She Overcame Her Shyness [MF]

I was just getting ready for my third date with Kassandra, or Kass as everyone called her, and I was excited about the prospects of the evening. She lived about forty minutes away, but happened to be in my neighborhood that day visiting with a friend of hers, so when she was done hanging with her she had called me asking if I wanted to get dinner. I was loopy about this girl – she was smart and witty, she had a real affinity for literature and writing like I did, and whenever we talked time melted away and we ended up just picking each other’s brains for hours. That was mostly what our dates up to that point had been, bar one night where we shared a brief kiss. Kass had warned me when I first made my move that she was a shy person when it came to intimacy, and to make matters a bit more complicated, I had been dating another good friend of hers when we met at a Halloween party that previous October. Shortly after that the relationship had ended, and when my paths crossed paths with her again a few months later, I had made sure to clear things with my ex before I asked Kass out. My ex said she didn’t have a problem with it, but Kass still had some apprehension, not wanting to step on her friends toes and risk harming their friendship. This level of consideration only made me like her more.

When I met up with her for dinner I hadn’t expected much in terms of physicality, though of course I was hoping for it. Kass had a body type I was a real sucker for – she was about 5’4″ with something of a flat chest but an ample ass and great thighs. To top things off she was a blue-eye blonde, and almost never didn’t have a wide, friendly smile that made her seem very warm and soothing. To fit her personality she looked overall bookish, the type of girl you had no trouble believing was well-read and thoughtful. But I wanted to respect her boundaries and so had resigned to maybe only a kiss goodnight again.

We got together for sushi, and right away I felt something a little different from her. She was getting much more comfortable with me in our conversations, and after we were done eating she had moved from her side of the table to mine to be closer to me. We talked so long the restaurant closed up and kicked us out, so we decided to walk over to a nearby bar and have a drink to keep talking. After another few hours of just chatting, we again got kicked out as the bar started to close up. Still wanting to be in each other’s company we opted for just sitting in my car in an empty parking lot, still rambling on.

I don’t remember who started it. But almost suddenly during our conversation in the car we had just grabbed each other’s faces and started kissing, all the passion that had been building up between us over the hours of just talking rushing out. It got intense very quickly, and she shocked me by at one point taking my hand off her cheek and guiding it down her body to her nice, round ass. I squeezed it hungrily through her jeans and groaned as she, in the most confident voice I’d heard her speak in, said softly, “I’m proud of my ass,”

“You should be,” I replied, laughing a bit on the inside, as I could still feel a little bit of naivety and inexperience in her dirty talk. But I liked that aspect too. Though Kass was twenty-two and had made mention of an ex or two over the course of our extensive talks it wouldn’t have surprised me if she was a virgin. Either that or she just wasn’t used to taking the lead in situations like this. I happily massaged her ass and she clearly enjoyed it.

Not too long after that I had unbuttoned her blouse and was caressing her small breasts. Upon my first touching them, she had said self-consciously, “I’m sorry there’s not more there,” to which I assured her she had nothing to apologize for, and I really meant it. I like big breasts as much as everyone, but sometimes smaller breasts just complement a woman, and this was definitely the case with Kass. She was definitely no more than an A-cup, and had what only can really be accurately described as eraser nipples. This was my first time encountering them in person, and it made me all the more eager to get my hands – and mouth – on them.

She was breathing hard after I had gotten her blouse and bra out of the way and gently started licking and sucking on her right nipple, at the same time using my left hand to roll and pinch her left nipple. We had lain the seats in my car back and she was sort of lying in my arms, fingers running through my hair and occasionally grabbing it tight as I sucked on her tits, trying to give equal attention to both. “I didn’t know I liked this so much,” she breathed.

As much as we were both enjoying ourselves, we realized we had to call it a night as it was at this point close to 3 AM and we both worked the next day. I was tempted to ask her to just come spend the night at my house, seeing as it would have saved her a drive, but decided I didn’t want to push my luck that night too far. And besides, breaking through as many barriers as I did seemed like enough of a success for me for now.

The next day I was texting her while I was at work and she at one point actually thanked me for the “nip stimulation” I had given her. Her apparent innocence just delighted me, and I was happy to be the one to seemingly break her out of her shell. Due to both working, we didn’t see each other for a few days, but made plans to get breakfast that upcoming Saturday. She had picked up a midday shift at her job that day so we didn’t have a lot of time, but I was willing to take all I could get.

We had a nice breakfast that morning, talking endlessly as we were want to do, and followed that up with sitting down in a coffee shop chatting more. We were getting closer and closer to the time where she’d have to leave for work, and after checking the time she asked me, “Is it okay if we go back to one of our cars? I thought we could do…something else,”

I knew what she was asking but decided to be something of a tease, “Oh, what did you want to do?”

She immediately turned beet-red. It was beyond cute. “I just thought…we could do something else before I go to work,” I laughed and asked her again to tell me what she wanted to do. She looked away shyly and didn’t say anything, and I thought for a moment that may have made her too uncomfortable but she still had a smile on her flushed face when she turned back to me and and just said, “You know…”

We got up and left and walked to her car in the parking lot, so she was in the driver seat this time. It was maybe a bit after noon and there were still plenty of people and cars around. We got into her car and I maybe assumed we were going to take it somewhere a little more out of the way, but she basically attacked me and kissed me hard as soon as the doors closed. There was even more fire to her this time, and she stuck her tongue in my mouth first thing.

“Grab my ass again,” she whispered to me, and I happy obliged her. Today she was wearing shorts, and I ran my right hand up her thigh and stuck in the left leg and was surprised to find no underwear underneath. I started kneading her left cheek and she started making soft moans into my mouth as we kissed.

“We’re so exposed here,” I said, suddenly feeling like shy one.

“It’s okay, I think I like being exposed,” she replied, and to emphasize her point she pulled down her sleeves and then her shirt and bra to expose her tiny tits. I was floored.

“You must be excited!” I exclaimed, and she responded by reaching over to start rubbing my obvious erection.

“I guess I’m just a hornier person than I thought,” she said, and as she did she started undoing my fly. I shifted in my seat to make it easier for her as she leaned across the console, moving herself so that she could get into a comfortable position. She had taken my aching cock out, and stroked it a few times while looking at me with these doe-like “fuck me” eyes.

“Tell me what you want,” she asked, and I was unsure if she just wanted to hear it or if she was slyly getting me back for teasing her earlier at the coffee shop.

“I want you to suck my cock, Kass,” I replied, stunned that I could manage to get that out, my mind was reeling so hard. She obliged and took the tip in her mouth. I turned my hips towards her so I could slightly thrust into her mouth as she sucked me. If she didn’t have a lot of experience, I could no longer tell. She sucked my dick with effort and vigor, in the front seat of her car parked in a public parking lot. At any time people could walk out of the businesses around us and there was a very good chance that if they looked the right direction they would have seen this bookish blonde girl sucking cock in broad daylight.

This all was vaguely running through my head as it happened, but what interested me more was the position she was in had her bent over in a way where I could still reach over with my left hand and play with her ass under her shorts as she bobbed up and down. I gave it one or two soft slaps and she seemed to enjoy it, giving off softly muffled grunts. I knew I was getting close and that we couldn’t carry on like this for too long, the risk of being caught an ever growing concern on my mind. But I decided I would take one more chance for myself, and I ran two of my fingers over her hot, soaking pussy, just needing to feel her wetness and know she was craving me. Being able to feel the slick lips and soaked bit of hair she had above her slit was enough to send me over the edge. I told her I was going to cum and she took as much of my load as she could, removing her mouth before I was fully finished and making a little bit of a mess on my pants and her passenger seat. She took a moment to swallow, putting her top fully back on and reaching behind her driver’s seat to grab a box of kleenex and offering it to me. We used them to clean up as much as we could, giggling at each other over our mischief.

“Now I’m going to have to go to work all stimulated,” she said, and I laughed at how she could have just swallowed my cum in her car and still opted to say that instead of just horny. I told her this and she just smiled a shy smile and said, “I guess I’m just leaning things about myself,”

Source: reddit.com/r/gonewildstories/comments/l3j67q/she_overcame_her_shyness_mf