Let me start off by saying that I'm a 26 year old cub living in Ottawa, Ontario and I have a criminal record. I'm under house arrest for a crime (non-violent) I committed back in 2003 and I can't leave the house except for work, medical emergencies, and community service or to attend meeting with my probation officer.
I had asked my probation officer earlier this week for permission to go out to actually look for jobs, instead of staying at home and sending my resume by email all day long. So she gave me permission to go out on Thursday morning and drop off my resume at a few places, she gave me 3 hours to drop off as many resumes as I could. I had to go pick up a letter at the probation office in the court house on Elgin Street.
When I got to the office a little after 10AM, I had to wait a little bit since there were people ahead of me who were still waiting to be served, so I sat down and took out a book I was in the process of reading.
When my turn was up, I was the only one left in the reception area. I walked up to the window and saw this guy that is usually there every month when I have to meet with my probation officer. He was very attractive, just the kind of guy that I usually go after. About 6 feet tall, he wore clothes that made it hard to tell if he was muscular or chubby. He had these really captivating brown eyes, the kind that feel as if they're looking right into you whenever he decides to set them on you, but they were partially hidden by his glasses, which only made him more attractive. He had short brown hair that were styled in a spiky/messy style that seems so popular lately.
I guessed his age to be around 35, which is actually younger than my last boyfriend.
Lately I've taken to wearing a hand made bracelet that sports the pride rainbow colours on my right wrist. When he handed me the envelope with the letter, I grabbed it with my right hand to put it in my backpack. He noticed the bracelet and said "nice bracelet".
So I replied, "Thanks, not everybody knows what it means though".
"Yeah, I know what you mean", and he showed me a tattoo on his left forearm that was hidden by his long sleeve shirt, it was a hand waving a rainbow flag.
So I asked him, "Are you?" and left the question open, hoping he would complete it for me, and he did.
"Yes, I'm gay. And I've noticed that you've been checking me out every month when you come to your meetings with Stephanie, wasn't sure why though, until now when I noticed your bracelet, guess you should know that I was also checking you out while you were busy reading your book".
I didn't know what to reply to that, I don't like the feeling of being caught red handed, so to speak. I just said stupidly that it was nice to know that he was gay too. Just as I was heading out the door, he called out to me and motioned me to come back to the window. I approached the window again, and he asked me in a very quiet voice if I was gay or bisexual. I said I was totally gay, to which he replied, "Ok, just wanted to know".
"I know there's probably rules here to prevent the staff from 'fraternizing' with the clients, but I'd like to know if you'd like to come to my place for coffee or something?"
"Actually, there are no rules like that for us that work the main reception area, but I have a personal rule that I don't date people I meet at work, sorry."
"Well then, if we meet somewhere else though, then would you accept my invitation?"
"Let me think about it and I'll let you know the next time you come for a meeting with Stephanie, okay?"
"Sure, take your time, it's not like I get to meet good looking guys all the time anyways."
And with that, I left the reception area and made my way outside. I spent the next few hours dropping off my resume here and there, pretty much anywhere that had a "help wanted" sign in the window.
Later that night, just as I was just sitting down to watch a movie when I heard a knock at the door. Since I don't have a peephole in the door, I actually had to open the door to find out who was there, which can be inconvenient at times.
When I opened the door, I got the surprise of my life. The guy from the probation office was at my door.
He must have noticed my surprise, what with my jaw hanging about 2 feet off the floor and all. He said that he had thought about it and didn't want to wait until my next meeting with my probation officer.
So I invited him in, offered him something to drink. He said that he would like that coffee if the offer still held. I kinda sheepishly told him that I don't actually drink coffee, that I would have gone out to buy some if I'd known he was coming. I told him all I had was some Pepsi, water and orange juice. He said that water would be fine.
While I got him a glass of water, I told him to go on into the living room and get comfortable. I heard him taking his jacket off and settling down on the sofa. When I walked back into the living room with his water, I nearly dropped the glass. He had not only taken off his jacket, but he had taken off his shirt too. And what a sight! His chest was entirely covered in dark hair, just how I like it.
He must of heard my gasp, cause he turned around and flashed me the most beautiful smile I've ever seen in my life. He asked if it was okay that he had taken off his shirt, he said that he usually gets completely naked as soon as he gets home from work since that's how he's most comfortable, but he felt that it might have been a bit too much seeing that we barely knew each other. Heck, I didn't even know his name.
I managed to stammer that it was okay with me, he could get as comfortable as he wanted, I wouldn't mind. He just looked at me with those gorgeous eyes and simply said "Maybe later."
He asked me what movie I was about to watch, I told him I was about to order something on Pay Per View, and I asked him if he had any suggestions. He said that he had read good reviews about this one movie and asked if we could watch it. It turned out that it was one of the movies I wanted to watch too, so I ordered it and a few minutes later, the movie started.
I was trying to focus on the movie, but it was getting harder and harder with him sitting on the other side of the couch, and he seemed to be getting closer every time I looked over at him. About an hour into the movie, I felt his hand on my leg, moving slowly towards my crotch.
I looked down to my leg and followed his arm up until I was looking right into his eyes. I really wanted to kiss those luscious lips of his, so I craned my neck a little bit until our lips were almost touching. He made the move and we kissed. It felt like a million volt of electricity was coursing through my body.
The hand that had started on my leg, was on fully on my crotch and caressing my package. I placed one my hands on his chest and started rubbing it through the fur on his chest.
I broke the kiss first and moved down to his nipples, I took the right one in my mouth first, and started playing with it with my tongue, and then I did the same to his left nipple. He seemed to be enjoying the attention I was giving his nipples, but I wanted something more.
First though, I went back up and kissed him again. While we were kissing, he started pulling my t-shirt up, we stopped kissing long enough for my shirt to come off.
He placed both hands on my now exposed chest and just explored it with both hands. He reached my back and moved his hands to my butt and then back to the front. He tried to undo my belt, but he seemed to be having some trouble, especially since we were still kissing like crazy.
I, on the other hand, had no trouble whatsoever undoing his belt and the button on his jeans, or the zipper. Pretty soon, I was pulling his pants and underwear off. He had an absolutely gorgeous body. He was semi-hard, and his dick was already at least 7 inches long and about two inches wide.
I got down between his legs and took his balls in my mouth, turning them in my mouth and playing with then with my tongue. He started moaning.
"Oh God, that feels so good. It's been so long since I'd been with anybody, I forgot what it's like to have someone pay attention to my body like that."
"I haven't even gotten to the good part yet". With that, I took his big dick in my mouth, by then it was completely hard and must have been around 10 inches long. First I played with the head with my tongue, licking up the precum that was leaking out and spreading it with my tongue over the rest of his hard dick. I then took the rest of his dick in my mouth, using every technique I ever learned to drive him crazy with pleasure.
From his moans and groans, I could tell that it worked. He finally told me to stop before he cums. I pulled off his dick and went back up to kiss him some more. After a few minutes, he pushed me off so that I was sitting on the couch, he then got between my legs and managed to undo my belt and untie my pants and pull them off, along with my boxers. I was already hard by then, so he looked at my 7 inch dick and looked back up at me with a smile on his face.
"I've been dreaming of this moment since the first time I saw you walk into the reception area a few months ago, but the dream doesn't even compare to the real thing."
He started sucking my dick like there was no tomorrow, pretty soon I was getting ready to cum and I told him so, he just kept on sucking. About 30 seconds later, I started cumming like I've never cum before. It had to be the best orgasm I've ever had. He swallowed every single drop and kept on sucking, after a few minutes, I couldn't take it anymore and sat up, pulling my dick out of his mouth at the same time.
I got up and told him to follow me to the bedroom. I walked up to my nightstand, where I keep my lube and such and bent down to open the drawer. I felt him come behind me and he started playing with my ass. It felt so good. He was rubbing his thumb on my hole, sending shivers through my entire body. I grabbed my bottle of lube and handed it to him.
I got in bed and got on my back and spread my legs. He poured some lube on my asshole and started pushing first one finger, then two, then three and finally four. I'd never been so aroused as I was at that moment. I told him I wanted his big dick up my ass, so he poured more lube on his dick and positioned himself so that his dick head was right at the opening of my hole.
He started pushing his dick in, first just the head, then he'd pull out, and then he'd push in a little more and pull out again. I'd never had a dick so big up my ass before, so it was a little painful, but he must have been used to coming up against a bit of resistance, so he was gentle. After a few more thrusts where he'd push a little bit more of his dick inside me every time, it was completely in.
By then, all pain had disappeared; it was all pleasure at that point. He rested with his dick fully inside me for a few minutes, and then he pulled out almost completely before pushing it all the way in again. We got into a really good rhythm, and after about 15 minutes of him thrusting his dick in and out of me, he said he was getting close to cumming and he asked me if I wanted him to cum inside me.
I told him to just keep going and to fill me with is cum. A few minutes later, he went almost completely rigid and I could tell he was cumming. I could feel his dick throbbing inside my ass and I could feel his cum spurting out of his dick and into my bowels. Just as he started cumming, I started cumming too, and I hadn't even touched my dick since he started fucking me.
After we were both done cumming he collapsed on top of me and we started kissing again.
When he got up, we were both covered in my cum, but we didn't care. He reached down to the hair on his belly and scooped up some of my cum and licked it off his fingers.
I sat up and I could feel his cum leaking out of my ass. We went for a shower together and took turns washing each other. We both got hard again in the shower and jerked each other off. By the time we got out of the shower, the water was almost completely cold.
After he got dressed, I asked him if he'd like to come over for supper sometime. He said that he'd like to take me out to dinner, then we could go over to his place afterwards. I had to remind him that I was under house arrest and couldn't leave the house.
He said that he worked in the probation office and could pull a few strings so that I could go out and my probation officer would have to look the other way.
As I was got to the door to escort him out, I remembered that I didn't even know his name.
"Nice to meet you, Daniel, and thank you for such a lovely evening."
"You're more than welcome, but wait until I take you out to dinner, it will make tonight seem like a solo jerk off session."
"Hmmm, can't wait"
But that's a story for another time.