Oh Captain, My Captain

This good sex story from Shore Leave by Bettina May is published with permission.

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Looking in the mirror, she checked that her lipstick was still on straight, then pulled down a tendril of hair to better frame her face. She’d seen the ship enter the Hudson River earlier that day, and she knew the captain would be making his way to her room any minute for their standing date. They’d been meeting up like this ever since he first enlisted in the service, and though she was happy for him with each successive promotion, she had to admit she missed him showing up in the classic service dress whites, part of what drew her to him in the first place.

Startled from her reverie by a brisk knock on the apartment door, she slipped into her long elegant faux mink coat to hide her nudity, just in case it wasn’t her captain, and opened the door a crack. She felt like she was still daydreaming about the early days of their occasional romance when she saw the handsome young man at the door, head to toe in navy whites, standing at attention. She stood there, speechless, smiling at her fantasy for what seemed like far too long.

“Surprise!” came a familiar voice from beside the entrance, and her charming silver fox bounded into the doorway and tossed an arm around the ensign’s shoulder. “I brought you a present, what do you think of him?” he asked. The younger sailor blushed, smiling down at the floor, too shy to make eye contact with the woman.

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“Well, he’s certainly handsome, but if he’s as shy as he’s acting, I’m not sure what good he’ll do me,” she teased as she pulled both men inside the one-room apartment, trying to mask her nervous excitement with bravado. She saw the captain only about once a year, but they stayed in touch, often sharing fantasies. At the top of her list was two sailors at the same time. While that fantasy was not at the top of his list, she knew he’d messed around with another man earlier in his career and that he was open to trying it again, especially with her. He was happily married to another woman, but they had an open relationship due to his being away. His wife was not interested in this particular fantasy, so it was one the captain and the woman talked about often, though she thought it was a long shot. 

“I hope you don’t mind, but I shared one of your letters with the ensign here, and he seems to think he’s the man for the job,” the captain stated, as though casually recommending the man for a promotion. Standing on her bare tiptoes, faux mink coat still clasped shut, the woman walked around the young man to inspect him. He had pulled himself up to his full six feet three, legs spread apart and hands clasped behind him as though she were a drill sergeant giving him a formal looking over. His broad shoulders and tight biceps strained against the crisp white uniform, and seeing no physical reason to reject this fine specimen, she walked toward her bed, dropping the coat on the floor and revealing her pleasing nude form to the two sea-weary men.

Sitting down on the bed, she arranged herself in a flattering pose, and enjoying the assumed role of superior officer, she turned to the now visibly aroused young man and used her most commanding voice. “Very well, then. You can start work here”—she gestured to the patch of dark brown curls at the V of her thighs—“and if you pass muster, we can have some more fun.” 

As the ensign started to peel off his tunic, revealing chiseled abs, she chided, “Uh-uh, sailor, that stays on for now.” He looked confused for a moment, then smiled and walked over to her, kneeling by the bed and softly kissing her knees before guiding them open to get in closer.

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She leaned back on one hand so she could tilt her pelvis up to him, putting the other hand on the charming white sailor hat on his beautiful head that made her heart race and sweetened her slit with moist anticipation. As his kisses came up her thigh toward her center, she looked over at the captain, who was casually leaning against the wall, unbuttoning his peacoat to reveal a thin white T-shirt and blue serge pants, and smiling at her with his own hunger and excitement. She wondered how long he would watch before he joined them, or if he would at all. 

Her thoughts returned quickly to the man between her legs, however, as his skilled lips and tongue made her cry out in delight and brought her to her first little orgasm. She had to push his eager mouth away, knocking his hat to the floor, as he would have kept working at it until she lost feeling, and she knew she had more fun in store. 

“All right, sailor, shirt off” barked the captain from his position in the corner. “Looks like you passed your first exam.” 

The young man jumped to his feet, wiped his face with his sleeve, and then peeled off his tunic as the older man strode confidently past him to the woman and scooped her quivering body up in his arms, kissing the top of her head tenderly as she curled into his burly chest. 

“Peel back those covers,” he demanded of the ensign, who quickly followed orders. The captain winked at the woman in his arms who was quite enjoying the display of command for her benefit. He lay her down gently, and was about to climb into bed next to her when a strong bare arm snaked around his waist, pressing his back against the hairless, bare torso of the young sailor.

“Don’t you think we should give her a little show while she catches her breath?” the young man breathed into the captain’s ear as he reached a hand up to the bristled chin of his superior officer to pull his head to the side so they were facing each other. 

For a moment the woman lay breathless, noting the stern look on her lover’s face as he stared down the bold young sailor, not sure if they were about to fight or fuck, but feeling aroused either way as she enjoyed the Tom of Finland scene coming to life in front of her.

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The pause lasted another tense moment, and then the captain mashed his lips so aggressively against the other’s that at first the woman thought he might have head-butted him. But when the sailor pulled up the shirt of the older man to reveal the thick layer of grayish-brown hair covering his muscular torso and started to kiss his way down the front, she lay entranced by the display of raw masculine passion in her room. She had never shared her lover with anyone before, and was relieved to find she enjoyed watching the beautiful young man take the captain’s balls in his mouth while he stroked the man’s thick cock. Her captain grabbed the back of the sailor’s head while he braced himself against the wall with his other hand, closing his eyes and raising his face to the ceiling as he became lost in the feeling of the younger man sliding the cock into his mouth still wet with her juices. 

She watched for another minute, then crawled to the edge of the bed to join them. Lying on her stomach, she ran a hand across the muscular shoulders of the young man while she kissed the captain’s hip, making her way to the mouth of the other man. One hand firmly gripping the cock as it left his mouth, the sailor turned his head to the woman as she kissed him, and then she let him guide the pulsing head into her mouth, teasing first with her tongue, then taking it in as far as she could. They took turns licking and sucking for a bit until the captain reached down to her, sliding a hand under her armpit to pull her up to kiss him so she was standing next to him. The kneeling sailor kept working the captain with his mouth as he put his large hand on the woman’s ass, holding her close to him, slowly working a finger into her wet pussy.

Suddenly the captain gasped and let out a low groan as he came in the sailor’s mouth. They all looked at one another for a second, and then the older man pulled them both onto the bed. He sat up by the headboard and spooned his longtime lover, whispering in her ear, “Would you like him to fuck you now?” 

She nodded, and he gestured to the sailor to take his pants off. The young man slid off the flared white pants and grabbed the condom on the nightstand as he climbed onto the bed, sliding his bent knees under her thighs as he sheathed his hard cock in latex. The captain licked his fingers and teased her slit until it was dripping wet again, caressing her breasts with his free hand. She grabbed the sailor’s cock and glided it inside her as he gripped her hips to pull her close. The three bodies pressed together, all self-consciousness melted to the floor as they writhed against one another, pumping and grabbing, kissing and moaning until the woman and the sailor each came in turn. They collapsed in a satisfied heap until the men’s shore leave ended early the next morning.

*

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To find out what happens next, buy Shore Leave here.

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