Sean and Roger

Story Info
A night on the town leaves 2 unlikely lovers together alone.
1.6k words
4.17
23.6k
1
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
ShadeyB
ShadeyB
2 Followers

"You know I'm not queer, right?" Roger was almost blushing at the attention Sean was lavishing on him. "You really are just that hot to night, by anyone's standards." He let himself lean into Sean's caress, but tried to manage his interest by looking about his dingy, cluttered apartment.

"I tried hard tonight. I mean, not especially for you. But I wanted to feel great when we went out. And it worked." Sean giggled as he realized how much the night's cocktails were staggering his speech, and brushed a stray lock of shoulder length chestnut from where a night of dancing and sweat had plastered it. He leaned in for a kiss and Roger hesitated only a moment before letting himself go.

After a long moment-- probably several minutes, he began to realize-- Roger pulled himself back, catching his breath. He gazed over Sean's body in wonder. His ultimately relaxed posture was pure androgyny; his dress-- the worn out combat boots over black, gray and violet swirled thigh-highs; the mid-thigh length pleated black denim and cordura skirt Sean had hand stitched himself with every chain, lace, clasp and zipper as functional as fashionable; the tight-knitted mesh shirt over the velveteen violet sports bra and under the black leather bodice; the fingerless gloves on each hand, soft black leather on the left and crimson red wool up to his right elbow-- it all oozed of female brutishness and wonton sexuality; his face-- soft hair left down and free; trimmed sideburns to the bottoms of his ears; the short spirit line crossing his strong narrow chin then split into a thin goatee; various shades of foundation applied here and there not to cover course features, but to highlight and accentuate the best-- effacing only the most refined male characteristics; his body-- taller than most men, but only just, with long limbs that were muscular but lean and lithe. That was Sean's strongest talent, to painstakingly arrange every detail to compliment each other, such that, when finished, he truly could affect near perfection with no further effort. Tonight he had achieved perfect androgyny, and it has been noticed by everyone who saw him.

Sean shifted restlessly on the old couch under Roger's stare. "I can go if you want me to." He looked away, pushing his hair behind his ear the way a teenage girl would when she's uncomfortable and unsure what to do about it, and for a moment that's how Roger saw him. Though Sean was taller than Roger by a head, and stronger, too, he seemed to shrink into a scrawny tween for an instant.

"No, no," Roger blurted, almost too loud. "It's just," He took a deep breath and sighed it out, working through his own drink-fogged mind. "It's just... You're so beautiful. I never saw you like that before. I mean, like, as something sexy." He blushed again and looked down himself. "I'd love for you to stay the night."

Sean looked up at Roger out of the corner of his eye. "I'd like that, too," was all he answered before Roger leaned in this time, planting a soft kiss on Sean's neck. Sean moaned lightly and leaned toward Roger with arms outstretched. He turned to him and, arms around Rogers shoulders, pulled him down over him across the couch and pressed his lips to Roger's. This kiss lasted longer than the first, the initial shock leaving Roger quickly, and he let his hands explore Sean's body, though unsteadily. Sean roughly stroked Roger's auburn hair and strong, square shoulders with growing excitement. After a few minutes, Rogers shirt was un-tucked and his trousers opened but not yet down. Sean's bodice was loose and his stockings had slipped to his calves. "Lets go to the bed," Roger suggested between breaths. He reluctantly pushed himself off of Sean and, one hand holding his pants, the other Sean's hand, led the way to a mattress resting on the floor of the next room.

Roger released Sean's hand to close the door behind them, then kicked off his shoes and let go of his trousers. He stumbled out of his shorts and socks while he watched Sean drunkenly struggle with his boots in the dark. "They won't come off," he giggled, falling back on the bed arms outstretched, like a drunken prom date. "Help," he demanded throwing a leg into the airs.

Roger, forgetting about the uncooperative buttons of his shirt, grinned and knelt down between Sean's legs, his stiff member jabbing the side of the mattress almost painfully as he did. "You can keep them on," he said with a chuckle as he ran a hand up each smooth leg and under Sean's skirt. He found his face buried in the course fabrics over Sean's lap as he clumsily felt around for the edges of Sean's boy shorts. When he finally found them he pulled them down a few inches and felt Sean's piece spring up suddenly against his cheek.

Sean drew a sudden breath at the release and moaned softly, "oh, god, please." Roger responded, using his face to push back the skirt and one hand to grip Sean's throbbing penis. He stroked a few times, hesitant, then pushed his mouth over the member with a breath as though diving under water. Roger focused intently on his actions, but heard Sean cry out, "god, yah." Encouraged, he lowered his hand on Sean's shaft and took more of it into his mouth with each bob of his head, ever so careful to mind his teeth and use his tongue, like he had told ex-girlfriends dozens of times before. Sean replied with gently thrusting hips and louder moans, his deep masculine voice taking a distinctly feminine tone.

A few minutes in, Roger brought his head up. "God, that was fantastic," Sean was saying as Roger tugged stupidly at the yellow panties around Sean's knees.

"They wont go over your tights," he whined, but continued tugging.

Sean grinned and grasped Roger's wrist, and tugged him down next to him on the bed and rolled into him for a kiss. After a few seconds Sean sat up, pulled the bodice off over his head, then flipped up the tails of Roger's shirt. He looked at Rogers member almost quizzically for a second then fell on it, taking the full length in the first swallow. Roger threw his head back, gasping at the sensations, throwing his hips into the air. Sean managed to keep in step, and continued as he gently cupped Roger's sack in his hand, massaging its contents while his fingers danced across Roger's taint and anus. Roger drew himself back with some effort and told Sean "yes" very deliberately. Now with Roger's permission, Sean gently pressed a finger into Roger's hole.

Roger jerked slightly at the unfamiliar sensation but controlled himself and raised his knees to give Sean better access. Over a few minutes, Sean had sunk the full length of his finger into Roger's rectum as he worked diligently on the stiff appendage, and Roger has responded with his own moans. Sean pulled his hand away, leaving Roger to gasp at the sudden change. Roger took hold of a lock of Sean's hair and tugged gently. Sean crept up and laid next to Roger kissing him. Roger marveled at the flavor of his own pre on Sean's mouth, circling Sean's lips and tongue for another taste. "God," Sean let out when they broke away. "I want it now. I want to cum," and he raised his legs to give Roger his shot.

Roger sat up looking over Sean's body again. "No," he said. "I want to do this," and he pushed Sean's legs down and threw his own leg over Sean's body to kneel over him. Roger reached behind him and took Sean's penis and positioned it at his ass and tried to lower onto it.

He winced but didn't give up. "Do you have any lube," Sean asked as he casually took hold of Rogers member and began stroking it softly, a concerned look on his face.

"No," Roger sounded frustrated, but then lightened. "I have some lubricated condoms," he suggested.

Sean smiled. "Probably a good idea anyway." Without leaving his position over Sean, Roger leaned over to a box near the head of the bed and retrieved the small square package and ripped it open. Working by feel with one hand going behind him and the other in front, Roger rolled the latex down over Sean's piece.

As he was positioning himself once again, Roger heard Sean ask "are you sure? You don't have to." He responded by pushing Sean's cock inside of him, slowly letting himself down the full length onto Sean's lap. Sean moaned and began pounding his fist over Roger's member harder. Roger pulled air sharply between his teeth as he began grinding into Sean's hips, gently raising and lowering himself. After a few minutes, Roger had found his rhythm and he leaned back and bucked his hips as he watched Sean jack him briskly.

Only a short dozen thrusts later Roger began to feel his orgasm building. "Oh, god," he moaned out and threw himself down over Sean as he came across his chest. Not finished yet, Sean wrapped his arms around Roger's shoulders, lifted his hips and began to drive into Roger furiously. Roger cried out at the sound of their flesh slapping together, and the over-charged feeling in his groin. "Oh, shit! Oh, shit," he yelled. Moments later, Sean came to an abrupt stop, forcing his hips as high off the mattress as he could manage, lifting Roger into the air as he did.

As their climax passed, Roger rolled off of Sean, the condom slipping from Sean's softening member and hanging from his ass. He reached down, almost disgusted, pulled the rubber out with a shutter and tossed it out of sight. Within seconds they were both asleep.

ShadeyB
ShadeyB
2 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
ShadeyBShadeyBover 12 years agoAuthor

Thanks. If nothing else, I like the characters-- at least as they are in my head-- so I think I'll have to do more with them some time.

AnonymousAnonymousover 12 years ago

romantically nice reading, hope there'll be more

Share this Story

Similar Stories

What a Friday Night A first discovery for a college man into exciting times.in Transgender & Crossdressers
City of Angels Kinky girlfriend dresses new boyfriend up for a night out.in Transgender & Crossdressers
A Tight Fit Three's a crowd on a camping holiday.in Anal
Swipe Right for Something New A change in app settings, a complex change in perspective.in Lesbian Sex
Popping His Cherry She finally makes him her woman.in Transgender & Crossdressers
More Stories