“Truth or dare?” appeared on the screen. Really, on a Tuesday morning?
“Ok, dare. But you know I have to go to work today.” What are the odds this is a bad one? “Wait a minute, I never asked you truth or dare so now it’s an automatic dare for you! Let me think about this one after what you made me do last time.” Then I signed off and got ready for work.
I was still confused about the last time we played and she brought me to a female strip club and then a tranny bar. Although I ended up having a lot of fun, I’m still sticking to being a straight dude.
Later on in the day I logged onto my personal email account and started typing her dare. “You will be on your front porch at 5 with nothing but an overcoat on.” I hit send and logged off. I’m not leaving her the option to argue.
At precisely 5, I was waiting in my car out in front of her house. Where is she? I started for my phone when she walked out the door in a long jacket. This was going to be fun since it was around 80 degrees outside right now and I could see her sweating from the heat and anticipating what she’s about to do.
“Hey, how’s it going?” I asked her with a big grin.
“I’m good. Maybe a little naked, but good,” was her reply nervously.
I started my car down the road and after about 30 minutes we arrived at a wide open sports park. When I stopped the car it was right in front of one of the soccer fields. We sat there for about 5 minutes before I gave her the instructions.
“You are going to get out of the car and throw your coat on the back seat. Then you will head out to the other side of the field and get yourself off under the goal post. Oh yeah, this is a 3 part dare.”
With that said she sunk down but moved to get out of the car complying with the first part of the dare.
What a hot sight as I had my camera zoomed in on her taking care of business. After 20 minutes she started heading back to the car. When she got back to the car I asked for proof of how good she was. She stuck her finger right in my mouth and I instantly knew she had completed the task. She stayed naked and sat in the passenger seat.
I pulled out of the parking lot and headed to the next spot. What a coincidence, we pulled into the same tranny bar as she brought me to.
We got out and she decided to put her jacket back on. Heading for the door, I handed her a strap on that I picked up for her at lunch. As she put it on, we drew a lot of attention from the patrons entering the club.
When we were inside, I went to talk to the MC. I returned to the table with the same grin on my face looking at the show.
She was called out by name and had to go meet the MC much like I had to do at the gay bar she brought me to for her dare. When she received her instructions she looked back at me with fear in her eyes.
There were beautiful semi-ladies dancing and watching the show everywhere. I was secretly looking around the crowd hoping to see Satin somewhere. I wasn’t going to get up and look, but I was really hoping to see her there. I had put her number in my phone, so I decided to see if she was here.
“Hello,” I heard the sexy voice answer.
“Hey, how are you? I was wondering if you were at the club tonight,” I asked.
“I’m planning on being there at 8. You there now?” she asked. “I can be there in 20.”
“I’m here and I’m daring my friend to get on stage and get used by a couple shemales and I was hoping to see you again.”
“On the way now. DON”T LEAVE.” Guess she liked me. So I sat back on my booth and watched my friend get used on stage.
She lost her jacket quick and the 10 inch strap on was lubed and used by 3 different guys before she was bent over her chair and screwed by a really well hung man, He hit her in her vagina and then loosened her asshole up and penetrated her there too. She was going to be so pissed at me. She had in no way a virgin ass, but I didn’t know if she’d ever received a punishment like this before. After about 15 minutes he pulled out and blew his load all over her back which the other guys were quick to clean up.
I must admit I was a little turned on and also a little disgusted at this sight. She got her jacket back and came back to the table to join me. She didn’t look mad at me at all. She actually was happy about the whole thing.
“What’s part 3?” she asked with some enthusiasm.
“You’ll have to wait for it. I’m waiting for someone right now,” I told her. I couldn’t help but be disappointed with her reaction to the whole night.
“You’re waiting for Satin?” she almost yelled.
I had told her Satin’s name the day after our last dare. A couple of the guys heard her in the next booth and they turned and asked if Satin was coming tonight. I nodded my head wondering why they were so interested in her coming here.
“There you are,” I heard from behind me. I turned around and saw a vision of beauty standing there. Satin had on a hot little mini skirt and a pair of 6 inch stiletto heals. I felt a little something in my privates that I hoped would not be ignored for very long.
“Holy crap, you look hot. Please come and sit,” I told her and she quickly seated herself beside me. She said hello to my friend and we made small talk for about a half hour and then decided we should go somewhere else.
Satin suggested a nice quiet place and we left the bar for the next place. When we arrived I told my friend that part 3 was to go dance again. It really wasn’t my plan, but I had to make an adjustment when Satin came into the picture. She danced and came back to the table and our dare is complete.
Satin was sitting right against me and looking so hot. She started rubbing my leg with an obvious reaction in my groin. When she reached my erection, she got a smile on her face and the excused herself to the rest room. She gave my hard on a squeeze and whispered for me to join her. I also excused myself.
I was confused which bathroom she went into so I chose the men’s room first. Lucky for me, She was there. We met in an embrace that was so much hotter than with my last girl friend.
How is it that someone with a body this hot and can kiss this hot and can make me this hot, has a dick? I didn’t care anyway. We were grinding our penises together through our clothes when she grabbed mine and started stroking. She pulled me into one of the stalls where she ripped my zipper down and my pants were off along with my boxers.
She wrapped her lips around my, what I thought was, fully hard member. She sucked with an energy I’d never felt before. She also immediately started playing with my butt hole. Was this what they normally did? I didn’t know. I was new to this, so I asked her.
“Only when I’m this hot baby. I can’t help it. I want to get you off and then I’ll need a little something myself,” she told me.
Uh oh. I hadn’t thought about that. What do I do now? Maybe I can just give her a hand job and go home. I sure as hell wasn’t going to stop her sucking me like this.
“Oh, you’re so good at that.” I wanted her to know how much I appreciated what she was doing.
“I’ll teach you. Soon I can compliment you the same. Now I’m going to sit on that hard slick cock.” She moved above me and slid down slowly at first and then all the way down onto my hard on. “I’ll teach you how to do this too. Now reach around and grab my cock.”
I hesitantly reached around and felt her penis. It was hard and bigger than I remember. I started stroking it like I enjoy stroking my own and she seemed to enjoy it.
I didn’t last long in her tight ass and I shot load after load right into her. When I was done, she lifted off me and stuck her ass right into my mouth. I had no choice but to eat my own cum mixed with her hot ass.
Not as bad as I thought it would be. Then she came right back down and sucked it back out of my mouth. Some how that was incredibly hot for me. My friend was watching this whole thing and was fingering herself madly. Me and Satin sat and watched her for another 5 minutes until she came again herself and we helped her clean up with our tongues.
We made our way to the door and to my car. Satin gave me directions to her house and it wasn’t far. When we got there, my friend told us that she was going to catch the bus home. I felt bad and told her that I’d give her a ride and could come back. She declined and then I told her we could give her a ride and hang at my place. She was a little more receptive to this idea so I pushed some more and she finally gave in. I had to make sure Satin was ok with this and she just said she would have to gather a few things for the morning.
I hadn’t thought about that part. Satin, an incredibly beautiful woman with a little extra was going to spend the night at my apartment. I didn’t know what this night would bring.
When we got to my apartment and all went in, Satin suggested we all have a drink and then play a game.
“Truth or dare,” she said, and we both laughed at this. We both said 'dare' without hesitation because we knew that Satin couldn’t come up with anything we hadn’t already done.
“Get over here and lick my ass then funny man,” she immediately said. I did not see that coming and we had never dared that before.
What could I do? I was a firm believer in the rules of truth or dare and couldn’t break them. So I got behind her and started eating her ass. It tasted pretty good as I licked it and started to stick my tongue in her sweet little hole.
“You, eat his ass,” she commanded.
She had the same respect for the rules of truth or dare and hesitantly went to my rear and slowly started to eat my ass. She didn’t seem to mind it either and soon was nose deep and sticking her tongue up my ass. I did not mind this at all which scared me a little more as to what was to come later.
When we were all satisfied that the dare was completed. I asked Satin, “Truth or dare?” I was pretty disappointed to hear truth.
“How many times have you gone home with someone that has never done this before?”
“Three,” she was quick to respond. “I’ve had two relationships that ended up with him going back straight and this one. I hope this one doesn’t end up that way.”
I didn’t know we were in a relationship and didn’t know my straightness was a question.
“Truth or dare?” my friend chimed in quickly.
“What do you think the odds are that my friend and you are going to be an item? “
“Easy one. We’re going to get on very well. I’ve been taking meds for years and have an awesome body that can pass for a woman’s without a problem. He’s already willingly grabbed my cock twice and I’m sure he wants to fuck my right now.”
After she said that my friend grabbed my groin and agreed that I had an erection ready for her.
“Truth or dare?” Satin asked.
I hesitated weighing my options and the possible outcomes of this one. I don’t know what to say. On one hand, I’m a straight dude that doesn’t want to do anything gay. On the other hand, this shemale is so hot that I’d probably do anything she wants.
My friend and Satin were waiting when I finally said, “Truth”
“How attracted to me are you?” Was her question. She looked a little let down with truth, but I didn’t want to jump right in and have to do something like suck her dick.
“You’re freakin hot. I’ve had an erection both times I’ve been next to you and have one right now. I never thought a woman with a surprise could be so hot and make me so excited as quickly as you have,” I replied without hesitation.
Satin seemed pretty happy with my response and I asked, “Truth or dare?”
My friend wasn’t sure who I was asking at this moment so I directed the question on her direction.
“Truth for me than,” she said.
“Have you ever had bisexual thoughts?” I asked.
“Hell yeah. I watch hot lesbian porn all the time. You’re little dare to go out and finger myself tonight was nothing but an excuse to finish myself off after chatting with a hot little chick with big titties.”
“Learned something new today. Thank you.” Her turn.
“Truth of dare?”
Fuck it. “Dare.”
“You know what’s coming now,” she said.
I did, but wouldn’t admit to it yet.
“Blow her,” was all she said.
It was bound to happen sooner or later and for some reason I really wanted to. I knelt in front of her and started to pull her skirt down when she stopped me. “Just my panties. Then you can get naked and put them on you since I know how much it turns you on.”
I did as she requested and was so turned on that she probably wouldn’t get them back.
Then I knelt down again and fumbled through the blow job pre game. She stopped me a couple times and gave me pointers and finally I was at the point of no return. I was looking at the head of her cock trying to decide if I could do this. Did this make me a complete gay man or just half.
It was the dare. I’ve never not fulfilled a dare before. Not stopping now I guess.
I opened my mouth and there was the first dick in my mouth. I have a strong gag reflex so deep throating would not be an option. I bobbed my head on the throbbing member for a couple minutes as I was getting more pointers. Finally after about five more minutes she came in my mouth. It didn’t taste that bad.
The thought that I was eating it was hard to accept.
Once the dare was complete and my manhood in full question my friend said she’d be leaving.
After she had gone Satin turned to me and asked where my bedroom was.
I led her in and she immediately threw me on the bed and pulled the rest of my clothes off. She left the panties on me and then proceeded to pull her clothes off also.
What a sight. Boobs that are the perfect size for me. If I didn’t have an erection already, I would have now.
Satin dove right down onto my hard on and sucked with an obvious experience. It seemed like an hour she was expertly working on me. She would bring me to the brink of cumming and then stopping and starting again.
When she lifted off my erection she rolled me over and started probing my ass with her tongue. Then I felt a finger go in followed by two and then they were gone.
I started to turn to see what she was doing when she pushed me back down and felt some lube being squirted up my butt. Then the fingers were right back in there for a couple seconds before they were gone again replaced by something else.
Am I gay? No way! At the same time I was thinking that there was a shemale penis being shoved in my ass. At first, this did not feel good and I was wondering why dudes liked this. A couple seconds in, I understood. She hit my prostate with precision knowing what she was doing. I came right away. She fucked me for what felt like an hour but was probably 20 minutes before she came. I had blown a second load onto my bed and already had another erection.
Once she came in my ass, she got on her back and pulled me around to lick all of her cum out of my newly devirginized butt hole.
When she was satisfied that I was cleaned out. She forced me to kiss her and taste the combination of my ass and her cum. Turns out I don’t mind that too much either. It’s not really gay if she has tits, right?
I was hard again anyway so I wanted to get inside her now. She sensed this and lubed up my cock and slammed herself down on me. Even though I’d blown 2 loads already, she brought me to cum within 2 minutes. That’s a talent that I’ll thank her for later. When I was empty, she made me eat her ass again and this time I liked it more.
We fell asleep in each other's arms after a little more caressing and kissing. In the morning we woke up and gave each other blow jobs each sharing our cum. Then we went out to breakfast and discussed our future. I don’t need her phone number anymore.
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with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/trans/surprise-dare-with-an-unexpected-result.aspx">Surprise dare with an unexpected result part 2</a>