Supplementing her income
[This is basically a true incident that happened to me this month. I've doctored the dialogue to make it run more smoothly and of course to make myself look more heroic- what the hell, it's my story!]
I am a 45-year-old single guy who had been suffering from a serious lack of sex during the Covid-19 shutdown. My only pleasure was walking down the street to get coffee to go from what used to be my favorite restaurant. One of the women who had been a waiter in the restaurant was now serving coffee from a makeshift window in the front door. She was pretty cute, about 25, slim with small tits, and had short black hair and a few tattoos. Her name was Jude.
After a few weeks of going steady with my fist, I was going crazy. The next morning at the coffee window I asked Jude if she was able to make ends meet on her income, pushing coffee 5 hours a day. She gave me a slightly scared look and said, "Fuck, No!" The barista ten feet behind her said, "Language, Jude, for Christ's sake," which made us all laugh. Then more quietly I asked Jude, "Would you be interested in discussing a way to supplement your income?"
She looked at me steadily for a long moment, then nodded. "Meet me down at the corner at 10:15," she said.
At 10:15 she showed up, and I said, "Which way are you headed?" She turned north and we walked along kind of slowly.
Finally I said, "Jude, here's the thing. My wife is really lousy at sex, so I need a regular outlet. I think you're really hot, and if we could agree on a regular schedule, I could supplement your income a little." (I didn't have a wife, but I always told women that so they didn't try to get into my wallet while they're getting into my pants.)
She kept looking at me as we walked, then she said, "You want to fuck me, right?" Jude needed to get a refund on those charm-school lessons.
I said, "Right. Maybe twice a week, if that works for you."
She went right to the point. "How much?"
I chewed on that for a few moments, then said, "That really depends on how good a fuck you are."
She gave me a get-lost look and said, "So you want to open negotiations by fucking me for free today, right?"
I replied, "No, that wouldn't be fair. How about $200 for 45 minutes or an hour today, then we can talk about a regular amount."
"Can you afford that? What do you do for a living?"
"I'm self-employed, doing IT work," I said, "working from home these shitty days."
A look of relief came over her face- I think she really needed the money. "Good," she said, "turn right here." A minute later we were going up the stairs to a third floor apartment at the back of a dumpy building. When we got in, she dropped to her knees, unzipped me, pulled my cock out- I had been hard since we agreed to come to her place- and began sucking me. As she did, I began undressing her, then pulled her up, took the rest of her clothes off, and said, "Strip me." She did, almost eagerly, then she led me to a single mattress on the floor in a corner behind a shower curtain. She went back to sucking me- she was good at that, then pushed me onto my back and sat on me cowgirl. "Do you want me to eat you?" I asked. "No," she said, "that's for my boyfriend only. I'll take you in my ass if you want, though."
An alarm bell went off in my head. "Did you say boyfriend?"
"Yes, but not to worry, it gets him really hard when I tell him about fucking somebody else." We went back to what we were doing, and in half an hour we both came- at least it looked and sounded like she came. She lay there with her legs spread rubbing her clit while I got dressed.
"That was good," I said, handing her the $200. "If we say twice a week I'll raise it to $250 each time."
"OK, good. When do you want to come back?"
"Let's make it every Tuesday and Friday at this same time. I like to fuck during the day." We traded phone numbers.
So this went on for 4 or 5 weeks, and I thought it was mutually satisfying. I would go straight to her apartment from my home if I wasn't at the restaurant door for coffee.
Then one morning she said, "Meet me at the corner at 10:30. We have to talk." Guys just love to hear that, right- is she pregnant? Is she quitting on me? Is she getting married? Does she want me to get a divorce and marry her? When we met and started walking toward her place she said, "Look, my boyfriend is at my place. He's going to be 'sheltering in place' with me."
"Does that mean you want to quit?"
"I can't do that, Mr. Johnson. I really need money. And it will be even more expensive to live with an unemployed boyfriend in the place."
"So what do you want to do?"
"If you can raise it to $300 a time, we can make it a threesome. Like I told you before, my boyfriend is cool with us fucking, however you want to do it. Or I can pull a train if you want to watch- I've got a next door neighbor who would love to join us all. If you want to suck anybody's cock, that's cool, and I know my boyfriend will suck yours if you ask."
I thought for a few seconds, then said, "Okay, for today let's try just the two of us taking turns on you, as many rounds as we can manage. $300 for you, nothing for the boyfriend, right?"
She grinned at me. "Right. Cool! Sounds fun!"
We got to her place and she introduced me to her boyfriend, Dice. He looked like a shifty-eyed thug, and I wondered what she saw in him. I started to ask where he got his name, but then I realized I didn't give a shit. She had sort of a whispered huddle with him, he nodded, and she began taking off her clothes. "You can ball her first, Mr. Johnson," he said politely. So I did, and she was unusually energetic and did me in several positions. We finished in missionary while Dice licked my anus. She wore me out, and I couldn't go another round, so after Dice fucked her he rested a few minutes, then she sucked him hard and he fucked her in the ass while she rubbed her clit hard. Good porn to watch up close. When they finished she stood up on the bed, held her hand out, and said, "Was all that worth $300, Mr. Johnson?" I told her it was and I handed her the money. That was Tuesday, the 28th.
On Friday, the 1st, I didn't see her at the coffee place. I came to her place and knocked on the door, but nobody answered. Then I called her phone, but she didn't answer. Then a few minutes later I got a text from her, with just a video clip inserted in it. I played it and saw parts of a cellphone video showing me fucking her, her riding me, her licking my anus, Dice licking my anus, her taking it in the ass from Dice, and then- the grand finale- me handing her $300 while she, naked, explicitly says it was for the wild sex we just had.
My phone buzzed again with a call from an unknown number, but I knew who it would be. Dice said with a smirk in his voice, "I hope you enjoyed our little movie, Mr. Johnson. Obviously, we didn't do it for fun, not with an old fatass like you. The thing is, Mr. Johnson, you really shouldn't use your credit card to buy coffee from desperate people. It took us all of five minutes to get your email address, which will come in handy for sending this to your wife. OR... you can pay us $1000 a week, and you can forget about fucking Jude any more. Or finding her at the coffee place. We are gone, and you will send your first payment by Monday to this Venmo account." He gave the coded Venmo address details. "Repeat it back to me."
I had heard enough to make the next ten seconds very enjoyable. "Repeat this back, asshole- I don't have a wife! I just told your stupid cunt of a girlfriend that so she wouldn't get ideas. And I'm self-employed. So I don't give a flying fuck who you send it to. And if you should happen to come to my house, I've got enough cameras around to give the police very flattering photos to match with this little video- like I said, I don't care who sees it. If they want to write me up for patronizing a prostitute, so be it. I figure that would cost less than $1000 a month forever. So goodbye now, and don't forget to fuck yourself!"