Best Friend's Secret

He paused, leaving an uncomfortable air between the two men.

"Look, what I'm saying is: you need to be ready for things to be different, 'cause *she's* different. You need to be able to go with things like we did. Okay?"

"I can do that. I was pretty surprised when she told me she was trans. I never even suspected it. But like you said, I went with it. I'm okay with who she is. I love her."

"Yeah, she's really turned into a beautiful young woman. I really am glad she's with you. She could do a lot worse... You can go now, that's all I wanted to talk about."

"Thanks Mr. Kramer."

"Call me Jim, Matty."

"Thanks Jim."

--------------------

Meanwhile, Cindy and her mother were having an awkward conversation of their own downstairs.

"So are you sure he's going to be okay with your, uh, condition. I mean, it's one thing to talk about it and say he's okay, but it's going to be different once he actually sees it."

"Mom, I am 100% sure he's okay with it. Alright?"

"I know honey. I'm just saying. He might feel different once you two are... intimate."

"**Mom**... we've already *been* intimate."

"I didn't even think you guys had the chance. You must have been very quiet."

"We haven't gone *that* far."

"...well... how far *have* you gone."

"He gave me a handjob an-"

"*He* gave *you* a handjob?"

"I decided to show him my, uh, *condition* and I needed to make it erect and he ended up helping me. That was the first time anyone touched me like that and I... well, you know."

"Where did you, uh-?"

"I think that's enough details mom."

"Sorry, you're right. That was going too far. And I'm sorry for badgering you honey. I just wanted to make sure you were safe."

"Well I am. I'm always safe with Matt."

"I know honey. Matt's a good kid, but you have some very special circumstances and I wanted to make sure it would be alright... But if he did all that then I guess I don't have anything to worry about."

"Well he did and, actually, he did more than that, but I don't want to talk about that stuff with my mom."

"Okay, I'm glad Matt loves you for who you are."

"Yes I do ma'am," said Matt reentering the room with Jim.

"How long have you been there?" asked Cindy.

"Not long... Just long enough to know you told your mom we did something."

"I told her about the handjob."

"Stop," said Jim, "I don't want to hear about my daughter giving handjobs."

The other three fought to suppress laughter. It was Linda that failed, letting out a restrained chortle.

"What's so funny? I'm being serious. I don't care what you guys do, but I don't want to hear about it and for the love of god I NEVER want to hear it."

"She wasn't laughing at you dad, it's just... what you said."

"What about it?"

"Well..."

Matt jumped in to save his floundering girlfriend.

"You had it backwards, sir."

"Backwards? What do you mean ba-," he stopped mid-sentence and his eyes went wide. "Oh, you mean you... I just assumed it would be... There's nothing wrong with that of course..."

"It's okay dad, we get it."

"Well if that's the case Matty, I guess I really was worried about nothing."

"I promise you, you've got nothing to worry about from me."

--------------------

Cindy's parents packed their bags and were soon out the door.

"Alright, you kids stay safe. Lock the door behind us. If you need anything call. I'll drive all the way back down if I have to."

"We know dad. You don't need to worry about us though."

"I know honey, but I will anyway."

Cindy's mother came up to each of the teenagers and gave them a hug. As she held her daughter she whispered in her ear:

"Don't worry, if we have to come back for anything I'll call first."

"Why are you so weird?"

"What?"

"Nothing. Thanks, mom."

"No problem. Have fun," she said now speaking out loud.

Her parents were gone and for the first time since they got together they were truly alone.

"Soooo..."

"Wait for me in my room. I'm going to take a shower first."

Matt needed no more explanation. He went to her room and waited on her bed. Meanwhile, Cindy was cleaning herself for Matt.

Cindy entered her room wearing nothing but a towel, with a very noticeable bulge in the front. She dropped her towel, revealing her fully nude form to Matt for the first time. He was speechless.

"Well say something!"

"Sorry, you're just... you're beautiful."

"Well take off your clothes. I don't want to be the only one naked."

Matt complied, losing his jeans, shirt, and underwear.

"Well, you're not so bad yourself."

"So... where do we start?"

"Well you can start by getting the bottle of lube out of my top drawer."

Matt retrieved the lube while Cindy laid down on the bed. He walked over to her and she spread her legs.

"Squirt some on me and use your finger to work it in."

Matt squirted the lube onto her rosebud and gently placed a finger at her entrance. He slowly pressed it inside her.

"I'm used to doing this myself. You don't have to be *that* gentle, just don't go crazy."

He sped up and soon was able to fit two fingers and then three. As he lubricated her hole, he leaned over and kissed Cindy, who kissed him back.

"I love you Cindy. I've always loved you."

"Me too. Ready to make love to me?"

"Of course."

"Then lube yourself up and go ahead. I should be pretty stretched from your fingers, but take it slow at first anyway."

He was gentle, as requested, when he pushed into her waiting hole. Slowly he sped up until he was really fucking her.

"So, am I doing okay?"

"Yeah. It's nice. Feeling you inside me is nice. You're warmer than my toys..."

"Just nice?"

"Well, you're not going to make me cum like that."

"Well how *do* I make you cum?"

"Well, option one is to play with my dick while you do me."

"Option two?"

"Did you not like option one?"

"I like option one a lot and would be more than happy to do that for you. I'm just curious what my other option is."

"Well, they're not mutually exclusive. You can always do both. Option two is you hit my prostate."

"I'm not hitting it now?"

"Do you know where the prostate is?"

"...no."

"No you're not hitting it. You're aiming down as you go in. You need to be aiming up."

Matt adjusted himself for her.

"Better?"

"Yes, but I think this might help."

She reached over and grabbed a pillow, listed herself up, and put the pillow under her, elevating her crotch. This made it much easier for Matt to enter her at that upward angle.

"Now that's it."

"Yeah?"

"Oh yeah."

He grabbed the bottle of lube next to him and squirted some on her massive cock. She winced when the cold lube hit her, but relaxed soon after as Matt began massaging her stiff womanhood.

"And I bet that feels even better huh?"

"Oh, Matt."

He continued fucking her and playing with her cock. He jerked her off, occasionally pausing to play with the head or the sensitive skin right below it on the back side of her dick. Eventually the stimulation got to her:

"Matt, I'm about to cum."

"Okay."

"W-Would you swallow it for me?"

She made a face. Almost a wince, but with puppy dog eyes. It was a face that said, "I know I'm asking for a lot, but please? For me?"

"Of course."

He pulled out of her, but continued jerking her cock. He put the head of her dick in his mouth and swirled around the tip with his tongue.

"It's cumming Matt!"

She exploded in his mouth, filling it with strings of sticky cum congealing together on his tongue. He waited until she was done and opened her mouth so she could see her own handiwork.

"Perfect. Now swallow for me."

He closed his mouth and swallowed, trying his best to produce and audible gulp.

"Thank you Matt. Now give me yours."

Matt once again entered Cindy plowing away at her tight asshole. Apparently, cum swallowing really did it for Matt, because he was soon ready to give Cindy the cum she had asked for.

"Are you ready Cindy?"

"Only since I was like fourteen."

"Sorry for the wait then."

He came inside her filling her with warmth.

"Matt, I feel it. I can feel your dick cumming."

He finished and pulled out, laying on the bed next to his girlfriend. Cum flowed from Cindy's well fucked ass.

"That was incredible gasped Matt."

"Me too. I love you so much."

"I love you too Cindy."

The two laid together for a while, relaxing and cooling off. Cindy turned to Matt with a smile.

"So it's my turn now, right?"

"I don't think I'm ready for that yet."

"Yet? You'd do that?"

"Well, yeah, if you want. But I'm pretty sure I'm going to need to stretch my ass a little before *that* goes in it. I think you'd send me to the hospital if we did it now."

"That would be an awkward conversation: 'So my girlfriend tore open my asshole. Can you fix it?'"

Eventually the two got dressed and went about their day, but for the rest of the weekend they fucked like rabbits. They didn't stop until Cindy got a warning call from her mother that they would be home soon. Even then, Cindy decided they had enough time for Matt to suck her off one more time.

## Epilogue

Matt and Cindy stayed together for the rest of their lives. Since they became boyfriend and girlfriend on the day of their highschool graduation, they decided to also become husband and wife on the day of their college graduation. They found jobs, rented an apartment, and were off on their own. Their parents couldn't be more happy. Of course with marriage and independence came talk of grandchildren.

Matt and Cindy told them they were planning to adopt after they had purchased a house of their own. And when his parents asked why they were adopting, he told them the truth. His father was angry and his mother confused. His mom didn't take long to come around though. Matt had made it clear that if they couldn't accept Cindy then they'd have no place in his or his childrens' lives. For his mom, that was all she needed. She didn't understand all this transgender stuff, but she had always liked Cindy and she wasn't going to lose her son over this. His father never did come around. The split caused a lot of tension in their family and eventually led to his parents' divorce. To this day he doesn't know where his father lives or what he's up to.

They adopted three wonderful children, two girls and one boy, who spent lots of time with their three loving grandparents.