Not exactly a cuckold experience in the strictest terms, but close enough for me!...
When I met my current wife and we began dating, she had a couple of regular boyfriends and a very young co-worker that were sniffing around for her scent.
On maybe our 3rd or 4th date, while we were taking a break during an all-nighter, she asked me, "What am I going to do about Jim"? I answered by asking her, "What about him"? She said he wanted her to take him to bed and "teach him how to fuck". (!)
She said she had been prick-teasing him when he would come over to her house during the week; wearing tshirts tied at the waist with no bra, or wearing a long men's dress shirt, no bra, and would leave it a little too unbuttoned, and 'accidently' giving tit shots when leaning over. I asked how far they had gone, and she answered just some light petting and kissing, but she was very apprehensive about the age difference (she was 37; he was 18/19) and the fact they worked together.
So I then asked if she wanted to fuck him and she confessed that she indeed wanted to ("I want to sit on his cock"!), and I told her to go for it. I told her I wanted to watch!For the next few weeks, she was dropping little hints, calling me and letting me know he was at her house, and laughing about me hiding in the closet and watching them. I kept encouraging her, but didn't pressure her about it.
She came to my apartment on a Friday night to spend the weekend, and as we were in bed that night, out of the blue, she announced, "I've been playing with Jim all afternoon"! I replied, "Ohhh...?" and she answered, "yeah, he thought we were gonna do the big nasty!". So I asked for the details and went down on her, and, sure enough, her inner lips are stretched. Nothing bad, but there's only one way they get that 'look'. As I began licking, she started by telling me that he had come over after his shift was over at work. She had worked earlier also, and said she was taking a bath when he arrived. She put on a towel to answer the door, let him in, and told him she was going to get dressed. She told me that she put on her thin cotton nightgown with nothing on underneath! I asked if he could see her good, and she answered, "Oh yeah, I made SURE he could see", and that she stood in the light so he see all of her. She then asked him to rub her legs, and she layed on the couch with her legs over his lap. Of course, it didn't take long before he was rubbing her thighs, and as he was working his way up with his hands, he was also working the bottom of her gown up. She said he eventually had it all the way up to her pussy, and was brushing it wiith his hands as he was rubbing and squeezing her thighs.
So I had to ask at that point, "Did you open up your legs so he could touch you"?, and, after a brief pause, she hissed, "yessssssss..." She continued by telling me that she WANTED him to touch her, and she could feel his hard on in his jeans, so she began rubbing his crotch while he finger-banged her, and they were kissing passionately. When she was ready to feel him inside her, she tolds him to take his pants off, and they fucked right there on the couch!
After he came, she took him to her bedroom, and they talked, laughed, and played around with each other until they were ready to get down again. She worshipped his cock and balls until he was rock-hard, then showed him the pleasures of having her "from behind" (doggy). She said he lasted about 15-20 minutes this time, and it was blowing his mind that he could cum in her with no fear of pregnancy, so he let her have his load.
They had to wrap it up because she had to leave to come to my apartment, and every once in a while she will drop another detail or two about that evening. But they met up a few times before this date, and a few afterward; as matter of fact, I surprised them one afternoon! It was the typical coming home for lunch unexpectedly, and finding both of them flushed and flustered. My point was, however, there's many more details of several meetings that she has never shared...yet.
he and his father (my landlord) have had a threesome with my drunken wife after a home party at their house. 
