Cassie's First Time

My wife’s sister Cassie was 19 and finishing her first year of college. Due to having a college budget, for her spring break that year she had decided to spend half of it back home with her parents, and the other half visiting my wife and me. Saturday was her last day with us; she was going to have to make the drive back later that afternoon. My wife had a big project she was working on and had to spend the day at work. That left Cassie and I alone for the day.

I was sitting in the Family room watching tv when she walked downstairs and sat on the sofa across from me. We sat and talked during commercials when she brought up her boyfriend. They had been dating for 2months and she said things were going well. Over the years I had known her, she hadn’t dated very many guys. She was quite attractive, 5’6, slender, long legs, long naturally curly light brown hair, and green eyes. However, she was pretty quiet and shy and very focused on school. She said she didn’t think he was the one and they were just having fun. I smiled and said I’m sure they were having fun. She let me know not too much fun, yet. She then let me know that she actually had never gone all the way with any guy. She said she had thought about it, but wanted her first time to be better than what she had heard from her friends. She really wanted it to be with someone she knew would be gentle with her and had experience. Then she turned red and stared at the floor.

I was shocked that she had told me this. We had always gotten along, but were never that close. I was looking over at her the way her tank top was stretching to cover her amazing 34C breasts and at how great those tight jeans looked. She really had me stirring and wondering if she meant what I thought she meant. She looked up from the floor, her face bright red, she saw I was staring at her and I pointed at myself to see if I was thinking correctly. She smiled and shrugged her shoulders. By this point the blood was draining from my head along with all reasonable thought. I got up and went and sat next to her on the sofa.

Cassie smiled as I sat down and leaned into me, resting her head against my chest. I wrapped my arm around her and looked down brushed my fingers over her cheek. She looked up and I leaned down and my lips touched hers for our first kiss. The sparks flew right away; her lips were so soft as she slowly parted them. She sat up straight and I leaned over to continue our kiss. My lips parting and my tongue gently running over hers, while a soft moan escaped me. One of my hands gently ran over her tank top, getting my first feel of her breasts. Her bra was holding them in place and I could feel it give a little as I started to softly squeeze. She leaned forward slightly, pushing her breasts into my hand, I could feel her heart beating as I played gently with them. At this point I was feeling as nervous as she was, hoping it would be the experience she had waited for.

I broke our kiss and slid down to the floor so I was kneeling between her legs. My hands ran up the side of her body, pushing her tank top up slowly. I leaned in and kissed the soft skin of her now exposed little tummy. I slid her tank top higher, until it was up over her breasts. I kissed up her body, each kiss a soft little kiss, my lips barely touching her skin. As I slid her tank top off of her and let it drop to the floor my hands came down over her breasts, tracing gently between them. I looked up at her and she had a very sexy little smile, appearing to enjoy this as much as I was. I looked back down, staring directly at her bra, it was very sexy, white with just a little lace at the top of each cup. I leaned back in and kissed what I could of each breast.

I wrapped my arms around her, my fingers feeling for the clasp on her bra as I looked up and told her that “I think it is time for this to go.” She nodded slowly, the smile still on her face. I unhooked her bra and slowly slid the straps down her arms. I slid up her body and kissed her soft lips as her bra fell from her arms. As our kiss was about to break I felt her tense up again. My lips still almost touching hers as I whispered for her to relax. I then looked down and saw her bare breasts for the first time. I struggled to whisper the word “Wow.” I then looked back down and saw how perky her breasts were, her nipples small for her breasts and how hard they were sticking out. “Oh Cassie, you look so amazing” I whispered, as my hands cupped each of her breasts.

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I took one of those nipples between my lips and began to suck on it. As I did, I could hear her begin to moan. I looked up and saw her eyes were closed and I began to suck harder on her nipple. I took my finger and slowly circled her other nipple, totally lost in her body. At this point I wanted to feel every inch of her and touch her all over.

I leaned back and slipped my shirt off, adding it to the pile of clothes that was growing quickly. I leaned back in, my body against hers, my lips kissing her nipple, then kissing between her breasts to her other nipple. I planted kisses all over her body as I started to kiss down lower. My hands ran over her jeans, finding the button. As I opened the button, I kissed the top of her panties which at this point I could only tell they were white. My fingers slowly slid the zipper down and I opened them up. I told her to rise up, that these needed to come off. She pushed her body up and I slid her jeans down, leaving her white bikini panties on. She kicked her jeans off her feet and then my hands slid up her legs, spreading them slowly as they went up.

I leaned in and kissed over her panties, burying my face between her legs. I was starting to lose all control, wanting her so bad. As my lips touched her panties I could feel how damp they were getting. I smiled as I brought my hand up and rubbed her panties as I kissed them. She really seemed to like this and her moans started getting louder as she pushed her hips pressing harder against my face.

Feeling her getting more excited, I reached up and slid her panties down, exposing her sweet little pussy. Her body was now naked in front of me. I rubbed my hand over her trimmed pussy, she was so hot and sexy I just had to taste her. I leaned in and licked, my tongue gently searching out her clit. As soon as I licked over her clit, she jumped and cried out, “Whoa!” I pulled my head back and said that I was sorry and asked if that hurt. She let me know that no it didn’t hurt and felt damn good and that I had better not stop. My answer to that was a big smile and I leaned back in and buried my face into her. As I licked, my tongue flickering over her clit, my fingers glided up her body back to those amazing tits, my fingers in rhythm with my tongue flickered over her nipples.

I licked harder and faster and her moans became louder and louder when she cried out not to stop. Within seconds after that she let out a cry that let me know she was feeling damn good. Her hips pushed her pussy up into my face and I tried to bury my tongue inside her as she came. I could feel her body tense right before, then just totally relax as she let go. As her moaning quieted and her orgasm faded, I looked up and saw the biggest smile I’ve ever seen her with. She was looking down at me and said “Wow, have never totally lost it like that, that felt sooooo good.”

I responded by kissing her tummy. I then looked up and told her that it is supposed to feel good. I then slid up her body and she leaned forward and gave me a kiss even though my chin was soaked with her juices. I brushed my fingers through her hair and asked her if that was as far as she wanted to go or if she wanted to keep going. As hard as I was in my jeans I was hoping she would say she wanted to keep going. Her answer was that she wanted to experience going all the way. “Oh good” I said louder than I had intended.

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I then leaned back and grabbed a blanket and spread it out on the floor, and had her come down and lay on her back. As she layed back, I knelt next to her and slipped my jeans and boxers off, finally freeing my hard cock. She looked down at it and I could see the nervousness in her eyes as she thought about it being inside her. I let her know I’d go gentle and as it started to hurt I’d stop. I then asked if she was sure she wanted to go through with this. She nodded slowly and I layed on top of her, holding myself up, as I looked into her eyes. I took my cock in my hand and slowly rubbed her pussy with it. Every time it would brush over her clit she would jump, it was still sensitive from me going down on her. I kissed her lips at the same time I started to push. Slowly the head disappeared inside her and I stopped. I asked her how that felt and she kissed me and said it was fine so far and that she really wanted this and wanted me all the way inside her.

I smiled and said ok, and started pushing in further. She was really tight, but as wet as she was I was able to go deeper and deeper. I felt her squirm a few times as it hurt but she wanted me to keep going. I stopped when I was all the way inside and kissed her lips. She was smiling knowing she had now gone all the way. I told her that it felt so good for me and she said it kind of did for her too.

I pushed a couple times in and out of her and then told her that I wanted her on top of me so she could control how far in I went. I pulled out of her and rolled onto my back. She straddled me and took my cock in her hand and pushed it up so it was pressing against her, I pushed up and she started to slide down. Not going as deep as I was, she rose up and we moved slowly together.

She rode me very slowly for about 5min. Because she was so tight and it felt so good, I had to tell her a couple times to stop so I wouldn’t cum. After about 5min she said it was starting to hurt more than it felt good. I let her know that was ok and we could stop. She smiled and said she wouldn’t do that to me and that she wanted to feel everything and that she had been taking the pill everyday for over a year so everything was ok. I looked up at her and smiled. I pushed in deep and pumped a few more times as I reached up and played with her nipples. It didn’t take long and I was cumming inside her. It felt so amazing, knowing I was the first. She smiled as she felt wave after wave shoot out of me.

As I layed back, drained, she rose up off of me and said that was a great first time. We ended up laying together and talked for most of the afternoon about what felt good, and what didn’t and both agreed this had to stay between us. Finally she said she had to be going back to school. We kissed one last time before she went and knew we would always share something special between us.

Updated: December 20, 2016 — 7:00 PM

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