Jenna and Greg were a highly sexual pair. They played and experimented together, and often in their tanglings, they would taunt one another with whispered depraved fantasies to add the spice that sent them both careening over almost every gushing edge.
And from their recent dirtier dialogues, it was clear to Jenna that Greg was longing and so very ready to try some playtime with his own sex, as long as his Jenna girl was with him at every naked turn.
But his constant hesitation was about other peoples’ opinions, taking his experimentation, and slapping him with a permanent label. He worried about how his business might be impacted if word got out, but Jenna knew that his concern was mostly in his mind.
"It makes you more of a man to me, babe", she would say. "I know, but not everyone sees it that way", was his oft-heard replied.
Then came the shining answer, the day that Jenna saw him rubbing his pretty big erection through his boxers at some gloryhole pics, as he surfed through his online visual smut world - something they often shared with one another to incite further sexual combustion.
She stood quietly, eyeing him and the lusciously perverted photos. It spun her brain about to the point where, even her own fingers were dipping into her dampening, hungry slit at what was brewing in her head.
The only words she spoke to him, when they saw the pics of a man pressing his girl’s face to the cock in the hole was, “Mmmmm, yessss…”
What she wasn’t saying was “I soooo want to turn the tables and do that to you too, mister!”
It’s not that she couldn’t say it. It’s that she had a real life plot thickening in her mind, and suddenly, she decided this could be the perfect fucking surprise gift for his birthday or their anniversary…. or for Christmas - whichever came first.
Jenna’s friend Christine, who often hooked her up with the latest masturbation toys, was a sex entrepreneur, among other things. A teacher by day, and an “adult party” organizer by the dark of nights. Jen had been to one of those gatherings before she met Greg, and she knew that some of them had gloryholes. It was time for a secret dirty conference with her naughty friend.
"How do you know that the cocks are clean, Chris? You know, disease free?"
"Darling Jen, first of all, I often use the same guys. I’ve known them and I’ve even blown them myself, and I’m healthy as can be. I have to protect my business, so they have to get regular tests. I promise, no sex cooties. You can suck and fuck worry-free. The other option is, you can supply the cocks, if you know the ones you’d prefer for you and Greg to play with."
"Oh God, no! I mean, I do know of a few I’d dare to invite, but the idea for Greg to get past his worries is for this to be completely anonymous. If he feels safe on that level, he won’t hold back. I know him. And I am dying to see him let loose with this bi-horizon he is perched upon."
"Okay Jen, I can get you a half dozen, certified-healthy hot cocks for those holes. I can host it at my biz pad. You were there once or twice, right? And you and Greg can be the only ones in the hole hall. I love that this is his first go-round with boys. I might even have to watch - and you don’t have to tell him that." Christine smiled her ‘our little secret’ smile.
The girls discussed fees and arrangements, and by the time Jenna left, her silken panties were soaked from the visuals in her head and rubbing against her swelling clit. Christine even tempted Jenna with the possibility of a video of the event, but again, the anon thing was the only reason Jen said no. “Next time, maybe, if there is one. I want him to feel safe.”
"Happy Anniversary, baby!" Jenna kissed Greg deeply with an extra-sexual hue to her assault, and in no time, her hand was rubbing the genie-in-the-lamp behind his zipper.
She thanked him endlessly for the gifts he had just given her, and as they readied for their special night out at a primo cafe, she whispered that she had some plans of her own for the later part of their evening.
"It’s my gift to you. One that will keep on giving." She wanted to say "keep on cumming", but she loved keeping the mystery of it all.
Dinner and wine and loving lust seeped into the early hours of their celebration. And as she and her beau were wrapping up to leave, Jenna texted Christine, “On our way”, and pulled Greg off of his beeline to the parking lot. She pointed to a limo and said, “That’s for us, baby.”
There was champagne in the back, chilled and ready for them, and before the driver pulled away, Jenna said with a wicked whisper, “This is my surprise for you, honey, so you’ll need to wear this.”
She put a blindfold on him, fed him champagne from her mouth, and taunted him with hints of what they were headed for. The one that had his mind spinning in wonder was, “This is something we’ve both been dying to try.”
At the destination, he was led into a pristine hall, still with blindfold intact, and before she let him see where they were, she assured him that this arrangement was completely healthy, utterly safe and totally private. She mentioned Christine as the purveyor of this, since Greg knew Jenna’s naughty friend, and knew that she, of all people, could be trusted. No one else could or would see them.
Jenna undid the blindfold, and wrapped herself around Greg from behind, unbuttoning his shirt and palming his cock as his sight adjusted to the light, and he drank in the surprise of his surroundings.
"Uh huh. The perfect place to play. Experiment. Taste. Everything. They can’t see you. You can’t see them. Just you and me, babe, and whatever pretty cocks come through those holes."
"Chrissy and I worked out little sound signals… so… you won’t even have to see her. What do you think, babe? Up for something dirty and daring?? I can share, or watch, or help you with the first… or with all of them. Mostly, I want you to do what you’ve been dying to try for awhile, and I’m going to fucking love every wicked minute of this."
"Oh my god…" he managed in a hoarse whisper. "Really?"
"You know Christine. They’ll be healthy, safe and anonymous. You can say ‘no’ if it doesn’t feel right… yanno, cuz I love you."
She tried not to let him see her biting her lip, praying for his “Yes”.
Greg kissed her hard and said, “Fuck yes. This is perfect.”
"Mmmm", Jenna purred, "I love you even more…"
Jenna knocked a pre-arranged signal on the wall with the holes, and the first beautiful long, thick cock slid through, semi-erect and glistening with the temptation of pre-cum. The game was on…
"Wanna solo your first, babe?" Jenna asked as she saw her man eyeing the cock that was clearly begging for touch.
"You can help. Errr, I mean, let’s share this one", is all he could manage in return.
Jenna took Greg’s hand and together they slowly stroked the protruding penis, as their bodies instinctively genuflected to the floor to ready themselves for their first shared carnal tasting.
Jenna went first to demonstrate, licking the wet slit, teasing the undercarriage, then lip-wrapping and taking in more than half its length. She suckled and teased it, then slowly unsheathed and let the cockhead “pop” out of her tightened lips.
And Greg mirrored almost everything that his girl had just showed him perfectly, adding a few manly taunts of his own, as she sensed he would. As he took that first taste of rigid male sex across his tongue, Jenna moaned softly to herself, and unzipped her man to discover that she was not the only one who was already wet. She whispered to herself “Fucking perfect!” This was going to go better than she’d hoped.
The first cock they played with in tandem, perfectly sharing the sucking and stroking duties for each other. At one point, they tried french-kissing with the shaft and head between them, then continued while sliding up and down its now rigid length.
When Jenna could feel the cock in the hole fighting those telltale pre-orgasmic tremors, she ceded the dick to Greg, and stroked both the wall-shaft and Greg’s hot rise as she whispered “He’s about to blow, babe. You take the first shots, I’ll take the last ones..”
With a mouthful of trembling meat, Greg had no way to answer, and before he knew it, he too recognized that point-of-no-return twitch in the cock he was swallowing, and as the first hot spurts spewed across his tongue, he heard Jenna groaning “Yessssss!”.
Greg boldly took as much as he could - this invasive sensation was all so new to his open maw - and the minute he backed off to orient himself, Jenna wrapped her mouth around the cumming cock and caught most of the seed it was still shooting.”
Both lovers, their faces full of a stranger’s freshly spouted sex cream, locked eyes and without a word, began to kiss like ravenous wolves trying to taste the spoils from the depths of the others’ soiled throats.
Jenna fought to speak between the sticky kisses “So. Fucking HOT…watching you. Sharing him with you. Tasting him inside of you. Fuuuck!”
They lapped up more warm gooey cum from each others’ lips and Jenna dared the question:
"Did you like it?"
"Enough to try more?’
"Oh yes. All safe. All yours if you want them."
His next words made her clit buzz and her cunt gush.
”I want to try the next one on my own.”
"Jesus H Fuck, Greg. I soooo fucking LOVE you!"
Another seed-glazed deep kiss.
"You won’t mind if I play with your ass and cock while you suck his, will you?", she taunted.
"I was hoping", he winked back with a knowing smirk.
That’s when he saw the other pre-arrangement in the corner - a bag of sex toys. Greg thought to himself, “Of course, it’s Christine.”
Jenna knocked another signal on the wall, and a nice big curved cock slid through the opening and wiggled into near balls-deep place for the suckling. Before Greg could start, Jenna stripped him of the rest of his clothes, humming something about needing complete access.
"Take him, baby", she taunted when he was finally naked, "This boy is all yours." Then she added "Make me proud!" which made her giggle lasciviously.
Jenna tore at her own clothing as she watched her man stroke and play and explore this new scimitar-like curved dick, thick and insistently hungry for a stranger’s mouth. Jenna could almost not concentrate on grabbing the right toys, because she as completely transfixed by her emboldened guy discovering his blossoming talent for flesh and blood sword-swallowing.
She managed to find her plug and the lube easily enough, and every now and then she’d run her palm under Greg’s rock hard cock to happily feel the puddles of pre-cum waiting to grace her fingers there. Every time she felt that, she knew that he was loving this more than she’d expected.
Jenna began to use his pre-cum to lube his anal opening, as her fingers plunged inward and added a unconscious moaning hum to her boy’s sucking technique. In no time, the curvy thick dick began to spurt its streaming wet bliss all over Greg’s face and into his willing cheeks, as he struggled to capture it all for the sharing.
As the cum-blasting orgasm began, Jenna moved to the wall, laced her fingers in Greg’s hair and cheered him on. “Take it all! Don’t miss a drop! I want to lick it from your throat, baby!” That make him swallow the hardened hose even deeper.
Greg was still getting used to the whole erupting spout in his mouth, but he did well for his first solo suck. And Jenna kissed him deeply afterward, lapping away at the spoils he had captured in his cheeks.
In between the bitten kisses, Jenna got very guttural with her declaration that “That is the hottest fucking thing I’ve ever seen!!”, which only set them both on further fire.
”Okay, babe, tell me what you want.”
Christine ordered six. We’ve had two. You do the dirty math”, she teased him, while she continued to taste the second stranger’s cum from his scruff-framed lips.
They’re all for you, babe. I can help. I can watch. We can share. But I have one request for me - I definitely want to fuck your hot ass with a girlcock while you take one down deep.”
#’s 3, 4, then 5
That set the couple into feverish motion. The third and fourth cocks, they decided were to be sucked together, side by side, both Jenna and Greg watching each other go down on a different cock simultaneously. The spoils of both would be running down their chins and bodies once they cause those dual explosions.
In the mix, they even decided to switch cocks once or twice, to see how the reactions changed to the differing touches of male and female mouths and grips and fervor. There was almost a game-play feel to this one, Jenna pushing Greg’s face to the base of the cock he had in his mouth, then him returning the favor when she wasn’t expecting it.
Finally, they staring pumping and and bobbing on the cocks they each began with, hoping they could make them cum at the same time, in twin creamy bursts of wicked goodness. And they very nearly succeeded, with the echoed orgasms hitting just seconds apart.
The clean-up got highly messy and heated, and cum was all over both chests and bellies, even smeared intently then devoured from both Greg’s cock and Jen’s sopping cunt slit.
The pair were so ramped up after this fiery wet-dream game, that Jenna didn’t wait for Greg’s okay for the next go-round. There was no need. The look on his face was one that said he could take on an army in that moment. She reached for the strap-on, grabbed a nice long girlcock in black, and rapped on the wall for one more loaded weapon to appear.
It was perfect size for Greg to learn some deep throat-ing skills, Jen thought to herself. He was going to get spit-grilled now.
Jenna licked and lubed and primed Greg’s ass as he fondled and kissed the new pretty cock.
"Wrap your lips around that drippy dickhead, sweetheart. I want him to feel your first ass-ride’s moaning hum."
Greg did as she asked, as Jenna popped her girlcock’s wide head into Greg’s willing anal clench. The growl that occurred stirred them both into further and faster motion, and by sheer instinct, Greg took 3/4 of that exposed cock into his widening gape in one hungry move.
As Jenna worked her strap-on into her man’s hot butthole, she nudged forward and leaned into him with whispered dirty talk while his mouth was full of raw man meat,
"Remember that photo of the guy pushing his girl’s throat onto a gloryhole dick? I’m going to do that to you, baby. Just open your throat, and when he starts to cum… and trust me, between the depth he hits, and your hot growls, he will in no time… just let that wash of seed jet right down your throat into your belly."
There was nothing else to say. Jenna reared back and began pile-driving Greg’s asshole with her rocking hips and plunging girl-dick. Her right fingers laced into his hair for the first pushes, and as things revved up, she had both hands pushing Greg into the cock on the wall, while the cock’s owner was desperately trying to fuck him back through the plaster.
Jenna had never fucked Greg this hard before, but the sight of him pressed forward to devour another man whole, while arching back willfully into her rutting invasion had her on her own dripping precipice.
Suddenly, she heard a different sound. Greg was trying to mouth the words “He’s cumming” with a throat full of swollen umbrella’d flesh.
Jenna cried, “Yes! Just open up babe. Take it all!!
She mimicked the photo, shoved him nearly past the wall’s opening, and she could hear Greg gurgling through a river of cum that he was allowing to stream directly into his gullet. That lewd noise alone sent Jenna into a ferocious orgasm of her own.
Then the sounds of the man on the other side, pounding the wall and roaring from being deeper in a throat than he’d ever imagined possible, had everyone wailing their orgasmic joy along with him.
They took a break. Greg needed a short one at least, but the degree of filth they had both already wallowed into had their carnal furnaces still on high, and wanting more.
"How’re you doing, babe?" she purred, as she stroked his beautiful body and nipped at his sticky chin. "All sucked out?"
"holy shit…" was all he could manage.
"No worries. I don’t think you could top that last one. You were fucking amazing! Did you like it? Love it?"
He smiled a wicked smile and purred. He didn’t need to say more. That Cheshire grin alone made her clit do a happy somersault.
"So", Jenna nuzzled into her dirty boy, "There’s one more cock, babe. And a few options. Or we can leave it."
"Tell me" he panted.
Well, I could suck it while you fuck me. Or… Christine said there is an option of reversing the wall.”
His quizzical look made her explain. “Just shove your cock through a hole, and one of them will return the favor. Maybe even two. or a boy and Christine if you prefer. Or maybe they can all take turns and see who wins your cum!”
He liked that last one, but didn’t jump at it.
(and yes, she had thought this out ahead of time)
"I was thinking…" She leaned in and whispered in his ear. Then pulled back for the rest.
"You’re already primed, and that would complete the fantasy, safely and anonymously, while you cum-dump down my throat like the last guy did to you. Your choice, babe."
She knew this would get him, and it didn’t take Greg but a moment to decide on the final obscene option.
When Greg was ready for the feral finale, Jenna knocked on the wall for the last erect cock, and god, it was fucking perfect for their plan. And, of course, that was no accident. Christine had helped in the sexual plotting. it was the longest yet, thick and cut a with a beautiful wide head.
Greg was already lubed and stretched from the girlcock ride. He and Jenna stood together, kissing sensually, while both gently stroking the pole in the hole.
"Let me give it some goo, babe." And lube the thick member she did, then added the leftover to Greg’s spread rear door. The lube on the cock told the man on the other side he was about to get luckier than the rest.
Jenna knelt and nipped at Greg’s ear as he bent forward toward her, aiming his hips toward the slippery probe in the wall.
"I am sooo glad you wanted to try this. Now you can feel what I feel when you fuck me. And even more, what you can’t get from my girlcock - those wild jerking spurts of cum filling you deep in your hot little asshole - UNF!"
Jenna aimed the slippery wall-dick and guided Greg’s asshole to slide back onto it.
"That’s it babe… now push back a bit." Greg was shocked at the ease with which he took this big thing inside of him, already forgetting that his ass was freshly fucked by his girl.
Jenna slid back and wrapped her soft hand around Greg’s very swollen pre-cum-soaked cock, knowing that he was not going to last long with a dick in his ass and her throat giving him a tight, wet burrowing place. She kissed the head of her boy’s cock and offered one last word of advice.
"Babe, when he’s about to cum, push back hard. Take him all the way in. Then tighten and hold onto him. You will feel that eruption so fucking deep, and he’ll be trying to break through that wall to get deeper."
He saw the wide eyed look, and she laughed “Don’t worry. He can’t break the wall. Or you. Go, babe…. fuck him like you mean it!”
And with that, Jenna lips encircled her man’s shaft and began to go to work on him.
Even Jenna was surprised at how long Greg lasted and how much he toyed with the cock in the hole - riding it slowly in lengthy strides, then slamming on it, causing Jenna to a to grab Greg’s hard-on until her mouth could recapture it.
All the while, the plug in Jenna’s ass was sending spiking pleasure waves through her entire body as she watched her man fall into the reverie of having his ass’s needy canal impaled by a big-dicked stranger. She lost count of her own O’s, since it only took some quick self-fingering to trigger even a small one at this point.
Sshe could feel Greg nearing the tipping point, and she knew that the intruder was skirting his edge as well from the sound of things.
All at once, with a strained wishful whimper, Greg cried out, “Jen. babe. he’s cummm…uhhhhhh”.
With one forceful move, she shoved Greg as far onto that exploding cock as she could, while thrusting her own lips to the base of Greg’s shaft and balls. Jenna could almost feel the first jets of cum shooting into Greg’s mancunt from the wall-fucker, but just seconds after that, she felt Greg’s own monster eruption begin to drown her in his blissful sex wash.
The two ravenous cocks continued to empty buckets of orgiastic cum into their respective warm wet cocoons, while the sounds that came from all three rutting hedonists could have made the entire neighborhood around them soak their sheets without a touch.
The rabid trio were grunting obscenities and trying to make the ride last longer than anything they’d ever experienced. In the end, it felt like they did, and then some.
When Greg finally slid his impaled, sated asshole off the still sparking anonymous appendage, the couple tangled around each other and kissed and bit and licked and and grunted like mating animals. In the midst, they declared their love for each other and for all the depravities they’d been brave enough to share together.
Had enough cock for one night, babe?” Jenna teased. “You were quite the little cumwhore, weren’t you?”
He swatted her butt playfully, and she turned serious for a moment. “I am so very proud of you and so fucking in love with you, Gregory. So anytime you need another cock to join us, just say so. But… you’ll have to share it with me more than you did tonight.”
She laughed at her own last comment, then added, “Good news. C’mon, Christine has a nice clean up place for us before we go.”
A new signaled rap on the wall, opened a door, and there was a pristine bathroom with all the accoutrement, eve a pretty bath and shower.
"Let’s not clean up too much", Jenna purred. I like the idea of licking the rest of the man-cum off of your body. Mmmm, shall we plug your ass to keep that deposit in there until we get home? I can fuck it out of you and you can suck it off of my girly cock."
As soon as those words left her lips, she knew that she was going to do that, no matter what he said.
Jenna texted their hostess to let her know that their Anniversary playtime was done. The couple dressed and wandered out to the limo in the dark, still unseen by anyone. As they reached the limo, Jenna got a text from Christine to come back in for a moment.
"Settle in, babe. Be right back."
Christine was all flushed when Jenna got back inside.
"Jenna, honey… that was the sexiest fucking thing i have ever seen a couple do together! And you know I have seen a lot.
Two things: First, I’m giving you a bigger discount than I mentioned. The orgasms were fucking worth their weight in gold! And no need to tell Greg that I watched. You know I’m the last person to spill the beans on anyone.”
"I know Chris, since I know all of your nasty secrets." The girls laughed.
"Second… ahem… I know you said no video, but… this was too fucking hot to not record. So, here’s a copy for your masturbation files."
Christine handed Jenna a thumb drive. “Trust me, this will keep you cumming for-fucking-ever.”
Jenna thanked Christine profusely, the girls hugged, and as Jenna turned to go, Christine said “If you two ever want to repeat that for a video to sell, you can always wear half-masks. Just saying. It would make a ton of cash with my folks alone. Think about it.”
Jenna loved the sound of that, but that was a discussion for another time. For now, she meant to have some more of her boy who’d just been had by all the other boys.
When the couple was back in their own car and headed for home, Jenna softly asked, “So, did you like the idea of that second option, of being on the receiving end of the gloryhole and being sucked by one or a few other guys?”
Greg stayed silent for a bit, which made Jenna a little nervous. Then he grinned and quietly said, “Maybe next time.”
Those two words “Next time” would spin in Jenna’s head and send her deeper into more plans and fantasies… until next time came.