My holiday weekend was planned a month ago. Memorial Day is always difficult for me. I lost my only child in Iraq, killed in action. I can’t believe it has been fifteen years since he was taken from me. My lifelong best friend knows this is a dark time for me and she invited me to join her for the weekend.

I traveled to New York knowing I was in for several nights of debauchery. Betsy and I met in the second grade and we have been best friends ever since. She and I have been like sisters for fifty-five years and although we don’t live close to one another, we always make time to get together throughout the year. We've always been there for one another in times of need. The things we’ve shared over a lifetime range from silly childhood secrets about boys to shaving each other’s pussies.

She was never what boys considered attractive when we were young. We looked like opposites. As a teen, she had severe acne and she struggled with her weight. Being short always made her look heavier than she was. I know this sounds terrible but it’s true, when we were together as teenagers, Betsy’s homeliness stood out. Our friendship never waivered though and she never showed any signs of jealousy.

What Betsy lacked in beauty when we were young, she made up for in brains. She may very well be the smartest person I know. While I married, had a child, and studied law in night school, she remained single, received a PhD in Economics, and concentrated on a career in finance. She is a senior partner in a Wall Street investment firm. I’ve done very well financially but Betsy is crazy wealthy. She does what she wants, when she wants because she can. She grew out of that childhood chubbiness, had some cosmetic surgery, and hired a personal trainer. She resembles nothing like when she was an awkward teen. Today she looks gorgeous.

One thing has never changed though; she is still the biggest slut I know. She would hump a tree trunk to get off. Another thing I’ve come to realize since I’ve discovered my own inner-slut; men don’t care where they stick their dicks so her past lack of beauty had not hindered her ability to enjoy half the boys in senior high school.

I caught a Friday afternoon flight from Tampa to Islip Airport on Long Island. It's the closest commercial airport to Betsy’s house in the Hamptons. The flight was uneventful; the way I like them. As usual, whenever I visit her, she had a driver waiting for me when I land. I climbed into the back seat of a black Cadillac Escalade limousine. It had a fully stocked bar with my favorite bourbon, and a small chrome vibrator with a note attached. It read, ‘This is to occupy your time while sitting in traffic. Think of me while you are pleasuring yourself. Try not to distract your driver.’ She is a piece of work.

It had been a few years since I visited Betsy at her vacation house. When I see her, it’s usually at her townhouse on the Upper West Side of Manhattan. The last time I traveled to Southampton, I was still in my torturous marriage. She was a good friend letting me bend her ear for three days, whining about being trapped in a loveless relationship. I already knew this trip would be very different.

The forty-four-mile drive from the airport to Betsy’s beach house took almost two hours. Friday afternoon traffic to Southampton is a bear. I was thrilled that I had the little gift for the ride. I filled my glass with ice, poured myself a bourbon, and leaned back in the oversized leather seat of the SUV.

Driving out of the airport, I had my dress hiked up around my waist and my silk panties were on the floor. The sheer delight I experienced as cars and trucks idled next to us was magnificent. The windows of my ride were blacked out for privacy. If those drivers knew what was going on in the back seat, it would have caused an accident. At one point, my blouse was unbuttoned and my bra unfastened. My right hand was working the toy as my left pulled and pinched my nipples. I was screaming out Betsy’s name as I had one orgasm after another. Even though the driver couldn’t see me through the privacy glass, I am certain he heard me. What I wanted was for him to stop the SUV and join me in the back seat. He didn’t.

As we traveled down Meadow Lane in Southampton, I rolled the window down; the salt air was blowing off Shinnecock Bay. There was a slight chill in the air compared to the heat of Florida. The last weekend in May is the unofficial beginning of the beach season in New York. It is usually the first weekend warm enough to frolic naked at the beach. I was looking forward to the possibility. I pulled myself together as we were getting close to the house. Betsy’s little vacation hideaway was a 7500-square-foot, six-bedroom house on the beach. It had an indoor pool in a glass sunroom and a small staff to care for her weekend needs.

The SUV turned through the gates of the house. The driveway is long and the house wasn’t visible from the road. She was waiting outside for me. I barely exited the SUV when she practically knocked me over with a tight embrace.

She whispered in my ear, “I’m so glad you’re here. We’re going to have so much fun. Did you enjoy your little welcome gift?”

I knew her well enough to understand that her idea of having fun would be a continuous party all weekend. I also know that she would do everything possible to take my mind off of the reason for the holiday on Monday. The last time I was at her place in the city, it took me a week to recover. It was shortly after my divorce was finalized and during that trip, I was ready to go a little crazy. This visit was no different.

“It did make the time pass quickly. I’m afraid I got carried away. Your driver may have heard me becoming a little enthusiastic. Oh wait, I left my panties on the floor of the car."

“Oh, don’t worry about him. I’m sure he heard you, and trust me; it wouldn’t be the first time he found underwear in the back seat. I’ll have Sylvia, my assistant show you to your room so you can freshen up. I’ll have your luggage brought to you.”

I let her comment about her driver go. I could only imagine what had gone on in that vehicle. We walked into the house holding hands. There were already a dozen people inside. I recognized several of Betsy’s guests from previous visits. One couple, in particular, was very familiar. Robin and Blake came right over to greet me.

Blake wrapped his arms around me, grabbing my ass and pulling me toward him. “It’s so nice to see you again.”

I could feel his cock straining the material of his pants as he pressed against me. It excited me. “Yes, great to see you too.”

Then Robin took her turn with a special welcome running her hand across my back. She is from Georgia and speaks with the cutest southern accent. It is so out of place in New York, I love it. “Oh sweetie, you look so beautiful. All Blake and I could talk about was if you would be here this weekend.”

The last time I saw the two of them was at a private club on the west side of Manhattan called the Dating Room. We spent an evening together living out each other’s fantasies. Betsy and I went to the club planning an evening of perversion. Neither of us was disappointed. She hooked up with two studs that used her in the bondage room. I wound up with Robin and Blake.

It was his birthday and Robin promised him a special night. She and I laid him out and made him our sex slave. She would mount his cock, bucking up and down while I straddled his head, making him suck my pussy. After we both came, she and I would switch positions. We ended the evening with Robin and me making love to one another, tongue-cleaning each other while Blake enjoyed having his dick sucked by a stranger that was passing. We watched as he coated her throat with his cum.

I said to Robin, “I’ll be down shortly. I want to change into something more comfortable. I’ll find you in a little while.”

In reality, I needed to clean up more than change. The physical activity on the ride to Southampton caused me to work up a sweat. My pussy was soaked. Sylvia handed me a bourbon on the rocks and took me upstairs. When we walked in the room she gave me a quick tour. My bedroom was amazing. It had a king-size bed, a bathroom with a large spa, and a balcony overlooking the Atlantic Ocean. There was also a small pantry with adult beverages and snacks.

Sylvia asked, “May I help you with anything?”

“No. I think I am all set. I’m going to take a quick shower and join the festivities downstairs. Thank you for showing me the way up here.” Sylvia turned and exited the room.

I threw my dress and bra on the bed. My panties were gone, never to be seen again. I’m certain still in the SUV. I turned the shower on; instant hot water. The water felt glorious as it trickled down my body. A dispenser with buttermilk body wash was mounted in the shower. As I started to slather my body, I felt a presence behind me. It was Sylvia. She reentered the room, stripped out of her clothes, and stepped into the oversized shower with me. Her skin was pale and smooth. She had brown hair, perky breasts, and a small patch of hair between her legs. I am guessing she was in her early twenties.

We didn't say anything. She carried a loofa with her. I turned away from her, put my arms in the air over my head against the marble wall, leaned forward slightly, and spread my legs for her to wash me. Sylvia sponged off my shoulders and back. Her touch was soft making me tingle. As her hands worked their way down my body, I spread my legs wide wanting her to scrub me clean. She took my lead. I shut my eyes tight and I felt myself building up. The loofa dropped to the floor. Her hand traveled between my legs, working my folds open. One, two, and then three fingers started to do a dance inside me. I groaned and my knees grew weak as I shuddered with an explosive climax.

Before I could gain my composure and return the favor, she was done with me and stepped out of the shower. Disappointed, I asked, “Where are you going?”

“I’m here for you. That's what I am paid for. Anytime through the weekend, you need some attention, whatever you need, I am here for you.”

It was just then that I realized Sylvia was bought and paid for; a professional. I should have known Betsy would do something like this. After giving it some thought, I knew this was going to be quite a memorable weekend. What started as a quick shower to freshen up, wound up being twenty minutes of pure joy. I finally turned off the water and stood for a few minutes to gain my self-control, dried off, and dressed. Sylvia was nowhere to be found. I slithered into a very tight black silk party dress; no panties or bra. My attire left very little to the imagination. I sauntered downstairs.

In the time I was upstairs, the party had tripled in size. About thirty people were milling about. I noticed several people in leather. One young woman was wearing only biker chaps and a leather vest. She was in her thirties, had great tits and between her legs, she was bald as a cue ball. The man with her was in a matching outfit, chaps, and a leather vest. He was well-hung. I couldn’t help to think, ‘Did Betsy hire these two to get the party started like she hired Sylvia?’

I wandered around, making my way to the middle of the house where the pool was. There was a naked couple, playing and splashing in the pool like children. It looked like fun. I knew at some point in the evening I would be there with them. I love the water. Betsy was across the pool when she spotted me. She waved for me to come to her.

“Nice dress. Did Sylvia show you around?”

I smiled. “Yes, she took good care of me. You know, that wasn’t necessary. I do just fine on my own.”

She giggled as if we were in the seventh grade. “I know. Sylvia lives here full-time. I call her my vacation administrator. She watches the place when I’m not here and arranges everything from making sure the kitchen is stocked to furnishing me with a companion when needed. And, on occasion, she goes down on me.”

Typical Betsy. Once a slut, always a slut. I just smiled and shook my head.

She continued, “Robin was looking for you. I’m pretty sure she wants to pick up where the two of you left off when we were at the Dating Room in the city. Don’t feel pressured into being with her. There are plenty of guests here to meet and have fun with. Come with me.”

She took my hand and walked me to a group of four men standing in a circle. Betsy has a way of interrupting people and does not come across as rude or pushy. That ability is what made her so successful on Wall Street. That, and as the saying goes, she can suck a golf ball through a garden hose. She is the queen when it comes to blow jobs. Although I don’t know for sure, it wouldn’t surprise me if she fucked her way into a partnership at her firm. Unlike her, I never mix business with my personal life.

“Gentlemen, this is Darlene. She is my friend that I’ve known since we were children. She divorced about a year ago and she is always looking for a good time. Be careful though, she’s an attorney, you might wind up being served.” She walked away laughing.

I wish she hadn’t said any of that. Men seem to be intimidated when they find out I’m a lawyer. I know I’m attractive and have no problem meeting men. Throw in my attitude toward casual sex and I do fine without an introduction like that. Between the ride from the airport and the help from Sylvia in the shower, I was ready for more.

One of the men, the one that was the youngest in the group, probably forty years old looked at me with a straight face and asked, “Want to go upstairs and fuck?”

You could see the others just cringe at his boorish attitude. If he spent two minutes making some intelligent small talk, I probably would have been the aggressor. He was a good-looking young man; just an asshole. Instead, I decided to turn my attention to the other three men.

“You really know how to charm a woman. I have no use for douchebags.”

Then I turned toward the remaining men. “C’mon, let’s go for a swim.”

They all looked at one another, not sure if I was serious. I turned and walked to the edge of the pool, dropped my dress on a lounge chair, and lowered myself into the water. Even though the pool was heated, my nipples stood at attention. One by one, their shirts came off, their pants fell to the ground and they followed me into the clear salt water of the pool. I was like the Pied Piper leading the group to an evening of perversion and depravity.

By now, there were several people in the pool, all naked. Independently, the men all came close to me, each one not sure as to how they should proceed with trying to get me into their bed. Little did they realize, I was ready to fuck any one of them. Why not? They were all good-looking mature men, all hung well and none of them were assholes like the youngest of their group.

I leaned on the side wall of the pool, my nipples were rock hard and pointing up. My eyes were closed enjoying the water when I felt a hand touch my arm. His fingers tightened, pulling me toward him. It felt wonderful. He had a confidence about him that I liked. He broke my relaxation as I stood to face him. He was the oldest of the group, I am guessing about sixty-five years old. He had steel blue eyes and obviously spent time in the gym. For a man his age, he was fit and muscular.

“What is your name?” I could feel myself start to throb with desire.

“Thomas. You are beautiful, I can’t help myself. I want to make love to you.”

That was all he had to say. He made me melt. I extended my arm, reaching for his hand. “Now that is how a gentleman gets me. Tell you what, I’m going to get out of the pool and dry off. I won’t be putting on my dress. I’m going to walk naked through the house, head up to my bedroom, the third door on the left, and wait for you. You have five minutes. If you aren’t there, I’ll find another stud to take care of me.”

My voice carried over the water. The young asshole heard what I said and stood in disbelief. I laughed as I drew attention to myself strolling proudly past him. By the time I reached the stairs, I could see Thomas drying off. ‘Damn, he looked good,’ I thought to myself. I couldn’t wait to have him.

Sylvia was at the top of the stairs. She giggled. “You lost your dress!”

I smiled. “Oh no, I didn’t lose it. I know exactly where it is. It is on a lounge chair next to the pool. Would you be a darling and go retrieve it for me? I’m expecting some company in just a minute.”

“Your wish is my command.” She dutifully scampered down the stairs and out of sight.

The sun was starting to set and the room needed to have a light turned on. The curtains were pulled wide open. Anyone outside could see in the room. I am a bit of an exhibitionist so I didn’t mind if we put on a show for all to see. There was a knock on the door.

I was sitting on the edge of the bed. “Come in!”

In walked Thomas. He brought the other two men from the pool. “I hope you don’t mind. I brought Chad and Mark with me.”

Three handsome silver-haired studs stood before me. They all put their pants back on to come to my room. I looked at them and just laughed. I was about to be ravaged in a gangbang and they felt the need to get dressed. Then I wondered, ‘Did Betsy have anything to do with this?’

The first thing that came to mind was, “What the fuck? Are the three of you shy or something? Take your damn pants off and get over here. What am I going to have to do, give you all a lesson? What do you think this is, Gangbang class?”

These stock broker-looking charmers didn’t need any schooling. Just then, the door swung open. It was Sylvia with my dress. She ignored the four of us, walked to the closet, and hung up my dress as if nothing was going on. At this point, I was sprawled on the bed naked. The three men were in the process of dropping their pants and joining me.

Thomas was the first to climb onto my bed. He started to kiss my shoulder. I took his head and guided him to my lips. We kissed. His lips had a hint of cigar taste, not strong though. It made him even manlier to me. Our tongues were locked together when I felt a hand on my left leg. Chad was spreading me. I could feel a sudden gush from between my legs.

I grabbed the headboard and held it tight. Thomas was still kissing me while Chad started to run a single finger on the outer edges of my pussy; I soaked his fingers. Mark stood to the side, stroking his cock. As this was taking place, I could hear Sylvia meandering across the room. When I was able to get a glimpse of her, I could see her sitting in a chair. She had no clothes on and was starting to massage herself as we put on a show for her.

The kissing, the fingering, and the cock stroking were all fine but, I needed more. I blurted out, “If someone doesn’t fuck me right now I am going to scream!”

I couldn’t wait any longer. It was as if a demon had possessed my body. I pushed Thomas onto his back and mounted him. He slid into me with ease. My bucking motion was causing him to grunt. Chad took advantage of my upright position and started to chew my right nipple. Mark, the guy stroking his cock, as if on queue took my left nipple and twisted it. Now Sylvia came closer to the bed. Within thirty minutes, I went from being introduced to this group poolside to a full-blown orgy in my bedroom. I love my life.

The attention my body was receiving was exhilarating. I started to lose myself as the first pulsating orgasm began.

“Oh my fucking God this is amazing! I love your dick Thomas! Harder, fuck me harder!”

Thomas didn’t disappoint. His body would pitch matching my motion causing him to embed himself deeper into me. Mark was kneeling next to us. His hand wrapped around the back of my head drawing me down to his cock. I took him into my mouth. He was thick. My motion with Thomas slowed as I tried to match the same rhythm with Mark. I could sense Chad positioning himself on the bed. The way I was riding Thomas made my ass a prime target for Chad to take.

Just the thought of being triple penetrated caused a flare through my body. Chad’s finger started to poke and probe me. Out of the corner of my eye, I could see some movement. It was Sylvia. I had forgotten she was a witness to this salacious rampage. She came to the bed and handed Chad a jar. It was a sweet-smelling lubricant. He coated his cock, spread me wide, and started to drill into my rectum. With Mark’s cock still in my mouth, I let out a muffled scream. The pain was great but delightful. I couldn’t move as the three men used me for their pleasure.

Mark was the first to let go. “Here it is!”

A thick stream of cum coated my throat. The flood cascaded out of my mouth, down my chin, and onto Thomas. Mark fell back onto a pillow. Chad and Thomas continued their assault on my body and now Sylvia was on the bed with us; watching. I was being stretched to my limits and about to erupt.

“More! More! More! Yes! That’s it!”

I was coming hard. Thomas came with me. I could feel him fill me with his release. Chad pushed me down onto Thomas and gave one hard thrust holding his position. Like Thomas, I could feel the warmth from sperm permeating my body.

As quickly as this started, it was over. Chad withdrew and I rolled off Thomas. Mark was already off the bed and pulling his pants on. I lay there, a sweaty, semen-soaked mess. I could hardly move. The rush of euphoria was still palpitating through my body. I love it when my orgasms last long after I am through. One by one, without saying a word, my three studs exited the room.

Then I focused on Sylvia standing over me. She was naked, waiting patiently for my instructions.

I was panting and all I could say was, “Give me a minute Sylvia.”

She understood, turned, and left the room. A minute later she returned with a wet washcloth and a dry towel. Betsy is so spoiled. She has this young servant trained well. Sylvia spread my legs and started to clean me. My clit was like a rock. She was fascinated with it as she ran the cloth over it. I flinched as her hand lightly swabbed the remnants of three men having their way with me.

After a minute of attempting to wash me, she said, “You need a bath.”

She left. I could hear the water running in the distance. When she returned, she took me by the hand and helped me to an oversized tub filled with suds.

“Be careful stepping in. I’m going to make sure you are clean so you can return to the party if you would like.”

Clean she did. The way she ran the oversized sponge across my body made me quiver. Her touch was light but effective. Several times, the sponge crossed my clit. Each time, it was a mini burst; a slight orgasmic rush. I didn’t want her to stop. Every square inch of my body was taken care of. Being bathed was heavenly. When she was done, she helped me out of the tub, patted me dry then finished the process by rubbing warm coconut body oil all over my body.

Instead of returning to the party, I would have preferred spending the rest of the night making love to this little vixen. After all, she was here to serve me. But, I didn’t want to be rude. After all, I was here to see Betsy. It was still early and I could hear music and the crowd downstairs. I had only been there for two hours and I had a dozen orgasms.

A new outfit was laid out for me, my third of the day. This was a skin-tight, royal blue dress. Sylvia helped me with it. She zipped the back and gave my ass a little squeeze. I stood in front of a mirror. She was admiring me. My hair was a mess. I quickly ran a brush through my hair, applied some lip gloss, and returned to the festivities.

In the time I was upstairs, the party had become a wild session of overindulgence. There had to be sixty people in the house now. Couples had paired off and were in different stages of undress. I was out of place being fully clothed. Betsy was on a couch on her hands and knees. She was being fucked doggie style, unaware of her surroundings. I started to become concerned that this party was getting out of control. Instead of worrying, I found Robin. She was wearing a tiny thong bathing suit and no top.

“Where have you been? I’ve been looking for you,” she said.

“Oh, I was upstairs taking care of some business I had with a few gentlemen. It took longer than I expected. This party got going since I left.” My smirk may have told the truth.

Robin looked hot. Since our moment at the Dating Room in the City, she lost a few pounds, her body had an even tan, and her hair a silver-white instead of the dyed blond when I met her. She’s younger than me by at least ten years. Usually, when a woman lets her hair color go natural, nearly white in her case, it makes them look more mature. Not Robin. Between the bronze color of her skin and hair color, she looked younger. I wanted to taste her in front of everyone.

My arms extended, reaching out to her pulling her to me. Just my hand touching her set off a chain reaction between the two of us. Her nipples became as hard as diamonds. The flood between my legs was out of control. We found a spot on a couch in the middle of the large living room. To our left, a young man was having his dick sucked by an older woman. On the floor in front of us, a woman was pleasuring herself with a stick-like vibrator. Robin and I watched as our hands started to explore each other’s bodies.

I leaned toward Robin and said, “I wonder where she got that toy from? It looks like she is enjoying it.”

The woman was alone, pressing the small tip firmly against her clitoris. She was having short spasms, her eyes closed tight. It was obvious that she was in another dimension. Her body would quake every few seconds.

Robin whispered, “Betsy has a toy box in the next room. It is filled with gear to enhance one’s experience when she has one of these gatherings. She keeps a nice assortment of dildos, vibrators, anal beads, butt plugs, and restraints for her guests to enjoy. All of it is brand new and you get to keep what you use. She is a very generous woman.”

That is the Betsy I know and love. All she ever had on her mind was boys. As I look back, I can’t believe she never got knocked up. I was her opposite, a good girl. I had only been with one man, my husband. That is, until I discovered he was a closet homosexual and had been cheating on me for years with men. That was when I came out of my shell and uncovered an alter ego that craved attention.

My dress was still on. Robin’s hand was up under it. With a single finger, she found my clit. It swelled to the size of a grape. My head rolled back as her finger made a circular motion orbiting my nub. It was driving me crazy. I lifted my hips and pulled up my dress around my waist.

I demanded, “Suck it! Go down on me.”

Robin ignored me. She continued to tease me, bringing me to the brink, and then stopping. When the urge to come disappeared, she would start again. Over and over, it was like striking a match that never lit. In the meantime, the guy getting a blow job next to us finished and moved on. The woman he was with was still next to us, fascinated at the way Robin was taunting me. The woman on the floor was oblivious to her surroundings as she continued to manipulate the wand.

Thomas was across the room sitting in a chair. A young woman had her head in his lap. I could see her bobbing up and down. I thought to myself, ‘I wonder if she can taste my pussy all over his shaft?’ Then the next build-up started again. This time the urge to come was too much to handle. Her teasing became unbearable. I reached out, grabbed Robin’s hair, and forced her head in between my legs.

I was out of my mind. “Suck it, you fucking cunt! Make me come!”

Her body twisted as I shoved her face into my pussy. I leaned into the woman next to me, but she didn’t move. Robin wound up on the floor almost on top of the woman with the wand. Both my hands had her by the hair and I pulled her into me. Her mouth consumed my clit sucking it in, flailing her tongue, stabbing it. I started to convulse, shaking uncontrollably. This went on for what seemed like hours. My hands finally released her and I was exhausted. The woman I was leaning against gave my left breast a firm squeeze.

I sat on the couch, not able to move. My body had all it could take. It was almost midnight and the party was starting to break up. Several people were heading for the stairs. Betsy was nowhere in sight. I just assumed that she made her way to her bedroom with one of her many admirers. Robin was still sitting with me, Blake was gone and the woman to my left was sound asleep.

Like magic, Sylvia appeared. She always seemed to be there when I needed her help. Her arm stretched out to help lift me off the couch.

Robin was ready to follow me. I turned to her, gave her a quick, passionate kiss, and said, “Good night. Maybe we can hook up tomorrow sometime.” I made it clear that she wouldn’t be coming back to my room for the night.

I turned to Sylvia. She took me by the arm and helped me to the stairs. We climbed together, side by side. When we arrived at the third door on the left, Sylvia did not attempt to say goodnight. It was quite obvious that she wanted to spend the night in my bed. That was fine with me.

The door closed behind us. The balcony door was open, and the aroma in the room was a pleasant beach scent. I love the smell of the ocean. The sound of the waves crashing on the beach was very soothing. Sylvia turned me and pulled the zipper of my dress down. Her touch was soft as she freed me from the thin material covering my body. For the second time tonight, I stood naked before this little nymph and watched as she shed her clothes. We settled into the king-size bed.

We lay for a short while, touching and holding one another. She ran a single finger over my body. It was relaxing and I could feel myself starting to doze. The last thing I remember was a light kiss on the cheek and Sylvia whispering in my ear, “Sleep well, tomorrow is a new day of fun.”

She continued this ritual until I was fast asleep.