As I left off I was saying how Shawn invited me to dinner that night. I went home and we texted back and forth on the plans for the evening. Shawn was't ready to risk being seen together around town so we made plans to meet just outside of town and drive into the big city. I got ready for the night and had Kaylin help me pick out something nice to wear. Shawn had said the place was semi fancy but more casual dress. Kaylin helped me pick out this long maxi dress that was blue and green with a swirl design on it. Since I figured we would pick up where we left off from, underneath I put on a red lace thong which had little heart cut outs on the waistband, and a matching red lace bralette. I picked out a pair of scrappy wedges and finished getting ready putting on my makeup. I came out of my room and went over to Kaylins. "What do you think?" I asked as I twirled around showing her my complete outfit. She stared up at me and said "You gave me a boner" jokingly. We laughed and I gathered my things and made my way to my car. I drove my car about minutes outside of town to a shopping plaza we planned on meeting at. I arrived first and my heart was beating fast anticipating him showing up. I waited a few minutes and the next thing I know this beautiful black Audi pulls up next to me with tinted windows and shiny tires. The window rolls down and Shawn pokes his head out. He got out of the car as i got out of mine and ran over and greater me with a kiss on the cheek. "Ready to go into the city?" he asked. "In a car like that? I already feel like a celebrity" i told him. He laughed and brought me to his car and we pulled out of the parking lot. We made small talk on the car ride into the city about minutes away. We got to the restaurant which was beautiful and had a lovely dinner chatting more learning about eachother and really hitting it off. He told me about his ex wife and how they mutually split up and I shared some stories about my own life. We to along really well but I could tell we both felt the sexual tension in the air from earlier in the day. We left the restaurant and he asked if I wanted to go back to his house to talk more. We both knew what that meant and go in his car to drive back to his house. The ride back was mostly quiet as he played some music and occasionally commented on house nice I looked. We finally got to his house and it was absolutely gorgeous. It was a large story house with a huge backyard that had a pool, a large garden, and a nice patio with a fire pit. It reminded me of my house back home and he certainly was doing well for himself. We walked inside and he offered me a drink as he went to the kitchen. I walked around the front hall looking at pictures on the wall of him in his younger days with some friends as well as his family. Shawn brought out our drinks and we headed into his living room and sat on the couch. We sipped our drinks as we talked more before he placed his hand on my thigh. Thats all I needed. I set my drink down and crawled over and straddled him. He immediately pushed his lips up to mine as we started making out slowly. His hands ran all over my back slowly as he lowered them and squeezed my ass gently through the fabric of my dress. We continued to kiss as I slowly started grinding ontop of him through his pants as I unbuttoned his shirt. We paused briefly to remove his shirt as I stood up and undid my dress letting it drop to the floor. I stood there for a second as he looked up at me from the couch and said "You look so fucking sexy right now". I grinned as I knelt infront of him as he sat on the couch. I needed his cock in my mouth badly and I was going to have it. I tugged at his belt as he undid his zipper. I looked up at him and bit my lip as I pulled down on his pants and lowered them to his knees. He now sat there in a pair of grey boxer briefs that clung to his strong thighs and growing cock. I ran my hand over the material of his briefs as he laid back into the couch. I ran my hand up and down his cock slowly as it pulsed and twitched. I kissed it through the material and gave it a playful and light bite as I looked up at his lust filled eyes. I knew he couldnt take the teasing any longer so I hooked my fingers into his waistband and lowered his briefs to the floor. His cock sprung up rested against his thigh. I positioned my head over the tip of his cock as I grabbed the base of it with my hand. I still couldnt believe that I couldnt fully wrap my hand around the whole thing. I spit on the tip and rubbed it in with my hand. He twitched in his seat as I played with the head with my fingers. I lowered my face down and stuck out my tongue as I flicked the tip of his cock as I stroke slowly up and down. He bucked his hips forward slightly as lowered my mouth more taking more of his member. I swirled my tongue around as I continued to pump slowly with my hands. I increased my speed before pulling off and licking from the tip down to his balls. I stroked him some more as I licked his balls. After a few minutes I heard him pant through his heavy breathing "Keep doing..just..that, I'm going to...cum". I kept licking his balls and stroking his cock as I felt him tense up. I lifted my head back up to the tip as I swirled my tongue around his tip and pumped at his cock furiously with my hands. He bucked up his hips one more time before shooting his sticky cum into my mouth. The first rope hit the back of my throat causing me to choke a little but i recovered and finished milking him. He looked down at me with heavy eyes and grinned. I smiled back up at him and put his dick back in my mouth to clean off the remaining cum. I finished up and he stood up and picked me up to my feet. He pushed me back onto his couch as he undid my bra. He lowered himself down and sucked on my nipples as the became hard. He slowly kissed down my stomach to the waistline of my thong. He took it in his teeth as he looked up at me and pulled them down my legs exposing my wet shaved pussy. He kissed back up my legs before he buried his face into my crotch. He tongue felt like magic as it danced across my clit causing me to moan and twitch into his couch. He inserted a finger while he kept licking my clit. He increased his speed and not long after my legs were squeezing his head as ate my pussy to orgasm. He softly slowed down allowing me to recover before standing up. I laid there looking up at him as his cock was now hard again. He lifted me to my feet and led me to the bedroom. I was behind him staring at his cute little toned butt walk infront of me to the bedroom. He laid me down in his giant bed as he walked over to his nightstand. He pulled out a box of condoms and rolled one onto his thick cock. I tried telling him I was on the pill but he said that he had other plans for the condom. He then took out a bottle of lube and lubed up his cock before joining me in bed. He flipped me over onto my stomach and spread my butt cheeks. Now I understood what he had planned. "Shawn, be careful I haven't done this a lot". He lowered his face down and licked my ass for a little before inserting a finger. It felt so tight but I adjusted and it started to feel good. Not long after he removed his finger and slowly replaced it with the tip of his cock. I pushed in slowly as I moaned out loud. To be honest it hurt but I knew he wanted this. He pushed in slow allowing me to adapt to his thick dick inside of my ass. After awhile I started to feel numb but it felt somewhat good. He thrusted in and out slowly as I moaned into the pillow infront of me in pain and pleasure. He took it slowly as he reached around and played with my nipples. After a few minutes I felt him tense up as he came. He pulled out slow and collapsed onto the bed next to me. "Sorry I don't know what came over me but your tight little ass just looked so sexy I needed to fuck it" he said. I kissed him on the cheek and went to the bathroom to clean up. We laid back in bed before drifting off to sleep. I woke up sore the next day alone, in his bed with him nowhere to be found. I hopped in the shower and put on my dress from the night before since I didn't have any other clothes and went into the living room. I could hear talking from the kitchen but didn't know who it was. I walked into the hall and saw some woman with her back to me and Shawn with a surprised look as he saw me. I figured it wasn't good so I quickly if behind a wall and snuck back to the room where I questioned myself on who that woman was and why Shawn was surprised. Obviously he didn't want her to know I was there. But who the fuck was she. I decided to go back out and face my fears. "Hey Shawn I gotta get going" I said announcing that I was there. She turned around shocked and said "Oh I'm sorry, I didn't realize someone was hear. I should get going too. Im Mallory, a friend of Shawns." She introduced her self. I don't know who she was but Mallory was stunning. She was about ', with long brown hair. She was latina and had sun kissed tan skin with B cup breasts and a round toned ass. She looked like she focused on her butt in workouts which she had clearly come from since she was dressed in a tank top and yoga pants with her hair braided down her back just stopping at the top of her butt. She mad her way out and said it was nice to meet me. As soon as the door closed I asked who she was and Shawn tried to explain that when he got divorced he started to gain weight so he hired a trainer and Mallory was that trainer. He admitted that they had slept together before and that they had grown intimate but are now just friends. It kind of boggled my mind finding this out but she seemed nice enough and their conversation was friendly. Shawn apologized saying he didn't know she was stopping by and then kissed me once more. We kissed for little before I said that I needed to leave. On the car ride back to my car he apologized about the previous night. "Its okay Shawn I just need some prepping before we do that again" I said. "I'll make it up to you" he said before dropping me off to my car. I kissed him goodbye and thanked him for the night out. He asked if we could do it again and I agreed. The next week we chatted more during work but kept it friendly so that other people wouldn't know we were a thing. That Wednesday he said he had a gift for me and told me to come into his office before I left for the day. Of course I stopped by and was pretty surprised. TheCosmicDust
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