Sex Diary: Playtime With A Pen Pal

Welcome to the Frisky “Sex Diary,” in which an anonymous person shares the details of her sex life over the course of a few days. Sometimes these entries are filled with revealing romps, while other times there is nary a naked moment in sight. Some of these diarists are frequent contributors. Want to share a page from your sex diary? Email diary@thefrisky.com. All entries will be anonymous.Diarist: An unattached, straight freelancer in her early 30s living in New York City

Back-story: I met Back Pack Boy (hereafter referred to as BPB) last summer when I interviewed him for work. We met on a park bench in Central Park. It was a scorching and unbearably humid July afternoon and I felt about as sexy as a truck driver. My face was sweating, my feet were smelly in my flats, and I was too hot in the shower to shave my legs. BPB showed up wearing all black – T-shirt, jeans, combat boots, and an extremely heavy backpack. He was cute, but clearly young and just out of the womb of college life. Plus, I haven’t slept with a guy with a backpack since the late ’90s … unless it was carried for the sole purpose of protecting his beloved MacBook Pro. But still BPB was on to something with those intense brown eyes and the little mole above his sexy lips. He had the “you want me, don’t you?” look down. But my libido wilted in the heat. Plus I had hairy legs (and saw him glance down at them). At the end of the very professional interview he gave me his business card and I emailed him a few days later to thank him. And he emailed me back. On the 5th day of every month for the next seven months without ever asking me to hang out. Odd but intriguing. On our eighth month anniversary of email correspondence, I broke the seal. “Wanna grab a drink sometime?” I wrote. “OK, cool,” he wrote back in less than a month this time. And then we switched to texting. And the rest …

THURSDAY at 8:45 pm: I stood on the corner of 59th Street and Broadway waiting for my BPB to emerge from the New York night. Every guy that passed was him since I totally didn’t remember what he looked like. Oh s**t, is he this 60-year-old with a cane walking toward me? Oh no, is that him with the nappy ponytail and the pug nose? No, he doesn’t have a ponytail. But he could have grown one in eight months.

And then I saw a dark figure trudging through the fountain at Columbus Circle. Is it a bird? Is it a plane? No. It’s BPB! And he is soooo much hotter than I remembered him. He somehow seemed to have gotten taller, broader, darker, sexier and younger since we last met. Also, his backpack seemed to have gotten larger. What the hell is in there? “How old are you again? 12?” was the first thing out of my mouth. “25,” he smirked. Old enough, I guess. Come to mama, BPB.

“Where should we go?” I asked. “You pick,” he said adjusting his backpack, “damn this thing is heavy.” “What the hell have you got in there, anyway?” “Maybe you’ll find out.”

About 30 minutes into beers BPB removed his faux hump, gingerly put it under the table, grabbed my neck, and pulled me in for a kiss. I had my hand on his leg, and within five seconds of tongue in mouth, I felt something else really big … his dick. That thing stretched all the way across his thigh. Jesus. “I’m not one for making out in public,” I said startled by the sheer velocity of his appendage. “Me neither,” he said, “Where should we take this?” “My place,” I said.

Once in the cab it was all hands on my ass while his backpack sat neglected on the floor. I was still dying to know what was in there. Once naked in my bedroom is when he really surprised me first by unzipping his pants and then his backpack. His porn star penis was even bigger without the pesky restraint of clothing and was still hard by the way. And the backpack? He pulled out a magnum condom, a bottle of vodka, and two glasses. He poured me a drink. No effing way. It was a sex backpack!

Then he ripped off all my clothes off and started kissing me gently all over my whole body. “I forgot to shave my legs,” I said sheepishly.

“I think hairy legs are sexy. I remember your legs were hairy when we first met.” This is the first time ever that my laziness won me sexy accolades. “Your body looks like a Greek Goddess,” he whispered into my ear while slapping my ass hard. That’s an advanced move. After another 15 minutes or so of foreplay, I pushed BPB’s head between my legs. “No, I want to f**k you,” he begged. I wasn’t thrilled that he wanted to skip oral, but OK.

The most climactic moment of our f**kfest was when he looked at me (I was on top at this point) and said, “Relax and take your time. I only come if you come.” Very sweet and he was super hot, but I couldn’t get off for some reason. After an hour of sex (I’m not exaggerating) in every position known to man, I had to beg him to come because his huge penis was starting to hurt me. And I started to remember that he was 25. And that he has a sex backpack. And that he didn’t want to go down on me. And that sex without love is just kind of boring nowadays.

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