She seemed to be enjoying the conversation, so I took a chance. Now you have to understand… This was more than ten years ago so my memory of this day isn’t perfect, but I think I said something along the lines of, “I don’t want to put you on the spot, but I have a question. If the answer is no, I promise I won’t be weird at the gym… Would you like to have coffee with me?”
She paused for a second, like she wasn’t sure, but then smiled and nodded. I grinned and said, “Great!” and then… well… then I experienced a total brain fart. I proceeded to pull the most awkward move of my life. My mind blanked, I couldn’t think of what to say next, so I panicked and simply said goodbye, then walked off. I was so jazzed up from our chance encounter, my mind racing with thoughts of her, that I even forgot what I was shopping for. About five minutes later I realized with horror that not only did I forget to get her number, I didn’t even get her name!
In a cold sweat, I did a lap around the store but she was nowhere to be found. My heart sank. I wanted to kick myself. Of all the times to be awkward! For the record, I have a long history of being awkward at critical times, but to this day that incident still takes the cake!
There I was, down in the dumps. I checked out my groceries and walked to my car. Suddenly I heard a honk. I turned around to see a car coming up next to me. The driver’s side window rolled down and there she was. She winked and said, “Hey, at least I didn’t hit you this time! Also, I’m Molly.”
It was my turn to blush. I told her my name and she handed me a little note with her number.
Molly smiled again and said, “Don’t forget, coffee…” as she drove away. It occurred to me that she probably waited in the parking lot until I came out. A very good sign!
I tried to play it cool, but I couldn’t wait. I was WAY too excited. I called her that very evening, and we arranged to meet for coffee on Saturday morning.
When the day finally came, she showed up in an outfit that was clearly intended to maximize her assets. She was wearing ass-hugging black tights and a green athletic jacket that was partially unzipped. Her boobs were barely contained by a low-cut sports bra. She was showing so much cleavage that I found it impossible not to stare at her breasts as we talked. I couldn’t help noticing she had those same cute freckles on her chest. I briefly found myself wondering if her boobs were fake like Diana’s, but then I forced myself to stay in the moment and not let thoughts of the past distract me.
We chatted for quite some time. Molly was an avid yoga practitioner and had just landed her first gig as an instructor. Teaching classes was keeping her busy so she’d canceled her membership at my gym. I listened intently as she told me about her life. She had an English degree and was trying to get some of her essays published. I quickly fell in love with her sharp wit and mischievous sense of humor. I told her, in all honesty, that I would love to read some of her stories. She blushed, which somehow made her even more attractive.
Our coffee date lasted long enough that we ended up ordering lunch. Things were going better than I could have hoped. There was so much chemistry between us that I knew it wouldn’t be our last date. When I asked her out again, she didn’t hesitate to say yes.
Our next date was an epic all-day thing. We went to a music festival together. She wore a floppy wide-brimmed hat and a flowing full length green dress to protect her pale skin. The material was so silky that it did nothing to hide her curves, and a few times I thought I saw the outline of a thong through the back of her dress. I couldn’t stop stealing glances at her amazing body.
We drank a lot and laughed even more. When sunset came she took off her hat and I found myself gawking at her. She looked angelic with her red hair haloed by the setting sun. Her smile was so pretty it was mesmerizing. She had full pink lips that I couldn’t help thinking would look amazing wrapped around my penis. I must have stared at her mouth for quite a while because when I came to my senses she was just looking back at me with a wry half-smile.
I apologized. She laughed and leaned in, and we kissed… and kissed… and kept kissing through the end of the show. As the evening went on I got more adventurous and I risked sliding my hands down her lower back onto her buttocks, and sure enough I could feel the outline of her thong. The dress was so sheer it felt like I was touching her naked body. I got rock hard against her and she grinned at me, a mischievous look in her eyes. Just then the final band started their set and distracted us. I didn’t want to push my luck so I kept my wandering hands to myself the rest of the night.
The next day I offered to make her dinner at my place and she said yes. I hardly got anything done at work, daydreaming about Molly and trying to plan dinner. I wanted to impress her but in all honesty it was a bad plan… I wasn’t much of a cook. Eventually I gave up on grandiose ideas and decided to stick to the basics. I went with the only recipe I was any good at, which, I will be honest, was nothing special. My diet at that time consisted mostly of chicken, rice and vegetables because I was trying to get back in shape, so that’s what I made. But I bought an expensive Cabernet, hoping that would make up for the uninspired meal.
That night she arrived wearing a tight blue mini-dress that floored me. I kissed her at the door and had to resist the temptation to tear her clothes off right there.
Dinner went by in a flash, and we moved to the couch with more wine. We were both tipsy. When we sat down I casually placed my hand on her thigh. Molly looked up into my eyes. Without a word we both put down our wine glasses. I slid my arm around her waist and pulled her in for a kiss.
Her mouth tasted like honey to me and her lips were incredibly soft. Our kissing grew more and more passionate and I got lost in the moment. My hand went to her breast almost of its own volition. I squeezed gently and broke the kiss to gasp. Her boobs were firm but, to my great surprise, obviously natural. She wasn’t even wearing a bra under her dress. I’d never seen large breasts stand up on their own like that!
The wine, her lips and her body were making me dizzy. I threw caution to the wind, pulling down the top of her dress to get direct access, and cupped her naked breast again. She moaned into my mouth. I slid my other hand down her side all the way to her waist, admiring her delicious squeezable curves. I let my hand trail further down, over her hip to her outer thigh. I was getting hard against her other leg and she made an appreciative sound in response. She spread her legs just enough that her outer thigh pressed firmly against my erection.
She was driving me wild and she was obviously ready to go, so I grew even more bold. I slowly ran my fingers inward from her hip until they rested directly on her pubic mound. I could feel the heat through her dress. She groaned and arched her hips, pressing up against my hand.
Molly reached down to rub the front of my pants where I was throbbing against her leg, feeling the shape of me with her fingers. She broke our kiss briefly to exclaim, “Oh! Mmmm…”
It was a pleasantly surprised noise, like she was happy with what she found. I grinned and kissed her again, sliding my fingers down until they reached the area where her dress had bunched up between her thighs. I hooked my fingers under the fabric and pulled her dress up to her stomach, then slid my fingers back down over her underwear. I let my middle and index finger rest against her clitoris. Her panties were soaked through, and I could feel her clit throb against my fingers. It was pronounced and firm, larger than most.
My mouth watered. I couldn’t wait to taste her, so I slid down to kneel on the floor and then pulled her thong down past her knees.
I took a second to admire what I saw. She had the prettiest pussy I’d ever seen. Pink and petite, it glistened below a defined and swollen clitoris. Her demure labia were slightly spread. She looked delicious and I couldn’t wait any longer. I slid my hands up her body as I moved in close.
I let the tip of my nose brush against her clit as my hands moved up to cup her perfect breasts. She gasped. I inhaled deeply, taking in her scent. She smelled amazing… clean, almost sweet, with a strong hint of arousal.
I reached out with my tongue and gently licked up and over her pronounced clitoris. Her reaction was very gratifying. She sighed and groaned, sliding her fingers into my hair. I licked again, gently, teasing, then circled around her clit with my tongue, testing the waters.
At this point in my life I knew from experience that every woman is different when it comes to clitoral stimulation, and I was determined to figure out what she liked. Did she want firm tongue pressure, or more gentle lapping? Or did she prefer less direct friction? I needed to know.
As a pleaser, this moment was as exhilarating to me as any part of the hunt. Most men focus entirely on the first moment of penetration. Don’t get me wrong, I loved that part too, but discovering what makes a woman cry out in pleasure was my favorite part. Especially when, in that moment, I could hear surprise in their voice… surprise at how quickly their body was responding to my touch. In my misguided youth, when I was obsessively pursuing women, this was the part I savored most. Yes I was out for conquest, but to me conquest wasn’t about getting a girl to fuck you. It was about giving her more pleasure than she realized she could experience. It was the ultimate ego boost.
Now, where was I? Oh yes, my face was between her thighs…
I flicked her clit with my tongue, kissed it, circled it slowly with the tip of my tongue, then licked it in one long slow stroke. She moaned and said “oh my god!”… I could tell I was doing something right. I kept experimenting, caressing her breasts as I licked, squeezing them gently, then I took a chance and pinched her hard nipples gently. She let out a shuddering moan. I grinned against her mound, then settled into a rhythm, letting her hips and hands and moans guide me, until I found just the right technique. When I did, I knew right away. Her breath caught, her fingers pulled at the back of my head, and she started panting lightly. I flicked her clit faster and a few seconds later she cried out, bucking her hips. I stopped licking to let her recover. Her clit throbbed against my tongue. I thought she would want a break but she surprised me by saying, “More.”
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