Dinner With a Client

Max visited his parents over the weekend. They were starting to notice Max’s changing physical appearance but didn’t comment. His hips looked wider and his face softer. His chest had obvious breasts, even if they were very small. His hair was getting longer and he had continued to get women’s haircuts which were hard to hide. They seemed happy to see him and they had a good time.

Dylan texted over the weekend and Max sent him some photos of his ass again but he wanted more.

“I want a video of you telling me how much of a slut you are.” The request was beyond what Max wanted to do but he felt he’d neglected Dylan and relented. He put on a face of makeup, a choker and some lingerie and set up his camera.

“Hi Dylan, I’m your nasty little slut.” Max stopped the video and put his head in his hands. He felt too embarassed to send it and tried taking the video a few more times.

“I can’t wait to see you on Monday. My slutty little body is all excited, look” max panned the camera down to his caged cock and wiggled his hips, the padlock clacking against the frame, “I’m just a dirty little cumslut, I can’t wait to feel your hands on my tight ass.” He pointed the camera at the mirror and bent over to show his butt plug and toned glutes. He ended the recording, cringed, and sent it to Dylan. He didn’t reply. Max liked the idea of him jacking off to his little teases.

The rest of the week flew by. Denver wasn’t in the office on Monday or Tuesday and the mood with the associates was much better on those days. They flirted with Max like normal and few of them groped him while he was busy with tasks. Denver returned on Wednesday and Max knelt excitedly at his feet, ready to start the morning. Denver however did not pull his dick out and dismissed Max without so much as a slap on the ass. Max was disappointed and his loins ached. He felt deprived of his usual release. Thursday went the same way, Max dressed particularly slutty to try and goad Denver into using his mouth but he ignored the advance and was polite. Harry was particularly handsy that day, he liked when Max showed skin and he pressed Max against the wall of his office and kissed him passionately. He groped at Max’s cage and plugged asshole. He placed Max’s hand on his cock over his pants as he pinned him and Max rubbed his dick through his slacks. Before long Harry backed off and let Max leave without any further advance. What was going on this week? Harry had not been shy about devouring Max two weeks ago but now he was holding himself back. Dylan hadn’t come in at all that week either so Max had to entertain himself with the gropings of the analysts. His balls ached and he rode his dildo particularly hard that night.

Friday came and the day went by quickly. Denver told Max to leave early that day so that he could get ready. Harry wished him luck as he left.

Max fretted with his outfit. The dark red dress was form fitting but went down past his knees. It was strapless and he was oddly pleased by the way it accentuated his small breasts. He put a black shawl over his shoulders and picked out a handbag in which he placed a collar and leather leash. He posed in the mirror and noticed that at certain angles the cage caused a noticeable bump between his legs. He looked really good. His tan skin popped against the dress and his legs looked toned and sleek. He put his hair up in a small bun and besides his bulge it would be impossible to tell he was actually a guy. His phone buzzed.

“I’ll be there in 10 minutes. Don’t wear any panties.” The text read. Max assumed this was Denver’s number. Max removed his panties and checked the dress. The slit up the side stopped at his mid thigh and he figured this would be fine. Max took a deep breath and went downstairs to wait for Denver.

Denver pulled up in a sleek looking BMW, it was somewhere between a roomy sedan and a sports car. He got out and opened the door for Max who slid into the leather passenger seat. Denver got back in the car and started to drive.

“You look lovely Maxine.” Denver said smoothly.

“Thank you, I feel a little silly.” Max said shyly. He admired Denver in his suit, it was a dark blue with a white collared shirt and a patterned tie.

“Don’t be ridiculous, you look perfect. Now tonight I’m going to introduce you as Maxine. We’re going to sit in a private room. It will be you, myself, the client, and his partner. They are part of a big account and we need to make sure they are happy. The client’s name is Jerry Gill, his partner is Michelle. You need to focus on Jerry. Jerry makes the decisions but Michelle is sharp and young and wants to prove herself. I will take Michelle, I need to get her on my side. Jerry is easy, he’ll be all over you and I just need him happy, you don’t have to talk shop or pitch him, just flirt and keep his attention on you. Do that, and this night will be smooth sailing.” Denver spoke with purpose.

“Yes sir.” Max said, not taking his eyes off his boss.

“For tonight, don’t call me sir. Call Jerry sir. He’s your target tonight.” Max felt like a spy. He was getting excited at the thought of teaming up with Denver for a big mission. Max imagined Denver ripping his clothes off on the drive back after winning the client over.

The car pulled up to a fancy hotel and Denver handed his keys to a valet. They made their way into the lobby and to the left into a dimly lit restaurant. Denver spoke with the hostess and she brought them through the restaraunt, past all the tables filled with fancily dressed people to a back room. Inside was a large round table with place settings for four and occupied by the clients. Jerry was an older man but in good shape. He had brown hair and a light beard. He wore a sharp suit and Max estimated that he was in his forties. Next to him was Michelle. She had long dark hair and wore a suit as well. She was gorgeous but had cunning eyes. They both stood to shake hands with Denver.

“This is my assistant, Maxine, Maxine this relic is Jerry and his partner at their company Michelle.” Max reached out and shook both of their hands. Michelle looked at Max and smiled knowingly. She knew why he was here and Max felt uncomfortable. They sat and ordered drinks from the waiter standing nearby.

“So Maxine, tell me, how long have you worked for Denver?” Jerry asked almost immediately. His eyes were already probing Max’s chest.

“Maxine has been with us for almost a year now.” Denver lied.

“Well lets let her say it. Maxine how long have you been with Denver?” Jerry asked in jest.

“It’s been a year.” Max said shyly.

“I know he rides his people pretty hard, I hope he hadn’t been too rough with you.” Jerry laughed.

“No he’s been very gentle.” Max felt nervous.

Denver nudged Max’s leg with his own as he turned to Michelle and began talking to her about an email she sent.

“Jerry, how do you know Denver?” Max asked quickly.

“We go way back but we’ve worked together for a long time. He’s a clever guy that Denver.” Jerry took a sip of his drink as he eyed Max up and down. “Tell me, what did you do before this? You look like you keep on good shape for office work.” Max took the hint and started to lie.

“I was a runner in college. This is my first job since then and I’m just trying to do my best to keep Denver happy, you know how he is.” Max played into what Jerry seemed to want to hear.

“I do know how he is. He always finds the best people.” Jerry hadn’t taken his eyes off of Max and he wondered what he knew of Denver’s tendencies.

“Jerry is feeling pretty shy about our earnings next year and we’re worried about costs.” Michelle’s conversation floated in to the rest of the table. They all began to talk shop and Max felt a little awkward. He sipped his glass of wine and picked at the appetizers on the table as Denver navigated the concerns Michelle raised. Denver seemed like he was having trouble cornering Michelle and Jerry was starting to participate more. Max decided he needed to help. He took off his heel and slid his foot to his right under the table towards Jerry. He placed his foot against Jerry’s shoe and moved it up along his leg, brushing lightly as though it could be a mistake but so that Jerry would know it wasn’t one. Jerry stumbled on his words and took a sip of water. His eyes darted Max who pretended not to notice, lookint at Michelle and Denver, acting like he was paying attention to what they were talking about.

“Let’s can the shop talk for a bit, poor Maxine must be bored to ****.”

“No, no this is good for me to hear.” Max jumped in, looking at Jerry now.

“No he’s right, I’m sorry Maxine.” Michelle cut in. “Tell me about yourself, I’ve been rude. In what capacity do you assist Denver?” Michelle emphasized assist, her words like knives.

“I handle all the scheduling and paperwork for the most part. It’s not super interesting but I definitely have my hands full.” Max held eye contact with Michelle. She smiled.

“I like this one Denver, you’re so good at finding help.”

“I think I’m good at seeing someone’s value.” Denver said smoothly, looking directly at Michelle. Max felt a pang of jealousy.

The food arrived shortly after, Max was starving but had ordered a salad as that seemed appropriate. Everyone was on their second or third glass of wine and Denver and Michelle were talking animatedly about trips they’d taken to South America.

“Are you much for travel?” Jerry asked Max.

“Not much, I prefer to spend my time here.” Max had never left the country before.

“I would love to take you and Denver out to Tahiti. It’s beautiful, I go every year. The beaches are wonderful and I’ll be you do well on a beach.” Max removed his shawl, he was getting warm after his second glass of wine. Jerry couldn’t take his eyes off of him.

“I would love to go with you. I need to work on my tan.” Max rubbed his arms.

“I think you look well tanned enough, but it couldn’t hurt to get some new tan lines.”

“I shouldn’t say this but I sunbathe naked, so my tan lines are already in a good spot.” Max lied.

“That must be a sight for sore eyes, where do you do that?”

“On the roof of my apartment building.” This was something Max had considered but never actually done.

“Lucky neighbors I’ll bet.” Jerry scooted his chair closer to Max. Both Denver and Michelle looked over at the disturbance, Denver smiled but Michelle looked annoyed. Suddenly Max felt a hand on his knee under the table. It was placed there with a casual pat but slit it’s way upwards onto his thigh. Max felt warm at the touch and Jerry leaned in to whisper in his ear.

“Denver and Michelle are so boring. They both want to talk business all the time.” He imitated them in a mocking voice. Max giggled at the joke and felt Jerry’s hand rub his thigh through his dress. “They don’t know how to have fun like we do. They’re perfect for eachother don’t you think?” Max laughed a little and nodded. “That just leaves us to have all the fun I guess doesn’t it?” Jerry’s lips practically touched Max’s ear and his breath was hot and smelled sweet from the wine. Max leaned in closer and placed his hand on Jerry’s thigh. His legs felt strong and muscular. “You missed.” Jerry whispered. Max ran his hand up Jerry’s thigh towards his inseem. Max lingered there without allowing his fingers to wander towards the heat between his legs. “You’re such a tease.” Jerry chuckled and slid his hand under Max’s dress, pulling it up a little as he did so. His hand caressed Max’s smooth thigh and he prodded and squeezed at him. Max’s stomach felt giddy, possibly from wine, and his fingers danced around Jerry’s thigh. He liked the attention.

“Jerry, we should probably get going, big day tomorrow.” Michelle spoke tersely.

“I think Maxine and I are going to grab a nightcap at the bar, I’ll be up to my room shortly though don’t you worry.” Jerry chuckled like a child being scolded. Michelle rolled her eyes and shot Denver a look. They got up to leave.

“Maxine, call me when you’re done if it’s not too late.” Denver said and he left with Michelle.

“Finally, we’re alone!” Jerry exclaimed as tossed back the last sip of his wine. “They are right though, shall we take a bottle back to my room so that I can get to bed on time?” Max didn’t know what to say. He’d expected Denver to give him an out but he just left him here. He couldn’t say no.

“Maybe you’ve had too much wine tonight.” Max said tentatively.

“Nonsense! There’s never enough wine when you have company as gorgeous as yourself.” His hand slid into Max’s inner thigh.

“You drive a hard bargain.” Max said unsure of how to get out of this.

“Excellent!” Jerry got up from the table and offered Max his arm. Max took it. They stopped at the bar to grab a bottle of wine and Max felt like the whole bar was watching him. He probably looked like a prostitute about to go satisfy a client. Max realized that might be what Jerry thought too. They made their way to the elevator and Jerry selected the 24th floor. The doors closed and Jerry was on Max in an instant. He swept Max up in an embrace and kissed his neck. His grip was strong and Max could feel his muscles through his shirt. His beard scratched at his face but Max let out a gasp as he sucked on his neck. Jerry’s hand dropped to grope Max’s crotch but he shifted his leg to prevent this. Jerry’s hand kneaded his thigh and his other gripped his waist as he devoured Max’s neck like a vampire. Max felt caught in the wave of Jerry’s lust, unable to disentangle himself from his overwhelming **** on his senses. Max felt himself succumbing to his own urges, the neglect of the week setting in and seeing an opportunity to get some release he allowed Jerry to grip and grab at his body in all directions. The elevator dinged and Jerry left his hand on Max’s thin waist as he led him to his room.

“Home sweet home,” Jerry joked. The room was fancy, it had a living room area with a small kitchen, a large bed tucked in a room in the back and a lavish bathroom. It was lit dimly by soft hanging lights and it smelled nice. “Please make yourself comfortable.” Jerry gestured to the couch. Max sat with a puff as the couch enveloped him. He could barely think as Jerry poured two glasses and sidled over. He removed his tie and jacket and unbuttoned several buttons from his shirt. He sat next to Max and handed him a glass.

“To business!” He toasted and Max chugged his glass. “Nervous are we? I would assume someone who looks like you sees a lot of action.” Jerry watched Max intently.

“I haven’t done this before.” Max said honestly.

“Mixing business with pleasure can be risky but it’s always worth it in my opinion.” Jerry said, missing Max’s meaning. Max offered up his glass so Jerry could pour him another. Max downed it also. His head felt light and his body buzzed with anticipation.

“So, how do you want me?” Max said, feeling the **** and anxious to get started.

“Ooh straight to the point, I like it. But let’s have a little fun. Let’s play a game.” Jerry shifted his body to face Max. “Never have I ever. Have you played?” Max had played in high school. It was an odd choice but he nodded. “Each time you have done something, you either take a sip or remove a piece of clothing.” Jerry filled both their cups. “I’ll start. Never have I ever stolen anything.” Max nodded and Jerry looked at him expectantly.

“Never have I ever slept with a business partner.” Max figured a coworker or boss wouldn’t count. Jerry laughed and he removed his shirt. His chest was hairy but muscular. He didn’t have as broad a frame as Denver but his chest was well defined.

“Never have I ever slept with my boss.” Max got what he was getting at but got away on a technicality there. “Oh I thought I got you there.” Jerry laughed.

“Never have I ever gotten anyone pregnant.” Max said slyly.

“Oh you’re a clever one. I’ll take the drink on that one.” Jerry took a sip of wine.

“Never have I ever sucked a dick.” Jerry chuckled at his clever move. Max took a sip of wine. “I had hoped you might go for the dress.”

“I thought I’d keep it on.” Max said coyly.

“Ooh okay. Show me a little leg at least.” Max hitched the dress up to his mid thigh to show off his leg. Jerry knelt and began kissing Max’s leg. He worked his way from the ankle to his thigh but Mx stopped him from going further.

“You tease me still?” Jerry complained.

“You sure you want to see?” Max said, losing himself to the drink. Jerry took this as consent and pushed Max against the couch and hiked his dress up to his waist. He kissed Max’s belly and groped at this legs.

“A pleasant surprise. This must be a gift frol Denver then.” Jerry commented seeing Max’s caged manhood.

“I guess I am.” Max thought about that for a moment as Jerry fumbled with the cage, suddenly a great relief washed over Max as the cage fell away.

“Much better, a gift is always better without its wrapping.” Max felt a warm sensation as Jerry took his shaft in his mouth. Max gasped and sunk into the couch as the pleasure washed over him. The warmth pressure eased on and off as Jerry sucked him. Max watched the man between his legs work from over his dress. He was clearly experienced as he danced his tongue around Max’s manhood. Jerry was able to take almost all of him at once, a far cry from the struggle of Max’s mornings in Denver’s office.

“Beautiful.” Jerry said as he released his suction. Max was dissappointed that he stopped. Suddenly Jerry lifted Max’s hips and pushed his legs over his head, exposing his bejeweled asshole to the older man. “Ah I see you were prepared for the night. Naughty girl.” Jerry gripped the plug and began to pull it slowly from Max’s virgin hole. He squirmed a bit but relaxed. His hole distended as the thickest part spread him wide and then collapsed, pushing the rest out with ease. Jerry’s hand came between Max’s legs and held the butt plug in front of Max, it dripped with lube. Max took it in his mouth, feeling the warmth and savoring the taste of his own cavity. Jerry pressed his face into Max’s ass and breathed deeply.

“You smell like sex.” Jerry said as he applied his tongue to Max’s winking ring. His warm tongue felt amazing as it prodded and explored his outer rim. Max couldn’t help but think of how different it was from Harry’s relentless ****. He was tender and Max’s cock began to twitch as Jerry’s tongue penetrated his innards. He lavished every curve and wrinkle and Max welcomed the warm sensation. Max let out a moan as Jerry pushed his tongue as deep as it would go. Suddenly Jerry stood and undid his pants. His cock flopped out, already full erect. It was smaller than Denver’s but still bigger than his own. He had a well trimmed bush and Max evaluated it to be just a bit bigger than the dildo he rode at home. Max sat forward and took him in his mouth. It was much easier than Denver’s massive snake and he was able to swallow almost the whole thing, gagging as he did so.

“God you’re well trained.” Jerry groaned as Max took him in and out of his throat, coating him in spit. Max tasted the familiar salty embrace of another mans precum on his tongue. “Woah, I can’t have it be over yet.” Jerry withdrew his shaft from Max’s eager lips. He grabbed Maxine, throwing him over his shoulder and tossing him onto the bed. He pulled Max’s ass towards the edge of the bed and pressed the tip of his cock against his virgin hole. Before Max could protest he gave a slight thrust and the head of his cock entered Max. It wasn’t much bigger than the dildo but Max cramped a bit and gasped. “Good girl, hold on, there’s more don’t worry.” Jerry held Max’s hips and plowed into him, his drunken lust taking over his earlier tender treatment. Max cried out as Jerry buried himself in Max’s tender hole. “Oh thats right, squeeze down on me, that’s incredible.” Jerry threw his head back as he skewered Max to the hilt. Max thrashed a bit on the bed but held in a scream. Jerry was in him now and he started to pull back to deliver another blow. The next thrust felt like it bruised Max’s diaphragm. Jerry was completely overcome with lust and began to pump his hips to a brutal rhythm. Max was pressed against the bed as the older man took his virgin asshole for all it was worth. Each thrust sent a familiar electric pleasure through Max’s cock and stirred the contents of his overfull sack.

“Denver clearly hasn’t broken you in yet, your asshole is tight as a virgins. I bet he’ll have you screaming bloody **** when he finally decides to make an honest woman out of you.” Max could barely breathe, each thrust turned his brain to mush and felt like it would tear him in two. He felt like he was above himself watching this man fuck him like a common whore. He was a ragdoll on the bed as the older man rutted him out. Jerry grabbed Max by the dick and began stroking as he fucked him. Precum leaked from his tip without any prompting from Max.

“You like having my cock in your ass Maxine? You look like you can’t get enough.” Max could only manage a moan as another thrust from Jerry sent waves of pleasure through his prostate. “Talk to me, you still with us?” Jerry asked as he pummeled the skinny man beneath him.

“Yes sir, thank you sir!” Max cried as Jerry mangled his insides. “I’m happy to take your cock sir.” Max was gasping for air.

“You’re gunna have to stay the night. This ass of yours is too good to let you get away.” Jerry was breathing heavily from the effort of rearranging Max’s guts.

“Yes sir, you can fuck my ass anytime you like sir. Please don’t stop!” Max begged as his loins felt like they would boil over. Jerry redoubled his effort, sinking his shaft deep into Maxine over and over again. Max screamed as his cock exploded, cum spattered on his stomach and across his dress. Watching Maxine’s violent orgasm pushed Jerry over the edge and be flooded Max’s colon with his seed. After a moment of pumping Max’s guts full of his essence, Jerry withdrew, cum splattering onto the bed as it gushed from Max’s now broken hole. Max lay there, covered and full of cum completely lost.