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The Weekend meeting - Part One

Gail and Mike meet for a weekend of sex
We met through an adult dating site. Gail and I were each looking to connect with others who had similar sexual interests and were seeking one-on-one or group sex. 

Now we were in Baltimore, closing the door behind us in a hotel room, anticipating a long holiday weekend of sex.

She was 31, from Kansas City, Kansas, a self-described geek with a passion for computers and programming.

She described herself as tall with short, blonde hair, average looking and with an average figure.

I had seen photographs of her, none of which indicated how tall she was or provided a good look at her figure. On the other hand, what she described as an “average look”, I would have characterized as cute; the girl next door type.

Gail was not a virgin, but did admit that she wasn't very experienced either. A strict upbringing, being an only child, her own shyness and her interest in all things computers had kept her somewhat isolated to a small group of fellow geeks throughout high school and college.

Her clothing preference had been retro, baggy, even hippie, and she did not wear make-up. She just liked being geeky, dressing as she did, and immersing herself in anything computer-related with like-minded friends.

Gail’s high school and college sexual experiences had been limited to guys groping her breasts, rubbing her pussy through her clothes and a hand job here and there for certain friends. When she did venture to satisfy her own sexual needs, it was usually a missionary style experience, lasting only minutes, with only his needs being met.

She graduated from college and graduate school without ever having really experienced the pleasures of oral sex, positions beyond some varieties of missionary, anything close to satisfying foreplay, or what she could honestly say was a worthy orgasm not brought on by her own attention.

At her first job, Gail quickly became the go to person for anything computer-related and that led to an expanding leadership role at work.

Changes were necessary.

Leading the tech section of her company, interacting with senior members of the company staff and meeting prospective buyers of the company’s product required a more sophisticated Gail; retro, baggie and hippie wasn’t going to get the job done. The geek, as she put it, needed to be more of a woman.

Gail began to pay more attention to her appearance. Her wardrobe became fashionable and hair more styled; her shoes more lady-like; and make up, manicures and nail polish became more of her standard.

At some point in this metamorphosis, Gail began to notice that men were looking at her differently, lustfully eyeing her body and smiling. Gail enjoyed men looking at her and began to dress in a fashion that highlighted her womanly assets. There followed an increasing awareness of her own body and increasing sexual feelings and thoughts, flirting, dating, and an interest in men, their man parts, and sex.

She bought a vibrator and a dildo by mail and learned the pleasures of a vibrator induced orgasm, the delight of a dildo sliding in and out of her pussy and just how sensitive and responsive her nipples were when she played with them. Along the way, Gail also learned that sex with another was not always as easy and pleasurable as it appeared to be in the books and articles she had read, or as portrayed in the porn she had watched.

Gail found some men too sexually aggressive and pawing. Some were prudish and just as sexually inexperienced as she was. Others were crude and rude or needed to learn about personal hygiene. Many skipped foreplay, moving directly to their main goal and many more attended to their own needs without any thought to her pleasure.

There were others, however, who had introduced her to wonderful sexual pleasures and those rare experiences whetted Gail’s growing interest and need for sex.

From the start of our relationship, Gail had been clear about her interests. She wanted an experience: as much sex as possible, in as many ways as possible. She wanted to be a slut for a weekend. More importantly, the more she got to know me and my interests, the more she wanted to be my slut.

Now we were in a hotel room in Baltimore, about to pleasure each other. It was 8:00 p.m. Gail wore a white, short sleeved blouse, tight jeans and sandals. Her short blonde hair was now longer, very blonde and tied back in a little pony tail. She wore no make-up and, to me, had curves in all the right places. She was on the thin side and tall, taller than me. She was all legs.

Standing there in the hotel room, I admit that I was nervous. Could I keep up my end of the bargain for three days? Gail could fake it. I either would have an erection or I dwouldn’t, I would either shoot cum or not.

The room had two queen-size beds, each with a terry cloth bathrobe on the pillows. At the far end of the room were a sofa chair and a small, round, glass coffee table. Along one wall, there were a desk, side-by-side bureaus, a television and a microwave oven sitting over a small refrigerator. It was your basic hotel room.

I had requested two beds. Hours of sex on a bed can get messy. It’s more than a wet spot. Think cum, lubrication, sweat, pussy juice and more cum. The solution is sex on one bed and sleep on the other.

Gail and I unpacked our bags while we danced around any references to the subject at hand. I was the experienced one and I knew Gail was looking to me to see how we were going to proceed.

She handed me a large purple vibrator. “I brought this,” she said.

The vibrator, I noticed, had been actively used as the purple color seemed to have worn/rubbed off on its business end.

She held up two large feathers, a red one and a yellow one. “I saw these,” she said, “and thought we might find a use for them.”

I nodded approvingly. I showed her the vibrator I had brought: a little silver bullet about the size of a lipstick case with a wire leading to a battery pack of four batteries. I had used a similar vibrator before with good results and many compliments. This one was new, bought just for this occasion. Gail looked it over and turned it on, feeling the tip vibrate on her fingers. “Yup, that’ll do the job!” she said.

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