“James, I want you to fuck my Rose,” “Whew,” I responded. “When you asked for the meeting and requested that I keep it between us, I was concerned.” He followed, “The only caveat being, I want to watch.” Relieved and realizing the cat was out of the bag, I chuckled, “Okay, but standard rates apply,” and I made sure he understood that he was strictly a cuckold in this scenario, but I’d give him the family discount.
This job is a bit different than business as usual. This request was made by one of my closest friend’s father. I’ve been friends with the family for over two decades, and his son obviously let my second job be known to his father, not thinking about the possible repercussions. He asked that I bartend his house party for her birthday the following weekend as a front and stick around after “To clean up.” I let it be known that I hadn’t made drinks in a decade, and he cut me short to let me know that there would be a real bartender and that I was more of a party favor. “No foul, no fuss.”
The family is a very prominent family in South Florida with very rich and booshie friends, as one would expect. I can’t say that I was surprised about the request because this wasn’t the first time I was approached by the father and the mother, for that matter. The wife had, on several occasions, come on pretty hard and aggressive. But at those times, I hadn’t made the career move, plus they were my buddy's parents. She is attractive and strong and, as I mentioned, frank about her wants, and this was an opportunity for her to put her money where her mouth was, quite literally. At one time in our past, she was groping my cock as I was driving her car and following her husband in son to a shindig, and she begged me to let her suck my cock while I drove and promised that she’d be the best head I’d ever had. I was eighteen at the time, and it actually required me to push her back and deny her, but I guess she’ll be able to have the last word and a bit of revenge for rebuffing her those many years ago. As it turned out, she had no idea I was hired for the night or the plan.
The night of the party, she was beside herself when I showed up at the house. I gave her a big hug and wished her a happy birthday, and I told her I was hired to bartend, plus I wouldn’t have missed her birthday for the world. She was so excited and already a couple of sheets to the wind, and she told me that she couldn’t wait to brag and show off “her other son” to all her rich country club girlfriends. The night turned out to be crazy as all get out; I forgot how the super-rich like to get down. There was everything under the sun to facilitate a good time, and everyone was partaking. At one point, She pulled me onto the dance floor and re-introduced me to one of her old familiar friends and her now-grown daughter. Both of them weren’t feeling any pain and were fighting over who had dibs or if they’d share as they both rode my thighs on the dance floor, and their skirts rode up on them more like belts instead of skirts while they both planted their flags as if I were new land to conquer; little did any of them know.
It only got crazier as the night went on, and the catch twenty-two was that after that night, my black book was going to no doubt grow exponentially because these people are super entitled, spoiled, and constantly keeping up with the Jones, not to mention, can’t keep their mouths closed. Rose had an amazing night and was getting a little sloppy, but she was so happy when I brought her a cup of coffee. She pushed me against the wall and attempted to kiss me, and when I reciprocated just enough, she sobered and lit up with a second wind. Her face told me as much as did her hand on my junk. “Drink your coffee,” as I gave her latitude with my cock long enough for it to swell and push against her hand, and you could see her battery charge in real time as she again asked if she could suck my cock right then and there. “You can blow out your candle later.” You have never seen someone end a party so fast and with so much gusto. She was literally pushing people out the door and throwing their coats at them while making it obvious to her girlfriends with head nods and crazy eyes towards me as to why. There was no sign or consideration given to her husband, but I knew the plan.
She was like a kid in a candy store, beaming with excitement once the house was clear of guests, and she dragged me by the hand upstairs and into their bedroom and pushed me back onto the bed. She frantically loosened my belt and pants and fished my cock from my briefs like it was that present she always wanted. She wrapped both of her hands around it and said, “Do you know how long I’ve wanted to do this,” before inhaling it, tonguing the length of it to the sensitive underside of its head before taking it into her mouth and sucking it as it grew in her hands and mouth like those party-favor blowouts. She can most definitely work some cock, and maybe that is one of the reasons I appreciate mature women. They take pride in it and have decades of experience, and there wasn’t any doubt that she loved doing it. I allowed her to continue her beautiful work until I felt my ball adjusting, my cock swell, and that initial twinge one gets that feels like if you let go, you’d cum, but I stopped her, and she was befuddled because she, too could tell I was close and looked at me dejected “Why did you make me stop” as I had to rip it from her mouth like a bone from a dog and tell her, “I want to take our time and enjoy it.” Her face again told me everything, like she couldn’t believe this was happening, and she jumped up surprisingly spry and asked if she could go shower real quick and, after a second thought, asked if I’d join her. Right on schedule.
The shower was a formality and my preference. She stood on business and wanted to get it out of the way, but I took my time lathering her and cleaning her while she continued with my cock. She lathered him up with soap and took certain liberties that only mature ladies understand. Her fingers cleaned my ass and massaged my balls as she pulled on my cock like she was starting an old lawn mower. We rinsed and half-assed, towel-dried before she again pulled me to her bed and pushed me back onto the bed to assume the position I rudely interrupted. “Where was I,” as she once again resuscitated my cock. She did so with even more vigor, and it wasn’t long before she was licking my pre-cum off the head of my cock, and once again, I pulled her off it and up to me for a kiss. She has amazing oral skills, and her kiss wasn’t too hard or soft, too hot or cold, and just right. Just as our kiss was breaking, she saw her husband come into the room, and he said Happy birthday my beautiful wife before he took up his position on the chase in the corner of the room.
She didn’t skip a beat and responded, “Thank you, thank you, thank you,” and continued as if this was normal, but you could tell she was extra happy that he took the time to arrange it. “Don’t mind him,” she tells me as she throws her arms around my neck and kisses me with renewed vigor. I stand up and turn towards the bed with her hanging on like a loose tie before I pick her up, toss her onto all fours on the bed, and pull her to the side, making sure our cuckold has a perfect view. She went downward dog and looked at her husband as I dove into her backside and spread her with my face. I love to eat pussy, and as some women mature past menopause, they will often have problems becoming wet, even when aroused. It's not a problem for me because I enjoy it so much that I drool like a big dog, and it helps. But to my surprise, she was plenty wet and happy to see me, and like fine wine, it just gets better with age. I smacked her ass cheeks and spread them more to get to her pretty, silky pearl. She was like a teenager again and pushed back to help me shuck her clam.
I love a mature woman’s stamina, and it is my experience that they can go as long as they want or as one persists. I love a challenge and could have eaten at her buffet all night, but she demanded more. “Fuck me, James,” as she backed up on my face harder and faster. I rose behind her and allowed her to push back onto my cock at her speed. Even being as wet as she was, there was still some delicious friction as I first broke deep. I made sure to pull out as far as I could to make for a better visual and so that we all could appreciate the repeated friction of breaking her. There was just enough light in the room to show my glistening cock bob in her pool. Nothing blows my mind anymore, especially with the more mature women, so it only turns me on when they do and say what they want. She reached back and teased her own ass before taking her own plunge. I always appreciate that feeling of brushing against the neighbor through the thin dividing wall and how it makes everything more snug. She was good and even reached down between our legs to conduct our concerto by directing and proving her dexterity by massaging and combing my balls with her other hand. I was so turned on and just waiting for permission.
A brother’s abs were burning as she challenged my endurance, and it was music to my ears when I heard, “I’m going to cum,” followed by, “Please cum inside me, James,” and that was all I was waiting for. Hearing her orgasm being imminent gave me the final wind I needed to hammer home. When it was evident she was over the edge, she pulled her finger out of her ass, and I could see her asshole hyperventilating and her pussy flexing and she gripped two handfuls of bedding to brace against my blows “Now!” I locked onto her haunches and tried to drive through her as her orgasm tried to expel me, and I came deep. She convulsed and fell onto her side in the fetal position before pulling me on top of her and panting a satiated “thank you, thank you, thank you,” and I replied “Happy Birthday.”
Happy Hump Day!
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