Talking to Jason and a Flirty Dare

As soon as Tiffany's parents turned out of the driveway and were out of eyesight, she dashed out to the car, retrieved all of her stuff, and stashed it away. Once she was certain everything was safely hidden, she took out her phone and looked at the texts she had received from Jason. Much to Tiffany's surprise the first message she saw was not from Jason but from her girlfriend, Amy.

Amy: I'm back from my retreat to Haiti!

Things had been so wild for the last few weeks that Tiffany had completely forgotten that Amy's two-month long retreat was over. Amy had signed up with a local nonprofit to go and rebuild houses in Haiti after a hurricane had ripped through the island. Now that she was back she was probably going to want to figure out their next steps and what to do in the gap year before college.

Tiffany: Welcome back! How was it?

Amy: It was amazing and so rewarding!

Amy: I can't wait to tell you all about it. I'm exhausted today but can we meet tomorrow?

Tiffany: Of course! My Dad got a new car, so he's going to teach me how to drive his old one tomorrow morning. Get lunch afterwards?

Amy: Perfect! Just text me in the morning and let me know when and where.

Tiffany had been so concerned with when her parents might find out about her secret or when she would break it to them that she had forgotten all about her situation with Amy. How am I going to handle this? She wondered and went over the different scenarios in her head. I think it's only fair to be open and honest with her. There's no doubt in my head this is who I really am and she needs to know that. If she supports me, great. If not, then we walk away and move on. Tiffany's thought process was interrupted by another buzz from her phone.

Jason: Shit! I'll do my best to save up a big load...but no promises.

Jason: It's a real shame that I'm going to be on the other side of the wall because those lips are going to look amazing wrapped around me.

Tiffany couldn't disagree with Jason on that and, despite some small trepidation, she was also eager to see what the final product will look like.

Tiffany: How long does it usually take from shoot to product on the shelf?

While she waited for Jason to respond she started sorting through the pictures she had taken, moved them all to her hidden folder, and queued a few to tease Jason with. Finally the three dots appeared and, like a high school girl with a crush, Tiffany found herself laying on her bed with her feet in the air and butterflies in her stomach.

Jason: Al is pretty good at getting the footage he needs. Editing it together and getting it onto physical media takes a few weeks, when there are multiple shoots to compile.

Jason: For this, since it is likely to just be this one scene he'll probably put in on the OnlyFans.

Jason: But if you're eager to see some snippets, he's always happy to share. He'll probably set up a group chat with the three of us to share.

Tiffany: Oh that's awesome!

Tiffany: Out of curiosity how much did he tell you about me?

Jason: He mentioned that you are trans but little else.

Jason: For the record it doesn't really make any difference to me.

Tiffany: OK, yeah he did mention that he shared that and it makes sense in the context of our business.

Jason: Can I ask what pronouns you use and how you would describe yourself?

Tiffany: Of course!

Tiffany: Day to day, in most contexts, I present and consider myself female.

Tiffany: For the purposes of Lacey Cream and filming, trans female fits. I don't want to deceive any partners or viewers.

Jason: Got it

Jason: Oh so that's really easy for me then.

Jason: No matter what I can always refer to you either by Lacey or female pronouns.

Tiffany: Exactly!

Tiffany: Can I ask how you got into this industry?

Jason: It was never a dream of mine.

Jason: I had a...what do the youths call it now? Situationship?

Jason: Anyways she used to work with Al and she convinced me to try it out and brought Al some homemade stuff we had done. I didn't need much convincing and Al was pretty sold after the first video or two. She moved away two years ago but I've kept doing it because it's a good little side hustle.

Tiffany: And the fact that you get to fuck hot chicks has nothing to do with it??

Jason: That's also a nice perk.

Jason: What about you? I know this is your first go around but how'd you hook up with Al and decide to do this?

Tiffany: I came into the store a month or so ago with a friend. Al, being Al, offered us the opportunity to appear in videos. I came back the next day and asked for a job at the store.

Tiffany: Just a few days ago I reminded him of the offer he had made. He got red with embarrassment but I told him I'd be interested. And here we are.

Jason: Damn you move quick!

Tiffany: Hahaha only when I really want to!

Tiffany: So...interested in another pic?

Jason: Are you kidding? Of course I am!

Tiffany: Good! Here's the back view...

Tiffany sent a photo of her squatting, facing away from the camera, her back to the mirror. She was wearing her schoolgirl costume and had flipped her skirt up to showcase the tiny red string of her thong and behind it her pink jeweled butt plug. After a few seconds Jason only responded with a peach emoji, an eggplant emoji, and the squirting emoji.

Tiffany: Hahaha did I short circuit your brain?

Jason: No you just hard wired all the blood in my body to go to my crotch.

Tiffany: Care to prove that?

Jason: You don't have to ask me twice.

A few seconds later, Tiffany received her first (but far from her last) dick pic. And what a way to start! Jason's was damn near perfect. His tip was bulging but not obscenely so, he had tantalizing veins running up and down his shaft, and it was glistening with just a hint of precum.

Tiffany: This time it's my turn to say damn because OMG!

Tiffany: Is it too much for me to say I cannot wait to taste it?

Jason: Definitely not

Tiffany: I cannot fucking wait to have that in my mouth and taste it!

Jason: That makes two of us!

Jason: Changing gears, do you have time to meet up tomorrow? I prefer to meet in person with my costars before we actually film together.

Tiffany: Ugh I wish you had texted earlier about that. I have plans tomorrow that are going to keep me busy until my shift.

Jason: Hmm...if it's not too forward, what if I came and hung out the store so we can chat during the quieter times?

Tiffany: As long as Al doesn't mind, that would be great!

Jason: Awesome! I'll text him and confirm no issues.

Tiffany: Any plans for the rest of the night? Just pizza and movie here, maybe a cocktail. Which reminds me the pizza guy might be here soon.

Jason: Is that right? Up for a little dare?

Tiffany: Depends on the dare.

Jason: I dare you to answer the door for the pizza in your lingerie.

Tiffany thought of the logistics and tried to figure out how much time she might have before the pizza guy arrived. She also checked her parents location to see if she would have time to hide everything before they got back. Shockingly, they were still on their way to the beach (Tiffany figured they must've stopped somewhere along the way), so that gave her a good 20-30 minutes before they were back. Even as she was typing out her reply she was already stripping down and picking out what to wear. Tiffany threw on a pair of 3" black, glossy pumps, some black stockings which clipped into her black, lace garter belt. For lingerie she picked out a pair of red, lace hip-huggers and matching red, lace bralette.

Tiffany: What's in it for me?

Jason: Aside from my respect? How about I'll bring some dessert by the store tomorrow?

Tiffany: Hmm...I think we can do better than that

Tiffany was playing hard to get with Jason, despite the fact that she was already putting makeup on her face and blending her breast forms in, which slightly spilled out the sides of her bra. She was also going to add the new blonde wig because it made her a touch more anonymous and also completed the look a little better.

Jason: Never take the first offer, very smart. How about after your shift tomorrow we can grab dinner? My treat.

Tiffany: Deal.

Tiffany: And before you say it, I'll get you proof of the completed dare.

Tiffany: I'm going silent for a bit.

With the deal locked in, Tiffany set about finishing her makeup and make sure she looked sultry and presentable. Medical tape and some uncomfortable pulling later, she managed to get a good tuck going in her panties that hid her clitty. With one last check in the mirror, she took a deep breath and headed down the hallway to keep an eye on her driveway. She only had to wait about three minutes before she saw a car turn in. Setting her phone up to record her and the door, Tiffany steeled herself for what she was about to do.

The knock on the door was startling, even though she knew it was coming. Before she could talk herself out of it, Tiffany grabbed the doorknob and opened the door. She recognized the face on the other side of the storm door as Reggie, one of the jocks she had graduated with a few months earlier. There was a split second where she left her body and died of embarrassment, but when he didn't bust out laughing and was eyeing her up and down, she realized he must not recognize her and did her best to recover.

"Oh, I'm so sorry about this you caught me right in the middle of changing and I didn't want to leave you hanging!" Tiffany lied, very convincingly.

"No problem ma'am." He replied while doing his best to stop his eyes from roaming. Trying to make a joke he continued, "It doesn't happen nearly as much as sitcoms led me to believe!"

"Oh that's too much!" Tiffany gave a genuine laugh before turning around to grab the cash off the counter giving Reggie a solid few seconds to check out her lace clad ass. Turning back to him she watched his eyes quickly dart back up to her. "Here you are, you can keep the change."

"Thanks!" Reggie replied, doing the math in his head to realize he got a good show and a generous $10 tip. "Say, the last name on the delivery is the same as a classmate of mine, John, you his sister?"

"What?" Tiffany asked, the adrenaline of being caught racing back through her veins. A lie was quickly on her lips, "Oh, no. I'm his cousin, Tiffany."

"Tiffany. Well, I hope we run into each other like this again!" Reggie said, somewhat joking but mostly not, as he waved goodbye.

"No promises!" Tiffany called out, before she could stop herself.

With her heart thumping against her ribcage, she slowly closed the door, stopped the recording, put the pizza in the oven to stay warm, and bolted up to her room. Before bothering to get undressed Tiffany once again checked her parent's location and, seeing that they were just now arriving to the beach, she opted not to get changed. She reviewed the video once and was shocked at how convincingly female she appeared, then she sent it off to Jason with the caption: Looking forward to dinner tomorrow!