tagGroup SexMy Playmate Ch. 04

My Playmate Ch. 04


PART 4: California


I looked out the window, observing white wispy clouds glide past my view of the brilliantly blue ocean beneath. And then the coastline came back into sight. We were almost there.

Months after graduation. Months of enduring the mental torture inside my own conscience. Months of dreaming about Courtney's face. And now we were almost there.

I glanced to the side to see Anna's face light up happily as she also saw the California coast, more clearly than I from her window seat. She turned and flashed me with a pearly white smile. "We're almost there." The tone in her voice was quite different from the tone in my head. I could feel her giddy anticipation.

"Almost..." I couldn't quite muster up the same enthusiasm. Sure I wanted to see my old friends. We had one weekend. Just three days and two nights to visit and catch up. I only had to keep my composure for that long, IF I could keep my composure for that long.

I felt the cloud of doom hanging over my head. What had happened graduation night was still fresh in my mind and stubbornly refusing to be forgotten.

**It's simple, just look at Courtney like you have any other day since you broke up. You can do it...** At least I told myself I could do it. **Forget what she looked like when you were making love. Forget that face and remember Anna's...** Easier said than done.

**Aww fuck... I'm going to fuck this up...**

Courtney had left right after the graduation ceremony itself. She'd never actually come to my room. It had all been in my head. I'd woken up the next morning to realize I still had several boxes to pack. The entire thing had been a dream (nightmare?) mingled with the reality of having sex. And that woman I had been REALLY making love to was sitting right next to me, content in the belief that all the passion I'd let out was meant for her and her alone. How could I have done that to Anna? And what was going to happen when I actually saw Courtney for the first time since that day?

A short half an hour later, we were in baggage claim waiting for our luggage when a familiar giggle lit off behind me. "You're here!!!"

I turned and there she was, more radiant than ever. Her eyes danced, her skin glowed, her hair was perfectly coiffed, and she was just as sexy as ever. It was HER. Just a slightly different HER than I remembered.

Gone were the casual jeans and no-nonsense baseball cap. In disguising herself from the general public, Courtney had dressed down for her visit back to school, showing us the old girlfriend we knew and loved. But now, now we were in LA. Now we were in Courtney's element. And she was glammed up to the max.

The outfit was rather risqué, a little Playboy bunny logo in the corner of her hoodie. She would never have gotten away with the microshorts that now almost exposed her asscheeks to the world. Her makeup was heavier than she ever used to wear to an Economics class. All this made her seem perfectly at home as a Playmate; a goddess stepped down to mingle with us mortals.

Of course, in my glancing around, I found that a dozen other hot women were similarly dressed. They weren't playmates. They were just ordinary Southern California girls. I was going to have to watch my own eyeballs to keep from ogling too much. Ah, California.

Anna stepped forward and the two ladies hugged warmly, the way old roommates do. And then Courtney turned to me, hesitating before taking a step in my direction. There was a desperate longing in her eyes as she stared me down, or at least I wanted to believe there was. A gleam of hope mirrored by a sense of loss. Without words, her eyes communicated so much to me.

We both stopped ourselves and I even glanced at Anna first before finally stepping in and giving each other a chaste hug. Awkward, but I detected no suspicion from my girlfriend.

"It's too bad Christine couldn't come," Courtney stated glumly. For a brief second I appreciated the change in subject. But at the same time, I wasn't sure how to respond. Christine and I still had a weird bit of unfinished business as well. On two more occasions since graduation, Christine and I had given into our lust and fucked each other senseless. It was an unfinished affair and yet one more thing in my head I had to hide from my girlfriend.

Fortunately, just then I saw Anna's bag come trundling off the conveyor and used it as my excuse to look away and lean over to grab at the suitcase.

I heard Anna sigh, "Yeah, well. You know how things are between her and Brian. Not all relationships can end as amicably as you two."

Courtney seemed suitably sad. Not all relationships end up with the parties wanting to get back together, either; but I wasn't about to say that out loud.

The moment passed and then Courtney was perky once again. "Well, I'll have to go to visit her. In the meantime, you're not here to get depressed. You're here to have fun! I hope you packed enough bikinis!"


Courtney drove us in a cute little Mercedes. Nothing too fancy, it wasn't like she was loaded or anything. But she was able to buy our plane tickets for us and she apparently wasn't in any debt, which was more than I could say for us poor recent college grads (well for Anna, a current grad student).

After a half-hour, we were winding through the posh hills above Hollywood. It was a strange dichotomy of ancient streets, hard cement cracked from years of abuse and built in the 1920's before anyone anticipated how many cars would be traveling over them. But just above the street level, gorgeous homes and lush greenery were all that the eye could see.

The car pulled into a little garage, sliding into the one spot next to a shiny red BMW convertible. Going in I could see a quaint house, bigger than anything I could dream of owning and yet not as grand as the mansions nearby.

We unloaded and then headed inside. "Hailey?" Courtney called out. "Brian?"

"We're in here," a female voice answered.

I followed the two girls into the house, carrying most of the luggage of course. The interior decorating was modern and elegant, but not overly garish or anything. Still, it was definitely a few steps up from IKEA.

I gaped at the granite countertops and maple cabinetry as we passed through the kitchen from the garage and into the living room. My old buddy was on the couch, a beer in one hand while he chatted up a gorgeous redhead who was clad only in a silk bathrobe. I didn't recognize her, but I knew I'd seen her somewhere before.

Brian came up and we exchanged our usual manly greetings. Courtney and the redhead embraced each other and then everyone rotated.

"Brian, you know. He practically lives here now." Brian shrugged at the comment and Courtney flashed another impish smile. "Now Hailey here you should remember, she was the magazine's Playmate of the Month in January."

I looked, then looked a little closer and suddenly her Centerfold spread popped into my mind. Pretty face, fake tits that were nevertheless absolutely fabulous, and a bubble-bath theme that had set my heartbeat racing.

I held out my hand to shake, but Hailey just laughed off my platonic greeting and instead stepped right up to me and dropped a quick peck onto my lips. "Hello," she husked at me in a low voice.

**Did she just kiss me? Did Anna just see her kiss me?** I was already starting to panic, my composure brittle after spending this little bit of time around Courtney.

I must have turned beet red because Brian was actually pointing at my face as he laughed at my expression. And then my competitive nature kicked back in. I was slightly annoyed at myself. Years ago I would have just taken the kiss in stride and done my best to flirt. But here I was trapped by my own inner turmoil regarding how both Courtney and Anna would react to seeing me flirting with another girl. However, both Courtney and Anna were similarly amused, at least until Hailey turned and planted an identical kiss hello onto Anna's lips as well.

Anna and I made quite the pair at that point as we both turned shades of red. Everyone had a good laugh and then we all settled into the living room to catch up.

The hours passed as beer turned into cocktails, and light buzzes turned into fully- fledged drunken stupors. We blitzed through the usual "what have you been up to lately" conversation in the first twenty minutes. The rest of it were flirty comments and sexual innuendos. Brian would boast about the things he'd seen going on at the Playboy mansion while the girls were slightly more demure about things.

"It may seem to be a non-stop hedonistic sex palace, but Playboy is really about the tease," Hailey explained. "We show more skin, a little softcore nudity. But we're not having sex out in the open or doing porn. It's more elegant, a little more discreet. The fun is all in the chase and the imagination." And in the middle of her mini-speech, Hailey slid aside her robe to reveal her deep cleavage. And in the last moment, for just a brief second, a nipple came into view and then was quickly removed from sight just as quickly as it had arrived.

I exhaled, not realizing I'd been holding my breath.

Courtney sat up. "You ARE a tease!" she complained. And then she moved forward across the couch and before Hailey could react, Courtney had flung open part of the robe and held out Hailey's naked tit for everyone to see.

"Hey!" Hailey exclaimed, sounding more surprised than angry, and after a brief struggle managed to stuff her breast back inside the robe. "Oh, you're going to get it for that." Hailey lunged over and tackled Courtney, leaving the two girls in a wrestling gigglefest that set my blood on fire to watch.

Anna turned out to be the voice of reason as neither Brian nor I was about to stop what was going on. She waded in and separated the two roommates who were giggling and laughing uncontrollably.

Once everyone had settled back down, it felt like the last bit of energy had been expended. Weariness and jet lag began to set in, and the first yawns announced to Courtney that she should get us to the guest room.

We'd been given the dime tour earlier, and I knew there were exactly three bedrooms in this house. One for Courtney, one for Hailey, and the third for Anna and me. Glancing over at Hailey stroking Brian's head as they cuddled on the couch, I didn't bother to ask where Brian would be spending the night.

I briefly wondered how Christine would react to the news. She had chosen not to come with us on this visit. No matter how much she wanted to see Courtney again, she couldn't bear to get within 100 miles of Brian. Brian, for his part, seemed to be moving on just fine.


After cleaning ourselves up and preparing for bed, Anna slid over to me underneath the sheets, molding her body around mine. She leaned in and kissed my cheek while running her hand around on my bare chest. The evenings were rather warmer here and I was clad only in my boxer shorts.

"You tired?" she asked me.

"Kind of. But I'm wide awake," I told her honestly. I hadn't been sleeping well for months now.

"Mmm, I know how to exhaust you..." her hand drifted lower until she was gently rubbing at my crotch.


"C'mon. It's been over a week since you last made love to me."

"Yeah, but here?"

"Why not? We'll be quiet. It's kind of naughty. And I know you like being naughty." With that, Anna slid herself all the way beneath the covers until her head was positioned just over my hips.

I sighed as she tugged my boxers down to my ankles. If only she knew how naughty I'd really been. And then I gasped as she took my half-hard cock into her mouth.

She blew me just long enough to get my rod hard enough and get herself turned on enough to start the waterworks. And once we were both ready, Anna slid back up and rested on her back next to me.

I rolled over her receptive body while Anna pulled up her nightshirt and stripped down her panties. Once I'd kicked off my boxers, we were both fully naked. I took in the beautiful sight of Anna's tight body, firm breasts still perkily upright and nipples hard with her arousal. Her pretty face shone in the moonlight while her dark hair splayed out across the pillow.

I blinked, and as I my eyelids descended, Courtney's gorgeous visage seemed to layer over Anna's features. And in guilt, I quickly opened my eyes. My cock on the other hand, twitched in eagerness at the notion.

And like so many other times over the past few months, I just surrendered. I closed my eyes, leaning down to kiss my love while my hips moved forward and my shaft sank down into "her" warm, wet pussy.

I turned my head to nibble at her neck. I pulled almost all the way out and ducked my head until I could rub my lips against her nipples. And after only a few more minutes, I thrust all the way in and unloaded jets of cum into her accepting womb.

I only wish I were sure which "her" I was with.


I could only have been asleep for a couple of hours. My eyes fluttered open and I fought down the momentary panic of an unfamiliar room. Anna slept quietly next to me, her angelic face so peaceful, so unaware of the turmoil in my head.

It was as if Courtney's image was painted on the insides of my eyelids. Every time I blinked she was in my mind. And sleep was a torture I could barely stand.

Slipping out of the bed as quietly as I could, I padded outside and into the hallway without significant noise, feeling my way in the pale moonlight.

I was passing Hailey's room when I heard a distinctly male grunt, followed by light feminine giggling. I rolled my eyes and kept moving.

The kitchen was lightly illuminated and I moved in, finding the wall switch and then squinting harshly against the unexpected brilliance of the kitchen lights. After a moment of getting my bearings I found the cabinet for glasses and got myself some water. I downed the first glass and then poured myself a second.

After slowly draining that, I managed to take a deep breath and sigh.

"You couldn't sleep either, huh?"

The voice startled me, and I turned to see Courtney coming into the kitchen as well, apparently wearing an oversized T-shirt and nothing else. She had her casual smile on, the impish upcurving of her mouth that I'd gotten so used to. It wasn't a radiantly toothy smile. Just an amused little tug of her facial muscles that only I or very few other people would immediately recognize.

"No, not really," I answered noncommittally.

Nothing else was said as Courtney moved in, poured herself some milk and then put it in the microwave to heat. I simply stood there waiting and watching her. I missed that simple pleasure of watching her. And somehow, no matter how many times I'd seen Anna doing the same sort of thing, it just wasn't the same. My heart was still bound to my first love.

It didn't matter that Courtney had broken up with me back during our sophomore year. It didn't matter that despite my most heartfelt professions of love, she'd never returned the sentiment. It didn't matter that when I'd pressed her, she'd told me she wasn't ready for a commitment. And it didn't matter now that she lived thousands of miles away from me. I knew right then that I would move to California if she would have me.

The microwave pinged and then Courtney was gliding out of the kitchen and over to the couches in the living room. I followed automatically, and the next thing I knew we were sitting side by side on the cushions and facing each other, only a few inches separating our knees.

"So, really, how have you been?" she asked sweetly. Her sky blue eyes glinted in the moonlight and her skin was a radiant ivory. She had no idea the emotional hurricane I was about to unleash upon her.

Seeing her face like this, in a dark room with no lights but the evening glow, reminded me of the vision still seared into my brain. The hopeless fantasy I still could not let go of.

**What am I doing?**

"I love you." The words half-choked in my throat. And then I jerked in place, barely believing I just sputtered it out. For years, I'd made that a really bad habit with Courtney.

"Excuse me?" Her eyes were wide with surprise, and she quickly set down the warm milk onto the coffee table.

My mind was racing. Did I really just blurt that out? It had been months since the Graduation vision, months of not being able to get Courtney out of my brain for more than a few hours at a time. The months of stress and pressure on my heart finally snapped something inside of me.

Before I knew it, I had leaned forward across the couch, holding Courtney's head in my hands as I lunged into her body and captured her lips with my own.

Courtney whimpered in my grasp, but her lips parted and her tongue willingly accepted mine. And then I was pressing her back into the cushions as we attacked each other with years of built-up tension flowing out of our bodies in a steady wave of energy and lust. Her leg came up and wrapped around my lower back, clutching me to her as if she would never let me go.

It was one of our trademark fully passionate kisses. A kiss I had sorely missed. The kind of kiss that no matter how much Anna and I tried, we could never reach this level of energy and sheer joy.

It was perhaps the greatest 30-seconds of my life. I only wish it had been forever.

But the sound of a door opening split the silent night like a gunshot. All of a sudden the illicit naughtiness of what we were doing descended into both our brains.

We split apart instantly, Courtney moving upright and me moving back two feet across the couch as fast as I could. If anyone were watching, there would be no way we could claim we were "doing nothing."

But fortunately, no one was around... yet.

In the dimness of the moonlight, a figure came around the hallway.

Brian looked up at us, and I could see the smirk on his face. It was an expression I had seen often, the shit-eating I-just-got-laid grin. "What have we here? Two old lovebirds alone in a darkened room? What are you guys up to?"

"Couldn't sleep," Courtney replied, holding up her mug of warm milk. She nodded to me. "We've got a lot to catch up on."

Brian strutted into the kitchen, shirtless and flexing his pecs, to get himself some water. "I'll bet you do." He mimed a pumping motion with clear sexual connotations.

I relaxed considerably. If Brian actually suspected anything, he wouldn't be joking about it.

Courtney and I made idle small talk for the next few minutes, just to keep up appearances. I was working hard to keep my own wide grin off my face, but Courtney's features were schooled and calm. I wondered what was really going through her head. Was she regretting what we had just done? Did she still have feelings for me? Was she concerned about Anna? What were we going to do?

But then a few moments later, Brian disappeared around the corner and then we heard the solid click of a bedroom door closing once again.

And in less than a second Courtney was suddenly straddling my lap. Then she whispered in a husky voice, the four words I'll never forget for the rest of my life, "I love you, too."

There were tears streaking the corners of her eyes. "I took me three years to figure that out. I wasn't ready for you then. Too young, to naïve. But I'm ready now, after three years of wanting you to be happy, giving Anna all my encouragement to make you happy. Three years of trying to deny what was still in the bottom of my heart. I love you." She kissed me quickly, and then pressed her forehead against mine. "I'm sorry I never told you that when you needed to hear it."

I was so shocked and yet so happy at the same time I was frozen stiff. And then her tongue was lodged in the back of my throat once again, and I ceased to care about anything else in this world.


Nothing beyond kissing occurred between us that night. The risk of getting caught was just way too high. At last we parted with a promise to talk about this. And then I was retreating into a bathroom to scrub away any possible evidence before returning to Anna's side in our guest bedroom.

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