Twice, in fact. I posted about the first occurrence here:
viewtopic.php?f=46&t=69810
Many decades ago, since we needed a break, my wife and I decided to take a small two-day vacation on the upcoming weekend. As we made plans, she asked me if we might be able also to find a new man to fuck her on this trip. (We had tried to invent "hotwifing" before it existed.) I loved the idea, but the logistics were all wrong. We didn't have enough time to buy a swinger newspaper and go through personal ads and write letters and wait for replies. (This was before the internet took over. If you were super lucky, the as would hold a phone number.)
Moreover, where we were traveling was sparsely populated, making suitable candidates all the harder to find. She mentioned that we would, however, be travelling through the town that her ex-boyfriend lived in and that he would certainly love to fuck her again. I listened with mixed emotions, as I loved to watch her being fucked by another man, but I was not at all sure that he was the right man. He was, in fact, her boyfriend prior to meeting me.
I asked her if he would want me there with us having a threesome. She was sure he would, as he was super kinky. After some more talking, I gave her the okay to call him. She did call and he did welcome our visiting him that Friday night. I still wasn't sure that this was a good idea, but I also longed to see her suck his cock and watch him fuck her. Early that Friday morning, he called us and asked me if it was okay for him to invite his best friend to join us, as his friend always liked her and found her unbelievably sexy. Well, my cock overrode my brain and I instantly said yes.
Soon after, I had many second thoughts. It was bad enough that he was her previous boyfriend, but now I would be outnumbered. As I saw it, there was a small chance that this was the perfect setup for him to seek revenge, as I had pretty much stolen her away from him. At the same time, I could not see how I could call off the big event, as my wife was eager for it to happen, especially as a new cock was in the offering.
I decided that I had to play safe, real safe. I would not join in, but only watch, while fully clothed and armed. None of my handguns were suitable for conceal carry, so I borrowed a smaller pistol from a friend, along with its special holster.
We arrived early at her ex's house. I had never met him before; short and skinny, he didn't look threatening at all. We were roughly the same age, yet I thought he looked five to six years younger. He seemed pleasant enough, but very nervous, which made me nervous. He was making mixed drinks, which I completely declined, explaining that I had lots of driving still ahead of me. Actually, I didn't want to risk being drugged.
His best friend showed up, and he, too, was short, but not anywhere as thin. I noted his wedding ring. I towered over the two men and my hidden weapon only emboldened my natural alpha attitude and demeanor. I concluded that I had nothing to fear; indeed, I concluded that I could easily take out both men with no weapons other than my hands. Nonetheless, I explained that I would only watch the three of them, not partake in the sex. She was disappointed, but they seemed relieved, especially her ex-boyfriend. I picked the chair in a corner, so no one could sneak up behind me, just in case he had a second friend (or friends) hidden in his house.
I watched the three of undress and romp. Her ex came once, while his friend came twice—all of the loads were bareback and all shot inside her vagina. Everything went fantastically well, which made me feel silly for my fears of potential harm. Afterwards, his best friend thanked me for the best night of his life and left, as her ex drove off to buy pizza. While she showered, her ex thanked me profusely for the opportunity to fuck her again, revealing to me that I could not imagine how often he thought of her naked body as he was fucking his girlfriend.
He offered to let us spend the night at his home, which we accepted. The three of us slept in his king-size bed, after she had her second threesome. I remember the bed shaking me awake, as her ex fucked her in the middle of the night. I remember my confusion in the dark, as my brain sought answers to why the bed was shaking rhythmically. Amazingly, I fell back asleep before they finished. In the morning, he fucked her one last time.
lol
).