Category: Transsexuals & Crossdressers Stories

The Naughty Coed Ch. 02

by necrotron©

Over the course of my freshman year at college, I had discovered I enjoyed sucking cocks. I never really considered myself gay, but I had found I really liked it.

Then at a party near the end of the year, I had turned a few heads in my tight pants and long hair. Enough to attract a hot senior and blow him in his car. He thought I was girl!

So I decided to try things on the other side and see how it worked.

When the school year ended I moved to a midsize city in the northeast to live at my aunt's house. My aunt Kelly had always been nice to me and when I told her of my plan, she invited me to stay at her place and attend the local community college. She was going to be away all summer in Europe with some boyfriend of hers. So I could housesit for her and experiment a little away from the judgmental eyes of friends and family.

I got to her house late in the evening and promptly fell asleep. The next day I spent unpacking the clothes I had bought on my way there. Being terrified of what people would say about a guy buying women's clothes to wear, I stopped at every mall along my trip to buy a few things.

What surprised me was the sales peoples' attitudes. They weren't surprised or anything. Some probably thought I was a girl and the others were simply tolerant of my lifestyle choice. Either way, I had a blast buying all new clothes.

I had bought some Nair, so I decided to take a hot shower and apply it to my legs and what was left of my pubes after trimming them with scissors.

After the shower, I put on a nice sun dress I had bought, tied my hair in a ponytail, and put on some nice girly sneakers. Checking my reflection in the mirror, I didn't look half bad. I added some lip-gloss and a little eyeliner a nice cosmetics lady had showed me how to apply.

Satisfied I looked pretty much like a girl, I went downstairs to eat a light breakfast. My aunt's house was great. A small craftsmen style one and half story, it was a wonderful place to stay.

After eating breakfast, I decided to go outside and wash the road dirt off my car. It was a pretty nice late model Honda Accord and I wanted to keep it nice.

Before I had even hosed it down decently I had a visitor. A very guy came walking up the driveway. He had on cutoffs and a pair of sandals. His tan body was to die for and he topped it off with nice brown hair and aviators. I was in love.

"You must be Ashley," he said to me in a nice warm voice.

"That's me!"

"Your aunt said you might be staying here this summer." He smiled and I about melted. He was good looking and boy did he know it. Guys like that know that all they have to do is be nice and girls will melt into their arms. Well it was working. "I'm Zack. I cut her yard and stuff."

"Hi. Nice to meet you Zack." I held out my hand for him to shake. He looked at me sideways for a brief moment, smiled, then took my hand and shook gently. "So are you going to do my yard this summer," I asked hopefully because I hated yard work.

"Well that's a good question." He took a moment to size me up I think. I kept wondering if he knew. I didn't care, but I did wonder. "I think I can help out a little this summer." He smiled warmly at me. "As long as my girlfriend doesn't get to jealous." I giggled. I actually giggled and probably blushed. "How about if I help you with this car?"

"OK," is all I could stammer out. He took the hose from me and started spraying the car down. Soon he had a bucket and sponge out of the garage and was washing the car like a professional. It hit me that he'd done this for my aunt.

After drying the car off with a shammie, he then waxed my car. The whole time I was staring at his amazing body. He was toned, not bulked. Every time he leaned over to get more suds or leaned over the hood to reach a difficult spot, I about fainted. Nice lean legs, a hard stomach and an ass so tight you could crack nuts on it, and boy did I want to.

Looking inside the car he just shook his head. "Maybe you might want to clean the inside as well," he told me. He was right. It was packed with all sorts of trash from the trip.

"OK," I stammered again. God he must think I'm an idiot. I ran inside to get the vacuum cleaner and he followed me inside.

"Mind if I get something to drink," he asked.

"Sure. Let me get it for you." I reached up and got a glass for him, feeling his eyes on me the entire time. After filling it with water, I handed it to him and watched him gulp it down. God he was gorgeous.

I went and grabbed the vacuum cleaner and a trash bag from the closet. Outside I opened the car doors and began emptying the car of trash. To do so I had to lean in, giving Zack and nice view of my ass. I looked back at him and smiled. He smiled back!

While vacuuming, I couldn't resist shaking my ass for him. I caught him smiling and admiring. Nice.

Once done I invited him inside for a soda. He sat on the couch and brought two glasses of Coke in for us. I sat down close him and tucked my legs underneath me, trying desperately to look at least a little sexy.

"So what do I owe you for washing my car," I asked him.

"Well you could pay me what your aunt always pays me," he replied with a smile. I panicked a little. I had spent most of my cash on the trip up and only had a few ones.

"How much is that?"

"Well it's not how much she pays me, it's how she pays me," he replied with a smile.

"How does she do that?" To answer he unzipped his shorts and pulled them down. He wasn't wearing underwear so his massive cock just flopped out. It was huge and not even hard yet. "Oh," was all I could say.

He just looked at me a little smugly. It pissed me off a little, but how could I resist.

I leaned down and picked up with my both of my hands. It had to be at least eight inches and it was starting to harden. I spit on my hands and began pumping him. It grew to about ten inches and wasn't real thick. Just a nice long piece of meat.

After pumping for about a minute I started sucking on it. It felt so good in mouth. A trickle of precum came out and it tasted great. Real sexy like. I started sucking in earnest. There was no way I could take this monster in my throat and thankfully he didn't force me. Why would he? He was used to being serviced and I was just the latest girl to do so.

I began to massage his nice thick balls with one hand while pumping him with the other. All the while my mouth was in full suction. God it was good.

Before long he began cumming. He pumped what felt like gallons into my mouth. I couldn't contain it all and about half spilled out onto his lap. I choked down the rest. After he finished I just looked up at him.

"Well you can't leave me all dirty like this. Clean me up," he said.

So I bent down and licked him clean. Every last drop. It took me forever and he began to get hard again.

"Maybe I need to get an advance for my yard work," he said. I wasn't sure what he meant, but I knew he would find out my dirty little secret.

"Umm, Zack I have something to tell you and you may not like it."

"What that you're a boy?"

I couldn't believe it! "How did you know," I asked.

"Well your aunt said that you were coming to stay this summer and that I should talk to you about payment for yard work and stuff. When I asked who you were, she just said 'he's my niece', I kind of figured it out from there." I about shit myself. My aunt had inadvertently ratted me out. "Plus, you can kind of tell if you look close and I looked really close."

"So you still want to do something?"

"I'm going to fuck that ass and I don't care what you have in front of it. Now bend over!"

I did as ordered. How could I resist. He lifted my dress and pulled my panties down. Spreading my ass cheeks, he spit a few times into my ass crack . Then he stuck a finger in there and started finger-fucking me hard.

I moaned with surprise and delight. I'd never had anyone do that before and it felt fantastic. My ass spread willingly for his fingers. It never once crossed my mind that they were no way near as big as his cock, but I would figure out the difference soon enough.

He kept spitting on my asshole and fingering me for a few minutes. Then he slid two fingers in and continued. Suddenly he roughly shoved three fingers in my ass. I about passed out from shock. Wow did it hurt, but I loved every moment of it.

Pulling his fingers out caused my knees to buckle for a moment, but he grabbed me by the waist and pushed me down onto my stomach. There I lay face down in the couch waiting for him to break my ass-cherry.

Then I felt it. Pushing against my asshole. It felt like a brick being shoved up there. Oh did it hurt. Finally it was in and I could feel it sliding deeper into me.

Slowly he began fucking my ass. The pressure was tremendous. I felt like I was shitting a Volkswagen! In and out he went. As he fucked me I began to get used to it. I remembered how most guys came quick the first time, but slowly the second. This was going to take awhile and it did.

For what felt like and hour, Zack fucked my ass. The burning sensation was almost unbearable and I thought I would pass out from the pain. It did feel good though. Oh did it feel good. He had his hands on my back pushing me down into the couch as he slid in and out of me. Just sawing me in half like the whore I was.

Zack sped up his motion and finally cummed deep in my ass. He pulled out and said, "stay right there." He left the living room and came back an few seconds later with some paper towels. "You're bleeding a little," he told me and shoved the paper towels into my ass crack.

Great. What a wonderful humiliation. Being ass-fucked for the first time by some guy you just met and then having him shove paper towels into your ass. And people say romance is dead!

"Well, I guess I'll see you tomorrow when I mow your lawn." With that he pulled up his pants and left.

This was going to be a crazy summer.

Written by: necrotron

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Story Tags: crossdressing, oral, coed, blowjob, anal, college, gay, transgender

Category: Transsexuals & Crossdressers Stories