tagTransgender & CrossdressersA Delicious Drug Deal

A Delicious Drug Deal


The building didn't appear dangerous, it just wasn't in the type of neighborhood Grayson frequented. Grayson parked and noticed as he came up to the entrance of the building that the intercom system was busted. The door had been propped open. Grayson walked in already knowing the apartment number he was looking for.

The young man was only there because he'd heard this was the closest place to score some weed off-campus. All the pressure he was getting from his parents about keeping his GPA up had him stressed out and desperate for something to help him calm down. A friend suggested that a little weed would do the trick.

Grayson found the correct apartment and knocked nervously at the door. Loud music from within the apartment blared through the thin walls and reverberated through his skull. A whiff of dark, musky air spilled out as the door opened up a crack.

"Are you Samantha?" Grayson asked.

"Who's asking?" A girl a little older than Grayson inquired from behind the chain.

"Uh, I was told you might have something for me to buy. Are you who I'm looking for?'" Grayson wasn't sure if he was more nervous about potentially making his first drug purchase or that the friend who referred him here had mentioned to him that Samantha was a transsexual. He'd never consorted with that type before.

"Come in." The girl unhooked the chain and swung the door open.

Grayson stepped inside and appraised his new surroundings. Samantha's place was a mess and it reeked of musty weed and old pizza, the latter he easily accounted for via the scores of old pizza boxes littering the floor. The piles of wrinkled clothing scattered around reinforced Grayson's impression that the place wasn't cleaned very often.

Grayson turned his attention to the girl herself. She was tall, full-figured and had her long black hair done up in a messy bun. She wasn't unpleasant to look at, but it was clear she didn't put much effort into her appearance. Grayson wondered if his friend had been conning him when he said that she had a dick. He didn't plan on staying long enough to find out.

"So you're Samantha?"

"Doesn't say that on my birth certificate, but yeah."

"I don't need much. I, I've got money."

Samantha smirked as she looked Grayson over. She sold to plenty of college kids, but none were as prim and proper as him if his sweater vest and khakis were any indication. She asked herself what he could possibly want weed for. A school project?

His obvious discomfort tickled her interest. "You go to college downtown? What's your name?"

"Yes, I do. I'm Grayson and I've got money." He reached into his pocket and started to pull out a wad of bills.

"Woah, where'd you get that kind of cash if you're a student?"

"My, my parents send it to me for school."

Samantha let out a laugh. "So your parents think you buy books with that money and you're trying to buy pot with it?"

"I just need a little. I wouldn't need any if they didn't stress me out about school so much," he confessed. He wasn't sure why he'd told her that.

"I wish my parents stressed me out with cash like that. Last time I saw my mom she was the one begging me for money."

"I, um, I'm sorry. So do you have anything I can buy?"

"Slow down, college boy. I don't know you well enough to do business with you. Take a seat and I'll see what I can do for you."

Grayson trudged over to the chair closest him, but froze in place, unsure of what to do next when he noticed a pair of panties blocking the cushion. Samantha saw them and chuckled. "Just put those anywhere," she said. Grayson bent down and knocked the panties off the chair with his sleeve before sitting down.

Samantha cocked her eyebrow, "You think I'm dirty or something?" She'd been toying with him up til now, but she really didn't appreciate these rich brats coming there in their nice cars with their fat wallets and looking down their nose at her.

"No, I, uh..." Grayson gazed up and noticed a pair of boxer briefs hanging from the ceiling fan. He thought they looked too small to fit around Samantha's curvy lower half and wondered how they'd gotten there. "Please, I just want a small amount. I'll pay well. I don't need the third degree."

"Well, I don't know you," Samantha sniped back. "And I don't do business with people I don't know."

"I'll tell you who sent me. You'll know them," Grayson said, afraid his deal was drying up.

"But you're asking me to sell to you. Not them. Understand?" Samantha sat against the armrest of her couch.

"Come on, I'll take whatever you have lying around. You can rip me off, I've got a lot of money here."

"You're really desperate, huh?" Samantha smirked, folding her arms across her chest.

"I'm cool, I swear. Let me buy some and you'll never see again."

"If I don't know you, I can't trust you, and if I can't trust you, I can't do business with you. You could be a cop for all I know."

"I'm not a cop! I'm in school."

"You could be an undercover cop, taking classes by day and catching drug dealers by night."

"That doesn't make any sense! I'm not an undercover cop!" Grayson exclaimed.

"That's exactly what an undercover cop would say," Samantha reasoned. She was having difficulty maintaining her serious exterior while cracking up on the inside.

"Please, that's crazy. I promise you I'm not a cop."

Samantha shook her head slowly. "We're stuck at this spot unless we can find a way to build some trust between us."

"What... like how?" Grayson asked tensely.

"If we were in prison you'd have to toss my salad first to prove you're not a cop."

"What the hell are you talking about?"

"The only way we can talk business is if I'm sure you're not a cop. The only way I'll be sure you're not a cop is if you toss my salad. You know, eat my asshole. Get it now?"

Grayson's eyes stretched open wide. "I, I... that's crazy! There's got to be another way."

"There's no other way. It doesn't matter to me, either we do business or we don't. You lick my butthole or you don't. Just make up your mind and let me know what you've decided," Samantha said.

"This is some kind of joke, isn't it? My friend put you up to this? I should have known this was a prank. They probably send all the freshmen here."

"Think what you want. You're the one who has to prove something to me, not the other way around. Maybe you can find another dealer in a worse part of town. I'm sure their terms will be fairer," Samantha said sarcastically, beginning to pick at her nails like she was getting bored.

Grayson felt desperate. He didn't know where else he could go. "Fine, damn it. I'll do it."

Samantha tried to hide her smile. She would enjoy putting this rich college kid's face between her cheeks. He'd been looking at her like she was dirty and now he was going to have to put his tongue up her ass. She wanted to savor the moment.

"Don't act like you're doing me a favor. I'm the one helping you. I could have just sent you away. This is no picnic for me," Samantha said. She had to suppress a giggle. The mischievous t-girl pushed off the armrest and spun her large butt toward Grayson.

"How do you want to do this?" Grayson asked nervously.

Samantha worked her pants and panties down her curvy hips and said, "Just wet your lips and try not to come up for air until I tap you on your shoulder and say you're done." Now that her face was turned safely away from him she could grin from ear to ear without getting caught.

Grayson got down on his knees and approached her shapely backside as she finished pushing her panties down. He noticed two large, low-hanging testicles swinging between her thighs. "Oh, god. He wasn't joking. You've got balls," Grayson muttered.

"Yep, big ones." Samantha reached behind her back and cupped Grayson's head. She pulled his face into her meaty ass.

The young man was disoriented at first. He hadn't expected to find himself embraced in the soft, warm unknown of her ass so quickly. Grayson struggled to get his mind in order and then pushed his tongue out and took a single lick of her crack. He attempted to wrench his face free after that from the grip of her ass, but Samantha shoved his face back in. She pushed him even deeper into her crack.

"You haven't even started. Any old cop could give it a little lick like that. You better do it to my satisfaction if you want my weed. Press your lips to my hole and kiss it like you'd kiss your girlfriend. I want to feel it! Now toss my fucking salad, bitch!"

Grayson was chilled by the thought that he could do all this and still end up with nothing to show for it. He had little choice but to comply with her every command. He buried his face deeper into the long crack of her ass and didn't stop until his mouth reached her most vulnerable of openings. He mustered up the courage and kissed her on her hot, rubbery hole.

An electric thrill went down Samantha's spine at the first touch of his lips to her pucker. The hot and bothered young t-girl shuffled her feet and stifled a moan. The feeling of his tender mouth against her opening shot straight through to her cock. She watched it stiffen as Grayson's lips pressed against her hole.

Grayson applied quick, gentle kisses to her asshole. It could have been worse. He found that the tastes, smells and textures of her anus weren't as displeasing as he'd expected. Her big, olive cheeks around his face brought a certain warmth and forced intimacy with them that wasn't altogether unpleasant. Grayson extended his tongue and rubbed it to her hole, causing the hair on the back of Samantha's neck to stand up like needles. She bit her tongue to mask a moan. Her hand slid down to her hardening cock.

Grayson's face nuzzled against the smooth insides of her plump cheeks as his tongue began to circle her anal ring. He ran it in long strokes around her little opening. He then decided to harden his tongue and press it with some force against her entrance, seeing how far he could get. Grayson managed to squeeze the tip inside. The intrusion caused Samantha's hard girl cock to swell bigger.

Samantha humped her meaty ass back at his face, like she was riding his tongue. She tried to inconspicuously stroke her cock while Grayson's pliable tongue wiggled zealously against the muscular confines of her tight, clutching sphincter. He figured by doing this there was no way she could plausibly accuse him of not having fully tossed her salad. He kept at it, eventually withdrawing his tongue and licking her hole up and down in long, wet swirls.

When Grayson's tongue began to tire, he resorted to using his lips and teeth. A few more flicks of his tongue and he switched to laying hot, steamy kisses on her tiny opening. He gently nibbled the outer ring, sending Samantha right to the verge of pain, into another world of vast, irrepressible pleasure.

Grayson realized he'd gone even further than she'd asked. He'd never kissed a girlfriend like this in his entire life. He'd never kissed anything so passionately, so intensely and devotedly as he was kissing this strange t-girl's asshole. Grayson cast aside his concerns because he knew he had to keep going until Samantha told him it was okay to stop. This wasn't going to be all for nothing. He'd get what he came for.

Samantha's whole body keyed into the pleasure she was receiving through her pucker, like her life depended upon the flicks and frolics of Grayson's tongue. And like a crazed animal she would have gone berserk if he were to have stopped right then, just when every tickling, tingling little movement of his mouth sent sparks rippling through her core, and leg-trembling jolts of pleasure surging through her cock.

Samantha struggled to stay on her feet as the pleasure pounded through her weakening body. Her cock could hold out no longer and throbbed powerfully, beginning to spew its payload. She cried out, "Ahhhh, FUCK, yes!" and yanked a pair of panties off the couch to catch her massive load. Her eyes shut blissfully as her balls emptied of sperm, Grayson's mouth still chewing and kissing her hot pucker.

Samantha allowed herself a minute to cool down from her orgasm, relishing silently the last teasing kisses of Grayson's tender lips before tapping him on the shoulder and telling him he could stop. If she wasn't mistaken, he seemed to plant a few more kisses on her hole even after he knew he could stop.

Grayson pulled his face from her cheeks and took a deep breath of fresh air. Samantha swiftly picked her pants up to hide her sticky, deflating cock, shoving her big ass back in his face in the process. She finally turned around and chuckled when she saw the state Grayson was in. His hair was a mess and his face flushed, he looked like he'd just come from a sauna. Samantha figured that in a way, he kind of had.

Grayson's legs were shaky as he attempted to stand up. Samantha helped him. He didn't feel too terribly awkward about what he'd done until he detected her glancing down at his crotch. He looked down and realized that he had an erection. Samantha graciously chose not to mention it. She decided he'd been through enough.

"Can we do business now?" He could taste her ass still on his lips.

"Yeah, all right, I can trust you. That mouth is so sweet it couldn't tell lies even if it wanted to." Samantha grinned. "Wanna stay and get high here with me? I'll give you a better price."

Grayson did stay. And then when he finally left he didn't stay gone for long. He came over a couple times a week to order pizza and get baked together. They watched bad cable movies, gorged themselves on pizza and argued over topics that seemed important at the time but were forgotten later. They developed a friendship. That time one friend licked the other friend's rosebud faded from immediate memory.


Grayson pulled up to his parents' house for dinner and took a deep breath. He'd been handling the pressure a lot better lately, but it was still going to be stressful to spend the whole night with his demanding parents. He got out of his car and dragged himself to the front door.

He was just about to ring the bell when he became distracted by another car pulling up next to his. It was a beat-up old Honda that looked out of place in the upscale neighborhood where his parents lived. Grayson was shocked when Samantha, grinning, exited the vehicle and joined him on the porch.

"You don't answer texts, you don't answer your phone. I followed you all the way from your dorm, even tried to flag you down on the road!" Samantha said.

"I have dinner with my parents tonight! You followed me from school? Why are you here? You can't be here."

"Cancel your plans," Samantha replied nonchalantly. "My guy just came through with some new product. It's like the best weed ever, you have to try it!"

Grayson was about to tell her that he couldn't get high because he was at his parents' house and that she shouldn't be there, but he never got the chance. The second his lips parted to speak the front door opened and he found himself staring dumbstruck at his mother.

"Grayson! I thought I heard voices," his mother said. She turned toward Samantha and added, "Hello. I don't think we've met." Then she turned back toward her son and asked with a smile, "Who's this?"

Grayson was stunned and caught very nearly speechless. "I, I, ummm..." he muttered emptily.

Samantha jumped in, "I'm Grayson's girlfriend. My name's Samantha." Grayson's stomach instantly churned.

"Oh my. Grayson has a girlfriend? He never told us! Samantha, it's so good to meet you. I'm Megan." The older woman took Samantha by the hand and led her into the house. Grayson barely managed the presence of mind to follow them inside.

"HAROLD! Grayson's here and he's brought a girl!" his mom shouted as she led them into the foyer.

Grayson began to regain his wits enough to say, "Um, mom, would you give us a minute? Samantha and I need to discuss something."

"All right, I'll go and get your father. You know him, always wrapped up in something."

Grayson took Samantha into the garage and quickly shut the door behind them. "My girlfriend? WHAT THE FUCK, SAMANTHA?!" he exclaimed.

"Pretty good, right?" she grinned, pleased with herself. "What did you want me to tell her? I'm your drug dealer?"

"...No, but... ...[i]Damn it[/i]!" Grayson threw his hands up and kicked at the air. "What do we do now?!"

"Now we eat. I hope your mom's a good cook because I'm starving."

Grayson thought about it. "Okay, we might be able to get away with this. Please, please, please, don't ruin my life."

Samantha grabbed him by the arm and began to walk back into the main part of the house. "You worry too much. I think your mom likes me. You don't bring girls over very often, do you? So cheer up, be a good boyfriend and treat me right and you might just get a kiss at the end of the night." She chuckled.

Grayson's stomach wound into knots as they rejoined his mother. His confidence that they could pull this off was already waning. He saw his father standing there. He knew he should try to smile, but he was far too perturbed to try.

"Hello, how are you?" His father said as he shook hands with Samantha.

"I'm just lovely. What a beautiful home you have. Grayson's told me so much about it and about you."

"Oh, that's sweet," his mother chimed in. "Our housekeeper is putting the finishing touches on dinner. We can talk in the living room while we wait."

The four of them strolled into the living room where Grayson took a seat on the far couch and was promptly joined by Samantha, squeezing in right next to him on the same cushion. Grayson's parents sat similarly on the opposite couch and began to hold hands. When Samantha saw that she held Grayson's hand in the same manner.

"So how did you two meet?" his mother asked.

"I, uh, I sold him a plant," Samantha replied, causing Grayson to gulp.

"You're a gardener? Oh, how interesting. How long have you been dating?"

"It's been about four months now, wouldn't you say, honey?" Samantha looked at Grayson and smirked.

"Yeah, around four months." Grayson's throat itched as the words came out.

"It's serious then. I wish Grayson would have told us. It's not as though he's had a million girlfriends that we can't keep track of them! Harold and I were racking our brains trying to remember the last one."

Samantha couldn't stifle her laughter as Grayson blushed and sunk lower into the couch. "I think he was just waiting for the right girl, Megan. Grayson was just telling me the other day how deeply he's fallen in love with me. Weren't you, sweetheart?"

Grayson glared icily at Samantha. "Um, yes, yes, I was," he nearly choked out the words.

"Go on, babe. Tell them what you were telling me the other day."

"Oh, um, I think that's best kept in private," Grayson replied.

"Don't be shy because they're here. Tell them what you said."

"Go ahead, dear. We're sure it was beautiful and heartfelt," his mother encouraged.

He gritted his teeth. "I said, uh, I said how much she means to me. How much I've fallen in love with her and how much I need her."

"And now the part about how I'm your sugar bear," Samantha pestered.

"And I called her my sugar bear," Grayson repeated tensely.

"Aww, that's so sweet. Isn't that sweet, Harold?" His mother nudged his father.

"Quite. I'm thrilled by how well you two seem to get along," Grayson's father said.

"Yes, and I call him my honey bun." Samantha leaned over and kissed Grayson on the cheek.

"Grayson seems very lucky to have found you, Samantha," his mother said proudly.

The housekeeper came into the room and announced dinner. Samantha did most of the talking during the meal, creating from whole cloth the entire history of their fictional romance and forcing Grayson to corroborate every embarrassing detail.

At one point Grayson's mother said, "It sounds like you really have your life in order, Samantha. I don't know what you see in our Grayson."

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