“Truth or Dare?” Really? That’s the first thing I see on a Sunday morning. I had just woken up after a night of beers and BBQ. We were out pretty late and I tied on a good buzz. Oh well, I agreed to play the game with her and it didn’t matter when or where. We had to answer as soon as we saw the message. So here we go. “Truth” is my response.

The question popped up right away. “How many times did you jerk off this week?”

Easy one, its Sunday morning. I responded with “Zero, the week is only a few hours old.” Do I want to ask the question of her? I made a pot of coffee and had a small breakfast to settle my stomach and went back to the computer. “Truth or Dare?”

It took a couple minutes for her to answer. “I guess a dare would be fun since I missed out on last night.” She must be upset because she had to spend Saturday night with her parents and knew that we were throwing a party at a friends house.

I had to think of a good one since the last dare she gave me had me naked in the middle of a parking lot at the mall until a woman offered to help me with something to cover up with. Let me tell you all that women do not offer to help a naked dude very often. Lucky for me after about a half hour a heavyset lady came up and offered me her panties if I did her a favor. I ended up taking the panties off of her and using my tongue on her until she came. It was pretty hot actually. The panties were a little on the large size but with my erection tucked in them, they fit quite nice. I have a thing for panties anyway so my hard on remained until I got home where I immediately grabbed on and shot my load right into them.

Thinking about that day, I actually got a little excited and now want another pair of panties to jerk off into. So I respond with “You need to put on your sexiest g-string under your shortest skirt and a tube top that fits real tight and no bra. Walk to my apartment, knock, wait for me to answer, take off the g-string and then show me you don’t have anything else on under the skirt. Then you may go home.”

Ten minutes later a new message appeared with a picture of what she was wearing. “Will this suffice?”

I quickly sent my approval and sat down to wait for the knock on my door. Football Sunday so I had something to keep me occupied. It’s about a twenty minute walk so I refilled my coffee cup and started to catch up on the games.

She must have been walking real fast because the knock came about 12 minutes later. That’s too soon for me so I decided to let her wait outside my door dressed like that. Wonder how cold it is outside. I opened the laptop again and saw it was about 62 degrees out. I know she has nice size breasts and large nipples and I wanted to see them. I grabbed my camera and headed for the door. It was quite the treat to see what was patiently waiting outside for me.

“Good morning, how was your walk?”

“F-ing cold you jackass.” She said in an annoyed tone. I snapped a picture of those boobs for my private collection and waited for my prize. She reached under the skirt that barely reached her thighs and pulled down one of the smallest g-strings I’ve ever seen. Another erection is forming. “Here, sexy and pink with a flower on the front.”

“Thank you. You have something to show me?” I asked

She proceeded to lift the front of her skirt and show me she had nothing else underneath. I noticed she needed to clean up some of that hair and made a mental note to bring it up next time she wanted me to dare her. I thanked her and told her to let me know when she made it back to her place safely.

After closing the door I took a close inspection of the tiny piece of fabric that I had been handed. She must have been pretty turned on because it smelled of her. The tiny scrap of material had a small rose on it and I decided right there that from now on I would call her pussy a rose in all of our dares.

I went back to the football game while I put the string in my pocket for later. I had decided it was to small to stroke with so I’ll just hang on to them and try them on later. Little did I know that it would be sooner rather than later. My computer beeped letting me know I had a new message. I got up to check it and was surprised to see her naked with a finger in her rose. “You’re a real asshole but I was so turned on I started this on the walk home and had to finish before I gave you a dare.”

Strange I don’t remember answering the truth or dare question. This should be a real good one if she didn’t even bother asking. “This is going to be a 3 part dare. First, since I know you aren’t going to give me back my g-string, put it on. No other clothes and send me some pictures.”

Sounds like a good start to me. So I stripped and put on the g-string. It didn’t cover anything and was real tight riding right up my ass. I took the picture and sent it to her. She quickly replied asking where the rest of the pictures were.

“Pictures of what?” I asked her fearing the response.

“Show me how it fits all the way around.” Damn, I wasn’t expecting that. Instead of snapping a bunch of pictures I decided to just make a video with a real close up of my ass cheeks spread apart. Upload and send. See how she likes that.

It took a minute for a response to come back. “Nice. Glad you got the video camera out. Now while I prepare for part two you can just sit in you’re panties and wait for me to let you know what you WILL do for me.” With this I started to get nervous. She must have been planning this for a while. I had no idea what was coming next but knowing her, it’ll be something outside with only this to wear.

“Can I at least relieve myself so I’m not sitting here with this boner?”

“Sure you can. I know it’ll just grow again soon. You can send pictures if you like. You know how I get off seeing a mans chest covered in cum.” I was happy to oblige her and quickly had the camera out snapping pictures of the huge load I just left on myself. Of course I had to make sure to get the shot with the tiny covering over one of my testicles looking up at my shiny cum covered stomach and chest.

“Pictures sent and thank you for allowing me relief. What do you think?”

Ten minutes later the computer beeped again and I was treated to another picture of her, this time with the skirt on, but her fingers deep in her rose again. “Love that it covers you so well. Not just your cum, but the panties also.”

There’s the beep again. Here we go. “Put on a pair of sweats and a jacket and get over here.” Clothing on and out the door I went. I drove even though it was starting to warm up because sweat pants don’t hide a hard on very well.

When I pulled into her driveway the garage was open and she came out and waved me to pull in. She was still wearing the skirt and top from this morning which I was pleased to see. I followed her into the house and up to her bedroom. Although we have been really close friends for a long time and play games with each other like this, I had never been in her bedroom before and we never had sex either. She pointed me to the bathroom and I saw the exact same outfit she had on in there.

“You don’t expect me to fit in this?” I asked shocked that she had the out for me to put on.

“Yes I do. At least you get to wear panties unlike me.”

I took the sweats off and then put her choice of clothes on. They weren’t even close to fitting me. The skirt was like a belt and the top was too tight and see through. It didn’t fit around my midsection while the chest area was quite a nice fit.

“Let’s go.” I wasn’t sure about this one. I’ve been naked in public, had to jerk off in a variety of places and even had to pick up a various older ladies. We never got into the idea of cross dressing.

I told her. “I’m only into women’s underwear, not the clothes.” She wasn’t going to let me out of this. And led me out to my car. She got in the passenger side and then got back out.

“Wait, I forgot something.” When she reappeared, there was a pair of fuck me boots in her hands. “You’ll be needing these.”

She programmed an address into the GPS and we headed out. About 20 miles outside of town we arrived at our destination. A women’s strip club? Oh well, could be worse. I put on the boots which were also way too small and hurt pretty bad. In through the door and cover charges paid. Surprisingly, they play the same kind of music in here as at the gentleman’s clubs. We walked in and found a table. The waiter took our order while checking me out.

Her camera was on the table already waiting for her chance to get me on stage. Then the announcer came on and called me out by name. I walked over and he instructed me to get on stage and let John and Doug remove my clothes and play with you for three songs. I looked at him in disbelief, I’m not gay.

I looked back at her and she smiled and spread her legs like she was going to play with herself and signed for me to get on with it. Then she picked up the camera and started snapping photos of me.

When I got on stage the two muscle bound strippers came out and the music started. They walked around me a couple times and thankfully, started with those boots. Both of them took plenty of time with the boots and looking up what there was of a skirt on me.

Finally they had all the clothes but the g-string off of me and commenced to rub themselves against my skin and grope me all over, and I mean all over. I think my butthole was raw from them trying to stick their fingers in. Luckily I can clench real tight. Even though I’m not into dudes, I couldn’t help but have another huge erection. One of the two guys grabbed it and started to stroke it while the other was still playing with my asshole and finally got a finger in and instantly went for my prostate. This was surprising but I actually liked how he was doing it. I quit fighting it and they brought another huge orgasm out of me in a matter of 30 seconds or so. At least I learned how to get myself off quickly. Finally the third song ended. They took the clothes with them to the back and I started to follow but was turned around and sent back to the table with just the panties on.

20 minutes later we had finished our drinks and it was time to leave. I asked her where the clothes were and was informed that I wouldn’t be needing them anymore. Now what am I going to have to do? So I followed her out the door and to the car.

We got in and was told to drive to another address. We pulled up in front of a tranny club. I’ve been a completely straight male for 28 years now. Today was my first gay experience and now she wants me to go into a club full of cross dressers and shemales? And dressed like this? She threw another small dress at me that she had in her purse and had me put it on. Small and a little see through.

We walked into the bar and I headed straight to the bar to get a beer. Not a minute later there was a tap on my shoulder. Turning around I saw a beautiful woman looking at me asking for a dance. No way this is a man. She must know I’m a dude so why not. We danced and talked for a little while when she grabbed my package and started stroking it. I looked surprised and she grabbed my hand and brought it to what I was expecting to be a vagina.

How the hell did a woman this gorgeous, have a cock? She was bringing me close to another ejaculation so I grabbed and stroked it like I do myself very often. Luckily it was smaller than average and was easy to conceal what I was doing until she got up and set herself down on my lap. With surprising ease, she let herself down onto my shaft and started riding me.

This was all new to me again, but it felt freaking awesome. She was moaning and came right down the front of her dress and onto my legs. She picked her cum up with her fingers and licked one of them clean and shoved the other in my mouth. Another first for me. She started pumping me faster and I blew my load right up her tight ass. That was one of my most intense orgasms ever.

As much of a man I claim to be and as straight I had always bragged about. I’ve had some great experiences today that felt amazing.

She cleaned me up with her mouth and handed me a napkin with her number on it.

“Thank you for a great time. You have an amazing cock and I would love to ride it again some time. Call me soon.” With that I was taken by surprise again when she moved right in and stuck her tongue down my throat. Again I tasted my own cum.

We left again and my friend informed me that part 3 of the dare was easy. Lose the dress and drive her to her house. Walk her to the door and then go home. When we arrived I walked her to the door expecting to be invited in and be able too put my sweats back on.

“You can have those later. I call your new girlfriend and give them to him. Go home.” She said with a little giggle and an evil look in her eyes.

I drove home all the way trying to figure out what I was going to do with my new found pleasures. There’s no way I was going to tell anyone about this. She better keep it a secret too.

Great, I had to go up the three flights of stairs to my apartment in a g-string. I made it with only a couple of neighbors noticing. Once inside I pulled the napkin out from the waist of my panties and looked at the name. Satin? That’s her name, Satin. At least she felt like satin inside.

I decided to take a shower. I got to blow another load. Then went for some more manly football and beers. I had a couple more beers and then picked up the phone….