{"id":54167,"date":"2024-05-07T17:30:05","date_gmt":"2024-05-07T22:30:05","guid":{"rendered":"http:\/\/idtryittwice.com\/?page_id=54167"},"modified":"2025-01-23T13:12:04","modified_gmt":"2025-01-23T19:12:04","slug":"the-boss","status":"publish","type":"page","link":"https:\/\/idtryittwice.com\/index.php\/the-boss\/","title":{"rendered":"The Boss\u00a0"},"content":{"rendered":"\n

Lynda had been employed as a secretary ever since she graduated from high school, nearly seven years. She had been working at the same company for most of that time, for a cadre of bosses. She had been promoted a few times, but still was part of a pool of secretaries, and it was not uncommon to work for an individual for just a few weeks. Although there were female executives at the business, up to now, she had male bosses. None had been unpleasant to work for, until she was assigned to work for Bob.<\/p>\n\n\n\n

Bob was a few years younger than she was, fresh out of Harvard business school. Lynda was pretty sure he had a relative in upper management, which helped land him a position higher in the echelon than might be expected for someone who just graduated from college. <\/p>\n\n\n\n

Lynda met Bob for the first time after she had been assigned to him. The first thing she noticed about him was how smartly he dressed in clothes that were more expensive that others wore in his position. She was quickly put off by his attitude, which was frat-like, and his sophomoric humor. Bob liked to tell off-colored, sexist jokes that marginalized women.<\/p>\n\n\n\n

For the first few weeks, Bob kept his hands to himself, but he soon began to touch Lynda. At first, he would just stand too close or touch her hand, but he also sometimes put his hands on her shoulders or around her waist. He seemed to be pushing to find the limit at which Lynda would protest. When he slapped her butt, Lynda snapped. While she didn\u2019t say anything at that moment, she started clandestinely recording her interactions her.<\/p>\n\n\n\n

After a week of collecting evidence, which included voice recordings of sexist conversation and video recordings of his physical assault on her, Lynda confronted her boss. She was looking for more than simply having her boss cease and desist his boorish behavior. She intended to upend the power dynamic. She was tired of standing on the low rung. Lynda blackmailed her boss.<\/p>\n\n\n\n

Bob was naturally frightened. His livelihood was being placed at risk. If he were to lose his first job under such scandalous conditions, he might not get another. Saddled with huge student debt, he would be ruined financially. His beta response to Lynda\u2019s attack did not come naturally to him. He had always been the top dog, but his meek response punctuated the terror he felt. He would do \u201canything\u201d to make things right.<\/p>\n\n\n\n

Lynda kept Bob on the hook for several days. This was part of her plan to sweat him. She was careful not to give him any physical evidence of her blackmailing him. He tried to discuss the matter with her via e-mail, but she did not respond in writing. The subject was only discussed by her verbally, randomly throwing out threats like \u201cI\u2019m still thinking about an appropriate punishment.\u201d<\/p>\n\n\n\n

Bob was on his best behavior, even bringing Lynda flowers and Starbucks. As Lynda carried out her secretarial duties, she noticed that Bob had lightened her workload. However, this was not enough. She really wanted to punish Bob. As the days pass, she began to enjoy her new-found clout. She began to daydream about the thinks she could make her boss do.<\/p>\n\n\n\n

Lynda\u2019s first overt dominant act was to insist that Bob refer to her as Ms. Jackson, while she started calling him Bob, rather than Mr. London. Soon after that, she started throwing in quips that challenged his manhood, including suggesting he needed to \u201cgrow some balls.\u201d <\/p>\n\n\n\n

The emasculation was pushed further when she suggested his \u201cpeepee\u201d was probably too small to satisfy a real woman. Later that day, she entered Bob\u2019s office, closed the door behind her, and challenged her boss to drop his pants so she could examine his \u201cweenie.\u201d Bob refused, but Lynda reminded him of his jam. Bob reluctantly dropped his pants. Lynda smiled at his \u201ctighty whities\u201d and urged him to get on with it. Lowering his underwear, Lynda broke out in a belly laugh when she saw he shaved his genitalia. \u201cYou look like a five-year-old.\u201d Lynda took out her cellphone and snapped a photo before Bob could cover himself. \u201cThis is going on the Internet for sure.\u201d<\/p>\n\n\n\n

Bob knew Lynda had him by the nuts. Bob\u2019s off-color jokes had been replaced in the office by Lynda\u2019s \u201csmall-dick\u201d quips. Lynda pulled her panties off, brushed some of Bob\u2019s stuff off his deck top, hiked up her skirt, and sat down on the desk. Suggesting the only thing he was good for was licking pussy, she pointed and demanded that he do down on her. He refused. Lynda took her phone out and threatened to send the photo of him standing with his pants around his ankles to his colleague. Bob got on his knees below her and Lynda pulled his face into her cunt. \u201cIf you don\u2019t make me cum, I\u2019m sending the photo to everyone at work.\u201d<\/p>\n\n\n\n

Lynda suggested Bob didn\u2019t have much experience performing cunnilingus. \u201cUp to now, you\u2019ve been more of a fuck-her-N-leave-her kinda guy, haven\u2019t you been?\u201d When Bob didn\u2019t reply, Lynda pulled his face away from her crotch and slapped him. \u201cAnswer me, cunt.\u201d Bob said he didn\u2019t have much experience. Lynda promised to change that. \u201cThe first thing you\u2019re going to do every morning at work is service my pussy. Got it cunt?\u201d Bob nodded his head in agreement. At one point, Lynda used Bob\u2019s hair to pull his face away from her pussy and snapped another photo. Fifteen minutes later Lynda experienced an orgasm. Bob started to wipe his face. \u201cNo, leave my cum on your face. The other secretaries will smell it and know who the boss is.\u201d<\/p>\n\n\n\n

\"\"<\/figure>\n\n\n\n

Later that evening, Bob received an e-mail from an address he did not recognize. The photo of him licking his secretary\u2019s pussy was attached. His face was slimy with Lynda\u2019s cum. The e-mail comprised one sentence \u2026 \u201cThere is something I want you to do for me in the morning.\u201d There were no other details.<\/p>\n\n\n\n

When Bob arrived at work in the morning, Lynda smiled as he walked past her desk and entered his office. Closing the door behind him, he saw a small package on his desk. It was wrapped in pink paper and had a pink bow. Bob read the note \u2026 \u201cPlease put on before you lick my pussy this morning.\u201d Inside the box was a small velvet bag that contained a steel chastity cage. Bob had never actually seen one before, but it was obvious to him what it was. He put the cage in his desk drawer.<\/p>\n\n\n\n

Bob had been seating at his desk for about half an hour before Lynda came in unannounced. Closing the door behind her, she asked if Bob liked his present. Bob didn\u2019t respond. \u201cShow it to me.\u201d Bob confessed he had not put it on. Lynda took a seat and pulled out her phone. \u201cWho should I send the photos to first?\u201d Bob knew if the photos got out, more than his career would be affected. He sat at his desk as Lynda continued to berate him. Bob was cornered. He had no choice. He asked Lynda to leave while he put the cage on, but Lynda said she wanted to watch. Lynda took photos as Bob struggled to put the cage on. When he finished, Lynda took the keys.<\/p>\n\n\n\n

After putting the cage on, Bob tried to put his pants back on, but Lynda told him she wanted to see the cage while he serviced her pussy. \u201cIn fact, take all your clothes off, Slut.\u201d Naked, Bob licked Lynda\u2019s pussy as he had the day before, except he was sporting a cock cage. When Lynda was done, Bob asked how long he would have to wear the cage, and Lynda told him \u201cforever.\u201d Bob was still naked when Lynda put her panties back on, adjusted her clothes, and started to leave. \u201cDo you want me to leave your door open.\u201d Bob begged her to close it. Another e-mail arrived that evening. Photos of him putting on the cock cage were attached. There was no message. He felt his professional life was over.<\/p>\n\n\n\n

The routine each workday the following week was the same. Lynda would come into his office about a half hour after he arrived at work. She would order him to take his clothes off. She would \u201cinspect\u201d his cage while tugging on it. After she removed her panties, Bob would perform cunnilingus until she experienced an orgasm. <\/p>\n\n\n\n

On Friday, after her orgasm, Lynda remained longer than usual to pile on some humiliation. \u201cYou\u2019re not really a man anymore, are you Bob? I mean, you no longer have a penis. But, you do have a pretty pussy, don\u2019t you Bob? Show me your pussy.\u201d At this point Lynda stands behind Bob. Squeezing a butt cheek, she gave Bob\u2019s bottom a pat. Bend over, Bob, and spread your cheeks. Show me your pussy, bitch.\u201d  Pushing Bob towards his desk, Lynda put the palm of her hand between his shoulder blades and pushed until Bob\u2019s palms were planted on the top of his desk. Kicking his legs apart, Bob assumed a frisk-like position. Lynda stepped back and admired her work. Bob\u2019s caged junk hung between his legs. Lynda snapped a few photos. \u201cYou have a very pretty pussy, Bob. It looks very fuckable.\u201d<\/p>\n\n\n\n

The humiliation weighed heavily on Bob during the weekend. There were no more messages from Lynda, but he of course knew she was not in possession of dozens of degrading photographs. When Bob arrived at work on Monday, he slipped past Lynda without saying anything. But, on cue, Lynda entered Bob\u2019s office. Bob knew the drill and undressed. As she had before, Lynda watched the striptease with a broad smile on her face. Bob waited naked for Lynda to remove her panties so he could get his service out of the way. <\/p>\n\n\n\n

\"\"<\/figure>\n\n\n\n

Lynda was wearing an overcoat. When she removed it, a strap-on dildo flopped out. \u201cWe\u2019re going to do something different this morning, Bob. I\u2019m going to fuck your pussy.\u201d Bob was speechless, but he didn\u2019t argue. Lynda had broken him. As she had on Friday, Lynda led Bob to the \u201cfrisk position\u201d. It was as if Friday was a rehearsal. \u201cBend over, Bob. I\u2019m going to make you a woman.\u201d Bob zoned out as Lynda forced her cock into his rectum. She laughed as she pegged him, pausing only to snap photos. At one point she moved him to the desk, fucking first doggy, then flipping over on his back. She made a film while fucking him, panning back and forth from the dildo penetrating his ass to his face, which had a pained, horrified expression.\u00a0<\/p>\n\n\n\n

Lynda\u2019s violation of Bob\u2019s ass continued for almost twenty minutes, eventually interrupted by a phone call. Her cock still in Bob\u2019s ass, she answered the phone professionally. \u201cYes, Mr. London is available. One moment.\u201d Lynda handed the phone to Bob. His immediate supervisor was on the phone. Answer the phone, Bob tried to speak intelligibly while Lynda continued to peg him. Bob tried to control his groans, but he was certain the man on the phone could hear the slap-slap-slap of Lynda\u2019s thighs bounce off Bob\u2019s butt. When Bob finished the call, Lynda pulled her dick out of his ass. Bob seemed to whimper while Lynda put on her overcoat and left.<\/p>\n\n\n\n

The next morning, Lynda was not at her desk when Bob arrived at work, It was a relief as Bob had come to dread the morning rituals. When Bob settled into his office, he found a letter on his desk. It was a resignation letter.<\/p>\n\n\n\n

Dear Bob:<\/em><\/p>\n\n\n\n

I would like to inform you that I am resigning from my position as your secretary, effective immediately.<\/em><\/p>\n\n\n\n

Thank you for the opportunities for professional and personal development that you have provided me during the past month. I have shared my positive experiences with the other secretaries and have encouraged them to reach out to you for mentoring.<\/em><\/p>\n\n\n\n

I have turned in the company keys. I have kept the \u201cspecial\u201d key.<\/em><\/p>\n\n\n\n

If I can be of any help during this transition to a new secretary, please let me know.<\/em><\/p>\n\n\n\n

Sincerely your,<\/em><\/p>\n\n\n\n

Ms. Jackson<\/em><\/p>\n\n\n\n

Bob had mixed emotions. He was certainly relieved, but he was going to have to find a way of getting the chastity device off. <\/p>\n\n\n\n

Calling HR, Bob requested a temp to cover Lynda\u2019s responsibilities. Susan Jefferson arrived later that morning. As they were getting to know one another, the temp said that she would prefer to be called Ms. Jefferson. She also said Ms. London had already provided some training. At that point Susan took out her cell phone and played the video of him getting pegged. \u201cPerhaps we could start with you taking your clothes off, Bob.\u201d<\/p>\n","protected":false},"excerpt":{"rendered":"

Lynda had been employed as a secretary ever since she graduated from high school, nearly seven years. She had been working at the same company for most of…<\/p>\n","protected":false},"author":1,"featured_media":54168,"parent":0,"menu_order":0,"comment_status":"closed","ping_status":"closed","template":"","meta":{"om_disable_all_campaigns":false,"rop_custom_images_group":[],"rop_custom_messages_group":[],"rop_publish_now":"initial","rop_publish_now_accounts":{"twitter_1636176473479581697_1636176473479581697":""},"rop_publish_now_history":[],"rop_publish_now_status":"pending","_exactmetrics_skip_tracking":false,"_exactmetrics_sitenote_active":false,"_exactmetrics_sitenote_note":"","_exactmetrics_sitenote_category":0,"footnotes":""},"categories":[324],"tags":[16,135,63,70],"class_list":["post-54167","page","type-page","status-publish","has-post-thumbnail","hentry","category-fiction","tag-chastity","tag-cunnilingus","tag-modeling","tag-pegging"],"aioseo_notices":[],"jetpack_likes_enabled":true,"jetpack_sharing_enabled":true,"_links":{"self":[{"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/pages\/54167","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/pages"}],"about":[{"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/types\/page"}],"author":[{"embeddable":true,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/comments?post=54167"}],"version-history":[{"count":3,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/pages\/54167\/revisions"}],"predecessor-version":[{"id":56210,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/pages\/54167\/revisions\/56210"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/media\/54168"}],"wp:attachment":[{"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/media?parent=54167"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/categories?post=54167"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/tags?post=54167"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}