Hi all thank you all for reading and waiting, hopefully patiently. I hope to get a few chapters done over the next two weeks and push them out here. The next few chapters will be Tyler and Alan on vacation, there will be several twists and turns, sex, fun, love, and kink. I hope you enjoy.
When ran to the store after the sale and grabbed a few things to cook dinner and some beer and other libations. We turned into the driveway of the house and there were a few other cars there. I recognized Myles’ car and Tyler’s grandparents car. He sighed and looked over at me, I just grinned and took his hand and said, “we will get our time together, I think they just wanted to celebrate a bit with you”. We pulled into the shop and he hopped out and walked over to my side and I was out getting stuff out of the backseat. He walked up behind me and wrapped his arms around me and held me tight, then he kissed my neck and ear and whispered, “baby boy I am so happy to have found you and felt you up that night during the keg stand”, I chuckled and said, “damn I knew I was right and you did that”. He then grabbed my nipples through my shirt and pinched them hard, I groaned and ground my ass back into, I immediately felt his hardness, and I began straining in my cage. He then hissed into my hear, “fuck babe”, I just said, “I know”. We extracted ourselves from each other, he set two bags down on the ground and I turned, he leaned in and kissed me, then said “pick those up”. As I knelt he turned around and I was immediately nose to ass with him, I could not resist, I inhaled deeply and put my face right in the crack of his wranglers just as he passed gas. “Fuck me” I groaned, he just laughed and said, “that’s the plan for the rest of our lives”. I snickered and stood and we headed upstairs. We opened the door and were greeted with a rousing cheer and hugs.
Tyler’s grandma had made some food there and Tyler grabbed a few things and placed them out. I put the beer in the fridge and the two special purchased I had made. My family tradition was always to celebrate with good champagne. I had bought two bottles of Pol Roger, one of my favorites. Tyler made the rounds talking to his family and friends, I talked to the ones I knew as well. We ate some of the food, which was of course delicious, had a beer or two. Then I grabbed the champagne and glasses our and poured them and played Mr. Fancy pants and put them on a tray and walked about handing them out. This drew a few chuckles from everyone and an interesting twinkle in Tyler’s eye, and smirk on his face. Everyone had a glass and Tyler spoke up and thanked everyone, and then his grandpa spoke, by the time he was done Tyler, Myles, and he were teary eyed. This was a good segue for Tyler to again thank everyone and say he was pretty tired, and politely hinted that it was maybe time for everyone to leave. Now this is the Midwest, so about an hour later everyone was finally gone. We cleaned up and and I loaded the dishwasher. Tyler walked over and locked the door, and immediately barked across the room, “boy strip”. I could not get my clothes off fast enough. I shucked everything and knelt immediately. Tyler slowly stripped as he walked across the room to me, teasing and tantalizing me. He reached me and hooked his finger in my new necklace. He then said follow me, I began to stand, he said, “crawl”. I did not hesitate I crawled behind him. He walked over to the bed and instructed me to lay on the bed on my back. He then pulled me with my head hanging off the edge. He then placed his hand on my throat and dangled his hard cock over my nose and rested the head on my lips, I opened and he slid in. He went balls deep, and then squeezed my throat. He just told me to relax. I struggled a bit at first, then I settled in, he would pull back and release his grip, then back in and tighten. He must have enjoyed the feeling because he stayed longer and longer. When he was fully lodged and squeezing I could not breathe. This was fine with me, I was comfortable and trusted him fully. It was in a way aggressive, but sensual. Soon I felt his grip tighten and he lodged deep in my throat, and the head of his cock spasmed. He was shooting down my throat, I could not taste anything, he blasted and blasted, and did not loosen his grip. I lay there and tried to stay calm. I am not sure how long he held his grip, his cock began to soften, but he held tight. I was beginning to feel like I needed to breathe, but I tried to stay calm. I gasped a bit and finally Tyler released his grip. I sucked in air and coughed a bit. He was still in my mouth with his flaccid cock. He began rubbing my chest and head. He said, “fuck baby boy that felt so good, it was like I was jerking myself off using your throat, it felt like velvet”. I croaked out, “thank you Sir”. He lay down beside me and gently kissed my torso, nipples up to my neck and ears, then he crawled on top of me and began making out. I groaned into his mouth. He reached down and grabbed my caged cock and squeezed my balls, I whined louder. We made out a bit more. Then we just lay there in bliss. I said, “Sir I need to pee, and maybe shower and get some sleep”. He said he could do the same. I went in and set on the toilet, and he turned on the shower. We both got in and he said he had to piss, I knelt and drank it all, then we showered and dried off.
We went back into the bedroom, and crawled in bed. We were laying there and he said he had made the reservations in Palm Springs and Vegas, I said I had taken care of the airfare. He asked which airline and I just said, it will be a surprise. He chuckled and said, “well Southwest is about the only option”. I said, “true”. The plan was to leave right after my class was over Monday and be gone until the following Sunday. I would only miss one class because there was a virtual assignment in there too. It was great timing.
We were both tired and we rolled to our sides and fell asleep. We awoke the next morning and had a few chores to do, which we did together and I headed off to class. Upon returning Tyler had packed all of his stuff and most of mine. He asked how many bags we could have and I said, “as many as you want, I have unlimited”. He gave me a discerning look, and I just smiled, and said, “the perks of having connections”. We finished packing up stuff and headed to the truck, I said, “I’ll drive”. He again looked kind of odd at me but just went to the passenger side and said, “my turn to be passenger princess”. I laughed and said, “ok we can get you a tiara”. We headed out and down the interstate. We were approaching the airport exit and I kept going. He said, “um you are going to miss the exit”. I said, “oh we are not flying out of that airport”. He said, “what”? I said, “you will see”. We headed on down and exited and headed toward downtown, I pulled off into the old downtown airport. He just said, “what did you do”? I said, “I took care of the flights”. I drove through security, and to the back of lot and pulled into a hangar that was open. I got out and was immediately greeted by Roy, Adam, and Janice. They began getting our luggage and talking to me, I gave them a hug and then said, “hey guys this is my partner, boyfriend, um yeah Tyler”. They greeted him, and said everything is ready lets head out to the plane. He just said, “what the fuck Alan”. I said, “well my family leases this thing and rarely use it so its ours for the week”. He then said, “ummm ok we really should talk”. I just laughed and said, “I said honestly it’s a hold over from my grandfather, he never liked flying and kept this”. Roy chimed in, “we sure do miss your grandpa”. I said, “man you have no idea, I do too”.
We got on the plane which was a black and gold Gulfstream G550. I led the way and we went back to the first seating area which was a set of 4 seats facing each other with a table between them. Tyler was still quiet. We set down and and buckled in. Janice came through and asked if we need anything and I just said, “not right now, give us a few to settle in, and once we are up to altitude we might take drinks”. She moved on through to the back of the plane, did some checks and walked back up to the front and talked to Roy and Adam. She then closed the door between the front and the main cabin and we were in private. Roy announced we would be taxiing out and were clear to take off.
I took Tyler’s hand and pulled it up and kissed it. He just looked at me and smiled and said, “spill it”. I explained in more detail that my family had kept the lease on the plane because my Aunt was older and did not navigate the airports well anymore and she really did not like to travel. I went on to explain that currently she was the President of the Board, but was retiring at the end of the year, and that meant there would have to be structural changes in the holding company. He had questions about the company, the plane, the board etc. I figured it was time he knew it all, so I told him everything. He knew a bit about my parents and their businesses but had no idea about the larger company that was my grandfathers. He had made a lot of money throughout his life in many endeavors, mostly the odd combination of oil and the dairy industry. It’s a long story that I did not go into much. Just that there is a holding company now and it was very diversified mostly in the Ag sector and it was run by the board now. When my aunt retires she is turning her shares over to me, which will make my mom, sister and I equal share holders each controlling 25% of the company and the board controlling the final 25%. He asked what my responsibilities might be then, and I explained basically meetings, reports, updates and keeping up with everything. We were not looking to expand anything so it would be minimal. I was a bit uncomfortable talking about this, but it was Tyler so I shared the value and what else I had going with my parents etc. He then said, “why are you not doing that full time”? I replied, “I want to be a professor not a CEO”. He understood, he also understood family responsibility. I did tell him that he would have to understand some of what I would have to travel and do sometimes once I was on the board. He agreed, and said that he would have no problem going with me, especially if we flew on this thing. Haha.
I then said, “we are on vacation, work will be there when we get back, lets discuss something else”. He smiled and agreed, and then said, “why do you think you get to tell me what to do boy”. I felt my face flush and said, “sorry Sir”. We reached altitude and Roy said it was about 3.5 more hours into Palm Springs. Janice opened the door and asked if we wanted anything to drink, I got a club soda, and water, and Tyler got coffee and water. Janice brought the drinks and went back and closed the door. I stood up and gave Tyler a wink and said, “want to do something fun”? He grinned and said, “if it’s with you absolutely”. We went around the wall and there was a couch, I slid the door shut behind us and locked it, then knelt and said, “please use me Sir”. He wasted no time in grabbing me by the scruff of my neck and holding my face in his ass. I felt the mesh of his athletic shorts and knew that was all that was between me and the scent I loved. He pulled his shorts down and the jock perfectly framed his ass, I dove in, it was clean, but still it was Tyler. He then stopped me and slid his sorts off completely, and told me to strip. I did so and knelt back down. He then removed his jock and I began to worship him. Once it was slick with my spit, he ordered me to kneel on the couch and he got behind me and began licking my hole, it was glorious. He got it wet and I begged, “please fuck me”. He then wrapped his arms around me and grabbed each nipple, I felt the heat from him and felt his cock slowly penetrating me. He kept steady pressure until he was buried to the balls. Fuck he felt good. He slowly started rocking his hips. This was not rough or hard, it was slow, passionate and methodical. He began hitting my prostate and a stream of precum escaped my dick. He just kept hitting it and hitting it, and tweaking my nipples. I was softly moaning and grunting. The precum began to pool on the leather and I was leaking heavily now. Tyler just kept his steady pace and I was beginning to feel my orgasm build. I tightened my jaw and said, “I think I’m going to orgasm”. He just said, “let it happen”. Slowly it built and soon enough I was spasming and cum spurted out of my caged cock. Just then my hole clamped and I felt Tyler’s dick pulse and he buried his head between my shoulder and neck and grunted into his orgasm. I felt him pulse no less than 6 times and knew I was full now. He just held me and and caught his breath. I came down from my climax too. Then he slid out of me and said, “lick up that mess”. I diligently licked the couch and all of my fluids, then spun around and cleaned him off. I went to the bathroom and began cleaning myself up and he joined me. We got our clothes back on and tried to make it look like we had just not joined the mile high club. I’m sure the area now smelled of man sex. So I got an air freshener and sprayed a bit. We kissed then returned through the door to our seats. We had our drinks and the flight continued. Janice popped back in a while later and said we have about 45 minutes left and asked if we needed anything else. I said we were good and she took away our cups. We set back down and chatted about what we were doing on vacation. Tyler said that he had booked us into a nice mostly private resort, and that Spence and his partner would join us there. We landed and got picked up. We arrived at a small mid-century modern looking building. The sign said Talvera Palm Springs. We checked in and went to our villa. Just as surprised as Tyler was about the plane, I was about the villa, it was beautiful and had a private pool and hot tub, with views of the mountains. I was in shock. We checked out the accommodations and Tyler said we have a small pool but there are 3 others too. He went on to say it was an adults only place. I looked at him quizzically, he then said, “not like that, just 21 and over”. I said, “ahh ok”. There was a knock on the door and it was our luggage. Tyler greeted him and he took the luggage to the bedroom, received his tip then left. Tyler suggested we change and maybe have a swim before dinner. I then thought, do I even have a swimsuit? We went to the bedroom, and Tyler set the suit cases up on the bed, and I said, “I hope you packed swim trunks for me”. He smiled and said, “of course”. Whew. So I opened the suit case and was looking for them and he said, “oh those are in mine”. He opened his suit case then stripped, so I did the same. He then looked pulled out his which was a square cut speedo. I fell quiet, he slid his on, and then handed me a matching regular speedo. I just said, “are you sure”? He said absolutely. So I pulled it on. Now remember I am still locked in chastity. The speedo did nothing to hide this, but I was ok it was just us in our private pool. Tyler then said, “model it for me boy”. I played it up, I flexed a bit, and posed. He ran his hands all over me which led to me straining. He said, “baby boy you look perfect”. He stood behind me and we faced the mirror, he fondled my nipples, and I leaned back into him and moaned. My eyes were drawn to my caged cock which was very visible again. He noticed this and cupped it and said, “be proud I have caged you”. I smiled and said, “yes Sir”.
We made our way outside and got into the small pool, it felt great, it was warm and very relaxing. Given we had just left the Midwest where it was 35 degrees. It was great here. We both relaxed and soaked up the desert sun. Tyler’s phone rang and he said, “yes we are here come on over and gave our villa number”. He then said Spence and Grant are coming over. I started to get up out of the chair and he said, “set down I will let them in”. I said, “I was going to change”, he said, “no, set down”. I started to say something else and he just looked at me and I set back down. There was as knock on the door and Tyler let them in. They came out and I stood up and I felt all eyes on me for some reason. We shook hands and I set back down and we began chatting. I know Spencer was sizing me up and I was him. Tyler got up and he and Grant went in to make drinks, Spencer and I were left outside. It was kind of awkward quiet and the Spencer said, “so is all going ok with you two”? I responded, “yes its great”, and then went on about the sale, and many other things. He asked about me and my family, my major and everything. He shared he was excited about baseball and I admitted that I knew some of his AAA career and how he was a very highly touted player. He moved over to the chair next to me and Tyler and Grant returned, I was drinking club soda, and they had some water. It seems none of us were “drinkers”. Spencer and I continued talking and I noticed his eyes trailed toward my speedo. He didn’t say anything but just smiled. I sort of began to be more comfortable. He took his shirt off and we jumped in the pool, it felt very nice. It was getting late and Grant said, they should head back to their room and clean up for dinner. We got out of the pool and I was handing Spencer a towel and I noticed the front of his shorts, and even though he was not in a speedo, the front clung to a noticeable chastity cage. I looked down and back up and our eyes met and we both smiled. I was even more at ease now.
They left and Tyler came over to me and said, “seems like you two hit it off”. I said, “yeah I’ll be honest I was jealous at first, but then we started talking and he is a really cool guy”. And then I said, “did you know he was um locked like me”? He said, “well he is more submissive, however that is not their main dynamic, since Spence travels and plays ball obviously he is only locked when they are together”. I said, “seems like you know a bit about this”. He just said, “well we have been very close friends and stayed in touch”. I nodded. He had the suitcases laid out on the bed, and one was full of toys and equipment. Tyler said, “we have a few hours before dinner lets get some play time in”. I stripped and knelt so fast my knees almost hurt hitting the floor. He chuckled. He then placed the collar on me and I thanked him. He did some work around the bed and got the restraints in place. He put me face down, and shoved his worn jock in my mouth. He then put on a spandex hood over my head, this covered everything. He then laid on my back with all of his weight and man that felt good. He said, “ready for some fun”? I replied, “yes Sir”. He then licked my ear and I shuddered. He then stood up and began. He started with the flogger, and went up and down my backside, he then went and turned on some music and turned it up a bit. He came back and said, “that was the warm up”. I said, “yes Sir, thank you Sir”. He then had selected the prison strap and gave my ass a thrashing, I was writhing and grinding into the mattress. Next I felt him set on my lower back, and what happened next was new. He said, “ready slave”? I said, “I think so Sir, yes Sir”. He then must have had two small paddles in his hands he began smacking them into my ass rhythmically, I felt the heat rising in my cheeks, and I could tell Tyler was enjoying hisself. This went on for a few minutes, and I had tears in my eyes and was grunting into the jock, even whining a bit. He stopped and then gently touched my ass and said, “it is a beautiful shade of pink”. I said, “thank you Sir”. He then put began tonguing my hole, and I was writing in the restraints. He released my ankles and had me get on my knees and he then entered me for the second time today. Fuck he felt great, he was not slow, or nice about this, clearly this was a fucking. He was as fast and furious as Vin Diesel. He slammed in my ass and shoved my face into the pillow, I was grunting and groaning in ecstasy. He was building to his crescendo. Then he stopped. Pulled out and said, “not yet baby”, he then went back to the flogger, and began again, then he placed something in my ass. It was a vibrator. He continued flogging and I was leaking like a faucet now. Thankfully he put a towel down. Then he stopped and he had me push my upper body up and place nipple clamps on, and then resumed my spanking, this time with his hand, then his belt. I felt an orgasm building from the vibrator and beating. He sensed this and yanked out the vibrator and mounted me with gusto. He slammed in and out and my orgasm built and then like a flash it was upon me and I was emptying my balls onto the towel as Tyler was filling my hole. Then he collapsed on me. I was still riding my high and convulsing. He reached under and wildly pulled off my nipple clamps, and I squealed, and more cum spasmed out. He then let me lay there and go a cool cloth and wiped my ass and back off, then slid home a rather substantial plug. It felt larger than I had worn before. He kissed a trail down my back and across my ass. Then he undid the cuffs and rolled me over, removed the hood and jock gag. He then leaned in and tenderly kissed me. I was a puddle and just whispered, “thank you Sir”, he replied, “no thank you baby boy”. He then said, “we need to shower and get ready”. We got up and went to the bathroom, he set me on the toilet and I relieved my bladder, he reached behind and pulled out the plug and that released too. We then got in the shower. We cleaned up and dried off then he put some lotion on my butt and it felt nice. We went out to the bedroom, we got clothes out and he handed me the jock that was previously my gag to wear. I put it on and my clothes, and we headed out to dinner. We were staying on property and got to the host desk and we were seated at our table. I had not asked if we were dining alone or not, just then Spencer and Grant showed up. That answered that. We had a good meal, and I was a bit squirmy in my seat from the spanking before. This just made me get hard, in my cage, thinking about it again. We had a bit of dessert and decided to call it a night, we said our good byes and headed out. We got back to the room and once inside we were both tired, we stripped off and hung up our clothes. Tyler asked if I wanted to relax in the hot tub, I said, “sure for a bit, then bed”. I stripped off and walked out toward the hot tub, he just chuckled and said, “naked huh”? I replied, “nothing to hide from you”. He concurred. We slunk into the water and wow it felt good in the cool desert, night air. We set and talked a bit and just enjoyed each other. I said, “I’m beat, I think I’m going to bed”. He said, “yes you were beat”. We got out, covered the tub and headed in the villa. I dried off and was was about to crawl into bed when Tyler, walked through to the bathroom. I said, “where are you going”? He said, “to use the bathroom and brush my teeth”. I followed him in. He walked to the toilet and set down, without hesitation I knelt in front of the toilet. He said, “babe you don’t have to”. I said, “as your slave I want to”. He spread his legs and I began worshipping his cock, he did his business and released his piss down my throat. I kept sucking him and finally he clenched up and shot a small third load of the day down my throat. He then reached to the toilet paper and I grabbed his hand away. He understood, he stood and turned around and I did my duty. To me this was heaven, I realized some of your find this gross or a limit, to me this was a deeper connection between us and I felt at one with him. I could do this all day every day for him. When done he stood me up and kissed me. Then we brushed our teeth and went to bed. We lay down, I was on my back and he placed his head on my chest and I wrapped my arm around him and we were asleep in no time. I was so fulfilled and in love with this man!
