Michael's Self Discovery (boyxboy)

Red

The Lady in Red

Warning there are suggestions of sexual acts and prostitution. 

School had let out for the holiday break, it was Christmas time. Michael and I were texting each other, back and forth, both of us excited for the break, and the relaxation that it would bring from the constant oppression of school. Christmas Eve passed, as did Christmas. We were nearing on the night of December 31st, or New Year's Eve; it was December 30th. Michael seemed a bit down in the dumps, and I was trying to lighten the mood (to no avail).

He was sad that he had lived his life, never knowing the touch of a woman, or a woman whom he would want to touch. I, jokingly suggested, well we'll just get you a whore, and you can just fuck her and get it over with.

Michael, lol'ed, and then suggest that the event should actually occur. I then figured he was joking, and tried to laugh it off, but he persisted in saying that he wanted a whore. As such, I did a Google search, as to how to find a whore. I got some answers, and before the night ended, and through an underground pipeline of information . . . I found a whore.

I messaged Michael, "All set. I'll be bringing her over at around 11 o'clock tomorrow night."

He replied, "K."

I didn't care if he did fuck her and I didn't care if he didn't fuck her. Either way, it wasn't a large dip from the bank.

I texted the girl at 9 o'clock, asking her where I'd pick her up. I got the answer, before texting Michael: "This is your last chance to back out, before I go and get her."

He replied, "I'm going through with it."

I replied, "Okay, we'll be there around 11."

"Bring condoms." He replied.

On the way to the place where the girl was, I stopped at the pharmacy, and grabbed a three-pack of condoms, in three different sizes. With the girl in the car, I drove to Michael's house, and escorted the lady of the night to the door, and then inside. I forewarned her that Michael might be emotional, and that he might not go through with it.

I knocked on the door, before just walking in. Michael was nowhere to be found. I directed the girl to a chair, whilst I looked for Michael.

I went directly to his bedroom, making sure to knock on the door before I entered. He was in his room, crying. He knew that my arrival meant the arrival of the girl, and subsequently the departure of his virginity.

"Last chance, Michael." I said calmly.

"Let's get it over with." He replied amongst his tears.

I walked back to the main room, and returned with the girl and condoms a few seconds later.

I then walked out to the living room, not knowing where else to go—and avoiding leaving, as I was responsible to take the girl Home. I sat on the couch, listening keenly for any sound I could gather.

Either Michael's room was soundproof or . . . "STOP!" I heard Michael yell.

I rose from the couch, preparing to take the girl Home. The bedroom door opened, and the girl walked out with an annoyed look on her face.

"Just one sec." I said, walking to Michael's room.

"I'll be taking her Home now . . . unless you're 100% sure that you want to continue."

"Just go."

"I'll be back, in about 15 minutes."

"K."

The girl and I got in the car, and were scarcely out of the driveway, before I asked her: "How far did he go?"

"Well . . . he managed to get it out of his pants, and get it hard. But I went to blow him, and that's when he yelled." She said quietly.