{"id":53593,"date":"2024-02-12T06:04:13","date_gmt":"2024-02-12T12:04:13","guid":{"rendered":"http:\/\/idtryittwice.com\/?page_id=53593"},"modified":"2025-01-22T07:47:23","modified_gmt":"2025-01-22T13:47:23","slug":"the-bet","status":"publish","type":"page","link":"https:\/\/idtryittwice.com\/index.php\/the-bet\/","title":{"rendered":"The Bet"},"content":{"rendered":"\n

Oblivious at the time, my fate was being decided by two young ladies at a party I was attending. Bragging about her prowess \u201ctaming men\u201d, Becky was a little tipsy as she regaled her friend Tiffany with her sexual exploits. When Becky finished a story about leaving a man tied up in his apartment after a one-night stand, Tiffany was determined to one-up her friend with a story of pegging a guy. Looking to regain her position in the conversation, while pointing at me, Becky said, \u201cI bet I could have that dude in a cock cage inside a week.\u201d Apparently, I was chosen at random as I did not know either of the ladies. Piquing Tiffany interest, she asked, \u201cWhat is the wager? What happens if you don\u2019t get him locked up?\u201d Becky said, \u201cYou can fuck me in the ass with your strap-on.\u201d Looking for further clarification, Tiffany asked, \u201cAnd, what will it cost me if you are successful?\u201d Becky said she would fuck Tiffany in the ass with her strap-on. Following up, Tiffany asked, \u201cHow will I know if he\u2019s wearing a cage?\u201d Becky had a simple answer, Becky would give Tiffany the key and the Dude would have to ask her to be released. The bet was on.<\/p>\n\n\n\n

Becky didn\u2019t waste time to try to pick me up with perhaps the most unique line I have heard, \u201cYour cock looks heavy, can I hold it for you?\u201d I almost fell over backwards. Becky was tall, had. long brunette hair, and perky tits. I was attracted to her immediately. My response was lame, \u201cHi! I\u2019m Michael. What is your name?\u201d After telling me her name, she continued with a barrage of sexy compliments, \u201cAre you undressing me with your eyes, Michael\u201d\u201d As a matter of fact I was, but I told her no. She followed up, \u201cWould you like to?\u201d It was clear Becky was picking me up, so I stepped up my game, \u201cI\u2019d rather undress you for real.\u201d Becky smiled, took my hand and led me towards the front door before turning around and asking if I had a coat to pick up before they left.<\/p>\n\n\n\n

Knowing she had a cock cage at her house, which had been left behind by a previous boyfriend, she suggested we go to her place. We took her car. It took about twenty minutes to get to the small two-bed adobe house with a carport. Before we got out of the car, she leaned over and gave me a passionate kiss. I was getting highly aroused, and I could feel my dick starting to swell. Before she unlocked the door, she unbuttoned the top two buttons of my shirt and unbuckled my pants. Once inside, but still in the entryway, she turned around, unzipped my pants, and pulled them to the ground, and finished unbuttoning the shirt. She then leaned over towards me and whispered, \u201cI like to play rough.\u201d I stepped out of my pants, took my shirt off, and stood in front of Becky in my underwear. She was still fully dressed.<\/p>\n\n\n\n

Leading me by my hand to her bedroom, she finished undressing me. First removing my T-shirt and then stepping behind me and pulling my underpants to the ground before telling me to lay down on the bed. Naked in front of a fully clothed beautiful woman, I was becoming self-conscious and covered my groin as I got into the four-poster bed. Becky left the room briefly, then returned with four pieces of rope. Smiling, she took my hands away from my groin, and expertly tied my arms by the wrists to the headboard. She then did the same to my ankles, leaving me spread-eagle. Crawling into bed and straddling my chest, she asked, \u201cAre you attracted to dominate women, Michael.\u201d I had no experience with dominant women, but my semi-hard cock spoke for me. \u201cDo you know what BDSM is, Michael? Do you want to play with me?\u201d I told her, \u201cYes, very much.\u201d She had me hooked.<\/p>\n\n\n\n

Becky got off my chest and took something from a dresser drawer. Showing it to me, she asked if I knew what it was. I feigned ignorance, even though I was pretty sure what it was, \u201cIt\u2019s a cock cage, Michael. Will you wear this for me?\u201d I wasn\u2019t quite sure what she was asking me. I asked for clarification, \u201cFor how long, Becky?\u201d Becky sat down next to me, then reached over and gripped my penis and balls, giving a slight squeeze. \u201cI like to be called Mistress when we play, Michael.\u201d Taking her cue, I responded, \u201cYes, Mistress.\u201d Then she explained, \u201cYou\u2019ll wear it until we\u2019re finished playing, Michael.\u201d I agreed to wear the cage and she put it on me.<\/p>\n\n\n\n

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

Once the cage was locked, Becky left the room for a minute, apparently to hide the key, before coming back to the bedroom and untying me. Confused, I asked, \u201cAre we going to have sex now?\u201d Becky smiled, \u201cNot tonight. You can put you clothes back on.\u201d Embarrassed by my situation, naked and sporting a cock cage, I looked for my clothes and dressed myself. I stood in the doorway totally perplexed. What have I gotten myself into. I didn\u2019t even have my car with me. Becky approached me she while texting someone. \u201cCome on, Michael. Let\u2019s go get your car.\u201d I asked if she could take off the cage and she said, \u201cWe\u2019re not finished playing yet, Michael. Come.\u201d I followed her to the car.<\/p>\n\n\n\n

When Becky dropped me off at my car, she simply said she\u2019d \u201ckeep in touch.\u201d I was beginning to think I was going to have to visit a locksmith, but before leaving, she handed me a piece of paper saying, \u201cThis is the person who will have the key.\u201d I looked at the piece of paper, it read: Tiffany, 301-265-9634. I drove my car home and texted Tiffany asking if she had something for me. Tiffany messaged back a few minutes later, \u201cWhat are you looking for, Michael?\u201d She knew my name. I wrote back, \u201cDo you have a. key for me?\u201d Tiffany clearly was playing a game with me when she wrote back, \u201cA key for what, Michael?\u201d Clearly she was in on it, so I wrote back, \u201cFor the cock cage.\u201d Tiffany wrote back with an address and a time, 7:00 PM the next evening.<\/p>\n\n\n\n

At the appointed time, I knocked on Tiffany\u2019s door. She let me in and she led me into the living room. With a simple command, \u201cStrip.\u201d, I took my clothes off. For the second time in two days I was standing naked in front of a clothed female stranger while wearing a cock cage. She looked down at the cage expressionless. I asked for the key and she said it was on the way. It seems Becky didn\u2019t give Tiffany the key and telling me she had it was a ruse. Becky sat on the couch and I stood in front of her for about fifteen minutes before I could hear a car pull into the driveway. <\/p>\n\n\n\n

Becky let herself in. She was carrying a small satchel. I looked at her expecting she would produce the key and instead she walked up to Tiffany and said, \u201cWe have a wader to settle.\u201d Tiffany got off the couch and they both went into the bedroom. I waited where I was standing for about ten minutes until I began to hear noises coming from the bedroom. There was a slapping noise and rhythmic grunting and screaming. Curious, I went to the room where the noises were coming from. <\/p>\n\n\n\n

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

The door was partly open. The room smelled and sounded like sex. I went inside. Becky was fucking Tiffany in the ass with a strap-on. As she penetrated her, Becky was slapping Tiffany\u2019s clit. This wasn\u2019t love-making. Becky was punishing Tiffany\u2019s asshole, and she seemed to be enjoying herself. Tiffany was not enjoying herself. This went on for about fifteen minutes. During that period, Becky turned around several times and smiled at me. When Becky finished butt-fucking Tiffany, she got dressed, put the strap-on back in her bag, and handed me a key. I took the key from her, freed myself, and threw the cage on the bed before getting dressed and leaving. I never saw Becky of Tiffany again.<\/p>\n","protected":false},"excerpt":{"rendered":"

Oblivious at the time, my fate was being decided by two young ladies at a party I was attending. Bragging about her prowess \u201ctaming men\u201d, Becky was a…<\/p>\n","protected":false},"author":1,"featured_media":53594,"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":[16,131,85],"class_list":["post-53593","page","type-page","status-publish","has-post-thumbnail","hentry","category-fiction","tag-chastity","tag-lesbian","tag-strapon"],"aioseo_notices":[],"jetpack_likes_enabled":true,"jetpack_sharing_enabled":true,"_links":{"self":[{"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/pages\/53593","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=53593"}],"version-history":[{"count":3,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/pages\/53593\/revisions"}],"predecessor-version":[{"id":56110,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/pages\/53593\/revisions\/56110"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/media\/53594"}],"wp:attachment":[{"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/media?parent=53593"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/categories?post=53593"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/idtryittwice.com\/index.php\/wp-json\/wp\/v2\/tags?post=53593"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}