I was feeling horny today. It had been awhile since I last jacked off.
I had just taken a shower, and while I was washing my dick, I began thinking of my ex-girlfriend. I was remembering how sexy she was, how perfectly my dick felt in her pussy, and how warm & wet it was. I remembered how I used to cum in her mouth and on her face so often, and how much it used to turn me on. After thinking of that, my cock was hard.
I got out of the shower, my dick no longer fully erect, but still pretty long and semi-hard. I secretly hoped my roommate was staring at me through the peep holes in the bathroom closet, which was connected to the closet in her room.
When I got out, I knew I had to masturbate. Since I no longer have a room in my house (I gave up my old room to my new roommate since I was unemployed, and having trouble paying rent), my options were a)Just jack off in the living room, on the couch where I sleep. This option seemed kind of appealing, since the exhibitionist in me sort of wanted to get caught by roommate, who always sleeps until at least noon in her room. But as perverse as I am, I had to be realistic. If my roommate caught me jacking off, it would probably just be embarrassing more than arousing.
So I chose option b)Go in my other roommate's room (he was at work) and jack off in there.
I went in, and turned on one of my favorite porn videos, and began to stroke my cock. Watching the video was turning me on, but as I watched, I still fantasized about my roommate coming in to ask me a question or something. If I had already made the effort to seek privacy, then it would be her fault if she caught me jacking off, and I would just lay there with my dick out, and she would say "Would you like some help", and I'd say "Yes".
But the chances of that happening, I thought, were probably about 1%...or less. So I continued jacking off, focusing on my porn video.
All of a sudden, the first part of my previous fantasy happened...my roommate did indeed enter the room, and without knocking. She seemed surprised and embarrassed at first, but she noticed that I did not seem either surprised or embarrassed, and I was laying there with my hard cock exposed to her.
"Jacking off?" She asked, giggling to herself.
"Yup." I replied.
"Do you need some help?" She asked.
"Yes, but just this one time." I said.
She walked over to where I was laying and knelt down beside me, looking at my stiff cock.
"I like to have some visual aide when I do this," I said, "So either I can just keep this porn on, or if you want me to focus on you, then you could just take your shirt off so I can look at your tits while you do it."
She smiled, and took off her shirt. Her tits were not very big, but they were big enough, and just the idea that my roommate who I had never had any kind of sexual encounter with, and had not really even thought about having a sexual encounter with, was about to give me a handjob while she was topless.
"Oh, also, if you want to do this, you have to do it until I cum, okay?"
"Okay." She said, smiling. This also turned me on immensely, knowing I was going to cum all over my roommate's hand.
