. I just remember the cold tile feeling sooo good on my back, and thinking I still had no clue what either of their names were.
I grabbed a towel, headed back for Cindy's room and got dressed. Her bathroom door was locked and I wasn't sure what to say after that so I just slinked away, expecting that was the end of a pretty solid story.
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CHAPTER 3
I got back to our hotel around 7or 8 and everyone was just getting ready to head out for dinner. I took an actual shower quick, got dressed, and tried to make sense of what just happened. Literally, as we were walking out the door for dinner, I'm just starting the story....."you guys aren't going to believe this, but..." and up walks Scott, Sandra and Cindy to the front door of our suite.
"Oh, do tell..." prodded Cindy
"I heard it was quite the afternoon" Sandra chimed in.
I immediately turned bright red, like I was caught cheating....on my very married Spring Break girlfriend? Really?
The ladies came in while Scott got changed, and I immediately noticed Cindy was dressed to impress. Her hair and make-up were done up and she had on a sheer black tube top with lace flower designs, which now in the bright lights of the hotel suite was almost entirely see through, and a tiny jean skirt that barely covered anything. As I made some drinks for the ladies, they played at the pool table and I caught Cindy giving me that eye again, as if to catch my attention. Right as I looked, she bent over the pool table, stuck her ass out, as if to make 100% sure I could see her ass, and flashed me her bare, fresh shaven pussy.....no panties, not even a thong under her skirt tonight. I nearly choked on my drink.
Dinner with the big group of guys kept Cindy distracted and her advances at bay, but as we wrapped things up and got the bill, her hand found its way to the inside of my thigh and it was clear that last round of drinks had done its thing on her impulse control. Walking out of the restaurant, now strolling behind the larger group, I couldn't help but ask:
"What's the deal here, do you just get off on teasing me or something?"
"Definitely" she giggled "What? You're not having fun? From the sounds of it, you had QUITE the afternoon thanks to my teasing.....but did you have to fuck both of them??" I wasn't sure if she'd gotten the whole story.....but seemed pretty clear now that she had.
I froze a little, not sure if she was joking or actually upset.
I think she sensed it, because out of nowhere she jumped in front of me, pulled down her shirt and flashed me. They were nice tits.
"C'mon, I'm just fucking with you. I wouldn't be here if I wasn't OK with it."
And she bounced off to see Sandra.
At the club, I was the last one in, greeted by Cindy with two tequila shots, one she handed to me, then downed the other one and dragged me out of the dance floor. Things started with her dancing with all my friends, and being 10 years or senior, it was clear both the ladies enjoyed the attention of a gaggle of handsome 20-somethings. But before long, Cindy found her way back to me and started grinding on me like the night before when we'd met. Again, her hands were guiding mine all over her body, only unlike last time, there was next to nothing covering her. She guided my hands up her tube top to grab a handful of bare breast, then down her skirt between her legs, and finally directing my fingers inside of her. She was soaking wet already, slippery inside and out, almost like she'd already been playing with herself at dinner. Now after two days of this, my sense of shame was gone, and I hardly tried to hide what had to be a lude display on the dance floor; pulling up her skirt now, I was pretty much openly fingering her on the dance floor, not to tease but to torture her like she had me. I wanted payback and for her to ache for me, like I had for her. At first she was into it, she'd wanted this after all, but as I moved my fingers to her clit and start rubbing fast and hard, I could tell she was losing control and didn't know how to handle not being in the driver's seat. She spun around to face me, likely an attempt to escape my busy fingers, but I reached down with two fingers this time and thrust them inside her. That took her breath away, she grabbed hold of my arms now hard, and stared up at me, her eyes begging me to stop and keep going at the same time. Finally, she reached down grabbed my hand and looked into my eyes: "I need you to fuck me now"
I grabbed her by the hand and started leading her out of club, scanning desperately for an exit anywhere, I saw a side door flash open and someone walk in, so I made a beeline right for it. We burst through the door into an empty alley, seemingly on the side of the club. I threw her up against the wall, lifted her up, and pulled my pants down enough to pull out my rock hard cock, guiding it in her thirsty wet pussy before she could change her mind. "Holy fuck" she muttered "Holy fuck" again "Holy fuck you're big". Honestly, it being my third fuck of the day and only 3-4 hours removed from the last one, I wasn't quite so overcome, but I was 100% getting off on winning our little battle of wills. The build up most certainly made it hotter for her, as I could tell she was completely lost in the sex and unaware of the people walking past the alley just ~30 feet away or our more than sketchy surroundings. Locking eyes with her now, I could tell that connection sent her over the edge, "I'm cumming, I'm fucking cumming" she gasped, wrapping her arms around me tighter and her legs so tight around me I could barely thrust any more.
As I held her up against the wall, my cock still throbbing inside of her, that post-sex clarity must of have it.
"You didn't cum inside of me, did you?" she pleaded.
"I didn't finish" I replied.
"I'm not on birth control, so I just....we have to be sure you didn't"
"I'm sure" I reassured her
"Blue balls again for you!" she joked as I set her down. "I can probably help with that" she smiled, squatting down to start sucking my dick.
Her technique wasn't quite as good as her friend, that chick was incredible, but Cindy was clearly so fucking into it, playing with her pussy and moaning with each stroke that it was way hotter. She was getting off on going down me and making a show of it, and that was sending me.
"Now can I come inside of you?" I asked
"Mmm hmm" she moaned, my dick still in her mouth.
After four to five more strokes I gave in and let go as the shudders of orgasm washed over me and my cock pulsed in her mouth, three, four, five times, she kept going and going through it though, slurping hungrily, until the sensation became too much and I had to pull her off me, her chin glistening with cum and devilish smile across her face like she knew exactly what she was doing.
"Fuck, even your cum tastes good" she laughed, licking a drop off her hand
"I guess 10 pina coladas will do that..." I offered.
As I pulled my pants up and helped her to her feet, she wiped her mouth and chest and rubbed my cum in across her tits before pulling up her tube top.
As we tried the door and found it locked, panic suddenly set in with her.
"No one can find out about this. You know?" she pushed. "Like, no one." -- "That was fucking incredible, you're fucking incredible, but that couldn't happen. It didn't happen, OK."
"OK" I agreed.
As we walked down the alley to get back in line for the club, we saw the rest of her group walking down the street towards the club.
"Stay here" she pushed, "They can't see us together" ushering me to the alley and walking out greet the ladies.
As a guy alone, it actually took me another 20 minutes to get back into the club, but when I finally did, Cindy made sure to keep her distance so as not to out her escapades. Funny enough, I couldn't even tell which two were the two from the shower, and now thoroughly spent from a wild couple of days, I only lasted another 30 minutes before heading home and mercifully going to bed alone to recover.
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