Finally Did It! (first Time)

About a month ago, I finally did it; I sucked my first ****. To completion too, using only my mouth! Here's how it all went down:

So, after watching more than my fair share of crossdressers sucking **** on various websites, and reading over these erotic stories on here, I decided to woman up and find a nice **** to suck. I posted an ad on craigslist, and in VERY short order got an overwhelming response. Guys were practically lining up to give me a penis to shove in my mouth.

So, I worked my way through the responses, and settled on the one I figured to be the nicest, most gentle one to be my first. We exchanged a fair number of emails, set our expectations and boundaries, and eventually set up a date (I admittedly chickened out once, claiming to be unable to make it).

The day prior, I shaved everything. I painted my finger and toe nails. And then, the day of, I spent an hour or two doing my make-up and fixing my hair. I wore my favorite brown leather wedges, a lacy black skirt that came to just above my knees, and a light orange top that accentuated (but concealed) my fake breasts. I tucked everything away into my black Victoria's Secret panties (that I asked the sales girl to help me pick out), and walked to my car.

Not even a few steps out the door, and my erection leaped from my panties. Luckily for me, no one was outside around my apartment complex, so as far as I know, no one saw the massive bulge in my skirt (if you're curious, I'm a thick, cut 7"). I got into my car, looked in the mirror, and despite being incredibly nervous, I smiled at how stunning I looked (when I go all out, I even fool myself into thinking I'm a girl).

I drove the short distance to the motel we agreed upon, and pulled up in front of his room number. Just my luck, the cleaning lady was outside just two doors down. I prepped myself in my rear view mirror, and stepped out, trying my hardest to keep my member under control. She looked my way; I smiled and waved slightly to her. She smiled back and went back to what she was doing... I'm pretty sure she assumed I was just some prostitute. One person fooled. :)

I knocked on the door, and was shortly greeted by the man I exchanged so many emails with. He looked almost more nervous than I was. We'll call him Bill.

Bill let me in, and I gave him a hug and introduced myself. I thanked him for meeting me, and we sat down on the bed. At first, I was pretty scared, and not sure what to do. We had some brief awkward conversation, at which point I realized he was unsure of how to proceed too. So, I asked him if he'd like to touch me.

He got closer, and started touching my arm, slowly working his way up to my neck. I could feel his breath on my shoulder as his hand moved down towards my chest. He felt me up for a little while, eventually moving down to my smooth legs. My hands wandered down to his crotch (he was only semi-hard), and began to message him.

After a bit of petting and groping, I asked him if he'd like to take his pants off and get more comfortable. He quickly obliged. I had him scoot to the edge of the bed, as I got up and stood before him. I looked down at him, and pushed him back so that he was lying down. I crouched down, and decided to just go for it. I came to suck ****, and dammit, that's what I was gonna do.

I gingerly lifted his slowly hardening member to my lips, and started to lick. (I noted that, even though my ad specifically asked for 6"+, cut, and shaved, he was none of the above) After a few licks, I went all the way, and pulled his **** into my mouth. I worked it, remembering the videos, stories, and tips I'd looked at leading up to this moment. He was rock hard instantly.

The biggest thing I wanted out of this was to try my hand at deepthroating. I have very little gag reflex, so I figured I could probably handle it. I was more or less right. I did learn quickly, however, that it must take a LOT of practice to be able to deepthroat like in the **** flicks. I did my best, taking him into my throat a number of times.

Eventually, I decided I wanted to feel what it's like to have hot *** spurt into my mouth, so I started to go faster and faster, working my tongue along the underside as I went. I also tried using my hand at the same time, but truth be told, there wasn't much **** left, so I simply held the base of his shaft.

As I got him closer and closer, I took my own **** out of my panties, and began touching myself. The way it felt having a penis in my mouth for the first time, coupled with the way I could feel my wig brushing across my cheeks and bracelets clanking on my wrist made me feel like I was actually who I wanted to be (a sexy woman), and that made me so incredibly horny.

Within moments, he warned me he was about to come (as if wondering if I wanted him to come in my mouth or not), and all I did was go that little bit faster. His warm *** splashed in my mouth as I kept on sucking and licking. When I could feel him stop ***********, I slowed down, and sucked and licked at his head, trying to get the last bits. I looked up at him, and swallowed it all down.

(It was really nothing like I had expected. I've came in my own mouth before, and this was no where near as strong as what I was used to. I didn't mind it at all, which I was worried that I would.)

After he came, I got up and went to fix my make up and get some water. I touched up my lipstick, brushed my hair, and after a short conversation, I gave him a quick kiss, gave his junk a quick squeeze, and headed out the door. (All told, I was there probably around 40 minutes, with the ******* lasting 15-20 minutes.)

I drove home, so horny and excited at what I had just done. I got in my apartment, started looking at some of my favorite videos, and came almost immediately. It's been a long time since I've had an ****** that intense. After I came, I cleaned myself up, got undressed and took a shower, transforming back into male mode.

...What I didn't expect was the overwhelming wave of shame and... Regret? I felt pretty weird about the whole thing afterwards. I told myself that I wasn't going to do that again, that it was a one time thing.

However, now that more time has passed, I REALLY want to do it again. I enjoyed myself leading up to, during, and immediately after giving head. I've never felt sexier in my entire life, and I want to feel that way again. The next time I get the opportunity, I plan on finding another guy to go down on.

Maybe this time, I can get him to *** in my throat! ;)
guy81385 guy81385
26-30, M
4 Responses Nov 26, 2012

I loved your story. I want to do that one day. I have sucked **** but I have as yet gotten one to *** in my mouth. Oh! Well. time will tell.

Great story. that was alot like my first experience that you can read about. I felt so guilty and shameful the next day that I threw away all the clothes/wig/makeup etc that I had collected and said I would not do it again. Over time that feeling went away and I really wanted to do it again. My problem was that it is/was always so hard to find guys. I didnt want to do it with just anyone, I wanted the type of guy I wanted and I was rarely successful with that. If I had found more of them men I liked who knows how often I would have done it. The shame does go away over time, but I still had some of it the more recent times I did it.

Wow! I wish I could be passable, and have an experience like this! It sounded amazing! I understand the feelings after. My first M2M experience, I felt so guilty and ashamed, and had the most horrific nightmares that night. :(

What a great experience. Your feelings are natural because of how you were raised. The more you do it though, the more natural it will become for you as a woman! Have fun!

Lisa