Tim and Jill
- 2 years ago
- 27
- 0
As Tim watched the last of Wilson's ten-inch cock bury itself between the welted cheeks of Jill, who was bound spread-eagle fashion to the bed, he thought about the first time he had ever laid eyes on her. You talk about a mess. That was Jill.
He had been invited to a sorority pledge event to check out the new meat. Although no scholar, Tim was well known on campus thanks to his impressive cock and his natural talent for using it. He'd gone down to the basement to get rid of some beer when he saw Jill. The girl was naked and tightly tied to a block of wood with her head hanging over the edge. Two enormous vibrators were churning away inside her cunt and asshole. Her mouth was wedged open with a fixture liberated from the dental department. Three guests stood around the mousy brunette, directing their streams of piss into her propped open mouth. Tim elbowed his way into the circle and directed his used beer into the girl's eyes, which were taped open. It was almost impossible for the girl to avoid the stinging stream he played over her face. He even managed to shoot some up her nostrils, forcing her to gag. When he was done, Tim zipped up and went about his business, leaving the girl to the tender mercies of the line of guys waiting to use her as a urinal.
The next day Tim got a call from one of the pledge masters who asked him to meet with her to discuss a problem that they were having with a pledge. It turned out to be Jill who just happened to be the daughter of retired general Nails Norton, one of the most famous graduates of the college. To add to the problem, her mother was a former member of the very sorority that Jill was attempting to join. In fact Mrs. Norton had been the sorority's sergeant at arms as well as its pledge master during her senior year. A legend in her own right, the former Gwen Goodbody made no bones about the fact that she went both ways and had bedded down with all of the attractive, openly gay sorority girls and nearly half the male faculty and in many cases their wives as well. It was rumored that Gwen had been the secret sex slave-lover of the Dean of Women.
" Jill's not smart enough to be a nerd, and she's not pretty or well-built enough to be a sorority playgirl. We've got a full quota of pledges that we really want; some of them even go both ways, another thing that Jill doesn't do. What we need is someone to take her off our hands so to speak."
Tim scratched his head and grunted. " Why not just kick her ass out onto the street and hope she goes away? " was his response.
" No can do, her dad is too well connected and mom would raise holy hell. We need some way to make her leave voluntarily," said the girl.
Tim's face lit up and he slapped his knee. " I've got it! Turn her into the sorority fuck pig. Volunteer her for every keg party on campus. Put her phone number on every men's room wall in town, and make sure she answers every call. Tell her its part of her probation. If she doesn't obey you have grounds for not pledging her."
The pledge master's face broke into a huge smile. "Tim, you may have saved my ass and as a reward you are going to get as much of it as you can handle for the next two weeks."
Tim grinned and grunted happily. " I'll be expecting you and that hot little freshman friend of yours over at my place tonight for a nice threesome. I hear the little sweetie goes both ways, and I want to make sure of that personally."
Jill Gets a MakeoverIn theory it was a good idea, but in practice Jill's execution left a great deal to be desired. In essence, Jill was a rotten fuck. Couple that with her average tits that already had some sag in them, her broad and less than firm ass, the ring of flab that circled her midsection and the fact that she didn't know what a razor was for, and you did not have a picture that excited most men. Add to that her mousy brown hair that was cut short, her lack of makeup and the plastic frame glasses she peered out at the world through, and she did not make a pretty picture. Even the sorority lesbians wouldn't do anything with her unless they were absolutely desperate. Once more it was Tim to the rescue.
He took over Jill's career as the campus punchboard in exchange for the services of a sorority nerd for his grades and a playgirl for his personal needs. One thing Tim was able to figure out about Jill; this mousy girl was perfectly submissive. She bowed down to authority, possibly the result of being brought up by a strong willed woman and a military disciplinarian for a father. Once she was convinced that Tim was the boss, she'd do his bidding, no matter what it was. He got the pledge master to ask Jill's mother to tell Jill that Tim was to be obeyed as if he were her father. When that happened, he had Jill just where he wanted her. As they say, the rest was history.
He made the frat guys an offer they could not refuse, Jill would be free and almost anything went provided they dragged what was left of her ass back to the sorority house whenever they got through with her. To broaden her sexual horizons, he also arranged for Jill to provide the entertainment at the weekly VFW post meeting, the bi-weekly UWL (United World Lesbians) celebration, and the monthly meeting of the senior citizens social club. It turned out those old folks really knew how to party. More than once he had to get Jill to the school infirmary after a meeting with the seniors because she had been used so hard that she went into shock.
Tim supervised a complete makeover for Jill, giving the girl a tramp-slut look that matched the pros that trolled for cock down town. She got contacts, a new do including streaked hair, learned to pile on the lipstick and makeup, and most importantly, a new wardrobe. The new Jill wore pushup bras, and tight bikini panties. Her tops were sheer to show off the black lace that cupped her sagging tits. She wore white capris that were a size too small, revealing the bikini panty line to all who weren't staring at her bare stomach which was always marked with lipstick announcing such information as which fraternity keg party she would be attending, how many men she had serviced at the last one, and the total number of times she had been fucked since becoming the sorority fuck pig. To complete her outfit she wore fuck-me pumps with lace anklets.
Except for the frats every other organization had to pay Tim an agent's fee. Since Jill was not getting anything for her considerable expenditure of energy, the groups could hardly complain about paying Tim for his trouble. Strange as it may seem, Jill developed into a cult favorite on campus. The frats vied with each other to see who could do the most damage to her. To keep everything on the up and up they took to taping the action as she was mercilessly fucked to a frazzle and subjected to all manner of punishments and humiliations for her tramp-like behavior.
Tim made an arrangement with a private company to export these tapes to the Far East where they proved to be best sellers. Jill received a number of offers to come to Japan so that she could be gangbanged and humiliated by experts. Tim started thinking about making a tour during the summer. Not only would he profit handsomely, probably he could get lots of Japanese pussy as well. The future looked bright.
Jill Becomes a Money MakerOne thing that Jill proved to be very good at was getting pregnant. Despite being fitted with a diaphragm and going on the pill, her forgetfulness and general ineptness when it came to maintaining her "catcher's mitt" as Tim called it, led to the inevitable. The sheer number of spurting cocks she was handling practically guaranteed getting pregnant if there was any breech in her birth control system.
Ever the idea man, Tim turned that to his advantage. First he made arrangements with the school's medical school to use Jill as a subject when the med students were taught to perform abortions. This revolutionary approach to campus medicine made him even more famous. During a typical year dozens of young ladies were usually in need of this costly, time-consuming procedure. Now thanks to Jill's example they could avail themselves of student practitioners for next to nothing and remain on campus as well.
Then he used her condition to create even greater rivalries between the frats. He found out that the actual date of conception could be accurately known thanks to information he got from one of the randy senior citizens. Armed with this knowledge, once Jill became pregnant, usually an every other month occurrence, he had her draw an arrow pointing toward her belly and the words " Alpha-Phi-Gamma (or whatever fraternity was responsible) Bastard on Board ". This caused a sensation on campus.
Once the medical school folks had done their thing he would raffle off Jill's services to the competing frats that were naturally eager to demonstrate the sexual prowess and potency of their membership. The raffle never failed to clear a couple of thousand dollars minimum, and Tim had visions of perhaps opening it up to other chapters of the various frats that entered each drawing. When the word got out, the townies wanted a piece of the action as well. It really got insane when the senior citizens' club and the VFW also demanded to be included. When the faculty fielded a team, Tim knew that his ship had come in.
.
Tim's decreed that she restrict access to her cunt to only the winner of each weekly raffle, but continue to build her reputation as the campus champion fuck pig by providing anal sex to the rest of her army of fans. To make sure that no one breached the arrangement he had Jill wear a custom made chastity belt designed and built by the school's engineering department. To express his appreciation he let the entire design and production team fuck Jill's asshole during one of her free nights.
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JACK AND JILL By Tammy Richards SYNOPSIS: When Jack's neighbor discovers his feminine alter ego Jill, it's the worst day of his life. But sometimes bad beginnings have happy endings. ------------------- Jack Williams rolled over and hit the snooze button on his alarm clock. It was 6 AM on Saturday morning. He lay in bed planning out his day. Saturday was Jack's favorite day of the week. From Monday through Friday he was the...
The room was old, so old the electric lights seemed out of place-it was a room for candles or gaslamps. Almost the only furniture in the room was a huge brass bed, a Victorian monster with brass head and foot posts of tarnished metal, like two prison gates. Only the sheets and mattress were new-they always needed new sheets. Jill led the boy into the room. He was 18, and shy, from California-backpacking with his sister across England. He had boyish features, straw colored hair, pale blue eyes,...
Jill was in that netherland of part asleep and part awake. She had been having pleasant dreams, so when her legs began moving apart she went with the dream, moving them wider as she stretched and began to fall back into the sleep side of her mind. Suddenly she came fully awake as Anthony’s tongue began circling her clit and his fingers began tweaking her nipples. Feeling and seeing his brown arms and head, she closed her eyes and just went with his sensual contact with her body. He was very...
InterracialGreg had been wearing his new gold chain for about a month and during that time things had again changed in his relationship with Jill. She had decided that he should become more of a sissy boy. He had evolved to the point where he enjoyed and looked forward to Jill’s sexual experiences with other men. He enjoyed licking and drinking their semen and had become good friends with Colby, always welcoming him into their home.To further Greg’s change in lifestyle Jill had gone to the mall on a...
CuckoldTim is happily married to a wonderful woman for the past 35 years. Tim, for the past 35 years has also been secretly having bisexual affairs. These affairs have escalated from meeting a guy in a bathroom and giving a quick hand job all the way to dressing up in girlie underwear and being the center of attraction in parties while several guys received great head and fucked him several times.This story is about what happened to Tim at that party.The week before, Tim made arrangements with Tom,...
Gay MaleCopyright© 2006 "I tell you I heard them talking about him," the short-haired brunette named Jill, told her best friend, Joan. "He's only a kid, maybe seventeen or eighteen." "That's awfully young. He's jailbait," said the lighter, long-haired, Joan. "That only applies to young girls, silly," Jill scoffed, knowingly. "I don't know, Jill. They sent that school teacher to jail, remember?" "Well, she corrupted a child's morals. We're talking about a full grown man,...
I was at home, playing online chess when my phone started to ring. It was Jill. I felt blood rushing to my face. My heart was already galloping. I hadn’t seen her more than three months. Back then she told me that we should stop dating and should just be friends. It was very hard for me, but there was nothing I could do. “I need your help, George,” she said. Her voice was strange. As if she had problems breathing. And somehow tremulous. That frightened me. “Jill, are you all...
Jon & Jill by JKChapter One Jon Folkkes was sitting in his office in the JF Air Services hanger at Love Field in Dallas Texas. He was bent over his desk busily completing US Customs forms. He had just piloted his Gulfstream 5 corporate jet air craft from Cancun in the Mexican state of Quintana Roo. He was tired. The instant coffee he was attempting to swallow was just short of being vile. He could hear the rain drumming on the hanger roof as he worked. He had just spend most of the...
I had nothing to do, so I went out for a walk. I was walking for about ten minutes when a woman came walking toward me. Our eyes met and locked. She had such eyes that spoke to me on a new level. It took me a moment to regain myself. My scope of vision panned out and I took the rest of her in. She was medium height. Her hair was brown and her face soft. The rest of her looked like a model. Her breasts appeared to be firm and were barely contained in her T-shirt as well. She was wearing a pair...
Jack and Jill by Vickie Tern ([email protected]) Authors foreword "Jack and Jill" is a novel in ten chapters averaging 30k each about a fictional cross-dresser like you or me in fact or fantasy or remote curiosity, or else why have you read this far, and how he or she became the person who is narrating the story. It's mostly TG and femdom, with forced or tricked or cajoled feminization, but of course also m/f and m/m and f/f in various u.c. and l.c. combinations, and also...