You Can't Help Who You Love Ch. 02

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Becky overcomes her uncertainty.
4.2k words
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Part 2 of the 2 part series

Updated 06/09/2023
Created 11/07/2019
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Disclaimer: All of the characters described in this story are fictional and over the age of 18.

Note from author: Thanks to everyone who voted or commented on the first chapter. It is always helpful to get feedback and I try to keep it in mind when starting a new story. The second chapter in this series is told from Becky's perspective in order to explore that character in a little more depth. Hopefully you enjoy it.

*****

Lurking beneath the surface

Waking to the soft light streaming in through the window, Becky felt a warm presence pressed against her side and a strong arm draped loosely over her midriff. As she glanced over to see Chris lying in her bed, sound asleep and lightly snoring, a deep sense of happiness washed over her. Unlike her few previous lovers, this was a kind, gentle man who wasn't looking to just use her for his own pleasure.

She re-positioned herself to rest on one elbow and watched him as he slept. The duvet and sheet had fallen down exposing his bare chest and she eased the cover down further to reveal his lean abdomen. Her sex stirred as she gently ran her fingers over his warm, tanned skin. Chris didn't have washboard abs, but he had a nicely defined, strong build that begged to be touched.

He was handsome too. When she first saw him standing in the doorway, her breath caught in her throat and it took a few moments to regain her composure. He seemed relaxed, with his easy smile and casual dress. His athletic frame stood a good half foot taller than her which she liked. The sexy green eyes and tanned complexion were framed nicely by his neatly trimmed, dark chocolate hair. A smattering of silver through the mat of dark brown above his ears were the only evidence of the passing of his 42 years.

When those lips had brushed hers in the lightest of kisses as he met her at the door, Becky had melted. But that paled by comparison with the effect he had on her when those lips explored her body later the same night.

Continuing to absently trace lines over his stomach with her fingertips, Becky happily watched Chris in his peaceful slumber. It was a strange feeling, but for the first time that she could remember she simply felt content. She could feel the remnants of their coupling between her legs and could still feel his touch imprinted on her body and it turned her on. She felt marked, branded as his, and she was surprised how comfortable she was with that idea so soon after meeting him.

She desperately wanted this to be more than just a one-night stand. The insecurities that had been held in check all night, suddenly resurfaced. She had been so proud of the confidence that she had displayed last night. A confidence that she didn't genuinely feel.

In truth, Becky had never been comfortable in her own skin. She had grown attuned to rejection and wary of attention. Becky. or Alex, as she had been born, had felt cut-off and isolated for most of her life.

Alex had always been short and his physique in his teen years might generously have been described as wispy. He had been athletic, but not strong. Nor had he revelled in the kind of rough and tumble that typified adolescent male behaviour. He had been an acutely intelligent child but even this was a curse at times. His perceptiveness let him pick up on the way he was viewed by the children around him, which fuelled his sense of isolation and insecurity.

He had some acquaintances, but few friends growing up and he yearned to have someone close with whom to confide.

Alex was a quiet child and his parents seemed oblivious to the emotional turmoil he was experiencing. They were not bad people, but their busy professional lives blinded them to the desperate need their only child felt for attention to fill the growing social gap with his peers. This, as it turned out, was something they were ill-equipped to provide.

Instead, Alex found refuge in study and he quickly established herself as a solid student. His natural intellect and an abundance of free time led him to be among the top few students in his year. This quiet drive and probing intellect would eventually see him become a highly-regarded economic analyst.

In early high school Alex became aware that he was attracted to boys rather than girls. Unfortunately, there were seemingly few opportunities for him to act on this attraction and learn the lessons about flirtation and relationships that most children are exposed to as they begin to explore.

However, in year 10, his interest in males found a focus as he developed a strong crush on a boy in the year above him at high school. To Alex, Ian was perfection personified. As a swimmer, he had developed a strong physique early, with broad shoulders and defined, muscular legs. His golden hair and blue eyes sealed the deal. Alex would watch him longingly from afar, never quite able to muster the courage to talk to him.

One summer morning, many months after the attraction had kindled, Alex found a note slipped in his locker. As he unfolded the note and began to read, his heart leaped into his throat. The note was from Ian. It made clear that he was aware of Alex's interest and that it was mutual. He suggested that he and Alex meet to talk away from school. Ian indicated that he would wait for Alex after school at a spot on the local river by an abandoned rail yard. He hoped that Alex would come.

To say that Alex was elated would be seriously underselling his emotional state. He hadn't dared to hope that this Adonis would even deign to talk to him, let alone want to be romantically involved. Alex had butterflies in his stomach all day through class and he took nothing in that his teachers said. When the bell finally rang, he walked briskly to the appointed meeting place.

Cresting a wooded hill that led to the rail yard Alex saw six boys from his school in the isolated meeting place. Surprised and confused, he approached them with trepidation. As they saw him approach, they burst into raucous laughter. The bile rose in Alex's throat as he began to understand that things were not as he had expected.

One large boy called mockingly to Alex, "hey faggot, were you expecting someone?" The terrible truth now dawned on Alex. However, the boys weren't going to miss their opportunity to revel in his humiliation. Between fits of laughter they told him that they had seen the furtive glances that Alex shot in Ian's direction and how they had conceived their ruse to lure Alex here.

However, Alex's focus wasn't on their story. His watery eyes were on Ian, standing there among the group, joining in the cruel mockery. Alex felt completely numb and hollow. He stood motionless as the tears fell silently down his cheeks. This of course only further encouraged the mob.

After what seemed like hours, his vision blurred by the torrent of tears, Alex turned and ran. He had been too paralyzed with fear and uncertainty to allow himself to be vulnerable with someone and the first moment he did his heart was shattered. It was this moment, more than any other in his life that built the wall around Alex.

Several years later, as a professional in a banking firm, he found himself far from the only gay man in the office place. While the workplace lacked the puerile behaviour of adolescent boys, he still felt 'apart' from many of his colleagues.

He lacked the confidence to go up to someone and ask them out. So after much hesitation, he put an ad up on a dating site tailored to gay and lesbian singles. He met a couple of guys who had responded to his ad, but they were just hunting for casual sex. In a misguided effort to make them like him he had acceded to their wishes. His first time was with a much older man who showed no regard for the young virgin. He took his pleasure roughly as Alex sobbed silently into the pillow from the pain. When the older man was finished, he wiped himself clean on the sheets and walked out of the room. Alex lay prostrate and confused.

More than anything Alex wanted to be held the way his father used to hold his mother. He could remember his mother snuggle into his father's protective embrace, her head resting against his chest. His mother exuded femininity and he would see the way her hour-glass figure was highlighted by the knee-length satin nighties that she favoured. He would also see the way that her father's gaze followed her curves. His Dad would often let a casual hand graze adoringly over her body.

Alex often pondered whether it was some unconscious association that his mind drew between the alluring femininity of his mother and the affection that it unfailingly elicited from his father, that had drawn him to cross-dressing in the first place. It was an affection that the young Alex coveted.

Either way, in his early twenties he began his first tentative explorations with women's clothing in the sanctuary of his one-bedroom apartment. The first garment that he tried on had been a pair of red lace panties that he had stolen from his mother's lingerie drawer when he last visited. His mother had a slightly larger build than Alex, but they still fit passably well. His head was light as he pulled on the garment. He luxuriated in the way the delicate fabric caressed his skin. He closed his eyes and ran his hands over his panty-clad body, pretending the touch to be that of a lover that he had brought home to seduce. The sensation felt...right.

As Alex opened his eyes, he glimpsed himself in the mirror and was disappointed to see a boy in knickers. Alex wanted to feel feminine again. To be the kind of girl that would draw a man's attention and not let it go.

It took a few months, but plucked up the courage and placed an online order for a basic make-up kit and some lingerie. He began to read anything he could find on cross-dressing and the art of cosmetics. His early efforts made him look like an extra in the Rocky Horror Picture Show. He was way too heavy handed with the make-up. However, he was a keen study, and with time he acquired an adept hand at applying make-up. It didn't hurt that he had naturally feminine features and a diminutive physique.

As his interest took hold, he bought breast and pussy prostheses, but found that he didn't like the feel of the silicon against his body. He far preferred the feel of expensive lingerie. He had greater success with hair pieces, which he adored for their look and the feel as the long locks fell softly over his bare back or shoulders.

While Alex wasn't particularly hairy, he nonetheless shaved his entire body. The feeling of cool satin kissing his skin as he slipped a black satin camisole over his smooth body for the first time was euphoric. He slipped on matching panties that barely cupped half of his shapely ass. Finally, he slipped on a pair of black thigh length, denier stockings with pretty lace leg bands. Standing in front of a mirror, Alex couldn't believe the transformation. He saw an attractive, confident young woman looking back at him in the mirror. The make-up was flawless and he couldn't believe how sexy the outfit made him feel. He wanted desperately to find someone who would appreciate this.

It had been many months later, after much further experimentation, that Alex had come to the realization that he identified more as a woman than he did a man. The lingerie only brought out the sensual girl hiding beneath. While 'she' knew that she lacked the confidence to reveal her transformation to the world, in her own world she became 'Becky'. A young Alex had once asked his parents what they would have called a girl if they had one and his mother had immediately volunteered that it would be 'Rebecca'. Becky now enjoyed the irony of becoming the daughter her parents had never had.

Becky would exclusively wear women's clothes around her apartment. However, it would be more than five years before she was again ready to reach out to someone and take a chance on being hurt.

New frontiers

With a start, Becky noticed her dishevelled hair laying in matted clumps across her shoulders. "Oh God, I can't let him see me like this! I don't even want to know how my make-up looks," she pondered anxiously.

Gently removing his arm, she eased out of bed and stopping briefly to select some appropriate items to wear, she walked hurriedly to the bathroom down the hall. She closed and locked the door and made a brief stop to empty her bladder. Carefully removing the wig, she carefully brushed it and placed it on the counter. "My God," she thought with shock. "I look a mess."

Her make-up was streaked and smudged from the night's sleep and the physical exertions of the night before. Becky quickly grabbed some make-up remover pads and methodically removed the layers of foundation, blush, eye-liner and lipstick. Then she padded over to the shower and within seconds had a stream of hot water beating a tattoo on her tired shoulders and back. She washed, dried and brushed her teeth hurriedly so that she could focus her time on re-setting her make-up. With deodorant and perfume taken care of, she stepped into the salmon pink, silk baby doll night dress, with lace trim along the v-shaped neckline and the short slit at the thigh. Next were the matching panties, followed by a simple gold ankle bracelet.

Setting her foundation, blush and eyeliner, she carefully chose a lipstick that was a slightly lighter shade of red than she had used the night before and applied it carefully. Lastly, she picked up her brushed hair piece and carefully fixed it in place. When she was finished she looked into the mirror and was happy with the beauty that stared back at her.

With her mask back in place, she smiled with renewed confidence. Walking with a gentle sway to her hips, she slinked into the bedroom to find Chris still asleep. Becky eased herself back under the covers and softly caressed Chris' chest and abdomen. The feather-light touch did not wake him, but Becky's attention was quickly drawn to a prominent tenting of the bed covers.

"I wonder what you're dreaming of," she mused to herself.

Pulling the duvet and sheet down the bed, Chris' erection sprung free, slapping against his belly.

"You have a gorgeous cock," she whispered to his slumbering form.

With a devilish smile spreading across her face, Becky moved down the bed, positioning herself between Chris' slightly spread legs. She gently pushed his thighs further apart so that she could lay directly below his groin. Resting her weight on her elbows, she bent forward and placed a soft kiss on the shaft of his cock. It twitched as her lips retreated. Looking up at Chris' unchanged visage, she traced her tongue along the underside of his shaft, finishing just beneath his slit. Retreating, she traced a wet line up the side of his penis. As she finished his cock twitched again. Leaning further forward, she took the tip into her mouth.

Becky let the head of Chris' dick rest in her mouth, enjoying the warmth, the weight and the texture of his smooth uncut phallus between her lips. Oral sex was such a deeply personal act with which he had limited experience and she relished the chance to pleasure this man. Her tongue lazily grazed the tip of his cock, eliciting a soft moan from the head of the bed. Looking up, Becky could see Chris starting to stir.

Now it isn't an easy thing to smile with a thick penis in your mouth, but Becky gave it an awfully good shot. Sensing that Chris was beginning to wake, she ran the tip of her tongue in gentle circles around the head of his cock. Periodically, she would break her rhythm to run the tip of her tongue over the slit at the apex of his manhood.

Becky watched as Chris' eyes opened and consciousness slowly returned to him. Looking down, Chris' gaze locked on Becky's and she took that opportunity to slide her mouth tantalizingly slowly down his erect shaft.

"Ooooh, Becky," Chris forced out between clenched teeth as his eyes closed involuntarily from the pleasure that she was giving him.

Hearing Chris moan her name made her tingle. Giddy with happiness, she increased the suction on his penis as she retreated back towards the head of his dick, drawing his foreskin back. Sliding her mouth back down his shaft, exposing his sensitive glans, she lashed the swollen head with her tongue extracting more of his manly essence and drawing forth a long groan. With each down-stroke, more of Chris penetrated her lips, leaving lipstick marks as a new 'high water mark' on the pale skin at the root of his shaft.

She paused her egress up and down his manhood and with just the tip of his cock between her red lips she feverishly swirled her tongue around the sensitive head of his cock. Chris' hips involuntarily lifted off the bed, pressing his cock deeper into Becky's hot mouth. Her hand took hold of his balls and gently caressed them as she again impaled herself on his thick rod. Chris' hands were in her hair as she again began to glide effortlessly up and down him. She desperately wanted to taste him, to watch his back arch off the bed as his seed gushed into her pretty mouth. But even more than that, she wanted to be held and made love to again the way he had last night.

Placing a final soft kiss on the head of his cock, she crawled up to straddle him and held herself above him, with her weight borne by the hands she pressed into the bed on either side of his chest. She looked down meeting his gaze as his hand crept up to gently cup her cheek. He smiled fondly at her and she melted into him, their lips locking in a tender kiss. His hands took hold of her waist, pressing the cool silk against Becky's skin. She pressed her groin down massaging his trapped cock and eliciting a guttural moan that filled the small room. Gyrating her hips, she teased him as his lips parted and his tongue brushed against her mouth. She welcomed his entreaty, meeting his tongue with her own and swirling it as they gently explored.

His hands found her buttocks as her hips continued to undulate on him. He squeezed her firm ass between his strong hands as his lips parted further and devoured her, the growing need in his actions becoming apparent.

His mouth moved down to her neck and drew her flesh between his lips. The suction he applied mingle with the feel of his hands plying her ass and his swollen organ beneath her, sending shivers through her. His hands crept under her panties and the index finger of his right hand spread her cheeks and ran softly along the gap between. Her throaty groan giving him the permission he sought and his finger began to lightly probe her entry.

Becky's hips began gyrating again trying desperately to press his probing digit inside her. At that moment Chris' teeth grazed her neck, the sensation driving her wild and forcing her hips down hard on his hand. The tip of his finger pierced the muscular barrier and Becky screamed from the intense pleasure. But his finger was dry and could not easily give her the stimulation she so desperately sought. And, she was beyond the point where his finger would be enough for her.

"I need you inside me Sweetheart," she breathed huskily.

Looking deeply into her eyes, Chris nodded and moved his hands so that she could shift her position. Moving with feline grace, Becky stood by the side of the bed, feeling the intensity of Chris' gaze on her. Meeting his eyes, she eased her hands underneath the hem of the baby doll dress and shimmied the panties seductively down her smooth legs. Moving to the bedside table she picked up the tube of lubricant that Chris had left there from the previous night and gently applied it.

Moving back onto the bed Becky held the hem of her silk dress so that she could re-position herself over Chris' rigid organ. With her legs in place above him, she reached back and guided him into position. She felt the delicious sensation of his hot, rubbery cock head contact the lubricated crevice between her cheeks and slide between. Moving her hips, Becky moved Chris between her mounds, wetting him and preparing him to penetrate her.

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