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.”
Samantha’s response sent Grayson’s blood pressure spiking. “Oh, he has hidden talents.” He felt a wave of relief when she laughed instead of elaborating further.
When Grayson got a bit of pie on his face during dessert Samantha leaned in and wiped it off, then unexpectedly she kissed him right there in front of his parents.
“The sugar bear likes her honey,” she said after the kiss.
“Would you look at that, Harold. Young love,” his mother remarked.
Mercifully, the night ended soon after that. Grayson’s mother took down Samantha’s information and said they needed to stay in touch and that she was invited over again any time. Grayson and Samantha left together and walked to their cars, aware that his mother was watching them from the front window.
“Not bad, huh?” Samantha asked him, deeply pleased with her performance.
“I felt sick the whole time. And you, you kept digging us in deeper!”
“Hey, I should be getting some appreciation here. I was this close to bringing up your talented tongue and taste for salad tossing when your mom asked what I saw in you.”
Grayson’s eyes bulged. “You wouldn’t have, you couldn’t…”
“It’s a miracle I managed to hold my tongue throughout the entire dinner about how we really met, especially when we had chocolate pie for dessert!”
“You’re disgusting!” Grayson exclaimed.
“Yeah, I sure am. Wanna come back to my place?”
“Hell yes.” Grayson laughed. “I could definitely use something to calm me down right now.”
“Meet you there,” Samantha said, leaning over and kissing him again lightly on the lips.
Grayson wondered about that kiss as he got into his car. He figured Samantha must have done it because she thought his mom was still watching them through the window. That had to be it.
A short time later he was back in the familiar surroundings of Samantha’s squalid apartment. A few weeks ago this place had seemed completely foreign to him and now he took a seat on the couch like he lived there.
Samantha popped out of the kitchen with a beer. “Want a sip?” she offered, slipping onto the cushion next to him.
“I didn’t come over for beer. Where’s the weed you were raving about earlier? I need something to relax after that dinner we just had.”
“About that…” Samantha said, picking at a crusty spot on the old couch, “I had an epiphany tonight.”
“You had a what?”
“An epiphany. Don’t you know what that means, college boy?”
“I know what it means. What does it mean to you?” Grayson asked.
“It means I won’t sell you drugs anymore.”
Grayson still wasn’t sure what Samantha was getting at. “So after what you put me through tonight you decided you’re going to start giving them to me for free?” He smirked.
“No!” she said, laughing. “I don’t want to be your drug dealer anymore, all right?”
“No, that’s not all right. With school and my parents, getting high with you was the only thing making my life tolerable.”
“Have you ever considered that maybe it wasn’t the ‘getting high’ part but the ‘with me’ part that did that?” Grayson noticed Samantha had moved closer to him on the couch. She put her drink down and looked at him differently than she ever had before. “I said I can’t sell you drugs anymore, I didn’t say I can’t help you relax.” Samantha’s face drew toward him and her lips careened into his.
There was a stunned expression plastered on Grayson’s face after the kiss broke. “What’s going on with you?” he asked.
Samantha smiled gently. “I’m supposed to be the dumb one. How much more clearly can I explain it? I don’t mind because you’re so cute when you’re flustered and not sure what’s coming next. That’s exactly how you were at your parents’ house. And that’s when I fully admitted to myself how much I really do like you, Grayson.”
Part of him was waiting for the joke but it never came. “You do?”
“Yes. That’s why I can’t be your drug dealer. Because I want a real relationship with you,” Samantha confessed to him.
“I don’t know what to say.”
“You don’t have to say anything. I can tell this is stressing you out. I can help with that, give to you the kind of relief that’s not plant-based.”
“I’m not sure if that’s wise,” he said.
“I’m not known for my wisdom.” Samantha kissed him again. Her tongue slipped into his mouth.
“Please, I need some time to process all of this.”
Samantha pulled back. “Okay, I’m going to make this very easy for you. All you have to do is sit back and relax. Process things and I’ll do the same.”
“All right, thank you.”
Samantha sunk to her knees and started to undo Grayson’s pants.
“What are you doing!?” he asked.
“I don’t know about you but I process things better with a cock in my mouth.”
“Samantha, come on, you aren’t going to…” Grayson silenced himself when he felt her hand encircle his shaft.
Samantha pulled his cock free from his boxers and warmed it in her hands as it began to grow. Receiving no further resistance from Grayson, who didn’t look like he could say anything right now even if he’d wanted to, she bent down and kissed the spongy tip. More kisses followed, her full lips kindly stimulating his sensitive nerves. Samantha held his cock in one hand at the base, brushed her lips along his shaft and tickled his balls still covered by his pants with the other hand. She waited until his six inch prick was fully erect before taking the swollen tip into her mouth.
Grayson’s eyes closed as she tickled his flared helmet with her tongue. Samantha devoured another inch of his pulsing dick. She sucked hard around his girth and stroked the rest from the base to her lips. The effects were powerful and immediate. Grayson forgot any and all objections. Everything else slipped from his mind. The world consisted only of Samantha and her hot, sucking mouth.
Samantha swirled her velvet tongue in generous circles around Grayson’s tip. She swallowed a dribble of pre-cum and then lovingly engulfed more of his length between her full, ripe lips. Samantha began a steady suction before softening and hardening her tongue in varying intervals as it teased and massaged his needy prick.
Grayson had received a couple blow jobs before, but he’d never experienced anything like this. He heard moans and realized they were his. He decided he preferred Samantha’s blow jobs to her weed. There was no contest. Her soft lips and wet mouth were like heaven to his rigid cock.
Samantha popped his dick from her lips like a sucker and lapped up the excess saliva coating his shaft. Messy blow jobs were the only type of messes she was willing to clean up. “How are you doing, honey bun? Feel calmer yet?”
Released from the wet, hot confines of Samantha’s mouth, Grayson’s cock braced against the sudden drop in temperature. He was instantly desperate to bury his penis back inside the heavenly refuge of her sucking mouth where it was warmed and loved. Samantha knew this. She was the type of t-girl that understood how to retain power whether she was the one giving or receiving the blow job.
“Yes, much calmer. Please, please continue,” Grayson said hastily.
Samantha lazily stroked his shaft in one hand. “Please continue… what? You do remember your pet name for me, don’t you?”
“Uh, please continue, sugar bear. Please.”
“My pleasure, honey bun.” Samantha enveloped his dick back between her smiling lips and resumed the blow job of Grayson’s life. She whipped her tongue up and down his length. Samantha concentrated all her efforts on pleasuring him, steadily picking up the pace and vigor of her oral assault, confident that it would soon culminate in a rapturous orgasm for the one-time college brat she’d grown so fond of.
Samantha planned on having no more teasing pauses, stutters, or stops. Her own cock was aching against her pants like a bar of pure steel and she expected Grayson to return the favor once she was finished. If he sucked her cock like he’d eaten her ass, Samantha would be curling her toes in orgasmic ecstasy in no time flat.
The t-girl’s tongue traced the fleshy outline of Grayson’s cock. Her lips sealed tightly around his engorged slab. She consumed his rod all the way down to the base and then fluttered her tongue like it was the hot, velvety wing of a butterfly against the sides of his manhood. Samantha held all six, pulsing inches in her mouth, bumping down the narrow channel of her throat, and glanced up at Grayson. They looked at each other as the slippery muscles of her throat massaged his swollen crown.
“Samantha, I’m really close to cumming!” Grayson warned. He started looking around for something to catch his load with but Samantha waved him off.
She alternated between sucking hard with hollowed cheeks and rhythmically bobbing her head up and down his pole. It felt like she was sucking the cum up right through his balls, as though his dick were a straw. A pulsing, fleshy straw. Grayson released a thunderous cry before erupting down Samantha’s throat.
Hot, milky sperm spurted from his cock in gushes and was just as quickly swallowed up greedily by Samantha. She couldn’t help but be impressed by his firepower. Samantha gulped his sticky seed down while continuing to tease his sensitive rod with her tongue.
Once he’d finished spewing, Samantha allowed his shrinking prick to slip from her lips. She gave the glistening stalk a couple kisses and then said, “Thanks for the after dinner snack.”
Grayson sat there with a big grin on his face. All was right with the world. He wanted to grab Samantha and kiss her, but she stood up too fast.
Samantha unfastened her pants. “What kind of hostess would I be if I didn’t offer you a snack in return in my own home.” She unleashed her big, throbbing dick in his face. Grayson suddenly found himself staring at a steel-hard, seven inch girl cock.
Being confronted by her intimidating slab of iron flesh left Grayson tongue-tied. “I, I don’t suck cock,” he tried to communicate.
“And I assume you didn’t eat ass until you met me, either. You also didn’t have a girl to bring home to dinner with your parents. I introduce you to a lot of new things. This one will be no different.” Samantha stroked her hand along her veiny, powerful shaft, her large, hairless scrotum filled heavily with creamy t-girl spunk. “Start with a kiss,” she said.
“I can’t. No, I, I can’t.”
“You sure?” Samantha asked, edging the fat tip, a glistening pearl of pre-cum dangling at the slit, closer to his ripe lips.
Grayson scrambled off the couch and started to back away. “I can’t do it. I have to go. I’m sorry. Thank you for tonight, Samantha. I just can’t do it. I’ll call you later.” Grayson zipped his pants up as he hurried from the apartment.
Samantha threw a bundle of dirty laundry at the door seconds after he’d shut it. She flopped down on the couch and rubbed her erection. His cum wasn’t even dry yet and he’d already disappointed her. Left her with a big, hard cock to take care of on her own. Samantha briefly wished she’d stuck to breaking his balls and ripping him off on weed. Instead she’d allowed herself to care for him.
Grayson tried to call and text, but Samantha was ignoring him. He decided to give her some space. A couple days passed and Grayson felt more stressed out than ever. School wasn’t letting up and his parents wouldn’t stop pestering him about Samantha. He scored some pot off a friend. It didn’t help. He began to consider that maybe she’d been right when she said that his sense of relief and enjoyment came from being with her rather than getting high with her.
The young man thought more seriously about the things Samantha had said the last time he’d seen her. That amazing blow job had overshadowed a lot of stuff, but it was just as important that she had admitted she liked him. He was discovering he liked her too and feeling guilty for the way he scurried out of her apartment with his pants down.
A few more days went by and Grayson still couldn’t reach Samantha. The flavor was gone from his life. All the verve and spice she’d brought to his monotonous routine, starting with him tossing her salad the first time they met, was absent. He hungered for it now that it was gone.
Nearly a week had elapsed since that night they went to dinner with his parents when Grayson showed up at Samantha’s building, desperate to see her. He saw her banged up Honda in the complex’s parking lot and knew she was home. Grayson pounded on her door, telling her through it that he’d come because she wasn’t answering his phone. He said he needed to see her.
The door creaked open. “Oh, it’s you,” Samantha said, unimpressed, but she let him in. “All my good stuff’s gone. I might be able to scrounge something up. How much money you got?”
“I’m not here to buy. I didn’t bring any money. I came here to talk to you.”
“What do you have to say? You want to be friends, you still want to get high with me. You think I’m pretty but you don’t like dick. I’ve heard it all before.”
“I shouldn’t have run out on you like that. I should have stayed,” Grayson said.
“If you stayed you would have had to suck my cock.”
Samantha remained silent and didn’t move for what seemed like a painfully long amount of time to Grayson. Then he watched as a smile crept across her face and the wait was worth it.
“Oh, Grayson. I wanted to believe you were different. I knew you were.” She leapt forward and hugged him. They kissed tenderly.
“If you want I could do it now,” he said.
“You think you’re gonna get off, I mean, get me off that easy?” Samantha took a playful bite at his earlobe.
“Yeah, why not?”
“Because of how much I like getting you flustered and keeping you on your toes. I bet you’ve been mentally preparing for the idea of sucking my cock for days. No, that won’t do. You’ll have to give me your ass.”
“You want to… lick my ass?”
Samantha’s lips curled into a smile. “No, I want to bury my fat dick in it, push in and out like I’m bouncing on a trampoline and coat your innermost insides with my seed. What do you say? Let me plant my t-girl flag inside you?”
Grayson’s face twisted. He didn’t want to tell her she couldn’t. He knew if he left now that she would either have something worse in store for him or wouldn’t let him back at all. He wasn’t crazy about the idea, more than a little afraid, but Samantha meant too much to him to say no.
“How do we start?” he asked.
Minutes had to have passed in between yet it seemed to Grayson to be the very next moment that he was lying, naked and helpless, face down on Samantha’s lumpy, old bed. Samantha stood naked by her nightstand, applying lubricant to her stiff pole and hungering over Grayson’s vulnerable body.
Grayson was getting his first look at her tits. They were full and beautiful, he wished he could feel them when Samantha mounted him on the bed, causing them to fall against his chest. She rubbed her big tip up and down his well-lubed crack, savoring the feeling of his hot flesh against her sensitive, hungry organ.
She drew her lips close to his ear and told him in a gently confident tone, “I’ll start slow. No surprises. It’ll hurt at first, but you’ll be crying in pleasure before I’m through. Just relax. Relax your hole for me. When I knock, let me in.”
“It sounds like you’ve done this before,” Grayson said.
Samantha pressed the head of her cock against his small, pink opening. Grayson’s asshole immediately seized the tip in a tight, unyielding grip when she made progress. It felt great, but she knew she wanted to get all the way in without hurting him.
“Untense,” she said softly against his ear. “Relax your muscles. Even though it feels really good when you squeeze. Your grip is incredible.” She moaned.
“I’m trying.” Grayson grunted deeply. It felt like a baseball bat and his instinct was to stop it in place or try to expel it. He could do neither and so he followed Samantha’s gentle directions and put his trust in her. He placed the safety of his most vulnerable orifice in her hands. Only it wasn’t her hands he was worried about.
Samantha pressed more of her immense girth into his slippery, clutching butthole. She had a powerful lower body and could have slammed her hips, sending the whole thing to the hilt inside him in one go, but she went slow. She figured that since he’d given himself to her freely, she had to take extra special care of him. And this felt incredible enough as it was.
“This feels fantastic, Grayson. I only have a few more inches to go. Let me in, honey bun. Just open up and let me in.” Samantha eased, centimeter by centimeter, the rest of her throbbing slab between his cheeks and through his tiny, inflamed pucker. Grayson gritted his teeth and let out a few wails into her bedspread. She didn’t stop until her body was flush with his and the entire length of her dick was buried inside his clutching hole.
Grayson had reached that point during the loss of his anal virginity where it was both over and only the beginning. Samantha was all the way inside him and she had no plans of leaving anytime soon. She reached under him and grabbed his cock. Her hands were still oily. She rubbed his penis, her own pulsing dick buried all the way in his guts.
Slowly Samantha began to inch her t-girl meat out of his sore ass, relishing the aggressive pleasures of his clenching, tender insides. Grayson bit his lip and groaned against the bed. He could feel the girth of her knobby, fat tip scraping along his fragile asshole lining as she withdrew.
“You’ve done this before, right?” Grayson asked through clenched teeth. The pain was intense. Now he wanted to know that she had experience doing this. If she’d done it before, she would know how to do it without making him have to sit on a pillow for the rest of his life, wouldn’t she?
“You’re okay. I have you. It’s going to get easier soon. Concentrate on my voice and my hand stroking your dick.” Samantha eased her hips forward, digging the thick, steely inches of her girl cock back inside Grayson’s tender anal walls. She fully immersed herself into his slick, hot insides and then smoothly gyrated inside him, forcing Grayson’s violated body to become accustomed to its large, throbbing invader.
Samantha pulled out and did it all over again. After four or five more repetitions like that something happened. Grayson stopped focusing on the pain. A new variable entered the carnal equation. Flickering lights of pleasure washed over him, dimly at first, but rapidly glowing brighter. Samantha’s harsh, damp breath coated his neck and the side of his face. Grayson’s eyes closed and his teeth unclenched. A moan escaped his lips. His ass humped gently back at her big cock.
The two horny lovers fell into sync. They had radically different parts to play, but there was a sort of harmony that developed between them. A rhythm flowed between their thrusting, twisting bodies. Like a sheet of music only they knew the notes to. An outsider would have heard raspy moans and seen sweaty humping, but to Samantha and Grayson, it looked like art and felt like heaven.
“You like the way I fuck your ass? Tell me you like it.” Gone were the long, slow strokes inside him. She went at his ass harder, ramming her cock into him until it could dig no further. Grayson’s hot, slippery inner muscles squeezed her rod from root to tip. Her big balls bounced against his.
“Yes!” Grayson gasped. “I, I love it! I love the way you fuck my little fucking ass. Please don’t stop!”
Samantha smiled broadly. “We’re going to change positions slightly. I’m not stopping for anything, honey bun.” Her sweaty breasts peeled off Grayson’s back as she planted her knees on the bed and grabbed his hips, pulling him up with her into Rocky(D)gy style. Now she had the angle she needed to really drill his sweet ass. From her new vantage point she could watch the way his pretty little pucker wrapped around and smothered her stiff meat.
Samantha pounded her hard member in and out of his hole. Her nails dug into his hips and the meaty edges of his butt cheeks. The tight heat and overwhelming friction created by their constant fucking motion would bring Samantha to the brink of orgasm before long. She huffed and growled, hammering her thick cock deep within his sweaty body.
“Tell me again you like the way I lay this t-girl pipe in your ass,” she said, feeling his hole clamping down and sticking to her like glue.
“Yes, fuck me! Fuck me, Samantha! Take my ass with your big girl cock!” Grayson’s own cock felt painfully erect. “I think I’m going to, I’m going to cum!” he cried, his dick spewing all over her sheets. He didn’t even need to touch it, Samantha’s throbbing cock buried deep in his embattled ass did all the work.
Samantha tried to hold out. She wanted this to last as long as possible. She never wanted to have to remove herself from within him. She wanted to stay there forever, until they collapsed from exhaustion and could copulate no longer.
“Not yet, not yet. Oh god, Grayson, I’m gonna CUM!” she howled. The young man’s asshole wound tighter around her throbbing pole as it swelled even thicker and lurched inside him. She erupted like a volcano, dousing his tender anal walls in t-girl cream.
Samantha’s breathing labored and her body trembled as she fired volleys of hot, sticky spunk like a cannon. She moaned like an animal, coating his sore ass with her thick sperm.
“Oh yes, yes! All my cum… take all my cum! Feel it filling you!” Samantha panted. She draped her body more fully over his again as her firing cock began to slow. The last few blasts of buttery semen boiled from her balls and raced through her shaft out the swollen tip into his overstuffed opening.
A minute passed and Samantha kissed Grayson on the cheek. “Thank you. That was wonderful. I think you’re pretty much the perfect man.” She reluctantly withdrew her shrinking rod from his pucker.
Grayson smirked. He tried to change positions and was seized by a piercing pain in his ass. “Owww,” he cried.
“You just took it up the ass for the first time. You can’t move yet. You need rest.” Samantha proudly surveyed her handiwork as cum dripped from his gaping asshole before fully dismounting him and laying down beside him.
Grayson laid flat on the bed and turned his head toward Samantha. Her lips immediately met his and they kissed passionately, but not so passionately that it might hurt him. Eventually as they laid there Samantha grabbed her phone. She surprised Grayson when she got up and started to put her clothes back on.
“What are you doing?” he asked.
“Your mom invited me to tea. She’s been texting me all week. I was ignoring her while I was mad at you.”
“You’re leaving now?” Grayson didn’t know how to take the news.
Samantha grinned, came back over to him on the bed and kissed him about a dozen times. “Stay here. I’ll be back in an hour. It might sound silly but now that you and I are a thing I want her to like me. We are a thing, aren’t we?”
“Yes.” Grayson smiled back at her.
“Then give me one hour. I’ll be a good girl. I won’t tell her you’re currently recuperating back at my apartment after having your anal virginity stolen by my big t-girl cock.”
“You better not!”
“Don’t worry. I’m sure my fat girl dick won’t even come up.”
“Don’t let it! If you think it’s important we’ll discuss how to tell my parents about that later.”
“You’d really be okay with telling them?” Samantha asked.
“Of course. I’m not ashamed of you. I’ve never met anyone like you before. I mean, just think, how many girls can fuck like you?” he joked.
“Be ready to fuck my ass when I get back. If you still can’t move, I’ll ride you and do all the work.” Samantha planted another tender kiss on his lips. “I’ll be back soon and you’ll be waiting, honey bun.”
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.