Cindy's hedonistic wedding (closed)

Cindy and I had met in college, pledged the same sorority and wound up rooming together. She comes from serious money, and was spreading her legs a lot back then, most often for me. We had our first threesome together, and she bought me my first strap on. We'd become close with a couple other girls who had equally high libidos and money.

College for most of us had been the first time we'd been unsupervised, and I wound up being nicknamed Popper, as I was the best with a strap on.

Cindy was Mouth, as she loved gving oral.

Denise was Titty, as she had an athletic build and very sensitive nipples.

Jessica and Laura were mostly involved with each other now, and even back then they only tolerated dick.

The Vegas bachelorette party had been a throw back to those wild days for me, not that I don't still love fucking, but I work in a job where being a slut would get me fired. Unfortunately my current boyfriend had been traveling and after I overindulged, he got really mad and we broke up.

The last time I had sex was at the bachelorette party, which had been 2 weeks ago and now I was faced with going to the hedonistic weeklong private tropical island paradise wedding alone. It would mean a target would be painted on my pussy and every man there would want in.

After Cindy's parents retired, their health had waned, plus with the expense of a destination wedding there were only a hundred or so confirmed guests and they were post college up to 45. None of Cindy's family was coming, they were happy to see her married to who they thought was a nice stable guy.

I knew from first hand experience that it was his stable cock, and willingness to share that had Cindy putting a ring on it.

Which brought me back to my dilemma, Cindy thought it was hilarious, as the guys were taking bets on who would fuck me first, and if I was bringing my toys with me, and if they could get me to convince the shy cousin of the groom to get pegged.

"It means they are not betting on who will be the last one to bone me before I walk down the aisle." Cindy said, and hung up.

I sighed, there wasn't an aisle anyway, it was an outdoor beach wedding, and I'd seen the skimpy swimsuit she was wearing, and the basically lace cover up that she was going to wear. As Maid of Honor I was wearing an slightly less skimpy bikini in dark purple. Denise was wearing danger orange, Jessica had pepto pink, and Laura was wearing neon yellow.

The men were wearing tropical print swim trunks.

I stared at the phone thinking hard of who I could bring, who would tolerate the level of flirting and fucking, and keep me from being involved in a bridal Sapphic orgy or a gang bang? I called a few exes, and most were sad they couldn't take that kind of time off at short notice.

I took a long shower, masturbating my frustrating out. Then I recalled a coworker who wanted to set me up, and I got off one more time before leaving the shower. I was 32, and we all still looked amazing, I had the biggest rack, and what the girls called birthing hips. I toweled off briskly, trying to keep my mind focused on the goal, but by the time I found the number and picked up the phone I was masturbating again, a vibrator between my legs, my voice husky as I said...

"Hello (insert name here later). I'm Megan and (name not important) from work gave me your number, and I was wondering if you could do me a favor?"

Will had worked until almost five that Thursday afternoon partly because of the backlog of calls
but also he really had no where to be. For no apparent reason he had been falling into a routine
of staying at home even on weekends. It wasn't all bad as he had a great apartment and full
cable. He had just been advanced to floor manager at the securities company at the age of
33. However, as is usually the case, not all portions of a person's life transition in sequence.

Will arrived at his place just before six. He had set his mind on eating at home. His first
move proved to be interesting --a phone message left from a missed call!

"Quite unusual.."

A bad habit came from trading shares of stock involved mumbling to himself when some
puzzling event happened. He quickly changed into a sweatshirt and fixed a microwave dinner
that he ate in the living room while watching the evening news. There was an NBA game
at nine, so his evening was accounted for and he seemed content. Except the call!

Barely had he finished his meal when the phone rang. He recognized the on ID screen digits! This would be Megan!

"Hi, Will this Megan and I know we never met but I know this sounds a bit unusual, but I
need an …..escort..for a wedding ..a wedding in the Bahamas! It's very close friend, we
went to college together....it's a very posh wedding I am sure.

I listened and attempted to picture the woman as she related the story. The authenticity
was apparent as no person could make up this type of story.

"Yeah, go on"

"..so it's ten days altogether. There's two formal dinners.. the wedding ...an after party.
umm..the hotel is paid for but airfare is on me. You really need only a few hundred just
for meals."

"OK, that sounds do able. But there is a few things. We would be sharing a room?"

"Yes, but I'm sure they have two beds...if that is a problem."

"These people in the wedding, do you know them?"

"Well, I know about twenty that we will be around most of the time. And Cindy of course..
I know her from college ….real well."

Will's mind was running wild to keep up, but it became almost a puzzle that needed to
be solved. He held back his answer, as he searched out the next move.

"OK, we need to meet up. Agreed? I mean it is ten days."

Megan AKA popper

I smacked my forehead, of course we should meet, I should have thought of that. I might have thought of that if I wasn't fucking masturbating.

"Dinner? drinks?" she paused and added "Pizza at my place?" She tried to recall what she'd been told about Will, well built, nice hands, also worked in money. Not that she planned to talk about business, but it would certainly help explain how they met.

She hoped for chemistry, after all her friends could spot a gay man from a mile away. She really hoped he wasn't gay. The flight was leaving in 4 days, surely that was enough time to figure out if he would fit in.

They agreed when and where to meet tomorrow, and she hung up and fucked her toy to a unsatisfactory orgasm. She wanted a warm living cock between her legs.

She sighed, rested for a few moments to catch her breath, then stood up, cleaned the toy and herself and dug into a murder mystery that she hoped would keep her mind off sex, before she went to bed.

Although her plan sounded a bit fragmented, Will continued to be intrigued and took the lead
in where they should meet. The idea would be at a neutral site, where if things did not go
well each would feel comfortable in "slipping out." He could sense some eagerness in her
voice and she did sounded quite intelligent.

"How about the Belfry Tavern on 38th Street?"

"Good, I could be there by 6pm."

"Perfect."

"The Bahamas should be lovely this time of year for your friend's wedding."

"Yes, and it's a beach wedding at 7pm."

" Good, I will see you tomorrow at six."

Will reviewed the whole concept of this seemingly wild vacation. What played on his mind
was meeting these people he didn't know, being out of town ten days and sleeping in
the hotel room with a woman he had never met! "Hopefully, she has a nice rack."

Will knew his decision would be based on what this mystery woman looked like at the
bar.

Megan AKA Popper

Megan brought a change of clothes to work, and was taking a third look in the mirror. My dark hair was cut in a bob that covered my ears. Cindy had pouted about my short hair at first, but admitted she liked the way it swayed when I was fucking. The dress was a simple wrap style, and I decided to shift the neckline down to expose another inch of skin. My breasts were confined in a demi cup bra, and now I was considering whether that was a good idea, as now that my nipples were hard they were above the cups. The thin knit material of the dress did not hide my nipples.

"Fuck it," I murmured, slipping a coat over my body before leaving the building. I took off the jacket in my car, and wondered what he looked like. My ex hadn't been gorgeous, but his cock had been a perfect fit, and the fact that I loved fucking him had shown when we were together. I'd been looking forward to him meeting more of my friend's. He'd met Cindy, and I had no idea she had a hand in our break up.

The dress was inky purple, and I told him that's what I'd be wearing. I was wearing heels, because at 5'4" I was a short stack, and I preferred to not have men looking down at my boobs when they talked to me. It was moments before 6, traffic had been a bitch.

I glanced around, glad my nipples had calmed down during the ride, and while still peaking over the top of my bra were not longer erect. That could change of course, depending on Will.

Will's work day ended at 4pm yet he stayed until 5:15 and tidied up a few files before leaving
for the cross town trip. He continued to be hounded by his decision for an idea that came
across as somewhat wild. His Uber ride dropped him off ten minutes early and he walked in
determined to hear more about the adventure. His nerves had him on edge until he
spotted the woman who had to be Megan standing back a few paces from the bar. By the
time he approached she had recognized his mannerisms and smiled.

"Hell-o....Megan?"

"Yes."

"I am Will." He gave her a moment to make an assessment as she continued to smile
giving him a sense of relief. It was the awkward nature of two people meeting for the first
time.

"Would you like a drink?"

"Sounds great."

They stepped up to the Mahogany bar with Megan taking a seat as Will stood off to one side
leaning on the bar. He put out a fifty and ordered the drinks as they began conversing
with Megan taking the lead. She stirred her Lime Rickey giving Will his first look at her
dress or the opening at the top where her smooth breasts were barely covered.

"Well, I know it sounds different. It's a destination wedding at the islands for a very
close friend. It will be high end but all expense paid AND it will mostly be informal even
the beach wedding! Aaaammm...You and I will have our own room."

Will took special note of that point.

Okay first impressions, not bad, did I want to fuck him? most definitely, did I want to wait for the wedding, probably not. Should I wait for the wedding? I didn't know. At the moment I was just enjoying having a drink with a nice smart guy, and nothing else.

He was standing, so he had a good view of my breasts, and I felt like I was babbling a little bit, "I know it sounds really silly, but showing up alone to this wedding alone. I mean can you imagine a beautiful island resort, happy couples, scantily clad staff. I'd go nuts trying to be happy for the bride and groom." I explained that Cindy and the other bridesmaids were all really close through college and we'd been getting together a few times a year since.

"And I'm sure Jessica and Laura are practically engaged and Denise's boyfriend is the kind of dick that wants to fuck his girlfriend's girlfriends if you know what I mean."

I placed a hand lightly on his chest, and stood up, pressing her body intentionally against his. "Do you think you could manage to shield me from unwanted attention." I looked into his eyes, finished off my drink, debating between suggesting dinner, or at least a table, as the bar was fairly busy.

I was also calculating what kind of condom he wore, I knew I was clean, and I figured he was clean, but better safe than sorry. I chuckled inwardly Denise had been treated for a STD more than once. We joked about her taste in men. Another part of my mind wondered how he'd feel bare and unencumbered inside me, I was feeling a little hot from my thoughts and the drinks, and had a feeling my nipples were going to show through my dress at any moment.

"Yes, I can see your point. To me, the idea of a destination wedding seems not only pricey
but really complicated."

Will paid close attention and took special note when Megan used the word "fuck" as it may
have been a clue to her ultimate intentions. Her friends sounded not only wealthy but a bit
on the wild side. He decided to draw her out to find more of her intentions.

"So, I can see where you would need a proper escort ...for the week."

"I know it seems like a long time but there are after parties and dinners. Plus day cruise
on a rented schooner which think is a sailboat."

"Do these people tend to get wild with more than just drinks because I do not do drugs?"

Megan perked up at the thought as I perhaps gave away the idea I might be considering
the whole idea of the trip.

I didn't realize what affect saying the word fuck would have on him. "No drugs, we like to remember our adventures, but we do indulge in alcohol to help," she paused the girls called wine a pussy liberator, but she didn't think she should say pussy at the bar.

"Well Cindy and Dave are very into showing just how much they want each other, Laura and Jessica get a little competitive about PDA, and Denise's boyfriend likes to run his fingers up her legs." He'd tried to run his fingers up my legs and I'd practically leapt in the groom's youngest brother's lap afterwards. I'd returned from Vegas with hickeys not only on my neck, but my boobs and my inner thigh. Plus I'd wound up fucking Denise's boyfriend in the ass while he was pounding Denise. It was supposed to be a punishment but had really gotten off on it.

Not to mention the time I'd spent with Cindy in the shower, and the hot tub, and in bed with a couple of strippers. Vegas had been orgasmic, but I came away feeling dirty, not because of what I'd done, but who I'd done it to, and with, and more.

I loved Cindy, but I was kind of glad for her to get married, and she'd drawn the line at her fiancée, and I had not fucked him, we'd kissed briefly, as he'd kissed all us girls even Laura and Jessica.

"Of course if you want to go snorkeling or something not on the bridal party agenda. I'd be glad to get away for some One On One time."

I was thinking about me on him time, or was it him in me time? I ordered a beer, I had a high tolerance for pain and alcohol which meant that of all the girls, I remembered everything, while Denise tended to be hazy on the details, Cindy didn't care as long as she had a good time, and Laura and Jessica kept each other from doing anything idiotic.

Will continued to have his picture of the intended festivities clarified as Megan spoke. He edged
closer to her as the crowd near the bar continued to build. He seemed sure that she had
not noticed his interest in checking out her chest.

"Yes, I recall a few of those Vegas trips. The gambling is often not the biggest entertainment.
I am really intrigued by boats and snorkeling. So, we would have our own room at the Resort?"

He watched closely as she answered.

Megan

"Well," I drew the word out debating what to say, "Originally my boyfriend was supposed to go with me, so Cindy booked an entire floor of rooms." I smile, debating if he was really inspecting my tits or not. "The rooms with king sized beds are at opposite ends of the hall. The bridal suite is just across from the elevator. I think Laura and Jessica have the room across from us, and Denise and her boyfriend are at the far end, and the grooms buddies and other assorted couples are in the rest of the rooms."

"I hope sharing a bed isn't a problem," I placed my hand on his arm. "The king sized rooms also have a Jacuzzi tub," hot tubs were my Achilles heel, which Cindy knew very well. I poured the last of my beer down my throat, stood up pressing myself against him. I leaned in to his ear and whispered. "Hot tubs get me hot, so you probably don't want to encourage me to use it." My lips brushed against his ear lobe, as I revealed this to him, even as I desperately hope he'll use the information to his advantage.

My breasts are pressed against him, and I smile as I feel his hips pressed against mine, and know that we are going to be sharing that hot tub.

"Well, I suppose so, if we were using our swimsuits!"

The momentary surprise across her face disappeared a few seconds later as she saw through
my joke. I could see her preparing to leave and stood beside her. There were other minor
clarifications that would be dealt with later.

"Now, here is my cellphone number. Perhaps we could meet once more before we leave?"

Will had decided to be adventurous. There were four more days to change his mind but he
had thoughts of this being a success, Already he began making a mental list of things that
needed attention at work. The next thought Will had consumed his mind as he had an
image of Megan getting naked and leading him to the hot tub as he had a clear view of
her ass!

"Of course," she pulled a pen out and wrote her number on his hand, "we fly out on early Thursday morning so we can recover from any jet lag by Friday, have a whole week to enjoy ourselves and get ride of any tan lines, than a sunrise wedding service the following Friday. Then we fly back late Saturday night."

"I'm looking forward to seeing you in your swim trunks."

She left the bar feeling relieved, relieved he wasn't a troll, wasn't a creep, wasn't disgusting. Now if he could just manage to convince her friends that they were crazy in lust to the exclusion of all other people.

Will finished his drink as he transcribed the number to his phone list then took an Uber back
to his apartment. He had off and on thoughts the next day at work, but he filed for vacation
starting on Thursday through the following Friday. His next move was to clear up existing
issues from his desk and set up arrangements with Larry to keep tabs on the office while
he was in the Bahamas.

By that evening he was at peace with his decision to be on vacation and began setting out
his items to pack. "A sunrise wedding? Who does that?" He had the basics then began the
task of getting casual shirts, sporty wear for the beach as well as evening casual. Will's
primary concern was a need to fit in with the others. He had only sketchy outline of this
group provided by Megan. He called her to get more information.

" Megan, If we are leaving early on Thursday, may I suggest we stay together on Wednesday night? That way we travel together without delay."

She had packed and repacked her luggage. First in anticipation of going alone, then going with maybe Will, then alone again before she met him, and then a final repack. Since it wasn't going to be hot, she had 5 swimsuits, a couple of which were bikinis, two nightie's, one midnight blue satin, the other a pale pink silk. One sleep shirt, in case she'd misjudged Will's interest in her. A couple pairs of shorts, and tank tops for outings. Along with the wedding shoes, a simple sheer wrap that was meant to be worn over swim suits, and one versatile wrap, that could be worn as a decent dress, or a long skirt.

She dealt with the push to get things wrapped up before leaving the office for 10 days, actually 11 as she would have Sunday to recover.

"Should we take a room near the airport and avoid parking and traffic?" Megan was feeling a little nervous that her friends would consider the lack of intimacy as an opening to pry into her sex life. Having the night before to get physically comfortable with Will sounded like a great idea.

"I know this great Chinese place, I could pick up dinner."

"A hotel near airport would be perfect, one with an airport shuttle."

He had one large suitcase and a carry-on with back-up clothes. The idea of the hotel seemed
great as it meant an extra hour of sleep. It would be a four-hour flight. Will sent a second text:

"I will pay for the hotel. Chinese sounds great."

Eating in the room would be just fine. Hopefully to get a few nerves out and make
plans about times and events. The wedding sounded to Will to be very informal as it
would be on the beach at sunrise! It left him to wonder what would happen next? Perhaps
there would be a formal breakfast?

Will reviewed his checklist one time. It would be a long time away from home.

She made a reservation in Will's name, texted him the name and address of the hotel. Wednesday seemed to be the day from hell, everyone seemed to have one more thing she should do before she left, or worse one small thing she could handle since she wasn't terrible busy after all.

She ended up skipping lunch, making what felt like a million phone calls, and by 6pm she was starving. She'd arranged to leave her car at work, as it would be simpler, and take a company car to the hotel, where one of the many co workers she'd done a favor for today would pick it up tomorrow, and she'd take a cab or something home.

She'd called in her usual Chinese order x2, and was relieved when it was ready when she pulled into the parking lot. She was a good customer, and she txted when she left the office, and she'd paid online so the moment she parked her food was being brought to her.

"Have good trip. Hope boyfriend nice." The server said in her usual broken English. Megan just smiled and waved. It smelled amazing and she took one last deep breath before navigating her way out of the parking lot and to the hotel. She nabbed a reasonable parking spot for a weekday. Nabbed a luggage cart so she could carry the food and hoped he was already there.

She hadn't thought to call, but entering the lobby she sent a txt.

"Room #. I'm here." She hated txtspeak and always tried to be succinct and proper spelling.

The airport hotels were in the same general area, directly off the exit ramp and Will got
the text in the Uber car while halfway there. The traffic was modest as it was nearly 7pm
when he was dropped off under the pavilion roof. He went directly into the lobby and
by-passed the desk. If anyone had noticed his amount of luggage they would have thought
he would be staying a week! Room 219 was on the backside facing the river so he
felt it would be a quiet room.

He knocked on the door with apprehension! Well, this it! No turning back!

Megan opened the door without checking, which caused him to smile. She looked
pleased to see him. Apparently she had been there long enough to change and set aside
a few items near the sink.

"Wow, great room."

"Thanks, I think it should be fun."

He liked the way she accented the word fun. He quickly noticed only one bed--king size!
Immediately his imagination took over as he had an image of Megan with her knees
pressed into the mattress while he took her for the first time--doggie style!

Megan had stashed her suitcase, hung up her clothes for the next day, and set out her toiletry bag. She had just started to pull food out, when she decided to discard her bra, which led her to discard the rest of her clothes, and she put on the night shirt, long white, worn from a decade of use, it said something along the lines of "It's bedtime somewhere." She pulled her hair back in a ponytail, and was just digging into the sweat and sour pork when he entered the room.

He looked as good as she remembered, "Hope you don't mind me starting without you, I skipped lunch." She didn't think about the fact that her old worn nightshirt clearly revealed the state of her nipples and lack of panties.

"Damn, I forgot to get anything to drink. Did you notice if they have Dr. Pepper in the vending machine?" She stuffed one more bite in her mouth, stretching across the bed to get her purse, flashing a lot of smooth slightly tanned flesh.

"I think I have a one," she fished out a couple of ones. One looked like it had been in a dog fight, another was very crumpled, but the third one looked pristine, almost virginal. "Do you mind getting me a drink. I'm not exactly dressed to go roaming the halls now am I?"

"No, probably not, even though the hall is empty. I brought cold bottle of Riesling for later.
be right back."

Will could hardly believe his luck. Megan had already put herself in the mood. He retrieved
a can Dr. Pepper and returned to the room. The food was secondary to his need to get
more information out of Megan. He took a seat and opened one container then began slowly.

"What time is the flight?"

"10:30"

"Good we can sleep in. That will be helpful."

"Are there any activities at the hotel for tomorrow evening?"

While Megan was answering Will watched her nightshirt which had ridden halfway up her thigh
where her tan had ended, providing a pleasant whiteness. She had leaned over on the bed
still eating as if she were alone at home. It felt good to Will that she could be so
trusting. He revised his guess about her cup size!

"So, I brought $15 hundred in cash for spending money. Hopefully, we can get by."

Megan

"I wouldn't worry much about the cash, Cindy's family is loaded. I'm pretty sure that most meals, outings, and the rooms are covered. It's probably because use girls are like family, and we never let money be a deal between us. If we had to pay our way, Denise probably wouldn't be there, and Cindy would have gotten married in Hawaii or somewhere more "affordable" " she put air quotes around affordable.

"Mentioning money, good bad or otherwise, would be considered crass. So feel free to tip generously, but don't offer to pay." She cracked open the can and took a long drink. "I don't tend to drink alcohol before flying, but I suppose as long as I stop before 10 pm and make sure to drink plenty of water in the morning I should be okay.

She had taken a good chunk out of the food, and was cracking open her fortune cookie.

"May your travels be interesting.....in bed," she added the last two words with a wink and a smile. "I hope you realize we're going to need to be rather comfortable physically with each other. My friends will be slightly suspicious of anyone I'm bringing since I broke up with Carl. He was upset about the Vegas bachelorette party."

She sighed, "He never liked Cindy," I chomped on my cookie, drained my soda, and stretched out my foot towards him, casually placing her bare foot in his lap. "I'm hoping you packed swim trunks, not that you wouldn't look great in a speedo, but Cindy made it clear that she would remove any speedos from guests." She laughed indicating it was not a joke.

"I know this is a personal question, but how long has it been since you were," she paused, "intimate with someone else?"

"Ok, I see it is time for being honest. It has been not quite a month. I have a casual
friend, Deb, who is an author writing anthropology. She travels often."

Will had finished eating and was getting a great view of Megan's legs while taking in all of
the information. It appeared that Cindy was a bit of an attention seeker, which was good
to know in advance.

"OK, comfortable physically, that should be easy. I hope you don't mind me being a
bit possessive with you in a crowd? I like to show off things that others can't have."

He waited for her reaction which was a quick yet thoughtful smile.

"Possessive would be ideal, as long as you won't feel threatened if Cindy decides to KISS me." She emphasized the word kiss. "It's been about 2 weeks for me, I didn't expect you to be a monk, but my friends tend to be really open about their sex lives."

Megan waited for him to be done eating and she plunked herself down in his lap. "I've never been quite so open, the joke is, the friend who talks the least about sex is obviously getting the most action."

She smiled feeling her nightshirt slide off her shoulder, "Would you mind putting a nice obvious hickey on me?" She leaned in, encouraging him to take his time. "It would help send the message that we are insanely involved with each other."

Megan was getting turned on by his easy going, relaxed manner. She had a feeling he was going to be a really good time.

Will had been clearly aware of Megan's attempt to escalate the sexual tension and had
purposefully down played his response. Megan was barefoot and as he finished the takeout
food he removed his shoes. He returned to the bed only to have Megan move to his lap.
Noticing her being braless was easy. "No, you needn't have that on you when you will be
getting in so many pictures next week!"

"Instead...."

Will slipped his hand along her knee and up her thigh only to find she wasn't wearing
underwear. He hid his surprise well and swooped his hand over her smooth ass without
seeking her permission! It felt so tender and smooth. Within the next few minutes his
cock would be doing the same.

Will pulled her close only at the very last moment did he slow his motions and kiss
her deeply! He took in her womanly scent as he caressed her skin underneath her
nightshirt.

"......we will be easily capable of getting your friends convinced. Now, all we need is
a few hours of …….practice! Take off your nightie, I want you to sleep naked tonight!"

Will stood up and dropped his Chinos to the floor without taking his eyes off his intended
conquest!