Redheaded Waitress



What’s your gender? Man
How old are you? 31
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA

Redheaded Waitress

How long ago did this hookup happen? Friday night this last weekend

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? She was around 5’6″ tall. She had dark red hair with black in it. Her hair was pulled into pig tails. She had a decent rack and showed her cleavage proudly. She was a little bigger but by no means fat. Shd had a lot of eye liner on and bright green lipstick. She came off goth at first glance. She was my waitress at this bar i went to while out of town. Her name was josie. She was really attractive.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I joked around with her and flirted with her taking my order. One of the other waitresses brought me a beer. Josie stopped back by and we talked some more and she asked where I was from. I told her and explained I was only in town for the night before I had to travel again. She seemed intrigued by that but had to go serve other customers. When she brought out my food we talked a bit more and I then asked when she was off and maybe we could grab a drink. She seemed caught off guard. She said you want to get a drink with me? She then told me she wasn’t old enough to drink and followed that up with why with me. I told I thought she was cute I liked the look she had going on. She smiled and then walked away. I didn’t see her until she brought me the bill I thought I had messed it up at that point. She handed me the bill and said to just leave the money on the table and walked away. I checked my bill and it had a note on my copy. It said she wasn’t allowed to give out her number to customers but she was off at 9 if I still wanted to hang out. I wrote yes on the bill and left my number. I got a call shortly after 9 from Josie. She asked if I wanted to come to her place And hang out. She gave me the address and I drove over.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end?  I arrived and knocked on the door. Josie met me and invited me in. She had changed clothes and was now wearing a yellow and black plaid skirt with black fishnet leggings and a red t-shirt that was cut down the chest area which highlighted her chest. She had alcohol sitting on the counter and said she had someone buy it for her quite often. She poured me a Captain coke and we sat down to watch a movie. I was on my 2nd drink when she moved closer to me. She asked if I brought protection. I had not and explained that to her. She smiled and said she had condoms if we needed them. She sat on top of my lap and we started to make out. I grabbed her nice tits and she was not wearing a bra. They were very nice. She laid down next to me on the couch and undid my pants. She pulled out my cock and wrapped her green lips around it. She looked up at me with her big eyes as she sucked my cock. She was pretty damn good at it too. She pulled off her top and let me look at those nice tits. They had the smallest nipples I had ever seen on a pair but they were round and big. She asked if I wanted to have sex. I said absolutely. She led me to her bedroom. She had whips on the walls, a couple vibrators on the stand next to the bed, and some handcuffs too. She opened the night stand and pulled out a glass bowl. She sparked it ans took a huge hit she offered it to me and I took a big hit too. I felt numb all over and asked what was in it. She said not to worry that it was the best kind of weed to smoke before sex. She pulled out a condom from the stand as well. She took my cock back in her mouth and sucked it. Holy damn was she right it felt so much better. She then handed me the condom. She crawled up on the bed and pulled up her skirt. She had no panties on. She grabbed one of her vibrators and started rubbing it on her clit. I was amazed at this girl. I has not opened the condom yet I was fixated on watching her. She told me to get the cuffs and hook her to the bed. I put the condom down and grabbed the hand cuffs and pulled her arms up to the bed post and locked them in place. Josie locked her legs around me and pulled me close. My cock ended up right at her pussy. I could feel the tip pentrating and thought about the condom. I ended up pushing in raw. It felt amazing. She was super tight and wet. We made out as I fucked her hard and deep. Josie ended up having an orgasm not very soon after we started. She released herself from the cuffs as they weren’t real and then pushed me over. She looked at my cock and saw I didn’t have a condom on. She didn’t seem mad. She got down and started to suck my cock again. She rolled my balls in her hand very softly as she blew me. I was getting close and I’m sure she could tell from my actions. I started to cum and she kept on sucking. It was probably the best orgasm I’ve had from oral due to her skills and whatever we smoked.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? She had me spend the night. We laid and cuddled for just over and hour. We both smoked more from that bowl and she sucked me hard. This time she rode me. We didn’t use a condom this time either. She rode me for almost a half hour before she came. Her pussy made me ready to cum and I filled her up with my cum. She stuck her finger in her pussy and licked it. She told me she was on the ring and not to worry.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol, Marijuana, hashish,

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol, Marijuana, hashish,

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? No one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

You have a hookup story to share? Submit it here!