A December to Remember Ch. 01

My mother eye's now had a look of love and passion that I definitely have seen before in Cassie's and Rachel's eyes before certain activities.

"Oh Matthew," my mother whispered as she closed her eyes and gave me a quick kiss on the lips. When our lips touched it felt very similar but in a way very exotic and different. My mother's mouth lingered on mine as I held her tighter in my arms. This was turning into more than just a mother/son kiss. I tried to pull away from her but she pressed with such passion against me that I was helpless in her arms and honestly didn't want it to end. A few seconds later my mother broke our kiss and took a step back.

"I...I'm sorry Matthew that was inappropriate of me...please forgive me..," my mother began as she tried to hurry away. "I just know that you and Cassie are so close and was hoping someday we could have the same type of relationship," she managed to get the words out obviously flustered about our kiss.

"Mother," I whispered. "It's completely fine...that kiss was perfect. Nothing to apologize for and it was very appropriate for our current situation. I love you so much and remember, I am here for ANYTHING you might need. Remember that", I stated.

My mother gave me a genuine smile, nodded her head and headed back into the kitchen.

My head was now swarming. Did she REALLY know how close Cassie and I were? Did she REALLY want the same type of relationship that I had with her? It sounds crazy to think she meant it that way but what about that kiss? There was definitely something there and when I tried to pull away she didn't want me to. Maybe she knew about me and Cassie from the way the three of us were laying in Cassie's bed this morning.

I knew I needed to clear my head so I headed upstairs and hopped in the shower. My member was now semi-hard as I imagined what it would be like to fuck my own mother. If she wanted that I would be there in a minute without hesitation. She was a more mature, experienced version of Cassie. Although she didn't have nearly as perfect body as my sister, she was still definitely a MILF and I'm sure she could teach me a thing or two about how to fuck. She was a surgeon after all and was very detail oriented. My cock was now becoming rock hard at the thought of this but knew I needed to relax and calm down to save myself later for Cassie and Rachel. I finished my shower, laid down in my room for a while, got dressed and headed downstairs to the basement to shoot some pool.

I opened the basement door and heard a few female voices chatting to each other. I instantly recognized Cassie and Rachel's and about a split-second later I heard the bubbly voices of my twin cousins, Becca and Stephanie. I jogged down the stairs and when I hit the bottom I was nearly tackled by the two gorgeous red-heads.

"Matty, we're so glad to see you," they whispered as they each clung to one side of me. "So sorry to hear about your dad," Becca said. "Yeah Uncle Will was like a father to us," Stephanie added as I could see they both had tears forming in their eyes. I had to bite my tongue from saying 'yeah he was apparently a father to a few other people too' but simply replied with a nod of the head.

"It's great to see the two of you though, although it's under shitty circumstances," I replied. "I can see you have been reacquainted with Cassie and the beautiful Rachel," I said as I winked at my girlfriend and sister who were sitting a few feet away. Cassie and Rachel both knew the wink was for both of them, but I had to maintain the illusion that it was for Rachel only. Rachel smiled back and rolled her eyes.

"Yeah Rachel and Cass are the best and we have so much fun together when we hang out at their place every once in a while," Stephanie commented. "I can see why you're with someone like Rachel," Becca added in. "She is gorgeous and so much fun to be around. Obviously has the brains too to get in to Harvard Medical School," she finished.

"Oh Beccs, you are such the flatterer," Rachel laughed as she threw her arm around her. "You're not too bad yourself," Rachel continued as she looked over at me and gave me a wink back.

I had the strange feeling that Becca and Rachel had some type of history. Maybe they were just good friends? Maybe the nights that Stephanie and Becca hung out at Cassie and Rachel's they were doing more than just hanging out...

I realized I needed to for once get my mind off of sex and to stop thinking that every woman in my family/ life is either interested in fucking me or is already fucking my girlfriend or sister. As much as I nearly burst through my jeans thinking about being sandwiched between the two redheads while Cassie and Rachel fuck each other on the same bed, I needed to take my mind off of that.

"Who wants to shoot some pool?" I asked. "Me and Rachel will take on whoever is brave enough to try to beat us," I added with some cockiness.

"You have no chance," replied Cassie. "The three of us will destroy you," she continued with her own flair of confidence. I had a flashback of the tennis match over thanksgiving and was reminded how competitive Cassie can really be.

"How is it fair that you have three people?" I asked.

"Well we're twins so we count as the same person," Becca chimed in right away.

The five of us shared a laugh and began to rack the balls. As I was racking the balls I couldn't help but wonder if Becca and Stephanie could rack my balls in their mouths...I mentally shook my head and focused on the pool table. The time passed relatively quickly as the five of us played a few games. I couldn't help but notice Rachel leaning on top of the pool table to make certain shots. I think she was purposely trying to mimic the same position we were fucking in on Thanksgiving weekend and it was driving me crazy. I felt like I needed my cock inside Rachel's pussy as it hadn't been there since Thanksgiving. The five of us shared laughs and had an overall pleasant time under the circumstances. I decided I couldn't wait any longer.

"Rach, would you mind helping me out with something upstairs?" I asked in a very serious tone to throw her off.

"Uh...yeah sure babe," Rachel replied as she followed up the stairs behind me. I walked at a quick pace through the house and up the stairs to the second level. I opened my dad's office door and stood to the side as I motioned for Rachel to enter. After Rachel entered the office, I followed her in and closed and locked the door behind me. The office was ornately decorated with rich mahogany wainscoting and a solid mahogany desk at the one end. There was a desk lamp that was currently providing the only source of light in the room. A family portrait hung on the wall behind the desk.

"So what did you want me to help you out with?" Rachel asked as she was leaning her butt against the desk and was casually flipping through a stack of papers.

I quickly walked over and surprised Rachel when she wasn't looking. I grabbed her ass cheeks, lifted her up and sat her on the edge of the desk. I dug my face into her neck as I kissed and bit on her silky smooth skin and ripped open her white blouse revealing a bright red lacy bra.

"Oh so that's how it's going to be eh?" Rachel queried excitedly while running her fingers through my hair. Rachel was frantic and was fumbling to pull my shirt over my head and yank down my pants. She was successful in removing the shirt but I didn't let her get further than that before I reached under her skirt and pulled down her red lacy panties. God I loved this woman.

As soon as I had knelt down and slipped her panties off of her feet, Rachel swung her legs over so she was now lying on the desk, knocking over papers and trinkets in the process.

"Oops!" Rachel mockingly squealed. "Looks like someone is going to have to punish me now," she grinned as she rolled across the massive desk and onto her stomach. She had her hands flat in front of her and her tits were pressing hard into the surface of the desk. Rachel arched her gorgeous ass into the air which caused her skirt to slide up to her hips.

I was left standing there staring at the wet slit and tight rosebud of my dream girl. She was sprawled across my recently deceased father's desk and she was BEGGING me to take her from behind and fuck her. She was looking back at me, breathing heavily and biting her lower lip.

"I've been very bad Matty...I need to be spanked," she whispered in the most seductive voice that has every graced my ears. I undid the zipper on my pants and let them drop to the floor. My cock was now hard as steel and was resting on the desk surface. I ran my hand down Rachel's spine from her neck to her ass cheeks and could see the goose bumps form on her skin as I did so.

"Mmmmmm," Rachel purred with closed eyes as she playfully kicked her legs back and forth and let out the occasional shiver. When my hand got to her ass I took my hand and gave her a light smack on her left ass cheek.

"Oh is that it?" Rachel mocked me as she looked back and smiled. I smiled back getting even harder that she was enjoying this and asking for more. I took my hand and placed it on her right ass cheek. I stared lovingly into her eyes and brought my hand up. Rachel was biting her lip in anticipation as she slightly nodded at me with a look of passion and desire in her eyes. I brought my hand down to a loud THWAP on her ass cheek as I spanked her much harder this time.

"OOwwww," Rachel whimpered with a smile on her face. "That was much better. I deserved that for being a naughty girl," she alleged.

I walked over to the edge of the desk so Rachel's wet pussy was right in my face. She crawled backwards to make sure she was as close to the edge as she could be to provide me more access. As I placed one hand on each of her ass cheeks and began to spread them wide, my cock was rock hard and twitching on the desk. I knelt down and in a quick motion ran my tongue from her slit to her tight little rosebud.

"OH MY FUCKING GOD MATTY!" Rachel shrieked a little louder than she had anticipated. "I've been waiting for those lips to taste my pussy again...it's been far too long," Rachel moaned. I grinned as I swirled my tongue around her clit and began to gently suck and nibble on it. Hearing Rachel's breathing and moaning become more ragged, I quickly slid two fingers into her tight pussy. I quickly sped up the pace of my fingers into that tight wet channel as Rachel's body was trembling on the desk.

With my mouth now free, I began to kiss and bite on Rachel's ass cheeks while my finger circled her tight rosebud. I let my index finger rest on her asshole while my other hand was still plunging in and out of her to the sound of wet slapping that echoed off of the wooden wainscoting in the room,

"Fucking do it baby! Stick a finger in my fucking ass," Rachel barked through clenched teeth, the pleasure and anticipation obviously building up. I licked my finger and then slowly started inching it into Rachel's unbelievably tight asshole. This is the first time Rachel and I had done anything like this with each other. I got into the first knuckle and could not believe how tight it was. I kept inching forward more. Every little bit that I stuck my finger in resulted in my cock getting harder and now the glistening of precum could be seen on my red tip. I was aching to stick my hard cock inside her tight ass and was hoping that she would beg for it. I didn't want to go there if she didn't want to but I had a feeling that she would ask for it any minute.

I stuck my finger the rest of the way in with one quick movement that caused Rachel to squeal out in a combination of pleasure and shock. She began to rock back and forth on my finger while I still worked her pussy with my other hand.

"OHHHH GODDDDDD BABE...I need your cock in me...I don't care where it goes, I just need it in me now...Fuck me baby...FUCK ME!" Rachel panted in between breaths. I removed my hand from her pussy and she immediately replaced it with her own until I could put something bigger in there...If I was going to fuck Rachel in the ass, I would need some lubrication and I knew where my cock had to go.

I climbed up onto the desk and knelt behind Rachel. I pulled her body against mine so my rock hard cock was resting on her lower back. I began kissing from her lower back all the way up her spine. I could see even more goose bumps on her skin as I got closer and closer to her neck and her perfect face.

"I am going to fuck you so hard in your tight pussy and then I am going to fuck and cum in your ass," I whispered to Rachel. I could see her eyes shoot open wide and a smile plaster itself on her face.

"I need it so bad baby," Rachel whispered back. "Fuck me Matty...fuck me good and hard." I grabbed a handful of Rachel's thick brown locks and gently yanked up a bit so I could kiss her passionately on the mouth. Rachel's tongue was immediately swimming inside my mouth as she tasted her own juices from my mouth. Rachel more than gently bit my lip which caused me to automatically jump back a bit. Rachel looked at me with a devilish look.

"I said FUCK ME," Rachel demanded. I could see her playfulness in her eyes but could also tell that she needed it right now. I straightened back up and grabbed my rock hard cock in my hand. I positioned the tip to Rachel's wet channel and without any warning or heads up, I shoved it all the way in and bottomed out inside of her tight cunt. I think this caught Rachel a little of guard as she dropped her head down and let out a primal groan of pleasure.

I grabbed onto Rachel's curvy thighs and got myself into the right position. I fucked her hard and fast like we both wanted. Rachel was working in time with me and slamming back on me as I was thrusting forward into her. The wet sounds of my cock in her pussy and her ass cheeks on my pelvis filled the room. Rachel and I continued at this pace for a few minutes. I could tell that she was getting close to cumming as her moaning slowed down and came in more sporadic moments.

I reached one hand down and began to furiously rub her clit. I then took my other hand and wrapped in her brown hair. With Rachel thrusting her hips backward, I didn't need to focus on holding onto her hips. While I was rubbing her clit I pulled her head back so I could whisper in her ear once again.

"I am going to make you cum and then use that wetness to fuck your ass," I whispered. "Is that how you like it?" I queried in a dominant tone.

I could see Rachel's face was flushed and she just bit her lip and nodded in agreement.

"Pull...Pull my hair harder," she managed to get out in between breaths. "Yank it hard when I say I'm cumming!" My face lit up at this as I continued to fuck Rachel's pussy fast and hard. I was pulling on her hair pretty hard which gave me some different leverage. Less than a minute later I heard Rachel scream.

"UGHHHH FUCK...FUCK IM CUMMING...OH GOD...FUCK!" Rachel's body shook under her orgasm as I really started pulling hard on her hair. I felt like I was going to cum inside her myself if I kept up any longer. I managed to hold it together while she came down from her orgasmic high. I could see her forearms trembling from keeping herself up through all of that. With a wet slurping sound, I slid my still stiff cock out of her wet tunnel and watched as her juices dripped onto the desk surface.

My cock was covered in her precious fluids and was creating the perfect lubrication for what we were going to do next. Rachel had her eyes closed and was trying to regulate her breathing as she had nearly stopped breathing altogether when she came. I placed the head of my glistening sock at the entrance to her asshole. Rachel's eyes shot open while she looked back at me in anticipation and desire. I slowly nudged my cock a little forward and was met with substantial resistance.

It was going to be tighter than I thought and hoped it wasn't going to hurt her. I looked at her for confirmation that she wanted to continue and she nodded. I pushed harder this time while grabbing onto her hips for fine control. I was pushing hard when finally the head slipped in and the resistance was substantially decreased. My cock head was now inside of Rachel's tight asshole.

"oh my GOD," Rachel hissed. "It feels so much bigger in there...I love the feeling!" I couldn't really focus on what she was saying as I was experiencing my own sensations. This was tighter than anything I have ever experienced before. It was to the point where it wasn't uncomfortable but if I turned to either side, It felt like I could have broken off inside of her.

"It's so fucking tight babe," I replied back. "This feels amazing" I began to put a couple more inches inside of her and was met with little resistance though the pressure still seemed to intensify. I started to gently rub Rachel's clit to increase her pleasure. Rachel let out a long moan.

"Holy fuck when you do those together it's insane!" Rachel said. As I was rubbing her clit I slid the rest of the way into her ass in one motion.

"OHHHH...OHHHH...fuck...oh my god," Rachel cried in between long deeps breaths. There I was with my cock buried deep inside one of the women I loved most in the world. Like earlier, Rachel began to move her body away from me and back as she drove the pace. I could see that her forearms were really shaking hard. I bent down on top of her and grabbed her shoulders. I kissed her between her shoulder blades and then pulled her arms behind her and held onto her wrists with my hands. I was now completely supporting her and she could remain focused on driving my cock into her incredibly tight ass. With her hands behind her, her tits were just rubbing the top of the desk and I had an amazing way to control the pace of this incredible moment while taking in the incredible view of my cock stretching her tight rosebud.

Using her wrists as leverage and having gotten used to the feeling and pressure, the pace quickly increased and I was slamming into Rachel's ass with so much force we were moving along the desk. Rachel occasionally looked back and I could see her flushed face in the throes of passion. Sweat was glistening off her brow and her hair was in quite the mess. She looked radiant and gorgeous in this moment and I couldn't imagine my life without her.

"ohhhh Matty I need you to cum in me...cum in my ass baby," Rachel purred which brought me out of my momentary epiphany of how much I really loved this woman. Rachel freed her wrists from my grasp and supported herself again. I placed my hands on her hips and thrust in harder and harder as we were both reaching the point of satisfaction we had been building towards.

"Oh. Fuck. Matt. Oh. GOD. Babe," Rachel would shout as each thrust of my cock plummeted into her tight crevice. I had finally reached my breaking point.

"uhhhhhh God Rach I'm gonna cum...fuck!" I shouted.

"Cum in me babe! Fuck me hard and spill all that cum into my ass! Fuck I'm gonnna...cum...too!" Rachel screamed back as our bodies shook with passion. I wrapped my arms around Rachel's chest and fucked her like a jackhammer until we both came into oblivion. Rachel and I each stopped talking and only let out guttural sounds speak for us as we came together as one. I could feel stream after stream of my seed shooting into her ass. I then lifted her up so we were both kneeling as we passionately embraced while our orgasms died down. I could still feel my cock throbbing and shooting streams of cum into her ass as we kissed with the passion of two lovers making love for the first time. I held Rachel tight against me until we were both back to breathing regularly and our flushed hot skin returned back to normal.

I finally let go as Rachel and I looked into each other's eyes and shared a moment that was extremely special. Rachel and I both began to get dressed. I threw on my pants but when I went towards the door to where my shirt had landed, I noticed a flash of auburn hair as the door shifted. I then heard hurried footsteps down the stairs. I paused for a moment to decipher what I thought I saw. Was it possible that one of the twins was watching us? Downstairs in the basement it looked like Rachel and Becca were really close. Maybe the four of them were as close as Rachel and Cassie were now? Maybe my sister had been fooling around with her twin cousins and girlfriend while they were away at University...