My Playmate Ch. 04

I suppose I should have felt guilty. After all, I was cuddling up to my girlfriend after making out with her ex-roommate. But all I could feel was the joy of blooming puppy-love with the woman of my dreams.

When Saturday morning came, I couldn't resist several sidelong glances at Courtney as we went about breakfast and prepared to go out. It would be a day of sightseeing around Hollywood and Santa Monica. We'd shop down the promenade and sun ourselves on the beach, then rest up before the crown event of our trip to California.

Courtney had specifically chosen this weekend because it was the Midsummer Night's Dream Party at the Playboy Mansion. We were all attending and it promised to be a bash that would far exceed anything Anna or I had ever seen.

But first, the shopping and sunning trip. We hit the shops before lunchtime. I couldn't believe how outrageous some of the prices were for the smallest scraps of clothing. Designer this and major label that for $300.00 screamed rip-off to me. But that didn't stop the girls from picking up several items.

Anna was relatively cost-conscious, but Hailey and Courtney kept fawning over her and eventually persuaded her to buy a designer set of sunglasses. I did have to admit, Anna looked rather glamorous in them. The whole time, Brian and I dutifully carried the bags.

After dumping our inventory back into the car, we headed off to find some surf. All three girls stripped down to bikini tops and shorts, and I had to struggle to keep my eyes focused in front of me as we walked back to the beach.

Even amongst a bevy of similarly clad young females, Hailey and Courtney were turning heads left and right. They soaked it in as if it were an everyday occurrence (which it probably was) and continued to stroll along, not even noticing the catcalls.

Even Anna had more than few guys whistling at her and her tight ass, but she blushed fiercely and gripped onto my hand even tighter.

The beach itself was magnificent. Warm, fine sand, absent of rocks or other detritus. Decent waves for bodyboarding if not full-blown surfing. And tanned, toned young flesh as far as the eye could see. I could not imagine having access to this every single day of the year.

The girls quickly lotioned up and then settled down to tan. Hailey wasn't too careful about covering herself before dropping her bikini top and then settling onto her stomach to sun her back, and I caught another long glimpse of her turgid nipples.

Brian pulled out a frisbee to toss around with me while we shouted guy things at each other. And after fifteen minutes of "sunning", Anna got bored and joined us. Casual tossing turned into competitive hurling, as things usually do around me. Then Brian and I ended up foot racing back and forth for a bit. He beat me most of the time, dammit. I wasn't used to running in sand.

We were drinking vast quantities of liquids to stay hydrated in the heat, which eventually meant that I had to go to the bathroom. I excused myself and headed off. But after hiking twenty feet away, I heard a "wait up" and turned to see Courtney bounding along the sand to join me.

My jaw quivered watching her breasts jiggling up and down with the running motion, and in that moment I fully understood how a crap-ass show like Baywatch could conquer the world.

When she caught up to me, she fixed me with a quirky smile. "I want to fuck you right now..." she breathed.

I shook my head and turn my head lest Anna see the gaping expression on my face. **I am getting in WAY over my head... again.** "Aren't you worried at all about this? About Anna?"

"I'm guessing not as much as you are," Courtney stated matter-of-factly. "I've missed you. You were the only guy who could ever keep up with me and the only guy who ever made me feel like more than a great body. I've already been away from you for 3 years. And now that I know what I want I'm not going to let anything stop me. Don't you want me too?"

"More than anything in the world," I stated, and it was absolutely true. "I just don't know how to break it to Anna."

"Don't take too long..." Courtney pleaded.

We walked side-by-side the rest of the way to the public restrooms, staying a good couple of feet away from each other in case anyone was watching. But that distance closed quickly the moment we were out of sight.

Courtney turned around once we reached the building to make sure none of our friends had followed us, and then ducking behind a conveniently located brick wall, she pulled me to her so our lips could meld into one.

I felt hours of tension flooding out of my body as we kissed, both moaning into the embrace. Here were the kisses I longed for. Our trademark fully passionate kisses. And it didn't matter how many people were around us, I wasn't going to be the first one to break our liplock.

After a few minutes, we finally parted to breathe. To their credit, no one paid us any extra attention. I guessed public displays of affection were rather more common here.

"I only wish I had time to blow you," Courtney giggled. I smiled and gave her one more peck, and then we split apart into our respective bathrooms.

After returning to the party, our fivesome lazed around for the rest of the afternoon, drinking iced teas and snacking on sandwiches while resting underneath the large umbrellas we'd brought. We also spent a good amount of time rotating massages for each other, and my hormones delighted in the opportunity to get my hands on all three beautiful women.

All in all, it should have been one of the most relaxing vacation days of my life. But all my muscles were tense from trying to look ANYWHERE but at Courtney for long continuous hours. The taste of her lips was still in my mouth, and I was dying inside with desire to kiss her once again. I knew that if I looked at her for even a few seconds, my expression would betray my disloyal thoughts to Anna. Even when it was my turn to give Courtney a massage, I had to be extra careful to appear chaste.

I was so tense; Hailey even gave up trying to work the knots out of my shoulders, handing me off to Anna. "I can't figure out how to make him relax," she muttered. Anna just smiled and then set in to our usual massaging routine.

In a way, apart from my internal tension, the atmosphere felt like our old comfortable group of five from college. Just trade in Hailey in place of Christine. Sure, they were different people, but the conversational rhythms were still our same old dynamic. However, Christine's absence was a constant reminder that these were different times, and we were all different people in a way. On top of that, I was hooked up with Anna now, not Courtney any longer. The nostalgic familiarity was tempered by the cold reality of change. And my brain was getting very tired trying to keep my memories in check.

I finally was able to give my brain some relief when we returned back to the girls' house to change and get ready for the party, a great weight lifting off of me as Courtney walked into her bedroom and out of my sight.

I sighed and then looked back to where Anna was disappearing into our guest room.

**I have to tell her, and soon. Before I go insane.**

***

We all emerged more than an hour later, the girls dressed to give men heart attacks, even Anna. Courtney and Hailey were clad only in what amounted to lingerie, revealing wide expanses of their full breasts and tight asscheeks.

Anna was about what you'd expect from a librarian gone Playboy slutty. Her dark hair was pulled tight into a single thick braid running down the middle of her back. But her makeup and black-rimmed glasses edged closer to trendy than bookish. And the long-sleeve sweater was raggedly cut halfway-down, leaving her slender belly and hips naked before the tiniest micro-miniskirt did its best to conceal her crotch while still skintight against Anna's wonderful bottom. Schoolgirl clogs and knee-high socks completed the ensemble and I had to admit that Anna was more enticing in a way than even Courtney or Hailey.

A Playboy limo came to pick us up, perks of being official Playmates, and soon we were sipping champagne while bursting with excited energy.

"We are gonna have FUN tonight!" Hailey crowed out the window at a passing car.

Courtney bounced in her seat and remarked, "We'd better. I haven't gotten off in two days!"

Hailey turned. "Oh, sweetie. I'll make sure of it. Personally." And then Hailey had leaned in and the two hot Playmates were swapping spit and moaning into each others mouths.

Brian grinned and Anna closed my jaw for me. But then very quickly we arrived at the Mansion.

I looked around in awe at the manicured hedges as we drove up to the estate. After circling the fountain the limo stopped, and we all stepped out. It was still late afternoon, and the party wouldn't be beginning for another two hours at least. But Courtney and Hailey had invited us to see something special. The limo then turned away to make its next pickup while we strutted up to THE Playboy Mansion.

Off to the side, I could see that the usual massive tent had been erected over the gardens and catering staff were running helter-skelter every which way to prepare. But Courtney and Hailey took us off in a different direction.

We wound our way through the Mansion grounds and soon came upon something I'd only ever dreamed of stepping into: The Playboy Mansion Grotto.

Right now, instead of a hundred naked girls waiting for us, there were a few fully clothed staffers and a photographer inside. The Grotto had been converted into a temporary photography studio. There was a football stadium worth of lights and wires and cables running around. But what immediately had my attention was the naked brunette currently posed in what must have been a really awkward position. But while it may have been awkward for her, I had to admit the view was stunning.

We tried not to intrude, but the nude model saw our entrance and then she flashed Courtney and Hailey a little smile and a wave. The photographer gave us a slightly annoyed sigh and then turned back to his camera as the brunette went straight back into her pose.

Two other girls, both blonde and both completely naked, came into the shoot, I could see where they'd just dropped off their own Midsummer Night's Dream attire to the side. Perhaps the party and these girls would be a pictorial in the next magazine. And so the blondes entered into the water where the brunette sat with her feet over the edge, and all three posed together for a series of additional shots.

Somewhere in the back of my head, I'd thought a photography shoot would fly by really quickly. The girls pose, you take 2 or 3 shots, and then move on. But this shoot was a lot more involved than that. It would take several attempts before the models were posed just how the photographer wanted, and once they was in place he would fire off what sounded like a hundred shots.

IF they were lucky, ONE of those hundred would be selected. A big "if". And for a magazine to wind up with, say, 12 good shots, there had to be dozens more poses that didn't make the mag.

And in the meantime, there were three different staffers running around setting up things and adjusting lighting and prepping cameras, etc. There was a lot of behind-the-scenes work.

And so we were watching for 30-minutes before they took a break.

So in that time, I found I was learning a lot more details about how much work went into a Playboy spread than I'd ever imagined before. The Playboy Mansion Grotto wasn't so much a mysterious, legendary oasis. It was a big jacuzzi that made for a nice backdrop. And after a while, I found I didn't even notice the models were naked any longer.

But a break finally came. "Let's come back in ten. I'll let the girls chat up and relax for a bit."

The models got up and dried off with towels, and so we had an opportunity to get introduced. Courtney and Hailey quickly bounded up, hugging their fellow Playmate in greetings, completely oblivious to their nudity. Then the rest of us were introduced.

"Everyone, this is Monica. She's been a Playmate for a little over a year, right? Monica, this is everyone!"

Monica shook my hand in a friendly grip, and up close it was almost impossible not to gawk at her nudity. But I don't think she minded too much. Then we got introduced to the two blondes, Tammy and Tawny, and there were handshakes and hugs and little air kisses to the side all around.

But what really got fun is when Anna pulled out a compact digital camera of her own. "Mind if I snap a couple of shots?"

Hailey lit up like a firecracker! "Ooh! Candids!"

She nearly tackled Monica and then turned and beckoned Courtney to join them. The blondes snuggled in together as well so Anna just started clicking away at the five hot babes.

At first, Hailey and Courtney stayed fully clothed in their skimpy lingerie, sandwiching the naked models between and around them. But then Monica snapped Hailey's bra, and that came off. So Hailey snapped off Courtney's bra. And after five minutes of play-wrestling, with Anna firing of photos constantly, all five girls were naked in a matter of minutes.

However, by the time Hailey shoved one of the Tammy's breasts (or was it Tawny's?) into her mouth, it was time to get back to work. A makeup artist came back to touch up the girls' bodies to get ready for round 2 of their photo shoot.

So Courtney and Hailey gathered their clothes up again and moved over to a hidden dressing room to find a mirror to primp and fix themselves back up for the party.

Brian and I just hovered over Anna's camera to scroll back through all the soft- core photos.

But then all too soon, it was time to party

***

Music was pumping, lights were flashing, and the Playboy Mansion grounds were decorated to the nines. Cocktails were being passed around and hors d'oeuvres were readily available. But most importantly, there were more beautiful women around than I had ever before seen collected in one place.

The Midsummer Night's Dream party was everything I had fantasized about and more.

We soon got our drinks and I was doing my best to appear the calm, confident male amidst a sea of chaos. I tried not to be obvious ogling the painted ladies, women completely nude except for semi-modest body paint. Other women were technically clothed, but they weren't very careful about making sure their outfits stayed properly in place.

We danced constantly, my ego forcing my steps into rhythm even if the alcohol did its best to make me look like a moron. Pool, bowling, even dancing; there's nothing I can't do.

We socialized with all the semi-celebrities who came, including several well known Hollywood actors. I had to pull Anna away from Charlie Sheen. After an hour, we even met Hef and his girlfriends for a few brief seconds before they were whisked away to some other more important people.

We had our own dime tour of the grounds, tactfully ignoring the people clearly having sex in the grotto or others making out in other dimly lit corners.

One drink turned into two and then four. The music's bass beat began reverberating in my ears and I was sweating from all the dancing we had done as a group. With thickness in my brain I was rather less careful of myself ogling other ladies, Courtney included. At the moment, she and Hailey had Brian sandwiched between them while I did my best to not obviously grope at Anna's ass.

And then the four drinks had caught up to me. "Man," I muttered. "I gotta take a piss."

"Not with this you can't," Anna moaned into my ear. Her hand was on my crotch, gripping my erection. Per usual, she didn't drink much alcohol, but she could still get as horny as anyone else.

Sigh... "Down boy," I muttered to my dick. We started pulling away from the party.

On the directions of an attendant, Anna and I found the main bathrooms only to find something of a line. Even the men's room had a line. But we were rescued by someone who knew the layout.

Courtney had figured out where we were headed and she'd followed us, and then with a matronly tsking she directed us deeper into the mansion. The security staff recognized her as a Playmate and we found another unused bathroom on the second floor.

Without another word Anna followed me inside where we found we had a view overlooking the party. Just below the window there was a group of five women all grinding against each other. I felt a new twinge in my cock at this sight and sighed again. I'd never be able to pee.

Again without speaking, Anna sensed what was going on and slipped her hand inside of my pants. The two of us continued to look out over the crowd, watching the hedonistic revelry while Anna's tight grip began pumping along my length.

I groaned while feeling the pleasurable effects of Anna's handjob, and she pointed further out across the grounds and calling my attention to a new sight. One woman was bent over at the waist, still wearing her underwear but clearly being fucked by a man pressed up tightly against her backside. The woman was also leaning forward, tugging bra cups away from a girl in front of her while she bathed the second woman's nipples with her tongue.

Anna's thumb swirled the pre-cum leaking out my tip along the head of my cock, and once she figured out the rhythm of the threesome coupling before us, her hand pumps began to take on the same steady beat.

Together we rocked, half hidden behind this upstairs window, in sync with the fucking before our eyes. And as I began to get closer, my hips started twitching. Anna simply turned and knelt before me, opening up my pants and dropping them to my ankles. She flashed a smile at me, so daintily pretty behind her glasses before she leaned in and took my hard erection into her mouth.

The pleasure was almost more than I could stand, Anna's tongue scraping the underside of my rod as her head bobbed back and forth. I wanted to cum so badly, but something was holding me back. A panic overcame me, what if I couldn't cum? What if she thought it was my desire for Courtney preventing me from cumming into Anna's mouth?

But just as that panic overcame me and I felt the first twitches of losing rigidity in my cock, the threesome I had been spying on sped up on their final approach towards orgasm. My hips sped up as the man's did, and just when he flung his body flush against the woman's asscheeks and his mouth gaped open in a grunt I couldn't hear, I too thrust myself deeply down Anna's throat and let my semen spew forth.

It wasn't that much, but it was quite a relief. Anna swallowed every drop I gave her and then finally stood when my cock had clearly gone soft. The urge to pee was now greater than ever before. Anna smirked and patted my spent member. "Do your thing. I'll be right outside."

***

After relieving myself, I emerged to find Anna waiting patiently for me. We were about to return to the party when Courtney came back down the hall. "Ah, so you ARE still here! That must have been a really long urination," she giggled, but winked as if she knew what we'd really been up to. "Come with me."

And so we followed Courtney down the hallway and away from the party. We finally came to what appeared to be a guest bedroom, and without further ado Courtney pushed us inside.

Hailey was already completely naked, her perfectly formed tits pointed to the ceiling while she lay flat across one of the two queen-sized beds. Brian was likewise fully undressed, his face buried in Hailey's crotch while he happily munched on her pussy, shaven back except for a thin stripe to prove that the carpet matched the drapes.

"Come on, join the party!" Courtney laughed and then started stripping herself. I wasn't sure how to react, and just stood there dumbly watching Courtney's body slowly become naked before my eyes. I hadn't seen this in person in so many years.