Sheryl had her rather little about the Free Republic of Alaska. Since she was in the re-location camp, there wasn't any access to radio or TV except from "Official Sources"-which meant religious programming in large part.
God Sheryl missed her old job, the resturants, talking with her friends. Here? Well, the days were long and opportunities for talk were limited. Matrons were, well everywhere--and even where they weren't, well, it was a little scary to Sheryl how many women much like those she had known had come to really identify with the Matrons.
Flashback Sheryl thought back to the first time she had sex with Gerald. She was fresh out of Smith College and had been offered a job at a brokerage in New York. She'd had a steady boyfriend in high school-and another in college. Both had been accomplished and athletic. Gerald, well, he was different. Swarthy, polished, smooth, suave-a partner in his New York brokerage. This was everything she had dreamed of. Her first weeks in New York struck her has much like college-lots of socializing with other women--except there were a lot more gay men around, and well, they were _just about_ like women.
Gerald, well, _he_ seemed different. those piercing black eyes, the wavey black hair. She'd been at the office for a couple months and didn't think he'd notice her. She'd _tried_ to get him to notice her-doing things she was surprised at. She even went to work one day with no panties and flashed him.
Then, her boyfriend from college was coming to visit. She'd asked to get off early that friday to meet him at the airport. Gerald had asked her for some help in his office. There was relatively little conversation. She was like a deer in the headlights. Hell, there was relatively little in the way of talk. As soon as the door was closed, he motion her to his desk, in an office with a panoramic view of manhattan, bent her over the desk and lifted her skirt. She froze, not resisted just froze. She was utterly confused. Part of her asked "Why now? I'm meeting my boyfriend in 2 hours, why now?" Still, she didn't do anything. She wondered, who might be watching? She could see several people in neighboring buildings as Gerald massaged her ass. Gently, she pulled her cheeks apart. Anal sex had always been a taboo with her-but, well she'd wanted this so bad, for so long".
"Relax" commanded Gerald, his finger approaching her tender office. She surprised even herself by simple relaxing. His finger entered her slowly, but firmly. Shortly afterwards, he substituted his bare, circimcised cock. She'd always used condoms with her boyfriend-she knew she should, but she was afraid to say anything here. Gerald's cock was larger than her previous two boyfriends, but not by a huge margin. There was something a little depraved, he was Sheryl, miss prim and proper-the high school valdictorian in a Catholic girls school, honor student at Smith, now having unprotected anal sex in full view of much of the New York financial community.
Still, there was something exciting here. Sheryl had simply never thought of doing anything quite like this before. Her ass hurt hurt as Gerald pummled her, then a different sensation started, and started to build. Sheryl foudn herself getting into it. "Fuck me, please, please fuck me. I want it, yes, I want it". Then, as suddenly as he started, Gerald ejaculated into her anal cavity. The entire encoutner, probably lasted all of 15 minutes.
Gerald, was, well a bit curt. Sheryl, was, wanted more still-but just wasn't quite sure out to ask for more. Before she could say anything, Gerald left the room.