Chapter 5
Timmy was waiting for another invitation to Miss White's place. Jerking off with his English teacher sure was better than doing it alone. And he still hoped she would let him fuck her.
Finally, Jan White did invite Timmy over.
"This is so nice of you," she said to Timmy when he arrived at her apartment. "I don't know what I would do without you."
"It's my pleasure," Timmy said.
He remembered how Jan had looked the last time they had jerked off together. None of the girly magazines he usually used as masturbation aids were a fraction as exciting as she had been. But having her suck his prick after school the week before had been even better. And sliding his prick into her pussy would be better yet. After all, he still hadn't broken the fuck barrier.
"Would you mind if we do it differently this time?" Jan asked.
"What do you mean?" Timmy asked.
"I thought it would be exciting if you jerked off in my bedroom while I peek through the door," Jan said. "I know it sounds weird, but that's what would excite me the most. Jerry absolutely refuses to do it for me."
His teacher was turning into more of a pervert than he'd expected. And Timmy began to wonder whether he should play her games. After all, it would be just like jerking off at home as he usually did. Having Jan peeking at him would give jerking off a certain kinky excitement, but it wasn't what he'd had in mind when he came over.
"You look awfully disappointed," Jan said. "I guess that wouldn't be too exciting for you, would it?"
"Gee, Jan, I thought we would at least jerk off together."
"I'll tell you what," Jan said. "If you do this for me, I'll let you do whatever you want to me afterwards."
This was a good deal, Timmy thought. In fact, the idea of being able to do anything he wanted to a gorgeous chick like his teacher was almost too good to be true!
"Really?" Timmy said excitedly.
Jan laughed at Timmy's boyish enthusiasm. "Well, almost anything," she said.
"Can I fuck you?" Timmy asked wide-eyed.
Jan laughed again. "Sure," she said.
Then Jan took Timmy into her bedroom and showed him where to lie on her bed.
"Now, don't go over to the other side or I won't be able to see you from the door," she said. "And if you'd like, you can look at those pictures of me again."
Timmy said he would like that. So Jan took them out of her drawer and gave them to him.
"Just do everything as you normally would," Jan said as she left Timmy alone.
She closed the door, but not all the way. Since Timmy had peeked at Sue and her boy friend fucking, he knew just what it would be like for Jan to peek at him. But he couldn't understand why she wanted to watch him jerk off when there were so many things that they could do to each other.
Timmy made himself comfortable. He leaned back against the headboard of the bed. Then he looked at the pictures Jan had given him. At first, he couldn't help glancing at the crack at the door where Jan was peeking. But before long the pictures captured his total attention.
Studying his teacher's cunt and tits in the photos, Timmy was soon panting. Now, besides her cunt and tits, her mouth excited him too.
Looking at the pictures, Timmy thought about what he would do to Jan after jerking off for her. Now, as he looked at her pussy in the picture, he couldn't wait until his prick would be plunging into it. And the sooner he jerked off the sooner he could fuck her!
But Timmy didn't want to rush. Jan had told him to act natural. Besides, he was beginning to enjoy having her peeking at him even though he hadn't even begun yet.
Timmy held the photos close to his face. With his other hand, he stroked the hump that was throbbing in the crotch of his pants.
Yes, this was going to be fun, but not as much fun as he would have afterwards. Timmy was beginning to understand Jan's fascination with these masturbation displays. As he readied himself to bare his prick, his lust reached new heights.
Slowly, Timmy unfastened his pants. He thought how excited Jan must be as she watched. If she were half as excited as he, she must be going out of her mind.
Timmy reached into his underpants and began fondling his cock. He decided it would be fun for both of them if he teased Jan a while.
Finally, Timmy raised his ass slightly and lowered his pants to his knees. Now his prick stood like a chimney from his crotch. He could almost feel Jan's perverted eyes on it. Jerking off at home without someone watching was never like this!
Timmy ran his fingers along the underside of his prick as he continued looking at the pictures. The pictures of Jan on her knees with her cunt showing beneath her ass was still his favorite. He began to wonder if she would let him fuck her doggie-style.
Just as he had all the other times he jerked off, he played with his prick for a while, then wrapped his hand around it and began pumping.
At first, his hand moved faster, but only very gradually. Timmy was enjoying this and he wanted it to last. If it wasn't for Jan's promise to fuck him afterwards, he would have made his jerking off last for an hour.
Timmy wondered what Jan was doing on the other side of the door. He imagined she was peeking with her hand on her crotch, tickling her cunt. And maybe she was holding her tits, too. He remembered the things she had done when they jerked off together. He wished he could see her. But he had to admit that having the door between them added a certain twist that was very thrilling. Besides, he did have the photos to look at.
Timmy found that the excitement of having Jan peeking at him made his passion climb faster than he expected. He had hoped to make the show last longer. But he was almost at the point of shooting his load.
With his hand moving quite fast up and down on his shaft, Timmy arched his back.
"Ahhhhhh!" Jan moaned.
Timmy heard her moan. She was coming! So he let his hand go at full speed.
The room seemed to be spnning. Strange flashes of light filled Timmy's head. The kinky situation he was in was making his orgasm a truly wild experience!
"Ahhhhhh!" Jan moaned again, louder this time.
"Haaa," Timmy groaned as his prick turned into a fountain.
He pumped himself dry. And as he did, he heard Jan moaning desperately at the door.
While Timmy's orgasm left him gasping and limp, Jan's moans continued undiminished. He listened to her coming with excited glee, even though his own ecstasy was over.
Then the door swung open. Jan was standing there naked and slightly crouched over. Her legs were spread and she was scrubbing her cunt furiously! She held one tit in her hand while the other swung heavily with her rapid rocking.
Still stimulating her cunt and tit, she began to move toward Timmy. She came at him with a strange bow legged stagger. Timmy had never imagined a sight as wild and kinky as this!
"Aaaaaaa!" Jan cried as she threw herself onto the bed beside Timmy.
Jan lay beside him as she finished fueling her ecstasy with her fingers. She trembled, shaking the whole bed. Timmy watched in awe.
Finally, Jan lay still. Now only her back moved as her ribs contracted and expanded with her gasping breath.
When Jan looked up at Timmy, she had a happy smile on her face.
"Thank you, Timmy," she said. "You must think I'm really crazy, but there's something about watching a boy jerk off that turns me on like nothing else!"
"I don't think you're crazy," Timmy said. "I like jerking off with you watching. It made it more exciting than it ever is when I do it at home."
"Really!" Jan gushed. "Oh, I'm so happy you feel that way!"
She really was happy, Timmy could tell. And so was he. But the best was yet to come. Here was Jan, naked, and all his!
As eager as he was to fuck her, Timmy forced himself to wait. After all, his prick had just had a work out. He would need a few minutes to recover.
But Jan went right into action. She dragged his pants off his feet. Then she helped him off with his shirt.
Just being naked and in bed with a naked chick stiffened Timmy's prick again. And as Jan began licking the spilled gism from his stomach, his cock began twitching.
As Jan cleaned Timmy's body with her tongue, her tits rested on one of his thighs, sending their magic right to Timmy's center of lust.
When he reached for her tits, Jan rolled slightly to the side, lifting her tits from his thigh so he could caress them.
Although Timmy had copped a few quick feels with girls his own age, he'd never had the chance to fondle a pair of naked tits the way he wanted to. So now he explored Jan's tits with all his crazed passion.
He filled both his hands with supple tit-flesh. Then he squeezed those globes of softness. As his fingers sunk into Jan's tits, they were heavy in his hands. Her erect nipples pressed into his palms.
When every puddle of gism had been slurped up, Jan moved up beside Timmy. He kept his grip on her tits as she kissed him.
Her mouth was already open when it covered Timmy's. When he opened his mouth, her tongue slipped into it right away. The way her tongue began writhing in Timmy's mouth surprised the boy. No girl had ever kissed him like this!
Jan ran one hand up Timmy's thigh to his balls. Then she cupped those big nuts firmly, just as she had when she sucked his cock the week before. Since that time, Timmy had tried to hold his own balls as she held them. But his own hand couldn't give the same effect.
As they kissed and grasped at each other, Timmy knew that this was what he'd been missing, what he'd been dreaming of. But the reality was far beyond anything he'd ever imagined. How could an inexperienced young boy know the thrill of having a chick like Jan in bed with him?
"Oh, Timmy!" Jan sighed as she brought her tits up to his face.
Still holding onto her tits, Timmy stared at her nipples which were now just inches from his face. Her big, round nipples had a powerful effect on Timmy-his mouth opened and sucked one of her pink nipples into it.
"Ahhhh!" Jan sighed with profound lust. With his mouth full of Jan's erect nipple, Timmy began sucking madly. As his tongue circled her erect bud, his teeth pressed into her soft tit-flesh. "Harder," Jan whispered hoarsely. "Yeahhh!" Timmy thought it would be painful to have his teeth buried so deeply into Jan's tits. But there was no doubt she liked it, judging from the way she held his head tightly pressed to her tit. Timmy could hardly breathe! But what was air compared to Jan's gorgeous tits?
Now Jan's hand had climbed from his balls to his cock. Timmy felt her skillful fingers climbing his prick. And when they arrived at his prickhead, they slid around the generous circumference of his bloated cock-knob.
It was obvious that Jan had had a lot of practice handling pricks! She was handling Timmy's now with more skill than he'd ever handled it himself.
"Your prick is so hard!" Jan whispered in awe, "even though you just jerked off!"
Timmy was proud of his hard prick. And he was glad it was ready. But for the time being, he was happy to suck Jan's tit while she held his prick.
Timmy dropped one nipple from his mouth, then gobbled up the other. Then he buried his face between Jan's big tits. Holding her tits to the sides of his face, Timmy kissed her breastbone. He never wanted to leave the warmth and excitement of her tits.
But Jan pulled them away from Timmy. He hated to lose the sensation of being buried in tit-flesh, but he knew that there were more exciting things coming.
Jan slid down Timmy's body again. She kissed and licked his belly button while her tits hung down and rested on either side of his prick. Then she continued down until her face was over his jerking cock.
"I love the way pricks throb!" Jan said with genuine passion in her voice.
A short time ago no girl had seen Timmy's hard-on. Now his teacher was studying it closely. She held her face near his prick head, so it tapped against her lips every time it twitched.
Then Jan stuck her tongue out, touching the underside of Timmy's prick. Next, she ran her tongue down his shaft. She kissed his balls. She even sucked them into her mouth.
Timmy watched all the wonderful things Jan did to him as his passion steadily increased!
Jan's mouth moved back up Timmy's prick. She took his cockhead into her mouth. Her tongue tickled it, then slid all around it.
By this time, Timmy was panting. The sight of her crouching between his legs with her mouth opened wide would have made him pant even if he weren't being treated to the incomparable thrill of having his prick in her mouth.
Not wanting to bring him too close to coming, Jan released Timmy's prick from her mouth. She crawled up beside him again.
Timmy was eager to fuck her. It seemed he'd been waiting all his life for this moment. So he pushed Jan down onto her back and began mounting her.
"Wait," Jan said. "I'm not quite ready."
As she spoke, she took Timmy's hand and brought it to her cunt. Timmy hated to have to wait, but he wanted Jan to be ready for him. Besides, fingering her first would be fun. So even though his prick was swollen to the point of splitting its skin and twitching wildly, Timmy began exploring Jan's pussy.
Jan had placed his hand over her hairy mound. Her wet cunt lay right beneath his middle finger. All Timmy had to do was bend that finger and it slid right into her hot, slippery pussy.
"Mmmmm," Jan hummed as her cunt was filled with Timmy's strong finger.
Timmy had never finger-fucked a chick before. He found that he loved it. And he thought if finger-fucking was so terrific, what would real fucking be like?
Since Jan's pussy was so wet and slippery, he let his finger swim right up her deep cunt.
Timmy had never felt anything as tender as the lining of Jan's pussy. It was so smooth and soft, not to mention tight, and he knew it was made to hold his cock.
Jan began wiggling her hips, rubbing her pussy on the boy's invading finger. So Timmy began stirring his finger around, increasing the friction between finger and cunt.
"Ooooo!" Jan cried.
She pulled Timmy's face to hers and kissed him. Licking each other's tongue increased their lust.
As Timmy reached high up Jan's snatch, he felt her ass cheeks lying beneath her crotch. What a wonderful place to explore! A woman's crotch was the most exciting territory on earth.
"Fuck me now," Jan whispered.
Her words shook Timmy to his soul. Trembling, he took his finger from Jan's cunt. He climbed between her legs and brought his prick to the drooling mouth of her pussy.
Timmy bore down on his prick. He could feel the hot, wet gash under it. His mind was burning with the desire to climb into her sweet body but soon he realized his prick was lying alongside Jan's cunt and not stuck into it.
He lifted his hips to try again. Then he felt Jan's hand grab his cock. Timmy followed her lead until he felt her tender lips surround his prick head.
Timmy thrust his hips forward. He was inside her!
"Ahhhhh!" Jan cried as she was impaled on the boy's prick.
At first, all Timmy was aware of was a wonderful, hot sensation. Being buried to the balls in Jan's cunt filled him with blinding passion. Not until he had been inside her for a few seconds did the full glory of her pussy fill him.
He was filling her body with his big prick. And her cunt hugged his prick with infinite ecstasy!
Instinctively, Timmy began sliding his prick back and forth. Now the full bliss of fucking was revealed to him. As the lining of Jan's cunt moved back and forth over his sliding prick, Timmy felt waves of joy rush from his cock to his brain.
"Oh, Timmy!" Jan gasped. "Oh, fuck me! Ahhhhhhhhh!"
With Jan's cunt tugging at his prick, Timmy would have come almost at once if he hadn't jerked off a short time before. Still, he couldn't keep his prick churning in her hot body for long without filling her with cream.
Timmy had his face pressed to the side of Jan's face. But now she grabbed his head and lifted his face above her own. When Timmy looked at her, he found she was looking back at him with passionate interest. He knew the look of lust on Jan's face was mirroring his own lustful expression.
Now Jan looked just like she had when she came staggering into the room with her fingers up her cunt. She was crying out again with ecstasy, too. "Aug, ah," Timmy moaned as he came. Both of them were writhing wildly, keeping Timmy's prick chugging up Jan's pussy. As Timmy's prick dove deeply into Jan's cunt, their pubic bones bumped. Again and again, they crashed together as Timmy's prick flooded Jan.
Again, Jan's orgasm lasted longer than Timmy's. Even when his prick ran out of cream, Jan kept thrusting her hips, sending her pussy sliding up over Timmy's cock.
"Eeeeeee!" Jan squealed as the last of her ecstasy echoed in her brain.
Timmy remained on top of Jan, letting his prick linger in her cunt. He didn't ever want to take it out of the tight grip of her body.
"Wow, that was wonderful!" Jan gasped. "Timmy, you're a super fucker!"
Timmy was too dazed to pay attention to Jan's words. He was in shock. Fucking was so much more than he'd ever imagined, he couldn't believe it. The pleasure had been so intense!
"I-I never . . . never knew . . ."he stammered.
But he was still too far gone to speak. Jan laughed at his condition.
Timmy didn't know how long he lay there. It was so wonderful to have his shrinking cock in her cunt, his chest cushioned by her ample tits, he wanted to remain there forever.
But Jan had other ideas.
"We have to get up," she said. "I have to get ready. I have a date with Jerry."
Not only did Timmy hate to leave his warm place on Jan's naked body, but he hated to hear Jerry's name mentioned. But there was nothing to do but climb off Jan and let her get up.
"You're not jealous, are you?" Jan asked. "You know Jerry's my boy friend."
Timmy didn't answer. Sure he knew it. But that didn't mean he wanted to hear that she had to chase him out of her bed because she had a date with Jerry.
"Now don't be silly," Jan said. "I told you, we're jerking off partners because Jerry won't jerk off with me. And I only fucked you because you let me watch you jerk off."
"I know," Timmy said. "And it was terrific. I loved it! I loved jerking off for you too!"
"Good," Jan said. "Now get dressed and go before Jerry shows up. What time is it, anyway?"
Jan reached for the clock beside her bed and turned it toward her.
"Oh my God!" she cried. "He'll be here any minute!"
Timmy jumped up. He grabbed his clothing and began jumping into them. The last thing he wanted was to be there when Jerry arrived.
"I'm going to take a shower," Jan said as she ran from the room. "See you later, Timmy."
Timmy buttoned his shirt as he ran to the door. But before he got to the door, he saw Jerry coming up the walk.
There was a back door, and Timmy would have to use it. He ran through the kitchen to the back door. But it was locked. He grabbed a knob on the door and twisted it. But the door wouldn't open. By this time Jerry was knocking on the door.
Timmy struggled desperately with the lock. But he was so scared now that he didn't know if he was opening it or locking it. In any case, the door refused to give.
"Come in," Jan called out of the bathroom door to Jerry.
Timmy heard Jerry come in. Should he hide until they leave? Or should he just pretend he'd come over to see his teacher about a homework assignment?
"I'm in the shower, Jerry," Jan called. "Help yourself to a drink."
As Timmy stood at the back door, struggling to open it, Jerry walked into the-room.
"What are you doing here?" Jerry asked in a booming voice.
"I was just leaving," Timmy said as he walked around Jerry, leaving plenty of room between them.
"I can see that you're leaving," Jerry said as he stepped into the doorway, blocking Timmy's escape. "But what were you doing before you were leaving?"
"Nothing!" Timmy said shrilly. "I just had to get a homework assignment. I missed school today and . . ."
"What's going on?" Jan said as she appeared suddenly with a towel wrapped around her.
"What's he doing here?" Jerry asked.
"He brought me a book he borrowed," Jan said. "Leave him alone. There's nothing to-"
"A book, huh?" Jerry said angrily.
The next thing Timmy knew, Jerry had grabbed the front of his shirt. Timmy was yanked toward Jerry, then shoved away. The kitchen wall suddenly slammed into his back.
"Leave him alone!" Jan yelled as she ran toward them.
The towel dropped from Jan's tits as she flung herself between Jerry and Timmy. She pulled the towel back up with one hand while she grabbed Jerry's hand with the other. She shook Jerry's hand off Timmy's shirt. Then she pushed Timmy toward the front door.
"Good-bye, Timmy," she said. "Thanks for bringing me the book."
"Don't let me catch you here again!" Jerry added.
Timmy had never left anywhere so quickly. All the way home, he expected to see Jerry again. He didn't feel safe until he was in his own house.
But when Timmy calmed down, he knew it had been worth it. After all, he'd finally gotten laid!