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Sorry for the delay on this chapter. As always, I hope you enjoy!
A few hours after we performed on the phone for Jenna, I took Claire home. We had watched a movie, cuddling contentedly on the couch, talking idly about the plot, the plot holes, and whatever else popped into our heads. Claire had a family thing the next day, Sunday, so I didn’t see her again until Monday evening, when we were both scheduled to work.
I was in the back, digging through a fresh shipment of boxes, looking for KISS bobbleheads and swearing quietly as I knocked over a box full of funny but crappily-made tshirts when one small hand covered my eyes and another pinched my ass.
“Guess who!” I heard in Claire’s soft, sweet voice.
“I deeply, desperately hope it’s not Pam,” I answered. My answer earned me a giggle and a swat across my butt. Pam was our manager, and she was at least sixty years old and a hundred pounds overweight.
I turned and drank in the sight of Claire in her work polo and a pair of tight jeans, her hands on her hips, her long blonde hair hanging straight and framing her smiling face. I slipped my fingers into the waistband of those hugging jeans and pulled her toward me, getting a squeal and a laugh as our lips met and our tongues glided across each other.
“If Pam catches us, we’re both fired,” Claire whispered against my lips.
“Nah,” I said, feeling her smile on my mouth. “If Pam catches us, you’re fired. She totally wants me.”
That got me another smack, this time on my shoulder. I pulled her lips back to mine, and felt her smacking hand grip my shoulder tightly, her fingers clawing gently as she moaned into my mouth. My hand slipped down her back, edging under the waistband of her jeans and gripping her bare ass, squeezing the soft, warm flesh.
“Jesus you make me horny,” she gasped. “Every time I see you I want to rip your clothes off.”
“So you’re telling me that our work productivity is about to take a nosedive?” I asked.
“Probably,” Claire replied with a giggle.
Our shift went surprisingly quickly, our newfound ability to actually talk to one another helping it not drag by. Even the few little rushes of customers went more smoothly than usual after we discovered that communication really does come in handy. We laughed and joked with each other in between flirty comments and just-shy-of-inappropriate lingering touches. As the shift came to a close, Claire found me stocking novelty coffee mugs and, with a quick glance over her shoulder to check for an encroaching Pam, slipped her arms around my waist from behind.
“So,” she began conversationally, “I take the bus to work after school, so I need a ride home. I was thinking I could walk along the highway with my thumb out, but if you’re interested I thought maybe you could take me. And that maybe we could swing by your place real quick before you drop me off.” As she finished, Claire’s hands dropped lower, sliding down my stomach to give my cock a quick squeeze.
“Well, I had planned to drive up and down the streets looking for young, impressionable hitchhikers anyway, but that idea simplifies the process,” I replied, reaching an arm behind me and running my finger heavily up and down the seam that was pressed tightly to her pussy.
“I was hoping you would say something like that,” she breathed in my ear. Her arms suddenly disappeared from around me as she moved away, headed back into the back to collect her stuff and clock out. I gave myself a few minutes to catch my breath and finish shoving coffee mugs onto the shelf before adjusting my cock and following.
In the parking lot, I opened her door for her, and Claire smiled at me sweetly, blowing me a quick kiss as she climbed into my car. I jumped in to the driver’s side and started the engine, looking down and grinning as she slid across the seat and nestled herself under my arm, pulling my hand around her shoulders. My fingers lazily traced circles around her stiff little nipple as I guided the car out of the parking lot and onto the street, accelerating toward my apartment as quickly as I could without having a cop interrupt our drive.
While I drove, Claire sank lower in the seat, her fingers dropping into my lap and scratching lightly across the length of my denim-covered cock. I let my hand slide down her side, caressing through the soft cotton of her work shirt as I walked my fingers lower, slowly gathering the fabric as I went until my fingertips brushed against smooth, warm skin. My fingers trailed across, following the shape of her hip bone until they bumped into the waist of her jeans, then following that hem across her belly, dipping just underneath until I reached the button. I popped it open, flicking the tab of the zipper upward, and tugging, hearing the buzz as her fly opened and I slipped my hand lower, tracing the gentle swell of her mound.
“Mmm,” she moaned as my fingers brushed against her lips, her legs spreading wide, stretching the crotch of her jeans between them, giving my fingers more room to work as I gently ran antep escort the tip of my index finger across her clit.
“You didn’t wear panties,” I observed belatedly.
“I was kinda hoping something like this might happen,” she confessed, her breath heavy and quick through her words.
“Oh, really?” I asked. I curled my middle finger inward, slipping effortlessly between her soaked and swollen lips. Claire cried out softly as my finger dove into her, hunching her hips against my hand, driving her clit into my palm as she tried to force my finger more deeply into herself.
“Yes,” she whispered. I plunged my finger as far into her dripping pussy as I could reach and curled it toward my palm, scratching my fingertip across her g-spot, trying to pull an orgasm out of her. She reacted immediately, her back arching, pushing her breasts upward, driving her head into my lap, her cheek against my denim-covered cock. Her pussy clung to my finger and pulsed, sucking at my fingertip and convulsing, pushing her wetness into my hand as I turned the last corner into the parking lot of my building and pulled into my space.
“Inside,” I said, half question and half order, as I tugged my hand out of her pants and popped open the door.
“Fuck yes,” she breathed. Claire did a fast sit-up and tugged her work shirt down, hiding her open jeans rather than doing them back up, and she scooted out the door and under my arm.
She reached across me, snagged my keys, and took off at a run. I followed behind, laughing as I jogged after her, enjoying the sight of her ass as she ran ahead and disappeared into my building.
She was already up the first flight of stairs by the time I got in the door, and a few seconds later I heard the keys go into my door and the door being flung open. When I rounded the corner and reached my doorway, I found a trail of clothes that led across my living room floor to Claire, standing naked and proud on my coffee table, her hand on her cocked hips, hair hanging down to brush just above her nipples, her smoothly shaven pussy blushing and ready. She was just over five feet of lust and sexuality, and she was waiting for me.
I peeled off my shirt and shoved the door closed behind me, kicking my shoes off as I crossed the living room, undoing my belt and shoving my jeans and underwear down. She giggled as my purposeful stride was interrupted by me having to dig my ankles out of my pants and peel off my socks. When I reached her, she grabbed my shoulders and shoved me to the side, pushing me off balance so that I collapsed onto the couch, my cock bobbing up from my lap like a flag in a storm.
Claire stepped from the coffee table to the couch, one foot on either side of my thighs, and wrapped one hand around the back of my neck, using me like a support pole as she bent her knees and squatted down, reaching behind herself to grasp my cock and guide me perfectly into her tight, soaked pussy. As the head slipped into her, she shifted, settling on her knees, before looking me in the eyes and kissing me hard, her lips mashing against mine, her tongue slipping into my mouth. She bit down playfully on my lip, and then dropped, burying my cock completely inside her with one fast, perfect move. Claire cried out into my mouth, her fingers tightening on the back of my neck, her eyes squeezed shut, her mouth open wide.
“I’ve wanted your cock in me all day,” she said, her eyes still closed. They opened slowly, focusing on mine, and she smiled, her hips beginning a slow, unhurried series of small circles. “My nipples were so hard when I went to school, and as soon as I saw Jenna my pussy started dripping, thinking about grinding myself down on you, just like this.”
With that, she began to fuck in earnest, her hips hunching faster and faster onto my cock, her pussy gripping me tightly as she gasped and moaned, her fingers digging into my shoulders and neck, her lips parted, lightly touching my own, my hands running up and down her back, pushing into her hair, lightly tugging, exposing her neck to my mouth and biting down. Her nipples pressed into my chest like two little pebbles, brushing against my chest hair as she moved. I cupped her ass with my hands, squeezing, pulling her onto my cock as I thrust my hips up to match her motion.
Claire’s breath quickened, coming in faster and shorter gasps as her pussy began to pulse around me. She threw her head back and called out her orgasm, her body blushing from her pussy to her neck. Her hips became erratic, jerking back and forth on my cock as she flexed her whole body to the task of her cumming.
She fell forward as her orgasm took her, her chest against mine. She kissed me over and over, mumbling nothing into my mouth as her fingers trailed across my arms and shoulders. Her pussy twitched on my cock, and her hips slowly regained control of themselves and she returned to a slow, teasing rhythm.
“Jenna really wants to watch us,” she said. Her lips curled into a naughty smile as she ground down onto my cock. “She asked again today after I told her about the shower sex.”
“Oh really?” I asked. Claire pushed down hard on my cock and rolled her hips. I groaned and squeezed her ass, my cock throbbing inside her.
“Oh yeah,” she replied. “She wants to sit back and watch me suck your cock, finger her tight, tan little pussy while you fuck me. Would you like that, baby? Watching my best friend fuck herself, all stretched out naked and wet while you drive your big cock into my tiny little pussy?”
“Mmhmm,” I moaned.
“You want to watch her cum like crazy when you shove your cock in me? Watch her sit on my face while you fuck me hard and finger my ass?”
“Fuck yes,” I grunted, and shoved my cock hard into Claire, straining to bury myself as deep as I could go as I came hard, erupting against her cervix as she cried out and came with me, my orgasm triggering her own. Her fingers dug into my shoulders, her hips jerking as she pulsed, pulling my cum out of me and deeper into her cunt, her lips open wide, her eyes half open as she stared into my own.
Her mouth closed on mine as her breath came rushing back, blasting through her nose and across my cheek as her tongue plunged into my mouth and explored, searching for my tongue and toying with it. Claire’s pussy gave little aftershock twitches around my cock, the last vestiges of her hard orgasm playing out along the length of my shaft as we kissed.
“You like the idea of Jenna watching us, don’t you?” she teased.
“Almost as much as you do, I think,” I responded, smiling against her lips. She giggled, and I gasped as I felt her laughter on my cock.
Claire pushed up, and slowly pulled my cock from her pussy before standing and walking to her clothes.
“I have to get home,” she said. “Mom is expecting me right after work, so I’ll already have to tell her that I had to wait for a ride.”
“Mmhmm,” I groaned, sitting up from the couch and reaching for my own clothes. “What are you doing tomorrow after school?”
“I was going to ask you the same thing, actually. I think we should talk about this whole Jenna thing a little more seriously, and with our clothes on. At least for the first part,” she finished saucily, and swatted playfully at my ass.
“Good call,” I said with a grin. “Shall I pick you up after school? Cranky’s?”
“Yes,” she agreed, stepping into my arms and kissing me gently. “Now take me home before my mother calls the police.”
The next afternoon, I pulled up outside the school and sent Claire a text, waiting somewhat awkwardly as hundreds of students poured out of the building and swarmed toward the parking lot. A few moments later, the passenger side door opened, and Claire popped into the passenger seat, her ass barely touching the fake leather before bouncing back into the air as she hopped over next to me and planted her lips to mine.
“God, I get wet just thinking about you,” she muttered against my lips. “My panties have been soaked all day.”
“I take it you think about me a lot,” I mused. I cupped my hand to the back of her head and pulled her close, my tongue swirling into her mouth as she moaned and pressed harder against my chest, her nipples so hard I could feel them through our clothes. As my hand started to slide down her back, the back passenger door opened and Jenna slid into the back seat.
“Wow. I thought we were gonna talk about it first, but if you guys are ready, I’m down. The school parking lot seems like kind of a bold place to do this, but it’s a kind of a thrill. Glad I wore a dress!”
We broke the kiss and looked back to see Jenna grinning broadly at both of us, the hem of her floral dress dangerously high on her slightly parted legs, her nipples poking prominently through the thin material.
“Smartass,” Claire giggled. “You would.”
Jenna and I both laughed, and I threw the car in gear. I drove us to Cranky’s where Claire told Jenna to just let me order, and we waited for our food, making small talk and sipping our drinks. Claire sat next to me, her hand gently rubbing my thigh, and Jenna sat across from us, holding her own in the conversation while managing to flirt with both of us.
Our food came, and we all tucked in, eating quietly for a few minutes, none of us really sure where to start.
“So,” Claire said slowly, “Jenna would really like to watch us fuck.”
“Jesus!” Jenna exclaimed. “Nothing like getting right to the point.” We all laughed.
“I, personally, have no problem with it, and it actually kinda turns me on,” Claire said with a giggle. “Jenna and I have some, let’s call it experience, in the area, after all.” Both girls blushed and giggled, and I felt my cock stiffen.
“I don’t have any problem with it either,” I said slowly. “I just want to make sure that all the ground rules are laid out ahead of time so nobody gets hurt.”
“That sounds like a good idea,” Jenna said, taking a bite of shrimp.
“Okay, so ground rules,” Claire mused. “Well, as I see it, I know that I love fucking you both. I’m completely comfortable with both of you, and I have no problem with whatever happens, whether it be just Jenna watching the two of us, or Jenna joining the two of us after watching for a bit.”
“So what we’re figuring out here is whether me joining the two of you means the two of us fooling around while he fucks you, or him fucking both of us?” Jenna asked. Her nipples were hard again, two sharp little points on the tips of her generous breasts.
“No,” Claire said. “I’m totally cool with him fucking both of us. I mean, I kinda want to watch him fuck you, too. I think it would be really hot to watch him make you cum all over his amazing cock after he’s fucked me silly.”
Jenna lips parted and she groaned, shifting minutely in her seat.
“What I think we need to figure out here,” Claire continued, “Is how well you two will get along sexually. I think having us in a threeway being the first time you two fuck is a recipe for an awkward threeway, and I don’t think anybody wants that.”
“You’re saying that Jenna and I should hook up before we do this?” I asked.
“Yeah. I think you two should have an actual date, really. I’m not going to get jealous or hurt. I think that my relationship with you, new as it is, is more than strong enough for me to not have to worry about whatever happens between the two of you, and I know that my relationship with Jenna is strong enough for the same. I think that you guys having a whole night with just the two of you will make our get together that much better.”
I searched Claire’s face for any sign that she was testing me, and seeing none, I nodded.
“That makes a lot of sense, actually,” I said. I shifted my attention to Jenna, who had come down from her glazed state a bit. “Jenna? Would you like to go out tomorrow evening? Grab dinner, maybe watch a movie at my place?”
“I can’t believe you’re actively encouraging me to go on a date with your boyfriend. Not only that, but you’re actually hoping it goes well, and that we wind up fucking. Also yes, Jay, that sounds lovely!”
We all laughed, and Claire squeezed my thigh. I leaned over and kissed her, tasting soda and shrimp and her lip gloss.
“You’re absolutely sure about this?” I asked, whispering in her ear.
“Completely. I trust you both, and I’m not worried. Besides, you’ll both have a great time, even if something goes wrong and you don’t wind up fucking,” she whispered back.
I smiled and kissed her again, wondering idly how my life had gotten to this point is such a short time, but also not questioning it too hard. Sometimes, I had learned, it was better to just go with it.
I dropped both girls off at Claire’s house after we finished our food, then went home to get some homework done. In the back of my mind I kept marveling at Claire’s absolute confidence in our new relationship, while resolving myself not to do anything to betray that confidence. She had given me carte blanc to do whatever I wanted, really, so my task wouldn’t be all that hard.
The next day, I had only one class. It went quickly, and I spent the rest of the time between it’s end and my date with Jenna getting a few things done around my apartment, doing some laundry, and generally making sure the place was ready to make a decent first impression. I showered and trimmed up my beard, dressing nicely, but not over the top, in a pair of light dress slacks and a blue button-up, leaving the top three buttons undone and rolling my sleeves up to just shy of the elbow.
I arrived at Jenna’s house promptly at seven, and she met me at the door.
Where I had gone for casually formal, Jenna had dressed to impress. Her ample breasts were displayed prominently a skin-tight black dress that stopped well above her knees, the front a sort of hanging, gathered cloth that gave her neckline the illusion of modesty while it plunged all the way past her navel. Her feet were held in a pair of black, strappy high-heeled sandals, and her hair was pulled back into a curly, bouncing ponytail coupled with just the perfect amount of makeup. The overall effect lent her a sort of sexy elfin look that was an immediate turn-on. She was a knockout.
“You look amazing,” I said, my eyes taking in every inch. Jenna turned side-to-side, cocking one leg slightly, showing off for me.
“Thanks,” she said with a naughty smile. “You look pretty good yourself.”
I offered Jenna my arm, and she looped hers through it, resting her hand lightly on my bicep as I escorted her to my car. I opened the door for her and she sat, prim and proper for a half second before winking at me and slowly turning, stepping her smooth legs one at a time into the car, giving me an all-to-brief glimpse of sweet, tanned, shaven flesh nestled between her thighs.
I took a deep breath and closed the door, exhaling through my nose in one long release as I walked around the car and climbed in. I looked over at Jenna, her gorgeous legs crossed, a mile-long expanse of thigh showing, the front of her dress spilling open slightly, revealing a generous amount of the curve of her breast, and knew that I was in for a hell of an evening, regardless of the final outcome.
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