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Overcoming First-Timer's Nerves

19:00
When you show up at your date's apartment early for your night together, she takes the opportunity to jump your bones. But soon after straddling you, you start to feel something poking you through her pocket. Or at least, that's what you thought! You've never been with a trans woman before, but she says you two can take it slow, and you end up very glad you kept going...
19:00
After going on a rant about the differences between guy and girl dick, your tomboy best friend agrees to let you try the difference out for yourself. But once you're between her legs, your natural submissiveness takes over, and she's more than happy to make it all about her today.
24:07
"Listen, stop me if I’m out of line, but I know you’re not the type to make the first move, so I’ll just ask flat out. Do you want to kiss me?" Your trans friend is crashing at your place while she's in town for your 10 year high school reunion. You thought you'd had a glow up, but it's nothing compared to hers. And when the pullout couch breaks, you two get closer than you have been in years...
18:38
A couple nights ago, your group of friends were at the bar, and a few pitchers in, you started playing “What Would You Do For A Million Dollars". Your friend challenged the boys with: “Would you suck someone’s cock?” and you surprised everyone, not so much by saying yes, but how low an offer you'd accept in the end. This caught your friend's eye, and after a night of board game and beers with the group, she decides to see just how serious you were.
23:28
You and your sister's best friend have been seeing each other in secret for a while and it's becoming too stressful for her. While at your sister's birthday party, she sneaks you away to your room. She wants to come clean and tell your sister about your relationship... Script by /u/ScriptsFromaSub on Reddit :)
14:50
You run into your younger sister's friend in the kitchen during one of their horror movie nights. You used to tease her back in the day before she transitioned, but it seems like she might have... liked it? You decide it might be fun to tease her again, but that looks very different nowadays...
28:18
When your girlfriend notices you stressed after a long day of work, she decides to help you unwind with Chinese food and a blowjob. But since she's seen how much you love turning off your brain and sucking her cock, she decides it makes more sense for you to be the one giving today.
19:10
You come home one day to find your hot, muscley roommate doing bathroom renos with bright red lips. She's found out about your lipstick fetish, and is gonna use it to your advantage to make her move. Turns out, this moment has been a long time coming for both of you.
27:32
She's been so stressed recently. Her job has been so demanding and you know what she's like. How focused, determined, and strong she can be. You love her for it, but perhaps she also needs to see that being a little selfish from time to time is healthy. You get up early to call in sick for her and quietly head back to the bedroom. Lifting up the covers at the foot of the bed you slowly crawl up between her legs and slide her panties to the side. You'll make her tell you what she wants, and give her what she needs.
14:44
"Now, I saw how well you handled the needle earlier. You think you can take a little more pain for me, sweetie? Good. Remember, pain can be fun too." After some flirting and a quick little tattoo, your artist refuses your cash tip. What she really wants is to bend you over a table and have her way with your ass. Expect spanking, licking, fucking, and a very happy ending.
23:34
while the same After your date night starts to get exciting, your girlfriend suddenly walks away to fetch a surprise. Walking back with a smile, she reveals the cock sleeve she bought. You're happy to play along; how could you say no to that excited face. Though, you can't imagine what she plans to do with just a single sleeve...
19:09
3(1)
On a late night phone call, your best friend manages to see through your façade of being a totally-in-control, no-bullshit domme. Only to then have you confess the truth through the most seductive phone conservation ever. Wherein she manages to make you surrender to your submissive side.
17:28
You and your friend are enjoying some ice cream, and she regales you with a story about the neurotic and finicky woman she went out with. Your friend still slept with her, but she's unsure whether the date faked her orgasm or not. When you reveal that no one has ever made you orgasm, she makes it their mission to change that.
31:56