My New Girlfriend

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He finds a beautiful cross-dressing college boy.
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I flew into Boston about an hour ago to visit my little brother in college. My brother well adopted brother Mike was supposed to pick me up at the airport but he must have forgotten. I took a cab to his apartment with the intention of giving him a huge rash of shit for leaving me there.

When I got to his place there was no answer at the door and I was getting more pissed by the minute as I paced back and forth while trying to call him. After about an hour (which made it 10:30 at night) a neighbor showed up. I asked him about Mike and if he knew when he'd be back.

"I'm not sure," he says "sometimes he's out late."

I was even more agitated at this point. "Y'know," he says "you can leave your stuff at my place if you want there's a bar down the street if you wanna just hang out for a while."

I though about it for a second and a cold one really sounded good. I left my bags inside his door and headed for the bar.

Well the bar wasn't just down the street. It was about eight blocks and was a welcome sight when I found it. I walked in and sat in a dark corner so I could people watch. A good looking guy came up to the table and introduced himself as Henry and the he would be serving me tonight. I giggled inside at the forced fake like introduction.

"Ok Henry I'll have a draft beer and with a whiskey back."

"Thank you Sir" he says and walked away with a little to much sway in his step. Once again I giggled to myself.

I looked around. There were a few people in the place, more guys than girls as you would find in any bar. Henry returned with my drinks and left.

I pounded back the whiskey and took a sip of the beer. As the warmth of the whiskey made its way inside I felt the agitation starting to subside and I slid down into my seat for a quiet evening.

There were about 15 guys and 8 girls all about college age. The music started up and this cute little thing came out of the dark corner opposite mine and proceeded to the so called dance floor in the middle. I was about half way through my beer already and starting to feel its affects. I was feeling good. Henry returned.

"Another round?" He asked.

"Sure" I replied without taking my eyes away from the gyrating hips of the sexy little dancer.

A guy dragged himself from the bar and started dancing behind the girl. "Shit" I thought "I should've moved faster." Truth be told though I was quite content with watching her.

Henry returned with my drinks and once again swaggered off back to the bar.

My sexy little thing on the dance floor was now up and close to her new admirer dancing to something slow and I was enjoying watching the sway of her tight ass in the sexy slinky dress she was wearing.

The song ended and the couple separated. I watched her smooth long legs carry her back to her dark corner on her 4" heels and quietly groaned to myself.

My drinks gone I tried calling Mike again. No answer. Frustrated I ordered another round. The music started up again and the object of my fascination made her way back out again.

I watch her move mostly focused on her body but eventually my eyes made their way to her face. She was truly beautiful. The more I looked the more I really liked.

The drinks were flowing into me on a regular basis now and I was really liking the way this girl looked. Through slightly blurred vision I starred at her and the more I starred the more she looked familiar. After about 3 hours of drinking and sitting with a semi-hard cock it occurred to me who my dream girl was.

I ordered on my whiskey back and pounded down the whiskey. I slightly stumbled to my feet and made my way through the dark areas of the bar to her table. I sat down across from her. She looked up shocked at seeing me.

"Hi Mikie" I said.

"Dave oh my god I thought you weren't coming 'til tomorrow" he or should I say she said.

"Mikie" I started to say

"Dave call me Michelle in here."

"Ok Michelle I think we should go home don't you think."

Mikie sorry Michelle picked up her purse and helped me up. On the walk home my brother told me how since he'd been in college he had discovered that he loved cross-dressing.

"So you don't want to be girl or anything?" I asked.

"No it's not like that," he said "I like dressing as a girl and being treated like a girl but I still want to be a boy."

"Well Michelle," yes I called him Michelle "you make one hell of a sexy girl."

"Thanks" she replied smiling softly at me.

We walked the rest of the way in silence with Michelle's arm looped through mine. When we got home Michelle made us some drinks and got me a blanket and pillow to sleep on the couch.

Michelle went in the bathroom to change all the while talking to me. I got up from the couch and walked over to where she was. I stood in the doorway as she pulled her dress up and over her head.

I watched as the hem slowly moved from just below her ass. Oh that ass. Her hips were slight wider than her waist giving her a sexy shape. Her red lacey thong sat sexily on her hips as a little string disappeared between her firm cheeks.

I put my drink on the bathroom counter and place my hands on her hips. Michelle looked back at me over her shoulder.

In a quiet whisper she says "Dave what are you doing?"

"Treating you like a girl" I said. I moved my lips to hers. I kissed her softly, tasting her sweet lips on mine. I moved my hands around to her front pulling her back to me. Her warm firm cheeks nestled into my jeans clad cock.

Breaking our kiss, "are you sure you want to do this?" she asks.

I nod my head at her like a virgin being asked if he wants a blowjob.

Michelle led me back to her bedroom. It's decorated just like a girl would. Lots of pink, her bed covered with a ton of pillows and teddy bears.

Michelle crawled onto the bed throwing the pillows and bears onto the floor. I watched as her cheeks spread while she was on her hands and knees. The red string from her thong laying down the middle and making its way around the front to the V-patch of material covering her most private area.

I reached out and traced the thin string with my finger. When I reached her private hole she giggled (just like a girl) and stood up.

In the back of my mind I knew she was a boy but what I was seeing was 100% pure sexy girl.

Michelle pushed me back onto the bed. Undoing my belt and jeans, she grabbed a hold of the sides and started pulling them down. I lifted my ass up to help and my hard uncircumcised cock sprang free slapping against my stomach.

She pulled my jeans from my feet and tossed them aside. She looked up and crawled between my legs running her hands from my knees to my hairy crotch. Jeeezus my crotch was hairy. Since I didn't have a girlfriend I had stopped trimming.

Michelle lowered her head and took one of my big hefty cum laden balls into her mouth. It was warm and wet and I loved every moment. Then she moved to the other, I might blow right now. She released and then I felt her tongue dive into my sweaty crack and lick my now puckered hole.

It was exquisite. I threw myself back onto the bed and lifted my legs up for her. She plunged her tongue deeper until she was inside. I felt incredible. She stroked my cock, rubbing my foreskin over my glands as she slowly slid a finger inside my waiting hole. Her finger went deeper and all of a sudden my cum rocketed out and up onto my shirt.

Michelle was wonderful. No girl has ever made me cum like that or that hard before.

I finally opened my eyes to see her standing between my legs smiling at me. "If you liked that you'll really love my blowjobs" she said giggling at me.

I pulled her down on top of me pushing my tongue inside her mouth. I tasted my own asshole on her. It was tangy but not repulsive. I rubbed my hands all over her body slowly, exploring ever inch.

I reached the sides of the thong and started to ease it down. She broke our kiss and grabbed my hands.

"You do know there isn't a pussy inside those panties right?'

"I know" I whispered in her ear.

I few of hours ago I would never have even thought of another cock but now I wanted whatever was inside this red thong. She let go of my hands and I eased it down past her ass.

I felt her hard cock lying next to mine but I just had to see it. I rolled Michelle over and stood at the foot of the bed. I removed my shirt and threw it way somewhere in the room. I leaned down her cock no more than 8" inches from my face. I looked into her eyes and pulled her panties all the way off caressing her legs on the way.

I looked down. Her cock was not what I expected. She was hard extremely hard. She was completely shaved, her balls, shaft everything was smooth. I kneeled to get a closer look. I spread her legs and moved between them. Her shaving didn't stop with her cock everything was silky. Her legs and ass were also a smooth as a baby's bottom.

I ran my hands up and down her thighs admiring the silkiness. I touched her balls, she moaned. I cupped them feeling their weight. They were so sexy. I ran a finger to her crack slightly touching her hole. She reached under and pulled her cheeks apart.

I took this as a sign of what she wanted and lapped my tongue over her pink little entrance. I lubed her up good before sliding my thick finger inside her. Finger buried inside I lifted her circumcised cock to my mouth wrapping my lips around the head.

Her pre-cum was sweet. I was lost I had never sucked a cock before. What do I do?

Flash backs of all the blowjobs I received flew through my head, the good and the bad. I quickly filtered through them picking out the things I liked and making note of the things I didn't making sure I didn't do those.

I pushed my lips down her shaft keeping my tongue pushed against her glands. She moaned, loudly. I repeated this several times. I wrapped my hand around her shaft under my lips so I wouldn't choke myself.

I stroke her a few times, licking the head with full vengeance. I wanted this girl to cum and I wanted to be the one to make it happen. I turned my head sideways and pursed my lips. Pushing them into her shaft I slid my lips up and down her shaft. Up and over her glands.

Michelle was panting hard I knew she was going to cum. I pumped her furiously lapping and licking her cock head as fast as I could. Michelle's hips were pumping, she was close now. I stroked her faster giving her long laps on her glands.

One hard grunt from her and there it was. Her cum flew out hitting me in the forehead, the rest landing on her chest and her matching lacey bra.

Michelle slowly opened her eyes as I placed my hands under her knees and lifted her legs. She smiled as I positioned my cock at her spit lubed hole and pushed inside. It was easier getting inside than I thought. Before either of us knew I was buried all the way in.

I wasn't going to last long, sucking Michelle's cock had made me so horny. I pumped slowly as I lay on top of her little body. I'd never fucked a girl's ass before and now knowing what it felt like I knew what I was missing.

My cock slid in and out of Michelle as my head was buried into the bed cover above her shoulder. Her arms wrapped around me I knew I wasn't fucking. I was actually making love to her. Treating her like a girl just like she wanted.

My paced increased as I felt my cum rising. I tried holding back until Michelle whispered in my ear "it's ok Dave cum inside me, please cum inside me."

I pounded her ass faster as my cum flew from my prostate to her insides where it would meet hers. I was exhausted as I lay on top of my dream girl completely drained.

We giggled together as she whispered "did you have a good flight?"

The flight wasn't bad but the landing was better.

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ShortyMacShortyMacabout 1 year ago

Great story, took Dave Long enough to figure out who the hot girl dancer was. 10 stars for this hot story.

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smoothed273smoothed273about 1 year ago

šŸ‘šŸ‘šŸ’–šŸ’–šŸ’–šŸ’–šŸ’‹šŸ’‹šŸ’‹āœŒ

Epic_ThoughtsEpic_Thoughtsalmost 15 years ago
More! More!

This is an amazing story! I wish you'd write more about Dave and Michelle, as this story just cries out for further installments. Thank you!

Epic_ThoughtsEpic_Thoughtsover 15 years ago
Thank you!

I liked your story alot. I hope we get to see more from you. Thank you for your work!

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