Complex Family Ch. 02

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Brandon and Ashley spend the holidays in Chicago.
2.1k words
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Part 2 of the 14 part series

Updated 10/30/2022
Created 06/09/2010
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Thanks to luvtaread for editing

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The tours the next day went rather well and Ashley seemed to impress both schools. It turned out that once you piece together all of the classes from the various schools she had started and not finished it added up to more than enough to graduate. All that was left was for her to do her student teaching and take a few certification exams in the spring.

The best part of this was that, provided she finish a few of the papers she had started in other classes, Ashley was cleared for student teaching that spring so she only needed to find a school that would take her. As Brandon's mom was fairly certain she could get Ashley a spot in the district she worked for this was not much of an issue.

A few days later Ashley met the rest of the family at Thanksgiving dinner. Brandon was relieved to find that she was well received and that pretty much everyone liked her. Gina especially got along with Ashley right off the bat and the two spent most of the day talking to one another. It was clear they were fast friends.

Brandon and Jack were not sure whether it was good or not that the two women got along so well, but Brandon was pleased they got along. He did note that at one point Gina was showing Ashley her ring.

As he noticed this his brother said, "Look out little bro, they're having the ring discussion over there. Better get a move on."

Brandon just nodded and was saved by the call for dessert. Rings were on his mind certainly, but as he had told Ashley earlier this week he wanted some time in normal life before making that particular purchase. Besides, he needed to get the money together for the ring first. Fortunately that was the only mention of rings the entire night and soon after desert Ashley and Brandon left for home. Full of food both gave in quickly to the tryptophan and fell asleep.

Over the next few weeks Brandon and Ashley enjoyed the holiday season together. When they were not working that is. Ashley set to work on her papers, which thanks to Brandon backing up his hard drive to a server nightly, had survived the accident. On days where she was busy working, Brandon earned some extra cash by helping a friend who owned a holiday decorating service.

Shopping too was more fun with Ashley along, though to be truthfully a far more time consuming process than if he had gone alone. He had to admit she was helpful especially with Gina, as her new friendship with his sister-in-law made it possible for him to give Gina something other than a gift card this year.

Brandon was just glad Ashley was not one of those day after thanksgiving shoppers. When he had asked her about it on Black Friday she had said that although she wasn't Katy was. In fact if not for his mom's invite she would certainly be waging war at the malls in Boston with the energetic blonde.

The first week of December brought work for Brandon. He would have liked to stay with her and show her the area, but he realized that would not be realistically possible. Fortunately Ashley had schoolwork she really wanted to finish up so it worked out for the most part. Her new friendship with Gina also helped because, as Gina was a stay-at-home mom, she was around a lot during the day and Ashley made frequent visits while getting her bearings of the area.

The best moment of the holiday season by far came about a week before Christmas. Brandon awoke that Saturday morning to Ashley saying, "Brandon! Brandon! Look darling it's so beautiful."

Brandon sat up and looked at Ashley standing next to the window looking as lovely as usual and thought, "It certainly is."

Before he rose to see what had inspired the awe, although he had a good idea. Sure enough he looked out to see the ground blanketed in a fresh layer of bright white snow as small white flakes floated down. It was a scene right out of a postcard. Brandon smiled at the childlike look of joy on Ashley's face and kissed her on the cheek before holding her from behind. They stood there a while until the wonder wore off and the need for breakfast took over.

At least for him it did as he left she asked, "Where are you going?"

"To make breakfast. If you want to join me I think the living room window has a much better view of the snow."

Ashley's spell broke and she said, "Oh, you aren't going to look with me?" a bit of disappointment in her voice.

Sensing this Brandon said, "Sure I will. I tell you what, you get set up in front of the living room window and I'll make some hot chocolate for us and we'll watch the snow together as long as you want."

She smiled and agreed and they both went to the next room. A few minutes later they were cuddled together on the couch sipping mugs of hot chocolate and watching the snow. While the snow held little awe for Brandon, after all this was around the twentieth first snow of the year he could remember, he enjoyed sharing Ashley's awe at her first snowfall. By the time the mugs were empty the awe had even worn off for Ashley.

The effect of the cuddling however, had not, for either party. Soon after the mugs were placed on the coffee table Brandon and Ashley were engaged in a long make out session. It did not take long before both were removing each others clothes. Once they were naked and back in the bedroom Ashley immediately went for Brandon's hardening member. He enjoyed the feel of her mouth on his cock. It was not long before he came hard into her waiting mouth.

Once he had recovered he picked her up and set her down on the bed before climbing on top of her and kissing her. He then proceeded to kiss his way down her body, paying special attention to her breast and hard nipples as he did. He proceeded to eat her already wet pussy out until she came.

When she had recovered from her orgasm he placed the head of his hard cock against her waiting pussy and proceeded to fuck her slow at first, but getting faster as he went on. Nearly a half hour later she cried out in orgasm and he released his load into her.

A few minutes later she kissed him and he said, "Well we had better get some breakfast, because we have a full day ahead of us."

Ashley raised her eyebrow and asked, "Oh really? Will I like it?"

"I think you'll love it. Today is your introduction to winter fun in Chicago."

Ashley's eyes lit up and she said, "Oh goody, that does sound like fun!"

That day, with they help of Gina and his nephews and niece, they did everything fun a snowy winter day had to offer, snowball fights, making snowmen and snow angels, ice skating, and sledding. When the day was over and Brandon and Ashley reached their condo, the exhausted pair sat cuddled under blankets on the couch again just enjoying the moment. As he had hoped, Ashley had enjoyed herself immensely.

The next day Brandon took Ashley out for yet another Chicago right of passage, driving in the snow. Ashley was a good driver under normal conditions and could handle rain, but had never had to drive under snowy conditions. So, with light snow falling Brandon took her to a parking lot to practice. To his surprise she only made a few mistakes and after little over half an hour was rounding the parking lot rather well.

Feeling she was ready he then had her drive around town for a while and after an hour she had a pretty good handle on it. By week's end she was so good she took a trip to the DMV, passed with flying colors and became proud owner of an Illinois driver's license.

The rest of the week flew by and before they knew it, it was Christmas. Brandon enjoyed the holiday immensely. Brandon got mostly clothes and supplies for his new job and was pleased that everyone liked his gifts. As much as he tried to claim he thought of them on his own, Gina for one was not buying it.

She even made a point to thank Ashley after opening the gift Brandon gave her. Brandon defended himself by pointing out that Ashley's necklace, which Ashley loved, was picked out without any assistance. Gina responded with a comment about maybe a ring being next and Brandon quickly changed the subject.

The necklace however, while beautiful, was not the highlight of Ashley's night. Hearing the news that there was a student teaching spot waiting for her that spring in Brandon's mom's district was. Ashley had already enrolled with one of the colleges and was only awaiting the news on whether she would be accepted by the district for her student teaching spot. What's more, it seemed the classroom she was placed in belonged to a young teacher that was moving, so if Ashley made a good impression there was a great likelihood she would be considered first for the vacant spot.

That night as Christmas Day drew to a close Brandon and Ashley took advantage of their last night in Chicago, at least until after New Year's. Ashley wasted no time in showing her appreciation not only for the necklace, but his role in helping her dream come true.

Laying on all fours over him on the bed in nothing but her panties she said, "You've put all of my dreams within my reach and for that I am forever grateful." She said before she kissed him.

"Well I had some help..." he said when they finished kissing.

He was surprised when she giggled and said, "Darling, not all of my dreams involve teaching. In fact, for a few of them, all I need is you my love."

She then removed his boxers, which were the only thing he had had on, before pulling off her panties and lowering herself onto his hard cock.

He watched her bounce there for a few minutes before he sat up and pulled her close and lowered her with him down to the bed. When they reached the bed she stopped thrusting and Brandon took the opportunity to roll himself on top. She tried to protest but driven by lust he fucked her hard and fast. Her protests died as a wave of pleasure swept over her and soon he felt her long legs cross behind his back as she cried out for more.

He fucked her to two orgasms before succumbing to his own release. Drained of energy he collapsed to the bed. He held Ashley close and they fell asleep together content in their post orgasmic state.

Brandon woke later to the feeling of a warm mouth on his soft cock. Dazed he looked around and discovered Ashley's mane of brown hair covering his crotch. He also noted that it was still dark out. He felt his cock hardening rapidly as Ashley's mouth coaxed it back to life.

Then he felt the mouth leave his cock and looked down to see Ashley making her way up his body. He then felt her softly kiss her way up until she reached his mouth.

After a long sensuous kiss she looked him in the eye and said, "Love me darling, please?"

There was a plead of longing in her voice and so much love in her eyes that he could only nod before managing to say, "Of course."

He kissed her and slowly lowered her to the bed. He then kissed and caressed every one of her favorite places, taking especially long at a few of his favorites and showering her with compliments as he did.

She was moaning in pleasure and he had not even begun to fuck her yet. He too felt pleasure from the love radiating from her and her reaction to his actions.

After a few minutes of this Ashley pleaded, "Brandon please, I need you in me darling, make love to me."

Brandon obliged and lined up his now painfully hard shaft at her entrance and slowly pushed in. After letting her adjust, he proceed to make slow love to her. Looking into her eyes he felt her love envelope him like a warm blanket.

How long they remained like that Brandon did not know nor did he need to know. All he knew was when they finally came together it was some of the best pleasure he had ever known, nothing else existed in the universe but the pleasure he felt in that moment. It carried them both into a pleasurable slumber where both cuddled together warmed by their love for each other.

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