Back in March I crossed a line I never thought I’d cross. It was just before my 22nd birthday. I’m a server at Twin Peaks in Scottsdale and March is a pretty good time for tips with March Madness going on and all. Which was good because I was trying to save as much money as possible because my friend and I were going to Coachella. These guys had come in and ran up a pretty big bill watching one of the basketball games. They looked a little older than my dad, so were probably in their mid fifties. Their flirting was kind of embarrassing but they seemed mostly harmless. At the end they left a $100 tip on a $150 bill so I was pretty happy.
The next night my friends and I were out in Old Town. After a mostly boring night my friend and I were waiting for our Lyft when two of the guys from the night before ran up to say hi. I was a little wierded out at first but they seemed mostly harmless. One of them, Tom begged me to have one drink with them. My friend looked at me exasperated so I said no. They looked so disappointed and walked away. Just before the Lyft pulled up my friend got a call from her boyfriend who’d called because he’d gotten off work early and wanted to see her. When the Lyft arrived I told her to take it and go see him and I’d get another and go home.
As she drove away I started to order my own Lyft. I happened to look up and see Tom and the other guy Shawn stopped about halfway down the block. I don’t know why, but I waived. They started walking back towards me and before I knew it we were in the bar doing shots. Tom started getting into my personal space and when I felt his hand on my ass I knew it was time to go. I walked out of the bar and Tom followed me. He apologized for grabbing my ass but kept saying how amazing and beautiful I was. His friend Shawn was standing there pretty quietly but then pulled out his wallet. He had a stack of $100s. Tom said “Please don’t be mad. You’re so hot. We’re at the W just down the street. Come back to our room. We’ll give you $1000 for blow jobs. Easiest money you’ll ever make.”.
I said “Fuck you” and started walking away but the thought of $1000 would make my Coachella trip so much easier. I don’t know what came over me but I turned around and said “ok let’s get this over with”. We walked down to the hotel and were in their room before I could think about it too much. I told them to give me the money first and Shawn counted out $1000 and gave it to me. I put it in my purse. Tom asked me to take off my top and I said no but he pointed out that I probably didn’t want to get anything on it. He had a point so I agreed. I was standing there in my heels, skirt, and sheer lacey bra when Shawn took off his pants and sat on the edge of the bed.
He had a small, thin dick. He has shaved all his pubic hair the way guys with small dicks do to make them seen bigger. He was not in good shape and his belly was resting almost on top of his dick. He looked older than I thought, maybe even 60. I got on my knees in front of him and reached out for his cock. He let out a little moan when I touched it. I took a deep breath to settle my nerves and leaned forward to put his dick in my mouth. As soon as my lips brushed his dick head I tasted the salty taste of cum. I thought it was just pre cum but Shawn started moaning and saying “Ya baby” over and over and I realized he was already cumming. He didn’t have much force and it was basically dribbling out. Most if it ended up on his own legs. I felt a small drop on the top of my boob just above my bra and was glad I’d taken off my top. Shawn was soft almost immediately and his dick almost disappeared.
Tom walked over and said “My turn”. His cock was already out and rock hard. It was much larger than Shawn’s. One of the biggest I’d ever seen actually. He sat on the edge of the bed, taking Shawn’s place. I leaned forward and took him in my mouth. He filled it and stretched me lips. I started sucking him and stroking his shaft at the same time trying to get him to cum as quickly as possible.
He pulled back and asked me if I’d fuck him for another $1000 but I said no. I leaned back in and worked his cock with my mouth and in less than a minute I was gagging on the salty ropes of cum hitting the back of my throat. I wasn’t expecting that much cum from an old man and pulled back. A glob of cum hit he in the forehead and I turned my face as another rope of cum hit my cheek. He was stroking himself and cumming all over my face and hair. I couldn’t believe how much cum he had. Finally he was done and I went into to bathroom to clean up. Tom told me they’d be in town two more days if I wanted to hook up again and handed my a paper with his phone number on it. I put the paper in my purse and said “No thanks not interested” and left.
As I sat in the Lyft on the way home I realized I was in the hotel room with them less than 30 minutes. Tom was right. It was the easiest money I’d ever made.
Source: reddit.com/r/eroticliterature/comments/cd34ug/crossing_the_line_mmf
Great story!
Very good writing, super hot story!