Sex Files: Part 11 (Sky)

So, I was living with my buddy D-Rail at the time, I had been in quite the dry spell. Working at Jimmy Johns, trying to get school back on, and my life back on track. Things hit me pretty hard, to be honest but, I wasn't about to give up on anything. D-Rail and Mah called my stressed behavior out as a, "You needa get laid kid" kind of moment so, D-Rail called up his girl, who called up a friend of hers to come out and play around. Sky was her name and she was a bad bitch for sure.

It had always been kind of weird for me to meet and just "hook up" with some random. I always felt like I had to know that person to a certain level. So, when Sky and Sierra (T-Rub) came out, things were definitely weird for a while. We kind of just sat around at the house and didn't really do a whole lot. There was a lot of silence throughout the few hours that started it. D-Rail and T-Rub would excuse themselves often to go fuck around in the other room. Leaving me with Sky to be awkward as it would be. It took a while but we got decently acquainted, once she threw that half cocked smile out there, let me put her arm around her without flinching and, actually looked me in the eye's while we talked, right before we laid back together on the couch... I knew I was in. It got darker out and, I, of course, agreed to take Sky back home if she didn't end up staying the night with me. So, we headed back to my dad's place, and straight up to the bedroom.

I didn't even try to get straight to the point with this one, I had literally only known her for a day so, it was going to be awkward before anything else. We kicked off our shoes and laid back on the bed. Sky laid up on my chest and we just held each other in our arms. With her head on my chest, curled up on my side I was holding her in close with my arm wrapped around her back. I threw the TV on and we worked out a good chill place. She played the back rub card so I rolled out and she laid on her stomach. I sat under her but on the backs of her thighs. Sky had a nice butt too, good curves in her figure, decent like C cup breasts, fairly perky but there was definitely room to grow. Anyway, so she's laying there in her skinny jeans, and I'm sitting on the backs of her thighs. Leaning into her with my palms out, I pressed down and rotated my wrists as I pulled my hands off to the sides of her back. Doing this all the way up her spine, then using my thumbs to get into those extra small spaces going back down her back. I got down to her tail bone with my thumbs, my palms rested on her ass. Giving her ass a good squeeze, she popped it up arching her back a hair. She lifted up the bottom of her shirt, revealing her lower back. I used my thumbs in the same way I had beforehand, going up the bottom of Sky's shirt I unhooked her bra and let the straps fall to the side. She promptly lifted herself up and threw her bra off to the side. Massaging under her shirt, wrapping my hands around her shoulders relieving the pressure as I break down the knots I find. You KNOW I had to pull the "give and get" card on her, I spent probably a good solid half hour just giving her a back massage. I wasn't about to let this all go one way so, when I was all wrapped up with doing her back, I sat up on my knees and gave her a good smack on the ass. Telling her to get up cause it was my turn, I laid up on the bed. On my stomach with my arms at my side, Sky sat down on my thighs like I did her. She wasn't the best at the back rub part, but she hit a good few spots where it was needed most. My back rub only lasted like 5 minutes or so, but I could tell she wasn't really into it anyway.

I stopped her and rolled myself over onto my back. Sky scooted up a hair when I rolled onto my back, now she sat on my dick. Grabbing her waist I slid her shirt up and placed my hands on her belly. wrapping them around her sides I slipped both my hands up and around her ribs, then bringing them together on her breasts. The shirt didn't feel right so I had to change that. Pulling my hands out of her shirt I lifted up the bottom edge, leaving Sky to take it up and over her head. She covered herself at first but I coaxed her out of keeping it that way. She told me for every piece of clothing that came off of her, I had to match it, and I did. Getting warmed up with each other, I pulled her in close and kissed her cheek. She didn't like my hands being on her neck so, I let that go as it was. As I squeezed on her sides with a massage like pressure, and Sky began to moan and grind on me. It wasn't too long until I was picking her up and rolling her off to the side. Swinging her off to the side and back onto her back, I hopped up and swung myself between her legs. Inching up her front, dragging my nose up from the rim of her pants, between her chest and up her neck. Sky still didn't like my hand being on her neck but, it seemed she was making a slight exception by this point.

We kissed deeply while I held my hand on the side of her face, keeping my middle ring and pinkie wrapped around the back of her neck, all while simultaneously stroking my thumb down her cheek. She would wrap her arms around my sides and pull me in closer to her, letting go of her neck I then used my hand to caress her. Running my fingers up her side and groping onto her breast. I slid myself down, keeping a handful of Sky's bitty C cup titty in my grasp. A handful would turn into a mouthful while I draped my tongue over it, swirling around her nipple. With my mouth encasing one, the other of her breasts was free for my other hand. Curling my fingers, I would pluck at Sky's other nipple, then twist it between the index finger and thumb. Sky's moans were very soft, which made sense as she was a soft spoken individual. While her moans were ascending, I slipped myself down between her legs. Wrapping my mouth around the crotch of her pants, lightly biting down, using my jaw as an underlined pressure point. While I did, I reached up and around, unbuttoning her pants. I pulled myself back and pulled on the rim of her pants. Sky lifted her butt up so I could pull them the rest of the way off. When she did, it revealed her little white thong. It wasn't anything fancy but it did have a nice little bow on it, right above the crotch. After I pulled her pants the rest of the way off, I threw her legs up and kissed up her thighs. Dragging my tongue back down them while I placed my hands firmly against her breasts, I then wrapped my mouth around her pussy, just toying with her. She didn't seem to be as into it as I'd hoped to be honest and, when I picked myself up to use my fingers on her, she put her hand in the way, explaining that she was afraid of what I was going to think. That she hadn't shaved that day and she was embarrassed. I reassured her that I wasn't worried about it in the slightest, telling her that we were here to have a good time, and that's what it was going to be. She let go and let me have my fun with it. So I pulled myself back and pulled down her thong bit by bit. Slowly slipping it over her thighs, and under her ass. I watched her freeze up in fear, throwing her hands over her crotch. I grabbed onto her wrist but she was not having it. So I sat up and told her flat out,

"If you don't want to do this, it's ok. We have gone a long way for you to try and turn back now though but, I will leave this up to you. 100%."

Sky then relaxed herself, giving me a little smile. So I continued, pulling her thong off and tossing it aside. Sky's eyes melted looking down at my while I finished pulling them off. Almost lost it completely when I brought myself back up and then slid down on her chest, dragging my tongue all the way down from her neck, between her breasts, down her abdomen, and finally I wrapped her legs up over my shoulders and leaned my face in. Sliding my tongue between her lips and dragging in slowing up and down, I added little dips and flicks while I played her clitoris with my thumb. The thing that struck me as odd... she was not wet... not even in the slightest. I thought it might have been cause I wasn't doing something right but when I went to pop up and bring it up, she grabbed the back of my head and pulled me back down letting out a lengthy sensual moan with it. I went with it for another few minutes, REALLY getting in there with my tongue, but it wasn't going anywhere still so I pulled out. Sitting up I tried to stimulate with my fingers but, it just wasn't working out. We ended up just saying fuck it and I took my boxers the rest of the way down and laid up on the bed. I told her,

"Seeing as we're neither of us are going to let this go one way, I think it's your turn to go down on me."

Sky took her sweet ass time with it but, as she re-situated herself down toward the end of the bed, I had to lean up and give her a good smack on the ass. Now Sky has a very small mouth, so small that she couldn't really fit my dick in her mouth. She tried, and she did get it in, but she could not get even remotely passed the tip. Her teeth had a certain sharpness to it too, which made it very hard to enjoy what was going on. I tried to hold my composer, she did have a few good moments where there were no teeth involved but, it didn't take long for her jaw to lock up and, immediately I would know when that was happening. So I kind of just said fuck it and pulled out of it.

I re-buttled asking her to ride first, she was hesitant upon answering, but she got herself propped up and climbed up on top. I grabbed on the underside of her ass and picked her up while she grabbed the base of my dick and crouched down trying to slowly slide it in. Mind you, she's not wet, so you can guess it, we got the tip through the lips and she hopped right back off. I spit on my 4 fingers and gave a good wipe from back to front, and she spit a bit on her hand, trying to lube up my dick. It went slow, but we worked through it. I was finally in and she sat down completely. I gripped 2 handfuls of her ass and picked her up thrusting into her, trying to get the juices flowing. It was tough but, she did get wet for a brief moment, of course, it didn't stay so I kind of just assumed she came so I just kept going. I wanted to switch things up again cause, well, I just wasn't getting anything out of it and, it didn't look like she was either. So I switched up into doggy style, we had a little trouble getting it back in but not as much as the first time. I would say I favor doggy more cause, well I don't know really... I guess it's the booty. Grabbing hold of her ass, spanking her while I switch up between love handles and ass cheek, all while I'm beating my balls against her cheeks with every deep, hard and fast thrust. I leaned in, putting my dick balls deep in her pussy. Grabbing hold of her waist I would pull her into it and thrust all in the same motion. A few moments went by and still nothing so I switched it up again. Moving into missionary, I then picked her legs up, crossing her ankles and holding her ass up off the bed. Thrusting as hard and fast as I could go, but STILL nothing. I felt her get wet very briefly but it was quick to fade, I had one hope left and it was scissor locking with my dick at a down angle, and our legs interlocked... So I went for it. Unfortunately, still nothing. All of this lasted a good hour and a half.

I had to level with her at this point, I pulled out and asked her if she was getting anywhere. She didn't have much to say about it at this point, just looked back at me and asked if I wasn't enjoying myself. I froze up briefly not really knowing how to respond to the situation, looked her dead in the face as she had curled up inside of herself hiding a bit and said,

"No, no no no no no. I just don't know what it is. You're not getting wet in the slightest, and you don't look like you're having a great time. I know you just got out of a shitty place relationship speaking, and I'm trying to respect that all in the same. If you're not into it, it's ok. I understand but, I don't want to be the reason you continue if this isn't what you want."

We kind of decided to just lay there for a bit, still naked, spooning. I had an idea suddenly, and she was up for it. So I had her lay on her stomach, arch up her booty a bit, and slid my dick in from behind. I grabbed hold of her love handles, thrusting deep down inside. I gave her ass a good solid smack and sped up. Sky kept her face buried in the pillow, I could feel her tensing up as I watched her clench her fists on my other pillows. I could hear her moans and I was finally getting there. She got wet again, and her legs started shaking vigorously. It only fueled my fire. Then the wet faded out again and her moans went kind of limp. I was so close to being finished so I just kept going. I pushed harder and gave her ass another few good smacks. She woke up real quick and the moans kicked right back up a notch. I worked her back into doggy style, crouching while I put forth all the force I could from this strange angle. Trying to keep things moving to stay in the moment, I flipped her back into missionary and went to town. I felt the build up coming but it was a fight to get there. Flipping her back into doggy, then dropping her back on her stomach, I got as deep as I could and held her arms up behind her back with one hand, and grabbed hold of her ass with the other. Thrusting hard and fast, I finally caught the build up. It took about 2 minutes to get there but once it kicked in, I had 3 short breaths and flopped my dick out between her ass cheeks, busting out a load on Sky's lower back.

Standing up I went to the bathroom and grabbed her a towel. I cleaned up her ass for her, gave it a little smack and even leaned in planting a little kiss on the cheek. Still a little light with the whole her not really having been wet through the whole experience, I had to ask if she actually came. She said she had a lot but I was so unsure about it. We both got ourselves dressed and I drove her home that night. It wasn't that pleasant of an experience to be honest, by the end of the night I felt I was lucky to have gotten off at all. The next day I drove over to D-Rails and busted open the front door, shouting for him the whole way. I told him all about how she didn't get wet at all and since I'm being brutally honest about it... it was like throwing a hot dog down a hallway. I found out in the same day from T-Rub that, apparently Sky was going around saying it was the best sex she had ever had. I felt shitty after that, and then was reminded of how shitty I felt years after when I found out that women's vaginas loosen when they are extremely aroused. I don't know how to explain the lack of moisture to this day and, I guess that ties into me really not knowing if she was just saying that so it would get back to her fucked up ex... or if it was genuine. Either way, it was a weird experience, but well done, and properly laughed off in time.

I will say again, as I've done in basically all of my writings. I urge you to keep reading, all of this is real and true. As usual, I hope you're entertained at the least, we'll see you soon.