Cuckold CEO Ch. 05

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Day three of our vacation started with a thud. I woke up rolled over and my wife informed me that she had started her period. Well at least I was getting unlocked from my cock cage for a week. Usually, when my wife has her period, she unlocks my cage and lets me jerk off to relieve myself for a week. Sometimes we play sexy games with each other, but mostly it’s me jerking off to internet porn. She rolled out of bed and hit the shower as I fell back to sleep for a while longer. At some point, she finished her shower and started fiddling with her luggage at the foot of the bed. I tore open my eyes and looked down towards her.

She was standing there, stark naked, looking absolutely stunning. I commented how lucky I was to have her in my life. She smiled shyly and told me she felt the same way about me. She grabbed a few things and slipped back into the bathroom. I closed my eyes again and drifted off to a semi conscience state. My wife exited the bathroom a bit later and stood by my side of the bed. Although my eyes were closed, I sensed her prescience. I opened my eyes to see what she was doing. She was standing about two feet from the bed smiling at me. She was naked from the waist up but was wearing a different kind of panties. They were the type that looked like boy’s underwear with the fly hole. They were from the famous lingerie store from the mall and were red. They looked incredibly hot on her. Her figure was perfect for this type of underwear. She looked down at me and asked if I they were cute.

I grabbed her by the waist and pulled her over to me and motor boated her pussy. She giggled and said that the answer seemed to be yes. She bounced like a like a baby deer back to the bathroom and shut the door. I stared up at the ceiling and marveled over how great my life was. A few seconds later, she came back out and stood back in the same place. I turned to her and she asked me what I thought about them now. I burst out laughing. She had taken her favorite dildo, she named Jimmy, and had stuffed it into her underwear. It didn’t fit at all. The balls pulled at the crotch and the shaft stuck out the top. I pulled her back over to me and told her to let a man show her how a cock should be worn.

I pulled it out and lowered her underwear. I pushed the shaft through the fly hole and adjusted the balls low in the crotch. I pulled her underwear back up and adjusted them and told her that it looked much better. She giggled and asked me if it looked good. I laughed and told her that she was the most beautiful boy I had ever seen. She smiled broadly, then went over to the drawer and removed my cage key from the nightstand an unlocked me. Fuck, it felt good to be out of that thing. I took a couple of strokes on my cock and it became semi-rigid. My wife stood there and watched me. She then looked down at me and asked me if I wanted to cum. I enthusiastically said yes.

She told me to get out of bed and to get on my knees. I hopped onto the floor as directed. I assumed she wanted her pussy licked first. She got right in front of me and asked me if I liked her hard cock. I played along and told her that Bayan Eskort I did. She smiled and told me to kiss it. My heart began to race. Wow, I thought, she knows how to push my buttons. I kissed her cock and she told me to do it again. I did it again. She asked me again if I liked her hard cock and I said yes. She grabbed my head and made me look into her eyes and told me that she wanted me to suck her cock. I shook my head no. She slapped me and told me to do it. Fuck, I thought, why did she slap me so hard? My mind told me not to do what she asked, but my body said something totally different as my cock sprung to attention. She placed the tip on my lips and began to push it in.

It felt so strange but incredibly erotic. I sucked it gently. She wanted more and she began fucking my face, like her lovers do to her. I relaxed my jaw and decided to play along. She looked down into my eyes and told me to jerk off while I sucked her off. I reached my right hand down and grabbed my cock. I was as hard as a rock. I hadn’t felt my cock this hard since I was in my 20’s. She told me that I was a bad boy and that bad boys got punished. My punishment was having to service her cock. She pulled her cock out of my mouth and asked me if I understood. I said that I did, totally. She immediately shoved it back into my mouth and demanded that I make eye contact with her. I looked deeply into her eyes as she used my mouth for her pleasure.

It was a strange feeling to be sucking cock on my knees. For almost 30 years I have been making women get in that position and telling them to do the same thing. I had never realized how much power I was exerting on them and how helpless they felt. My wife was teaching me what it felt like to submit and to service a man’s cock. It was a total 180 for me. At work, I am the Alpha Male, large and in charge and all powerful. Yet here I was, on my knees, with a cock shoved in my mouth being told to take it deep. The total relinquishment of control was frightening but intoxicating. In fact, I found myself jerking off furiously as she fucked my mouth. She could tell I was getting into it and actually getting close to cumming but she wanted to remain in control. She pulled Jimmy from my mouth and told me to get into bed.

I laid down in bed. She told me to get on my hands and knees. She got on the bed and knelt in front of me and started fucking my mouth again. She reached over my back and slapped my ass a few times real hard. I let out a muffled scream, she told me to shut up and take it like a bitch. Wow, I thought, she was getting into this bigtime. She got me close again and once again pulled Jimmy from my mouth. She pulled my head up by the hair and kissed me roughly and deeply and asked me if I liked being a bitch. I told her yes.

She reached over to the night stand and grabbed something out of the draw and repositioned herself behind me. All of a sudden, I felt cold wetness on my asshole. I asked her what she was doing and she told me to shut up. I then felt what seemed like her thumb enter my ass. I yelped and she told me not to be a pussy. She worked the lube she had poured on my asshole in, with her thumb, a couple more times, then rubbed the balance on Jimmy. She then told me to tell her how much I liked her big cock. I told her no and that she was pushing it too far. She demanded that I tell her that I liked her big cock. Again, I protested. Without warning, she grabbed my waist and pushed Jimmy into my tight asshole.

I howled in protest. She told me to shut up and take it, then slapped my ass hard. She pulled back, then thrusted again, gaining more depth than the first thrust. It hurt like hell and I begged her to stop. She refused, telling me that women get raped all the time and men don’t stop when women beg. My wife was in a zone I had never experienced before. She was in total control, stern and in charge fully. I decided to just relax and let her do what she needed to do. She obviously had a motive behind this and I wanted to get to the end as fast as possible. She started talking dirty to me, calling me a bitch and asking me if I was a big cock slut. I played along and told her yes. It was then Jimmy hit my prostate. My cock jumped. The feeling was strange. My ass hurt like hell but the dildo on my prostate and felt weirdly nice.

I tried to relax more and the results were better. My asshole started to stretch and the constant pounding on my prostate produced a slow dribble of pre-cum from my cock. My wife reached around to see if my cock was hard. I was semi-rigid. My cock oozed pre-cum on her fingers. She pulled my hair and made my head fling backwards. She got close to my ear and told me that I really was a big cock slut. She said my cock was obviously happy because it was drooling and so now I needed to cum for her. She told me to reach down and start jerking off. I took my tool in my right hand and began to stroke it. It popped to attention without a great deal of effort. She reached down and found my rock-hard erection. She told me that she was going to fuck my ass hard until I had an orgasm, so I should get jerking quickly.

She grabbed my hips and pounded me hard. I jerked off furiously. My cock continued to produce a long stream of clear sticky goo. She kept demanding that I cum. The more I delayed, the more she demanded. Then she slapped my ass and called me a bitch and told me to cum. The whole thing was overwhelming. The cock in my asshole was pounding my prostate into submission, while my wife was going postal on my ass. I began to tremble. My orgasm did not start as usual. Usually, there was a build-up, then the tell-tale pulsing in my balls, the stiffening of my body and then explosion. No, this time, my body started to tremble, my ass cheeks tightened and cum began to drool from the tip of my cock in a long rope without any sensation of a release. Then the orgasm hit. It was like being electrocuted. My toes curled, my hands turned into fists, I let out a loud involuntary scream and began to convulse.

Each convulsion forced Jimmy deeper into my asshole, generating even more pressure on my prostate. My wife tried her best to bury Jimmy as deep into my hole as she could. Her hands had a death grip on my waist. My formerly caged penis, made a huge puddle of cum mixed with clear pre-cum on the sheets. My wife waited until I stopped cumming before she released her grip. I fell to the bed trembling and shivering. She laid down beside me and held me in her arms. My prostate was so over stimulated that it had two more aftershocks. Both resulted in an inch- long ribbon of additional cum on the sheets. She reached down and scooped up the last one and rubbed it on my trembling lips, then kissed me. It took forever to breathe normally.

As I began to calm down, she whispered in my ear. She asked me how it felt to be totally at the mercy of someone else. She asked me if I now knew what it was like to be a woman. I was still shaking as I told her that my orgasm was the most intense of my life. I had never had my cock produce cum before I felt the release of an orgasm. She asked me again if I understood how a woman felt when a man fucks her hard. I told her that it was the one the most uncomfortable things I had ever done yet it was the most erotic feeling I had ever had. Yes, I now had a small understanding of what it was like to be fucked hard by a man. The loss of control was frightening and yet very liberating. I had to put my faith in a leader, then go to where she wanted to go without questioning. Was this what my employees felt like, I wondered? I trusted her and she took me to a place that, an hour ago, I would have never thought I’d be. I had given up all sense of control and it felt good even though I had a cock shoved up my ass against my will.

My wife rolled over and faced me. Jimmy poked my stomach and we both laughed. She pulled him out of her underwear and tossed him off the bed. We kissed and hugged for hours afterward. She finally was the first to get out of bed. She told me to stay in bed, she had a gift for me. I love presents. I sat up and waiting like a kid at Christmas. She handed me a bag from the lingerie store and told me to open it. It was a very sexy pair of pink, silk thong panties with a red heart on the crotch. I loved them. I pulled them out and unfolded them. My wife is 5 foot 2 inches and 100 pounds soaking wet. These were extra-large. I told her they were really sexy but she got the wrong size. She smiled slyly and to me that they were for me. What, I thought? I must have looked confused because she repeated it again. I asked why she wanted me to wear them.

She told me that they were cute and from now on when she was having her period, she was going to wear boys underwear and she wanted me to wear the girl panties. I laughed a bit and said ok. I put them on. The silk felt really nice against my skin. My cock and balls bulged in the front and the strip of silk up the back caressed my asshole. She told me to spin around. She cooed as I did. She giggled like a school girl at the sight. My wife then jumped into my arms and told me how much she loved me. She planted a wet kiss on me then told me to take a shower, it was time to go take a walk on the beach. I turned and entered the bathroom. I looked into the mirror. What I saw was a full-grown man who had just been fucked up the ass in a pair of woman’s underwear. My life had taken a very strange turn and I think I liked it. I love my wife to death.

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