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Awkward Stories

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Nerdy Girl Episode 5: Choose Wisely

Her virginity gone, my nerdy friend presents choices as to how to help her become more adventurous.

Kathryn and I walk out of the bathroom into the bedroom, still naked from our post-shower sex. I find my clothes while she digs into a drawer and puts on fresh panties and a bra. She steps into a pair of pants and rummages through her closet for a shirt w...

A Great Day

Clay finds his true love.

Slowly I raked the leaves out of the pool, my mind occupied. I heard the chatter of Carlita, my stepdaughter, and Bradley, a supposed friend. They were in the hot tub. It was a cool Saturday morning, and I was getting the pool ready for summer. My name is...

Nerdy Girl Episode 3: Staying The Night

Why not spend the night with the nerdy chick who just gave me her virginity?

I looked at Kathryn in my groggy state, trying to figure her out. Was she offering to put me up for the night because she was concerned that I might fall asleep and wreck out on the way home... or because she was getting addicted to sex and wanted to try...

Nerdy Girl Episode 2: A Second Serving

The nerdy girl's first time was quick. But what did she say about “again later"?

Dinner was done cooking, but needed to rest a while before cutting into it, so Kathryn and I chatted some more. “I'm glad you enjoyed having sex with me,” she told me, awkwardly. “Ummm... yeah,” I replied. “It was a bit of a shock you asking, to be honest...

The Passed Note

Will love have a second chance to bloom?

  Ten years earlier…   I plucked up my courage and stepped in front of Alison as we filed out of the Year Nine Civics class on the last day of term before the winter holidays. In my hand was a handwritten note, folded up. I called for her attention and th...

New Year’s Eve

The last night of the year is a time to reflect on the past… and make good the future.

Eve. A name that, for three years, had sent my head and my heart on a rollercoaster. The simple mention of her would evoke a flurry of emotions in me, of joy and of pain. How could a girl of such sweet disposition have me cursing her existence, other than...

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The Babysitter II: Distraction

After a frustrating failure, he needs a distraction. She knows what he needs.

When I woke up the next morning, I first had to recall where I was and how I had ended up there. The environment seemed familiar, yet unusual. That was until I vaguely remembered I was lying on the living room couch—alone. Drowsy as I was I tossed and tur...

When Social Misfits Find What Fits -- Part 1

Our heroine reveals the tawdry inner secrets of a woman who rejects the pursuit of social status.

I think we all know that one strange nerdy girl that's a little twisted, maybe even a little too insecure and bordering on scary-desperate. Like Michelle, the flute playing, band camp character from American Pie, or maybe more like Osgood, the scarf weari...

My Wild Anal Exam, Part 2

Part 2 of the true story of my doctor's awkward exam

I didn't think I could take any more of this embarrassing ordeal, but the doctor told me he needed to examine farther in than his fingers could reach. But none of his instruments would suffice, as they weren't biological or whatever, and my body in its cu...

My Wild Anal Exam, Part 1

The true story of my doctor's unusual exam that made this straight college boy very uncomfortable

I was having some weird pains and my roommate convinced me to see a doctor. So I found one and made an appointment to have it checked out. The doctor was very friendly, and he had a way of putting you at ease and making you feel comfortable. He was probab...

Two Best Friends (chapter one)

Two best friends have their first sexual moment

Josh had just gotten home from school, which was a 8 minute walk for him. His Josh and his mom lived in a three bedroom apartment. He set his book bag next to the door, heading to his room. He hopped onto his computer chair, wheeling over to his bedroom d...