Anonymous Encounter

This story came to me as I was talking with someone on Adult Friend Finder. It is a great place to meet (sometimes) people. There are a lot of wierdos there, but there are a couple of nice people and you can find something that will fit your taste. Anyhow, I was talking with him and he suggested an encounter that was sort of like this one in the story. A lot has been changed, but he will know what he suggested if he reads the story 🙂 Anyhow, I hope you enjoy it!

XOXOXOXO Cin

Well it was a boring day. It was fairly hot outside, somewhere around 93 degrees. The sun was shining, there were very few puffy clouds in the sky and I was home alone. As usually happens when I am bored and home alone, I was horny as hell. I wanted to jerk myself off, but I wanted to do it to something different than the normal porn that I usually watch. I figured since no one would be back at the house until tomorrow I would take the time and dress up and do my makeup and hair and really go all out for it today.

I went upstairs and got out of my regular house clothes, shorts and a t-shirt. I warmed up the water in the shower and took my hair down and brushed it out, getting the tangles out of it from the night before. I took a razor and put it on the edge of the tub and put the brush down next to it. I’m not allowed to shave my arms or legs due to work and my wife wouldn’t let me anyhow, but I am allowed to shave my ass and crotch and since I love the feeling of the panties on my naked cock and ass, I figured I would go ahead and shave all those areas bare today. It isn’t like I didn’t have time!
I took a long hot shower, being sure to shave my crotch, balls and ass completely bare. It took a long time as the hair was a little long since it had been a while. Once I was satisfied with my shave, I went to work on my hair. I used a stripper with beer and soap to get all the grime out of it, then used a regular shampoo and strong conditioner to get it nice and shiny. I then washed up completely with a nice floral body scrub and lotion. I loved the smell and it was very feminine so as to complement the look I was going for after my shower.

I stepped from the shower and dried off moving my cock from side to side to check that all the hair was gone and there weren’t any nicks that I had to worry about. I patted my body completely dry and wrapped my hair up in another towel. I needed to shave my face, but of course I wasn’t allowed to shave my goatee. I could shave everything else, just not the goat, so that kinda kills the image for most people (including me!) But, since I was still allowed to dress and I didn’t get a divorce for being a freak or anything, I took what I could get where I could get it!

After everything was done with my face I did what makeup I could without really being weirded out with the goatee, just really my eyes and lashes, lipstick made me feel uncomfortable since the hair around my lips made it look very funky! I quickly put together a medium smokey eye look and put on black mascara then lengthened my eye liner out a little giving a slight cat eye look. It was as good as it was going to get with the facial hair, so it would have to do!

I went to the closet and got out a pair of tights that would be opaque enough to cover my leg hair and a pair of pink Victoria Secret cheeky panties with black lace around the top. I love these panties and have them in all different colors. I grabbed a long sleeve top that came down over my ass and wasn’t too tight. I still had to lose a few pounds to make my tummy how I would like it to be in a tight outfit. I went back out to the bedroom and started to get dressed. I put the panties on first, pressing my cock down between my legs, though it wouldn’t stay there long. I pulled the tights up over my legs and panties, they did a great job of covering my leg hair, but still let it show through just a little bit. It was perfect for my feet and the type of shoe that I enjoyed wearing, so I could show my toes. I decided not to paint my nails since everyone would be back tomorrow.

I stood up and put the top on, it felt so good to wear it was like a cheap cashmere, but obviously wasn’t. It still felt good to have on. I pulled my hair out of the towel and let it fall down my back. It still wasn’t dry, but was starting to get its curl back. There wasn’t anything that I could do to straighten it. I have tried for years to straighten my hair, but it always goes back to curly in a few minutes. I shook it out and let it fall again. It was really curling up now and would be back to its full curl very soon. I looked at myself in the mirror. I didn’t think that I would need to wear the breast forms or the bra for what I had in mind.

I sat on the corner of the bed and started to put the shoes I had picked out on. They were black patent leather, open toed, platform heels. They were about a six inch heel. I love those shoes. They were hot as hell and comfortable to boot! I can’t count the times that I had masturbated and shot my load over them on camera for people to watch! They always love it when you shoot cum all over your shoes and stocking covered feet! Maybe I would do that today too! We will just have to see what they want to see in the video chat rooms. It had been a little while since I had done anything like that and this was the perfect opportunity to do it!

I stood up once I was done putting the shoes on and making sure they were tight. I walked around a few times to make sure everything was in place and stopped in front of the mirror. I checked everything and straightened out the top and the tights. I looked myself over one last time in the mirror and figured I was as hot as I was going to get. I went back downstairs to my office and turned the computer on.

I decided to get a glass of wine while the computer warmed up and I figured out where I was going to log into for my little day of fun. I decided that I was going to log into Adult Friend Finder. Everyone knows about that one and there are a good number of cross dressers that like to cam on there. So I got my wine and sat down at the computer and logged in to the site. It had been a little while since I logged in there and there were a lot of new people nearby. I checked out the online matches and flirted with a few people and then decided to check out who was on camera.

There was about twenty-four cross dressers or transgendered people on camera. Of course there was over a thousand guys on cam, not sure who they were all talking to or if they just like showing off their cocks. Not that I mind, I enjoy watching a good looking guy jerk off every now and then too! I checked out a few of the other cross dressers, but they were either just chatting or were done getting off for now. I decided I would start up my cam and wouldn’t be showing my face. I would start out fully clothed and tease people every now and then by showing my panties or rubbing my cock.

This was pretty much how the first hour went. I watched a few people come and go, there were a few that started chatting also and they wanted to see more. They were really horny and I was getting there myself. They enjoyed the peeking panties and pressing the tights around the outline of my cock so they could use their imagination and rub their own cocks to the thought of wrapping their hands or their lips around it. Some wanted me to jerk my cock and cum in my panties, others wanted me to jerk myself through my panties and have the cum seep through them. I wasn’t ready to do that yet, I just wanted to chat and play with myself for a little while and see what people were really into.

There was one person that just kept giving support for everything that I did. He wasn’t pushy, didn’t ask me to do anything, just said how nice my panties were, how nice the vision of my cock through the tights was. He told me that he was jerking himself off to my video. He was very polite, but very different from what normally happens during a video chat. The thing with Adult Friend Finder is that you can only see those who are broadcasting their own streams on the site, there isn’t really a way for two to chat together on camera. So I wasn’t able to see anyone that was watching me, but I could guess what I would see with most of them.

This one person, let’s call him Doug, was enjoying the video and just letting things happen and enjoying things as they did. The others were all asking to see something specific or just plain being jerks. I was used to this on the site, but there was something very different about Doug, so I started chatting him up.

“So, what is it you like to see honey?” I asked him as I lifted my top a little and ran my hand over my cock through the tights and panties.
“I like exactly what I see.” He wrote back. I wasn’t sure exactly what he meant, though I knew what he was seeing. So I took it a little bit further and pulled my tights down slowly letting my panties show completely. My hard cock was pushing against them making them tent upward and showed the outline of the bottom of my head against the tight silky fabric.

“Mmmm, I like that very much.” He wrote quickly before I even touched myself. So he was really enjoying the fact that I was dressed as a girl and my hard cock showed through the fabric, but did he like the cock, or just the way that it was encased? I wasn’t ready to take my cock out just yet, so I started to run my hand lightly over the underside of my cock through the soft fabric.

“Do you like that too, you like seeing me touch it?” I asked him. I kept moving my hand over my cock lightly, sometimes tickling the bottom of my cock just under the head where it was really sensitive. The people watching could see my cock jump under the panties every time I did this. I was still getting various messages about how they wanted to suck my cock, or wanted to shove their cocks deep in my ass, or have cum shot down their throats. These were the normal ones that I was used to ignoring since most of them were way far away. I was really waiting to see what Doug would say.

“Yes, I really do. I enjoy seeing you jump every time you run your nail under your head. I really have a thing for anonymous encounters and love having a cock in my throat and sometimes deep in my ass. Are you into this sort of thing?” He finally replied.

I think he is really enjoying the show and probably doesn’t live close by, so it is fine, he is being a nice guy and sounds sincere. I figure I may as well go ahead and tell him the truth. “Yes, I do enjoy that,” I kept rubbing my cock as I wrote to him, “I love the thought of glory holes, but I haven’t been able to try one yet. I like the idea of anonymous sex too, a blow job or a good quick fuck and then leave without a word said. I would love to try that sometime with the right person.”

I was really hard thinking about it by now. I thought about the glory hole thing and the anonymous sex where you would never see the other persons face, just their ass or their cock. That would be so hot! My cock was so hard that the head started to peek out the top of my panties. I couldn’t hide it under the small, thin fabric any longer and started to run my finger around the tip that was peeping out.

“Mmmm I can see that you really do like that idea. Love the sight of your head sticking out just a bit above your panties. Would you like the chance to try that anonymous encounter? I would hate for you to shoot your load on camera if you could shoot it down my throat.”

Now that caught me off guard. I wasn’t expecting him to talk that way, though it still was a little different from the other horny ass people on chat. He was more confident and kind about it, like he really did want my cock down his throat or up deep inside his ass. I have to admit I was really thinking about it. “I’m not sure, I think I would love to try it sometime, but I haven’t had the chance to try it. Where do you live?”

There was a bit of a pause and I kept running my finger around the tip of my cock making it jump every now and then and come out a little further from underneath my panties. Finally he replied, “I live down at the ocean front. The website says I am about six miles from you.”

Holy shit! I wasn’t expecting that! Ok, now what? Do I blow him off or go and blow him? I am horny, especially now. I never go out dressed, especially since I can’t shave my goatee! What the hell was I going to do!? I really wanted to go try an anonymous encounter of some sort, but do I get changed, do I just say not now and talk more or do I just go?!

“Umm wow, I wasn’t expecting that. I don’t know. I don’t know you well and well I don’t go out dressed.” I finally wrote when I could think straight.
I had already stopped stroking my cock when the shock hit me. The other people in the chat were bitching that I wasn’t going further. Right now I didn’t give a shit about them, I was waiting to see what was going to happen with this guy that I never met, and that lived just a few miles from me! I couldn’t believe I was in this situation.

“Well, I have a shower in the back yard for when I come back from the beach or out of the pool and the curtain goes up and down. You can control the height of it. How about you come over and get in the shower and raise it just above your cock and let me take care of that for you?” He wrote back.
I was seriously considering that. It sounded perfect. Neither of us had ever seen either’s face so it would be completely anonymous. He was close by, I was already dressed and horny as fuck. Hell with it, why not? What is the worst that could happen? Ok, I didn’t want to think about the worst that could happen because that could be pretty bad.

“Ok.” That was the only thing that I could write. I couldn’t think of anything else to say. I mean what would you say to something like that? I was about to go have sex anonymously in my own city dressed as a girl. I was nervous as hell by this point and stopped the video. I wrote back to him in regular chat and asked where I should go and how to get to the shower.

“Just park in the drive way walk around the back to the left and it will be by the house next to the back door. When you are ready, just reach out and knock on the back door and I will come out. Nobody can see into the back yard of my house and it is very private from the beach as well. Don’t worry, I go out nude all the time to my pool.”

“Alright, I am on my way.” I told him as I got the address and closed down the computer. I pulled my panties up and straightened my tights again. I had never driven in high heels before, but I figured now was a good time to learn. I couldn’t stop shivering. I was excited and nervous and scared out of my wits all at the same time! I still couldn’t believe I was doing this.

I grabbed my wallet and keys and went out and quickly got in my car before any of my neighbors could see me. I started the car and put my wallet in the glove box. I figure I would need that if I got pulled over, but I really really hoped I wouldn’t! I would have a lot of explaining to do to the cop if I was! Finally I was on my way, I pulled out of the driveway and headed toward the beach. He wasn’t far down, but he wasn’t in the main drag either. I knew the houses in this area were fairly well laid out and apart from each other, so he was probably telling the truth about the back yard being very private.

The trip went by way to fast. I guess it was from the thinking and the worrying that I was doing. I couldn’t remember most of the drive, but I could remember the various situations going through my head and the way my body was still shaking as I pulled up into his driveway.

I checked the address three times to make sure I was going in the right back yard, and not into some un-expecting persons backyard dressed as a girl, trespassing and getting arrested and thrown in jail like this! Could you imagine the things that they would do to you dressed like this in jail?! Whew, I really was hoping that wasn’t going to happen and I was really shaking at this point.

I got out of the car, walked around to the left side of the house and back through the gate. It was open like he said it would be and at the back corner of the house was a walk in shower that had a curtain that could either pull sideways or up using a draw string inside the shower. It was a really nice house and the pool looked extremely inviting in this weather, but that isn’t what I was here for this time. I got in the shower and pulled the shower curtain closed to my right and made sure it was completely closed. I pulled my top down to make sure it tight and covering my ass and cock.

It was time. I hoped he was waiting just inside the door or at least really close by. I reached out and knocked on the door and quickly drew my hand back inside the shower. I almost immediately heard the door open and a voice called “Cindy?” I answered “Yes,” very softly. I heard him step out on the patio, and close the door behind him. Was he naked? Was he fully dressed? I don’t know! It was exciting and excruciatingly nerve wracking at the same time!

“Are you ready? Lift the curtain as far as you want, when you are.” He said quietly, and patiently. I was nervous, but I was ready. At least I think I was. I reached over and grabbed the string of the shower curtain and pulled on it lightly, the bottom of the curtain began to move up. I don’t know how long my legs could last, so I quickly pulled the string the rest of the way, until the curtain was just above my waist. I could see the bare feet and legs of Doug when I looked down. He was starting to kneel and I moved close to the curtain so I didn’t see his face and he couldn’t see up to mine.

I looked up at the sky as I felt his hand reach out for my top and lift it just to the edge of my tights. He then ran his hand over my hard throbbing cock through the fabric of the tights and the panties. He did this a few times before leaning in and kissing the tip of my cock through them. He nibbled with his lips on the head of my cock then moved back and hooked his fingers in the top of my tights. Slowly he moved them down, leaving my panties in place to barely cover my cock. He pulled my tights down just below my balls and kissed my cock from the tip down to the base and licked my balls through the fabric of my panties.

It felt so good I had to reach up and grab the pole that held the shower curtain in place and check to make sure it would hold my weight as I used it to steady myself. He continued to lick my cock through my panties until the head peeked out again above the black lacy waistband. He moved down a little and took the fabric around my balls into his mouth teasing them slightly as he pulled down moving the waistband further down my hard cock letting it free.

I could feel the breeze as well as the heat of his breath on my cock. He reached his tongue out and licked by balls lightly, then drug the tip of his tongue up the length of the underside of my cock. He flicked the tip of my cock with it a few times before taking the tip into his mouth. Oh my, it felt so good! The naughtiness of it, the excitement, the fear all at once gone with the feeling of his mouth wrapped around my cock. I completely forgot that I was dressed as a girl in the back yard of a strange guy in the same city that I live in. All there was right then was the feeling of his lips wrapped around the tip of my cock and his tongue pressing on the bottom.

I couldn’t help but moan and push my hips forward trying to get more of my length into his mouth. It felt incredible. I held on to the curtain rod above me tightly to keep myself from grabbing his face and just fucking the hell out his mouth. I wanted this to last a little while and didn’t need to shoot my load so fast that I would be embarrassed, and a little heartbroken that it was over so soon.

I gripped the bar above me and slowly thrust my hips toward his face. He was sucking lightly at first and running his tongue the length of my cock the whole time. This went on for about five minutes. I knew he could tell that I was really having a hard time holding my orgasm back.

He slowly let my cock fall from his lips and stood up. I could see his hard on poking out underneath the shower curtain next to mine. It was about the same size and girth as mine and didn’t have the curve to the left that mine did. He reached out and wrapped his hand around both of our cocks and slid it back and forth, jerking us off together. It felt amazing feeling his skin slide across mine and his grip wasn’t so tight as to make it hurt. He did this for about a minute then let go.

I was just about to kneel down to return the favor to him for the amazing blow job he had just given me when he turned around and bent over pressing his ass against my still throbbing cock. I was taken by surprise, but quickly recovered from it and looked around the shower. There was a bottle of lubricant next to the shampoo.

I grabbed it and spread some on my cock and then put some more on my hand. I spread the slick liquid all over my dick and then spread some all over his ass hole as he pushed back against my finger. I pushed a finger through his tight opening spreading the lube inside of him. I pushed and pulled a few times and pulled my finger out, replacing it with the tip of my cock. I didn’t just push in though, I ran the tip up and down his crack spreading the lubrication around before I place the tip at his entrance and slowly began to push in.

He was tight, but with all the lubrication my dick just slid right past the tight ring of his ass and was quickly embedded inside him. I heard him moan as I slowly began moving deeper, pulling him back against me. His ass felt so good, wrapped around me, I knew I wouldn’t last long inside him.
I pulled him back until I was all the way inside him, his ass was pressed hard to my crotch. The feeling of being inside him was amazing. I was moaning right along with him with every throb of my cock. I held it deep inside for a few seconds before I started to slowly move it back out. Once I had just the head inside I began to push back, all the way down and then pulled back again. Soon he was moving his hips to meet mine and I was fucking his ass with a good steady rhythm.

I could feel my orgasm coming on quickly and after only about a minute I told him I was going to shoot my load. He pressed back against me, inviting me to cum inside of him and I was more than happy to do so since I didn’t think I was going to be able to get out in time as it was. My orgasm hit me hard, my knees started to shake and my cock throbbed deep inside his ass. I let go of his hips and held tightly onto the curtain rod as he continue to fuck me and his ass sucked the cum from my cock. It felt like I would cum forever, and he was more than happy to keep fucking my cock while I did.

Once there was nothing left, and I started to soften, he slowly pulled forward and let my cock slide from his ass and my juices dripped out slowly after it. He turned around again and still had a raging hard-on. I quickly dropped to my knees as he pushed it forward, and licked it all over. I moved my tongue from the base, to the tip, on all sides, and then flicked his balls lightly with the tip of my tongue. I wanted that cock and I wanted it bad by this time.

I wrapped my right hand around the base of his dick and took his balls into my left hand. I pressed the tip of my tongue into the little slit at the top of his cock and then made little circles around the tip. He was moaning as I started to move my hand, still covered in lubricant, back and forth over his dick as I took the tip into my mouth and ran my tongue around in circles, paying particular attention to the sensitive area under the head.

I was really out of practice I guess since I could only take two to three inches into my mouth before I could feel the gag reflex starting to kick in. I kept working my hand over his skin as I bobbed my head in time with it. I gently massaged his balls at the same time and turned my head sideways every now and then to give a different angle to change the feeling.

After all the fucking and sucking from earlier, I knew he wouldn’t last long, but I really wanted to feel him inside me and have him shoot his cum deep inside my ass. I slowed down and after about another minute I pulled his cock from my mouth and slowly stood back up.

My panties and tights were still up around my thighs, but my ass was completely out in the open. I took the bottle of lube and spread it over his cock and my ass then turned around and put my hands on the wall of the shower and presented him with my lubricated entrance.

He placed his hands on my hips and the tip of his cock at my entrance. Just as I did, he spread the lubrication over my ass with the tip of his dick before letting it slide inside me. Oh my God the feeling was amazing. I hadn’t had a cock in me in at least a year and his was the perfect size. He slid right up to the hilt in one slow thrust and it didn’t hurt at all.

My cock started to grow again as he began to move his in and out of my ass slowly at first and then picking up the rhythm. I reached down and started to jerk myself off as he fucked my ass steadily. My strokes were matching his strokes and I pressed back in time with his thrusts, he was moaning and breathing hard. I could tell he was close. I was getting closer, but not as fast as he was.

Soon he gripped my hips tightly and thrust himself as deep as he could go and I could feel a warmth spread inside of me as his cum filled me, flowing from his cock deep inside my ass. I used my muscles to grip him over and over, trying to coax as much of the juice as I could out of his throbbing dick as I stroked mine. I could feel my peak coming on quickly as he began to slide slowly out of me.

As soon as his cock was free of my ass I turned and jerked myself as hard as I could. I saw him get on his knees and I knew he wanted me to cum on his face. I moved as close to the curtain as I could and my cock exploded for the second time. I shot my seed, but since it was the second time there was only two decent streams and a few dribbles left. The rest of my juices was somewhere deep in his ass. I just didn’t have any more to give.

I saw him stand up and his soft cock was visible next to mine. He pressed his against mine and wrapped his hand around them. He squeezed them together a couple of time and said, “Thank you! That was great.”

“Yes, it was, thank you very much.” I replied as I heard the door open and close again. I quickly cleaned up as best I could using a little water from the tap, and pulled my panties up. I made sure they were on straight and covered everything before I pulled my tights up and centered those as well. I pulled my top back down and made sure I didn’t have anything showing, cum stains and the like and peaked out from behind the shower curtain.

The backyard was empty and was just the way I remembered it as I came in. I saw that the shades were still drawn on the back door and no one was peeking out through them, though I don’t know if he watched me from another window. At this point I really didn’t care, he could have taken me inside and kept me there all night for all I would have cared at this time!

I walked around front, a little wobbly, and a little tired, but thoroughly fucked and sucked. It was a great feeling. I got back in my car, and as I sat down, I could tell that his juices were dripping from my ass into my panties. “I will have to keep these as a little souvenir”, I thought as I started up the car and pulled out of the driveway.

The trip home was about the same as the drive there, I didn’t remember much of it since I was still mostly day dreaming about the encounter. I am really glad that I went, even though I was scared as hell I still did it. That wasn’t like me at all, usually I am scared shitless and don’t do stuff like that. I don’t know what was different this time, but whatever it was, I hope it sticks around and I also hope that Doug wants to use that pool of his in the near future!