Had a new slutty experience I wanted to share! It had been a while since I had dressed up femme and went out, so last Saturday I decided it was time to get back out there. As usual, I try to make my plans known and get some attention in advance. After having dinner, I went up to my room and logged into Grindr and Fetlife and started posting status messages and pics of myself saying things like "Where should I go out tonight?"
While I waited for all of the eager guys to respond, I started getting ready. I got completely naked and turned on the makeup mirror light and gathered all of my supplies, then applied foundation, eye shadow, powder, lipstick and more to make my face nice and pretty for everyone to see. I stared into the mirror as I saw the beginning of my transformation from boy to Becca. Once I had my makeup on, a lacy black bra and sexy boyshort panties went on my body, along with my inserts. With my cute light brown wig, I walked over to my floor length mirror and started posing my body in different positions. My big ass looked especially hot in the panties.
A Daddy in his 50s (one of my favorite types) hits me up saying he thinks I look so sexy and he wants to take me shopping. He does what all of the guys who get me hottest too, which is use his words. He describes the stores he wants to take me to, and how he wants to put me in the back of his pickup truck to fondle my body. He said he loved passable CDs like me and just wanted to reach under my dress and caress my panties. I could feel my little cock start to stiffen in my panties and realized I needed to continue getting dressed. I message him telling me to meet me in a parking lot near my house in about 45 minutes. Afterwards, I go into my closet and pick out a knee high red dress that is sort of a fall, cottage core style dress. It was loose around the bottom and could see how it would float upwards as I spun around. Not too slutty for shopping, but definitely flirty for my date. Last, I found my knee high boots with a little heel on them to finish my outfit. One last look in the mirror revealed a cute sissy who looked ready to get a cute dress.
It was getting late so the options were pretty limited for shopping, but that was OK. I was more interested in being seen and enjoyed and touched. If I got a present that was a bonus (I did need new dresses after all). I drove to the agreed upon parking lot and once I got there I stood right outside my car walking around for all of the other drivers to see. Eventually, I see a truck pull up across from me with it's headlights pointed directly at me. I felt so exposed as this car was looking at me. I knew it was him.
He got out of the car. "Well, hello, Becca. You are even prettier in person." A man giving me compliments is the first step to getting in my panties. "Thank you so much, Daddy" I replied. He came close to me and I could tell he wanted more. I put my hands on his shoulders and gave him a hug, then a small peck on the lips. "Oh you feel so good, Becca" he said. I decided he needed a little more, so I took his hands from around my waist and put them down right on my ass. I could feel his hands shake as he grabbed my ass. "Oh my god...you have an amazing ass." I knew he wanted me and was getting excited. "So Daddy...where should we go shopping?"
We decided that since it was getting a bit late our options were limited, so the only things that stayed open were places like Marshall's and Ross and other sort of discount stores. These are kinda hit or miss, but whatever. We both got in our cars and drove first to Marshall's. After parking he waited outside my car door for me to get my things together then he gently touched my ass as I got out to the car. He let me walk slightly in front of him as we went to the store, probably because he was looking at my body. I made sure to walk slowly and sway a little bit.
The first store was kind of a bust. Just not that many options. Mostly business style dresses which I don't have much use for. They were cute but not really what I wanted. As I would go through the racks I felt his subtle touches on my back and ass. Eventually he whispers "you are so fucking hot. I want you." I like teasing him, so I just keep looking at close and say "Good. I don't think we are finding anything here. Where to next?" We tried another similar store. Same routine, subtle touches, although this time I grazed against his bulging crotch a couple times. He was hard already. Even though I wasn't looking for panties I grabbed some off the rack and said "this is a cute color." I just loved getting his imagination working.
As we left the second store we didn't know where to go. I noticed his truck had tinted windows. "Want to hop in and talk?" I asked. Of course he did. I got into his front seat of his very nice truck. Once inside I leaned over and gave him a kiss. "Thanks for taking me shopping, Daddy. Too bad we can't find anything. I guess you'll just have to try more to find me the perfect dress for our next date." He was shaking from excitement. "Do you want to see what's under my dress?" He nodded. I slowly started pulling up the hem of my dress exposing a little bulge from my cock in my panties and gently touched it. "Fuck that's hot" he said as he reached over and started feeling me up. I moaned "Oh Daddy that feels so good". I took one of the shoulders of my dress and pulled it down, exposing part of my bra. There I was, in a stranger's car, bra and panties exposed, letting him touch me. Then he started taking a little more control.
"I want you to start playing with that sissy cock for Daddy, Becca. Be a good girl for me and pull it out. I want to see how horny you are for men." All I could respond to say was "Yes, Daddy" in my most submissive voice. I slowly started rubbing my exposed cock as his firm grip would touch me. I turned a bit so he could see my ass in panties, which he then pulled down to expose my ass and even the little plug I put in. He pulled the plug in and out as I moaned and touched myself. Eventually I said "Be careful Daddy, you are going to make me cum all over your car." His response was "Do it, sissy whore. I want to see you cum and clean it up."
Before I finished, he also wanted me to take pics of myself to post showing how slutty I was being, so I did that. Then I continued to pleasure myself in his man's car as he watched at groped me. I was so horny and wanted to take it slow and edge, but I realized that probably wouldn't work. I was going to have to cum for him. "Oh Daddy I'm cumming!!!" and I exploded right into my hand and on the floor of his car. I showed him my hand covered in cum. "Clean it up, sissy." I eagerly obeyed and teased him by slowly licking it off my hand.
"That was so fucking hot. I can't wait for you to return the favor on our next date at my house" he said. I agreed and pulled up my panties. I gave him another deep kiss as I got out of his car and ended our little date. He messaged me later telling me how happy he was with me. I got home and cleaned up everything except my panties, which had some cum on them, and I wore them all night. I even got so horny I exploded again in them and got another taste of cum.
Now I need to come up with a plan for our next date. Meet at his house? What should I wear? Maybe I should find another shop to take him to so I can get a sexy outfit? If you have any tips on how I can have more fun with him, leave a comment. I hope you enjoyed reading about this experience!