Cuckolds, Covid, and Anal Sex

The vast majority of cuckolds I know will never agree to have anal sex with a bull, but every single one that I’ve known has enjoyed it when they do. Here is the story of my Covid-Cuckold Justin and his first anal experience.

I began seeing Justin, my latest cuckold, just before the Covid-19 lockdowns began and as a result, our relationship was more vanilla than normal until recently. I introduced him to chastity, prostate massage, and other pretty typical cuckold concepts, but I didn’t really feel safe seeing my usual bulls much less meeting new ones. That changed the other day during a happenstance meeting at Starbucks.

I had been checking out this tall guy ahead of me his mask hiding the fact that I actually knew him, intimately. It was David a bull I hadn’t seen in almost two years. He recognized me and we chatted while we waited for the baristas to fill our orders. That night I was in bed with Justin who had dozed off earlier watching a Netflix movie when I got a text from David. He wanted me to come over. I told him that I wasn’t alone, but if he wanted to come over and fuck me he could let himself in and join us in bed. I gave him the code and he was climbing in bed less than twenty minutes later.

Justin was passed out having finished almost 3/4ths of a bottle of Pinot Noir after dinner and didn’t even stir as David fucked me. God, it felt good. The next morning David wanted to fuck once more before he had to leave for work. Unlike the night before David wasn’t holding back and before long Justin was wide awake watching us. He didn’t say anything but his eyes were as big as saucers. I pulled down the comforter and saw that he was completely erect so I told him to masturbate for us. David was used to my cuckold’s so he didn’t think anything of it and just continued as if this was totally normal.

Soon David was gone giving me time to update Justin on my history with David and how I had run into him the day before. He was turned on by the whole thing and I let him have ‘sloppy seconds’. The one thing I hadn’t told him about David was that I had convinced him to have anal sex with two of my previous cuckolds and I was pretty sure he would again.

Not wanting to miss a chance I told Justin I wanted to peg him. We had played with anal toys and experimented with prostate massage with no real success in the past. Justin’s fairly submissive so it didn’t take long for me to get him to install the restraints on the bed so I could tie him up while I pegged him. I made sure to use the smallest ‘peg’ as to not freak him out and he seemed to like the power dynamic.

Over the next couple of weeks, I normalized the experience by tying him up and pegging him several more times adding in a blindfold to spice things up. Eventually, I decided Justin was ready and texted David explaining what I wanted him to do and when to arrive. Just as I had Justin restrained I heard David letting himself in downstairs. Blindfolded, Justin heard him too and asked me what that was. I told him it was David and that I had a surprise for him. After I explained what was about to happen Justin started freaking out.

Justin was adamant that he didn’t want David inside of him. After about twenty minutes of coaxing, manipulation, and blackmail Justin began negotiating and I knew I had him. He wanted David to wear a condom. I explained that David already fucks me without one and that it wasn’t really necessary, but eventually, David told him he would wear one.

I think I had mentioned that I hadn’t seen David in almost two years and I don’t think he is the least bit attracted to men so it took him a LOT longer to get hard than I remember. I had to suck on his cock forever to get him hard. By the time I got him lubed up for Justin, he would be soft again. It was frustrating. Finally, he was hard enough and lubricated enough to fuck Justin, but Justin’s anus was closed tight. He was in pain, David was annoyed, and I was frustrated. Eventually, David rammed his cock inside of Justin who was in so much pain he was begging for him to stop. It wasn’t sexy. I had David stop for a moment so could loosen the restraints on Justin’s legs and have him get up on his knees.

In one hand I held David’s cock and in the other Justin’s as I tried to get them both aroused. I guided David’s cock and had him press it softly against Justin’s anus. Justin was softly asking us to stop. I explained to him that as long as he resisted it was going to hurt. To prove that fact David took over and rammed his cock inside of Justin who fell forward and cried out in agony. I told David not to stop fucking him and told Justin that if he’d listen to me it would stop hurting.

I told Justin to get back up on his knees and to arch his back to give David clear access. He complied and I could see him trying different angles to reduce the pain and discomfort. In a few moments, I could tell that Justin and David were almost working together to get through this. I reached for my phone and began recording. Shortly after I noticed that Justin’s penis was erect and he was pressing backward when David was pulling away.

Justin was completely silent, but clear semen was now dripping from his erect penis and he was breathing heavily. I removed the restrained from his wrists and ankles and his blindfold. Then I told him to get on his back. Without comment or complaint, Justin did as I asked and I helped him lift his legs so David could penetrate him again. David filled him up easily and I could tell he was hitting Justin’s prostate when he began leaking again.

Justin grabbed David’s arms and my little cuckold was having his first of many orgasms. David, for his part, was taking forever. How long was this going to go on I thought to myself. Finally, I told David to pull out and Justin looked like he was in pain. I asked Justin if he wanted David to keep going and he struggled to say yes. I told him that if he wanted to keep going he’d have to let David take off his condom so that he could finish. Justin said one word and with that, David removed his condom and began fucking Justin again.

Now that I had Justin’s attention I told him to beg David to fuck him harder. Justin was very compliant at this point. Then I told him to beg David to fill him up. David was pressing his weight on top of Justin as I saw his buttocks flex and he began filling my cuckold up with cum. When David pulled out and sat up we both saw that Justin had ejaculated all over both of their stomachs.

Justin was emasculated and the gravity of what just happened seemed to take hold. He got up to put on his clothes and had his back to us when I noticed David’s cum leaking down Justin’s leg. Justin gathered his clothes and escaped to the bathroom. After he left I didn’t hear from him for a week until I sent him the video… (to be continued)