Chapter Seven

 Bailey

 

Every smack from Tyler’s hand sent me closer and closer to orgasm. “You like getting spanked don’t you?” I loved the caveman like attitude Tyler had gotten since seeing me stripped bare.

“Yes, Mr. Cress,” I answered, right as another smack landed against my ass. My pussy pulsed with every movement, making me crave his touch that much more.

“Good, because your ass has never looked better than it has now. Hell, I wish you could see how beautiful it is, in this shade of red.” He soothed the sting from his smack and landed another blow on the other ass cheek. Oh, my Lord! I could feel the build up of my orgasm in my belly, as it worked its way higher, and higher…and just as I was about to fall over the edge, Tyler stopped wiggling two fingers in front of my face.

“What are you going to do?” My voice cracked as I questioned him, out of breath and on the verge of pleasure I had never felt before. I wasn’t sure what to think right now, all I knew was that I was almost there, and he had ripped that pleasure from me.

“Watch and learn sweetheart. By the time I’m done with you, you’ll never want to miss out on this inventive way to climax ever again. It’s not only about the pussy you know…There are tons of other pleasure points on the human body, and the asshole is one of the best.” He soothed me letting me know he knew what he was talking about but from the way he had been touching me, there was no denying he knew what he was doing.

“I need more… I was so clooooseeeeee…” I panted, wanting him to do whatever it was that he wanted to do so that I could climax. Though, doubts did start to form in my mind as I waited to see what would happen next. How far could we really take any of this with them being my bosses and would I end up hurt in the end? Could all this just really be no strings attached sex? Part of me thought I might be ok with that, but then the other part of me wondered if I would end up wanting more from these guys emotionally if we delved into a sexual relationship, but I didn’t know if they were willing to take it that far. If I was ready to lose my virginity, twin brothers were certainly the way to go since not everyone got such an amazing opportunity.

“You just breathe, and I’ll do all the work.” Tyler had me right where he wanted me, and if I was being honest I would admit that I didn’t want to be anywhere else.

Without saying a word he walked over to his desk pulling out what looked to be like a tube of lube. “Um, do you normally have a bottle of lube with you, handy to just whip out at your convenience?” I laughed. 

His eyes sparkled with excitement as he laughed at my comment. “This ain’t just any old lube Princess. This stuff is golden. It goes icy hot, for extra sensation.”

“Hmmm, I guess. I just hope it doesn’t hurt.” I admitted unsure why I felt the confidence to tell him I was worried.

“Baby, one thing you will learn about me is I always come prepared. I want to make sure you are comfortable and I don’t want to hurt you on your first experience with having fingers in your ass. I want you to feel only pleasure, so that’s why were using the lube. If anything it would hurt without it. ”

“Thank you, for vowing to take such good care of me,” I spoke softly, before sucking in a deep breath. With two fingers that he lubed up for better pleasure for me, he slowly and gently pushed them into my asshole as I bent over the couch. Pain and pleasure both seared me, as he wiggled his fingers back and forth stretching my tight hole. Cries of pleasure escaped my lips as he pushed deeper and deeper inside of me until he had both fingers seated as deep as he could inside my ass. I shifted my body back and forth for enhanced sensuality and as soon as I started moving I could hear Tyler’s moan of pleasure enter my ears.

“Oh God, Princess. Your asshole is so tight and I can see your little pussy starting to turn wet with need.” Tyler’s dirty words just added to the pleasure.

I was enjoying this just as much as he was. I tried to speak but the pleasure was becoming too intense to talk through. All of the sudden I heard him unzip his pants, heard the shake of his belt unlatching. I turned my head around and watched as he tore his pants off with a hunger that I now understood. Holy fuck was his cock huge. My eyes bulged out of my head. Had it been that big the first time I saw it?

I wasn’t sure, but now that I was really looking at it, I noticed how veiny, and thick it was and I wanted it. I was filled with so much pleasure in that moment that I moaned out that I wanted him to fill my asshole with his cock, because I knew then that he was headed and aiming in that direction anyway, and I had no issues with it now. I wanted to be fucked in the ass by this handsome stud on the couch in his million-dollar office.

“Tyler, please,” I cried out, not even realizing at first because of the amount of ecstasy that was consuming me.

“You want this ten inches in your tight as fuck ass?” He slapped my ass with one hand as he continued to move his fingers in and out of my asshole.

“Yes, please, I need it. I need more.” My face was flushed with passion, as I begged for more, more of anything, whatever he would give me.

“What you ask for Princess, you receive. I promise you’re about to have the best orgasm of your life, you may end up wanting to always have anal sex instead from now on.” With that, I could feel him center his cock at the entrance of my asshole as his fingers disappeared leaving me almost cold.

“I want you…” I gasped for air because right then, he started to push in fulfilling every single pleasure I had asked him to meet.  He worked the head in, and then every last inch of himself until he was seated with his balls against my pussy. At first, it stung a little even with the lube on his dick, and tears filled my eyes as he rubbed with his thumb small circles against my clit, while stretching my asshole impossibly wide. But once he was fully seated, further in and started to open my ass cheeks wider and wider, I began to love the new sensations that were running rampant through my body.

 I could feel the icy and hot combination blending together inside of my ass and I loved the way it made me feel, along with having his huge cock move in and out of me ever so slowly.

“Your fucking ass is so tight, and my balls are pounding against your pussy… I bet you like that don’t you?” He growled, his teeth nipping at the back my neck. I had never felt such intense pleasure before, and as I started to moan louder, he started to move faster his movements going from slow to a hunger that couldn’t be met. Every thrust into my ass became harder and faster until I was torn over the edge with a climax that rocked my entire body, and axis off, just with the way he had opened my hole so incredibly wide.

“I’m not finished with you yet baby. You deserve multiple orgasms today. I bet you’ve never felt this much pleasure in your entire life before now?” Tyler purred, wrapping my hair around his hand, and pulling my head back, forcing my ass to make more of his huge cock.

I purred like a kitten, rubbing my ass against his balls. He was right, in fact, I’d never been sent to sexual heights like this before. I was breathing fast, and my heart was beating so hard I was sure it would beat right out of my chest.

 “Take your hard cock and fill me some more, I love the feel of you in my ass. I want you deeper, and harder, give me your best Mr. Cress.” I took the leap because I knew I needed him. If this was the way pussy sex felt too, I knew I would be in for a treat once it actually happened, and there was no turning back now. Was I ready to completely lose my virginity here in this office?

“You want it deep don’t you? I always knew you were a bad girl?” He pulled his cock all the way out slapping it against my ass as if he was going to spank me with it.

“Yes, I’m ready. Take me,” I exhaled ordering him to give me more, so much more.

Seconds later he was plunging into my ass, his hips thrusting back and forth, as he placed one hand on my hip for support so that he could to rock up and down move his hips in the perfect motion inside me.

“You asshole is mine,” he growled, thrusting harder, so hard that it almost hurt.

“Fuck me, Mr. Cress,” I responded, enjoying this more than I could have ever imagined I would. I felt an instant attraction to both twins, but now that I was in the middle of my first anal experience I couldn’t help but notice how raw and strong the connection between all of us was becoming. My feelings were beginning to take root, and it both scared and thrilled the fuck out of me.

Then, to my pleasant surprise, he was back to playing with my asshole with his fingers while his ten-inch cock still explored the inside of me. His touch was maddening as he rubbed the rim of my hole with his index finger right as his balls slapped against my pussy. I screamed in pleasure as he took his hands and spread my ass cheeks wider.  

“I wish you could see how beautiful you look on this end, with your asshole filled to the brim with my cock,” he moaned out, spreading me, so wide it almost hurt. “My cock looks so good in your asshole. Mmm, fuck yeah, this is hot, just like I knew it would be.” He panted, alternating between grunting and growling. He was spreading me as wide as I could go and I loved it every fucking minute of it. We were both wet and slippery from my juices. “You’re so wet,” he moaned through his own pleasure.

Suddenly he gripped me on the hips and pulled me back so that I was sitting on top of him. The penetration made his dick go even further into my ass and I was going wild from the intensity of it. “Ride me, Princess,” he panted, obviously in as much ecstasy as I was at the moment.  He leaned in to kiss my neck and it sent chills down my spine. His breath smelled like mint and it was intoxicating, to say the least.

 He nibbled on my earlobe and continued to rock me on his lap. Then he hugged me close to him and squeezed my tits in his hands as they bounced up and down. Tyler continued to hug me close to him and I rode him harder, as I moved my hands behind my head and dug my fingers into his hair from the back with a need I wasn’t even aware I had. I wasn’t expecting the anal sex we were sharing to be so engaging but as we held on to each other in the heat of the moment I could feel the potential for a wonderful relationship to bloom.

He took hold of my hips, taking charge and helped me bounce on top of him. His dick went further and further into my tight asshole and as he plunged in and out, the deepness of his huge cock hit me all at once, and I knew that I had just discovered what it felt like to have my pleasure climax points hit from the inside of my ass in just the most perfect way possible. I fell over the edge seconds later, my entire body trembling, as droplets of sweat dripped from my forehead and down my face.

It wasn’t until after I had recovered from my second orgasm that I noticed that Logan had entered the office and was frantically locking the door behind himself. I had no idea how long he had been there with the door open or if he had been watching Tyler and me cum together in a frenzy of sexual peaks.

“Could you hear us from outside the office door?” Tyler asked his brother as he looked up and noticed his twin coming into the room. He had a fleeting look of concern in his eyes.

“Nope, there was not a word on the outside, so please, do carry on.” Logan grinned and began to frantically undress from the waist down. His slacks came off in a heap as he practically ran towards us. He had the hunger of a wild lion in the Sahara who had just found its prime meat and was ready to pounce for an epic feast.

“You look so sexy, Bailey.” He spoke to me directly and came to go under me while I sat on top of him, with Tyler still in my ass.

“Oh wow, what a view.” Logan smacked his lips and looked ready to dive right into the fun.

“Look up at me baby. Yeah, that’s right. Look at this ten inches right on display for you. Look at how hard you’ve made my cock. You did this to me; you are so sexy and beautiful. Why don’t you give my cock a little reward for waiting so patiently for you? How about you give it a little suck?”

I looked at his throbbing cock. It was beckoning me, and I couldn’t help myself. The door was locked, and I knew that nobody could just walk in here. We were having our private moment, the three of us, together, becoming one. I took his cock in my mouth and began to circle it around the head. It must’ve been doing something for him he arched backward with his hands behind his head. “Oh yeah, let me fuck that dirty little mouth of yours. For a little virgin, you sure seem good at sucking dick.”

He made me feel proud, wanted and needed and I loved that about both of the guys. They never slacked on giving me compliment after compliment. My self-esteem had tripled in size just in the few days I’d worked here.

But I knew that he now would want to have his own way with me. Now that Tyler had fucked me in the ass I knew I was ready for anything. I knew that Logan would want to get his fill of me, to experience what it was like having sex with a very inexperienced little virgin. They both seemed to get off on the thrill of taking me as their own, and who was I to argue? I got to have multiple orgasms because they weren’t shy about giving those out either.

 I just didn’t know how sure I was about letting them both take me at once. I was still feeling a little overwhelmed, and I knew I had the job solid but something made me think I couldn’t go all the way twice in a row. I stared up at Logan as his eyes rolled back in his head as I continued to work his cock in and out of my mouth, all while Tyler was still seated deep inside my ass. Could I get used to this? Or was I giving away too much at once?