Smack! My hand comes down hard on Jocelyn’s bare ass.
“Seb, owww!” The blonde thirtysomething pulls forward off my dick, rubbing the afflicted cheek. “What was that about?”
Oh, shit! Don'elle is the one who likes it rough. She’s the hardbody I met at the gym last year, the one who carries her strength and aggression over into the bedroom, frequently batting and biting my dick, growling and grinding like an animal.
But Jocelyn is the demure housewife down the street, about a biweekly fuck in the mid-morning after she sets her kids off to school. She doesn’t say anything bad about her husband, Cade or Wade or something, so I don’t know if he’s lacking what she needs, or if she just likes extra dick. I haven’t asked. Either way, I’m happy to be giving her whatever satisfaction or variety she needs or wants.
This is the first time Jocelyn has let me do her from behind. I hope my blunder won’t make it our last doggy fuck. Maybe I was imagining Don'elle’s tight clenching butt cheeks when I closed my eyes in ecstasy, smacking the hard ebony glutes in my mind rather than the pillowy pale flesh of my real-time partner.
“Oh, sorry, Joss.” I lean forward to plant soft, wet kisses on her shoulders, gliding a soothing hand over her ass. “Got carried away. You do things to me!” Evidently satisfied that I’ve recalibrated back into tender lovemaking mode, she lets my dickhead nudge her labia open again, and within seconds I’m back to deep and steady strokes.
For those endeavoring to live a lifestyle of juggling multiple women, make no mistake: philandery sure can have its share of challenges. Not only do I need to keep straight different lovers’ sexual preferences, but there’s also the matter of managing schedules. I’m in no real hurry to be done with neighborhood MILF duty, but I do have one eye on the wall clock, calculating my tight schedule. Ten minutes later, after grunting and spewing in my condom (yes, Jocelyn is on the pill, but her awareness of my promiscuity makes her understandably cautious), I check my phone before our customary wipe-and-cuddle. I should have enough time to finish up some work shit at home, make a run for building materials, and down a sandwich before my mid-afternoon date.
· - ~ | ~ - ·
The drive back from across town in shitty traffic is especially shitty today. When I’m still fifteen minutes from home, Ellen texts me to tell me she’s close. She’ll be there before me, so I wait till the next red light and text her back, apologizing. She teases me by asking if I’m backing out, and follows up telling me she should just have a key.
Ellen is a local commercial real estate mogul in her late forties. Mature, confident, successful, and elegant, sex with her is the perfect mix between the thrill of fucking a fashion maven and living out a dirty fantasy with a high-powered executive. My truck sits high, so I run little risk of being caught as I unzip my pants to straighten out my cock, which has stiffened uncomfortably sideways as I’ve begun my countdown to my first threesome.
Ellen puts on a professional façade, but over the drinks we shared after she showed me a few properties for a client, she related a few deviant sexual experiences. Not sure if it was the cocktails or weed, or both, that affected her mind as we were draped naked over my patio chairs after a vigorous session a few weeks ago, but, aware of my other fuckbuddies, she’s the one who suggested meeting one of the others for a ménage à trois. Not knowing their names or anything about them other than “neighbor” or “coworker” and such, she apparently trusted my judgment.
I’d probably have to work on Jocelyn for another year before she’d be willing to entertain any notion of bisexuality, and she’s fearful enough of STIs that she doesn’t even do oral sex with me, and who’s heard of threesomes without oral? But fortunately there were other options.
Josafina is the best cocksucker, a Costa Rican beauty who used to cut my hair. I can’t get enough of the cute mole above her plump, perpetually wet lips when they’re clenched and bobbing around my shaft. Eye contact, hollowing cheeks, humming sounds, tugging balls, plenty of spit, and a tongue that won’t quit till she swallows my natilla — she personifies the complete blowjob package. Her language swaps from Spanish to English, from sweet to dirty, as her heavily-mascaraed lashes flutter and large hoop earrings dance in time with her strokes and slurps, even while attending to her own pleasure with her fingers up her hairy panocha. She’s called me a different name in the heat of our fucks, and mentioned sharing a cock more than once, so she must have plenty of partners and not necessarily one at a time. But when I asked Josafina about joining me with a hot real estate agent, she only responded “maybe.”
The aforementioned Don'elle joyfully owns her promiscuity and has no filter when it comes to mentioning sex acts that have yet to be realized. How sweet it would be for another chick’s mouth to slurp up all the dollops of my thick pearly white jizz after it sits in contrast on her dark skin for a few seconds? But the black beauty’s idea of fucking more than one person at a time is more like a spitroast on a gym bench or popping by my place on poker night to grind on one guy’s lap while blowing another and jacking cocks three and four with her free hands. Not my thing.
Anna (or Ana? She’s never spelled her name for me) is a neighbor whose dog actually gets along with mine. We pass each other frequently on our walks, eventually having timed things right so that we each got to know which house the other lives in. Discussions about neighborhood gossip and yards and doggy playdates turned into setting up our own doggy-style playdate, and it went so well that we made it a regular thing. Since she loves being on her hands and knees, I scoot face-up under her for some sixty-nining almost every time, wondering how the fuck her last boyfriend could have been put off by the soft light thatch of pussy hair that she swirls around on my face. In the last two weeks, she has steered the conversation away every time I’ve slipped in a mention of girl-girl sex, threesomes, sharing, or FFM porn, so she didn’t get on the threeway-with-Ellen shortlist.
When I gave my late-twenties coworker, Julie, a ride home a few months ago while her shitty car was in the shop for three days again, she offered a thank-you blowjob. Being the gentleman that I am, I refused to accept a sexual encounter from which only I would derive pleasure. Not having any condoms on hand, and unwilling to try to find and steal any that her roommate may have had, she agreed to postpone any amorous activity until we could confirm our mutual attraction outside of the heat of the moment. That weekend, we started in on a box of SKYN Supreme Feels, finished it a week later, and have gone through several boxes since. Trading stories with her roommate (yeah, they have heard each other!) has increased her sexual desires enough to have given a threesome some consideration when I brought it up — just not with her roommate. But a Julie-Sebastian-Ellen sandwich has become a real possibility.
When my ex and I broke up before the holidays last year, her friend Lina moved in on me. Since she’s a single mom, I was afraid she’d try to hook me as a replacement dad during that time of year that makes people do some crazy shit. But I can’t resist the offer of MILF pussy, and once I got some of hers, I couldn’t stop. Thankfully, though, our relationship has remained only sexual. Her pleasantly plump mommy tits have twice been the recipient of my gushes of sperm, but she put a hold on the tittyfucks when I accidentally glazed her hair and chin. She wasn’t upset, keen to keep fucking, but we agreed that we’d keep my ejaculations below the belt. It’s good to have honest healthy communication. I stopped by her place with some take-out and fucked her silly three nights ago, giving her a slimy vaginal creampie at her request, but left without thinking she was the right one for a threesome conversation.
Brooke drew a heart on my cup when I stopped by the coffee shop last week. The “arrow” that pierced the heart was rather blunt at the tip and had a wrinkled sack instead of feathers at the tail end. This is why she’s my favorite barista, and why I keep spending $7 on the coffees she makes for me twice a week instead of brewing my own for under a dollar. We’ve formed sort of a bond, as I commented on her braces having come off just a few weeks after I stopped in there the first time, and as I have verbalized my awareness of each new piercing and tattoo and hair color change during her unusually-long two-year tenure at the Bean & Brew. It took us a long time to hook up, but I’m glad we did. Indulging in a joint and a drink or two turns her loose, and her night shifts seem to make her horny. So when we fuck, probably more than once a week on average, she wears me out at my place, at her place, in my truck, or wherever — even in the lot behind the coffee shop after she closed one shift last month.
Barista Brooke’s talk about trying some lesbian kissing and fingering with a couple of community college classmates opened the door for me to ask about a threesome. Her telling me she has a crush on Rachelle, her seasoned coffee shop manager, swung the door wide open for me to ask about a threesome with an older lady.
So, here I sit in my truck at yet another fucking red light, stroking the stiff cock that’s been in inside Jocelyn, Don'elle, Anna, Julie, Lina, and Brooke all within the past two weeks. Recalling my last time with each of them is just not quite as exciting as looking forward to fucking Ellen again, for the first time this month, especially since my oldest and youngest fuckbuddies are about to double up on me, if all goes well. Brooke’s evening shift starts at 5:00, and Ellen and I make our own work schedules, so a taking time for a mid-afternoon two-on-one made perfect sense.
Only four minutes after Ellen’s “I’m here” text, I guide my truck through the alley behind my house up to the rear-facing garage. It takes a minute and some concentration to pull past her gleaming Lexus SUV and back in beside it without scraping her bumper or taking out the neighbor’s fence — just enough of a fuss to cause my dick to deflate down to sufficient flaccidity to get zipped up in my pants without too much trouble.
“Tight fit?” The classy-looking woman greets me as we come together between our vehicles once I’m parked in the garage.
“Yeah, but slipping into tight spots is kinda my thing.” I crush my mouth into hers and grab her ass, pulling up the snug and stretchy pencil skirt that’s no doubt sealed a deal for her today. “You had to get the biggest fucking Lexus, didn’t you? Gotta entertain the clients, I guess, but you could have left a little more room.”
“You could not be late next time.” She’d be a bitch if she wasn’t such a hot piece of ass.
“Not late. Right on time.” We enter my house through the door from the garage into the kitchen.
“If you’re not early, you’re late. Speaking of late, your little plaything isn’t here yet?” She sets her purse on the counter. “Hello?” she calls out in a loud sing-song voice. “Sweetie, are you here?”
“She’s a feisty one. Maybe you’re our plaything.”
“We’ll see.”
“Would you like a drink?” I ask. “Water, juice? Wine? Something stronger?”
“Our third… is she even old enough to drink?”
“Legally?”
“Touché.”
It takes less than two minutes for Ellen and me to start making out and groping each other on the couch. She undoes my pants and offers her tits to my grasp through her silky blouse. “If I wear you the fuck out before our little guest gets here, that’ll teach her to be late next time.”
“She’s young,” I reply. “Give her a break.” Against my better judgment, I let Ellen get my cock out as I stand at the end of the end of the couch, with her lying on her back, her head hanging over the armrest. In this position, she can tease my shaft to full stiffness while tonguing and sucking my balls, and I can unbutton her top and pop the front clasp of her bra open.
The doorbell ringing interrupts — no, intensifies — our foreplay just as Ellen shrugs off her blouse and bra to give me unencumbered full handfuls of her glorious breasts.
I’m pretty sure it’s Brooke… sure enough that I don’t bother to try to hide my sloppy boner any better than just pulling the zipper up over the elongated bulge as I unlock and open the front door.
Pushing past me after a cheerful “hiya, Seb,” the tight young barista stops in her tracks.
Ellen hadn’t bothered to put her tits away when I went for the door, but she’s now standing in a posture of modesty unlike anything I’ve ever seen from her, arms crossed, hands covering her boobs. “Oh, honey.”
Huh!? I’m confused.
“What the actual fuck?” Brooke stands with her hand on her cocked-out hip, her voice equal parts indignation and laughter. “Mom!?”
