Eileen’s First Mistake

This is my first attempt at writing from a third person point of view...

It was a warm summer night. The humid southern air cast a shiny glow on the skin of the crowd of teens crammed together in Eileen Becker's house on Elm Drive. High School had just ended, Eileen's parents were away for the weekend and tonight she had every intention of becoming a woman.

Valedictorian, accepted to Harvard, state championship in cross country - on paper the year couldn't have gone better. Inside it felt like a trap of expectations that left her envying "real" teens as they stumbled through their stupid mistakes.

Butterflies filled her stomach both from nerves and from the beer she had consumed to help suppress her inhibitions. In true type-A form, Eileen had spent weeks planning her mistake and now she stood anxiously scanning the room for him.

Eileen had only two criteria for her first time; a nice body and discretion. She didn't want the entire town to know about her "mistake" and in Bakersfield that was tricky.

Mike lived three towns away and he was her best friends Kali's adopted cousin. They had met once over the holidays and in recent weeks she had carefully stalked his Facebook profile. Single, into video games, on the cross country team, not into partying and no slutty girls commenting on his wall or pictures. Perfect choice.

Scanning the room, Eileen spotted Mike on the outside deck. Tall, skinny, with smooth black skin wearing a t-shirt that revealed tone arms that she imagined pinning her to her bed. Eileen knew the stereotype about black guys but that had not factored into her choice.

Boys were an alien species to Eileen. As she navigated through the sweaty obstacle course of teens she wondered what she should say. Looking around crowd none of her friends were within sight to advise her, which was probably for the best since she hadn't shared her plan with anyone.

As she walked through the open slider door her heart fluttered and the butterflies in her stomach tried to escape. For a moment it felt like she may faint. Standing three feet away from the man that she had chosen to take her virginity, the muscles in Eileen's throat seized up as a million possible things to say raced through her head.

Eileen melted inside as Mike broke the ice for her. "Hey, thanks for inviting me, have you seen Kali around?" Kali hadn't arrived yet which was good because Eileen had worried how she would get Mike alone. Aside from a few casual Facebook messages and the party invite, Mike had no a clue about Eileen's plan for the night.

The cross country championship helped create easy small talk between the two. Eileen was small (most would say tiny), blonde, with blue eyes and unusually pretty in an understated way. Conversation quickly began to flow easily between the two. Eileen was not a girl that giggled much, especially around boys, but every word Mike said seemed tuned directly to her sense of humor.

Laughter evolved into casual touching, the pair gravitated closer together and the conversation became more personal. Both virgins. Both stressed out over achievers. Both nervous about college. Both trapped in a life under a microscope. Standing inches apart, talking in hushed voices their hands touched and Eileen whispered quietly, "do you want to go to my room?"

The bedroom door closed behind them and Eileen felt a sudden twinge of embarrassment for her pink, frilly room. Flustered and unsure of the appropriate etiquette Eileen mumbled an apology for the decor. Before she could say more Mike leaned toward her and pressed his thick lips against hers. Eileen's mouth opened to release a deep sigh and their tongues touched. The feeling was electric.

In a subtle move, Mike cautiously lifted Eileen's t-shirt over her head revealing a sheer yellow bra holding her pale white full b-cup breasts. Before she could register the newness of being exposed for the first time, her denim skirt fell to the floor. Stepping back, Mike looked down in awe of her body and matching underwear, his eyes full of panic and lust. Unsure of what to do next, Mike took her hand and they moved toward the bed. Eileen could not help but notice the contrast of her delicate pale hand wrapped in his oversized black fingers.

Standing next to the bed the pair intertwined in a long kiss. Their hands cautiously exploring each others bodies. Eileen's ambition for the night was being realized. Pausing from their kiss, desire and uncertainly radiated between them. The room was quiet as they stood breathing heavily together. "Can I go down on you" Eileen asked coyly, the look in Mike's eyes was all the approval she needed.

Moving boldly Eileen put her hand on the bugle beneath Mike's shorts. Her eyes widened as she tried to estimate the size of his penis. She moved her hand down the shape of his manhood and looked up to his face with her wide eyes. Their gazes met. His eyes eagerly encouraged her to proceed and he reenforced the message by unzipping his fly. Carefully Eileen reach into his shorts and released seven inches of thick, semi-hard black cock. There was a pause as reality set in for both of the teens. Growing harder and more eager Mike took his large tool in his hand and offered it to Eileen.

Being the good student that she was, Eileen had watched more than one porno movie to ensure that she knew how to perform. The movies had not prepared her for Mike. She wondered if she should have watched movies that featured black guys. She wrapped her small hand around his large black penis. His dark skin was smooth and the texture of his thick veins felt sensual on her innocent fingers.

Eileen opened her mouth and took in his thick round head. The shape resembled a small tennis ball. It seemed to grow in her mouth, and she felt his shaft harden in her hand. She could not fathom how it was possible but his already overwhelming penis continued to lengthen as she coated it with her saliva.

Carefully observing his body language and responding to each subtle cue Eileen tried her best to deliver the type of pleasure she had viewed online. Mike ran his hands through her hair and motioned her head toward him as he moaned. Eileen wondered if Mike could sense her knees and jaw tiring as he gently placed his hand under her chin and motioned her to rise.

Eileen unclasped her bra allowing Mike an unobstructed view of her hard, dime sized brown nipples. Mike positioned Eileen in front of the bed and lowered her onto her pink flowered sheets. Eileen lay on her bed shivering with anticipation as Mike slowly explored her body with his tongue. He devoured her perfect round breasts like a thrilling new treat.

Making eye contact to confirm approval, Mike hooked the sides of Eileen's panties with his thumbs and slid them down. For a moment Eileen felt a rush of vulnerability. The feeling faded as Mike parted her legs and positioned his fully erect manhood at her carefully trimmed opening.

Their combined innocence rushed through her mind and she wondered if she should get a condom from her bedside table. His penis was enormous, she doubted the condom would even fit. She had never imagined semen inside of her. When she watched dirty movies, semen leaking out of women was gross and demeaning. In that moment Eileen craved nothing more than to feel his smooth bare skin against hers.

She relaxed her legs and pulled Mike toward her. The wetness helped his thick manhood inch between the smooth milky folds of her unexplored womanhood. Eileen grimaced from the discomfort, tears formed at the edge of her eyes. Eileen noted the look of conflict in Mike's eyes as he cautiously explored her. Her tightness was stimulating Mike and every ounce of his instinct wanted to drive into her with all of his strength. Instead Mike gazed into her eyes and gently worked his penis more deeply inside of her. Eileen reached her hands to his cheeks and pulled his lips to her. The pair kissed softly as they adjusted to each others bodies.

Eileen, the over achiever that she was, pulled him close and whispered playfully in his ear, "fuck me." It sounded like a line from a porn and it probably was, but she wanted him to feel good. It took three strong thrusts to finally enter her fully. Her body pulsed with euphoria and she bit her lip to prevent the entire party from hearing her screams.

Mike was clumsy and each thrust seemed to drive more deeply into her. Eileen glowed and her cheeks flushed with emotion knowing that she had made the right choice. Wrapped in lust, Eileen eagerly played her role scratching at his back and biting at his shoulder as he found his rhythm sliding in and out of her. His bare skin felt better than she imagined and Eileen felt surprised to hear herself verbalizing her most dirty thoughts.

Out of breath from the intensity of the action Mike panted "I'm going to cum soon." The tone of his voice inferred that he was asking for permission or guidance. Eileen approved and her voice rang of urgency as she moaned out "from behind, from behind."

It thrilled Eileen to give up control and the instruction was all Mike needed to hear. Like a far more experienced lover than he was, Mike repositioned her leg and rolled her over onto her stomach without his long shaft leaving her tight body. Gripping her slim runners ass, Mike looked at his dark black penis stretching her white flesh and with almost primal instinct he drove himself into Eileen.

Her face buried in the pillow, Eileen clenched her teeth on a mouth full of cotton to avoid screaming out. Mike's gigantic tool was pushing against her insides, each powerful movement taking her breath away. Eileen wanted to yell out for him to stop. Her body felt like it couldn't take any more but an electric tingling radiated from every inch of her insides out to the tips of her fingers and toes. Mike thrust roughly and Eileen arched her back, willing to take anything for his enjoyment.

As his movements became harder and more erratic Eileen knew Mike was going to finish. That thought combined with the unpredictable movements inside of her her set off a chain reaction. Eileen's body involuntarily began to straighten and twist as she was consumed by her orgasm. Trying to hold onto her was too much for Mike and he began to release his semen deep inside of her. Each powerful contractions of his shaft filled her more with his fluids.

Black on white their sweaty naked bodies collapsed onto the bed. His large softening penis still deep inside of Eileen. Mike stayed on top of her until is softening cock finally slid out. Eileen felt his thick semen leaking from her body - instead of feeling grossed out Eileen felt a wave of giddiness.

Eileen felt like a woman. Mike kissed her gently on the back of the neck and rolled off of her. Eileen wondered if mistakes always felt so good.