Deedee and Brittany

Deedee finally got a good look at her son’s girlfriend. It did not surprise her that Trent would go after a tiny blonde pixie of a woman. In fact, the venn diagram of the way that Brittany looked and of how Jessica looked was a near circle. Brittany was a girl growing into her womanhood. She exuded the girl next door that doesn’t know she is beautiful yet, but in a few years will shatter hearts of men around her. Yet, she held none of the raw sensuality that Jessica had. Or even the magnetism that Tiffany was beginning to display. To put it plainly, Brittany was cute. “You must be Brittany, Trent said I should expect you. He had to make an emergency run to help a close friend of the family. But he should be back soon. Why don’t you come inside and wait?”

Brittany looked at the older woman before her, surprise in her eyes. Trent had said he would go visit his father after leaving school so suddenly. In the few times that he had talked about family at all, Trent had never mentioned a step-mom. And with how beautiful this woman was, Brittany was sure he would have. Taking in her sexy vacation beach vibe, she couldn’t help but feel inadequately dressed in Chucks and pale green summer dress. Trent was never one to dress up, so she had always been able to keep it lowkey while they spent time together. Plus he hated it when she wore heels, in anything taller than a kitten heel and she would threaten to overtop the young man. Finally finding her voice, she managed to nervously squeak something out. “Yeah that would be great! Thanks!”

Deedee stepped back, letting the girl into the house and closing the door behind her. “You know, I was about to pour some coffee, would you like some?” Moving towards the kitchen, Deedee swung her hips back and forth with an exaggerated wiggle. Looking over her shoulder she smirked as she caught Brittany watching her walk.

“That would be great. I uh, I never caught your name.” The 18 year old girl blushes as she realized she had been caught watching the MILF’s ass. Scurrying along to catch up, her typical defense mechanism to anything embarrassing was to keep talking. “But yeah, do you think Trent will be back soon? Not that I mind hanging out with you or anything but I just don’t want to impose, you know? And Trent, he seemed like it was really important that I showed up today. Said he had some really big news about his dad.” The words came out in a jumble, all the thoughts trying to escape from inside of her at once.

Deedee couldn’t stop herself from smiling. The girl was infectiously cute. It was astounding how her son had ended up with someone like this. “It is really nice to meet you hun. My friends call me Deedee. As for the rest, I don’t know when he will be back. But really, you are totally free to hang out here as long as you would like.” Stepping up to the coffee maker, she put in one of the small pods and watched as a perfect cup of hot coffee poured out. A second quickly followed.

Carrying both cups of coffee over to the table that Brittany had sat down at, Deedee set one in front of the cute girl and then sat down in a chair right next to her. Turning so she was facing Brittany, Deedee slowly crossed on bare smooth leg over the other. The slits in her skirt opened up to show all of her tanned and toned legs. “Oh, I’m sorry hun, I didn’t even think to ask. Did you want some cream in that?” Standing back up and turning back to the refrigerator put Deedee’s plump ass right in the girl’s face.

“I’d love some. Sugar too please!” Brittany’s eyes were glued to the mature woman in front of her. There was something about her, something that oozed sex. The way she wore such revealing clothes around the house. The way that she moved in such tall stiletto heels was astounding, she looked like she had been born to wear them. “You know Deedee, I love those shoes! I love heels but I can never find a reason to wear them.”

Pulling the creamer out of the fridge and wandered back. Setting it on the table she pointed out the sugar dish that already sat in the middle of it. Sitting back down, she put one leg out and looked down at the stiletto sandals on her feet. “Aren’t you sweet! They are brand new, first time I’ve ever gotten to wear them. As for not wearing heels often hunny, who needs an excuse? A cute thing like you is surely short enough you could wear anything. Unless of course Trent can’t handle a girl with confidence.”

Brittany’s eyes widened as she took a sip of her now lightened coffee, she used the spare moment to try and hide the surprise at hearing someone dare to speak badly of Trent. “He’s just kinda sensitive about his height is all.”

Leaning forward conspiratorially Deedee reached across and laid a long nailed hand gently on the younger woman’s arm. “I have found that men sensitive about height are really just projecting being sensitive about other bodily measurements. If you know what I mean.” Winking, she leaned back and took another sip of coffee. Uncrossing her legs and then switching sides to cross her other leg, Deedee managed to rub the toe of her shoe against Brittany's bare leg. “And I have found those kinds of men aren’t worth the effort. I’m sure Trent has nothing to be worried about there. Right?” Sipping her coffee, her eyes locked onto Brittany’s. The smile on Deedee’s lips and the look in her eyes let Brittany know that she knew better.

Brittany was now blushing from head to toe. Not only was this beautiful older woman obviously flirting with her, but she seemed to know the exact things about Trent that were driving Brittany crazy lately. Taking another drink of her coffee, she tried to organize her thoughts. “So how do you know Trent’s dad? Are you his girlfriend or something?” This question seemed like a good way to get out of such personal waters.

“Tell you what Brit, can I call you Brit?” Accepting Brittany’s nod of confirmation, Deedee continued. “You said earlier you were into fashion? I think I heard Trent mention you were majoring in it?” Another nod joined the first. “Why don’t you come look at my closet? I find that I’m having a hard time keeping up with some of these trends, and I would hate to be that girl who wore last year’s trend to this year’s function.” Standing up, Deedee reached out and offered the girl her hand as she smiled down at her.

Not quite realizing just how much Deedee was sidestepping the question, Brittany eagerly accepted. Reaching up she laid her own hand into Deedee’s and stood up to follow along. “I don’t think you are ever going to have that problem Deedee, they say that trends follow the beautiful and so I think you will be fine.” The words slipped out of the young girl before she realized she was uttering them. The blush from earlier deepend as it became clear that she was flirting back.

Turning to look Brittany in the eyes, Deedee smiled softly and squeezed the hand she held. “That is the sweetest thing anyone has said to me in a long time. I can see why Trent likes you.” In no time the two girls had stepped into Deedee’s closet. Looking over at the vanity table, Deedee sighed sadly. “Oh my, I’m so sorry about that. Here let me put those away. It seems like my girlfriend Tiffany left something out she shouldn’t have.” Stepping up quickly, Deedee set her coffee down and collected the shiny butt plug and lube before depositing them both into a drawer quickly.

Brittany wasn’t sure what stunned her more, the references to a girlfriend, the buttplug laying out, or the fact that the closet in front of her was like some fashionista's wet dream. Deciding that the clothes were significantly safer to talk about, she managed to set her own coffee down safely before she began to nerd out over the shoes and clothes. “Holy cow! How many pairs of Louboutins do you have? I don’t think I saw this many in the store. And Jimmy Choos. Oh my god!” The girl looked to Deedee with glee in her eyes. A nod from Deedee was the silent signal to Brittany to begin picking up and looking through anything and everything.

“I don’t really like flats. And I have to project a very fashionable look for work. Plus, shoe shopping is fun.” Deedee giggled as she settled onto the stool in front of her vanity and sipped her coffee again. “As for your prior question, about how I know Trent’s dad? Well, the simple answer is I know him better than anyone else could. I used to be him.” Deedee casually let the bomb drop into the room, curious how Brittany would deal with it.

Brittany had in her hands the exact shoes her boyfriend had worn the day before, the pink So Kate 120’s, when she heard what Deedee had just said. Turning around confused, she locked eyes with Deedee. “Wait, what? Like…” Fumbling around for the right words, Brittany became worried about how to proceed forward without being offensive. As the thoughts jumbled in her mind, one stuck out more than the others. “But Trent doesn’t…” She knew Trent didn’t deal well with surprises.

Deedee laughed lightly while standing and setting her coffee down. She walked up to the girl and gently pulled the designer heel out of her hand. “I’m sorry to drop that on you like that. I really am. There really isn’t an easy way to go ‘Hi, I used to be called Derek.’ Trust me, I’ve tried.” Giggling at the absurdity of the situation, she placed the heel back in the cubby it belonged in. “Please feel free to ask any questions you might have, I really am open about it.” Pausing for a moment she smiled in a sad way before getting to the last unfinished question. “And yes, Trent took it poorly.”

The sad look in Deedee’s eyes haunted Brittany. She knew her boyfriend could be a dick, and she had certainly experienced him being trans and homophobic. But to see that he had acted that way towards his family amazed her. Emotions battled on the girl’s face openly. Anger, sadness, pity, and even a little self recrimination were all present as the girl’s mind spun out of control. Finally, she couldn’t take it anymore and threw herself into a hug. Her arms wrapped around Deedee and pulled the two of them together tightly. “I’m so sorry!”

Suddenly, there it was again. The crack in Deedee’s armor. The feeling of this young, naive, and perfectly adorable girl hugging her and caring about her for no reason was so alien to the life that Deedee lived. Of course she knew that people in her life cared for her. Miss Jameson had proved she truly cared for her, Jessica was currently proving it, even Trent in his own distorted ways was proving it. But each of those was predicated on something else. Or at least that is how it all felt to Deedee. Yet here was this person who was showering her with affection for no reason other than because she wanted to.

Squeezing her eyes shut tight Deedee managed to keep the tears down in the box that they had stayed in for so long. “Careful hun, you are gonna make me ruin my makeup.” Hugging her back, Deedee gently kissed her on the side of the head and whispered into her ear. “Thank you though.” Before standing upright and disentangling herself.

Knowing that this room likely wasn’t the best place for this type of conversation, she led Brittany back out into the living room, the pair of them settling onto the same couch as Deedee continued on. “We are working on it though. He has to figure out a lot of things about himself before he can figure out how he feels about me though I think.”

The exasperation was evident in Brittany’s sigh before she spoke up. “He… he isn’t really a bad guy. He just is trying so hard to be who he thinks he has to be. And he ends up just being so terrible to people. But sometimes you get him alone, and then he finally shows you who he is deep down.” She shrugged and took another sip of her coffee before going on again. “Maybe I shouldn’t be in a relationship for just those moments, but I don’t know if breaking up with him now is a good idea.”

Deedee nodded sagely, as if she had any good experience in a relationship in the last 20 years. “It is hard hun. What I can tell you from experience is that staying for someone else is never the answer.”

Taking a deep breath, Brittany tried to breath out all the negativity that was crowding inside of her. She was a naturally upbeat person and the last few minutes had truly sapped her will. Turning back to Deedee, she decided to change the question back to something she had a more concrete understanding of. “Ok, so I know you weren’t this far into transition when I met Trent. So how did you get that big of a collection in like a year?!”

Deedee giggled and reached out to lay a hand on Brittany’s knee. “Well, a couple of things happened there. One, I really do love shopping. Two, I managed to pay off this place. Three, my ex got remarried so I no longer have to provide her alimony. It all kind of became a necessity. That closet is my zen garden. I want to fill it with the prettiest things. Then when I leave it, I feel powerful enough to do anything.”

Brittany’s eyes looked down at the hand on her knee and she smiled before locking her eyes onto the beautiful green orbs in front of her. There was a confidence in the older woman that she wasn’t used to dealing with. So many of the people she interacted with who tried to act confident typically came across as egotistical instead. Reaching down with her hand, she laid it over Deedee’s and squeezed it gently. “I wish I could feel like that. I mean, look at you. You are gorgeous. I’m just a frumpy teenager compared to a woman like you.” Shaking her head, she continued in a deprecating tone as she broke eye contact. “And you have only been doing it for a year!”

For a single second, Deedee considered the path she was about to traverse. How it was immoral to so many. Taking another sip of her coffee, her thumb casually rubbed across the back of Brittany’s hand. Could she do this to her son? She knew that it was most certainly rationalization, but college relationships hardly ever worked out. Not to mention if this girl was used to the tiny dick that she had seen from Trent, then Brittany had been truly deprived of good sex. Setting her coffee down, she leaned towards Brittany before speaking up. “My dear, you are stunning. Nothing about you is frumpy! I’ll tell you what. Why don’t we go back to the closet and pick you out something special to wear? I’m sure we can share clothes.”

Nodding along Brittany stood up, her hand still holding onto Deedee’s. “Ohh, I thought I saw some things we can try.” Almost pulling Deedee along behind her, the younger woman missed the devilish smile that flitted across the older woman’s lips.