Had a wild night with a waitress at a resort… [MF]

Basically, I’ve (m29) been going to the restaurant of a small resort just out of town for about 6 months or so. It’s amazing with great food and wine. There was a waitress there (20f, let’s call her M) who was from another country, very cute and perky. Not super pretty or anything, but definitely grabed my attention. She was very nervous the first time I visited, because she was new, and I tried my best to make her comfortable and ended up chatting with her quite a bit.

I went back 2-3 times more and she always used to come talk to me, even if she wasn’t serving my table. Once I went there with a girl I dated for a short time. I thought M seemed a bit jealous and I saw her looking at us from the other side of the restaurant. But I really didn’t think it was true, and I was just getting ahead of myself. Then she followed me on Instagram late that night out of the blues. I followed her back, and her photos were really cute, with her friends, and family back home. I started to have a bit of a crush on her.

I helped arrange a small office party with stay at the resort one evening. She kept coming over and talking to me, touching my arm and trying a bit to flirt. I was really looking forward to staying that night and may be spend some time with her, but I suddenly came to know of a small emergency at home and couldn’t stay. She was really disappointed when she found out. But the resort offered me a one night stay whenever I wanted as compensation.

I went back to stay alone, on purpose, a few weeks later. I didn’t know what to expect but was excited. When I reached for lunch, she was nowhere to be seen and I thought, I’d blown it and she must be on leave or something. I went back for early dinner in the evening and there she was!! I hadn’t told her I was coming, she got very happy and seemed quite excited when I told her I was staying there alone. I started flirting with her seeing how excited she was and she kept blushing and shyly tried flirting back. I invited her to join me for coffee and she said, she couldn’t as she was working. I asked her when she got off, she said, really late at 1 am. I said, well, that’s really late but we could have a drink together. I jokingly said she should come to my room when she’s free. She laughed, but blushed and said, ‘may be’ and left. She didn’t come back. I thought I went too far and I didn’t know what to do.

I went back to my room and got a bit restless. I thought may be she didn’t like me being so forward, I contemplated messaging her but didn’t. Finally at about 11 pm I messaged, saying, hope she didn’t mind, I was just joking. No response.

I put on a movie and had a drink, tried not to think about it. It was about 1 pm and I kept hoping to hear a knock on the door. 1.30, but still nothing. I gave up and I thought I should just go to sleep. Suddenly after a few minutes, I heard a knock. My heart jumped. I rushed to the door, and it was her! I couldn’t believe it! She said, so where’s my drink?

I invited her inside and poured a drink. She had left her hair open, she looked tired but pretty and she kept shyly staring at me. I slowly went close to her, held her hand and went in to kiss her. She let out a gasp and kissed me back deeply. I couldn’t believe how nice it felt, I put my hands in her hair, held her and kept kissing her, deeper and with more and more tongue! She pulled back, looked at me and said, she had been wanting to do that for a long time. She said, she had decided she was going to gather all the guts she could, ask me if I was single and kiss me after the party last time, and she was so disappointed when I left early. That was one of the cutest and nicest thing, I’ve ever heard.

We went over to the bed. Our hands going all over each other. I started touching her boobs and she started breathing really heavily. We slowly got rid of our clothes. She was curvy, just about 5’2, slightly plump but had a great body. I sucked on her perky brown nips and then went down, she had a bit of a bush, she smelt so good. She apologized, she wasn’t shaved, she wasn’t expecting this to happen. I said no need to apologise.

I went down on her for quite a while and she was super wet, and moaning like crazy. She came shuddering. She then started blowing me very softly. She kept taking me in her mouth, going up and down slowly, not very deep, but it felt good. After a while, we had sex. Plain old missionary as she moaned and sighed. I came in the condom, it was simple but felt amazing.

We chatted and cuddled for a bit and she said, she had only a couple of boyfriends before, back home, and she had never cum from sex or oral, it was her first time. I asked her if she enjoyed it and she said, a lot. She said she was a bit shy and wasn’t very comfortable with blowjobs, she hadn’t done it a lot much before. I said she did great and she had nothing to worry about. I had really wanted her to go hard but I didn’t want to pressurise her. So I didn’t say anything.

After a while we got going again, she was a lot more enthusiastic this time. She was opening up and seemed a lot more into it. I went down on her again, she moaning and slowly grinding on my face and as she came, she was soaking wet. I pulled her on top of me and made her go down on me. She was sucking and blowing me a lot harder this time! It felt freaking amazing. I held her head and directed her and made her go a bit deeper slowly. She gagged a bit but kept going.

I pulled her up, and she got on top and started riding!! As it was the second time, I was lasting longer. She found her rhythm and was riding amazingly. I played with her boobs and then put my fingers in her mouth and started talking dirty. I told her how much I loved being inside her. How good she felt and how good her mouth felt. She started moaning like crazy. I said I wanted her to go down again and not stop. She sucked on my fingers even more and moaned louder. I pushed her down and she went all crazy on my dick. I kept talking dirty and kept moaning and telling her how hot her mouth felt and I wish I could fill it up. She moaned hard and just kept going deeper and harder.

It was so hot, and as I got close, I told her, as I didn’t want to force her. But she kept going. Her moans getting even louder as I started moaning and then suddenly fired a load in her throat almost. She gagged a bit, but she immediately went back to it. I shot even more into her mouth. She slowed and kept sucking for a bit more, as I was moaning and shaking, it felt so good.

She looked up at me, then got a bit shy again, smiled and looked at the bathroom. I said, go. She ran, spat and cleaned her mouth and came back and layed on me. She hid her face in my chest and said, she didn’t know what got into her, she had never done this before and didn’t think she would like it so much. I said , I loved every bit of it and kissed her. She said she had never been so turned on before!! We chatted a bit again. I asked her to stay but she said, she couldn’t. I asked if she was gonna get in trouble. She said, that she didn’t think it was going to be too much trouble as there weren’t too many strict rules, but it’s definitely not something she wanted others to know.

But she said she would try to meet me before I left. I said I couldn’t wait.

I slept like a baby. I woke up the next morning at about 8 or so. I couldn’t believe the kind of night I had. Frankly it wasn’t very often something like this happens to me. I got so horny thinking about her. I wished I could have her again. I messaged her saying I missed her. She said she did too but couldn’t come over as she had some work and as it was day, she didn’t want to risk being seen. But she said she would try to meet me before I left. I was a bit disappointed but I started thinking about the night again. I got so hard and started jerking off slowly.

Suddenly after 5 minutes, there was a knock on the door. I asked who it was, I though probably cleaning. No response so I looked through the peep hole. I couldn’t believe it, it was M! I opened the door just a little. She looked around nervously and came in. She started laughing and said, she couldn’t control herself, she had to see me, as she looked down, she saw my hard cock. She blushed a bit and naughtily said, ready for me already? Before I could respond, she jumped down on her knees and started me sucking me off hard!! I almost lost my balance. It was shocking and so good!!

We had amazing sex again. Missionary, doggy and then her on top again. We started talking dirty again, then she said, moaning, she couldn’t wait to feel me finish in her mouth again! She jumped off, slid down my body and took me in her mouth! Going so hard again, this time looking at me! I was going crazy and I just went with it. I came hard in her mouth, and she kept kept sucking, looking at me shudder and shake as I came. She smiled naughtily again, ran to the bathrooms and came back.

She said she couldn’t stop thinking about the night. She was planning to come over in the morning and surprise me anyway, before I messaged her! She said, she felt very shy at first but she enjoyed me cumming in her mouth so much, she couldn’t wait to do it again. She just loved watching me shake and moan when I came.

I was spent but so happy!! She had to leave, so did I. I don’t know how but I’m seriously planning to keep this going. Let’s see what happens….

(Okay, this ended up being a lot longer that I intended. And I know it’s not super slutty or like a crazy story. But I had a great time. This was 3-4 years ago. Did this a few times more but couldn’t keep it going too long.)

Source: reddit.com/r/gonewildstories/comments/csln3y/had_a_wild_night_with_a_waitress_at_a_resort_mf