Breaking in the Pledges

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 save 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.

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