Milo and Gela: Further Questions

Story by TastesLikeGreen on SoFurry

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#4 of Eric and Milo

Milo Thompson has a lot of stuff on his mind, which is understandable, given the past few weeks. But when he gets a call from his best friend Angela, he has no idea that it's only gonna lead to... more stuff on his mind.

I bet you thought I was gonna say "further questions", didn't you?


Further Questions

By Green

Milo Thompson lay back on his bed, just thinking. He wasn't ordinarily the introspective type, but he'd been doing this a lot the past few days. It had started before that, of course, when he started fooling around with his brother Eric. After he got over the immediate 'gay panic' mental barrier, he realized it didn't feel like "sexy touching" so much as it felt like stress relief, something the two of them did to make the other feel better. That feeling had continued until a few short days ago, when they'd actually had sex for the first time. Eric, as the older of the two brothers, had pulled rank and made Milo be the receiver, and Milo, to his extreme shock, had deeply enjoyed the sensation. In fact, he'd enjoyed it so much that he'd managed to get off from being taken without ever touching himself.

That had raised a lot of questions in Milo's mind. He hadn't even known it was possible for a male to climax without touching his genitals in some way. And here he was, blowing a load from getting slammed by his brother. He'd played it off like he'd masturbated, so Eric didn't know about it, but Milo was still troubled, unsure of what it meant. Just yesterday, he'd repeated an experiment he'd tried once, looking at gay porn to see if it did anything for him. He didn't react with outright revulsion the way he once had, but that was more likely due to the fact that he'd actually done those acts than any major change in his preferences. Confusingly, the video still didn't turn him on in the slightest. He just wasn't sure what to think. If he was straight and what he did with Eric was just stress relief, why had he come when he was the bottom? And if he was bi, why didn't he feel anything for any male other than his brother? He was pretty sure he wasn't in love with Eric, so he could find no answers.

The original arrangement they'd had was that after Eric took Milo, they would trade places, although Milo had put it off after he'd lost control of himself. It was probably for the best, because the very next day, Eric had come down with a really bad cold, so they'd been taking a break from their shenanigans. Right now, Milo was staring at his ceiling, idly thinking of things he could do with the afternoon. His thoughts were interrupted by his cell phone ringing on his desk. He rose and headed over to it, not one to screen his calls. He'd never been one for popular songs playing from his pants; his ringtone was and always had been the sound of a phone ringing. Glancing at the front display as he picked it up, he saw that it was his friend Angela Taylor, or "Gela" as she preferred to be called, since in her opinion nicknames like Annie or Angie were too "girly". They had been born only a week apart, and they'd been neighbours when they were extremely little. As a result, they'd known each other forever and could comfortably be referred to as best friends.

"Hi, Gela. What's up?"

"H-heya Milo. Not much, you know, slow day."

Did she just stutter? That's not like her.

"I know what you mean, not much going on over here either."

There was a moment of silence.

"Milo? Are you gonna be doing anything this afternoon?"

"No, not really."

She definitely sounded hesitant.

"Could... could you come over to my place? I really need to talk to you."

"Sure thing. Is something wrong?"

"I... don't wanna talk about it over the phone. See you soon, then?"

"Of course. See ya, Gela."

"Yeah, bye Milo."

Milo frowned as he closed his phone. Something was definitely up. Angela Taylor was normally one of the most confident, outgoing people he knew - despite being a mouse, there was no way the tomboy could be described as "mousy" - but just now she sounded incredibly subdued, unsure of herself. He hoped he could help her with whatever was troubling her. As he looked for his shoes his mind drifted back to various memories from their long, prolific friendship. Running around the park playing all kinds of games. Concocting elaborate plans to take over the world from the treehouse in the forest behind Angela's house. Belching the alphabet. Egging houses on Halloween. Sharing the blame for egging said houses on November 1st. Watching in awe as Angela picked a fight with three older boys - and won. And later on, getting drunk for the first time, together, on hard lemonade. As he finally found his shoes under a T-shirt and went downstairs, he once again wondered what was troubling his friend so much that she would be so anxious.

The Taylors had moved out of the house next door to the Thompsons when Milo and Angela were eleven, but their new house still wasn't very far away, so Milo just walked, since it was a fairly warm day. As he approached the front door, his phone buzzed as he received a text. It was from Angela, and it was short and to the point: 'It's unlocked.' This was more unusual behaviour from his friend, who had always greeted him warmly at the door. Milo was starting to worry, although a part of him was more concerned with wondering how she'd had such perfect timing with the message. Sure enough, the door was open, and he let himself inside. The place seemed to be empty.

"Hello? Gela?"

The response came immediately, from up the stairs.

"I'm up here, Milo, and no, there's no one else home today."

Leaving his shoes by the front door, he headed up to her room on the second floor. She was standing by the window, gazing out onto the street as if she expected to find the answers to life's problems. It at least explained the great timing on the text message; she'd have been able to see him coming all the way down the block. She looked normal enough, wearing a loose-fitting T-shirt and a pair of baggy jeans, her shoulder-length blonde hair, wrapping around her large grey ears, looking slightly unkempt, as her idea of 'styling' generally ended after a good combing. No, her appearance didn't bother Milo. What bothered him was that she didn't even turn around when he walked into the room.

"Gela? Are you okay? Is something wrong?"

"No, nothing's wrong, I just... I just wanted to talk."

"I don't remember the last time you were this serious, Gela. Did someone die or something?"

Finally she turned around to face him. She didn't look upset, and she hadn't been crying, so there was that at least. But at the same time, there was something off, she looked... unusually calm. She moved to lean against her desk, and looked him in the eyes, brushing a lock of blonde hair out of her eyes.

"No, nobody died, I just need to get something off my chest."

She gestured at her bed, which was directly opposite the desk.

"I think you're gonna want to sit down."

Milo, who was quite concerned by now, stifled the urge to let out a whine as he did as she asked, tail tucked between his legs. Angela closed her eyes and took a deep breath before speaking.

"We've been friends a long time, right Milo? We can be honest with each other, right? Don't have to keep any secrets?"

"Of course, Gela, you can tell me anything!"

"Right. Well... let me ask you something then."

Mouse fur being shorter than most other kinds, Milo realized when she turned her head a certain way that she was blushing. Before he could dwell on this, she turned back to him.

"Milo, do... do you think I'm pretty?"

Milo was blown away by this simple question. He couldn't have been more surprised if she'd said she had cancer, or was moving to New Zealand. His mind went absolutely blank, and the shock showed plainly on his face, so despite the fact that he was unable to answer, Angela read his expression pretty clearly. She looked decidedly unhappy, turning away from him and crossing her arms over her chest.

"So you don't, then. Real subtle. Thanks for softening the blow there, Milo. Great job of improving my self-esteem."

The confused shepherd now had the twin jobs of pacifying his friend and getting his reeling mind back under control.

"N-no, it's not that, I'm just surprised, you know? Why would - why are you asking?"

The mouse sniffed indignantly, looking almost as embarrassed as she was angry.

"Maybe you forgot, but I am a girl, dumbass. We're allowed to care about how we look."

"Um, Gela, do you remember the last time I complimented your looks?"

"What?"

"Early teens, you were upset, ring any bells?"

A strange look came over her face.

"You mean..."

"You were all embarrassed and stuff because your boobs were coming in and you didn't want them. So I told you not to worry, that they were very nice."

Despite herself, the mouse girl smiled.

"...And I put you in a headlock and told you never to talk about my boobs again."

"So you can see why I'm surprised. Gela, why are you asking me if you're pretty? It's not like I'm an expert on pretty. If you want a makeover or something, why don't you talk to your sister?"

Catherine Taylor was far more versed in things like fashion and makeup and such than her younger sister. Angela shook her head dismissively.

"That's not what I meant, dude."

The mouse cleared her throat and looked intently down at her feet, as though she had never seen socks before.

"Milo, I'm not wondering if I'm pretty... I'm - I'm wondering if you think I'm pretty."

For a moment it seemed he didn't get it, furrowing his brow in confusion like he didn't see the difference between the options. Then, suddenly, his eyebrows shot skyward, his eyes widened, and he leaned back slightly, a shocked expression coming over his features.

"Wait... you don't mean..."

For the first time Milo could remember, Angela Taylor was looking at him in a manner that could be described as "shyly". She was a lot more soft-spoken than usual, too.

"It's like I said Milo. No matter how I may act, I'm still a girl. And you're still a boy."

The German shepherd swallowed hard.

"...Holy fuck."

Angela went back to staring at the floor as she continued.

"I suppose it's not that surprising, we've been best friends since kindergarten. You're not like a lot of boys, Milo. You're sweet and sensitive and... stuff. You've never, ever broken my trust or told anyone a secret I've given you. When that asshole on the soccer team was telling lies about how I sucked him off, you went right in to fight him."

Milo was still having trouble dealing with the basic concept of the conversation, but he was still aware enough to make a comment.

"And he totally kicked my ass."

Angela shrugged.

"Well, yeah, you're not the physical type. But it's the thought that counts. You didn't even think about it, you tried to, you know, defend my honour or something. Aw jeez, this all sounded so much better in my head."

Milo shook his head in disbelief.

"But Angela, are you really saying this? That you, uh..."

He trailed off, unable to even say it.

"I didn't know you felt that way about anyone! Actually, uh, I kind of thought you were gay."

He wouldn't have said such a thing if he were fully composed, and he immediately clamped a hand over his mouth, the expression on his face just as easy to read as if he'd actually written "oh shit" on it. But instead of freaking out, Angela just frowned.

"Dammit, why does everyone think I'm a lesbian? So I like watching hockey more than chick flicks, and I played with G.I. Joes as a kid instead of Barbies. That doesn't make me a dyke!"

She stopped leaning on the desk, obviously upset.

"Look Milo, I'm sorry I brought it up, it's obvious that you don't think of me as a girl, so no wonder this is a surprise to you. I - I need to go."

She started to storm out, despite the fact that they were in her room, but Milo caught her hand as she passed him.

"Gela, wait!"

She whirled around, fire in her large brown eyes. Milo found himself wondering if her large front teeth could bite through his neck. He swallowed and forced himself to speak.

"I... The reason I didn't think of you as a girl was that I was trying not to."

She tilted her head, her anger seemingly gone, but still on edge.

"What do you mean?"

"You're... aw hell, I'll just say it. Even though you dress like a guy and act like a guy, you're really good looking, Gela. I thought that if I had feelings for you, it would only end badly for me, since you never cared about that kind of thing. So I tried to think of you as just another guy."

This time he neglected to add that he'd thought she was gay. She still didn't look totally sure of herself, so he added something on the fly, rubbing her palm with his thumb.

"I never noticed how soft your hands were before, Gela... please, don't leave."

He spoke without thinking, and realized afterward what it meant.

"Please, stay with me."

Suddenly she wasn't the only one blushing.

She came and sat down next to Milo on the bed, looking down at her feet once again. For some reason, his mouth suddenly became dry. After a moment of awkward silence, Milo spoke up.

"So how long have you... felt like this, Gela?"

"I first noticed it around the time my Dad had the car accident."

"Wait... that was more than a year ago, Gela. Do you mean you've... that all this time..."

"Come on, Milo, haven't you ever had a secret you couldn't tell anybody, not even me? Are you really surprised that I didn't say anything?"

Suddenly the mental image of himself being taken from behind by his own brother popped into his head.

"...I guess not."

Angela took a deep breath and then continued as if she hadn't heard him, almost as if she was simply narrating her thoughts. She was, oddly, somewhat more eloquent than usual, almost as if she'd practiced this speech before.

"Dad was in the hospital, he was beat up so bad. They weren't sure he was gonna make it. I've never seen my mother so scared, she left for the hospital right after she heard. She wouldn't let me go, didn't want me to see my father like that. And my sisters were all away... I would have been all alone, all by myself with the fear and the pain, but you stayed with me the whole weekend until Dad came out of critical condition."

"Well..."

"You held me when I cried, you made sure I ate when I wanted to just stay in bed, and you told me over and over that everything would be alright... that no matter what happened, you would be there for me. Milo, I've never felt more weak or pathetic in my life than I did those nights. And you weren't just helping me because you felt obligated to... you wanted to help me feel better. You let me lean on your strength."

"That's what friends are for, Gela."

She sighed and rubbed her forehead absently.

"I know. That's the problem."

"What do you mean?"

"Milo... you're my best friend. You've always been my best friend. I can't imagine life without you. But now that I... you know... I've been worrying. I know plenty of people who started dating their friends, and when they break up, it destroys the friendship. I..."

She swallowed audibly.

"I want to be with you, Milo. But I don't want to risk wrecking what we have."

He reached over and took her hand in his once again. Finally, she looked up at him. He smiled in what he hoped was a reassuring manner.

"So we'll take it slow. It's not like we have a time limit."

She returned his smile, but there was something in her eyes he couldn't place.

"There is one other thing, Milo."

"What's that?"

She moved very quickly, before he could react. Suddenly, she was kneeling on the bed directly in front of him, her legs outside of his. He leaned back in surprise, very, very aware of the warmth of her body next to his; she was practically sitting in his lap, her thin, hairless tail whipping back and forth behind her.

"Gela?"

"I want us to just stay friends for now, Milo, and not do anything crazy, you know? But I've thought about it for a long time now, and I... we... aw shit, this is embarrassing."

"Angela, what's..."

She reached up and wrapped her arms around his neck, giving him a loose hug. Then the mouse took a deep breath and looked him straight in the eye.

"I - I'm still a virgin, Milo. And I want you to be my first."

Every time he thought he had his mind back in order, she did something that sent it back into chaos.

"Wh-what?"

She laughed at the completely shocked look on his face, sounding more at ease.

"You see, Milo, when a man and a woman want to feel very close, they -"

"I know what you meant, I just thought - didn't you just say you didn't want us to do anything?!"

He cursed himself for letting out an involuntary whimper as she leaned in still closer.

"I said I didn't think we should jump into a relationship just yet. That doesn't mean we can't be friends with benefits. Come on Milo, I know you've thought about it. Have you ever been with a girl before?"

Milo counted his lucky stars at this point; Angela had always been able to tell when he was lying, and if she'd just asked 'are you a virgin' he would have been in trouble, as she would never let up until she found out the truth.

"Well, no..."

She started gently stroking his furry cheek with the tips of her fingers.

"Look, I know this is sudden, but I've been thinking about it all year, and I didn't want to lose my nerve. You remember all that stuff I said earlier, about how you're sweet and kind and everything? I can't think of anyone else I'd rather give it up to, Milo."

He swallowed and reached a trembling hand forward, mirroring her movement and brushing his fingers against her cheek. It was fuzzy and oh-so-warm, and he smiled slightly as she nuzzled against his hand.

"I never thought I'd be touching you like this, Gela."

Angela's smile widened.

"Oh, Milo, Milo, Milo. You ain't seen nothing yet."

She leaned forward, obviously angling for his mouth, and, deciding that it was now or never, Milo moved to meet her lips.

It was so simple, he almost missed it. Their lips pressed together, and both teens quivered slightly as they experienced the warmth of the other's mouth. Milo inched his tongue forward hesitantly, but Angela boldly set forth to explore his mouth, as though she planned to claim it in the name of her country. Milo shivered at the feeling of her warm, wet tongue rubbing against his, and just let his instincts guide him, wrapping his arms around her, holding gently onto her shoulders. Suddenly it hit him: this was it. This was his first kiss. And, just as he'd always hoped, it was with someone he cared for deeply. It had never occurred to him it would be with this someone, but still... A part of his mind considered the fact that he would now be free to kiss his brother, but he chased it away and focused on the mouse girl who was reaching under his shirt to run her hands over his back, occasionally being brushed from the outside by his madly wagging tail. He wasn't quite that bold himself, but as he continued making out with her, he started to slide his hands down Angela's back, feeling her nicely-toned muscles beneath her shirt since her fur wasn't very long. He shivered with anticipation as his fingers passed over the rear band of her bra. Meanwhile, her fingers were beginning to squeeze and knead at his back, and he was starting to feel very good indeed. He eventually reached her belt, and only hesitated for a moment before sliding his hands onto her jean-clad rear end, daring to give a squeeze. She let out a sigh and sank down, now actually sitting in his lap, her crotch pressed against his. He tensed up as he realized that he was at half-mast and she surely knew it, but she broke off the kiss with a smile.

"Relax, Milo. We want that to happen, remember?"

He blushed and grinned back at her.

"It's not my fault. You should have warned me that you had such a nice ass."

He squeezed her cheeks again to punctuate his statement, and she wiggled on his lap, pressing his hardening length between their bodies. They stopped for a moment as she pulled his shirt over his head and tossed it to the floor, and he helped her out of her own. He took a moment to admire her, her slender, shapely abdomen lightly covered in the same grey fuzz that adorned the rest of her body, her breasts covered by a simple white bra, as if she'd deliberately picked the plainest model she could find. He meant to compliment her, but before he could say anything, she leaned forward and kissed him once more, pushing against him this time so that he fell backwards, lying flat on his back while she lay on top of him, kissing him hungrily, her tail whipping from side to side to gently lash at his legs. His member was now achingly hard, and being sandwiched between them didn't help it any. They only remained in this position for a few minutes before Milo could stand it no longer, fumbling with the latch on the back of her bra before accidentally getting it right. As it popped open, Angela opened her eyes and gave him a look.

"Are we in a hurry, Milo?"

Suddenly remembering that this was someone who had kicked his ass on a few occasions (only when he deserved it, naturally), he panicked.

"S-sorry, Gela, I just -"

She laughed, mussing up his hair.

"It's okay. Just messing with you. You wanna see? Take a look."

She pushed herself into an upright position, removing the brassiere as she did so, and sure enough, Milo stared with youthful intensity at the first bare female chest he'd seen in person since he was young enough to breastfeed. He wasn't looking at her face, so he didn't see the unusually shy expression there.

"What do you think?"

He reached up and tentatively touched one, as if making sure they wouldn't bite, before covering it with his hand and squeezing gently. Then he nodded approvingly.

"Looks like I was right. You do have nice boobs."

She laughed and briefly kissed him again, letting out a quiet churring sound as he continued to play with her breasts.

Before too long she got off him and stood up, fiddling with her belt. Taking the cue, he went to work on his own buckle, trying not to look too hurried as he worked his pants down his legs. At first he was surprised to be so embarrassed, after everything he'd done with Eric, but then it occurred to him that this was with a girl, that this would be for real. He glanced over at Angela, then did a double take and laughed, causing her to blush all the way to her wide, thin ears. She was wearing boxer shorts.

"Shut up! They're comfortable."

"They're cute. It suits you."

To put her more at ease, Milo decided to finish undressing first; taking a deep breath, he took a firm grip on the waistband of his own boxers and then swiftly tugged them down his legs. Angela grinned and walked over as he moved to lie along the bed's length instead of across it. His heart was beating like a jackhammer, and he was actively fighting the urge to hide his package with his hands. Still wearing the boxers, Angela sat down on the bed beside him, openly leering at him.

"Wow, Milo, you're pretty good looking."

"Th-thanks."

Calmly, almost casually, she reached down and took hold of him, her grip firm but not painful. Milo suppressed a whimper, but couldn't stop his breathing from speeding up, or his hands from balling up fistfuls of the blanket. She turned him this way and that, peering at him like she had never even heard of penises before, frowning slightly.

"What's wrong? Is it - am I - um..."

He couldn't bring himself to say 'too small'.

"No, no, nothing's wrong, it's just... I thought you had, you know, a sheath and a knot and stuff."

He was slightly taken aback.

"Um, not every canine dude has those, Gela."

"Oh, I know, it's just I seem to remember seeing that when we played doctor when we were really little."

His best friend was already holding onto his penis, but if he could have blushed any harder, he would have.

"You remember that?"

It had somehow always seemed less embarrassing when he thought she had forgotten.

"Oh sure. 'You show me yours, I'll show you mine' and all that. I guess I don't remember it as well as I thought I did, though, since all this time I thought you had Inherited all that dog stuff."

She looked up, saw the look on his face, and smiled.

"Hey, relax, it's fine, I'm actually glad, since we won't be stuck together for, like, half an hour after we finish."

"Heh, that's a good point."

"Yeah."

Still looking him in the eye, she began to stroke him lightly up and down, her slender fingers trailing along his straining flesh from his very tip to his base, hidden away amongst the longer fur. He shuddered under her touch.

"G-Gela, what are you doing?"

She casually took his balls in her other hand, massaging them gently as she responded.

"I'm playing with your junk, what does it look like I'm doing?"

"No, I mean -ah!- I mean I - I don't know how long I can last, okay? And this isn't helping things any!"

Like a lot of teenage boys, Milo Thompson worried about premature ejaculation, worried about how he'd perform when it came time to prove himself.

"Well, why do you think I'm doing this?"

He whined quietly as she trailed a fingernail along his taut flesh.

"Gela, quit screwing around! If you don't stop you're gonna make me... you're gonna finish me off, and I - I really wanted to be with you."

"Relax, Milo. If I make you pop like this, you'll be able to last longer when we actually are together, later. At least, that's what it said on the Internet..."

It made sense to Milo, so he relaxed and lay back, trying to will himself to stop blushing. He found it was very difficult to sit still while Angela, who was both his best friend and a hot, topless girl, gave him a handjob. His tail was squished between her bed and his back, but it was still doing its best to spaz out and wag like crazy. His feet began to twitch as she squeezed his testicles together and rolled them around in her hand. As she kept going, Angela gradually squeezed his length harder and increased the speed of her strokes. With a throb, a single dollop of pre emerged from his darkening tip and was quickly massaged into his flesh, slightly lubricating her strokes. Soon, he could feel himself hurtling towards the edge, but he wanted to hold on just a little longer so he wouldn't look premature in Angela's eyes. However, the mouse clearly saw the strain on his face and worked even harder to finish him off. Soon enough, he started lifting his hips off the bed, clenching his teeth with the effort not to give in, his breath hissing through his black, wet nose. Finally, he could fight it no longer, and his whole body spasmed as he came, grunting with each release, spurting jets of hot seed all over his torso, his genitals throbbing in Angela's hands as he experienced a tremendously powerful orgasm. Eventually, he relaxed, lying back and staring at the spots in front of his eyes, wondering when the room would stop spinning.

"Damn, Milo, I've seen porn where the guys didn't come that hard!"

There was just a touch of awe in her voice. He tiredly lifted his head and grinned sheepishly at her.

"Thanks, Gela. That was a really good one."

"Don't move, I'll go grab a towel or something."

She left the room, leaving him lying there covered in cooling goo. A few moments later, she walked back in, wiping her hand off.

"Here you go."

She tossed him the towel and came to sit down beside him as he cleaned himself off. Once he was presentable, he pushed himself up and leaned in to kiss her once again, a kiss she eagerly returned.

After a minute or two, Angela broke off the kiss and stood up.

"Okay, I've put it off long enough."

Quickly, roughly, as if she was yanking off a band-aid, she pulled the boxers down and kicked them across the room. For just an instant she seemed unsure of herself, and then she placed her hands on her hips and stood up straight, her expression almost defiant, only her twitching tail betraying her nervousness. Milo's eyes were immediately drawn to her girl bits, almost totally hidden by the well-trimmed tuft of blonde between her legs.

"Well, there you go, Milo; Angela Taylor, the whole package. What do you think?"

He didn't hesitate at all. He opened his arms and beckoned her over.

"I think you're beautiful, Gela. I've always thought that."

She smiled wide enough to show off her molars. That was the right answer.

"Then let's not put it off any longer."

She stepped back over to the bed and joined Milo. As she made herself comfortable next to him, he suddenly moved down the mattress, bringing his face towards her groin. She blocked her treasures off with a hand and moved away from him.

"Whoa whoa whoa! What do you think you're doing?! I said I'd sleep with you, none of this... extra stuff!"

He shrugged and avoided eye contact.

"I, uh, still don't know if I can last long enough to make it good for you, so I wanted to make sure you came, too."

Obviously taken aback, Angela relaxed.

"...Oh. Well, okay. Just, uh, don't think this means I'm gonna suck your dick or anything."

He thought about adding 'yet' to her statement, then decided the suffering wouldn't be worth it.

She moved her hand out of the way, and he leaned in towards her, staring intently as her delicate folds came into view. This was something new to him, and he hoped improvising would have the right effect. Letting out a breath he hadn't realized he'd been holding, Milo extended his tongue and gently touched it to Angela's outer lips, causing both of them to tremble in excitement. At first he just traced her cleft with the tip of his tongue, stopping for a moment to follow the advice of most of the porn he'd read in his life and circle around her clitoris. Then he grew bolder and pushed between her labia, beginning to explore the inside, while she reached down and took hold of his head, churring quietly. Her juices began to flow quite copiously as he bathed her sensitive inner walls with his tongue. It was a curious flavour; he'd wondered pretty much since he hit puberty what it would be like. Oddly enough, it almost tasted like salad dressing, something he'd never expected. He lifted one of his hands off her thigh to massage her outer parts while he continued lapping at her insides. Angela moaned as he gently squeezed her clit, and he felt her vagina clench down on him for a moment.

"Fuck, Milo, this feels so damn good... are you sure you're a virgin?"

She obviously meant it as a joke, but he still decided to sidestep the question, pulling out for a moment to answer her.

"I swear I've never done this before. Not with a girl, anyway."

He said it like that, too was a joke, but she might have been able to tell there was more to that statement than there appeared to be. Fortunately, she was a little preoccupied at the moment.

As he pushed his tongue back into her welcoming depths, she let out a little whimper of her own, and moved a hand from his head to her breasts, squeezing and massaging them in turn. Milo was momentarily distracted by this, seeing his best friend the tomboy acting like the girls in his video collection, but she encouraged him to keep going by pressing on the back of his head, and he focused on his delightful task. He licked harder and faster at her, pushing his tongue as far into her as it could go, feeling her juices beginning to soak into his fur and absolutely not caring. Meanwhile his nimble fingers kept playing with her love button, sometimes squeezing, sometimes rubbing, sometimes barely caressing, and her legs kept twitching as her pleasure built and built.

"Oh God... a little to the left, Milo... Yes! There! Right there! Ahhh, fuck..."

He wasn't sure if he'd found her g-spot or not, he wasn't exactly an expert on these things. All he knew is that the spot she'd directed him to had a slightly different texture than the rest of her tunnel, and she shivered from head to toe when he pressed his tongue against it. Being a gentleman, he focused his efforts onto that spot, and she churred once again in bliss as her feet reached up around his back and hooked together, as if preventing him from running away. As he continued, Angela's breathing grew faster and heavier, and her trembling grew more pronounced.

"Oh, shit, Milo... I - I'm so close... don't stop, oh God, please don't stop..."

Milo increased his efforts, moving faster and pressing harder, though his tongue was starting to get seriously fatigued, and it wasn't long before Angela's thighs clamped shut on his head, and she arched her back, shuddering. From all the 'research' he'd done into the subject, he expected her to let out a long moan, but instead, as her pussy clamped down on his tongue, her juices gushing out to finish soaking his face, her whole body going rigid, she just made a single, loud, extremely high-pitched squeak. He kept toying with her clit while she came, hoping it was making it even better for her, and he kept lapping up her juices, now quite fond of the flavour. Angela's orgasm seemed to go on and on, and he was finally interrupted when she started pushing on his face.

"Ok-kay, Milo! Okay! If you k-keep going I'm gonna g-go fucking crazy!"

Totally and completely spent, she collapsed to the mattress, curling up on her side, shivering with aftershocks, her fur glistening with sweat. Milo, intensely proud of what he'd done, moved back up the bed to lie down beside her, grinning like a Cheshire cat. He was about to make a comment about said pride when she turned over and buried her face in his chest, groaning. This was unexpected. As she nuzzled into his chest, he automatically wrapped his arms around her, a part of his mind noting that her hair smelled quite pleasant this close up. Pushing that thought aside, he voiced his concern.

"Gela? Are you okay?"

She tilted her head up just enough to make eye contact, and he realized she was blushing again.

"I'm fine, it's just... ah hell, nobody's ever seen me come before, okay? I'm kind of embarrassed, is all."

He grinned and hugged her tighter. He'd said almost the same thing recently, but it was probably for the best not to tell her about it, given that he'd said it to his brother.

After a couple of minutes to get her body back under control, Angela was ready to go forward. She reached down to her jeans on the floor, took out her wallet (She refused to carry a purse on principle) and retrieved a condom, which she slipped into his hand. Silently nodding his thanks to her, he ripped it open and rolled it down over his member, which had gotten nicely stiff again while he was eating her out. Angela raised an eyebrow over his skill with the prophylactic.

"That was quick."

"I've, uh, practiced."

She snorted in amusement.

"Boys."

With nothing left to delay the inevitable, Milo threw a leg over her, positioning himself for The Deed, trembling with anticipation. He reached down and got a grip on himself, attempting to align his gift-wrapped shaft with Angela's opening. And failed. He thought he had it lined up, but he was slightly to the left, his erection bumping against her pubis and sliding down her thigh as he pushed forward. He tried again and got the same result. The third attempt, rather than being the charm spoken of in the idiom, merely saw him sliding off to the right instead. Without warning, Angela, who had grown tenser and tenser with each of Milo's tries, reached up and took a firm grasp on his shoulders.

"Okay, screw that."

Before he could react, she suddenly spun him to the side, continuing the movement so that she ended up on top of him.

"Yeah, this is more like it. If I'm the one this is gonna hurt, I wanna be the one in control."

Milo was secretly relieved that the pressure was no longer on him, but tried not to let it show on his face.

"Fine by me."

Angela positioned herself above his groin, then reached down and grabbed his cock, angling it upwards and lining it up with her entrance fairly easily before taking a slow, deep breath, and then sitting down on him, letting out a yelp as his erection parted her folds and pierced her hymen on its way inside her. She trembled atop him as he reached up and took her hand.

"You okay?"

She shook her head slowly, then composed herself and looked up at him, an unhappy look on her face.

"...Holy fuck that hurt."

"Do you wanna stop?"

"No, I'm good, just gonna take it slow."

He nodded, and she leaned forward and placed her hands on the bed in order to give herself better leverage. Then she pushed with her thighs, slowly sliding off her friend's pole, before sinking back down, her body eagerly welcoming him back. Up. Down. Up. Down. Before too long, she had a rhythm going, the movements flowing smoothly into each other. Milo noted that she was starting to grin instead of wince when he sank back into her. He reached up and began to play with her breasts, and she laughed and picked up the pace. He loved the feeling, even through the condom she was so warm and tight, it felt like she was embracing his penis, a far cry from the rough grip of his hand. And a glance up at the blonde mouse girl he was enjoying the sensation with made it even better; this was someone he cared about. He smiled gleefully, unable to help himself.

"Ohhh... I can't believe we're doing this, Gela... I can't believe we're actually fucking!"

She giggled.

"Oh my God... Who's we, Thompson? I - umf - I'm the one who's doing all the work here!"

It was the strangest sensation, laughing during sex, but her giggle was infectious, and as he laughed, the shepherd pulled her down to him so that she was again lying on top of him, her legs doing the heavy lifting (so to speak) now. Milo kissed her with a ravenous hunger, one she returned at least as strongly. He placed a hand on her head as they made out, running his fingers through her surprisingly soft hair. She was still his best friend, still the smart-ass he'd known for all those years, but she was also so feminine, so soft when she let herself be. If he wasn't careful, he might really fall for her. Letting those thoughts, like all the others, drain out of his head, he moved his other hand to her shapely ass, squeezing a buttock before teasing the sensitive base of her tail with the tips of his fingers, earning him a shudder and a gasp for his troubles. About the time he was tracing her buck teeth with his tongue, he realized he was, once again, closing in on the edge. This wasn't what anyone would call premature, he was surprised at how long he'd been able to last (score one for the Internet), but Angela didn't seem to be anywhere near his state of arousal.

"G-Gela, I'm so close... I'm gonna c-come..."

He said it with an apologetic tone, but she moved one of her own hands to his head and scratched behind his ear, whispering encouragement in it.

"It's okay, Milo. Go ahead."

Having been given the all-clear, he stopped trying to resist and felt himself plummeting towards release. He grabbed her hips with both hands, though it wasn't clear whether he was holding her down on his dick... or just holding on to something for the turbulence ahead.

"Oh God... oh my God... oh - Angela!"

Moaning out her name as his climax began, Milo shuddered as he ejaculated hard, deep inside her, painting the inside of his protective sheath with his hot semen. His orgasm wasn't as strong as the powerful one he'd experienced at her hand, but something about the fact that it was through real, honest-to-God sex made it so much more satisfying. As he continued helplessly spurting his cream, he tilted back his head and howled, the way his distant ancestors would have howled at the moon. A tiny portion of the part of his brain that still functioned was aware no one else was home, but at that moment he was surrounded by pure bliss, and he didn't give a damn if the whole country knew it.

Milo's climax lasted an unusually long time, his penis continuing to throb even after his supplies of sperm had been taxed, but all good things must come to an end, and finally he went limp on the bed, his fur soaked in sweat, his tongue lolling out as he panted like a feral. Angela lifted herself off him, his softening member falling against him with a wet slap, and lay down beside him, gently scritching behind his ears.

"That was certainly an experience, puppy. I've never heard you howl before."

She hadn't called him 'puppy' since they were eight - they used to play a game where one of them would pretend to be a feral and the other would treat them appropriately.

"Well, mousie, I've never heard you squeak. That was super cute, by the way."

She told him to shut up, but her smile revealed that she really didn't mind. He tilted his head up to look down at his groin.

"Oh, crap."

"What?"

"Look for yourself."

The condom itself was mostly clear, if glistening with her fluids, but the fur around his penis, and his mostly bare scrotum, were stained with blood. Not a whole lot of blood, but it was noticeable. While Milo tugged off the condom and slipped it into a trash can, careful not to spill any more bodily fluids, Angela reached gingerly between her legs, looked at her hand, and frowned.

"Shit. Guess I shouldn't have been so rough."

"It's a good thing your family's out, you're gonna want to wash these sheets."

"Yeah, better get on that pronto."

He started to get up, but she placed a hand on his chest to halt him.

"Wait..."

Then she leaned in and kissed him again, this time slow and undemanding. It didn't last very long, but it was so much more tender than before, it felt better somehow.

"You were great, Milo. I knew I made the right choice."

"Thanks, Gela. You were awesome. Sorry you didn't get off."

"Well hey, thanks to you being a gentleman, that's not a problem."

She grinned naughtily.

"There's always next time, isn't there?"

Milo took a quick shower to wash the blood and the dried come out of his fur, while Angela loaded the sheets into the washer. She jumped into the shower when he was done to rinse herself off as well, before starting the wash cycle and praying nobody would arrive before it was done. With that done, they sat down on the couch and talked about what had happened between them. Despite the subject matter, they once again sounded like 'just friends', though it seemed to Milo that both of them felt something more towards the other. Once they'd finished discussing the dramatic new change in their lives (though it did take quite a while), they went on to more normal conversation, talking about movies and video games and such. Around the time the wash cycle finished and they switched the sheets into the dryer, Milo decided it was time to get going. Angela saw him to the door, told him she'd had a great time, and asked if he wanted to go see the mindless action movie that was coming into theatres that weekend. He agreed, kissed her lightly on the cheek, and left with an enormous smile on his face.

That evening, Milo once again lay on his bed, pondering life. He was no longer a virgin in any sense of the word, and he'd seen a whole new side of his best friend. Literally. As he thought about his situation, he began to frown. None of the questions that were bothering him that morning had been answered. He still didn't know why he came when he was with Eric. He still didn't know if he was secretly bisexual (He decided it was fairly safe to say by this point that he wasn't gay, however). In fact, the events of the day had even raised more problems. Did Angela really have feelings for him? How strong were they? Did he now have feelings for her? She'd suggested they become friends-with-benefits, and he was okay with that, for now at least. Would it be possible for them to "officially" hook up without ruining their lifelong friendship? Did he want to? If he got himself a girlfriend, what would that mean for him and Eric? He really enjoyed what they did together, but they would probably have to stop if he found a Significant Other. Would Eric be okay with that? Milo didn't think of what he and Eric did as a "relationship", but she'd probably see it as cheating if they didn't stop and she found out, even ignoring the fact that it was with another male, who happened to be his brother. Most girls would flat-out abandon him if that were the case, but he'd known Angela his whole life... would she be able to accept it? He shook his head, chasing these problems out of his mind. He'd slept with his best friend. He'd slept with a girl. And he'd done pretty well, if he did say so himself.

That eventful day may have brought him further questions, but he didn't regret it for a second. He might be a bit confused, but he was very, very happy. And when it came right down to it, that's what mattered to him. So when he went to bed that night, his sleep was untroubled, and there was a wide, satisfied smile across his muzzle.