Bob Love Diaries
The Romantic Confessions of a Virgin Prude

Part 13
Virginity Lost

Yes, eventually I lost my virginity. And I lost it the best possible way: To a slut. It happened when I was.... ahem, ak. Fuck. Okay... I was, ah... rats. 25 years old. Christ.

There are many factors that lead up to someone not losing their virginity until so late into the game (religious hang-ups, low self-esteem, unpopularity, acne, scrawniness, cowardly, uncool, bad grooming habits, anti-social behavior, weak in body and mind, unattractive, prude, quirky, awkward and a touch effeminate). I was desperately looking to lose the cherry, and I wasn't going to be able to do it without help.

Chicago, 1995 and my brother Rick had finally talked me into going out regularly in the evenings to a bar. The "Smart Bar". This was something that I didn't necessarily enjoy doing due to the aforementioned defects, but he got me out and assured me that I would forever remain a virgin if I didn't leave my apartment.

By this point I was believing that I had been jinxed. I felt that I was more likely to be killed in a car accident before I was to have sex. And not only had I never had your basic penis/vagina intercourse, but I was also free of spooning, blow jobs, naked-bed-pals, face sitting, kitty licking, titty fucking, poked-with-a-ten-foot-poling and even your basic hand job (besides my own). I was a complete and utter mess to say the least. Then along came Nancy. Nancy was loose. She was a big breasted, sleazy girl who hung around in bars and slept with the boys she met there. My brother and I were at the bar, probably talking again about how I'd never get laid, when, down at the other end of the bar appeared Nancy... in all of her wonderful cleavage.

Portrait of a 25 year old virgin. I'm the pink one.

Now my brother is a good looking guy and has never had much of a problem getting girls. Nancy had flirted with him in the past but he was not interested in her. This is where the scheme hatched. I was a desperate man, and Nancy, not getting a reaction from my brother, began flirting with me!

Rick said to me this: "Bob, Nancy will sleep with you, I assure you that. We just have to play this right."
Nancy was clearly giving me the eye from accross the bar. This was going to be the evening that I would be cured of my virginity. You see, Nancy, not being able to get Rick, thought that she could make him jealous if she pressed me.
"Bob, the more she flirts with you the more irritated I'll act."
Nancy thought that she was coming in between two brothers.
"I'll just pretend that I don't even notice you and could care less about your reactions."
"No problem. This'll be easy. You watch."
I motioned to the flirtatious and smiling Nancy to come over, while Rick pretended to be bothered that I was doing so, turning his shoulder on me ever so slightly. The game was on.
She approached us and said "helloooo" quite sexily.
"Who is this, Rick?" she asked.
"I'm his brother Bob." I played it as cool as possible.
"You never told me you had a brother!"
She faced me, heaving her giant bosom into my face. [Note to ladies: I admire and respect this maneuver very much]

I tried to play it cool, but there was no hiding my interest at that point. Rick who? And my brother stayed true, letting out a perturbed sigh, and sunk into his drink.
She worked herself in between my knees and seemed to get more and more aggressive with each make-believe glare from my bro.
"Is everything okay with your brother?" She asked with a devious smile.
"I dunno." I said without even looking at him,
"He's fine. Whatever." I was gazing into her cleavage like a love sick puppy. Rick periodically looked over his shoulder at us like a jilted friend.

By the time Rick returned, Nancy had me embraced in her thighs and my nose buried deep between those lovely honkers. Semi loudly to us both, Rick stated "Okay, I'm outta here" while gathering his things. Then, as he set his drink onto the bar he said into my ear, "I'm very happy for you. Have a great night." Then he switched right back into pouting mode, threw some change on the bar and left.

"Are you sure everything's all right between you two?"
"I couldn't care less!" I stated. "I'm sure he'll be just fine."
And then Nancy invited me back to her place.

She had no idea I was a virgin, and that night she took my cherry many many different ways.
So that's the story of the night that I got popped. I was now king, and my crown had been mounted.

Nancy made it very clear to me that she adored my penis, complimenting me on its size often. She told me that she loved to suck dick and that I was welcome back whenever I wanted to come, and I did return, for a few weeks, until I met my first girlfriend-to-be, Julie.

Lose it to a slut. That's what I say. They'll do all the work and never even notice that you've no idea what you're doing.

Thanks Rick.

All opinions, writings, illustrations & designs are that of Normal Bob Smith (C) 2000 - 2008
NORMAL BOB SMITH DESIGN NEW YORK