Femboy Roommate Punished

(Disclaimer: All characters displayed are above the age of 18. Kinks include: tickling, male on femboy, worship/kissing, nipple play)

My college roommate's a femboy. His name's Jess. Jess is always wearing makeup and constantly dresses up in girly clothes. Lots of sweaters, mini skirts, crop tops, booty shorts, even nylons and fishnets. His black hair has always been cut long and purposefully messy too. Even his figure is feminine and his skin clear like glass. He insists he's still as much a guy as me though. It becomes super distracting when I'm trying to study and he's prancing around all done up, or coming home extremely late with some satisfied look on his face. We get along fine besides everything, I guess. It wouldn't be until recently that it finally pushed me over the edge, however, and that I really got to know my roommate.

I was up doing an assignment, cramming as usual, and it was late; maybe around midnight when Jess finally got back. Our door opened and light flooded my desk. Jess had on a sweater and a mini skirt that rode forcefully high, showing off the sheer black stockings that hugged his legs. Pink bows sat throughout his hair too, and his eyeliner was sharp. Stressed out already by crammed schoolwork, seeing Jess come back with that needlessly careless grin completely took me out of my zone. I rolled my eyes in frustration as I greeted him. "Big night, princess?"

Jess spoke with a giggle as he kicked off his shoes. "No bigger than usual". His feet looked soft wrapped in that dark nylon. My focus ran up his body to see him looking back at me, an almost triumphant glaze in his eyes. "Did you just check me out?" he said through that dumb smirk. "No," I responded, annoyed, "and I wish you'd stop staying out so late, or at least come back in the morning so I can study easy at night."

"Not my fault you're stuck inside. You should manage your time better." Jess moved to stand behind me in a slouch while we talked. His arms came to rest off my shoulders, dangling down in front of me while his chest pressed the back of my chair. I felt his hair brush my face as he scanned my work briefly. "You so eyed me up," Jess said softly in my ear. "Nuh uh," I replied defensively. He chuckled while I tried to nudge him off me. Jess had always been very touchy with me, weaseling himself into my personal space. This time he was really getting to me, even more than normal. I was so frustrated already, and now Jess' obnoxious presence anchored any productive chain of thought. Then I felt his hands move up my torso. It took me by surprise. Flush filled my cheeks. Jess moved with purpose, not loose and careless like before, his dainty hands having a steadfast weight about them. I tensed but little more as Jess' fingers came quickly and began groping my chest and playing with my nipples through my shirt. "Mmmmm," he moaned in a soft expression of pleasure, and as he toyed with me I became awfully aware of my own delicate skin.

In a flustered panic I bucked from my chair, pushing Jess off me as I came to a stand, red plastering my face. "DUDE," I yelled, "WHY ARE YOU SUCH AN ASS?" Jess stared for a second, still smiling, but seemingly a little embarrassed now. "I'm just playing with you, man," he shyly answered. "You're always playing with me," I responded. He shrugged a little as he went on nervously, "I like to play. If you're not in the mood though I'll quit it, I guess."

I was too mad to just let Jess off now, and I wanted to prove a point, better yet just get him back. Any care for studying now was out the door. I darted towards him, not reciprocating a word as I did so. I steered Jess back in an instant. Then surprise took his face in a gasp. With force I pushed him on to the foot of my single bed where we both collapsed, me on top of him. Jess, taken aback, parted his lips to speak, yet not before my hands found his waist in a squeeze. His eyes went wide in frightful shock as I began to knead his sides through his sweater.

"WAIIHTEHHEHA," Jess squealed, arching his back while I tickled him mercilessly. His laugh was awfully girly and came in rolling giggles. I began to mock Jess as he often did me, really rubbing in the flipped dynamic. Now I was the one messing with him. "Coochie coo. You're so ticklish Jessie. Listen to you scream. Is it too much for you, Princess? Tickle, tickle, tickle."

"YEEHEHSSSAHAHH, IMMM SOHHORREHHEH" Jess yelped playfully while I explored his torso. "You better be," I snarked back. He tried to kick me off but seemed much weaker than me. I had him pinned completely. Yet hidden underneath my passing revenge was a bubbling desire to just keep going. Keep tickling Jess, tease him more. I looked at his body in my arms and his begging eyes, listened to his cascading laughter, and realized how attractive my roommate was.

Soon I moved my hands down and under Jess' sweater. In between staggered laughter he cooed an, "OooOohh," welcoming my advance too with a warm smile. My fingers grazed his bare skin, smooth and supple, and I began tickling him again, nicer now. Jess quickly dissolved back into giggles and squirms but embraced my teasing happily, no longer fighting back. Like spiders my digits crawled up his sides, driving him insane the whole way. I was slow, soaking in Jess' titters and taking my time to hover extra sensitive spots for a moment longer. Eventually my hands lay before his underarms, my nails scrawling his top ribs in wait. Jess' giggles perked slightly and he got the message. He lifted his arms up, allowing me into his pits. My hands danced in, forcing gentle cries out of Jess who struggled to keep his arms up for me. "Tickle, tickle," I whispered sensually.

Jess was noticeably enjoying his suffering, glancing at me with doe-like eyes and a bitten lip waivering against laughter. Tears had welled in the corners of his eyes too. Parting our stare, I looked down to notice Jess' sweater had ridden up with his raised arms. Skin from the low hem of his skirt to the top of his waist lay nakedly exposed. Almost on instinct, I bent down and lowered my face to Jess' bare stomach. My lips met his torso and I began kissing across the area. Jess moaned faintly amidst his giggles as I worshiped his midriff and tickled his armpits at the same time. "I didn't expect this," he uttered barely, his mellow words taken by a distant wind. "Neither," I said back. We shared a chuckle.

Jess' skin had a flowery aroma and tasted subtly sweet on my lips. Sweeter than that yet was his intimately-matted voice. I wanted to hear this boy orgasm. Like rainfall my hands trickled out from Jess' helpless armpits and down his chest. My fingers found his nipples and began to tease, rubbing each one between my thumbs and forefingers. Jess whimpered loudly under my treatment. Listening to him, ravaging his bare stomach, I pondered on how sweet this revenge had turned for the pair of us. My kisses pathed down, following his light happy trail to where skin met his skirt's hem. In a glance I noticed Jess's erection stood like a mast under his clothes. While kissing along his hip I let my hands roll off Jess' now erect nipples down to meet my head. I reached for Jess' skirt with both hands, pulling it down slightly and exposing largely his hips.

"I don't need that," Jess said lewdly, motioning to his skirt. I sat up and helped him kick it off along with his underwear. He then took off his sweater and me my shirt. Aside from his nylon stockings and the bows in his hair Jess was naked, and me half so. I admired him gorgeously for a second, sex polluting the hot air of our room. His cock made my palette wet and my eyes bright. It was bigger than mine, though not by much, and like most the rest of him it bore little hair. Jess waited patiently, perhaps taking me in also, before I dropped my head back down to pamper him once again.

This time my lips and hands found his delicious thighs. Jess spread them himself. My lips fell first onto his left leg. Like a dog I lapped at the bare skin peeking from the lacey fabric of Jess' stockings. Flowing moans and whimpers escaped Jess' mouth revealing a surprising sensitivity even for him. Intricately I teased at his thigh with my tongue and lips, soon using my hand to survey the other one similarly. As I moved closer towards Jess' pelvis, both thighs began receiving equal treatment, worship and kisses moving fluidly between them. Both my hands also tormented Jess' supple legs with massages and tickling. He was in heaven, giggling and moaning, and I was pleasuring an angel.

Jess was spent though, his thighs ravaged by play and his erection aching and desperate for attention. I chose to sympathize, my kisses now landing on his pelvis, closer and closer to his hard cock. One of my hands cupped Jess' balls while the other found its way to the innermost part of his thigh and tickled it with a squeeze. Jess bit down on the second knuckle of his index finger, failing to contain a squealing laugh as he bucked. "MMEHERCEHHEYY," he cried out. I stopped quickly, scribbling away softly with my nails instead. He settled but continued through giggles. "Ihihii n-need tohoho cum. Plehehease let mehe c-cum."

"Have you learned your lesson?" I asked coyly while fondling his balls, deviousness shaping my smile. "Mmhmmm," he said with an exhale. I moved that hand up where it met the base of his dick in a hold, after which my mouth found his tip. A puddle of precum had formed on his cock's head. I licked it off and took Jess' erection into my mouth. Instantly his head fell back, sinking into my blanket with a whimper. "So sensitive," I slurred, my mouth full. With another accompanied cry he nodded roughly in agreement.

Taking in Jess' manhood, it tasted mild but clean, a freshness oddly reminiscent of avocado. I felt his heartbeat on my tongue, and a pale twitching as I tested to pleasure him. I began to enjoy his tip in a slobber. My hand had begun to move up and down his shaft now too, jerking him in a firm grasp. With my spare hand I found his nipple again. In its neglect it had turned more flaccid, and so I took to pleasuring it attentively. From all angles I worked to make Jess blow. Jess was not shy in his ecstasy either, I alone there to adore his reactions. As he got closer his moans became loud and careless, filling our bedroom entirely. "I'm about to cum," he announced in an erotic glaze. I egged him on. " Please come for me," I said against his cock, almost begging.

Jess soon came crashing over the edge. His body convulsed under mine as a wave of pleasure flooded through him. Hardly with time to react a shot of cum filled my mouth. I pulled my face away, finishing Jess instead with my hands alone. Load after load arched onto his stomach in orgasm. The one in my mouth was almost hot, tasting richly salty with a creeping sweetness under my tastebuds. Jess groaned as his orgasm died off.

A welcoming smile now pressed his cheeks. "You're good at that," he hushed romantically, heavy breaths raising his chest. "Thanks, first time," I said back. Jess raised an eyebrow. Embarrassed, I was quick to explain, "With a guy, I mean."

"Oh," Jess said, "good?"

"Good," I smiled back genuinely. It was good, though unexpected. I gazed upon him lying there, my hand still holding his cock. It was soaked and now had turned a little flaccid, cum dripping on to my closed fist. I let go and went to lower my head. He giggled cheerfully, accepting my last bit of fun. I ran my tongue up Jess' body, licking his stomach clean of his warm cum. Once more my hands explored his torso too in a spider-like tickle. Jess let himself laugh comfortably. "Behehhee nihihhice," he sang. Goosebumps speckled his teased skin. I kissed him back up his torso, finding myself at his chest where his eyes were radiantly closer to me. His long nails began raking through my hair as I rested my head still against him, finally retiring for the night.

I was drifting off as Jess spoke. "I can finish that assignment of yours if you'd like." A relieved sigh left me as I nuzzled Jess' chest lovingly. "Please."

"Okay," he said in a chuckle, "But you owe me. Next time, you're getting tickled."

"Fine," I laughed, laying a single smooch into the center of his sternum.