The response to my first story was pretty good, so I decided to post another one for you. I have way too many of these, lol. This one is a little long, so I hope it's not too much. It's another of my JO fantasies that comes up once in a while. One version of it, at least. I really appreciate all the positive feed back on my last story. As I said, I'm not a professional writer, and I'm sure there are going to be plenty of errors I'm asking you to look past. Hope you enjoy.
After my divorce, I decided to lean into my crossdressing and bi-sexuallity. I was done with women for a little while. I even made a profile and paid for the premium membership on Adult Friend Finder. It wasn't long before men started reaching out, telling me how sexy they found me, or how they jerked off to my pictures, and always asking to meet up. I'm a pretty introverted and shy guy, so I always tried to keep the the internet between us. After a couple months of chatting with foul mouthed horny guys and playing by myself with dildos and plugs, it was no longer enough. I craved the touch of another human being, and I knew hooking up with one of them would be easier and more satisfying than trying to find another woman. Eventually, I decided to meet up with one of the men I had been talking to. We agreed to meet at a seedy little motel an hour away from me. He rented the room and gave me the address and room number. We had been chatting enough online by then that I felt he was an okay guy and should be safe enough to meet IRL. He requested that I show up fully dressed and with my medium sized plug already in my lubbed asshole. He said he didn't want people to get the wrong idea if they saw both of us enter the room, and the plug would be just the right size to loosen me up for him while still keeping it tight enough to give him pleasure. Besides that, he said I'd be sucking his dick first, and he wanted me doing that with the plug in my ass. It sounded hot, so I was fully up for it. I was a little nervous to drive there and have to get out of the car fully dressed, but pushing myself this far outside of my comfort zone was also a big part of the turn on for me, so I agreed to do it.
Driving an hour fully dressed with my plug shoved deep inside me by my car seat was an experience in and of itself. It was easier to drive with heels on than I imagined. I felt so fucking sexy and nervous at the same time, it was so exciting. All I could think about was that I was actually going to do it. Take a cock in my ass while dressed like a slut. And he had a big one. It was at least twice the size of mine. I've played with dildos that were bigger, so I knew I could handle it. It was the interaction between him and I that made me the most nervous. What if I didn't like him, or if he was dirty and smelled bad? I thought I'd just try to push through it and get it done either way, but if he was really bad, I'd just leave. He wouldn't want to cause any commotion and be outted just as much as I wouldn't, so it shouldn't't be too difficult to just walk out. It'd be really awkward, but that's it.
I arrived at the motel just a couple minutes early. When I got there I thought to myself that this is definitely a seedy little joint, but it didn't look too bad. That boosted my confidence a little bit. I still sat in my car in front of the room taking a few deep breaths before stepping out. He told me that he would be driving a blue Ford pickup, and I had parked right next to one. I knew I was at the right place. I even backed my car in with my drivers door facing the side of his truck. This way I'd at least be covered between the two vehicles as I got out, and it would make it easier to leave if I need to do so in a hurry.
When I finally worked up the courage, I opened the car door and stepped out. I started walking towards the motel room door. I was so fucking nervous being out in public dressed. It definitely helped that it was dark out and the motel room was in the back corner of the plaza, but I was still so nervous that I was trembling. When I got to the door I knocked and looked around to make sure no one else was around. I didn't see anyone, thank god. I heard a deep voice say "Come in!", so I opened the door and entered. Splayed out on the bed, completely naked, was a slightly overweight and unbelievably hairy man. He had shaved the area around his big cock, but the rest of his body was covered in thick black and grey hair, including his face. I was really trembling now, and stuttering as I said hi. Everything in me was telling me to turn around and get the hell out of there, but I fought through it for now. He looked me up and down as I turned to close the door, and climbed out of the bed as I had my back turned. When I turned around, he was right in front of me. He immediately reached up under my skirt and started gropping my ass and rubbing the bulge in my panties. Holy shit, I thought, this is really happening. Alarm bells started going off in my head. A second later, the bathroom door opened and another large naked and hairy man stepped into the room. "Wow, good find Bob! You out did yourself with finding this slut.", he said as he walked up to the two of us. I was practically having a panic attack. He didn't say anything about inviting another guy, and I didn't know this guy at all. "This wasn't what I agreed to.", I stammered. "Just take it easy, princess. George is a friend, and he needed some company, so I decided to invite him along. You'll enjoy this even more with two of us.", he said. I tried to pull away from them. By this time both of them were lifting my skirt and feeling me up, and I could clearly see both of them were ready to get down to business. "No, no, no.", I said trying to push their hands away, "I didn't agree to meet two of you. I don't know him, and I don't want to do this anymore. I'm leaving!". I tried to turn and head for the door. Big mistake. Bob grapped me by the arm and spun me around back towards him. When he got me turned around he slapped me hard in the face with his free hand. "You aren't going anywhere, bitch. Just shut the fuck up and do what we tell you. You can go when we're done with you. I paid for this fucking room, and we're going to fucking use it.". My face stung and I was so scared that I just started to ball. "Please don't do this.", I begged. Both of them started laughing. "It's too late for that, sissy. You're getting fucked like the faggot you are tonight.". There was no point in trying to fight them off, they were both much bigger than me, so I decided to plead again with them to let me leave. "Please, just let me leave. This was a mistake. I don't really want to do this. Please!". "Too late. You're here, we're here, and I had to pay in advance for the entire night. We're getting or money's worth out of you.", Bob said. "Besides, you know you want to do this. You didn't dress up like a slut and shove this plug in your pussy for nothing." George said as he grabbed the base of my plug through my panties and jiggled it around. "We're going to give you the best night of your life, even if it doesn't feel like it right now. You'll look back on this night, and wish you could do it all over again.". Bob walked me over to the bed by my arm. He told me to grab his dick and jerk it as we walked. I did as I was told. I was now thinking of other ways to get out of this. I couldn't do shit in these fucking heels, and with the double straps around my ankles, I wasn't getting them off quickly enough to be of any help. Bob pinned me up against the edge of the bed. "Take your panties off slut, then let's get a good look at you before you suck our cocks.". Maybe if I blow them and make them cum with my mouth they won't need to fuck me in the ass. That won't be too bad. They do smell a little, but not really in a bad way. I'll just play along a little, and hopefully this doesn't have to go all the way. What the fuck am I thinking, not in a bad way! I'm about to be fucking raped! Why am I not fucking terrified? I mean, it's great that I'm not, but I probably should be, shouldn't I? I still don't want them to fuck me, but I think I can handle sucking their dicks. Yeah, I'll just play along for now, then try to get out of here before they get to that point.
I pulled my panties down over my nyloned legs and feet, and off my heels. Bob didn't move as I bent to pull them off, so my face came very close to his cock. I could smell his sweaty crotch as my nose passed it. The air around it was warm and musty. I could feel my little cock stiffen up and my plugged asshole twitch as I breathed it in. George was alongside me now rubbing his thick fingers in-between the base of my plug and the edge of my asshole. I hated to admit it to myself, but I think I was starting to enjoy this. As I stood back up, I grabbed Bob's big hard cock and continued jerking it, while George sneaking the tips of his fingers further and further between the stem of the plug and my tight asshole. Without thinking, I felt myself pushing back against his hand, wanting him to go deeper and use two fingers. It didn't go unnoticed by the two of them. George said, " I think the slut is starting to like this. She's pushing back against my hand. Aren't you, slut?". I moaned, "Mmm hmm.". "That's it slut, push back on me.", George said as he pushed two fingers inside me. The stretch he gave me with those fingers alongside my plug was unbelievable. It was all I needed to convince myself that I needed to do whatever they wanted.
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