I am generally a good judge of character and can tell who I can poke fun with and who to steer clear of. My house is in an area with very little traffic. On warm mornings I take walks down to a skimpy male bikini and like to tan on my fenced-in deck in next to nothing or completely naked. I also get to see ladies in well-fitting attire as I drive or walk to work, which is always a plus. Every now and then I come across a woman who is special in her own way and has a little devil inside of her. Such was the case at the local grocery store.
Sherry was at the register checking out my items and we talked a bit. A short redhead with a wink in her eye for any male who is on the fun side. After a few shopping trips, I gave her a note to read at her leisure. She thanked me and liked my letter.
Over time, I gave her more letters, confided different things to her and got a bit spicier. She eventually began handing me notes and we looked forward to the exchanges. There were days when I would not have a note and she would be upset. If I did not get one from her, it didn’t bother me much. Her face would light up when I handed her a note and I always smiled when she did the same. Always nice to see – just as much as how her cute little ass filled out her jeans.
One of her workers saw me talking to her and got upset. “Okay, young man. Behave or I will beat your ass!”
I laughed it off, but did mention it to Sherry in my next note, adding that a former co-worker did spank me and that I was a bit scared when she said that she had forgot her paddle. I also added that even though I was thirty at the time, I told my mother and her response was that any woman is more than welcome to do this with her blessing.
She replied back and made me hard as I read it.
“Don’t mind Susie – she is more into public humiliation. I could never do that. However, don’t be so sure I wouldn’t punish you. In private and between us. And, to play into our little joke, definitely bare! I would want you to get the full experience. I don’t want to inflict ‘real’ pain, but rather just a slight sting. And, as an FYI, I would use my bare hand on your bare behind. I think you would like that – far from being ‘punishment’. I’m sure we could make time to do this, if you dare. Also, your mother is correct – you deserve all the punishment you get! Punishment doesn’t always have to be in a physical sense, either.”
Upon my next trip to the store, I snuck a note to her, which included my address and phone number, letting her know that anytime she needed a good laugh, she was more than welcome to stop over. I hinted that my place was quite private and that nobody else could see us unless they were true perverts, knew where I lived and how to spy on me. And, sure enough, my phone rang within a few days. It was Sherry. She wanted to stop over, check out my pad and get to know me better. As I was hearing this from her I became super-charged and went to the restroom to release my sexual urges as soon as we hung up.
She arrived on time and I had my place all set up. She liked what she saw. I wore jeans with a male thong beneath so that they fit my form. Her jeans hugged her caboose, as well. We talked as I gave her the ten-cent tour. As we made our way to the back, I showed her the deck and joked about what I often do.
“I like to tan in the nude.”
“What if someone sees you?”
“Then they see me in all my glory, so what?! Plus, it is my place, not theirs.”
She blushed at the idea of me naked. I decided to show her my collection of bikinis, thongs and the like. Her eyes lit up as I teased her with the idea of me modeling them for her. I then told her that I was wearing a certain one under my jeans as we spoke.
“Yeah, right. Prove it!”
Without hesitation, I unzipped my jeans and lowered them to let her know that I wasn’t bluffing. I then turned around and bent over as if to invite a spanking. She gave me a mild slap, which did provide a ‘slight sting’, just as she had said in her letter. She also dug her nails into my ass check and pinched me, sending waves of pain thru me. I became quite hard as she did this, but luckily she did not see this. I then pulled my jeans up and secured them.
“You certainly are a naughty boy, David. Just like I always thought you were. And you did need punishing! Did I hurt you?’
“No, although your pinching me did catch me by surprise. Still, I’m sure you could do better over time.”
She blushed, spun me and swatted my jean-clad behind.
“Thank you, mommy.”
“What did you just say?”
“I said “Thank you, mommy.” You swatted me on my bare ass and that’s what a mommy does to her naughty boy, right?”
Seeing the look in her eyes made my comment worth it. She is a few years younger than me, but it didn’t matter.
“Yes, Davey, and you deserve much, much more. After all, Mommy knows best.”
I don’t like being called ‘Davey’, but decided since I called her ‘Mommy’ that it would be okay, but just from her only.
We agreed on no sexual conduct, although her swatting me ‘counts’, nonetheless. I gave her cute ass a gentle pat over her jeans, as well, causing her to blush.
Before leaving, she gave me her phone number and address, as well. When I went by a few days later, I noticed that it is on a side street, while still in a somewhat busy section of the area. She included a line that made me climax as soon as I read it.
“Just remember, Davey, that if you ever visit me, I can do whatever I please. Your house, your rules and my house, my rules.”
The idea of stopping by her place did interest me and who knows what sort of naughty fun we could get into.
And thus began what has turned out to be a fun friendship…