I'm 21 years old and I have a thing for older guys. Not all guys, just good looking in shape older guys. I got a job right out of high school, and it is a great job. I'm 5'5" tall, 118 lbs. and I'm in great shape. The thing I don't like about myself, is my tit's. I'm an A cup, but I guess it's kind of in proportion with my petite body. I've been told a million times I look like a young Elizabeth Hurly. I have long auburn hair and a nice tan completion. I get lots of looks and stares from guys, but the one's near my age don't interest me at all.
My story begins with my partner at work. His name is John, he's 65 years old, 6' tall, I guess about 215lbs. and in great shape. He has great hair, it's a little longer and its salt and pepper, a really good-looking guy. Most people would think he's in his early 50's. Our job requires lots of traveling, and for a 21-year-old woman, I couldn't ask for anything better. The reason we are partnered together is that we rate hotels and resorts, and our company wants both the young and older thoughts on the resorts they have us rate. Our first trip was to a resort in South Carolina. It was great, but we both agreed it was a little boring. the next stop was California, it was a little more fun because we had more leisure time to enjoy it.
It was our third trip where things started to get a little more interesting. John and I had 3 days in the keys, and we literally had about 8 hours' worth of work, the rest was our time to relax and make some mental notes. I decided it was time to flirt with John a little, and since he was a widow and I was single I figured, why not. I was 21, and I was always horny. On this trip I put away my more conservative bikini's and brought all my thong bathing suits.
After our first day we had a nice dinner and went to our rooms. The second my door was closed I was naked and laying on my bed masturbating. My thoughts while I was playing with myself were all about John. I would pretend I was masturbating for him, and it would get me off instantly. The next day I put on my thong, a long cover up and meet him at the pool cafe for breakfast. John was already there and looking more buffed than usual. I figured it was time to turn on the flirting, so I said, "Johnny, you're looking good, you been working out more?" He explained he was and also just lost 10 lbs. There was very little fat on this man.
We had a very nice breakfast mostly talking about exercising, and dieting, no doubt we both had great bodies to show for it. We finished breakfast and headed for the pool. When we got there, I said, "I'm not trying to embarrass you, but I brought my skimpier bathing suits this time, I hope it doesn't make you uncomfortable." I opened my cover up and took it off.
John said, "You think me looking at you ass is going make me uncomfortable, trust me, it's not." I just smiled and started to put on my lotion. I teased him a little more by asking him to do my back. We laid in the sun, swam, drank and killed the whole day at the pool. We even had dinner in our bathing suits at the cafe. By the time we went upstairs, I was drunk, horny as fuck, and needed to masturbate. I assumed he was doing the same thing, so once again, a pretty quick orgasm. I forgot to mention, I always travel with my vibrator and dildo, so my orgasms happen pretty quick.
The next day we repeated what we did the day before. The only exception was, the entire day while I was looking at John, I was trying to figure a way to have him fuck me, and when I say fuck me, I don't mean a nice romantic one with candles and music, I mean a hard, nasty do everything kind of fuck! I came up with a plan that after we went upstairs and showered. We would meet in my room to watch a movie. My plan was to be in the shower when he got there and also leave my toys out where he would see them. I told him I would leave the door unlocked and he could just come in if I was in the shower.
I left my toys on the nightstand where he would see them as soon as he walked in. I only brought a pair of panties in the bathroom with me. I showered, put in my lacy panties and waited on the bed. I heard him start to open the door and I quickly ran into the bathroom so he would think I was still in the shower. I waited about 5 minutes and came out. I had a towel on and said, "Oh sorry, I didn't think you'd be here so soon."
He said, "I'll come back if you need more time." I told him no, it was fine.
Then I turned and pretended to be shocked that my toys were out. I said, "Uhhh, sorry about that." then I walked over and put my toys in the drawer. Then I said, "well I guess you know why I wasn't showered yet, again, I'm sorry about that."
He said, "not to worry, I think we were both doing the same thing about 20 minutes ago." He gave a little laugh, then he said, "it's pretty normal, I don't think there's anybody who doesn't. do it." I loved how honest he was, and I figured I would push it a little.
I said, "well to be 100% honest, I'm usually thinking of you when I'm doing it, again, I'm sorry if that embarrasses you, but it's the truth."
He said, "and who do you think I'm thinking about when I'm doing it? So, we can both be embarrassed, or just be adult about the fact that we find each other attractive." That was when I decided I would go for broke. I undid my towel and let it fall to the floor. I was standing there wearing only my panties and my small tits were on full display for him.
I said, "I think we can watch something better that a movie if you're willing." He was just staring at me, mostly at my tits. He never answered so I walked over to the bed and sat with my back against the headboard. I reached in the drawer and grabbed my vibrator. With his eyes were still glued on me, so I scooted down a little, turned the vibrator on low and put it on my clit over my panties. I looked right at him and just started enjoying the feeling. I only took a minute before I saw the bulge in his short, so I asked, "Do you want me to stop? " He slowly shook his head and just kept watching me. I felt for the button and turned it up a notch to medium. I was really starting to feel it and heard myself softly moaning.
I waited a couple minutes before saying, "feel free to lose those shorts if you want." Still without saying a word, he stood up, unbuttoned his shorts, took off his shirt and sat back down wearing his tight boxer briefs, damn he looked good! His cock he was really straining to stay inside those tight briefs. While continuing what I was doing I asked John, "You don't have to answer, but how long has it been since you've had sex? it's been over a year for me."
John simply said, "A long time." I knew right there; I was going to get my wish tonight. I looked down and saw why he couldn't take his eyes off me; my sky-blue panties had a big dark spot forming from my anticipation. I turned it to high and went onto my first orgasm with John watching me. When I caught my breath, I turned it off and put it on the nightstand.