She Liked It - Kristen

This happened. If you find reluctance off-putting, you may want to pick a different story.

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My first job out of college was at a small technology company. I was 22 and had a steady girlfriend. I quickly became friends with a girl in the office who was just a year older than I was and who was already married.

Kristen, my new work friend, was cute, but a little bit on the plain side, and not someone I'd ordinarily notice. I was happy with my girlfriend, and Kristen loved to go on and on about how amazing her husband was. She seemed to enjoy "one-upping" everyone in the office when it came to her relationship, and how it was so much better than everyone else's.

I'm sure you know the type.

We quickly settled into a kind of brother / sister dynamic, where we'd make fun of one another all the time. While she wasn't my type, I'd still find myself checking out her body regularly, as she was petite and curvy at 5'5", 115 lbs, and had full, C cup boobs.

Within a year I'd started working on a project on the other side of the country, and while Kristen and I would still instant message one another, we weren't as close as we'd been. My girlfriend and I broke up around this time, and I soon left the company altogether.

One day, months later, Kristen emailed me confiding that she'd found out her husband was sleeping with another woman, whom he'd gotten pregnant. She was as devastated as one would expect, and I genuinely felt sorry for her as she went through the divorce process. After a few months she was ready to start dating again, and I set her up with a good friend of mine, thinking they'd be compatible.

Kristen and my friend dated for a couple of months before breaking up. I'd found myself missing my friends back home on the east coast, and moved back after a three year stint out west.

I was grabbing drinks one night with the friend I'd set up with Kristen, and was curious about why things had fizzled out between them. I really didn't think of her romantically, which is why I'd set them up in the first place, but what he told me began to change my perception of her.

Kristen and I would see one another from time to time among other friends, or go out for drinks where she'd be my 'wing woman' and / or I'd be her wingman. It felt very easy and platonic, but I couldn't get what my friend and said about her out of my mind.

She and I were both obsessed with a particular TV show, and had talked about watching it together. I invited her over to my apartment one night to watch the show. She was happy to come over, and I'm sure she didn't think twice about it being anything like a date. I'm still not sure how I was viewing it.

We were sitting on opposite ends of my couch drinking wine and catching up while we waited for the show to come on. I still hadn't gotten her side of the story as far as why things hadn't worked out with my friend, and I had a smile on my face as I started to ask her about it. She gave me the standard, anodyne "Oh, you know, sometimes things just don't work out..." answer but as she noticed my expression she smiled and said "Why? Did you talk to him about it? What did he say?"

I liked playfully mocking her in general, but it felt particularly fun to feel like I "had" something on her. And the wine helped me make the decision to test out a new way of teasing her.

"He said that neither of you was really ready for a relationship, but he also cryptically described you as being 'a lot of fun.' When I pressed him on it, he said that he's never been with someone as sexual as you are, and that you seemed like you were constantly in heat."

Kristen had this endearing habit of putting her hand close to her mouth when she was surprised by something, and she gasped and said "WHAT?!?! He told you that?!?!" She'd drawn her feet on to the couch and had her knees pressed against her chest as her face turned bright red. She was laughing a little, but was also clearly mortified.

"Yeah... he told me that it seemed like you 'needed' it. That you could never get enough." As I continued to smirk at her she covered her face with her hands. I added "judging by your reaction, I'm guessing he was telling the truth."

I'd paused the TV and just let my comments hang in the air while she half-jokingly said over and over words to the effect of "I can't believe he told you all of that!"

Seeing her on my couch, wearing short denim shorts and with her knees pressed up against her chest while her face was covered with her hands allowed me to get a nice long look at her legs and thighs and the wonderfully soft flesh just below her ass cheeks. I also found myself aroused by her vulnerability in that moment, and enjoyed watching her squirm, figuratively.

She composed herself long enough to uncover her face and to take another sip of wine, but she was still blushing furiously while looking away from me with a half smile.

She said "Let's talk about something else," and I continued smirking at her and replied "Why? We're just two friends talking. Who knew you were so much fun!"

When she continued to quietly look away with a half smile on her face, I decided to raise the stakes to see how she'd react. And, to be honest, I felt like I knew her well enough to know just how to manipulate her.

"The walls here are pretty thin so try to keep it down. You trust me, don't you? Relax, there's something I'm curious about, and I'll stop in a minute."

She turned to look at me with a bewildered expression, and before she could say anything I casually came across the couch to grab her by her bare ankles, and pulled her towards me in one motion so she was laying flat on her back while I positioned myself over her.

She looked shocked and quietly said "omg what are you doing?!?!" I knew she wouldn't want to draw attention by crying out, especially after I'd just commented on the thin walls, and I also knew that deep down she trusted me.

I had her arms pinned down over her head and started to put my weight on her. I shushed her and said "Just relax, I'm not going to do anything." I was already turned on from talking about her sexuality and seeing her reaction. I stared at her and smiled knowing she was starting to feel my big cock getting bigger and harder against her.

She was looking away from me, red as a beet, and was clearly embarrassed.

I leaned down and whispered "Who's bigger?" as I started to slowly grind against her.

She'd gone from squirming figuratively to literally, but I was enjoying watching her still not wanting to give in.

Her breathing was getting shallower and she said as she looked away from me "I don't think we should do this." I kept smiling at her and teasing her by saying "We're not doing anything... I just asked you a question. I think you know the answer, I just want to hear it from you."

I could smell her arousal at this point. But I didn't want her to give in. So as she breathlessly said "You're bigger..." I pushed myself off of her and went back to my side of the couch, grabbed my glass of wine, and took a sip while doing my best to act as if nothing had happened.

I think this surprised her as much as anything. She was still laying down but propped herself up on her elbows and asked "what are you doing?" to which I responded with "nothing! I was just fucking around."

She stared at me in disbelief before saying "You're so mean" while looking annoyed.

"How am I mean? I didn't do anything."

She repeated "You're just... mean."

Kristen had drawn her knees back up against herself while sitting up, and I teased her by saying "you're so wet right now aren't you?"

When she didn't respond the second time I asked her the same question, I climbed back over to her side of the couch and yanked her legs back towards me. This time she kicked a little, but I quickly forced myself on top of her again with my 6ft, 200 lb well-muscled frame. She was staring at me now with a combination of anger and lust. I told her she needed to just go along and not cause a commotion as I started unbuttoning her small, tight shorts with one hand. When she tried to stop me I grabbed a fistful of hair and pulled hard enough that she brought both of her hands up to her hair to ease the pressure. It gave me the chance to use my free hand to unbutton her shorts and I then let go of her hair so I could yank her shorts all the way off of her with both of my hands.

I was now kneeling on the couch looking down at her splayed, naked legs revealing a bare and desperately wet pussy. Seeing her still wearing her small t-shirt only further emphasized how vulnerable she was between her legs. She was breathing very hard.

I was too turned on at this point to continue playing games, and needed to be inside of her. She quietly complied as I leaned down to scoop her up into a fireman carry and threw her over my shoulders on the way to my bedroom. I tossed her onto the bed, told her to keep those legs spread nice and wide, and undid my pants while she stared at me expectantly.

As I mounted her again I slid the fat head of my cock up and down her wet slit and whispered in her ear asking her if she always gets this wet. She was just moaning and whimpering at this point and pleading with me to fuck her. I slammed my cock all the way into her as she let out a gutteral "unghhhhhh." Grabbing a fistful of her hair, I slowly slid all the way out and all the way back in as she began pleading "please I'm going to cum I just need to cum please please please fuck me faster!"

Hearing her desperately beg for my fat dick I knew that I wouldn't be able to hold out much longer myself, and I started to jack hammer away. Within minutes I felt her body starting to convulse beneath me, and I pulled harder on her hair as I felt her cumming all over my dick. I subsequently shot my load deep inside her with one of the biggest orgasms I'd ever had.

We were both nice and sweaty at this point and I collapsed on top of her.

In the ensuing, slightly uncomfortable silence, I found myself thinking that it was odd that her t-shirt was still on. As I started to absentmindedly lift it up to take it off she tried to pull it back down. I told her the modesty ship had already sailed, and that I wanted to see those bouncy tits. She wouldn't look at me but didn't try to stop me from sliding it up over her head and taking it off.

Or when I took off her bra to suck on her tits.

She was still facing off to the side when I looked up and decided to kiss her neck and her ears. Watching her ignore me and just "letting" me do what I wanted was turning me on again, and I could feel myself getting aroused as my mouth made its way closer to hers.

Feeling my cock grow bigger and harder as it made its way back towards her cum-soaked pussy, Kristen turned to face me, let out a soft moan, and started to kiss me back.