Tug of War 69.3

"Come in, Tiff. Please, feel at home."

Timothy felt utterly astonished. There he was, alone with the Kate in the girl's bedroom. He had longed for a chance like that since forever... Now that it was happening, though, he didn't know exactly what to do, and just kept looking down awkwardly.

The room was small but cozy, with a bookcase and a desk in a corner, a window overlooking the garden on the other side, and lots of black and white art on the wall behind the bed. But Timothy only noticed all this much later, considering how nervous he was.

"You okay, Tiff?" Kate asked, caressing his arm.

"Umm... yeah."

"You sure?" Kate insisted, clearly not buying it. "You can be honest with me, sweetie. There is no reason to hide anything."

"Everything is fine, Kate. I swear! It's just that... like... I'm a little nervous. I've never been with a girl before, if you know what I mean" the feminized guy admitted, blushing furiously. He felt stupid for saying something like that at that moment, but he just couldn't help it. All the courage he had mustered to ask Kate to go to a more intimate place had simply vanished into thin air, and he was as scared as a kitten.

"Listen, Tiff" Kate lifted Timothy's chin and looked deep into his eyes. "We don't need to do anything you're not comfortable with, okay? Actually, we don't need to do anything if you've changed your mind."

"Gosh, no!" Timothy hurried to reply. "I didn't change my mind at all!"

"I'm glad to hear so" Kate smiled sweetly, although her eyes were full of lust. "Just one more thing... I understand that you are experimenting with your sexuality, to find out what you like and dislike, and this is exactly why I'm not going to demand anything from you, no matter what happens. I'm okay with it being just a one-time thing, in the case if you find out you don't like to be with girls. So no pressure, okay? You and Martin just broke up, after all... you may still have feelings for him and..."

"Kate... could you just shut up and kiss me, pretty please?"

"You don't have to ask twice, honey" Kate winked, just before kissing Timothy deeply. The two girls started rubbing each other's bodies, slowly taking their clothes off.

Timothy was enjoying the whole thing a lot, but something in the back of his mind kept bothering him. It took some time for the feminized guy to figure out what it was, but when he was wearing only his lingerie, about to get naked, everything made sense... The truth was that Timothy didn't know exactly what he was going to do Kate in bed. Not only was his member much smaller these days, but he also couldn't remember the last time he had managed to get an erection. Since he was planning to regain his manhood, being unable to get hard while in bed with a hot girl didn't seem like a good start in his troubled mind.

But that wasn't all... if Timothy was really going to sleep with Kate, he felt that he needed to be honest with the girl once and for all, so that she wouldn't feel deceived and used in the future. With great effort, he finally started talking... "L-listen, Kate... I need to tell you something, too."

"Really?" Kate commented while she kissed the feminized guy's shoulders and was about to take his lacy bra off. "Are you sure it has to be now? Having a conversation didn't seem to be your top priority a second ago... and you kinda convinced me that we have more urgent things to do."

"Yes, it totally needs to be now, Kate. Sorry, but I promise it will be quick, okay?"

"Alright, sweetie. I'm listening" Kate assured him, although she kept caressing his body.

"Earlier today you asked me why Martin and I stopped dating. Do you remember?"

"Of course, but you were a little vague in the answer, and I didn't want to push you."

"What truly happened was that... w-well... Martin found out the truth about me."

"The truth about you? What does that mean exactly?"

One more time, Timothy needed to take a deep breath before continuing. It was almost impossible to know how Kate would react to that. "On the night of Miss Charming contest, Martin overheard a conversation I was having with Mom, I mean, Susan... we were talking about everything that had happened to me since I started living as Tiffany... Do you remember the first time you saw me dressed as a female, Kate? That day at the mall?"

"Yes, I do. But I'm still not sure I know what you're getting at."

"Trust me, everything will make sense soon. So, that day I explained to you why I was wearing women's clothing. Gosh, it was all about a crazy game to piss my father off. We never talked about it again, and you started treating me like I really was a trans girl. But I was telling the truth that day, Kate. I swear I never wanted to deceive anyone! But after a while, I simply found myself totally stuck in my female persona, with no way to go back... Anyway, Martin heard all this, and we concluded that we could no longer be together. I thought I should remind you about it before we go ahead."

"It's okay, honey."

"Really? Is that all you have to say? 'Cos I thought you would, like, totally freak out and..."

Before Timothy could finish, Kate interrupted him with another hot, wet kiss, and Timothy gladly kissed her back. If Kate was okay with what he had just said, then it was all good... but maybe... just maybe... she had accepted it too easily...

The girl then finally took off Timothy's bra. "They are beautiful" she said, stroking and kissing the feminized guy's breasts. "So, so beautiful..."

Timothy bit his bottom lip as a soft, feminine moan escaped his mouth.

"I see you are enjoying it, aren't you?" Kate giggled, licking Timothy's nipples.

"Y-yes" it was all that Timothy managed to whisper, as he became more and more aroused. Before he realized it, Kate had already got rid of her own underwear, and then her hands went to Timothy's thong, which made him anxious.

Realizing that, Kate kissed his ear and whispered, "It's okay, Tiff... Just relax and enjoy."

Timothy thought it was a lot easier to say than to do. He was apprehensive about how Kate would react when she saw him naked. Would she look at him in disgust like Matt? Or would she be perturbed? Maybe shocked? The truth, however, was that Kate acted quite naturally, as if she wasn't seeing anything unusual between the legs of the woman in front of her.

"See, honey?" Kate said, holding Timothy's hand. "I told you everything would be alright. So... are you ready?"