Long Distance Fantasy

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I dressup when a friend cums to town fantasy.
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BigChubT
BigChubT
16 Followers

Our story started out when I met this older gentlemen named Robert online. He admired a story I wrote on a very erotic literacy website. From the first e-mail he had me wanting to know more about him. Hes taller than me and more mature by about 30 years. He has nice brown hair with some grey distinguishing it.

He was very honest with me and told me he was married. And sometimes he likes to be naughty. He likes men on the side. Or does he really prefer men? I haven't totally figured that out yet. The only thing that matters is that we have become friends. And that we had sex together several times.

Now when I say sex, its just cyber-sex. We live too far apart to see one another in real life. It would be nice one day if we could see each other for real. And act out on the fantasies we have for one another. I'm about to describe the best one I had about Robert thus far. He was really naughty in it. And I'm also going to send this story for him to read too. I hope he enjoys it.

To start with, my name is Ted, but my female name is Maria. I'm a male cross-dresser from West Virginia. Robert became very interested in me when I told him I was one. It was a part of his fantasy and he had always wanted to sex with a cross-dresser. It would be nice if I make his dream come true. Maybe someday if I could move closer to him.

My fantasy starts out when I arrive at a motel room to get ready for Robert. I am expecting him in a few hours. I set out my wardrobe for the night before I took my shower. A nice sexy black dress with matching panties and stockings. I decided to go bra-less just in case he wanted to feel my breasts through my dress. I also brung along a sexy white nightie for later if I needed it. If I have my way I wont need any clothes after he gets here.

After I took my shower I wonder if I should shave my body hair off. Would he like that or would he like to feel the natural me? After a short debate I decided to shave it all off except for my pubic hair. I hope this pleases him. I know I feel very good right now and gave my cock a little stroke before I got dressed.

I also brung a dark brown wig and my makeup bag to make myself more presentable to him. I can't really pass for a woman on the street but it makes me feel more feminine when I put it together with the clothes. I'm also a big woman and its been hard to find clothes in my sizes most of the time. I also sprayed myself with a little perfume that I hope he likes too. It smells great to me.

I didn't have much longer to wait for Robert to show up. He was very prompt and got here early. "Yikes! I hope I look good for him!" I thought.

After the first knock on the door, I waited a second and took a deep breath before opening the door. I was very anxious and nervous about this moment. And there he was standing looking better then I had pictured him.

"WOW! Hello Ted . . . I mean hello Maria" he said the moment he seen me. "Can I come in, its getting chilly out here?"

"Oh yes. Sorry. Please come in and warm up those bones." My face flushed red when I said that. And all he did was smile at me, knowing what I really meant by that.

I smiled back at him and for some reason I felt speechless. I haven't really perfected my female voice yet. And I was trying play a little hard to get and tried to head for the bathroom. But he caught me. "Where are you going?"

"I thought I freshen up one more time." I looked back into his eyes. He had nice eyes. Kind eyes. Eyes that was undressing me already.

"You don't need to do that. You look beautiful as you are. And you smell great." He got very close and took in a deep breath of my scent. My face turned red again. But this time I didn't mind. He was making me feel very good about myself. And I was getting very turned on by it too.

"Thank you. You are very kind and sweet. Im glad we could finally meet."

"Me too. I love the dress. Turn around for me so I can see you." As he sat down on the edge of the bed.

I started to twirl around for him so he could see all of me. "Hows that?"

"Great! You look great in it. Now please come over here." He stood up as I approached him and reached out his arms to wrap them around me. I could feel his hands groping my big ass in his hands. It was a wonderful feeling.

"How about we take this off? But not yet." And then he kissed me on my lips very passionately trying to open my mouth. Our tongues danced. It was the first time I have ever been kissed like that. At the same time I could feel his hands move up my back and start to pull the back of my skirt up. He never missed a beat in our kiss and I could feel his hands feeling my ass through my panties.

And then he slowly started to pull the back of them down over my butt cheeks. Hes quick I thought. And then I felt a finger play in my crack, rubbing my asshole and poking at it until it got inside. "Oh my God! You naughty boy!" I said as I broke away from his lips. He just giggled a little and kept his finger in for awhile before he slipped down on his knees in front of me.

I lifted up the front of my dress and held it up while his hands pulled the elastic band of my panties down to my knees. I looked down to see him starring up at me and then my small cock in front of him. "I'm hungry for your cock now." He licked up under its head as it twitched to life. I could feel his hand wrap around it and then split my pee hole with his tongue. He soon engulfed my cock and started to suck me hard.

His warm moist mouth felt great. He sucked me slow and I wanted more and tried to fuck his mouth as I moaned out loud. To my disappointment he stopped me with his strong arms and started to lick my small shaft until he got to my balls. I was in for a real treat when he took one of them in his mouth, savoring its taste before he moved to the other one. For awhile he just teased and sucked on them before going back to my cock.

Shortly afterward, I felt him pull my panties all the way down and I stepped out of them. And then he got up and said, "Turn around and let me help you out of that." I just did what he said and my dress hit the floor too. I was almost naked in front of him, except for my stockings. I soon felt his hands reach around me under my breasts, lifting them and teasing my nipples between his fingers. I could also feel his lips kissing my shoulders. I let out another moan and I could feel his cock in his pants rubbing in the small of my back.

I wanted to see him naked too and turned around slipping my hands under his shirt and pushing it up. He took into his hands and pulled his shirt off while I undid his pants and zipper and started to pull them off until they hit the floor too. His boxers soon joined them. And then I went down to help him take off his shoes and socks as he sat on the bed.

Thats when I seen his cock. Not much bigger then mine. And it was just as hard too. I licked my lips wanting to taste his too. I went for it right there, taking its head in my mouth and slowly jerking him off. Words really couldn't describe how it tasted, but I loved every second I had it in my mouth. He soon stopped me and pulled me onto the bed on my back beside him. He started to rub and kiss my chest. My nipples got hard as he sucked on them and soon he started down my stomach until he got to my cock again.

He took my small cock in his hand and started to lick right under the head again. I moaned like crazy when he engulfed it into his mouth and sucked it. His tongue danced on the underside making me boil inside. He had the whole thing in his mouth too since its only about 4 and half inches long. He had no trouble with it at all.

I thought I was going to cum any minute when he pulled it out of his mouth. He licked up and down the shaft until a drop of pre-cum started to drip from the tip of my cock. He stabbed at my pee hole with his tongue again tasting it. "Yummy," he said. "I hope you have more of that."

I was so breathless I just looked down and said, "Yes! There's more coming soon." And then I pushed him back down on me. He slid his tongue back down my shaft and started licking my balls again. "Oh my God! That feels good!" My hands and fingers slid through his hair messing it up as I tried to pull him closer to me. But he kept up his own pace before he slid my cock back into his mouth and began to suck me very slowly. I wanted this to last a long time too but thats when I burst. Shot after shot of creamy cum into his mouth. He swallowed most of it too as he kept my cock in his mouth until I went completely soft. He then licked me clean of any cum he missed.

"That was delicious." He grinned with a dirty smile of his face. I could see a dribble of cum he missed running down the side of his mouth. I quickly pulled him up close to me and licked it off and kissed him. "Yummy. You are right. I do taste good." I just giggled like a little school girl.

He laid his head on my stomach for a while as I tried to straighten his hair for him. I was wondering if he was resting or something but he never said a word. After a few minutes I started to feel the urgency to pee but couldn't move with him on me. I really couldn't wait and my cock started to dribble some pee. I guess Robert was watching cause the next thing I knew he was licking and sucking me clean again. I fought off the urge to pee in his mouth. I didn't really know if he would enjoy that or not. But his mouth felt good again and my cock got hard.

I couldn't wait any longer and started to get up until Robert said, "Where are you going again?" "You know, I have to go pee. I will be right back." I said with some urgency.

And then he surprised me when he said, "let me watch?"

"What? You don't want to watch me pee, do you?" I was very surprised. But didn't think it was a disgusting thing. It was only me peeing. If he really wanted to watch it might even be exciting. So before he said another word I said, "Yes, you can watch. Come on. It might be exciting." I smiled at him as I took him by his hand and led him to the bathroom.

When we got into the bathroom I started to sit on the toilet. Its not lady-like to stand up and pee I thought. But before I could sit down he stopped me and said, "I have a better idea." He had a big grin on his face and pulled me towards the shower.

"What are you doing?" I asked.

"I want you to give me a golden shower. Its something I thought about it when I tasted your pee in there and I like to feel it splash on me. What could it hurt? It might be even more fun than watching."

After some debating again I thought it would be fun and said, "Okay. I will do it." And followed him into the shower.

He started to kneel down in front of me and decided I should take off my stockings so they wouldn't get wet. He got up and placed them on the sink for me. And then came back and got on his knees. "Okay. Let me have it. Shower me with your golden liquid."

I was feeling very excited hearing that and I noticed his nice cock waiting to be washed over by my pee. I reached down and pointed my cock towards his chest letting it flow slowly at first and then let it out full blast. I sprayed his chest, his stomach, his neck and then right down to his cock. I had a lot of pee saved up and didn't think I would ever stop. But like all good things, it does come to an end too with a trickle.

"Wow Hon, that felt great." He rubbed his hands all over his chest and stomach. "Lets take a shower together and get me cleaned up?"

"Okay." I didn't need to be asked twice. So I turned around and turned on the water spraying us both. Oops, I almost forgot about my wig, but didn't really care if it got wet or not at this point. We switched places and I got behind to wash his back. I felt his back and his buttocks. He had a nice ass too. I kissed his back and rubbed his ass for a while.

He then turned around to face me and embraced me with a kiss as his hands felt my back and down to my ass again. He then began to finger me again, but I had the feeling he wanted to do something else now. And I was right.

"Can I fuck you?" he asked. He looked at me as if I would say no any minute to him. But I have been wanting him to do that to me since he got here.

I answered him by turning around and bending over and leaning against the wall. "Please be gentle with me. I'm still a virgin."

"I promise I will." And then spread my cheeks with his hands. "You have a nice ass too." I felt him his tongue on my hole and licking me and probing inside. Getting it really wet. That felt even better then his finger. I can only wonder what his cock feels like. And my wish was about to come true when his tongue disappeared.

I felt something push against my hole and it certainly wasn't his finger or tongue. He slowly pushed his cock in and I relaxed as much as possible until it was all the way in. He stopped at that point waiting for me to get used to it. And then slowly fucked me. It was incredible. I felt myself burning up on the inside like I was on fire. And at the same time I was being cooled off from the water running off him.

"Oh fuck! You feel so tight!"

"Shit! You feel good yourself." I barely was able to say that much when my moans interrupted me.

I didn't know how long we were fucking. It felt like hours. And then I felt it. His body and dick jerked inside and I could feel his cum jet into me.

When he finally stopped, Robert pulled me close to his chest and held me. "That was great. we have to do this again sometime."

"Can we do it again? Later on?" I asked him wanting to be close to him again like this. And also really wanting him to stay the night.

"Sorry Hon, I will have to get back on the road soon. My wife will think something happened to me and worry." He then started to pull away from me and I could feel his cock slip out of my ass. But I grabbed him from behind me trying to keep him for as long as possible. He stayed for a few minutes longer holding me as his cock slipped out on its own.

He walked back to the bedroom to get dressed as I stayed in the bathroom to wash my makeup off and then started to get dressed in my mens clothes. Robert watched and waited the whole time seeing my transformation from Maria to Ted in a matter of minutes. If I had only one wish, it would be to stay as Maria for the rest of my life. I loved being a woman. And I loved the way Robert looked at me when he seen me as Maria too.

That was my fantasy night with Robert. It may never happen in real life. But it was very enjoyable to me and I hope Robert will like it too. My next fantasy I lived next door to him. But thats another story for another time. I hope you enjoyed the story.

BigChubT
BigChubT
16 Followers
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AnonymousAnonymousalmost 20 years ago
go all the way

excellent story, my cock is hard as a rock. however, having been in that position a few times, you should take that cock on the tip of your tongue, close your liups around the tiup so you dont lose any, and swallows that golden champagne eagerly. most of the time it is delicious.

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