I am Ray, a 31 year old single bi crossdressing male. I am not passable, I just love dressing up in cute girly clothes. I live in a small coastal community, about 5 miles inland from the beaches. Between my house and the beaches is a large wooded park area that is almost all a series of small trails through the woods. Now that the weather had warmed up I decided to go explore as I had not ever spent any time there since I moved into this area.
While on an early evening walk one day, I noticed quite a few young couples (mostly high-schoolers) hanging out and making out in various spots and it hit me that this was a good quiet out of the way place for them to get away and and be alone, make out, screw, whatever! I made a few more late afternoon and early evening walks through the trails, kept seeing the same things, but I wasn’t daring enough yet for a late night walk to see if I could catch any of these young cuties in various stages of undress and whatever fun activities they were engaged in.
I was up early on a beautiful Saturday morning and decided on an early morning walk. The whole park was completely empty everywhere as I expected it to be. I walked through a small maze of trails and picked a small offshoot with a bench and small grassy area to refill my coffee from my thermos. I was enjoying the trees and birds, still not a soul anywhere but myself, and out of the corner of my eye, I saw something white by the clearing. It looked like clothes of some sort, I got up to check it out. Sure enough, clothes, even better panties! White, bikini style with pink trim and pink hearts, and small. I could only imagine the little cutie that had these on last night. I also couldn’t wait to get home and slip them on. I picked them up and slipped them in my pocket. After nosing around a few more trails and clearings, I could tell this place was full of activity. After making a small journey around a few out of the way places that these kids might duck into for a quickie I noticed a few condom wrappers, empty beer bottles and a few other bits of discarded clothes, even a nice bra. I knew I would be making this place an early morning habit.
I headed home and immediately stripped when I walked into the house. I slowly pulled the panties on, they were a little snug, but felt great. I slipped the bra on next, just a simple little sports bra, but still very cute. It took me all of about 2 minutes to bring myself to orgasm. I kept the panties pulled over my cock so I could fill them with cum.
I decided that Saturday and Sunday mornings were the best times to take my early morning walks, as the kids would be there on Friday and Saturday nights. Over the next few weekends I found 4 more pairs of panties and 3 beautiful bras. I also found a cotton training bra, which was too small for me to wear, the others fit great.
I went up early one Saturday morning, about 6:30, it was almost time for summer break, so I knew the evenings would be a lot busier. I went straight to the first clearing area, which is way off the trail. Apparently it was a good night there, I found 2 cute little pairs of panties, a nice mint green Victoria’s Secret t-shirt bra, and a light blue cami top. I could hardly contain myself, almost a whole outfit, probably from 3 or 4 different girls, as they were scattered around the small grassy areas. I walked back out to the trail, and wandered around some, making sure the area was still free of people. I took the main trail down towards the end, there was another little out of the way place back there. I walked to the small grassy clearing, very small, about an 8 foot by 8 foot area nestled in the woods away from everything. I started my search along the edges and found a cute little black thong and a pair of powder blue boy shorts. This place must have sounded like an orgy last night. I sprawled out on the edge of the grass by the woods and poured a little coffee from my thermos and pulled my earlier finds from my knapsack. I was hard as a rock going over my treasures and decided I was so horny I wasn’t going to make it home. I looked around, all quiet and just after 7 in the morning and immediately started taking my clothes off. I started with the bra, sliding my arms through and reaching back to clasp it. Next came the cami top, I pulled that over and adjusted everything to fit, lining up the spaghetti straps with the bra straps. The molded cups in the t-shirt bra under the cami top made it look like I had small breasts, which made me even hornier. Last came the panties. I picked a pair of green silky bikini panties and slowly pulled them on. They fit perfectly, even over my raging hard on. I looked around again, still all quiet. I laid back and slowly started rubbing myself through the silky panties, imagining the cute little thing that was in them last night. I started running my fingers up and down the crotch of the panties, teasing my ass a little, using my other hand to stroke my cock. I was laid back like this for about 5 minutes in pure bliss when I thought I heard a little noise. I looked around and off in the opposite corner of the clearing was a guy standing there. I started to scramble when I realized I was busted. Then i noticed his cock was sticking out of the top of his jogging pants and he was stroking himself too. I laid back again, rubbing my cock through the panties and watching him stroke his cock, hoping he would come join me. He was real nice looking, about 30, longer sandy blonde hair, and real slim. He was in a blue jogging outfit, and it looked like he had about 7 inches with a real big mushroom head. As I was rubbing and watching him I thought I saw a flash of pink where his cock was sticking out, I was really curious now. He kinda nodded towards me like he wanted to come over and I of course nodded yes. He came over and got down on his knees in front of me and continued to stroke his cock. I kept seeing little flashes of pink and I think yellow. I stopped rubbing the crotch of my panties and reached my left hand up and started stroking his cock. It felt amazing, long, wide with huge mushroom head on the end. Just thinking about that monster in me had me on the brink. I noticed that flash of pink again where his sweatshirt had rode up. I reached out and pulled his sweatpants down a little. Through the gap I saw pink and yellow lycra pulled to to the side, I pushed his shirt up some to reveal the pink and yellow vertical stripes went all the way up, he had on a cute 1 piece swimsuit! He stopped playing for a second and pulled his shirt over his head. Oh my, how sexy it looked. The swimsuit had wide pink and yellow vertical stripes, nice formed padded cups to give the illusion of small breasts, a halter top clasp and as his pants had shimmied down some, I reached around and felt an open back and a high cut full bottom. He scooted the rest of his pants all the way off and kinda posed a little.
“I was hoping to find someone else down here that liked this” he told me. “I have been coming down here since last summer, since I discovered all of the hidden treasures this place has”.
“I have been coming here for a few weeks, but I’ve never seen you here”.
“I am usually over by the creek, the kids all swim and skinny dipping over there, the girls must leave half their clothes around there. I have seen you here”.
“Creek? Didn’t know there was a place to swim around here?”
He said “ yeah, go towards the left when you come in, all the way in back. That’s where I got this”, rubbing his hands up and down on his swimsuit.
“How did you know I was scouting the area for panties too?” I asked.
“Well, remember the pink bra and panties you found last week? I left them there”
I must have blushed a little, because he was smiling at me now.
“The important thing is we both found each other here like this”.
I was just smiling in amazement and slowly stroking myself. He leaned over and slowly took me in his mouth. His mouth bobbed down all the way and back up, and just kept going that way, driving me crazy. Then I felt his hand pick up where I left off, rubbing the crotch of my panties. This was bliss, his warm soft mouth slowly engulfing my cock, his fingertips lightly stroking my panty covered crotch, his fingertips just brushing my eager hole. He slid his mouth off my cock and was back on his knees in between my legs. Both of us were back at rubbings our dicks. I had slid my panties over my cock and was teasing it through the soft material when he slipped his dick inside his snug swimsuit. He looked so hot with the tight pink and yellow one piece swimsuit, tightly clinging to his body, his cock now encased inside, flat against his belly. He leaned over me, nestled between my open legs and lowered his cock onto mine. I felt his hips move, rubbing our cocks together through the slick material, then he reached his hand around and grabbed my ass, humped in harder and planted a huge open mouth kiss on me. I responded by wrapping my legs around his waist and my arms around his body, drawing him closer to me and kissing back even harder. What a sight we would have been had someone walked up on us. I was so hot and on the edge, we were both humping each other furiously, tongues dancing in each other’s mouths. I felt his breathing get harder, he reached his other hand around and had grabbed my other ass cheek, buried his face in my neck, I could tell he was close. With on strong grind, he grabbed my ass tight and started grunting into the crook of my neck, he was coming hard, spilling his load in his swimsuit. That’s all it took for me, and I was filling my panties with hot cum as we kept grinding our cocks together through our girly clothes. When we both stopped spewing our cum, he sat back up on his knees so we could see each other. The way my panties were pulled tight on my cock, the cum just squirted right through the material and gobbed up on the front. Where his one piece bathing suit had pulled his cock flat on his belly there was an enormous wet spot at the tip. I just had to have some of that, so I got up and sucked on the wet spot and the end of his cock. I knew there was more cum in there, I pulled the swimsuit aside and licked the cum off of his belly and cock. There was a lot there and it was delicious! When I was done cleaning off his cock, we both sat there on our knees lightly rubbing each other and admiring the messes we had made.
“That was some of the hottest sex I had ever had” I told him. he agreed with me.
“My name is Scott” he said, “ but think of as Savannah like this”
“I’m Ray, but consider me Ramona for now”. There was a handshake followed up with another very hot deep kiss.
He said “I have to run, besides it’s getting late in the morning, we don’t need anyone finding us like this”
“That’s how we found each other” I laughed.
“Well, we may not get so lucky next time. I have noticed another guy lurking around a couple times, probably late teens, pretty good looking guy, so maybe there is another one like us”.
As Savannah/Scott was standing up to get dressed, he said “ there’s a dance tonight at both middle and high schools, this place will probably be wall to wall horny teenagers tonight, you may want to make a trip back in the morning”. He gave a quick wink to let me know he would be here too.
I said “ you bet, I’ll be here!”
He was dressed in his boy clothes, thanked me for the fun time this morning and took off. Time for me to get dressed and go too. I was already hard and horny again and couldn’t wait to get home and masturbate, so much to think about!
I was still a horny mess when I got home, I changed into a cute 1 piece swimsuit I had, a black halter style that was French cut. I crawled on the bed, grabbed a pillow with a satin pillowcase on it, slid it between my legs and tried to duplicate this mornings amazing hot sex. I balled up the pillow and lowered myself on it and began to slowly hump the pillow, The feeling was incredible, likely what he felt as he was humping away on me earlier. I was already on the verge, I balled up the pillow some more and started furiously humping down hard. The feeling of the silky bathing suit and the slick pillow case was too much. In one hard lunge I pushed in as hard as I could, and grunted, releasing another huge load of cum today. I could feel the whole front of my swimsuit instantly become saturated with cum. I laid forward, curled up in a ball on my pillow, twitching and quietly whimpering to myself as the last few drops of cum oozed out of me.
I must have dozed off, I woke up a couple hours later, in the same position. As I uncurled and sat up I looked down at the moist spot still on the pillowcase and the damp spot on my swimsuit, clinging to my stomach, I instantly got hard again. I was ready for another furious pillow humping session, but stopped. I wanted to save some energy, and cum, in case Savannah showed up at the park the next morning. One thing I knew, I was famished. I got out of bed and headed for the bathroom, I really needed to pee. I started to push aside my swimsuit and pull my cock out to pee, and thought to myself, dressed like a girl, pee like a girl. I sat down, pulled my cock out the side, and peed. I was ready to go make some lunch now. The tight swimsuit was starting to rub where the damp spot was, and I decided I needed to change and be comfortable. I picked out a cut pair of yellow cotton boy short panties, my light gray Victoria secret lounge pants, loose fitting, but snug up top so my ass is cupped nicely and my panty lines show through. Next I slipped on a yellow sports bra with shaped cups, and I dropped in my silicone falsies which gave my a nice B to C cup, and topped it off with a snug pink tank top. Now I felt complete. I don’t always dress up in girly clothes just hanging out at the house, usually just to masturbate, but I felt like being girly all day today. I made up some lunch, and ate quietly, enjoying the peace of living away from the hustle and bustle. The rest of my day I relaxed mostly, as I was getting ready for an early bedtime I hopped in the shower and decided to shave some body hair. I knew if my new friend showed up in the morning I wanted to look as sexy as possible. Now I am not passable, nor do I try to be, just really love my girly clothes, especially these cute little high school girls clothes. This time I wanted to look as cute as possible. I was shaved up as much as possible, put on a little pastel purple babydoll set I had (a pilfer from a laundry mat), and in bed early. I had to exercise great restraint to not masturbate that night, I wanted to be hot and ready, and have a nice load ready, for what I was hoping for a sex filled early morning.