Finally Did It And Now I'm Hooked
By sissythrowaway42069

Posted with permission from sissythrowaway42069

Original Post

So I was particularly horny the other night and decided to take some pictures and post an advert on Craigslist, just to see if anyone would be interested. I was expecting maybe 4 or 5 responses overall, which I got within the first five minutes. I think in total I ended up with around 200 messages, which was a huge confidence boost for me, and I can honestly say I didn't get a single mean-spirited reply. I got so much encouragement from guys and other sissies in the area. This is what really pushed me to finally give it a try, knowing there were guys out there who were jerking themselves to me. I decided to rent a hotel room for the following night so I would be able to spend a few hours fully sissifying myself. I didn't want to be cheap and just wear a wig and lipstick or something, so I did everything I could: freshly shaved my whole body, did makeup, wore perfume, etc. I lined up six guys to invite over, knowing that a few would probably bail (which turned out to be the case).

Everything that follows felt completely dreamlike and unreal. I didn't have to wait long before the first guy arrived. He immediately complemented me on how hot I looked and went to take his jumper off. I timidly sat on the edge of the bed, staring at the carpet and adjusting my outfit. Suddenly I felt him grab my head and start to kiss me, and from that moment I knew I was his little slut. We made out for a bit as he pushed me against the bed and we felt each other's bodies. Then he took the rest of his clothes off and sat back on the bed, inviting me to suck his cock. Without hesitating I began to blow him, massaging his balls and taking him as deep in my mouth as I could, all the while he grabbed and slapped my ass. He told me I give amazing head, so I guess all the practice I've done on my toys has paid off! Before long he told me to stop or else he would cum, so he bent me over and I was rimmed for the first time, which felt incredible. He sat back on the bed and I gave head to him again, this time with him cumming in my mouth. Tasting his cum as it rushed from his cock nearly made my little caged clit leak as well. We cuddled for a while afterwards, talking a bit about each other, until he eventually got up and left. I just sat on the bed for a while, still not quite able to believe what I’d just done.

I had another guy on his way, so I had to quickly reapply my lipstick, which had mostly worn off from beforehand. Having to quickly get ready again between servicing guys made me like such a slut. As it turns out, the next two guys didn’t turn up, which was a bit disheartening. Luckily though, another did about an hour later. He asked me to leave the door slightly ajar and sit on the bed in doggy style, so he’d be able to fuck me as soon as he showed up. I obliged, and I eventually heard the sound of the door open and shut, him walk over to the bed and slap my ass. He told me to beg for his cock, so I begged for him to fuck me like his slutty girl. I felt the head of his cock rubbing against my pussy, then suddenly plunge all the way in. I don’t remember much here, other than moaning without even trying, and thinking he was going way too hard and fast, but being unable to tell him through the waves of pleasure I felt. Basically, it felt like heaven, and I remember vaguely feeling my clit leaking cum, but hardly even noticing from the intense pleasure of his cock inside me. Eventually he pounded me harder and faster, slapping my ass again and feeling his cock tensing up before cumming. Since he was wearing a condom, I felt him dribble the cum down my pussy and then leave it on my butt, and he called me a ‘good girl’ before leaving. The fact I never even saw him and was just a hole for him still makes me feel so fucking hot.

The next two guys didn’t show up either, so I’d started replying to some of the more recent offers. I invited two more people, and only one showed up. Like the first guy he was also really into kissing, and made me stroke his cock as his tongue played with mine. Then he grabbed and pulled me to the edge of the bed, watching him lubing his cock as I held my legs up for him. He shoved it all the way inside me and leaned over so we could kiss as he fucked me hard. This was probably my favourite position to get fucked, he had total control over me and I could wrap my legs around his body. Unfortunately he came pretty fast, but he stayed for a while to make out some more before getting up to leave.

I ended up checking out from the hotel early and going back home. The following few hours were completely unreal. I’ve done acid, weed, ecstasy…but nothing has ever made me feel more high than getting fucked as a sissy. I’m now completely hooked, and have made plans to meet up with more guys later in the week. I can’t speak for every sissy, but all three guys were extremely accommodating and nice (all things considered!). I was pretty picky about who I chose to invite (wouldn’t invite anyone who wouldn’t talk on the phone or send a face pic), so maybe that was what made it such a good experience. I can honestly say I have only one regret, which is wearing nail polish, because I spent like an hour with acetone and qtips trying to get that shit off. Otherwise everything was absolutely perfect. For any other girls still anxious about taking the step, I can’t recommend it enough. I am absolutely not the skinniest or most feminine person in the world, and I think sometimes the constant porn on this sub makes people think they need to be tgirl models to hook up with attractive guys. Yet two of the three guys I met were very attractive, and all three were young and fit. It’s almost entirely about the mindset and effort you go to; things like learning how to do makeup and buying a wig that isn’t from the dollar store really elevate you above the average crossdresser who just wears panties. If you made it this far, thanks for reading, and to all the other sissies whose experiences pushed me to finally give this a go!