Cupcake in Parking Garage Fantasies

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Solo Male

After I got home Anya and I texted for hours. Neither of us had ever done anything so sexy and exciting before. I wrote the whole story in my journal.

We both agreed how exciting it was to be in public, or kind of in public. Something we both want to try again in some way.

It feels so good to be so open about things and be accepted and appreciated. I told her how I used to play dress up with my older sister. She loves dressing me up cute and pretty.

“So you like cross-dressing?” She asked, “Did you and your sister ever go out in public dressed up?”

“No, not really. I have been a little scared too. Maybe at some point.” I replied.

“Yes that is something I would like to help with at some point.” She said, “I think we should also go back to the parking garage to play some more.”

I agreed of course and we planned to meet a few days later. Days that dragged on forever.

I live at home with my Mom and my step sister. She is 2 years older than me. Growing up my sister was my best friend and if I were going to tell anyone about Anya it would be her.

I walked into the living room where my sister was lying on the couch under a blanket watching TV.

“Hey make some space, Toilet face.” I said and she lifted her feet up for me to sit and set her feet down in my lap. I adore her feet and she knows it. She gets free foot rubs and I get off by it, I think she does too.

“What are you so happy about?” She asked feeling how hard my dick was with her foot.

“Yeah I been texting with a pretty hot and sexy lady.” I explained rubbing her foot on my erection.

“Anyone I know?” she asked.

“No, someone I met online. Just a friend so far but I am hoping for more. We had a great first date and are bahis siteleri gonna see each other again.” I told her.

She slipped her foot in my pants and started teasing the tip of my cock, getting precum on her toes. “I hope your new girlfriend is cool with how close we are.” she says. “I don’t want to lose my personal foot masseuse.”

Sliding my pants down to free my throbbing cock I told her, “No chance I would ever give up your gorgeous feet.”

She put the soles on her feet against my cock and I started moving them up and down, stroking my cock. I was already so close what I would normally drag on as long as possible ended quick as I came on her feet.

“Whoa dude!” She exclaimed, “What the hell man? I hope you can last longer for your girlfriend!” She was obviously disappointed and she rubbed the cum off her foot onto my face.

“Jeez I’m sorry!” I whined, “I been edging all day ya know.” I wiped the cum off her feet and my face. “Next time I will make it up to you.”

The next day I was meeting Anya again. We were meeting at the mall again. She parked in the same spot and I met her at her van. I got in the passenger side.

“Did you bring William?” I asked.

“Yes my little cupcake, have you missed him?” she asked, and I smiled in response. “I want the first time I take your ass with William to be special. I mean we are both virgins in that respect.”

“I am picturing myself in a wedding dress and you carrying me over the threshold with rose pedals on a heart shape on the bed.” I said with a laugh and a big smile.

She giggled along and said, “Can I be wearing a powder blue tux with ruffled and a huge bow tie?”

“Oh I would love that! Maybe wear a sexy Nurse costume, or Sexy Doctor actually canlı bahis siteleri and I am the unruly patient?” I asked.

“I like how you caught yourself there cupcake, maybe you wear the sexy nurse outfit and I’m the Domme Doctor.” She said back. “We could make a gloryhole at my place and have you suck him for me. I really want to see you suck a dick at a gloryhole. Maybe even a real one. How do you feel about that?”

“Well the be honest I have fantasized about sucking dicks for awhile. More than just at the gloryhole I mean. I know there are a few in town here but I have never been brave enough to go. I would love if you were there to watch me do it. I have a fantasy where I am dressed real sexy like a school girl, and I am sucking this big meaty dick at the gloryhole and he thinks I am a girl. He finds out I am a trap and breaks down the door to the gloryhole and put me over his shoulder and carries me off. He is like 6 foot 6 and he carries me like I’m a little doll.” I told her with a gleam in my eye. “Oh Jeez, we should be writing this down! Make a To Do list.”

“Oh we will my little cupcake, you have got me a little horny are you wearing panties today? Of course you are lets see them.” She said as she reached over and undid my pants. “Wow you are hard as a rock little boy, you got precum all over your pretty panties.” She rubbed the tip of my dick, driving me crazy.

“Come here baby,” she said bending me over the back seat of her van. “There we go sweetie, lets get these cute little panties off.” She pulled down my pants and sweet blue panties exposing my bare ass and my cock and balls pointed down. “This is how I like you my cupcake, on display and totally in my control.” she seemed very happy about that.

Anya canlı bahis reached and rubbed the tip of my dick again, It was an exquisite torture. Her other hand she spit on her two fingers and rubbed them on my hole and it made me get a shiver up my back.

“Oh you like that huh little boy, such a pretty little rosebud huh. You like it played with.” She stated, “We gotta play and play more and more to get your ready for William don’t we little cupcake?”

“Oh yes, all day every day I hope.” I moaned loving her rubbing my rosebud and the tip of my cock. “I cant wait to feel you slide inside of me.” Having said that, she slid her finger in my little bud. My cock throbbed and I gasped. Then she slid her little fingernail on the tip of my cock. Like she wanted to slide her finger inside my cock as well as her other finger in my ass.

“I can tell how much you are loving that my boy. Before you know it I will be able to slide my whole fist in your ass and my little finger in your peehole. How does that sound?” She asked.

“Oh Momma! I cant wait.” I gasped out, “I feel like I’m gonna cum any second!” after saying that she pulled her hands away. What a feeling of want and longing once it was taken away from me. I realize I want to do anything for her to feel that again.

“Sorry cupcake, you don’t get to cum yet. Not until you earn it. Not until I say. You agree?” she asked.

“I would agree right away but my sister likes to make me cum sometimes, what about her?” I asked, not wanting to miss out of my footplay with my sister.

“Oh I will talk to her, we will work it out. Don’t worry. Why don’t you think about it for a bit, in the meantime pull up your pants and maybe we can buy you some new panties, come on they are on me.” She said.

I had a lot to think about here. A little mindless shopping would be fun. And of course shopping for panties with a lady everyone will just assume they are for her I’m sure. So we went on a shopping spree.

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