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Jessi's coming out party

Jessi comes out to several friends and has an interesting night.
Hi everyone. My name is Jessi, I'm 23 and I have been a crossdresser for over three years. Recently I decided to go full time and was going to met up with some friends to come out to them. I arranged to go hang out with them at my friend Derek's house, them thinking I was still coming as my old self. My roommate, who started my path into crossdressing (that's a whole other story), told me if I was going to come out to friends that I should do it in style. She lent me her cream colored dress with a black mesh flower print overlay and I grabbed my 4 inch black pumps. A little back story, I am only 5'1 and about 112 pounds.

I arrived at the house and my friend Derek answered the door. "Hey there," I said in my feminine voice.

"Can I help you?" he asked me.

"Yes, you can let me in and I can tell you what I have been up to the last few years," I said in my guy voice.

"What the fuck...." He stuttered out. "Jess... is that you?"

"Yup. And I go by Jessi now," I replied back in my female voice. "So can I come in?"

"Ugh yeah... come on in," he said as I caught him checking me out. I started to walk in and he shut the door behind me.

"Don't tell them it's me right away," I said as I giggled. I could feel him staring at my ass as I walked by.

"Um... ok," he replied. "Hey guys, look what came to the door," he said as we entered the next room. My other friends, James and Drew were sitting on the couch watching tv. They turned and saw me walk on. I could feel their eyes staring me down.

"Hi there," I said as I smiled.

"Hi, I'm James and that's Drew," James said as he stood up.

"I'm Jessi," I said in my girl's voice still.

"Aw cool name, we were actually waiting for our friend Jess....... what the f?" Drew said. "Jess?"

I started to giggle and said, "Did I fool you guys?"

"Damn straight you did," James said. "Sit down and have some beer and tell us about how all this happened," he said as he made room for me on the couch. I sat down and began to explain to them about how I started crossdressing and went full time. (Again a story for another time. Hehe.) All while we continued to drink beer and mind you all I'm a light weight.

"So do you play for the other team now?" Derek asked me.

"What do you mean?" I replied.

"You know, do you..." He paused. "Have relationships with guys?"

"Haha, you could have just come outright," I said. "And yes, I do."

"So have you ever sucked a cock?" Drew said as he looked me over.

"Why do you want me to suck yours?" I replied. I could see his penis grow in his shorts. That's when I lost it.

"No... no," he replied. As he said that I got up and got down on my knees in front of him. I pulled his zipper down and he said, "What...what are you doing?" I pulled his pants down and his underwear too. His full erect penis was out and up.

"Giving you what you want," I said as I took his penis in my mouth and began to blow him.

"Oh my gooooddd.. Thats amazing," he said as I continued to give him head. I could imagine my other friends freaking out. That's when out of the corner of my eye I saw James masturbating right next to me. I reached my hand over and wrapped it around his cock and began to stroke him. As I did that Drew put his hands on my head and began to bob my face up and down.

"Damn, this feels so good," James said as he leaned his head back.

"Derek come here," I said in a sexy voice as I pulled my head off Drew's cock. He walked over to me. "I want you to fuck me," I whispered in his ear. As he got his pants down I pulled my thong down and hiked my dress up. I then licked his cock and told drew to spit on my hole. He did and I turned back around and I felt Derek's cock enter my ass. As he did that I went back to blowing Drew and giving James his handjob.

"She is so good," I heard Derek say as he pounded my ass hard and fast. It hurt at first but the more he did it the more pleasure I felt.

"Oh man I'm gonna cum," James said as he came all over my hand. I never stopped and continued to blow Drew.

"Ughhhhh," Drew let out as he began to shoot his load in my mouth. I swallowed it and then focused on Derek doing my ass.

"My god.... this is amazing," Derek said as I could feel him tense up.

"Cum inside me," I said as I started to shudder in pleasure. Just then I came and it dropped all over the floor in front of me.

"Yesssss," Derek said as I felt him cum in my ass. "Wow, that's the best sex I ever had."

"You guys wanna switch?" James asked every one. Everyone waited a few minutes until we all recovered. I then started to give James a blow job as I took Derek's cock in my hands. As they started to get hard I felt Drew enter my ass.

"Mmmmmm," I started to moan as I was pleasing all three of my best friends from high school.

"Yes," they all said one by one. After a few minutes of this all three of them came again. Drew in my ass, Derek on my hand and James in my mouth.

"You know it's only fair if all of you get to do everything once," I said a few minutes later. As I was saying that they all switched positions again. I began to give Derek a blow job, Drew a hand job and James wasted no time entering my ass. Almost instantly I came again making another spot on the floor. I continued working on them till I could feel them ready to cum for a third time. Just then Derek pulled out of my mouth and came all over my face. James and Drew both came at the same time.

"Wow," Derek said. "That was unexpected."

"Yeah," James and Drew said.

"So I take it you guys have no problem with me this way?" I asked.

"No," they all said. "We liked it before the sex." We all laughed. We hung out a little more after I went to the bathroom and cleaned up. James and Drew fell asleep on the couch.

"Can I sleep here tonight?" I asked Derek.

"Of course, you can use the guest room," he replied.

"Thanks," I said as I went into the room.

"I'm going to bed. Night," he said. he then went into his room.

I ran out to my car quick and grabbed some purple lingere and 5 inch heels. I went into the bathroom and changed. I then knocked on Derek's door. He answered and his jaw dropped.

"I wanted to thank you for accepting me this way," I said as I wrapped my arms around him. He then kissed me on the lips and I returned the favor. He then led me into his room and laid me down on the bed. What happened after that, well that itself is another story.

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Comments(6)

sweetmc
Posted 13 Dec 2012 11:38
Great story, want to hear lots more...
sammy_CD
Posted 19 Aug 2012 18:35
loved it......more please
tinytit
Posted 15 Aug 2012 22:50
wounderfull story and would love to here more of your crossdressing stories
mredd
Posted 14 Aug 2012 17:24
Good story just wish you finished telling what happened that night.
irishfella
Posted 14 Aug 2012 07:44
please write the next story and the one on how you started loved it 10/10
nazhinaz
Posted 14 Aug 2012 05:36
A good story of a crossdresser.
 

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