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I think it's normal to have a sexual bucket list. Maybe it's not, but hell, everyone likes to think they're normal, right? The point is, I have one. Over the years I've added and scratched off items on my list. Some of those things being: A threesome involving two women, a threesome with another guy and a girl, get laid two by women within the same day, sleep with a tall girl (I'm an average 5'7" white guy), and many others. I've been lucky enough to achieve all but one of the items that are listed above, and this is the story of how one of them happened:
I've been able to make some money over time playing music in bars and restaurants. I would guess that 90% of my sexual encounters are a result of this (seriously guys, learn to play 25 to 30 popular songs decently, and start playing them out). The other 10% is pure dumb luck. 100% of the time its a total surprise. I'm on the shorter end of an average in every way white guy with no game.
I was playing at a restaurant when I met a nice woman named, Sarah. She was a middle aged lady who came into the restaurant. She seemed to really like the songs I played, I knew almost all of the ones she requested, and I would learn the ones I didn't. Sometimes she was with her husband and kids, and sometimes she would just come in with her girlfriends. Eventually she asked if I played private parties. I sometimes did, and she arranged for me to play at her house.
Sarah is a doctor, as was her husband, and they lived in a GIANT house. They would throw little parties with their friends every month or so, and I became the regular entertainment. It was always fun.
Christmas time comes around and it turns out that the country club that Sarah belonged to was doing a fundraiser for who-knows-what and wanted some live acoustic music during the dinner. I had agreed, since it's always fun getting paid to be the loudest person in the room.
The day of the fundraiser arrives and I'm told to talk to a "Cindy" about where to set up my equipment. I find her. The thing that struck me about Cindy was she was clearly in her mid-to-late forties, but everything else about her was "young". She was a very attractive woman, with a chin length hair, platinum hair. She was in great shape and was wearing a little glittery pink dress with purple swirls all over it. It looked sort of plastic, but I have no idea what it was really made of.
Cindy shows me to the hall where I'm gong to set up and informs me that the check from the country club is in her office and to not let her forget to give it to me before I leave.
I start to play, and it's going well. Before too long Sarah comes in with some friends, and they mingle. Everyone is having a good time. A couple hours into the gig, I'm asked to stop playing for a presentation for whatever it was they were raising money for. Cindy says it's going to be a good half an hour, so we might as well go to her office to get the check.
We take the walk down the hallway to her office. She has a wine glass in her hand. She's clearly a little tipsy, as am I. She makes some idle chit chat about how much she is enjoying the music, and how she appreciates being able to play last minute. I tell her I'm happy to do it, and that I'm having a great time. We get to her office and she unlocks the door. Her office is small. She has a small desk with a computer facing the door. She sets her glass down on the desk as she walks around it and finally sits on the chair. Her head disappears behind it as the sound of a desk drawer open then shuts. She reappears with a envelope in hand, and extends her arm to hand it to me. I walk closer to grab it, and as I reach out to take it, she pulls the envelope back towards her with a playful smile. That's when it clicks in my brain what's happening (again, I'm pretty slow most of the time).
I don't have a thing for older women (although I seem to do well with them), nor do I NOT have a thing for them. People can be sexy at any age, and Cindy was sexy. She stands up to meet me at the other side of her desk and puts the envelope in the inside pocket of my blazer. She runs her fingers down my arm and grabs my wrist, and puts my hand on the small of her back. Instinctively, I pull her body against mine, and she starts kissing my neck. I feel her fingers pulling down my collar as she nibbles and kisses her way up to my ear. I waste no time and slide my hands up her dress and grab a cheek in each hand. I can tell she's wearing a lace thong as I massage her ass. We kiss, and I explore her body with my hands. She sits leans me against the desk and undoes my belt without ever removing her lips from mine. After my belt is undone, she drops to her knees, the bottom of her dress pulled up to her waste revealing her tiny white panties. She gets my raging hard-on from my pants and puts it in her mouth. She sucked my cock like someone who just really buca escort enjoys having a dick in her mouth. Enthusiastic, but patient. After what seemed like seconds, she's up on the desk. She removes her thong as she rocks back on the desk in one graceful motion.She opens her legs to reveal the smoothest waxed pussy I've ever seen. She pulls my tie to bring me closer and I put my hard cock, still wet from her mouth, inside her and started thrusting as hard as I could.
I'll admit, I lasted MAYBE five minutes. I told her I was going to cum, and she pushed me off of her, put her mouth back on my swollen head, and swallowed every last drop of cum that shot out of me.
She decided we should get ourselves put back together and check on the party. We walked back into the hall, and I didn't say another word to her. She went back to acting like she was just the lady who payed me to lay music, and I have to honest, it was kind of hot.
The presentation was was wrapping up, and I saw Sarah, sitting alone. I figured I should say "hi". I walked over. We made some chit chat. The presentation ended, which was my cue to start playing again. As I got up, she said her friends had left and asked if I could give her a ride home after the event. I said of course, and played the last hour of the show.
I packed up my gear into the car, and Sarah hopped in the passenger seat, and away we went. It was only a 10 minute drive to house that was mostly silent. I pulled into her driveway, and she offered a place for me to crash, since it was late, and I had a good 45 minute drive back home. She said nobody else was home and it wouldn't bother anyone if I stayed. Being as oblivious to the signs as I always am, I asked where her husband was. She said they had been separated in the last few weeks, and would love someone else to be in her giant empty house with her. Then it clicked in my dumb brain what was happening (remember that thing about me being really slow to see these signs?).
Then I got nervous. If Sarah were to end up going down on me, would she be able to tell I was very recently with another women? Maybe she didn't even want sex at all! Maybe she just wanted to feel safe with someone who's never made a move on her. Was my ego still inflated from recent events to think that every body wants me? So I told her that a drink and some hot-tubbing sounded amazing. Surely she knows I don't have a swimsuit! Plus, the hot tub, would hopefully wash away the any evidence of the Cindy.
Her hot tub was on the second story deck. It was up high, in a house on a hill, so even though it was in the open air, there was plenty of privacy. She walked me to the hot tub and said I can get in while she grabs some beers. I strip down, and jump in and await. After what seemed like forever, she appears with a bottle of beer in each hand, and as naked as one could possibly be naked.
Sarah wasn't as fit as Cindy. She had the body of a 43 year old mom, who had a job, but worked as much as she was able. She wore it well. Her nipples were standing at attention in the night air, as she walked towards the tub. She handed me a bottle. I took it trying to act as cool as I could (not very). She draped her legs over the edge of her hot tub, put them in the water, and just sat on the edge. She just sat there, on the other edge of the hot tub, looking over me with a smile. She told me she had thought about this for while and that she was hoping I'd come home with her. I stood up and walked over to her and kissed her. It was light and gentle. Pure lips. She rubbed my half-erect cock as she looked at me with that same smile. I kissed her again. Then I moved to her neck, to her chest, and down her landing strip hair. I moved my fingers into her vagina as I licked her clit. Her hips rotated around and around ever so subtlety. Her hand pressed my head further into her crotch while she sighed. She grabbed my hair to pull my mouth off of her and pushed me back to the other side of the hot tub while finally getting all the way in the tub. She kissed me some more while she lightly jerked my dick, then turned around. She slipped my cock into hot pussy while riding it reverse cowgirl style. I sat back and just let her ride me. It was perfect.
After, she got up, and bend over the side of the hot tub and told me to fuck her. I could feel the cold air hit my wet body as I stood up my myself inside her. I grabbed her shoulders as I thrust in and out of her. She reached around and started playing with her asshole, and that the image was too hot for me to hold on any longer.
I told her I was about to cum. She told me to cum inside her. I exploded in her. I pulled out and a dribble of cum followed out of her. We sat in the tub and drank our beers.
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