Chapter 2: Best Present Ever: Milf Neighbour

It was the 31st of December and other than a quick blow job from my baby sister Sandra, life returned to normal. The family had done our traditional double feature at the movie theatre we did every December 27 (I have no idea why, but it had become a tradition nonetheless), I met up with my old buddies for an all-night Marathon of Dungeons and Dragons on the 28th, and spent the 29th working on a paper in the day and played board games with the family and grandma, minus sis who was working.

That night, while the family played taboo, Sandra texted me.

Allison is back and she will be coming to meet you tomorrow afternoon ... she is dying to learn more about Harvard.

I smiled, although I hadn't met her yet, there was something about her I couldn't quite place. Oh sure I enjoyed fucking my sister and Beth, but their shallow personalities and vapid intellect was annoying. Allison was an intellectual and obviously a submissive sexual being ... maybe I could have the best of both worlds ... a submissive girlfriend who I could actually converse with at a higher level than 'I need shoes to match this outfit.' I hated stupid and vain people.

On the 30th, I shot an early load down Sandra's throat and continued on my research paper until Allison arrived later that afternoon.

Her shy smile enhanced her adorable dimples, her crystal blues eyes sparkled behind her too nerdy for her own good glasses and her brown hair in pigtails had me smitten the moment I met her. Unlike Beth who I just wanted to fuck, Allison I wanted to get to know before I fucked her.

Sandra introduced us. "Allison this is my big brother Matthew," she said slyly stressing the word 'big'.

Allison shyly said, "It is very nice to meet you."

"You as well," I smiled, "I hear from Sandra that you are hoping to attend Harvard."

"That is my dream," she replied, a sudden twinkle in her eyes.

The next hour we talked academia and I was instantly smitten with her. Unlike most insipid girls, I could actually have an intellectual conversation with her. I asked her if she would like to come down to Harvard for a tour sometime. She was giddy at the offer and we agreed on a date in February if her parents approved, which they would, and I asked if she would like to go out to a movie tonight.

Her face went flush as she stammered, clearly surprised by my offer, "I-I-I can't. I am spending New Years babysitting."

"Oh, ok," I replied.

She quickly added, "But otherwise I would love to."

"Well, I fly out on the second, so are you free tomorrow afternoon for a matinee and dinner," I asked.

"S-s-sure," she stuttered, clearly excited by the idea of a date with me, something I was not accustomed to.

"It's a date," I announced, clarifying any doubt she may have had of my intentions.

"Ok," she said, seemingly as surprised at my request for a date as I was to have a girl say yes for a date.

We chatted some more before she had to head back home to get ready for babysitting after she said goodbye to my sister.

Once she was gone, Sandra popped into my room and said, "You sly dog, a date. What are you planning on doing, adding her to your harem of whores?"

I instantly got defensive. "No slut, I actually want to date her."

Her face went red, but she didn't respond like she would have a week ago before she became my little sister slut slave. Instead, she asked, "So what is the plan for tonight?"

"Mrs. Raske is my New Year's Eve gift to myself," I answered. Mrs. Raske is our hot MILF neighbor and mother of my high school nemesis Tyson. But, best of all she is Sandra's lesbian pet and has guaranteed she will obey me.

"She will love you," Sandra said, before adding, "but doing her at her son's party may be a challenge."

"I want to have my cum leaking out of her while she talks to him," I added.

"You really are a conniving bastard," Sandra smiled, clearly liking my plan.

"Make it happen," I ordered.

"Will do, big brother," Sandra agreed.

...

Although still farfetched I had also began planting the seeds for the potential seduction of my mom. I had been complimenting her, giving her hugs, kisses on the cheek and spending more time around her. She noticed, "What has gotten into you, Matthew? You haven't paid this much attention to me in years?"

"Living at college makes one realize how much motherly nurturing is critical to proper psychological development," I said, which was true, although I knew that years ago.

"Well anytime you need me, I am here for you," Mom offered, giving me a hug.

I smiled thinking what I needed her for as I said, "I plan to take you up on your offer very soon."

...

At the party, I came in with cheerleader Beth, who a few days earlier would have rather died than have been seen with me. She had her arm hooked in mine with a big smile on her face, feigning to be oblivious to the surprised looks she was getting.

Having a popular cheerleader on your arm changes everything. Suddenly I wasn't the geek kids mocked, but the college dude dating the hottest chick at their school. It was extremely gratifying, especially when Tyson saw me at the party.

"What the fuck are you doing..." he began than froze when he saw Beth holding my hand."You got to be kidding me."

Beth spoke for me, "Matthew is here with me. Do you have a problem with that?"

Tyson glared at me, but said, "No, no problem at all."

Beth smiled, "I thought so."

Once Tyson walked away, Beth whispered, "He acts tough but he is a pussy with a small cock."

"You fucked him?" I asked,

"If you can count his cock in me as fucking," she shrugged, which had me laughing hard.

Beth said, "I am going to find your MILF slut-to-be."

"You do that," I said.

The next hour I learned what high school parties were like, all the ones I hadn't been invited to. Although dancing with Beth in such tight quarters was fun, the whole scene was not. Getting bumped into by drunks, having drinks spilt on me, the loud repetitive dance music was annoying. Finally Sandra gave me a nod from afar, her hand in the air to imply five minutes and my cock grew instantly. A song later, Beth and I squirmed our way through the throng of drunk, insipid high schoolers.

Eventually we meandered our way upstairs. Beth knocked on a door three times and a moment later it was opened by Mrs. Raske who was clearly nervous and uncomfortable. She stammered, "C-c-come in."

We quickly did as she closed and locked the door.

"Get back to your task," Sandra demanded, sitting on the edge of the bed, her legs spread open.

"P-p-please my husband will be home in half an hour," she pleaded.

"Then you better hurry," Sandra demanded.

She looked at me, humiliation all over her face, dressed classy in a red cocktail dress, black pantyhose and three inch heels. She turned away and went to my sister, dropping to her knees and leaning forward towards my sister's pussy.

Beth surprised me also dropping to her knees and retrieving my fully erect and awkwardly positioned cock from my pants. Without a word, she took my cock into her mouth and sucked like the pro she was.

Sandra said, "Matthew, I hate to rush you, but we sent Mr. Raske out for more ice and appetizers. We don't have a lot of time to use our slut."

Deciding to impress Mrs. Raske with my control over two of the hottest girls around, I said firmly, "Sandra come and get my cock ready."

Sandra didn't hesitate as she moved off the bed and joined Beth on the floor, both cheerleaders now worshipping my cock.

Mrs. Raske turned around, but remained on her knees as she watched the two girls take turns sucking my cock.

"Hungry, Mrs. Raske?" I asked, smiling with the newfound confidence that the past week had given me.

Surprisingly, her earlier shame had disappeared completely as she crawled towards me with a hunger in her eyes like a predator going in for the kill as she answered, "I am famished Matthew."

Reaching me, Beth and Sandra moved away and the sexy MILF looked up at me as she reached for my cock. "How long have you fantasized fucking me Matthew?"

I groaned, "Since I was old enough to stroke myself off."

She opened her mouth and took my cock between her lips. She bobbed hungrily for a couple of minutes, deep throating me with ease, and somehow creating a tornado like sensation in her mouth with her lips, tongue and excess saliva.

Taking my cock out of her mouth, she looked up and said, "I want to feel your cock in me sexy, but my husband will be home soon. So please fill my mouth with your cum and then meet me at midnight across the street at the Wilson's for the best New Year's Ever."

I looked at my sister and she explained, " Apparently the Wilson's are gone for the week and she has the keys because she is sort of house sitting."

"What about your husband?" I asked, moving my cock around her sexy lips.

"Don't worry about him," she smiled, taking my cock back in her mouth.

Her lips were like a vacuum as she gave me the most amazing head I had experienced in my brief experience. I knew I wasn't going to last long and moaned as she bobbed back and forth with such beautiful perfection. "Does my new fuck-toy want my cum?"

She grabbed my ass cheeks and pulled me deeper into her mouth than I thought physically feasible and then grabbed my hips and moved them back and forth.

I was confused at first until Sandra laughed and said, "Fuck your slut's face."

Catching on, I grabbed Mrs. Raske's head and began pumping my cock in and out of her perfect lips. The cocksucking sounds were loud and the tornado sensation, plus the reality of a long held fantasy coming true was too much and I shot my load into the MILF's mouth.

As I slowed down, she returned to her hungry bobbing, retrieving every last drop of my cum.

"He's home," Beth called out from where she was standing by the window, she had been keeping lookout for Mr. Raske.

Mrs. Raske slowed down, swirling her tongue around the top of my now sensitive cock head, not panicking about being caught in such an act. Finally, she allowed my cock to leave her mouth and she stood up smiling. "That was delicious, Master."

I tried to hide my awe as I replied, "That is nothing my pet. Wait till I get you alone at midnight."

Looking at me, she purred, her tone dripping with submissive sexiness, "I can't wait."

I pulled my pants up just as there was a crash at the door, thankfully locked, followed by Tyson's voice, "Mom are you in there?"

I could have hid, but instead made sure Mrs. Raske was respectable before I opened the door.

"Hey, Tyson," I greeted, smiling smugly. The look of confusion on his face was priceless.

"What the hell are you doing in my parents' room?" He asked, instantly pissed.

"Just helping your mother with her," I paused, causing anxiety for all I imagine, "computer issues."

Tyson's anger quickly faded as he said, "Well get the hell out of here."

Mrs. Raske, her tone clearly in mother mode, scolded her son, "Tyson apologize this second. Matthew comes here and helps me selflessly and you treat him with disrespect."

Tyson went from tough and smug, to weak in a heartbeat, as he said sheepishly, clearly embarrassed by being scolded in front of his peers, "Sorry Matthew."

"No problem," I shrugged, "I will always be available if your mother needs her system looked after."

Sandra laughed at my sexual innuendo, but Mrs. Raske surprised us both when she added, her meaning dripping with naughtiness, "Thanks a lot Matthew, you really have a way with the mother board."

"I'm still learning," I shrugged.

"Well practice makes perfect," the MILF quipped back.

I laughed, looking smugly at Tyson, "I have learned that is always the case."

I turned to Beth and said, "Let's go babe, l am sick of hanging out with these children."

Beth quickly joined me, adding, while looking directly at Tyson, "Yes, Iets go somewhere we can be alone." She stressed the word 'alone' in case Tyson was too insipid to catch on to the obvious implication.

I grabbed her hand and led her past my ex-bully, down the stairs and out of the house. Once outside, I burst out laughing. "Shit, that was fun."

"The look on his face was priceless," Beth agreed. "By the way, watching his mom gobble your cock got me all hot and horny." She grabbed my cock through my pants and gave a firm squeeze. "Think you got enough for me, sexy?"

Playing coy, I replied, "I don't know."

Surprising me, Beth pulled me back into the party, back up the stairs, passing Tyson as he headed down the stairs back to the party, and into the bathroom. The hunger in her eyes made her intentions obvious. As I passed Tyson again, I shrugged, giving him a 'what can you do' look.

Reaching the bathroom, I turned and gave him one last wink before I disappeared into the bathroom with my beautiful cheerleader plaything.

As soon as the door was closed and locked, Beth's body crashed into mine, my back crashing into the door. Her firm breasts pressed against my chest and her tongue swirled inside my mouth. A minute of intense passion was finally broken when she said, "Please, Matthew, fuck me."

"I could use a snack first," I quipped, pushing her to the sink counter and them lifting her up on it.

I parted her stocking-clad legs apart and buried my face in her sweet, already very wet, nectar. Her scent was addicting and I lapped hungrily determined to get her off with my tongue. Pleased that she had done as instructed and gone commando.

She seemed to like it as her moans got louder exponentially in just a few seconds before she began to get animated. "Oh yes, baby, your tongue feels so good on my cunt."

Hearing the words, especially in her sexy English accent, had my clock rock hard and I was determined to get her screaming with pleasure. I explored every inch of her pussy lips, inside and out, before focusing on her engorged clit.

"Fuuuck, oh God, don't stooooop," she moaned, wrapping her legs around my back and grappling my head pulling me deeper into her oasis of sin.

Her clit between my lips, I shook my head sideways and seconds later was rewarded with a gush of Beth's cum.

"Fuuuuuuck, yeeees, I'm comiiiing," my fake girlfriend bellowed, loud enough that anyone in the hallway would know exactly what we were doing.