Date Coach
Chapter 5
The door slammed open, startling the doctor, “Dr. Chantry! I need your help, like, I think I’m in trouble!” Danni quickly came through the doorway, with elbows at his waist and forearms bent upward, arms swinging left and right, and the doctor took a quick look at him. Danni wore open toed 2 inch platform sandals, his toenails painted black. He barely fit in his skin tight girls jeans, which had rhinestones on the ends of the pockets and tears horizontally across the thighs. His dark shirt was a bit loose, but silky and clingy as one end was falling off of his shoulder. As he used his hand, painted with black nail polish, to sweep back his now-bleached hair, the doctor saw his black stud earrings, and got a good look at his face. It was all the doctor could do to hold himself back now, seeing his perfectly made-up skin, thin, slightly arched brows, and lips shiny with lipgloss, but he held back. It will be worth it, he thought, as Danni came up and tugged on Dr. Chantry’s sleeve.
“They fired me from work today! Like, I was just doing my work, and my boss totally called me into the office and said he’s like, letting me go for causing a distraction at work. Me! Like, I know I look good, but like, I was just working, I don’t know what to do now!” Danni broke into tears as Dr. Chantry responded, “now now, here, have a seat. It’s difficult to have a conversation and help you when you’re crying, so why don’t you have a bit of rum to settle you down.” Danni didn’t think twice as he took the rum, still laced with Dr. Chantry’s special chemical, and gulped it straight, being used to drinking heavily now. Water or alchohol, it still took effect just as fast and Danni was in a trance.
“First, when you awaken, you will immediately stop crying, fix your makeup, and feel happy. You’ll feel happy because you know if you follow my advice, everything will be alright again. You won’t care about that job anymore. In fact you’ll take a break from finding a job for a few weeks. You need some relax time. It’s a turning point in your life, you’re going to start dating again soon, so let’s take the opportunity to really start making you a new man. For the next few weeks, I want you to spend every night in the gay clubs. You need to get as much practice as possible. You should be flirting and dancing with as many guys as possible to maximize your potential. If they want to kiss you, let them. Lips are lips, and you can practice too. And now that you’ll be talking to much more people, we want you to keep stepping up your look. Now that you don’t have work you don’t have to worry about keeping up appearances, and we can go all out with your edgy, sexy look. I want you to start buying shoes with taller heels, you’re still too short, you need to look more impressive to get women. So from now on I want you to never wear any shoes with heels lower than 3 inches. Also try to make sure many of them show off your toes, you want to make sure every knows you take care of your feet, and that they aren’t gross. Black is getting too dark too, so when you go to the salon ask them to change your polish to an electric blue, something that will really catch the eye. And speaking of catching the eye, those earrings are nice, but you really should switch to hoops, they’re a lot more noticeable. You should also get a second set of piercings too, to really help. To round out your rock look, I want you to buy some eyeliner. Lots of rock guys wear them, you know, guyliner. It really makes you look edgy. Don’t be afraid to get it on there dark, with a nice smoky eye look. It’ll help you look more mysterious. Finally, you’re going to be practicing kissing a lot more. We don’t want to let people feel those little thin lips of yours. So I want you to go to a doctor, and get them enlarged. Remember, the bigger they are, the better your kissing will be, and ladies love that. So, then tell me, how’s your practice understanding women?”
“Going...well. Watching porn, understand feelings of woman in sex. Hard...to talk...in person...no job.”
“Ah yes, about that. No problem, you just have to start following the advice from the magazines you read. In fact I’ll subscribe to a few more for you to help make up for the lack of women to talk to. So now it’s not enough to study trends to talk about. I want you to start learning about the advice they give you for fashion, life, and sex. You’ll know all about women. Except for how a woman feels during sex. Do you know how it feels for a woman? Do you think you can understand how to pleasure one if you don’t know how to make her feel?”
“No...I don’t think so.”
“Right. I can help you with that. I want you to keep watching porn, but now while you watch the woman, I want you to get a small buttplug, and use it on yourself. It’s just to aid the feeling of the experience. There’s nothing strange about it at all, and you’ll leave it in for the rest of the night afterwards, only taking it out in the morning when you wake up. Soon you’ll be an expert. Alright? ‘Banana hammock’.
Danni woke up sniffling, “like, thanks for all the great advice doctor,” he grabbed a tissue from his small black handbag and wiped his tears, and took out his compact to begin fixing his makeup,“I know I can totally turn things around if I follow it! And now I’m like, super excited to go on more dates,” he smiled broadly, eyes still slightly shimmery from crying.
“Excellent then Danni. I’ll see you in a few weeks.”
Danni was feeling better about himself. He knew now that he had a lot of time on his hands, he’d really be able to work up to getting some dates going. He knew a lot about women, and soon he’d be applying it. Pulling the buttplug out of his ass, he put on his black thong and slid into his stretchy white jeans. It was his first day recovered from surgery, and he was going to give it his all practicing in the clubs tonight. He checked his makeup, and touched up his already-generous lipgloss on his newly enhanced lips. I’ve got this down better than any woman, they’d be so hot for me right now. He puckered his lips, I’d better get some good guys to practice on tonight, wouldn’t want the ladies to think I’m a slouch in the make out department, they already know I’m not in the make-up one, he said as he giggled to himself. He primped his hair, admired his new blue nails, and strutted off. Getting a glimpse of his legs in the mirror, he was delighted at his look. Dr. Chantry is so right. Not only do these make me look taller, but they make my ass look better!
“Omigawd Dr. Chantry! How’s it going?” Danni walked in confidently on his 3 inch ankle boots, one leg in front of the other, as he sat down and placed one leg gingerly over the other. “I totally had tons of fun this week!”
“That’s great Danni. Oh, I can see you got your lips done, ladies will love those,” Dr. Chantry responded.
“Yeah, I wanted them to be as big as I could get, so I could really do some good kissing. My mouth, like, kind of doesn’t close all the way now, but I did get to practice using them a few times at the clubs.”
“So everything’s going alright then?”
“Well, like, not reaaaally. I’m kinda like, running out of money now, from all the clubbing and stuff. Also, like, all the guys kind of know me now in the clubs, and it’s getting kind of boring...” Danni pouted, as he played with his hair.
“Hm I see. Well I have the solutions to your problems, so shall we begin?”
Danni brightened up, “totally!”
“Well to get some money, obviously you need a job. But you don’t really need that much, just enough to get by. So there’s no need to work that hard. I want you to try and get a job as a receptionist. They have it easy, and the pay’s not bad.”
“Ooh that sounds totally cool!”
“Yeah, and for the boring clubs, well, I have some news for you. You’re no longer going to go clubbing.”
“Oh no way, like why??” Danni asked, getting worried.
“No need for concern. I think it’s time we moved on to real practice dates. I’ve signed you up for this gay dating service I want you to start practicing with. I think you’re ready to handle this next step.”
“Why not a regular dating service?”
“Why not? There’s no way a woman would go out with you yet. You’re not really ready for that, and I’m not going to let you fail, so you’ll practice first. I’ve set you up for about 4 dates this week. I want you to go out with them, and try to make sure they have as good a time as possible. If you can entertain guys this much, you’ll have no problems with women. Remember to try and get in some make out practice as well. We can’t have you slacking off there. Because this is just practice, I want you to never go on a second date, there’s no point for you. Got it?”
“Alright doc! Totally can do!”
“Good to hear. Now let’s amp your style up some more. We’ve been going for edgy, but now that we’re doing real dates, we should shift gears. We don’t want to scare women off. We’ll go for fun and sexy. That will definitely work for you. With all that excercise you’ve been doing, we really haven’t shown off enough of your body. But I can tell from your jeans, compared to how your guys shirts fit, that you really need more women’s clothes to pull this off. Your size and stature make women’s clothes fit you perfectly. Don’t even worry about the fact that you’re a guy, clothes are just clothes, cut to fit different size people. Women tend to be smaller, so they cut them for smaller people. You just happen to be smaller, so it works great for you.”
“That sounds awesome, I should totally be doing that then.”
“Right, so I want you to go pick up some shirts and jackets from the the misses section. You really need to show off those great legs you worked hard for too, so buy some shorts from there while you’re at it. The more leg you can show off the better you’ll be. Black won’t do anymore, it’s too dark. We want to show that you like going out, and you’re not some gloomy person. So tell the salon you want a french manicure. They’ll know what to do. You should also get some more arm jewelry to show you know what it means to be flashy. Just pile it on your arms and don’t worry about it. Now we want to draw attention to your eyes some more, since your mouth stands out now, it might distract women. So we need to balance things out. You should darken in your eyebrows some more, after you get them a bit thinned out of course. It makes it easier to have them stand out clearly when you darken them in. Make your lashes stand out too, women love men with great eyes, and you can help yours with some mascara. You should keep those things in your handbag too, so you can do touchups when you need to.”
“Hm, I was worried my mouth would stand out too much, and like, make my face look all wierd. Okay, I’ll get those things.”
“So tell me how the porn has been going. Do you understand how it feels for a woman to have sex?”
“I think so. Like, my butt is starting to get used to the plug, so I’m not sure if it’s like, the same thing when a guy with a huge penis has sex with her. Sometimes the woman also gives head, and I’m not sure what to do.”
“No problem, all you have to do is get a bigger buttplug. You also just need to practice the same motions they’re doing for giving head, so you can understand how it works. Just buy a dildo, around the same size as you see in the porn you watch, and practice doing what they do. The better you get at it, the better you’ll be able to understand how it feels when your date gives you head.”
“Ooh, I’m, like so excited for head!”
“Haha me too. I mean I get excited when I recieve it as well. Ahem, anyways, I’ll see you in 2 more weeks, alright Danni?”
Danni stood up, and surprised the doctor as he came up to him and gave him a quick kiss on the cheek. “Byeee doctor! I can’t wait to see you again!”
Danny laid in bed, watching a dvd of a woman sucking off a guy while taking it in the ass. Danny followed along, sliding his buttplug in and out of himself as he used his free hand to give a mock blowjob to the dildo. As he was doing this, he thought about the past couple of days. I’m pretty sure I’m ready to date girls now, he thought, saliva running down the dildo and his hand. I’ve managed to make out with all 4 guys this week. I got them all off too. I should have tried to practice blowjobs at least once, but I don’t think my technique is ready yet. I guess they were satsfied with handjobs though! He was giddy and hot as he teased his asshole with his 1/2 inch long french manicured fingers. He remembered when the nail technician asked him if he was sure he wanted it done. After he convinced her, he had no trouble convincing them to arch his eyebrows paper thin. They looked really good to him now, and when he had his face done up, and his cute shorts on with his highest heels, he knew no woman would resist him. He began moaning aloud as he was reaching climax, staring at the penis on the screen, and how the woman’s mouth interacted with it. That’s it, he thought. I’m going to ask Dr. Chantry to let me go out with a girl next week. I think I deserve it, and I’ll show him I do! I’ll dress up so hot he’ll cream his pants on the spot! He finished up convincing himself with his own special logic as he set aside the buttplug, and pressed the dildo deep into him, causing him to scream out in pleasure as he cummed on himself. He didn’t even bother cleaning it off as he dozed off with the dildo inside him, dvd credits rolling.