This happened about 10 years ago.
One afternoon in Miami I was driving in my newly purchased sports car. I was 24, loving life, windows down listening to 80s dance music. At the red light the music caught the attention of a Late 30s stunning blonde. She proceeded to ask me to lower the music to talk. I complied. We talked briefly about music, the car and my eyes (green eyes). Green light and we continued slowly, I asked her to turn into the plaza so we can continue chatting without causing traffic. We pulled into the plaza and chatted for about 10-15 min. We exchanged #s.
Next day she text me that she was married and we would have to chat on AIM while her husband was at work. So for a few weeks we chatted on AIM, all day at work I was on AIM chatting with her. Swapping stories, swapping NSFW pics, etc. What an amazing time to be alive. We never talked on the phone, always on AIM. Finally she told me she confessed to her husband and told him that she wanted me to join them for drinks and maybe more if he complied.
We set a date and continued chatting, I set boundaries/ground rules (no bisexual stuff) sexual tension building up till that faithful night. They had rented a hotel on the beach and we had drinks/dinner at some restaurant. We instantly hit it off (her husband and I), he loved sports etc. During dinner they mentioned that they wanted to document the encounter with video and pictures. I agreed to it.
After dinner we head up to their room. And the fun begins. (Around midnight)
The husband just sit on the couch and allows us to start. We undress. WOW what an amazing body on this woman. I could hardly contain myself. She promptly gets on her knees and says "finally i can taste your cock". She proceeds to wrap her lips about my throbbing cock. She blows me about about 10-15 min and i throw her on the bed and start eating her out. I swear it was the best tasting pussy I've ever had (even to this day), I went down on her about 45 min. Totally lost track of time, it was that good. All while her husband was taking pictures. He would take pictures then sit back down and jerk off then get back up and take more pictures. So finally it was time to put the condom on, but for some reason I was having performance issues because of the husband. I was way bigger than him (i'm about 6.5 inches) so it wasn't that. I don't know, maybe it was the alcohol. Well he noticed and asked if we wanted some privacy to get me going? I said yes. So he went to the bathroom, it worked. I was hard as a rock again. He was in the bathroom for about 10 min then came back out for some more pics/video. I pounded her soaked pussy for at least an hour before I blew my load in her mouth. She took it all. Massive load after edging a few times during the session. We then went to shower. She cleaned me up and I cleaned her up. Then she started to blow me again, wow. I got hard as a rock again and she told me to fuck her. This time the condoms were on the nightstand but oh well, I went for it. I fucked her for a few more minutes when her husband walked in, he watched us with his cock in his hand. We then we to the bed and hubby finally wanted a piece of his wife. Well I gave her back and he went doggy on her. She called me over and started sucking my dick. Wow she was loving this. He finally finished and it was my turn fuck her again. I fucked her in so many ways so many positions, at this point I don't know how many times she's orgasmed on the night, but she was aching for another load. I finally unloaded in her pussy. What a beautiful creampie. Her husband jerking all again unload his load on her tits. Perfect timing. It's like we were boys from college.
At this point it's 3am or so and we clean up. She goes to shower (barely being able to walk to shower). My knees are weak from the 3 hour session. Around 4am or so after we're getting ready to finally get to bed, we head to the balcony for one last drink and chat. Well that chat turned into a another blow job. WOW. Blow job turned into a rim job (my first ever). Unbelievable. She then turned around and lowered her pussy onto my cock and let it slide in. I fucked her for a few minutes on the balcony but we took it back inside. Her husband was already asleep. I then ate her out for about 10-15 min. Started fucking her again. Blew another load into her tight pussy. We had to clean up again.
Finally we get to bed (she slept with her husband). We wake up in the morning and we were spent. No morning fuck session, they had somewhere to be later that morning.
We went our separate ways and kept chatting on AIM. For the next few weeks her and I regularly had sex. This turned into a full blown affair. Month or so later she told me they moved to Tenn because her husband found out about our extra encounters.
What an unbelievable night this was. By far, to this date my best sexual encounter.
Source: reddit.com/r/gonewildstories/comments/40h8ir/m34_my_first_milf
Always hard to find a milf