I (41m) was 24 at the time. My best bud and I went out to a nice dinner to celebrate a promotion I had received. We went to a nice restaurant, which was on me as I got a good raise. It was an Italian joint and we were drinking lots of wine.
Our waitress was a tall blonde with an amazing ass and some perky C tits in her early 20’s. She was super cute and her and I started flirting almost immediately once we were sat. My friend and I talked about how hot she was and I told him I was going to take her home with me. He laughed and thought I was full of shit. After we ate my friend had to go and I told him I was going to stay for another glass of wine. When the waitress came back she asked where my friend went and I said he had to go. She said, “well I hope that doesn’t mean you’re leaving too” I told her I could use another glass of wine or two.
Even though the place was busy at the end of the night she kept coming by to chat and make sure I had a new glass of wine to try. I asked her what her plans were after work and she said she didn’t have any. So I asked her to hang out after. She said it would be an hour or so before she got off work so I told her I’d meet her outside then.
I picked her up and asked her where she’d want to go. She said she wanted to have some wine and maybe we could just go buy a bottle instead of going to a bar. We did so and ended up back at my place.
We chatted and flirted for a bit while we polished off the bottle. I remember she had this cute laugh and her nose would scrunch up. (For some reason little quirks like this really turn me on) she laughed again and I just couldn’t resist anymore so I kissed her. The kiss was super passionate, the kind that lasts a long time as we started touching each other all over. I broke away only to pull her shirt over her head and then kissed her again while I unlatched her bra. I pulled back to remove her bra and saw her amazing perky tits. Her nipples poked out hard and were perfectly placed on her breast. I immediately took one of them in my mouth as she let out a moan.
I kissed back up to her clavicle and to her lower lip sucking it into my mouth. I remember thinking this woman is absolutely stunningly hot! I then kissed down her body and removed her pants and underwear as I moved. Following with kisses, as I liked to do, all the way to her ankles. Then kissing and licking back up her legs to her inner thighs and then to her pussy. I didn’t even care that she just worked a full shift, I had to taste her. It was a lot more delicious than I would’ve thought.
I ate her pussy until she came in my mouth. She then wanted to return the favor. I sat up on the couch and started to undo my pants and she took over. I remember her gasping a bit when she pulled out my cock (See Profile) she dove right in taking as much into her mouth as she could. She was excellent with her mouth and sucked me for a good 15 mins before standing up and then sitting backward onto my cock. Her ass looked so amazing as she slowly moved down and eased it in a little bit at a time. Moaning and telling me how it felt. Once she adjusted to it she started bouncing on it and I could see those perfect tits in a mirror bouncing the whole time. She came again on my cock and then I picked her up and took her to my bed.
Once there I laid her on her back, licked her pussy a bit more and then fucked her hard with her legs on either side of my head. She finally started to climax again and I asked her if she wanted me to cum. She could only get out “Yes! In me!” (Which I’ve heard over and over in my head to this day.) I let loose and filled her pussy with my cum and she came hard at the same time. We laid there panting and catching our breath.
Afterwords we talked, laughed and made out before passing out in my bed. In the morning we fucked again and then showered together before I took her back to her car. I gave her a kiss goodbye and called my friend when I got home. “Guess what I did last night?” Lol
The waitress and I actually ended up becoming friends and fucked here and there until she moved away for college. I lost track of her, but damn was she sexy.
Source: reddit.com/r/gonewildstories/comments/s15r8b/dinner_with_a_friend_turned_into_a_night_with_a
I think the question was ‘Guess _who_ I did last night” 😋