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After-school Taboo by JT

After-school Taboo

Part 1: The Mother's Son

"Baby, you are getting better at this every day, I swear," Mrs. Rupert said in the afterglow as she washed the back of her young lover's shoulders.

It was a quiet, comforting moment for 18-year-old Tim as he sat in the bath tub, leaning back against Mrs. Rupert. The water was warm and her soft flesh soothed his mind. She may be 28 years older than him, but her 34D breasts still felt plump and firm against the small of his back.

Her arm slipped around him and her hand caressed his thigh. His dick stayed limp, but certainly not because she couldn't turn him on. Mrs. Rupert was beautiful for a 46-year-old. Her body was voluptuous and tight and her cute face and blue eyes were framed perfectly by the shoulder-length blonde hair. Tim and every single high school boy who took Mrs. Rupert's 12th-grade English class deemed her "hot." Those boys had never seen her naked like Tim had, though. She was more than "hot."

So no, it wasn't a lack of excitement that kept Tim from getting a hard-on right now. It was the fact that they had been fucking since 11 a.m, when Tim woke up to feel her lips around his penis. Five orgasms, three ejaculations and two hot-cooked meals later, and it was already 5 p.m. Tim had to get going, he realized, as he stepped out of her embrace and got to his feet in the tub as he grabbed a towel.

Mrs. Rupert remained sitting in the warm water, as she reached out and caressed his soft, wet buttocks while he dried. "Do you have to go right now, baby?" she asked. "Yes, Mrs. Rupert. I haven't been home all day and my parents said that the only way I could stay the weekend was if I went home for dinner. I won't be more than two hours though," Tim replied.

Most of what Tim was saying was true. His parents did say he could stay the weekend, but not here. He told them he was going to spend it with his friend, Jason. That was the plan he had thought up almost a month ago, right after Mrs. Rupert pulled him aside after class and told him that her husband and son were both going to be away on the weekend of the 12th. The house would be all theirs, and they could carry out the torrid affair that had begun almost 5 months ago. It was Saturday, and so far everything had gone smoothly.

"Awww, hon. I'll miss you," Mrs. Rupert said as she kissed him playfully on the rear. "I'll make sure to cook up something real nice for you when you get back..."

Tim couldn't help but snicker. When she said that yesterday, she didn't actually mean she was going to "cook up" a meal. She meant she was going to "cook up" something sexual for them to do. Yesterday he returned to her house and they had a hot session of teacher/ student role-playing for most of the night. It ended nicely for Tim, too. He got to come all over her tits.

Tim stepped out of the bath and put on his clothing. "I'll be back no later than 7. Promise."

With that, he leaned down and kissed her full lips. He couldn't help but stare at the cleavage of her tits, which soaked in the warm water. She caught his peaking and gave him a playful spank on the butt before their kiss ended. Tim smiled back at her as he walked out of the bathroom.

Tim had to walk home, because Mrs. Rupert didn't want any suspicion over a strange car in the driveway on the same weekend that her husband was on a 5-day road trip and her son was away at a hockey camp. Tim didn't argue the point. After all, Mrs. Rupert's husband was a 6-4, 220 pound defenseman on a conference champion IHL hockey team. He certainly had no wish to be caught by that man. He was intimidated enough last night when he was fucking Mrs. Rupert doggy-style while she was half-watching a replay of her husband's game on ESPN2. Tim found that he couldn't even orgasm until the intermission commercials.

But despite the risk of having such an affair with his fourth-hour Creative Writing teacher, she was well-worth it. It was his senior year of high school, and thanks to her, he had experienced things most men would never see in their lives.

Just last month, she had secretly taken him to a strip joint three towns over. That was cool enough of her to do, but Mrs. Rupert wasn't finished there. She got one of the strippers to sit down at their table, and slowly Mrs. Rupert seduced the stripper with her good looks, charm and a bit of wine. Not even an hour later, the three of them retreated to one of the secret back-rooms. From there, Tim took part in a steamy threesome that outdid any porno he had ever seen. After two hours of the hot-and-heavy, Mrs. Rupert had worn out both him and the 21-year-old stripper.

She was simply an animal in bed. Tim had never left one of their fuck-sessions without needing a long shower or a relaxing bath. He didn't realize the male body could produce so much sweat and semen.

As he sat down for dinner with his mother, father and two sisters, his cock twitched a little at the thought of what Mrs. Rupert might be "cooking up" for him at this very moment. He ate his potatoes and steak quickly.

"Slow down, Timmy," his mother said. "Haven't you been eating well at Jason's?"

"Oh yes, I've been eating just fine, ma," Tim said as he laughed on the inside.

His parents seemed to be having no doubt that he was actually at Jason's. But just in case, Tim had told Jason about the cover-up, and Jason had agreed to help his friend out. In case Tim's parents called Jason's that weekend, he had a story to explain why Tim couldn't be reached at that moment. But even Jason didn't know where Tim was. Mrs. Rupert made Tim promise not to tell anyone, and Tim always kept his word. As Tim walked out of his home and started on his 10-minute walk back to Mrs. Rupert's, he could feel himself becoming aroused. This weekend had been an adventure so far, and it was only half-way over. He picked up the pace as he began fantasizing more and more about what Mrs. Rupert might have in store for him. Maybe she even invited the 21-year-old stripper over to share the fun-filled evening. God, he was so fucking horny for Mrs. Rupert right now.

It was hard to believe that just a year ago, he was in such an innocent relationship. Tim had fallen in love with Suzy when he was just 14. She was 13, and she had felt the same way for him. It took them a whole year, but their love was so pure and sure, that they decided to take each other's virginity. Not even the sexiest of sex that Tim had with Mrs. Rupert could have matched up to the love-making he and Suzy shared. She was his soul-mate, it seemed. But one day she had to move away, and their attempts to keep in touch with letters and phone calls dwindled. It had been one year since the last time he heard Suzy's voice and two years since he had touched her. And for a long time, he had been lonely and depressed.

It was when he tried to describe his loneliness in a class-assigned poem that Mrs. Rupert had first become attracted to him. She had read the poem first at home, and was so moved by it, that she called him at home. After suppressing over the phone for an hour, he finally broke out in tears. Mrs. Rupert convinced him to come to her house so that they could talk about it more personally. And when he arrived at her doorstep, neither one of them had any idea what would happen. But as he opened up to her more and more, the vulnerability and sensitivity of the situation created an awkward sexual attraction. Both could feel it immediately, but neither wanted to act upon it. It wasn't until Mrs. Rupert took Tim in her arms when he began crying hysterically that the spark turned into an explosion.

Their lips suddenly met and so it began. Mrs. Rupert undressed herself and then him, and proceeded to straddle him and ride his cock. The encounter was raw and dangerous. Although her husband was at practice, her son could have walked in any moment. But they fucked and Tim felt so relieved that he was finally getting his emotions out, even if it was in this way. And Mrs. Rupert felt years of sexual suppression come loose on this handsome 18-year-old student of hers. Her husband was a killer fuck, but he was rarely in the mood these days after taking on duties as the hockey team's captain.

So for five months now, Tim had received calls on his beeper at least twice a week from Mrs. Rupert. Tim didn't even need to call her. He just slipped on his jacket and walked over. In the beginning, they would talk for a while and enjoy each other's company before undressing. But for the last two months or so, they had barely said a word before or after. Their unusual friendship had turned strictly sexual. Tim didn't mind so much. Mrs. Rupert was an incredible fuck and besides, he wasn't in love with her. Not even close to how he was with Suzy.

Tim finally arrived at Mrs. Rupert's house again and was surprised when he found the door was locked, so he knocked. As he waited, Tim suddenly noticed that Mrs. Rupert's car was gone. But she may have decided to put it in the garage. He was starting to get worried nonetheless. His cock was already slightly erect, and there was no way he was going to like going home and beating off after all this anticipation. He went to knock again, but the door opened.

"Daniel??" said a surprised boy in the doorway. He looked as if he had seen a ghost. The shocked look on the boy's face made Tim forget how pissed off he should have been that someone else was at Mrs. Rupert's. It took a minute for Tim to regain his composure.

"Um, no, I'm not Daniel," Tim said. The boy seemed to realize this just by the sound of Tim's voice. The boy was visibly disappointed. "Uh... um... I'm sorry. I must have the wrong house," Tim said as he started walking away. He knew this was the right house, but he wasn't going to admit that he was here for Mrs. Rupert.

"Wait!" the boy shouted, and Tim turned. "Ar-are you here for my mom? She said that... somebody would be coming by to speak with her." So this was her son, Gerald. She had mentioned him in some of their conversations. Gerald was 14 and still in middle school. And like his father, he played hockey. He was supposed to be at a hockey camp over 100 miles away right now. But here he was- and obviously visibly shaken by Tim's resemblance to this "Daniel."

Tim decided he had better play along. "Um, yes. I'm Tim. Your mom is Mrs. Rupert?"

"Yes. She left stuff for you," Gerald said. "Um... it's in here." Gerald opened the door wider for Tim and he walked inside.

Tim walked past Gerald and tried his hardest not to look as if he had been inside the house before. And yet he had fucked Mrs. Rupert right there on the welcome mat this morning. "Um... where is... the stuff?" Tim asked. He had no clue what he was talking about, but it was obviously something set up by Mrs. Rupert, who was obviously not here. So he was careful to go along with it.

"Right here..." Gerald led him to the kitchen counter, where a book was sitting. "She said you left this at school accidentally and you needed it for homework."

Tim understood what was going on now, and he took the book as if it actually was his. "Yeah, thanks." But he was still curious. "Where did Mrs. Rupert go?"

"Oh... I just got in trouble with someone, so she went to talk about it with them. It's a ways from here, so she might not be back until after midnight."

"Oh," Tim said, as his anticipation and heart sank. He really was going to have to jerk off by himself now. "Well, I guess I'll be going then. Tell her I said thanks."

Gerald grabbed Tim's shoulder before he could leave. "Wait."


"Those aren't the books my mother wanted me to give to you. She didn't even want me to give you books. She gave me a bunch of corrected papers and some notebook to give to you."

Tim was trying to hold back the panic. Gerald had tricked him. He had to get out of this somehow. "Oh... well... um, where are they?"

"You're fucking my mother, aren't you?" Gerald said with a straight face.

"What??" Tim said, doing the best acting he could. "No! She's like... what? 50??"

"She's 46. And you don't have to lie. I know you've been with her. Probably a lot of times."

Gerald didn't seem angry, but Tim started to deny it again.

"You don't have to lie. I've wiped cum out of the shower drain a bunch of times. And I don't jerk off in the shower, so I know it's not mine. And my dad always uses the upstairs bathroom to shower. And when I walked into the house today, I found two used condoms by the couch."

It was true. Tim and Mrs. Rupert had sex twice last night while watching the Playboy Channel on the couch. Tim hoped she had managed to throw away the other condoms that they had used before her son had found those too.

Tim didn't really know what to say at this point. He played the part of gentleman. "Listen, I'm really sorry. Please don't tell anyone. It's really not as bad as it sounds. Please don't tell anyone."

"Oh no, I'm not going to tell anyone. I love my mom and I wouldn't do anything to hurt her. But I need to know why she did this. Tell me why."

Tim felt awkward discussing this with Gerald, but maybe he had no choice. "It's... a long story."

Gerald sat down on a kitchen chair. "Sit down and tell me."

Tim looked at him to make sure he wasn't kidding. And when he saw that Gerald was dead-serious, he sat down too and let out a long sigh.

"It's not all about sex, Gerald," Tim said, and Gerald looked somewhat surprised that he knew his name. "Your mom was just helping me through some bad times and... well, we got caught up in it. But... she still loves her family, believe me."

"What 'bad times?'" Gerald seemed determined to know everything.

Tim hesitated. Was he really going to tell this stranger about Suzy? He almost certainly would break out crying, and Tim doubted that Gerald would comfort him. And yet, Gerald looked generally curious. Tim had fucked this 14-year-old's mother. Maybe he deserved to know everything.

"I was 14 when I met this girl named Suzy. She was 13..." Tim went on about how he and Suzy fell in love right away at such a young age. He told Gerald all about the roller rink Friday nights, and the lunches spent together in the school cafeteria. He told Gerald about the kiss at the Christmas dance. He even told him about the time they had lost their virginity together.

And finally a tear slipped out of his eye. And another. And another. "And I-- don't talk to Suzy anymore."

With that, Tim put his face in his hands and sobbed. He hoped Gerald was happy now, after putting him through all this hurt again.

"It's okay," Gerald said, as he wrapped his arms around Tim. Tim couldn't believe that Gerald was actually comforting him. "It's okay..." Tim didn't care why. He just wrapped his arms around Gerald now and cried even harder. Gerald should have been so mad at him, but yet here he was, acting as a shoulder to cry on. And it didn't matter that he was a guy. Gerald's caring ways seemed to radiate a trust that went beyond the boundaries of male and female.

"Thank you..." Tim sobbed into Gerald's shoulder. "But... why?"

Gerald took his arms from around Tim and looked at him, before sitting back down, and Tim realized he was about to share his own story. "I've been in love too. And that person was taken away too."

Tim leaned in, concerned and wanting to comfort Gerald the same way that he had been comforted. "You can tell me..."

"Well, it was only last year. We had known each other since we were little, but we didn't realize we were meant for each other until last year. We did everything together. We gave each our first kiss... We had sex with each other for the first time... We just did everything. But when our fathers found out about it, we were split up. It was so quick. I didn't even get to say goodbye."

"Why were you split up?" Tim asked, as he reached his hand out and took Gerald's, sensing that he was about to cry too.

"Because we were both boys."

Tim was shocked at the sudden revelation, but tried hard not to show it. He had no idea that Gerald was gay or bisexual or whatever. Tim suddenly felt odd that he was holding Gerald's hand, but decided it would be rude to take it away.

"I've never been attracted to any other boy than him. That's why I know it was love. We were just meant for each other, no matter if we were both guys. But our father's both disagreed, and he and his family moved away."

"I'm so sorry, Gerald."

"Me too, Tim. I miss him so much. At night, I think about him all the time. He's always on my mind. And I don't care to let people know it. That's why the bus hauled me all the way back here from hockey camp. All the boys there know about us, and so I get teased a lot. My mother understand me though. She's very protective of what I did. That's why she's on her way there now, hours away, just to tell off the instructors for letting all that teasing happen."

"Oh my God, I'm so sorry."

"No, it's ok. It was wonderful while it lasted. And I've never given up on him. I still think that some day he could come back to me." Gerald began to sob a little now.

With that, Tim leaned forward and hugged Gerald. "I'm sure he will someday."


The moment suddenly turned silent as they held each other. Tim felt an awkward attachment to this younger boy, and all he wanted to do was comfort him right this moment. Gerald's pain seemed so much like his own. Not even Mrs. Rupert's sympathy fucks matched the power of Gerald's embrace.

Then Tim felt a disturbing thought overcome him, and he let go of Gerald. Gerald seemed to notice something was wrong, but decided not to inquire.

"D-do you drink, Tim?" Gerald asked, trying to break the silence.

Tim picked his eyes up off the ground and allowed a smile to cross his face. "Yes, I do."

Ten minutes later, Gerald had fixed up a fancy daiquiri drink. Tim liked champagne the best, but then he remembered that he had drank the last bottle in the house off of Mrs. Rupert's tits last week.

"Hey, do you know what else we have in common?" Gerald said, a bit tipsy already.

Tim swallowed. "What's that?"

"We've both been in my mom's pussy."

Gerald busted out laughing. Tim was hesitant at first, thinking how odd it was that Gerald was joking about such a sensitive subject. But then the joke crept up on him, and Tim finally burst into laughter too.

Gerald smiled at Tim, glad that he found the joke funny. "So do you drink very often, Tim?"

"No, not really. I used to a lot with Suzy."

"Yeah. I did with my baby, too. You know what else I use to lo-o-ove to do with him?" Gerald asked.

Tim let out a slight snicker, thinking he knew what Gerald was getting at. "What?" Tim finally asked.

"We danced. A lot."

Tim felt stupid for assuming Gerald was going to refer to sex. Especially after he had given the answer he did... "I did too... With Suzy. I use to love to dance with her..."

Gerald smiled.

"I remember the last school dance we were at. I wouldn't let her leave the dance floor..." Tim smiled as he reminisced.

God, he wanted to dance with her right now. He could almost imagine Suzy right there, waiting for him to take her onto the floor. Tim couldn't hold himself back any more. And the drink wasn't helping. He got up out of the chair and wrapped one arm around air, and held his hand out for a phantom hand. And slowly he began to dance with nobody-- just the memory of Suzy.

Gerald sat where he was, watching Tim. Gerald saw the happiness on Tim's face, despite the sadness of the situation. And he recognized it as his own happiness. Suddenly Gerald felt the need to share this moment with Tim, as he got up out of his chair and walked to Tim.

Tim looked at him for a moment, half-knowing what he wanted. And even though it felt wrong, Tim's need to feel a warm body next to his overwhelmed him. Even if it wasn't Suzy's body. And so he wrapped one arm around Gerald, and took his hand in his, and the two began to slowly dance.

Gerald rested his head on Tim's shoulder as he let the older boy lead. Tim's mind started racing. This was just the way Suzy rested her head on him. And Gerald's surrender to the dance was just what Suzy would do. Tim felt 14 again- and in her arms.

As for Gerald, he felt the same. When he and his lover danced, he would always submit to his lead. And Tim's shoulder was so sweet against his face, just like his former lover's.

"What was his name?" Tim finally said, breaking the silence. They continued to dance.

Gerald hesitated for a moment. But then he said softly in Tim's ear... "Daniel."

Tim swallowed nervously. He had suspected this ever since Gerald had told him the story. Daniel was the name that Gerald had accidentally called him when he knocked on the door. Tim almost didn't want to know any more, but he couldn't help himself. He had connected with Gerald, and he had to know. "Do I remind you of him?"

Gerald responded softer this time, slightly sobbing. "You are just like him..."

Tim stopped dancing, but didn't have the heart to let go of Gerald. Gerald lifted his head off from Tim's shoulder and backed up slightly, looking into his eyes. "What's wrong, Tim?"

Tim looked back into Gerald's eyes. "You... remind me of her."

Gerald was silent. He wasn't expecting that. The two young men never lost eye contact though. And almost at the exact same time- like thunder coming down and striking at their hearts- they moved desperately toward each other.

And they kissed.

Suddenly all the pain of the past was freed in this single moment. Their lips smacked together passionately, and their minds were only focused on the present. Suddenly, to Tim, it didn't matter that Gerald's lips were that of another male's. And for Gerald, it didn't matter if Tim wasn't Daniel. They were together, and they had found each other, and that was all that mattered.

Gerald pulled away his lips, almost panting out of breath with passionate excitement. "God, make love to me, Tim."

"Yes..." was all Tim could think to say, as he reached forward and yanked Gerald's sweater off of his body. Gerald then returned the favor, and the two of them pressed against each other again for a kiss, only this time they were bare-chested. Gerald ran his hands across Tim's naked back. Tim felt the sexual electricity flickering between them when Gerald's hands slipped inside his Levi's and cupped his warm buttocks.

"I want it," Gerald said, almost desperately.

Tim moved his own hands quickly down to his Levi zipper, and undid it. Then he dipped down for a moment and pulled his pants and boxers down. When he stood back up to face Gerald, he stood completely naked, with his penis standing out proudly. Gerald looked down at it and smiled, before pressing himself against Tim again for another kiss. Tim's cock sandwiched between his stomach and Gerald's as the two kissed. Gerald's hands went back to Tim's ass and fondled it.

Finally, Tim reached between himself and Gerald, and unbuttoned Gerald's pants. Gerald smiled against their kiss as he felt his pants and underwear being slid down his hips. Gerald kicked them the rest of the way off, being careful never to lose touch with Tim's lips. There, the two boys embraced naked, with their cocks pressed against each other.

Gerald finally broke the kiss and said, "Let's go upstairs..."

Tim nodded with a smile, and Gerald took him by the hand and led him up the stairs. As Tim trailed slightly behind him, he looked over Gerald's back-side. He had never been attracted to another male's body before, but the thought that this was Gerald's body aroused him enormously. That sweet boy who had touched his heart so intensely tonight had an incredible ass, and powerful legs for a 14-year-old. Undoubtedly Gerald's cock was bigger than his own. Tim was a bit over 5 inches, while Gerald was easily nearly 7. And his upper body was toned as well - probably thanks to the hockey conditioning.

They had finally reached Gerald's bedroom. This was the only room in the house that Tim had not been inside yet. On the walls were posters of hockey players, and in the corner of the room was the bed. It was a single-sized bed, with soft black covers.

Gerald turned to him. "Go to the bed, and I'll show you heaven..."

Tim gave him a devilish smile, and proceeded to crawl onto the bed on his hands and knees. Gerald looked over Tim's fine ass, which was smooth and round as it stuck out in the air. Tim's anus peaked out from inside the lusty crevice of his buns.

Gerald finally reached his hands out and ran them across Tim's ass, measuring his new lover. Gerald pulled up tight behind Tim, with his cock coming ever-so-close to Tim's behind. Finally Gerald brought one hand up to his mouth and spat on it. He then reached down and smoothed the saliva across his penis, lathering it up. God, he was ready, was all he could think. His body... his heart... everything was ready for Tim.

And so he pushed forward.

"Oh God!" Tim cried out, as he felt the 7-inch penis head pop into him from behind.

He inhaled deeply as he felt Gerald begin to move farther inside of him. Tim gripped the bed sheets tightly as he braced himself for this new feeling. On one side, it was uncomfortable. Like shitting a brick. But on the other hand, it was beautiful. This young man, Gerald, meant so much to him now, and it felt so good knowing he was inside. Tim puckered his ass tighter at the thought.

Meanwhile Gerald grit his teeth in ecstasy. He held Tim's hips to him as he soothed deeper inside his ass slowly. Gerald had almost forgotten this feeling, but it was coming back to him now. The tight warmth of Tim's ass held Gerald inside of him. Gerald wondered if Tim would let him go if he tried. But right now, all Gerald wanted to do was hit... the bottom.

"Oh!" Tim howled as he felt Gerald's entire penis inside of him now. "God... DAMN."

"Oh Tim, you're so beautiful," Gerald said to his lover, as he gently pulled out. But before his cock slipped out, he pushed back in. Tim felt the penis hit bottom again.

"Yes!" Tim's hips lurched forward slightly, almost resisting the quickening of the sex, even though he wanted it more now than ever. But Gerald grabbed his hips, and pulled Tim to him tighter. Softly at first, Gerald's hips slapped against Tim's. Then Gerald began to quicken the pace, thrusting into Tim's backside faster and faster.

Gerald looked down to see his own dick vanish inside of the fine ass before him, and noticed that Tim had begun jerking himself off. Gerald smiled. "Baby, let me do that..."

Tim looked over his shoulder to see what Gerald meant, and just then Gerald took one hand off his hip and reached around, grabbing Tim's cock. Tim couldn't help but smile back at Gerald as he was being both buttfucked and jerked-off by this young lover. His body was beginning to tremble as this sex was coming closer to a head.

Gerald hips continued moving back and forth at a steady pace now, while keeping his concentration focused enough to masturbate Tim. Both of their nuts slapped together as their panting got heavier. "Yes, Tim, yes!" Gerald could feel the semen knocking to come out. "It's going to happen!"

"Do it, Gerald. Do it!" Tim rocked back at Gerald, helping slick his cock in and out of the penetrated asshole. Tim's insistence finally got to Gerald, and he felt his face get warm. And then... "Ohhhh!!"

Gerald pulled out of Tim's ass quickly, and reached over to his own cock and jerked at it desperately. Moments later, the first spurt of come shot out onto Tim's back. It was followed by another pearly string that reached farther than the first had. Tim smiled at the warm sensation across his back, and began masturbating again.

"Ooooh," Gerald moaned as the rest of his ejaculation oozed out. He was completely spent and entering an incredible afterglow. He laid himself on his side on the bed, and watched Tim stroke himself. The two new-found lovers watched each other. It was Gerald's gentle gaze that finally sent Tim over.

"Fuck!" Just as suddenly, Gerald watched Tim shoot his ejaculation onto the bed covers. "Yes, yes, yes..." His body got weaker and weaker with every shot of come.

"That's beautiful, Tim," Gerald said to him with a smile.

When he was done ejaculating, Tim let go of his own cock and quickly threw himself next to Gerald. The two young men smiled at each other, sharing this afterglow together. After a moment of looking into each other's eyes, they kissed passionately. After that, they wrapped their arms around each other tightly, never wanting to let the other go...

Three hours later...

Tim and Gerald had never let go. And their moment of afterglow had turned into several minutes, until they had both fallen asleep in each other's arms. They were so lost in the embrace that they had allowed themselves to become careless and clumsy. Now it was nearly 11:30, and a pair of eyes were peaking through the doorway at the sleeping bodies of the two naked boys.

Mrs. Rupert had never seen a sight quite like this before.

To be continued...

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