My Mistress and Her Cuckold Boyfriend

Big shout out to Blackstallion21 for helping edit and proofread my rookie mistakes.

*****

I have been in hell lately. I'm in a sexless marriage. My name is Paul. I HAD a little plaything that I used to fool around with to take the edge off, named Sharon. But, my wife found out about her through my own carelessness; so, now I'm constantly being monitored and checked up on.

After that I can now only email and occasionally Face Time with Sharon. I knew she is going to move on because as "I" know, it is really difficult to hang on to something you love, but can't have.

One of the last times I emailed with her, she said we have to talk about something on the phone or face to face. I carved out some time on the ride home that night and with a new burner phone I bought, Sharon told me that she had really never stopped "dating" her ex bf Jon. I kinda figured that in the back of my mind. She has a high enough sex drive and wouldn't have been content just getting it from only me every few months for an hour at a time. Her ex Jon knew about me, and that I was the reason that they broke up 3 years ago... She needed someone close and Jon was there for her. They had continued on as friends with benefits over the last 3 years because of me.

Sharon told me that Jon had a particular fascination about the time she spent with other men since they had been broken up, specifically me. And his interest grew stronger and stronger over time. He would ask Sharon about the times that she and I were together. Ask for details, etc. He actually got turned on hearing about her pleasure in the arms of another man... To each their own; I suppose...

She wanted me to know that she was going to rekindle their relationship and just be with him since he had always been there for her through the thick of things over the last few years. BUT, she also wanted to see me and fuck me one last time before she committed completely to him. That last part made my cock twitch. But, what she said next caught me off guard to say the least.

"So, here's my proposal. I want you to come here and fuck me one more time, but I want Jon to be there too so that he can watch everything."

She laughed and went on to say that she wasn't doing this for his sole benefit. She knew that I would fuck her brains out and make her cum on my cock over and over. Jon just wanted to see me fuck his girlfriend and watch and listen to her reactions. She had relayed all of our past sexual details to him, so he was always horny and always thinking about ME fucking her and her squirting on my cock and me cumming on her face ALL the time. She even admitted and told me that he was there was one time when I visited her apartment unexpectedly one time. Jon was hiding in the bedroom and listened to us fuck. What a mind-fuck that must have been for Sharon. Knowing he was in the next room.

I thought about this for a little while and tentatively agreed, but then I came up with and gave her a list of rules. Since I was the most important cog in this machine, it was going to go exactly the way that I wanted or not at all...

I knew I would only get a short time away from my nag of a cold dead fish wife, so we couldn't go out for dinner or anything before I fucked her. Sharon happens to live in an apartment above a bar now, but with the short free time I have before the GPS trackers got turned on to find me, we would have to skip the pleasantries. She was disappointed, but understood as long as she got to see me and feel and taste all of me one last time.

It took a few weeks to free up some time, but we agreed on a day. It was midweek, so there would be less suspicion. On the chosen day, I left work early and face timed Sharon from the parking lot. She was already waiting for my call and answered it after about a half a ring. She had her hair all done up in pigtails and had some extra slutty makeup on her face...

I asked her, "Are you ready?"

"Yes. We are..." she replied.

"Yes, what?...", I asked sternly.

"Yes, Daddy... We are ready..." she said with a sparkle in her eyes. She bit her bottom lip and I could tell she was very nervous... Not so much from me coming there, but because Jon was right next to her.

"Give the phone to Jon.", I said to her. She passed the phone over and Jon said hello.

"Jon... Moment of truth here buddy. Do you really want this to happen? I am NOT coming there and wasting my time if you are not 100% into what's about to happen. I don't want Sharon stopping halfway through because you get upset or jealous or whatever. That will be a complete waste of my time and that will be unacceptable."

Jon lowered his head a little and said, "I really want it to happen..."

"And what DO you want to watch me do if I come over there? Hmmm... Remind me again...," I asked with a considerable grin on my sarcastic face... Sharon giggled a little bit in the background.

After a brief pause of him weighing things over in his mind, he exhaled a nervous breath. Sharon just leaned into frame and pulled his chin towards her and said, "It's ok. Tell him... Today is YOUR decision. Paul and I can meet up some other time and fuck our brains out and I'll tell you all about it after. BUT, if he comes over here TODAY, he is GOING to fuck me. So, I ask you, do you want to hear my story sometime in the future about how he fucked me? Or do you want to watch it happen in about an hour when he gets here?"

I swear he was holding his breath while she said all that. But, when he found his voice, he turned the camera back on his face and said directly into the camera, "Paul, I want you to come here and I want to watch you fuck Sharon. I've been so turned on for SO long because of her descriptions of you two when you're together. I want to see it TODAY and watch you two pleasure each other."

I smiled at the camera and said, "Thank you, Jon. Now was that SO hard? Ha ha. OK, you two horny people. 2 final questions and I'll be on my way to you. Sharon, is Jon hard?"

She reached her hand out of frame and felt his cock because Jon closed his eyes and moaned a little. "Yes, Daddy he is, very hard. The hardest he's been in a long time."

I continued on, "Jon, is Sharon wet? Stick your finger in her pussy as deep as you can and then pull it and show me."

Sharon stood up to give Jon easier access and she gasped when his finger pushed her panties aside and plunged into her pussy. He purposefully wiggled his finger and she moaned and squeaked a little. He then removed his finger and held it up to the camera. It was indeed wet and shiny. Sharon then grabbed his hand and brought his finger closes to the camera and then sucked his finger into her mouth, moaning as she did it. "I am SO wet, Daddy because I can't wait to see you..."

"OK, see you soon." I ended the call and started driving. I was very hard and throbbing that I was going to finally get to fuck Sharon again, but a bit apprehensive as to what role in this fuck session that Jon would play.

So, it took me about 30 minutes, but I got there and Sharon let me in and led me upstairs. I appreciated the little shorts and tight top with no bra she was wearing.

Jon was upstairs finishing a beer. In fact, it looked like they both had quite a few before I showed up. Loosening their inhibitions I guess. I sat down and Sharon went to sit on my lap. I smacked her ass and motioned for her to go sit next to Jon.

I pointed and wagged my finger, "We have something to discuss first...The Rules...These are MY rules, I have the most to lose by even being here, so it's going to be my way or I'm leaving. If it gets weird or too emotional, I'm getting dressed and leaving. So, who would like to start? Rule # 1?"

Sharon said, "Jon can only watch, except if I want to kiss him."

"Correct... Rule 2?" I continued on.

Jon piped up and said, "Rule 2 is that you can do whatever you want today." I nodded at Jon. I was even happier to have it confirmed that I would get this sexy woman all to myself, not to mention that I can do whatever I want to her! She always loved my cock and I knew that she would beg me for more later. She's always so transfixed with my dick when it's in front of her. And if Jon has a fetish of watching his hot girlfriend getting fucked, well hey, as long as I am the one banging the hell out of her, who cares, right?

"Rule 3? Anyone?"

Jon answered again and said that Sharon has to do a striptease with a blowjob to start things off... (I love that rule)

I finished up by saying, "ANND finally, Rule 4?"

Jon said, "Rule 4? I never heard that there were 4..."

Sharon seemed a little sheepish but said to Jon, "Yeah, Paul and I thought of that one but didn't tell you until now." She paused a moment, but continued, "When Paul is fucking me, we always talk dirty, I mean filthy... Jon, I don't want this hurt your feelings, but I cannot be held accountable for the things either one of us says while his cock is inside me."

I chimed in and said, "You know, if the verbal stuff or anything else is too much for you, you can always leave the room and listen to us like you did before." My voice dripped in sarcasm. "OK. Enough rules.. Come here and dance for me, little girl"

Well, you would think she did this for a living before, because with some music already playing from the bar downstairs, she did a nice seductive striptease and ended up in her panties, but still did some butt wiggles and hair flops and close proximity rubbing on my cock. Then, she got on her knees in front of me. I stood up and asked Jon to come over. I asked him to get my cock out of my pants and put in into her mouth. It was a little weird asking and a little awkward feeling, but look at where my cock was going. I'll take a strange hand on my cock if it's immediately going into a mouth like Sharon's.

Jon went to sit back down, but Sharon moves her finger in a "come here" motion as my cock is in her mouth. She removes my cock from her mouth and after she licks the head of it, she tells him to kneel close and just watch. She looks him right in the eyes while she puts the head of my cock back in her mouth and moans. She takes my cock very slowly but very deep, and all the while when it comes out of her mouth, she licks the head and plays with my balls. She moans all over my cock and takes it deep over and over again.. Jon is kneeling and can't help pulling his cock out and starts rubbing it... Every time Sharon does something different, she stops for a minute and kisses Jon. Her hand is still on my cock jerking me, but she tongue kisses him and they both moan. She sends him back to his seat after a few minutes.

And then as she always does, she asks me, "Daddy, will you fuck your slutty girl's little mouth?" She holds her head still so I can grab her pigtails and fuck her face. I love her mouth and all the naughty things she can do with it...

"Do you want my cum, little girl?" as I am breathing heavy after only a few minutes of feeling my cock deep inside of her throat.

"Yes, Daddy..." is her breathless reply between deep throats of my cock.

10 more trips down her throat and my cock is ready to explode. Sharon is the BEST at sucking cock... "Here it comes.. Take it..." I pull out of her mouth and start spraying my cum, "...all over your FACE..." After I stop shooting my thick salty cum all over her, I hold her head and force her to take me deep one more time and then I really have to sit back down. She is literally covered and dripping with my cum. It's dripping down her forehead onto her cheeks and off of her lips onto her tits. Hey, I haven't gotten any for a long time. A big load was to be expected... She got a lot of cum with her fingers and ate most of it, and then cleaned herself up with a handy towel nearby.

We both look over at a noise and watch Jon jacking his cock off and breathing heavily until he shot cum straight up into the air.

Sharon laughed and said, "If either of those cocks were inside of me when you came, I would be pregnant already!" We all laughed.

Sharon moved as I stood up and then I kissed her. My hands were in her hair and I kissed her slow and gentle and deep. Sharon opened her eyes and saw the lust burning in mine. I lowered my hands to the waistline of her panties. With both of their eyes following, I finally pushed them down, removing the last remnants of Sharon's clothes as they pooled around her feet. I grabbed her by the waist and pulled her hard against me, squashing her big tits flat against my chest and pressing my cock into Sharon's stomach. A deep, moan escaped her lips. She almost forgot that she wasn't single and that her own boyfriend was in fact a couple of feet away and was watching her every move. She was so incredibly horny, and I was turning her on so much, what, with my big dick, my teasing and assertiveness, not to mention our past. Sharon didn't know whether this whole thing was more for her now than it was for Jon and his fantasy.

Suddenly I broke the kiss and with a look of utter lust spun Sharon around so that her back was pressed against my body and turned so that she was standing facing Jon. "Look at your boyfriend, Sharon." I said as I ran my hands from her slim waist onto her stomach and pulled her back against me.

Sharon breathed heavier as she stared into her boyfriend's eyes. His eyes were burning with the same lust. My huge dick was pressed against her ass and I began kissing down her neck before turning just her face towards me and once again kissing her but making sure that Jon could see our tongues dancing together. As the hot kiss continued, I slowly slid my hands up her body to cup both of her large, heavy tits. My hands squeezed the soft flesh of her 38D's. My fingers sank into them. I kneaded them and kissed her hard and passionately right in front of Jon's face. Sharon couldn't stop herself from moaning into my mouth as she reached back and ran her hands through my hair, giving me perfect access to take liberties with her tits as she arched her back slightly, pushing her ass back towards me and pushing her tits hard into my hungry hands.

At first, Sharon had her eyes closed, reveling in how hot she felt and how good I was kissing her, not to mention how amazing my hands felt on her body. However, before long she opened them, wanting to look in to her boyfriend's eyes as he watched me, her lover, doing all this hot shit to her. Sharon kept her hands over her head in my hair, and my hands were still roughly groping her tits, as she once again locked eyes with Jon. He had undone his jeans and had his hand down them as he watched her being taken like only he should be right doing, but right in front of him. Sharon obviously felt a thrill rush through her as they watched each other for a few minutes while I continued to enjoy her body with my hands and lips.

"Enjoying watching me turn your girlfriend on, Jon?" I asked as he looked up, as my hands were still squeezing Sharon's large tits roughly. "I think she likes it. No, I KNOW she likes it..."

Jon could see the smug smile on my face and he looked a little pissy, but he looked back and his eyes rarely left Sharon's for a few minutes while I continued. She did see his face after I finished speaking and she saw that lust rage on Jon's face. She then decided to join in on the verbal front to my surprise and joy.

Turning her face half to mine, she gently kissed my lips lovingly. "I love the way your hands feel on me. It's so hot having you take me in front of my boyfriend...ohmm fuck...you're making me so horny!"

Our lips locked for a brief moment before I broke the kiss again. Sharon looked like she was about to beg for my cock. My huge fucking cock was pressing roughly into her ass as she was staring into my eyes as I continued groping her big tits. Glancing at Jon, Sharon turned completely to look at me. "I think he wants to watch you fuck me Paul..." Sharon said, running her hands over mine and helping me to roughly squeeze her tits. "...I think my boyfriend wants to watch you push that big...dick...into my pussy...and fuck me." She was breathing so fast now it was like she had run a mile!

I had to keep going. This was too good to pass up, "Is that what you want Jon-boy?" I asked and saw Sharon get a shiver of electricity through her when her boyfriend nodded.

"You want Paul to give me his hard dick baby?" Sharon asked Jon, teasing and very horny.

Once again Jon nodded, lust raging on his face and his hand pumping in his jeans. Turning her face to mine, Sharon said, "Well then, do you want to fuck me in front of my boyfriend, Paul? Want to bend me over and pound me?" She asked with a very husky voice.

I had to get to the heart of the matter, right this second. No fucking around. "You tell me now Sharon, do you want me to fuck you in front of your boyfriend? Do you want my dick inside you right now, right here?" Biting her bottom lip, she nodded definitely, however I wasn't quite finished yet. "Then you better beg me to give it to you."

Sharon's eyes sparkled and she smiled dirtily and looked over her shoulder at Jon. "Oooh honey, Paul wants me to beg him for his big dick...beg him to fuck me with it..." She said as she looked into Jon's eyes and watched how hot he got from it. This was so fucking evil, mostly because we were both enjoying teasing her boyfriend "...Mmmmm...I think I should..."

She turned back to me once again, "I want your big cock so badly, Paul, I want you to put me on this bed and fuck me with this big, hard cock all you want. Please baby, please fuck me in front of my boyfriend. Please give me your big dick." She said and heard Jon groan beside her. "But, I want to ride you first, please... I want you and my boyfriend to watch me while I fuck myself on your big cock."

Jon's dick looked rock hard as he watched Sharon straddle me, and their eyes locked. Jon watched his hot girlfriend kneel over me, her pussy over my dick as she knelt watching Jon and breathing heavily. "There's no turning back now baby, you're going to have to watch your girlfriend ride Paul's big cock. Isn't that what you wanted? You wanted this, right? You've certainly turned me on enough with all your fantasies about me and him." Sharon then reached down between her legs to wrap her fingers around my hard cock, positioning it before slowly lowering herself down.

As Jon watched my hard cock first touch his girlfriend's hot pussy, his hand flew in his jeans. If only he had known what a Pandora's box he had opened by saying he wanted to watch us... Stupid fuck...

Sharon fixed her eyes onto her boyfriend's own and moaned deep as she watched him as my thick cock continued to fill her up. "Ohhmm, this is soo fucking hot!" Sharon moaned. My hands found her hips and began to pull her down the rest of the length of my dick, all the while Sharon kept her eyes fastened on Jon's. This was insane, but oh so fucking hot!!

"Fuck! You're so big!" Sharon moaned in my ear. "I missed your cock SO MUCH. Oh My God.. I'm going to cum already..." she hissed and whispered "fuck ME..." And all of a sudden, she slammed her body down on top of mine and sat up with her hands on my chest. She started breathing heavy, moaning and then screaming, "...CUMMMMING!!" Her eyes closed and her pussy seized all over my cock as she came harder than ever before with me. She started shuddering and I had to hold her up eventually.

She managed to say in an shuddering but half comatose whisper to Jon, "Did you enjoy watching your girlfriend cum on this ...ohhhh...ummm...big fucking cock!" She kept grinding on me though.

I saw Jon staring hornily into both of our eyes. Why the guy was enjoying watching his girlfriend stuff herself full of my cock I will never understand, but it had gotten me back into Sharon's pussy, so I wasn't going to stop now.

"Fuck man, you're girlfriend is one hot fuck!" I grunted out still holding a firm grip on Sharon's slim waist. The words made Sharon moan loudly and she began to bounce up and down again. The bed was lightly rocking back and forth. Sharon was driving herself up and down on my hard cock, and her eyes had closed. Her beautiful face contorted in ecstasy as she relished in the feel of my big, thick cock pushing in and out of her, one that she knew didn't belong to her boyfriend. The whole thing had me struggling to not shoot my load inside Sharon right then and there.