How it all began...
I have fantasized about being a cuckold for many years. I've had a few girlfriends over the years that would participate in my "weird" fantasies but never go all the way. The closest I had until recently was a girlfriend in my early 20's who we'll call Jessica. Jessica loved to constantly tease me about having a small dick and would tell me how badly she wanted to have sex with other hung men. She was extremely good and dominating me and making me do humiliating things. She would regularly use a 10 inch life like dildo when we would fool around and she would make me hold it in my mouth while she fucked me. She also loved when I would lick her ass which I absolutely loved as well. Jessica was the typical young blonde with green eyes a body to die for, perfect round tits and a nice full ass. She was extremely turned on by my best friend Nick and we would use him in our bedroom fantasies often. One of her favorite things to do was tie me up on the bed and then she would ride my face facing me so I could look up at her. She would then take her phone and act like she was texting Nick of course telling me everything she was typing. It got to the point where she saved a fake number under his name in her phone. She would then type out a long message about how she had always wanted to fuck him and how she was tired of my little dick. She would also mention that she wanted to make me suck his huge dick. She would then show me the message and point out the contact name "Nick" before she would hit send. I would melt into ********** under when she did this. I was terrified but at the same time it just made me go crazy for her. Obviously after a while I figured out that it was a fake number but we still continued it as a fantasy and it was extremely hot even knowing the messages weren't real.
Jessica and I had moved out of state and my friend Nick had decided to come visit. The weeks leading up to Nicks visit was incredible for me and Jessica in the bedroom. She would tease me and tell me how she was going to seduce him and fuck him. In the heat of the moment one night during her riding my face and telling me she wanted to fuck Nick I told her that if she wanted to she could. She stopped riding my face and looked down at me with the serious look on her face and asked "Are you positive? There won't be any going back after this". I was so hard and wanted to cum so bad and I'm sure it was mostly my little dick talking but I told her that it was completely up to her and that if she wanted to, I wanted her to.
We continued our nightly talks in the bedroom about Nick. I could tell she was getting excited as she was becoming more and more dominant and cruel with her teasing. Nick arrived and after a few days of normal friendly stuff we all decided to *****. It was Nick, Jessica and I in the living room sitting around a coffee table just joking and telling old stories. As the night progressed Jessica began flirting with Nick in front of me. Nick would look over at me with this look on his face like "aren't you going to stop her man!". I let it continue and eventually she was sitting in his lap and they were giggling and whispering. I knew the moment was coming and as I patiently waited they just continued their simple flirting. Nick got up to pee and as soon as he was out of earshot Jessica ran over to me where I was laying back on the couch and grabbed hold of my hard dick through my pants. She whispered in my ear "I want to fuck him so bad and according to your dick you want me to fuck him too." I couldn't say anything as my tongue was like sandpaper as the nervous energy ran through my body. Jessica finally broke the silence and said "I tell you what. If you want me to fuck him then when he comes back you slowly act like your falling asleep on the couch here and I'll let that be my cue that you want this as bad as I do." Without saying a word she stood up and took all of her clothes off except for her thong and walked into my bedroom which was just off of the living room. Just about the same time Nick who was obviously feeling the effects of the ****** came wondering back into the room. I watched as he noticed Jessica's clothing on the floor and he looked up laughing and said "She couldn't wait for me to come back could she?" I just laughed and acted like it was just a joke. Realistically I had no idea what to say. I was so hard and turned on but at the same time I was unsure if I was really ok with this happening. I knew I wanted to be a cuckold but at the same time I was terrified of my best friend knowing my deepest perversions. Nick had sat back down on the opposite side of the living room from me just as Jessica walked back into the room with her life like dildo that we had named "Nick" after fantasizing numerous times to her fucking him. I could not believe that here my almost naked girlfriend was walking into the room with me and my best friend with her favorite toy which we had named after him. Jessica completely ignored me walked over to Nick and stood in front of him and asked him "Like what you see?" Of course Nick, being a macho ladies man just gave her a sly little smile and said "Of course I do baby. Are you going to show me what you do with your friend there?" as he looked at the dildo which she was now rubbing as if it was a real dick. Jessica smiled laid down on the coffee table with her open legs facing Nick leaving me with a view of only her back and the back of her head. She then slowly began moving the tip of the toy ever so slowly around her nice tight stomach and around her tits, stopping to circle each nipple. She eventually slid her panties to the side and slowly began inserting "Nick" into her unbelievable pussy. She was moaning in pleasure and really getting into it. I couldn't see her face but I could tell by the look on Nick's face that she was staring directly at him the entire time. Nick was completely oblivious to me even being in the room. Nicks enormous dick started pushing up on his jeans and he reached down to re-position it. Jessica noticed this and asked him if he was enjoying the show. He nodded and she stood up and straddled his lap. Without knowing what to do and afraid that I would look completely like a coward if I was willingly allowing this to happen I closed my eyes so that they would look shut if either of them happened to check but I could still see enough of what was going on. I saw what looked like Nick looking over Jessica's shoulder to see what I was doing. I could barely hear him whisper "what about him?" Jessica now moaning and kissing Nick's neck stopped long enough to say "I don't care, I want your big dick." Without saying another word Nick grabbed her hands helped her off of him and led her to the guest bedroom which was where he was staying. The last thing I heard was the door closing and more moans.
As I sat in the now empty and quiet room I was frozen in fear and lust. Was this really happening? I couldn't believe how quickly it had happened. I started thinking about everything and what struck me the most was that Nick hadn't even tried to stop her. Even if he did think I was ******** which I prayed to God he did. He didn't try to stop his best friend's girlfriend from seducing him. I looked over at the coffee table I noticed Jessica's favorite toy "Nick" lying motionless on the table and it ironically made me think of myself. Just left behind and forgotten for something better. As I was sitting there thinking I had an incredibly sexy thought. My house at the time was a small one level house. The guest bedroom had two windows that faced an empty field and the street I lived on was pretty quiet. It was late enough that I wouldn't need to worry about any cars. I quietly walked to the front door terrified that any noise I made when cause them to rush out of the room to investigate. I opened the front door and walked around to the side of the house where the guest bedroom was. I got to the first window and the blinds were pulled down. "Dammit" I thought as wanted so badly to see what was going on just inches away from me. I made my way to the other window and although the blinds were also pulled in the second window the slats were positioned just right to where I could peek through the cracks and get a sliver of a view. The lights were on in the room and I carefully moved around trying to get a view of what was going on. I suddenly found a set of feet. I knew those feet well. Jessica was on her knees. As I slowly moved to change my view up I could see Jessica's sexy ass sticking out towards me as she was bent forward slightly. I continued upwards and saw that Jessica was kneeling down in front of a completely naked Nick. Her hands were in front of her face and her head was moving slowly back and forwards. I was hard before this but now my dick was practically ripping the seams of my jeans. I pulled my zipper down and slid my "lil guy" as Jessica always called it, out and began playing with it. I sat there and tried to see what was going on inside the bedroom just in front of me as I continued to furiously rub my own dick. It was difficult to keep the right position to see inside but I tried my hardest. I was wishing that they would move so that I could see Nicks large member sliding in and out of Jessica's mouth but all I could see was his hands on the back of her head guiding. After a while the quiet moans from inside the room began to get louder and he was pumping faster into Jessica's face. I knew that I only had a few seconds to decide my next move. I quickly ran back to the front door, closed it as quietly as I could and got inside. My bedroom door was right next to the front door and as I stood there trying to decide If I should get back on the couch I heard commotion coming from the guest bedroom. Terrified that I would be caught by Nick standing in the living room with my little dick poking out of my pants I hurried into my bedroom and jumped into bed.
The main bathroom in the house was directly in between my room and the guest room and there were doors leading into the bathroom from both rooms. I quietly took my clothes off and laid in bed playing with myself, listening to Jessica and Nick giggling. I then heard the bathroom door open, a light came on and I heard the toilet seat come up. This was followed by a loud powerful sound of liquid filling a bowl of water. I was amazed at how strong and masculine the sound was as Nick pissed. I couldn't help but think how much quieter my own stream sounded when I would pee. My thoughts were interrupted as the bedroom door opened from the living room and in walked a smiling Jessica. She apparently grabbed her favorite toy from the coffee table on her way in. She laid down next to me and quietly whispered in my ear "I was wondering where you were hiding." She began slowly playing with my dick which was standing straight up as we both looked at the door to the bathroom and listened as the strong stream of piss slowly came to a stop. Almost as if she could read my mind she said "He's a lot bigger then you. He's probably twice the size of this little thing." She squeezed my dick hard as she finished her teasing. She then leaned over and began kissing me passionately. I had kissed her many times after she had gone down on me and I could taste the familiar dick taste in her mouth. I had never been allowed to cum in her mouth but I had tasted my own in her pussy many times and I didn't think that there was any cum in her mouth. Still just the idea that she had just had my best friend's larger cock in her mouth mere minutes before she was kissing me was extremely erotic. She then leaned over and showed me her breast. They were covered in cum. Some of it already beginning to dry. She gave this devilish smile and grabbed the back of my head and pulled me towards her chest. As I slowly licked every square inch of her tits free of my best friends cum, she just laid there quietly moaning.
Nick must have come looking for us and knocked on the bedroom door. As I laid there licking Jessica's cum covered tits she told Nick that she would be out in a minute. She looked down at me smiling as she said it. When I finished cleaning her she told me that she had really wanted to fuck Nick but he seemed a little reserved about letting her. She told me that she was going to back out there and try again. With that she left me in the dark room with the hardest erection my little dick had ever had.
I wish the story continued but sadly when she went out to find Nick he was in the kitchen on the phone with his girlfriend. He apparently had felt guilty about what he had done. Nick and I never spoke of that night and we are still best friends today. I'm pretty sure he thinks I was asleep. If he ever knew that I had cleaned his cum off of my girlfriend that night I'm not sure he'd react very positively. Jessica and I relived that night many times during our bedroom fun. Eventually for completely un-related reasons we decided we were better off as friends and we broke it off. We still communicate occasionally but only as friends.
This was merely my awakening to the lifestyle that I had desperately wanted to live. Eventually I found another girl much more beautiful and sexy and we have been together for five years and married for two. It hasn't been easy convincing my wife to cuckold me. We have, what I like to call an off and on cuckold relationship. However more recently it has become increasingly more ON and not so much OFF. I would love sharing the rest of my progression into this lifestyle if anyone's interested.
Jessica when this was all going on
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