Fulfilling James

Sam put his coffee mug by the sink and sighed. His foster son James had just gone back upstairs to his room for the third time that day and he was starting to worry. Sam and his husband Carl had become known around the city as the best placement for gay teens and he'd thought he could handle pretty much anything at this point, but James had him stumped.

They'd gotten the call about James 3 years before, when he was 16. Carl and Sam had just started to say that they were done fostering - after 20 years, they were looking toward retirement and were committed to staying involved with all 12 boys they'd raised through high school. They'd always said that they were real parents and that meant that their former placements would always have a bed if they needed it, even after they'd aged out of the system. Most of their boys stayed at home with them for at least a year or two of community college or finding a job after high school. Then, just as they were deciding to raise their current crop of 3 teenagers and be done, the social worker called saying that she had something interesting: a trans boy who'd been kicked out of 3 foster homes and two group homes. So many foster parents were doing it out of a sense of Christian goodness, which was no help at all to the queer kids. But James was apparently adamant that he needed to transition to male and he definitely needed a safe place to stay. Carl and Sam had debated a bit over whether they were prepared to meet the needs of a trans kid, but they'd gone for it and had never looked back.

James was a great kid, once he'd realized that they knew he was a guy and supported his transition. He'd had his share of bad grades and illicit beers, but he was good natured and fundamentally honest with them. He was about to turn 19, had just finished the last of his high school credits, and was going to start trying some college classes in a few months. On the surface, everything looked good. But something about him just seemed off lately. As soon as James had turned 18, he'd started taking testosterone. Within a few weeks, he'd been spending a lot of time shut up alone in his bedroom and the bathroom. At first, Sam and Carl had smirked at each other every time he excused himself upstairs - they'd seen enough boys through puberty to understand the sudden need to "nap" and "shower" a few times a day. The problem was that when James came back down, he didn't have that slightly sheepish but satisfied air about him that Sam would have expected. He seemed anxious, sometimes looking wan and desperate. And he really was spending a lot of time alone in his room. Sam had been worried for weeks that something else was going on, but Carl kept cautioning him to give James space. But it had been long enough, he decided. He'd have to talk to James and make sure that he wasn't in any sort of trouble.

Sam went upstairs to find James's door tightly closed. He knocked lightly, but there was no answer. He knocked again, a little more firmly, but still nothing. Finally, he turned the knob, cracked the door, and froze. James was lying on top of his bed, naked, with headphones on and his computer on his chest. On the screen was a closeup of a cock being vigorously blown and James had one hand down between his legs, rubbing his dick furiously. Sam was about to sneak away when he looked at James's face - he expected pleasure, or enjoyment, or at least concentration, but what he saw looked more like consternation and pain. Without quite thinking about it, he walked in to the room.

James started as soon as Sam walked into his line of sight. He began to close his computer, but Sam put his hand up and said "No, no - it's ok. I'm sorry to interrupt. But I'm worried about you, James. Are you ok? You're up here all the time and honestly, it doesn't look like you're having fun."

James stared at him for a minute, but then said tightly "I just - need to get off."

"Can't you?," asked Sam. "If you really can't, maybe we should see your doctor."

"I can cum, I guess, but it never feels like enough." James's voice had a touch of desperation in it. "There's always something missing! I just, I need something. I thought that after you were done, you were supposed to feel satisfied or something. But I'm up here all the time and it doesn't matter how many times I cum, I just feel- I don't know - empty."

While James was talking, Sam noticed that he'd never really removed his hand from his cock and was still idly rubbing his fingers along the shaft as he spoke. He had a gorgeous little cock, Sam thought - it had grown to about 2 inches and was right now jutting up nicely, with visible veins along the shaft and a swollen pink head emerging from James's foreskin. When James had started t, Sam had googled a bit about the effects, but this was much more penis like than he'd imagined an "enlarged clitoris" to be.

"You mean you feel emotionally empty? Like it's meaningless?," he asked, not sure what else to say.

"No! I feel -- empty empty. Like, I don't know, like I'm itchy and I can't scratch it. Like I'm not really cumming, not the whole way. I'm always up here rubbing my dick and it feels good at first but then I just start feeling empty and when I cum, it barely takes the edge off."

James's frustration was tangible. Sam paused for a minute and then suddenly began to understand. "So, you're rubbing your dick," he paused and flushed a bit at saying those words as calmly as he was trying to seem. "But then you start feeling empty? Or like you need something more to really cum?"

James nodded at this. Sam took a deep breath and continued as delicately as he could. "Have you tried, you know, touching yourself somewhere ... else?"

Suddenly, James was angry. "No! That's not what I mean. I'm a man - I don't want to be touched there. I don't need to use that. That's not me."

"But is that where your body wants to be touched? Enjoying your body doesn't make you less of a man. Plenty of cis gay men would kill for a - " Sam broke off momentarily. He wasn't sure what word to use and he didn't want to offend James further. Finally, he decided to avoid the clinical terms. " - a pussy."

"No, they wouldn't. That's stupid. You're just trying to make me feel better." James bit back at him.

"I mean it! A hole that's always clean, doesn't require any preparation, and lubes itself? You don't think there are some cis guys who would find a use for that? Hell, I'd use it if I had one!"

James looked up at him, but didn't say anything.

"Look, you might as well try it. You're miserable up here. If you don't like it or it freaks you out, you don't need to do it ever again, but it is your body and you deserve to enjoy it."

Finally, James said quietly, "I don't think I know how," and fell silent.

Sam sat down on the bed, suddenly aware that his own cock was responding to this ridiculous situation. "Well, I guess you just, I don't know, try putting a finger in and see what you like?"

James, not breaking eye contact with Sam, raised one knee a few inches and slid his hand down further between his legs. Sam couldn't see what he was doing, but James's hand bent inward and it seemed like he was trying Sam's advice. After a few more seconds, he pulled his hand up and threw his head back in frustration. "It isn't helping! It doesn't feel right."

"Well, it will probably take more than few seconds to figure out what feels good", Sam said, sensibly.

"No! It wasn't right - it wasn't deep enough. The angle was wrong. I need more inside."

Sam looked at James for a long moment. Then, finally, purposefully not thinking about what he was suggesting, he said, "Do you want me to try to help you?"

They were both silent. Sam was tempted to run from the room and forget this had ever happened, but James was staring up at him, expressionless. Sam's own cock throbbed in his pants and he was trying hard not to think about what that said. Then, slowly, James's spread his legs, bending them at the knee. Below his cock, his swollen lips separated to show his wet pussy. The entrance was almost impossibly small and twitched occasionally. Beads of liquid had collected below the hole. James stared at Sam almost defiantly, daring him to comment, or do something.

Without breathing, without meeting James's gaze, Sam cautiously extended one hand, one finger, in between James's legs. He started below the hole, collecting the hot pre-cum on his finger. James inhaled raggedly as he made contact, but didn't move or say anything. Gently, Sam moved his finger up, just circling the entrance, rubbing it delicately, feeling it open slightly beneath his pressure.

"Rub your cock while I do this," he instructed. "And tell me what feels good."

James moved his hand back to his cock and circled one finger around the head, then nodded. "Keep going."

Sam slowly pressed harder - James really was tight - and pushed the tip of his finger inside James's pussy. Once he got part of the way in, it was easier going. James was soaking wet and hot around him. Reaching up further, Sam felt the rough ridges of James's G-spot. It was a surreal feeling - he'd only done this a few times before, with his last-attempt-at-straightness high school girlfriend, and physically, his finger felt the same, but externally it was all different. Above the waist, James looked like any other twink. He'd had chest surgery 6 months before and the keyhole procedure he'd had done had left minimal scarring. He had a few hairs around his nipples and then a thick line of hair down his stomach leading to his trimmed pubic hair and an utterly male cock, albeit small, sticking up hard and swollen. There was nothing feminine about him and Sam felt none of the apathy he'd felt for his old girlfriend's body. On the contrary - he was worried about how much harder his dick could get without injury. He pressed upwards at the rough patch and James shifted slightly. "Is that good? Is that where the itch is?".

"Almost - up higher."

He pushed in further, James exhaling as the tight hole accommodated Sam's second knuckle. He bent his finger slightly and pressed up just past the ridges and James gasped. "Yes - there- oh, there." If possible, James's pussy got even wetter and Sam began rubbing harder. James's cock seemed to swell a little more and James left off the slow toying with his head and began rubbing up and down the shaft in earnest.

"Shit, Sam, there - that's good," James stammered. "Keep going, please, keep going."

Sam maintained his rhythm and tried to keep breathing himself. Taking a cue from how verbal James was being, he experimentally said "You like that? Does my finger feel good filling up your pussy?"

For a moment, Sam was sure he'd ruined everything, as James went stiff. But then James actually clenched around his finger and gasped out "Oh god yes, please, fill up my pussy. Go deeper, Sam, please -- Deeper!"

Sam pressed his finger all the way in, splaying the rest of his hand flat against James to reach in as deeply as possible.

"Oh, fuck it, Sam. Fuck my pussy with your finger!"

From how easily the words came out, Sam started to suspect that James had been trying unsuccessfully to not fantasize about this for a while. He began pistoning his finger in and out of the grasping pussy, always pressing up firmly as the tip of his finger ran over the sensitive ridges.

After a minute of this, James began writhing underneath him and rubbing his cock hard and fast. "Are you going to cum soon, James? Are you getting ready to cum hard with my finger inside you?"

"Fuck, yes. Fuck! Sam, I'm cumming. Go all the way in - fill me up. I want to cum on your finger."

Sam quickly drove his finger in up to the hilt and James tensed and froze, his pussy clenching hard on Sam's finger while cum positively flowed out of him. Sam stayed still, finger sunk inside James as far as it would go. He couldn't breath, watching James shudder underneath him. Finally, after what seemed like hours, James relaxed and opened his eyes.

"Better?" Sam asked, smirking at him a little.

James nodded a bit shyly - it seemed like his frank verbal side in the heat of the moment had given way to some embarrassment. Sam slowly withdrew his finger from James's sopping pussy, getting one last shudder from James as the hole stretched around his knuckle.

Seeing Sam's hand drenched in his cum made James flush further. Sam took pity on him and put his dry hand on his shoulder. "I'm glad," he said fondly. "Now get some rest. And think about what you want to do for your birthday tomorrow! I'm going to go start dinner."

Sam excused himself from the room and almost ran to his own bedroom. He peeled his pants off and released his hard cock. He was torn for a moment about whether he wanted James's cum on his dick or in his mouth, but quickly decided, sucking his wet finger like it was a dick while fisting his own cock with his other hand. James tasted remarkably like semen and Sam came within moments, spurting into his hand and onto the floor. Wondering what, exactly, he was getting into, he spread a little of his own cum onto the hand that had been inside James just minutes ago and licked off their intermingled cum, imagining what it would be like to suck his cum directly off of James's dick - or out of his pussy.

--------------

That night at dinner, James was shy but seemed happier. All their older boys had moved out, although they came back to visit regularly. That night, though, it was just Carl, Sam and James. After dinner, while they were cleaning up the kitchen, Carl turned to Sam and asked, "What's up with James tonight? Did he seem a little quiet?"

Sam paused. He'd been thinking about how to handle this all night. He and Carl had been together for 25 years, but complete monogamy had never been a part of their relationship. They practiced honesty instead - being forthright about what they did and bringing the fun home to their own bedroom. They had never even considered getting involved with one of the boys, but Sam didn't think Carl would be too horrified over that either. Their home had by necessity been a place for all their foster sons to be casual and open about sex and in some way, maybe this was a natural extension of that. Holding that thought in his mind, Sam answered, "I had a talk with him today - about how I was worried about how much time he'd been spending alone."

Carl must have heard something in Sam's voice, because he only raised his eyebrows and waited for Sam to continue. "I followed him upstairs this afternoon. I knocked, but he didn't hear me - so I went in and found him trying to jack off, but looking totally miserable about it. I probably should have snuck back out, but then he saw me and started talking. Apparently he's been mired in shame all this time because - well, he'd been wanting something, internal, you know, but figured that wasn't manly enough. So he's been trying desperately to be satisfied with just rubbing his cock but feeling, in his words, 'constantly empty'."

"So what did you say to him?" Carl asked.

"Well, I told him that I didn't think it was feminine at all to enjoy his body and that plenty of cis gay men would be happy to have a convenient orifice like that. So, he... tried. While I was standing there! I was about to leave, but suddenly he's giving up and saying it's no good, that he can't do it right. And the whole time, giving me this hopeless look."

Carl broke out laughing, "Oh, lord, Sam. Don't tell me you fingered our foster son!" Seeing Sam's expression, he said, "Well, he's 19 tomorrow and not legally our foster son since he turned 18. I assume you made damn sure that he wanted you to?"

Sam nodded. "I asked if he wanted help and he spread his legs right away. Then he, ah, directed the action the whole time."

Carl grinned. "Did it work? Did he enjoy it?"

Sam nodded again. "It seemed to .. do the trick. He certainly came hard enough. I think he's a bit shy around me now, but don't you think he looks a little less closed off and ashamed looking? And he's down in the basement playing video games, not up in his room again."

Carl put down the dish towel he'd been using and came closer to Sam. He snagged his fingers in Sam's belt loops and pulled him in. "And how about you?", he asked quietly. "Did you enjoy it too?"

Sam's dick twitched at Carl's closeness and the memories of that afternoon. "Yeah," he answered, pausing to kiss Carl. "I had a pretty good time."

Without saying more, Carl led him to the bedroom and pushed him on the bed. Between kisses, he said "Tell me more - what happened after he spread his legs?"

"He's got a gorgeous little cock - just a mouthful. And his pussy was soaking wet. I just put one finger in him - that's all he needed, he's so tight. I started by rubbing his G-spot, but then he wanted me deeper. He's a verbal little thing - I asked him if he liked me in his pussy and he couldn't stop talking, begging me to fuck him with my finger, go deeper and harder. Finally he asked me to go all the way in, so I drove in hard and he came like you've never seen. I thought he was going to pass out and his pussy was grabbing onto my finger like he wanted me to stay in there forever. So I did, until he could breath again, then I pulled out and left."

While Sam was talking, Carl had been undressing them both, interspersed with kissing Sam's chest and neck. As he unbuttoned Sam's jeans and began to slide them down, he asked "That's it? You just left? And it was over?"

"Well, James looked like he needed a nap. But I, ah, came down here for a bit."

Carl waited expectantly. Sam's cock was hard and jutting up, but it was clear Carl wouldn't continue until he did.

"His cum was all over my hand - he was so wet! I thought my dick was going to explode when he was begging me to fill him up. I could barely control myself. As soon as the door was shut in here, I couldn't stop myself from licking his cum off my hand. I came in seconds."

"Which hand?"

Sam extended his right.

"Middle finger?"

Sam nodded. Carl took the hand and sucked in Sam's middle finger. Sam couldn't breathe. "Can you taste him?"

"A little bit. I bet he's delicious. Did you think about sucking him?"

"I wanted that little cock in my mouth so bad. And then I wanted to drive my tongue as deep into his pussy as I could get it."

Carl began slowly rubbing Sam's cock as he talked.

"He was just so needy, Carl. He couldn't help himself, he was so turned on. He might be shy now, but when I was up inside him, he had no filter. He was saying the dirtiest things about fucking his tight little pussy."

Carl reached for the lube they kept on the bedside table and Sam shifted and raised his legs a bit. As Carl lubed his own cock and then Sam's ass, he said "And were you thinking about fucking his tight little pussy too? Maybe with more than a finger?"

Sam nodded, not trusting his voice as Carl's fingers slipped inside him to spread more lube around.

Carl knelt over him on the bed and lined the head of his cock up with Sam's ass. As he pushed inside, he asked "Did you think about pressing your big cock head right in that tiny hole, filling him up all the way with your dick? Is that what James needs? To get his tight little pussy fucked by big daddy cock, to get stretched wide open and hammered until he can't breath? To ride a big pole until he cums all over it? To get filled up with cum, then have it sucked out of his hole and then filled again? Is that what you were thinking?"

Sam moaned at Carl's words, remembering James with his legs splayed so wantonly under him that afternoon, and imagining him with his legs not just splayed but raised up, holding his pussy wide open while a big cock drove into him, James gasping and whimpering and talking about how full he was and how much he needed that dick inside him. James shuddering and squirming and cumming over and over, rubbing his perfect wet little dick and begging for more.