Slept with a man 33 years older than me...

So on Friday night I slept with a man who is 56 years old. I won’t get into details on how I met him but we exchanged numbers and started talking. He’s in the professional field I’m hoping to get into so we were talking about that field and the careers in it. We spoke about grad school and how I’m starting in the fall and how expensive it is. I told him candidly I was in the market for a sugar daddy but I was kind of scared to actually do that. He told me about having sugar babies in the past and how it worked for him and how it’s all about being comfortable with the person. How it’s not really about money but more-so the enjoyment of being with an older man and for the older man, the enjoyment of being with a younger woman. We had really nice and kind of philosophical conversations about it. He offered to take me out on a date to see how I would like it and I agreed. He’s a tall, slim, white man with grey hair but he looks very good for his age.
We met up in the village at a nice restaurant. Our meal and drinks were super delicious. I couldn’t help but wonder what everyone who was siting at the tables around us thought or even our waiter. I mean you couldn’t tell it was a date since we were just acting like friends having dinner. The dinner was expensive since when he paid the bill I sneaked a peak at it. It was over $100 for one appetizer, and one entree that we shared between the two of us since I wasn’t hungry and didn’t want to order a whole dish for myself. We had two drinks each also. But neither of us were drunk. He gave me the option of us just parting ways after dinner, which he was totally fine with since he enjoyed our time and didn’t want me to feel any pressure. He also said we could walk around the city or go back to his place and just cuddle and that it wouldn’t go any farther than what I want.
I agreed to walk around with him. After maybe 5 mins of walking we sat down on a bench and he pulled me close into him and I laid my head on his chest. He was rubbing up and down my arms. We kept talking about my comfortability levels and how he wouldn’t pressure me into anything. That if I wanted him to take me home he would gladly do that. He made it clear I was calling the shots and he would be okay with whatever I decided. I told him I’m very inexperienced sexually so I was embarrassed. He told me I had nothing to worry about. I decided to go back to his place with him. We held hands on the walk to his car and again I wondered what people thought when they saw us. This time though we held hands so you can tell we were “together”. I wonder if I was being judged without actually knowing it. I was avoiding looking at anyone who passed by lol
On our way to his place he stopped and got the amount I told him from his bank account and gave it to me. He made it clear the money was mine with or without sex. When we got to his place he set the mood with the lights and put on some music. He made me a drink and we cuddled and started making out. He had me sit on his lap while caressessing me and kissing me all over. He asked if I wanted to stay doing that or do more. I told him I wanted to do more so I then followed him to his bedroom. There he sat down on his bed and positioned me standing between his thighs and asked me to unbutton his shirt and take it off. I was really nervous so that didn’t go quickly lol. He then asked if he could take off my shirt and bra which I said yes too. As soon as my bra was off his mouth was on my nipples. He licked and sucked each one so lovingly. He then had me lay down and asked if he could touch my little pussy which I said yes. While I was helping him pull off my pants and panties, he quickly took off his pants and boxers. He laid next to me and started fingering me soooo good. He had two fingers inside me. While fingering me he was kissing me all over and sucking on my breasts. I asked him if I could taste myself and he took his fingers out of my wet pussy and put them inside my mouth. I licked and sucked them clean. He said he wanted to taste and then got off the bed and pulled me to the edge where he got on his knees and nestled his head between my thighs. This man was extremely oral. I’ve never been eaten out the way he ate me out. I couldn’t handle it and made him stop because I needed a break lol I asked him if I could suck on his cock and he said yes. I started blowing him and he was so complimentary. Which made me feel good because I’m insecure about my oral skills since I have such a small mouth. He was average size in length and width. I loved it because I eventually was able to fit all of his cock inside my mouth. He then asked me to sit on his face which is something I’ve never done before. O. M. G. It was amazing. He kept tongue fucking me...I could feel his tongue going deep inside my pussy. It felt sooooo fucking good. When I finally had him stop because I couldn’t handle that I started to blow him again but I just went for it without asking lol he then brought out a magic wand which I’ve never used before and used it on me. It was on the lowest setting and after about a minute or two I had to beg him to stop because I couldn’t take it. I originally asked him to force me to take it because I knew I couldn’t be able to but I couldn’t do it even when he tried to keep it on me like o originally asked lol
After that he just asked me to lay on top of him and just rub my pussy up and down his hard cock that was laying flat against his stomach. He said he wouldn’t insert it and that he wasn’t going to fuck me. He was fine with what we were doing (again he knew how nervous I was and didn’t want me to feel any pressure at all) but I felt comfortable and safe with him. I asked him if he had a condom and if he wanted to use it. He obviously said yes to that haha. Once he put it on I got on top of him again like he asked and it took a little bit to get him inside me since I was tight but once he was in it felt so good. I’ve never ridden someone before (except that one time during car sex cause the car was too small and the guy I was with nor I couldn’t lay down lol). He had me rocking back and forth and just fucking him. He would occasionally stop me to thrust himself as deep inside me as he could possibly get. We kept fucking all while kissing one another. I leaned down at whispered in his ear that I wanted him to cum inside me. He asked if that’s what I really wanted and I said yes. Almost immediately he came (inside the condom of course). He stay inside me because as he was cumming I kept moving slowly up and down his cock trying to squeeze every drop out. I told him I loved feeling his cock inside of me so he buried his cock as deep as possible inside of me and we stayed like that for a couple of minutes. I got off and we cuddled and talked for a little bit. I kept bringing up insecurities about my performance but he kept telling me I was a natural and I knew what I was doing lol
I don’t know if I’ll see him again or not. He’s traveling for business the next couple of weeks so maybe when he gets back...even if it was a one time thing I enjoyed it so much. The expensive dinner made me feel special, the money and sex itself made me feel powerful.
Sorry for the super long post and the typos I’m sure I have in here lol I’ll keep you guys posted on if I see him again :)
Thanks for reading. Happy pleasuring to you all! :)
Published by jenniev
5 years ago
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viciou5
viciou5 4 years ago
Clap Clap BRAVO.....nice story
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NaughtyParamedic 4 years ago
Such a hot story
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jenniev
jenniev Publisher 5 years ago
to namaste65 : Yeah that’s definitely something I’ve learned haha 
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namaste65
namaste65 5 years ago
Older men have experience. Younger guys primarily are looking out for themselves. Older men will look out for your needs first...
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The167
The167 5 years ago
damn I need to meet a girl like you
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pjny21
pjny21 5 years ago
to jenniev : Hahaha, had to ask.  It seemed like quite an experience for you!
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jenniev
jenniev Publisher 5 years ago
to pjny21 : Lol nah
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pjny21
pjny21 5 years ago
So....are you going to see him again, Jennie?
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ur2lipsonmycock
ur2lipsonmycock 5 years ago
Yes. Very glad you had enjoyed your experience! I love feeling touching kiissing licking all over a womans body. Each woman has different arousal n stimulation zones. You are. Learning them.  Mmmmm
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shyguy6ix
shyguy6ix 5 years ago
Wow very hot!  Lucky guy
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ehecatl999 5 years ago
Great story...
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