How did I let it get to this situation? My head was locked into the stockade at the foot of my bed. Wearing a blue latex Playboy bunny costume, a remote-control vibrator shoved deep in my ass, and my laptop open to Facebook Messenger. My arms have enough room to push them forward and move the mouse on the bed. The computer is far enough out of reach that I can’t touch the keyboard. I have been like this since Lori Beth left me here, as she left for work at 5:30 this morning. I guess to answer that, we have to start at the beginning.
Lori Beth and I have been married for twenty years now. When we got together, she had already had two boys by other men. She told me that in her teenage years, she was exceptionally sexually promiscuous and that she had a body count of over a hundred. Sometimes, with multiple guys. Sometimes with men and women, but when we had gone together, all that had stopped, and she had settled down.
Our relationship was fast-moving. We spent six months writing letters back and forth to each other while I was deployed overseas before we ever met. On our first date, we ate a Benihanas and then quickly went to a hotel. We both got drunk and made love three separate times that night, never wearing a condom. Lori Beth hated condoms; they didn't feel natural to her.
We spent the next three months dating very quickly before I proposed. Three months later, in July, we were married, with our first child on the way. It wasn't long after our first son was born that she was pregnant again with our daughter, bringing us to a family of six.
I would work long hours and travel a lot to make ends meet while Lori Beth was a housewife and mother at home. Our sex life slowed down, but the desire to be with her never did, and the thoughts of her during the wild days turned me on.
As a child, I would frequently steal my stepmother’s lingerie and dress pretending to be a woman. I loved the feel of silk and lingerie across my body. This carried onto my adult life. So, whenever I was away for work, I would buy Lori Beth silky lingerie to have her take pictures of herself in it for me. I would fantasize about me wearing it as well or her using a strap-on on me while I was wearing a matching outfit.
Eighteen years later, I was in a car accident and had to stop working. Lori Beth had to step up and become the family’s provider. She took a job at a Target Distribution Warehouse, operating every Saturday, Sunday, and Monday and then doing mandatory overtime during peak season. She was now away from home frequently, leaving me to fantasize even more.
While Lori Beth was at work, I would often find myself cruising the internet looking at porn and reading cuckolding stories. I would often fantasize about Lori Beth having sex with her coworkers at work or wearing the lingerie that I had purchased for her while she was with someone else. I even found myself going into men's chat rooms and telling them about my wife. I would send the men I spoke to pictures of her, knowing they were getting off to my wife. My next step down this road was to wear her lingerie, which was very tight fitting as I was more significant than her. I would take pictures of me in it and send them to the men that I was talking to.
Unfortunately, this would lead to Lori Beth finding out. You see, I wasn't always the best at clearing my history. One day, Lori Beth was on my computer checking her email and found the pictures. She then looked through the browsing history and saw what I had been doing. To say that she was mad that I had been wearing her clothes was an understatement. She ripped up the clothing that I had worn, shut herself in our room, and didn’t come out, and I slept on the couch.
The next day, Lori Beth was having coffee and told me to sit at the table. She told me that if this is what I want, this is what it will be. I couldn’t say a word and just hung my head low.
She said that I would never wear her clothes again. Those were for her and her alone, but she would pick out my outfits from now on.
Later that evening, she got dressed in a tight red mini dress with a lace top that showed off more of her cleavage and stopped extremely low, showing off just the hint of her ass. When she bent over, I noticed she was not wearing any panties.
Our first stop for the evening was at Target in Savannah, where she picked out a silk burgundy thong, matching bra, a flax leather black skirt, and a silk burgundy button-down blouse. After checking out, she told me to go to the restroom, put the outfit on, and meet her in the car. I begged her not to make me wear them in public.
“Too fucking, bad, Alex! You wanted to dress in my fucking clothes! Show strange men online! Be happy that I let you ride in the car with me! That I don’t make you catch an Uber to the rest of our stops this evening or make you walk home in them.”
I had nothing more to say and did as I was told. When I came out of the stall dressed as a woman, a man was using the urinal and stared at me. I kept walking, holding my head low in shame, hoping no one who knew saw me.
The sun was setting, and our next stop was Sunset Novelties on Abercorn Street. Lori instructed me to go inside and get an AcmeJoy Bluetooth Remote Control 9 Thrusting Vibrating Prostate Massager with Penis Ring. I was to put it on before I returned to the car, or she would leave me there. I was so nervous but didn’t want to upset her again.
Once inside, I got many stares due to my outfit, but I found what I was instructed. At checkout, I asked if they had a restroom but was told it was only for employees. I was left with little choice, and after leaving the store, I walked around to the side, unboxed the anal plug, pulled the panties aside, and worked it painfully into my ass. I then went to the car, where Lori Beth was laughing. “You know, a guy came out and watched you from his car while you put that in. Maybe you should go get his number?”
“Lori, please. I am so sorry. Let's go home.”
“Hell No! You wanted this, and the night is just getting started. Mary is over at her friends, and the boys are at work. I plan to make you suffer tonight, which is only the beginning.” With that, she unlocked the car, and I got back in. Our next stop was at a parking garage off Bay Street. Lori Beth instructed me that we would go to the Electric Moon and Skytop Lounge, which are three blocks away. She taught me that I would be walking alone, and she would be a long shortly. I was to get a table by myself where I could see the bar but not to come up to her. The walk only took eight minutes, but it felt like a year with everyone I passed turning and staring.
When I arrived, I took my seat, and a few minutes later, Lori Beth entered and found a spot at the Bar directly in my line of sight. I waved to a waitress who gave me a quick look of annoyance and asked what I wanted. I ordered a bourbon and coke and prayed that Lori Beth wouldn’t take it too far. Little did I know how far she would take things on that night.
It didn’t take long before a drink was sent to her, and the bartender indicated a tall, tanned man with black hair, wearing denim slacks and a low-buttoned shirt, who waved at her. She smiled back, had a sip, smiled even more profoundly, and waved him over.
Lori Beth and the man seemed to laugh and talk for an hour before she looked back at me and pointed. The man looked over and laughed. She then pulled out her phone, and I looked at mine, hoping for her to message me telling me she was ready to go home and that this night would be over, but was I wrong? I started to feel the plug in my ass begins to come to life, and I jumped from my seat. The man with Lori Beth looked at me, squirming, and laughed hysterically, almost falling out of his seat. Lori Beth then handed the phone over to him. The make took it, and the vibrator started to shake even faster and began to thrust in and out uncontrollably. Lori Beth and the man started to see me struggling to keep my composure, and they began laughing hysterically.
Satisfied at my torment, the man handed Lori Beth back her phone with the plug remaining at full speed. She placed it in her bag, and the man led her to the dance floor. She quickly wrapped her arms around his neck and began to sway in front of him, giving him a great view down her dress. A few songs later, she had turned around and was grinding her ass on his dick while he was kissing and sucking on her neck, leaving marks on her while his hands were groping her breasts. Occasionally, she would lower her top and expose her massive areolas so other men on the dancefloor could see, driving me crazy.
It wasn’t long before two other guys approached them and started to grind. I could see bulges growing in all of their pants. A few songs later and covered in sweat, Lori Beth and the first man left the dance floor and returned to the bar. Lori Beth pulled out her phone and began to type.
A few seconds later, my phone lit up with a message. I am ready to go home, but Joseph here has a problem. I got him all worked up, and he needs relief. I told him you will be waiting in the restroom to service him. You have twenty minutes after I leave to make it back to the car with your mouth full of his cum. If you don’t make it on time or don’t finish him, he has my full permission to invite the other two men dancing with us to follow you back to our car, and I will get all three of them off however I feel like.
I looked up and saw Lori Beth kissing Jason, and I knew my timer had begun.
I could feel panic grown in my stomach on top of the vibrator still pounding inside of my ass. I know I didn’t have a choice at this point. I left a fifty on the table to cover my drinks and went to the men’s room to wait in a stall.
A minute later, the door opened, and I heard the man call, “Hey Bitch Boy, your wife sent me to get serviced by you. Where the fuck are you?”
“I am in the middle stall,” I could only reply.
The door to my stall opened, and there he was with a massive bulge in his pants. “Your wife said you would probably chicken out, and I hope you do. She deserves a real man, not a panty-wearing small dick cuck like you. I have never had a little Bitch Boy service me, so I will probably lose my hard-on and get the bigger reward of bringing Mike and Sam to follow you. All three of us will fuck her sexy ass body, maybe even give you another child to raise that isn’t yours. Well, Bitch Boy, my dick isn’t going to take itself out and suck itself.”
With that, my heart sank, and I knew what to do. I unbuttoned his pants, lowered his zipped, and reached in, pulling his massive veiny dick out. I started to wrap my hands around his shaft, only to have them smacked away.
“Listen to me, Bitch Boy; you are only to use your mouth. I don’t want to make this easy on you. You are going to have to work to keep me from having my reward of having your wife as my cum dumpster tonight.”
I sighed, closed my eyes, and put my lips around the tip of his penis. It smelled of musk and sweat. I could tell Lori Beth had gotten him worked up and could taste the saltiness on his dick. I tightened my lips and worked them around his shaft and started to bob up and down, working my tongue around the safter. After a few attempts and many gags, I was able to work enough of him in that I could stick my tongue out and barely touch his balls. It took a few minutes, but I finally felt him begin to tighten up. He grabbed the back of my head and pulled my face deep into his shaft, forcing me to gag again. With a loud groan, he sprayed his cum inside my mouth, with some going down my throat, forcing me to gag but the rest filling my mouth. He finally released my head, and I was able to pull my lips off his dick and open my eyes, only to see him with his phone out, recording me.
“Not bad, Bitch Boy, but you are only halfway free. You see, you only have five minutes to get back to your waiting wife and hope that you can hold that cum, before she texts me and tells me and my friend to go to her and show her what real men can do. I would wish you good luck, but I don’t want you to make it. See you soon, Bitch Boy.”
