It was going to be a first for me by far. The year was 2011 and Craigslist was still open for the "casual hook-ups" business. I had hooked up with a few people and serviced them orally. However, I wanted to push myself further and a new posting seemed like an interesting opportunity: "Wanted, oral slave for 4 hour window while I work. You can't leave, you can't speak, do everything you're told. I do not negotiate with subs/slaves. If you can commit to being under my desk for 4 hours, message me." Also included were the usual strings of letters and numbers giving the stats (often a bit smudged) "ddf, swm,19yo, hwp/thin, avg cut" and so on, but this post also had a picture. Head-to-toe, fully clothed was a guy who looked like the quintessential nerd. Mostly skinny, unkempt hair, acne, very large nose and baggy clothes.
I was not physically attracted to him at all, but that was one of the ideas that captured me. I had never thought of servicing anyone younger than me or smaller than me. I could even be dominant in the bedroom, when I wanted to explore submission I sought men who had strong dominant characteristics. Choosing to obey and service this smaller, younger nerd would be a true act of submission. I thought about it for a few hours, jerked off thinking about being under his desk sucking him off but surprisingly I didn't lose interest after shooting a load. I replied to the message.
"Hello Sir, I have a little bit of experience orally servicing men. It would be an honor to serve you for hours. I am ddf, 25, hwp - maybe a few extra pounds (played a lot of sports). I hope to hear from you."
I didn't receive a reply. A week went by, then another week and I was jerking off regularly rereading this nerd's post. I loved fantasizing about this little geek cumming in my mouth. I even crawled under my own desk just to get a feel of what it would be like to be under his desk for hours. It was a little uncomfortable, cramped and I realized I probably wouldn't be able to touch myself once you added his legs and feet to the equation to take up more room in the already very enclosed place. Additionally, once a chair was pushed in with his lap right there, I would basically be smashed into position with my face stuck in his crotch and my body locked into position. I was going crazy fantasizing about being so helpless to this pip squeak.
I didn't want to message him again - I thought that would seem too forward if he took the dominant/submissive thing very seriously and his "no negotiation" line made it seem as if he didn't want me, then I probably couldn't change his mind. I began reading other posts looking for a new opportunity before the message I was waiting for landed in my inbox.
"Couple weeks ago you said you wanted to serve me and you could do it for hours. This isn't a joke. I have tried 2 others and they failed. I am a live streamer. I am doing a 4 hour stream this Thursday night. If you fail - I have to shut off my camera and mic and that costs me. I get penalized and I can lose sponsors. I shouldn't have to explain myself to a sub, you should do as told, but after 2 failed attempts I need to impress upon you dumb fucks that this isn't sucking me off and then you get to go. I want your mouth on my dick for the entire live stream. Reply with your number and I'll text you my address IF and ONLY IF you can follow my orders."
"I'm incredibly sorry about the 2 who failed you, Sir. I even practiced by crawling under my own desk and I vow 100% service to you for 4 hours. I will not let you down. Here's my number. I am thankful you chose me, Sir."
I was hard as a rock, before I could get my cock out and start stroking I got a text. "I'm going to give you a shot jock boy. Show up at 7:45. I'll get you situated under my desk, I'll be logged in playing video games, camera and mic on at 8. You will keep my dick in your mouth until I shut down at midnight. Do. You. Understand?"
"Yes Sir"
I had 2 days to kill before this fantasy would play out. I beat my cock raw over the next couple days. I reread the original post, the email, the text 1000s of times and every time my mind would spin out of control and my cock would reach new levels of engorged. I crawled under my desk a few more times and I pulled my chair in to get as accurate of a feel as possible. I realized I could only leave my arms by my sides or maybe rest them on the bottom of the armrests where they connect to the seat. I was so excited. Even at work, I spent half my time looking at desks and thinking about being underneath them. I had his email and his number - I thought about contacting him a million times to further add to my excitement. Tell him how much I want to serve him - maybe he'd say something demeaning to me, say something that would increase his role of domination over me. However, I knew it could blow the whole thing so I bit my tongue and waited. It was an excruciating 2 days to say the least.
Thursday, I left work and as soon as I got home I jerked off and took a shower. I dressed very casually - I wanted to be as comfortable as possible under a desk for four hours. My heart was racing as I drove to his address. Can I suck cock for 4 hours? My mouth has definitely gotten tired after 15-20 minutes. I guess, I wouldn't be putting in the full hard sucking for four hours, I just had to keep my mouth on his cock for hours - that could include licking, kissing, or even just lightly nursing it for stretches of time. Can the rest of my body take being cramped for 4 hours? I think so - if I focus enough on what I'm doing with my mouth, and only shift slightly when I absolutely have to, I could pull this off. I was parking. He lived in a large apartment complex - not cheap, but not really nice ones, they had been built within the past 5 years though so they still looked nice. I knew this complex was primarily college students as it was only a few blocks from the state university campus. They have been building housing constantly for years around the campus as enrollment was skyrocketing during the recession.
I followed signs on buildings to find his apartment number - ground-level. I knocked. This was it. The door opened and there was the nerd. He was at least 5ish inches shorter than me and half my bulk. His picture was unattractive and in person, he was not much more attractive. His hair was long, but not styled and was a little greasy. His large nose was even more pronounced in person and his acne took over patches of his face. He backed up and used one finger to motion me in. He closed the door behind us and I began to say, "I'm super excited..." before he cut me off with a "Shhh" I fell silent immediately and looked into his eyes - I was raised to always make eye contact and I have found out over my lifetime that it makes some people uncomfortable.
He reached up and put his hand on my shoulder; he was guiding me to my knees. I was getting hard as I lowered myself in front of him. I noticed his Mario Bros t-shirt and he was wearing black athletic shorts and I would guess no underwear as I could perfectly see his cock outline. He began, "I have a bit of personality disorder - I am only comfortable talking to people when I am in a position of authority. It just makes me a lot more comfortable with you on your knees so I can look down at you. If you are really submissive, you should be more comfortable in this position too, right?"
"Yes, Sir." I replied but I did not make eye contact this time. I looked down toward his feet. He rested his hand on my head.
"I like you jock boy. We only have a few minutes before I have to be online. Let's test a few things out to make sure this is going to happen." He pulled my head into his crotch, my lips fell onto his cockhead. I could faintly smell it through his shorts. "Kiss" he said and I began kissing his cock all around the head and up his shaft. I could feel he was at least semi-firm. He pushed my head back. Abruptly, he turned around pulled his shorts down and bent over like he was mooning me. "Kiss" he said again, I leaned forward and kissed his left cheek a few times, then his right. "Crack" he commanded. I didn't want to hesitate because I knew this was part of the test. Do exactly as I'm told, when I'm told. I kissed the top of his crack and then another kiss lower and another even lower. I kept licking my lips between kisses and I didn't want to kiss his asshole. The idea of making actual contact with his asshole made me sick to my stomach but I wanted him to believe I'd do anything and I did love his power over me. I left my lips parted as I connected them to his crack directly above his asshole and I exhaled hot air which I know he felt directly on his puckered hole. I lowered my mouth again and kissed directly below his asshole. I enjoyed the feel of the soft skin against my lips. And his ass didn't smell bad, just a bit musty and a stale sweat.
"Good" he said as he straightened back up and pulled his shorts back to his waist. You said you don't have a lot of experience submitting to men, but you didn't hesitate to do what you were told. I want you to remember that for the next four hours. You exist to serve me. Don't hesitate, don't think about it - your mouth is actually mine for the next four hours. I own it." He started walking down the hallway and I crawled behind him. I didn't dare stand up and make him uncomfortable. On my hands and knees I followed him into a bedroom he had turned into his gaming office. I could tell he definitely gamed professionally by the room. His desk was a bit larger than mine, which was nice, it looked like I could probably move back and forth between sitting and kneeling. He pointed to under the desk, it was carpeted so at least I didn't have to worry about being on hardwood floors for hours.
I crawled under the desk and was situating myself as he sat in his chair. He was still a couple feet back and he looked at me underneath the desk. As if he had read my mind, "I don't mind if you shift around as long as you can do it without breaking contact between your mouth and my dick." He shed his athletic shorts and he wasn't wearing underwear. He pulled his wheeled chair up to the desk. This was it.
