Day 100: The Big Four-Oh
written by:
Chellee Big Cannons

This is my eighth story. You don't have to read the others first, but they all deal with the same subject--the fact-based events of my sexual awakening after years spent being a stereotypical "good girl!" I hope you enjoy and that you'll check out my earlier stories, too! As always, I love feedback and try to respond to everyone!

"Stop it!"

"But I feel so guilty," I said.

"Just stop it," Sky repeated. "You're damn near forty years old. There's no reason to feel guilty for having some fun."

I'd just finished telling Sky about my latest sexual conquest. I'd gone back to my alma mater to speak at a library class and ended up in bed with some of the students.

It had been open, consensual fun between adults, but I couldn't help feeling guilty! I'd spent my whole life being the "good girl." I never had one night stands. I dressed conservatively. I worked in a library. Sex was almost always done in a bed, with the lights off, with a guy I considered "husband material."

But lately, things had been different. Three months before my fortieth birthday I was alone at an out of town wedding and craving male attention. I'd been charmed by the advances of one of the groomsmen and ended up going to bed with him—even though he was young enough to be my son.

I'd promised myself it was a onetime adventure. When I got home I'd go back to dating age-appropriate men and looking for a steady relationship instead of having one night stands with guys who weren't even born when I graduated high school.

But it was like a new world had opened up around me. I kept seeing sexual opportunities in everyday life. And I kept taking them.

I didn't tell anyone about my adventures except Sky. We'd been best friends for two decades and I knew I could trust her with anything. Like me, Sky was a bit old-fashioned and conservative when it came to sex and dating, so I worried that she would judge me when I told her what was going on in my life. But I'd underestimated my best friend. She wasn't just receptive to hearing about my sex life. Sky was downright curious. And curious enough to participate.

And so the two of us had experimented together a couple of times. We'd kissed and fondled and tasted one another. And we'd brought home boys to share.

Unlike me, Sky didn't seem to have any guilt about what was going on. Although she agreed that it should just be experimentation and not become an ongoing thing.

We hadn't carved any rules in stone, but after our last time together we had an understanding that we wouldn't do it again—unless some special circumstance arose.

"Seriously, Chellee," Sky continued. "You're just having fun. Nobody knows about it. You shouldn't feel guilty."

"I know, Sky," I responded. "I just start feeling uptight about things. Like what if I'm standing 10 feet away from the man of my dreams and don't notice because I'm too busy throwing myself at a teenager like a desperate old maid?"

Sky laughed.

"You're no old maid," she said.

She gave my body a long, salacious look.

"And you don't have to throw yourself at anyone," she continued.

I knew that was true. Genetics and years in the gym have given me the kind of comically curvy body that men lust after—tall, blond, with tight legs, a flat stomach, a firm ass, and large chest. Though I've never been confident around men, I'm also not foolish enough to think I go unnoticed.

"Why don't you just put all the worrying out of your head until after your birthday?" Sky suggested. "We can just go and have fun and not worry about anything. Then you can get back to husband hunting," she added with a wink.

It wasn't a bad idea. My birthday was coming up in a week and Sky and I had been planning the celebration for months. We'd booked a suite at an all-inclusive resort in Cancun. The idea of just cutting lose with no repercussions for one more weekend was appealing. Plus, there was some symmetry to the idea; my first wild weekend started out of town, so it made sense to finish it on another trip.

"So what kind of fun were you imagining?" I asked playfully.

"Oh, you know," Sky said with a smirk. "You, me, the sun, open bar. And maybe a Mexican pool boy for each of us?"

"That sounds lovely," I admitted.

"And if that doesn't work," she said, "we can always just rub each other down with lotion and see what happens."

I flashed her a wicked smile. I was tempted to end our weekly happy hour routine at that moment and invite her back to my place. Or maybe I hoped she would suggest going somewhere else. But neither of us brought it up. Instead, we finished our drinks, talked about the week ahead, and kept mentioning how relaxing it was going to be in Mexico.

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There is nothing quite as comical or foolish as a the swagger of a confident man. It's like they actually believe they have every woman fooled and that they're controlling the situation. In truth, it's just the opposite. Every woman knows that she is in control. And all the machismo and lame attempts at humor are either annoying or puppy dog cute.

With Jose, it was the latter. He was a rich, tall, athletic good-looking boy from Mexico City whose parents owned a timeshare at the hotel that they were allowing him to use with his friend. It was obvious that he was used to having his way in life. And he probably did great with the ladies. So it was only natural that he thought that his charm would work the same on me.

Of course, that was after I approached him first. Sky and I had been sitting at an outdoor bar for an hour. She was encouraging me to have fun. And, for once, there were no qualms or second thoughts on my parts. I knew it might shock my friend if I didn't show at least a little hesitation, but I didn't care. I was about to turn 40. I was in a foreign country. And I saw something I wanted.

Jose was at the bar with his friend, Ram. They were ogling every single woman under 25. Chances are, they never would have noticed me. I wasn't in their target age range. But when I strolled up and took a seat they both noticed.

I was dressed fairly conservatively. A black sundress with a floral print and a halter top. It wasn't tight enough to show off every aspect of my fit body, but I knew my cleavage was on display. And neither of the boys minded looking.

"Why are you guys here all alone?" I asked.

They made some rambling excuse that I didn't even listen to.

"Do you want to buy me a drink?" I asked Jose directly.

He nodded. Of course, the hotel was all-inclusive and the drink was free. But he got the point.

"So, it's my birthday," I said to Jose.

"Are you here with your family, then?" he asked.

"No. I'm not married. Just here with my friend," I answered.

"How old are you?" he asked.

"Why don't you guess?" I suggested.

He looked me up and down. His eyes lingered on my taut arms for a second. Then they locked on my tits. He had a hard time pulling his big brown eyes away.

"I don't know," he said. "I don't want to insult you. I'm not good at this."

"Just guess," insisted.

He shook his head and said he didn't want to.

"If you get close, I'll give you a kiss," I said with a wink.

He seemed intrigued by that.

"Alright, but don't be offended," he said. "I'm just guessing and I'm not good at this. It seems like a special occasion. So, are you thirty five?"

I tossed my head back and gave a throaty laugh.

"Close enough," I said.

I leaned forward. Jose turned his head to offer me his cheek, but I quickly grabbed his face and turned it back. I put my other hand on his thigh for balance. And then slowly moved upwards toward his crotch.

There was nothing innocent or playful about the kiss. I caught Jose by surprise when I slipped my tongue into his mouth. He sat stunned for a second, but then she kissed me back.

He was wearing a button down Hawaiian shirt and board shorts. I let my hand come up higher until I found his bulge. I gave it a long squeeze.

"Where's your room at?" I asked playfully.

He nodded to a room on the north side of the pool area.

"Oh, mine is way over there," I said with a nod to the south. "I bet the view is completely different from your room. Can you show me?"

Jose stammered a few times. He'd been taken completely off-guard and was off his game. But he didn't resist.

I waved across the bar at Sky as he took me by the hand and told Ram to stay out for a while.

Jose was shy on the quick elevator ride up to the fourth floor room. He didn't say a word. I could see the outline of a nice, hard cock in his shorts. And I was eager to have it in me.

Sky had made a joke on the flight down by saying I needed to celebrate turning 40 with 40 orgasms. We'd both snickered, since it seemed preposterous. But the odds were suddenly looking good.

"So show me the balcony," I told Jose after he'd opened the door.

We crossed through a small living room and kitchenette. There were two bedrooms off to the side—just like the room I was sharing with Sky.

Jose opened the sliding glass door and I stepped out onto the balcony. I put my hands on the rail and looked out over the bay. He stood quietly watching me.

"Come closer," I said.

He stepped toward me. I took his left hand and put it next to mine on the rail. He got the point and stood behind me. He put his right hand outside mine on the rail. We were pressed closely together. I could feel his hard-on against my ass.

I turned my head and looked back at him.

"Do you want to kiss me?" I asked.

Jose nodded slowly.

Our lips met. It was a slow, wet kiss. Our tongues danced together.

"Do you like my body, Jose?"

"Yes, very much," he responded.

"What do you like most?" I asked

"I like it all," he said.

"What about my titties?"

"Yes," he nodded. He kissed the back of my neck. He removed his hands from the rail and put them on my torso.

"I like your titties," he said in his thick, Mexican accent.

"Have you fucked a lot of girls?" I asked.

He shrugged.

"I've fucked a few," he responded.

"What's the oldest woman you've been with?"

He shrugged again.

"I don't know," he said. "Early 20s?"

"Did she have titties like mine?" I asked.

He shook his head.

"Definitely not."

"Do you want to fuck me? I'm a lot older than 21," I said.

He nodded.

My dress had big black buttons going down the front.

"Unbutton my dress," I said.

"People will see us," he said.

The courtyard area had multiple pools, restaurants, and bars. Plenty of people could see the balcony area. And the sun was still up.

"They'll just think it's my swimsuit," I assured him.

His dick was rock hard and planted against my ass as he opened the buttons on my dress. I reached behind my neck and untied the halter strap. It fell to the ground around me. I stood on the balcony in lacy black panties and a matching strapless bra. I looked across at the bar we'd been in and wondered if Sky was watching. It was too far for me to make out faces in the shadows.

I rubbed Jose's dick through his shorts. I turned around to kiss him.

"You're going to fuck me on this balcony," I said. "Later tonight. I want you to fuck me right here. With these titties hanging over the rail."

Jose nodded. He eagerly felt at my tits. I kissed him again and pulled away.

"Sit down," I commanded with a nod to a chair.

There were a couple of towels folded on another chair. I hung them over the rail as if they were drying to obscure the view below waist level. And then I dropped to my knees.

Jose untied the draw string on his shorts and I quickly pulled them down.

His cock was amazing. It was long and brown. It wasn't fat, but I worried it would go halfway down my esophagus when I deep throated him.

I reached behind my back and unhooked my bra.

Jose's eyes tripled inside as my luscious tits fell free. I grabbed them and shook them a bit for him. Then I pulled his cock between the two of them. I spit on the head a couple of times and rubbed my saliva down his shaft with my hand. Then I held my tits together for him to fuck.

He was over-excited and awkward at first. He kept thrusting at odd times and seemed unable to get the time right. But he finally got control and started fucking my big titties. I put a hand around the base of his shaft and tugged while my lips were wrapped around the head of his long rod. His salty pre-cum filled my mouth and I swallowed it down anxiously.

He started groaning and whimpering like a needy child. I pulled my tits away and tried to deep throat his big dick. I almost gagged on it! I bobbed my head up and down his lengthy shaft and tugged at the base with both hands.

Jose's ass was up off the chair and he was bucking his hips. He was fucking my face. I thought I would choke, but I didn't stop working his cock.

Finally he grunted loudly and his giant dick exploded. Gobs of hot cum hit the back of my throat. I pulled back and some splashed on my titties. I wiped it up and licked my fingers clean.

"Now it's your turn, stud," I insisted.

We went inside and I saw in the middle of the couch. I spread my legs while Jose knelt before me. I lifted my hips so we could slide my panties off.

I ran my fingers through his shaggy dark hair and guided his face to my furry little slit.

Jose knew exactly what to do. He licked my pussy up and down. He swirled his tongue around my clit. He put two fingers in my tight hole and started banging me.

My whole body was shaking. My tits bounced up and down. Now it was MY turn to lift my hips and force myself toward HIS mouth. I came hard.

"You want to fuck now, mami?" he asked.

"No! Again!"

He kept going. He pounded my pussy with his fingers and slipped his tongue inside me. He circled my clit with the thumb on his free hand. I started grinding my pelvis into his handsome face.

I came a second time. It was even more intense than the first.

"Now we fuck," I said, breathlessly.

We switched position. Jose sat on the center of the couch while I stood in front of him. His beanpole dick was pointing straight to the sky. I straddled him on the soft and worked my velvety pussy down his dong.

From the expression on his face, I didn't think Jose would be able to handle it. For a full 15 seconds it looked like he would lose control and come right away. But he managed to hold off. He buried his face in my massive jugs and started bouncing me on his cock.

He was amazing to have inside me. His cock was long like a tent pole and stretched my insides. It was almost painful to be impaled on his dick. I bounced up and down like I was on a pogo stick. My titties kept hitting Jose in the face.

"Fuck me, Jose," I said. "Fuck me hard!"

Both hands were gripping my ass. My long, blond hair was starting to stick to my face from all the sweat. I reached between us and rubbed on my own clit. And then I started cumming.

"Oh. Oh yes!" I called out. My cum drizzled down his joystick.

"I'm not done," he insisted.

"Good," was my only response.

I started riding him harder. I leaned forward so his shaft rubbed my clit every time. I could feel another orgasm building quickly. I was in the zone and barely noticed the sound of keys jingling in the door. It swung open and Ram walked in.

"Ah, shit!" Jose shouted. "I told you to stay out."

"I thought you'd be done," Ram protested.

Jose tried to push me aside as he looked frantically for something to cover up with.

"Don't you DARE!" I commanded.

I pushed his shoulder hard back into the couch.

"Don't stop. I'm about to cum," I said.

"But my friend just..."

"Who the fuck cares?" I asked in frustration. "He can leave. Or he can watch. Who cares?"

I started pushing my hips into him. I just wanted him to settle down before I lost my orgasm.

Jose reluctantly put both hands back on my hips. He kept glancing over my shoulder at Ram and seemed less into it, but his cock was still rock hard. I closed my eyes and focused on the sensation of his big snake sliding in and out of me.

Ram was genuinely amused. He probably would have walked away sheepishly if I hadn't said anything. But he apparently felt encouraged by my last statement. I heard him pull up a chair.

"Are you really going to sit there and watch?" I heard Jose demand.

I placed a finger to his lips to shush him.

"Who cares?" I asked again.

"Focus on these."

I rubbed my titties in his face.

"You like these don't you?"

He nodded.

"Suck on them."

He took a nipple in his mouth.

I started riding his cock hard again.

"Damn, bro," I heard Ram say. "She knows what she wants!"

I glanced back over at him. He wasn't as tall or handsome as Jose, but he was built like a brick house with a broad chest and layers of muscle. His shirt was unbuttoned to show off a waxed, sculpted chest. He winked at me while I rode his friend's dick. And then he pulled down his shorts.

He had a dick like a soda can. Short and impossibly fat. And it was swollen hard. He started jerking it.

Jose was totally focused on fucking me again. I turned back and wrapped my arms around his head. His face was smothered in my tits. I rubbed my own clit again and felt the orgasm coming back.

Jose started shuddering. He shoved is cock in with frantic little micro-thrusts. A minute after I started to cum, I felt him unload inside me.

I caught my breath and moved off of Jose. I looked at Ram. He was still slowly stroking his pole.

"Are you going to just jerk it, or do you want to use it?" I asked.

I got up and strolled to the balcony on wobbly knees. I swung my ass like a cheap stripper when I walked.

The sun was down. I rested my elbows on the rail and dangled my tits over. My legs were spread and my ass was up.

Ram fucked like a bull in a china shop. By the time he'd made it through the door he was completely naked. He ran his fingers roughly over my slit. Then he rubbed the head of his cock in my juices until it was nice and wet. And then he started fucking me on the balcony.

I could see shadows of people passing below but couldn't make out faces. I was certain they could probably see the same. Even if they couldn't see us, I knew they could hear me. I tried to bite my lip and stifle my cries, but every few strokes a loud whimper would escape and echo through the large courtyard below.

That fat dick would have been tough for an elephant to take. It stretched my tight pussy to the limit—and then some. At first it was just uncomfortable. There was very little pleasure. But gradually I started getting used to it his girth and his brutish strokes.

Jose had come out to the balcony. Now it was his turn to watch. His cock was semi-erect, like he was getting ready to go again.

"I thought I was gonna fuck you on the balcony, Chellee," he said.

"You can get next, bro," Ram responded.

He reached around and gave one of my titties a rough squeeze. I slid my hand between my legs and massaged my clit while he plowed into me from behind. I knew I was close. I tried biting my lip, but it didn't do any good. I squealed loudly into the night. I could hear it cross the courtyard and echo back off the opposite building. I screamed and whimpered all through the orgasm.

Ram pulled his cock out with a loud pop. I turned around and my knees buckled. I fell in front of him.

"I want you to taste yourself," he said. He wagged his dick in my face.

I opened as wide as I could and got the head between my lips.

"What about on me?" Jose asked. He wagged his beanpole in my face.

I turned to him and took his dick in. He tasted like sweat, cum, and pussy.

I nodded my head.

"I can still taste me," I said.

I started alternating dicks. I tugged them both while I turned my head from left to right to leak each boy's pole.

"Yeah. Suck that dick, mami," Ram said. "I'm ready to blow all over you."

I frantically started tugging them both off. I heard a loud knock on the door to the room.

"What the fuck?" Jose said.

But I didn't stop working their cocks. I wanted both boys to cum at the same time.

The knocking got louder and I heard someone say in Spanish—and then English—that they need to open up.

Even Jose started ignoring it.

Both boys were groaning loudly. Ram was closer. He must have been dying to cum. Jose had already popped twice and needed more finesse. I wrapped my lips around his dick and swirled the head with my tongue. I tugged on both cocks at the base.

It was Ram who blew first. His cum shot off in my general direction. Some hit my tits and arm.

Jose unloaded in my mouth. He was almost drained from the earlier activities, but still had a good deposit to send down my throat.

Both boys were focused on my and I was still holding their cocks. We hadn't noticed that the door was now wide open. Standing there was a nervous looking young man holding a radio and dressed in a security uniform.

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"Fuck them. What are they going to do? You're a paying customer and some adults were having consensual fun in their room. They can't do a thing to you!" Sky said.

Of course she was correct. But I was still nervous about the situation. I didn't regret anything that had happened. Not even being walked in on by security. I wasn't naïve when I went on that balcony. I wanted the risk of people hearing.

Still, I was nervous about the aftermath. The boy who'd walked in had quickly decided that the situation was beyond his pay grade. He told us that we needed to keep it down since we were disturbing the other guests. Then he got the hell out of there quickly.

I'd gotten dressed and gone back to my room. Sky was already asleep, so I didn't wake her. Instead I went to bed feeling sore and satisfied.

Worry didn't set in until the next morning. The front desk called and asked us to be in our room at 9:30. Someone from hotel management was coming up to speak with us.

Sky was already awake, so I told her all about my evening. She listened with a mix of shock, amusement, and titillation. Then she laughed at the end.

"I can just picture it," she said. "The large breasted Amazon woman on hands and knees jerking off two boys who just got out of high school. And Mexican Barney Fife just standing there with his jaw on the ground!"

"I know they can't arrest us or anything," I said. "I'm just worried about them giving us our money back and tossing us out of the hotel."

"They're not going to do that," Sky said. "And, if so, we're in Cancun. There must be 300 hotels between here and Riviera Maya. Someone will give us a room."

I agreed with her. We sat drinking coffee from room service.

"So what do you think the manager is going to be like?" Sky asked. "Old guy with a potbelly? Maybe even American? I think American companies run all these resorts and keep the profits from the locals."

"I don't know," I answered. "I suppose we can always hope for a debonair gentleman type."

"The kind with big muscles who wouldn't mind forgetting things for a BJ from two American women?" Sky asked.

We both laughed.

Sky was planning to go into town for some shopping and had already dressed. I knew that any gentleman would think twice before turning down an offer from her. She was wearing a pink ribbed tank top and trashy looking denim skirt. The straps of her black floral bra were showing.

Sky and I always joke that she has the body of a teenage girl and I have the body of an Amazon woman. I'm all curves and muscle. Sky, on the other hand, is lithe and lean from years of teaching yoga classes before and after work. She'd pass for 25 if not for the silver streaks in her ass-length blond hair.

I hadn't dressed yet and decided to use the last few minutes before our guest arrived to shower. I still smelled like sex and sweat and I knew there was cum on parts of my body.

When I emerged from my bathroom I heard muffled voices in the living area. It was a little before 9:30, but I assumed the manager had arrived.

I stepped out dressed in nothing but pale yellow panties and a white, silky dressing gown covered in a light floral print. I knew the thin satin fabric would hug my tits and do nothing to conceal my nipples in the air-conditioned room. I was hopping Sky's idea to use a little sex appeal would help dissuade management from throwing us out. I strode into the room with the gown still dangling open as I tied the sash—something our visitor didn't fail to notice.

It turned out it was an assistant manager. And I a blow job wasn't going to be an option I realized when I saw Cat staring at me. Her eyes were bulging behind her glasses.

She looked to be in her mid-twenties. She was wearing a tight gray skirt, a white button down blouse, and a blue blazer with a nametag on it. She had thick, dark hair and dark fashionable glasses.

"Excuse me," she said loudly. She wasn't sure how to proceed.

Sky had a little smirk on her face. She was definitely amused by the situation.

"It was me," I said to the young lady.

"I'm already aware of that," Cat responded. "The young men gave us your name and what they knew about you when we threatened to involve the parents who actually own that unit."

"I apologize. Things just got a little out of hand. We didn't break any laws, did we?"

"No. Of course not," Cat said. "And, to be honest, this kind of thing happens frequently here. Of course, it's typically between a couple in their own room. This situation is a little more unusual except during spring break. Even then, it might be the first threesome I've heard about."

Cat's eyes were roaming my body. I didn't know if it was curiosity, disgust, or admiration. Even with the sash tied the gown opened in a deep-V shaped that showed plenty of cleavage. I knew she could probably see the trim on my lacy yellow panties through the thin fabric.

"You're not going to throw us out or anything are you?" Sky asked. "Things just got a little out of hand. We just got into town yesterday."

"No, of course not," Cat responded again. "Obviously, we can't condone the behavior. But you are paying customers and adults. We have a little more leverage to threaten the boys with. But we're not in the habit of tossing out guests unless they've done real damage."

"Thank you," Sky said. She jumped and hugged the assistant manager. I couldn't remember ever seeing her so giddy and affectionate. I noticed she was ogling the girl.

Cat smiled. Her eyes returned to me. Again, I saw them dart up and down my body.

"Hey, maybe you can suggest something fun for us to do tonight," Sky said. "So we stay out of trouble."

"Well, the resort has a couple of shows tonight and several restaurants and bars to choose from," Cat answered automatically.

"Don't give me the sales spiel," Sky said. "What do you do for fun? Better yet, when do you get off? Where can we hang out with you?"

"We're discouraged from socializing with guests," Cat said quickly.

"Come on," I said with a wink. "We want to see where the people who live here go for fun."

"Ok," she said slowly. "I can maybe think of a few options today and get back with you. Let me ask you a question first," she added cautiously. She glanced from me to Sky and back to me again. "I know you're here together. But I'm guessing from last night's activities, you aren't TOGETHER. Do you know what I mean? You're not a couple? Because that could change the list of options."

Sky flashed her a smirk again. She came over and playfully draped an arm around me. Then slid it down my silky gown and cupped my ass.

"We're not together like that," Sky said. "Unless it means the company or scenery will be more interesting. I mean, we HAVE been together like that. And we may be again if things get too boring."

She gave Cat a playful wink.

"I see," Cat said. She made a few more comments, but she was obviously flustered. She asked us again to refrain from being too wild in public and promised to drop a note to us about where we should go and when she'd be there to meet us.

"What a piece of ass!" Sky said in mock-manly voice after Cat had left.

We both giggle.

"Yeah, I saw you ogling her. That's something new!" I said.

"What can I say?" she asked. "You opened up new desires for me."

She came closer to me.

"Plus, I didn't get lucky last night like somebody here! My libido is out of control after hearing about your adventures. Tell me about it again."

She draped her arm over me and caressed my tit.

"I know she couldn't stop looking at you, either. I think she might be into girls."

I blushed.

"I think it was just shock. She probably expected some young silly girl. Or at least someone who was dressed when she came to interrogate us."

"I like you like this," Sky said.

She gave my dressing gown a tug to the side so my left nipple was exposed.

"Or maybe more like this," she said. "Tell me about the boys again."

I started re-telling the story of the previous night. I lingered on every detail. Like the size of Jose's cock. Or how I had controlled the situation.

Sky gently ran her finger around my nipple until it was erect. And then she flicked it with her tongue. Chills shot through my body.

"So, we're doing this again?" I asked.

"I think so. Today's your birthday, right? Let me please you," Sky said. "Keep talking."

"Well, he felt so good inside me."

"Where?" she asked.

"You know where," I said.

She just stared at me.

"Inside me," I said.

Another stare.

"In my pussy."

She pulled the sash on my robe and ran her hand over my flat stomach. Her fingers grazed the yellow nylon of my panties. And then touched my sore cunt.

"You mean right here?" Sky asked playfully.

My whole body was tingling.

"Yes," I whispered.

I leaned in and kissed my best friend. She pushed my robe off and onto the floor.

I pulled her tank top over her head. Her hard little tits were stretching against her black bra. It clasped in the front. I quickly unfastened it and started kissing her curves.

"I got you a birthday present," she said.

"This trip is my present. You being here with me," I protested.

"I'll be right back."

She ran topless to her room. When she came back she was holding a box. She stopped long enough to lift her skirt and slide out of her little black thong. She tossed it on the floor.

I unwrapped the box. Inside was a strapon. It was leather straps with a long, flexible black dildo.

I laughed.

"I have no idea how to use one of these things," I said with a smile.

"Neither do I. But I think we can figure it out."

"OK," I said. "But I'm going to do you."

"I want you to fuck me like those boys did you last night," she said.

"Well let's go to the balcony," I said with a wink.

"Let's just do it right here."

I shed my panties. Sky pushed her denim skirt up until it was bunched around her waist. Her smooth pussy was glistening. I strapped on the toy and sat down on the couch.

"I rode him on the sofa," I said.

Sky mounted me.

Her little tits hung in my face and I kissed each of them. I spread the lips of her cunt and guided the tool inside.

Sky gasped with delight.

"It's so big!" she exclaimed.

She lined her nipples up with my own and we rubbed them together. We kissed like passionate lovers. Then she started riding the big fake dick.

I twisted and kissed her nipples. I bucked my hips up and down like a man. Sky gasped and moaned loudly.

"Yes! Fuck me! Fuck me good!"

I cupped her ass cheeks and placed my index finger in her rim. I pushed a finger in and she exploded. Her cries filled the room as she came.

I was dying to have my pussy touched, but I wasn't finished playing out the game.

"Stand up," I told her.

I guided her behind the couch and told her to bend over. She leaned on it the way I had leaned on the rail the night before.

I found her entrance and plunged the fake cock back into her twat.

My tits bounced wildly as I gave her to toy dick. I tried to fuck like Ram. I gave her a hard, steady pounding. Sky's knees buckled.

"Fuck me. Fuck me. Fuck me good!" she pleaded.

It was easier than I imagined. Once I had the hang of it I fucked her rough while she was bent over the couch. She couldn't stop moaning. She came twice in the span of ten minutes.

"Should I do you now?" she asked.

"I'm still sore," I said.

"Well then maybe you need something more tender."

She helped me unstrap the toy. I sat back down on the couch. Sky got on her knees in front of me. She licked my slit up and down. She teased my clit. She fingered me with slow, steady intensity. It was gentle, but it made me anxious. I begged her to go faster, but she took her time. My orgasm built up for several minutes. I started pushing my hips toward her, but she resisted the urge to go faster. Her tongue kept teasing my clit.

Finally, I exploded. Sky lapped at my juices eagerly.

She stood up, unzipped her skirt and let it fall to the floor. Then she went toward my bedroom.

I quickly joined her between the sheets. Sky was on her back and I was on top. I rubbed my furry mound against her smoothness. We teased one another for 15 minutes. Then I finger-fucked Sky to orgasm and she did the same for me. We ended with a 69. Sky ass on my face and her mouth on my muff. We each got off another couple of times before we finally decided to cuddle and take a nap.

!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

The place Cat recommended turned out to be close by. We were able to walk there and got Mexican food and drinks. She'd ditched her blazer. She just had on the tight skirt and white short-sleeved blouse with puffy sleeves.

The three of us got on well. We learned that Cat had started in sales. The local resorts hired attractive women right out of college to push timeshares and snorkeling and other things to make the resort money. She'd been very good at it and had used that to get a position as an assistant manager by the age of 25.

Technically, she was young enough to be of our daughters. That didn't stop Sky from flirting with her and making it very obvious that she was open to fun. She had put on a tight little white sheath dress with a big black belt.

For her part, Cat didn't seem to dissuade the flirting. And I caught her still looking me over. I was wearing a tight tropical looking skirt with a thin white silk camisole. My tits were practically spilling out of it.

"You keep staring at me," I finally said after several drinks. "Did you just expect someone younger when you heard what happened?"

"Yes," Cat admitted. "But that's not it. Sorry, I don't mean to stare."

"I don't mind," I said.

"You remind me of someone," she said. "You're build. A college professor. We were very close. She had your body. But she was Mexican. So no blond hair."

"So you want me to put on a wig?" I joked.

Cat smiled.

"That would be silly," she said.

"Why?" Sky asked. "Because it would just end up on the floor with the rest of her clothes later?"

Cat was drinking enough to not be put off by Sky's advances.

We had several more drinks and decided to walk back to the hotel. Cat had left her car in the employee lot. We walked by way of the beach. The energy between us was good. I knew Sky was going to make a play for Cat to come to our room, but she seemed to concerned about her career to let that happen.

As we got close to the beach we noticed two guys hanging out on chairs. I recognized Jose's long, lean body and Ram's bulkiness.

We quickly decided it would be fun to play a prank on the boys. Cat was all in for approaching them and suggesting they'd had to contact their parents after all—at my request.

It worked for about five minutes. Ram didn't seem to care, but the place belonged to Jose's parents and he was freaking out. Cat talked about revoking membership. He started to plead with her.

Finally, I broke up the routing.

"She's just messing with you," I said. "I don't have the heart to go on. They're just jealous because they didn't get any of this last night."

I boldly reached down and stroked him through his shorts. Like most younger men, he responded immediately. I could feel him stiffen in my hand.

The three of us sat down with the boys. It was dark and late and nobody was around except one fit looking guy closing up a seaside bar.

I sat in a chair with Jose. He was 18 years old. I had a full 22 years on him. And yet I was cuddling with him like a school girl.

Ram was on a chair alone.

Sky and Cat were on a third chair. And Sky was making her move on Cat. She had her arm draped around her. She whispered things that made Cat blush and smile.

The tension was unbearable. Neither boy knew what to expect or what was happening. I don't think Cat did either. I joked easily with the girls, but the guys had turned into nervous school boys on their first date.

I kept rubbing Jose through his shorts. His dick was rock hard. At first I was discrete about it, but I soon had everyone's attention. They watched quietly. They were absorbed.

"I think I'm going for a swim," Sky finally said.

She stood up and turned her back to Cat.

"Unzip me?" she said with a wink.

Cat pulled the long zipper on the dress. Sky wriggled out of it and dropped it on the chair. Then she shed her white bra. Everyone's eyes were on her gorgeous, firm titties. She started toward the bay in her panties. Then she paused long enough to strip them off and throw them back in Cat's direction.

"I'm going with her," Ram quickly said.

He stood up and quickly shed his shirt. He went toward the water in his shorts. Then, like Sky, he paused and tossed them back. His fat dick was fully erect.

I tugged Jose's shorts down. I stroked his hard prick.

"I should go," Cat suddenly said.

"No," I answered. "You should come here."

Cat tentatively walked toward me. I nodded at the chair and she joined the two of us.

Thirty feet away, Sky and Ram were standing in the waves. Her athletic body was pressed close to him. She looked tiny in comparison. I watched her drop to her knees and start blowing him.

On the chair, I took Cat's hand and guided it over Jose's cocks. The boy gasped and moaned. I kissed him. Then I took Cat's other hand and put it on my tit. And I leaned over to kiss her full, luscious lips.

Cat kissed me hungrily. We each had a hand on a tit and a hand on Jose's cock. He kept moaning and groaning. Otherwise, we may have forgotten he was there.

Jose fondled our tits and kissed us. We kissed him back.

I looked to the waterline and saw Sky's head bobbing up and down Ram's fat shaft. The large man groaned over the roar of the tide. Sky pulled her head away and jerked him furiously. He groaned again and erupted on her titties.

I managed to open two buttons on Cat's blouse. Her bra was thin pink lace. I could see her hard brown nipples.

I kissed the top of her breasts. Then I wrapped my lips around Jose's dick. When I pulled away, Cat replaced them with her own. We took turns serving him while we both jerked him off. Cat had her mouth on him when he finally blew.

Sky was standing by and nodding with approval. She picked up her underwear and dress. Then took Ram's button down shirt and put it on. It covered most of her body.

"Why don't we take this to our room?" she suggested.

Cat started to protest, but her heart wasn't in it. Ram pulled up his shorts. Jose did the same. And we rushed upstairs.

As soon as we were in the room Sky shed all her clothes again. She went right to Jose and pressed her naked body to him. He was already getting hard.

Ram came over to me.

"I want to fuck you again," he said.

"Undress," I commanded.

He stripped off his shorts. Cat gasped at the sight of his thick piece.

"Now you know why I was so noisy," I said with a wink.

Cat was obviously still looking at me, but Sky had other plans. She pulled the woman to the couch and pushed her into a seated position. She dropped on her knees in front of her.

"Are you going to fuck me, or what?" she said to Jose.

He stripped down. Another gasp from Cat at the sight of Jose's long dick.

He started fucking Sky on the floor. At the same time, she rested her hand on Cat's knees.

"Pull your skirt up, honey," she whispered.

Cat obeyed.

She pulled the tight skirt up to reveal her little pink panties. Sky ran started licking her pussy through the thin fabric.

Jose was watching the action while he slowly fucked Sky from behind.

"Unbutton your blouse," he told Cat. "I want to see your tits."

She opened the remaining buttons on her blouse and pulled the cups of her blouse down. She had deceptively large tits with dark brown nipples.

Sky fingered and kissed Cat's pussy while Jose fucked her.

Ram was sitting in a chair opposite them and I sat down my back to him. His thick dick felt like it was ripping my tender pussy apart, but I loved every minute of being stretched out by him.

My skirt was bunched around my waist and my panties were pushed to the side. I pulled off my camisole and bra. Cat openly lusted after my big tits. She watched them bounce up and down as I rode Ram's dick. And I watched her get fingered and eaten by my best friend—who was taking Jose's dick at the same time.

I cupped my breast and jiggle them with a smile. Ram reached around me and rubbed my clit while I rode him.

I was the first one to cum. It was impossible to hold out with Ram's fat cock inside me.

Cat seemed to get off just from watching. As Sky pounded her pussy, she made a whining sound and then climaxed.

Jose started giving it to Sky rough.

"Oh yes," she moaned. "Fuck me like that! Fuck me like a whore!"

Jose went faster. He slapped her perfect little ass. I recognized the sound of Sky cumming. And Jose didn't last much longer. He popped inside her pussy. His jizz ran down her thighs when he pulled out.

Cat got up from the couch. She was walking with confidence.

"I want you now," she said to me.

She took my hand and started pulling me to my bedroom.

We collapsed in bed and started kissing like old lovers. I fumbled getting her clothes off.

Cat took charge and worked her way up and down my body. We rubbed our curves together. Then we rubbed our furry mounds. Finally, she started kissing her way down. She lingered on my big tits. She sucked and teased my nipples. And then she moved down my abdomen until she found my waiting muff.

As she ran her tongue around it, Sky appeared in the doorway with both boys. Ram was still hard. Jose was recovering. And Sky was wearing the strap on.

She approached and rubbed Cat's ass while Cat ate me out. Sky put the fake dick inside Cat's pussy.

Cat groaned a wiggled.

"Your turn, Big Boy," Sky said to Ram.

There was a cutout in the leather strap that left her bare pussy exposed. While she fucked Cat doggie style, Ram moved in and crammed his monster cock in my best friend.

He fucked her hard. Sky seemed pushed beyond the limit by his big dick. Each of his thrusts went into Sky so forcefully that it also crammed the strapon up inside Cat, who cried out and moaned like she was being ripped in half.

She kept fingering and licking my hot cunt.

Jose laid down beside me and kissed my tits and played with my nipples. I came hard from all the action, but nobody slowed down.

Cat's head collapsed into my snatch as she started to cum from the strap on. Sky came once and then a quick second time. And Ram kept driving into her pussy relentlessly.

Finally he pulled out and gave his tool a few good tugs. His hot jizz splashed on Sky's ass cheeks.

We all repositioned. Sky took off the strap and I quickly took it from her.

"I'm going to fuck you now," I told Cat.

I put on the tool as she rolled to her back. I mounted her and started fucking her missionary style.

Ram got behind me and started snacking on my cunt while I fucked beautiful Cat.

Now it was Sky's turn to watch the show. Jose pulled up a chair and she mounted him reverse-cowgirl style. She cupped and teased her own tits while she rode Jose's big pole.

It was impossible to count the orgasms. I came from Ram's tongue. Sky came on Jose's pole. Cat came on my big strapon.

We switched around again. Cat put on the strap and fucked me doggie style while I licked the taste of Sky's pussy off Jose's cock.

Sky planted her pussy on Jose's face while I went down on him. Ram drove his big cock into Cat from behind.

Again, the force of Ram fucking a woman wearing a strap was enough to drive Cat's tool deep inside me. Cat feasted on my titties. She was almost along for the ride in between me and Ram.

I had back to back orgasms. Sky came on Jose's face. And Cat kept whimpering and cumming from Ram's pussywrecker up inside her.

"You know, it's Chellee's birthday, boys," Sky said. "Why don't you finish her off with something special."

We repositioned once again. I was on all fours on the bed. Jose's baseball bat dick was up inside my pussy. And I was tugging and sucking on Ram's fat dong.

I thought the two boys would rip me right open. Ram fucked my face just as hard as Jose crammed it in my cunt. Cat fucked Sky right next to us with the strap on.

"Oh please. Please fuck me harder," Sky almost cried.

I started cumming from Jose inside me. Seconds later, he did the same.

Ram pulled out and I jerked his cock for him. I aimed it to the girls next to me. His gargantuan load splashed all over Cat and dribbled down onto Sky. Cat ignored it and kept making Sky cum.

We were loud, but nobody interrupted us that night. At one point, Cat abruptly ushered the boys out the door. She still had leverage on them, so they weren't going to argue.

The three of us took turns rubbing each other's tits and going down on one another. Sky eventually needed to get some sleep, but I was insatiable. And so was Cat.

We cast the toy aside and finger-banged each other until almost sunup. She eventually decided to slip out so she wouldn't be noticed by her employer in the morning.

I went and climbed into Sky's bed and entwined my naked body with hers. The next morning we made love to one another in the bed and again in the shower. And then we got dressed to catch a plane home.

At that point it seemed pretty obvious that my birthday weekend had been great. It was also obvious that neither of us were ready to quit experimenting with our new found sexual freedom.