Winter - A Day of First

CW: Knife play, blowjobs, anal

In a strange twist one October afternoon I get a message from Winter asking me if I know if there are any kink clubs in the area. She was in town on break visiting a friend and she got it into her mind that she wanted to explore. At that point I was never getting messages from subs directly and I was not about to let this chance pass me by. She was a young college girl who was a little cutie so I offered to show her around town. I am not fully sure how we never got to that part, but the time we did spend together was golden.

We chat a bit and I get her number. We start texting and she agrees to let me pick her up for some time to hang out. At this point I am working the late shift so we had to meet earlier in the day. So I get dressed and roll up north to go get her. Now, as a lot of my stories go, she had no business getting into a strange man's car in a town that she was not familiar with, but she did and thankfully it was just me and she was safe. She came out in a cute little date outfit and we set off for my place. Again, no idea how that came to past, but I was down.

We get to my place and we sit to watch some TV show or movie or whatever. Basically I just wanted to hang out and get her clothes off. So the entire time I am making my moves. Asking her about kinks, increasing touches, getting consent, and making sure she was feeling comfortable. It was clear she was new to all this, so I wanted to make sure that she signed off on each step we took.

I started taking her clothes off and playing with her cute little boobs. Nice little B-cups with pink nipples and plenty of perk. She seemed to respond well to me pinching and pulling on them and as I rubbed them she got more turned on. Next were her pants and panties. As I slid them off I noticed she had a nice little red bush. Clearly never bothered to shave it once. Not that I was complaining. I don't mind them at all, but I took a chance to do something I enjoyed doing to subs to put them in the right headspace. I grabbed my trimmers and decided she didn't need it anymore.

I laid her back on the couch and put her legs in the air. She was a bit nervous so I told her to cover her face with a pillow and I will do the work. I was very careful as I trimmed all her hair and left her nice and smooth. Took my phone out and snapped a few after shots. Her labia were super pink and she was clearly wet from all the attention I was paying her. Afterwards she sat up and took a look at her new smooth pussy. I let her put her panties back on as I had another bright idea. Why not go right into knife play... whew.

She was curious about it so I grabbed my knife and walked her through what I wanted to do. She gave the go ahead and I had her hold them up as I wrote my name into her right titty. It was slightly painful but I went slow and made sure she was enjoying it still. She was so I pushed on. After I finished with the right I moved on to the left and made a little heart on it.

I was ready to be inside her one way or another. She was ready to go and so was I. I lifted her up and placed her on her knees in front of the couch. I made her take my pants off and let my dick spring out at her as my pants fell to the floor. She grabbed it and slowly started stroking it, but was hesitant to put it in her mouth. Nerves were finally sitting in. I didn't rush her and coached her through it. She confessed to me that she has only given head one other time before me and was still a bit nervous about her skill. I stroked the back of her head and told her to close her eyes. I forget what I said to her exactly, but it eased her and mid-sentence she opened her mouth and started blowing me.

It felt good for a rookie. I knew almost right away that it was not going to get me off, but training her to get better is part of the excitement. I watched her and played with her hair as she listened to my simple corrections. I made sure she didn't neglect the balls and to use her saliva to keep the shaft wet. Told her to come off the head from time to time to pay attention to other parts. To use both her hands and her mouth in sync to increase pleasure. She got better before my eyes.

I stopped her and led her to the bedroom where I took off the rest of my clothes. I climbed on the bed and spread my legs and she got on her stomach in front of me to keep giving me head. I took this chance to record her giving head for the first time. Looking back at the video she barely got the head into her mouth and her stroke was lacking, but she did keep my balls warm in her other hand which was nice. Her messy hair was all over and her tight bottom stuck in the air behind her feet dangling over the end of the bed.

I let her continue for a bit and then we got up. I moved her to the edge of the bed and laid her on her back. Her titties flopped to either side of her and her ponytail laid to the side of her head. Her chest was still red from playing earlier and her pussy was visibly wet and ready. I placed my dick over her lips and took a picture before sliding a condom on. Her eyes closed and rolled back as I slid inside her. After checking to make sure she felt okay I started slowly fucking her as she gabbed onto the bedsheets under her. She was incredibly tight and it took a fair amount of willpower to not cum so fast but I held on. Even with her being so wet it felt incredible.

Our time was coming a bit short but there was still one more hole I had to get into since I had no idea when I would see her next. She was super hesitant as she was an anal virgin, but she came this far with me and I had been treating her well. I think she trusted me enough at this point to keep going with me so I got my lube. Now reader, do not judge me for this, but we haven't gone over safe words at this point and since we would be doing something super new I decided to make sure she knew the stoplight method. Thankfully I did because as I pushed into her butt she called red and I slowly backed out. I let her relax and thought maybe doggy would be easier for her to manage. She flipped over and I added a lot more lube. As I went inside her she tensed but I was able to bottom out and she started to get used to it.

I fucked her like this for a long time. My camera was in one hand and her hair was in my other. I made her tell me where my cock was and how it felt. She could barely get the words out but the look on her face told me all I needed to know. She was having a great time. I made her tell me how many cocks had been inside here as well to which she told me none and that it belonged to her. Surprisingly enough I pulled out of her without cumming as I had to get her back.

We took a picture together and she got dressed. As I drove her home we made small talk and made plans to meet again that never happened. She went back to school and when I tried to reach out some more she was cold and distant. I asked her if she had a good time and she said she did, but between college and other stuff I was very low on her priority list. I remember our time together fondly and wish there was more, but life happens.