Walking Miss Daisy

My wife works 1st shift. I work second. We don't see much of each other during the week. Our children are away at college. When I haven't been left with too long of a honeydo list for the morning I like to get online for a few minutes and look at a little porn. I like a lot of different things, but one of my favorite subjects crossdressers. Today I had a little extra time. I got ready, then turned on my webcam and went to a crossdresser chatroom. It wasn't long before a guy started chatting with me. He said he liked what he saw and asked if I did Skype. I told him I don't do it much, which is true, but I could meet him there for a few minutes. I logged off the chatroom and went to over Skype.

I consider myself to be straight, but very bi-curious. The only experience I've had with another guy was with a friend in high school. One day we were talking about some girls we knew, but didn't have a shot at. We were both a bit nerdy. We had never had much luck with girls. We could only wonder what they would be like in bed. My friend said he would love to find out what a blow job felt like. I agreed, saying I'd like to find out too. I think he was waiting for that opening. He asked me if I would try sucking him for just a minute, and then he would do the same for me. After the initial shock at the request, I reluctantly agreed. We did it. Just for a minute. It felt wonderful, but that's as far as either of us was willing to go. Over the years I've thought more and more about trying again, and trying more than a blowjob.

I started wearing panties about five years ago. I love the way they make me feel. I love feminine things. I just can't let anyone know that. I don't want to risk losing the life I've built. Fantasy will have to fill the void. I don't often have the chance to dress more fully. Today I was wearing a pair of pink cotton bikini panties that I bought on a slow night at Walmart. And I was wearing one of my wife's bras. I am not passable, but below the chest I have somewhat of a feminine appearance. I'm not all that hairy. I'm tall and slim. And I have more of an hourglass shape than my wife. When I tuck I can almost pass on a webcam.

Our session connected, and there he was. He was already stroking himself slowly. He was average sized and uncut. Nothing remarkable, but seeing him play with himself sure did get me excited. I twisted in my seat a little and started to rub myself through my panties. He asked me to stand and pose for him. Turn, so he could see my ass. A side view. Stand closer to the camera, facing it. I did so, all the while watching him stroke himself. He asked me to turn around again, bend over, and pull down my panties far enough so he could my pussy. I did. I looked back. He was stroking more quickly now. I could feel my clitty starting to swell. It felt like I was going to lose my tuck soon if it swelled much more. He asked if I had any toys. Sadly, I don't. I told him my wife has a conditioner bottle that I use sometimes. He said to get it. I retrieved it, and released my tuck. I rubbed some lotion on it, and my ass. The end is flat, and thicker than my own dick, so it took a little work to get it in. Once it broke through I pushed it in slowly, then out, and rubbed my cock as well. It felt so good. Before long he was stroking furiously. I worked the bottle and my cock faster. Moaning and breathing loudly. We both came at about the same time. Then we sat and caught our breath.

He told me I was amazing. I love hearing that. No woman has ever said that to me, not even my wife. A few guys have told me that online. Hearing it only makes me want to do this more. And my curiosity about trying it for real gets stronger every time. He asked if I had any pictures. I don't. He said maybe I could take a couple and email them to him. He typed in his address. He asked if I had ever dressed in public. I told him that all I've ever done is wear panties under my clothes when I'm out in the yard or taking my dog for a walk. I didn't tell him I've worn them to work once too. He told me he would love to see anything, but would really like to see me outdoors. Even if it was only panties it would be wonderful. Then he said he had to go. He said goodbye, and that he hoped we could chat again soon. And please try to send some pics.

I went to get cleaned up. Looking in the mirror I wondered just how passable I could be if I only had the chance to work at it. I thought of how I would look if I could lose my beard, shave all over, learn how to use make up, find a decent wig. I don't want to look slutty, like a lot of crossdressers do in pictures online. I just want to pass as the girl next door type. But as long as I'm married I have to settle for wearing panties when my wife is at work. Sigh.

I thought about my Skype partner's request for pictures. I could take the standard crotch shot wearing my panties. I really didn't think I could do anything in public. Getting caught would cause way more trouble than it was worth.

It was time to take the dog for a walk before getting ready for work, so I put the thoughts aside, tucked my clitty away, pulled up my panties and got dressed. I grabbed my keys and phone and called Daisy. She loves going for walks and was immediately at the door bouncing and crying to go out.

I live in a rural area. There are lots of rolling hills and trees with the occasional open field. My next door neighbors are several hundred feet away. There are a couple side streets nearby with a few houses, but not many houses on my road. Daisy and I usually walk about 2 miles. I like to walk more quickly than she does. She wants to stop and sniff at just about everything. We were about half way to our turnaround point. We had just come down a small hill and were approaching a tight set of s-curves.

That's when it hit me. I looked around behind me. I didn't see anyone. We kept walking through the first curve, and through the second. Looking ahead, the coast was clear. We walked back to the short section of road between the curves. There's a path there that leads to an abandoned house and barn and on into the woods. No one has lived there for about 5 years. It's getting harder to see the house through the weeds and privets that are taking over. The path is kept from growing over by pickup trucks that go back into the woods occasionally for hunting and who knows what else.

The street to the sides of the path is lined with trees. So I walked to the edge of the tree line. If any cars were coming I would be able to hear them before they got too close. I pulled out my phone and set it to selfie mode. I pulled down my shorts. Made sure my tuck was still in place. Then I turned away from the street. I wanted the street to be in the background. I held Daisy's leash off to the side. I held my legs together, one knee just slightly in front of the other, held up the phone and took the picture.

I pulled my shorts back up as quickly as I could. Daisy and I turned around and walked back to the street. Then I looked to the right and froze. Between the curve and the path was a cyclist. There's no way I could have heard him coming. I don't know why I didn't think of that. I do some cycling too. That's how I keep my girlish figure. He was coming up a slight hill, not very fast. Maybe he didn't see anything. Oh, God I hope he didn't see. Daisy and I turned and walked the other way. As he passed, he looked toward me and blew a kiss.

I've seen him out riding before, but only on weekends. Sometimes when I'm out working in the yard he'll ride by and we'll wave to each other. So he knows where I live. This could get really awkward. He disappeared around the next curve. Daisy and I turned around to walk toward home hoping we could get there before he came back. Our luck wasn't that good. We had only walked less than a minute when he came up from behind us. We could hear his wheels braking. He stopped just in front of us.

"Hi", he said. "Beautiful day for a walk. Don't you live in the blue house up the road?"

"Yes", was all I could say. Lying would be pointless. He had to live somewhere nearby and of course he knows where I live.

"My name's Jim. I live down Ramsey Road. Just built a house there last year." He paused for a second, then said, "I couldn't help but notice your little show back there."

I was blushing so badly now it probably looked like I was sunburned. I couldn't think of anything to say except, "Hi, I'm Rick."

"I sure would like to see that again," he said. "A little private viewing."

I wished I could have dropped dead right then and there. If he told any of his neighbors, everyone within 5 miles would probably know within a week. And this isn't an area where people take too kindly to anything even remotely gay. "I don't know," I said. I really have to get back and get ready for work."

"You can do it," he replied. "Just for a couple minutes. It will be our little secret."

"I can't."

"Yes. You can," he said quietly, but firmly. "Now. And nobody will find out."

I just looked at the ground. Daisy was sniffing at the back wheel of the bike. She's never met a stranger. I think she would go home with anyone, tail wagging all the way. Not much of a watch dog. She wasn't going to bark our way out of this.

"Let's take a walk over to that barn", he said. "You first."

I couldn't think of any way out of it. Honestly, the embarrassment was so strong I was having a hard time thinking at all. I stood there for a few seconds and looked up at him. Then I turned toward the barn and started walking.

It's about 200 feet from the road. Like the house, it's surrounded by tall weeds and privets. Vines are growing up the walls all the way to the roof. Half of the roof on the side facing the road has collapsed, and the wall underneath it is gone. We walked though the weeds to the opening. He laid his bike down. It wouldn't be visible from the road. We stepped in and over the debris to an open area to the left. Daisy was not cooperating. The smells must have been overwhelming her. I practically had to drag her.

"Give me the leash", said Jim. I handed it over and he tied it to a fence post. Daisy didn't seem to mind. She was too busy sniffing.

Jim said, "Ok now, let me take a look at you. Turn around." I turned and paused with my back to him. "Now turn back." I did. "Not bad. Now let's see what you're hiding. Pull your shorts off."

I was starting to shake a little. I was wearing a pair of gym shorts, so I reached inside the waistband and untied the knot. Then I pulled them down. I held onto a railing as I pulled them off and placed them on top of it. I stood there with my pink panties just visible below the shirt.

I stood there and let him look. Then I looked up at him. We may both do some cycling but he must do more than that to keep in shape. He had a much more masculine build. He had broad shoulders and well muscled arms. The cycling jersey on him was stretched tight over his chest, the zipper down far enough to reveal a thick patch of hair. His thighs were huge and looked hard as stone. And there was no mistaking the bulge in his shorts.

"Ok, now the shirt." I pulled it off as well. "Nice," he said. As nervous as I was, my tuck was starting to betray me. I could feel my dick beginning to grow. I squeezed my thighs together to try and control it. As much as I've thought about doing things with a guy, this was not how I wanted to do it. I didn't want him to know that I was getting aroused.

"Well don't you look pretty," he said. "Those look good on you. Turn around and let me see that ass." I turned." He didn't say a thing. I just stood there and could practically feel his eyes looking over me. And then, I just couldn't hold it any longer. My dick popped out from where it was held. He could see my panties move in response.

"Hmmm, what was that? Turn back around baby", he said. "Well, that wasn't there before. You must be enjoying this." He stepped over and stood in front of me. He reached out and touched my belly. He slowly moved his hand down to my waist line. "What a pretty girl you are. Turn back around for me sweetheart."

As I turned away from him, his hand slid over my waist. Then he reached down and cupped my ass with both hands. I could feel his breath on the back of my neck. My dick was now standing at full attention. How did I ever get myself into this mess?

"Please, stop," I pleaded.

"No! You want this and you know it, sissy." But he removed his hands. I heard him take a step back. After a few seconds he said, "turn around!" I turned to face him again. He had pulled down his shorts halfway over his thighs. His cock was rock hard. It looked to be at least an inch longer than mine, and a little thicker. "Touch it!" He commanded. I hesitated a little too long. He sternly said, "now listen sissy, do you want your neighbors to know what I saw on the road back there?"

I reached over and touched him gently. He was so hard. And a little moist from sweating on his ride. He must not have been riding long though, he didn't look to be dripping in it. And he still smelled fairly fresh. For the first time in 30 years I was touching another man's cock. I was half terrified and half excited. But I got the feeling the terror would fade before long.

"That's right sissy. Now, you know what to do. On your knees."

Without letting go of him, I got down on my knees. His cock was just inches from my face. He put a hand on the back of my head and pulled me in until it touched my lips. I pushed out my tongue and tasted him. Oh, my. After all these years. It felt so wrong, but at the same time so good. My tongue started to explore. I felt the slit on his tip. Tasted the precum oozing out of him. Then drifted down the side of his shaft. Back and forth. I played with his balls. Then he guided the tip of his cock to my lips, and with his hand still on the back of my head he pushed into my mouth. My jaws opened up and I felt him gliding over my tongue. So smooth and delicious. I started going back and forth on him and reached up to put my hands on his hips. I couldn't believe this was happening. Part of me was saying that this was where I belong.

We went on like this for a couple minutes, then I could feel him start to tense up. He pushed me back to free himself. "That's a good girl. You do seem to like this. Stand back up and turn around. Lean against the railing."

Oh my God, is he really going to do that? I wanted to resist, but my body had other things in mind. I looked up at him and saw the determination in his eyes. I stood up and turned around. He pulled my panties down to the ground and told me to pick them up. I placed them on the railing. He spit into his hand and reached down to my pussy. He rubbed it and got it wet. Then he pushed a finger into me. I was still lubed from my Skype session and he went in with no resistance. Then a second finger. He reached in deep. He finger fucked me slowly and my knees started to shake.

I closed my eyes and rested my head on my arms, leaning on the railing. He gently kicked the inside of one foot to tell me to widen my stance. He pulled his fingers out. Then I could feel his cock rubbing up and down in my crack. He stopped rubbing. And there it was. He touched the tip against my hole and pushed in. He went in slow, and it didn't seem to stop. He went deeper and deeper without pulling back. Nothing I've ever used has been that long. It was starting to hurt. He finally stopped when his hips were pressed against my ass and stayed put. No movement. He stayed there for at least minute and the pain slowly disappeared.

He started moving again. In and out, slowly at first, but picking up speed. I couldn't believe how good it felt. He went faster, and faster. The urgency was building with every stroke. I was getting so excited. I opened my eyes and looked down. I could see his hands on my hips. His feet between mine. His legs thrusting back and forth. His breathing was getting louder. My own dick was bouncing up and down. I instinctively reached down to grab it but he slapped my arm away and commanded, "NO!" So I pulled my hand away and completely gave into him.

He pulled me in tight and held me there. I could feet him shooting his cum inside of me, pulse, after pulse, after pulse. He pushed as deeply inside of me as he could possibly go. He held me there for a minute till his breathing started to slow down, then he leaned down against my back. He rested his head on my shoulder. Still breathing hard. But he was looser, more relaxed. I reached down again and touched myself. He didn't object this time so I started stroking. As I did, he started going in and out of me again gently. I've never felt anything that good in life. I didn't want it to end. But there was no holding back. I came so fast and so hard. And then we just stood there. Breathing. Sweating. Completely lost in the moment.

He pulled out of me and pulled his shorts up. I got dressed. Daisy was quiet now, lying on the ground staring off into space. Jim said, "that was amazing sweetie." I melted.

He said, "you know, I've seen you out riding a few times. Maybe we could ride together once in a while."

"I think I'd like that," I said.