"Eenie, meenie, minie, mo" (closed)

[The_gladiator]

This had been quite the strange day, but apparently sometimes strange was a good thing because it wasn’t long before Will felt the soft hands of Diana guiding his hands to cover her breasts. They were soft, the skin supple and despite the sag that gravity gave them, proving indeed they were real, her nipples were very hard and poked against his palms. At her urging he allowed his fingertips to brush in small circles until he found the protruding nipples, like little eraser tips poking out from her full breasts. “The skin is softer than I imagained.” He told her in response to her question.

Next thing he knew she was kissing him. He had done that before, but never with such…passion. Unconsciously one hand slid from her breast and up into her long hair as they kissed. The kiss left him a bit breathless as almost zombie like, he walked to the door, fumbling with the lock.

He had been following her bases analogy and though he was familiar with the concept he did not stop her from explaining. At her condom question he shook his head. “Sorry, I don’t. I guess I could only steal third base, then?” He joked and then looked a bit shocked at his own boldness. Had he really just asked for oral sex from this beautiful woman, one of his sister’s friends no less. It wasn’t even from Terry the one he was sure was gonna strip him bare and ride him into the sunset in his father’s truck. This was Diana, his sister’s good friend. A Diana that was grown up, and had just kissed him, let him touch her breasts, had let her own hands roam up his arms as he had touched her, like his touch was truly welcome. God, he wanted more, even if that meant he could just touch her breasts again.

 

[PollyWannaCracker]

“Sorry, I don’t.”​

Diana didn't know whether or not to be surprised at Will's reluctant confession that he was packing a condom. So many of the 'boys' at school carried them in their wallets 24/7, as if any more than just one or two of them had ever had an opportunity like this.

"I guess I could only steal third base, then?”​

She smiled at Will's obvious and hopeful suggestion that, short of getting to fuck her, he was going to get something more than just a handful of boobies. After he returned from locking the door, Diana kissed him again, turned him so he was standing immediately before the bed, and began unbuckling his pants as she kissed him yet again.

Suddenly, there was a knock at the door, followed by the jiggling of the handle and Polly calling out, "Will! Where's my laptop? We got thirsty girls out here."

Diana saw the panic in Wil's face, but quickly she explained, "It's okay, she knows we're in here together."

She snatched up the laptop, ran it to the door, unlocked and opened the barrier, whispered to Polly for a moment, then closed the door and returned. She looked into Will's face and asked, "Should we continue?"

It had occurred to Diana that after telling Will that his sister knew she was here, that things might change regarding what had initially appeared to be a spontaneous encounter. She hoped not, but she wouldn't know until Will either confronted her or told her to take his pants down. If he said nothing at all, Diana would simply resume to stripping his lower half, eager to finally see the cock about which she'd been dreaming to see and feel for almost four years.

 

[The_gladiator]

Will felt her stear him until his back waas to the bed. Her hands slid down his chest to the belt of his jeans. Was this actually about to happen? She had just gotten the tongue of the belt free, and there was a pounding on the door, and the handle jiggled. Will felt his heart skip a few beats adrenaline shooting through his body as it happened.

Diana tried to sooth him, confessing his sister knew he was in there. Will felt very conflicted. If she knew, then obviously this was a setup. When she returned he hesitated. He wanted this to happen, this was an opportunity he might not get again, with a woman who was beautiful, a young woman he trusted. “Isn’t it weird that she knows?” He asked, “I mean did you plan this with her, because Terry was acting forward in the car too. I mean she and I didn’t do anything like what you and I have done but…” he very much looked confused.

 

[PollyWannaCracker]

Diana was hurriedly working Will's buckle and the snap of his pants as he talked about his sister's knowledge of this moment and of Terry's earlier involvement in Will's weekend of adventures. He told her:

"...Terry was acting forward in the car too. I mean she and I didn’t do anything like what you and I have done but…”​

"Polly would never have let that slut take your virginity, Will," Diana blurted out defensively. She looked up into his eyes with wide eyes, shocked that she'd actually said that out loud. "I mean, what I, I mean Terry, she's nice'n'all..."

Diana had no idea of whether she'd just damaged her chances here, and she didn't know how to talk her way back into Will's pants if she'd just fucked up. So, the obvious course was: get into Will's pants.

With one quick jerk, Diana whipped the zipper of his pants all the way down, then reached down through the waist band of his underwear to grasp his cock firmly. She had expected it to be hard, of course, but what she found even surprised her, It was hard to tell with just a single hand down his pants and no view of the thing, but Diana was feeling and impressive girth to a cock that was at least 7 inches long and maybe even a couple of more beyond that....?

 

[The_gladiator]

He was surprised at her vehemence about Terry. “I didn’t know she was known to be a slut, well I mean after today I could have guessed but…” he stumbled over his words. “She does approve of you? I mean I’ve known you a long time,” he sounded a bit hopeful. He wanted this to happen, but he wanted it to mean something too. He was now suspecting his sister had set him up to take his virginity. Clearly that was the case. He wanted to lose it to someone he had feelings for. Could Diana check both boxes.

His thoughts were swept away as her small hand slid in to cup him through his briefs. Her fingers traced the outline of his cock. He hadn’t been into measuring himself like some guys but had never been embarrassed in a locker room. At about 7 inches long and 2 inches wide give or take in the best ways he was well proportioned, with a slight curve, though that wouldn’t be obvious until out of his underwear.” He gasped at even this touch. “Diana, oh god… you’re touching me… Are you sure about this?”

 

[PollyWannaCracker]

“Diana, oh god… you’re touching me… Are you sure about this?”​

The bosomy redhead answered Will's question by dropping to her knees before him, grasping both his jeans and his boxers, and pulling them in one movement all the way down to his ankles. Her eyes opened wide as his rock hard cock flopped out before her, bouncing a couple of times before settling down, pointing directly at her face.

"My God," she murmured, leaning left, then right, then returning to looking it straight on. "It's so 'fat'!"

Diana was no Terry, but she'd seen a dick or two or four during her two years of sexual activity. Not all of them had found their way into her pussy, and only one of them had been lucky enough to find comfort in her mouth. Two of them had been longer than Will's, but not a one of them had ever had the girth of his 'pants monster'.

She reached up, grasped it firmly in one hand, and squeezed tightly as she began slowly stroking much of its length. She looked up into Will's face and asked, "You 'are' a virgin, right?"

 

[The_gladiator]

She yanked down his pants by way of answer. There it was, his cock pointed at her face, up and out at a 45 degree angle, with it’s slight downward curve. Before he knew it her hand had corcled him and stroked him.

Will almost jumped, he’d never been touched by another hand before, and it felt good. He looked down at her kneeling before him and answered softly. “Yes, Yes I am. Is that a problem Diana?” He asked, using her name as if to see if this moment was truly real. She looked like she was about to put him in her mouth and he never dreamed about being at this point with anyone this weekend, let alone her.

 

[PollyWannaCracker]

"No, it's not a problem at all," Diana responded in answer to Will's own answer about being a virgin. "I'm happy you are."

She lifted her haunches from her calves and pushed the man back onto the bed. In a flash, his shoes, socks, pants, and boxers were tossed away, and Diana had moved up in between his knees, which she pushed apart with her hands. She didn't hesitate to take Will's cock into her mouth, first just the head (which she sucked on powerfully for a moment) and then it and a couple of inches (which went in and out, in and out four or five times).

Then, grasping her tits and pushing them together, Diana spit into her cleavage, looked up to Will, and said, "I don't think that's enough. Spit here. Where I did. We need more lube."

 

[The_gladiator]

She pushed him to a seated position on the edge of the bed. He was able to look down and watch as she spread his knees with her hands and then took the head of his cock into her mouth. “Oh, wow,” he breathed at the feel.

As she lifted up and surrounded his cock with her breasts he was a bit surprised. He’d seen that in porn but really wasn’t aware people really did that. “Uh, ok,” he said and leaning down let saliva run out of his mouth onto her chest. “Might have been easier if I just licked them but hopefully that helps,” he offered.

 

[PollyWannaCracker]

Diana's DDs were more than sufficient to get done what she wanted to do to Will. As she enveloped his shaft in the cleavage of her generous, 'squished' together orbs, she looked up to find him with an expression of awe.

“Oh, wow.”​

He spit as she requested, hitting absolutely perfectly where the 'fore' of her tits wrapped around the 'topside' of his length. She spit once more on the 180 degree opposite side, shifted the 'mamms' about to spread the saliva, then went to it: raising and lowering her body with her back leaning forward, the bending back, then repeating, Diana was very quickly getting a 'titty fuck' that she knew wouldn't get her pregnant.

She looked directly into his face, into his eyes, wanting to enjoy his reaction, to see it and hear it and feel it as he exploded for the first time with someone other than 'Rosy Palm'.

 

[The_gladiator]

He watched her continue to spread lubrication. The sight of her breasts around his cock were exciting. He found the feel did not compare to her hand or mouth, and yet the slipery slide of her breasts still felt good. He still suspected he would finish quickly from the sight alone. “Wow, I can’t even believe…” he again did not finish his sentence as hewatched her head dip down to tease the head of his cock. “Oh My,” he whispered hands clenching unconsciously in her long hair.

“You should probably stop soon, I’ll make a mess,” he told her shyly.

 

[PollyWannaCracker]

“Wow, I can’t even believe … Oh My.”​

The effect on Will of his cock slipping up and down in the vise of her clenched tits was oh so obvious to Diana. It made her smile with delight. She'd waited so long to pleasure Polly's brother, so many years while he 'languished' in that relationship that hadn't seen his cock get anywhere near his Ex's 'treasure chest'.

This was only the first step, Diana told herself. She wanted him inside her, of course, and he would already be there if they'd had a condom. It pissed her off that Polly hadn't told her Will was coming to the rental house until they'd actually arrived here. Will's sister had known about Diana yearnings for her brother almost as long as those yearnings had existed.

'Tomorrow', she told herself as she continued to manipulate her massive mamm's up and down his shaft, spitting once more into her cleavage to lube the working parts and telling him to do the same. 'Tomorrow, I'll get a condom and Will will be mine.'

Of course, tomorrow was a long, 'long' ways away, and there were plenty of other young women in the beach house with designs on Will's virginity. 'Is he still a virgin?' Diana thought to herself, knowing he was only moments away from spewing a load of cum all over himself and herself. She guessed he was, technically. She wanted to mount him, to make her claim to his V-card official, but she was dead in the middle of her most fertile days having quit the pill after she and her boyfriend split up months ago.

“You should probably stop soon, I’ll make a mess.”​

Again, Diana laughed, not slowing but instead tightening the pressure and increasing the speed. She told him, "Make a mess, Will. It don't mind."

His brain must have heard permission begin given, because just seconds later, Will's cock twitched hard within its confines, sending a massive wad of cum straight up in the air. Diana's eyes opened wide in an instant and instinctively she looked upward, just in time for the glob of whiteness to plop down on her chin.

Also in shock, her mouth opened wide; the second volley of cum landed partially on her lower lip, partially inside her mouth. Diana had never liked the taste of cum before, thus the reason she'd abandoned sucking Will's cock and giving him a titty fuck instead. But she knew men liked to see their lovers take their semen into their mouths, so without thinking about it, she left her mouth open in case there was anymore of his thick stuff coming her way.

The resultant streams and then smaller globs of Will's cum ended up just about everywhere. Another spurt of it did in fact land right on her tongue, but by the time his cock had settled down and was only just trembling slightly between Diana's tits, it was all over her tits, her hands, and Will's lower belly.

"What a mess!" she laughed when finally all that remained of his climax was his cock's version of post-party night dry heaving. She looked to him, asking with hopefulness, "Did you enjoy that Will?"

 

[The_gladiator]

Will had never imagined he would have been in this situation, and yet, there she was giving him permission to release, to make a mess. Just those words made something happen to will inside, and he let go. It was a lot more than he typically produced. He felt embarrassed, and though she chided him about the mess she laughed, so clearly she wasn’t too upset about it.

He sat there panting, slumping back on the bed after a moment watching her. “Wow, that was, pretty awesome.” He said. He reached for the box of tissues and began to wipe himself up. He watched her head to the attached bathroom to clean up. He couldn’t muster the energy to get up more than to grab them. “Thank you,” he called to her, “I’ve never…”

 

[PollyWannaCracker]

“Wow, that was, pretty awesome.”​

Diana giggled, agreeing, "Yeah, it was, wasn't it. My god."

She couldn't believe how much gooey stuff was all over them. Diana moved back slowly, letting his still rock hard cock free from its confines; it sprung loose, slapping against his belly before rising again at an angle over him. She looked at it and giggled again: it was still twitching every few seconds without anything coming out, like a gun being fired with blanks.

"I need to clean up," Diana told him, "And I'll bring you a wet rag, too."

She reached a finger to her chin where a glob of cum dangled. Despite her lack of pleasure in doing so, she licked the thick goo off her finger and swallowed it. Surprisingly, Will's cum tasted good, at least compared to that of the one man whose jizz she'd ever intentionally swallowed.

She rose from her knees, heading to the bathroom. She warmed a washrag under a stream of water, wiped face, chest, and fingers clean, then returned to look at Will through the open door. She marveled at not just how good he looked there with his 'still rock hard' cock in the air above his abs, but at how sated he looked from what she'd done to him.

"Here, let me help," Diana finally said, going to Will to begin wiping the warm cloth over his skin and, particularly, all around his cock. She purred to him, "You have no idea how long I've been waiting to do that."

 

[The_gladiator]

He lay breathing hard still, his cock still twitching. She returned to begin wiping him clean. “Thank you,” he told her, laying a hand over hers. “You’ve really waited to do that specifically, or just be intimate with me?” He asked curiously.

He let his thumb trail over her skin, smiling.

 

[PollyWannaCracker]

“You’ve really waited to do that specifically, or just be intimate with me?”​

Diana didn't answer immediately, unsure of just how to explain her infatuation with Will. She didn't want to sound desperate, because honestly, she'd had other lovers during the four years that she'd yearned for this man. But at the same time, she wanted him to understand what it meant to finally be with him like this.

"To be with you, Will," Diana finally said, moving up to kiss him again for the first time since his cock had been in her mouth. "I've wanted you for a long time."

There was another pounding on the door, and suddenly there were at least three female voices calling out for the party's bartender. Diana's name was called out as well, along with lewd comments about what she and Will were doing in there. Laughter abounded, and it was obvious that some of the girls had already made a dent in the booze without the need of someone to mix drinks for them.

Diana stood, found her bra and blouse, and said with a smile, "Your public requires your presence, Will."

But then, with a more serious expression, she added, "I don't expect you 'not' to, you know, with some of them. I just--"

A shot of emotion caused the words to stick in Diana's throat a moment, then she finished, "I just hope that when this weekend is over, maybe you and I can go out for coffee or to dinner or a movie or something?"

 

[The_gladiator]

He smiled at her. “I never knew you were interested,” he told her quietly. “They seem to be intent on getting us to come out of here.” He said reaching for his underwear and pants.

He looked at her surprised she wouldn’t have been possessive expecting her to tell him not to be with the others. “I would love to have dinner with you sometime,” he told her stepping close to kiss her softly.

 

[PollyWannaCracker]

“They seem to be intent on getting us to come out of here.”​

Diana had to divert her eyes, actually turn her face away, at Will's understanding of the situation beyond the door. She would have loved to have the young man to herself for the entirety of the night, and when Polly had first arranged the 'spontaneous encounter' earlier, Diana had thought that that was what Will's sister had wanted, too.

But after realizing that Will had arrived surprised at her presence in the room, Diana had known that she would have to take what she could for now.

“I would love to have dinner with you sometime.”​

She looked back to him for just a short moment, smiling to him, showing her pleasure at his words before saying softly, "Thank you, Will. It's a date."

Diana headed for the bathroom, saying over her shoulder before she closed the door behind her, "I'll see you out there after I clean up."

Behind the door, Diana would plop down on the padded toilet seat cover, contemplate what had happened between her and Will as well as what was destined to happen between him and the other girls, and then cried softly.

Out in the bedroom, though, the door knob jiggled as a key was inserted and twisted, and suddenly a flood of female bodies filled the room. Laughing and teasing and generally being boisterous, they grabbed the barely redressed Will and manhandled him back out into the larger living area of the house.

"Get to work," Polly said when her brother was presented to her. The laptop she'd retrieved prior to Will getting his rocks off was opened to a cocktail making site on the internet, and the girls surrounding the kitchen's large prep island were already calling out their chosen drinks. Playfully, Polly patted her own brother's ass as she whispered into his ear, "I hope you enjoyed Diana, but don't think for a moment that that's the only 'meal' that's gonna be presented for you to eat."

She stepped away, held two liquor bottles into the air, and called out loudly, "PAR-TEEEEE!"

 

[The_gladiator]

He smiled to Diana, and as she walked off he got dressed fully. It didn’t take long for people to bust in.

He good naturedly let them stear him into the kitchen. He stook at the counter and began to take orders. He blushed at some of their compliments and began to work to mix drinks for them. He was slow at first but sped up. However, he jumped as a woman groped his ass. “You’re making this difficult,” he told her playfully smacking the hand away. The woman who was just a couple inches shorter pressed closer. “What would you like?” He asked, meaning a drink, forgetting he might be on her menu.

 

[PollyWannaCracker]

Polly wandered away to tend to other drink and snack issues as her brother was mobbed by her friends. She had feared initially that his presence at what had been billed to be an 'all girls weekend' was going to rub some of the girls the wrong way, particularly those in relationships with boys back home. But so far, even the 'taken' ones were having more fun than they should have with Will.

"So what do you think happened in there with Diana?" one of the girls asked the party's hostess surreptitiously.

Polly turned to find Carmen Delgado up close to her with a hopeful expression on her face. Despite having no facts while also knowing that her bosomy friend and Will had been in the room plenty long enough for him to have lost his virginity, Polly answered, "Not much, I would imagine. I mean, they've been friends for years, since we, Diana and me I mean, were in middle school."

"So..." Carmen began, not asking the question for a few seconds, wondering whether or not Polly would answer her imminent question without her having to actually ask it. When Will's sister only returned to pouring some dip into a bowl and mixing in extra ingredients, Carmen asked with a desperate tone, "So...! Do you think he's still a virgin?"

Polly let out a guffaw, responding, "Well, of 'course' he is. Really?"

To be honest, Polly was hoping that the lone male at the party had gotten lucky a few minutes earlier. Diana was a good, faithful, and trustful friend, and if she and Will had been 'bumpy uglies', Polly didn't have to worry about the girl spreading the news all over the party, the school, and the town.

"So...?" Carmen was again urging replies without asking actual questions.

This time, though, Polly knew what the girl wanted and said without hesitation, "Sure, if you want to fuck my brother, go for it. But...!"

She looked to make sure no one was eavesdropping before bringing up one of the popular jokes back at school, "I 'know' where in the world your pussy's been, Carmen, so 'condom'!"

In truth, the sexy Latina wasn't as much of a slut as Polly's comment made her out to be, but she had in fact had a dozen lovers over her three sexually active years. The slender yet taller than average girl from south of the border smiled broadly, kissed Polly on the cheek, and declared, "I 'owe' you!"

Polly let her eyes drop to the small but well rounded bosom of the dark skinned girl, then looked her in the eyes and suggestively told her, "And I'll be calling on you to settle that debt this weekend if you get anywhere with Will."

Carmen acted shocked, but she (like most of the girls here tonight) knew full well that Polly was known to 'play both sides of the net' at times. It was something she'd kept from her family thus far, including Will, because it was only this past year while he'd been away at college that Polly had discovered the joys of eating pussy and being eaten by pussy.

"If I get lucky," Carmen acknowledged, "you'll get lucky, too."

The cute Latina hustled off, weaving through the bustling, ever moving amoeba that was Polly's party goers until she was at Will's side. She looked for prying eyes and, believing no one see her, gripped the man's ass tightly in one hand, causing him to leap in surprise.

“You’re making this difficult.”​

Carmen very conspicuously looked to his crotch, then back up, asking just loud enough to be heard by him over the music and loud girls, "But am I making 'it' hard, too?"

She laughed and patted his ass again as he tried to turn Carmen's attention to drink making

“What would you like?”​

Remembering one of her favorite 'Big Bang Theory' scenes (when Penny was training to be a bartender), she used Howard's line, "How about a 'Slippery Nipple'?"

One of the other girls heard and laughed, calling out her own order: "I'll have an 'Afternoon Delight'."

Suddenly, the ring of girls around the island were calling out all sorts of suggestive mixed drink names: 'Between the Sheets', 'Ménage à Trois', 'Silk Panty Martini', 'Full Monty', 'Virgin Cherry Climax', and the obligatory 'Sex on the Beach'.

"You'll all have 'Rum and Coke' or beer if you don't give my brother a chance to work!" Polly chastised the 'herd' as she pushed her way up next to her brother to deliver chips and dips to the island. There was laughter and more lewd names and comments. Polly told Will to ignore them and just do his best, then looked past him to the smiling Latina. Putting her mouth up so close to Will's ear that he would be able to feel her breath on and in it, she whispered, "Carmen wants to fuck you. There're condoms in the bottom drawer of the 'blue' bedroom upstairs."

She pressed a key into her brother's palm, telling him, "I sort of reserved that room for you, bro'."

And then kissing him on the cheek, she turned and headed off to take care of more tasks designed to keep the 'animals' calm.

 

[The_gladiator]

Will blushed at her follow up question. “Not yet, though I’m sure you could manage to if you tried.” He told the dark skinned beauty. He laughed along with them as they listed off their drink orders, one even making him raise his eyebrows. “Sex on a dryer? Is that even a thing people do? I mean laundry equipment?” He laughed.

Before he knew it Polly was there, whispering in his ear. He shivered at the feel of her breath in his ear. He put that out of his mind for study later. Though it could have been what she said. His cheeks went read as he nodded his thanks. He offered a shy smile to Carmen. It wasn’t a yes, but it certainly wasn’t a denial either. How would he feel doing that when he’d just fooled around with Diana. However as fun as things had been with Diana, she didn’t feel as experienced as Carmen did. Just by the way she carried herself. “One slippery nipplle,” he said delivering it to her, “Though, I’ve heard saliva works just fine to make those too.” Was that too forward? He did not know but enjoyed his atempt to make a tease.

 

[PollyWannaCracker]

“Sex on a dryer? Is that even a thing people do? I mean laundry equipment?”​

Will laughed at his own joke, and many of the girls laughed as well, some at the joke and some at him. Oh, they weren't being cruel or anything, but those in the know about his inexperience (which was almost all of them) found it 'cute' that there was likely so much about the sexual world that Will didn't know.

And that was horribly ironic, of course, because he was 2 to 3 years older than all of them. Oh, what that celibate relationship had done to him. Many of the girls (all of them non-virginal anymore) simply thought it had been a waste of good material.

“One slippery nipplle,” he said delivering it to her, “Though, I’ve heard saliva works just fine to make those too.”​

Carmen laughed, slapping him on the ass yet again as she accused playfully, "Will, you're horrible!"

Others were clamoring for their own drinks, even as a couple of the girls had hopped in to help mix their own. Carmen stood on her toes, leaned in, and kissed him on the cheek as she whispered, "I want you, Will. And I think you know what I mean by 'want', don't you?"

Carmen touched him again, but this time it was in front as (beneath the level of the island) she let her hand grasp his crotch for a couple of seconds before she backed away, staring into his eyes as she sipped her drink. She giggled, turned, and joined some others in dancing to the music blaring from the surround sound speakers.

He may not have noticed because it had been very subtle, but as the event proceeded and the temperature (the literal temperature) in the now closed up house rose, a few items of clothing had begun to be shed by some of the girls. Blouses had been shed by some, revealing everything from bikini tops to sports bras to much sexier brassieres that featured lace and push up cups and even semi-sheer fabric. There were at least two pairs of nipples that could be seen through thin cloth while many other excited pair were on 'high beam' as well.

Some of the girls had shed or swapped lower clothing as well, and while most of them were now in some form of shorts or bikini bottoms, a trio of them all dancing together near the floor to ceiling, ocean facing windows were down to their panties, one of which was a very sexy, very small thong.

Polly sidle up next to Will as he was continuing with his drink making, slipped her arm around his back, and asked simply, "Having fun?"

 

[The_gladiator]

Will laughed with the women, but got the feeling he was a bit naive in comparison to these younger women. He blushed at Carmen’s words and touch. His body responded to her touch pressing against her palm. He nodded to her. He understood, he just wasn’t making any commitments at this time. He was needed here doing drinks, he told himself.

“The scenery is quit distracting,” he told Polly. “I feel a little out of place, you know I don’t party much, but everyone is very nice to me,” Will told his sister.