Sorry about the format, I still haven't learned how to change it on here. Hope you like the story.
Why did she have to be so hot? She’s been one of my best friends for years, but unfortunately, so was her boyfriend. All three of us went back to the days of college when we were wild and free. Well, at least they were. We were the three amigos, though the problem with that is obvious to the people who were the odd man out like I was. For years I’ve watched them frolic and play right in front of me. We all talked about sex like it was just an everyday conversation; and to their knowledge, it never bugged me; but deep inside, my cock was aching for my best bud’s girl. You can only hear so many stories about how great she is at sucking cock, and how much she loves to be fucked up the ass before you start looking at a woman differently.
I still remember the first time it got the best of me; I was in a movie theater sitting next to Jill when she had decided to be naughty and start sucking Brian’s cock. The movie was an action flick, so at least it held my attention a little, but the fact was, this woman did wonders to that man’s dick. She bobbed up and down like it was her last time to ever get to suck a cock. But half way through was when she got me; she reached one of her hands over and placed it on my thigh. Now I don’t know if it was intentional, but with every thrust downward on to Brian’s cock, her hand squeezed and massaged the upper part of my leg. She never grabbed my cock or anything, but just watching her work and feeling her on my thigh was enough to give me a raging hard on. As she finished up, she sat back up and used the same hand to wipe her mouth clean of the remaining cum and spit then just went back to watching the show.
I went home that night and masturbated twice to the image of Jill. I felt guilty both times, but the fact was that from that point on, all I wanted was to feel her lips on my cock. Imagine that frustration for all these years eating me up from the inside. I hid the feelings away though, and worked hard to not dwell on them too much. But I have to admit, I don’t think I’ve masturbated since then without having her face come into my mind. A few years later I accidentally walked in on her in the shower. We had all been sharing an apartment for a while, and she wasn’t expecting me home, and I didn’t know that she was home. I had come in, turned on the stereo, and then decided to go relieve myself. I guess that’s why I never heard the water running. I opened the door, and her beautiful naked body was staring back at me through the clear glass of the shower. She just stared at me for a few seconds as I found myself trapped in the doorway unable to leave. She finally gave me a wicked little grin, threw her towel at me and told me to go away. The desire to urinate had passed, and once again I found my hand pumping feverishly up and down on my cock in my bedroom. We never talked about it.
Well, that was about two years ago, and brings me to my current awkward situation. Jill is asleep on my lap in my living room. Brian decided a couple months ago to go into the army, and has been gone at basic training. I know that things were getting a little old for them before that, because it seemed neither of them really talked about sex as much as they used to. Last night Jill called and said she was lonely and wanted to come over and watch a movie. Who was I to argue? When she showed up, she was wearing a white tank top and some boy shorts…normal wear for her…but I haven’t had sex in six months, and this was not helping the situation. We watched a movie and somewhere in the dark, thanks to a few glasses of wine; she passed out on my shoulder. She wasn’t drunk, just sleepy. I felt her arm drop into my lap, and even though it was still, her fingers were resting perfectly on the hardon that I had managed to keep hidden till now. I was so fucking horny, and losing control by the minute. I decided to at least get away with a little, and slowly began to slide my hand down her soft silky shoulder. I rubbed her arm for a few minutes, finding that it only made my cock twitch against her fingers. She moaned a little, but didn’t really stir. I moved my hand to her back and rubbed it a little, and then slowly slid up the back of her tank top enough to feel the naked skin there. She rolled forward a little, cuddling more against my chest than my shoulder. I slid back in my seat, allowing her to rest more comfortably as I continued to slide my hand further down her body. My fingers came to rest at the top of her ass cheeks where her skimpy shorts had slid down a little from her scooting on the couch. Just the feel of that tight little crack made me want to feel more.
I started to hesitate, but figured that even if she woke up pissed, our friendship would be strong enough to handle a little perverted advance. I slide one of my fingers down beneath the snug waistband of her short, half expecting to find a thin band of the thong panty I had heard she was accustomed to wearing. NO PANTIES! My cock twitched again. I had to have more. I knew it was wrong, but I was lost. I pushed the rest of my hand downward, and before I knew it, I found myself massaging my way around her ass, allowing my fingers to search for the tight little hole. Jill just moaned some more, and once against lowered herself further down my stomach. If I would have undone my jeans, I knew my cock was long enough to reach her soft luscious lips. The temptation to go there was overwhelming, but I opted to wait and see how much more I could get away with first. My heart was pounding as my middle finger found her tight asshole. I didn’t want to stop…not that I could have anyway. I start teasing the hole, probing gently at it without pushing my way inside. Jill was moving her hips around, almost as though she was pushing against my finger instead of pulling away from it. She was moaning even more too, which was making my cock ache as it pushed against the thick denim of my jeans. I couldn’t help myself any longer. I just had to feel her lips on my cock.
I reached my other hand down and carefully stretched back enough to help me to undo the fly of my jeans. I quietly and carefully unzipped my zipper and pulled the flaps apart. My cock was pressing hard at my briefs, and I eagerly worked my cock out of the small flap in the front, allowing it to spring to life right in front of Jill’s face. I was right. As it slapped against my stomach, I could feel the tip brush directly against her perfect plump lips. I’m talking Angelina Jolie lips here. I froze in place for a minute, knowing that the small drops of pre-cum that had already begun to leak from my cock had to be oozing onto her lips. I wasn’t sure which was going to wake her up first, the cock pressing at her mouth or the finger pressing at her ass. To be totally honest though…I didn’t care anymore. I just wanted her. But then it happened…just when I was worried it was about to end, I felt her gasp out a small breath against my swollen cock. I could feel the warm air as it cascaded all around my sensitive member. But her mouth didn’t close back up. It wasn’t open wide, but it was open.
I was already pushing all the limits, but the thought of actually pushing my cock into her mouth had me very nervous all of a sudden. I knew as soon as I got inside, she was sure to wake up and bite my pecker off. But believe me when I say, I just wasn’t thinking clearly enough to stop now. My free hand moved to the top of her head, and I gently began rubbing her hair at the same time as I pushed my hips upward just enough to press the tip of my cock between her silky lips. I didn’t even get the entire head in, but I immediately felt the warmth and wetness of her tongue. I knew she had to be tasting my cum by now. I pushed gently down on her head, pleased that it seemed to slide downward easier than I expected. My cock disappearing a little more inside. At the same time I started to tease and play with her ass again, only now pressing my finger a little more aggressively against the tight hole, hoping to get it inside her before she stopped me.
And then she woke up.
As I felt my finger start to slip inside her tight asshole, I felt Jill squirm a little beneath me. My cock fell out of her mouth, and my hand froze against her ass.
“What are you doing?” She looked up at me with more of a shocked look than an angry look. I couldn’t speak. Jill looked down at my cock, and then down at my hand disappearing into her shorts…
“What are you doing Jack? Because if I’m not mistaken, it seems like your trying to finger fuck my ass and make me suck your cock?”
I still couldn’t talk, and I started to pull my hand out of her panties when I watched her free hand reach back and pull it back tight to her ass. I was confused to say the least.
“I didn’t say to stop…I just wanted to make sure I had your intentions correct.” She said, smiling up at me. “Force that finger deep in my ass, I do love a good rimming.”
I was shocked, and found that I was still frozen for a moment. And then to my delight watched as she lowered her head back down into my lap and engulfed as much of my cock as she could handle. I was in heaven as I felt her tongue begin to slide all around my shaft as she forced even more of it inside. I heard her gag a little as it moved into her throat, and for a moment, just sat there as still as could be as she began to suck my cock like no woman ever had. She moved up on to her hands and knees , giving me even better access to her ass as she began to really get into sucking my cock. I finally snapped back to reality and began forcing my thick finger into the tight grasp of her ass. She sucked even harder on my cock as I pushed my big fat knuckle inside her. My other fingers stretched down to her wet pussy and began rubbing at it each time I fucked my other finger into her asshole.
I was getting worried, because I could already feel my orgasm reaching a peak, and was scared this was going to be over way too fast. The problem was that six months was six months. I just had to cum and cum I did. Without warning I fired a thick hot steaming load of cum deep into her throat. Jill was awesome at this though, and she eagerly feasted on it. She sucked me as deep as she could, letting her throat muscles milk more and more cum from my balls. I felt her fingers sneak between my legs, fighting to get into my jeans and find their way between my asscheeks. Her mind finger started rubbing that tender spot behind my balls, pushing me even more over the edge. I was so far gone, I didn’t even realize how feverishly I was finger fucking her ass now. The faster and harder she sucked on my cock, the deeper I tried to dive my finger into her ass.
Jill never let up. She sucked me harder and longer than I ever would have thought possible. She had so much suction on my cock, I didn’t have a chance to get soft. I wanted more though. I removed my finger from her ass, and reached over and grabbed her hips and pulled them up to my face. I straddled her legs over my shoulders, bringing her little boy shorts right in front of my face. I guess lust gives you strength, because I ripped those shorts right of her ass, revealing the prettiest shaved pussy I’ve ever seen; Her tender asshole staring me right in my face. Jill was now impaled on my cock by her mouth. She couldn’t have gotten off if she wanted to. I dove right into that lovely pussy and ass, thrusting my tongue in and out of both holes. She tasted incredible. I had never tongue fucked a woman before, but for some reason, I found my tongue forcing its way inside her tight asshole as deep as I could get it. My hands were sqeezing at her ass cheeks and grabbing at her pussy lips. I could feel my cock still rock hard inside of her as she continued to try and suck it in this awkward position. Finally I just slide sideways, laying down on the couch with her still grinding her ass and pussy against my face. Her breathing was getting harder against my cock, and I knew she was close to cumming. I thrust one of my fingers deep in her ass as I sucked hard on her swollen clit. That was all it took to finally push her over the edge, and I was treated to this delicious fountain of nectar all over my face and mouth. I devoured every drop of her fluid, then finally pulled her back up off of my cock. I spun her around on top of me, and for the first time finally had a great look at my friend. She was beautiful. Her face was red from sucking my cock, but there was pure lust still in her eyes. I glanced down and realized that this was the first time I had ever come without getting to see a woman’s breasts first. I had been wanting another chance at those since the day in the shower. I ripped her thin tank top off of her chest like it was paper. Her incredible perky B tits shining back at me. I reached up and grabbed both of them into my hands at the same time as I felt Jill lower her ass down on the tip of my cock.
Jill smiled as she thrust her hips downward, forcing my thick hard cock deep inside her eagerly waiting asshole. As I felt her squeeze my throbbing dick like a vice, I realized how glad I was that I pushed the envelope.