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Hi everyone. Long time lurker, first time poster. I have been reading the stories here for close to a year, and it really aids with my self-pleasure, if you catch my drift. Please forgive formatting errors, and be gentle with me! It's my first time. (: So a little background about me: I'm 26 and blonde, with hazel eyes and a round face. The more important stuff: I am curvy, with wide hips and big breasts (36DD), and I am right around 5 feet tall. By day I am a Kindergarten teacher, but by night I turn into a super sexual being who finds herself insatiable. Reading hot stories, watching any and all kinds of porn, and thinking back to some of the fun times I've shared with different men. I had broken up with the love of my life back in May, and I'd been in a slump ever since. I found myself incredibly unattractive, filled with anxiety and regret over the painful breakup. Our sex life wasn't the greatest, for whatever reason we just never got our groove down. And with our incredibly conflicting schedules we just weren't able to make it a regular thing to try and fix the sex. It made me feel really insecure in bed, especially when I've never had complaints before. I have always taken a lot of pride in being a super sexual woman in a relationship, wanting to be touched all the time and instigating sexual encounters with my previous boyfriends. He and I have since begun talking again; not sure where this will lead, but I am being super cautious this time. About a month ago was my 26th birthday, and my friends decided to take me to the local dive bar that we sometimes go to to get trashed and dance. We are usually a few of the only ones there, so I wasn't going and expecting to meet anyone. The usual clientele were not my type: older, sketchy, murderer-esque. After pregaming HARD at my place, we took an Uber and headed over. We danced and drank, danced some more and drank some more. I was wearing a button-up dark green army flannel shirt (yes, I know how hot it gets in SoCal in August, but it was laundry day and I wasn't aiming to impress anyone that night), skinny jeans and flat sandals. I had straightened my long hair and was just ready to forget about my ex and dance the night away. A little while later, my friend Katie (who gets wild when she drinks) started chatting up a guy named Joe at the bar. I remembered thinking he was cute, but since Katie had spotted him first, he was off-limits to me. I went back to dancing with my other friend Cassie while Katie continued talking to her new friend. Shortly afterward, I went to use the restroom (small bladder and all), and came out to find Joe sitting at the bar alone. Looking around, I saw Katie and Cassie on the other side of the room, talking to some other people. I walked up next to Joe and he smiled. "Oh, I was waiting for you!" He beamed. "You were?" I asked, drunk and confused, but pleased. Suddenly I didn't feel as though he was as off-limits as he was a little while earlier. We ended up talking for a while. He found out we were there celebrating my birthday, so he bought me a vodka cranberry and a birthday shot to celebrate. We did our shots and it immediately went to my head. In my drunk stupor I don't remember a whole lot of details of the subject matter we chatted about, but I did remember we talked about the typical stuff. Occupation, age, hobbies. He told me he was a musician in a band that was on tour, and he was just in town for the night. When he found out I was a Kindergarten teacher, he licked his lips and smiled. "Oh, a teacher? That's so hot" he cooed. If I wasn't so wasted I might have found that kind of creepy, but I was so into him that I immediately felt my panties get wet. I'm not the one night stand kind of girl, not by a long shot. In fact, I have never had one before. But this guy was super sexy, in a totally geeky sort of way. He was so appealing to me, the way someone is after you put your drunk goggles on and take your inhibitions off. Tall with glasses, a button-up shirt, skinny jeans and a whiskey in his hand, Joe was the epitome of all things I found attractive (at least in that moment). He was sweet and attentive, but I got the feeling he wanted more than just to buy me drinks and talk about boring stuff. Pretty soon it was last call. Joe and I looked at each other. Katie and Cassie were having fun hanging out with their new friends, but were going to head back home when the club closed. I wasn't sure if I wanted this handsome stranger to leave already, so I told him I was going to go to the bathroom to freshen up and then we could make a game plan. I guess while I was in there he found my friends and asked if I was single, and furthermore if it were alright if he took me back to his hotel to take care of me. Sweet, he was asking for permission. He definitely didn't need mine though, I already knew I wanted him inside me. My friends and I parted ways and Joe and I walked to his hotel room. I remember feeling very slutty, never having hooked up with a complete stranger like this. I can't say it didn't turn me on though! As we walked I knew my panties were soaked. I was going to be fucked by this guy, and the anticipation was building like crazy. We stopped at his front door and as he was searching for his key, he suddenly stopped and pinned me against the hallway wall and kissed me feverishly. I was so taken aback but I practically gushed in my panties. "I really want you" he breathed into my ear. Even through both of our jeans I could feel that he was hard. I echoed his sentiments and told him I wanted him too. He finally broke free of kissing me and found his key, opening his hotel door and closing it behind us. Before I could walk to the bed he pulled me into the bathroom. "What the-?" I started to ask, but then he put his hand over my mouth and shut the door behind us. "I have to tell you something first", he whispered. "My bandmate is sharing a room with me." My eyes widened. He couldn't have told me this before we got here? I might have changed my mind! Now I was freaky, but not THAT freaky. I could never fuck someone while someone else was in the room- Could I? He could tell I wasn't entirely comfortable, so he took the opportunity to stick his hand down my pants. Before I could make any decisions about what to do with the roommate situation, I concentrated on his hand rubbing me through my panties. Fuck, I was his, I didn't even care about the other guy. I just needed him inside of me. He put a finger to his mouth to shh me, and we tiptoed to his bed just 2 feet from where his friend was sleeping. We both got naked really fast; the anticipation was building for so long that I didn't want to wait anymore. I climbed on top of him and started grinding my wet pussy on his dick. It felt so good just to be desired by another man, and the fact that I was desiring someone else other than my ex was amazing. I asked Joe if he had a condom, and he responded with "unfortunately, I don't." I was heartbroken. The pill had given me horrible cramps so I had gone off of it. Plus with my relationship ending, I saw no point in getting back on it. I stopped grinding on his dick and tried to think of what to do (multitasking is hard to do when you're wasted). "Are you clean?" He nodded and asked if I was. I nodded in response. I paused for a moment and he said "Let me fuck you, baby." That was all it took. With one swift motion he was pushing his dick up inside my slippery pussy. He had to go slow, as I am very tight and I hadn't had sex in a few months. He groaned loudly, but covered his mouth to make sure his roommate didn't hear it. Something about that drove me wild. Here I was, the good little teacher girl with a strange man's (bareback!) cock up in my pussy while another man slept less than 3 feet away. It was so erotic and sexy that I could have just cum right there. I was grinding on his dick until he was all the way inside of me. "Oh fuck, you are so tight," he moaned. I rode him some more, getting increasingly turned on by the fact that I was being so deliciously naughty. I was drunk and fucking a stranger, and had never felt so confident in my life. Joe had his hands on my ass, squeezing and grunting every few seconds. I didn't care about the roommate waking up, I was concentrating on the awesome feeling inside my pussy. A few seconds later, I noticed Joe's hand starting to wander down my ass. I thought he was just looking to get a better grip, but before I knew it, his finger was circling my asshole. I didn't think he was going to try anything, but next thing I knew, his finger was inside my asshole up to the knuckle. I let out a gasp; it was such an incredible feeling of taboo, pleasure, and pain that I came around his cock hard and fast. I have always been curious about anal sex. The few times I've brought it up to ex boyfriends it never seemed to go anywhere. And the other boys I was too bashful to ask because I thought they would find it gross. But this guy, this stranger just put his finger in my virgin ass and I absolutely loved it. As my orgasm subsided, he told me his was going to come any second. I guess a night full of drinking, flirting and teasing won't make you last very long - it didn't for me! He pulled out and came on my stomach, breathing hard and rubbing his dick until it became soft. I popped the head into my mouth and licked it clean. He looked down on me and smiled and called me a naughty girl. I smiled back and looked him in the eyes as I licked the cum off his cock. It was past 4am at this point and we were both so exhausted that we fell asleep. The next day I woke up and attempted to get dressed, but I couldn't find my underwear anywhere. I decided I would leave that for him as a reminder. I tried to escape before he could wake up, but he heard me rustling and insisted on taking me home. Sweet guy, I thought. He ended up dropping me off in a cab, kissed me, and thanked me for a fun night. The most important thing about this story is how sexually charged I am now. Before that night, I was sitting at home, hung up on my ex and feeling sorry for myself. Now, I am coming to terms with how sexual I feel. Today I masturbated four times thinking about Joe's finger up my ass while I was fucking him. I had a dream about having my ass fucked for the first time and I have never wanted it more. I have been feeling like I should just slut it up a little more, and if I do, I will make sure to share my fun times here. xx Redlipsandhighheels

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