My First Time Dressing
A True Story By: Krissy4u
http://www.krissy4u.com
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.
Unfortunately, I was young and easily excitable at the time. It wasn't very much longer that I could feel the waves building to a peak and then come crashing down all around me. It was incredible...so much better than when it was just me and a magazine. I was breathing heavily when I felt a warm wetness on my stomach. Surprised, I looked down and saw Rick's head over my stomach... he was licking the cum off my body with short strokes of his tongue. He glanced up at me and smiled...I smiled back and let my head fall back to the bed. Rick continued until he was satisfied there was not one spot of cum left on me and then began kissing and licking my thighs and my now deflated cock. I continued to lay there, not quite knowing what to do.
After a few minutes, I felt a warm sensation that took my breath away. Rick had slipped my limp cock all the way into his mouth and was slowly sucking on it. I could actually feel myself getting harder and harder again by the second. Soon, his efforts were rewarded with a second load which he took completely in his mouth. Strangely, I remembef feeling so honored that he would go through all this effort just to make me feel this good.
As we both lay there panting, the thought of what had just occurred hit me like a ton of bricks, followed by a flood of tears. "Hey hey hey," Rick whispered, running his hands up my body to my face. "Don't cry... didn't you have a good time?" I think I managed to sniffle out a pathetic sounding, 'yes'. "Well, what's the problem then?" Silence...I just couldn't bring myself to say what I was feeling. "Well, if you want, we can keep this a secret... would that be ok?" I nodded. "Ok then, it's settled, I won't tell a soul." Somehow, that made me feel a whole bunch better. I felt Rick's hands caressing the side of my face, wiping away the stray tears that had fallen there and then, he leaned close and kissed my forehead. "Would you like to meet again?" he asked. An affirmative nod from me started a summer of meetings that found me exploring my blossoming sexuality...
It was easy to meet with Rick since the club was only a few miles away. I soon took to riding my bike to the club and Rick where we would invariably end up in the 'Guest Room' exploring each other's bodies. It was probably ten or so meetings down the wire when I called the club asking if Rick was there. When he got on the phone, I asked him if he'd like for me to come over in the afternoon. He said that he had a better idea, asking me if I knew where the ********** hotel was in Monterey. I told him I did and he gave me a room number and time to meet him there. I have to admit, I was VERY intrigued.
I showed up at the room at the specified time and knocked lightly. Rick opened the door and ushered me inside. It was a VERY nice room and on the bed I noticed several packages. "These are for you," Rick said, coming up behind me. "But, you have to open them in order." He handed me the first package. It was simply wrapped and very light. I opened it carefully, not quite knowing what to expect. It was definitely nothing I ever expected. Inside was a black garter belt with a very familiar logo on it, 'Victoria's Secret.' Also, was a black, lacy bra and matching panties, and a package of black, seamed stockings. My confusion was probably pretty obvious as Rick's voice quickly broke the silence, "I just think you would look adorable in these. You can try it once and then if you don't like it, you don't ever have to wear them again. But, would you do this for me, just this once?" I gave a nervous laugh and asked, "But, aren't these for girls?" He laughed, "Well, girls wear pants don't they?" Silly logic I know, but in my confused state of mind, it seemed to be enough of an answer. "Well, ok then."
He handed me a second package off the bed which I opened with even more curiosity. Inside this one was a very sexy black corset (which i still have to this day!). At the time, never having seen a corset before, much less worn one, I was actually wondering what it was and had to ask Rick to explain it to me. After he had finished explaining all the ins and outs of corsetry, he handed me the last package. This one felt a bit heavier and I knew what it was even before I opened it. "I guessed at your size so I hope they fit." Rick said. I think this last gift was what really hooked me into the whole crossdressing thing... a beautiful pair of black patent pumps. I slipped one on to see if it fit or not and it seemed to magically slide on... it looked so natural on my foot...definitely love at first sight. "Well, what do you think?" Rick asked. I think subconsciously I already knew I was hooked, but I gave a very political answer... "Well, I suppose it can't hurt to try it once." I headed to the bathroom with the gifts to try to figure out how everything went on.
In the bathroom, my heart pounding, I opened up the package of stockings. They felt so smooth against my hands that I couldn't wait to get them on my legs. I pulled them up, and in hindsight, it's a miracle I didn't put runs in them in my naivety! It took me some time to get the seams straight but eventually, I got them running vertically along the back of my leg. In the mirror I definitely liked the way the line accentuated every lean muscle of my lean calves and thighs. I ran my fingernails from my knee to the top of my thigh along the stocking and could feel myself getting harder and harder. I had to stop or else I was going to cum right then and there!
I pulled on the lacy panties and again looked into the mirror. My butt looked so cute framed in the lace that I couldn't help but be jealous of the women who got to wear such things every single day! The bra was easy after figuring out the fastener... I'm not sure if Rick was thinking of me or himself when he bought the bra, but it had a fastener in the front which made things very easy for my first time dressing. The corset was a whole different matter... I tried to figure out all the strings and hooks but was just getting frustrated so I called out to Rick, "Ummm....I don't think I can put the corset on alone?" "That's ok," he called back, "Just put everything else on and I'll help you with that." I slipped on the black pumps and took my first step in heels. Turns out, I was a natural. I half expected to fall on my ass after the first few steps but found walking in heels not a difficult challenge at all. So, after one last glance in the mirror, I grabbed the corset and headed for the door. "Here I come!"
As soon as Rick saw me I knew his cock was rock hard underneath his pants. His eyes said it all. I can't say that I can totally relate, but, I at least have a pretty good idea what a woman feels like when men are 'undressing' them with their eyes. I found the sensation to be extremely flattering. I threw the corset at him and teased, "Stop staring!" "Baby, you look so hot," he replied, "I can't help it!" I looked down, feeling my cheeks crimson at his words. He got up off the bed and walked over to me. "Turn around," he said. I complied and soon felt his hardness pushing against the small of my back. I moaned, reaching back with my hand and rubbing the front of his pants. "Oh baby," he said, "I can't wait to make love to you today." Now, thus far, 'making love' had only consisted of lots of foreplay, rubbing, kissing, and sucking. This time, I knew exactly what he wanted... he wanted to make me his girl.
The change that came over him was incredible. Before, he was always very gentle and slow... this time, he was much more intense. He pushed me towards the bed and in the high heels, I tumbled easily on it. He slid over me and I could feel the weight of his body pressed against mine. It is an incredibly sexy feeling having the weight of a man pressing you down into the mattress and feeling a rock hard cock poke against your skin. We kissed for a while, slowly and then building up until he was fiercely ramming his tongue into my mouth. I have to admit, I was just a little bit scared with this change in his behavior...but, it also really really was starting to excite me. His hands were roaming up and down my body, the corset now just a piece of clothing discarded on the floor. Every time they passed my over the bra, I could feel the fabric rub against my nipples making them more and more sensitive and hard.
My knees were now bent and my legs wrapped around his back as he moved on top of me, kissing everywhere. His mouth found its way to my little nipples and he sucked eagerly at them, first one and then the other. The explosion of feeling from his sucking was enough to start the pre-cum oozing from my hard cock. His hands moved over the panties and rested on the ever increasing wet spot now developing there. "Mmmmmm..." he moaned, "Is my little girl getting all wet for me?" The next words were so natural they just leaped from my lips, "Yes, Daddy! You're making your little girl so hot!" He whispered in my ear, grazing the lobe with his teeth, "Do you want to be Daddy's little girl?" "Yes, Daddy," I moaned, "Please make me your little girl." "Are you going to be a good little girl?" At this point, he could have asked me anything and the answer would have been, 'yes'. But, without even giving me time to answer, he moved onto the next question... "Are you going to be a good little slut for Daddy?" Now, this was a new word. I mean, I knew what a slut was...but he had never used it in reference to me and somehow being called one just about threw me over the edge. My panty covered cock now started thrusting upwards against his palm. "Mmmmm.....good little slut!" he whispered. "I'm going to make you Daddy's little fuck slut today." "Yes Daddy," I begged, "Make me your little fuck slut!"
I felt his hand slip lower and a finger playing with my virgin hole. Out of nowhere he produced some lube and proceeded to squirt a generous amount right down the crack of my ass. The coldness of the liquid suprised me and I let out a breath that I'm sure he took for pleasure. I suddenly felt my hole being penetrated by what felt like a massive rocket trying to shoot it's way into me. I squirmed underneath him and he said calmly, "Just relax and it will feel good soon...it's going to hurt a little first though...it always hurts for little girls the first time." DAMN RIGHT! I thought the finger was bad...but, it was nothing at all compared to what was coming next.
After a few minutes of having his finger assault my tender ass, he finally decided it was time to 'take my cherry.' He moved my legs from around his back to the top of his shoulders and I couldn't help but feel very vulnerable with my ass exposed and my legs in the air. I also couldn't help but notice how sexy my legs looked encased in nylon and topped off with those black heels that just screamed, 'FUCK ME!' Which was exactly what happened. Rick's cock was hard... HARD. And, I felt every millimeter as he pushed it slowly inside me. It hurt so badly I thought about screaming but was able to hold it back. Instead, I concentrated on watching Rick's face as he took my virginity. The look on his face was incredible... he was totally wrapped up in this little fantasy... fucking a cute, little Asian girl for the first... he looked down at me and I swear it almost made me cum. It wasn't very long before I felt the 'pop' as the head of his cock broke past my opening and slid down inside me. then, little by little, he pushed further until the entire length of his cock was buried deep in my ass. Then he began pulling out...
After all these years, this still remains one of my favorite things. I love having a cock buried deep inside me to the balls and then feeling it slowly being pulled out. It's so hot because it makes you want to be filled back up again...then, when he pushes back inside you...man! pleasure city. But, that was just a side note. Anyway... he turned out to be right after all. For all the pain in the beginning, it wasn't long until I began to realize that every time he entered me, something inside me punched the pleasure button in my brain. Soon I was thrusting back against his cock as much as I possibly could to try to maximize that feeling with every thrust. From our past experiences, I could tell that he was getting close to cumming and this brought up a whole new set of questions for me to ponder. Please remember, I was young AND STUPID! I didn't really even think about condoms or anything even remotely resembling safe sex at that point in my life. I was just wondering where he was going to cum. Well, that question was soon answered. I could feel his whole body tense up in a pre-climax quiver. And, then, with a couple of hard thrusts, I knew he was filling the inside my ass with his cum.
I'm not sure if it was the pure submissive feeling of having my ass pumped full of cum or just the fact that I was so turned on by that time; but, with just a couple jerks on my own hard, panty covered cock, I quickly emptied my own load. The spasm my ass made around his cock must have felt pretty good because with each wave of pleasure rolling over me and echoing in my ass, he moaned in my ear. "Mmmm... you're such a good little girl," Rick breathed. We lay there until I felt his hard cock getting soft and finally falling out with quick pop. It felt strange...being empty. He kissed me lightly on the cheek and rolled besides me, wrapping his arms around me. I lay there until suddenly I could feel his cum oozing from my tender hole.
Embarrassed, I unwrapped myself from his arms and made my way to the bathroom door. I could feel the cum dripping down the inside of my leg and onto my new stockings. I suppose there was no turning back now...I was completely hooked. And, ever the girl, I remember my last thought as I entered the bathroom being, "Damn, now I have to wash these!" A girl's work is never done.
The End
