It’s difficult for me to keep casual sex casual. If I’m having a sexual relationship with somebody it’s because I really like her. Lindsay was somebody with whom the relationship started out purely casual. Over a couple years of on again off again the casual veil fell away for both of us but especially me. This is the story of how we met up until our first hookup. We don’t have piv sex in this story, but I’ll post sequels of our pseudo relationship.
Lindsay and I met when my buddy took me to a bar to meet up with a couple of his friends. Lindsay was with them teasing one of the guys with sexy slutty dances every now and then. I was turned on by the way she was moving. Throughout the night I got a chance to talk to Lindsay a bit and got her number. Nothing happened between us that night and we went our own ways.
I called her a couple days later and met up with her and her girlfriend at another bar in town. The three of us hung out and after a while her girlfriend took off. On her way out, she and Lindsay exchanged a knowing look that communicated I was all right. Earning the friend’s trust never fails to boost my ego. Lindsay was wearing jeans and a low-cut white sleeveless blouse. She had a blonde bob, brown eyes and was about 5’-7” tall. She was cute in an endearing sort of way. She was 21 and I was 24. I had never been with someone that much younger than me and she teased me about being old. She teased me about quite a bit in her flirtatious way. As we got to know each other I could tell she was super intelligent and knew how to press all my right buttons. She seemed a little bit annoying and clingy but in a charming way. Most importantly, she was there and I sure as shit didn’t have any other options at the time. As for me, I’m 5’-10”, 170 lbs. I’m not muscle bound but I take care of myself and I’m in good shape. I have dark eyes and I had dark brown hair then.
As we were hanging out at the bar we got closer and closer until we were sitting with our arms and legs touching. She gave me a devilish grin when she caught me looking at her cleavage. We were both succumbing to the alcohol and my previous concerns about Lindsay being annoying seemed like ancient history. When it got noisy she talked into my ear letting her lips brush against my skin. I could feel my cock getting stiff and wondered if she knew. When we turned to face each other, she would brush her breasts against my arms. Our lips were as close as they could get without touching and eventually I leaned in just a little further for that first kiss. She put her hand on my neck and pressed her breasts against me as our tongues intertwined. I’m not the biggest fan of public make out sessions, so the kiss didn’t last too long but long enough to decide it was time close the tab and walk to my place together.
On our walk we agreed that we wouldn’t have sex because she was on her period. When we got through the door, I pressed her against a wall and we were full on making out with my hard cock grinding against her through our jeans. We had our hands all over each other. I didn’t take off her top just yet, but I lifted our shirts because I wanted to feel her warm stomach against mine. She was squealing not too loud but in a way I have never experienced from making out like that. I was totally turned on and in the moment. I almost came in my pants, but she told me she needed a bathroom break just in time. After the pee break, we cooled off a bit on the couch with some water and enjoyed light kissing and teasing. I traced the outline of her blouse across her breasts along the top of her bra and then ran my fingers along the top of her jeans and just underneath, so I could feel just under the waistband of her panties. She felt my inner thigh and gently brushed her hand against my hard cock outside my jeans.
I stood up, took her hand, and led her to my bedroom. We were standing up facing each other. I lifted her shirt and undid her bra. Her B cups were gorgeous. She had pierced nipples which was a first for me. I fondled her breast with one hand while I caressed her back and side body with my other hand. I pulled her close, kissed her lips and then kissed along her jaw bone until I was kissing her ear. I kissed along her neck until I got to her collarbone and lingered there. She moaned softly. I sat on my bed and pulled her on top of me so she was straddling my lap. I kissed her nipples and continued to enjoy her soft moans and squeals. She grinded on my rock-hard cock. She reached under my shirt, pulled it off, traced her hands down my sides and got off me and on her knees, all in one graceful motion. She undid my belt and unbuttoned my jeans. I pressed myself up, and she slipped off my jeans and underwear. She placed her hands on my cock and squeezed it hard. She licked a dab of precum off my cock. She squeezed out more precum which served as lubricant for her hands working up and down my shaft. She kissed the tip of my cock and spent some time licking it and taking just the tip in her mouth. Gradually she worked most of my cock in her mouth. It felt amazing how she worked my cock with her hands and mouth. The air was filled with my moans, the beautiful sucking sounds, and her moans. I couldn’t take it much longer and told her I was cumming. She sped up her motion, squeezed harder and took my load in her mouth. It was so intense I felt the orgasm all the way in the tips of my toes.
She got up to spit and rinse out her mouth. When she returned from the bathroom she playfully pushed me back, straddled me, and we made out some more. It took me by surprise and it was the first time I made out with a girl right after a blow job. I rolled with it because I loved her energy. After kissing and playing on the bed for a bit longer we drifted off.
The next morning, we shared a toothbrush which was another first for me. I made her breakfast and we took a walk, continuing to enjoy each other’s company. We made plans to see each other in a couple days, and I took her home.
Source: reddit.com/r/gonewildstories/comments/7czzgr/mf_my_first_encounter_with_lindsay