Sex Blog Roundup: Virgin Territory

They say you never forget your first time(s): your first flash, your first client, your first anal, your first fuck before a crowd of admiring onlookers ... .good times. In honor of busting cherries, we've scoured the best sex writing on the interwebs this week to bring you bloggers who view the fertile land of sex not just as virgin territory waiting to be plowed, but the object of their manifest destiny in their right to pursue happiness. When you look at it that way, it'd be downright unpatriotic not to do it all. At least once.

It's all "Westward, Hos!" as we join the wagon train with your pioneer Chelsea Girl after the jump.

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Sex Blog Roundup
by Chelsea Girl

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First Client

I wait in the park, on the sidewalk near the transit station, watching businesswomen eat hotdogs. August, still a little warm, I'm still a little jet-lagged from the eight-hour flight last week. Wearing, from the top down: pigtails; genuine-but-off-the-back-of-the-truck Chanel sunglasses; a smirk; orange spandex tank top; orange lacy bra with visible straps; low-slung black skirt, barely covers my ass, two little vinyl buckled straps, three pleats; fence-net stockings; black patent spike-heeled knee-high boots.

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Where It All Began

I was living in a two bedroom apartment in downtown Denver. At the time, I was living with my girlfriend, up on the third floor - the top floor of the building. We faced out back, towards two lush, green courtyards. Towering acacia trees, in their phototropism, pushed their way up and out of the courtyards - reaching for the sun.
And then there were the windows.
All around us they were....

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Interlude: How I Lost My Virginity

I hooked up with JC behind the large shed, and we kissed for ages, fondled and she played the "experienced" hand very well, commenting on my penis so forth, but when I snuck my hands down her pants to stimulate her, she hushed into my ear that she had her "rags" and it probably wasn't a good idea. I stopped, and we continued with various other petting exercises. At the same time I was enjoying it immensely I also couldn't wait to be by myself to regale in its glorious memory, selfishly in the most hedonistic of satisfactory self-smugging ways. My quieter moments of contemplation and theatrical masturbatory activities.

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First Orgasm

I start to exit the cooler, but he comes up behind me and whispers in my ear that he thinks I'm hot. His hands grip my hips and his breath is hot on my neck, causing me to shiver. My clit clenched, and I remember thinking that I might be in trouble. Since I don't move, he leans in and presses his body to the back of me. I can feel his cock against my ass, and he's definitely happy to be there. I took a step back, and let the cooler door close on us.

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Down Time, True Story

TW had finally agreed to do a little flashing, after years of my trying to get her expose herself to others. We were headed down the ramp onto westbound 80. The truckers had spotted us coming down the ramp and had seen TW adjusting the straps of her bikini. I merged onto the expressway and listened as the drivers tried to spot us.
"Where'd she go?", one driver asked.
"Probably out to the hammer lane," replied another.

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Doin' the Butt, Ow!

Much like my most expensive pair of shoes, I really like the idea of anal, but when put to use, it really hurts.
I hope the shoe analogy wasn't too Bradshaw, but it's totally true. And I don't care what people say about getting what you pay for—expensive shoes hurt, even the Tara Subkoff for Easy Spirit wedges that I have. Oddly enough, those were the shoes I was wearing the first time I had my back field plowed.

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I Think It was the First Time...

i think it was the first time fingers were wrapped tightly in my hair while i gave a blow job, that something inside of me snapped open. Those tiny hairs on the back of my neck being pulled, the discomfort from that, the firmness of a strong hand guiding and pushing my face down on a cock. This small act was being controlled, and i loved it.

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Thumbnail via ATK Hairy (atkmodels.com)

Previously: Sex Blog Roundup Archive

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