3 comments/ 39658 views/ 14 favorites Surprise Dare With An Unexpected Result Ch. 01 By: tomc327 "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.... Surprise Dare With An Unexpected Result Ch. 02 "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. "Truth again." "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. Surprise Dare With An Unexpected Result Ch. 03 After breakfast Satin heads back to her place and I head for mine. When I arrive and sit down on the couch, I open my laptop and see" "Truth or Dare?" Dammit, not what I want to see right now. The hell with it, I'm in a good mood. "Dare." I wait what seems like hours for a response. "Come over now." She must have written the email last night because of how long it took her to reply. I started getting excited all over again in anticipation of what's to come. After a quick shower I grab my keys and head over. The garage door is open again and I know what to do. Once I put the car in park and head for the door I notice a note on the door. "No clothing allowed past this point!!" Sweet, I get to see her naked at the same time I am. Maybe I can get her to trim up Rose while we're at it. I strip and walk in. Once through the door and into the living room. I'm a little surprised to see she is not alone and I'm the only naked person in the room. As I look around I see Satin is already here along with my friend and another good looking woman. "What's going on?" I ask while still looking around. "You'll find out. Now start serving us. Your dare is to be our maid all day, dressed as you are." she says in a surprisingly stern voice. No problem for me. I like being naked especially in front of three hot chicks. I start serving them what they request throughout the afternoon. After a couple hours the wine runs out. I'm told to go get some more and Satin will go with me. I get an instant hard on which of course is noticed by all. "You keep that thing up for us, I want to see what Satin can do with it when you return." With that, I turn to towards the garage door. My thoughts are hoping Satin will let me get some practice in before we return. Once outside I figure I can put my clothes back on, but there's a problem. They aren't where I left them. "Where are my clothes?" I ask Satin starting to get concerned. "It's still light out and the only store open to get wine is a grocery store. I can't go in to a grocery store dressed, or rather not dressed like this." "You don't need them," is her reply. That is not what I want to hear from her at all and she has a slightly dominant tone to her also. I didn't expect that from her. We get in the car and pull out of the garage. We make some small talk on the way and then she puts an address into my GPS. "Truth or Dare baby?" "Dare," comes out of my mouth before I have a chance to think about my current clothing status. She hits the go button on the GPS and tells me to drive. Why didn't I get gas on the way over? "I need gas. I don't know how far I can go without refilling the tank," I tell her, hoping we can just go back to my place and hop into bed. "So stop and get some. We have a ways to go. I wouldn't want you to have to walk all the way to get a gas can filled while you're naked. Or would I? I like what I'm seeing." she replies with an evil grin across her beautiful face. Of course I have an erection and she grabs hold of it to make sure it stays. "Why don't you get naked and pump the gas?" I ask her hoping she will just get out and fill the tank anyway and I can sit in the car shielded from the world. I would love to see her do it naked, but I'm not very optimistic that this will happen. "Ok. But you have to go in and pay." Is her reply while I remember that I have no way of covering up and I don't know what this part of town is like. This is quite the predicament now. I can make it to a filling station outside of town where nobody will know me."Sold. Take your clothes off so I can see that hot body of yours," I say as I hit the gas a little harder wasting more gas than I cared to. "I'll take them off when I'm ready. You just keep driving with that beautiful cock hard as it is," she tells me as I hit the gas a little more. Next thing I know I'm speeding out of town looking forward to seeing her standing outside my car completely naked. How many men would be turning their head and staring only to see her hot little surprise. Then the lights come on in my rear view mirror. "Holy shit. I need something to cover up with quick." Of course I keep my car clean so there aren't any clothes or towels anywhere. "Oh well. Maybe he'll feel bad for me and let us go." As the State Troopers door opens, my heart drops. That's a lot of hair for a male cop. I watch as a hot set of hips and very large breasts starts walking towards us. I sit there staring at the way she sways toward the car with her gun belt accenting her curves beautifully. I have to remember to get one of these for Satin. She gets to the window and looks in. "Nice day for a drive, isn't it? You realize you were going 82 miles an hour? And would you mind explaining why you are naked to me before I write you this ticket?" she asks me as I turn a hundred shades of red. "It was a dare. I'm supposed to go where the GPS tells me in the nude so I can restock the wine for the girls that I'm serving another dare for and being their servant all day long." I reply thinking that was a pretty good excuse and maybe an embarrassing one also. "I'm gonna need you to get out and step to the rear of the car. Your cute little friend too." At least she has taste I think as I slowly open the door making sure no cars were coming. We both make our way to the back of the car and she tosses me across the trunk. Then something weird happens. I feel something slippery and round at the entrance to my ass. Then with some pressure, it starts entering me. It keeps getting bigger and is spreading my hole open wider and wider until finally it pops in and stops. That hurts a lot. "What the hell are you doing? What is that? It's hurting me." I yell at the cop. I'm really confused right now as I'm stood up straight and handed a ticket. I read it slowly. "For the offense of speeding while in the buff: you are to leave this butt plug in your ass until Satin feels you have paid your dues to society. For the offense of having a nice cock: you will suck my dick right now." Another hot chick with a surprise and this one's a cop with a gun? I look around at Satin and she's smiling and shows me her hard on as she begins stroking. I've been set up. What the hell, I drop to my knees and undo the zipper of the cop's pants. A monster pops out of her uniform. That's an inch bigger than mine and much wider. And it's still growing. I better hurry and get this over with before it's ripping my mouth apart. I grab onto it and start to take it in my mouth. I start to gag immediately but hold it there and keep going as far as I can. Sucking and pumping this huge cock as hard and fast as I can. My practice on Satin pays off as the lady boy cop shoots in my mouth. And shoots, and shoots. Her cum starts leaking out of the corners of my mouth and Satin is kind enough to clean it up with her tongue. When she's finished she pulls out of my mouth and tells me to "Put my cock back in my pants and slow down, driving and blowing." With that she turns to leave. Satin comes up to me and kisses me, feeding me the cum that she cleaned up off my chin. She laughs and tells me that the cop is one of her good friends and is always happy to have a little fun with her. I grab Satin's cock and suck her off too. I don't know what came over me but I want it right now. She didn't argue either. We head back out on the road looking for a gas station and then I see one. It's a small little mom and pop kind of place and I pull in. I grab some cash and head inside. The clerk looks disgusted and takes the money quickly so I can get out of there. With his look, I decide I want a drink too and grab us a couple waters just to stay in there longer. I take my time looking around picking up a couple magazines and went back up to the counter to pay. As I'm walking back to the car I noticed Satin has her shirt and bra off but is looking concerned about her panties. After I tell her how the clerk acted towards my nakedness, I bet he'd be overly enthused to see her naked too watching that hot ass pumping the gas. "Just make sure you don't turn around enough for him to see your surprise until the tank is full. I bet he'll be yanking his cock the whole time until he sees that hot piece between you legs, or maybe he'll keep jerking it while he watches you" I instruct her as I stand on the other side of the car glancing inside every couple seconds to see what's going on. Satin drops her panties and gets out of the car to pump the gas. She puts on a show acting like she's humping the nozzle in and out of the tank and turning enough so the clerk can see her boobs while she plays with her nipples. I can tell he's jerking off at the sight of her. When the pump stops, she pulls it out and hangs it up. Then she turns to the clerk and starts jerking herself off right at him. I see him fall off whatever he was sitting on and then get up and start for the door. "Time to go, hurry," I shout at her as he's heading for the door. As we speed out of the gas station we both flip off the clerk. "Remind me to never stop there again. He's not very open to public nudity." "So that means we're going for naked drives more? And I'm sure he didn't like my little surprise either," she replies to me while grabbing her penis and stroking it. "Hell yeah we're going for more drives. Naked or not. He might have liked it and that's why he was running after us," I say with a little chuckle at the end. "I forgot I had this thing in my ass while I walked around the store. Must not be very large." She laughs at me and bends down and starts to give me head while playing with the butt plug. "It's not big and it's made flexible so it fits and moves within you while always massaging your prostate. It keeps you hard and makes you ready for me." I almost wreck as I come so hard. It feels so good what she's doing to me. "Guess you liked that. Don't worry, there's more to come," she replies as she wipes some of my cum from her mouth and feeds it to me. We drive for another half hour until the GPS tells me to pull off onto a dirt road and a mile later we pull into a trailer park. I look at her nervously as she is telling me to get out of the car. We walk up to a picnic pavilion filled with men and she males. "Get on your knees." She ordered me as she walks over and starts to talk to an older gentleman. When she returns, she instructs me to get up because we're next. "Next for what?" I ask not knowing what was going on. "Trust me. We're going to have sex and if we're good enough to get the most votes, we win a case of wine. That is what we left the house for, isn't it?" She tells me with that devilish grin. When we get called, we walk to the center and up onto a picnic table. She starts pulling the plug out of my ass and it hurts on the way out but leaves me feeling empty at the same time. Her cock surprises me at my mouth, which I take in quickly and begin to suck her manhood. She keeps pushing it farther and farther in my mouth until it's all the way in and entering my throat. Gagging is the natural tendency for me but I fight it off for a short time and then I pull off of her cock looking up at her apologetically. She moves around behind me and lines up with my asshole and without warning is buried all the way in me. As she starts fucking me, I reach around and try to play with her ass to give a better show. Next thing I know I'm shooting my first load onto the table. She is working me so expertly, I am quickly hard again and feeling another load getting ready to blow. I don't care who is around us watching me get pounded up my ass. I'm starting to get more and more infatuated with this woman pumping her surprise in and out of my ass. I can't wait to get her alone. I start to push back on her and squeeze my muscles to give her a tighter fit in my recently loosened ass. She moans in appreciation and pulls out of me. I feel hot shots of her cum on my back. She must have coated me with her juices. I blow another. Then a tongue starts lapping it all up. I am rolled over onto my back and she has her mouth a couple inches over mine. I know what's about to happen and open my mouth ready to receive her sperm that was recently licked off my back. She opens her mouth and lets her cum mixed with saliva drip into my mouth and we kiss. I am expecting to get my turn, but surprisingly she gets up, rolls me over and slowly pushes the plug back in my ass. I feel another hard on arriving. Everybody is applauding our performance and a case of wine is awarded to us. We both hop in the car naked and head back to my friend's house. "You knew that was going to happen all along?" I asked already knowing the answer. "I'm not sure I liked the fact that we did that in front of all those people very much. But, it's ok because I enjoyed what we did and I feel we are getting closer with every minute and experience we have together. I like that you have an exhibitionist side too. We are more alike than I thought. Maybe someday we can take a vacation to somewhere nudity is accepted." "Yes, I knew what we were going to do and today was all planned. Your friend called me after you accepted her dare and asked me to help her set you up. I was afraid of how you would respond to the whole thing, but now I know you aren't going to run. I don't do that kind of thing normally. Guess I kind of wanted to show you off. I had a lot of friends in the audience. I however do love to get naked every chance I get but as you can see, it's a little difficult for someone like me. A vacation would be nice. Just the two of us." Forty-five minutes later we're pulling into my friends garage. They meet us at the door asking what took so long, both of them giggling and also naked. My friend's friend is hot. Lucky for me I was already hard and Satin took notice. They moved out of the way and let us through with the wine. My friend grabbed hold and gave a wiggle to my new butt plug. "Go shave your rose. That thing is a mess down there." I sarcastically tell her. She looks down and back up and asks what's wrong with her bush. I grab Satin's hand and spin her around. "This is what the perfect trim looks like." I tell my friend as I move Satin's cock back and forth to show how well groomed she is, and gives me a chance to hold her package for a minute. I can feel her growing in my hand. "Fine, we'll go take care of our problem. You have to take care of the one you just created. Haha" Both of the women were laughing as they headed for the stairs. I looked at Satin's beautiful face and she pulled me in close for a tight and exotic feeling hug and kiss. We separated, I look her in the eye and started to caress her nipples. I kneel down and take a nipple in my mouth and then the other. Then I get behind her and start to lick down her back all the way to her ass. I make sure she is ready for me and stand up to start making love to her. To my surprise, as soon as I am about to start pushing into her, she pushes against me and has me buried inside her in one fast movement. She lets out a little moan and then starts to gyrate her ass against me. This feels amazing and I know I won't last long. And I don't. A couple seconds later I shoot inside her. I drop to my knees and suck as much of my cum out of her ass as I can. I grab her and kiss her to share and she kisses me back with more passion than any girlfriend I've ever had before. Now it's time to take care of her. After the fucking we just did, I get to taste her cum quickly. I also share this with her with another passionate kiss. We go sit in the living room and wait for our friends to come back downstairs when I hear, "MAID, WHERE'S MY WINE?" Crap, we're still playing is all I can think. I grab a couple glasses with a bottle and head up to serve the wine. Once up there I see two completely shaved women. My friend bends me over and asks me to inspect her to make sure there isn't any areas that they missed. I inspect around her ass hole and stick my tongue right in. She yelps and jumps while planting her face right into her friend's pussy. They seem to like this and I never knew this side of my friend. I thought tonight was going to be me and Satin pleasuring the two ladies and each other. "I'll just leave you two here and Satin and myself will be heading home. Where are my clothes?" I ask. "Fireplace" is the muffled response from my friends friends pussy. "There's a drawer full of panties in my room. Help yourself." Not again. I head to her room and look in her drawers. Seeing her collection of vibrators, I select a few to borrow. I learn that she doesn't wear anything but thongs and g-strings. I find the hottest pair and put them on and head for the stairs. "Ready?" I ask as Satin looks me up and down. "They're going to be busy for a while up there so I excused us for the evening." "Let's go. Where to?" She replied. "My place, your place. Doesn't matter as long as we're together and not dressed like this in public." I grab a couple bottles and we leave adding, "I live closer." "Sounds good. I don't need anything for tonight. As long as you have a shower for the morning I'm good." "You sure, it could be a long weekend." "It's not like we're going to need clothes. We have a couple bottles of wine and I already checked out your cupboards and fridge. Essentials are covered for a couple days." She replies with that same devilish smile I'm starting to like, a lot. When we arrive in my parking lot a strange familiarity comes over me, but the sun is out this time. "You can run up and grab me some sweats?" I ask. With that question, the grin is back and she throws me her dress. "Bring ME back some sweats baby." Crap. She knows how to get me worked up. Now I have to wear a small dress with a hard on all the way up the 3 sets of stairs and back with sweats for her. I get up to the apartment without incident and start looking for something for her to wear back up here as embarrassing as my current attire. "Got it, white boxers and white t shirt. Oops, did I get them wet?" I'm laughing as I look out the door to make sure the way is clear. Back at the car I hand the clothes through the window trying to from keep laughing. I feel her punching me as she puts on the wet and very transparent underwear. Only a couple people saw us on the way back up to my apartment. I'm sure the rumors of my past antics have already circulated the complex so I'm not too embarrassed. I don't know if they saw her surprise, and I really don't care either. Once inside, we are naked again and jumping all over each other. This is going to be a great weekend. Hope I can keep up with her. We spend the rest of the weekend naked and exploring each other in every way possible time will let us. I learn as much as I can about her and she learns everything about me. I think I want to ask her to move in with me and make her my steady girl friend. I even look at vacations for us to enjoy a nude holiday.