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So begins Oliver”s first date as a woman.

Tick-tock, tick-tock. Get out of there before it”s too late!

Oliver finds himself getting wined and dined by a hot and successful male model. Man has his life flipped.

If Oliver”s changing taste buds are anything to go by, he should have quit while he was ahead.

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What Holly said or didn”t say to Kayla is causing a serious fight between her and Chris. She says that her words were taken out of context, and that she would never think about cheating on Chris. However, how can Chris trust her? Things will be complicated until this is all sorted out.

Homecoming has passed. While Chris and Holly were pretending everything was okay between them at the dance, they were robbed of Homecoming King and Queen by a snobby rich kid. Scarlett butts into Chris and Jessica”s discussion, with something she”s very excited to find. What could it be?

Scarlett has found a box containing clothes she wore back in her high school and college years! While showing her 80″s fashion sense to her kids, Chris has the same thought all of us had. Will wearing Scarlett”s old clothes turn him into a young Scarlett?

That sneaky Chris is at it again. He gets his hands on Scarlett”s twenty year old clothing. If you think modern day Scarlett is hot, wait until you see her in her prime.

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Probably not a good thing for Oliver to experiment with the night before his date with Lorenzo.

Oliver comes one step closer to trying out the real thing.

Practice makes perfect!

Oliver better hope that he can keep control before his date with Lorenzo is over.

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With Holly deciding on her dress, she leaves Chris on his own for a minute. It”s a good thing she did, because look who also needs a dress for the dance…

The good news is that the real Holly was able to hide before Kayla saw her. The bad news is that Chris is now stuck with Kayla. How is he going to get out of this mess?

With Kayla thinking this is Holly, she has no really to hold anything back. She says does a number of things that sets of alarm bells, and one thing in particular that sets Chris off. Is this a misunderstanding, or is there something going on between Holly and Kayla?

Chris is really pissed off at the thought that Holly has been secretly dating Kayla while using him as a cover to hide her being a lesbian. Is he right, or is he overrating to nothing? Things could get rough.

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This misunderstanding with the big lump in Oliver”s pants leaves Grayson to conclude that Oliver is bisexual. Unfortunately for Oliver, Grayson admits that he himself is bisexual.

Man what”s a less awkward outcome? Telling Grayson the truth about the dildo or lie that it is actually his erection?

Great, now Oliver has to watch out for Grayson as both a man and a woman.

The next day Oliver comes home from work. Only now his opinion on the one-eyed purple monster has changed quite drastically.

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Holly sure knows how to tell a story.

Hey! Do you like TG comics? I bet the answer is yes. Well then, I have good news! Mimi decided make her own short comic in her free time after being hired here on the site. I didn”t have any role in making it, and it”s all her work. Here”s the first page:

This idea of Holly”s now doesn”t seem like a good idea to Chris. Not only is he her doll for playing dress up with actual dresses, but there”s the risk someone they know could see two Hollys.

Holly”s having a lot of fun with her twin/doll/changeling/boyfriend. She has him put on everything dress she likes until she finds a winner for the Homecoming dance. Chris will be happy when she”s finally the one wearing the dress.

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Oliver thinks about leaving, then considers that his weight as Caroline may change if he doesn”t eat right and exercise as her. If he wants to keep the figure of a model, he”ll need to start regularly working out as her, which means even more time spent as her.

Lorenzo and Jayden may have found a new workout partner. However, don”t expect Caroline and Oliver to show up at the same time.

Gee, I wonder what”s in the box?

The funny thing is that this might only be the second most embarrassing situation involving Grayson and an erection that Oliver”s been through.

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Chris is going back into Holly form, but with Holly”s help for the first time ever. She”s going to enjoy having a pretend sister for a while. Although, this is a pretend sister she could “experiment” with later on if she wanted to.

Holly”s amazed with not only his transforming body, but the end result. He”s a perfect clone of her. Even Mr. Jingles is amazed, that or wildly confused about what”s going on.

Chris and Holly pull a funny trick on her dad as the two of them leave. Little does he know that one of them actually isn”t his daughter. Good thing he doesn”t look outside and see two Hollys making out.

On the way to the store, Chris asks Holly something he”s been pondering for the days. What was her first lesbian experience like? Now we all get to know.

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Oliver gets a call on his pink phone. Thinking it could be the casting director for Erica”s Secret, he rushes to the bathroom to change into Caroline. Unfortunately for him, it”s not the call he was hoping for

Well this is awkward. At least Lorraine”s new clothing transformation feature works properly.

Oliver sure knows how to find himself in embarrassing situations of having to turn into a woman. Chris Young would be so proud.

Oliver finds himself wearing a sports bra and yoga pants around his two friends. Why does this reminds me of the scene in Jurassic Park when they lowered the cow into the Velociraptor cage?

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Chris is having an increasingly awkward time at work. Not only does he have to work with Mark (who he still has problems being around after a few weeks ago), but now he also needs to work with his girlfriend”s ex-girlfriend.

While having a causal conversation with his new coworker, Chris experiences something he hasn”t before: female thoughts as a guy! Thoughts all sound the same to Chris, so he can only tell if they aren”t his based on what they say. He”s not sure what he was thinking, but doesn”t suspect Christina.

Holly calls Chris back over to her place a few days later, but won”t say why. It soon becomes clear why she was being so secretive.

As much fun as two Hollys would be, Chris really doesn”t want to go out dress shopping with her. However, Holly really knows how to get her man interested. Hook, line, and sinker.