The night was cold, and a little damp. Hamish was going to a party at one of the nicer pizza palaces in town. He was single, a bit larger then average in body size, but a decent looking guy. Miles deep blue eyes, dark brown hair that reached almost to his ass. It was a party for a local bulletin board computer group he belonged to. One of the girls there had a super crush on him, and was wanting to get to know him better. She was an attractive lady, but Hamish just wasn't interested in Dee. He liked her as a friend. He did however have a major crush on Sally. Known online as Nightstalker. She returned a little bit of his flirtation, and was interested, but not ready for anything at this time.
Hamish had brought along a friend of his, someone whom he'd introduced to the group online and brought in as a friend. Hamish was looking for a girl. At least until Sally came up free. So Hamish's friend, Darren was there for moral support. While waiting in line to pay their bill Hamish noticed one of the waitresses. She was unbelievably beautiful. Long straight black hair that was just past her shoulders, and just slightly curled under. It shined almost dark blue under the light, almost a comic book look, but much more beautiful. She had small but full red lips, and some of the most beautiful green eyes he had ever seen. Hamish was almost in love. However he hadn't the guts to say anything himself. He was quite shy in person, but a regular Don Jaun over the phone or over the net. His friend Darren however, would do almost anything, say almost anything to anyone. So Darren had walked up to her and said asked for her phone number for his friend Hamish. She got this very flattered but sorry look on her face, and turned to Hamish, and said, "I'm so very sorry, you're really kinda cute, but honestly, I'm gay, and have no interest in men."
This caught Hamish a bit off guard, and he somehow gained a sudden confidence, handed the money to his friend to pay, walked up to her and ask, "So why is that?"
"Because a man doesn't, well...... Doesn't really know how to properly please a woman."
"You might be surprised."
"I doubt it."
"I bet you 200 dollars, I can prove you wrong, and I won't have to open my pants, and use that equipment."
"Normally, I'd slap you and tell you to fuck yourself, but I'm feeling like a real bitch today, and am up for putting a man in his place, and getting money to do so, you're on. Here's my number, I'm off work at 8:00, I expect my phone to ring at exactly 8:20, or the deal is off."
"Great, see you at 9:00."
"Right........... Oh, don't forget to stop by the bank to get my money."
Hamish laughed, and turned back to Darren who had finished paying, and was looking at Hamish with an astounded look on his face. "What are you looking at me like that for?"
"I've never heard you do or say anything like that before, that's something that would come out of my mouth, and get me a busted jaw, where the hell did that shit come from?"
"Well..... It pissed me off, and at that point I figured what did I have to lose. She talked down to me like I was some kind of lower life form."
"What if you can't perform your miracle pussy eating?"
"Fine, then I still win."
"How do you figure? Dude she's way out of either of our leagues."
"Simple, you saw how gorgeous she was, I saw you looking at that body."
"Yeah no shit, talk about a tight little ass, and perky tits."
"Yup, worst case scenario, I go to her place, I get to see that body, those tits, that ass, and best of all that pussy. Someone that looks like that, and not only do I get to see all of her, I get to feel her, and I get to taste her."
"Yeah, but yer out 200 bucks."
"So what, I may not be the richest guy in the world, but I have everything I need, except a woman, my bills are paid, it's only fuckin money man, and I've worked plenty of overtime this month. Besides look at her."
"Yeah, I guess yer right. Lets blow this popsicle stand huh?"
Hamish didn't figure on headed home just yet, it was only 5:30, and he felt like being out. So they drove down to the Mall in Hamish's Camaro, so he could pick up a new game, and few new items of clothing.
After buying what he was after, Hamish noticed it was 7:00. "Time to jet man, I don't want to miss my, uh, date with um what was her name anyway?"
"HAHAHA Her name was Lindsey. You make a bet and a date to eat this Lesbians pussy, and you don't even get her name?"
"Well I was too pissed off at her attitude, and besides I was admiring her uh yeah. WOW."
Darren just started laughing hysterically at this.
Hamish smacked him upside the back of his head. "C'Mon Darren you jackass, lets get moving, I don't wanna miss this chance and I want a shower, before I go."
Hamish had taken a shower, and and dressed. He was looking fairly nice in his new digs. "Whaddya think?"
Darren looked at him and said, "You look fine, but she's a Lesbo, clothes ain't gonna get your dick in her pussy, or get you a second date or a girlfriend. How you lick her will."
"True, but I don't want to show up looking like a slob, and have her shut the door in my face, I REALLY want to see her."
"Well it's 8:19 Romeo might want to pick up your phone."
"Right." Hamish grabbed his cellphone, and called Lindsey.
"Hey there Lindsey, it's 8:20, ready to lose that 200 bucks?"
"Hey look I was just in a fucked up mood earlier, I'm not really into this shit, so why don't you just imagine how I look naked, and go in your bedroom and FUCK YOURSELF." Then she hung up.
"Fuckin bitch, told me she isn't into this shit and hung up on me."
"HAHAHAHA, Now that's some funny shit man."
"Yeah like hell, watch this." Hamish Dialed her again, it rang 5 times and she picked up.
"Look here whatever your name is I told you....."
"No you look," Hamish started, "I will not be treated like some lower fuckin life form, just because you feel all high and mighty because you only munch carpet, I don't give two shits if you are gay or not, but just because I'm not doesn't give you the right to treat me like a piece of shit, now either hold up your end of the bet, or drop off your fuckin money."
"Well I see someone's panties are on too tight and they aren't mine, since I don't generally wear any, but fine. My address is 3375 North Lyndon Avenue."
"Nice, the other side of town."
"Really? Well in that case you have 15 minutes to knock on my door, I know you won't make it, but I'm gonna get ready anyway, because in 2 hours I'm calling my girlfriend and going out on a date, and I'm gonna get some pleasure tonight."
"Yes you will be getting pleasure, and you might be getting it from her, but you'll be feeling my tongue first."
"Yeah right, your time starts now, clock's ticking bitch boy." With that she hung up.
"My god she's a major BITCH, but I think I like her."
"HAHAHA Oh great, douche boy is in love with a lesbo. Enjoy your lick while you can because it's the only one you're gonna get."
"Yeah eat shit, I best get out of here she lives on the other side of town and now I've got less then 15 minutes to get there."
"Heh, you used to drive racecars, and you have a fast, car man, but I don't know that's pushing it."
"Well if you don't hear from me in 15 minutes, just know that in 20 I'm in her bedroom."
12 Minutes later, Hamish arrived on her doorstep. Turns out she lives in a house. A rather nice house. Hamish thought she must have rich parents. Hamish walked up to the door and rang the doorbell. Lindsey opened the door dressed to kill. She was wearing VERY tight black minidress, with a slit going up one side and a zipper going down the other. It had a nice low neckline, showing just a hint of cleavage. Her hair was mostly down, but held back out of her face with a couple of clips on the side of her head just above her ears. A gorgeous diamond encrusted, 2 inch wide, black leather choker adorned her neck, and the entire ensemble was topped off with a pair of black fishnet stockings. "HOLY SHIT, how in the hell did you make it here so fast?"
"Well," he said pointing to his Sapphire blue Camaro Iroc, "That's my personal car, and I used to drive racecars."
"SHIT. Uh damn I didn't want to get out of this thing until tonight, but a bet is a bet, and I WON'T go back on my word. Come on."
"Lead the way love."
Hamish followed her into her bedroom. Once they entered, Lindsey closed the door tightly and spun around. "Now look, the deal is you are ONLY eating my pussy. I've never had a dick inside of me, and don't plan on ever having one there. If I could just hike my dress and spread my legs I would, but this thing is too tight to allow that so you get to see the whole package. I need to be a little bit turned on, before anyone gets anywhere near my pussy. So you have feel around, and you can suck on my tits a little bit, before you eat my pussy, but THAT'S IT! PERIOD! If anything other then your jacket and your shirt come off, I'm going to assume you intend to rape me. I have a gun where I can get to it, and I will shoot you, I will not be raped, got it?"
"Look, it's my bet, I bet you 200 bucks, I can eat your pussy as good or better then any woman, and that's all I intend to do. Granted you are one of the most beautiful women I've ever seen, but I'm not a rapist. Although later on, I wouldn't mind knowing what kind of piece you have, I'm a collector of guns, but don't worry I don't have anything with me."
"Sorry, I'm just a little defensive you know. I had some guys back in highschool thought they were gonna rape me. The groundskeeper of the school came just in time, and hit the guy who was about to put his dick in me with a shovel. I've never trusted men since."
"Is that why you're a Lesbian?"
"God I can't stand that word, but more or less that is why I am gay. I used to like both men and women, but after that, I've stuck with women. Before that I wanted a boyfriend and a husband, and all that good stuff, with an occasional woman to join us."
Hamish walked up and gently laid his hands on her shoulders, "look Lindsey, a lot of men are scum, but not all are. My friend who asked you for your number for me, is a bit of a jackass, but he's no rapist, and neither am I. There are quite a few decent guys out there, and I'm one of them. I can't stand rapists, or woman beaters, or anything of the like. I may yell, I may swear, sometimes when I'm extremely pissed off or treated like shit, but that's the extent of it."
"I'm sorry, I guess I kind of deserved it, I was a bit of a bitch to you."
"Ok a big bitch to you."
"Yeah you were."
"You just don't pull any punches do you? Just straight to the point with no sugarcoating eh?"
"Yeah I guess so sometimes, but I forgive you."
"Yeah fine whatever." Lindsey began unzipping her dress, "Now just stand over there and watch, and get prepared to lose 200 bucks. I might even be nice enough to let you look at me naked and beat off."
"Gee thanks, but I'd rather not get shot."
"Look I know now you aren't a rapist, but still unless I let you beat off, the pants stay ON, and your dick stays in them."
"Of course, I understand you're are technically a virgin, so if you change your mind, I won't be rough, I'll be really gentle, and I promise to go at your pace and not hurt you."
"Thanks, but don't get your hopes up, don't even pray because it's not gonna happen. I don't now, nor do I ever want a boyfriend or a husband, let alone to have sex with a man." With that Lindsey began pulling her dress down, revealing that surpisingly she wasn't wearing a bra, let alone a pushup like Hamish thought she was. He would guess if she wore a bra it would be about a 36 or 38, and a C cup. MAYBE a D, but more likely a C. They were unbelievably smooth, with dark pink nipples, and small dark pink areola. Her stomach was flat and she had a slight sixpack. Despite her extremely slim body, she had some shapely full hips on her, and she wasn't boney anywhere. She was wearing black lace panties, despite her claim of not wearing panties, but then again she said generally, not never. As she slipped them off she turned around fast enough where he couldn't see if she was hairy, trimmed, or bald. He did however gasp when he saw her bare ass. It looked even better nude. "What was that for?"
"I don't mean to sound crude, but you have perhaps the nicest ass I have ever seen. I mean it looked GREAT in your uniform, but never in a million years would I have guessed it looked THAT good nude."
"HAHA, thanks, I never really liked it, I always thought it was too small and scrawny, but if you like it, I'm glad I can be of service, now take off your jacket and if you want your shirt, and get over here and lose your money." With that she turned around as she lay down on her expansive bed, and laid back on her pillows, and gently spread her legs.
Hamish could see she had a short but defined black heart shaved in above her pussy, and that her pussy itself was completely hairless. "I can see you shave the heart in, but do you shave your pussy too?"
"No I don't, it's naturally like that. I do grow quite a thick bush if I let it, but it's an almost perfect triangle, and is above my pussy, the hair doesn't extend down to it."
"Nice, I think I'm in love."
"Keep wishing, it's NOT going to happen. You can however start at any time."
Hamish, climbed up over her, and began to rub her breasts gently, and Lindsey began to respond a little by moving slowly. He then leaned down and started licking around her nipples, and occasionally flicked his tongue across them. He then took one nipple into his mouth and sucked gently, while flicking his tongue back and forth across it. Lindsey let out a soft moan and whispered, that it felt good and he was doing a good job. He slowly began to lick down her body and across her stomach. The flicked light kisses down the inside of one of her legs until he got to her ankles, and then switched sides and kissed up the inside of her other leg, until he got to her ultra smooth pussy. He noticed that her labia didn't stick out of her slit, but were just inside, making a very nice looking pussy. He licked in between very lightly with his tongue, from bottom to top, barely touching her clitoris with the tip of his tongue. He then traced his tongue along the edges of her labia, up one side and down the other, before running his tongue around the outside of her labia several times. Then he slipped his tongue right up in between her labia, and let the tip slip just inside of her, before licking all the way up to clit, which again he flicked with the tip of his tongue, just a little harder this time. Lindsey let out a quick yelp of pleasure. He then began to lick all around her clit, and flicked his tongue back and forth across the top of her hood, making her start to buck her hips.
He then moved back down and started to lick outside of her labia again. "OH GOD GO BACK PLEAAAAAAAAAAAAAAASE. You were about to give me an orgasm."
"I know, but it's not time yet, it would be just another orgasm. Just wait, now shush, I'm the one who made the bet that I could do it as good or better, now let me do the driving."
Lindsey started to object again, but Hamish flicked his tongue across her hood again, and she instead moaned a quick "OH GOD." Hamish continues his assault on the outside of her labia, before beginning to lick up the middle again, but this time he stopped and slipped his tongue deep into her pussy. She tasted so sweet, better then he could have imagined. It was natural tasting, with no foulness. No dick had ever been here before, and it showed with it's sweet taste. When he began to wiggle his tongue inside of her pussy, Lindsey started to buck her hips, fucking his tongue, and started to whimper. Hamish knew this was the right time, and licked his lips before bending them in to cover his teeth, as he used his fingers to pull back her hood exposing her clit, and drew it between his lips and started to suck on it, while very gentle rubbing his tongue across it. This sent Lindsey into a very intense orgasm, she started screaming "OH GOD" over and over again at the top of her lungs. She was bucking her hips violently into his face, and it was all he could do to keep his lips wrapped around her clit. When she was starting to come down, she began to push his head away for a breather, but he pushed her hand away, and then let go of her hood with his fingers, and then wrapped his lips around her hood, and began pressing down on her clit through her hood with his lips with a decent amount of pressure, then started sucking on her clit hard. Lindsey almost went through the roof, she was screaming louder and louder, incoherent words, and squealing uncontrollably at the top of her lungs, bucking her hips, with her arms up behind her clawing at the walls. For a minute or two Hamish thought she was going to push herself through the wall. It was as if she was trying to get away from the pleasure, but she kept bucking her hips into him, so hard he had to grab her little ass, and shove her pussy into his face and hold on to keep from being thrown off the bed. Lindsey managed to get one hand on the back of his head and shove it down harder, while still clawing at the wall with the other hand, incapable of screaming now, she was squealing, and running her head back and forth against the wall. After about 10 or 15 minutes, Hamish started to slow down, until he finally backed away. His penis was raging harder then it had ever been before, and he knew she was in a state where he could probably get it inside of her, but true to his word he never did. He sat up, and asked, "well?"
Lindsey just half laid there against the wall her eyes wide open, and breathing very deeply, heaving her sufficient bosom in and out a good 6 inches, with her eyes wide open. She was unable to respond.
"Well I can tell you enjoyed yourself, or you're the best actress I've ever seen. I don't know if I succeeded or not, but this is what I am going to do. If I failed, here is your 200 bucks," and he folded it up, and opened the drawer to her nightstand, and laid it right on top of the Kimber .45 she had laying in there. If I succeeded, then my address is in there too. Just put this 200 along with my 200 in winnings in an envelope and drop it in the mail slot in my door with my name on it. If however you changed your mind about the whole boyfriend thing, AND the dick thing, then leave your house key in there as well, and I will know that I now have the most beautiful woman in the world as my girlfriend, and I will keep my word." With that Hamish grabbed his shirt and jacket, and opened the bedroom door. He looked back over his shoulder at Lindsey who was still in the same position, the only thing that had moved is her eyes, which were now looking at him but she hadn't turned her head. He smiled, as he walked out, closing the door behind him. On his way home, he knew he had succeeded, but he also knew that there was no way in hell there was going to be an envelope from her, let alone one with a key in it.
When he got home, Darren, who he had been let stay with him since he was between addresses, asked "How did it go?"
"Well I'm pretty sure I succeeded."
"What do you mean pretty sure?"
"She didn't say. She just laid against the wall and looked at me. Didn't say a word."
"Man you may have, but what about the money?"
"Just in case I left her 200 bucks if I failed, and the address in case I succeeded."
"You know you just lost 200 bucks right?"
"Yeah probably, but she was more then worth it, she's really not such a bitch, and I understand her hostility, we did talk a little beforehand. She's actually a pretty sweet girl with a decent sense of humor. She was all I dreamed she was physically and more. Not to mention turning out to have a good personality."