Will My Humiliation Win Over Mona?

Story Info
My inept and futile attempts to bed Mona result in my shame.
2.6k words
3.85
4.4k
3
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Mona had me wrapped around her little finger. She was getting married to Ray in a week and I was begging her to let me clean her toilet. With my tongue.

I met Mona at work in May of 1980, quite a while ago. I was working at WT Rogers in Madison and she had just started. I immediately fell in love with her smile, her dancing eyes and pert, little breasts. I was often able to talk her into an after-work drink and we invariably ended up in the car making out. Well, sort of making out. We'd kiss and she'd grab at my crotch but whenever I even attempted to touch her breasts or crotch, she'd quickly stop me. "I'm engaged," she'd remind me, then passionately kiss me and grab my dick again. I was confused and frustrated and loved it.

Mona had been married at 18 but got divorced a couple of years later. Rumor had it that she had repeatedly embarrassed her husband in front of his friends before divorcing him. Men at work thought she was pretty hot but typically commented "in bed, she must be all whips and chains." This all made me want her even more.

But Mona was engaged and had gotten engaged just before I met her. For some strange reason, her fiance, Ray, had joined the Air Force to become a pilot or something. I though that was unusual for a 27 year old, but I was happy when he left in June for some sort of training camp. I at least had the summer alone with Mona and maybe I could change her mind. As we were necking one evening, I asked if there was any chance she would break off the engagement and she said "Maybe. For the right reason. Think you're reason enough?" I tried but I was to find out I wasn't even close.

Mona and I quickly found out we shared one passion: pot. We both liked to get high ... a lot. So soon our after-work drinks were after-work smokes at my apartment. After getting high, Mona would almost attack me, pushing me to the floor, getting on top of me and kissing me passionately. I immediately realized she just wanted me to lay there and kiss her back. Again, she would frequently grab my cock to be sure I was hard. "You want me bad, don't you? You want me to take this cock out of your pants. You want to get me naked and shove your cock in my wet cunt, don't you. Tell me how much you want me." I'd beg and plead and in general was quite pitiful and then she'd get up laughing, ready to leave. Before leaving, she'd kiss me, rub my cock through my pants and tell me "keep this hard for me, ok?"

We went to a couple of parties together and Mona insisted on driving. Before we'd leave, Mona would spend 15 minutes or so getting me hard and horny, then tell me to wait until after the party. At the party, she would totally ignore me, mingling with everyone else. She explained "I'm engaged you know. I don't want people to think I'm running around behind my finance's back!". On the way home, she grab my cock as she was driving and ask if it was hard for her. Of course it was. At home, we'd neck for a few minutes in the parking lot with her hand grabbing my cock, then she'd tell me she had to leave. I'd beg her to come in, but she just laughed, then would kiss me again passionately. I'd go home frustrated and happy.

Returning to work the Monday after the second party, I found out that immediately after Mona had left me with blue balls, she headed over to Elliot's apartment. Elliot was a large, well built and attractive black man at work. Elliot made comments that got back to me that Mona was a great cock sucker and had the wettest little hot pussy. At least I had the satisfaction of knowing that I helped make her pussy hot and wet for him.

Even I was smart enough to realized I wasn't going to get anywhere with Mona, but it was fun to keep playing her game. The second half of August I had a two week vacation and asked Mona if she'd watch my cat and plants while I was gone. I wouldn't have trusted her, except she did love cats and was great with plants. She agreed and I gave her the house key. I also told her that I'd leave some pot and she could help herself. When I returned, I found Mona had done a good job: the plants never looked better, the cat was happy and most of the pot was gone. I made sure not to get the apartment key back.

A week later I heard Mona was out of pot and looking to score Saturday morning. I told her that if she wasn't able to get any, to come on over, that I could front her a few joints. I said that I may not be there, but to let herself in. The pot was in its usual spot. On Saturday I was sure to leave and when I got back late in the day, I found that she had taken about 1/2 my stash. Ok with me. On Monday, she told me she had taken enough to last the whole week and was sure she could score on the next Saturday and she'd pay me back then. I said no problem and told her again that if she didn't score, that I had gotten a little more and she was welcome to it.

I knew all of Mona's contacts and found out that most were out. A couple did have a few bags and I bought all they had. I asked them not to tell Mona and no matter what, not to give her anything this weekend. Everyone was nice (they love good customers) and agreed.

I had a nice surprise planned for Mona on Saturday. I had played some with self-bondage and had a pretty good routine. I had eye-bolts in the corners of my bedroom door and using ropes and hand-cuffs, was able to very effectively tie myself spread-eagle to the door. I had also gotten quite good at using ice cubes to time my escape. On Saturday morning, I got ready for Mona. Of course, I didn't expect any change in our relationship, but did want one last good chance for Mona to tease, humiliate and laugh at me.

First I carefully cut off all my pubic hair with a scissors and carefully place the hair in a neat pile on top of a note that read "I dedicate my pubic hair to Mona's beautiful smile." I then shaved by cock and balls smooth. Remember that in 1980 everyone had pubic hair, even beta men.

I figured she'd be over around noon, so at 10:30 I got ready. First I set out a disposable camera in the living room. I set my ice cube timer for 4 hours (which was the longest I ever went), attached small wooden clothespins to my nipples, wrapped a rubber band once around my balls and cock, then twice again around just my balls. I tied myself spread to the door, putting on a blindfold just before I fastened my last hand. And I waited. At first my cock was quite hard but then it settled a bit but I could feel it remained quite full and plump.

I actually didn't have long to wait. I heard the buzzer ring a couple of times and I started to get hard and breath fast in anticipation. A few minutes later I heard a key in the door and my cock jumped to rigid attention. Then I was shocked: I heard Mona talking to someone. Then a woman's voice replied. I quickly tried to think of all Mona's friends: who might it be? It didn't matter because I wasn't going anywhere and it only took Mona about 15 seconds to find me. In fact, I kept the pot in the bedroom and she couldn't miss me.

I knew she saw me when I heard her laugh. Then laugh again, louder. She called her friend over then asked me "Who tied me up and left me alone? Who's your friend?" I told her no one, that I had tied myself up. She laughed and squeezed between me and the door to get to my stash. She saw my note and laughed again. "He shaved just for me," she told her friend. "Or at least he shaved for my smile. I guess he knows my smile is the only thing he'll ever have." She squeezed back past me, swatting me hard in the ass, then shook the baggie of pot and said, "Well, I might as well take all of it." I asked her to leave me a little and after some begging, she agreed to get me high before she left. She and her friend went to the living room to roll a few and I heard them whispering and laughing. They came back with a lit joint and we shared that one, then another. Mona would hold the joint to my lips, nibble on my ear and play with the clothespins as I took a hit and her friend would laugh.

Mona's friend mentioned the camera and asked if they should take some pictures and before Mona could respond, I said "Yes, please. As many as you want." Mona laughed and slapped my face a couple of times. "You're a bad boy. You want to be spanked, don't you?" I agreed and she swatted my ass a couple more times. Then I heard her friend snap 3 pictures of me and Mona stopped her. "Don't want to spoil him." Her friend replied "I wasn't going to spoil him, I was going to do this." I felt her hands grab my sides then she kneed me hard in the nuts. I groaned and choked and my knees sagged. Good thing the eye bolts were strong, because I was dangling from my arms. Mona's friend asked if it hurt and I could only gargle and choke. "If it didn't hurt, I'm going to try again." She kneed me twice more and even though she was relatively gentle, it hurt like hell. I was dangling from my wrists and the handcuffs where starting to cut into my flesh, so Mona thought I should be let down. "But only if you keep the blindfold on." I nodded. After she released me, they took me to the living room and had me lay on my back but wouldn't let me hold my aching nuts. "We want to see your aching cock and balls," her friend said.

They sat around and had a beer and chatted. Finally my balls stopped hurting so bad and I started to get hard again. They noticed and said "ooops, time to leave, but before we do ..." They had me stand and spread my legs. I knew what was coming and couldn't help getting harder. Then, slam, one of them got me REALLY HARD I fell to the ground with a scream, grabbing my balls and groaning in serious pain. I barely heard them say 'goodbye' before they left.

I laid there for what seemed like an hour before I could move, and then only to roll over. Finally, later in the day I was able to get up and decided to get the photos developed. I took them to a one hour place and because my 3 bondage photos were the only thing on the roll, they looked at me pretty strangely when I came to pick them up.

When I returned to work on Monday, my balls were still sore. I found Mona and she smirked when I told her I was still sore. I showed her the photos and she decided to keep them. I asked who her friend was but she wouldn't tell me, but did tell me that her friend laughed about it all Saturday afternoon. I said that if her friend could have a repeat performance anytime and that I would do anything for Mona. "Like what? Prove it!" she challenged me. I thought for a moment said I would be her maid, keep her apartment clean and do what ever she asked. Pretty lame, I know, but it was all I could come up with that I thought might interest her. Mona thought about it and I added "I'd also like to do it in the nude." Mona laughed and said she knew that and that she would talk it over with her roommate.

I checked back with Mona later in the week to see if I could be her maid, and she said it was ok with her roommate and to give her a call Saturday morning. But on Saturday Mona said "Not this weekend, have things to do. Maybe next weekend." This continued for several weeks.

Meanwhile, Ray was getting done with his training and coming home for a 2 week leave. He and Mona decided to set the wedding date for the middle of his leave, a Saturday in early October. I didn't have much more time with Mona.

Finally the Saturday before Ray was to return, Mona called me over to clean her apartment and she told me I'd better be clean myself. I figured she meant shaved, so I carefully removed all my body hair and showed up at her apartment. Her roommate was there and I wondered if she had been the mystery woman, but when I heard her speak I knew she wasn't. They had me get naked and showed me what to clean. Basically, everything. Then they took my clothes and said they were going shopping. That wasn't what I had in mind, I was hoping for a jeering audience. But it was better than nothing.

I carefully cleaned everything in the place but decided to leave the toilet. It was just plain hard work and wasn't that much fun, but at least I was doing one last humiliating thing for Mona. They returned late in the day and inspected the apartment. They were pleased but asked about the toilet. I said I had saved that, that I wanted to clean it in front of them, that I considered it very humiliating and degrading and wanted them to witness it. Mona wasn't easy and made me beg and plead and finally they relented. So with the two of them watching, I slowly licked the seat and bowl and floor clean. It was hard to do the bottom of the bowl, so I used my fingers and licked my fingers clean. They both watched with disgust on their face, then made me leave as soon as I was done.

The last I saw Mona was on her wedding day. She looked great and I hate to say it, but when I met Ray, I did like him. Poor sap. I may have also finally met the mystery woman. At the wedding, Mona introduced me to her older sister, Kay, and when Kay talked it sounded just like the mystery woman. Kay was slim, fit and very cute. And I knew from previous conversations with Mona that Kay was a lesbian. I spoke with Kay a bit at the reception and it was clear she did NOT like men. After about a minute of conversation, Kay quickly left saying she had better things to do "than kick around here all day." I wonder if that was a hint?

I heard later that Mona abused Ray too and just got married to have a child. A couple years later they were divorced and Mona was shacking up with a truck driver. I wonder how many guys she was fucking while he was on the road?

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

Similar Stories

Mia's Master Plan Ch. 01-02 A closet sissy hatches a plan to lose her virginity.in Transgender & Crossdressers
Saving Him from Himself Ch. 00 - Prologue Meet The Hawthornes, a wealthy but troubled family.in Fetish
Wedding Night Cuckold Bride cucks her husband on their wedding night.in Fetish
Going Out of Business Sale A sissy now alone in life falls under the influence of a dom.in Transgender & Crossdressers
Entrapped: Landlord to House Slave Lauren catches you out, using it to take FULL advantage.in Fetish
More Stories