A normal relationship turned into a wild weekend orgy

I was living alone for the first time in my life. I found a decent job, did good in college, and had good friends, but I was always bored with my life. I have always liked to watch porn and experiment, and even though I considered myself to be heterosexual, I was watching more gay porn and porn with trans women than normal. Also really liked the idea of dressing in woman’s clothes, so I started ordering some panties and stockings, a bra, and a dress just to check how I would look in them. Then I began ordering butt plugs and vibrators to try, what it was like to have something more than a toothbrush stuck in your ass. It was different but not what I imagined.

After a year of experimenting and still bored with my life, I decided to take the next step even though I was afraid. I downloaded grinder on my phone and made a profile with no face picture just my body. There are not many gay people in my area, and I wasn’t the best-looking guy there, got matched with some dudes, and started chatting, but that was all, maybe I was too afraid to ask for more. After 2 weeks I matched with this guy let’s call him Ted. He was very nice, we chatted a lot, I told him that I have never done it with a guy before, he was very charming and excited to be my first, and finally, I agreed to meet for a drink. We met in a local bar and hit it off it was going great, after that, I invited him to my place, I put on some gay porn on the TV and we started to make out. It was getting really hot, he took my pants off and started sucking my dick, he was amazing I almost came in like 3 minutes. Then he stood up and pushed me down to my knees. I started to unzip his pants and there it was my first cock, it wasn’t too big around 6 inches, the same as mine. I didn’t know what to do, so I lightly kissed the head, then started softly to lick it all the way down, then I tried to take in my mount and he pushed my head so it was all in. I choked for a second at the surprise, but I was also kind of nice. After that, I started sucking it all over on my own, there was saliva dropping out of my mouth, I had no idea if I was doing a good just, but he seemed to enjoy it. After a few minutes he stopped me, he started kissing me and whispered in my ear “Fuck me”, then he laid on the couch head down, ass up. I didn’t need a second invite so I stood behind him and put some lube on my dick and on his ass, it went in very easy it wasn’t his first time. I started fucking him slowly and he was breathing heavy,” ooh yes, fuck me”, then he pulled away pushed me down, and started to ride on top of me, his dick was slapping on my belly, and he was jumping up and down on top off me, then he stood up and started sucking my dick again, this time I could hold it for much longer and I came in his mount, he didn’t mind and swallowed everything.

After that, we lay on the couch and talked about life:

“That was amazing, my first time fucking a guy, you have such a nice body”

“I enjoyed it too, I normally like to be the active guy, but I liked the way you fucked me, maybe next time we can try the other way around “ – said Tom.

The movie, I put on was still running and I was watching 2 guys fuck each other with a dildo. I was getting kind of hard again and was thinking that if I’m going to do it has to be tonight. I didn’t say anything I just got up and laid on top of Tom and started kissing him again, while my hand was rubbing his dick. I started going down until I reached his cock then started sucking it again, taking it all in my mouth. He didn’t mind just laid there watching me in my eyes while I sucked his dick. I was getting really horny and my ass was ready to take his cock in. I stood up and told him “ I want you tonight, I want you to fuck me”. Then I got on all fours on the floor with my ass up. He was standing behind me and started to lick my hole. It was amazing, he was pushing his tough in and out, then he put 1 finger in, then 2 fucking me slow. I had been sticking dildos and plugs in my ass before so I had no problem with the fingers. In the meantime, I saw on the TV they were in the same position as we were fucking, I couldn’t believe that in a minute we were going to be in the same situation they are. He got the lube we used before and rug some on my ass. Then he started to slowly penetrate me, it was hurting at first, but I want it so bad I ignored everything. He was standing there with his head inside and asked me if I was ok. I didn’t say anything just pushed myself back on his dick until it was all the way in. He started fucking me very slow, in and out in and out. It was amazing the feeling of his dick inside me I just stood there enjoying every second. He started to pick up speed, in a moment he was fucking me at full speed with his dick and balls slapping on my ass. In a minute or 2 he stuck it all the way inside and started to scream, I felt his filling my ass with creamy goodness. Then we lay on the floor tired, not talking just breeding heavy. He went home and I laid in my bed, ass still pulsing and thinking about how much more fun my life will be from now on.

The next day he texted me how amazing it was and that he was hoping we can do it again. I just told him to come later tonight. We were in my apartment again and started talking, normal casual conversation about work and so on. After a few drinks, we laid back and started talking about sex and the fantasies we have.

Tom: “You know last night was amazing, I have to say that I love your ass, it is so soft and tight”

“Really, I never found myself to be very attractive, but I have to admit I love it having you inside me”

We fucked again all night, I fucked him he fucked me it was amazing, but I started to enjoy more taking it in the ass than fucking him.

We kept seeing each other 2-3 times a week, talking and fucking, fucking and talking it was amazing. After 2 weeks, we lay in bed, and I admitted to him that I sometimes like to wear women’s clothes, but I don’t think I look really good in them. He got excited and said he would love to see me dressed like a girl. The next time we agreed to meet, I told him to come to my apartment. I ordered some new clothes, and spent all day preparing, shaving my whole body, got some cute black thongs, black stockings, and put on a cute white top and a short skirt, with cute not very high heels, and I waited for him. I even got a blond wig. He rang on the door and I told him to close his eyes. I opened the door and guided him inside. I lay on the bed and told him to open his eyes. “Wow, you look amazing, just like a naughty school girl”. I put on some music and started dancing for him so he can see the whole outfit. I was doing a lap dance for him and he was grabbing and squeezing my ass really hard. Then I found myself on my knees in front of him and started sucking his cock, it was doing a very professional blowjob. Then he grabbed me and threw me on the bed, pushed me down with one hand, and took off my panties with the other, he stuck his face in my ass whole pinning me down. Pinned down he locked my arm behind my back and stuck his dick in my ass, not being able to move with a dick fucking me hard I felt like a real whore. Then he laid on his back and started to ride him, he picked me up we got up with his dick still in me, pinned me against the wall, and keep fucking, he was so strong. He let me go and I was on my knees in front of him, waiting to get my reward. He came so hard and I swallowed it all, even cleaned his cock after not wasting a drop, it tasted so good.

After that night I became the girl in the relationship, I still fucked him from time to time, but mostly was dressing in girls’ clothes and serving him. I didn’t mind, it was like a dream come true, I loved dressing for him, playing roles, and getting fucked like a slut every time we met. Started to put on some makeup as well, and bought new clothes and wigs, I even fucked him from time to time dressed like that. I thought he was a great guy and I was so lucky to have met him. We kept this going for the next 2 mounts, it was the best time ever, and no one knew about us. We were mostly meet in my apartment, almost never at his, we once went to a hotel for the weekend, where I wore only women’s clothes all the time and acted like his girlfriend, which to be ones I was.

One day he invited me to his apartment for the weekend, he said he had something special planned.

More in chapter 2