An Unexpected Birthday Gift

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Best friends celebrate with 1st time trans sex.
2.9k words
4.36
51.1k
19

Part 1 of the 2 part series

Updated 10/30/2022
Created 12/18/2011
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It was my best friends birthday and I was taking him out for a night on the town. We have been best friends since we were kids and I was going to give him a special present. We started the night out with dinner at a nice sit down restaurant where we had a few beers and some really good steaks. This was his first birthday since he had finalized his divorce so I wanted him to have a good time.

After dinner we headed to a local strip club to check out the girls and have some fun before we went to try to find some pussy at one of the local clubs. We were there for only a few minutes when we had a couple girls hitting us up for some dances. There was a 6' blonde named Mercedes that had really caught my buddies eye. This girl could have been in the magazines. She was an Amazon with a body that should be worshiped. She was dressed in this tiny denim outfit that didn't leave much for the imagination. She had the most beautiful breasts I had ever laid eyes on. The g-string she was wearing barely covered her bare pussy when she was bending over whispering in my buddies ear.

I decided that it would be a good start to the night if she gave him a lap dance. I slipped her a 50 and told her to take her time and make it extra special. The dance lasted about 20 minutes and by the time she was done the g-string was laying on the floor by my feet and my buddies pants were soaked by her juices and being stretched by his hard cock. As soon as the dance was over she was called to the stage for her set. She left in such a hurry that she forgot all about the g-string that was laying on the floor. I picked it up and put it in my pocket for a souvenir. I had plans for it later.

We watched her set and let me tell you she was amazing. I never saw a stripper that could work a pole like that and command the attention of the entire club. Beautiful and athletically gifted. When her set was over my friend was read to go and hit a club so we stuffed some more money in her garter and hit the door.

Once we picked a club it was on. We started slamming beers and hitting the Kamakazi shots like a couple of sailors who hadn't been off the ship in months. The night was getting along quite well and my buddy was having fun. I don't think he thought about his ex the entire night. We drank a lot of beer and danced with a lot of fine women but we ended up striking out for the night. By the time we closed the club and headed out, we had to leave the car and take a cab back to our hotel. While in the cab Steve started talking about Mercedes and how much he wishes he could have hooked up with her. Through the street light pouring in I could see that his cock was getting hard again thinking about that lap dance.

We arrived at our hotel and we stumbled to our room. Steve was pretty trashed and I was really buzzed but my plans were not complete for the night. He said he was ready to crash and pass out so I told him to go ahead. I told him that I wanted to take a shower before I went to bed so I grabbed my beg and went to the bathroom.

The one thing that I have not mentioned so far is that I am a cross-dresser and my good friend Steve has no idea. He may have been curious about me at times but he has never said anything and he knows I love women. What he doesn't know is that I love cock as much as I love pussy. When I booked our hotel room I booked it with a King size bed and told him we would have to share it because it was the only room available.

To describe myself, I am about 5'7" tall and about 145 pounds. I have shoulder length brown hair and green eyes. My body and looks are neither feminine nor really masculine. I am lucky in that I can transform myself to lean whichever way I want to go. If I have a purely feminine feature it would be my ass. If I am in a pair of tight jeans combined with the long hair you would have a hard time telling I wasn't a woman. I have been complimented on my ass by many embarrassed men.

Steve is about 6'3" tall with blonde hair and blue eyes. He has a rather large cock from what I have seen in the showers growing up but I have never seen it erect. That is something I am about to remedy for his birthday.

Once I was in the bathroom, I turned on the shower and got it nice and warm. I stripped out of my clothes and wrapped in a towel while I laid out the outfit I was going to be putting on. I had been planning this night for many weeks and I wanted it to be special. I shopped online and found a beautiful black strapless corset. I was lace and it fit my very well. It had attached garters with a lace up back and hooked front. I laid it out on the counter and placed with it a set of lace topped thigh highs with a line up the back of them. I had also purchased a pair of "C" sized falsies that actually managed to push up my chest and make it look like it was all me. I had also purchased a sexy pair of black lace boy shorts that hugged my ass perfectly but they were going to be replaced by the skimpy little g-string that Mercedes left behind. To top it all off I had a black Nylon mini dress that fit like a second skin and a pair of knee high black leather boots.

Just laying everything out that I was going to put on had me aroused. It was now time to get in the shower to clean up for my present. I washed my self from head to toe making sure I got myself very clean and girly smelling. Next I shaved my pubic area, balls and I took extra time to make sure I had a smoothly shaved ass. My cock was begging for attention after this pampering. I decided to relieve myself prior to my adventure with Steve.

It didn't take long before I sprayed a huge load of my cum all over the shower curtain. Now I was ready to get dressed. I turned off the shower and toweled off. My hairless body felt wonderful as I admired myself in the mirror. I covered my body with jasmine scented lotion and started to get dresses. I put on the corset and laced it up tight. It squeezed my body into a very sexy feminine form. Next I slid the thigh highs up my legs and attached the garters. I installed the falsies and adjusted myself until it looked like I had a nice set of cleavage. I was trying hard not to get aroused because I knew the stripper's g-string would not hide my excitement. I pulled on the g-string and admired myself in the mirror.

If I do say so myself I looked very hot. Since my hair was rather long for a man I didn't have need for a wig so I took some time to style it into a feminine look. After the hair was done I applied some makeup and mascara and topped it off with some bright red lipstick. I slid on the painted on mini-dress and put on my boots. I looked so fucking hot that I wanted to fuck myself right there in the bathroom. As I finished getting ready, the nerves finally hit me. I couldn't believe that I was going through with this. I had never been with a man but I have fantasized about this moment for years. I hope it worked out the way I wanted it to. I hoped he would not react badly and make me feel like a fool. I almost stopped myself from opening that door because I valued our friendship so much. I decided to put my faith in beer and Kamakazi and the dreams I am sure Steve was having about Mercedes.

I opened the door and left the bathroom. I turned off the bathroom light so that I didn't wake him before I got into bed. I strode to the bed and turned back the covers. Steve was lightly snoring so I knew I hadn't disturbed him so far. Once I was under the covers I decided the boots were not a good idea so I swung over the side of the bed and took them off. As I was doing so Steve rolled onto his back and murmured some gibberish but went still. I laid back down and pulled the covers over me. I lay there for awhile gathering my nerve for what seemed to be an eternity. I decided to go for it and I slowly reached over and laid my hand on Steve's penis. It was limp and slumbering just like he was.

I lightly played with it for awhile growing bolder and bolder. The whole time his cock remained flaccid and Steve kept lightly snoring. I decided to be a little more courageous. I slid down the bed until my head was waist level to Steve. I pulled his boxer briefs down as gently as possible and he did not wake up. I moved my face closer and prepared for my first taste of cock. I used my left hand to grab the base and lift him upright. He was only about 3" when he was limp. I could not wait until I brought him to his full length and girth.

I had seen Steve in the shower at the gym but never erect. I had no idea how big his cock was but I was guessing 8" in length and an inch and a half in girth. I leaned over and licked my first cock. I could not believe how my cock twitched when I licked him the first time. I slowly took his cock into my mouth and loved how soft and warm it felt in there. I started to swirl my tongue around his cock head and felt a stirring in him for the first time. He was still lightly snoring but his member was waking up to say hi to me. I started moving my mouth up and down his shaft very carefully and I could feel his cock growing to my work. First it was 4" and I started going a little bit faster. Within a couple of minutes it had grown to 6 and it was nowhere near done.

After 5 minutes, he was at 8" and very thick. The more he grew in my mouth the more I wanted of his cock. By the time he was fully erect he was 10" long and at least 2" thick. I was going to love every minute of this night.

I had been working on him for about 10 minutes when he finally moved a little bit. He moved a leg off to the side which gave me access to his huge shave balls. I couldn't resist pulling one of them into my mouth for a swirl. This elicited a groan from him and I believe that is when he started to wake up. I played with his balls for a few minutes and then moved back to his cock. I licked from the bottom of his balls up and around both of them to the base of his cock. I was licking and kissing my way up to his swollen cock head when I felt his hand grab the back of my hair and say, "Shannon". Shannon??? He thought I was his ex wife.

He pulled me lightly by the hair and brought me to the head of his cock. I took him in my mouth once again and took as much of him in as I could. I could only get half of his length into my mouth before I could tell I was going to gag so I backed off. I spent some time licking the head and his shaft as I tried to relax my throat muscles. Once I felt a little more relaxed I tried it again and was able to take a little more.

I had practiced head many times but it was always on toys and never one as big as my best friends cock. I keep at it until I was getting 8" inches into me and sliding into my throat when I heard the light click on. I hadn't realized it but Steve had pulled aside the covers so as soon as the light came on and I looked up I was looking right into the eyes of my best friend and his cock was in my throat.

He said, " What the fuck are you doing?"

I got scared really fast and wasn't sure what to do. I slowly pulled my mouth off of his cock and said to him, "What does it look like I'm doing?"

After I said it, I took his cock into my mouth until he was buried into my throat and my lips were around the base of his cock.

His eyes rolled back a little bit and he said, " I know what you are doing, but why the fuck are you doing it?"

I pulled him from my throat again and said, " This is your birthday present." And then I deepthroated him again. I fucked my throat with his cock a few times and released him again.

I had his cock in my left hand and was stroking his cock while I asked him if he wanted me to stop. I pulled one of his balls into my mouth while he thought about answering that question. I was working on his balls when he said, "What if someone finds out?"

Right then I knew i had him where I wanted him. I told him, "No one is going to find out unless you tell someone about this."

I kept stroking his cock and swirling my tongue around the ball in my mouth. I could tell he was having a hard time concentrating thanks to my oral skills and the booze. Next he said, " What the hell are you wearing?" I released his ball from my lips and slid off the bed so he could see my entire outfit. As he got a full look at me I saw his cock jump with excitement.

" My god, you look amazing in that outfit." he said. "I can't believe that that is really you!"

"If I was you on the street I would never have guessed it was you and I probably would have hit on you." he said.

I looked him in the eye and told him, "Just pretend I am some hot little stripper you picked up and brought back to the room and we are going to have a good time."

I watched him think about it as I seductively crawled back up between his legs and took his cock to the base in one swift motion. I used my throat to fuck him for a few minutes before I had to come up for air. Once I had my mouth off of him I used my hand while I licked and kissed his beautiful cock. I was stroking him and milked up a huge drop of precum that formed on the head of his cock. I licked his cock head clean and started sucking him again. It wasn't long until I could feel his balls tightening up and his cock started to spasm. I was about to get my first mouthful of cum and I didn't want to miss a drop. I took his cock to the base and felt the first hot stream of cum hit the back of my throat. He had a hold of my hair and was forcing my head down on his cock as he was thrusting into my throat and shooting load after load into me.

I could feel the g-string I was wearing getting soaked from the precum that was oozing from my cock. As Steve went still I let his cock slide from my mouth. I took some time and made sure there wasn't a drop of cum left in that heavenly cock of his. Steve looked spent but I was nowhere near done with him for the night. I laid there with my head on his stomach just lightly running my fingers up and down his cock. I kept making him twitch and jump and it was nice to be on the giving end of that for once.

After about 5 minutes Steve said, "That was the most amazing blow job I have ever had. Is that the only present that I am getting tonight?"

I looked up at him and said, "We haven't even gotten started yet!"

to be continued.....

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7 Comments
AnonymousAnonymousover 11 years ago
me horny

im dressed in drag and want cock

AnonymousAnonymousover 12 years ago
MEMORIES

I seduced my friend in a similar fashion, your story brought back great memories, I shot off very hard, thank you.

lleannelleanneover 12 years ago
Sexy!

Very hot! I can't wait to read the continuation. Oh, the trouble I could get into with a girly butt!

AnonymousAnonymousover 12 years ago
Very Hot

Very hot story, had me wanting a cock in my mouth and a mouthful of cum!

dilly1964dilly1964over 12 years ago
great start

id love you to be my best friend,speed dial for sure

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