Country Club Delight

From late in spring to early fall in my college years, I would work at the golf course of a local country club. Once the New York weather would improve enough for the members to golf, they would be out. In the late summer when I was 19, something happened at the country club I'll never forget.

For the past few years prior to that, I had gotten into the habit of wearing girl's clothing. It was usually pretty harmless, I would just sneak away some of my sister's clothing and try it on. The feeling of it all would give me such a rush and make me so excited that I would get horny at just the thought of wearing that sexy clothing. The year before that, I had some encounters with a close friend of mine, and they had marked my only sexual experiences, with either men or women. He was the only one who knew that I liked to dress up, so my secret was pretty safe.

Well, I was working later into the night on one late summer day when the secret added a new member. I had been almost completely done with work for that day, but I still had to wait for the last member to come in from golfing, and he was apparently waiting until there was not a ray of daylight to come in. After a half hour of waiting, he finally came in from the dark golf course and I went on my way to take his golf bag from him and the other usual stuff.

He handed me my tip and as I turned around, the money fell out of my hand, so I bent down to pick it up. I guess I had un-tucked my shirt while I was waiting for him, because when I bent over, my shirt came up a little bit, and I felt a tug on my waist. I was absolutely horrified. I was feeling a little adventurous that day before work, and thought it'd be fun to have a little secret, so I put on a pair of panties underneath my shorts and golf shirt uniform.

"Is this part of the uniform too," the member asked as he let go of my panties and I stood back up. I was so embarrassed, and my face was red. I put my head down and nodded "no", trying to avoid the embarrassing eye contact.

He told me to look at him, and I looked up to see him grinning down at me. Now I was just a very small young guy. I was 5'4'' and a slim 115 pounds. My hair was long, and I had a little bubble but, making for an overall very effeminate build. The member on the other hand was a big, strong 29-year-old man. He stood at over 6'4'' and weighed in at around 240 pounds of mainly muscle. The member was a specimen of a man, and I won't lie and say I was not intimidated by the size difference.

He stepped a little closer to me and held my chin up, telling me there was nothing to be embarrassed about, that not every guy was made to be a big alpha man. I started to feel a little better about it, like he wouldn't tell anyone, and smiled a bit. Then he asked me if I had any more of those clothes where that came from. I got caught up in the tension of the moment, and told him they were in my car. So I went and got the non-descript bag out of my trunk that had a few girl's clothes that I snuck away from my sister piece by piece so she didn't notice. He smiled and told me to get on the golf cart, and drove me out onto the dark golf course, making sure to go in the middle of it, so we were out of earshot or anyone happening to go by.

My heart raced and my mind was flooded with thoughts as he drove out onto the course. I had been with a guy before, but it was my best friend, this guy was just a member where I work, I only had made small talk with him. I was lost in thought and didn't notice him stop the cart, so he shook my shoulder to put me back in reality.

"Well....are you gonna go change?" I shook my head and snuck off behind a tree, still not believing exactly what was going on. I took my work uniform off and began to get the new outfit on. My panties were already on, so I matched it with the pink bra I had, and then slipped a short, loose, white dress on overtop. I put on some white heels to give me an extra inch or two on the large man waiting, fixed my hair, took a deep breath, and stepped from behind the tree. There was a small light from one of the little buildings on the course, so he was able to admire my transformed body, shaved, smooth legs, and perky ass trying to escape from the short dress. His eyes widened and in his deep, booming voice said "I never knew that the little club cleaner boy was so....sexy."

I was so flattered by this as he walked closer to me, and I could see the wheels in his mind turning with the things he wanted to do. He ordered me to my knees and dropped his shorts. Under his boxers, I could see his thick ten-inch cock itching to break free. I pulled those down and it shot right up to my face. I looked up at him, down at his cock, took a deep breath, and went to work.

I sucked on the tip of his cock until I could tell that it finally stopped growing, and then worked my way down his shaft slowly, my hands tickling his large, full balls along the way. When I would shoot my eyes upward, I could see him staring down, watching the person he knew as a small, effeminate boy please him.

This went on for a few more minutes, when he stopped me just before he came. I knew where he wanted to go with this, and I also knew that a person my size stood no chance of stopping him. Luckily I had no intentions of stopping him. He pulled me up and turned me around, telling me to lean against the mound of grass we were near, and as I complied, I felt him lift my dress up. He ran his big hands over my tight little ass, and continued to pull my panties to my knees.

I turned around to see the hulk of a man preparing to make me his bitch. His cock was still dripping wet with my saliva as he put the big head of it into my tight little hole. I took a deep breath and prepared for the ride of my life as over the next minute, he worked himself, inch by inch into me, until he was all the way in.

My ass handled it with surprisingly little pain, to my relief, but when he started to pump back and forth, a mixture of the worst pain and best pleasure rushed into my body. His hands grabbed onto my hips, and from then, I was entirely under his control. He started to pound away at me quickly, and from the strength of his thrusts and power of his arms, I could feel myself being lifted up at his will. My 115 pounds must have felt like nothing to him, a mere ragdoll meant for his pleasure.

On the other hand, I felt like I was being handled by a bear. He lifted me from the ground and dropped me down at whim and all I could do was moan, with tears of pleasure starting to stream from my eyes. My lack of control in the situation brought out the deeply submissive side of me, and it made me so horny to think of what was happening. My hard little three inch cock shot a little load onto the grass as he was pounding away at me, but he didn't seem to notice or care.

My body was shaking in ecstasy for the next thirty minutes as he opened up my tight hole. I loved it so much that my little cock came again without him noticing. By this time, we were both pouring sweat from our bodies as he would fuck me doggie style, turn me around so he could see my face, then flip me back again. I did anything he ordered and he grunted loudly with approval if he really liked a certain thing. I was amazed that he could possibly last this long, and knew that he had to come at any minute, whether from pleasure or exhaustion.

While getting me doggie style, I felt him start to slow down and get a little more tense, so I knew that it was finally time for payday. He clamped his hands on my hips like a vice, forced his cock all the way in, and let out a deep breath. Immediately, I could feel his seed erupt into my body. It was like a fire hose was going off inside my ass, but instead, shooting off hot, thick liquid. He held onto me for a minute as wave after wave of cum drained from his balls into my ass. How a man could have this much cum absolutely baffled me, as I could probably only fill up a shot glass on a good day. But he seemed unaffected by the amount he was shooting into me, and finally after the minute, he eased himself out of me.

I collapsed down to the ground in exhaustion, catching my breath and clenching my ass to hold his torrents of seed inside. I rolled over to my back to see what he looked like after such a session, and he seemed almost unaffected. His body was sweating, but he wasn't out of breath, and his muscles seemed to swell even larger, perhaps because of the testosterone surging through his body. He just turned me, an effeminate employee at his country club that he hardly knew, into his own little toy. From the look on his face, I knew that tonight would not be the last time he had his way with me, but I didn't mind, and I was in no position to put up a fight.

As he put his shirt and shorts back on, he looked at me and said "would you like to get a ride back in, or should I give you some time to yourself?" I couldn't believe that he was already fit to go back towards the clubhouse, but there was no way I could get myself up. I told him to go along without me, and he just grinned and said "Okay, well I will leave your extra tip with my golf bag, good night." I waved at him as he walked back to the golf cart and rode back towards the club house.

As I watched him go, I could not believe what I got myself into. I was lying on a grassy mound in the middle of the golf course, exhausted from the hour that had just occurred. I had only one heel on, the other was laying a few yards from me, kicked off in a fit of passion, my dress was all the way up, bunched up just below where my bra was, hair tousled with bits of grass in it . My panties held my ankles together and my ass had never felt the way it did before. It was slowly shrinking back to its regular size as his cum was oozing out, bound to harden inside me soon. My body had just been ravaged in the throes of his orgasm, and I could hardly move a muscle, but I had never felt better in my life.

I laid there for about an hour, the gentle breeze caressing my sensitive body, until I thought it was time I should get going. Just a few hours earlier, I was finishing up a regular shift of work, and now the night had turned into one of the best in my life. I took off my outfit, just leaving the panties on, and began to put back on my uniform. As I took the long walk back to the clubhouse, the cum finally plugged in my ass, and I thought of the next time I was working on the schedule, and how from now on, I plan on asking for some more late shifts.