Vacation Nightmare - Pt. 04

Three years earlier: Bob arrived at the office. The night before Sheila had asked him to stay late and they had fucked in her office. She was a very attractive and sexy older woman. She was also a senior and managing partner where he worked. It was a large and successful law firm and she exuded the self-assuredness and confidence that came with the position. People around her, including Bob, could sense her power. She was a woman who got what she wanted..

Sitting at his desk in his office, Bob was having trouble concentrating. He felt a little bit guilty of cheating on Rebecca. He knew that most people considered him very lucky, Rebecca was truly a 10 with her extremely prominent natural breasts. Behind Bob's back, co-workers and friends would comment to each other, "How would you like to fuck that." Reality was very different, Rebecca had never had a very strong sex drive, it came nowhere near matching Bob's.

When they first married, Bob was okay with that because she was just so damn beautiful. He was aware that everyone envied him although he honestly knew that Rebecca was a bit of a dud in the bedroom.

Her interest in sex had only decreased over the years of their marriage. She never initiated or exhibited much enthusiasm. She seldom said no, instead she just sort of lay there below him or in the morning would offer him entry from behind in a spoon position. Twice a year, on his birthday and their wedding anniversary, she would dutifully and mechanically suck him off. It was the major tension in their marriage. He would complain, "You are like a jellyfish in bed. God damn it, can't you at least show some creativity or enthusiasm?". She would cry and say she was sorry and that she would try harder, but nothing ever changed.

Sheila continued to execute her time consuming and elaborate plan to enthrall Bob and capture Rebecca. She had her assistant create an invitation to a mythical "associates" meeting to be held every Wednesday evening That gave Bob an easy way to explain his whereabouts to his wife. Bob was the only associate to ever attend the "associates" meeting and for the first six months Sheila was the only other attendee.

Sex with a man, even one as reasonably talented as Bob, was pleasant but not particularly exciting for Sheila. Not unless they were tied down and ready to be a toy for Sheila's amusement. It was way too vanilla, and as a natural Domme, there was only so far she was willing to go to please Bob or anyone else for that matter. His first seduction had included a blow job, although she had stopped before he had shot off in her mouth. "Thank God," she thought to herself. Male cum in her mouth was really out of the question, even in order to gain access to tits as luscious as Rebecca's. She didn't mind the taste, it was the implied submissiveness of the act that made it unacceptable to her.

She planned to keep a strict limit on how often she would treat Bob to oral sex. She had made a mental agreement with herself that she would only be willing to have his cock in her mouth at most three times. There would be no fourth time. She had a rule that Domme's do not perform oral sex on submissives. She was not planning to turn Bob into one of her submissives, so she was willing to grant him the three exceptions.

She told Bob to come to her office Wednesday at 6:00 for their first meeting. At 5:30 she used her private bathroom to change into sexy lingerie. The silk and cotton material she was putting on was not completely to her taste, it was too conventional. She would have preferred a leather corset but she didn't want to scare him off. She also knew that she had a great body for a woman of 50 and she enjoyed showing it off. She stripped off her office clothes and slipped into the black garters, fishnet stockings, thigh high leather boots and a black lace brassiere. She liked her look but also knew it was straight out of a whorehouse handbook.

Bob buzzed her office door, she pressed a button, her office door lock clicked open, and Bob entered. She had positioned herself in front of her desk so that he would get an eyeful immediately upon entering. She saw that she had the desired effect. Bob was a young man, barely in his mid 30's, and she could see his hard erection through his suit pants. She reminded herself that he did have a good size penis and he had done a good job satisfying her with his mouth, so although this evening might not be exactly her cup of tea, it was still going to be pleasant enough.

She sat down on her desk and motioned with her arms for him to come over and stand between her wide spread legs. She was not wearing any panties, just the garter, and her vagina was completely on display. She had another rule that as a Domme she was not going to subject herself to shaving or waxing her pubic region, that was for subs. She just kept herself neatly trimmed, which she had one of her girls take care of in her office during lunch. The girl took care of some of Sheila's other needs over lunch as well.

Sheila reached down with her hand and started to stroke Bob's cock through his suit pants. She lied and said to him "I have been thinking about this cock all day." The truth was that when she wasn't preoccupied with work or engaged in sexual fun with others, she was daydreaming about all the things she was going to do to Rebecca's tits someday.

She ran her hand up and down his member, stroking it and making him even harder. She used her free hand to reach over to find and open his zipper. She reached through the opening, found the button in his boxers, opened it up and slid his cock out through the boxers and pants.

"Goddamn it, fuck, me, fuck me now!" she insisted, only half meaning it. Bob could barely contain himself. He pushed his hips forward, while Sheila guided his cock into her wet hole. "Oh yes, so good," she said softly, as his cock entered her. She meant what she said this time, his cock did feel good as it entered her. She wrapped her long legs around his hips and pulled him into her deeply. Sheila then set the pace by pulling and pushing with her legs. For the second time, Bob was fucking the firm's most senior legal partner.

Bob was totally excited by Sheila's aggressiveness. It had barely been a minute from when he stepped into the office until she had her legs wrapped around him, begging him to fuck her. He also found her extremely attractive despite the 15 year age difference. She pushed and pulled strongly with her legs while moaning quietly with gasps of "oh yes", "that's it", and "keep going." Sheila sensed that Bob was about to come, and she suddenly stopped and pushed him away with her legs.

"Oh no, not yet, you naughty boy" she said to him while waving an upright finger in the air. Sheila wanted Bob totally addicted to having sex with her, and she was going to edge him several times before letting him finally come.

She got up from the desk, grabbed Bob by his cock and led him over to the couch in the office. They sat and she gently stroked his cock, barely touching it, just teasing him. What she really wanted to do was take her long nails and scrape them up and down his cock and listen to him plead for mercy, but that did not fit into the plans she had for Bob.

Sheila was sitting to Bob's right, so she took his right hand and guided it to her crotch. "I want you to gently start rubbing my clit with your index finger." He slid his hand down into the space between her legs, found her opening and slid his finger upward finding her hard button. Sheila was relieved that he knew how to find a clitoris. This vanilla evening wasn't going to be that awful, she decided.

The two of them sat side by side, Sheila gently sliding her hand up and down Bob's cock, while Bob rubbed her clitoris. With her free hand, Sheila unbuttoned Bob's dress shirt, and slid it off his free arm, and then lifted his hand off her clit for a second to get the shirt completely off. She unbuckled his pants and she released his cock for a moment so that he could scoot his pants down to his shoes.

Sheila wasn't going to let Bob come, but she had no intention of delaying her own gratification. "Press harder" she ordered Bob. Bob pressed down with his finger while rubbing in a circular motion. After about a minute, Sheila moaned and then ordered "harder!". Bob pressed down hard. "Yes, that's it," Sheila gasped. Another minute and then Sheila reached down with her own hand, pressing it hard against Bob's, and moving his hand in an up and down direction. "Oh god, yes" she moaned, as she came. Bob felt some fluid shoot from Sheila's vagina. He had just discovered that Sheila almost always squirted when she had an orgasm.

After Sheila calmed down, she grabbed some paper towels and wipes she kept handy in a filing cabinet drawer and sponged up her mess and cleaned it with a wipe. The couch was leather, making cleanup easy and leaving no stains. She would have preferred to order Bob to clean up her squirt with his tongue, but again, that was not part of the plan. For the fourth or fifth time she thought to herself "Ugh, this is soooo vanilla."

It was now time for her to edge Bob for a third time. She got up off the couch, and then lay down over the sofa arm, with her feet on the floor. The middle of her body was supported by the couch arm and she grabbed the back cushion and turned it perpendicular to support her head. Her ass was sticking straight up in the air.

"Your turn, lover. Shove that nice hard cock up my cunt please." It was quite unlike her to ask nicely. Oh the sacrifices she was making to get Bob under her control.

Bob stood up, and lined his cock up with Sheila's cunt and slid in. He was terribly frustrated having been toyed with continuously since he entered the office. His cock felt warm, wet and surprisingly tight inside Sheila's cunt. Sheila always tightened up after an orgasm. He knew he wasn't going to last long, but Sheila knew that as well. To keep him from coming, she would wait about a minute and then ask him to stop and pull out so that she could unnecessarily adjust her position. After about 5 adjustments, she asked him to stop and she stood up. She lied to him, 'This is just too uncomfortable. We have to try something else."

Bob stood there with his cock rock hard. He had been denied cumming yet again. Sheila took her time on purpose. She slowly and carefully started to clear her office desk. When cleared, she told Bob to lie down on top, facing upward. It was a six foot office desk, and Bob fit on it nicely. Sheila took one of the couch pillows and placed it under his head. She then placed a pillow on each side of his hips. Those were intended for her knees. She slid his shoes off and then she slid his pants off. For no reason at all, she left his socks on.

She then climbed up on the table and taking his cock in her hand, she slid it up into her pussy. What she really wanted to do was put the pillows up by his head and smother him with her cunt until she squirted again, but it was all about Bob this evening.

Sheila's thighs and calves were in great condition for riding Bob because she invariably straddled someone or something almost everyday. It was a classic position for a Domme to hover above a slave. She found it terribly exciting to have so much control over someone as she pressed down hard onto their face, having complete control over their every breath. Cocks and strapons were also things she lowered herself down on regularly. She started to move herself up and down slowly and with great control onto Bob's cock. Achingly slowly as far as Bob was concerned. She took his hands and guided them to her breasts.

"Pull my nipples gently." she ordered him. Bob did as requested. He closed his thumbs and index fingers around Sheila's nipples and pinched. Then he started to pull on them. Normally Sheila would have slapped a lover for such a transgression, pulling without permission, but instead she put her hands on his and pushed his hand back towards her body indicating that pulling was not desired.

His cock did feel good in her cunt, and he was doing a good job squeezing her nipples. She wanted him to last at least 15 minutes before she was going to let him come, so she mostly just pressed her body down hard against him and rocked with small motions back and forth with her hips. That left his cock deep inside her which was very pleasant for her, but a bit frustrating for Bob. When she felt enough time had passed, she started to move up and down rapidly on Bob's penis. She would lift herself up till just the tip was left in, and then drop quickly. The rapid friction was exactly what Bob needed after the long buildup and it wasn't long until he shouted "I'm coming". Sheila could feel his warm ejaculate deep in her pussy.

She let herself drop onto his cock, while it jerked a few more times inside her. Bob was truly spent. Her second meeting with him had gone as planned.

Sheila lifted herself up from Bob's cock. She was done with him for the evening. If he was still horny, oh well, that was what his wife was for. She hurried off to the bathroom but not to clean herself. Instead she slid a long slim metal dildo with a wide flat base up into her cunt. This was to hold Bob's cum in place within her pussy. She was not done for the evening, just done with Bob. She quickly threw her dress clothes over her lingerie and stepped back into the office.

Bob was sitting up on the edge of the desk. He was still recovering from his powerful orgasm. Sheila went up to him and kissed him passionately.

"That was great, lover. You are great. There is a shower in my private bathroom if you want to clean yourself off and then do be a good boy, and get yourself dressed and let yourself out. I will be thinking about you everyday until we can get together again next Wednesday. And make sure to close the door behind you." She hurriedly left the room and practically ran to the elevator.

Bob stepped into the shower and ran some soap over his penis and scrotum. He then got dressed, left the office, took the elevator to the garage and headed home. He again felt guilty about cheating on Rebecca. Sheila's passionate exuberance was quite the opposite of his wife, and he decided, "Hey, if Rebecca isn't interested, then I am going to enjoy Sheila, because she clearly is."

Sheila was anxious to get home. She did not want to waste the cum she had trapped in her vagina. Jane, one of the paralegals from the office, was at home waiting for her. Assuming that she had followed Sheila's specific orders, she should be completely naked and spread eagle on the bed with cuffs around her ankles and wrists.

Sheila hurried in from the garage. Jane had properly followed orders. Before even undressing, Sheila grabbed the straps tied to each of the bedposts and clipped them, one by one, to each of Jane's cuffs. She then pulled the straps tight so that Jane's body was taut against the bed and she could barely move.

Sheila quickly took off her outer layer of office clothes revealing the lingerie underneath. She reached between her legs and slid the long steel dildo from her cunt and placed it carefully on the side table. She was excited to see that it was covered in cum that had started to harden on the metal. That would come into use later. She placed her hands on her headboard and without any preamble pressed her cunt down onto Jane's face. "Lick me, you slut", she commanded Jane.

Jane pushed her tongue up into Sheila's pussy. She immediately noticed that instead of Sheila's normal slippery fluid, instead she encountered a sticky and gooey mess. Jane started to gag, which is exactly what Sheila wanted. "That's right my lesbian slut, you are eating fresh sperm, just deposited there by Bob from work. I knew a lesbian slut like you would hate the texture and the taste so I brought it home as a special treat."

Humiliation was a big turn on for Sheila. Not quite as exciting as listening to a woman scream, but close. She squeezed her vaginal muscles, trying to force the stale jizz to leak from her cunt into Jane's mouth. Jane was repulsed, but she was tied down tightly and had no opportunity to get away. Sheila lifted herself up slightly using the headboard for leverage, and squeezed again. A large sticky string of cum slid from her cunt right onto Jane's mouth. Sheila loved it. She stood up, and using her finger, pushed the white goo from Jane's lips into her mouth. Jane's eyes were practically popping from her face; she was so completely disgusted. Once all the cum on her lips had been pushed in, Sheila reached over to the side table and picked up the steel dildo.

"I have one more treat for you." she said, holding the dildo covered in hardened cum above Jane's face. Jane twisted her head from side to side. She did not want that thing in her mouth. Sheila was prepared for Jane's disobedience. She slid the drawer of the side table open, reached in, and pulled out a small set of pliers. Jane couldn't see what Sheila was doing, but the next thing she felt was her nipple being crushed in the jaws of the pliers. She screamed out in pain, which was just what Sheila was waiting for. With Jane's mouth wide open, she took the steel dildo and slid it deep into her mouth, pressing down hard with her palm against the flat base to hold it in. Jane's eyes were wide open in a combination of pain and disgust.

Sheila let go of Jane's nipple, and talked to the young paralegal, "That is so much better. Now do a good job sucking because you know I like to keep my toys clean. If you do, I won't have to use the pliers again." Jane did exactly as she was told, anything to avoid the pliers, but she was thoroughly grossed out as the flakes of cum dissolved in her mouth.

Sheila waited a minute, enjoying Jane's obvious dislike of having the soiled dildo in her mouth. Sheila pulled the dildo out to inspect it. "Almost clean" she said as she pushed it in a second time causing Jane to gag. She waited 30 seconds and inspected it. "You have done a good job, and now you get your reward."

Sheila went into her walk-in closet, and slid her long legs through a harness for holding a dildo in place. She pulled open a drawer containing her collection of strap-on dildos all neatly arrayed in their place. She knew that Jane loved being stretched open, so she choose a life-like cock that would have been the envy of most men. She slid it into place and stepped out.

She stood by the bed so that Jane could see the long toy sticking out from Sheila's pubic region. She looked up at Sheila's face and said in an excited voice."Oh, yes, thank you for my reward, mistress." Sheila started to release Jane to get her bent over the bed face down for a rough fucking with the large dildo.

Sheila was very pleased with herself. Her plan was on track, and she was having a great deal of fun carrying it out.