An Unusual Gift

Jack's day went fairly quietly. He attended his classes, which was made more fun by Miss Jameson bending over. This time it was clear she was wearing a plug, although Jack seemed to be the only one to notice. Maybe it was because he was looking for it. Other than that exciting event, his day was quiet until he arrived at work. He stuck his head in to see Sarah, just to test if his command worked.

"Hey Jack," she smiled at him.

"Hey, I was just checking how you were doing," he replied.

"I'm good, although these order forms are doing my head in."

"I know of a way to take your mind off them for a bit," Jack suggested, wondering if Sarah would take the bait.

"If you're wanting a quickie, I can't, these forms really need doing now," Sarah replied. Dashing his hopes. "Although, I was always good at multi-tasking."

Jack wondered what she was talking about, until she stood up and leaned forward. She bent over and reached back, pulling up her skirt. She hiked it up until her ass was exposed before pulling her underwear to one side, revealing her pussy. Jack didn't need asking twice as he stepped up behind her and unzipped his pants. His cock was already hardening and only needed a few strokes to bring it to full attention.

Sarah continued tapping away at her keyboard as Jack pushed his cock against her entrance. He watched the head slowly spread her large labia before it settled into her entrance. Slowly pushing forward, he enjoyed the sight of his cock sinking into her inch by inch. She gasped slightly as he filled her slick tunnel, but she continued with her work.

Jack took it as a challenge to distract her as much as possible, so he pulled back until just the tip was left inside, before slamming back into her with force. She groaned, but still didn't break from her work. Jack began thrusting, slowly at first, but quickly picking up the pace.

Sarah's office filled with the sound of his hips slapping against her pert ass as her she studied the screen. She was no longer typing, but Jack didn't know if that was because she couldn't while he was thrusting or she was just busy reading. Either way, she was leaving all the work to him, which he was fine with. Her cunt felt like velvet around his cock, smooth and soft, massaging every inch of his shaft with each thrust.

He wished he could spend his whole shift with his cock buried inside his boss, but he knew eventually someone would notice he was missing and come looking for him. Or they'd come looking for Sarah to report that he hadn't shown up for work. Either way, it'd involve someone discovering them.

Knowing this would be the only chance he had to fuck her today, Jack savoured the feeling. The heat and tightness of her tunnel, the firmness of her petite ass as he massaged it. Sarah started moaning and he looked up, seeing her hanging her head as she began to push back, meeting his thrusts half way. She groaned and Jack picked up the pace, ploughing into her with as much force as he could muster.

"Oh fuck..." Sarah groaned. He saw her hands gripping the desk tightly and knew she was getting close. He was also getting close, but he wanted to make her cum first. He tried to think of anything to distract him and delay his orgasm, but he was careering towards it like an out of control freight train.

"I'm gonna cum!" He warned.

"Me too! Oh fuck! Don't stop!" Sarah replied. He groaned and thrust into her faster, finding a burst of speed as he reached his peak. He slowed down and instead thrust in hard, forceful thrusts as his cock began to empty its load inside his boss. She cried out, louder than she should have if they didn't want anyone hearing and gripped her desk as her legs trembled.

"Fuuuuuuuuckkkkkkkkkk!" Sarah groaned as her orgasm washed over her. Jack pushed deep into her, his own orgasm spent as she rode out hers. She hung her head, panting hard as her orgasm faded. Jack slid out of her and Sarah reached back to return her underwear to it's usual position before pulling down her skirt.

"I should start my shift," Jack grinned.

"Yeah, you should before anyone asks where you are. Plus I need to finish these forms, seems I'm not as good at multi tasking as I thought."

"You just need practice."

"And I presume you'd be happy to help with that?"

"Just making sure we're all working to the best of our ability! I thought you'd be pleased with that," Jack teased.

"Go and start your shift," Sarah replied, rolling her eyes. Jack laughed and left the office, heading towards the bar. He marvelled at how instantly the collar had changed his relationship with his boss, even when she wasn't wearing it.

The next afternoon, Jack had just finished college when he heard a banging at the door. He went to answer it to find a very annoyed looking Abby standing there.

"What's wrong?" He asked.

"Fucking Mark Thomas, that's what wrong, the sexist prick!" Abby complained, barging her way into his home.

"What did he do now?" Jack asked. Mark was a typical jock, thought he was better than everyone because he coasted through college on a football scholarship. Bullied anyone he perceived as being a nerd, which was everyone who wasn't a football player and he viewed women as pieces of meat that only existed for him to try and stick his dick into.

"He made a joke about how I wasn't really a woman because I didn't have big tits, when I told him to go fuck himself, he said I could prove I was a woman by going and making him a sandwich. Then as I stormed past him, he slapped my ass and told me what kind of sandwich he wanted."

"Wow, that's a lot, even for him."

"Yeah, well I'm going to get him back."

"The collar?"

"Exactly."

"While I'd usually be against getting revenge on people, I have a collar that let's me control people, so I might as well use it. Or rather you use it in this case," Jack smiled. Abby grinned at him.

"Well I happened to know he's going to be at a bar tonight, let me take the collar and have some fun with him?"

"How are you going to get him to wear it?"

"I'll just hint there might be a blowjob involved if he puts it on, he's such a douche he'll probably do it straight away."

"Yeah, I expect you're right."

"Want to come with me?" Abby asked.

"Nah, I've spent the last two nights working in a bar, I don't really want to hang out in another."

"Even if it means seeing Mark under my control?"

"Even then. I'm sure you'll tell me all about it."

"That's true."

Abby hung out for a while before she went to the bar, with the collar tucked in her bag. The box stayed with Jack, that way if she lost it, it'd return home to him. Jack meanwhile ran himself a bath. He'd had a busy few days and a hot bath to relax sounded like a good plan. Before he'd moved into his step-sisters house, he'd never been interested in baths, but when there's a tv on your bathroom wall with surround sound speakers, it's suddenly much more appealing.

He finished an episode of his show, got out of the bath and went downstairs to have his dinner. Just as he was washing up his dishes, he got a text from Abby asking if she could come over and that she had something she just had to show him. He told her to come over and waited until the doorbell rang.

When he opened the door he couldn't believe his eyes. Abby was standing there with the biggest grin on her face, while Mark was kneeling behind her. He was wearing a long dress with nylons stockings and high heels.

"What have I just opened the door to?" Jack asked.

"You won't believe this."

"What? That you collared Mark and made him dress up like a girl?"

"Nope. That wasn't me!"

"Then why is he dressed in women's clothing?"

"Tell him Mark," Abby ordered.

"I love dressing in women's clothing, it makes me feel sexy," Mark stated.

"Wait, so even before wearing the collar, Mark was a cross dresser?" Jack asked in disbelief.

"Yep!" Abby grinned.

"Holy shit. I would never have guessed!"

"I know, now Marky Moo, go into the kitchen and make me a sandwich," Abby ordered.

"Yes Mistress!" Mark replied happily. He crawled past Jack on his hands and knees and went to the kitchen.

"Holy shit," Jack repeated.

"I know. I had so much planned to get back at him, but as soon as I put the collar on him, I told him to tell me his secrets and the first thing he said was that he loved cross dressing."

"That's amazing."

"I know! It's not even the cross dressing that's the good part, I mean these days who really cares? But it's just the fact it's Mark. The huge womanising jock that looks down on anyone that's not a bro is currently in your kitchen, wearing a wig, a dress, stockings, panties and high heels while making me a sandwich. It's incredible."

"This is now how I expected my night to go, I'll admit," Jack smiled.

"Well how about this?" Abby replied, stepping inside and pushing Jack against the wall as she kicked the door shut. She kissed him forcefully, which he happily returned, as she slid her hands down his stomach. She undid his pants and sank to her knees, taking his soft cock in her hands. She kissed and sucked on it, bringing it to life. Jack sighed in satisfaction as his cock hardened in her mouth.

She bobbed her head up and down, running her tongue along the underside of his swollen head with each movement. She pulled her head back, sucking in her cheeks until his cock popped free from her mouth. She looked up at him and grinned as she stroked his slick cock.

"Your sandwich is ready Mistress," Mark said from the doorway.

"Come here, kneel," Abby commanded as she continued to stroke Jack's cock. Mark crawled over to her and knelt next to her, watching her hand go back and forth.

"Before I collared you, did you like guys at all?" She asked.

"No Mistress."

"But look at his cock, it's the most delicious, juicy looking thing you've ever seen and you just want to suck it," Abby smiled.

"I do Mistress, it looks so good!" Mark replied, staring at Jack's cock in fascination.

"Abby...?" Jack asked, nervously.

"Then help me," Abbey grinned at Mark.

"Wa-" Jack began before groaning as two sets of mouths suddenly engulfed either side of his cockhead. He had no interest in guys, he definitely had no interest in Mark, but something about him being controlled by Abby and make to want to suck his cock was hot. Jack didn't resist, he let them work his cock together, closing his eyes and trying to forget one of the mouths belonged to Mark.

Jack grunted as suddenly one of them took a testicle in their mouth. He'd never had someone suck on his testicles before, let alone having it happen while someone sucked his cock and the sensation was amazing.

"Oh fuck! I'm gonna cum!" He warned.

He felt both pairs of mouths leave him and he looked down to see Abby grabbing Mark and holding his head towards Jack's cock. She stroked it with her hand, pointing the tip at Mark's face as Jack came hard. He watched as he covered the jock in rope after rope of cum. Mark just grinned up at him as more and more of his face was coated in the sticky fluid.

"Holy shit..." Jack groaned as his orgasm faded.

"You love having cum on your face, it turns you on so much. In fact, from now on you'll love sucking cock and getting covered in cum, even when you're not collared," Abby commanded.

"Yes Mistress!"

"Also, from now on, you'll be respectful to women. You'll never want to do anything to disrespect or upset them again. You'll make sure your friends don't do anything either and if they do, you'll call them out on it."

"Yes Mistress!"

"Oh and no more being a jerk to people just because they're not jocks. That's not ok."

"Yes Mistress!"

"Good, now go and wait in my car."

"Yes Mistress!" Mark repeated. Crawling towards the door. He opened it and crawled outside.

"Wow, you really did a number on him," Jack commented.

"Yeah, but it's for everyone else's benefit."

"Even the sucking dick part?"

"That'll be someone else's benefit, he was a good cock sucker. Made you cum quickly."

"That was mostly you."

"I was sucking on your balls, that orgasm was all Mark."

"Oh well, then yeah, he knows how to suck dick."

"I thought you were going to stop me."

"I was so caught up in the pleasure of it all honestly."

"Well I thought it was really hot. Seeing Mark with your cock in his mouth, something I never thought I'd see, but I'm so glad I did! Anyway, I should probably take him home. As tempting as making him walk home dressed as a woman while wearing your cum on his face is, I'm not so mean to ruin his entire life."

"Well aren't you just lovely."

"I know. I'll pop round tomorrow okay?"

"Yeah sure."

Jack watched Abby leave and went to bed. When he woke the next morning, the first thing he did was check the collar. It was back in the box, just where it should be. He picked up his phone and scrolled through the numbers. He found his grandparents, but couldn't call as his was broken and wouldn't pick up his voice.

He presumed the microphone had broken, which meant he was stuck only texting people. Unfortunately his grandad refused to embrace technology and would never reply to text messages. A phone was for speaking, not typing, he would say.

He got up and showered before making a quick trip to the local shopping mall. He walked out with a new phone, something he had been wanting to buy for ages, but had been hesitant to spend money on. That didn't matter now, not with his new and improved contract at work. He arrived home and after transferring everything over, he called his Grandad.

"Hello?"

"Hey, it's Jack."

"Jack my boy! I thought I'd be hearing from you soon. How are you?"

"I'm good, how about you?"

"I'm fine, I'm fine, still ticking along. So, how do you like the collar?"

"It's incredible. How did you get it?"

"It was many years ago, me and your grandmother weren't having the best time. Your mother was young and she was about to see her parents get a divorce. Well I went on a work trip to restore an old mansion, I was gone for six months, but while I was there I was ripping out the basement to replace with a more modern one. At the back I found a heavy stone wall that had a slight gap underneath it."

"A fake wall?"

"Exactly. I knocked it down and found a small room behind it. The room was empty except for an extremely old wooden table with a box on it."

"The collar?"

"Indeed. At first I didn't know what it was, but it was nice so I took it as a present for your Gran. Figured maybe I could use it as an olive branch, begin to patch things up. While I was looking at it, I accidentally bound it to me. That's when I knew something was unusual about it, a blue light going into my thumb definitely wasn't natural," his grandad explained.

"Yeah, that's understandable."

"So, when I got home, I gave it to your Gran and she put it on. As you can imagine, she instantly changed. At first I thought she was just messing with me, but then we had the most crazy sex we'd ever had," the old man continued.

"Alright, I don't need to hear that."

"Ah those were the days. I do miss your gran, god rest her soul," his grandad chuckled.

"This suddenly explains why you're with Tiffany," Jack said suddenly.

"Yep, like I tried telling your mother, she's not some gold digger waiting for me to die."

"You used the collar on her! That makes so much more sense why some thirty year old real estate agent suddenly moved in with you."

"So it couldn't be just for my charm and good looks?"

"Sorry Grandad, I might think you're hilarious, but I don't think that wit would land you Tiffany on it's own."

"You're probably right. Anyway, that's how I found the collar."

"So why give it to me?" Jack asked.

"I'm old and content with my life. I've had my fun with it and now It's your turn."

"Thank you. This is the most amazing gift I have ever received," Jack said earnestly.

"You mean you don't get magical collars from all your family members? Pah, pitiful!"

"So what else can the collar do?"

"What have you learned so far?" His Grandad asked, curious to see how far his Grandson had pushed things already.

"That if you put the collar on someone, they'll do whatever you tell them to. They see you as their master and you can even implant commands that'll effect them after the collar comes off."

"Anything else?" His Grandad asked with a hint of amusement in his voice.

"No. What else can it do?"

"Oh, many things, but I won't be telling you what they are. Half of the fun is figuring out how far you can take things."

"Oh come on, you won't even give me a hint."

"Nope. Maybe one day, but for now, I want you to figure it out. Now, Tiffany has just arrived home and she's kneeling in front of me, so unless you want to listen to your Grandad getting his dick sucked, I'll talk to you another time."

"Fucking hell, yeah bye!" Jack replied, quickly hanging up the phone as he heard a zipper being undone. He looked over at the collar, wondering what other secrets it held.