A business man

by Ultratropical

15 Aug 2019 15403 readers Score 8.3 (130 votes) PDF Mobi ePub Txt


I am probably the nicest guy in town and I am very well liked buy everyone. I work for a coffee shop downtown and I knew people from all places. I get complements on how nice and cute I am which not only make me feel better about myself but it only fuels my thrive to be nice to everyone and do favors to close friends and even strangers. This has obviously landed me in a few awkward situations like having to cancel a night out with my friends because I had agreed to take care of someones dog or child. The extra money I made doing favors was exclusively for my college fund for the following year. I had taking a year off of college to save money for the expensive classes and even more expensive text books. 

I was 21 at the time, 5'11, Hispanic and had a nice body. I always got compliments at bars and almost always before the club closed someone would slap my ass or try to grab my nipples. I was very popular as you can tell. All my friends knew I was gay and my roommate never seemed to care. Although I am a very simple guy in the outside I really enjoy things I would never discuss with my friends in fear they would think I was a freak. I have always had a thing for underwear. Wearing a thong or a jockstrap has always turned me on and I had a small collection of naughty underwear I loved to wear when I sleep. 

A Saturday night out with my friends turned into a night out by myself when both of my friends had to go home early due to their schedule at work the next day. I was mad but I understood and decided to stay a little longer. I was not sure if I wanted to get more drunk, go home and change into a thong to touch myself or if I wanted  to try to end up on someones bed. All of the sudden my favorite song came on and I had the right amount of alcohol in my system to be able to dance crazy without caring who was watching. After a 3 minute dance I walked back to the bar to get my last drink. I must have not seen the guy in front of me when I ran into him spilling his drink all over his suit. He was a beautiful business man about 6'5, nice muscles and beautiful blue eyes. I was so embarrassed I couldn't stop apologizing.
"Wow buddy are you OK, I'm very hard to miss, you must be a bit drunk aren't you?"
"I'm so sorry I can't believe I'm this clumsy. Oh god I totally ruined your shirt with your wine. Please don't kill me" He smiled a bit frustrated but I could tell he was not mad at me, it could have happened to anyone really. 

"It's alright really but this was my favorite suite though. I'm Jay by the way"
" I'm Leo I'm drunk I'm sorry I am extremely sorry I don't know how I can fix it I'm so sorry"
"Well this ain't a cheap suit kiddo. It's very expensive... but hey you look young and I'm sure you're in college"
"I'm actually taking a year off to save money"
"Well I'm not going to take money away from your future, I'm sure we can figure something out. Tell you what, I've been very busy lately and my house is a complete mess. How about you come over tomorrow and clean around for me?"
"Of course I'll do anything"
As soon as I said that his eyes got wide and he smiled as if he was satisfied with the image of me cleaning for him. He gave me his address and gave me a handshake. 

The next morning I got up early, watered my plants, fed my cat and got ready to clean Jay's place. As I arrived to his house I was amazed with the size of the house. "Fuck. This was going to take me a while to clean." I thought. I rang the bell and J opened the door wearing a pair of jeans and a white tank top. He looked amazing, his muscles were even bigger or so I thought. I felt tiny next to him. He smiled and showed me his house. It was huge, specially for a single guy like him. I quickly began to clean the kitchen which had lots of dirty dishes. I always found washing dishes a calming activity so I enjoyed it a lot. Close to when I was finishing the last of the dishes I accidentally spilled some water on my shirt. Jay was nearby and offered to let me borrow some of his clothes since mine were now wet.
"I'll let you borrow some of my old clothes if you promise not to spill wine on them" he laughed and gave me a nice wink with his beautiful blue eyes. I followed him to his room which was also a bit of a mess. He gave me a pair of running shorts and a small T-shirt that was more of a crop top. 

As I was cleaning the rest of the kitchen I couldn't help to notice Jay was constantly starring at me and that began to get really hot. I couldn't help but to get a bit hard. I was wearing his clothes and he was watching me clean which I found very erotic. He was doing work on his laptop and drinking wine. Close to 5 P.M I could tell he was a bit drunk. Once the kitchen, the dinning room and living room were clean I asked if I could go into his room to clean it. He got up and told me to follow him. When I came into his room he was starring at me with lust in his eyes. I asked him if he was OK.

"Are you kidding me? I'm more than OK. I'm fucking great I mean look at you you're a sexy little thing cleaning my house."
I was blushing and trying not to smile like an idiot. "Thanks but you're a lot sexier than me" This made him smile a lot harder.
"Hey would you mind, for my entertainment you know, wear something else maybe? I've got something that's going to make you look a lot better. " He handed me a black and orange harness and a pink thong. I did not think twice about it and changed quickly. 

As soon as I came out of the bathroom he walked up to me picked me up and threw me in bed. He grabbed my chin and spit on my face and said "You ruined my shirt and now I'm going to make your sweet ass mine!" He tied my hand to the headboard and began to touch me and kiss me in the most sensual ways. I was enjoying every moment of it and I wanted him inside me so bad. After playing with my nipples and licking them he raised my legs up to reveal my ass. He slapped me hard and several times. A few tears came out my eyes but I loved it. The thong I was wearing was only making me hornier by the second.

 After both of my cheeks were red from the spanking, began to fuck me slowly and kiss me passionately. His dick was huge, about 10 inches. I was in so much pain at first and wanted to scream hard for every inch he put inside of me but he was covering my mouth. Once I got used to his huge dick I was only begging him to fuck me harder. Suddenly he stopped. He took my thong off  and walked into his closet to bring multiple pairs of underwear. " Im going to fuck you in every single one of this. If I cum you are gonna have to come tomorrow and do this all over again" "Yes sir!" He had so many thongs and jockstraps I knew I was going to enjoy every second of it and I was hoping he would allow me to keep some of them only to feed into my fetish for underwear. 

We went through about 7 jockstraps and thongs when he finally filled my ass with his cum. He didn't pulled out right away, instead he kept fucking me slowly kissing my neck and playing with my nipples. We were both sweating and smiling. His dick still half hard inside of my ass. He finally pulled out, untied me from his bed and offered me a shower. I was having a hard time walking since he had fucked me so vigorously. I kept going almost every day to clean his house and we always ended fucking in a different room and with different underwear which he unfortunately did not let me keep. I still dream that one day he'll let me keep a thong or two. Also I hope he never runs out of underwear because I love having his dick inside me and feel it pump his cum deep inside me. 

by Ultratropical

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