My First Time

Everything in me was saying no. I wasn't ready. He was my boss. I was slightly tipsy. But that part of me didn't have the perfect cock in its mouth. "Mmhmm" I managed to get out without missing a beat. I finally backed off. He opened the door and motioned for me to enter. As I did he slapped me playfully on my ass.

"I wish I knew about you sooner Brian. We could have been having a lot of fun." It stopped me dead in my tracks. "What's wrong?" He asked. I turned to him.

"Could....could you please call me Brianna?" He smiled. He had a great smile. I realized when he did that he was the first man I was legitimately attracted to. I just let it all out. The alter ego, the online chatting, the old man in the parking lot, my ruined plans for the week, all of it. He listened and then put his hands on my arms,

"Do you want to go become Brianna right now?" My insides were fluttering. I nodded. "Go ahead then, I'll be here when your done."

I went into the bathroom and did my makeup to the best of my ability. I wasn't that skilled at it, but did a good enough job. I secured my wig, took a deep breath and went back out. He was reclined on the bed, a fresh scotch, and had ordered some gay porn on the TV. "Wow!" He exclaimed as he stood up, "Brianna....your very sexy." I could feel myself blushing. I don't know if he meant it or was just being nice but I didn't care.

"Thank you John."

"Why don't we go back to you calling me Sir when we're in this setting ok?" I nodded.

"Yes sir."

"Now...why don't you loose that thong." This is where my nerves really kicked in. I hadn't been naked in front of another man ever. And my cock was about half the size of his. But I wanted it. I slowly peeled them down until they were at my ankles.

"Sorry it's not-" I was going to say bigger but he kissed me again. He started kissing my neck and ear and sent shivers down my spine. Then, the unexpected happened. He slowly kissed down my body and got on his knees. He helped me step out of my thong

"I'm keeping these" he said as he tossed them to the side. Then, he took my cock in his mouth. I had never even thought about getting a blowjob from a man before. I always wanted to be the one giving. But man, he knew what he was doing. He had his hands on my sides and just started sucking. It felt so good. Eventually one of his hands made its way to my ass. I instinctively spread my legs for him. I heard him chuckle under his breath. His finger made its way inside of me. I moaned. He started thrusting it up further. I had done it myself before but it definitely didn't feel as good as him. He must have sensed I was close because he stopped. When he came up he kissed me again. I could taste myself on him. He spun me around and started kissing my neck again, his cock now nestled in my crack. My body told me it was time.

I moved away from him and got on the bed on all fours. He came over and and started lightly rubbing my ass. It felt so good. He walked around to the night stand and got some lube and a condom. "Your not the only one that had plans for this week" he remarked. I heard him rip the wrapper and my anticipation grew. The lube was cold when it hit me. "Are you sure your ready?" He asked.

"Yes sir. Please. So ready." I replied. I may or may not have been, but I know I needed it. He started with a couple fingers again. It felt good but I wanted his cock. I was in such a mental state at that moment that fingers weren't gonna do it. "Please" I moaned.

"I like it when you beg Brianna" he said.

"Please sir...please" I begged.

"Please what?" He was gonna make me say it.

"Please sir....give me your cock." Those words. Wow. They felt so good to say out loud. He put just the tip in first. I was obviously very tight. Again, I had done stuff to myself, but it's different. You know when it's coming. You know now hard your going to do it. This was different. I was scared but excited.

"More?" He asked.

"Yes sir. More please." I begged. It took a few minutes but he inched all the way in. He stopped once he was and just sat there.

"Doing OK?"

"Mmmm. Yes. It hurts, but in a good way." I answered. He grabbed my hips and began to thrust. He started slow at first, letting me adjust. But he eventually picked up the pace. Once he started going faster, it was over for me. I had my first sissygasm. I came all over the comforter. I didn't ask him to stop though. Mentally, I felt like I wanted to(later finding out its what referred to as post nut clarity), but I didn't think it was right and didn't want to ruin his night. He came not long after I did.

It was awkward at first. We were both laying there naked. He was my first. But I was also experiencing guilt, regret, whatever you wanna call it. It was clear he knew. He suggested I take a shower so I did. I took off my wig and makeup and hopped in. I was sore. I felt like crying but didn't know why. My first thought was that I wasn't Bi. But then I realized I liked it. I liked how it made me feel. I liked how he made me feel. I replayed it in my head. Over and over. I turned off the water and looked at myself in the mirror. I took a deep breath and then smiled. It hurt, but I was happy. I did want it. I did enjoy it, in fact, I wanted it again! I came out at sat on the end of the bed. John propped himself up and we just talked. He told me about his first time and how nervous he was. It was very comforting that he knew what I was going through.

At his suggestion I spent the rest of the week(when we weren't at work functions) as Brianna, just like I wanted. I may have gone in a virgin, but felt like an old pro when we checked out. We were like high school kids! Monday we both did our best to act normal, but we knew we wanted each other. We fucked for almost 4 years. I wouldn't say we were in a relationship, only a couple people ever knew, but it felt good to have someone. I was sad when he got promoted. I was happy for him, but sad that he would be transferring to a different state. We still talk and flirt, although we're both married now(him to a man, me to a woman). But he was my first and ill never forget those few days.