4 Wealthy Middle Aged Men.
After highschool I worked as a waitress for a handful of years at a Chiles in the Chicagoland area. I quickly learned tips were better when I wear a pushup bra, low cut shirt, and make sure to bend over and put on a bit of a show. One day I waited on particular a group of 4 middle aged men and I could feel them checking me out every time I was out in the dining room. Aside from staring at me, they never made any lude remarks (atleast to my face), and overall seemed like respectful gentlemen.
I was estatic when I saw the tip, as between the 4 of them they had tipped 1,300$ for about 80$ of food and drinks. The recipt also had a note saying "This is only part of the tip. If you want the rest call (Phone Number)" I ended up sending a text to that number and they asked if I was free to meet at a nearby hotel bar when I got off work. I agreed and at this point I knew it was going to be something sexual but the potential payday was still too tempting and after my shift, I made my way for the hotel. I texted a friend to let her know where I was going and that I planned to meet a guy I met on Tinder. I also sent her the phone number of the guy and asked her to call and check in on me in an hour or so to 'get me out of the date if it was going poorly.' I didnt tell her the truth, that if the price was right, I was probably going to be playing with the cocks of 4, mediocre looking, middle aged men.
I was trying to hide my nervousness as I waked into the hotel lobby. As soon as I could see the bar, I saw the 4 men sitting and drinking around a table. They noticed me right away and waved me over to come join them. They asked if I wanted a drink, and then followed that asking if I was old enough to drink. I let them know I was 22, and they got me a margarita. They let me know that they were from out of town and here on work. They kept asking how much I liked the tip, what I would spend it on, how much that kind of money would help me, if I wanted to work as a waitress forever, ect... Then they asked how much 5000$ would help me and I said "that would pay almost 6 months of rent." They said "Well why dont you come up with us for a little bit, help take care of us old guys, and then we can help take care of your rent." I swallowed down the rest of my drink and thought about it for a breif moment, and then decided 5k was too hard to pass up.
We got up into the room and it was a pretty standard looking hotel room with a king sized bed. One of the guys grabbed the TV remote and said, "You dont mind if we put a little something on do you?" He started to search through the adult films that could be ordered and put on a porno of a couple chicks satisying some dude in a pool. They told me to get on the bed and make myself comfortable. One of the guys stood next to the bed to rub my shoulders saying he would help me relax and enjoy the video. After brefily rubbing my shoulders a bit his hands quickly passed over my back and to my side under my arms. He was starting to sneak up and rub my side boob. I was not not feeling very turned on at all at this point and more nervous than anything, but I was worried that if I resisted at all, I could forget about getting that cash. I had come this far and gave into him putting his hands anywhere he wanted.
The thought crossed my head that if I just pretended to get really into this and not waste time, I may be able to get this over with quickly. He was not working quickly still trying to gauge how I was going to react as he slowly worked his hand onto my boob. I said "Here let me help you with that" and pulled the straps of my shirt and bra off the sides of my shoulders, so it was just wrapped around my stomach with both of my boobs now hanging out. I could sense the excitement of these men and I told the guy who was now sitting next to me on the bed that "I am here to help you, let me give you a massage." He laid on the bed and I crawled between his legs and started to unfasten his pants. Once I got them down past his cock I tied my hair back and went to work. I dont know if my mind was playing tricks on me, but his cock tasted like old man. The other men had started to gather near the edge of the bed, and I could feel hands start rubbing around my pussy. Followed by thumbs sliding under my thong at my hips and pulling my pants down to my knees. Now my bare ass and pussy were up in the air as I knelt on the bed and I could start to feel fingers rubbing around a poking at my clit. All the men had started to pull their cocks out at this point and were giving themselves a nice slow stroke. A 2nd of the men laid down on the bed but his head was right near me and he told me to sit on his face. I stood up to get my pants the rest of the way off and lowered myself right onto his mouth. I could feel his tongue poking around at me as I bent down to return the favor.
I was 69'ing him for a few minutes but lost track of my surroundings for a moment because I recall being distracted by his hairy and wrinkly nut sack, when suddenly a cock plunged into my pussy. The guy I was on top of was still licking me while the first man I had sucked started to thrust his hips into me. I actually was enjoying myself a bit at this point and was surprised that the guy was still using his tongue despite a dick being in me. The 2 men I had not yet touched had gone from groping at all of my body to getting up infront of me and putting their cocks in my face. I took turns on each of them giving a few strokes in my mouth and switching between theirs and the guy that was still laying beneath me. I actually got pretty close to cumming a few times while we were in this positon, but it was all down hill from there.
Eventually the men rolled me over so that I was laying on my back, with my legs hanging off the bed. They pulled me near the corner so that they were able to access my mouth by just standing near the edge of the bed. They just kept cycling around going from jerking themselves, to fucking my pussy, or sticking their dicks in my mouth. One of the guys while thrusting his hard cock into my pussy said "I was 31 when you were born, this cock was already fucking other women before you could even talk." Another one said "you are lucky, you are getting over 200 years of dick today." (yea right... im the lucky one...) The guy pounding me quickly pulled out, slid his condom off, and sped around the bed up near my face and told me to open my mouth, spurts of cum started shooting directly into my mouth and I could taste a bitter saltiness pooling around my tongue, with more spewn across the outside of my cheek. Once he was done spraying into and around my mouth, he rubbed his dick across my face to get the last little bit of cum off him, and onto me.
The other 3 men all finished is similar fashion and by the end I my face was both sticky and slimy. They handed me a rubber band wrapped around a roll of 100's and it ended up being 6,100$. They let me take a shower and freshen up before I left. I have never done anything like that again, but if I could get paid that much, I would do it again without hesitation.
