Watching Chrissy

I was Chrissy's roommate for a year or so. I was more or less stuck in "the friend's zone" with her as they say. She trusted me though, and I was always happy to keep her company.

She had a few dates now and then, though usually they didn't lead to anything serious, and most guys were kind of turned off by her having a male roommate in the first place. But she considered those guys too insecure to be dealing with her in the first place.

I moved in with Chrissy for what other reason than to sleep with her, maybe have a relationship with her. She was a brunette, kind of skinny, decent sized breasts, but a pleasant smile, warm personality and nice legs. Her legs were her pride. Anyway, she came home to the apartment one day, pretty tipsy. She got a beer from the refrigerator to get a little more drunk, apparently. She told me, "glad to be home."

"Why?"

"These old guys keep hitting on me. I've been kind of frustrated lately and they aren't helping. I need to get laid."

I figured this would be my opportunity. This was the first time she even mentioned something sexual like that to me. I told her, "I can help you out there."

She responded, "no, I like things how they are." But as the night dragged on, she stayed in her room, but drinking more.

She came out of her room and entered my room. She stated, "I want to see your dick."

Nervous, I asked, "why?"

"I just do. Show it."

I pulled it out, it was soft, and kind of dull with me just holding it, shaking it a little. I didn't have much experience with girls, but the few times I've did anything with girls in the past certainly didn't start off like this.

"Make it hard, I want to see how big it is hard," she demanded.

I started shaking it, and fantasizing about everything I could, eager to impress her. "How about you help me out with that?" I said, trying to get more action out of her.

She responded, "why would I go to you if I need to get laid when it takes you so much effort just to get a stiffy?" I was kind of embarrassed from her response, but my dick did begin to grow at that point.

She looked at it closely, like she was inspecting it. I tried to tense my muscles and do everything I could to make it bigger, but she had a blank face looking at it. She demanded, "I want to see you cum."

"Why don't you just suck it?" This was kind of awkward for me.

"That's gross, don't you want to cum? If not then I'll just go back to my room."

I definitely didn't want that, so I started masturbating right there on my bed. I kept wanting her to join in somehow, but she got her point across already that wasn't going to be happening.

After a few minutes, which I intentionally tried making it last, I came. I thought about her showing me her breasts, or riding my dick, whatever, despite her staring at me with a cold glaze the whole time.

I asked her how big I am.

She told me, "not bad." She left after saying, "good boy," and that was that.

An hour later, we both came out to the kitchen at the same time. "I feel so much better," she said.

"Me too, I guess, why do you feel better though" I asked.

"I used my rabbit, never fails."

"You should have did that in front of me, since you watched me get off." I responded, kind of frustrated.

"Yeah but you were already finished getting off by then, so what's it matter?" I didn't want to push it, so I left it at that.

Some time went by, she teased me a little about me wanting to sleep with her now and then. She came home one drunken night, very happy. After some small talk, she explained to me that she found a regular fuck buddy, Derrick. She bragged about him having a real nice, muscular back, and how that's a big turn on to her.

I felt getting into a relationship with her being pretty hopeless. I told her, "well you know my dick isn't bad though, and that's what matters for a fuck buddy."

"No offense, but he's black and packing. Besides, I have a thing for attracting guys with big dicks." I hoped she meant that to include me at least, but she continued, "and he shot a huge load. I couldn't even swallow it all. Sorry if you didn't want to hear that, but it's true."

"Oh well, you're missing out," I told her, just out of jealousy.

Time went by, and my sex life was pretty much revolving around fantasizing about her.

She texted me, asking if she minded Derrick coming over after their haunted house date together. I responded saying I was fine with it.

I stayed in my room for hours, unsure of what to say or do when meeting this Derrick. I heard them enter the apartment, but I stayed in the room. They went to her room, and I just put on a movie. After some time though, I could hear them Chrissy moaning, and moaning, and moaning, for some time. It lasted off and on for about 20 minutes, ending of course with the loudest moans. I had never heard her quite like that, but then again she rarely brought guys back to the apartment. I heard her door open, and some small talk. After an hour or so, I opened my door, figuring that he left. I went into the kitchen to grab something to eat one last time before going to bed.

But I saw her door open, and through the door I saw her on her bed bobbing her heard on an enormous black dick. Obviously they this was round two. He was completely naked, laying there completely relaxed. She was putting forth a lot of effort, moving her head up and down his dick, then licking one side and the other, and licking his balls too. She kept her eyes closed and moved fast. I stood there frozen. My dick went completely erect, immediately. I had never thought about it before, but his huge dick was an awesome site to see in her little white hands and mouth. I wanted to have it to taste myself. She was wearing a bra, and little white panties. I pictured myself in her position, bobbing my head up and down his glorious black dick while wearing panties. After a moment I stepped away and headed towards my door. I barely got into my room before I pulled my pants down, and rubbed my dick for a second and came right on my bed, the fastest, and hardest I've ever came.

I couldn't get it out of my mind for a while. I thought about our dick sizes, how his made mine look so small and weak by comparison. I heard him leave, and I eventually went to sleep thinking about how bad I wanted it.

Well nothing came up of it with Chrissy. She asked why I never came out to meet him, but I just told her I was asleep or some excuse. In reality, I started looking on the internet at pictures of well hung men, thinking about me sucking them.

I finally worked up the nerve and ordered a large black penis shaped dildo to a PO box I had. I was a nervous wreck sneaking it into the apartment, even though Chrissy was gone at the time and it was in a bland looking box with no labels or anything.

I opened it up, and washed it quickly. I didn't know how to go about this, but needed some way to satisfy my craving. I put it in my mouth, and held it there, pushing it deeper. Holding my mouth that wide open was a little difficult, but it wasn't particularly exciting. I figured I'd try the next step, and got out some lube. I spread the lube on it, and put it in my ass. Slowly at first, because entering my asshole proved to be a little bit of a challenge. After a minute or so of wiggling it around, it entered me, and I pushed it much deeper. I felt it widen me, and though it was a strange sensation, I embraced it. I moved it back and forth in me, faster and faster. My dick was hard the whole time. With my free hand, I grabbed my dick and started stroking it. I came pretty intensely.

I thought this felt great and all, and did this several more times over a month or two. Chrissy always went to Derrick's, so I never got to see her with him again or even hear them. But I felt like I needed to take it to another level. So what I did was when Chrissy had been gone for about 20 minutes, I sneaked into her room. I looked for her dirty laundry, and found a pair of panties and a bra. I sniffed the panties, picturing all the juices that must be in them. I put them on with the bra. I kneeled on her bed, and bent over and began sucking the dildo like it was Derrick.

"What the fuck are you doing?!" Chrissy demanded to know.

I was shocked. I didn't expect her back so soon, or to not be able to hear her enter at the very least. I didn't know what to say and just froze.

"Are you gay?" she asked.

"No," I replied, kind of unsure about myself at this point.

"Just a sissy?" she asked.

"No, I just like to fantasize about it. I don't know."

"Why are you wearing my clothes?" she demanded to know.

"I like fantasizing about being a girl."

"I'm not surprised, with a dick like yours you should have been a girl."

I mumbled something, but she cut me off simply saying, "shut up. I could kind of tell you aren't like other guys, and that's why I never sucked your dick when you we were horny. Do you want to taste a real man's cum?"

I nodded my head, being obedient now. She pulled down her pants while laying down on the edge of her bed. I started to lick her thighs first, but she stopped me saying, "start with the panties first."

I noticed, Derrick must've left his mark there, because it was gooey looking. I licked the fabric though, with my dick rock hard. It was a little salty, and warm, but overall the experience was probably the most sexually exciting thing in my life. I moved higher, to her vagina's lips. The cum there was spread out and kind of messy. I just kept licking everything and swallowing it, a little at a time. Chrissy just watching me, like she was making sure I didn't miss a spot. I eventually cleaned her vagina pretty well I think, and started penetrating it with my tongue. At that point, she pushed me away though and told me to get out.