Jackie Makes Things Rightbyescriterra©
It had been a very long time since the last really good sex for Jackie. What was the guy's name? Oh, yeah. _Brandon._ Spring break Brandon. Miami Beach Brandon. Nice, thick, seven-inches-of-delectable-hardness Brandon.
"Mmmmm," was Jackie's unconscious response to the memory as she idly flipped through the pages of the current _Vogue_ in her tiny Atlanta apartment to the soundtrack of _E! News_ on her TV. The pictures of haute couture clothing passed before her unfocused eyes, and the latest celebrity mama drama faded to mental white noise as she went to Miami Beach in that part of mind where this yummy memory resided.
"You like it when I lick your clit, don't you, Jackie?" Brandon had said, raising on his elbows to look at her with gorgeous, deep brown eyes that she loved gazing into. He was lying on his stomach between her splayed legs, the thumb of one hand tugging back the hood of her clitoris to expose the pink, erect point of pleasure where his tongue had seconds before been lapping insistently. She was reclining against the headboard in her hotel room. "You like being eaten, don't you?" he grinned, his middle finger sliding up and down the slippery folds of her pussy lips.
The pseudo-anonymity of spring break, the knowledge that the next day everyone would go back to Whatever U., and no one would have to answer for previously unthinkable shared intimacies with strangers made spring break flings possible. That and plenty of tequila shots.
But Jackie had never experienced anything like what Brandon had done to her the evening before with his cock and so far that night with his tongue. It was only midnight. What else would he do?
She wanted to find out, and knowing that neither of them would ever see the other again vaporized the normal barriers, the normal embarrassment of such actions with people met only the day before. She smiled at him, reaching her hands to her hardened nipples, and rolled and tugged on them shamelessly before she answered.
"You lick pussy great, Ace" she said, using the nickname she'd heard one of his friends call him earlier in the day. "Damned right I love it. So don't stop!" she giggled, releasing one nipple to reach a hand to the back of Brandon's head and push his face back to her crotch.
He resumed his delightful task. The brief break interrupted Jackie's closed-eyes experience of pure pleasure while Brandon's tongue worked its magic, and now she gazed at the smooth globes of his pale, muscled asscheeks contrasting against the ruddy darkness of his tanned back. He slid a finger inside her. He sucked her distended clit back into his mouth and raised up, reaching a hand beneath his torso to readjust his cock. Jackie saw the muscles in his glutes flex with the movement.
_Damn!_ she thought. Brandon was a hell of a stud. Too bad he had turned out to be such a perv.
And that thought brought Jackie back to her current reality, back to the sad state of her love life and its post-graduation succession of inept lovers and/or jerks. Back to her post-graduation life in Atlanta, her job doing copy editing on a neighborhood newspaper, and her modest--—very modest—--living quarters as she whiled away yet another evening alone.
If only she knew then what she knew now about the difficulty of finding men good at sex, perhaps she would not have written off Brandon so quickly. Maybe he was a party boy, but wasn't everybody on spring break? Maybe he was a little arrogant about being a stud, but didn't he live up to his own reputation? Maybe he was from Minnesota where no one sane lived during the winter even though he said he loved it, but couldn't he be persuaded to move?
And maybe, just maybe, that last night in a Miami Beach hotel room, she should have done what he asked her to do after his skillful oral manipulation of her pussy and clit brought her to an intense, satisfying climax.
"You want me to what?" she had said, thinking she must surely have misunderstood Brandon's request.
Looking up after rolling the condom down his stiff cock, he raised a knee over the mattress and prepared to position himself for a classic missionary humping. "Slide your finger up my ass when I'm fucking you," he said, his hard cock bobbing as he jostled onto the bed. "Use some of that lotion on the nightstand."
She didn't do it, and his cajoling only distracted her, spoiling what would have been a great fuck, if Brandon's performance the night before was any indication.
Why had she been such a prude?
"Eeeewww," said her best friend Melanie as they drove back to Atlanta the next day. "That is so gross!"
Tabitha spoke up from the back seat. "Did he go down on you?"
"What's that got to do with it?" Jackie asked, looking in the rearview mirror at the junior who lived across the courtyard in their apartment complex next to campus. Tabitha's money added into the trip's pot meant the two close friends had been happy to bring her along in spite of not knowing her that well.
"Was he good at it?" Tabitha pressed.
"He was fucking great at it," Jackie said, looking at Melanie and laughing.
"So there you go," said Tabitha nonchalantly. "Any guy who eats me and is good at it--—good enough to make me come—--can get me to put my finger up his ass any day, any way. Hell, if he's really good at it, I'll lick his asshole, too."
Jackie and Melanie had just looked at each other. They didn't have to say a word to know what the other was thinking: Freak. Tabitha was freaky.
Maybe because her best friend felt the same way Jackie did, Tabitha's comment was a non-factor and did nothing to prompt any thoughts that penetrating the male ass was anything but disgusting. So the forbidden zone—--a guy's asshole--—remained off Jackie's radar for fantasies as well as for the frustratingly few sexual encounters she'd had since graduating last spring.
So Jackie had not given it much thought after that. She was open-minded about most things sexually (well, some things, mostly), but sticking her finger in a guy's butthole? No way, José. Wasn't gonna happen.
But, what if . . .
At that moment the words, "Craig Ainstock" broke through her mental musings, and she looked at the TV, always interested in seeing this newly anointed sexiest man alive. One of _E!'s_ anchors was talking about the paparazzi's just-published photos of Ainstock's romp in the surf with his latest squeeze, and those pictures were displayed on the screen.
Jackie was happy to play voyeur to the photographer's "candid" shots (surely these things were staged, right?) The setting sun cast the right mix of shadow and illumination on Ainstock's lithe yet muscular body. His board shorts were down just far enough to tantalize with the hint of firm glutes rounding out as the material of his shorts clung to his cute butt under the spray of water he was kicking up.
It was a very short mental step for Jackie to imagine Ainstock nude, his naked ass on display for her. It would be muscled, but not too much—--just enough to be firm yet still delightful for grabbing and squeezing.
_That's it, darling Craig,_ she thought as what she saw on the TV screen prompted the poses she wanted to see of this gorgeous man in the nude. _Oooh, yes, very nice like that. You have a beautiful cock. Can you let me see how big it gets when you stroke it?_
And then the next story flashed into rotation, Anchordoll Two took over from Anchordoll One to ooh and aah over a different celebrity couple. Jackie sighed, disappointed that there wasn't an interview on the beach with Ainstock. That would have been nice fantasy material, too. He would, in her imagination, be naked on that beach as he spoke to her.
Such was the incongruous nature of Jackie's sexuality. She delighted in the visual aspects of sex, of seeing men naked, and that made her very much a modern woman. Modern women realized that they _were_ turned on by seeing attractive naked men and that it was _not_ "inappropriate" to think of sex in terms other than romance novel euphemisms. Twenty-first century American women college grads had grown up in times that made access to most sexual interests relatively easy (except, thankfully, for the exploitive crap like bestiality and child porn).
Male strip clubs? On occasion for Jackie, the modern woman. No-strings sex? Definitely, when the opportunity arose but the guy wasn't long-term material. Role-playing? She would consider it, though the opportunity hadn't thus far presented itself. Porn videos for women? She had a modest collection (not that much good stuff out there, after all), and she enjoyed watching them as she played one of her vibrators across her nipples and clitoris during especially arousing scenes. _Playgirl_? Not a subscription but the occasional purchase with a thank-you-yes-I-look-at-the-pictures smile when handing the clerk her credit card. Internet sites showing naked men with hard cocks smiling into the camera, even masturbating? Jackie had a few favorite sites bookmarked (though, again, not that much good stuff out there that was meant for a female audience). A threesome? Well, maybe . . ..
So why not finger-fucking a guy in the asshole? Go figure, but Jackie had always steered clear of even thinking about it before Brandon's surprise request. Her conversation with Melanie afterwards reinforced her attitude toward the activity, and the occasional mention of it in the "Letters" section of _Playgirl_ or on a web site was easy to skip without a second thought.
At least until several months passed without any sex near as good as she'd experienced with Brandon that first night. What if he had wanted to stay in touch, maybe visit her in Atlanta after graduation? What if he turned out to be a decent guy? What if she had done things differently that evening? Would the fucking have been even better than the night before?
The questions nagged at her.
Jackie's education was launched with those questions. A week later, in spite of clubbing with a group of co-workers over the weekend, the only upcoming dates on her calendar were with guys she knew she would never sleep with (but whose money would pay for a very nice meal at a nice restaurant in exchange for a good-night peck on the cheek after which she would feign a wicked headache from the wine at dinner).
Frustrated, Jackie spent one night with a vibrator and the DVD _Miranda's Search_ from her collection, then a second night in a soothing bubble bath, her fingers roaming over her breasts, belly, and gently massaging her hardened clit. Her thoughts drifted to Brandon's luscious cock as her fingers became more insistent. What if? What if on that second night in Miami with him, while he was humping her the way he did the first night—that first, glorious, satisfying night—she had done what he wanted? Lotion on her finger. Sliding her hand between his muscular glutes and into the valley between his firm flanks. Then, god . . . touching it. His asshole. Working the tip of her finger inside . . .
She allowed herself a small, teasing orgasm, then rinsed and rose from the tub to step onto the thick rug in front of the mirror in her small bathroom.
Appraising herself in the mirror, Jackie struck different poses after toweling herself dry. Sandy hair, green eyes, workout-toned body, she was proud that she had never put on the "freshman 15" pounds in college. Thrusting her tits forward, nipples protruding with a satisfying hardness, she lifted her B-cup breasts up and forward, offering them to the reflection in the mirror. _I am hot,_ she thought, turning to a side pose and running her hands down her ribcage and onto her hips. Arching her back and shimmying slightly to make her firm tits jiggle in a manner she knew would drive a guy wild, she nodded approvingly. _Very hot._
So where were the guys who would appreciate this body by being damned good in bed?
Moist from her orgasm tease, Jackie drew on a robe, went into her bedroom, and sat down at her computer. Typing "anal sexplay" into the search engine, Jackie hit "Enter" and was immediately presented a dizzying array of possibilities.
Maybe it would be easy to figure out Brandon's kink.
Jackie started web surfing at 9 PM, and even though the clock on the computer advanced minute by minute, hour by hour in her peripheral vision, she couldn't stop reading through the accounts from blog posters about how thoroughly they enjoyed asshole play and how they did it.
There certainly seemed to be a lot of people into it, both men and women.
"The first time he asked," one woman posted, "I was grossed out. But he promised me that I would _love_ a gentle asshole massage—--no entry, just a sensuous and light caress to relax me. He wanted me to find out how much the asshole is an erogenous zone if you let go of your hang-ups."
This sounded like someone who had taken a very different course of action than Jackie had taken with Brandon.
"He let me know that he wasn't asking to do it because he was kinky or into weird scatalogical activities. He wanted me to experience as much pleasure as he could give me. So I let him, and let me tell you, it was fuckin' great. I felt like a queen when he played with me there. It was sexy in an intimate, naughty way, and it felt wonderful."
Jackie's thighs unconsciously pressed together as she continued reading, moving to a different description, this one from a woman describing the first time she put her finger up her boyfriend's asshole.
"So I did what he wanted. I had absolutely no idea what would happen or how it would feel up inside him. It was tight and warm and a real power trip to actually penetrate him. Not a power trip like I wanted to dominate him or anything, just a feeling of being able to cause and control his pleasure like that."
_Jesus,_ thought Jackie, _this is way different than how I've thought about it._
"Maybe he didn't tell me on purpose, but when he came from the handjob I was giving him at the same time, his asshole spasmed and gripped my finger—--gripped and released, gripped and released, just like I know my pussy does around his hard cock when it's buried to the hilt inside me and I have one of those intense orgasms that feel so good. That just blew my mind! My man was taking my finger inside him and I could feel his orgasm in a way I'd never felt it before. It was incredible!"
That description moistened Jackie's pussy.
After riffing through a couple more confessionals on the web site, both of which fell into the "fuckin' great!" category, Jackie's sexual discoveries about the male anus and the way women use it blasted into completely new territory.
Before tonight, the thought of women doing men with strap-ons . . . well, that was so far beyond a finger in the ass during a BJ or fucking that Jackie didn't even have a frame of reference for the possibility. She'd probably seen or heard mention of such a thing in a magazine or a blog somewhere along the way, but it must have created the same reaction for her as seeing an article about quantum physics: nothing except an automatic, uninterested focusing of her attention on something else.
Yet, tonight . . .
"I had wanted her to do it to me for so long, but I was always afraid of what she'd think. Finally, though, I got up the courage and just blurted it out one night after we'd made love and both had great orgasms. I guess I figured that was as good a time as any. And I gotta tell you, it was a completely different response from her than I expected. She said she'd do it! A couple weeks later after the strapon arrived from the online store where we bought it, I was naked and face-down on the bed with my ass up and my beautiful wife behind me, dripping lube between my flexed open cheeks (lots and lots of lube, we found, is a very good thing). When she slid that strapon inside me, it felt every bit as good as I had been fantasizing about for years. After a little bit of getting the hang of it, my wife was soon really stroking into me, withdrawing, and then plunging the strapon back in all the way to the bottom. She grabbed my hips and really started fucking me, and I could tell by her breathing that she was heading to a climax just like I was. She came with a yell, and that pushed me over the edge. I spurted buckets, and she collapsed on top of me, the strapon slipping out in the process. We lay panting like that for a couple of minutes, trying to focus on anything but the stars in our heads brought on by that first, incredible time when she screwed me in the ass."
_Damn!,_ thought Jackie, _what must it have been like for that woman, her man naked in front of her like that? Talk about a doggy style role reversal . . ._
Fingers up the guy's ass when he came. A strapon cock harnessed onto a woman's crotch in order to fuck her guy in the asshole . . . and then coming as a result of doing it. These were things that Jackie was starting to see in a whole different light.
With her new interest, she went ahead and clicked on some of the hotlinked videos on the pages she was surfing. Most were . . . interesting, but not her cup of tea—--too much "Take my cock, bitch!" stuff where the women weren't really into it as a means of bringing themselves and their men to orgasm but were on some kind of power trip/BDSM-type of thing.
But there were a couple that warranted more than only a single viewing, especially when she somehow clicked through to a site purporting to be "FOR WOMEN BY WOMEN WHO LOVE STRAPON-FUCKING THEIR MEN." Jackie immediately bookmarked the URL.
One video was a 3-minute clip from a DVD that the site was selling. _Allison and Jeremy, Vol. 3_, was most assuredly a title she would add to her collection:
"Ummmm, baby, you look so hot like this, naked in front of me. I like that your cock is really hard," said the woman in the video, fully clothed in office attire, her auburn hair stylishly up in a manner that communicated professionalism keeping tight rein on smoldering sensuality. "Let me see that pretty hard cock bob around in front of you when you move. You know that excites me."
_Oh, my,_ Jackie thought, watching the action in the frustratingly small frame on her computer screen, _he does look sexy moving around with his hard cock bobbing in front of him like that._
The woman then reached out and grabbed the guy's erection, wrapping her fist around it as she smiled at her naked male. She turned and led him by his cock to their bedroom as the camera followed. "I've been eager to get home to you, hoping so much that you'd already be back from your conference by now and waiting for me naked like you said in your email yesterday. It was a tough day dealing with clients, and I thought about our playtime tonight more than once right in the middle of a meeting. Why don't you help me with my strapon?" she said, releasing him and standing expectantly at the foot of the bed. "You know where it is, don't you?" she asked with a sly grin.
The guy in the video was really hot. He had a tanned, toned body, and the camera caught the sexy way his asscheeks moved as he walked to the chest of drawers in the room in order to open a drawer and pull out a dildo and a harness. "No, Jeremy. Why don't we try the other one in the drawer tonight?" the woman said, shaking her hair loose behind her and then unbuttoning her teal-colored silk blouse. She drew the bottom of the blouse out of her black skirt.
The guy stood nude, strapon and harness in hand, a puzzled look on his face.
"I love seeing my strapon slide into you," the woman said, shrugging off her blouse, "and if it's the longer one I bought last week as a surprise for you, then I'll get to see that happening even more, don't you think?"
The woman had placed one hand on the bed to steady herself as she lifted a leg behind her in order to slide off one of her shoes. She was looking at Jeremy naked in front of her, his cock hanging heavy between his legs. He was still frozen in place after hearing the words, "the longer one . . .."