[M/M] Finally got to experience my fantasy | 2016

Despite being a straight guy I've had one very dirty fantasy for a long time: sissy sex. Last weekend I finally got to try it.

A few weeks ago I met a guy on fetlife, we'll call him Mark, who happened to live in my area. He ended up offering to make my fantasy happen, and we made plans to meet on the 12th. As the day approached I got more and more excited and nervous. I was scared that I would get cold-feet and back down. Finally, the day came and I drove over to his house. He met me at the door and briefly showed me around his house. Then he lead me to a side room where he had laid my outfit out and told me to change. He had me put on: pink platform shoes, white thigh high socks, pink lacy panties, a skirt like this: http://www.thesissystore.com/petticoats/lil-princess-petti-skirt?cPath=4& , and a tiara. When I came out he had his dick out and was stroking himself. He gave me a look-over and told me to come over to him.

My heart was pounding, I knew this was the moment of truth. He slowly pushed me down onto me knees, and cupped the back of my head with his hand. His penis was right in front of my face, and I wasn't sure if I could do this. Mark slowly pulled me in, saying, "C'mon baby, you can do it." At that moment I decide to just go for it. I wrapped my lips around him and started to suck. Mark let me warm up for a while before forcing my head all the way to his base. That caught me by surprise and I choked a little, but I managed not to vomit. I grabbed on to his legs as he started to face fuck me, starting to wonder just what I had gotten myself into. In a bit Mark got close to cumming and pulled out, then came on my face. He told me to leave it on, and pulled me up off the ground. He then told me to do some chores while he watched tv.

For the rest of the day, I did chores around the house, still wearing my sissy outfit, while Mark relaxed. I vacuumed, did his laundry, cooked lunch, that stuff. Whenever he felt like it he would come over and have me suck him off, and then cum on my face. I wasn't allowed to clean any of the cum off.

After lunch we did something new. Mark called me into his room, and told me to bend over the bed. My heart started to pound again, I knew what was coming this time. His bed was pretty high, so I was bent over just about 90 degrees at the waist. He came up behind me and slipped my panties down around my ankles, then he started smearing some lube around my hole. All he said was "Alright baby, get ready" before sticking his dick in. He did go pretty slow, but it was still rather uncomfortable. He started pumping slowly while I adjusted, and it started feeling pretty good. After about 10 minutes, Mark grabbed my arms at the elbows and pulled them behind me. He started pumping a lot faster. I'll admit, it felt amazing, and I actually started moaning. Mark started talking dirty to me, calling me a little sissy slut and telling me to beg him for more. I started to yell out oh, daddy fuck your slut harder! He dropped me arms and pushed my face down into the bed, pounding my ass. When I came I did scream, it was the most insane orgasm I've ever felt. My asshole clenched hard, making Mark come too. We were both panting as he pulled out (he was wearing a condom of course.)

Mark told me to pull up my panties and get back to work. After that sometimes he would bend me over instead of just having me suck him off. Either way, he still made sure to give me a good facial, and I was getting a thick layer of cum on my face.

I was at his house from around 10 to 8. By the end of the day my face and hair was plastered with Mark's cum, and his house was spotless. My throat and butt were both super sore, but I felt amazing. Mark was exhausted, so instead of fucking me himself, he told me to ride a big thick dildo for him. It had a suction base, and he put it on the kitchen table and told me to hop up there. He told me to wait a moment, and stepped outside. When he came back in, he had three friends with him. They all sat around the table while I sat down on the dildo. Luckily my ass had been stretched out by Mark, and I was able to fit it in without to much trouble. I rode the dildo while Mark and his friends watched me. I knew I looked like such a slut in my tiara, dress, and face full of cum. I started to moan loudly as I rode that dildo faster and faster. I managed to cum again, and I shot all over the table. Mark had me lick it up, and then took me to the bathroom where I cleaned up and changed back into my normal clothes. He and his friends said goodbye at the door, and Mark suggested letting them get in on the action next time. I walked with a noticeable limp as I headed to my car, and sitting down was uncomfortable. I felt wonderfully used as I drove home, and I think there will have to be a next time.