Bachelor party

If you haven’t read “caught by roommates” read that first.

So my one roommate who was the so called big man on campus; rich, hot and popular could have had any girl he wanted. He started dating a smoke show the only problem was she was a bitch and rarely had sex with him.

At the beginning of their relationship he cheated on her with the slutty college girls. She caught wind of it and freaked. He denied it and now had to be more careful. So he would then fuck me before and after almost every date he went on with her. I became his cum dump. He would even make me wear her clothes and panties when he fucked me.

Then it happened he got her Preggo. She freaked and insisted they get married. He agreed and proposed. Then it came time to plan his bachelor party. One of our other roommates started planning a spring break bachelor party. The bachelor’s fiancee said no way. That we could go rent a cabin and get drunk and play games or something. One of the guys said what about a houseboat on Lake Michigan. She agreed to this.

So all 8 of our roommates were gonna be in a houseboat partying for three days. I messaged the best man saying I couldn’t make it. Thats when the bestman came to me and said you’re gonna be the stripper and girl on the boat. For that you won’t owe any money for the boat, food or drinks. We will also provide you with your clothes for the boat. You just need to get to Ohare airport. I said ok.

I didn’t know what to do now I was commited and I was excited and nervous at the same time. I mean I now had my ass plowed everyday by my TS GF in Miami but I hadn’t dressed as a girl and been fucked in almost a year. I also was unsure what I should do since I was falling in love with my TS GF. But my little penis and ass were telling me do it.

So I booked my flight and planned to see the guys in a month. The months came and the morning I flew out my TS GF said you be good up there. I joked and said what am I gonna do at a bachelor party in the middle of a lake with straight guys. She said I know you can seduce guys with that booty so I am gonna put a mark on my territory. I laughed and said oh really how? She said let me fuck that sexy booty to get started.

As always she grabbed a pair of her dirty panties and said put these on. I slide the pink lace VS thong on and she told me to get on my back and then she ate my ass and the slide her big cock in. Making love to my ass as we made out. She said do you love me babe? I moaned yes as she thrust in and out. She said are you willing to do anything to show me you love me? I moaned yes. She said mmmmm so you will wear my panties while on this trip? I moan yes. She says good as she keeps thrusting.

Then she says ok babe are you gonna fuck while on this vacation? I said fuck who? She said oh babe hot girls. I said no honey I have you and she said do you do t want pussy? I said I want your girl dick she said swear? I said yea she said good babe then you are willing to wear a cage for me? I said a cage? She said yes babe if you aren’t planning to fuck girls why not? I said babe really and she pulled out and said yup as she kissed me and played just the tip. I moaned and said ok honey.

She started grinding into my ass again as we kissed and said so you’re gonna wear my panties and a cage I moaned yes babe as she exploded in my ass hitting my prostate I started cumming too. She said I love you babe and you are mine. She pulled out and said let’s shower and get this on and pulled out a chastity cage. I said oh you are for real? She said yes then I know you won’t fuck girls. I know you won’t fuck a guy with Rusk your buddies caught you and they are all straight you said. So my risk is a TS but you will be caged so I will take my chances. I moaned babe cmon and she said do it for me and I will make it worth it when you get back. I sad promise and she said yes.

So I put a chastity cage on she licked it and then helped me pack my bag. All my underwear were her panties. It all fit in a backpack. She drove me to the airport and kissed me bye. I flew out to Chicago and was picked up by my buddy the best man. On the way to the port he handed me a bag with a miniskirt, belly shirt, wig, lipstick and panties and said put this on. I said dude cmon. He said we are all paying for you do it. I pulled my shirt and pants off and he saw I was wearing panties and said who are those. I said my gf and he said wear those.

He also saw my legs and chest were shaved and said dude owning this girl thing good. I then got dressed and we got to the port. Once on the boat he said since the grooms wife to be wouldn’t let us have girls we brought our own girl wanna be. I walked out and the grooms eyes got wide. The guys said yup your fuck buddy when you first started dating her. I then gave him a lap dance on the boat and could feel his cock getting hard between my cheeks under his shorts.

The other guys said fuck her now fuck her now. I reached around and pulled his cock out of his shorts at this point no one knew j was caged. So I lifted the skirt enough and slid his cock in my ass. I let out a moan as k bounced on his cock until he exploded in my ass while all the other guys watched. I went to the bathroom and text my TS gf I made it and we night nit have service on lake. She said ok have fun babe and if you get Uber horny get your straight buddies to fuck you just take pics or vids for me. I laughed and said oh yeah by text. She said yeah do it. I said if you say so. She said I bet you can’t get the groom to fuck you. I said if I do? She said reward if I get a pic or video. I said ok.

I walked back out and the guys were digging in my bag. I said wtf? They all laughed you packed panties and a dildo? I said no dildo and they held up. I knew my gf packed it, I said my gf put those and the panties it. They said she knows you like cock? I said ughhhh she had a cock they were all shocked. So I told them about my gf and they all laughed. I said she wants a pic or vid of me getting fucked and they said if we do that we will show her at the wedding so you gotta bring her.

Then we set sail. Once out a ways all the guys and I were drinking and playing drinking games. As we got drunk we all loosened up. The guys started spanking my add in the skirts then someone said take that skirt off and just walk around in your panties. I said why can’t a few of you fuck me wearing the skirt.

Then they had me sucking dick while they were also taking turns on my sissy ass. I was moaning as they filled me over and over with cum in both holes. That’s when one was gonna give me a reach around and grabbed my cage. He said what the is that? I said nothing and then he said the sissy has some metal thing in his cock. They all said show us and I showed them the cage. Every guy started laughing.

I said my GF made me wear it. They said did you tell her it was your ass that was gonna get destroyed with us and your cock wouldn’t even be touched. I moaned and said she told me to let you all fuck me and send her a pic or video. They all said really? I said yes. Then they said let’s FaceTime her. Unlock your phone.

I unlocked it and they FaceTimed her as I was riding two dicks sucking a third and had one in each hand with her panties on and pulled to the side. She answered hey babe with camera off I stoped and said no and s guy said we wanna show you your sissy bf. I moaned I can’t they said yes. Then she saw two dick in my ass and one in my mouth. She said babe omg so hot fuck. Then the best man says to my GF, we are gonna destroy his or her holes this weekend and leave them sore, cummy and gaping.

She said mmmm yes make him your bitch boys. I want him to be a slut this weekend for all of you. The groom said oh we are gonna destroy his ass in the panties you sent him in. She said please and send me a few pics or vids. The best-man said we will but without our faces if you send us a pic of you naked to his phone. My GF said I have one better I will text any one of you a big of my dick going in his ass. Bestman said perfect and gave her his number. She sent a video of me in her panties begging her to cum in my ass.

All the guys laughed as they fucked me and made me suck them. Then the best man sent her an old video and said did he ever show you this? She FaceTimed him back and said omg no you have all fucked him before? He responded yes he was our whore in college for like 3 years. She texted wtf I didn’t know that explains a lot. Then she texted him and said I want you to double stuff his ass and send me a video of him begging for your cocks and cum. He said ok want us to do that in the morning on the rooftop so maybe other boats see? She said do hot yes perfect. They all fucked me the rest of the night and then we went to bed.

In the morning we woke up and they said to me today we are gonna make you beg for it and fuck you on the roof. I was so horny because I hadn’t came in the cage and only had leaked to this point. I said ok done. The bestman said good you are gonna wear this and showed me a white lingerie outfit, he said this is the same outfit my wife bought the bride for the wedding night. I thought it was so hot.

Then they took me to the roof wearing it. And they started fucking me and then double stuffing my ass. I was unaware they were taping until my gf told me when I got back. But they were taping. I was so horny I moaned I am a naughty whore fuck me. Then one of them said tell us what you want? I said I am so naughty and such a slut I want every cock to fuck me and cum in my ass. Then I will suck it clean and when you get hard again fuck me again. The best-man said you would rather have cock than pussy is that why you are locked? I moaned yes I love cock. He said girl cock or any cock? I moaned any cock I don’t care. He said any cock or every cock what? I moaned I want every cock I can get to fuck my slutty ass and cum in me.

That’s when I felt a second push in my ass with the first. I moaned and was told I was being double stuffed. I moaned yes two cocks in my slutty ass. I felt my ass start to spasm and legs shake as I came in my cage and squirted in the lingerie. The rest of the weekend they continued to fuck me and make me suck cock and I came in my cage two more times.

Then the morning before I flew back out they came 13 times in my ass between the 8 of them and handed me a butt plug I wore to the airport and home. My GF text me and said that plug better stay in til you get home. When I got home my GF picked me up. Multiple texts and vids were sent to my TS GF and wow was I in trouble when I got back to Miami.