My First Boyfriend Part Five

By cindytranee

Original link: https://www.lushstories.com/stories/crossdressing/my-first-boyfriend-part-five.aspx

Tags: oral, anal, gangbang

Added: 08 Feb 2012 Views: 8938 Avg Score: 4.57

I step out on my boyfriend and end up getting gangbanged
Things had pretty much gotten back to normal after our wildweekend a week or so before. My boyfriend Steve and I had our unofficial “honeymoon” where I had dressed in a wedding dress and we made love. I had been out dressed as a girl for the first time and had gone to a party where I sucked off a bunch of guys for money. Steve and I had taken two of those guys home with us and they all banged me all night until their dicks wouldn’t get hard and then had started putting other stuff up my butt. I had also been spanked by them and loved that. It took a week for the bruises on my ass to heal but my asshole felt better after only a few days so I was already fucking Steve every chance I got.

Even though I lived right next door to Steve we had to be careful about hooking up. We met up at least once a day for me to blow him and sometimes a quick fuck. We would usually meet in the fort but sometimes we would meet between our houses and go behind a huge bush there and I’d suck him off and maybe drop my pants and bend over for him to fuck me. Sometimes if his mom wanted something from the store he’d pick me up on the way out and I’d blow him in the car. We had almost been caught a few times by my brother and Steve’s mother; that kind of made it exciting knowing we could be caught.

My hair was getting longer and easier to style and I had practiced my female voice so much I started using it all the time; something which concerned my father very much. I wanted to get on hormones but was not quite sure how to go about it so for now I was happy just being a flat chested girl with a surprise. It kind of sucked having to go to school dressed like a guy and around the house too. I longed to be feminine full time but knew it would be a while before I could do that.

One day I was going through my girly clothes and found the purse that I had brought with me to the keg party where I sucked all those guys off and upon opening it found a slip of paper with a number on it. Underneath the number it said. “Call me some time, Dale” and had a smiley face on it. Dale was one of the guys we brought home from the party who had fucked me all night. He was the one who made me cum three times that night while fucking me. He was the one with the huge cock! I guess he slipped his number in there when no one was looking. I dismissed any thought of calling but still kept the number though I didn’t really know why.

The thing is that I couldn’t stop thinking about Dale and that huge cock of his. I had only been fucked by Steve mainly. I had fucked Dale and Tom that night but other than that it had only been Steve and up until now I had never considered fucking anyone else. I tried to forget about it but I couldn’t stop thinking about Dale’s cock. It was the biggest I had ever seen (later I found out it was a little over eight and a half inches long and a little under six inches around) and it was circumcised unlike Steve’s. I mean I like Steve’s turtleneck and the way his foreskin slides back and forth when I suck or fuck it but Dale’s big mushroom head being exposed made his cock look beautiful! I tried like hell not to think about it but it was practically all I could think about. I supposed that there was nothing wrong with calling him. I just wouldn’t hook up with him but calling seemed innocent enough. I almost called him but chickened out and threw the piece of paper in the trash.

The next day after a whole day in school thinking about Dale and his cock I rushed home and retrieved the number from the trash and called it. Dale answered and was very happy to hear from me. I had promised myself that I was just calling to chat but he kept saying such nice things about me. His voice was so sexy and he was persistent so I eventually caved and agreed to meet him. I had to wait until my parents were in bed asleep then I would sneak out and go meet him. We decided to meet the very next night.

I could barely sleep that night I was so nervous about it and couldn’t concentrate the next day at school either. That night I told my folks I was tired and went to bed early. It seemed like it took forever but eventually everyone went to bed. I had already gotten dressed in a black cocktail dress and stockings and wore a red thong. I waited until I figured everyone was asleep and got up and did my make up. I threw some black pumps out the window and climbed out. I waited until I was around the corner before stopping and putting on the pumps then headed down the street to wait for Dale.

I turned the corner and was pleased to see dale was already waiting for me. I let myself in and he gave me a kiss before putting the car in drive and taking off. I asked what he had in mind and he said we were going to his house but not to worry; he would have me home by morning. I was a little unsure but lost all control when he took my hand and placed it on his hard cock. I rubbed it for a while before laying my head in his lap and fishing it out of his pants. I spent the trip to his house slowly sucking his big dong. I loved the way it felt and tasted! I licked every little bit of him including his big balls. He was rubbing my ass the whole time and my little cock was rock hard by the time we got to his house.

We walked around to the back of the house and went in the door to the basement where his room was. We passed through the laundry room and opened the door to his bedroom. I stepped in and stopped in my tracks when I realized that he had six or eight guys waiting for us in there. I was about to protest when he grabbed me from behind. One hand was over my mouth while the other arm wrapped around me pinning my arms to my sides. He quickly grabbed my arms and pulled them behind my back and tied my wrists together. I was gripped with fear as I looked around at the room full of horny guys. And I was terrified! Panic set in and I actually pissed myself right there. The room fell silent and you could hear it dripping onto the floor. I had also gotten the front of Dale’s pants wet. I was sure they were going to kill me!

All the other guys looked to be in shock and Dale let me go and said “I can’t do this!” He explained that they had planned to gang rape me but he could not go through with it. The other guys started saying how relieved they were and that they had not really wanted to do this either. Dale untied me and got me a towel to dry myself off a bit with and after wiping up as much pee as the towel would get I sat down still visibly shaken. One of the guys handed me a smoke and they all apologized for what they had done. I picked up a bottle of whiskey from the table next to me and turned it up. I eventually calmed down and stopped shaking. We then sat and smoked weed and drank whiskey and talked.

All the guys seemed nice enough and they all kept apologizing and telling me how hot I was and how horny I made them. Eventually the whiskey got the better of me and I told them that we could probably work something out. We talked a bit more and after a while agreed that for fifty bucks each I would let them gang bang me. I guess I was a real slut. Actually since I was doing it for money I was a whore and it excited me beyond belief! I started off by taking my wet panties and stockings off. I left the dress, suspender belt, bra and heels on. I walked over to the table in the middle of the room and lay across it with my head hanging off one end and my ass the other and said OK guys here is how this will go. One of you come here and let me give him head and when I’m done sucking go around and get my ass while the next guy fills up my mouth. When the first guy cums the second will take his place and fuck me while guy number three gets head and we can just keep going until everybody is happy.

They all were happy with the plan and I soon had guy number one’s cock in my mouth. He was average sized and it didn’t take long for me to get him to the point of cumming. I pulled my mouth off and he went around back to fuck me. By the time he was inside me guy number two was in my mouth. He was not any bigger and I just let him fuck my face while guy number one pounded away at my ass. The other guys were standing around us so I reached out and grabbed a cock in each hand and stroked away. I had to do a double take when I realized that one of the cocks I had grabbed was very big. I looked to see who it was and to my surprise it wasn’t Dale. I was very pleased to find out that there were two huge cocks coming my way that night. Guy number one soon came in my ass and pulled out so guy number two could come around and fuck me, then three, then four and so on.

For the next two hours I had cock in my mouth and ass nonstop. As soon as one guy would shoot in my ass and pull out he was replaced by another. Dale and the other guy with a huge cock each made me cum when they fucked me and I ended up cumming four times that night so they each must had had two turns at me. My ass was so loose by the end that it made obscene slurping sounds while I was being fucked and cum was running down my legs and pooling in my heels. My make up was smeared and my hair was a mess. I probably looked pretty bad by the time Dale dropped me off and I barely had the strength to climb back in my window. I had made $350 that night though and had a good time doing it. I just hoped that Steve didn’t find out.

I faked sick to stay home from school that day and after soaking in a hot bath just slept the day away until Steve got home from work and I met him between our houses to give him head after dinner. He wanted to fuck but I told him I had stomach troubles and couldn’t. My ass was way too sore and still loose from all the fucking I had done. After a day or so I was back to normal and Steve and I were fucking regular like usual. We had a routine of just quick blow jobs or a quick fuck during the week and on the weekends we would go out and fuck in the car or at a park or something. Things were going great until one day I got a letter in the mail and when I opened it I got a shock. It said- HI Sissy, I know what you’ve been doing. You better do what I say or I’m telling everyone you are a Sissy Faggot Cocksucker! The letter was not signed and I had no idea who had written it but I’d find out soon enough.