This is 100% a true story.
First, I am an engineer, not an author, poet, or writer, so forgive my poor writing skills.
I am a 34-year-old divorced man which loves to workout and spend weekends sailing. I have always been open sexually and have been a swinger from time to time.
Last month I was at a pal’s house attending a small party. The circle of friends I have are very diverse. I have straight, gay, and trans friends.
While at the party many of my friends have been trying to hook me up with wife #3. I am not at all interested in getting back into a serious relationship. One of my gay pals made a joke that I should try the “dark side”. I have zero interest men. Then, my pal’s wife said I should try Jill. Jill is a trans friend who is very beautiful, but, not what I need.
Later that night we were playing a game. It was basically a sex game asking about what you had done, and your inner secrets. I was drunk and we all dove deep into our kinks and discussing the craziest things we have ever done.
Around 1am there was only five of us left and we were getting crazy with our games. We then played a dare game where if we didn’t tell a story that would shock everyone, then they had to do the dare. Most dares where showing tits, dicks, and a little touching. Then Jill was out of good stories to tell and took a dare. Jill was dared to show her trans dick. Jill pulled up her skirt and slid her panties to the side and let a big dick flop out, and it was slightly stiff. I was totally shocked that a gal with such a nice boob job, and great legs would have a big dick. It was really weird seeing a sexy gal with a dick.
At around 2:30 thing took a crazy turn. I was dared to suck one of Jill’s nipples. I was very nervous as it could not get out of my mind that she was really a guy. When I sucked on it she reacted just like a horny gal would. It was crazy.
As the game went on the dares got more intense. My pal’s wife was dared to go into the bed room for 5 minutes and suck one of our other pal’s dicks. They went in there and you could here hard breathing and slurping. She was drunk, but you could tell she was really horny and loved the dare. We then heard our friend grunt, and about two minutes later she came our laughing. She said, “My god he came a lot.” My pal just laughed at his wife and called her a slut while smiling.
Then came the strange. I have never ever not taken a dare. I was the one who would always do anything. When everyone voted my next story a dud, I had to take a dare. Jill said, since you did such a good job sucking my tits, you have to go to the bedroom and suck my dick for two minutes. Keep in mind, I am very sexual, have had three ways, and DP’ed my ex-wife. Being around another dick has never bothered me. But, sucking one, not sure I could do that.
Jill took me by the hand and led me to the bed room and closed the door. She walked me to the bed and asked me to sit down. She stepped up close to me and said, “Its ok baby, just two minutes, it won’t make you gay.” I laughed and must have looked terrified. She then unbuttoned the side of her skirt and let it fall to the ground. She then slides her panties down and her dick popped up nearly hard. She took her fingers and traced my lips signaling me to open my mouth. With her other hand she stroked her dick and it became very hard. Next, she stepped even closer and then she rubbed her dick head on my lips. My heart was exploding. Jill pushed her swollen head hard against my mouth and I opened it. I would guess her dick was 7” and very thick. Jill then put her hands on each side of my head and started moving my head as she took very small thrusts. I could not believe I was sucking dick. To be honest, it was very strange, but not bad. I got her dick wet with my spit and it was sliding in and out when I tasted a bit of a bitter taste, I knew it was pre-cum. Then I freaked out, was she planning on finishing in my mouth? Who was timing this “two” minutes. Jill then said, “Fuck, I am so horny, I am getting close, yes baby, suck it.” I am not sure what happened to me, but for some reason I may never know, I wanted to please her. I started sucking and moving my head on my own. I felt her dick swelling and could hear her breathing harder. Jill said, “Fuck yes. I am getting close, I really am. I feel it building baby.” I just kept sucking. She then said, “Oh god, yes, I am, keeping doing just like that, yes, oh, here, I, I, I am going to cum.” I felt her dick head swell and get really hard, then, it happened, 4-5 sharp and forceful squirts went right into my throat as her dick twitched, then 2-3 smaller ones, and then oozing. Her cum felt really slimy and thick. There was so much it was only reflex that made me start swallowing.
Jill stood there running her fingers through my hair. Her dick was still in my mouth but was softening.
Jill the took a step back and giggled and said, “Fuck, you are good at that baby, fuck that was good.” I could only smile and think, “I just gave a girl-dude a blowjob and swallowed, what the fuck have you done?”
We walked back into the party and everyone started laughing and said, “That was a great show, too bad it was made up.” Jill said, “No shit everyone, he just gave me one of the best blowjobs ever.”
Now, I know she was drunk, but there is now way my first time was that good.
As I reflect on that night I have no idea what came over me to take a dare like that. Honestly, I liked sucking her trans dick, not saying I would ever date a trans, but it was something I will never forget.
Next week is the next party, however, I heard Jill is in London for a month.
