Trying Him On For Size

Story by Anicha on SoFurry

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Unsure about a new guy friend, Karen joins him for a picnic in the woods, and is pleasantly surprised.


Josephine and Karen were enjoying their weekly Sunday brunch, at the usual place downtown. Jo, a brown furred, zaftig mouse was paying this time around, and the pair were discussing the week's events, as they were known to do. Karen, a russet furred vixen, stirred her coffee slowly as the pair awaited their food.

"I went to a movie with that boy you introduced me to," murmured Karen, bringing a paw to her muzzle to stifle a yawn. Jo gave a knowing smile and asked,

"Oh, and how was that?" To which the vixen replied,

"The movie was awful. I'm surprised they could take such a great idea as giant alien robots who punch one another, and turn it into such a bore." The two shared a laugh and Jo offered,

"No, I mean the boy. Blake, was it? What did you think?" Karen smirked a little, looking up in time to spy the waitress bringing around their food. She speared a piece of scrambled egg onto her fork and took a bite before continuing her story.

"Well, he's very nice, I'll give you that," she said, "But I can't help but feel like I'd get bored of him very quickly. How did you say you knew him again?" Jo busied herself spreading some whipped butter over her pancakes before she spoke up,

"We shared a few classes in college, and dated briefly. I remember him being a lot of fun, and very sweet. Maybe he's mellowed out a bit since those years." Jo shrugged and spooned some strawberry jam over her pancakes before she cut off a piece and took a bite. Then she got a sly smile on her face and said,

"He has a way with his tongue, or at least that's what I remember. Nice dick, too, especially for a mouse boy. What did you do after the movie?"

Karen brushed a bit of her blonde hair out of her eyes and took a sip of her coffee. She held up a paw to indicate she was forming her thoughts and then finally, she spoke.

"Well, he kept his hands to himself during the movie, as I'd expect for a first encounter. He was a little clueless, though, and at first declined to come into my apartment with me when he dropped me off. Said it was getting late and that he shouldn't be up watching movies with me," mused Karen with a roll of her eyes, "He changed his tune at least when I got more blunt about what I wanted to do with him... for a second I thought he was gay." Jo erupted into giggles and said,

"Oh, no... well, he is very well-kept and soft-spoken, isn't he? What did you two do?" The sly smile returned to the vixen's face as she ate for a few moments, then she answered,

"Mmmn, well, I did end up putting on a movie just to cut the awkward silence. He moved his hand to mine and I sort of took it, and put it under my skirt. He took the hint and started stroking his fingers along my crotch. He seemed so nervous. Especially when I reached over and helped his dick out of his slacks." Jo licked her lips and leaned in closer,

"Well, he's always had a hard time with the ladies, and you.... you can be kinda intimidating. What then?" Karen smiled and leaned back.

"Well, that finally got him looking at me, and not what was on the TV. He got rock-hard really fast. I swear, I could hear a thump when his dick fully hardened and slapped against his stomach. Nice bit of cockmeat, too. He slid his fingers under my panties and started to finger me as I stroked him a little bit, then I kissed him. First kiss of our date. Anyways, I told him I wasn't gonna let him fuck me on our first date, but that if he ate me out I'd return the favor." Jo looked intrigued, but for a moment focused on her meal. Their food, after all, was getting cold.

"Did you like it?" asked Jo finally, and Karen nodded her head, chewed her food and swallowed. She took a sip of her coffee, glanced around for any in earshot who might take offense, and then continued telling her lurid tale,

"He did a pretty good job, I have to say. Didn't rush things, really made me feel like he would do it all night if I let him. Really put to rest my suspicions that he wasn't that into me, the way he just... worshipped my cunt. Kept going after I came, and so I let him get me off again before I'd had enough. I considered pushing him down further and telling him to lick my ass, but I didn't want to scare him off... not yet." Jo had her eyes closed, like she was just picturing the whole scene, only chiming in to say,

"Oh, he licked mine when we were fucking around... but I did kinda wave it in his face and tell him to. The boy follows directions at least."

"Right, so then it was my turn. He got really into it when I was sucking his cock, and he was leaking everywhere by the time I got to the task. Called me all kinds of nice names when I was down there, and warned me when he was about to bust a nut, which took a long time... my lips were going numb. I didn't back off when I was warned, and oh my..." said Karen, lifting her brows and giggling, "He cums buckets. I almost choked. He looked like he was about to apologize, but just thanked me when I swallowed it all. We cuddled for a bit after that, and he went right to sleep in my arms. He was gone in the morning when I woke up, though." Karen looked up from her plate and saw a mortified face. A couple and their two children had just been seated nearby. Jo and Karen exchanged pleasantries but ate mostly in silence, paid quickly and left the cafe in a hurry. They continued their discussion walking down a scenic street in the nearby park.

"It sounds like you enjoyed yourself. Are you really thinking of not calling him back?" asked Jo. Karen sat at a bench and shrugged a bit, saying,

"Well, you know me. I like a guy or a girl who will surprise me in the sack. Someone who will take initiative from time to time, and do the kinky shit without being told. He is nice, though, drives a nice car, has a good job... if only I knew there was more to him than that encounter. It was fun, however vanilla it was."

Jo smirked and said, "Honey, you just need to get him out of his shell, and show him what a dirty girl you are. We did some pretty wild stuff together once he knew he could trust me not to judge him. Maybe I'll tell you about it sometime. Anyways, my car is pretty close to here. Mind if I cut off? Promise you'll give him a chance?"

"Fine, I'll give him another shot. Maybe even clue him in to what I want, and try to bring him out of his shell. It won't take too long, will it?" asked Karen with a sigh.

"You were the one that started it with that 'first date' nonsense... anyways, bye!" said Jo, seizing this opportunity to break off. Karen was left alone with her conflicted thoughts, and wondered how she would swiftly make Blake prove himself worthy.


The following Saturday came, and Karen realized that she forgot to return his call, having sent the first to voice mail. There wasn't another. She dialed him up and he didn't answer.

"Karen here," she said after the tone, "Listen, I'm sorry I didn't call you back sooner, I was just working through some shit... Think we could get together soon? I wanna talk, and maybe a little more..." She ended the message and her phone rang right away. It was him. Blake spoke up on the other end,

"You said you wanted to talk?" His voice wavered a little, like he was expecting some bad news. Karen didn't want him on the defensive and so she said,

"Oh, not like that! Listen, could we just do something together real soon? I can be a real bitch to boys like you, but I don't want to scare you off."

"How about later today?" asked Blake on the other end, "We could go to the park, have a nice picnic, and you can tell me what's on your mind. If uh, that's alright." Karen wasn't much into the idea but she figured his company was pleasant enough, and that maybe she could lure him back home to her bedroom, and 'accidentally' leave out something scandalous.

"Sure, we could do that. Say, around 3?" she asked, trying not to sound too apprehensive.

"Sounds great. I'll see you at 3," he said. That gave Karen a few hours to get ready. She showered, shaved, put on some cute underwear and some sexy perfume on her pulse points. Then after thinking about it, she chose a casual green sun dress and decided not to wear her panties after all. She left them out on the bed and opened the drawer of her nightstand. Then she spent entirely too long arranging the toys within the nightstand drawer in such a way to make them properly visible while left slightly ajar. Butt plug and lube at the front, her go-to vibrator tucked away in the back.

It startled her when 3 rolled around and the doorbell rang promptly and urgently. She greeted him at the door. He was dressed nice, in slacks a lightweight button-up shirt and a tie done into a perfect windsor knot, his brown headfur carefully combed to a part at the side. He was carrying with him a picnic basket. An idea struck Karen as she met his eyes and said,

"The park sounds nice, but I have a better idea. Go for a drive with me?" She yanked him inside and led her into her apartment garage, he got in the car and they drove off.


The drive wasn't too long, but it was mostly silent until Blake finally broke it.

"So uh, how do you know Jo?" he asked, and Karen shrugged, turning the corner as she drove off to the undisclosed location she hadn't told him about yet.

"Met her at a yoga class. We have brunch most Sundays, sometimes cocktails together back at my place," said Karen, and saw this as an opportunity to slip in a little, tempting detail, "We talk about boys, mostly. Girls on occasion. She agrees with me that you're pretty good at eating pussy." He swallowed and said,

"Yeah, she is kind of my ex... what else did she tell you about me?" Karen slid her stick-shift paw over to run it along his thigh and said,

"Oh, nothing much. Told me you just need to come out of your shell." Just then, Karen stopped the car, having pulled it over to the side of the road. This was a bit off the beaten path, the street surrounded by woods on either side, though not too terribly far from civilization. "We're here. Come on, I want to show you something," said Karen.

He was a bit reluctant to follow, but the trail through the woods was a bit muddy, and his shoes looked like he'd spent the better part of the afternoon shining them to get ready. Nonetheless, he soldiered through, not having much choice, as Karen had the car keys.

"What do you mean 'come out of my shell?'" he asked, and she paused, turning to look back at him,

"Oh... well, I like you, Blake, but you're a bit timid with me. I want a guy who's good to me, but I also want a guy who's wild in the sack. But I don't want to talk too much about it on an empty stomach... or sober, for that matter. I saw some wine in that basket, so be a dear and get it open." He looked taken aback, and had to pause to get out the corkscrew and wine bottle, but he caught up to her with picnic basket and wine bottle in hand. She snatched the bottle from him and took a swig, then handed it to him. Here, a bit off the trail, over a fallen tree was a large, grassy clearing. About as private as nature ought to be.

"I know you're supposed to let merlot breathe... but that's sort of my point, Blake. I'm not a proper lady. Let's set up here," said the vixen, with a playful look in her eyes. He seemed to have softened some, having had a few swigs himself. After he laid down the blanket, he loosened his tie and sat down, leaving his muddy shoes aside. He took a breath and spoke up, meaning to explain himself,

"I just didn't want to put you off, is all. I thought you wouldn't like me if I was too forward, too... presumptuous." Karen shushed him as she opened the picnic basket, then took out the tupperware container of salad and for a moment, she admired the fancy bottles of balsamic vinegar and olive oil in the basket, before adding a measure to each. She speared some greens on a fork and brought them to his mouth, and he ate, obediently.

"Jo speaks highly of you, so you can't be too offputting. It's just that you're the only guy she set me up on a date with, instead of just bringing you over for a nasty three way. Why is that?" she cooed.

"We have a bit of rough history, maybe," said Blake after swallowing the salad greens, "We don't play around anymore, had kind of a messy break up. I only just got in touch with her when I came into town, and she told me she would set me up with a friend of hers." Karen blinked a few times and leaned back, taking a bite of the salad for herself.

"Well, well. I didn't know she got emotionally involved... she only seems to keep fuckbuddies around. Didn't think she was much for romance." Karen looked like she was about to continue, but saw the topic was making him uncomfortable,

"Don't worry, we don't have to talk about her." He reached for the wine bottle and took a swig, forgetting the travel cups packed away in the basket.

"Good, I'd rather not. How can I convince you I'm not a bore in the sack?" said Blake, watching Karen's eyes gleam with mischief. She chose this moment to shift her stance and uncross her legs, then let her skirt ride up enough to show him that she had shaved just for him.

"Let's keep drinking and just let it happen, baby," said Karen. And they did, for a while, avoiding the subject that was on both of their minds. It was obvious enough to Blake, for example, why Karen had chosen the location for their date - privacy. The salad finished and the sandwiches neglected, they got close as the afternoon went on, and as the wine bottle slowly emptied. Before long he had his hand up her skirt, and hers were down his pants. That was when she asked,

"Did you bring any condoms?" and soon he was frantically searching his pockets.

"Shit. I left them in the car. My car. Just bought a fresh box." Karen tsked and looked up at him, shaking her head.

"We're both too drunk to drive, and probably will be for at least another hour. I was gonna let you fuck me, but I don't know you well enough yet for bareback," she murmured, looking up to him with a playful grin, "At least not in my pussy." It didn't make much sense to him, as he knew he couldn't impregnate a vixen no matter how hard he tried, being a rodent... but he caught her hint at something dirtier still than an outdoor fuck at a romantic picnic.

"You could blow me again," he suggested, "That'll give us something to do... or, I've got an idea. Get on all fours." She did so quickly, pleased that he was starting to catch on, and beamed when he pulled up the back of her skirt, then flagged her tail. It was a perfect sight - sundress lifted, tail lifted, a perfectly smoothly shaven vixen twat... and that snug, clean pucker between two soft, redfurred buttocks. He grunted at the sight, leaned forward, and spit onto her tailstar. Karen gasped and did her best to look scandalized, but he was not discouraged, rubbing his thumb over her anus. He spoke up,

"I didn't bring condoms, but I did bring condiments. The olive oil should lube you up nicely for a dick in the ass." She looked over her shoulder, then reached for the wine bottle, and took a swig. She had to hand it to him - he was better prepared than she was. Karen lightly nodded her approval, and spoke fairly huskily,

"That's more like it, stud. Gonna warm me up first?" He spanked her and laughed, saying,

"You seem plenty warmed up already, but...." She inhaled sharply as he leaned in and ran a slow lick up her asscrack, paying particular attention to that small hole. Another few slow licks followed as he stroked his fingers over her sopping wet mound. The fancy bottle of no-doubt expensive olive oil was opened hastily and he drizzled some over that vulnerable opening. While not as thick as water-based lube, it did the trick, easing the passage of his pinky finger as he drove it into that forbidden hole. Karen wailed, and the fur on her tail bristled. She slipped a paw down between her legs and shamelessly splayed her folds before him as he prepared her ass.

"It seems you found the way to my heart," said Karen, her tone half whispered. Out came the pinky only to be swiftly replaced by his thicker middle finger.

"The way to your heart is up your asshole? I'll be the judge of that, Karen," chimed in Blake as he soon worked her tense anal muscle open around a second finger. More of the oil was added, and then out they came. Karen closed her eyes and sighed, opening them again when she felt something thicker pressed to her butthole. He had his pants around his knees, his dick was greased up, and nestled sweetly against her backdoor. She drew in a sharp breath when he first started to push into her, then yelped as the wide glans popped within, and veiny inches followed. He grunted under his breath, muttering profanity as she opened up around his prick, brought his arms around her hips and pulled her back. She felt him slip deeper, lowered her chest to the blankets and pressed to him until she could feel his balls resting their weight on her sopping pussy.

"I,,, I take back what I said earlier, Blake, I---" she began, before being interrupted.

"Shut up and take it," groaned Blake as his hips pulled back and rebounded, slamming into her fully with sufficient force that his pendulous scrotum bounced off her muff with the impact. If he had to prove himself, he was going to rise to the challenge, and he did, building to a slow, but deep and hard, pace, each stroke drawing out agonizingly slow only to plunge into her bowels blindingly fast. Each testicular collision with her pussy made a wet, percussive sound that rose up above the heavy breathing and also sent jolts of electric pleasure through her body. By now Karen had stopped masturbating, instead simply holding her folds apart to properly expose herself to the battering dealt out by Blake's heavy balls. As he picked up speed, she felt herself nearing her peak, and soon came crashing over the other side, gasping and trembling and crying out. Her hot insides churned and gripped, milking at his dick until at last he hilted in her and began to spend his hot, copious payload in her belly. She was only just beginning to come to her senses again when she felt his dick pumping and spurting, and his semen draining into her bowels. He held onto her through his climax, panting to catch his breath. When she felt him softening within her, she pulled away from him and turned on all fours, mouth pressed forcefully to his in a longing, desperate, needful kiss.

"So, did I pass the test?" asked Blake after the kiss ended. She huffed, wanting to slap him, but said simply,

"Yeah... you made the cut. We should get back to my place before it gets too dark." They hastily packed the leftovers and blanket in the basket, and made their way back out of the woods toward the car, with Karen walking more cautiously this time. In the car she fell swiftly to sleep, knowing that she and Blake still had a lot to talk about, but for once... the vixen was satisfied with her date.