A Life-Altering Weekend

Hey guys, this is the first story I've ever written. I always make up little stories while I'm wanking, this is the first I've written down. Hope ye enjoy. Oh and constructive criticism is always welcome.

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Well...I had to tell someone. When you go through a life altering experience like I did last week, it's very hard to keep it inside of you. You have to let it out, tell somebody, explore it further.

Let me start at the beginning.

My name is Tom, I'm 25, 5' 9", regular build. Pretty much your average guy, I like sports, HBO dramas, rock music, the usual. My love life hasn't exactly been stellar so far, but it's not nonexistent. I've had three girlfriends in my time, one of those relationships was fairly serious, but it ended about six months ago as she had to move away due to work. Pretty standard stuff, pretty standard girls in all honesty but there's one thing they all had in common, they were girls. My next sexual experience (little did I know it) was going to be vastly different, it was anything but standard and it didn't involve any girls.

I've been without work going on three months now, and as you can imagine it's near impossible to try to make rent and keep myself fed and internetted on my social welfare. My savings had dried up the previous month and because I don't speak to my parents I wasn't really sure where to turn. I had really gotten desperate when I tried my brother. He was struggling himself to make ends meet (which I knew), but I'd hoped against hope he'd have something to throw my way. Which he did as a matter of fact, advice. He suggested that I talk to an old school mate of mine, James Finchley. James and my brother had become good friends in recent years and I knew that James had given my bro small loans from time to time, or at least that's what I thought they were.

I was really embarrassed at the idea of asking an old classmate for a loan, especially since we weren't exactly great friends. Not that we didn't get along ar anything, we were friendly, but not friends. I was desperate though, and had no other ideas so I headed straight to James' house. I knew the way as I'd been to a BBQ at James' place last summer (I was invited through my brother). I remember, walking up the steps I had butterflies in my stomach, I was so nervous. I actually at the time hoped he wasn't there so that I wouldn't have to go through with it. But just my luck, he answered the door immediately, almost as if he'd been waiting for me.

At the time I noticed nothing off about it, my mind was preoccupied by far more important things. Anyway, James invited me into the living room, asked me to sit down and offered me a cup of tea. I half jokingly responded "Do you have anything stronger?", he just gave me a smile and said "sure". He poured us two whiskeys, sat down opposite of me and asked what was up.

I decided to just come out with it and not pussyfoot around it. I told him that I was looking for a loan of €500 until next month (I'd a few interviews lined up and I was hoping to land one of those jobs by next month). He, without batting an eyelid, said "Sure, I'll pay you €500". I wasn't sure if he just used the wrong word so i just tried to reiterate that it was a loan I was looking for. He replied that he doesn't give loans, but that he does offer brief employment contracts for varying types of services. He clarified, "I will pay you €500, you never have to pay it back. If you work for me this weekend." I was totally taken aback, I couldn't fathom what he'd want me to do over the weekend. He was a very successful architect, maybe he'd want me to work as his secretary or p.a.? As I was trying to figure this out he grabbed a piece of paper and said “Here's the contract, sign right now or the offer is retracted, never to be offered again.” (The fact that he had a prepared contract didn't seem strange at the time) It was very short really, it just said that I would have to do whatever work he required me to do over the next 48 hours, no questions asked.
I was still slightly shocked as I signed my name and handed it to him. “How hard can this be” I thought. He took the contract and almost nonchalantly said “Strip” I laughed and said “What?” “Strip” he repeated, I laughed again, but not as much this time. I asked, seriously what he wanted me to do. He said very slowly and clearly (I'll never forget it) “Strip naked” “I want you to strip naked”. I looked down at my copy of the contract, back at him, back at the contract “whatever work is required to do over the next 48 hours, no questions asked.” 30 seconds must have passed as I read and reread the contract, I looked back up at him. “Strip”.

I was thinking and thinking, “How do I get out of this?” “What do I do?” and then “Even if I can get out of this, I still need this money”. To this day I somewhat can't believe I did it, as I was doing it I couldn't believe I was doing it. I took off my t shirt and then unbuckled my jeans and pulled them down. As I did, my boxers slightly came down with them at the back. I went to pull them back up, “Leave them” I heard. I proceeded to take off my socks and shoes with my jeans and nearly fell over (I didn't know what I was doing, I was still in shock). I then stood there in my boxers, arse hanging out the back, head down. I couldn't finish it. “Everything” (he never sounded angry or annoyed, he was merely conducting me in a calm, clear voice). Trembling I tucked my thumbs under the waistband and slowly pulled them down, to my shock in the half a second or so between being covered and exposing myself, I went from completely flaccid to fully erect. I couldn't understand it, how was I turned on? This isn't far from rape, I'm not gay and yet, there I was standing to attention.

James slowly got up, walked a circle around me and then sat back down, he had this smile on his face, he looked so content, but not overexcited, just happy. He then looked at me and and amazingly said in a most reassuring way “We're going to have some fun Tom, we're all friends here, just do as I say and we'll both enjoy this I promise.” He then told me to start masturbating, I can't explain how or why, but this was so erotic and felt just...right. As I grabbed my member and stroked up and down, precum forming within seconds, James came over and then took over from me, stroking slowly but firmly, stopping at the the tip, getting the precum on his palm and then use that as lube. After a few minutes he then told me to strip him. I had almost no hesitation. I removed his top and shirt and then his socks and shoes. I stopped at his belt and slowed my pace. I unbuckled his belt, opened his jeans, pulled them down to his knees and just stared at what was barely restrained by his underwear, I slowly rubbed his decntly sized cock through the material, he must have been about 7” I myself hover just under the 6” mark. After removing his jeans I quickly yanked down his underwear, shocking him slightly and myself when his dick plopped right onto my face. I slowly ran my hands along it and then just gave the tip a gently kiss, I looked up at him, he looked down at me and nodded.

I engorged myself on his dick, taking the first 4 inches immediately and inching the rest down gradually (I couldn't believe how well (and quickly) I had taken to cock sucking). Using my tongue I would make “s” shapes around the head, poking into his pee hole and then take him fully again, repeating this for the next ten minutes or so. Eventually he asked me to stop and stand up, and then told me to bend over the side arm of the couch. He inspected my arsehole, pulling my cheeks apart, probing and caressing. Suddenly I felt something really hot on my anus and then, in the blink of an eye every hair on my arse came out, well except for a few stragglers which he proceeded to wax off. I shouted out, asking what the hell that was. He simply said he needed me hairless and thought it was best to surprise me, it would hurt less. He may have been right but before I could give out further I felt his tongue probing at my entrance, then forcing it's way in, he tongued and licked my arse offering me unknown pleasures. I had experienced nothing like this before. Then, again without warning I felt a really cold gel on my puckered anus, he did warn me this time though, saying “I'm going in now, I'll take it slow”. He was true to his word, slowly he pushed his throbbing cock into me, it hurt like fuck at first but then when he passed the ring, Oh my God! It felt amazing, like the explainable combination or pain and ecstasy. I never wanted him to pull back out, every slight movement just escalated my pleasure. I was very close to coming, just from being penetrated. After a couple of minutes he slowly picked up pace, and went deeper in and out of me, I got so into it I pulled my arse cheeks apart so as to get as much of him as possible into me. He took this as a sign and began fucking me like an animal, he was like a dog in heat, I lasted about 90 seconds of that before I exploded all over the side of the couch, and as soon as I had come down from my orgasm he unleashed a load into my guts. He then quickly told me to squat down, open my legs and to squeeze out his cum, he had a wine glass held under my exit and waited for it to creep out of me. It came in a few dollops, he then offered the glass to me and I downed it in one. As I'd finished swallowing, the fact that I'd just drank another man's semen that had oozed out of my arse and had been fucked up there by him, flashed across my mind. For a millisecond I felt disgusted and then my cock started rising again.

He smiled and directed me to his downstairs bathroom, and then told me join him in the shower. The warm water felt great, but then his hand stroking my cock felt better and his mouth wrapped around my cock felt unbelievable. This was by far the best blowjob I'd ever been given. His mouth was like a vacuum cleaner sucking with such force, not enough to hurt, just enough to feel FUCKING INCREDIBLE!! He then got up and proceeded to soap me up, my chest and legs and off course my cock. He also soaped up my back and fingered my arse with the soap. I then reciprocated, his arse was completely hairless and I could see from the way he was arching his back and sticking it out there was only one thing he was looking for, a good hard case of cock up the arse. I drove it in so fast, it almost took him off his feet and rammed it into him over and over again (again I briefly got a “moment of clarity” I wondered what the hell I was doing, but decided I didn't give a fuck). I fucked him and fucked and then...stopped, turned him around grabbed his dick and came all over it. Before he gave any instruction I then started licking my cum off his cock. He never mentioned anything about my aggressive buggering or coming on his cock (I assumed he liked it). But instead waved for me to towel him off, then toweled me off and instructed me to head back into the living room.

He followed me in soon after, in one hand he had a can of whipped cream and in the other he had a can of deodorant. I could guess, what the cream was for but not the deodorant can. He told me to get on my knees and then said that wherever he sprayed cream I had to lick it off. He firstly sprayed it on his finger (I remembered afterwards it was the finger he used to finger me in the shower). Then he sprayed it on his balls, I licked it off with glee. After this was his cock, which tasted better than ever and finally his arsehole he bent over the couch so I could like it properly, I proceed to lick and tongue him and was getting really hard as I was doing it. I realised I had always been fascinated by arses, but my previous exes never allowed me to investigate that interest. Another thought crossed my mind “Thank God I needed that money” thinking of that I smiled as I pulled back from his arse. He then told me to lie on my back on the couch with my legs pulled up exposing my arsehole completely. He proceeded to spray whipped cream into my arse and onto the deodorant can. My eyes doubled in size, as I realised what it was for. This can was about four times the girth of James' dick. I couldn't see how it was possible to take it, he gave me a reassuring look though, and since this had been the greatest sexual encounter of my life so far I went along with him. He gently pressed it against my hole, pushing with more force on one side, then the other, and repeated this for about five minutes until the first half inch was in me. I'm not going to lie, it hurt, but I could feel the beginning of that exhilaration kicking in as well. He continued the technique, cm by cm until he came up to my ring, with a little more force it popped in and I had a second of agony followed by minutes of “flaming ecstasy” is probably the best way to describe it. He then shoved that in again half inch at a time, but it went in a lot faster now, when it went in as far as it would go, he got me to sit up and dropped his erect cock onto my lips. I swallowed him whole continuing my technique from earlier but also taking a leaf out of his book, sucking with just the right amount of force. After about then minutes he pulled out and then exploded over my face, some went onto my eye closing it, some on my nose, into my mouth and the proceeding loads landed on my hair and chest. While he was unloading on me, the can plopped out of my arse, this shock made me pop my own load. Some went onto his leg but most of it landed on the floor. We both then lay on the couch, panting trying to catch our breaths.

After a couple of minutes James and I recovered. He left the room briefly and when he came back handed me a maids apron. One of those frilly ones, it came down to just below my balls and covered practically nothing at the back, it just had a string going along my waist to tie it. James Explained that for the rest of the weekend I would be his maid and that the absolute most I'd be wearing I currently had on. He told me to go into the kitchen to make him a cup of tea. Suddenly I heard the doorbell ring and I froze. I listened carefully, waiting for James to dismiss whoever it was, until to my utter shock I distinctly heard the words “come in”. “What the fuck is he doing?” I thought. Just then Jame shouted in, “Make another cup while you're at it and bring them in to us, you're brother Tony is here.”........FUCK!!

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I haven't written a sequel yet, but if this gets a decent enough rating I'll definitely write another.