Elisabeth
by sheepisheyes » Tue Apr 30, 2024 9:30 am
Elisabeth is an interesting woman. At first you would think she is very timid and shy, but the better term is passive aggressive. She gets what she wants, and you don’t even see it coming. Elisabeth is a very attractive woman, average height, kind of small breast, beautiful ass and a pretty face. Definitely someone you could jerk off to at night (or anytime).
We work together and the other day she came to my office to ask a question. Unfortunately, I did not hear her coming and was busy rubbing myself through my pants reading loser jerkoff captions. My work blocks porn but I can somehow get to these. Anyway, I was feeling really pathetic just as she walked in and saw my monitor with a picture of a girl making a jerking motion with the caption “your hand is all you’ll ever get”. Then she looked down at me rubbing myself through my pants. I realized that she just saw everything I was doing, as a wave of humiliation washed over me. I felt so pathetic as I looked at her and to make matters worse, I started cumming in my pants. My mouth dropped open as my orgasm face took place and I was spurting. I watched her eyes go from my face to my pants and back as a large wet spot started to form. She stood there with a condescending smile on her face and told me she’ll stop back in a while so I can clean myself up. She turned and left, laughing.
I quickly tried to sop up the cum stains with a napkin, but I was so humiliated and turned on, there was just so much cum. My pants leg near my crotch was a wet sticky mess. About 30 minutes later Elisabeth came back, this time knocking first. I placed a notebook on my lap. She laughed and said, “Don’t bother trying to hide it, I saw the whole thing”. I moved the notebook and my cum stain was clearly visible. She started to crack up. “I want to ask a work question, but I just can’t take you seriously” she said as she laughed more at me. “I can’t believe you are jerking off looking at humiliation porn and then cum in your pants right in front of me! That is so pathetic! And you get caught doing it!” I looked at her and said I was sorry. She laughed some more “Give me a break. You’re not sorry at all. When I caught you, you started cumming. That didn’t look like you were sorry. What about your wife? She must see your cum stains. Can you even get it up for her?” she asked. I told her we don’t have sex anymore. “No wonder look at you. If my husband spent his day jacking off and cumming in his pants I wouldn’t have sex with him either”.
I told her that it’s because we don’t have sex that I do that not the other way around. ” Oh please. She’s not having sex with you because you are a masturbator. Believe me I am a woman, and no woman is attracted to a man that is a chronic masturbator, especially one the gets off on humiliation. You’re not a real man, that’s why she won’t have sex with you. How long has it been?” she asked. I told her we haven’t had sex for 10 years. “Jesus! That’s insane. 10 years! Are you a cuckold? She must go out and get laid a lot” I told her I didn’t think she did. “Oh, she does, trust me on that one. No woman is going to go 10 years without a hard cock in her pussy unless she’s a lesbian.”
“Maybe you’re right” I said. “Oh, I’m right. Let me guess, she goes out at night to trivia, or a ladies night. She has coffee in the morning with the ladies” She snickered. She was absolutely right my wife did all those things. How stupid am I. I guess it’s my fault though. I am pathetic and a chronic masturbator. I started to get hard thinking about my wife getting fucked and having this conversation with Elisabeth.
“You’re getting turned on by this aren’t you?” “Yes” I squeaked. “Go tell your wife to cuckold you, what are you waiting for. She should not have to sneak around; you are a pathetic chronic jerkoff and deserve to be cuckolded.” She said “I can’t look at you right now I’ll ask my question later” and she walked out. I watched her cute ass sway as she looked over her shoulder and caught me checking out her ass. She shook her head and chuckled.
The next day I decided I needed to confront Elisabeth and plead with her not to tell anyone. She shares an office with Mark who comes in later. “Shut the door and come here” She ordered. “Please don’t tell anyone. I’m sorry” I begged. She was wearing a skirt and her tanned legs looked so sexy. She looked at me with such a condescending look. I felt like a little boy getting in trouble. A smile came across her face “You are such a loser. You’re turned on again aren’t you?” she said as she looked right at my crotch. My face turned red. “Take it out and play with it” she said. “I want to watch” “Here? Now?” I couldn’t believe it. I dropped my pants and underwear as my mostly hard cock bounced up and down. “Make it harder. I want to see how big you are” she said as she squirted lotion into my palm from a bottle on her desk. I stood there and started stoking getting rock hard in seconds. “Stop. Move your hand away.” She examined my hard cock. “You are what we call a pin dick. Your length is fine but your girth is pathetic. Yet another reason your wife doesn’t want sex. I bet you have never really given her an orgasm. All you do is poke her womb like pencil with no friction on her pussy lips. How sad”. I was crushed and humiliated. I always thought I was at least average.
Having Elisabeth berate me and watch me play with myself, brought on an orgasm pretty quickly. She saw my orgasm face start and my hips thrust and quickly handed me a wad of tissues. “Cum in these not on my rug. I don’t want your nasty spunk in my office”. I pointed my cock at the wad of tissues and started spurting into them. She just sat there with her legs crossed watching my pulsing cock. Once my orgasm was done I became very self-conscious standing in front of her with my pants down. “My I go now” I asked. She laughed and with a dismissive gesture waved me to leave “Yes you may”.
It was very difficult facing Elisabeth at work after this. She ignored me and would look at me like I was a naughty child. It was very demeaning but also quite a turn on. As far as I could tell she did not tell anyone what I did. That was a relief, but I knew her enough to know this was not going to be the end of it. She came to my office again and of course I was looking at humiliation porn. She said, “Don’t close any windows I want to see”. So, I lifted my hands up and she came over and saw a caption of a woman with a man on his knees licking her pussy. She looked down at my pants and could see my hard on. “Playing with yourself again?” Come to my office.
I have to admit I was excited. I got there and she said I needed a spanking. My cock almost exploded. The thought of lying across those legs and have my ass exposed was major fantasy material. I locked the door and walked over to her. She said “Well? What do you say?” I didn’t know what to say. I just stammered “Spank me please?” “Pull down your pants and lie across my legs. I did as I was told, and she secured my now very hard penis between her bare legs. You better not let your wife see your ass tonight and SMACK her hand came down and it hurt. She was way stronger than I thought, and this was not a flirty kind of spanking. SMACK, SMACK, SMACK … 20 times as hard as she could. I tried not to scream and worried someone would hear her hand hitting my ass. My ass was on fire and red as a tomato with hand prints. My penis was rock hard. I stood up and my hard on was pointing straight out. “My God you are pathetic. Look at that hard on! Even after a spanking?” Go stand in the corner with your ass facing me.
I stood there for 15 minutes praying no one knocked on the door. “Turn around!” she ordered. My cock was still at attention even though I doubted I could even sit. “Really! You are still hard! Come here and open your hand” she then squirted lotion in it and handed me some tissues. “Go back to the corner and jerk off, that lotion is not for your ass either.” I went to the corner and started jerking off. She paid no attention to me as she worked on her computer. The stinging of my ass made everything more sensitive as I came very quickly, grunting and thrusting and filling the tissues with cum.
I couldn’t stop thinking about my spanking and realized I was falling in love with Elisabeth in a weird way. She made me feel like a little boy and I wanted her to be my mommy. A couple days later I went back to her office and told her I was naughty again. She raised her eyebrows and looked at me. “What do you mean naughty?”, she asked. I told her I played with myself again in my office and asked her to please spank me again. She laughed. “Fine come over here and pull your pants down and lean across my desk” she ordered. I did as I was told and this time she stood up and SMACK SMACK SMACK “You are going to regret this. I know this turns you on and that’s why you’re asking for me to spank you.” It took everything I had not to howl in pain. She really let me have it.
When she finished she ordered me to turn around. Even with a flaming tender ass my penis was standing at full attention. She laughed “I cannot believe you can stay hard after that spanking. Here” she handed me a handful of tissues and lotion, “Sit your sore ass over there and play with yourself”. I had to sit down very tenderly and start jerking. I was directly across from her desk and could see up her skirt if she were to uncross her legs. Then suddenly the most wonderful thing happened. She uncrossed her legs, and I could see her white lace panties. Behind the lace was her bush, and the little white gusset covered the rest of her pussy. I was sloshing my hand up and down. I could hear her clicking on her keyboard as I peeked at her panties. “I know you are looking up my skirt” she said as she opened her legs a little bit farther giving me a perfect view of her panties and even a little camel toe. I came. It was too much for me. She giggled and leaned over to watch as I filled the tissues.
It turned out that Elisabeth and my wife went to the same gym. That night my wife told me she met a woman from my office named Elisabeth. I got really nervous, but she did not react at all. The next morning, I ask Elisabeth and she said “Oh yes, I met Kathy see is very pretty and nice. I think she needs to have sex though and I am thinking about hooking her up with my cousin. He is quite the lady’s man and I hear he is packing” she giggled. I just stood there looking at her as my penis started to harden. Her eyes went to my crotch and back to my face “Figures” she laughed.
Over the next few weeks, they became friends and my wife talked about how nice Elisabeth is. She said they are going out after the gym for some drinks. I knew what Elisabeth was up to and spent the evening jerking off. My wife came home and said they had a good time but said nothing else. That morning I asked Elisabeth, and she said my wife met her cousin and they really hit it off. A lot of flirting and he told her my wife gave him her number. She looked down at my crotch again and said “That was quick! I think you are going to be cuckolded very soon. I’m close with my cousin so I will let you know how it goes. Looks like you approve.” I looked at her with puppy eyes, feeling angst and horniness. “Aww you poor thing you look so pathetic knowing there is nothing you can do to stop this. Not to mention given that tent in your pants, I’m pretty sure it is exactly what you want”. She was right of course, just picturing my wife going on a date was making me almost cum without touching myself.
A couple days later Elisabeth told me my wife had a date with her cousin. She laughed and told me she was going to cover for Kathy and say they are going out with some of Elisabeth’s girlfriends. Sure enough when I got home that is exactly what my wife told me. “Honey I am going to met up with Elisabeth and meet some of her girlfriends for drinks”. “Ok have fun, don’t stay out too late” “Oh about that I might end up sleeping on Elisabeth’s couch if we get too drunk. She is picking me up shortly. I’ll text you and let you know”. My stomach was turning over. My wife just lied to me and might be spending the night with another man. I didn’t know if she had cuckolded me before but given how easily she lied I suspected she had. Either way it was definitely going to happen tonight. A car pulled into the driveway, and she quickly went out the front door before I could see who was driving. The glimpse I got did not look like Elisabeth or a woman for that matter. At 11pm I got the text. “Sorry honey spending that night at Elisabeth’s. I’ll see you in the morning.” That morning I heard a car door slam and ran to the window as the car was backing out. It definitely was a man dropping her off. She came in the front door all disheveled looking, she totally looked like she just got fucked. Just to give her a hard time I said “Who dropped you off? That looked like some guy”. She looked at me quizzically for just a second and then said “Oh that was Elisabeth’s cousin Vinny. He stopped by to say hello to Elisabeth and offered to drive me home”. Boy that was a quick answer. She didn’t even flinch. I was getting the impression not only has she done this before but, she really didn’t care if I found out.
Monday morning, I couldn’t wait to talk to Elisabeth. I went in her office, and she looked at my with pity. I asked “What happened? Do you know?”. She laughed a little and said, “Well I talked to my cousin and your wife spent the night at his house.” My cock was rock hard, and she noticed. She moved the lotion and tissues to me and smiled “Go ahead I know you want to. I’ll tell you what I know”. I pulled down my pants, lubed up my cock and started stroking. She just watched me for a few minutes. “God you are pathetic.” She laughed. “He is my cousin, so he didn’t share intimate details, but he did say your wife was sex starved. I guess see was very vocal and as he put it, limber. I’m guess that means she spread her legs wide”. I was so close to cumming picturing my wife who no longer does any of that with me then she said “It turns me on to set up your wife with my cousin while all you get to do his play with yourself in front of me” then she put her hand under her skirt and traced a circle on her white panties. I barely got the tissue in place when I started squirting. She rubbed her panties a little more as she laughed at me spewing into the wad of tissues.
The next week I came into her office and asked her if she would spank me. “Why do you want to be spanked?” she asked. I told her “Because that’s what happens to little boys, and I no longer feel like a man anymore. All I do is play with myself all the time just like a little boy while my wife is getting fucked by a real man!” Elisabeth laughed “I guess you have a point. Poor baby. Pull down your pants and lay across my lap. I guess I am the one that started this situation for you at least I can spank that little boy bottom.” SMACK SMACK I was always amazed at her strength. She squeezed my hard penis between her legs as she rained down on my ass. I started humping her legs as she spanked me even harder “What do you think you are doing humping my legs? Little boys play with themselves they don’t hump! Not even mommy’s legs” When she said mommy my heart stopped. I wanted her to be my mommy and nuzzle me when I’m good and spank me when I’m bad. I squirted between her legs. “I’m sorry mommy” I squeaked. “Oh, my goodness, you naughty little boy now you are getting a longer spanking” By the time she was done I couldn’t sit at all. My ass was flaming red and I could hardly pull my pants up. “Thank you for punishing me mommy” I said. “I don’t know about this mommy thing. I’ll have to see about that. You are welcome. Now run along”.
Things started spiraling out of control when Elisabeth decided to tell my wife how she spanks me sometimes. My wife confronted me and called me a wussy. She asked you can a grown man ask to be spanked and do nothing to stop his wife from fucking other men. I has no answer. She started openly dating Vinny and not trying to hide it. She went over to his house on the weekends and didn’t come home sometimes. She called me a little boy and told me to go ahead and play with myself all I want; she had her own outlet for sex. So, I did. Openly masturbating as she headed over to Vinnie’s house. Listening to her laughter as she got in the car to drive away. At work Elisabeth ridiculed me about jerking off and not being a man. She was not interested in being my mommy because I was just too pathetic. Finally, one night my wife decided to bring Vinnie to our house. We were all standing in the kitchen. He was a big guy. Very Italian looking and in great shape. He looked at me and said “I am going to fuck your wife tonight. If you think you can stop me then I suggest you try right now otherwise I’m bringing her upstairs”. I looked at my wife and she had a tiny look of expectation like maybe I would man up and throw Vinnie out of our house. She watched me as I looked down at the ground and back up at her. She smiled a knowing smile and knew I was already defeated. She reached over and grabbed a bottle of lotion which she then handed me. I turned red. They both watched me. The humiliation was too much as I pulled down my pants and played with myself. They laughed as Vinnie put his arm around my wife and led her upstairs to our bedroom. I moved to the couch and played with myself to the sound of my wife moaning and the bed thumping. I could hear her begging to be fucked and telling him he was huge.
My relationship with Elisabeth started to fade. Not that it was a relationship. She got bored with me and found me to be just too pathetic to be around. She finally reported me to HR for masturbating in my office and I got fired. My relationship with my wife, as was inevitable, ended in divorce. She left me and moved in with Vinnie and as far as I know getting laid every night to make up for that last 10 years. We sold the house and I live in a small apartment constantly playing with myself over my complete destruction at the hands of Elisabeth. Meanwhile, Elisabeth lays there at night playing with her pussy getting off on how she destroyed my marriage, my job and my life. She pictures my pathetic existence in my tiny apartment full of tissues and lotion as she gushes on her fingers. As my ex-wife takes Vinnies massive cock, she is thankful to have a real man and has no regrets leaving a loser like me. She only wishes she did it sooner.