Yesterday was a really fun day. Me and my Daddy have been trying to arrange a day for us to play and it all worked out. After exercise, shower, and shaving my body, I worked on my makeup including some purple eye shadow and hot red lipstick, along with my shoulder length pink wig. I wore my favorite black bra with white dots along with skimpy black panties (see my recent pics for an ass shot). Topped it all off with a black A-line dress with a top that has a sheer part around the collar, along with some tall black boots, a choker, and my purse. Definitely had that goth girl at the club look which I like. I had also packed a suitcase with a few dresses, since Daddy requested to see me in other outfits too and wasn’t sure what he wanted to see. Finally, I left the house and drove about 30 minutes to see him in the middle of the day…I’m getting more used to that :)
I arrive and he’s waiting at the door for me where he tells me he missed me and gives me a big kiss as usual. I begin to melt for my Daddy as he kisses me and reaches behind my skirt and grabs my ass in my panties. “Well, Becca, let’s get you to the bedroom and get you comfortable”. We go through the suitcase and he asks me what I want to wear and I tell him whatever he wants to see. I definitely get very submissive when I dress up for him and honestly already just wanted to play with his cock.
He picked out my pink lolita/sissy dress with a petticoat. He said it was the girliest thing I had and he wanted to see me at my sissiest, which of course made me want to do it. I told him I needed help out of my dress so I leaned back against him with my ass leaning against his hardening dick as he unzipped me and pulled the dress over my head, leaving me in my lingerie and boots. He continued to grope me as I moaned. My smaller cock started to get aroused in my panties and he teased and eventually let go. I put on the petticoat and asked him to zip me up and tie the bow on the dress. He walked me to the mirror and showed me in my pretty pink dress and kissed me. He continued to tease my cock and had me grab him as he was hard and said “Why is this hard?” until I said “Because I get Daddy hard”. We went into his living room where he had me pose and he took pics of me in my phone. I thanked him and we sat on the couch and cuddled for a while as we made out and he continued to tease me. I was feeling very horny by now…I was in such a feminine feeling with a guy who was turned on by me in this. Eventually he told me he wanted to see something else, so we went to the bedroom and I changed into my Junko costume I got recently from the anime Danganronpa (also some recent pics up on Reddit), with a short plaid skirt and a cute jacket. I switched to high heels for this. Daddy loved it and had me pose some more but this time made me take slutty pics. He grabbed my small cock and put it up against his much bigger cock and rubbed them together and said “look how hard you get me sissy”. Eventually he stripped me down to everything except my bra as he got completely naked and told me it’s time to get on my knees and suck him.
I eagerly was down on the floor, looking at myself in the mirror with this big dick in my mouth that I eagerly sucked. He demanded his balls be licked, which I did. He continued to grab my phone to take pics of me being a total slut for him and I looked at the camera like a true porn star.
Before he came, he told me to stand up and get on the bed, which I did. He took out a big black dildo and had me lay on my back as he lubed and fingered my hole. I couldn’t quite take the whole dildo but I felt a little of it enter me as he kept telling me “Good girl take as much cock as you can in your sissy training”. I don’t think I was getting the whole thing in. He sometimes would take his big dick and slap my face or lay it on my hard cock as I laid there submissive and horny for this man who was emasculating me so much…so much for being a straight guy.
He laid down on the bed and told me to get on top which of course I did. I started grinding my ass on his cock as it was very hard and so was I. He kept saying “Good girl Becca keep going”. I was feeling so horny as his cock poked at my hole and I told him I was going to cum…he told me to let it go and I came all over his chest, which I of course cleaned up with my mouth as I laid down next to him and saw his still hard cock there, with some of my cum on it. I grabbed it and kept stroking until I was ready to fully suck it eagerly. I needed to make my man cum so bad. Eventually he said he was cumming and grabbed my head and held it as ropes of jizz filled my throat. He really came hard for me, so I knew I did a good job. We both laid there spent for a few minutes, before I wiped myself off and got a little cleaned up.
I worked on my makeup because it was time to go, and I knew I was going to have to drive and walk through my neighborhood filled with Daddy’s cum still in daylight. After getting prepared, I gave Daddy a kiss and left for the day. Of course, I’m already thinking about what kind of outfits I want to get for my next visit, and other things I can do out en femme. Really want to flirt with a guy at a bar now :)
Source: reddit.com/r/gonewildstories/comments/10p1gox/39_mm_sissy_crossdresser_tried_on_different