tagAnalBreaking in the Pledges

Breaking in the Pledges

byJagFarlane©

Anna bore a sheepish look as she entered into Alex's apartment, gingerly walking due to her sore inner thighs. Quietly she stepped towards the kitchen, trying not to disturb Alex as he played Madden on his Xbox, sipping at a beer in between plays.

"So, I see someone went out to have a little fun this afternoon," his voice called out in a teasing manner. He had a feeling she was going to be heading out this afternoon to take care of some of her more physical needs and as always took it in stride though he couldn't help but tease her whenever she ended up a little sore afterwards. Fingers wandered to the pause button, the game was getting a little boring anyways, and he turned around on the couch to face her with a shit eating grin on his face. "I take it the afternoon's activities went over well then?"

Anna's face blushed bright red, she disliked the teasing but he was so good natured about their little arrangement and she was the benefactor of it so she did her best to take it all in stride and let him have his fun. Besides, it wasn't like she didn't get in a few good zingers every now and then, but for now her thighs were a little sore so once she nabbed a sour apple Smirnoff from the fridge Anna hobbled over to the couch and plopped down. "Well they were certainly enjoyable," a swig of the malt was taken to rinse out her mouth and she leaned over to press her lips to Alex's, "as always thanks for being so understanding."

He returned the kiss and gave her a little smile, "Sure thing, I just want you to be happy after all." Alex took another sip of his beer and settled back into his seat, resuming playing his game. "I have a pot roast in the oven for dinner going, if you would be so kind as to make the gravy later that would be great."

Anna laid in bed next to Alex's sleeping form, a touch bit restless that night as was usual for the nights after she'd gone and had her fun. For the most part she blamed it on a guilty conscience for her exploits even though she had full permission from Alex to stray and actually it had been his idea. Still though, she couldn't help but mull over what had brought her to this. A fairly straight laced girl was what she'd been through high school, losing her virginity to her Senior Prom date in the back of his SUV at the age of eighteen but kept her activities pretty well secret and few and far in between. College had changed all of that.

Alex had been a friend of hers for a few years, and to be blunt he had been friend zoned by her early on. Anna just hadn't realized his interest so much, or at least that is what she told herself till one drunken night their college freshman year. He finally got through her thick skull and for the last year they'd been an item. The relationship was, well since she'd told him enough of everything she'd ever wanted, just about perfect except for one thing. Alex was for a lack of better words, not as well endowed as she would have liked. He was smaller than average in every way, length and girth, though she found his uncut member quite attractive looking as it was well built just small.

At first he hid it from her as best as he could, sexually he never let her touch him though he went down on her regularly and had proven to be well skilled in his oral abilities. However that had frustrated her by not letting her return the pleasure and led to the inevitable, her discovering his smaller member. To say she was a little disappointed would be an understatement though she had expected him to be no more than average considering the size of his bulge when aroused.

That had led to one heck of a long talk between the two of them, and her deciding to just try to work with it, she valued the relationship too much. He bought her a kegal exercising dildo and she did her best to tighten up her muscles, which helped a little but not a lot. The breakthrough came when she was reading a story and found the characters having anal sex. The idea was tempting, without a doubt she was infinitely tighter back there. Anna kept her discovery a secret while gathering information and anything she thought would help ease her into the idea.

When the first night finally came Alex at first was surprisingly against the idea, but she soon talked or rather suckled him into the idea of taking her anal virginity. As she felt him going in, a grin split across her face, finally she could really feel every bit of his cock penetrate her and actually fill her. Anna had gambled that the anal starter dildo she'd found was about the same size and was pleased to note she had been very close, enough so that he comfortably fit within her ass.

That night she had him take her rear three times, just savoring the fact that she was actually enjoying getting fucked by her lover. When morning came her ass was quite sore, but she loved knowing that he had done it to her. By the weekend Anna had come to realize that what he lacked in size, Alex more than made up for with stamina. His ability to go five or more times in a day both delighted and yet disappointed her. She only wished that the vaginal sex was more fulfilling, while they regularly had it, she just never felt quite satisfied.

She wasn't quite willing to lose everything else that made their relationship special and so Anna dealt with the lack of satisfaction until late one night they were laying in bed, him spooned up behind her. She felt his fingers slide back the hair upon her ear soon followed by a whisper, "I know you're not fully pleased with this, you don't have to hide it."

She sighed and rolled over to face him, "It's fine, really. I can deal with this, and this relationship is worth it to me."

"No, it's not okay. It's cliché but I want you to be happy too so... I was thinking that I would be ok if occasionally you went off to have a little extra fun if you know what I mean." His top teeth came to grasp his lower lip and gently bite it, as if he was the one who was asking something nearly impossible.

She blinked then blinked again, jaw dropping open as the shock of him even suggesting that she would want something of that nature. At first she thought he might just be teasing her, no matter how mean that would be, but she could see that he was dead serious and so the need to slap him was restrained as she confronted the topic so suddenly thrust upon her. Anna had to admit to herself, the need to be stretched and filled was there but the idea was so wrong, so totally wrong in a very naughty way. Before her mind made its decision her body gave its own answer in the form of a totally drenched pussy. "Well...I guess I could give it a try."

That night had been six months ago and she had taken her time finding someone suitable. In a lot of ways she found finding the right guy, or in this case, several guys had been harder than finding love. Most guys seemed to want to believe they had the size of cock she craved, but only a few really did, and from there she had the weed out for personality. No, she would explain to each one that her beloved was not being cuckholded and that this was more just for her to have a little fun on the side with no further intentions. Finally she narrowed herself down to three men, and for the last four or so months had enjoyed random meetings with the trio. Still, it bothered her that she was allowed to go play and yet he remained faithful to her alone.

Hand came up to stifle a yawn, these council meetings tended to get rather boring but as the Treasurer of Theta Phi Anna got stuck attending every one of them. This was the second meeting of the year and so all of the pleasantry of greeting old friends not seen since the Spring Semester was now over and they were getting down to business. The first half of the meeting was to cover the normal side of the sorority, those things that the public got to bear witness to but later they would be discussing rushing incoming pledges. That alone was worth enough to chug down an energy drink and force herself to stay awake. Everyone always looked forwards to the pledge rushing, granted it was a lot of planning to do, but it was oh so much fun.

The fact that Theta Phi's rushes tended towards the sexual side wasn't a hidden secret and potential pledges were checked out in advance to not be so adverse to that idea. Last year's group was split in two and made to use double ended dildo's on each other then eat out an existing sorority sister's pussy until she came. That had been quite the night and when they were through about fifteen of the twenty girls who had started had now become sisters and in some cases, bed mates. A slow grin formed on Anna's face as she thought of that night and wondered what sort of trickery they would get up to this year.

Once the Homecoming Project was finalized, with some major discussion in regards to finances, Suzy never could quite get it through her head that funds were not unlimited and no they couldn't make the pledges prostitute themselves for the funds. Anna rubbed her temples, trying to wish away the migraine and debating the wisdom of more caffeine when Lauren announced those magic words, "So, how shall we torture those poor pledges this year?" Anna's lips twisted to a grin, finally they were at the part of the meeting she'd been waiting for.

It took Lauren a few minutes to calm down the rest of the girls as ideas had been immediately shouted at her. It was obvious many of her sorority sisters had been contemplating this at least since the last meeting, if not longer. She, of course, had a few of her own ideas and this being her last year on the Theta Phi council Lauren wished to leave her mark upon the sorority. Late last night an idea had struck her, one she'd not heard the like of before and had led to quite the satisfying masturbation session before sleep finally overtook her.

"Ladies please, those are all wonderful ideas. However, I have an idea that I would love for you to listen to. So if you would be so kind, bear with me for a little bit that would be appreciated. This year there seems to be a bit of swell of girls willing to do what it takes to enter our little group and so we should use a method a little harder to pass to really thin out the crowd. I want to know what girls are so desperate to join Theta Phi that they would take a dick up the ass for us." She paused with a grin as the chatter broke out.

Anna felt her jaw open wide and quickly shut it. Lauren's boyfriend, Bruce, was one of her playmates. Of course the play was open, Lauren had even joined them once, and she knew exactly why Anna and Bruce played together. Her eyes narrowed a bit, she wondered if Lauren specifically had included Alex in her plans, and while a hint of jealousy arose within her, she felt it squashed by the arousal and the thought that finally she could pay back Alex for allowing her the freedom to tend to her needs.

Lauren watched Anna's reactions, she'd fully intended to ask to "borrow" Alex for the plan. Best to have a guy they could more or less trust to handle this, plus they could assume that he would be clean, both in hygiene and disease. A slight shudder crossed her as she recalled her freshman year and the failed rush attempt when the guy that the pledges were to blow showed up reeking from lack of bathing. Fortunately one of the sister's boyfriends was available to take his place but Lauren didn't need a repeat of that incident. That and she knew Alex was at least practiced in anal sex, of course she'd have to verify that herself.

Once the chatter had settled down, it seemed that most of the girls were in agreement it was at least a decent idea and primarily agreed with doing something new. There were a few who were a little more reserved with the idea but once Lauren assured them that the guy would be checked for size and perhaps even skill they reluctantly signed on. With the rush decided, Lauren called an end to the meeting but pulled Anna aside under the presumption of discussing the costs for Homecoming. "I'll presume you figured out I would like Alex for this, from what I understand he would be about perfect. Though, of course, I want your permission before asking and well I would also like to umm...try him out first." She blushed a little, Lauren herself was an anal virgin and there was no way she'd ask Bruce, he just was a bit intimidating in size for that.

Anna nodded at first, she'd had the feeling that was why she was being pulled aside but couldn't help but feel a bit of shock at Lauren's sudden bit of embarrassment. She'd never seen Lauren this way in four years and couldn't help but be a bit surprised. It had been Lauren who had been the first of the pledges to wrap her mouth around the man's cock and Lauren who seemed to be always knowledgeable about any sexual topics. Heck Lauren had been the one that Anna went do with her frustrating problem of finding a fuck friend and helped her locate her current bed warmers. This was a new feeling and Anna enjoyed it for a moment before moving on, "Of course, but I'd like to be there and help you out." She smiled and softly hugged her friend, besides maybe she could get Lauren to eat her out for a bit, the girl had an amazing tongue.

Lauren let out a little squeal, she had expected Anna to agree since the girl seriously owed her but the offer to personally help was a nice touch. She would have to rethink her relationship with Anna in that regard, maybe there was more there than the occasional bed warmer. "So, how should we go about doing this? You're umm, a bit more of an expert..."

"Well, when I was working my way up to taking Alex I ran across a great little dildo meant for anal. It's not too expensive and wasn't much smaller than Alex is so maybe we should have each of the pledges wear it in them for an hour or so before the rush. Also, Alex is usually good for up to five or so times a night, more if we haven't fucked in a day so maybe we should break up the girls into groups and do the rushes over Labor Day weekend? There's enough money in the treasury to fund the dildos though I might need some company over a long weekend of not getting any.." she grinned at Lauren.

She couldn't help it, a little giggle slipped her lips, "Well, I suppose Bruce and I could work something out. After all, wouldn't want you to unnecessarily suffer." That and the memory of Anna's tongue on her clit while Bruce had filled her needy cunt was one that needed to be repeated at least once. "So, maybe this Thursday night after Thirsty Thursday rounds we could get onto my test of Alex and his talents?" The alcohol would be a welcome help to relaxing her, though part of her was already excited at the idea of finally popping her anal cherry.

Anna just nodded in agreement, already concocting how she was going to explain all of this to Alex. Well, that probably wouldn't be very hard, unlike his cock, she mused and giggled to herself. This was going to be one fun start to the year and with a little luck it would continue through the rest of the school year.

By Thursday night Anna had everything setup, the dildos were on order and she'd rather easily talked Alex into it. As expected, it wasn't so hard but actually broaching the idea had given her pause in just not knowing how he would take it. So, she did what any logical hormone crazed college girl would do, she asked him in the middle of giving him a blowjob and had to act fast to prevent getting choked when the idea caused him to orgasm nearly instantly. She'd neatened up the room and put various toys and lube out in easy reach, grinning to herself as she went about readying things.

Alex was, as usual, crashed out on the couch and sipping a beer while Anna was in the bedroom. Part of the reason was simple, she only had on a pair of lacy purple panties and he was already horny at the thought of what the nights activities were going to be. He'd been quite surprised at Anna's proposals, he'd had a sneaking feeling she was up to something, just a vibe he'd gotten off of her well that and normally she preferred to give him head after she'd gotten eaten out. It was rare she started off with oral, just a tendency of hers that he didn't mind. Either way his mind had been blown to find out someone wanted to bed him because of his under-endowment. He'd have been a fool to turn down the opportunity, especially since he'd been asked by his girlfriend, damn. Screw a bunch of eighteen and nineteen year old freshmen and have a threesome with one of her sorority sisters? He needed to figure out what he'd done way right and keep doing it.

When the knock on the door came, he rose up from the couch to open it and let in Lauren. His eyes followed her as she made her way into the room, admiring her curves. While Anna was more of an athletic build, with a smaller chest, small but pert rear, and her red hair cut into a bob Lauren was the more typical bombshell type, with a slightly bigger than average chest, blonde hair that reached to mid-back, and a set of hips that begged to be grabbed while being taken from behind.

Lauren had spent the last five minutes standing at the door, nerves stopping her from knocking despite the two rails she'd had at the bar. She didn't know what exactly it was that made her so nervous, she'd been less so when losing her virginity. Finally though knuckles met steel and she anxiously awaited the door to open. Considering the nights activities to come, Lauren hadn't dressed up too much with just a pair of jean shorts and a t-shirt and was relieved to see Alex had taken a similar approach. She had to admit, he was an attractive guy, not very muscular but toned and while he didn't look like it at first blush he seemed to care just enough about what he looked like to take care of himself. She could do a lot worse than to be in bed with him. When Anna came bounding out of the bedroom, just in that pair of purple panties Lauren giggled, "Gee, just in the door and already undressed." She wrapped her arms around Anna and gave her a soft kiss on the lips. "Shall we just head straight for the bed then?"

Anna wasn't sure what had come over her, perhaps just as simple as the anticipation brimming over, but she responded to the question by grabbing Lauren by the wrist and half dragging her to the bedroom. She spun about on the balls of her right foot, wrapped Lauren up and planted a deep kiss on her lips. Tongue pushed through to part her friends lips and greet her tongue. Gently she pushed Lauren into the bed and onto her back. Alongside of Lauren she lay, left hand caressing Lauren's torso while lips came back to press against lips, tongue reaching for her mouth and tasting the rail that had been consumed earlier.

Lauren savored the feeling of another woman kissing her, she'd learned over the last couple of years to appreciate the different ways that men and women kissed and right now Anna was a little more aggressive than the last time. So wrapped up in the kiss she was, that she didn't feel the bed shift as another weight was placed on it until she felt a second set of lips, this time on her neck. A soft groan was pushed into the kiss as she felt Alex press his tongue against a nerve junction, damn if he ate pussy as good as he worked her neck she was in for a long night.

Alex worked her throat gently but firmly, tongue seeking and pressing little spots where it would invoke the most pleasure. A hand slid up her torso, under her shirt, to seek a bra covered breast and gently squeeze it. Fingers sought out her nipple and gently he traced the tip of his finger around the nipple, feeling it grow hard against the material. When Anna began to pull Lauren's shirt up, he began to kiss his way down her torso, then paused the look over the sight before him. Granted he'd seen her in a bikini, but this was different and he wanted to enjoy every moment of it. Slowly he lowered his head towards that lovely bust and gently began to kiss the tender skin along the top of the bra.

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byJagFarlane© 3 comments/ 81633 views/ 20 favorites

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