The next few weeks were uneventful, I was able to spend a considerable amount of time focusing on school. I had a number of assignments, most were one hour sessions with businessmen in their respective hotel rooms. I had one assignment where I was asked to whip a guy with a riding crop, he wanted me to leave red marks on his ass. This really turned him on, because when he took me, I could almost not walk afterwards. My ass was getting used to being assaulted, but some cocks felt better than others.
The only unique assignment that I had during this time was a married couple. Yes a married couple, this would be my absolute first time with a woman, well almost. It was an anniversary present for each I was told. The couple I found out were both openly Bi-sexual, and the woman was a very dominant individual who got off watching her husband submit to her and others. She wore a black leather dress, almost like a dominatrix. She instructed me to lie on my back and she lowered her pussy to my face, while at the same time ordering her husband to suck my cock.
This continued until I was about to cum, when she stood up and ordered me to stand as well. Her husband was on his knees as she gave my cock a few last strokes then shot my cum (like it was her cock) into her husband's waiting mouth. She yelled until he swallowed, calling him all sorts of demeaning names. She then ordered her husband onto his hands and knees and had me mount him. She put on a strap-on and invaded my ass at the same time. The three of us fucked for a while, until I came inside her husband. I was then removed from him, as she continued to fuck me now even harder. Her husband moved around to my face, and I took him into my mouth and sucked him off until he came into my mouth. She was a bit crazed and had long fake fingernails, which she used to leave a few marks on my back.
That was a different experience to say the least, she was a total top. Not once did anything enter her, not her husband, a toy or even me. The husband for the most part, I think would have been happier in an all male relationship with a dominate top. He came across as a total pussy, and no pun intended but she seemed to be a total dick.
It was just before Valentines Day and Kevin called me with an assignment that would pay $ 5,000 for the night. It was a Valentines party given by a gay couple for their friends and they wanted to do something extra special this year. It seems that a dear friend of theirs had just passed away leaving them a nice sum of money. I could tell that Kevin was a little unsure about them, as he told me that he had made sure that everyone at the party would practice safe sex. That was something that was never discussed nor practiced during any other of my assignments. The mere mention of this made me a little uncomfortable, but I was intrigued about the party, plus the money was really motivating me by now. It had been just over a month and a half, and I had already managed to save over $ 20,000. I was told to be open to some new idea's, and Kevin asked me a few times during the conversation if I was willing. For some reason this turned me on and I said yes. I found myself totally into guys now, and the one experience I had with a woman did nothing more than to strengthen that decision.
I was not sure what to wear to a gay Valentines party, so I went on the internet at the college library. I only had a few moments of privacy, and much to my displeasure, nothing jumped out at me as gay while looking at costumes online. I did not understand why, but I wanted to wear a special costume, it was almost like I was the guest of honor instead of an employee at the party. It finally dawned on me to be cupid, so I purchased a white sheet and manipulated it into a large diaper.
I found it hard to focus on school that day before the party, thankfully nothing important was taking place. The day of the party, which was scheduled to start anytime after 5pm and last until well no one knew for sure, I went to a pharmacy a good distance from my rented room and purchased a large 36 pack of condoms. I made sure to purchase the most expensive box, they came in different colors and according to the box were well lubricated. I did not eat to much that day, and showered just before I left. I packed my costume in a bag and went to the site of the party dressed in jeans and a t shirt.
