This happened a few years back in my sophomore year of college. I had just broken up with my first ever girlfriend who I had lost my virginity to and was browsing craigslist personals sections (RIP) for cuckold couples.
After talking with one couple for a bit, they offered to pick me up from my apartment near campus and take me back to their house to meet and play. I had been toying with this as a fantasy for a while but then when it could become a reality right before my eyes I was nervous and uncertain. But you know my horny ass said yes.
So they pick me up, I hop in the back row seats in their SUV and the wife gets out the passenger seat and hops in back with me. She really hit the nail for MILF image I was going for at the time. Blonde, petite but curvy (a little thicker ass/thighs) and a cute and young looking face as well.