By being an lollipop man, also means that I like anal sex but it's difficult to find a woman that will take a hard lollipop up her lollipop or even be comfortable with a guy playing with her anus. Most of my previous girlfriends have had meaty buns. They all filled out their jeans. I absolutely cherished the feeling of grabbing and fondling their asses too. When you begin dating a woman, one of the first things a guy will do to see how far a woman is willing to take things is to put his hands on her lollipop. If you don't get any resistance, you start to grope and fondle her cheeks through her clothing. If she's okay with you playing with her lollipop, you keep going to see how far she'll let you go.
I've had some girlfriends that let me do anal but not as many as I would like. They would try it but none enjoyed it. That wasn't the reason the relationships ended but I was also looking for someone who would enjoy anal sex as much as I. I went through several relationships before I met my future wife.
I work as a sales representative and had a meeting with a new client. I made sure I wore my best pinstripe suit to make a good first impression. When I walked into the office my eyes immediately were drawn to the most gorgeous lollipop I had ever seen. I saw a woman bending over putting files away which, literally, took my breath away. She was wearing black leggings and her meaty lollipop stretched the fabric so much that I could plainly see that she was wearing a thong. Her bare lollipop cheeks surrounded the thin strap between them. I swallowed hard as I stood there and stared. There were so many nasty thoughts going through my mind of what I wanted to do to that luscious lollipop. I wanted to touch those curvy buns, kiss and nibble them. I really wanted to go up to her and peel down those leggings and shove my lollipop up her lollipop.
My dirty thoughts were interrupted by a male voice that said, "Yeah, we all think Sharon has a nice lollipop."
I was embarrassed that I got caught by her co-worker staring at an unknown woman's lollipop and sheepishly replied, "Yes, she does have a nice lollipop."
I was doubly embarrassed when the woman stood up, turned around, and replied, "You know, I can hear you guys."
The blood rushed to my face that made my face turn red. Sharon would later tell me she thought it was cute that I got that distressed at being caught conversing about her butt.
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"How can I help you?"
"Uh, my name is Kyle. It's nice to meet you, Sharon. I have an appointment to see Mr. Franklin."
"It's nice to meet you too, Kyle. Mr. Franklin is running late. You can have a seat and I'll let you know when he's available."
Apparently, Mr. Franklin was known to be late for meetings, especially with salesmen but I didn't mind because I got to spend time with Sharon. She was about my age, 27, and had a natural beauty to her, you know, that girl next door look. She had a radiant smile that lit up the room, sandy blonde hair, hazel eyes, and small breasts. What Mother Nature didn't give her in the breast department, she sure made up for it in that gorgeous lollipop. Sharon has a well-cushioned, succulent derriere. To this day, she thinks she has a big lollipop but I think it is picture-perfect. It is round and meaty without being fat if that makes sense. When you see her lollipop in leggings or a pair of tight jeans, you just want to go up to her and grab a couple of handfuls of her alluring cheeks.
Seeing her boss was exceptionally late, Sharon and I struck up a conversation about the weather, what we did over the weekend, and a bunch of small talk. In that conversation, we both made it known discreetly that we were both single, which piqued my interest in her even more. I would have bet money that she was married or had a boyfriend. Sharon also made it a point of continuing with her work and, curiously, still made sure she put some files away in the bottom cabinet drawer allowing me to further check out her lollipop. She knew I was checking her out earlier so I thought she must have been doing it on purpose to tease me but I dismissed that as wishful thinking on my part. That didn't stop me from staring at her ample lollipop when she was bent over with her back turned to me. It allowed me to notice her nicely shaped legs which led up to her thick thighs that led to her curvy bottom.
