[GroobyKrissy]

My First Time Dressing
By: Krissy4u

Please do not reproduce without permission. Thanks!


My first time didn't actually start out as a 'solo' experimentation as it seems like so many other girls' first times. It didn't start out as raiding the laundry basket of a mother, sister, neighbor, or girl down the street; finding a pair of pantyhose in some trash container; or even reading about crossdressing in some stashed away porn magazine. In fact... my first time was actually like something out of a fantasy story somewhere... you know, those stories you read where boy meets man... man likes boy... man wants boy to be more like girl... man changes boy into girl :-) OK OK... let me explain...

It was the summer of my 18th birthday (actually, I was a 'just a little' bit younger than that but...for the sake of being legal). It was a hot summer day in Monterey Bay, California where I grew up and my parents had put together a little beach party to celebrate the beginning of summer. They had invited a bunch of friends and family and the turnout was expected to be pretty large. Normally speaking, as an awkward growing teenage boy, I wouldn't really be interested in going to these parties of my parents as they almost always dragged on and on and on and on... Plus, being from a rather large family, it was really easy for me to get lost in the crowd and forgotten about...so, I usually just skipped out. However; the weather really was quite nice and a refreshing day at the beach sounded like a great idea... so, I decided to go. Now, I'm so glad I did!

Stillwater Cove is a small, private beach in Monterey right besides a little yacht club of which my parents were members. I've always thought the club was one of the best, and possibly, only perks of having wealthy parents. It was a fun place to walk around and I knew a lot of the staff members by name and they enjoyed (I think!) having me around. I especially enjoyed the company of Rick... one of the many staff members who's only job, as closely as I could ever figure out, seemed to be walking around and talking to people. What a job! Anyway, Rick and I had developed a good friendship and especially since he and my father were very good friends outside the club.

Rick was probably in his mid-40's and it seemed like he was always talking up some beautiful woman in the club... bringing them drinks, towels, and I suppose anything else they desired. The nice thing was that however busy Rick seemed to be, he always had time to take a break and show me the newest boat, take me to the kitchen to taste the newest dish the chef had prepared or, just sit and talk about absolutely nothing. So, on this particular day, while my parents' guests were arriving, I told my Mother I was going inside the club. She waved good-bye and with a kiss on the cheek, I was soon wandering around hoping to run into Rick somewhere.

Lucky for me, he spotted me a few minutes later and waved me over to where he was holding some binoculars by one of the big windows overlooking the bay. 'Come here,' he said. 'There's a bunch of sea otters playing around in the water!' Now, growing up in Monterey, it's not like I had never seen a sea otter before...but, one just doesn't get tired of seeing the little guys splashing around like they didn't have a care in the world... so, I rushed over. He handed the binoculars to me and sure enough...not far off the beach there were about five sea otters playing in the waves. "Cute, huh?" he asked. "Definitely," I agreed. I watched them play for a couple minutes before handing the binoculars back to him. "Hey! You want some cake? There was a party here last night and there's lots of cake left over in the kitchen. Let's go get a slice!" I, never one for turning down free cake followed him to the kitchen.

Once we got to the kitchen, Rick went to the big three door refrigerator and brought out two slabs of chocolate cake. He handed one to me along with a napkin and fork. I took a generous bite and was amazed at how chocolately it was... yummy! But...needed... "Want some milk?" It was as if he was reading my mind. Rick got some milk from the fridge and we made our way to an unoccupied table in the dining area. I was about half way through my piece when I accidentally knocked over my glass of milk. It began running off the table an onto my lap. I jumped up and began using my napkin to help stop the flood. Rick came over and began to help with his napkin. "Don't worry about it," he said. Well, we got the milk under control and then I looked down at my lap. The milk had caused the khaki to turn a deep (and embarrassing) brown. "Need to change?" Rick asked. "Ummm...yeah, I probably should," I replied. "Ok... follow me."

I followed Rick down a maze of hallways until we came to a door with the words 'Guest Room' stenciled on the door. Rick took some keys out of his pocket and opened the door. Once inside Rick pointed me towards the bathroom. "I'll go and round up a change of clothes for you," he said. "There's a TV in the back room if you want to watch something in the meantime. I'll be back in a few minutes. I'm going to lock the door so no one will bother you." I couldn't help but think that Rick was a very nice guy to do all this for me...

Once Rick was gone, I wandered into the back room, which was actually a bedroom, and turned the TV on. There wasn't really anything on but I just settled on watching some sitcom. About ten minutes later, I heard the door open and Rick stepped through with a bundle of clothes in his hand. "I ran into your parents while I was outside and your Mom gave me these clothes for you to change into," Rick said, handing me a small bundle of clothes. "I'm going to change too since I'll be off in about fifteen minutes. Do you want the bathroom or the bedroom?" Rick asked. "It doesn't matter," I replied. "Ok, why don't you just change here," Rick replied as he headed off to the adjoining bathroom to change.

He must have been a really fast changer because when I was just about to pull up the clean pair of pants, he came out of the bathroom dressed in faded jeans and a t-shirt. The next thought that came to my mind was, at the time, shocking... "He's really good looking." "Need some help?" Rick asked laughing. I suddenly realized I was standing there in my underwear without a shirt on and holding a pair of pants. "Ummm...no!" I replied quickly, pulling the pants on with two quick jerks. "Do you play any sports?" I remember thinking that was an odd question to ask given the circumstances. "I play a little soccer," I replied, "Why?" "Oh, just wondering...you have a nice slim figure."

The next few thoughts that raced through my mind were a whirl of confusion. Here was this very attractive man standing a few feet away from me telling me I had a good figure. What was I to think? to do? All I knew was that suddenly my cheeks were burning hot. I was completely at a loss...well, not completely. To my horror, the front of my pants were rapidly expanding. Now, I had masturbated before...jerking off to the 'missing' Victoria's Secret catalog from my sister's room...but, never had any thoughts about guys before. So, you can imagine the confusion and horror I found myself in that day. I wondered if Rick had noticed the growing bulge in front of my pants. "Ummm...you want to watch some TV?" the way that he asked that told me that he obviously had.

He stepped over to the bed and flopped down. "What's on?" he asked. "Ummm...I'm not sure...just a show." I replied clumsily as I sat down on the edge. There was complete silence except for the TV. After a few minutes, Rick spoke. "You know, it's ok." Even with no explanation, I knew exactly what he was talking about. "It's completely natural." I found myself wishing I could curl up and die. He sat up on the bed next to me. "Has that ever happened before?" To say I was at a loss of words would be the understatement of the century. The next question left me completely stunned. "Have you ever played with it?" I'm not sure if it was just pure shock that made me nod my head 'yes' or maybe some subconscious desire tucked away deep down...

"Have you ever let someone else play with it?" I nodded my head, "No." "Would you let me?" and with one simple nod of my head, my whole world changed. Rick slid closer to me and put his hand on my thigh. He began rubbing it slowly and I could feel with each rub, the heat on my thigh rising higher and higher. The bulge in my pants was now very pronounced, my teenage hormones rushing blood to the area, making my cock harder and harder. I must have been shaking because Rick put his arm around my shoulders and whispered, "It's ok... just relax." It's hard to describe the feeling that came over me as I felt that arm go around my shoulder and hold me tight. But, somehow, I knew he was right... it was ok. I made a conscious effort to relax and enjoy the waves of pleasure his ever creeping hand was giving me.

Soon Rick's hand was right on the inside of my thigh pressed against the 'V' of my legs. I felt his fingers push my legs apart and his hand slid right over my cock. I shuddered as pleasure rushed to my brain. He began rubbing my cock through my pants more and more vigorously and I let a small moan of pleasure escape my lips. Then, I felt his hand at the waistband of my pants...slipping inside and down to my bare privates. "Mmmm..." I heard him moan softly in my ear... "You're still smooth!" Yes, I was a late-bloomer. He slowly unzipped my pants and pushed me back on the bed so that he was sitting besides my now stretched out body. I don't remember exactly what thoughts were going through my head at that moment but I do remember wishing the feelings I was experiencing would last forever.