Breaking Out of Boring 3

I looked up into those dreamy blue eyes and smiled. He brushed a strand of hair from my eye and then, just as I had hoped for all night long, he kissed me. My body melted into him as every ounce of tension I had in me left. It was perfect. He was perfect. 

“Goodnight gorgeous.” He said as he started to pull himself away from me. 

“Wha-? Wait! You can’t just kiss a girl like that and then leave!” I protested. 

“Haha oh I’m sorry. I’ll stay as long as you like. I just thought you’d be ready to pass out after being tipsy and all.” 

“Well I was…until that. Now I’m about as awake as I could possibly be.” 

“Ok, well then…” he said as he slipped his hand around the back of my neck and pulled me in for another kiss. 

My hands found their way up over his sculpted chest and around his neck as I stretched up on my tiptoes to meet his kiss. I pulled him further into the room as I kicked off my shoes and fell back onto the bed. 

He kicked his shoes off and hesitated, “You sure about this? You did have quite a bit to drink.” 

I smiled up at him, “Just shut up and kiss me will you?” I was surprised at how confident I sounded. I wasn’t normally so demanding, but it felt good. It felt sexy. 

I felt so comfortable with him. I felt sexy, I felt desirable, and I felt like I could be myself without worry and it showed. We made out furiously. Our hands roamed one another’s bodies up and down and I could feel myself getting more and more turned on. His large hands on me made me feel small and delicate and the way they massaged and grabbed at my body drove me crazy. His body was perfectly toned beneath my hands, feeling his back muscles flex and move as he did, his arms hard and strong, and finally, I was able to feel his forearms ripple beneath my fingers. He was the sexiest man I’d ever met and here I was on a bed with him on top of me. 

Eventually I grabbed at the hem of his t-shirt and hoisted it up over his head. He did the same to me, before hovering over me staring down at my body. “You’re absolutely gorgeous you know that?” He said as his fingers gently danced their way down my neck and sent a shiver down my spine as they traced my collarbone. I reached behind me and unhooked my bra, tossing it to the side, and pulling him back to my body. 

I wanted to feel his skin on mine, his hard body against my breasts, his sculpted stomach pressed to mine. I wanted to feel him on me, I wanted to feel him in me. 

I gasped as he moved lower and took my nipple into his mouth. His warm tongue danced and flicked over my hardening nub expertly before moving to the other side. My nipples tingled and sent a rush of pleasure down my body with every flick of his tongue. Slowly he kissed his way down my stomach before getting to the edge of my skirt. I wanted him to keep going, I didn’t want him to stop. I lifted my hips, giving him the ok to pull my skirt off. He obliged and also took my thong with it, leaving me completely naked before him. I spread my legs to give him access to everything he wanted and closed my eyes waiting for him to drive me wild. 

But it never came. I opened my eyes wondering why he hadn’t started eating me out to find him hovering above me, looking into my eyes. 

In a sultry tone he asked, “What do you like? What drives you crazy that you’ve been too scared to say because you worried you’d get judged? I know there’s something, I could see it on your face earlier.” 

“I…I don’t know.” I lied. 

“Sure you do.” He said as he kissed my neck and let his hand run up my inner thigh, brushing just past my pussy but not letting me have what he knew I wanted. “If you’re not going to be honest with me, I can’t make you as happy as I want to and I’ll just be left teasing you until you do tell me.” 

“I…” His fingers traced the edges of my pussy lips making my breath catch as I hoped he would give me any sort of stimulation other than the soft teasing brushes of his fingers. “I don’t…I can’t.” 

“Yes you can. I know you want it, all you have to do is tell me.” 

My inhibitions were paper thin. Between the alcohol and how incredibly aroused I was, I couldn’t hold out much longer. His teasing hands were chipping away at me and I knew I was going to break. 

“Ok, ok, I…I like butt stuff” I mumbled. 

“You’re going to have to speak up a little more than that if you want my tongue on your clit anytime soon gorgeous.” He prodded 

I broke, I couldn’t take it anymore, I wanted his tongue on my clit desperately and without even thinking about what he might think of me, I blurted, “I like butt stuff. I like having my ass filled.” 

James didn’t miss a beat, he reacted as if I’d said the most simple and obvious thing in the world, “See, that wasn’t so hard was it?” He replied as he moved his way down my body. 

He dove between my legs and proceeded to eat me out in a way that I had never experienced before. I couldn’t even tell what he was doing, all I could tell was that it felt amazing. His tongue seemed to be everywhere at once and he knew exactly when to apply pressure and when to back off to the gentlest of touches. I was lost in it and found myself moaning and my hips thrusting my pussy into his mouth, desperate for more. I came quickly, and then came again shortly after. I wanted his dick inside me, and just when I was about to pull him up to get just that, it happened. 

His tongue was still lapping at my clit when suddenly I felt his finger, slick and coated with my cum, pressing against my ass. I gasped, I couldn’t believe this was about to happen. I’d been fantasizing about this as I fucked myself for weeks and now it was actually happening. As James applied pressure with his finger I relaxed and he plunged inside up to his second knuckle. I let out a long moan and began gyrating my hips up and down, fucking my own ass on his finger. 

He got the hint pretty quickly and soon he was thrusting his finger as deep as possible in and out of my tight hole. It didn’t take long for him to add a second finger which was more than I’d ever taken with my toy. It felt incredible. The pressure was even greater and his thrusting was driving me to my third orgasm of the night. I was a complete wreck, I couldn’t think straight, I couldn’t form a coherent thought, I was just writhing, moaning, and losing myself in the pleasure. 

Just when I was about to cum for the third time, James pulled his fingers out of my ass and stopped tonguing my clit. I lay there catching my breath, my breasts heaving, and slowly opened my eyes. James had left the bed and was now pushing his shorts and underwear off. His dick sprang into view and I got my first look at him totally nude. 

He was toned all over, his six pack visible as his labored breathing clenched and unclenched his stomach, his arms built and flexing as he moved to grab something from his dresser, and then his dick; his dick was beautiful, it was bigger than I’d had before but not huge, it was proportionally perfect, with a thick shaft and a head that was glistening with precum. I wanted to taste him, but I suddenly realized that would probably have to wait as he generously spread lube up and down his shaft. 

Oh my god. He was going to fuck me. He wasn’t just going to fuck me, he was going to fuck my ass. I suddenly got nervous. Could I take something as big as his dick? It was quite a bit larger than the dildo and I’d only just started using that. I wasn’t sure if I could do this. I wanted this, I really did, but I wasn’t sure if I could physically handle it yet. It was worth trying at least, and if it didn’t work then, fine, I would tell him to stop. 

He walked back over to the bed and pulled me to the end of it with my legs up in the air over his shoulders, spread so he could see my glistening pussy, and my ass at the very edge. I felt so submissive. I was his to have as he wished. 

My breath caught as the head of his cock pressed against my ass, gently at first, then with more and more pressure. I didn’t think it was going to fit until suddenly I felt my ass stretch open and the head of his cock slip inside me. There was a slight twinge of pain as I stretched to accommodate his girth but as soon as he had entered me I was overwhelmed with how big he felt. 

Slowly James began thrusting short shallow thrusts working himself deeper and deeper into my bowels. I lay there gasping and moaning as he went, feeling him stirring depths that had never seemingly been reached by the dildo. 

“Oh my god, how deep are you?” I asked, expecting him to say he was almost bottoming out. 

“I’m about halfway, want me to stop? It’s ok if you want me to back out.” 

“Holy shit that’s only halfway? You feel huge. No don’t stop. Keep going. I want it all, give me every last inch.” 

“Mmm…Yes ma’am,” he said as he leaned forward and the second half of his cock sunk into my ass in one fluid motion. 

My eyes bugged out of my head as I sat up and my mouth dropped open wordlessly while the sensation washed over me. “Oh my god, Oh my god. Holy shit that feels big.” I gasped collapsing back onto the bed. 

“You ok?” He asked. 

“I’m good,” I laughed, “I’m so very very good.” 

With that he began slowly thrusting in and out of me with long smooth strokes. The sensation was similar to when I used the dildo but the pressure was amplified 10x and made me feel so incredibly full with every thrust. I felt like I could cum at any moment. 

He built up speed and soon I was receiving my first real assfucking. His balls slapped against me with every thrust and I could hear the wetness of my pussy as his pelvis pressed into me. I sat up on my elbows and looked down to see his cock disappearing into me. I couldn’t believe I was taking this huge cock, and yet there it was, fucking my ass for all I was worth. 

I fell back on the bed and began kneading my chest, playing with my nipples, and not worrying at all what James thought of what I was doing. Suddenly I felt James’s hand on my clit and that was it. That was the final sensation that pushed me completely over the edge. 

“Oh my god I’m cu- ahhhhh!” I cried as I felt my pussy spasm and my ass clench down on his pistoning cock. 

He thrust deep inside me and remained there as I rode out my orgasm. It was the most intense of my life; the intensity of the moment, James and his gorgeous body, knowing his cock was inside me, knowing his cock was inside my ass, his fingers on my clit, my hands on my chest, it was almost too much to handle. I felt like my body might explode as it clenched, spasmed, and writhed uncontrollably. 

When I finally stopped squirming and opened my eyes, James was looking down at me with a smile. 

“That was, without question, the hottest thing I’ve ever watched in my life. I hope to god you enjoyed that as much as I did.” He said. 

“Phew, did I ever. That was unbelievable. Did you cum? Sorry I couldn’t tell, I was a little…overwhelmed down here.” 

He slowly began thrusting again, “No, not yet. But I don’t need to if you’re spent.” 

“Oh no, you just gave me that and you think you’re not going to get to cum? I’m not that mean. But I wouldn’t mind changing positions if you don’t care.” 

“Absolutely not, what’d you have in mind?” He asked as he continued to slowly slide in and out of my ass. 

“I want to be on top.” I said confidently. I felt sexy as hell, and I wanted to ride this man until he came, knowing that I was able to drive him as wild as he drove me. 

Without a word, he slipped from my ass and laid back on the bed. I turned around to face him and climbed on top. I reached back behind me and guided his large cock to my asshole. I slowly impaled myself inch by inch until my ass sat against his pelvis. The angle was slightly different in this position but felt equally arousing. I placed my hands on his chest, looked into his eyes, and slowly began moving my hips up and down. 

I couldn’t believe how hot it made me to stare into his eyes as I used his cock to fuck my ass. Knowing that he knew exactly what was happening and that he was enjoying it as much as I was turned me on to no end. When I felt his hands grab my ass and help me bounce on his cock, I knew I was going to cum again; his strong hands gripping my ass cheeks, spreading them so his dick could fuck my asshole while he lifted and lowered me in time to his thrusts, his lust filled eyes staring up at me, yes, I was definitely going to cum again. 

Our pace built and built until I was just hovering over him as he pistoned in and out of me faster than ever before. I screamed in pleasure with every thrust. Just as I was getting close to cumming again, James dropped me down onto his cock and I felt him twitch inside of me. I couldn’t believe that I could feel him cumming. I clenched my ass around him and I felt his dick swell and spurt his cum deep inside. I was so massively turned on by the feeling that my hand dropped to my clit and I masturbated furiously while I felt him shooting rope after rope up my ass. A few moments after he finished cumming I brought myself to my fourth orgasm of the night. It wasn’t as intense as the first, but it was still enough to make my body shake and my knees weak. 

When I finally came down from my orgasm I looked down and realized I had dug my fingers into James’ chest so hard that I’d left deep marks in his skin. 

“Oh my god, I’m so sorry I didn’t mean to hurt you!” I said. 

“Hurt me? You’re fine. Holy shit are you fine. I’ll take a few marks on my chest any hour of the day if that’s what I get in return.” 

“I’m free all day every day for the next 3 weeks before school starts. You can call anytime.” I said with a smile. 

I leaned down and kissed him; a hard, passionate kiss. I had never felt so incredibly satisfied in my life. I’d finally broken out of my shell. No one could possibly tell me what had just happened was boring.