A couple of weeks after Mom passed away, Jenny called me from work one afternoon and told me not to bother picking her up after her shift ended, because she was going to catch a ride home with her boss.
It was late in the afternoon, but the twins were still at school in their after-school care program, when Jenny showed up at the house with her boss in tow.
She walked into the house, and yelled out, “Honey, I’m home,” mainly to warn me that I was no longer by myself in the house. “I brought someone special with me that I want you to meet.”
I came bounding down the stairs just in time to see a 40-something-year-old, obviously-Hispanic man enter through the front doorway behind Jenny.
“Sweetie, this is my boss, Jaime Hernandez, but you can just call him ‘Joe,’ because that’s the name he likes to be called.”
“It’s a pleasure to meet you, Joe,” I said, shaking the middle-age man’s pudgy hand.
“The pleasure is all mine, believe me. I can’t believe you’re okay with this,” Joe said to me cryptically.
“With what, exactly?” I asked Joe, feeling very confused.
“With letting me fuck your wife in front of you,” Joe replied, shaking his head, acting as if he didn’t understand why I would allow such a thing.
“Please don’t get mad, sweetie, but I brought Joe home with me so that he could fuck me in front of you. It’s been years since we’ve done any cuckolding, and I figured that it was high time that we get started again. You’re okay with that, right?”
“Of course. It’s just that I wish you would’ve warned me in advance that you were going to be cuckolding me with your boss this afternoon.”
“Why? Would it have made any difference? Besides, I just made the arrangements with him right before Joe gave me the ride home. I thought you liked good surprises,” Jenny said me. “And Joe’s a wonderful surprise. I didn’t think he’d say ‘yes,’ but he did! And so here we are.”
“Yeah, here we are,” I replied to Jenny half-heartedly.
“Don’t worry, Joe. My husband is just in shock right now. That’s all. He’ll warm up to you once we get underway. Speaking of which…I have to pick the twins up from school in about an hour and half. So we’d better get a move on, if we’re still gonna do this thing,” Jenny said, taking Joe by the hand and leading him up to our bedroom, with me following the two of them the whole way.
Looks-wise, Jaime “Joe” Hernandez was definitely nothing to write home about. He had an average-looking Mexican-American face. He had chubby cheeks, and a large hook-shaped nose with overly-wide nostrils, and a triple chin that folded over on itself. He was maybe 5’5″ tall, and was overweight by I would estimate at least 60 pounds or more. I know, because I was staring at his fat ass as I was following him all the way up the stairs and into our bedroom.
The reason why I was in shock was mostly because I never thought in million years that Jenny would pick this type of man to have sex with. But she did. And I knew it wasn’t because his looks turned her on.
So all I could assume was that this was going to be a pity-fuck on Jenny’s part. She must feel sorry for this man for some unknown reason, and now she’s trying to offer up her tits and her pussy to him to help make up for something bad that he’s going through right now in his personal life.
Once we all got into the bedroom, I sat down on one of the easy chairs across from the foot of the bed, and Jenny motioned for Joe to sit down on the side of the bed.
Then, while she was standing up in front of him she asked him, “Would you like to see my little boobies?”
“Yes, ma’am,” Joe said to Jenny, eagerly nodding his head.
And as Jenny was slowing pulling off her Wendy’s smock and opening up her collared shirt to expose her bra-less breasts to Joe, she said to him, “Now, don’t expect too much. My boobs are tiny. But they’re all I’ve got, and they are 100% real. I promise you that.”
Jenny was now naked from the waist up and letting Joe stare at her tiny breasts with their puffed-out nipples while she was methodically undressing him from the waist up, until he was sitting on the bed with his large belly and his super-hairy chest exposed. Joe’s man-boobs were at least two-to-three times the size of Jenny’s little breasts, and it actually made me laugh when I made that observation.
But then I stopped laughing when I heard Jenny tell Joe, “Would like to see what my pussy looks like?”
And of he said, “Yes, ma’am,” and nodded some more.
“Well, I’m not gonna show you my pussy unless you show me your dick first,” Jenny said, toying with the man. I knew that what she was doing was testing Joe to see if he was serious about having cuckold sex with us, or if he was going to back out on her at the last minute.
But when he stood up and pulled down his pants and underwear to expose his package, Jenny knew that Joe had passed the test, and she told him, “Oh my God! You’ve got the cutest little dick on you. Have you ever gotten a woman pregnant with that sexy dick of yours before?”
“Yes, ma’am. I have two kids at home, and they’re definitely my kids.”
“Go ahead and step out of those pants, and sit back down on the bed, and spread your legs apart, okay?”
Jenny stepped between Joe’s bare spread-apart thighs, and she reach around the back of his head, gently pulling it towards her as she leaned her chest towards his face.
“I want you to suck my little titties right now. I also want you to reach around and squeeze my ass while you’re sucking on ’em. Would that turn you on?”
I couldn’t believe it, but Joe said, “Yes, ma’am,” to Jenny for the third time straight, and then placed his mouth down around one of Jenny’s nipples.
Jenny immediately corrected him, “My name is Jenny–not ma’am. And if you call me ‘ma’am’ one more time, I’m going to put my clothes back on and send you home. Do we have an understanding, here?”
“Yes, Jenny,” Joe replied, and then went back to sucking on her nipple.
“Good. Now grab my ass and squeeze it, like I asked you to do,” Jenny reminded him.
And Joe reached around Jenny’s hips, with a hand on each side, and grabbed one of her buttocks in the palm of each hand, before he began squeezing her small flat boyish butt.
While Joe was doing that, Jenny reached down into the front of her pants, undid the button at the waist of the pants, and unzipped the zipper at the front of the pants, before pulling the zipper wide-open to form a “V” shape.
“Would you like to touch and feel my pussy through my panties?” Jenny asked coyly.
If there was one thing that Jenny knew how to do, it was how to turn a man on. Watching her from the easy chair across the room, it was truly amazing how easy it was for her to work her magic on a man. I wasn’t even the man she was seducing, and my just watching her in action was making me get a hard-on inside my pants, without me even having touched my own dick yet.
Joe’s right hand pulled away from Jenny’s left butt cheek, and immediately slid into the “V”-shaped opening at the front of Jenny’s pants, so that he could touch and feel Jenny’s vulva through her thin cotton panties, while he continued sucking on her nipples and squeezing her right buttock with his left hand.