My Second Time as a Sissy

I'm coming out of a seriously fucked up relationship and decided now is a great time to experiment a little more wildly...to that end I left town, got a room, dressed up, took pics, made a Grindr account and waited to see what kind of replies I'd get.

I should note that I've only done anything like this, or anything homosexual / cd before, one other time (see my prior story), but I can't get enough of sissy porn, hypno, FPOV VR, etc. Everything other than last time up to this point in my cd experiences had been playing with my gf's panties when she was at work. Incidentally, I kept a lot of her stuff in the split, including makeup, a wig, some lingerie, etc. Aside from activities with men was chatting online.

Shortly after posting, I got a message from a reasonably attractive dude with a very attractive cock. We chat. He's from out of town too. Long drive. I offer a massage and say I'd like to try blowing him, but I'm nervous and new to this and if he's not okay with that, I'm not the right gurl. He's down, so I tell him my hotel room number and get things ready. I apply an extra layer of slutty makeup to my already bimbo clothes.

Real quick, my outfit: fishnets, a hot pink sports bra, a hot pink and blue short-ass skirt, pink heels, zebra striped panties, and some trashy jewelry, like teen girl heart necklaces and rainbow bracelets. I had rosy pink cheeks, pink nail polish and lipstick, gold sparkly and blue eye shadow, mascara, a blond wig, and pig tails with pink ponytail holders. I looked like a trashy fucking whore.

He messaged me, "I can't get in to the building or elevator floor without your key". This was not part of the plan. I did not want to go out in public like this, much less into a very busy hotel from the 10th floor to the central lobby...but a gurls gotta do what she's gotta do, right?!

I put on my lame boy clothes but kept the makeup and wig. Embarrassed af before seeing any other judgmental or mean human beings. Immediately I'm in a crowd of six or seven people in the hall. I power walked away and down and endless hall full of people. I kept my head down and hit the elevator button. Bam the door opens and it's like nine people going down. 7ish macho dudes and two slutty dressed women in their 40's - 50's. I felt like the wig covered me up and I just looked like a dude with longer hair, but I started feeling like maybe they were laughing at me or their faint whispers were about me. Of course though, I was probably just paranoid. Except, I realized then that I didn't have shoes on, showing the fishnets, I forgot the bracelets, and still had pink nails. Fml. My cheeks must have really turned bright pink then. We reached the bottom floor and before I could get out to put the spare card in the potted plant (I wanted to be in the room to meet him, not the lobby and weird walk back..), one of the dudes, in a fucking muscle shirt, board shorts, and flip flops, Holding a bud light, like some kinda frat cliche, shoulder checks me. His friends laugh as they all leave the elevator. The ladies giggled a little too. Wow, this was so intense already and so much unexpected heart-pounding humiliating craziness. I won't lie, it was 50/50 love/hate. I tossed the key and ran back to the elevator. I only encounter one person on the way back. Yay.

I get back to the room, lay sleezily on the bed, and await "daddy". Daddy being the only name he referred to himself by and what he told me to call him. Fun!

At this point, I want to restate that this is all 100% true. I feel like it sounds like literotica, but it's totally true.

Daddy arrives. My door opens and I for real had a mini orgasm right there. Lights were low and I could barely see him. In a deeper than expected voice, he states that he is going to use my shower and disappears to the bathroom. After an eternity and a brief scare in which I thought he let someone else into my room, he came out, clothed, and laid in bed next to me. He said he wanted to cuddle. Fun. He's bigger than I thought from the pics and extends his big ass arm around my shoulder and kid of guides me to where my head is resting on his upper belly. I instinctively wrapped my leg around his calf and my arms around his thighs. This earned me some words of praise that also practically made me cum. I can't remember what was said when, but he was on point with the way he talked to me. Lots of fun ones that made my heart fucking pound....

I started to rub his thigh and he stopped me and told me to cuddle him. I liked this, but i couldn't help but groan and squeeze him tighter and gently hump his leg. I guess that did it for him because he reached down and flopped his dick out like one inch front of my face. It was a pretty mighty cock with a big fat head and a kink upward like it's meant to pound a prostate. It was probably 7 or 8 inches full.

In a slightly condescending tone, like asking a question that isn't really a question and is more of an instruction or command, he says "why don't you put that in your mouth, and at the same time begins to gently but firmly press his big hand onto the back of my head and here we go. I opened up and he slid it maybe 1/3 of the way in and stopped, keeping my head firmly in place." Dick, or at least his, has such a fun set of textures. So smooth in some spots, veiny elsewhere, squishy, hard, throbbing, pulsing...

"Work your tongue" he instructed. I gladly complied and he moaned, told me I was a "good little cocksucker" and led my head up, only to then gently but surprisingly start to dribble my head like a basketball, even pointing out that what he was doing.

"Good slut" "Good bitch" "Whose bitch are you?" "Say it with my dick in your mouth" "I didn't say you could take it out yet" "Suck harder slut" "You really are my bitch now, you know that right?" "You'll always be my little sissy bitch now, no matter what"

I have a wimpy gag reflex and couldn't go too far with him...at first, but he pushed me, literally and metaphorically, and by the end of our session I'd say I got 6 out of 7 inches down. He kept pushing and started to get more aggressive, which I fucking loved. I got real submissive. "Time to get your face fucked." He starts thrusting while hiding my face to his belly. Bam bam bam then hold. I gagged almost puked and pulled off of him, which he resisted a bit. As soon as the head passed over my lips and I pulled my head back, he fucking slapped me and pushed me back down. Cue another mini-orgasm. He then pulled it out of my mouth and started slapping my face with it. #heaven

He called me a little bitch and scolded me. I apologized profusely, slapped myself with his cock a few times (more praise, and I feel my precum dripping out of me. I forgot about my dick this whole time. I reached down and touched it, only to be slapped again. "Wtf when did I say you could touch yourself". This got me so fucking hot I swear I wanted to have his fucking babies. I forgot the rule 20 minutes later and was instantly grabbed by my neck and dragged to the edge of the bed as he stood up. Hands on my neck he semi chokes me head down in the mattress to the right height and pops his cock back in my mouth, ALL THE WAY IN. I wretched and gagged, and tried to tap out, but he held me in place for maybe just a second or two, but it was scary and mean and hot AF.

He fucked my face like this and tea bagged me as he jacked off towering over me. He was probably 6 foot to my 5'7 and maybe 200-230, thick but not fat to my 140. "Suck my fucking balls you dumb bitch" he apparently repeated, slapping my crotch. This felt good and bad. I coughed and he did it again. Bam, I didn't exactly cum like normal, but I came. He noticed and did it again, three more quick taps and I fucking came for real.

We spent the next hour or two him positioning me in different ways and me following his directions on how he wanted me to suck. He was super creative in how he mixed being sweet with being nice but firm, then being almost too dominant for my comfort, but not over the line, my line st least.

When we started I asked him to cum on my face. I wanted to swallow but was scared. Unknown to me, Daddy made the adult decision that I was wrong to not eat his cum, and he started taking more control. He gripped my head and worked it like a flesh light. Suddenly his dick seems bigger, then I feel pulsing and taste almost buttery or slightly salty goo. Not bad. I swallow and daddy tells me I'm a lucky little bitch. I agree emphatically and thank him

We chatted after that as two dudes that could have been normal male friends at work or school.

I gave him an hour then started running my fingers up and down his thigh. He puts me back into position wrapped around his leg, Head on belly and tells me to "suck it". So I did for like another, what turned out to be 2 hours!! This time he came on my face. I went to clean it off and was stopped and told he'd kick my ass if I washed my face. (Last mini orgasm of the night). He stated that he was going to sleep. This was not our plan, but like he said, he made me his bitch. I didn't object and he slept while I stayed awake not wanting to sleep while a stranger was with me. I let daddy snooze for two hours and then woke him up.

"Daddy, I need you to fuck my butt". He said he was too tired. I begged. I offered to ride him. He had driven 10 hours prior to arriving in our city that day and insisted he was exhausted and needed to sleep...so I kicked him out and went to sleep.

Again, this was 100% true and a whole lot of fun. More to come...I'm sure.

The end.