Pilates with Jake

My name is Alex. I was 25 and had just recently finished graduate school, broken up with my long term girlfriend, and was taking the summer off before starting a job in the fall. I had plenty of time alone, and I was taking the time to get my life in order and to get into better shape. While I had always been slim, I was running a lot more and getting more toned - a friend of mine even convinced me to try a Pilates class for strength and flexibility, and I figured it might be a fun way to meet girls as well. At first I thought it was working, as some of the girls would invite me out for drinks after class, but we always hung out as a group and they mostly treated me like a friend. They would talk a lot about hooking up with different guys, different positions, how to give a great blowjob, which of course interested me quite a bit as most of them were in shape and pretty hot.

One girl in particular talked about how her muscular boyfriend would pick her up and he'd fuck her standing up while she wrapped her legs and arms around him. I knew I could never do that with a girl, but instead of being upset I have to admit I couldn't help thinking about what it would feel like to be lifted up off the ground like that, to be helpless. I wasn't even thinking about her boyfriend - or any guy in particular - but just the idea of being held and controlled by someone else was a huge turn on.

Some of the girls in the class seemed to prefer guys who trimmed or even shaved their pubic hair, so one day I tried that out as well. I have an average sized cock, and when I shaved it definitely looked bigger. But what really surprised me was when I turned around and noticed how round and firm my ass had become thanks to the Pilates. I don't really have any body hair, and with my pubic hair shaved I was mostly smooth all over. I ran my fingers along my recently shaved crotch and along my ass, and got so horny that I had to masturbate pretty much immediately. I even started to moan a bit right before I ejaculated, which is something I never did before.

The next day at Pilates class, another trainer from the gym had stepped in to replace the regular female coach. His name was Jake, he was in his early 40s, much taller than me (I'm pretty short at 5'9"), muscular and handsome with salt and pepper hair. Of course all the girls were happy with the temporary change. Oddly enough he kept staring at me: as I was the only guy in the class I was worried he thought I was some pervert or something! I couldn't help staring back at him. He was in great shape, and admittedly had a significantly larger bulge in his shorts than I did. I'm sure he caught me looking at least once, and I blushed and looked down into my exercise mat.

One of the exercises we did involved lying face down on your stomach and lifting your upper body from your hips, which kind of pushes your crotch area into the ground a bit. For whatever reason, today this exercise really had me turned on, and I got so hard that I was worried I would accidentally cum right there in class, grinding into the floor. I was getting really flushed and embarrassed, so I left the class early, trying my best to hide my hard on. I may have imagined it, but it seemed like Jake noticed how hard I was as I was leaving the class. Once I got into the dressing room I managed to calm myself down a bit, but I couldn't jerk off in the shower for some actual relief as there were too many guys around.

I just wanted to get home as quickly as possible so I could play with myself, but as I was walking out of the dressing room I noticed Jake in the shower, naked and rubbing soap on his cock, which was huge, thick and bigger than mine even though he was only semi-hard. I must have stood there transfixed for a second or two, and he noticed me looking and smiled. I was so embarrassed that I ran out as fast as I could. When I got home I stripped down and immediately started masturbating, but this time, instead of just sitting down or pretending to fuck a girl, I bent over in some of the Pilates positions I had learned in class, with my ass sticking out.

I started moaning again, and I couldn't get Jake's huge cock out of my mind. I was so horny that I wasn't thinking clearly, and all of a sudden I realized that I needed to taste the precum that was all over my fingers. I put two of them in my mouth and started sucking - the taste was weird but not bad, and I was getting even more worked up. Without even really knowing what I was doing, I took one of my fingers and slowly put it in my ass, moaning as it went in. As it slid in deeper I sat up, slowing pushing it all the way in, stroking my wet hard cock and moaning even more as I rode my finger back and forth. I only lasted a few seconds until I came all over my chest, immediately embarrassed and ashamed about what I had done and that I had been thinking about Jake's cock the whole time.

I decided to skip the next two Pilates classes, hoping to avoid Jake until the regular teacher came back. After the second class I got a message from a random number - apparently Jake had noticed I wasn't there and one of the girls from class had given him my number. He said a bunch of them were going out, and that I should join them because he thought that Chloe - one of the girls in the class - was into me. I was so relieved to hear that a girl found me attractive, but even more so that there was no confusion with Jake after I had seen him naked.

I met them at a bar close to the gym, Jake was at a table with Chloe and another girls and he waved over to me. "How are you doing man, we were missing you in class this week," he said while making room for me to sit down next to Chloe. They were already a few drinks in, so they had me take a shot right away and I was soon up to speed. After a few more drinks, Jake suggested we go hit the dance floor. I'm a pretty terrible dancer, but I think I impressed Chloe by making fun of myself - or at least I made her laugh. I was feeling great and had completely forgotten about what I had done earlier in the week. I barely even noticed when Jake's hand brushed up against my ass a few times while he was dancing with the other girl.

I was already pretty excited because Chloe started dancing up against me, and I just assumed it was an accident. We danced for a while, and then the girls got an Uber to head back to their place because Chloe had to work early the next morning, but we made plans to meet up for dinner later in the week, just the two of us. "Up for a night cap at my place?" Jake asked me "I live right around the corner." I had a nice warm buzz going, and was really grateful to Jake for inviting me along, so I said "Sure, why not!" It was a hot, humid evening and just starting to cool off a bit, so we walked back to his place. He had a nice house close to the gym with a big, secluded backyard and a swimming pool.

Jake went to go get a few beers in the kitchen, and when he came back he had changed into a t-shirt and some loose shorts. We were sipping our beers when he asked me if I wanted to smoke a bit. I don't usually, but I was feeling comfortable with him and so I smiled and said "Sure, why not!"

We went out to his back porch, he lit up the joint, and we smoked while talking about the girls in the Pilates classes. I was getting pretty stoned and felt warm all over, when Jake asked me "Hey, do you want to try some Pilates positions? You can really get a good stretch going when you're high." I told him I wasn't really dressed for a workout. Not to be deterred, Jake ran back inside with a spare swimsuit, which just happened to be a white Speedo.

"I'm not sure," I said, "I'm pretty tired and kind of just want to relax right now." He wouldn't take no for an answer, saying that it would help me to unwind, and besides, I had missed the last two classes. Finally, I relented, and he told me I could go to the bathroom to get changed. I stripped down and pulled on the Speedo, realizing that it was actually a bit tight and that it didn't really fully cover my ass in the back. "Oh well," I thought, "It'll only be for a bit and I'm sure he's right that it'll help me to unwind."

When I came back to the backyard, I saw that Jake had laid out two exercise mats and told me to come join him. I also noticed that he had taken his shirt off: he had a muscular torso with barely any fat, and even though I had quickly seen him naked, I was shocked at how much bigger he was than me. He was definitely the kind of guy the girls were talking about: the kind who could lift a girl up and fuck her in the air. We did a few leg raises and then some stretching exercises. During the leg raises, I realized he wasn't wearing any underwear and his massive cock kept falling out of his loose shorts. Getting a glimpse of his cock made me think about what I had done a few nights ago, only this time I wasn't feeling ashamed or embarrassed, but oddly excited.

At this point we were both pretty sweaty and getting a bit tired, so he suggested we do one last exercise and then cool off in the pool. "Why don't we try some torso raises?" he said smiling, "You seemed to really enjoy them during our last class." I was so embarrassed that all I could do was nod and get into position. After about two or three reps I felt a light breeze on my ass and realized that the tight Speedo was covering even less of my ass than before. I also had gotten extremely hard, and when we finished I was doing my best to hide the outline of my hard cock in the swimsuit.

Jake didn't seem to notice, and started to walk towards the pool. I got up to join him, only to realize that my white Speedo had become semi-transparent with all my sweat, and that I was now pretty much fully exposed. He smiled and said "I told you those exercises would help you to relax," then stripped off his loose shorts and jumped into the pool, naked. "Now we're even," he said, "And you don't need to be embarrassed, I swim naked all the time." Not wanting to disappoint him, but also hoping that he still hadn't noticed how worked up I had gotten, I turned around and stepped into the pool backwards to hide my now extremely hard cock.

The water felt amazing, and I was really relaxed after the exercises and stretching, so I didn't notice Jake swimming up behind me. With a wicked grin, he picked me up out of the water as if I weighed nothing, and threw me a few feet away, making a big splash. "Oh now it's on!" I said, swimming towards him and jumping onto his back to try and pull him underwater. I could barely even move him, and with no effort at all he pulled me over his shoulder, playfully spanking my ass a few times to show me who was really in control. My hard on, which had subsided a bit after getting into the pool, came back with a vengeance after he spanked me. On the last slap, he pulled me down so that my crotch was grinding into his shoulder, and to my horror I let out a small, involuntary moan. I was trying to wrestle my way out from this humiliating position, and when I reached down to try to get some leverage I accidentally grabbed his cock, which was now hard as a rock.

He put me down and - with his hands on my sides - moved me up against the side of the pool. He had me pinned, and I felt his massive cock against me. My heart was beating so fast, and I tried to laugh and move but he wouldn't let me go. His hand slid down and brushed the tip of my penis through the tight swimsuit, and I shuddered and let out another moan. "I know it turned you on to see me naked in the shower", he said, "I bet you went home and jerked off thinking about my cock, right?"

Finally, I was able to speak, "Listen Jake, thanks for inviting me out, but I think you've got the wrong idea, I really should get going."

When I went to pull myself up on the edge of the pool, Jake just smiled and said "Fine, but leave my ex-girlfriend's swimsuit to dry on that chair by the pool. I have you admit, it looks much better on you than it did on her!" I froze, halfway out of the pool, finally understanding why the swimsuit was so tight and kept riding up my ass. "In fact," he said, "You've probably got one of the hottest asses I've ever seen."

I should have been upset at what he said, but it had been ages since anyone seemed interested in me, so being complimented by this sexy, muscular, handsome man made me flush and happy. Instead of taking off the Speedo and walking back into the house to leave, I bent completely over and pulled it down slowly, exposing my ass to Jake. I had no idea what I was doing or where this was going, but I was feeling so turned on and I wanted to show off for this man who had just said I had a great ass. Jake pulled himself out of the pool and came to stand next to me, his huge cock fully erect and dripping, right in front of me. "That's more like it," he said, "Do you want to touch it?"

I was just staring transfixed at his muscles and his thick, glistening dick. I reached out to touch it, but he grabbed my hand and said "You have to tell me what you want to do." He saw that I was embarrassed, so he told me to repeat after him. "Tell me that you want to feel my cock," he said.

"I... want to feel your cock in my hand Jake," I whispered.

"No, not 'Jake'," he said, "'Daddy.'"

I blushed: how did he know? "I want to feel your cock in my hand, Daddy," I finally said, moving towards him.

"Good boy - or are you more of a girl? We'll find out later..." He took my hand and guided it towards his cock. I wrapped my fingers around it and started playing with it, stroking it up and down. "Good" he said, "Now down on your knees, baby."

I knew what was coming next, and was down in front of him in a second, still stroking his dick with my hand. My mouth was watering, and I leaned forward to suck my first cock, not even thinking twice about it. I could barely fit him in my mouth, and did my best to imitate what my ex-girlfriend used to do with me, licking and sucking the tip of his shaft, while using my hand to keep stroking him.

Jake seemed to appreciate my efforts, and let out a few satisfied grunts. "Yeah, just like that baby. You're such a good little slut." Without thinking, I moaned on his cock when he called me a good little slut. "Oh, you like that?" he said, "Maybe you are more of a girl after all..." My own smaller dick was leaking precum, and I couldn't resist anymore so I started stroking it hard as I sucked him. I was so horny that I knew it wasn't going to take long for me to cum. "Oh no, not like that" Jake said as he pulled me to my feet, "I want to see you cum like a good little girl." I was so dizzy that I could barely stand.

He pulled me close to him, kissing me, invading my mouth with his tongue. I had never been kissed like this before, to have another man take control. I lost my balance and fell into his strong, muscular arms, my hands pressed against his torso while he kissed me deeply, making me his. Finally satisfied, he pulled his head back. Seeing how dazed I was, he picked me up in his arms and carried me inside to his bedroom.

He placed me delicately on the bed, still in his arms, and kissed me again. He broke off earlier than before, and began to kiss my chest all over, working his way down to my crotch. "Good, you're nice and shaved, just the way I like it" he said.

I could only look up at him and bite my lip as he wrapped his tongue around my smaller but very hard cock and started sucking me. He was amazing, and I was moaning again, almost out of control, running my fingers through his hair as he deepthroated me. His hands worked their way back up my chest and found my nipples, and when he pinched them I moaned again, but this time I realized I was sounding more and more like a girl.

"Oh," he said, "Do you like that baby?"

"Yes Daddy," I moaned, "Oh god yes."

He kept going for a while, until my moans sounded completely feminine. After a while I saw him reach for a container beside the bed. He dipped his finger in, then slowly and gently started rubbing it against my ass. Everything was happening so fast, and I wasn't sure that I was ready for what seemed to be coming, but my entrance was getting so warm and hot as he rubbed me. Maybe it was the weed and the alcohol, but when he finally slipped his finger in it felt amazing.

He opened me up a bit, and then hit a spot with his finger that sent shocks running through me. I moaned even louder than before, and he started massaging this magical spot as my legs fell completely open. He had two fingers in now, and I was pushing back against him, wanting more. "Oh god Daddy, that's so good, I feel like I'm going to explode."

He saw how close I was getting, and gently but immediately pulled out. "Not yet, I want to be able to cum with you." He pulled my legs apart and started rubbing his wet cock against my now eager hole, stopped, and then started again, teasing me. I was going crazy, and tried to pull him into me, but he stopped and pulled back, saying "I need you tell me what you want."

Blushing, I managed to whisper "I want you to make me cum," but he wasn't impressed.

"No, I need you to really convince me."

I was embarrassed and a bit upset, but I could tell that he was perfectly okay to stop right now if I didn't offer myself to him completely, and I wanted it so bad. "Please Daddy, I need you to fuck me hard until I cum like a good little slut," I finally said, realizing that by saying this I was giving up completely to him.

He smiled and said "Good girl," and slowly and gently pushed into me.

He was huge and it was uncomfortable for a few minutes, but he had warmed me up and what was initially a feeling of being too 'full' turned into something else entirely. As he pulled in and out, he was slowly loosening me up and his cock was rubbing against every part of my ass. It felt even more amazing than his fingers, and each time he rubbed against 'that place', I moaned like a girl. He kissed me again and I wrapped my legs around him, pulling him into me, taking him deep inside.

My moans got louder and louder, until I was almost crying. "Oh god Daddy fuck me hard, fuck me like a good little slut" I moaned. He pulled me up to his chest so I was sitting impaled, his arms wrapped around me holding me up, bouncing me up and down on his cock. He started grunting more frequently, and started spanking me. Each time I moaned louder and louder, feeling something building up inside me. Finally, after the fifth spank, I came harder than I ever have before, exploding all over his chest, moaning and falling into him. He pulled out and with one final, loud grunt sprayed an enormous amount of cum all over me, hitting my chest and face, marking me, making me his.

I collapsed against his chest, completely spent. He wrapped his arms around me and kissed me, then asked me if I was Daddy's little girl. I nodded and said yes, looking up at him, knowing that I was now his and that tonight was only beginning.

Jake was gone when I woke up, but he had a left a note saying that I was to take a shower and go home, where I would find a package with a present and some instructions for tonight, but that I was not to touch myself until he told me I could. I was a bit out of it when I got up to go to the bathroom, but thinking about last night got me really excited, and I had to hold back from playing with myself in the shower.

I got dressed and walked out through his backyard. As I passed by the pool, I saw the tiny Speedo he had made me wear the night before and blushed, realizing now that it was obviously a girl's swimsuit. Still, it turned me on to think of how hot Jake thought my ass was when I was wearing it, and as I walked out the backyard gate, I was swinging my hips for him, pretending he was watching me, and I squeezed my ass around what I imagined was his hard, thick cock. I couldn't wait to get home!