[MF] My Shy, Nerdy Date Secretly Loves Anal Sex

I've been thinking a lot about a girl I dated for just a year, back when I was in my late 20's. I'll call her Claire. She was a shy girl, with a small waist and petite hands and feet, but curvy breasts and hips, especially on her frame. She had a heart-shaped face and wore her bleach-blonde hair just to her jawline. Claire spoke quietly and didn't like to talk about herself without prompting. But early on I was pleasantly surprised by how open she was in bed. I think, for Claire, she felt more comfortable expressing herself sexually. Once we had our clothes off and we were under the sheets (or against the wall, or on the kitchen counter, or on a walk in the woods…) she revealed a whole other side to herself.

This is a story of when I first discovered the other side of my shy, nerdy date.

I'd gotten to know Claire online, and we'd traded messages back and forth, mostly about nerdy topics like comics and video games. We'd met up for coffee, too, but I could tell that Claire did not want to be pushed into anything too quickly. Sexually, we hadn't done much, other than making out in the car and once masturbating together online.

My roommates were going to be gone for the weekend so I invited Claire to stay over for the night. I offered to make her dinner and drinks, and we'd watch some Studio Ghibli movies.

Claire came over dressed in a tight t-shirt and black jeans. She had on large glasses that made her eyes look even larger. I couldn't help but kiss her right there against the door, and we made out for a while before she even came inside.

All during dinner and the movie there was that great energy where you just know you're going to fuck for the first time. Claire and I kept laughing, touching each other. Every time we passed each other we'd kiss. We put on How's Moving Castle but didn't make it even halfway before we were half-undressed, kissing and touching each others' bodies.

I led Claire to my bed and we kept making out and undressing. Claire had these amazing full breasts with large nipples, I sucked on them while touching Claire through her little white panties. She was already incredibly wet.

Claire laid down on her belly and pulled down my boxers. She sucked my cock and I held her head while admiring her small body and round ass. When I couldn't stand the pleasure any more, I laid Claire back on the bed and we fucked. For being a shy girl, she was so fun in bed. She loved to talk dirty, whispering in my ear to fuck her harder, deeper.

We wound up in doggy style. Claire's pussy was so wet, an she kept touching her clit, shaking as I pounded her from behind. I was admiring her little pink asshole when she reached back and started fingering her ass! I asked Claire if she wanted me to fuck her ass, and she practically shouted yes.

And let me tell you. If Claire was a dirty talker before, anal sex brought her to a whole other level. I was so glad my roommates were not home because Claire was moaning and begging me to keep fucking her and even calling me Daddy (which is a huge fucking turn-on for me).

Claire had been fingering her asshole using her own pussy juices as lube, and my cock was so wet that it just slid right in. I loved watching her asshole stretch over my swollen head and the girth of my shaft. Grabbing her big ass cheeks and spreading her, driving her into the sheets, hearing her moan and cry out for more. Even now typing this up I'm getting hard, but not as hard as I was when I was fucking Caire in the ass. I could have drilled into concrete with my dick.

Claire came, rubbing her clit as I fucked her ass. I did not last much longer. Claire told me in no uncertain terms that she wanted me to cum in her asshole, and I shot load after load into her.

As we spooned together on the bed, shy Claire returned. We'd kiss and snuggle and laugh.

I dated Claire for about a year before she moved. We had some of the best sex of my life, and I loved knowing that behind the veil of this shy, nerdy girl was a wild woman who would push my boundaries in the bedroom and make me cum time and time again.