tagTranssexuals & CrossdressersGiving My First Blowjob

Giving My First Blowjob

bySLMaid©

After a few beers and chicken wings, I left Jim at Gunny's. As I got up to leave I handed him an envelope and told him to give me a half hour then come over to my hotel room. As I left I wondered if he would go through with this. In the envelope was a pair of black nylon full brief panties with a note that said "Put these on before you come over", Sara.

After Sara left the bar Jim opened the envelope. Inside he saw the panties and the note. He thought about it for a moment and figured , "Why not, I'm about to have sex with my brother-in-law while he's made up like a woman." Jim went into the men's room and took his briefs off and slid the panties on. He had never worn woman's panties before and the thought of it and the silky of the nylon gave him an immediate erection. He had another beer before he went to meet Sara, his crossdressing brother-in-law.

I hurried to the hotel and went straight to my room. They call it a suite, bedroom, living room, kitchen and 2 TV sets with VCR players. I quickly stripped off my man clothing. I had worn panties, red stockings and red garter belt under my clothes so I was half dressed already. I attached my 32b silicone breasts to my chest and put on my sexiest lace bra. I grabbed my flowered miniskirt off the bed and slipped it on. It was actually a full skirt but in a girl's size 12, it barely covered may ass. I took the long sleeved white sheer nylon blouse I had picked out and quickly buttoned it up and tucked it in the top of the skirt. I stopped long enough to look in the mirror and straighten my skirt. I thought I looked hot from the neck down. My silicone nipples were sticking out firm and hard and the blouse was sheer enough that I could see my red bra underneath it. I had to hurry. In to the bathroom.

I had been carrying a hard on for the past few days thinking about this meeting, but now my dick wasn't even half hard,it was it's normal little button.

In the bathroom I grabbed my makeup bag and found my foundation. I shook the bottle and poured it out in my hand. I applied the foundation all over my face and neck. I made sure that I completely hid my eyebrows. My God I only had 10 minutes to finish. I put my long false eyelashes on, a lot of blue eyeshadow, bright red lipstick, mascara and finally I drew on my eyebrows. I clipped on my gold pendant ear rings and grabbed my wig. I quickly ran the brush through my long blond curls and sprayed them in place. A touch of perfume and I was almost ready. I went back in the bedroom and slid my 3 inch black patent leather heels on to my stockinged feet. I looked in the mirror, I looked like a cheap whore, but a female whore. Now I was starting to get hard.

I lit the candles around the suite and turned the lights off. I popped a porn tape that I knew Jim liked in to the VCR in the living room,lit a cigarette and waited. Now my stomach was doing flip flops thinking about what I was about to do. My wife had been the only person that had ever seen me dressed like this. I was about to suck my first cock and hopefully get fucked. Then there was a knock at the door.

I looked through the peephole and Jim was standing there. This was it, it was really going to happen. I stood behind the door and let him in. The door closed behind him. When he saw me in the dim light his eyes got huge and he snickered as he handed me the 6-pack he had brought. I took the beer and quickly turned to put it in the refrigerator, I felt the back of my skirt go up as I turned. My mind was spinning now, what am I doing, I'm made up like a woman and am about to have sex with my brother-in-law. This is the most perverted thing I've ever done. I had a full erection now. I felt Jim's eyes staring at my ass when I bent over to put the beer away. I grabbed 2 beers. Jim had walked over by the couch and was standing there watching the movie. I handed him a beer and sat mine on the coffee table. As he opened his beer I put my hand on his crotch and dropped to my knees in front of him. I could feel his cock, it was rock hard. I was turning him on. Here I go this is it!

I rubbed his crotch and pulled his zipper down. I slid my finger inside his zipper and felt silky nylon encasing his erection. He had worn the panties. I was ready to come right there. Quickly I undid his belt and unsnapped his jeans. I pulled them down to his knees. I looked up at him and in the light of the TV I could see that his face was red. Then I looked directly in front of me, there was his swollen cock being restrained only by the panties he was wearing.

All thought what I was about to do left me. It was pure lust that drove me. I closed my eyes and kissed the head of his cock. I ran my lips up and down his panty covered cock, feeling the soft silkiness of the nylon and the stiffness of his cock against my lips. I cupped his balls in my hand and gently felt them as I continued kissing up and down the length of his cock.

I whispered "Sit down". Jim sat down and I pulled his shoes and socks off, then disposed of his jeans. The only thing between his cock and my lips was his panties. I took the top of the panties and slowly slid them down. Jim lifted his ass and I pulled them completely off. I leaned forward and in the dim light I could see his hard cock. It was about the same size as mine and surrounded by curly dark hair.

I took his cock in my hand and stroked icy up and down a few times then kissed the head. My tongue was pressing against his cum hole. I gathered my saliva on my tongue and licked the length of his cock. He shuddered each time as my tongue passed over his most sensitive spot. Finally his cock was all wet and shiny. I opened my mouth and slid the head of his cock into my mouth. I bobbed my head up and down and sucked on his cock until I had the length of it completely in my mouth. Then I remembered my teeth. I curled my lipstick coated lips over my teeth and continued to slide his cock in and out of the depths of my throat. The lipstick made his cock slick and sweet. I felt Jim's hands on my back feeling my bra, he slid his hands around until he was cupping my silicone breast. I swear it felt like he was actually feeling my tit, squeezing my nipple. I moaned around his cock and started working my tongue over his sweet spot. Jim moaned "Oh yea Sara, suck on it" as he put his hands on the back of my head. He started to move his hips and slide his cock in and out of my mouth. He was fucking my mouth with a rythmic motion of his hips.

Jim groaned as I felt his cock swell in my mouth. I knew he was about to cum. This is what I have fantasized about and now it was to happen. I was ready to cum myself. I wanted to grab my own cock as I tasted his first drops of precum on my tongue. I grabbed Jim's ass as he fucked my mouth faster, then suddenly his cock pulsed and hot cumshot into my mouth. The taste was similar to the taste of my own cum. I held my lips tight around his cock as his hot cum slid down my throat. I put the tip of my tongue over his cum hole, him cock spasmed again Jim's cum pushed against my tongue. Jim's cock was wet and slimy with his cum as I continued slide my mouth up and down his cock. My own cock spasmed, I could feel my precum making my own panties wet, oh how I wanted to cum. Had I not been sucking Jim's cock I would have jacked off right there. I wanted more, after 4 or 5 shots of cum in my mouth Jim started to relax. I felt his cock begin to soften as I continued to suck and lick the cum that coated it.

Jim lifted my head and pulled his cock out of my mouth. I could feel his cum glistening on my lips, a mix of lipstick and cum, the most erotic lip gloss ever. I stood up and grabbed my beer from the table and took it to the fridge where I got 2 fresh ones. When I returned Jim had put the panties back on and was sitting on the couch. I handed him a fresh beer and sat in the chair across from him. In the dim light he was staring at me, trying to look up my skirt. I would give him a brief flash of my panties as I crossed and uncrossed my legs.

After we both calmed down and talked for a few minutes about nothing I suggested we go back to the bar. Jim just looked at me and said, "Your lipstick is smeared" we both laughed and I told him I would be there in about 20 minutes. Jim got dressed and left.

I immediately reached under my skirt and released my cock from it's damp nylon prison. I sat on the couch and madly pulled on my cock. After just a few strokes I felt my cock swell as I began to shoot my cum onto my stockings. Hot globs of cum soaked into the sheer nylon. I continued to gently stroke and milk my cock until it shrunk in my hand. I opened my eyes and saw the mess I had made. I brought my hand to my lips and licked the cum from my fingers. I was in heaven. But I wasn't finished with Jim yet.

I went in the bathroom and stripped out of my clothes and too a quick shower. I got a fresh pair of panties and put my man clothes back on and hurried off to the bar. When I walked I saw Jim sitting at a table back in the corner with a beer and they were just brining a basket of hot fresh wings. I went over and sat down. There was an errie silence between us. I broke the silence by asking how the wings were. After that we were fine. Jim started asking about my crossdressing and the conversation went on from there.

I had 6 more days here.................

Report Story

bySLMaid© 5 comments/ 120059 views/ 5 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartalien55, bravow01 and 3 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (5 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (5)

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel