[FM] My [18F] first time having someone [22M] fuck me with a strap on [trans]

[I hate writing notes at the beginning of stories, but this one is important. Before you write a transphobic comment questioning or joking about Ben’s gender – don’t. Just don’t. Trans men are men. Trans women are women. Transphobia and/or fetishization will not be tolerated in the comments. I’ll be monitoring them closely, and I will block and report you faster than you can say “[J.K. Rowling](https://www.thetrevorproject.org/2020/06/08/daniel-radcliffe-responds-to-j-k-rowlings-tweets-on-gender-identity/).” Happy to answer questions if they are politely phrased and coming from a place of genuine curiosity, but you have to remember that I am not trans, and I am not representing the trans community. [Here](https://www.thetrevorproject.org/resources/trevor-support-center/a-guide-to-being-an-ally-to-transgender-and-nonbinary-youth/) is a good introduction to being an ally to trans and nonbinary people. Enjoy the story!]

From the moment I met Ben, I thought he was hot as fuck. He wasn’t much taller than I was, but he oozed confidence with every smile. It helped that he always dressed like a French author on a jaunt on the Riviera and generally looked as if he belonged in a black and white film with a cigarette dangling from his lips and a typewriter in front of him. His short blond hair was always coifed, his scruff impeccably trimmed. I wanted to cut my lips on his jawline.

Ben was the TA for my first semester freshman seminar, and I quickly developed a fat crush on him. I’d lean on my hand during class and watch him talk while fantasizing about him burying his face between my legs until I’d cum against his tongue, his scruff tickling my inner thighs. But he was my TA. And he clearly took his job seriously enough to not sleep with a student. I settled for being a suck up, going to every single one of his office hours and making damn sure he knew my name and face. And the sight of my tits pushed up to my neck in a low cut top. I obviously never touched or overtly hit on him, but I couldn’t resist being a tease.

We developed a solid friendship during the semester, or at least as solid as possible when one person has a say over the other’s grades and refuses to give out his number in the name of professionalism. He’d give me advice about adjusting to college. I’d flirt as much as I could without crossing any lines. He was intimidatingly well-read, and I found myself checking out authors he recommended so I’d have more topics I could discuss with him. At his encouragement, I read about race, gender, and sexuality and began to understand my own identities more. For a while, I thought he might be gay, but then he mentioned a recent ex-girlfriend. Just maybe I had a chance after the semester ended.

Over winter break, I got my grade for the class. Finally! No more conflict of interest! I was determined to fuck Ben as soon as the spring semester started. Our first full week back, I “happened” to bump into him in the campus gym (meaning I saw him walk up to the entrance through a window and cut my workout in half so I could intercept him near the front desk), my cheeks flushed and my body barely covered in a skin-tight sports bra and leggings. “Hey, stranger!” I panted, dabbing at my face with a towel, “How was your break?”

“It was good! Saw some high school friends, procrastinated on my thesis. The usual. Did you go home?”

“Yup! Only wanted to murder my siblings a couple hundred times each, so I’d call that a success,” I kidded, shaking out my limbs.

He laughed, his eyes crinkling at the corners. Fuck, he was handsome. He had grown out a winter beard, and it suited him well. Our month apart had done nothing to quell my interest in him. “Glad you didn’t follow through,” he chuckled, “We’d miss you around here.”

“I never said I resisted the temptation,” I joked, choosing my words intentionally, “I’ve never had a lot of self control.”

He chuckled. It was something! We chatted comfortably, and he responded more to my flirtations than he ever had before. I began stretching innocently, pushing my tits out as I extended my arms and oh-so-casually showing off my ass and legs in a lunge as we spoke. His eyes almost imperceptibly followed my movements. Maybe he wasn’t impervious to my charms? I desperately wanted to just bluntly ask him out, but his skittishness made me think a more subtle approach was necessary. It didn’t end up mattering.

“So listen,” he said slowly, not meeting my eyes as he fidgeted with the zipper on his gym bag, “I’m not your TA anymore, so I don’t think I’d be in trouble if I invited you to a party I’m throwing on Friday?”

FUCK YES. IT WAS ON. “I’d love to come!” I beamed, “I’ll give you my number so you can text the details?”

“Oh, uh, yeah, that works!” he stammered, getting out his phone.

I was a little thrown by his surprise. Was he not indicating interest by inviting me? Or was he just nervous about getting in trouble for drinking with an underage former student? I gave him my number, my eyes flickering across his face for any hints. With an awkward, one-armed hug, we parted ways, leaving me confused but excited for Friday.

We texted somewhat during the week, but he went back to ignoring my flirting. I figured it was either disinterest or having no idea how to flirt over text, but the end result was that I still had no idea where we stood by the time I left my dorm room Friday night. Music filled the courtyard of his apartment complex, and I shivered nervously as I opened the door to his unit. Waving at some of the partygoers I recognized and dropping my coat on a chair, I scanned the living room for any sign of Ben. He was nowhere to be found.

As the youngest person in attendance, I felt a little on edge. Liquid courage was necessary. I helped myself to a cup of jungle juice, introducing myself to the closest group of people and sipping on my drink as I tried to stay calm. “Lily!” Ben’s voice called out, “You made it!”

He wrapped me in a warm hug from behind, his chin on my shoulder. “I told you I would!” I laughed, my heart pounding with delight as I rotated in his arms and hugged him back tightly, careful not to spill my drink on him.

What the fuck? He was weird the whole week but suddenly I was the guest of honor? Not that I was complaining. FUCK his body felt good on mine. “Great, you have a drink already!” he smiled as he pulled away, his hands lingering on my waist, “Can I get you anything else?”

“What a considerate host!” I teased, plotting a way to assess his feelings, “But I’m all set. Maybe instead you could introduce me to your hot, single friends?”

He laughed, but one of his hands held the small of my back possessively. “You’re way too good for any of them,” he whispered, leaning in with vodka-scented breath.

My eyes flickered down to his lips. “Oh really? You sure you’re not just saving me for yourself?”

He let me go. Fuck. I pushed too far. “Come on,” he smiled softly, gesturing ahead of me, “I’ll introduce you to my freshman year hall-mates.”

The rest of the night, I drank copious amounts and tried to ignore my disappointment. His friends were lovely, but they weren’t the reason I got dressed up. It was also clear they weren’t particularly looking for new friends in their last semester. I wasn’t offended; I was frustrated over spending an evening with a bunch of people I’d probably never see again while the boy I liked avoided me. Why did he even invite me, a freshman, to a party with his close friends if he wasn’t going to talk to me?

After a couple hours, I stumbled into the kitchen to get some water and found myself alone with Ben, who was rinsing out some cans and bottles in the sink. I leaned against the counter next to him and waited. The combination of his thin but muscular frame clothed in a white button-down and his short, straight, blond hair perfectly coifed as usual made him look exactly like Draco Malfoy with a beard, so I obviously told him as much. I didn’t have anything left to lose by being clear about my interest. “Has anyone ever told you that you look like Tom Felton?” I slurred, placing down my empty red solo cup and struggling to hop onto the counter.

“The guy from *Harry Potter*?” he laughed, dropping a can in the sink and gripping my waist to help me up on the counter.

A jolt burst through me at his touch. “Yeah, the sexy mean one,” I flirted shamelessly, smiling down at him as he stood between my legs, his hands slowly trailing down my hips to squeeze my thighs over my tights.

My panties dampened, his hands far too close to my pussy to be unintentional. “No, that’s a new comparison,” he murmured, “I hope I’m not that mean.”

“That’s not the part I was comparing,” I whispered, grabbing his shirt collar and gently pulling him towards me.

Ben turned bright red, his dazzling smile taking up the majority of his face as his face stopped mere inches from mine. “You’re drunk,” he breathed, his hands slowly dragging up my legs until they slipped under the hem of my dress, his thumbs gliding down to my inner thighs.

Oh my fucking god. He wanted me. I spread my legs more. “And you’re hot,” I countered, my breathing turning into pants as his fingers got closer and closer to where I needed to be touched.

“I’ll get you some water,” he deflected, grabbing my cup and turning towards the sink.

Fuck. Well, that was a clear rejection. At least I had my answer. After months of flirting at him and two clear moments this evening where he could have taken things further, it was clear he wasn’t interested. Disappointment and confusion flooded my veins. Why did he invite me? Why had he been so excited to see me? Why had he kept touching me? I hopped off the counter, took the cup of water without making eye contact with him, and walked back into the living room as the world spun around me.

The next day, I woke up but kept my eyes closed, a slight hangover tightening in my forehead. Shit. Jungle juice, my old enemy. After a moment, I opened my eyes, rolled over, and saw Ben asleep next to me. Wait. Where the fuck was I? I looked around to find unfamiliar posters. The fact that I wasn’t in a tiny dorm twin bed also gave away the fact that I probably wasn’t in my own room. “Ben?” I whispered, touching his shoulder.

“Hey,” he murmured sleepily, smiling softly as he woke up.

“We didn’t have sex last night, did we?” I asked nervously.

“Oh my god, no,” he assured me, suddenly wide awake, “You were too wasted.”

“But I still crashed here?” I laughed, confused by drunk me’s actions.

“I didn’t think I could get you home safely, so I made you drink like a gallon of water and let you sleep here. You insisted on taking the couch, but then you came back in my room after half an hour and asked me to cuddle you.”

I blushed and buried my face in my hands as the entire evening came flooding back, peeking at him through my fingers and cringing with embarrassment when I remembered my obnoxiousness. I am comfortable expressing my interest, but I do NOT chase after people. Either they want me or they don’t. “Shit,” I murmured, “I’m so sorry if I made you uncomfortable. It’s really uncool how aggressive I was last night.”

“No, Lily, not at all,” he placated, his eyebrows raised in surprise.

“I came on so strong. I feel like such an asshole. And then I made you cuddle me?”

“You didn’t make me do shit. I really wanted to,” he insisted, pulling my hands away from my face and squeezing them once before dropping them, “And I liked how assertive you were. You were just too drunk to do anything more once we were alone.”

He… liked it? Liked me? Oh my god! I beamed despite my embarrassment. “Thank you for taking such good care of me,” I whispered shyly, “Did I humiliate myself in front of your friends?”

“You held it together. I didn’t even know you were trashed until you were suddenly the last person here and couldn’t stay upright.”

“You’re sure I didn’t cross any lines?”

“I’m sure,” he insisted, “You kept your distance after you left the kitchen, and I actually thought you were really fucking pissed at me until you asked me to spoon you.”

“That’s because I *was* pissed at you,” I laughed, “You flirted with me hardcore and then turned me down the second I made a move.”

He flushed and didn’t meet my eyes. “Yeah. You’re right. I’ve been giving you mixed signals, and I’m sorry about that. I just, um, well, I needed to talk to you about something before we thought about hooking up. And a party wasn’t the best setting.”

“Ok?” I murmured, adjusting myself against the pillows.

He took a deep breath. “I’m trans. I was assigned female at birth.”

“Oh!” I exclaimed, “Ok! Thank you for telling me.”

“Does that change anything?”

“Of course not. You’re Ben. You’re hot. I want to hook up with you.”

He let out shaky laugh that was more a sigh of relief and smiled at me again, tentatively reaching a hand out and stroking my hair gently. “Have you slept with a trans person before?” he asked softly.

“No,” I replied honestly, scooting closer to him, “But I’ve slept with people with all kinds of genitalia. Not that it’s my business what you have going on down there. Just know, if this ends up happening, it’s all good with me.”

“I don’t mind talking about it with you. Especially since I’d really like us to have sex, and you should probably know what’s ‘going on down’ there before we do,” he laughed.

“Then tell me already,” I smiled eagerly.

He laughed again. “I came out to my parents right after graduating high school, got on T shortly after, and they told me over my first winter break that they’d pay for top surgery once I’d been on hormones for a year. I had the procedure during the nexts summer, and that’s the extent of the surgery I’ve had.”

“I’m so glad they were supportive!”

“It wasn’t that much of a surprise to them,” he laughed, “I came out as queer years before, and I’d been telling them I was a boy since kindergarten. They just thought I’d grow out of it or end up a butch lesbian. They’d never really heard of someone being trans outside of shitty Hollywood tropes.”

“It must’ve been scary to learn about it on your own,” I whispered, lacing my fingers through his.

He squeezed my hand and shrugged. “There was a queer youth center on my walk home from school. I had to make sure I wasn’t followed whenever I went, but they helped me learn the vocabulary for everything and get resources and understand who I was.”

“Still.”

He rubbed his thumb across the back of my hand. “Honestly, I don’t want to dwell on the shitty parts. Transphobia and self doubts obviously pop up, but I’d rather talk about that with my therapist or my trans friends, you know?”

“Totally understandable,” I smiled, slowly dragging one of my legs up his to drape over his calf, “Let’s focus on the good parts, then. Did you start college having transitioned?”

He scooted closer, dropping my hand to wrap an arm around me, his hand rubbing my back and then resting just above the curve of my ass. “Yeah, everyone here knows me as Ben. I used binders for my first year and passed well enough. The school used my chosen name on my ID, and none of my professors have ever deadnamed me.”

I lifted a hand to brush back his hair and then cup his face, my thumb skimming across his cheek. “I’m glad. Do all your friends think you’re cis or are you out to them?”

He pulled himself even closer until we were flush together, my leg still draped over his. My lungs tightened. I had never been this close to him before — somehow he was even more handsome with my face centimeters from his. My heartbeat slid down my body to thump in my clit. “I’m out to my good friends and the women I’ve dated,” he whispered, “But I’d rather not have the whole campus know. You never know when somebody’s gonna cause a problem.”

“Also understandable,” I murmured, hitching my leg higher up his and pausing before running my fingers along the chest hair that was peeking out over the top of his shirt, “So does that mean I’m your good friend or a woman you’re gonna date?”

He blushed wildly under his beard and locked eyes with me, smiling from ear to ear. “Both, I hope.”

“I hope so too,” I whispered, grinning as he tangled a hand through my hair on the back of my head.

Ben’s expression changed a little. “But I’m graduating at the end of the semester. I don’t want to start something if you’re not cool with having an end date,” he insisted, his eyes flickering between mine.

“Honestly, I’m not looking for something serious. It’s my first year of college. That sounds kind of perfect.”

“Well, then, good,” he stammered, flustered by how well this was going, “I, uh, then, I’d like to kiss you now, if that’s ok.”

“Kiss me, Draco.”

He laughed and closed the remaining distance, pressing his soft lips against mine as his beard scratched my chin. I hummed quietly and kissed him back deeply, parting my lips and running a hand through his silky hair. He pulled back and smiled at me, running a hand up and down my back. I bit my lip and smiled back at him. “I should probably shower before we take this any further,” I whispered, “As much as I’d like to get started this second, I’m practically sweating jungle juice.”

He shoved his face in my armpit and inhaled deeply, laughing as I giggled and shrieked and tried to pull away. “You smell fine to me!” he exclaimed.

“You’re so gross!” I cackled, turning away from him.

Ben grabbed my waist and pulled me against him to spoon, wrapping a firm arm around me. He kissed my cheek and whispered in my ear. “Do you really want to get out of bed already?” he murmured, his hand teasing at my nipples over my slutty dress from the night before.

My panties flooded. “No,” I admitted, trying to figure out how to outmaneuver him before I just gave over to my animal instincts and fucked him while feeling gross, “But I want you to bury your face in my pussy and lick me until I cum, and I need to shower before I’d feel comfortable with that.”

I turned my face and pecked his lips as he froze in shock. For all my flirting, I had never been so overtly sexual – I don’t think he expected my particular brand of outright raunchiness. This was going to be really fucking fun.

Getting out of bed, I pulled my dress over my head and unhooked my bra, letting it fall to the floor as I bent over and took off my tights and panties, displaying my ass and letting my pussy peek through my legs. Turning around, I smirked at his expression of disbelief and horniness at my confidence and suddenly naked form. “You’re welcome to join me, though,” I offered, gathering my long hair and pulling it over one shoulder.

He shot out of bed, whipping his shirt off and pulling down his boxers as he kissed me hungrily. Our naked bodies pressed together, our tongues tangling. I moaned against his lips and wrapped my arms around the back of his neck, pressing my tits against his chest. My nipples brushed against his faded surgery scars, and I paused. “Where can I touch you?” I asked breathlessly, “Is there anything I should avoid doing or saying?”

“You can touch me anywhere,” he murmured, kissing down my neck as he cupped my ass with both hands and pulled me tightly against him, “Head’s up that my clit’s bigger than you’re probably used to, and I might need lube since I don’t self-lubricate as much now. You can use anatomically descriptive words, but don’t use feminine words like ‘pussy’ or ‘cute.’ Ok?”

“Definitely ok.”

“And I’m kind of a dom. Nothing too crazy, but I like to take charge.”

“Take charge, then,” I whispered, tilting my face up to his.

He captured my lips roughly, biting down on my lower lip and then nibbling it as his hands slid up my body and tangled into my hair. Fuck, I was in heaven. He kissed up my jaw and sucked on my neck for a moment before teasing my earlobe with his tongue. “What about you, Lily?” he whispered, sending shivers up my spine, “Any warnings, kinks, or preferences?”

“I love dirty talking and can get really loud if I’m not careful,” I admitted, my eyes closing as I rolled my head to the side to provide him with better access.

He chuckled and bit down softly on my earlobe. “Get loud, then,” he whispered, turning my face to devour my lips again.

We stumbled over to the bathroom, barely detangling ourselves enough to turn on the light, bathroom fan, and shower. We washed each other slowly, massaging soap into each other’s skin and gliding our tongues together every time we were face-to-face. I couldn’t get enough of him. This wasn’t just triumph over finally confirming that he wanted me as much as I wanted him. This was something even better.

I felt clean within the first ten minutes of being in the shower, but I lingered, wanting to draw out our time in the warm water as long as possible. He groaned softly as I rubbed his back, following the soap and water with soft kisses as I slid a hand around his body to start rubbing his clit. He guided my hand to pinch it gently between my thumb and pointer finger and jerk it softly. “Like that?” I asked quietly as I began doing the motion on my own, pressing my tits against his back.

“Yes,” he whispered, his head falling backwards to expose his sharp jawline, the facial hair on his cheeks and jaw a reddish, darker blond than the hair on his head.

I kissed his cheek as I continued stroking him, scraping my teeth along his jaw and then running my tongue up his neck. “You are so fucking sexy, Ben,” I moaned, “Can I suck you?”

He turned to face me and helped me lower myself to kneel on the shower floor, his hands holding my hair back as I leaned my face towards his center. I took his hardened clit into my mouth and suctioned my lips against it, bobbing my head a few times while maintaining eye contact. Moaning softly, I buried my nose into his pelvis and flicked my tongue against his clit rapidly, teasing the soft tip.

“Oh fuck, do that again,” he groaned.

Trailing one hand up his happy trail to run my fingers through his chest hair, I brought the other hand around to cup his ass and pull him harder against my face, swirling my tongue around his clit and looking up to meet his gaze. A genuine smile crossed his lips, an expression of pure bliss on his face. “Can you finger me?” he asked softly as he watched me suck him.

I pulled away for a second to speak. “Front hole or back?”

“Front.”

I slid my fingers in my mouth to lubricate them and started teasing his entrance. He spread his legs slightly. Pushing one finger inside and smiling as he groaned, my mouth enveloped his clit again as I alternated sucking it and flicking my tongue against it. “Oh my god, Lily,” he hissed, pressing my face against him, “Please don’t stop.”

I pushed in a second finger and curled against his g-spot over and over again, loving the way his knees buckled as I pleasured him. I became more confident as I worked him, pulsing my fingers inside him as I lavished his clit with my tongue. Closing my eyes, I hummed contentedly against his clit. His hands tugged on my hair, his hips gently thrusting as he groaned. “I’m getting close,” he murmured.

My movements stayed consistent, and I earned Ben’s deep orgasm within another minute. He called out my name, the sound bouncing off the shower walls as he pressed my face against his pelvis, his legs trembling as his hole clenched around my fingers. Triumph coursed through my veins, my pussy getting wetter and wetter as he came. As soon as his orgasm slowed, he yanked me to my feet, his hands cupping my face as he devoured my mouth, murmuring praises between frantic kisses.

Without warning, he spun me around so that my hands braced me against the wall, and he held me from behind, his hands gripping my tits and pulling my nipples roughly into hardened points as he rubbed his pelvis against my ass. “Fuck, Lily,” he groaned, “I’ve been wanting to fuck you for months.”

One hand trailed down to my clit, and he began rubbing me gently. I moaned softly as he continued talking. “Do you think I didn’t notice the way you’d always show up to office hours in tiny skirts and flirt with me? I’d get so fucking turned on that I’d have to run home to jerk off every time. Fuck, you have no idea how hard it was to stay professional when all I wanted was to make you scream my name.”

“Ben…” I moaned, arching my back and pressing my ass against his pelvis.

“What do you want me to do to you?” he whispered.

“Everything?” I whimpered breathlessly.

He removed his hand from my clit, turned me around, and pressed me against the shower wall, pushing two fingers into my pussy and scraping his teeth against my neck as I moaned. Fucking hell. He pulsed his fingers inside me as he sucked on my neck. My legs buckled, his firm body the only thing stopping me from sliding to the shower floor. All too soon, he removed his hand, kissing his way up my neck to my lips. Turning off the shower and pulling a towel off the rack, he wrapped me up in it and kissed me softly. He slid his tongue against mine and then pulled back to kiss up my jaw. “Get on the bed face down, your ass in the air,” he whispered in my ear, “You can touch yourself while you wait for me to put on my strap on. But don’t cum.”

My pussy was wetter than I ever thought it could be. I did as I was told, drying myself off, handing him the damp towel, and padding back to his room to get on the bed. I started off on my hands and knees but then tilted my chest to the mattress, bringing one hand between my thighs to gently circle my clit. I was so sensitive that my abs spasmed softly whenever I pressed too hard. My pussy dripped at the idea of Ben coming back in his room to see me like this, displayed for him and desperately ready to be claimed.

He returned soon after, closing the door behind him. “Look at you,” he murmured, dragging his hand up my thigh to squeeze my ass.

Sparks followed his fingertips. I stopped touching my clit, breathlessly waiting to see what he’d do next. He knelt on the ground behind me, kissing along my inner thighs and dragging his tongue up and down the outside of my vulva, never once pushing inside me or touching my clit. I panted, arching my back to give him better access. He lightly nibbled my labia with his lips and teeth and then pulled back, spreading my cheeks and staring into me. “Fuck, your pussy is beautiful,” he murmured, pressing a soft kiss directly on it, “I can’t believe I made myself wait so long to see it.”

“Ben…” I whimpered, needing more.

He pushed his face between my cheeks, his nose pressing against my ass as his tongue finally slid inside my cunt, his beard scratching my inner thighs. I let out a soft cry and pushed back against his face, grabbing the sheets with both fists as his tongue pulsed inside me. His arms looped around my legs, one of his hands reaching up to gently rub my clit. “Oh! Oh my god!” I shrieked, my legs shaking as he expertly worked me.

He groaned into my pussy, his long tongue pushing deeper inside me. “I — I think I’m gonna cum?” I moaned, my orgasm arriving far too quickly.

Ben’s tongue immediately withdrew. “Not yet,” he whispered, kissing my ass cheek again as he slowed and stopped his fingers’ massaging of my clit, bringing his hand around to rub up and down my labia, spreading my juices to my clit.

He pushed two fingers inside me from behind, immediately locating my g-spot and pressing hard against it. I moaned loudly, my face pressing against the bed. “Oh my god, Ben,” I groaned deeply, pushing back rhythmically against his movements as he fucked me with his fingers.

He laughed and placed a soft smack against my ass with his other hand. “You have the sexiest moans,” he whispered, scraping his teeth against my ass cheek and then kissing it, “You’re gonna inflate my ego.”

“I’ll do whatever you want as long as you keep going,” I whimpered, my hips moving desperately.

He laughed again softly and kept working me, his delicious fingers somehow touching me exactly where I needed before I even knew I needed it. My soft whimpers were honestly a little embarrassing in their desperation, my legs spreading even more for him as I begged for him to keep massaging my cunt. “I could keep going. Or, I could fuck you with my cock now?” he murmured after another minute of my mewling and panting.

“Please fuck me,” I begged.

Removing his fingers and giving me another deep lick with his tongue, Ben stood up and aligned his lubricated strap-on with my entrance. “Talk about it as if it’s a part of me,” he whispered, pushing in the tip and then removing it a couple times, teasing me and preparing me for his girth.

“Please, Ben,” I moaned, “I need your cock.”

I reached behind myself and spread my cheeks for him, looking over my shoulder and biting my lip. He groaned softly, staring at my pussy. Grabbing my hip with one hand and using the other to guide his cock, he slowly pushed into me to the hilt. “Fuck, you’re tight,” he hissed.

“Oh! Oh fuck!” I whimpered, pushing back against him as he started thrusting slowly, “Can you feel how wet I am for you?”

“Yes,” he groaned, tightly gripping my waist with both hands as he began pushing into me rhythmically, “Fuck, Lily.”

My body jostled with the force of his thrusts. I moaned loudly. “Fuck me, Ben, oh my fucking god, fuck me harder!”

He began pounding into me, pushing deep inside me and stretching my cunt. “Your cock feels so FUCKING good,” I screamed, my hands leaving my ass cheeks to grab fistfuls of the bedsheets again.

“Ohhh my god,” he moaned, his pelvis slamming against my ass over and over again.

I reached a hand between my legs and rubbed my clit roughly, the orgasm from earlier returning with a vengeance within minutes. “Ben! Ben I’m gonna cum!”

He stopped his thrusting. I let out a loud whimper, and he placed a hard smack on my ass cheek. “You’ll cum when I’m ready to stop fucking you,” he whispered, slowly dragging his cock out and then just as slowly pushing it back in, “Because you’re a tease. And teases get what they deserve.”

I moaned into the bed, all the tension leaving my shoulders as he slowly, painstakingly massaged my cunt while we both caught our breaths. Each inward push sent sparks shooting up my pussy all the way to my fingertips. Each outward pull sent pleasure dripping down to my toes. I could have stayed like that forever — my ass displayed for him as he built up the pressure and anticipation to unbearably high levels.

“Get on your back,” he ordered, pulling out all the way.

Flipping over and centering myself on the bed, I spread my legs and grabbed my ankles. He covered me with his body, kissing me deeply before pulling back to slide his cock up and down my labia. His harness was tied around his hips, his cock a perfect replica of his skin tone. I watched his abs ripple as he isolated his hips. “Ben,” I moaned, “You are so fucking sexy.”

He smiled at me. That heartbreaking, wonderful, handsome smile. My pussy flooded even more. I stared at his cock as he tapped it against my clit, sending jolts of pleasure up my body. “Fuck, you’re big,” I whispered, biting my lip, “I could feel it, but damn that’s an incredible cock.”

His smile turned arrogant as he aligned his tip against my entrance and pushed in with one fluid thrust, watching me with pride as my eyes fluttered closed with pleasure and I let out a long, deep moan. He rested his body against mine and buried his face in my neck as he began thrusting again, his scruff delightfully scratching my skin. I released my ankles to rake my fingers down his back, moaning into his ear. “Will you please let me cum this time?” I begged, “I want to cum on your thick cock. Don’t you want to feel my pussy tighten around you?”

He groaned and turned his face to kiss me, his tongue pushing forcefully into my mouth as he pounded me into the bed. I wrapped my legs around his waist and held onto his back, my eyebrows knitting together. Small gasps and moans of pleasure spilled from my mouth with every thrust. He broke the kiss so he could pant heavily, his cheeks flushing from exertion. “You can cum this time,” he promised breathlessly, “I’m also close. Can you suck me again?”

“Do you want me to suck your cock while I rub your clit?”

“Oh, fuck. Yes. I’ll have to loosen my harness a bit after you’re done.”

“Don’t worry, you’ll know when I cum,” I laughed, my giggle turning into a moan as he tucked his face back into my neck and fucked me harder and harder as he bit and licked and sucked on my skin.

Our bodies smacked together loudly, though the slick sounds of his cock filling and emptying my pussy were drowned out by me screaming his name, my fingers clawing at his back as he thrusted on top of me. “Ben! Oh my fucking god!” I called out, momentarily forgetting that his neighbors might hear.

Fuck it. Let them hear. He deserved the knowing smirks and pats on the back from the frat bros in his apartment complex. I didn’t mind being the reason his hand would cramp from high fiving. I slid my fingers between our bodies and rubbed my clit aggressively, that same orgasm coming back within seconds. “Cum for me, Lily,” he demanded.

It took very little coaxing before I was finally, blissfully tipping over the edge, my exhausted, overly teased body exploding with pleasure. “Ben! I’m cumming! Don’t stop! Oh fuck! Don’t stop don’t stop don’t stop! Oh my GOD you feel so fucking good!” I screamed, my throat hurting from the exertion of my yelling.

He groaned loudly and kept pounding me through my orgasm, his thrusts becoming harder to maintain as my pussy tightened violently around his cock. I buried my face in his shoulder as I let out a sob of pleasure, the hand not rubbing my clit grabbing onto his back and holding him to me tightly as I came harder than I could remember. This was ecstasy. I would worship at his feet if it meant he would keep fucking me until the moment he had to leave for commencement. He kissed my cheek as he maintained his rhythm as much as possible, whispering my name and murmuring words of encouragement to coax me through my peak. My spasming body finally slowed and relaxed against the bed. He kissed me deeply and remained docked inside me for a moment, slipping his tongue into my mouth and slowly stroking mine with soft movements. I pushed on his chest to get him to break the kiss. “Fuck my mouth,” I demanded, exhausted but determined to make him cum again.

He pulled out and straddled my hips, loosening the harness a bit before bringing his body up mine to rest on my chest. I took his cock into my mouth and sucked it eagerly as I slipped a hand under the strap-on to jerk his clit again between my thumb and pointer finger. Matching my rhythms to each other, I increased my speeds, my fingers and mouth working in tandem. “Oh, fuck, Lily, I’m gonna cum,” he groaned.

I moaned and suctioned my cheeks against his cock, locking eyes with him. Ben’s face contorted with pleasure and he shook roughly on top of me, his torso spasming as he came. He groaned loudly, his cheeks flushing. He looked so fucking handsome that I felt my heart clench, disbelief washing over me that this had finally happened. As he came down from his high, he gently removed my fingers from under his harness, swinging his leg over my torso and collapsing on the bed next to me, still panting and occasionally spasming with pleasure. I immediately wrapped myself around him, peppering kisses on his neck, his jaw, his cheeks, his lips. He kissed me back just as eagerly. I never wanted to leave his bed. “Holy shit, Ben,” I whispered, giggling and burying my face against his chest.

He laughed softly and cupped my face, tilting it so he could kiss my forehead. He smiled at me, both of us flushing as we stared at each other and realized just how severely we had crossed a line we couldn’t uncross. “Not bad, huh?” he smirked.

“You’re packing heat AND you know how to use it,” I marveled, running my thumb along his lower lip.

He scraped his teeth against the pad of my thumb and then kissed it as he retightened his harness. “I’ve been using strap ons for years, even before I came out as trans. It feels natural for me at this point.”

“I’ll fuckin’ say!” I giggled, running my fingers through his hair, “I could have taken it for hours.”

“An interesting proposition,” he murmured.

One of his hands suddenly grasped one of my breasts and teased my nipple as his mouth captured the other. I gasped as he scraped his teeth against it. My nipples tightened into sharp points, my cunt flooding again from his harsh but loving movements. He released my tits and pushed me gently against the bed until I was on my back. “I know we tapped out early this time so I could cum, but you haven’t even experienced the best part about my cock,” he whispered, smiling wickedly at me as he climbed back on top of me, his wide, heavy tip resting against my clit.

Excitement pooled in my belly as I opened my legs for him again, my panting breaths getting harsher. “What’s that?” I breathed, spreading my labia for him as he lined up his cock with my entrance and smoothly pushed inside me, eliciting a slow moan from deep within my lungs.

“No refractory period.”

Source: reddit.com/r/gonewildstories/comments/ht5yli/fm_my_18f_first_time_having_someone_22m_fuck_me