Sorority Initiation Spy

My sister Debbie could talk her way out of just about any predicament.

Cute, precocious, innocent, Debbie had an arsenal of effective weapons. She could smile, bat an eyelash, tuck her skirt a bit higher and flirt with the best of them. She could kill with kindness when she had to, and when all else failed, turn on the syrupy sweet charm that could melt men’s hearts and turn them into putty.

Being a couple years younger than she, I watched her learn her craft through her high school years, then excel at in her collegiate days.

She had my parents wrapped around her fingertips, her teachers too. By the look of her grades at the University, she apparently had her way with the professors, and the fact that she was named Homecoming Queen and student government in her sophomore year let me know that none of her charisma had worn off as she had gotten older.

I had the good fortune of trailing my big sister at the University, and have to admit she steered me to the right teachers and classes. Everyone knew pretty Debbie, and being her little brother helped in non-scholastic ways too --- it got me laid.

But I am ahead of myself.

As popular as Debbie was, I was just the opposite. I was shy throughout my high school years, never even getting the nerve to ask a girl for a date until late in my senior year. That near disaster, prissy Mary Ann Constantino was a match made by our mothers for the senior prom, was made good only when after an unbelievable several hours of misery and pain in the decked out gymnasium we gave up on all pretenses of a romantic evening and changed into our knock around clothes and stealth down to the lake.

There, while other couples were making out, we sat and skipped rocks and spoke of sports, school and the weather all the while suffering through long periods of quiet.

When I dropped her off at home before our extended curfew of 2 a.m., I felt I had wasted an evening. The conversation was merely nice, like talking with your sister about the weather. We never made it into the backseat for any groping, nor did we embrace in the front seat. Heck, at the end of the night I barely got a good night peck on the cheek. What hurt worse was that several of my friends disclosed to me that Mary Ann had been bad-mouthing me to several of her girlfriends, going so far as to say I couldn’t even get it up for her that fateful night. The gall of the girl, she had a force field around her that night which kept my hands away from her. I didn’t even have a light case of blue balls.

Like I said, it was a disaster. Why she had to make it worse by trashing me I didn’t know, but there wasn’t much I could do about it after the fact. Needless to say, Mary Ann didn’t get a call for a date from me again and I insisted my mother stay out of my dating life.

My sister consoled me, telling me that Mary Ann was merely a mistake, a pothole in the garden of love. Her words soothed me, but it wasn’t easy getting over the bards of my friends who rode me mercilessly on my disastrous prom affair. I could swear some girls looked at me as if I was a geek or pervert or something.

Life went on. I changed the style of my hair, bought some new clothes, and even learned a few jokes, complete with punch lines. Nothing seemed to work.

Everyone said there were other fish in the sea, so I plowed on in the love department. The closest I came to sampling a woman’s favors came that summer when I dated a girl with a “reputation”. Lisa Marie was known around the guys in my class as an E-Z lay. Several guys openly spoke of bedding her, while others intimated they had. Somehow I got the courage to ask her out, and we had several nice movie dates. On the third date I got the nerve to kiss her, and it was fantastic. Her lips were soft, and I held her tight mashing my face against hers. But somewhere between kissing her perfect lips and attempting to go a little further, my hands and plans were derailed.

“I’m not that kind of girl,” said the girl known around the schoolyard as a slut. “Stop!”

My hand had barely copped a quick feel of a sweater-covered breast when her words stopped me in my tracks. No meant no, and I pulled back to my side of the front car seat. I begged and pleaded but no fire was kindled. Shot down by the loosest girl in my class.

If you had taken a poll the following Monday, most would have assumed I had scored that night, and I said nothing to dispel the thought, but of course I knew the truth.

Debbie knew it wasn’t the case. My sister sympathized with my plight, giving me encouragement, telling me it wasn’t about sex but love. The right girl would come along and the sexual escapades would follow. Easy for her to say, she was Ms. Popular and had the pick of the litter of college guys while I couldn’t even find leftover girls who couldn’t beg for a date.

Still, she would support me when I was down, lifting my spirits.

At State I, at Debbie’s insistence, joined several clubs, as she felt my interacting with girls would lead to something. But if anything, it sent me the other direction as none of the girls who interested me were at all interested in me. Truth be told, I was still a bit geeky, lacked confidence, and just didn’t carry a conversation.

I poured myself into classes, and did carry good grades that first semester. I’d go to a few mixers, a couple frat parties, and I actually did get a little bit better with my interactions with the fairer set. Still, no girly action, just a self-sympathetic reaction.

Sitting in the cavernous student union, I’d people watch, and invariably would notice guys and girls sitting together, joking, studying and so forth. Some would hold hands, some kiss, and I’d gaze on with envy when a guy or girl would pat her partner on the butt or swing into a hug on their way out of the building. One day…

Student mixers weren’t much better, I’d asked a few girls to dance and actually spazed my way round the dance floor with some, but nothing came of it.

Debbie laughed at my predicament. “Ah, come on Jon, it’s not the end of the world.”

“Sis, couldn’t you fix me up with someone?” I begged.

“We’ll see, we’ll see,” she’d reply, shaking her pretty head, but nothing seemed to come of it.

My sexual activities included reading passed on Hustlers and Penthouse magazine, with an occasional Friday night blue movie at the x-rated theater in Danville, a town about 15 miles away. A couple times I spied young lovers making out down at Lover’s Point, an out of the way spot where kids parked. Several times, from a secluded spot just yards away, I spied a young woman giving head to her beau, and once actually saw a couple having sex in the back seat of a Toyota Camry.

Then came the call.

“Hey, sluggo, you heading home for the weekend?”

It was Debbie. Her voice was more syrupy than usual, leading me to believe she was up to something. As she continued, I quickly realized she was.

“If you are around town I’d like you to help out in some of the sorority initiation activities. Are you game?”

I asked if it involved me dressing up in a stupid costume, or being made fun of, or other embarrassing task.

“Nope,” she said with a laugh. “I guarantee you’ll love it. Who knows, it could be a lot of fun and a little exciting too!”

“What do you mean?” I quizzed?

“Friday night, 10 p.m., meet me at the back door of the Ti house.”

Why not? Heck, I had nothing better to do. It would give me some time to study and who knows, it just might be fun.

Over the rest of the week I wondered what evil Debbie had thought up for her potential new “sisters”. Probably putting them in some embarrassing position, one which she couldn’t trust just any guy with participating. She knew I’d keep my mouth quiet to the death.

Just before 10 on Friday night I approached the back of the Ti House, and seconds later Debbie appeared. “You’re on time! Way to go, Bro.”

I smiled at Debbie’s attempt at poetry. She looked a bit different, wearing pants, a white men’s shirt, and a baseball cap. Heck, she looked more like a guy than a girl.

“Part of the costume, you like?” she asked, twirling in the shadows of the building.

“Uh, it’s not you,” I replied, “but whatever lights your match.”

Debbie waved me into the old Victorian house. We scooted down a hallway, hearing some sort of mood music in the living room, and went down to the barely lit basement. There she un-hatched her diabolical plan. “It’s pretty simple, the potential sisters have all been grilled and quizzed on why they want to join our sorority, and they’ve had every bit of their lives scrutinized by the counsel. It’s amazing how open they can be when under the gun.

“Your job is to join me down here and do what the girls ask. Each has been given an assignment, like going up to a guy and ask for his underwear, or to yell out stupid statements at town square, or to perform some juvenile prank at the mall. The other sisters will be working with those girls, ensuring they are up to the task, while you and I will be the leaders here for three of the problematic girls. These two are prissy, girls with an attitude, who I’m not sure deserve to be in our sorority. Each is sitting in a different room upstairs, and each will be given an envelope of an assignment they are to complete as their last facet of the initiation.”

I looked at my sister, thinking this could be fun. “So what can I do?”

“Listen carefully and do exactly as I say! Your job is to stay behind the boxes in the back of the room over there. Each of the girls will come down to the basement. I will lead them down here, I will be wearing a Mardi Gras mask. The girls are to follow the script we’ve written for them. Once in the basement they will put on a blindfold, so they will not be able to identify you. But to be on the safe side here’s a mask for you…it’s a former president you might remember. The one who was caught with his fingers in the intern. You just do as they ask, nothing more. If they say jump, you jump. If they want a drink, get them one. Get the picture?”

Confused as to what kind of initiation this would be, I began to ask Debbie what in the world she was talking about. She shushed me and just told me to simply do as the girls said and all would be well.

She twirled and made her way back up the stairs as I move to the back of the room behind the boxes. I moved things around so that I could stay in the shadows yet still see the women come down the stairs. Then, looking to the left, I could spy the desk and chair in the center of the room. A bright ceiling light lit that area of the basement, but all of the surrounding areas were in the shadows.

The wait seemed like an eternity. I could here music upstairs, a little bit of side clatter, but there was no activity in the basement for a half hour. I amused myself by reading through some old Cosmos and Brides magazines, spending more time with the former than the latter.

Finally, I heard the creaky basement door open, and I made sure I was secure in my hiding spot. I couldn’t see anything for the longest of time. My curiosity was driving me nuts, but finally, through a small opening in the stacked boxes, I saw a young girl, holding a lit candle and wearing a long toga style robe slowly walking toward the small area where a green stuffed arm chair and a wooden desk stood. There was a pillow on the desk, and nothing else. The area was lighted by one powerful bulb, and the girl came to a stop in front of the desk.

She turned and faced Debbie, an unsure look upon her face.

“Oh sister, oh sister, I have come into this den to reflect on my actions of the week,” the girl said in a practiced voice. “Thank you for your concern about my behavior. This pledge week has been a learning experience for me.”

The girl was about five feet, five inches tall, but the robe did not reveal much about her body. She had long brown hair, with rosy cheeks. Irish, most likely, and I bet she had a wonderful smile. But not this day, as her face was a bit flushed.

“Well, Erin, you have been a little bit, well, unhelpful this week.” My sister was speaking to the girl as if she were a child who had been a bit contrary. “You know the rules. I will say no more. This is your final test for membership in our association. I hope you perform your role well.”

The words, which were missing from the speech, were “or else” as it was clear young Erin would have to perform the predetermined duties well or she would not be admitted to the sorority.

I spied as the girl blew out the candle, placed it on the floor, then reached over to the desk and put on a mask. She then tightly secured a blindfold she pulled from somewhere within her robe and placed it tightly around her head, blinding her eyes. She felt around, ultimately sitting down into the armchair. With her eyes blinded, I stood and looked at my sister, who put a single finger in front of her lips to silence me.

Debbie walked to the corner and turned on a CD. It was some sort of medieval melody, the kind you heard as background music on the History Channel when Knights were sitting around a table or young damsels were stroking their long blond hair. It was then I noticed the long wooden paddle Debbie was holding in her hand. It was a sorority paddle that the pledges were required to carry around campus.

The quiet of the basement was ended when Erin cleared her throat, took a deep breath, and began to speak.

“Oh ladies of the house, a group I hope to call sisters, I have been afoul of many of your rules and regulations. I have spoken out of turn, and I have failed several of your assignments. But I am here to ask your forgiveness. I am here to throw myself upon the mercy of your good hearts. I want to join this wonderful group, to be one of you.”

She paused, words forming in her brain but not coming out of her mouth. I wondered where this was going, but it was fascinating being a voyeur of this ceremony.

“I have been bad,” she quietly said in a voice just above a whisper. “I must be punished. I beg of you, please punish me and let me prove I am worthy of membership.”

Speech over, she uncomfortably stood. She reached out and felt the desk, moving toward it. She bent over the desk, placing her midsection on the pillow, then reached back and lifted the toga up her legs, thighs, and bunched it around her midsection. She stood with only beige thong panties covering her behind.

“I have been bad,” she repeated. “I must be punished. Please spank me. Please make me pay for my indiscretions. I deserve 50 swats. Please, sister, start the process which will heal me of my improper attitude and behavior.”

My eyes bulged, as did another portion of my anatomy, as I observed the Kodak moment in front of me. The girl’s ass was bared to Debbie, and as I silently moved around the boxes, to me as well.

Debbie waved me closer and I watched as she slowly rubbed the paddle against Erin’s perky white ass. This girl obviously worked out, as her thighs were well formed and not an ounce of fat was on her 18-year-old ass. The angle she was over the desk accentuated her butt, and it was a pleasure to observe.

“Please, sister, please spank me.”

“If you insist,” said a firm Debbie. “Don’t forget to count, because I might forget.”

“Yes sister!”

Debbie moved to the side of the girl and moved the firm wooden paddle horizontally away from objective. She then pulled it toward the ass, striking it firmly in the middle of the virgin white ass.

The resultant swat was followed by a cry from the lips of young Erin. “Ouch!”

“What did you say, pledge?”

A meek voice replied, “That’s one, thank you sister.”

“That’s better, I don’t think you want me to remind you again!”

“Yes, sister.”

Debbie gazed intently at the girl, pausing for effect. Erin sort of trembled, just one step along the way of 50 that undoubtedly would be humbling and hurtful. I could swear her ass wiggled a bit before the second, third, fourth and fifth swats from the paddle struck her behind.

Erin began crying after the eighth swat, and her counting became more like begging. I could tell her butt was stinging as her hold on the sides of the table got more pronounced and her ass began reddening. The early swats started blood rushing toward her ass cheeks and soon they were a bright shade of crimson.

“That’s 10,” said Erin with what I assumed were tear stained eyes. The blindfold kept any moisture from cascading down her face, but the sniffles and yelps of pain were there.

After 20 swats Debbie turned to me and mouthed that it was my turn! I couldn’t believe it. I was going to get a chance to spank the helpless soon-to-be sorority sister with the cute but red ass.

As I stepped closer to the girl, paddle in hand, I spied her defenseless ass and got a peek at her pussy. She was a natural brown haired beauty down there, and my already hard cock got harder as I observed her wiggling ass.

“Oh please, sister, 20 strokes of the paddle are not enough for my insolence. Please spank me some more.”

I willingly obliged, sending one, two, three and four slow, easy strokes against her ass. After each Erin counted, and hearing her passionate cries of pain was music to my ears. I am not a sadist. Heck, I had never struck a woman before. But the intense naughty behavior of spanking a co-ed was so very hot.

After 40 strokes I stopped, looking over at my sister. She was sitting on a box, watching intently. I began stroking Erin’s ass, and she sort of shook at my touch. Her ass was hot, red hot, and I knew she must be in a little pain.

“Sister, please continue,” she uttered. Underneath that statement I could clearly hear the word “bitch!”

Insolent girl, I thought, and swatted her ass hard. It was the first hard spank I had given her. “I’m sorry,” she cried.

I struck her ass again before she could count the first, so she would be receiving more than 50.

Swat!

“Thank you, that’s 40.”

Spank!

“Thank you, that’s 41.”

Debbie took over at 45 and I went back to my hiding place. When the spanking was complete Erin lay over the desk for several minutes, regaining her composure. She rubbed her pained ass, and soon stood up, head bowed, and turned around. Her toga fell toward the ground, and she reached down to pull up her panties giving me my final glimpse of tender, prime, teenage pussy.

It took everything I had not to jerk off. Smartly, though, I kept quiet as the two girls marched back upstairs.

I was speechless at the spectacle, which was hotter than any of the porno flicks I’d seen from the Resident Assistant’s special cabinet. My mind wandered back toward the spanking, and how I had managed to control myself while still inflicting the required punishment. Then I heard the upstairs door open once more.

Again, a girl walked into sight wearing a white toga and carrying a candle. Debbie was right behind, and I couldn’t help but wonder if I would be spanking another young lass. This girl was a bit heavier, had short red hair, but there was no doubt about it. I realized that it was none other than the prissy Mary Ann Constantino, my high school prom date. She appeared nervous as she stood in front of the desk and chair, but of course she knew what was to happen next. I sat back and spied the two as they went through their ritual.

Then I spotted another person, a guy. I knew him, his name was Richard, and he was one of the guys who dated my sister. I had no idea what he was doing in the room. Still, the pre-set plan was in place and I observed while the main participants in this sensual play interacted.

The room was still as the girl handed Debbie the candle, and my sister blew it and sat it on the desk. “Mary Ann, are you ready to perform?”

The once holier than thou red-haired girl nodded her head.

“I am, sister, I am ready to open myself up to you. You are a wise junior, while I am a mere unworthy freshman. I know what you caught me doing with Richard, and it was wrong. I know that we were to keep our hands away from pleasuring ourselves during the Rush, and I surely knew the rules about messing around with a sister’s boyfriend. I couldn’t help myself. I thought you two had broken up. I know different now, and I know I must be punished.”