Awkward Stories

44,618 results
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Innocent Nicole Becomes a Porn Girl

by Ernesto_Lyon on Sep 14, 2017
Exhibitionist & Voyeur

Nicole was a good girl, the kind who ate her vegetables, drank plenty of water, and exercised daily. A redhead with eager brown eyes, sharp nose, and a pretty smile, she stood an inch or two over five feet, and typically hid her respectable figure under plain jeans and loose fitting tops. She was to graduate with a Psychology degree in June, with a minor in...

Las Vegas: The Sequel

by gimmie_your_load on Sep 13, 2017
Erotic Couplings

I shuddered with orgasm for the fourth time in under an hour, my eyes locked on the television screen in front of me. The same image that had already given me so much physical pleasure did its job again, and my hips rocked as I rubbed my fingers up and down my clit wildly. I let out a long slow moan of unimaginable ecstasy, certain that my body couldn't take...

Teen Spirit

by bradley_stoke on Sep 12, 2017
First Time

Chris' first time didn't happen until he was nineteen years old. Indeed, until that time he'd never even kissed a girl, though there'd been the odd time when he fancied he'd been close. But nothing he could ever be sure about. He was always very awkward with girls. In fact, he was awkward with everyone. He only had a couple of friends, Pete and Stu, who s...

Justin's Secret Ch. 06

by ameliawrites1 on Sep 19, 2017
Transsexuals & Crossdressers

The following Monday after he went out with Jason, Justin tried to make himself as presentable as possible for obvious reasons. He'd even gone as far as getting up forty minutes earlier without an alarm -- his excitement that he was going to see Jason woke him up as if he was a child on Christmas morning. The pair had been texting almost nonstop the whole w...

Car Accident Ch. 09

by pedic7717 on Sep 1, 2017
Fetish

9th Day "Heavy Duties" It was beginning to dawn when I woke up, by a light push on my head. It took me some time to realize where I was and why I was there. As I was coming to my senses, I remembered that last night I didn't go to bed. As my vision cleared, I saw Miss Kate still sleeping on the couch. Her right foot was under my chin, while the left one re...

Gorgeous Grace

by Daexe on Sep 16, 2017
Mature

Until I'd met Grace, I'd never really been sexually attractive to an older woman, especially those old enough to be my mother. Sure, plenty of older women are attractive, or in some cases, far sexier than their younger counterparts. Perhaps it's an age and confidence thing, I don't really know. In her mid forties Grace certainly was old enough to be my mot...

Choosing a Second Chance

by ScreamngInfidelities on Sep 16, 2017
Romance

Well everyone, this will be the last story I write about Ryan—there are three total, if you would like to check them out. I'll have to look elsewhere for inspiration if I wish to write more; all these memories of him are starting to get to me a bit. All that girly stuff aside, I hope you enjoy this one. It's a little slow to start off, but it's got the heart...

Posture and Imposture Ch. 02

by fireballxl5 on Sep 17, 2017
Loving Wives

I kept replaying what I had seen in my mind - the scene in the forest, with Ben fingering my half-exposed wife to orgasm followed by her giving him a blowjob. It was sexy and exciting almost beyond belief, but it lacked closure. I knew that my wife would not allow penis-to-vagina fucking, but there were a lot of degrees of physical intimacy between what they...

Boston Strong

by sbrooks103x on Aug 20, 2018
Romance

I want to thank my sweet inspiration blackrandl1958 for the kick in the butt I needed to write this story, and for her usual expert editing. ***** My legs were like lead weights as I tried to have something resembling a kick; I kept my head down and powered to the finish line of the Ocean State Marathon in Newport, Rhode Island. It was only as I crossed...

The Birthday Present

by WifeANympho on Aug 22, 2018
Group Sex

John and Amber had been married for over 8 years. They had a great relationship, a wide circle of good friends, and a healthy sex life. John liked to spend time looking at and reading porn. He did not make a secret of this and, at times, even did it when the two of them were sitting in the family room at night. Amber noticed that his favorite "thing" seemed...