Hello Darlings
I posted a repeat story this morning by mistake! Here is the real story!
April 2017 - Spring break was upon us! We planned to visit my family on a nice week-long road trip and soon, Rose would be making the trip to me so we could begin. On top of spending a week with my gf away from school, we were planning on doing something kinky on the first night. We had put out another ad, and we were approached by an older guy named Tim.
Tim was about 55 years old and very interested in playing with us. He got a room at the Hilton in the city and wanted us to swing by. We were super excited because we wanted to experiment with her sugar baby interest. He was gonna order room service and everything for us. So, the morning before her trip to me, he mentioned that he prefers his women to be hairless. Rose had never shaved it all before, normally just keeping it neat and tidy. But, she was so excited that she shaved before loading the car.
When she arrived, we had a couple of hours to ourselves to spend. We made out, fooled around, and cuddled on my bed, knowing that the rest of the trip we'd be spending on couches and futons. Then we decided to shower and get ready for Tim. I went first, then she asked me if she got all of the hair around her pussy. I sat her down on a coffee table and spread her legs to inspect her work. She missed a couple of spots, so I offered to help. I shaved away what she missed, leaving a perfectly bald and fuck-ready pussy. I literally just shaved my girls crotch because another man wanted it to happen.
She got worked up too and offered to blow me while she used her vibrator. She came a couple of times and then finished me on a towel before she jumped into the shower. I let Tim know that we were gonna be there soon and started loading the car. When I came back inside, she was wearing the same outfit she had worn for B almost a year before. A black sundress with flowers and her hair tied up.
The drive to the hotel was very much full of giggles and touching. When we arrived, we made our way inside and practically jogged to the elevator. We were alone though, and it was hard not to imagine that the guys in the elevator behind us were enjoying the view of Rose. Afterward, we made our way down the hall and knocked on the door.
Tim opened the door, greeting us both with the manors of someone his age, then invited us to sit on the couch. He ordered up room service for us, and we chatted about life a bit before the food showed up. It wasn't much, because everyone was a little nervous, but it was pretty tasty! As we ate, he gradually geared the conversation more and more towards sex. What did she like, what I liked, and what our experiences were so far. The food and the little bit of wine he served us to go with it pretty much quelled our nerves and now Rose was as chatty as ever.
Inch by inch, they got closer during the conversation till he put his weathered hand on her thigh. She immediately went quiet and looked up at him as he smiled. He said, "follow me." And led us into the bed area of the room where he took her hand and guided her down onto her knees. I was standing about five feet away, with a full view of everything. He told her to undo his belt and drop his pants, to which she complied. His cock sprung out and was just inches from her face. It was pretty much the same as mine, so not terribly impressive, but he was confident nonetheless. And Rose liked confidence.
He pulled her head onto his cock and she got to work. While she did, he turned to me and continued the conversation about expectations and rules. He was so calm and normal-seeming while she bobbed her head on him. But, her skills wouldn't take long to make him stop her, stand her up and tell her to strip. She obeyed, turning around when he told her to, then, letting us both soak in her fully naked body. He motioned to the bed, where she laid down. He spread her legs and began eating her pussy. She later described it as not great, but still nice. While that went on I started kissing her and teasing her nipples.
After Tim determined she was wet enough, he stood up, put a condom on, and slid inside of her while I was still kissing her. He began pumping her pussy, causing her to moan into our kiss, then she broke lips with me and asked me to sit back for a minute. I watched as a man the same age as her father took her body in front of me. He changed position one time. He laid down on the bed, but just his upper body, and told her to sit on his cock facing out. I could see why. He then had an amazing view of this blonde college girl riding his cock, while he got to stare at her ass and sexy back.
Shortly into that, he came, and she jumped off, quickly coming over to me as I lay at the head of the bed. She climbed on top of me, helped me put a condom on, then guided me into her. She rode me slow and deep and kissed me passionately as she did. It felt amazing to have her body on mine and to touch her as she fucked me. She picked up the pace and we both ended up cumming together.
We made small talk for a few minutes, before getting dressed and heading out. He gave us somewhere around $200 for gas money (unexpected) on the way out. We talked about it and determined that, though his confidence and orders were nice, he wasn't very good. She also enjoyed the pampering and being told to shave herself for him.
Until next time ;)
~Rosie