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Disclamer:
All characters are consenting adults (over 18). This story is loosely based on
my actual experiences, however the names are fictional.
Story background:
Mike is a 45 year old married (to a woman) man who has secret desires to explore his sexuality with other men. Mike is athletic and fit and generally alpha in his daily life. But for some reason, Mike has secret thoughts about being a bottom for other masculine men.
During the day, while is wife is at work, Mike sometimes visits gay cruising sights to explore his fantasy and consider potential hookups. Mike works from home and works for himself as a tech business consultant. Since he is self-employed, he can set his own schedule.
We catch up with Mike mid-morning on a weekday while his wife is at work. Mike has logged into a gay cruising sight and he's looking for potential hookups.
Mike's profile is pretty straight forward: "Bi-married male, 45 yrs old, ddf/neg masculine bottom with just under 7 inches looking for masculine ddf/neg tops."
Mike is logged in and waiting to see if he is approached...
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On-line Temptation
I sat at my computer waiting for someone to approach my profile on the cruising site. While I waited, I browsed the map displayed on my large work monitor. The site listed other cruisers by their location and a single profile pic. Most tops showed pics of their cocks; most bottoms showed pics of their asses.
My profile pic was a standing ass pic my wife took once as a joke and sent to me during a playful texting session. She took the pic when I was getting out of the shower and was an unsuspecting subject. I thought it was a good pic, so I was using it as bait for any tops that might need a masculine bottom.
I was getting turned on viewing some of the profiles that were within 5 miles of my house. I fantasized about the potential of finding a regular, sane, top that could host during the day so I could meet and explore my desires freely without concern about being discovered or arrested (in a public place).
I was happy to see a lot of guys my age or older that where online looking as well. This improved my chances of finding someone who is OK with an older guy. I didn't need to wait long for my first bite.
A 61 year old top started a chat with me. His stats were 6' 210# 7 cut ddf/neg gay top:
Him: "Hey"
Me: "Hi"
Him: "What are you into?"
Me: "I like to get naked, suck cock, and get fucked."
Him: "Do you bareback?"
Me: "No, I can't bring anything home to my wife."
Him: "Sorry man, that's a dealbreaker for me."
"Damn!" I thought, "I hate it when guys demand bareback."
It seemed so inflexible to me that a guy would demand bareback sex on a first anonymous meeting. The guy had a pretty hot profile and pic too. I didn't have to wait too long for my next interaction.
His profile said he was 37, 5'5," 6.5 uc, Top:
Him: "Hey bud, you looking?"
Me: "Yes, but I can't host."
Him: "No worries, I can host."
Ok, this was good, I looked at his location details; he was just 2.4 miles away.
Me: "I'm usually available during the daytime, will that work for you?"
Him: "Anytime between 10am and 3pm works for me. What are you into?"
Me: "I like to get naked, suck cock, and get fucked."
Him: "Hot! Do you swallow?"
Me: "If you are ddf/neg, I love to swallow, it's a huge turn-on for me."
Him: "You little slut, LOL"
Me: "Guilty, LOL"
Him: "I have a few fetishes; are you ok with that?"
Me: "Usually I like them, what are they?"
Him: "I like to pay you for sex, like you are a hooker."
Me: "Um...are you a cop?"
Him: "Fuck no, I just have this weird turn-on. I like to pay you for each sex act I want from you."
Me: "I don't need payment, and I don't want to get arrested."
Him: "So donate the cash if you want...."
I started to wonder if this might be a cop trying to get me to ask for cash. At the same time, I was getting kind of turned-on thinking about being paid to do sex acts for another man.
Me: "How much would you pay me?"
Him: "Let's negotiate when you are here. I will ask you to do something for me and tell you my price."
Me: "And that turns you on? Even if you think I might do it for free?"
Him: "It helps me to think of you as an object, something I paid for."
Me: "That is kind of kinky, you want to objectify me?"
Him: "Only if you want to. If you take the money, it tells me that you are willing to do a task for me at a price. It gets me really hot."
Me: "Well, if you swear to me you're not a cop or something. I'd be willing."
Him: "I'm a 5'5" Nicaraguan, I can't be a cop even if I wanted to be, LOL"
Me: "Are you ok that I am almost a foot taller than you?"
Him: "Fuck yeah, I'm paying your big ass to do things for me."
Me: "Well if you insist, I will play along."
Him: "Are you serious about meeting?"
Me: "Yes, with some planning."
Him: "Are you available, now?"
I looked at the clock. It was just after 11 a.m. and I knew my wife wouldn't be home until after 4 p.m. My cock was rock hard thinking about being paid to do things for this Latin top.
Me: "I can be available soon, are you inviting me over?"
Him: "How about 12:30?"
I had to pause to consider if I would actually follow through with this. I was so horny, I hadn't had sex in weeks. But was I really willing to take this step.
Me: "That works!"
Fuck, I was thinking with my cock now. It had taken over. I was too curious about this guy's fetish. I wanted to see what it would be like to get paid to serve another man at his request.
Him: "Here's my address:
"
Me: "So you want me there at 12:30?"
Him: "Park in the driveway and come in the side door to the garage. The door to the house will be unlocked. Just knock and come in. If possible, don't let the neighbors see you enter."
Me: "See you then."
We both disconnected from the chat. I was now committed to meeting my new friend in person.
I was already rock-hard thinking about meeting my new top that was only a short 2 mile drive away. I liked that he was a Latin guy, and he had an uncut cock. I'd never had an uncut top before. I assumed that my new top would want both holes so I headed upstairs to get prepared and shower before heading out.
My hands were shaking with anticipation as I prepared myself for our meeting. I was forty-five minutes away from being a pay-to-play sex worker. I was so curious to experience
Mike Meets His "Customer"
I hopped in my car wearing only a pair of Jeans, a button-down shirt, and a pair of slip on shoes. It was early spring and in the temp was in the low sixties. I felt like I didn't want to be overdressed since I was hoping to strip as soon as I got in the door.
I made the quick drive to the next neighborhood over from my own. Our town was hilly and wooded. The yards were generally spread out and private. I liked that he wanted me to be discrete with my entry. The last thing I wanted was for someone to see me entering or leaving his place. I didn't want any suspicions.