My First Taste

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He's caught crossdressing outdoors.
1.5k words
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The first time that I tasted a mouthful of male sperm was last summer. I have been a crossdresser for many years and had started to venture outside, always away from the public view. Usually in the woods or on a long since used back road. One afternoon last summer I went to one of my favorite spots. About 40 miles from my house is a national forest. There are hundreds of small trails that lead on for miles. I found a secluded spot about a year ago that I cleaned and groomed into a perfect place to dress and enjoy myself. It has a spectacular view overlooking a small pond. I kept a blanket hidden in a plastic bag that was hidden in a hollow tree.

The day started like most that I had been at my special place. I removed the blanket from its hiding place and spread it out on the grass. I slowly stripped off my male clothes and started to prepare for my transformation into "Becky", my female persona. I removed a mirror from the small bag that I brought along with me. I carefully applied the make-up starting with the foundation followed by blush, eyeliner, mascara, and finally bright red lipstick. I check a last time before I was satisfied with the job before I pulled the mid-back length black curly wig out of the bag. I adjusted it into place and started to brush it out. Once I was happy with the way it looked, I began to concentrate on getting dressed.

I sat down on the blanket and started rolling the sheer black nylons that I had just bought. I slowly pulled them up my shaven legs and smoothed them into place. This was followed by a black lace garter belt, which was attached to the nylon tops. Next I pulled out the silicone breast that I ordered over the Internet. I spray the medical grade adhesive onto the back of each breast before pressing them into place. Minutes later I now had a set of breast that several women that I know would be jealous of. Next I opened the clasp on a beautiful black lace half bra. I quickly but carefully positioned the bra into place and closed the clasp. (A task that I have become quite good at)

Next I stood and pulled the black lace thong panty into place. Being careful to pull my now hardening cock between my legs and wedging it between my ass checks. I slowly lifted the black lace slip over my head and let it drop into place. My short black leather mini skirt and then my white sheer blouse followed this. The black bra and my enhanced cleavage were clearly visible through the sheer material. The last thing was my 4" black leather stappy pumps. I was now ready to be a woman. What I was not aware of was that two guys were down at the pond and heard me rustling through the bags and decided to investigate. I had just laid down on the blanket and started licking and sucking on the rubber dildo that I had brought with me.

I was lost in what I was doing when the guys came up beside me. One of them cleared their throat to get my attention. I looked up in horror to find to guys watching me suck the dildo. I went to stand up so that I could run and fell flat on my face. They both laughed at me. I made my way to my feet and began to run until my heels got stuck in the grass and I fell again. The taller of the two helped me up and dragged me back to the blanket. The shorter of the two said, "Well what do we have here?" I stood there and said nothing. That's when he said that I shouldn't be wasting my time sucking on a rubber dildo when there was two perfectly good cocks there. I started to protest when he said that if I wanted to dress like a woman that I should be treated like one. That's when he unzipped his fly and hauled out a fat wrinkly cock that was at least five inches long and two and a half inches around and still completely flaccid. By far the biggest cock that I had ever seen. He grabbed my wig and pulled me to him. He pushed me to my knees on the blanket and started moving closer. I started to pull away and he informed me that if I didn't do as they said that they would beat the shit out of me and cut off my dick.

He told me to start sucking and he pushed his cock into my face. I had no way to escape so I slowly opened my mouth. He told me to lick it first. I slowly run my tongue across the head and then up and down the sides. His monster cock started to grow and kept growing until it was over 10 inches long and more than three inches around. Once he was fully erect he grabbed my wig and forced the head of his cock into my mouth. I had to stretch my mouth open as much as I could to allow the mushroom shaped head to enter.

Once he had the head in, he started to force more in. I felt it hit the back of my throat. That just spurred him on and he pushed harder until he was entering my throat. I started to gag and he pulled back for a second before slamming his cock forward again and soon he had atleast six inches in my mouth and throat. I thought that I was going to die. He continued to push more until he realized that I couldn't handle anymore. He told me to use my throat muscles to milk his cock. I slowly started to swallow and managed to get another inch in my mouth.

By now the taller of the two guys was getting impatient and wanted his turn. The shorter one pulled his cock out and slapped me in the face with the monster. As soon as he stepped a side I had my first look at the taller man's already erect cock. It was much shorter and no where near as thick but was uncircumcised. He stepped forward and slowly pushed the head of his cock into my mouth. My jaw was burning from the monster that was just removed so I was actually happy to see that he was only average sized. He slowly continued pushing until his balls were touching my chin. That's when he started really giving it to me. He would pull out all but the head and slam it all back in again. I was actually starting to enjoy servicing him when the shorter guy climbed behind me and pulled up my skirt. He could clearly see my erect cock through the lace panties and commented on how I must enjoy being a woman. Then all of a sudden he yanked down my panties and spit on my ass. I realized what he was about to do and wanted to stop him but there was a part of me that was really enjoying it.

He worked a finger into my ass, then two. Soon he was reaming me with three fingers. He was stretching my hole to accommodate his monster tool. I was so enjoying the cock in my throat that I didn't resist when he started pushing his cock into my ass. I had to stop sucking the taller guys cock to keep from biting him as the shorter guy showed no mercy as he pounded my ass until he had every last inch of his cock in my ass. He stopped long enough to scoot forward so that he could grab my hips. I had just started sucking the cock in my mouth again when I felt the cock in my ass pull out until just the head was in and then he slammed back in time and time again. With every forceful thrust of his hips I was impaled at both ends. Soon we had all worked out a rhythm and I was in heaven.

Only moments later I felt the cock in my mouth start to jerk and soon I was swallowing my first taste of semen. Just when the last trickle was sliding down my throat I felt the shorter guy pick up the pace as he neared his release. I regretfully felt the cock slip from my mouth only moments before I felt the sensation of the load being deposited in my ass. I almost passed out from the pleasure and for the first time I really felt like a woman. Both guys thanked me for the good time and said that they hoped to meet again real soon. I informed them that I would be back next weekend. They laughed and said "Same time - same place."

I lay on the blanket and drifted off to sleep as the cum leaked out of my well-abused ass. When I awoke, I cleaned up, removed the make-up and got dressed. I had to wear the breasts home because I forgot the adhesive remover. Not that I really minded, I enjoyed being a woman even more now.

This is a true story. The names were left out to protect everyone's privacy.

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13 Comments
AnonymousAnonymousalmost 8 years ago
Lucky Gurl

You are a very lucky gurl, I would like to exprerince that.

AnonymousAnonymousover 8 years ago
I love threesomes

I too am a CD and I love cock. I suck cock as much as I possibly can and I truly enjoy getting fucked. I've had some threesomes (4 of them) and I love sucking a big cock in front of me while another big cock is fucking my man-pussy. Please tell more stories like this one. Continue your adventures outdoors. That really turns me on.

AnonymousAnonymousalmost 10 years ago
I'm so jealous

If your story is true, I'm so jealous. I too am a cross-dresser but I haven't yet ventured out in public. Your story has inspired me to do the same thing -- troll the park just outside the city and have 1 or 2 hot guys feed me their cocks and fuck me. Wish me luck. Please tell more stories like this one. It's so hot it made me so hard.

AnonymousAnonymousover 10 years ago
true confessions

Wow, so many true and some perhaps, not so true forced encounters.

I had none of those close encounters. But, these I've done...

Been chased by small dog on hike in woods thinking it was a large male predator.

Whistled at.

Ogled through my car window wearing low-cut mini dress over very slow bridge.

Chased on the sidewalk and invited to "party".

Inhibited to go to a restaurant by vulgar jesters of the young males in the parking lot.

Shopped for new clothing (many times)--walmart, goodwill, others, ...

Bought beer with nice cleavage, heels and short skirt. She smiled and was nice--I made sure it was girl at checkout. (she knew)

Shared the ladies room at movie theatre with no problems.

Held the door open for lady and her kids as I was exiting ladies room. (convincing cleavage, surplice white top and black miniskirt)

- K

kathyann0026tskathyann0026tsover 11 years ago
First cocks

Honey, it's been such a long time ago that I had that first cock pumped into me. It was a black guy that found me out. I was very young but, I was dressed up in one of my sister's outfits. I was walking around outside in a vacant lot where my buddies & I use to play. It was overgrown there with bushes & trees & we had built a nice shack there at the time. This black guy followed me into the lot, to make a long story short, he first made me suck him to completion. Then after waiting a bit, he managed to use my sissy pussy then. It hurt like hell at first but, I soon grew to enjoy it. I really love it when I felt him shooting his cum up deeply in me. I didn't know what it was at the time, but all I knew was that it felt soooo nice.

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