“Melissa, we’re home.” Mrs. Blake called as she opened the door.
The 14-year old got up from the couch in the living room where she was studying.
“How were the boys?’
“They were OK. Bobby gave me a little trouble about going to bed, but I read him an extra story and he went right off. How was the movie?”
“It was hilarious. You should see it.”
“I’ll see if I can talk my boyfriend into it.”
“Great. Here’s your money. Mr. Blake is in the car and will drive you home.”
Melisa took her seat on the passenger side. As Mr. Blake backed out of the driveway, she slid over, undid the zipper on his pants and fished out his already erect cock.
It all started a couple of babysitting assignments ago with her rubbing her hand along his right leg and then feeling the lump there. When he didn’t stop her she got more aggressive step-by-step until she was rubbing her hand up and down his naked penis, fully masturbating the 36-year-old man.
Last time she forgot to use the tissue making a mess of the front of his pants. She simply giggled at him and told him to “deal with it like a big boy.”
Jack Blake sighed as the girl’s hand moved up and down his shaft. “Don’t forget the tissue this time, sweetie,” he told the girl.
Melissa giggled, “Don’t worry Mr. Blake. We won’t need it this time.”
Jack wondered what she meant by that.
As he drove towards her house she slowly brought him to the brink of an orgasm and then suddenly stopped.
“What are you doing?” he asked.
“Just keep driving,” she told him.
She leaned over and touched the tip of his penis with her pointed tongue. She wiggled it gently into the pee hole. Mr. Blake nearly drove off the road.
She removed her tongue and used it to flick at the rim surrounding its head. Then slowly, she lowered her head and moved her lips over it.
“Hurry, hurry,” Jack pleaded as he approached her house. Janet Blake wasn’t one for oral sex; giving it, that is. Without the prospect of reciprocation, Jack was unwilling to go down on her.
Melissa pulled her head off his penis and looked at it, glistening in the street light. She sat up and said, “Take me home. If you want me to finish this properly, meet me at my house after school on Tuesday. I get home at 3:15.”
“But what about your sister?”
“She’ll be at band practice. She won’t get home to almost 5. Mom and dad get home later than that. We’ll have the house to ourselves.”
He pulled into the driveway. She looked towards the house to check if anyone was looking and then turned and kissed Jack on his cheek. “Good night, Mr. Blake. See you Tuesday.” She had already made up her mind that he would be there.
Jack Blake sat in his car watching the girl walk towards the door. Already running through his mind was the timetable. Two more days. She waved at him as she closed the door. He pulled out of her driveway and stopped at the end of the block to tuck his penis back into his pants.
-=o=-
Sunday and Monday were a tumble in Jake’s mind. He couldn’t get Melissa off his mind. Whenever the flashback of her head bobbing up and down in his lap came back he’d harden immediately.
Tuesday came, and armed with an excuse about a doctor’s appointment, he left work and headed towards Melissa’s house. He was having second thoughts. It was one thing to have a teenage girl jerk you off. It was another to have her perform oral sex one you. Was that statutory rape? It certainly was a step up from a simple hand job. Where would it go from there?
Against his better judgment he pressed on. He parked in her driveway, walked up to the door and rang the bell. Melissa answered it with a scowl. “You idiot. Don’t park in the driveway. Park down the block and walk here.” She slammed the door in his face.
Jack knew she was right. He felt embarrassed at being dumber than a 14-year-old girl. Nonetheless, he did what she said. The second time she answered the door, she smiled at him and welcomed him in. His penis swelled to even bigger and harder proportions as he looked at her in her school uniform.
“Why don’t we go up to my room,” she said without hesitation.
Jack soon found himself in the girl’s room. It was a girl’s room, painted in pink with posters of celebrities adorning the wall and clothing adorning just about everything else.
“Stand over there and strip!” Melissa commanded with confidence, pointing to a point on the floor in her bedroom.
“But I …”
“No buts. I want to see the whole thing. In the car all I get to see is your dick. I want to see it all.”
“Aren’t you going to get naked too?”
“That all depends on how this goes. If you’re a good boy, you’ll see me naked – eventually.”
He knew he didn’t have a choice if he wanted the blow job. He slowly got undressed. As he stepped out of his underwear, Melissa giggled, “Your poor wife. You actually got her pregnant with that?”
Jack blushed, just how many penises did this girl see to know that his was on the short side?
“I’ll do the best I can with it. Turn around. Let me see what else you have.”
Melissa whistled as he turned his back to her. “Cute buns, I bet Mrs. Blake would have fun smacking them.”
Jack shivered. The thought of his wife spanking him got him excited even more. But it would be a forlorn fantasy; Janet never did anything exciting in the bedroom. Meanwhile here he was fully naked and displaying himself to a fully-clothed teenaged girl.
He came to rest facing Melissa again. “Hands on head,” she commanded. He obeyed, not quite knowing why.
Just then her cell phone rang. She looked at it and then texted something back. Jack thought, at a moment like this? How could she? A teenager’s addiction to her cell phone is legendary but Jack expected more out of her.
He didn’t even ask who it was. Melissa just smiled at him. “Is that as big as it gets,” she asked.
Jack just nodded.
“It’s OK, it’s cute. I like it.”
She stood in front of him and fondled it for a couple of minutes. She was teasing him and driving him insane with the anticipation of his pleasure. He knew that as soon as she got her lips on it he would explode. Did she know about premature ejaculations too?
Jack was getting close and was about to stop her. He didn’t want another hand job. He wanted to feel his penis inside her soft mouth. The mood was suddenly interrupted by the ringing of the door bell.
“See who that is,” Melissa giggled.
Jack looked at her in horror.
She broke out in laughter. “Silly boy. You stay right here and keep your hands on your head. I’ll see who it is.”
She wasn’t really at the task very long when he heard her coming back up the steps. He wasn’t sure, but he thought he heard more than one set of footsteps. He didn’t have to doubt for long. When the door opened again there stood Melissa, another girl about her age, and Melissa’s 12-year-old sister Mandy!
Jack was frozen in shock and didn’t even think about covering up for several long seconds during which the girls got a good look at him. When he finally did reach for his clothes, Melissa slapped his hands away. “Chrissie has something to show you.”
Chrissie poked at the display on her phone and then turned it around to show Jack. There he could see his entire stripping act, and Melissa feeling him up.
“I’ve been streaming the whole show to my friends,” she said, pointing to her computer. Jack was so focused on the attractive girl and what he thought she was going to do with him that he didn’t notice the little red light on the webcam indicating that it was active.
Melissa continued, “So don’t think about trying to erase anything from the phone or my computer. Right now there are girls all over town watching you. Now I want you to walk up to the computer and give us an inaugural wank. All the boys have to do it.”
“Boys? What boys?” he managed to ask.
“Show him Chrissie.”
Chrissie brought up another video. It showed a man jerking off. Jack thought he knew the man, but couldn’t place his name. Chrissie went through a number of videos showing several different men jerking off and doing other things with the girls. In one a man was being ridden like a horse, and the girl was smacking his red behind with a riding crop. When the couple turned around to face the camera, Jack saw that it was Melissa and the manager at the bank.
“There’s lots more. It’s a pretty big club. We have men all over town. I was getting kind of bored with Billy and got tired of sharing him with my sister, so that’s why I got you.”
Mandy giggled, “He’s cute. A little on the short side. Some of the guys in my class are bigger than him.”
“OK, Jack-boy. Time to jack off. Get your butt in front of the computer and do it.”
Jack had no choice. He stepped up, put his hand on his penis and started to masturbate. Melissa turned on the monitor so he could position himself to fill the screen with his penis and hand. All the anticipation and stimulation prior to his “capture” overcame his embarrassment at being made to perform for three live girls and who knows how many on the other end of the camera. He shot off in a minute.
“Wow, that was pretty impressive. He may be short, but he sure can shoot. Look how much there is and how far he shot it!” Mandy said.
“I told you he was a cummer.” Her sister responded.
“Can I have him?” Mandy asked.
“No, I’m giving you Billy. That should be enough for you.”
“But Billy’s an old man.”
“So get a boy of your own.”
“Can I at least play with him?”
“Of course. Haven’t I always shared my toys with you?”
“Thanks, sis.”
Melissa turned her attention to the naked man. “Now let me tell you how things work around here. Mandy, Chrissie, me and about a dozen other girls are in this club. Each of us have at least one man now that I have you and gave Billy to my sister. We put on shows for each other and put them on the web. You are going to be one of the stars in these shows.
Every now and then a couple of us girls get together in person and have our boys play with each other. Chrissie lives nearby and we share our boys a lot. Her boy is Mr. Ericson, the assistant principle.
Oh, and there’s one more thing.” She said pointing to his penis. “That’s now my property.” She reached into a draw and pulled out a chastity cage.
The girls giggled at Jack’s shock, “Where did you get that?”
“We girls have our ways. Remember, we have male slaves all over town. They’re adults and have the money and the resources to buy us girls whatever toys we ask them for. This cage belonged to a boy who has learned his lesson and now serves his girl very faithfully. He doesn’t need it anymore. Your turn will come, but for now, we’ll just put this on you.”
“But my wife …”
“You’ll just have to find an excuse not to have sex with her. Maybe you can distract her by pleasing her in other ways.”
“But …”
She laughed, “But we have pictures of you wacking off. Multiple copies with girls all over town. It would be a shame if that video went viral, wouldn’t it?”
Jack bowed his head. He was defeated.
As she locked him up, Melissa explained. “You’re a good boy, Jack. I like playing with you. If you want to get out of your cage, you will have to make sure that you and Mrs. Blake use me as a baby sitter more often. I like to think of our arrangement as ‘job security’ for me.
You can get dressed now and run along like a good boy. I hope to see you soon; all of you that is,” she added giggling.
-=o=-
Jack punched at the blinking light on his phone. After pressing the appropriate buttons, he listened to his voicemails. The first was routine business. The second stopped his heart cold.
“Hello, Jack-boy,” Melissa’s voice said. “I have an assignment for you. I want you at 15 Rockport Place at 3:30 this afternoon. Be a good boy and maybe I’ll give you something you want. Disobey, and … well … maybe Mrs. Blake will get a surprise picture sent to her phone.”
Jack looked at the phone until it buzzed indicating that it was off the hook too long. How did she get his work number? What was worse, it was already 2 PM and he had to come up with some sort of excuse with his boss to get out of work. He made up an illness for one of his children and a story that Mrs. Blake was out of town and the kids daycare insisted that the boy be sent home.
It was good enough for now.
Jack arrived at the house at the appointed time. This time he was smart enough to park down the street and walk in. He rang the bell. A naked boy answered it. He looked to be about 16.
“Come in. I’m Mark, Melissa’s boyfriend,” he said, extending his hand. “Melissa’s told me about you and she’s expecting us upstairs.”
Jack was surprised when he entered the bedroom. Melissa was naked on the bed. He had never seen her naked before and was not disappointed. She still had some growing and developing to do but her girlish figure was erotic nonetheless.
“Take your clothes off. We’re going to have sex.”
Jack couldn’t believe his luck until she said, “That is, Mark and I are going to have sex. You’re here to help, but if you do a good job, you’ll get that blow job you’ve been waiting for.”
She waited until Jack was naked and continued, “Mark’s got a problem. He’s a premature ejaculator. Cums almost as soon as he gets in me. I find that he lasts a lot longer the second time around. So I need to have him milked before I let him in me.
So why don’t you get on your knees in front of him and suck him off.”
Jack protested, “I’m not gay.”
“Neither is Mark. Did I ask you if you were gay? You’ll do it because I asked you to do it. Don’t do it and I’ll never take that cage off you. Now kneel and suck!”
Jack took the teenaged boy’s penis into his mouth and did the best he could do with it. He was by no means a world-class cock sucker, but when you’re dealing with a horny 16-year-old boy, any amount of stimulation no matter how awkwardly applied will get the job done.
Melissa was right, Mark came after just a couple of minutes of sucking.
“That’s a good boy, Jack. Now do me. While Mark is recovering, let’s see how many orgasms you can give me by licking me off. Now don’t be shy,” she said seeing his reluctance. “A real man knows how to please a woman with his tongue. I normally don’t like breaking in rookies, but I’ll train you if I have to.”
Jack bent over and brought his face to the girl’s pussy. It was covered with fine blonde hair unlike his wife’s unruly tangles. Melissa seemed to take pride in grooming it. He stuck his tongue out and went to work. He found her clitoris and dueled with it with his tongue, pushing it from side to side and swirling it around.” Melissa was not hesitant to provide feedback and tell him exactly how she liked to be licked. Jack was a fast learner: he was rewarded with a gush of her fluids.
Judging from her reactions, Jack gave her at least two orgasms before she pushed him off.
“I’m ready, Mark,” she said as she scooted fully on the bed and opened her legs. Turning to Jack, she said, “You stand in the corner with your hands on your head and watch. See how a real man with a bigger dick than yours does it.”
Mark mounted Melissa and the couple were soon engaged in intercourse. Even with his previous cumming, Mark didn’t last long, but Melissa didn’t seem to mind. The foreplay Jack provided her was enough that even Mark’s brief stimulation was enough to bring her off again.
As he dismounted, Jack could see Mark’s cum dripping at the opening of Melissa’s vagina. She snapped her finger at Jack and pointed to her sopping pussy. “Down here and clean me up boy. I need another orgasm.”
As Jack positioned himself between her legs she told Mark. “He’s all yours.”
Jack didn’t know what to make of the statement until he felt a finger at his anus. Mark was wiping the cum off the shaft of his penis and smearing it at the opening. Soon he felt the boy’s organ there as he pushed it in.
At first it hurt, and then it just felt like a full sensation but as Mark pumped into him, his penis made contact with his prostate. Jack could feel semen trickling thought his balls and into his penis. It wasn’t exactly an orgasm; it wasn’t as explosive, but it was a pleasant sensation or would be if it weren’t for the boy’s penis disrupting his bowels.
Melissa grabbed Jacks hair and mashed his face into her sopping pussy. “Hey, don’t forget about me! LICK!”
Jack’s tongue made love to Melissa’s clitoris.
Mark came and went and still Melissa clutched onto Jack’s head. Three times she screamed in ecstasy and three times his face was awash with her discharge. Finally, she pushed his head aside and collapsed.
Melissa lay there like a rag doll, completely drained. Her breathing was deep and for a moment, Jack thought that she might have swooned, but she gradually recovered her strength. “You boys did a good job. I think you earned that blow job, Jack-boy.”
She removed the chain from around her neck and inserted the key into Jack’s chastity device. Jack felt relief as his penis was released from his prison for the first time in almost a week. He looked at Melissa and she laughed. “Oh no, not me. I’m not giving you a blow job. That’s what I have boyfriends for.
I want to see the both of you give each other a blow job – 69 style.”
Jack was no stranger to Mark’s dick, having taken it already orally and anally. It was difficult enough to suck it off before and that was before it was up his ass. Nonetheless, he could not resist Melissa’s order. He took the teenaged boy’s cock in his mouth. He felt the boy do the same to him.
Out of the corner of his
eye, he could see Melissa taking pictures of them with her phone.