After lunch our first day we buckled down and started getting some work done. It was clear that Rick was also a brilliant lawyer with a legitimate serious practice. It dawned on me that it was a deadly combination to have these deviant connections and a great reputation in the mainstream legal community. The practice mostly centered around complex litigation, but he explained to me that over time he had gotten pulled into more transactional work based on his reputation as being a straight shooter. Ironic.
We wound down our work by about 6 in the evening and we headed to the garage together. We were the last ones out from the "Rick floor" of the building and we rode alone down to the garage. Rick and I were building a bit of a boss/worker dynamic too that made our attachment feel more natural.
As we settled into the car Rick was being warm and charismatic. Talking to me like a boss and a leader without any obvious undertones. He gave me more of the lay of the land of the work that we would be doing and shared some war stories and gossip. Rick made a few references to "getting me set up for the summer" and things along those lines but it was pretty straightforward.
When the driver dropped us off, Rick told him the schedule for the following day and sent him on his way. I stood next to him with timid anticipation of how things would turn now that we were alone at the house. Would I be able to sleep inside? Would I be eating like a normal human? Was I going to be subjected to some type of torture? It was a mix of excitement and actual nervousness that I felt. I also was feeling the pull of Rick treating me like his mentor and leader. There were a lot of feelings involved.
Rick kept his calm and pleasant temperament when we were alone. He told me we had a few things to work out before it was "time to relax." He told me that my trainer was coming by. I sort of felt shock and anxiety from this. It seemed inevitable that he was going to reveal to my trainer somehow that I was a little fucktoy for Rick. My trainer and I had a good relationship and it had been normal and unremarkable as far as I could tell. It made me wonder once again what he had known all along. Rick seemingly read my mind and told me "Josh is cool and trustworthy --- trust me on that he is completely cool' referring to my trainer. Josh was a younger black dude who was fit and built. I had never thought of him in any way as anything other than a trainer that was helping me get great results. Why was he coming?
When we got in the house Rick brought me into the guest room and pointed me to the laundry basket. I took off the suit and was down to my underwear when Rick handed me a pile of clothes "for now" he said and it was gym type clothes with some boxer brief underwear and a tank top. I got changed as Rick watched and he told me to go to the living room and wait for him. I could hear Rick shower and make a few phone calls as I sat on the couch in his nice living room. I didn't dare touch the TV or do anything other than sit and wait. I was appreciative that I was allowed to relax comfortably.
Rick came down dressed in some jeans and a polo, looking fairly casual. Pretty soon after the doorbell rang and Josh came in. I gave him an awkward "what's up" and he responded with a "hey man" Rick started up some small talk about how great of a job he was doing with me. He talked in a way that tread very close to objectifying me without being overtly clear that he was doing that.
"Let's go take a closer look" Rick eventually said and he walked us out to the garage area of the house. There was some gym equipment and Rick's sports car, that I had not seen yet. There was a clear area near the weight equipment with a mat and some mirrors set up. Rick directed me there.
"He's leaner than when you started and has developed a little bulk." Rick started, pointing to me like a product on a showroom floor. He tapped my belly and pulled at my shirt indicating I should take it off, which I did. "shorts too" rick said and I pulled those off as well. I pointed to my underwear and looked at Rick quizzically and said "we should be good." I stood there in my underwear and Rick and Josh discussed my physique. Rick wanted to see a little more development of my chest. He was happy with my arms and shoulders. Back could use a little work. He then stood behind me and help my hips softly and said "looks like decent leg work, would like to see a little more bulk in the back but you are heading in the right direction." Josh was responding mostly matter of factly throughout and was actually taking some notes on his phone. He was being very professional despite the seemingly obvious situation. They discussed my diet a little bit and involved me a little bit in the conversation. I tried to be cool and loose but it was a bizarre situation.
After they were done, Rick and Josh shook hands and Josh said goodbye to me, Rick said "I'll walk you out." Rick and Josh left me alone in the garage. I took the time to check out what they had discussed in the mirror, I got a gameplan in my head of what Rick wanted and I felt motivated to work on those things.
Rick came in a few moments later and struck up a conversation "Josh is really great, isn't he? He will keep working to get you in perfect shape." Rick walked in front of me and put his hands softly on my shoulders. "I know you know I'm not suggesting you aren't fucking hot as you are. We are working on making you world class." He rubbed my chest and then kissed me on the forehead. Chillingly gentle.
"Josh owes me his fucking life, so he will be cool with you no matter. He knows to mind his business completely. I could tell you his whole story but suffice to say I got him a second chance at life and he has been on the right path since." Rick was gauging my reaction. I kept my head up and smiled. Rick could tell I was somewhat uncomfortable. " He actually has no idea what the hell is going on with us. He thinks you're a kid that I'm trying to help out and he doesn't ask questions."
"You ever take a big black dick before?" Rick asked, pressing playfully. The truth is that at that time I had not.
"Actually no." I answered with a little smile of my own.
"I know Josh is the wrong age bracket for you. Ive never involved him in that, so don't worry." Rick said quickly. "But that answer won't be the same when I get done with you."
I was still in my briefs and was sort of waiting to see where this was going. I didn't respond much.
Rick started to walk out of the garage and waved me in the house. "Few more things. Can you got throw on the button up that I left on the bed, we need to talk to a few potential clients on a video call I'd like you to be on. After that we can have some dinner and spend some time together."
I went and put the Brooks Brother button up shirt on and went downstairs into Rick's work den. I was still in just underwear beneath. Rick had a chair next to him at his desk and he called me over. He did something that he would do a lot that summer: he put me into a situation that I had no idea if it was business or "business" and I had to improvise. We hopped on the video call and we were soon in a conversation with an older gentleman -- in his late 60s or even 70s -- named Stan. The conversation started with discussion of Rick and Stan's long history and some catching up. Stan noted that Rick seemed to have another "young bright star" in me and Rick always seemed to know how to pick them. Rick said "he's got the makings to be one of the best." I played it straight- coy and humble - because I had no idea what level we were discussing this on. There was then discussion of what Stan's legal problem was - trying to get out of all his business interests so that he could cash out completely and finally wind down. This seem to be legitimate but it was unclear if it was mixed in with code. There was discussion of me working with Stan all summer if it was a "good fit." Rick told Stan that before we made our way to Arizona to start working, Stan should come into town as soon as he could for the 3 of us to meet. It started to become clear that I was going to be spending some time with Stan. Once I figured out that I was going to be hooking up with him as part of the business that was going to be taking place, I got a bit more animated and interactive, but I tried to be carefully as to not fuck things up. I started to feel the energy of Stan wanting me. I felt invigorated.
After we wound down the call, Rick turned to me and told me that I did great on the meeting, and that it would be a really huge win for us if Stan wanted to work with us. Rick explained, just a little bit, that Stan had been reaching out to Rick for young guys to fuck for decades and that he was extremely picky -- but that he thought Stan would be into me. Rick told me that Stan was kind of a "sick fuck" but that he was also willing to compensate anyone that he shared his sickness with very handsomely. "You probably can't even imagine how much money you could make us if you impress Stan." I was getting very excited.
The next meeting was a little less ambiguous. The guy on the screen was in his office of some sort and was also an older gentleman. After very little small talk he said "we've been doing this long enough to get right to it -- let me see this piece of ass you've been raving about." Rick smiled but he also seemed a little uncomfortable, like he wanted everyone to be careful. Nonetheless, he waved his hand to me indicating that I should get up and show the goods. I thought that meant to lean into the camera and show my face and talk a bit. "Your ass, kid." The man on the video said sternly as soon as I started to interact with the screen. I complied and showed him my ass and he responded pretty quickly "Rick, you're the man, I'll be in touch soon. See you kid." That was that.
"We can eat in about an hour, go get a workout in and then clean up and meet me down here." Rick told me. I complied. I went to the garage and did my best to push myself with a serious chest workout. Then I went to the room that I had been dressing and showering in and took a nice warm shower. Rick had left another change of clothes for me. This time it was some very tight jeans and a nice button up shirt. Similar to what I had worn for our "date" a while back. This times the clothes were nicer but much tighter. Again no underwear.
After getting dressed I headed to the dining room. The lights were dim and the table was nicely set. Rick was bringing food over to the table. "I have a chef in here most days but I know you aren't completely comfortable with you knowing that you are the boss's live in boy. Hopefully this will do."
Rick had put together a nicely presented dinner of salad, chicken, rice, and vegetables. Rick had a bottle of wine near his spot. I was not a drinker at the time and I would not be allowed to have alcohol given my dieting regime at the time. I got water.
Rick had obviously been drinking a little. When we sat down he told me that he wanted to have a nice and romantic dinner for my official first day in the office. He did this thing where he kind of toasted me but it was just the two of us. He told me that he felt super lucky to have found me, and that I had the right attitude and was also "super talented" and that he was feeling very strongly about me. He told me that he was happier than he had been in a long time and that he was grateful I was willing to do anything to show him my commitment to him.
I felt captivated by this. I was 22 years old and I had always thought of myself as a straight guy with a little bit of a sexual deviance. I never expected that I would feel something as strong as this towards a man. But here I was feeling completely taken into Rick's orbit.
He took the time to explain to me that there was going to be a lot more testing of my limits with him. He told me that I had not completely "earned" my place in his bed for the summer, but that tonight he wanted to treat me like royalty. He told me that I shouldn't get used to it because he didn't want to get the wrong impression about how things stood -- I was still very much working my way up the ranks of loyalty. He also told me point blank that he enjoyed torturing me and that he knew that I enjoyed it, but he wanted to make this a night that could serve as inspiration for what was possible if I kept following the right path.
After we finished up he said "now, baby, why don't you go freshen up and get changed into what I left for you and I will come by in a few minutes." I started to get up "but baby, one last thing before you go, I wanted to get you something to show how I feel for you, even though we are still getting to know each other." Rick pulled out a box that looked like an expensive jewelry accessory of some sort of was inside. He handed it to me and I opened it up, it contained a specially made leather collar with some sort of gem spelling out the word "Rick's"
"I had it made so you can wear it under a collared shirt and tie without it being observed. It will fit pretty nicely to avoid detection, but you should take it off when you go to the gym and other times that i tell you, but I want it on you most of the time." He took it out of the box and put it around my neck. It was tight but just right. He gave me a little kiss and said "now go get ready for me beautiful."
These last few comments of baby and beautiful seemed out of the ordinary for Rick. I was turned on and also confused, a state that Rick seemed to like to try to keep me in.
I went in for another shower and to clean out again. I didnt notice any items on the bed when I went into the bathroom but when I came out about 15-20 minutes later there was a very peculiar set of articles on the bed. A black leather strap harness / garter bottom that strapped around the thighs, ass and crotch, and covered absolutely nothing. Next to it was a pink lingerie slip. Both items looked to be fine lingerie but sized to fit a guy like me. Next to the gear was a note that said "I believe you can find a way to be sexy in anything. Love to see you in these - R." It took me a few minutes to figure out the bottom harness but once I did it looked pretty sexy as I checked my ass in the bathroom mirrow. When I slipped the "nightie"/slip on it also looked good, but in an odd gender bending way. It was the first time I had seriously dressed in anything other than a man's clothes, and it was another slight thrill that I felt. As I started feeling the lust rise I heard a soft knock on the door and Rick saying "I'm ready for you baby, come see me." As I started walking towards the door I noticed a pair of large "heels" that were more like elevated platform shoes. Oddly, this is what transformed me from slight thrill to full on submissive euphoria. It took me a minute to strap them on and I finally got them on. They weren't too extreme but they definitely stepped me up. I could immediately tell that they would make loud heel thud sounds when I walked. This made me very self conscious about exactly what I was doing. I was into it, but it was an odd feeling.
I took a deep breath and walked out of the guest room. I had not seen Rick's room yet and I could hear some sort of smooth jazz music playing from down the hall and I followed that. When I got to the threshold of Rick's bedroom I spotted him on a loveseat that he had near the window, facing his bed. He was sitting in his bathrob with a glass of wine in his hand. "Absolutely stunning baby" he said to me as I pressed myself against his doorframe, trying my best to do a sexy person impression.
"Goddamn" Rick said after a few more seconds and threw back his drink. "Come here baby let's really celebrate." Rick said inviting me to the loveseat with him. He eyefucked me as I walked up to him and I was sort of unsure of what to do to get started with Rick. I went to kneel next to him on the loveseat so that I could rub his chest and ask him how he wanted this to go. As I started to move into the kneeling position Rick smoothly grabbed me by the hips and guided me to straddle over him. I had my knees on the coach and he placed his hands on my ass. "Kiss me my sexy baby." I leaned in and we had another very romantic make out session. As it grew more intense Rick was rubbing and squeezing my ass quite intensely. I was extremely hard and I could feel Rick was even harder as I started grind on his cock with my ass. Partly on my own volition but mostly because Rick was guiding my ass into his cock with his firm grip on my cheeks. I draped my arms around his neck and off the back of the seat. He eventually pulled my nightie up so that he could apply some playful but firm smacks to my ass. He was rubbing his cock on the outside of my asshole but every time I tried to actually push myself so he would be in me he would rub away.
"Let me taste that sweet little pussy." Rick wrapped his hands around my body and I instinctively wrapped myself tight around his shoulders. In one movement he lifted me up and stood up and walked me the few feet to the bed. He dropped me on the bed and leaned over me and gave me a gentle kiss before aggressively pulling my legs back over my head and almost tucking them behind my neck. He started to rim my asshole like he was eating pussy. It felt amazing and knowing that Rick was getting me wet so that he could fuck me was a major turn on. He at my boy pussy for a few minutes. We made eye contact a few minutes in and kept our eyes locked in what felt like the height of eroticism.
He eventually rolled me over and put me on knees so that he could bury his tongue in my ass and slap my cheecks as he was eating my ass. He grabbed and squeezed and smacked as he ate me for a while longer. He eventually got up and kneeled behind me and slapped his hard cock against my asshole. He leaned in like he was going to start fucking me but instead he pressed against me and leaned over and kissed my neck and licked my ear. I shivered with delight and pushed my hold against his throbbing meat.
"slow baby slow." Rick said as he eventually twisted around next to me on the bed. He pulled me back over him to straddle once again and we resumed our passionate kissing. It was wild to me how half an hour before I had never even thought about dressing up and suddenly Rick was making me feel like his wife or fiance. It was invigorating. Eventually Rick opened his robe completely and guided me to suck on his nipples. That seemed to turn him on but that only lasted a few second before he guided my head down to his cock.
While Rick was taking me to new levels of eroticism that summer, I had long considered myself a master cocksucker. In my mind what I gave was the most sensual blowjob that I had given to date. I took my time and focused on licking and eye contact and working the head for a significant amount of time. Rick would occasionally push my head down gently to indicate I should take him completely into my throat.
After working Rick's cock for at least 15 minutes, he pushed himself up a bit so his back was up against the head board of the bed and gently pulled me to straddle him again. He pulled me in for another brief kiss before guiding his dick with one hand and my ass down onto it with the other. My ass was still a bit impacted by the earlier fucking, and I had never had a cock in me without lube, but his cock was wet and my pussy was wet from all his licking. I was so turned on by the romantic nature of this hook up that I hardly noticed the shock him shoving his cock into me. I started riding him right away. I am a tall and bulky guy, so I was a bit uncoordinated as I rode my first cock. My legs were tucked back under me and under his legs. Rick helped by pumping his hips into me and I grabbed the headboard a few times. Given that Rick was sitting up I was able to occasionally lean up to kiss him although it was a little awkward given my size and lack of coordination with cock riding.
Rick looked at me like I used to look at some of the hotter girls that I had fucked in my day, with almost amazement that he was so lucky to have me. It was hot. I tried every move I could think of to be sexy as I rode his dick.
Eventually Rick pulled me off and laid me on my stomach and pounded for a while he lay across my back, kissing my neck, occasionally gently squeezing my throat. For the next hour or more Rick rotated through every possible romantic position. He grew increasingly sweaty. About 45 minutes into it I realized that his balls had probably been pretty drained from our festivities earlier in the day and the night before.
Finally, he put me on my back at the edge of the bed and stood over me and pushed my legs back as far as they would go and started pounding. As continued I could tell that he was really focusing on cumming and was struggling to get there given the drainings that had already occured. He was pouring sweat as he stood over me holding my legs back. He got to the point that he was pounding so hard and so fast that I almost felt like I was going to pass out from the intensity. Those feelings became literal when he eventually leaned forward and placed his hands tightly around my neck as he violently fucked me. I felt the lights start to flicker as he started groan as he came inside me. "Cum in my pussy" I gasped to him as he squeezed and groaned. "Yes baby" he said as he continued to squeeze. He kept pumping for a few minutes even after he finished. He eventually pulled out and leaned in for a kiss, covered with sweat. Immediately after he reached down to my asshole and pulled out a few fingersfull of cum and fed it to me.
Soon after that, he fell into bed and I wrapped up to cuddle under his arm. We chatted briefly about each others respective hotness and sexiness, and I soon fell asleep in his arms.