In the first few days of being Rick's summer meat a few things became clear about Rick: (1) he had an insatiable appetite for sex and I was a genuine target of his lust and (2) Rick was super connected to a lot of wealthy and weird people.
To the first point, working and living with Rick was like being a guinea pig for his sexual depravity. I could tell that he was really turned on by me, but I also could tell that he was quite entertained by the fact that I was committed to complying with all of his demands in order to be the best possible sub and summer associate. There were times when I could tell that he knew I was being pushed beyond my comfort zone but I was complying in order to keep him happy.
That relates to the second point as well. Rick explained to me how early in his career he had sort of stumbled into a community of wealthy perverts who were constantly searching for higher class sex toys. Many of these guys could not take the risk of engaging with lower level sex workers and so they gravitated towards a guy like Rick who was a bona fide professional that had all the cover that came with that status. The way that he had stumbled into it was when he was much earlier in his career he had a chance encounter with a younger associate at the firm where they ran into each other at an underground sex club. The associate was horrified and begged Rick to not make an issue of the situation. Rick had no intention of making it an issue but the associate was so insistent that Rick ended up fucking the associate regularly as the "hush money" for the run in with the associate. Another chance situation ended with a client of Rick's sniffing out the sexual energy between Rick and his associate. The client, who Rick was trying to sell on six figures worth of work, requested that Rick allow him to fuck his associate. Rick was young and ambitious and talked the associate into letting Rick and the client spit roast the associate in the client's hotel room. That client just happened to be connected with some other similarly minded individuals who started reaching out to Rick to work on "deals." He explained how he had a small network of Dayton employees that would act as super high level escorts for clients across the world. He made it clear to me that I was operating at an elite level because I was directly connected to Rick and I was his "fresh meat."
Sometime during the middle of the first week working for Rick he told me that I would be flying to Chicago on Friday afternoon. I assumed that we were heading somewhere to work on a deal together and I was fairly excited. I asked him for more details as the end of the week approached and he cornered me in my office to discuss. "Be ready to for the driver around 5:30 tomorrow. You'll be flying into O'Hare. Our friend Bill will have a driver ready for you to take you back to Bill's place." Rick explained.
"Who is Bill?" I asked.
"Bill is a nice guy that has some business he is taking care of out there this week and he wants to wind down with you this weekend before he heads back to his family." Rick explained. He could see the look of nervousness on my face. "This is the gig, boy. Bill knows a lot of the right people too so he is a good person to impress. Just be sexy and follow his instructions. Your only purpose is to make him happy. He shouldn't be looking for anything too weird. It will be fine."
"I can do that. Maybe it will be fun." I said, smiling.
"whether its fun or not, you need to make Bill believe its fun for you. Even if it isn't really doing it for you, remember its only for a few days and you'll be back with daddy." Rick said and before I knew it his hand was on the back of my head jamming my face into his crotch. He rubbed his hard dick on my face through his pants for a few seconds before he quickly unsnapped his belt and pants and quickly pulled his pants down around his knees. He put both hands around my head and forced his cock in my mouth, tilting my head to look up at him while he fucked my throat. "This will be kind of a nice low key weekend for you with a relatively vanilla guy. When you get back from this trip we are going to start to really ramp things up with you. I have a lot of ideas... and hopefully a lot of horny friends assuming you get the right reviews from Bill." As Rick fucked my face he started listing off a few of his nasty ideas, but it was hard to really concentrate.
"Look at me and open your mouth." I complied. Rick pulled his cock back and leaned over and spit into my mouth. He took a few more pumps before he unloaded into my mouth "Look at me. Look at me." he repeated while he let out a good sized load - extra impressive considering he had fucked me in one way or another at least 10 times since I had started. "Tell me you're not going to fuck this up this weekend" he said with his cock still on my lips and my mouth still full of his cum.
"I will make you proud." I told him as I started to swallow his load.
The flight to Chicago was exciting and fun for a number of reasons. I had never had the convenience of having a car service pick me up and drop me off and Rick got me first class tickets, also a first for me. When I got to Chicago there was a driver at the airport with my name on a placard who brought me to the hotel in a private car. The driver handed me a room key and gave me the room number when he dropped me off. The hotel was swanky and Bill was staying in a suite towards the top floor. When I got to the room I gave a timid knock. I was actually nervous showing up for an assignment like this. Just as I started to unlock with the key I heard footsteps and the door opened. I was greeted by a 5'8" man who was 40 pounds overweight. He was out of breath and clearly was suffering from the summer humidity and heat despite the benefits of hotel air conditioning.
"Well holy shit you're hot." was the first thing that he said, which made me know it was the Bill I was looking for.
"Hello its realy great to meet you - beautiful place here." I said, stepping in and looking around kind of shyly. As soon as Bill closed the door he took a few deliberate steps to walk around me and step right in front of me. He pressed his body on mine and took a deep breath. He looked up at me and said "kiss me, boy."
Whatever my reaction was to the aesthetics of Bill, I tried to remember what Rick had told me and I closed my eyes and complied. Bill was not a sensual kisser, he greedily mashed his face into mine and pushed his tongue into my mouth. It seemed like he was being purposefully abrasive and intrusive. He grabbed around my neck and pulled as we kissed. It was awkward and uncomfortable. Despite my desire to be a good employee for Rick, I was feeling uncomfortable and even a bit disgusted. At my young age at that time I still felt like a kiss was "gayer" than sucking a dick or taking it up the ass. I was feeling the crushing weight of that feeling in this first extended kiss. To remedy, I moved my hand down in search of his cock. I had to search a bit through his shapely body before I found it in his pants. It was a average to below average sized tool, fully erect. He moaned a little as I started rub but after a few seconds he pulled back and looked at me and sternly said "we don't need to rush, I have you for the weekend." Then he continued to kiss in his unsexy manner, now almost pecking as he would pull his head back after few seconds to look at me and express his arousal. I did my absolute best to play along.
The eroticism of the moment did kick in as I closed my eyes and tried to survive the discomfort. I realized it was pretty hot to have been shipped halfway across the country as a prized piece of ass. After all the stress of the year in law school and the more difficult legal work I had been doing with Rick, I allowed myself to relax as I recognized that there was very little stress involved with just being Bill's entertainment for the weekend. At the time I had no idea the potential benefits that it might bring and besides, Bill wasn't the most disgusting guy I had ever hooked up with (one of the first guys that I had met off Craigslist at the beginning of law school was morbidly obese and him and his apartment smelled terrible when I went there to meet him - I was super horny at the time and followed through with a blowjob and swallowing his load before slinking off into the night -- and truth be told I had banged a few fat chicks in my era as well).
Moments later, Bill started pulling me towards the bed area. When we get close enough he hopped back on the bed and sat back, while I was still standing. He removed the gym shorts and underwear he had been wearing to reveal his hard dick surrounded by an unkept bush. I was always ok with sucking dick so I was relieved to move to that stage of the game. I dropped down so I was draped over the bed, knees on the floor, belly on the bed, between his legs and face to face with his cock. My natural habitat. As soon as I went to work on his dick Bill lifted his legs and pulled his knees back, placing his asshole in front of my face. "Not yet boy" Bill said as he pulled his cock away from me. "You gonna show me how you eat ass first boy." Bill said. The truth was I had only eaten ass a few times before this and I had not enjoyed it for the most part. One guy had me eat his ass in his car as a break from sucking his dick when I was quite a bit younger and I thought that was fine. However, my first year of law school I had a less than clean experience with it and had been completely turned off by it.
"My ass is shower and bidet fresh dont worry boy get to eatin'" Bill said. While it was probably shower fresh from any toilet related matter, it was clear that Bill had been sweating the last few minutes and I was aware of that from my vantage point. He did not smell horrible but he also wasn't soapy fresh.
As much as I wanted to vomit, I remembered what Rick said, and I remembered what the mission was. I looked at Bill as I let out my most seductive moan and ran my fully exposed tongue over his asshole. Bill put his head back and rolled his eyes in delight. The energy was hot but the ass eating was not appealing. Part of the issue was that I felt like certain things were "top" behaviors and other things were "bottom" behaviors and it always felt like eating ass was like eating pussy and being a bottom was like giving up some pussy. Getting my "pussy" licked was a turn on for that reason. When pursuing my hetero side I was never afraid to eat some pussy and honestly had really enjoyed eating a few girl's asses when I was able to assess that they were into it. I tried to build a mental model for this moment that allowed me to feel like the sub bitch I am and not like I was eating pussy. I tried to focus on how humiliating it was to be told to eat a guy's ass. That was the right mindset.
The right mindset was important because for the next 30-45 minutes, perhaps longer, Bill instructed me on how to properly eat his hole. At various times I was instructed to lick vigorously, dip my tongue all the way into him as far as possible, or to lick him from back to taint slowly and sensuously. He talked a lot to me, both encouraging and demeaning, and sometimes a mix. At times he laid back with his arms over his face, and other times he gently (and a few times firmly) grabbed the back of my head for strict guidance. It was actually work to keep up with his demands and to keep myself at least acting enthusiastic and compliant with his wishes.
By the time he grabbed me by the head and forced me onto his cock so he could blow his load my mouth was quite tired from working on his ass. Bill didnt even really let me suck him as much as moved my mouth to the location of his load once he pulled me off his ass. He was jerking vigorously and shot almost right away. He quivered for several seconds after the several spurts were done. He was sweating saying things like "oh shit" as he caught his breath. He soon got up and went into the bathroom and washed up. When he came out with a wash cloth he handed it to me and also noted that I still had all my clothes on. He hovered over me as I washed my face a bit with the cloth. I handed it back to him unsure what he was looking for. He took the towel and tossed it into the bathroom area. He then turned back to the bed and grabbed my shoulds and pressed me down.
Again he came and started kissing me again. He was wearing a pair of tighty whity underwear that he had thrown on when he went to wash up and he was grinding against me as we made out. He eventually pulled my shirt up and started licking and sucking my nipples before pulling off my shirt. He then started to work on my neck and my ear, trying to turn me on completely. It tickled and felt uncomfortable but it had its erotic elements. Pretty soon he had me fully disrobed and was back to making out. I eventually got myself into the "guard" position with my legs wrapped around him. I tried to move my ass up to press on his cock like a good bottom.
Bill was a chill guy but he was consistently fighting against my sexual instincts. As I tried to rub my ass against his cock he started working his way down to my cock. Historically, I had gotten the most eroticism out of pleasuring men - older men- without reciprocation. There were a few reasons for this including the fact that I just enjoy being used and when someone pleasures me it becomes something else. I think I would tell myself that if I wanted my dick sucked I would hook up with a girl. However, luckily, my cock was able to stay hard during most encounters with guys, and I was pretty hard from the energy of this situation - being a whore on a mission for Rick.
Bill sucked dick about as I would expect from his kissing and appearance - not great. He seemed to struggle with my dick, which is above average in length and girth but by no means a "giant dick." He also used too much hands and seemed afraid to all out suck. He seemed to enjoy the taste of dick and he was certainly enjoying himself. He told me I had a nice dick and repeated a lot of the compliments about how hot I was. He sucked my dick for a few minutes and I was actively holding back cumming, mostly because I had no idea what I was going to do if I did cum. I was afraid that Bill would want to keep on going.
Bill sucked, jerked, pecked, kissed my dick, massaged and worshipped my lower body, and just generally enjoyed my body for 15-20 minutes before he decided to creep back up on top of me again for another kiss. "God you're a hot boy, Rick always finds the gems. You're so big and strong and yet so submissive and shy. So hot." He said between awkward kissing and rubbing. He sort of collapsed into a roll next to me and I faced him, our naked bodies close, in an intimate face to face. Bill was seemingly overjoyed to have me with him. It was a mix of hot and awkward feelings. He rubbed my chest with his hands and bumped his head against mine. Soon we embraced again and returned to heavy making out. Bill seemed obsessed with kissing me. It was starting to wear on me.
Eventually Bill started pawing at my ass and I eventually was able to roll over to cuddle up against him, him spooning me. He wasn't back to being erect yet, as he seemingly hadnt recovered from giving me his load less than an hour before. He pushed up against me and kissed my ear and neck. Eventually he moved the arm that was under me around my throat a bit, not quite in a chokehold, but close to one. He soon reached around and got a grip on my cock and started stroking. For a while it wasn't turning me on all the much for him to stroke me, but then he started to apply a little pressure to my neck. He immediately felt the reaction as I started to moan and thrust my hips. It got me much harder. Bill seemed tentative about what I was clearly requesting: to choke me. He pressed only lightly with his arm as he stroked. I had to force his arm down on my throat to get him the message. He eventually complied and my dick got harder than ever. The harder he pressed the harder I got. Bill was getting the message and soon he had me in a full blown choke hold as he tugged on me. I started to cum a major load - shooting honestly 2 feet or more in front of me on the bed - as I lost consciousness. I could tell that he was marveling at my load and that he was still squeezing. I heard myself let out a snore as I came while choked out and Bill quickly eased up. I was still shooting as Bill started asking me if I was ok. It took me a few seconds to actually wake up and Bill was actually freaking out. As soon as I was able to open my eyes I turned to Bill a bit and draped my arm around his neck as I looked at him "that was so fucking hot daddy" and I gave him a sensual kiss. Soon we both fell asleep.
Waking up in Bill's arms in a hotel room in Chicago brought on my first uncomfortable thought of the summer. For a moment I thought to myself "what the fuck am I doing?" I was completely out of contact with everyone and here I was with a sloppy dude who wanted to make out and have me eat his ass. It may have been the fact that I finally shot a load and I was less insanely horny. I didn't know what time it was. I was completely in the control of my host. It started to have me reeling a tiny bit.
I was only awake for a few moments before Bill pressed up a bit against me and kissed me neck asking "you getting hungry boy?"
The truth was that I was very hungry. "Yes baby." I said to Bill snuggling back up to him trying to play my little whore role appropriately.
"Good" Bill said with a chuckle and he untangled himself from me and pulled himself up. He pressed my shoulders against the bed a bit and then swung his legs over my body, with his face directed away from me. He adjusted himself awkwardly on his knees and proceeded to ram his ass into my face. He found a way to pin me down and plant himself with his asshole directly over my mouth.
I went to work as I understood my assignment, but my stomach was turning and my anxiety was starting to rise. I was on the brink of being miserable in the moment. I thought about pushing him off and telling him I was done. Of course, I had no money or real way to get home. I only had the clothes packed for me by Rick. I did have my ID but nothing else. That seemed like it would be a brutal mistake.
So I ate. And ate. Bill was getting mor and more comfortable with being aggressive in facesitting me. After a while of him being on his knees and grinding his butt into my mouth, he slowly adjust himself so that his legs were more straight and he was in more of a hovering position, grabbing my chest with one hand and the headboard with the other as he ground on my face.
Eating his ass was miserable in its own right, but the extended crushing and choking of his body made it downright painful. I tried to convince myself it was fun pain but it was not working very well. But I took it. I never resisted. I squirmed to avoid being crushed completely a few times, but I never pushed him off and I never stopped licking his ass.
The dirty talk from Bill kept ramping up as he attacked me with his ass. At various times he told me what a faggot pig piece of shit I was, he told me that I was a disgusting whore, he asked me if my parents knew I was a gay whore, he told me that he could kill me if he wanted to. He would occasionally ask me to tell him how good his asshole tasted or how much I liked it. I would answer with smothered assfilled mouth the best I could that "love it daddy" and "your ass is so delicious." I could tell that Bill absolutely loved it and I don't think he knew I was hating every second. At one point, as he was vigorously rubbing his asshole across my mouth, he told me that he loved me and he was going to buy me from Rick, but that he was going to buy me to be his special boy forever. He asked me what I thought of that, it was particularly tough for me to register a positive answer to that, but I did.
Eventually, mercifully, Bill told me that he was getting hungry. I thought he was going to eat my ass for a while but he meant that he was actually hungry. He rolled his sweaty body off of me. He gave me a brief kiss before he got up to take a shower. After he was in there for a few minutes he called for me "come on boy let's get you cleaned up" I entered the shower as ordered and Bill passionately soaped me and washed me up. I reciprocated when he handed me the soap, taking especial care in cleaning his ass at his request.
I had no idea what time it was when we got out of the shower and got dressed. It was dark. That was about all I could tell. I looked in my bag and found the clothes that Rick had packed for me. All of it was what at the time I perceived as being gay or fruity outfits: salmon shorts, cut off jean shorts, tank tops and some preppy tops. It seemed to me that Rick knew what Bill liked and that was the reason that I was being dressed this way.
Bill was a little talkative as we were getting ready to go out. He told me some things about himself but none of it was particularly interesting. I engaged the best we could but it was clear that there was an age and interest gap. I could tell that I was doing a decent job in keeping up and making Bill feel like I was engaged.
I had a bit of a knot in my stomach as we got ready to go out. I could tell with my outfit and the way Bill was that he was likely going to want to show me off a bit as his "Trophy Boy." Conceptually it was appealing but I was worried that somebody would somehow recognize me and my cover might be blown. I didn't really have a choice.
I was right. Bill took me out on the town to walk, eat, go to the bar, and basically do everything you could think of for a night in the city. At various times he put his hands around my shoulder, held hands, and he even insisted on making out in the streets of Chicago a few times. The overwhelming discomfort that I had with it eventually simmered into something slightly hot as I realized that people were looking at me not because I was gay but because I was a whore and they knew it. The visual disconnect between me and Bill made it clear to everyone that gawked at us that I was a paid companion. There was something very hot about that once I picked up on it.
There was something also painfully erotic about being in Chicago, with no money, no means of communication, no resources, and just being attached to a random horny rich guy for my existence. It was painful because it was almost like being in jail - no sense of time or freedom -- but it was hot because it was living out the thing that had always made me feel the attraction to sex with men - wanting to be the center of masculine attention - like when I would watch the porn and feel jealous of the girl. Well now I was the whore who was the center of attention and it was fun.
After our night out things were much the same back at the hotel. Bill and I showered again and he wanted to make out, cuddle, and make me eat his ass. He was hard again and he spent a lot of time trying to cum again - having me suck his semi hard cock for a very long time or him jerking off near my face trying to give me a facial. He was getting frustrated and embarrassed, so of course he started to blame me. Eventually he collapsed down next to me for a break and fell asleep. I did too.
The next morning Bill woke up horny, apparently from the blue balls of not busting the night before. I awoke from him rubbing his cock against my ass and after the initial feeling of discomfort realizing I was waking up in the situation I was in - in the arms of a guy that kind of grossed me out - I allowed the slutty whore part of my brain to kick in and enjoy myself. We had fallen asleep naked and so Bill was tightly squeezing my bare body from behind. I did everything I could to reciprocate the energy of rubbing our bodies together. Bill was talking about how hot I was and kissing my neck and ears. I felt like I was starting to find my groove in being enthusiastic about the experience even if it was sort of unappetizing in some ways. Being into it without being too into it was tricky but I was enjoying learning on the job.
Bill was poking his cock into my ass and grinding quite a bit. I could tell he was ready to go in.
"You gonna fuck me baby?" I whispered as he was kissing my neck.
"I will fuck you boy." Bill said in his best attempt to be dominant. He then rolled over to the night stand and fumbled around: "gotta wrap it up with you whores even though you are fuckin' hot, plus Rick will charge me an arm and a leg for the boyfriend experience with you." I could tell he was putting a condom on. I was sort of taken aback. Not that he was going to put a rubber on, but that he was literally thinking about me like a street prostitute. The whole time with Bill had been a learning experience, and an adjustment period, to getting used to being a rent boy. Hearing Bill say that drove it home even more that I was truly in a place where I was a law student AND a sex worker. I had let guys suck my dick for money in undergrad, but that was kind of just for fun, but this was different.
Before I knew it, Bill was awkwardly ramming his dick into my ass, back to talking romance into my ear while I thought about things. Bill eventually started jackhammering me from behind with deliberate violent strokes in a way that was actually intense despite him being less than hung. While he was drilling and grunting I was thinking about being a whore and Rick being my pimp. There was something almost unreal about the situation in my mind, but at some point Bill's slamming of his cock into my ass as I thought kind of lead to a breakthrough. Whatever anyone might think of what I was doing didn't matter. This was a life changing set of opportunities that were unfolding and I trusted Rick that I could earn my dues working for him, reap those benefits, and not have it exposed beyond the circle that I would be dealing with. I also thought about the fact that even though Bill was kind of cringe it was just a weekend of work and that I should treat it like work.
Bill, who had been awkward and sloppy in bed all weekend to that point, actually gave me a substantial fucking. Maybe it was the genuine energy that I started giving back to him after I had my breakthrough, but Bill found his moxy and plowed me for a good half an hour, in a number of positions before finally pumping his load into condom while he was banging me face down on the bed.
After the pounding, Bill was fairly sweaty and out of breath. I cuddled up to him and rubbed his chest. I told him how good it was and how much fun I was having. I gave him a kiss and then we started talking about his work and his life a little bit more. We passed the time chatting and watching TV for a bit before we finally decided to get ready and get out of the room. Bill picked out one of my outfits and despite the fact that I hated the look I embraced the fact that Bill was dressing me up the way that he liked it. We spent the day in the city and in the evening we went to the casino and I was at Bill's side while he drank a bit and gambled. There was something about the fact that Bill had given me a good fucking and the fact that I had finally clicked with him that seemed to make the time pass a lot easier. I knew my job was to submissively stay a half step behind Bill as we maneuvered around. Once I fell in line by his side he was less inclined to go over the top with public displays of affection. It was only occasionally throughout the day that Bill would grab my ass or pull me in for a kiss.
When we got back to the hotel it was fairly late and Bill was at least buzzed if not more. He was getting pretty handsy in the cab on the way back and was telling me that we would shower when we got back to the room. When we got into the room Bill was quick to guide me into the bathroom and turn on the shower. There was lots of making out in the shower as we soaped up and got cleaned up.
"Better clean me out real good because your going to be chowing down" Bill said as he handed me the soap and turned around and spread his cheeks. I complied and spent a few minutes really lathering up his ass and lathering up my fingers and working them into his hole to get him ultra clean. I was actually looking forward to giving him the rimjob of a lifetime since I had been feeling inspired to get a top notch review from Bill. Eventually we rinsed off and got out of the shower. We brushed our teeth and then jumped into bed. Bill sat on his back and once again pulled his legs back and presented his ass to me "bon appetite my big sexy bottom bitch."
Bon appetite, indeed, I dug in and started devouring his hole. Bill was active for a few minutes and then he started to relax and let me work. Soon he was snoring and was clearly fast asleep. I tried to stroke his rod while I licked for a bit but it wasn't waking him up and a gave up. I crawled into bed next to him and cuddled up and fell asleep too, happy with my work for the weekend.
The next morning I woke up to Bill telling me that my flight was in less than 2 hours. "Gonna need you to swallow a load before I send you off, boy, show me you wanna earn that tip." Bill said as I was starting to get up to get my stuff packed. I could suck dick and swallow cum all day every day, so this was a welcome send off. I dropped to my knees next to the bed as Bill walked over and approached. I gave him a nice sloppy BJ, making unnecessary gagging noises, spit rolling out the sides of my mouth, looking up at Bill and making eye contact. He asked me a few questions about being a cocksucker and I answered them with his dick in my mouth. It was only a couple of minutes before Bill was holding the back of my head and thrusting his hips and letting out a loud euphoric groan. His cum hit my throat and I knew it was a first assignment well done. Bill walked away and I got dressed and packed the small bag I had brought.
Bill walked over to me with an envelope and pressed it into my hand. "I am going to be giving you rave reviews baby, and maybe I will have you back." Bill said as he leaned into one last kiss. "I will call you the car. Be safe. Thank you so much for all the hard work. Tell Rick I said he is fucking crazy." Bill said as he walked me towards the door. He opened it and nudged me into the hallway. He let the door close hard and it was almost like a slam. With that the weekend was over. I sitll had the envelope in my hand and put it into my pocket as if someone would piece it together if they saw me carrying it.
As the car was heading to the airport I looked into the envelope and there were five $100 bills. If that was my tip I could only imagine my rate. I wasn't sure what I was supposed to do with it when I got back to Rick, so I decided I was going to tell him everything to avoid any possible issues. Plus, you never know when you're being tested, and its better safe than sorry with sometime like that. As I sat at the airport and then took the flight home I couldn't stop thinking about the many different adventures that could be possible the rest of the summer.