Losing My Virginity to Brandon Ch. 01

Chapter 1: The Videotape

I was up late trying to finish up this romantic comedy script that I had been working on for the past year, and finally, I got a great intimate scene set up for the two characters. Once I worked on the intimate scene, I had my roommate, Brandon critique the scene, but he thought it was too slow.

"They need to have sex." He said to me bluntly.

At first I was shocked to hear him say that, but then I realized after a couple of reads and editing, he might have been correct. See the problem is, I'm still a virgin and I really don't know too much about sex. The way they taught us in sex education class.

I was a little afraid to ask anyone how to have sex because that would seem odd for me to do that (and for anyone at that matter). I was going to ask, Brandon because he is very experienced, (knowing that he slept with two women in one night) but I just didn't have the nerve to do it.

Then one day when I was working on another scene, The fight scene where the two character's argue for the second time, he looked at the script and asked, "So where's the sex scene?"

Once again a little shocked for him being some direct but I tell him, "Well I decided not to put one in the story."

He looked at me with confusion written all over his face, and then he asked, "Why wont you put one in the story?"

"Well, I feel that it's better to make intimacy more important then just sexual activity. You know, sex is not always that important." I said.

I felt that was a great answer but he looked at me like that was a bunch of bullshit that just came out of my mouth.

It was quiet for a second, then he responded, "Have you fucked a girl before?"

I looked at him once again amazed that he would ask me that.

"Excuse me? That is none of your business, and what does that have to do with this?" I said with attitude.

"Shawn its alright... if your virgin then its not a big deal." He said.

I sat there contemplating whether or not I should tell him my big secret or not.

"Alright, I've never had sex before." I said sounding depressed.

He stood there quietly trying to figure out what to say or do, and then he replied, "Do you ever want to lose it?"

Again with the direct questions.... "Yes, I do." I said to radiate the irritation off my voice to let him know that I didn't want him to ask me any more questions.

I could feel his eyes staring straight at me while I was trying to work on the fight scene. It was like he was in shock, or maybe he was trying to think of what to say. Or maybe he's laughing at me in his head.

Whatever he's doing he needs to stop before I go off on him.

Then from the silence that was in the room, he disturbed it by asking, "Would you like me to take it?" I stopped typing and sat there in stunned from what he just suggested.

Then I pretended like I didn't know what he meant, "What do mean?" I asked.

"Were still on the same subject aren't we?" he said.

"Brandon, why would you ask me that? I don't go that way..." I said trailing off as watched him taking his shoes off.

"What are you doing?" I said.

"I've noticed your stares at me Shawn... don't even try to play me like that." He said completely ignoring my question.

"What? You don't know what you're talking..." My voice trailed off again as he took off his shirt and exposed his beautiful, lean, muscled body to me.

I sat there speechless that I was witnessing this in front of me. There had been times where I thought of being with another man, but I never thought of actually doing it for real.

Plus, I always thought that I was straight like the next man, and that those were just dirty thoughts clouding my mind.

"Brandon... you really... don't have to....... do this." I stuttered while watching him take off his pants showing me his jockstrap.

He was almost naked, all he had on was his white socks and his jockstrap. He didn't say a word back to me but he just stared at me.

"I'm gonna leave this last part for you to do." He said after shaking off his socks.

"What?!" I said getting up from my seat. He moved over to where I was standing and he blocked me from moving anywhere.

"Brandon have you been drinking? Cuz you are acting crazy. This is crazy!" I said.

"No I haven't been drinking, I'm just trying to do you a favor man."

"A favor????" I said growing angry.

"Yeah, do want to be a virgin for the rest of your life." He asked.

"Well.... No." I said thinking about it. "But I don't wanna do it now!" I said.

"Man you are 26 years old and never had pussy before, all you do is study cant you just relax and have a little fun? I assume you never gotten head from anyone either, probably never even jacked off?" He said.

I was astounded that he was digging himself in an even deeper hole.

"I thought so... here all you gotta do is rub my crotch." He said moving closer to me.

"No! Look Brandon this..." He grabbed my hand and put it up against his jockstrap, making me feel up his warm crotch.

He starred at me with a sexy smirk on his face and he whispered to me, "How does that feel?" I couldn't say anything and all I could do was stare at my hand rubbing his incased dick, bunched inside of the tight jockstrap.

He opened his jockstrap a little and put my hand in opening, making me feel the heat radiating from his dick inside.

"Brandon I don't know about this..."

"Shhh just do what I say and it will be over before you know it." He whispered to me. His dick jumped in my hand and started to expand from my squeezing.

"Take it out for me." He whispered in my ear.

I pulled down his jockstrap and his dick flopped out. It was definitely a nice size, he probably pleased almost every girl (and maybe some guys) on the campus with this and here I am holding his prized possession in my hand.

"Go down and lick the head for me." He said.

I knelt down on my knees, and jerked his dick off in my hand to get it completely hard. I looked at his massive black stick in my hand, and started getting a little scared.

He sensed it, "Don't be afraid Shawn, all you gotta do is lick the head." He said trying to relax me.

I stared at his dick again noticing the clear fluid seeping for the head. I licked it up before it dropped to the ground.

"Yeah that's it... Do it some more." He said.

I squeezed his dick like I was squeezing a tube of toothpaste, watching his juice leak from the small hole. I licked up the juice that covered the head and sucked on the head, tasting the salty, sweet substance. It was almost like I was a child being taught how to suck a dick, and my roommate as my teacher.

It was different but its worth it.

"Alright try taking some it in your mouth." He said, I glanced up at him and noticed his smile and trying to comfort me.

I sucked on the head again, this time I took it slowly in my mouth. It was different feeling this huge leaking stick filling my mouth like I was eating a piece of steel.

I backed away from it, then slowly slid it further in my mouth. My mouth was getting wet and I could feel the dick head touching the back of my throat.

I coughed and backed away from it. "Don't worry Shawn, just relax your throat." His voice was so soothing comforting I had to trust him.

I did my best on relaxing my throat and sucked him back in. I heard him moan when it started to go down my constricting throat.

"Damn your mouth feels so good." He said. That made me excited and I tried to suck more if in my mouth.

"Oh man your doing so good for your first time. Go on and try and take it all man." He said looking down at me, with his dick half way down my throat.

Once again I tried to swallow more of him but I coughed and gagged again.

I pulled him all the way out, trying to relax my throat again. Then I swallowed it again, this time taking more than half.

"Ooohhh Shhhiitttt... Damn that's it." He moaned out. I felt his juices lubricating my throat making it easier for me to swallow him.

His dick was firmly lodged down my throat and I was losing my breath. I was willing to try and take it all though. So I quickly jammed it all down my throat all the way to his pubic hairs.

The hairs tickled my nose and my air supply was leaving me, so backed away from him to regain it back.

"Damn nobody's ever swallowed the whole thing." He said.

"Really?" I asked shocked that nobody has ever done it to him.

"I'm serious every girl I've had said they didn't want to choke or they were too scared to do it. You're the only one that didn't complain about it." He said.

I found it strange that I was happy about the complement but I wanted to do more to show him that I was better then those other girls.

"Do you wanna keep sucking it or do you wanna go to the next step?" He asked.

"What's the next step?" I asked.

He smiled and said, "I'm glad you asked..." He got on the table and laid on his back.

He lifted his legs and exposed his anus to me.

"What... What are you doing Brandon?" I asked sheepishly.

"Shawn, I want you to lick my ass." I looked at him like he was crazy.

"Lick your..."

"Yes lick my ass." he repeated.

"But that's dir.." I begged.

"Nope this ass is clean just got out of the shower after working out." He said. I moved over to him and stared at his ass.

It was tempting, his ass was perfect but this was definitely something I've never thought of doing.

"Let me make it easier on you." He got up and left the room for a second.

I stood there waiting for him to come back. Then he walked back in the room with a videotape in his hands.

"I just borrowed this from a friend, I want you to watch it with me. Maybe you would be more comfortable doing it after watching this."

He slipped the tape in the VCR and made me sit down next to him....

(To Be Continued)