Skyler
I first met Skyler at the anytime fitness down the road from my place. She actually approached me and introduced herself. She said she was co owner of a health food store down the road from the gym and asked if I wanted to check it out sometime I should stop in. When I met her she had on super baggy sweats and an oversized sweater. She was younger looking and it seems to be the way the younger generation now dresses in the gym. We stood around and talked for a while and she asked for my number first. I gave it to her and she texted me a link with the address to the store and we went our separate ways from there. I did think about stopping over but didn't really make the time. I ran into Skyler in the gym again the next week and she came up to me and asked if I had stopped in yet to check it out. I told her I had not yet. She asked if I had time today she was actually going over there in about 20 minutes when she was done working out to cover a shift. I said okay since she would be there I would come check it out and gave her a slight smile. She said okay cool and walked away and didn't react to the smile. I finished up my workout and then went to the address she had sent me. I walked in and it was a pretty nice place. Skyler was behind the counter talking to another girl when I walked in. The other girl turned around and looked at me and then turned back to Skyler. I seen Skyler look over at me blushing a little it seemed. The other girl said she would talk to her later and left the store. Skyler said hi and she was glad I had stopped in to see her and the store. She showed me the menu and walked me through what items that they sold there. I noticed that Skyler had changed into a crop top type sweater and she had a very toned and solid midsection. It looked like she was wearing yoga pants but couldn't quite tell as she was about the same height as the counter. I decided on a protein shake and she said okay and walked over to the blender on the counter. That is when I got a clear look at her. She was wearing white leggings that hugged her small amazing ass very tightly. I did not see any outline or colors underneath the white so I figured she must not have panties on. I felt myself starring a bit too hard and could feel myself getting stiff so I looked away. I walked around a bit looking at the pictures on the wall. Skyler asked how much ice I would like and just said whatever the normal amount was for a shake that size. I then watched as she leaned over into the ice bin and scooped ice. I caught myself starring again but I could clearly see her lips as she bent over and it was so fucking sexy. I backed up a bit and let her finish up making the shake. She brought it over and told me it was free since it was my first time in. I thanked her and then she asked if I wanted to hang out a bit and keep her company and I could also let her know what I think of the shake. I took a seat at the counter and tried the shake, it was really good and I let her know. She asked me where I was from, where I worked, what I like to do in the area just standard things. She helped another girl who came in and then she came back over to me. She asked if I was married or had a gf. I told her I did have a gf and she said okay. I asked her the same and she said she didn't have bf or anything like that. She then asked me to guess how old I thought she was. I said early 20s and said just because she was running this business. She smiled and said she was about a week shy of being 19. I honestly thought she was like 16 by how she looked. She said her mom started the business and she helped her run it. We talked a bit more before I finished my shake. She asked what I planned to do with the rest of my day. I said I had a bunch of stuff to do today and tomorrow I wasn't sure yet. She said maybe she would see me in the shop or at the gym tomorrow and I got a small smile from her. I wasn't sure if she was giving off the vibe of wanting to hook up or not but figured I would test the waters. I said I was thinking maybe I would work out at the gym in my apartment complex. She said oh and kind of trailed off seeming to be sad about that. I asked what her plans were tomorrow and she said she was working at the shop around 2 but was free in the morning and wasn't sure what she was going to do. The way she said she was free made me feel she was looking to hook up. I said she was more than welcome to come over to the gym at my apartments if she wanted to. She smiled a little and said what time was I thinking. I said probably like 9ish or so. She said cool yeah that could be fun and told me to send her the address. I put in my address and said she could just text me tomorrow when she gets there as it's a locked entrance. She said okay that sounds good to her and we said goodbye. I honestly didn't really expect her to come over. I got up in the morning and had some breakfast and headed down to the apartment gym. It was shortly before 9 as I walked in. I started out with stretching and doing some light lifts. It was about 10 after 9 when I looked at my watch. I started to set up the bench when I got a text from Skyler and she said sorry she was late but she was outside if I could let her in. I went to the entrance and there she was. She had on a baggy sweater and black workout shorts that looked like booty shorts to me. I let her in and she followed me to the gym. She said she was surprised it was actually kind of big she was expecting it to be smaller. She asked what I was doing today and I said little bit of arms and lower body. She said she was doing legs as well. We talked the whole time we were in there together. I got plenty of chances to check out her nice ass and I think she may have caught me a time or two. About half way into our workout she took off her baggy sweater and she had on a sports bra. She had an amazing toned, tan body with a nice set of small tits on her. We finished up working out and she thanked me for inviting her and said it was nice change. I was walking with her towards the exit and she was walking rather slow. I asked if she wasn't busy did she want to come up and hang out for a bit. She said that sounded nice. We went up to my apartment and I made sure to mention my roommate was at work. We walked in and she asked to use the bathroom. I went and got us a couple waters out of the fridge and she came and joined me on the couch. She thanked me for the water and we sat and watched TV for a bit. I looked over at Skyler and she asked me why I had invited her over to my place. I said I thought maybe we could talk some more or whatever she wanted. She asked me if I had invited her over to hook up? I was going to think up some answer but she didn't give me the chance. She told me she was down for whatever and she would be discreet. She said she wasn't quite honest earlier about having a bf so she would want to keep things on the down low. I said I was cool with that and also added the amazing shape she was in how attractive she was. She blushed a little and said thank you. Her blushing reminded me of the previous day and I asked about when I had walked into the store. She said that was her friend Abby and she was actually telling her about me when I walked in. We had a little a little laugh about that. I scooted closer to Skyler and she looked at me very sexy like. I leaned over and gently pulled her towards me so we could kiss. She almost immediately shot her tounge into my mouth as we made out. We sat on the couch and made out for a couple minutes before I pulled her onto my lap and stood up. My boner was pushing hard against my shorts as I carried her to the bedroom with her legs wrapped tightly around my waist. I laid her down on the bed and we kept kissing as I pressed my hard cock up against her through her shorts. I kissed my way down her body and grabbed her little booty shorts and rolled them down her legs. She was not wearing any panties and have a nice shaved pussy. I kissed my way up her legs and licked the insides of her thighs and nibbled a little bit. I grabbed her legs and spread them apart and lifted them up. I got clear view up close of her pussy and could see her little butt hole too. I stuck my tounge against her asshole and made circles and licked it. She jumped a little and said that felt good and she had never had that done before. I worked on her asshole for a little bit before I licked my way up to her pussy. I swirled my finger in circles inside of her and sucked on her clit. She said holy shit that felt amazing and she had never been licked like that before. I kept working on her and eventually moved my finger up to her G-spot and put some pressure on it matching the strokes with my tounge movements. She could hardly sit still and said it felt so damn amazing. I kept my pace and she grabbed my hair and said don't stop. I felt her start to shake some and could feel her tighten up. I kept doing long pressured strokes on her G-spot as I licked her clit. She kept shaking and almost riding my face. She said holy shit she's so close and she feels like she wants to cum but felt a weird sensation. I asked if she had ever squirted before and she said no. I asked if she felt like she needed to pee and she said yes and also like she had to cum. She kept jumping a little as we talked. I told her she was going to squirt for the first time and to just relax and let it happen and not try to hold it back. She said she would try and I went back to working on her G-spot and licking her fast. She kept taking long deep breaths and holding them. She said she was so fucking close and the pressure was getting stronger. She kept shaking and said she was going to cum. If you have ever eaten out a girl that squirts you know that wet sound when they come right before they start to squirt, that't exactly the sound she made. I got excited with it being her first time doing that. She let out a very loud moan and said fuck just as she started to squirt. It ran down my beard as she kept cumming and I snuck a finger around to her asshole and stated to rub that as well. She fucking lost it and started to push my face into her hard and ride me and was moaning so loud. Once she was all done she was breathing super hard and just laid there. She said wow that was amazing I didn't know I could cum like that. She got up and took off her sports bra and told me to lay back on the bed. She pulled down my shorts and boxers and starred at my cock. She said I had a nice one and then lowered her mouth down onto it. She just slowly sucked up and down and gently massaged my balls. She didn't seem too experienced in what she was doing but it still felt good. She stopped and moved up me so she was sitting right above my cock. She rubbed me against her a couple times and then guided me inside of her. She was super fucking tight and so fucking wet. She leaned down to me and we kissed as she slowly rocked on top of me. She took her time riding me and it felt good but I wanted to go deep and kind of fast. I grabbed her leg and rolled over on top of her. I pressed in all the way deep and she just moaned and said I was damn deep. I brought her legs up and gripped her ass and started to pound her deep and hard. She said that felt so damn good and not to stop. I switched between fast and slow in this position for about 15 minutes before she came again but didn't squirt this time. She told me I could cum inside of her if I wanted as she was on the pill. I had been holding back enjoying myself to that point but hearing her say that I was ready. I started to pound deep again and told her I was going to cum inside of her. As I started to cum inside of her she told me she could feel it and it was so much and how much she loved feeling it. Once I was done I stayed inside of her until I softened and slid out. We kissed some more and then she headed off to the bathroom. I put on my boxers and she came out and got dressed. We went out to the couch for a bit more and watched some TV until about 1130. She told me she should probably get going so she could go home and shower and change for work. I said okay and I walked her to the door. She said she had a great time and we should do this again soon. She came in for hug and then she pulled back but came back in for a kiss. We kissed for about a minute and made sure to get a couple good squeezes in on her amazing ass. She slowly pulled away and looked down and seen I was rock hard again. I asked if she wanted to go in the bedroom quick again. She said she did want to do it again soon so yes. We walked in and she said we would have to hurry. I pulled down her shorts and bent her over the bed. I felt her pussy and she was still wet so I lined up and pressed in from behind her. She had the sexiest little ass I had ever seen and I gripped her sides and started to fuck her pussy from behind. She grabbed the sheets of the bed and told me to slam her. Before I did I asked if she liked anal at all. She said she honestly had never tried it before and maybe we could try it another time. She told me to slam her hard and cum inside of her again. I grabbed her sides and slammed her deep and as hard as I could she was saying lots of dirty stuff to me which I liked. I said I was getting close only after a couple minutes. She said she wanted me to cum inside of her again and to give it to her. I pushed in deep and came hard again inside of her. I slowly pulled out of her and pulled up her shorts. She said that was super hot and wanted more but she needed to leave. We went to the door again and kissed some more. She then headed out. We texted on and off for a while throughout the day. She added me on snap and sent me a couple pics of her working and then also sent me a picture of her ass with her leggings pulled down. She asked when we could meet up again and I had to work a couple long shifts in a row and wasn't able to meet for a couple days. I had plans with my gf on the weekend and couldn't meet either. She sent me couple nudes over the weekend and said she really wanted me. I told her I was done at 5 on Monday if she was free. She said she had to close down the shop and would be done by 7. She asked if she could come over after and I said yes. She showed up a little after 7 and we went straight to the bedroom. She asked if I could make her squirt again. I repeated what I had done with her the last time and she came super hard again and it ran all down my chin. She said that felt so damn good to cum like that. She laid there for a bit and then asked if I wanted to maybe try anal with her. I said I was down if she was. She said she had tried with one of her dildos at home and actually it felt good. I grabbed a bottle of lube and started off with my index finger first. She was laying on her back with us kissing to ease her a bit and I worked my index finger in and out her asshole. She said it felt good and was just a new feeling for her. I moved to two finger and went slow. She started to rub her pussy as I fingered her asshole. She told me she wanted me to put my dick in her ass. I lubed up my dick and her asshole. She kept rubbing herself as I pushed against her tight hole. She told me to go slow and I pushed ever so slightly and the head popped inside of her and she let out a startled gasp but then a slight moan. She said it kind of hurt but also felt good. I kept working myself inside of her as she rubbed herself. I was about halfway in when she said she was going to cum and told me to push in. I pushed inside of her and could feel her asshole clenching on me as she came. I started doing long deep strokes in and out of her and it felt super good. She asked if maybe she could be on top if that was possible. I laid down and she straddled me. She found her asshole and after a couple tries she got me back inside. She seemed to be doing much better now and started to ride me quite fast. I got close relatively quick and she sank down deep as I shot my cum inside of her ass. We both went and got cleaned up and she headed out. She stopped over once more that week, she had me make her squirt again and we did anal sex again. The following week she came over late on a Tuesday night. I got her to squirt again like she liked and then we fucked for about 2 hours. She came 3 more times and I came inside of her pussy . She asked if maybe it would be okay if she stayed over as it was quite late and it said sure. We ended up cuddled up naked under the covers. I woke up at around 2 and used the bathroom. When I got back to the bed, I just looked at her naked sexy body. I woke her up and we had sex for another hour with both of us coming once more. We slept in until about 9am the next morning. She asked if she could shower at my place quick and I said sure. She showered quick and then came back in my room in a towel. I was rock hard watching her taking the towel off to get dressed. She said really again? I asked if she wanted to have sex again and she said no she couldn't but did offer me a blow job. She did the same as before very light sucking not a lot of movement. I asked if I could give her some pointers and walked her through what I licked such as light stroking, using alot of spit, deep throating and the pressure to suck at. She took my advice well and I filled her mouth up with my cum shortly after. She said she had never made a guy cum that was before and was excited. We ended up hooking for about a month more before she told me her and her bf were getting more serious. We did end up hooking up in her car in the gym parking lot about a month later but she did not come back over to my place after that.
