This is the second story I have written. Thinking about doing more parts.
It was the start of a long weekend for me, I had to drive across country to see my wives Mum and Dad for a family party. Trouble is it was a 12 hour drive and I had to do it on my own, or so I thought. See, my wife and her sister wanted to get there early so she could see all of her family the day before and catch up with people. But I had to work during the day so I would be going on my own. That’s when my wife asked me to take her little sister Milly too. Milly was 15 and too be honest a bit of a recluse. She spent most of her time playing on her computer and looking at manga. She was a sweet girl, but very quiet and very hard to get much conversation out of. She was ok looking, wore glasses all the time and had dark brown hair, medium length. For her age she had big-ish boobs too. I would guess at a 36D and a medium build. All in all not a bad body. I did feel wrong for noticing it as I have seen her grow up. But I suppose its all just in my head.
Time came to leave, I was planning on doing the journey in one long hit, as long as kept the coffee coming I would be fine. Milly would sleep most of the way too so no problems there. I picked her up after school at about 5ish, and we set off. Milly had gotten changed from her uniform into something more comfortable. Jogging bottoms and a tshirt that was just a bit too small for her. She was quiet when she got in the car, more so than usual too. She would talk to me about things normally for a little bit before going silent, but this time all she said was “Hi”. I tried asking her a few questions but all she said was that she was tired and then closed her eyes.
An hour passed and she woke up again, still not saying a word, this time I decided I was going to push it because I was starting to get bored and needed someone to keep me entertained on the journey. So I again said “Are you alright?” All she could reply was “Meh”. So I asked what that was supposed to mean, and all she said was “you wouldn’t get it, you don’t go to school” I kept asking questions and coming down to her level for about 20 mins and it turned out that all the other girls in school were teasing her for being a bit of a geek and never having a boyfriend. I told her that this didn’t matter and that in time it would all just happen on its own, but she didn’t seem to buy it. It was at this point she went quiet again, so after another 2 hours of driving I decided to stop off for some food and a break. She got out and followed me into the service station.
Our food came, and while we were eating I tried to get her to open up more. I asked her if she had ever kissed a boy, she hadn’t. She told me that she wants too and that its no big deal. She seemed more at ease with me now, and was being a bit more honest. I told her she was a pretty girl and that any guy would be lucky to have her. She blushed at that and went red in the cheeks. We finished our food and paid up and headed back to the car. It was at this point she grabbed my hand and held it as we walked back to the car. Usually I would have not done this, but I felt for the poor girl after a horrible day, so I let it go.
We got back in the car and headed off, driving for another 3 hours and it was midnight. My eyes were starting to flag at this point, and the coffee I was drinking didn’t seem to be having any effect. I decided the best thing to do was to check into a motel and get up early and finish the final leg of the journey. So about 3 miles down the road we came across a decent looking motel. Fairly modern and welcoming. I went up the desk and asked for a twin room so we could both get some kip. They only had a room with 2 double beds, so I booked it and told Milly to go up to the room while I got the bags.
I got up there and dumped the bags on the floor and decided to go for a shower. After 10mins I was ready to get into bed and go to sleep, but it was at this point Milly decided to tell me she didn’t have any Pajamas. Now, I couldn’t let the poor girl sleep in her day clothes, so it was up to me to give her a t-shirt and shorts I had packed. She went into the bathroom and changed and get washed up. She came out and I first noticed that she didn’t have a bra on, and that she was “cold”. I think she caught me staring, as she coughed and got my attention. “Thanks for the Pajamas Alan. “No probs”.
She sat on the edge of the bed and started to thank me for making her feel better today, she said I made her feel like a woman with what I said. Which surprised me as she had never been this straightforward before. She then asked if she could sleep in the same bed as me, I hesitated and thought no harm could come of it, so I let her get in under the covers. Usually I sleep nude, but tonight I thought ahead and put on some boxer briefs and a vest. We turned the lights off and I flipped over and faced away from her and wished her goodnight.
I don’t know how long I was asleep before I woke, but it cant have been much more than 30 mins. I woke to find Milly still awake, staring straight at the ceiling. “What’s up Milly?” I asked. She couldn’t sleep as her mind was thinking too much apparently. She asked if she could have a cuddle off me, so I hugged her for a bit and she seemed to chill out a bit. She next asked if I could cuddle her while she faced away from me (Spooning). I did, but then became aware of what was going on and what I was doing in bed with a 15 year old. I put my arm over her anyway and pulled her into my body. She seemed to push back too, wedging her ass into my crotch area. Then out of no where I felt my cock begin to grow. I tried to pull away from her so she didn’t feel anything but she kept pushing back into me. It was pretty much fully erect, so she must have noticed it.
She then started to slowly rock back and forth into my crotch. I didn’t know what to do, what was happening? Was she sleeping, did she know what she was doing? Then came the words I never expected from this reclusive geek. “Does that feel good Alan?” My body froze. I refused to believe what she said. She then stopped and turned round so we were face to face. “Alan, did you hear my question” I stuttered a reply “Ye ye yes it fells good, but you cant do this with me, your too young and im married to your sister” Then out of no where she lunged in for a kiss….To my surprise I kissed her back, it got quite passionate before I broke it off. “Why did you stop Alan?” Milly said forlornly. “Because we cant” I said back. She then got out of the bed and went over and put the light on.
She told me no one had to know and that it would be our secret. I asked her why she was doing it all, and she looked to the ground and said “Because I wanted my first time to be with someone special” At this point I was sitting in the bed and my cock was hard as a rock. Everything in my head was saying don’t do it, but my body was telling me to go for it. Just then I made a snap decision and got up from the bed and walked over to Milly, lent in and gave her a kiss on the lips. She got up on tip toes and kissed back, far more passionately then before. “If we are going to do this, I want to do it right Milly” I said. Get changed into your party dress for tomorrow and ill put on my suit. We can have a mini date here in the hotel room.
I went and got changed while Milly was in the bathroom doing the same. She came out and I was stunned. She was wearing a medium length dark dress and some 4” red heels. She looked amazing. Which I told her and made her blush again. I said to her that we were going to skip the date part and go straight to what happens at the end of the night. So we both went downstairs and then met in the lobby. I took her by the hand and kissed her on the cheek and asked if I could walk her back to her room. We did, and when we got back to the room I said “id love to come in for a drink” She said “Sure thing Alan, id love a drink with you to end the night” So we went in the room and she poured me a class of coke from the minibar. Which I topped up both of our glasses with some vodka. We sat down on the couch and started to drink. Making small talk I decided to lean in for a kiss. A nice soft kiss on the lips and then I put my hand on her thigh.
She jumped a little at this but was fine with it, I continued kissing her and she then put her hand on my thigh and squeezed. She seemed to be following my lead. I broke off the kiss and sat back for a second, looking at her like I never have before. She was beautiful, the glint in her eyes made her even sexier. I told her to tell me if she wanted to stop and if I was going too far. She just told me to shut up and kissed me again. It was then her hand wandered up to my cock, it was semi at the moment, but growing all the time. I felt her squeeze it, and then her hands running around it too get a sense of its size. Let me be the first to say, im not massive, but 6” is enough to satisfy most women. So it would surly be enough for Milly. Sensing her eagerness I let my hand do a bit of wandering its self. Slowly working up her thigh under her skirt until I felt the lace of her underwear. She moaned a little, so I took this as a sign to continue. My fingers began to brush on the fabric of her panties softly stroking. I could feel them getting a little damp too, which is always a good sign. My other hand at this point was making its way up her side to her breasts. These as I said before were a very nice size, so I had no trouble in getting a handful. She seemed to enjoy this too, so I rubbed them a little until I could feel the nipple through all the fabric. She stopped kissing me and looked into my eyes and said “Alan, I want to be your woman tonight” This made me fully hard, and she could tell. Her hand was rubbing the outside of my trousers faster than before. I was going to cum in my pants if she wasn’t careful.
I took both my hands away from her and asked if I could take her dress off. She said she wanted to keep it on for a bit like the women she had seen in porn (So she had been looking at porn all the time she was locked away in her room) So I said ok, and just pulled the top part of the dress down. Exposing her yellow lace bra underneath. She unclipped this and then threw it to the other side of the room. I stared at her young pert tits for a while and then went to work again on her now exposed erect nipples. My mouth went down and started to slowly lick and circle them, occasionally putting them between my teeth. She seemed to like this, as while I was doing it she undid my fly on my trousers and put her hand in, and fumbled around for my cock. She did this for a moment until she found her way through, and when she eventually grabbed it I gasped. I couldn’t believe, my little sister in law was touching my hard cock. She stayed there for a few moments just holding my cock, then kissed me deeply. Slowly her hand began to stroke it up and down. My head was spinning again, this cant have been happening. While she was doing this I decided to venture down to her virgin pussy with my hands too. So I slip my hand up her soft thighs, and under her skirt. I got to the fabric again and gave it a tug. She lifted her ass and I slipped them off. When I put them to one side I couldn’t help but notice how familiar they were. I asked Milly about this and she said that they were Julie’s(My wifes) pants. Turns out that the dress and shoes were hers too. Milly said she stole them from her when she borrowed the dress. So now, I was in a hotel with Milly, dressed in my wives clothes. After an initial wave of guilt pleasure returned as Milly’s strokes on my cock got faster.
It was at this point I had to ask her to slow down as I was about to cum. But this only made her go faster still, and kiss me deeper. She refused to stop even after my pleas. Until I couldn’t hold back much more and came all over her black cocktail dress. Ropes of white cum were plastered all over the dress and stomach of her. She smiled at me and asked if she did good. I couldn’t believe it, she was brilliant. She then wiped her hand into the cum and licked it off. Telling me she always wanted to taste cum, and that was better than she imagined. She then stood up and told me she had to get out of her dress. She slowly slipped it down over her stomach and then past her ass. Her body was almost perfect, nice boobs and a shapely backside. The perfect looking curvy woman. Standing there naked apart from her shiny red heels. I couldn’t take it much more and decided I was going to give this girl the night of her life. I took my clothes off too, and freed my now limp cock from my boxers.
I pushed her back onto the bed and laid next to her. Kissing her softly and caressing her boobs. I then moved down to her pussy, which had hair on it, but it was defiantly trimmed. It was neat and short. Perfect. I kissed the insides of her legs, slowly making my way to pussy. I could smell the sweet scent coming off of it, and see it was wet. I eventually kissed it, she jumped a little, then put her hands on my shoulders, almost making me go closer. I kissed it a bit more, then began to lick the lips of her perfect little pussy. She started to breath heavily, and I could see her nipples harden again. Her hands also now moved to the back of my head and she was beginning to grind her pussy into my face. I started to work the clit, and it became even wetter. Her legs where in the air now too, wrapping themselves around my body. She told me she was close, so I went harder and faster on her clit. Flicking it around and then licking her pussy lips. She then suddenly exploded in my mouth. She even squirted a little on my face. She was in heaven. Shaking a little and letting out a low moan. She pulled my face off and made me get up to kiss her. My face covered in her pussy juice was pressed against hers in an incredible erotic kiss.
She slumped onto the bed, breathing heavily and sweating a bit too. She could not have looked any sexier than she did at that moment. She looked me in the eyes and said to me “This has to be our secret, I want it to continue forever” This was music to my ears. Buy this time my cock was getting harder and she could see it. Her eyes became fixed on it again. She grabbed it and started rubbing. This time making her hand wet from her pussy and rubbing it that way. She looked at me and said she wanted me to fuck her. I didn’t have to think twice, I got into position put the tip of my cock onto her pussy. She said to me not to worry about hurting her as she had been using dildos in her room for the last 3 years. So she was all ready for her first real cock. So with a deep breath I put my cock into a already drippy wet young pussy. It slipped in with relative ease. So I pushed deeper, eventually all the way in. She let out a small gasp and then kissed me. She looked into my eyes and said “Fuck me…..hard” With that I began pumping away inside her. Starting off gently so as not to hurt her. But all she kept saying was “Harder” so I got faster and harder. She put her legs over my shoulder so I could get deeper into her too. (She clearly had seen a lot of porn) We were both a hot sweaty mess when I decided to change positions. I got on my back and she hoped on top. I let her do this so she could control the pace.
Boy did she control the pace, I could feel her getting faster and faster all the time, grinding right down so her clit was touching my pubic bone. We were in ecstasy. She was fucking my brains out while I played with her nipples and grabbed her tight ass. Running a finger up and down the crease of her ass, she said to me “Save that for another time” With he saying that I came right there. I filled her full of my cum. I really should of pulled out but I didn’t have time. She kissed me again and told me she loved me. She then rolled off and the cum started to drip out of her pussy. She again scooped it up and licked it off her fingers. I thought to myself, I not only had a little slut, but she was filthy too.
She rolled over and looked at me and said “Alan, can we do this more often. I have loads of things I want to try and we can do them together” With that I pulled her into my arms and we both drifted off to sleep. We woke up in the morning with my alarm going off. There was a patch of dry cum where Milly had been sleeping. She looked and it and gave me a smirk. We packed up and got changed, then hit the road again. Stopping off briefly to get Milly a new unspoiled dress. While we where there we picked up a few other things. But that’s for another time. This sweet little geek that I knew from the start of the journey had turned into a little slut over night. Life was good again.
