Straight Male / 27
Rich Guys At A Golf Resort Paid To Watch My Sister And I Fuck.
I have a twin sister and over a summer when we were 20, we worked at a golf resort. It was an incredible scottish style course, cost about 150$ to play 18 holes, over looked a lake, and had very nice lodging and restaurants. A silver spoon kinda place. I was a caddy, and my twin sister was a bartender. One day I caddied for 2 older men, probably 70+. They were very nice to me, lots of cigars and whiskey. They tried to get me to partake, and I had a swig or 2 of whiskey, but I was working so I didnt go nuts. They each tipped me 200$ after 18 and I told them to go to the bar and let the bartender know that they both got a drink on me, and that my twin sister was working the bar.
When I was done for the day I went up to the bar myself and got a drink to hang out while my sister finished her shift. My sister looked a bit flustered to see me and asked if we could talk. We stepped out near the cart corral and she told me that 2 old men had offered her 10,000$ cash, for us to go up to there room and they wanted to watch us get it on...
For me it was a pretty easy yes, because of the social implications, under normal circumstances I would never have touched my sister, but I had jerked off thinking about her in some less proud fapping scenarios. I told her that it was entirely up to her, and I would support her decision, and then also hinted at how far 10,000$ would get us.
We mulled it over for a bit, she told me to follow her to the bar, that we would get really drunk while she finished her shift, and go do it. She just kept topping off my whiskey coke with whiskey. When she was done she slipped a bottle of tequila under her servers apron and we went back to the cart corral where she pulled a few big swigs. We were both pretty drunk and I got so turned on when she said, "Fuck it, lets just have some fun with this, sex is fun, money is fun why not."
They had given her their room number, we went to the building they were staying in, and she knocked on the door. One of the old men answered and let us in. He said he had to go get his friend and left the room. A few minutes later they both came into the room. They re-arranged the armchair and desk chair in the room around the bed and pulled out about a half inch thick stack of 100$ bills and said "If you kids want, this is all yours, just give us a good show." I asked what they wanted to see first, and they told me to take her clothes off. So I did, and then they wanted to watch her please herself on the bed for a bit. she did and I just stood against the wall wondering what I should do next.
They broke their old wrinkly cocks out and started to stroke themselves. They told me to start licking her, and that I couldnt stop until they could tell she was enjoying it. I got between her legs and we looked at eachother and I said, Let just enjoy it. I went down on her for a bit. at first i had feelings of WTF am I doing right now, but those switched to feelings of excitement to get my dick wet. She was giving exagerated moans of pleasure to the delight of the older men. Then they told her to return the favor to me, I took of my pants and we re arragned ourselves on the bed so that I was laying and she knelt over me. She took my dick in her mouth and I just kept looking at the old men's dicks to keep myself from cumming.
These guys had a specific fetish. While she was still blowing me, they told me "Now put your seed into your sisters gash, and then we will give her ours." a phrase I never though I would hear... But I was drunk and horned up, so I looked to her for approval. She shrugged as if communicating that we have come this far, lets get the money. She knelt on the bed and i pressed my cock into her doggy style, probably not even a minute into it, one of the older guys said "Spill your seed." That took me a few steps away from cumming but I just closed my eyes and felt my dick in a wet pussy and it happened. I felt my dick pulse for 20 good seconds, and was balls deep when I released. I pulled out and aside from a string stuck to the tip of my cock, creating a bridge to her pussy, the rest was deep in her. They told her the last thing we had to do for the money was for her to lay on her back and take their seed as well. I went in the bathroom while they did their part. Cleaned off my cock and saw a very fancy looking watch that I grabbed off the bathroom counter. I regretted that choice for a few months, but I was drunk and just though, "im taking your watch pervert." They didn't let her shower up at all and shoo'd us out of the room once they were done with her. We lived together nearby. When we got home we drank a bit more and I asked how she was feeling. She just said "Sex is fun, lets leave it at that." We never brought it up again, we've never hooked up again, and everything has been the same between us since.
When I was done for the day I went up to the bar myself and got a drink to hang out while my sister finished her shift. My sister looked a bit flustered to see me and asked if we could talk. We stepped out near the cart corral and she told me that 2 old men had offered her 10,000$ cash, for us to go up to there room and they wanted to watch us get it on...
For me it was a pretty easy yes, because of the social implications, under normal circumstances I would never have touched my sister, but I had jerked off thinking about her in some less proud fapping scenarios. I told her that it was entirely up to her, and I would support her decision, and then also hinted at how far 10,000$ would get us.
We mulled it over for a bit, she told me to follow her to the bar, that we would get really drunk while she finished her shift, and go do it. She just kept topping off my whiskey coke with whiskey. When she was done she slipped a bottle of tequila under her servers apron and we went back to the cart corral where she pulled a few big swigs. We were both pretty drunk and I got so turned on when she said, "Fuck it, lets just have some fun with this, sex is fun, money is fun why not."
They had given her their room number, we went to the building they were staying in, and she knocked on the door. One of the old men answered and let us in. He said he had to go get his friend and left the room. A few minutes later they both came into the room. They re-arranged the armchair and desk chair in the room around the bed and pulled out about a half inch thick stack of 100$ bills and said "If you kids want, this is all yours, just give us a good show." I asked what they wanted to see first, and they told me to take her clothes off. So I did, and then they wanted to watch her please herself on the bed for a bit. she did and I just stood against the wall wondering what I should do next.
They broke their old wrinkly cocks out and started to stroke themselves. They told me to start licking her, and that I couldnt stop until they could tell she was enjoying it. I got between her legs and we looked at eachother and I said, Let just enjoy it. I went down on her for a bit. at first i had feelings of WTF am I doing right now, but those switched to feelings of excitement to get my dick wet. She was giving exagerated moans of pleasure to the delight of the older men. Then they told her to return the favor to me, I took of my pants and we re arragned ourselves on the bed so that I was laying and she knelt over me. She took my dick in her mouth and I just kept looking at the old men's dicks to keep myself from cumming.
These guys had a specific fetish. While she was still blowing me, they told me "Now put your seed into your sisters gash, and then we will give her ours." a phrase I never though I would hear... But I was drunk and horned up, so I looked to her for approval. She shrugged as if communicating that we have come this far, lets get the money. She knelt on the bed and i pressed my cock into her doggy style, probably not even a minute into it, one of the older guys said "Spill your seed." That took me a few steps away from cumming but I just closed my eyes and felt my dick in a wet pussy and it happened. I felt my dick pulse for 20 good seconds, and was balls deep when I released. I pulled out and aside from a string stuck to the tip of my cock, creating a bridge to her pussy, the rest was deep in her. They told her the last thing we had to do for the money was for her to lay on her back and take their seed as well. I went in the bathroom while they did their part. Cleaned off my cock and saw a very fancy looking watch that I grabbed off the bathroom counter. I regretted that choice for a few months, but I was drunk and just though, "im taking your watch pervert." They didn't let her shower up at all and shoo'd us out of the room once they were done with her. We lived together nearby. When we got home we drank a bit more and I asked how she was feeling. She just said "Sex is fun, lets leave it at that." We never brought it up again, we've never hooked up again, and everything has been the same between us since.
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