Hardship Brings New Beginnings

All right, here's the story. My name is Dave; I'm nineteen, 5'9, 160lbs, short brown hair and greenish eyes. I have a very attractive girlfriend, in my opinion anyways; she's 5'3, 98lbs on a 'good day', brown eyes, brown hair that stops just above her shoulders, B sometimes C cup tits, and an ass just big enough for each hand. She goes to a catholic school and is extremely intelligent, even though sex is almost the number one thing on her mind. Yes, she does wear the uniform everyday to school and even a few times when we have sex.

Now Katie is more assertive than most girls are, if she wants something bad enough, she'll get it. And she's pretty good at manipulating most people. Hell, she's even done it to me a few times. She won't go out of her way for other people unless she's getting something out of it. Oh yeah, she also thinks that lesbians are disgusting and immoral, but homosexual guys are perfectly normal. Weird, but it plays a key part in my story.

Katie is the first girl that I've ever hard sex with, but I'm the fourth guy to ever score with her. So when it comes to our intimate relations, she likes to be in charge. She teaches me the dos and the don'ts when it comes to sex, well, with her anyways. She wasn't a fan of receiving oral until my persistent curiosity came along. Wow, I love pussy, I love the smell, the look, and most of all the taste. But she started taking things to another level.

Almost every single girl out there has asked their boyfriend to let them put make up on them at one point or another. It came to the day in our relationship where she asked me that. I didn't think much of it; in fact, I wasn't thinking at all and said go for it. So she jumped up and took me up to her room and sat me down in front of her vanity. She started plucking my eyebrows that hurt like a bitch, then mascara, eyeliner, blush, and some dark red lipstick. She finished up and let me look, weird, if I had longer hair I'd probably want to make out with myself.

Katie leaned down behind me, put her face next to mine, looked in the mirror and said 'smile'. It was a nice goofy picture I thought.

"I bet guys would love to make out with you" she said. "In fact, I bet Tom would make out with you if you asked him nicely."

"Oh hell no, I know you'd love to see guys make out, but I'm not going to be one of those guys. And besides, he's you're brother, wouldn't that be a little weird for you?"

"Which are you freaked out by more, kissing a guy or kissing my brother? Besides, if you grew your hair out and wore some of my clothes, it wouldn't be gay since no one would ever think you were a guy. You look so cute right now. If you were a girl, do you think that you'd find Tom attractive enough to make out with him?"

"Well yeah, if Iwerea girl, I'd defiantly want to make out with him. Hell, I know if he wasn't your brother you'd probably be going out with him instead of me. Am I right?"

"HA! So you do find him attractive even though you're a guy?"

"Fuck no! That's not what I said. I said if I were a girl I'd find him attractive, as you can see, I'm not a girl so I won't be making out with him anytime soon. So just drop the subject, I'm not kissing him."

"I'll only drop the fact that you think Tom is hot and you'd love to make out with him on two conditions. First you have to admit that you think he's the hottest guy ever, and secondly, you have to let me dress you up."

"No never."

"Oh come on, you know what, I'm going to go tell Tom right now—"

"OK! Fine, you win."

"Say it."

"Tom is the hottest guy I know, and you can dress me up anyway you'd like. There, happy?"

"That's a good little girl."

"I'm not a fucking girl."

"Just wait until I'm finished."

During the time that I was taking off my clothes, Katie was going through her closet and pulling out all sorts of outfits. Now since I was taller than her, any pants or jeans were out of the question, but she had plenty of skirts for me to try on. She even found a wig that she used for Halloween a while back.

First was her school uniform. I could remember all the times that I fucked her while she wore it. I'd pull her panties off, open her blouse and bust my load all over her chest. Then she'd scoop up my cum and lick it off her fingers. Now it was my turn to wear this innocent whore outfit.

I put on the white cotton panties, then the bra which she stuffed for me. Then the thigh high white stockings, followed by the blue pleated skirt and white blouse. The blouse was rather tight so only the middle two buttons were done, leaving a lot of mid drift showing. She went and got a pair of heels from her mom's room that I could wear. With the panties rubbing against my dick, and the memories of the amazing sex while she wore this outfit was turning me on more than I imagined.

"I'm done, how do I look?"

"If I were a guy, I'd fuck you."

"Really? So I look pretty damn good then?"

"In my opinion hell yeah, but if you'd really like to find out I could always go get..."

"NO! That's ok; I'll take your word for it. Tom doesn't need to see me like this."

"Why? Are you afraid that he'd want to fuck you, you know, just the way you give it to me? Pull your panties off, line up his dick with your ass and fuck you until he's about to cum. Then pull out so you can savor his man juice sliding down your throat. Is that what you're afraid of?" As she said this, she walked toward me, backing me up until I backed into the bed and fell.

"Well, I was really just afraid that he'd try to make out with me, but since you put it like that; that too scares me."

She pushed me on my back and straddled my hips. "Hmm...are you more scared of that happening, or that it's apparently turning you on?" She started rubbing my dick through the panties. "You know you want to. How about this, if you make out with Tom, I'll make out with any girl you'd like.... and maybe more. Well, I'd do more as long as you were willing to do more."

"So, you're saying that all I have to do is give Tom a little lip-lock and you'll make out with any girl thatIwant you to make out with?"

"Yeah. But after you're done, you have to honestly tell me how you felt about it. Deal?"

"Deal."

"TOM!!! Could you come up here for a few minutes?"

A second later you could hear footsteps coming up the stairs. My heart began to race in anticipation. Tom walked in the room and saw me sitting on the bed. Katie whispered something in his ear.

"All right lets do this."

Before I begin, I feel that you, the reader, should get a good idea of what Tom looks like. He's 6'4" and 230lbs of pure muscle. He competes regularly in body building competitions, and from what Katie tells me, he's got the biggest dick she's ever seen. I'm not sure why or how she saw it or even exactly how big it is, just that it makes me look like I haven't even reached puberty yet.

He pulled me off the bed and immediately put both arms around me and started wrestling with my tongue. This took me by surprise but I wanted it to look good so I wouldn't have to do it again. I wrapped both of my arms around his neck and he took it as encouragement to keep going. He moved his hands from my back down to my ass and picked me up, slid his hands down my naked thighs making me wrap my legs around his waist for support. With this done, he put his hands back on my ass, pick me up more so I was higher than him and began to caress each cheek. I began running my fingers through his hair and held on to his face forgetting what I was actually doing, and who I was.

'Click', Katie had taken a picture of the two of us getting into it. Tom slipped a finger under my panties in an attempt to finger my ass, but as soon as he touched my anus I started giggling like a little schoolgirl and broke off the kiss. Smiling, I looked over at Katie, "was that good enough for you?"

"For now. All right Tom, that's all we wanted. Stop by anytime you'd like."

Tom kissed me once more before he left the room and I sat down on the bed with a devilish grin on my face. Katie sat on the bed facing me, grabbed my forearm and said, "Spill it. You can't tell me that you didn't enjoy that or that you wouldn't do it again. Remember, a deal's a deal."

"Ok, ok, I'll tell you. Hell yes, I want to see you make out with another girl, especially after that. And I want that picture; no one is to see it. If it weren't for you dressing me up like this, I probably wouldn't have done it. Honestly, these clothes made me start to forget that what I was doing is way wrong. The fact that they're so skimpy made me feel so exposed to him; but because he's so much bigger and stronger, I felt.... I'm not really sure what I felt."

"First off, you two make the perfect couple. Second, Tom took the picture with him when he left. And third, that strange feeling you were getting while making out with another guy dressed up as a girl, that's the feeling I get when I make out with you. The feeling that tells you, you want him. You're willing to do anything he wants you to do. So what I think is going to happen from now on, is that you're going to be doing what I tell you to do otherwise everyone you know and don't know is getting that picture along with a nice caption and your name and address, ok?"

"You wouldn't."

"I would and you know it."

Feel free to write me about what you think should happen next.