"What is it that you need, pledge?" I asked the young man standing in front of my desk.
Jeff was a new pledge to the frat and was fitting in nicely. His bringing in ceremony was in almost 2 weeks and he seemed to be handling the pressure very well so far.
"I am having trouble with something, sir." He stood straight, his hands behind him, and stared at the wall behind me. He had been taught well.
I was sitting at my desk, Carl sitting at his. We loved our office in the attic of the frat house, it was perfect! It made us feel so important, and would later on mold us into the positions we had in the business world.
"What is the problem, pledge?" I waited for him to say something, but he hesitated to talk. This annoyed me, even though I had nothing to do, I was wanting to get out of the house and head into the game room on campus.
"It has to do with a woman....sir." His eyes wandered for a moment and I knew this was a serious problem for him. I sat up straight in my chair and rested my elbows on my desk.
Since Jeff had began the pledge process to get into our frat, rumors had been circulating through the other members and pledges that Jeff was either gay or still a virgin. For a few weeks I had seen him walking around campus with a freshman girl in his class named Claire Thessby or something like that. "Is it about Claire?" I asked.
"Yes sir," he replied. He paused and then continued, "She is wanting to be my date for the ceremony of my official membership to the fraternity."
"That is fine," I said, "we would love to have her be our guest for the evening."
"Thank you sir," he said, but then coughed. "I've heard stories though....sir."
I knew what he was getting at and considering his uptight position, I gave him a break. "Sit down, Jeff," I motioned to the chair in front of my desk and he nodded and sat down.
"Thank you sir," his voice was quieter now. "Sorry if I am speaking of something that is supposed to be a secret, but," he looked towards the door to the stairs to the second floor of the house and then looked back at me. "I've....I've heard that if you bring a guest that you have to...well, share her with the head members of the house."
I chuckled. Last year, a few pledges girlfriends and guests got a little tipsy after the ceremony and ended up taking part in a glorious mΓ©nage a trios, which I was happy in taking part in. I figured at the time that Jeff talked to me about the situation, I felt that if he really liked Claire, he wouldn't bring her to the ceremony and risk something happening. I explained to him the ceremony from the year before and he nodded, understanding what I was trying to say.
"So," I finished up, "if she wants to come and you are willing to understand that she's an adult and if she wants to break loose and have fun, you need to let her and not get upset with your "brothers" if she does anything with them." I waited for what I said to sink in and then asked if he understood.
He nodded his head and looked at me square in the face. "Then I'll really need your help, James."
Jeff then confided in me that he was wanting his first time to be with her, that he felt important with her...and oh la da la da la da. I ended up not listening to most of explanations about his feelings towards her. I shook my head to let him know that I understood and that he could stop explaining it.
I told him that he could use the guest quarters with her if he liked, but to understand that the door is stay unlocked for in case of emergencies.
He thanked me over and over and I gave him a few self help books about sexual positions and proper ways to lead up to the special event. He was thankful again and left the office. After door closed and I could hear his footsteps descending the stairs, I looked at Carl who had a giant smile across his face.
I nodded, already knowing what he had in mind for the pledge.
* * * * * * * * * * * * * * * *
The next week, Jeff came to me again and asked a few more questions. This time, he was worried about oral sex. I laughed a bit and said, "Hey, if she's wanting to suck your cock, let her. Right?" but he shook his head no.
"I mean how to give her oral sex, sir." He sat there and waited for me to give him answers.
"Alright, Jeff," I leaned back in my chair. "You wanting to test out some techniques you think will work, or are you asking for some ways to help her cum?"
He waited a moment, thinking over what he really did want to know. "I would like to hear about any techniques you use," he looked over to Carl who was filling out some tax reports for the house.
Carl looked up, realizing that Jeff was looking at him. "And same with you as well, Carl. I would like to hear what you guys do because I hear so much from many girls on campus about you two. You guys are notorious for being good in the sack and well..." he sighed. "Like I said, I really, really like Claire. I want to make her feel good---"
"Alright," I interrupted him. I was getting sick of his babbling about his feelings towards the girl, I figured I'd give him a short cut through talking about it. "I'll give someone a call, she can help." I picked up the phone and started dialing a "maids" service. I asked for Charlotte and when she got on the phone, I cleared my throat and talked low so Jeff couldn't hear me. When Charlotte and I agreed on a time, I said good-bye and hung up the phone.
"You are in luck, Jeff," I said. "A good friend of mine will be over to help you out."
Jeff smiled, but it soon faded away. "I am not going to have sex with this woman, am I?"
"Nah," I said. "Unless you want to....but no, she'll be here to help you out with some ways to give Claire the best oral she's ever had." I smiled at the poor guy and he nodded and said thank you. "Now just be here at nine tonight, that's when she's available. So come back up here at nine sharp, tonight. See you then, pledge you are excused."
Jeff left the office and I told Carl what was going to happen with Charlotte. He offered to watch and help "critique." I laughed along with him and we started to get the attic ready for the "study session" for Jeff that night.
***************
Sure enough, at nine sharp, Jeff knocked on the door to the office and Carl let him in. "Have a seat, pledge." Jeff came in and to his surprise, the office was completely different. A massage table was set up where my desk usually was and all the chairs were out of the room, kept away in the basement until we would be finished. Jeff looked around for a chair then realized Carl had meant on the table. Jeff scooted onto the table and looked around. That was when he first noticed Charlotte.
She stood by the doorway in a maids outfit, a pink dress that clung to her skin and was way above her knees. A cute apron helped to accentuate her hips and her breasts nearly fell out of the top of her dress, just a few buttons helped to keep her contained.
Jeff mumbled something and began to get off the table, but Charlotte walked up to him and pushed him back on. He sat there, dumbfounded.