She was the sexiest, nerdiest, most awkwardly adorable Doctor in the world and we fucked like porn stars [MF]

I was dating a lot. OkCupid was my dating site of choice based on the raw number of people, the ease of use, ample photos, and profile sections which let people highlight the things that they liked about themselves the most. I met at least a hundred women over the course of eighteen months. Most I would categorize as wasted effort on my part — just a drink at the bar, a walk in the park, or some other meet-and-greet leading to an obvious lack of chemistry or interest. There were a few people that I met that led to some short or long-term friendships. Then there were a bunch that led to a good fuck. This is one of those fucks.

She was really, really cute. 5’2”, auburn hair, blue eyes, nice smile, petite frame. She was studying to be a doctor — both an MD and a Phd — and was one of the most brilliant people I ever dated. That said, she was also one of the most socially unaware people I ever dated which is the main reason things never went anywhere.

Our first date had been eventful, but not in a good way. Sure, she was cute and a little feisty, but I wasn’t into her. We had gotten a few drinks at a spot two blocks from my apartment and her awkward energy wasn’t speaking to me. My neighborhood got a little iffy at night so I offered to walk her to her car where I was intending to thank her for her time and let her know I wasn’t feeling the chemistry. Well, her car was gone. Completely missing. Vanished. We uncovered it had been towed away because she parked somewhere she should not have. I felt horrible, so I spent the next few hours tracking the car down, taking her to the impound, loaning her a few hundred dollars and getting it back.

As you might guess, I did not tell her there was no chemistry since she owed me $400 bucks. Also… she was chill as hell the whole time. 99% of the people I had dated to that point would have lost their absolute mind in that situation, but she was calm, patient, and cool the whole time. I was intrigued and decided that I could look past any initial first impression I wasn’t vibing with.

Our second date — where she promptly repaid me and offered to take me out to dinner as a gesture of kindness — was really nice. I decided that I was interested and made a move as we reached the front door of her house. She responded with enthusiasm and she was an incredible kisser. Her almost manic energy was unbridled as she pulled me into her foyer and invited me to her bedroom. I was thinking it was going to be a long game of dating to get her to bed — this was a very welcome surprise.

We skipped the nickle-tour, roommate introductions, and any other standard ‘hey, this is my house’ stuff that people normally do and headed directly for her bedroom. Her eagerness was incredibly sexy and I was getting more and more turned on by the minute. As soon as the door was closed and locked she told me how glad she was that I had kissed her.

“So, I really, really wanted to thank you for being so awesome the other night.” She reached for my belt and began to undo it. “Dinner was only the first part of me thanking you.”

“Oh yeah?” I grinned slightly — but I was barely holding back the ear-to-ear smile that really wanted to show up.

“Uh huh.” She started to undo the button and fly of my pants. As my jeans hit the floor she got on her knees, ran her hands down my legs, and began to kiss my cock through my underwear. “Is this okay?”

“This is very okay.” She pulled down my boxer briefs and my cock was as hard as rebar and finally free.

“Oh my god, you are so big.” Her eyes got wide as she blurted that out. She didn’t say it in a sexy way, it was very matter-of-fact. I still liked hearing it. “I don’t think I can get it in my mouth.” She made her attempt anyway and she was successful. Her tiny hand wrapped around the shaft of my cock and she got at least two inches of me into her mouth. I moaned for her as a little encouragement and told her how sexy she looked with my cock in her mouth.

I sat down on the bed and she continued to blow me. She was deeply enthusiastic, but not the most gifted person to take me in their mouth. I realized very quickly that she was the kind of person that would take instruction and constructive feedback very well. I started to offer pointers, hints, and personal preferences and she added them to her actions immediately. I knew she wanted to make me cum, but that wasn’t going to happen from head and instead of skirting around it I decided I would just be blunt.

“That is fantastic, but I can’t cum from a blowjob.” Not entirely true, but in essence it was. “I can jerk myself off if you want to watch?” I offered as an option.

“Is there anything I can do that will make you cum?”

“Just sex.” I said it in an ‘I know that is jumping the gun, I’m not trying to push my luck for tonight’ kinda way.

“Oh, great, do you want to have sex?” She asked in in the most confusingly innocent way.

“Uhm, if you do, yeah. I’d love to eat your pussy.”

“Ohmigod, I would love that.” She stood up and started to get undressed. I was blown away. Her social awkwardness was actually an amazing character trait apparently. She had a great body, much bigger tits than I expected, and a firm ass. I took one of her little pink nipples into my mouth and swirled my tongue around it as I grabbed her butt with both of my hands and squeezed. She moaned — loud. I kissed my way across her chest to her other nipple and did the same, then worked my way up her chest to her neck. She was panting for me. I started to run a hand up her leg until I found the wetness of her pussy with my fingertips. She melted in my arms.

“You are so fucking sexy.” I confessed. “I want to lick you so bad.”

“Yes, please. I want to feel your tongue.” She whispered back with lust.

I picked her up off the floor and placed her on the bed. She pushed her pillows out of the way and spread her legs for me showing me her cleanly shaved pussy, dripping with her sex. I got on her bed and kissed my way down her thighs. When I found her pussy I extended my tongue and flicked the length of her slit. Her pussy tasted wonderful and she let out the biggest moan for me as she reached down and grabbed two fistfuls of my hair.

I liked her at this point. I acknowledged how wrong I had been about her and was looking forward to wherever this would go. I really liked the way she responded to the way I ate her pussy. She was very vocal and very physical. She moved her hips where she wanted them. Grabbed my hair and moved me where she wanted me. Told me what she wanted when she wanted it. All very hot. I made her cum and she told me not to stop, so I just kept going and she came again, then again.

I wanted her bad at this point. She was so wet, and her pussy was so tight on my fingers, that I just need to know how she felt. I moved up close to her and presented my cock like a trophy. I always enjoyed showing a woman how deep I was going to be inside them by placing myself on top of their mons. With her tiny frame it looked like I went from pussy lips to belly button and it was glorious. She got a condom for me and I put it on deftly. It was tight and a little uncomfortable, but I didn’t care. If she fucked as good as she got licked it was going to be a fun time.

I spit on my cock and rubbed it over the condom to get it wet before starting to rub the head up and down her slit. She was staring intently into my eyes, but that isn’t what I wanted her to watch. I demanded she watch me enter her and she changed her gaze right away. I alternated between watching her face and our combining sex trying to decide which was a hotter sight. Normally, I preferred to watch as I entered someone for the first time, but her reaction to watching me was infinitely better. I could tell that it hurt, but in the good way… the new worthwhile experience way.

We started to fuck, but her pussy was so tight, and she clamped down so hard with her vagina, that she pulled the condom off of me. We got a new one and tried again with the same result. I told her that I wanted to fuck her faster, but that I would need a bigger condom next time; so this time I would just have to go very, very slowly.

With the third and final condom on, I did just that. I moved so slowly and deliberately it was like we were making love and not just fucking. We made out the whole time and it was very tender and actually quite nice. It took a long time before I felt like I was ready to cum, but when I did it was incredibly satisfying as she came with me at the same time.

We agreed to see each other again in a few days, she had a lot of work at the hospital over the next few days and wouldn’t be available. I was eager to fuck her again, but understood the importance of her work. She did spend a lot of time sending me naughty text messages and emails, however. One of my favorite things that she said was a post script to an email exchange we were having about our time together and how she couldn’t get me out of her head: “Ps – is this feeling of utterly insatiable lust what its like to be a teenage boy?! Because if so, how the HELL do we ever expect them to pay attention in school?”

Over the next few weeks we got together several times and had several awkward / amazing dates. The two highlights that stick out in my memory are the following. The next time we went out, we went back to her house again afterward. I met her roommates and got the full tour the second time before we retreated to her bedroom. She had gotten some magnum condoms for me and we thought that would cure the problem we had before, but it didn’t. Her compromise was to just let me fuck her raw. It was a very good compromise.

We had incredible sex that night. I took her fast and hard in every position. At the end, after I had made her cum several times, I asked if I could cum on her face. It wasn’t necessarily my thing — I had a thing for cumming on tummies — but she agreed. I wanted to cum on her glasses for whatever reason, so she put them on as she got on her knees in front of me. I unloaded hard all over her pretty little face and glasses. She responded well to it and I was in heaven. She later wrote in an email to me “I’m being bad again but I can’t seem to help it… I was just thinking about the time when you wanted to cum on my face and how surprised I was when I really loved how hot that was.”

The last big highlight was a few dates later when she came to my apartment on the other side of the city. My roommates were out for the night and had just left a few minutes before my date arrived. She had told me once, in passing, that she had always wanted to be fucked against a wall. Unfortunately, none of her prior boyfriends were quite large enough or strong enough to manage the task. I knew when she said it that I was exactly the type for it, so when she walked in the door of the house, I closed and locked it, then grabbed her purse and tossed it onto the couch.

She looked at me questioning ‘why?’ as we were supposed to be going out. Then I started to undo my shirt and tossed it aside as well. I reached over to her and started to strip her right there in the living room. She caught on and we were both completely nude in a matter of moments. I started to kiss her and finger fuck her where we stood. Then I moved her over to the armrest of the couch, sat her down, and pushed my hard cock right into her. She gasped and I fucked her just a little bit to make sure my cock was completely wet from her juices. Once I was happy, I picked her up and she wrapped her legs around my waist and her arms around my shoulders.

I walked over to the front door of the house — the only wall space not covered with art or blocked by furniture — pressed her into it, and began to fuck her like an animal. I was incredibly fit and very focused, so I was able to maintain that position for quite a while ensuring that she came for me. I then moved us to the shared living room couch and she rode me in a reverse cowgirl as our combined wetness dripped out of her pussy, down my legs, and onto the hardwood floor.

She reached down and fondled my balls — no one had done that before and it surprised the hell out of me. “Oh fuck!” I cried out.

“Are you okay?”

“Oh my god, yes, that is going to make me cum if you keep doing that.”

“Good.” She moaned for me as she reached back down to do it again.

“No, really, I’m going to cum if you keep doing that.”

“Cum in me.” She responded and that was that.

I started to cum inside her pussy for the first time as I bucked my hips harder and harder. When I was done she jumped off of me, got on her knees, and sucked my cum and hers off of my cock while I watched in shock and amazement. She told me later that she had watched a porn the other night while she was masturbating and saw someone do that. So, since I had given her what she had always wanted, she wanted to give me something special from the porn.

We fucked twice more that night and didn’t end up going out as planned. We dated for a little while, but I ended things one day when work became particularly stressful for me. She would email me late at night sometimes and tell me she was using her vibrator on herself while she thought about me. It led to a few random hookups over the next few months until she started seeing a guy more seriously. She wasn’t the one for me, but I think of her often and miss her sex all the time.

Source: reddit.com/r/gonewildstories/comments/n9w03e/she_was_the_sexiest_nerdiest_most_awkwardly