The First Timers Club Pt. 06

Chapter 28 - The First Timers Club

"Wait! Back it up, like, fifteen seconds. No, you went too far. Stop! Forget it, just play it from there. This is fine."

We'd watched Courtney's video for the past hour, and for the sixth time, my cock penetrated her pussy for the very first time and for the sixth time, Courtney cried. Kayla rolled her eyes and hid her face in a pillow, while Ashley and Brittney quietly discussed video game strategies they planned to employ later that evening.

"I think we've watched it enough. How about we do something else now?" I suggested.

She glanced at me and sighed. "Fine. Let me just watch the money shot one more time."

I fast forwarded to a medium shot of her jacking me off onto her tits, and I had to admit that Kayla had done a great job of capturing the moment, even incorporating a slow-mo effect to draw out the ejaculation and splashdown. And Courtney's onscreen tits did look spectacular covered in my cum.

When the video finished, I resumed the porn playlist and lowered the volume. The sun had finally set and we all pretended that in a few short hours, we wouldn't have to disband and go our separate ways until the next day. I could have hung out with the four of them for days and days, and the realization of that made the looming melancholy even worse.

I stood and winced from the pain in my shoulders. Carrying Courtney to the lounger had proven to be the proverbial straw, and it now felt like a troop of tiny cub scouts had built a campfire between my shoulder blades. I rotated my arms and took my spot in front of the television. The idle chatter diminished until they all sat quietly waiting for me to say something.

"Hopefully, this doesn't sound too stupid," I began, and Brittney flourished her hand.

"Just say what you feel," she said, impersonating my voice, and I pointed a finger gun at her and winked.

"That's really great advice," I said and collected my thoughts. "I just wanted to say that the past couple of days have been amazing, and I'm grateful to have gotten the chance to meet the four of you. You're some of the smartest, funniest, kindest, and sexiest women I've ever had the privilege to know and I feel honored that you invited me into your circle. There's no doubt I'll cherish this experience for the rest of my life."

I watched four smiles fade as they exchanged glances and my stomach sank. Had I said something offensive? Had it been too much? Why were they looking at me like that?

"What's wrong?" I asked.

"Are you leaving us now?" Ashley asked.

"What? No! I was just thanking you all for an amazing time so far. Why? Do you want me to leave?"

"No!" Courtney shouted, leaping to her feet. "Are you fucking kidding, dude? I'm trying to figure out how to sneak you into my bedroom. You're really not leaving?"

Reassured that I hadn't said something stupid, I laughed. "Fuck no, I'm not leaving! We've just gotten started."

The look of relief on their faces sent a flood of emotions coursing through me that I hadn't felt in ages. I contemplated that I would have to leave them at some point, and the realization of that filled me with an overwhelming sense of impending loss. I didn't usually form these kinds of bonds with the women I slept with. If any one thing defined me, it was my stubborn refusal to get attached to anyone. I cherished my independence and preferred to remain aloof and emotionally unavailable. But at that moment, and for the first time in a long time, I imagined a future that included these four girls and it shook me.

There could be no future for us, of course. I was well over twice their age. I'd already lived out my youth while they still had theirs ahead of them. We just happened to share this particular slice of time together, and when it ended, that would be it. We'd go our separate ways, and only remember each other during particularly sentimental moments that would inevitably fade from memory for months at a time to start, but then for years thereafter.

What the fuck is wrong with you?

"What's the date today?" I asked in an attempt to distract myself from the horrific emotional morass in which I'd become mired.

The four girls raced to check their phones, but Ashley crossed the finish line first with the information.

"March fifteenth!"

I grunted. "The Ides of March."

"Hey! Julius Caesar!" Ashley said.

"That's right. Anyway, mark your calendars, because on this date, you all accomplished something pretty fucking significant, in my opinion. And you did it for the last time."

"Wait, what did we do?" Ashley asked, and the other three pelted her with pillows.

"We got laid, genius," Courtney said derisively.

Ashley looked at me confused. "But you said we did it for the last time."

"I meant you had sex for the first time." She still didn't get it. "You can't have sex for the first time ever again. You can only...you know what, forget it. You got laid, and I'm certain you'll get laid lots and lots more times in the future."

"OH! I get it now!" she said and fell backwards in a fit of giggles as more pillows flew her way.

I had a thought and went to the fridge to collect the last of the beers. We'd gone through most of a twelve-pack, but two remained. I brought them with a sleeve of red Solo cups back to the table and distributed the contents of the cans between the five of us. When everyone had a cup, I lifted mine to offer a toast.

"Here's to your first times."

"The First Timers Club," Kayla said.

"The First Timers Club!" everyone shouted.

I drained my cup and suddenly felt incredibly weary. Kayla had kept me up for most of the previous night and I'd had vigorous sex with the rest of them for most of the day. I knew I wouldn't last much longer. Brittney noticed the second time I yawned and gave me a look, but I tossed her an okay symbol and she grinned and quietly clapped her hands.

Why had I agreed to have sex with her tonight? It had seemed such a no-brainer idea at the time, when she'd clung to me with that dreamy post-orgasmic look on her face and fuck-me eyes, with my cock throbbing for release, but now I regretted it. Maybe she'd be up for a cuddle? She could be the big spoon.

Kayla and Courtney received numerous text messages from their parents until, finally, they had to pack up and leave. Brittney tossed Kayla her car keys and the four girls hugged and promised to meet back at the pool house by noon the next day.

When they'd gone, Brittney and Ashley attempted to teach me to play Magic the Gathering, but I had no idea what I was doing and they easily mopped the floor with me until I begged to sit out and just look at the artwork on the cards while they played against each other. This turned out to be a good idea, because it was far easier for me to pick up on the nuances of the game's strategy by watching two proficient players go at it.

Finally, the time had come for the two of them to go as well. Clay would be home soon and it would be better if they were in the house when he did, so there'd be no excuse for him to come looking for Ashley. I gave them hugs and whispered to Brittney that she shouldn't leave the butt plug in for too long. After a quick pitstop to the bathroom, she emerged and subtly let me know she'd left it in there.

I flicked off the lights and climbed to the mezzanine, thoroughly exhausted. After plugging in my phone, I set my head on the pillow and promptly fell asleep.

Chapter 29 - Irish Massage

A series of message alert awakened me from one of the deepest sleeps I'd had in years. I peered at the screen's dim glow through a barely cracked eyelid and knew who it would be. Another alert brought me closer to full consciousness and I reached for the phone to check the messages.

Ash is asleep

U still up or did u crash?

Packing up to come over

Be there in a few

Bringing goodies

I went downstairs to unlock the slider for her and then crawled back into bed to wait. I heard the slider open and shut and the click of the lock and the creak of the stairs as she ascended to the loft.

"Oh, you're awake," she whispered when she found me browsing my phone. It amused me that she and Kayla had both felt the need to whisper.

"Your messages woke me up," I said in a normal voice, setting the phone down and turning on the bedside lamp. I noticed she had a large reusable shopping bag in her hands. "What's that?"

She looked at it and her face brightened. "Oh, I noticed your shoulder seemed to be bothering you earlier." She reached in and pulled out a bottle of baby oil. "Thought you could use a massage."

I could have kissed her. I'd almost texted her back to ask for a rain check and now I'm glad I hadn't. She set the oil on the bed but more items filled the bag.

"That sounds amazing. What else you got?" I asked.

"Some snacks and stuff from the kitchen. I noticed the fridge here was just about empty and you've barely eaten anything for days, so I brought you a bunch of chips and cookies and stuff. I know it's not very healthy, but hopefully it's better than nothing."

It could have been rendered hog fat for all I cared. My stomach grumbled at the mere mention of food and I held out my greedy hand for the bag of cookies she pulled out. While I stuffed my face with shortbread chessmen, Brittney sat primly on the edge of the bed to watch me. I held out the bag to her and she took a cookie to nibble on. I tilted the bag back to slide the last two into my mouth, then tossed the trash onto the nightstand.

"Oh man, that was great," I said. The carb hit perked me up and I felt more energetic. I noticed Brittney's outfit. A matching set of pink fleece pants and a zip up hoodie. "What's up with you and sweats?" I asked her as I dug into a bag of pretzel sticks.

She looked down at her attire and shrugged. "It's hard to find clothes that fit my body," she said. "Plus, they're comfy."

I lifted my eyebrows and tilted my head from side to side. "Makes sense, I guess. You look way better naked though. Why don't you take them off?"

Her eyes twinkled and she stood and unzipped her top, then pulled down her pants and kicked them both under the bed. She hadn't bothered with underwear. She took the shopping bag from me and pulled out a box of tampons and a large beach towel. The tampons went onto the nightstand, and she waited with the towel for me to move.

I stood while she pulled the duvet and top sheet down to the footboard and spread out the beach towel in the center of the bed. Then she picked up the oil and flipped open the top.

"Lay down."

I didn't want to let the bag of pretzels go, but I wanted a massage more. I laid down on my back and put my hands behind my head.

"On your stomach," she laughed.

"Just come here."

She tilted her head and then crawled onto the bed next to me. I tapped my pelvis.

"Right here," I said. She smirked and lifted her leg over me to straddle my hips. "Put oil on." She tilted the bottle over my chest but I stopped her. "Not on me. On you."

She lifted one of her russet eyebrows and smirked. "Okay..."

Clear oil cascaded over her breasts and belly, spilling over her thighs to pool in the space between them. I held out my hand for the bottle and she gave it to me.

"Rub it in," I said.

Brittney breathed a laugh from her nose and said, "I'm supposed to be giving you a massage, remember?"

Her hands went to her chest and glided over the swells of her perfect breasts and down over her soft belly. Her pale, freckled skin glistened like a freshly lacquered Rubens painting and I felt myself growing beneath her. She felt it too and glanced down to see the head of my cock peaking from between her thighs. Her smile grew.

"I could watch you do that all day," I told her, squirting more oil over her chest. "You missed a spot."

She laughed and worked the oil into her skin, her hands moving effortlessly over her breasts, cupping them, lifting them, her palms and fingers sliding over her nipples. She seemed to enjoy watching me watch her.

She shifted her hips and discovered the ease with which the spilled oil allowed her to glide over my pelvis. I added a bit more, and soon she had her hips rocking back and forth, her fine pubic hair brushing over the head of my pinned cock. I coated her thighs and then set the oil on the nightstand. When she tried to move faster, I put my hands on her hips to slow her down.

"Slow," I said. "We've got all night."

She breathed a deep sigh and rhythmically rocked her hips back and forth, sliding her pussy over my cock and distributing the oil between us. Her hands continued to move over her breasts and she looked down at me and smiled again.

"What is it?" I asked as I spread the oil over her thighs, her smooth skin taught, her muscles stretched.

"I can't believe I'm here right now," she said quietly.

"I'm glad you are."

She closed her eyes for a moment and breathed deeply. "This is like a dream for me. I've thought about a moment like this for so long. To be with someone. Alone in a bed with a man, touching him, pleasing him." Tears welled in her eyes. "You've made my dreams come true." A tear broke free and she hiccupped a sob. "I'm sorry."

I thought to respond, to soothe her and tell her not to be sorry, but I didn't. Part of me thought it would just invite more tears. But another part urgently wished to remain detached. To not feed into the emotional bond that could so easily develop. Instead, I moved my hand between her legs and gently rolled my thumb over her clit.

"I want to fuck you, Brittney, but not like earlier. I want to fuck you slow. I want to take my time with you. I want to use my tongue and my fingers and my cock and anything else I can get my hands on to make you feel so much pleasure that you giggle uncontrollably like you did this afternoon. I want to cum on you and in you, as often as I can until I can't cum anymore, and then I want to fall asleep with my cock inside you and dream about fucking you."

She stared down at me and her face and chest reddened as I spoke. I slid my hand up her belly and between her breasts to the hollow of her throat as her hips continued to grind against me.

"But first," I said, "I would love that massage because my shoulders are killing me."

She bit her lip and smiled. "Turn over then," she said and dismounted to let me do it. My cock popped up and she gazed at it longingly. She put her oily hand on it and slowly jacked me off. "Unless you'd like me to suck you off first."

I would have liked that very much, but it could wait. I got up off the bed and headed downstairs.

"Where are you going?" she asked.

"Just getting some things." I returned with the black sinch bag. "How did wearing the butt plug feel today?" I asked when I'd settled back onto the bed.

She gave me an embarrassed smile and shrugged. "Different than I expected."

"How so?"

"I thought it would hurt and be gross."

"But it didn't?"

She shook her head. "No. It felt...I don't know how to describe it. Sexy? Naughty, maybe? Like I was doing something I shouldn't be."

"Dirty?"

"Yeah, dirty. But in a good way."

"Like having sex on your period."

"Exactly! I never thought, you know, that I'd like anything like that."

"Having things in your butt?" I asked, and she nodded. "I've noticed that you have a hard time cumming from vaginal stimulation alone, but when you're anally stimulated, you cum easily."

She looked away for a moment. "That's weird, isn't it?"

"No, not at all. Remember what I said earlier? It's pretty common, actually." I squared up to face her directly. "I think you would enjoy anal sex a lot, Brittney, and, if you want to try it, I'd love to do it with you."

She looked at the bag in my hand and then at my cock and the lines on her forehead deepened. "I don't know..."

I set the bag aside. "That's okay. You don't have to if you don't want to."

She grabbed my wrist. "No, it's not that. I think I do want to. I mean, I definitely want to. A lot. I just don't know how you'd...fit inside there."

I opened the bag and pulled out the larger of the two butt plugs. "This is how. Put this in for a while and it'll help open you up." She took it from me and appraised it, while I removed the smaller red one she'd used earlier, which I'd cleaned and sanitized before getting into bed. "This one's an inch and a quarter wide, which you took pretty easily."

"How do you know how big it is?"

"It's stamped on the bottom here, see? The one in your hand looks like it's a little less than two." She checked the bottom but didn't find any markings. "My cock is only about a quarter inch bigger than that, so if that one fits, you'll definitely be able to take me."

She handed the plug back to me. "I guess we can try it and see."

"You sure?" I asked, dropping the small butt plug back into the bag and removing the anal lube.

Her eyes moved from the plug to my cock to my eyes and she nodded. "I want you to be able to put your dick in there and fuck me. I didn't think I'd ever want that from anyone, but I want it from you."

"I won't hurt you," I assured her. "I'd never do that. If this doesn't fit, we'll just skip it, okay? We'll only do it if you think it feels good." I held out my pinky. "Promise?"

She smiled and hooked her pinky around mine. "Pinky promise."

"Speaking of pink, why don't you get on your hands and knees so we can get this baby into your ass."

It took inserting the smaller one first before she loosened up enough to accept the larger one, but after a couple minutes of clitoral stimulation and slight pressure, the large butt plug rested snugly inside her rectum.

"Stand up and walk around. How does it feel?"

She did and pressed her hand against her lower stomach. "I can feel a little pressure right here," she said, "but only just." She did a quick out and back around the bed and looked at me with a smile on her face. "I can't believe it fits."

"Does it feel okay, though? Does it hurt at all?"

"No, not at all. It feels kind of good, actually. Especially when I'm walking around, it kind of moves a little."

"Good. Just think about how my cock's going to feel, all lubed up, sliding in and out of there. I think you're going to fucking love it."

She smiled at the image and then twirled her finger over the bed. "Alright, enough shenanigans. You need a backrub asap. Lay down, on your stomach this time, and let me make you feel better."

I set the sinch bag aside and laid on the bed. My stiff cock felt like a tent pole. I adjusted it around, trying to find a comfortable position until, finally, I pushed it straight down between my legs. I put my hands down at my sides and turned my head toward Brittney. She looked at the way my cock pointed down between my legs and laughed.

"I didn't know you could do that," she said.

"I didn't either until just now."

She reached down and ran her oily hand over my balls and the bottom of my shaft.

"Mm, well that's wonderful. I can get to you whenever I need to."

She mounted me from behind, straddling my thighs once again, but found balancing herself on top of my ass too precarious. She slid forward to the small of my back, but that didn't leave her much room to work, so she settled onto the backs of my thighs.

The baby oil felt cold on my skin as she squirted far more than she needed all over my back and even on my ass. Then I heard more oil squirting out of the bottle but didn't feel it, and realized she'd oiled herself again. She set down the bottle and laid on top of me.

"I just need to spread this around," she said. She moved her body over mine, rubbing her tits against my back. Then she sat up again and giggled. "Perfect."

Her massage ended up being much better than I expected. Her strong hands penetrated deep into my muscles to work out the knots she found there. She explained that she'd taken a sports medicine class once during summer school, when she'd considered going to college to be an occupational therapist, before she'd settled on medicine as her goal, and she'd learned several deep tissue massage techniques from that.