The woman in particular seemed to be enjoying the sex to astonishing degree. She was on her hands and knees, with one man entering her vagina from behind, and the other thrusting his penis into her mouth, to which she responded with great enthusiasm. She was groaning loudly and reaching for the man’s hips to suck him deeper. As she watched, Gabriele’s fingers were exploring her clitoris and the neighborhood around it, and making exciting discoveries. And unlike in the movie, the sex in this video kept going on and on. Now one man was squatting and thrusting his penis between her breasts as she straddled the other man, with his penis penetrating her vagina. Who knew there were so many ways to have sex?
And then, without warning, it hit her, her first orgasm. She cried out and convulsed, her whole body trembling. And just like that, in one long afternoon, Gabriele Gehres became a sex demon.
Gabriele approached her new sexual awaking with the same relentless, methodical focus that she applied to other things in her life. She systematically reviewed videos on the porn sites of women masturbating, in order to improve her technique. When she learned about sex toys, she immediately ordered a large selection of them online. In her own mind, she dispensed with biological terms like “penis” and “vagina”, bypassing the cute names like “dick” and “pussy” in favor of the more earthy and raunchy “cock” and “cunt.”
Before long, she discovered Literotica, and became very well read. She also joined a number of porn-oriented chatting sites, which became her new social life to fill the vacuum left by the demise of her job. She took intimate photos and videos of herself and posted them, taking care not to expose her face, but showing everything else.
It now seemed unfortunate to her that for so many years she had worn modest, professional clothing that obscured her rather attractive body. Gabriele now took a bit of pride in her full breasts and hips, and the luxurious growth of hair around her big clit and plump cunt lips.
This is what kept Gabriele occupied during the first weeks of her vacation. One afternoon she received a call, and the person on the other end of the line was Carolyn Ransom.
“Hi, Gabriele. I’m just calling to check in. Are you OK?”
“I’m fine, Carolyn, thanks for asking. I’ve been keeping busy with some… new projects.”
“You have a new job already?”
“No, I decided to take some time off from working. I’ve got some new stuff I’m interested in… you know, research.”
“Well, that sounds interesting. I’m sure you’ll be very successful. You always are.”
Gabriele thanked her and signed off. But just at that moment, a disquieting realization came over her. She needed to find a way to have sex, in person, not just at home with her fingers and toys. And she was 44 years old! Who would want to have sex with a 44-year old virgin?
But Gabriele was not in the habit of throwing up her hands in the face of a difficult problem. She began by visiting her gynecologist, who told her that her hymen had naturally worn down and the loss of her virginity should be painless (confirming what Gabriele had already concluded, after conducting many experiments with dildos). She also prescribed contraceptives.
So, next Gabriele considered what sort of person she might look for, for her first sexual encounter. Before her recent erotic revelation, she had accepted the old-school notion that sex was inextricably bound to love, and that therefore the ideal situation was for a woman to “save herself for marriage.” This notion she now rejected out of hand; she was quite satisfied with being single, it had worked well for her all her life, but she was now fiercely committed to experiencing all the erotic excitement that sex had to offer. In searching for a suitable partner, her inexperience was an obvious liability.
She pondered how to get around this. She knew that there were online personals ads where you could search for a compatible person. She could roll the dice with one of those. But what if the moment of truth came, and she made some clumsy, embarrassing mistake? That would be normal for teenagers, but for a woman her age, it could be a ghastly humiliation. Still, what choice did she have? She could try to pick up a man in a nightclub; she knew that that sort of thing does happen. But she would be running the same risk of embarrassment.
So, Gabriele decided to register with an “adult dating” site and hope for the best. She paid the fee, and posted some provocative photos of herself. She was rewarded with a flood of inquiries and propositions, all of which she considered carefully. Some of them, in her estimation, were obvious fakes. She did a reverse image search on some of the hunkier photos and found that they had been lifted from porn sites. Finally she sent responses to two of her suitors who seemed convincingly real. One of them, who called himself “Justin”, promised her a good time and made a date to meet at a hotel that Friday night.
Gabriele, on pins and needles, arrived ten minutes early, and waited. She waited for an entire hour beyond the agreed-upon time, before finally giving up on Justin and returning to her apartment. She was in a dark mood when she sat down in her living room and opened her laptop, prepared to send an angry email to Justin, but she was heartened to see in her inbox an email from Bachelor #2, who called himself “Steve.” He said he was eager to play with her and included photos of his rather impressive endowment.
A few emails were exchanged, and date was made for the following Friday. Steve said he could host, so Gabriele arrived punctually at his cozy suburban home at the agreed-upon time. Steve closed the door behind her, then kissed her. His kiss seemed a bit tentative, but Gabriele liked it. The feeling of a tongue moving against hers was new and exciting, and she felt her cunt getting wet. She didn’t know that could happen just from kissing.
Steve was now lifting up her blouse to expose her tits. She had not worn a bra — this was unprecedented for her, and on the drive over she was acutely aware of her breasts jigging and rubbing against her garment. Steve was now sucking her nipples, and that was making her cunt even wetter. She felt intoxicated by arousal, and she felt emboldened now to undo Steve’s belt and pull down the zipper of his jeans. She couldn’t wait to get his pants down and see the monster cock he had shown her in the photos.
What she saw was a tiny nubbin of a cock, barely visible in its neatly trimmed nest of pubic hair. Gabriele was suddenly very angry. It had nothing to do with sex, per se — she hated dishonesty and fraud, it was a value that Momma Gehres had inculcated in her, along with her dedication to professional excellence. Gabriele was not a heartless person — she also felt a twinge of sympathy for poor Steve, who must feel pretty inadequate if he had to engage in such egregious false advertising. But she kept both her anger and her sympathy to herself — she made up an unconvincing excuse about having left something in her car, then hurried out of Steve’s house and went home.
Well, two disappointing weeks had gone by, and Gabriele was still a virgin. She needed a different strategy — she wasn’t looking forward to a third strike in the dating game. She needed a situation where she was guaranteed to get fucked, and she now had an idea which she believed could work.
One of the raunchier websites which Gabriele was frequenting featured ads for gangbangs. They were typically held in a hotel room, there was an admission fee for the men, and they had to submit photos of themselves in advance. She knew, from the response to the photos that she had posted online, that men found her attractive and she would be more than welcome to participate. And with her now-extensive experience with porn and masturbation, she knew that sex with multiple men was a thrilling fantasy for her, one of her favorites.
She turned the idea over in her mind. With a lot of men handling her at once, her lack of experience would not be so obvious. And the thought of all those cocks! Gabriele suddenly felt an intense urge to masturbate. She hurried to get one of her toys, her purple rabbit, and reclined on her couch, opening her laptop where she had bookmarked her favorite raunchy videos. She selected one where a young woman was being defiled by a small army of swarthy men, and began to fuck herself with the rabbit until she brought herself to a shuddering climax. Then she began to send messages to some of the women who were listed as organizers for the events.
It didn’t take long to line one up, after which Gabriele once again masturbated to orgasm, this time watching a man fuck a woman’s mouth and cum all over her face. The date was only three days away, and she spent those three days in a constant state of arousal.
The event was scheduled for Friday at 6:00 PM at a hotel about 20 minutes from Gabriele’s home. She had selected her apparel carefully, and even went shopping for a see-through blouse she felt would highlight her bra-less tits. She thought about wearing no panties, but it occurred to her that there might be men there with a panty fetish and she wanted to please them. She was confident that the panties would be very wet by the time she arrived. She tied her light brown hair in a ponytail, and put on heels, even though that might make her taller than some of the guys — but she assumed it wouldn’t matter, because she would be lying down anyway.
As the time approached, she got in the car and inserted her wearable egg vibrator, then set off on exciting drive that kept her too stimulated to be nervous. She let the thing continue to pleasure her as she parked her car. She came hard as she rode the elevator up to the second floor, where she found the right room, switched off her vibe, and knocked.
The door was answered by a somewhat skinny bottle-blonde woman with boob implants. She introduced herself as Angie, and they went into the main room where there was a balding, muscular man with horn-rimmed glasses whom Angie introduced as Rob. He was apparently Angie’s husband/boyfriend/security guy. There were two king-sized beds in the spacious room, along with an ice chest and an impromptu bar set up on a desk.. Angie and Rob sat on one bed, and Gabriele sat facing them on the other.
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