tagTransgender & CrossdressersHow Dicks ended up in My Mouth Ch. 01

How Dicks ended up in My Mouth Ch. 01


My name is Joe. I am a married, successful business man with a pretty wife. I lead the life of an upper middle class guy. I grew up in a small Texas city and had a great childhood. I was a football star in high school and college and dated lots of attractive women. Most people would say my life is ideal. However, I have some secrets.

The story begins when my first marriage was rapidly falling apart. I did not think it was possible, but I came to despise my wife. I had no interest in having sex with her. Truthfully, I had no interest in being anywhere near her. I had reached my lifetime limit on her screaming at me.

I started working late every night and then drinking with my buddies after work. After we left the bars, I would drive to a part of town where I could find hookers on the street and in nearby apartments. I enjoyed the game of picking an attractive whore while avoiding the police.

I picked up a lot of young hookers and had a good time. I would usually get a blowjob from the girls in the front seat of my car. Occasionally, I would fuck them at a nearby house or apartment always using a condom. The hookers liked me because I was nice to them and had plenty of money. It was actually a lot cheaper and more fun than a few drinks at a topless joint.

My wife would scream at me if she was awake when I got home, but I truly did not care at that point. She found purple lipstick on my boxers one day and was going ballistic. My explanation was simply that I did not even know anyone who wore purple lipstick. You can't have much of a fight when one person really and truly doesn't give a damn.

One night I picked up a girl who was very attractive, but different. You will say that I must be a dunce, but I could not figure out how she was different (or maybe I couldn't admit it even to myself). Her name was Maria.

She was Hispanic with long dark hair, a hot slim body, nice small boobs and a pretty face. She was around 20 years old and always wore sexy short dresses. She sucked my dick and let me cum on her face (not in her mouth). I really liked her. I made note of where she lived when I took her home.

I went to visit my new friend several more times. She never took off her clothes, but was awesome with my cock in her mouth. She loved my cock and was really hot.

Soon, I started fucking Maria up the ass. She would bend over the bed and let me take her. I have a fairly large cock and she loved to be fucked. Maria would not get naked. She would just pull up her skirt, pull down her sexy panties and let me fuck her (wearing a condom).

Almost anybody would have realized that Maria was a shemale right away. I honestly didn't for the longest time. Then, when I suspected that she had a dick, I just did not think about it. I have an amazing ability to put things in compartments in my brain and just not think about it. This comes in handy in school or at work. I can concentrate on some project completely and intensely and other thoughts never enter my mind.

In any event, I did not consciously realize she had a dick for a long time. I had never had sex with a man and considered myself 100% straight. I did not even like to look at gay porn out of curiosity. I sort of liked shemale porn, but I did not look at it very often and looking at it embarrassed me even though nobody knew I looked.

I finally figured out that Maria was a shemale or a guy. One night, I reached around her as we were fucking and gently grabbed her small, but stiff, cock as I fucked her cute little ass. I could tell that it scared her that I had discovered her secret that she started life as a guy, but I did not care that she had a dick.

I never gave any serious thought about having sex with a shemale. I did not feel like I was gay or something. Maybe I should have, but I didn't. Maria was just a hot girl who could suck a mean dick and was willing to take my cock up her small tight ass. Her little dick was just another fun aspect of our "relationship."

Whenever I could not find Maria, I would pick up female hookers or shemale hookers. Apparently, the word had gotten around the shemale hookers that I was a nice guy, had a nice cock and would pay them. So, I had a few more experiences with shemales sucking my cock.

One funny experience involved this tall blonde that I picked up. I had never seen her before. Up close, she did not look completely like a woman(unlike Maria). I went with her to her apartment and we took care of the financial aspects of the transaction. She was extremely tall and thin, had a good muscular body and big boobs.

I was about to have the tall blonde suck my cock when she said, "I know you from somewhere."

I said, "I sincerely doubt that."

She put my dick in her mouth and then suddenly said, "Wait! I know who you are! You are Joe Johnson. You were the star running back for Lincoln High School. I played defensive back for Madison. I never could tackle you. You made me look like a fool trying to catch you in the secondary."

I laughed and tried to picture what she would look like without makeup, long blonde hair and big boobs, but I could not do it. Madison High was our big rival, so I might have known him back then.

I did have some fun though. I paid her a little extra, had her strip and fucked her up the ass. I had her sing the Lincoln High fight song while she took my cock up the ass. I loved it and she was good natured about it. She didn't sing very well while taking a dick up her ass.

Shortly after I first hooked up with Maria, I met Maria's roommate, Angie. Angie was slim, fit and blond. She had big tits and was very sexy. In a dress, she looked like a very sexy young girl. One night, I came to see Maria, but only Angie was home. She was also a hooker and gave me a great blow job. Another night, I fucked Angie up the ass. Angie knew the drill from Maria, so she also did not get naked when I fucked her. I had never seen her naked and I had never reached down between her legs when we had sex. She always thanked me when I fucked her.

Late one night, I stopped by their apartment on my way home. I knocked on the door and I heard Angie call out to me to come in. I opened the door and came into the living room. Angie was in the back. I stood in the living room waiting for her for a few minutes.

Angie appeared from a room in the back. She was clearly expecting someone else because when she walked into the room she was completely naked. Her blond hair was wet. Her tits were large and the perfect shape. Her stomach and legs were muscular. However, mostly I noticed that she had a semi-hard nine or ten inch cock swinging between her legs.

I had heard the expression "weak in the knees", but I had never experienced it. My reaction to seeing Angie naked with her huge cock made me weak in the knees to the extent I really thought I might fall down. I was totally breathless at the sight.

My reaction scared me. I was straight. I had sex with transsexuals because I wanted to fuck someone and they liked to suck dick and be fucked up the ass.

This was different. I wanted to be on my knees in front of that magnificent cock. I wanted to suck it. If she wanted to, I would have let her fuck me with it. I wanted to be taken.

As I said, my reaction scared me. So, rather than get on my knees in front of her, I had her bend over the couch and I fucked her up the ass like there was no tomorrow. I came in no time.

I could not get Angie's big cock out of my mind the next day. As soon as work was over, I headed back to the apartment. Maria met me at the door. I was very, very nervous.

Maria was getting ready to suck my dick in her bedroom. She was pulling down my pants when I finally screwed up the courage to tell her what I wanted. I told her that I wanted to suck Angie's cock. She was very surprised because I had always been a dominant masculine top. However, she offered to suck me while I sucked Angie. I told her that would be great.

Maria went to get Angie. They came back in a few minutes. Angie was naked and her cock was hard. I felt weak again at the sight of that big dick sticking straight out in front of her. My cock was as hard as it can get.

I had Angie wear a condom on that beautiful cock. I got on my knees in front of Angie and started kissing a cock for the first time. I was unbelievably excited when the big dick entered my mouth. Maria was on the floor in front of me with my cock in her mouth. Angie looked gorgeous with her big tits showing and her hard cock in my mouth.

I usually lasted a long time when receiving a blowjob, but this time I was so excited to be sucking a dick I exploded into Maria's mouth after just a few minutes. I had never cum in Maria's mouth before, but I could not control myself. She was so surprised by the cum exploding from my dick, she gagged on the cum. She was also a little angry that I had cum in her mouth without warning. I didn't say it, but I thought to myself that cum in your mouth is one of the risks of putting a dick in your mouth.

I continued to suck Angie's cock until she came. I kissed both girls goodbye.

I could not think of anything other than Angie and her dick the next day. I went to their apartment right after work. Angie was dressed for the evening in a sexy short dress. She assumed I wanted a blowjob or to fuck her. However, I wanted her cock again.

For some reason I was extremely nervous about telling her what I wanted. I asked her about her health and she told me that she always used a condom when she had anal sex, that she had just been tested that week and was disease free. She showed me the lab results.

For the longest time, I could not bring myself to tell her what I wanted. I was embarrassed to say it. I had always been the dominant top. The last time I had been very drunk and had told Maria what I wanted. Finally, I swallowed my pride, blushed and said, "Angie, would it be okay if I suck your dick again?"

I felt like I did the first time I asked a girl to go on a date. I had not thought it through, but I was nervous because I was basically saying, "Let me get on my knees and worship your big, hard cock." I felt like I was agreeing to be a submissive slut.

Angie was great. She smiled sweetly and said, "Oh, I would love that!"

She stood up. I got on my knees in front of her. I reached up under her dress and pulled down her pink panties. Her big heavy cock fell out when I pulled the panties down. It was getting hard. I could barely breath I was so nervous.

Her cock was so long that when it was just a little bit hard, it showed below her dress. I loved that!

I started licking the head of her cock beneath her dress. She sweetly asked about a condom, but I told her I did not need one. I then started licking up and down the shaft of her giant cock. It was so exciting.

As her dick got hard, I took it into my mouth. Her dick was long and thick. I thought it was beautiful. I felt like such a slut and I loved it. My mouth was full of dick and I remember thinking, "I am sucking a cock!" I found entire idea completely amazing.

I wanted to give Angie the best blowjob she had ever received. I did everything I could think of to make it feel good for her. I did everything that girls did for me when they sucked my cock. She was gently rocking back and forth to pump the big cock into my mouth.

I started bobbing my head up and down on her dick. I pulled out my hard cock and was furiously whacking it as I sucked. I had never been more turned on.

Finally, again feeling nervous for some reason, I looked at Angie and said, "Angie, will you please call me a cocksucker?"

She smiled a knowing sort of smile and said, "Of course, Joe."

Then she grabbed the back of my head, pushed it gently down on her cock and said, "You are a cocksucker. You are my cocksucker!"

As soon as she said that, I started furiously sucking her dick and started to cum all over her carpet. Angie rather gently face fucked me for a minute and then filled my mouth with cum. I was stunned by how good it tasted. I swallowed.

I lost track of my shemale friends and only had sex with women for years after these experiences, but the desires returned years later. I will tell you about it in the next episode.

Report Story

byret123© 9 comments/ 87612 views/ 61 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

heartJb423, EyesOfHentai and 59 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous05/25/18


I love the feel of a huge cock cumming in my mouth and down my throat

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

Show more comments or
Read All 9 User Comments  or
Click here to leave your own comment on this submission!

Add a

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

Post comment as (click to select):

Refresh ImageYou 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: