Out by Myself

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Getting more than expected when I go out alone.
3.3k words
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Ben and I continued to see each other when we could. But as with a lot of relationships, things began to become routine. I needed some excitement in my life. I found the opportunity when I was called into my bosses office. He told me that I had to go visit a supplier for our company. He needed me to go asap. That night if possible. I told him that I could, and since they were a couple hundred miles away, I would drive, and be there in the morning. He gave me the day off so I could pack and drive there.

As I drove home, I decided to take the opportunity to have some fun in a place where nobody knew me. I packed two suitcases. One with my work clothes, and the other with my night time clothes. I pondered the idea of driving while dressed as a woman. But thought better of it. Maybe when I come home, I thought.

The drive was boring, except for the thoughts of what I could do while I was there. That helped me to pass the time. The fun I could have while dressed up. The possibilities were endless.

I got to the motel, and discovered that it was pretty much a dive. I thought about calling my boss and complaining, but then I thought it could work to my advantage. It was on the outskirts of town. I didn't have to pass through a lobby. I doubted that anyone would care what I did. And it seemed to be mostly empty. I checked in and went to my room. It was on the second floor, with a nice view of the parking lot. Well I wasn't here for the view. The room was less than I expected. It looked like it was straight out of the seventies. I settled in and put my things away. Well most of them. I stripped down, and sat on the bed. I proceeded to side into a pair of leg's pantyhose (I didn't want to start with my fancy ones). Then my breast forms, followed by a red lace bra. Since I wasn't planning on doing much tonight, I put on a tight black t-shirt and a jean skirt. I sat down and put on some make up. I applied just enough to make me look feminine. I put on my wig, and made sure that it looked good. I gave it a few brushes to smooth it out. Lastly a pair of black four inch stilettos. I was all set for a boring evening.

As it was getting dark, I decided to go for a little walk. I grabbed my purse and put the room key in it. I checked my make up, and stepped outside. The cool breeze felt good as it wrapped around, and up my legs. I made my way to the stairs, and went down. I walked through the parking lot, away from the office. I made my way down the quite street the motel was on. At the corner was a convenient store. I was thirsty, so I decided to get something to drink. I walked in, and the three guys in there. They all turned and looked when they heard my heels clicking on the tile floor. I strutted past them and went to the coolers. I bent over to get a 6 pack of hard lemonade. When I turned around, they were all starring my long legs. i noticed that they all seemed to be in a state of arousal. One even had to adjust himself. I strolled up to the counter. One of them made his way to the register so I could pay. I paid for my drinks, and gave him a little wink, he was kind of good looking. I turned on my heel and left, giving my hips a little extra sway as I walked out.

I walked back to the motel. I saw a few more cars in the lot, but nobody outside. As I made my way to my room, I noticed a few open curtains. As I walked past one of them I noticed a man in his underwear laying on the bed. I chuckled to myself. He looked pitiful laying there. I went into my room and had a few drinks. I looked at the clock, 8:23. Damn, this night was dragging on. I opened the last lemonade, and drank it. Nothing on tv, and now 8:46. I opened my door, and stood there for a minute. a few more cars were in the lot. But still nobody around. I leaned over the railing looking at the city skyline, trying to figure out what to do.

"Beautiful, isn't it." a deep voice suddenly said, startling me.

"Yes, it is." I replied. I looked over to see an older man standing next to me.

"Not just the sunset." he said, looking at my backside. He made no attempt to hide the fact that he was looking at my ass. "It truly is a magnificent sight." His eyes were locked on my rear.

I stayed bent over for him, letting him have a good look. I glanced at him, giving him a quick once over. He appeared to be about forty five, and very tall. Maybe 6'6". A bit of a gut, but not too big. He had a black button down shirt on with blue jeans. 'Not a bad looking man. This night just took an interesting turn.' I thought. I stood and turned to face him.

"I'm Edward. But you can call me Ed." he said as he extended his hand. I took his hand and as I began to shake it, I went into a panic. I couldn't tell him my real name!

"I'm Colleen." I said, the first name that came to my mind.

"Pleasure to meet you Colleen. Would you like to go for a little walk with me?"

My mind settled down enough to agree. I got my purse, and we slowly walked around. I noticed a few more open curtains, and a few open doors. These rooms seemed to have men in them. And they all looked as I walked by. Then it dawned on me that this motel must be a local hang out to get laid. And Ed was showing me off. We got to the end, and began to walk back. I saw that more guys were standing outside now. Ed was showing me off! The guys were leering at me as we walked back. A few even had their hands in their pants! I was disgusted, and intrigued at the same time.

As we walked past them, they openly leered at me. I felt like a piece of meat on display. When we reached the other end, Ed led me to the other side of the motel. I saw the same thing on the other side, maybe fifteen, or so, men standing either in their doors, or outside, all looking at me. Subconsciously I began to walk more seductively. Slowly I became aware of the sound of my pantyhose thighs swishing together. My heels clicking on the cement floor. I began to feel my breasts wiggling. Ed put his hand on the small of my back. He clearly was claiming me in front of all the men, and showing me off. Ed guided me down the stairs, and did the same thing. He paraded me around the motel before a lot of men. All of them paying no attention to him. All eyes locked on me. And all of them in some state of arousal.

'My God! Did they call each other?' I thought? Finally we stopped at a door.

"This is my room." Ed said as he opened the door. He gave me a light push, hinting for me to go in. I wasn't exactly pleased with him treating me like he did. But as tall as he was, I was curious about the size of his manhood. I did notice a rather large bulge when I first looked him over. But still I hesitated. Ed pushed me a bit harder, almost forcing me in. I was struggling with the thoughts of, what an ass, and I bet he has a huge cock. I bet he has a huge cock won out, and I stepped into his room.

Ed closed the door and the sound of him locking it rang in my ears. He sat on the bed, and patted the space next to him. I walked over and sat next to him. Ed wasted no time, he leaned over and placed his lips on mine. He kissed me hard, very hard, as he held me next to him. He put a hand on the back of my neck, holding my head in place. He parted his lips and jammed his thick tongue into my mouth. It tasted like cheap whiskey and cigarettes. His tongue ran all over inside my mouth. Ed began squeezing my breasts. I had to get control of the situation, and fast.

Eds hand then gripped my lower thigh. He squeezed it tightly. My mind was racing as I tried to think of someway to gain the upper hand before he discovered my secret. Now his hand was going under my skirt! I tried to stand up, but Ed pulled me back onto the bed. I fell back so I was now laying on the bed. Ed laid next to me, and resumed kissing me. He was now across my upper body, holding me down. I squirmed a bit under his weight. My leg brushed against something rather large and stiff. Was that what I thought it was? Could he be that big? He felt me relax a bit, and took advantage of the opportunity to slide a hand up my thigh. He found my secret! He gripped it and began to stroke it. I was shocked, but pleasantly surprised. Ed sensed that I relaxed, loosened his weight on me.

I reached for his belt, but couldn't quite reach it. He moved up a bit so I could. When I put my hand back I ended up grabbing his hard tool. Oh my God was it huge! I undid his belt, and then his pants. He pushed them down, and his cock flopped out onto my thigh. I felt like it was at least ten inches long. I swear it was alive. I felt it twitching and throbbing as it continued to grow up my leg. The head lifted my skirt up as it went under it. Not only was it long, but it was thick. Ed moved and straddled my legs. His balls were equally large. When he dropped them on my lower thighs, I thought he dropped a couple of heavy golf balls on me. They were the biggest I had ever seen. I watched Ed drag them up and down my thighs, while his cock stood up like a flag pole.

He undid the button on my jean skirt, then pulled the zipper down. Ed grabbed the hem in his big hands, and pulled my skirt off with one strong yank. He tossed it aside, and rolled me over. He sat on the back of my legs, and his dick fell on my ass. Ed leaned forward, pressing it in my crack. It felt like it was longer than my crack.

"I love the feel of pantyhose, especially on my cock."

All I could do is moan as he ground his massive tool on me. I pressed back, trying to make him reach orgasm. Ed moved around a bit, then he sat up. He just sat there for a minute. I was wondering what he was doing, then I felt something drip onto my ass. Ed then pulled my pantyhose down to mid-thigh. I heard something clatter onto the floor. I looked over to see what it was. As I tried to read the label, Ed was moving around. Then one word on the bottle stood out. Lubrication! My eyes went wide and I gasped. Before I could form any kind of protest, the thick head of Ed's long penis penetrated me. My rear stretched to accept him. He had lubed himself up well, and could slide in easier than I thought he would. Ed went slow and steady, making his way further and further up me. It was all I could do just to breath.

"Thats it Colleen. Relax. Half way in now."

Only half! Oh crap! It already felt like he was in my stomach! Yet I was yearning for more. I wanted, no, needed to see if I could take all of him. I had to have Ed in me all the way. I felt his balls slowly inching up my thighs with each thrust. I gasped and moaned as Ed continued to stretch me, going deeper than I ever thought possible. I couldn't wait any longer.

"Give... me...all...of...it...nnnnooowwww!" I croaked out.

"You want the rest if my big cock?"

"Yesss!"

"Should I just slam in all the way in? Plunge it deep in you? Just one hard push? Is that what you want?"

"God yes! Give it to..." was all I got out. All the air suddenly left my lungs. My brain suddenly went blank. My body stiffened up. Ed gave me what I wanted. The rest of his massive cock plowed all the in me. I tried to scream, but nothing came out.

"Is that what you want?" Ed said. He didn't move his pole. I was impaled by his monster. My ass was on fire. Ed began to back out. It seemed like forever as he eased almost all the way out. Then Ed suddenly went back in. He began to fuck me with a steady rhythm. Slow at first, then fast, then slow. My brain was loosing control. Ed then pulled out, and rolled me onto my back. He lifted my legs onto his shoulders. I looked in between my legs as he grabbed himself, and lined up to enter me again. My eyes rolled back as he plunged all the way in. Ed's big hands held my calves. He gave me a very hard thrust, going very deep, and held it there. My legs began to shake uncontrollably. Ed flexed the muscles in his cock, sending waves of pleasure radiating through my body. I shook so much that my left heel flew off. My hands gripping the sheets as Ed brought me to new pleasures.

My head was spinning as he pushed my left foot into his mouth. He pressed his tongue against my little toes, and began to suck on them. Ed pushed almost half my foot into his mouth. He licked and sucked on it. His saliva soaking my pantyhose covered foot. I lost control and reached orgasm. I has never cum so hard. I shot all over my t-shirt. Ed saw this, and he began to fuck me. He quickly picked up his pace. My foot slid out of his mouth as he focused on pounding my ass. Ed gave one last deep thrust. Then I felt a flood of cum filling me. Ed came for over a minute straight deep in me. I thought he would never stop! Finally Ed finished, and began to soften. He slowly pulled out of me. I felt a void when he finally slid out. I tried to catch my breath as I came down from my sex high.

I noticed the clock. 12:38. I jumped off the bed.

"Ed I gotta go. I have to get up in a few hours. Thank you. You were great!" I said as I pulled my pantyhose up.

"Colleen, you weren't too bad yourself."

I grabbed my shoe and slipped it on. Ed pulled me over and gave me a long passionate kiss. After a few more minutes, I broke the kiss, and left. I walked toward the other side of the motel, and my room feeling very satisfied. The only sound was my heels on the cement. I was on cloud nine.

As I strolled past the room with the vending machines, a voice suddenly called out.

"Hey sexy."

It caught me off guard. I didn't even notice anyone around. I made the mistake of stopping to see where the voice came from. I turned and saw a guy standing there looking at me.

"I got something for you, sweetie" he said as he grabbed himself.

"Well, let me see what you got?" I said thinking it would shut him up. But I was wrong. He yanked his shorts down, letting his dick spring free.

"You wanted to see it. Now what are you going to do with it?"

I walked over to him, and took his dick in my hand. I began to stroke it until it was stiff. Then he pushed me down. I was crouched down with my face directly in front of his hard dick.

"Suck it. You know you want to."

I found myself leaning forward, and wrapping my lips around his cock. I ran my tongue all over it. Then I started to get to work on it. I took it all the way to the base. I wrapped my tongue around it. He started to fuck my mouth. As I sucked hard on it, I grabbed his hips for balance.

"Thats it bitch. Suck my hard cock. I'm gunna full your mouth with my cum, and you better not spill any."

As he said this, I felt a wad of Eds cum drop out of my stretched ass. It soaked my pantyhose almost immediately. But it also drove me on to suck harder.

"You must really want my cum, you whore. Get my balls in your mouth too, you slut."

I was loving him calling me names. I opened my mouth wider, and he pushed his balls in. I gagged a bit when they went in. Once I got used to them, I started to lick them. They tasted salty as they rolled over my tongue.

"That feels great bitch. You are one horny cunt."

As he said this, another wad of Ed's cum dripped out. It sloshed in my pantyhose as I rocked on my heels. I sucked harder on the dick in my mouth, driven on by Ed's cum dripping out.

"That's it. Suck me good. Make me cum in your mouth. I'm getting close. Harder birch."

I did as he said, and sucked harder. This had an unexpected effect on me. When I gave his dick a hard suck, I felt a flood start down my tunnel. I tried to stop it, but I was to stretched to do anything. Ed's discharge gushed out as I sucked again. It ran through my pantyhose, and landed on my ankles. It continued down into my heels. It dripped into shoes, and made its way into the toes. I sucked even harder on the cock now.

"Thats it slut! Here it comes!" He pushed his dick in as far as he could, and started to cum as I started to gag. My mouth quickly filled with his cum. I pulled back, allowing it to pop out of my mouth. I spit out the cum in my mouth as I gasped for air. He continued to shoot all over my face. Cum was dripping off my face and landing on my skirt, thighs and on my shirt.

I quickly stood and left.

"I told you you couldn't handle it bitch!" he said as I quickly went around the corner, and went into my room as fast as I could. I stripped off my clothes and took a quick shower. Then went to bed.

The rest of the week, I focused on my work. But when I talked to my boss Friday morning, he said that I needed to stay until Monday or Tuesday. What was I to do for the weekend in a strange city?

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AnonymousAnonymousalmost 2 years ago
First Timer

I have been dressing as a woman for a long time now.I have changed my body to a full on woman with a cock.My breast are a firm 38d cup and with a hairless body i look good.Over the years i have become a real cock whore.Feed me a hard cock in my ass and down my throat filling me with cum.How i do love the taste of sweet cum.I have been known on a good night at the adult movie to deep throat as many as eight or more hard cocks for their loads of cum.But i would never pass up a hard cock in my ass for a good load of cum.

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