Authors note.
This is a story based on Chuck and takes place during Season 4.
*
"Exc... excuse me." Ellie stammered, convinced she must have been more drunk than she thought because she couldn't possibly have heard her brother's girlfriend right.
"I said, get on the bed and bend over." Sarah said like this wasn't something completely out of the ordinary, the blonde then stepping forward moments later to comfort her friend, "You wanted my help right? With Devon's little... request?"
"Well yes but I was expecting... I don't know, some advice or something." Ellie said.
"And I told you, there's nothing I could say that you can't find on the Internet, and no words could really prepare you for the feeling of taking a big hard cock up your ass." Sarah said, "Which is why the best way I can help is to, well... show you what to do."
Ellie's eyes almost popped out of her head, "Oh, erm, I, thanks but I'm not gay."
"Neither am I, and that's not what I was suggesting." Sarah said, quickly cutting Ellie off before she got the wrong idea, or more accurately the right idea, "I'm not suggesting we have anal sex, just that I show you how to properly loosen up your ass hole. Because trust me, no matter how much instructions you give them even the nicest of guys will awkwardly shove a couple of fingers up your ass, and then their cocks, and you'll probably hate it, but let him do it now and then when you really want something. But, if you let someone who knows what they're doing take their time to gently stretch your ass hole out it can be one of the most pleasurable experiences you'll ever have. And trust me, if you let me help you practice for a couple of days by the time you're bending over for Devon your ass hole will crave the feeling of getting fucked. You'll be a total anal whore, ready to fulfil everyone of your husband's desires."
It may have been the three glasses of wine Ellie had consumed to work up the courage to ask the blonde's advice about anal sex but Sarah seemed to be making a lot of sense. Ellie was still a little worried though, "O, ok... what... what exactly would you do? To help me practice I mean."
"Oh, just use my fingers, and maybe a small dildo, to stretch you out back there. Get you used to the feeling of something sliding in and out of your ass hole. Show you it isn't as scary as you might think." Sarah said, a little smile crossing her face, "Hopefully show you why I love anal so much... show you how good it can feel to have something inside your ass... moving in and out... fucking your little ass hole."
Ellie blushed and silently thought this over. It was crazy she was even considering something like this, but if Ellie was going to try anal sex it seemed to make a lot of sense for her to dip her toe in the water so to speak. This way she could feel what it was like to have something invading her ass hole without getting Devon's hopes up, and she would be in the hands of someone who had taken it in the ass before as opposed to someone who'd only dreamt about anal sex.
So Ellie pretty much made up her mind, but she was still nervous about it so buying herself a little time to calm her nerves she asked, "Have you done this before?"
Sarah smiled, "Maybe once or twice."
"Ok... ok, ok let's... practice." Ellie said, very slowly getting on all fours on the bed.
For a moment Sarah lost control of herself, a look of lust crossing her face as Ellie presented the spy with her ass. Luckily Sarah was able to come to her senses before Ellie could turn to catch her staring or licking her lips, which only happened briefly, Sarah able to keep herself in check as she quickly retrieved a bottle of lube and then got on the bed behind Ellie. When she slowly, carefully pulled down Ellie's pants and panties revealing the other woman's ass Sarah lost control again, this time Sarah reaching out and grabbing two handfuls of Ellie's perfect butt before gently caressing the prize in front of her.
"You have a beautiful ass Ellie." Sarah said softly, squeezing the round but firm cheeks of Ellie's butt.
"Thanks." Ellie blushed, not sure what to make of Sarah's actions.
"Devon is a lucky man." Sarah said, able to stop herself saying anything further as she pulled apart Ellie's butt cheeks and lustfully studied the other woman's ass hole for a few seconds. Oh how Sarah would have loved to lick that puckered hole, or slide her mouth and tongue all over those beautiful cheeks, or even go after Ellie's pussy which looked encouragingly wet. But one thing at a time.
"You're going to have to relax, ok?" Sarah said, as she let go of Ellie's cheeks and quickly applied a generous amount of lube to the fingers of her right hand. Once there was plenty of lube on her fingers Sarah used her left hand to gently spread Ellie's left ass cheek, the blonde giving herself as much room as possible to get at the brunette's ass hole.
Ellie gasped as she felt a wet finger gently touching her virgin rosebud and immediately tensed up. Luckily Sarah didn't try to force her way into Ellie's butt. Instead the blonde just gently rubbed some lube onto the brunette's back hole, Ellie finding the soft caressing of her butt hole oddly comforting, the touch slowly coaxing her to relax.
Of course that was Sarah's plan, the spy waiting until she was convinced her friend couldn't be more relaxed before firmly sliding a finger into Ellie's back door.
"Ah!" Ellie cried out, more in surprise at the suddenness than actual pain. In fact there wasn't that much pain at all. It wasn't the greatest feeling ever, but it wasn't unpleasant. And for the most part that was how it continued. Even when Sarah added a second, then a third, then finally much later a fourth finger the experience was far from what Ellie had expected. Then she moaned. She couldn't believe it, but it actually started feeling good. Really good.
It took a while for Sarah to get a moan out of Ellie, but it was totally worth it. That little sound meant Ellie was Sarah's. She might not know it yet, but she would very, very soon.
Of course getting that moan had been a lot of fun as Sarah had loved every second of slowly stretching out Ellie's shit hole. She had adored fingering her friend's ass, only adding additional fingers when she was absolutely sure the other woman was ready, working then gently to further open the brunette's butt hole, gently caressing the soft yet tight walls of Ellie's rectum. It was marvelling at the tightness of the other woman's back passage which was Sarah's favourite. This was partly because it proved to Sarah she really was doing Ellie a favour by stretching out this tight little hole, but in truth Sarah just liked the way Ellie's butt felt clamping down on her fingers. It made her horny, made her want to give this cute little virgin ass a real stretching.
"Ellie... I've stretched your ass hole as wide as I can with just my fingers. I could fist you, but I think what we really need now is depth. So I'm going to get a nice long dildo so I can stretch the deepest part of your ass, make sure it's nice and ready for your husband's big cock. Are you ok with that?" Sarah smiled as Ellie moaned a enthusiastic response. Deciding to push her luck Sarah added, "Good, I'll go get one of my toys... in the meantime, you don't have too, but it might help if you fingered your ass hole. That way your ass hole stays nice and loose."
Following another positive moan from the brunette Sarah removed her fingers from Ellie's ass, a smile crossing the blonde's face as she watched as one of Ellie's hands immediately shot to her backside and inserted two fingers into her already loosened butt hole.
Sarah watched Ellie shamelessly finger her own ass hole for a few moments before quickly yet quietly sneaking over to her toy draw, opening it up and retrieving her favourite type of toy, namely a strap-on. It was extremely tempting for Sarah to pick one of the bigger models, but for her boyfriend's sister she chose a nice 8 inch model, expertly strapping it around her waist after removing her pants and panties, and then moving back onto the bed so that she was kneeling behind Ellie again without making a sound loud enough to disturb the moaning brunette.
By now Ellie had three fingers in both her pussy and ass and was using the palm of one of her hands to rub her clit. From the way Ellie was moaning Sarah guest it wouldn't be long before her friend came. Sarah could let that happen, put her strap-on away, hand Ellie a vibrator and leave her to it, or something like that, but Sarah just couldn't resist. She had resisted going after Ellie for so long, too long, and now Sarah was going to make Ellie hers.
Grabbing hold of Ellie's hands Sarah used enough pressure to stop their movement without hurting her friend. There was a whimper of disappointment from Ellie before Sarah quickly said, "Ellie, I thought you wanted to practise for Devon. Make sure you're ready to take his big cock up your ass."
"I do." Ellie whimpered.
"Then stop trying to make yourself cum like a little slut." Sarah said deliberately firmly before then just as deliberately softening her tone, "Trust me, I'll let you cum soon enough, if that's what you want, but we need to get this big cock of mine inside your ass while it's still nice and loose and ready to be fucked. But it's up to you. In a second I'm going to let go of your hand. You can make yourself cum if you want and we can call it a day, maybe try again tomorrow if you want. Or you can spread your ass cheeks for me. Make it easier for me to get my big cock in your tight little ass. You choose."
Letting go Sarah watched with bated breath for a few seconds, and then smiled widely as she watched Ellie slowly reach back and spread her ass cheeks, submitting to the butt fucking Sarah so wanted to give her.
Sarah took longer than necessary lubing up her dildo, admiring the sight of Ellie offering up her ass hole to be fucked. It was a beautiful sight, one which Sarah wanted to commit to memory, something she would treasure forever. Then Sarah did something else that she would treasure forever, that being taking Ellie's anal virginity. Sarah took Ellie's anal cherry slowly, placing the head of the dick against her friend's previously unviolated butt hole and then gently increasing the pressure so that the tight ring of flesh was slowly forced open until the first few inches of strap-on cock slid deep inside Ellie's virgin ass.
Ellie let go of her butt cheeks and cried out in pain, but it wasn't as bad as she feared, and for that she was very grateful to Sarah, who unnecessarily apologised, "I'm sorry. It always hurts at first, but trust me, you'll be begging for more in no time."
