6 Times a Day

Iveyflame Special [ 4 / 5 ]

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Amy though, seemed unworried. She immediately repositioned, lying between his legs since he was sitting on the floor. Seeing that he was too aroused to stop her, she pulled his shorts all the way off while she was at it. Mere seconds later, she had his boner trapped in her cleavage. "Cool! It's just like what we were talking about Christine doing to you. But the question about Christine is: you like her, but do you LOVE her?!"

Alan sighed, even as his body was buzzing with pleasure from feeling his boner trapped between Amy's big tits. "I don't know. It's so hard to say. I mean, I'm not sure how 'love' is defined. I love you, Sis, Mom, and Aunt Suzy as family, as well as sexually, so I don't think it's fair to compare to that. I've never had a girlfriend, so I don't have much to compare things to that way. I do know that my feelings for her are really strong, and I've had them for a really long time. If I don't love her now, I'm sure I would if she felt the same way toward me and things developed between us."

"Good answer," Amy said. So far, she'd just kept his shaft in her cleavage, but now she started the titfuck in earnest. "But you can't say you don't have a girlfriend. I mean, you're totally fucking Heather. You admitted that. And Kat and I are NOT happy about that, as you know!" She frowned at him, but she didn't stop sliding her tits up and down over his boner.

He sighed, although again he was so overwhelmed by the titfucking pleasure that it was hard for him to feel upset about anything. "I know. And I'm sorry. But like I tried to explain, it's complicated. Besides, Heather is definitely not my girlfriend. No way! She won't even say 'boo' to me at school. Just think of her as one of the girls helping me with my dick problem."

"M'kay. I understand. But still, why don't you get someone else to help out instead of her? If you need help at school, why don't you go for one of the other cheerleaders, like Kim? She's become one of your helpers too, right? And she's nice."

He didn't know how much Amy already knew, and he didn't want to reveal more than he had to. So he said carefully, but truthfully, "She has, and she is. And if she helps me out, that's great. But she doesn't really inspire me that much. She's short and skinny; her body type doesn't match what I really like. That's a taller, fuller figure, like you have, and like the other women in this house have."

Amy asked, carefully, "So you don't think you could fall in love with her?"

"Kim? No. Remember, she's two years younger than me. That's a big deal. Maybe in a couple of years, when she's matured both physically and emotionally, but by then I'll be a couple of years older too, so who knows. Besides, I think she's mostly lesbian."

"M'kay." Amy was still steadily sliding her tits around his shaft, while keeping up a very tight squeeze. "What about Janice then? Or Joy?"

He grunted with lusty need. "Um... It's kind of hard to talk when you're doing that." He nodded down at her titfucking action.

"Oh. Sorry. I'll stop for a minute." She repositioned out of the titfuck, but only slightly. She resumed jacking him off with both hands.

He winced, because that was very nearly as pleasurable. But he decided to soldier on, because it felt too good to ask her to stop. "Anyway, regarding Janice and Joy... Nah to both of them. I mean, I wouldn't kick them out of bed for eating crackers, as the saying goes, but I don't have any reason to think I'd have a special spark with either of them. A special spark is, well... special. What I feel for Christine... nobody else in school even comes close to making me feel that way. Not counting you and Sis, of course, 'cos that's a different thing; I've known you two all my life. But even just thinking her name makes my heart beat faster."

Amy was fondling his balls with one hand, like she'd seen Katherine do earlier. Her other sliding hand was soaked from all the pre-cum. "So why don't you ask her to help with your thingy problem then? She's a nice person. I'm sure she'd be glad to help."

"It doesn't work that way. It's complicated. For one thing, she's not that nice. I mean, she is to me, since we're friends, but she's also kind of prickly. I have to be really careful not to offend her. She didn't get the nickname 'Christine, the Ice Queen' for nothing, you know. Remember, she turned me down very recently, and that was just asking to spend time together outside of school. Playing with a guy's thingy is much more intimate."

Amy asked, "So, in that case, how is it you're getting help from everyone in this house, and Heather and Kim besides? Plus who knows how many others. ARE there others?"

He looked away shyly. "Um... no comment." Amy's handjob had him thrilling to an endless wave of sexual arousal. But the downside to that stimulation was that he wasn't as mentally sharp as usual, so he couldn't deftly dodge that question like he normally would have. In fact, his facial expression gave him away.

Amy said, "A-ha! There ARE others! I can totally read it on your face." She giggled. Then she blew fresh air on the tip of his cockhead, making him shiver with arousal. "M'kay, who? Let's hear some names. I'll bet Ms. Rhymer is one."

"What?!" He tried to act surprised and offended, as opposed to caught. "Why would you say that?"

She giggled. "Oh, come on. We know you've been moony for her for a couple of years now. You may think you hide it at school, but you never really hid it at home." She blew air on his cockhead a few more times between words, getting a good reaction each time. "Your face lights up when her name is mentioned, same as Christine's. In fact, let's see if Mr. Thingy responds in the same way."

She leaned in even closer and stuck out her tongue, lightly brushing it against his cockhead. That tantalizing feeling gave him goose-bumps. As her fingers kept on sliding over his sweet spot, she spoke to his erection, while making sure to continue blowing air on it. "Gloria Rhymer. Gloria Rhymer. Glory, Glory, Glory!"

She pulled her head back and felt his cock in her hands. "A-ha! That totally worked! Your thingy is all extra tingly! It's burning hot and practically jumping in my hands!"

He said with exasperation, "That's because you've been stroking it for a while and it feels really damn good! You're like a natural at that already. It's uncanny. And then when you blow heavily on it on top of that, of course it's going to react. It's the puffs of air, not your words, that are making it twitch so much."

Amy grinned slyly. "You say that. But I noticed you haven't actually denied that she's helping you out."

He protested, "Aaaaammmy! She's my teacher! How could I get involved with my teacher?"

She replied while trapping his throbbing hard-on in her cleavage again. She resumed titfucking him, and with extra vigor, "I see; you're going to play hard to get. M'kay. You probably think you need to do that to protect her and her job. Fair enough. But let me ask you this. We all know you've been crushing on her the past two years, kinda like you have for Christine. How do you think your feelings compare between those two? Or between either of them and the four of us here at home?"

Alan groaned, both from frustration and from sheer arousal. "Amy, why are you asking me such tough questions?! And while you're distracting me in such an arousing way at the same time!" He looked down at her titfucking with sheer disbelief.

She giggled with impish glee, but she certainly didn't stop or even slow down.

He griped, "I don't know! I don't like comparing people like that; I really don't. I don't think it's fair for anyone involved. But let's put it this way. Both Christine and Glory are very, very special to me. I've had a crush on both of them for a long time now, and not JUST because they're both so beautiful. What I was saying about Christine, how I feel a special connection emotionally, intellectually, and other ways, that goes for Ms. Rhymer too. The other girls at school don't interest me at all because I have not one but two major crushes there already."

Amy pointed out, "And yet you're fucking Heather, and doing stuff with Kim."

He groaned, again from frustration and lust. "It's complicated. Both those things were total flukes. You probably know how things started with Kim. That was completely by accident, especially since she's mostly lesbian. Bizarre stuff like that isn't going to keep happening to me, I'm sure. As for Heather, I'm just the 'flavor of the month' for her. I'm sure that'll die out soon."

He continued, "In Kim's case, she just has a minor curiosity about penises, and I'm a safe way for her to experiment. That'll end soon too. Christine turned me down, so that's over. End of story. She's not interested in me, I can tell. As for Glory, well... No comment there."

"A-ha again!" Amy giggled gleefully, while her tits kept on slipping and sliding over his pre-cum soaked shaft.

He ignored that and tried to continue. "My point is, I'd be lucky to have just one woman to help me out with my special penis problem. I'm unbelievably lucky that I have the four of you here at home. I'm not going to be picking up more and more helpers, like some kind of... pied piper of penis tenders. Look at me! I'm just a guy; I'm not some kind of hunky Adonis."

Amy beamed at him. "Hey! You're a pretty special guy to me."

He smiled right back. "And you're very special to me too. And now we're going to get to know each other in a whole new way with this penis-helping stuff. But it's not just my dick; there's no reason we can't get touchy-feely in other ways too."

Amy said enthusiastically, "I totally love touchy-feely! Let's get all huggy!"

He chuckled. "Yes. Let's. Amy, you're so adorable that I could just eat you all up." He opened his arms invitingly.

Breaking the titfuck, she immediately moved in closer and sat on his lap, wrapping an arm around him and cuddling in close. But she was careful to position herself so she could still at least keep one hand pumping up and down on his boner.

Amy purred happily as she rested her head against his neck. "Aaaah! I like this. And playing with your thingy is totally fun too. How long do-"

She froze in mid-sentence, because they heard the distinctive sound of the sliding glass door to the backyard opening. They both instantly knew that meant Susan was coming in.

Alan whispered, "Quick, Aims, run! Towards the bathroom!"

She started to get up very quickly indeed. She whispered, "M'kay!" Then she took off like a rocket past the foyer and the base of the stairs towards the lower bathroom.

Alan pulled his shorts up immediately. That was no problem. But then he noticed Amy's clothes scattered on the floor.

Susan called out, "Tiger? Angel!"

Oh shit! Since he was already sitting on the floor, he crawled the few feet to Amy's clothes and picked them up. Only then did he respond, "Hey, Mom! Over here!"

Susan had already started walking towards the living room. He just had time to hide Amy's clothes behind his back before she came into view.

She walked into the room and saw him kneeling on the floor, a few feet from the video game console but pointing in the wrong direction. She asked, "What are you doing?"

"Oh, I was just starting to come to you."

She chuckled. "It would help if you stood up then." She was so trusting with her family that she didn't suspect anything.

He nodded, but didn't get up because he didn't want her to see that he had a lewd bulge in his shorts. She would have been delighted to see that, but undoubtedly she would have slid his shorts off shortly thereafter and he wouldn't have any good explanation as to why his hard-on was already drenched with pre-cum.

Luckily for him, she'd been working hard on the garden and she wasn't paying close attention. She said, "I think you've had enough time playing around. I've got so much to do in the garden that I realized I could really use some help."

"I'd be glad to help, Mom." He was relieved that his fear of getting caught was causing his erection to go down.

"Good. Get ready to sweat. Would you get your sister too? If she's not doing something important, I can use her help as well."

"Sure. No problem."

A few moments later, as soon as Susan turned her back, he pushed Amy's clothes under one of the sofas and ran upstairs to Katherine's room.

He would have had his sister hurriedly help him get his rocks off, but by the time he got upstairs his penis was completely flaccid. That opportunity had passed. He briefly explained to her how Amy had jacked him off, which she seemed glad to hear. But they didn't have much time to talk because Susan called for them to "stop lollygagging and come help."

Alan, Katherine and Susan went outside and worked on the garden together. It was all shockingly normal, like a trip back in time. Alan was slightly disappointed that he hadn't gotten to cum, but he figured that he'd climaxed so many times lately that it was probably for the best. Besides, he found doing physical work outside to be a refreshing change of pace.

He never did find out what happened to Amy, given that he'd unthinkingly hidden her clothes under the sofa. But he figured she must have located them and gone home unobserved after he and his mother and sister had gone to the garden, because there was no sign of her, or her clothes that he'd hidden, when they came in from gardening an hour later.