It’s Friday, and I’ve been desperately waiting to get home and see if my package was delivered. When I finally rushed home from work, I was delighted to see it had arrived on time.
“Oh fuck yeah.” I said aloud.
I grabbed it and quickly ran inside my apartment. I tore the package open to reveal an XXL t-shirt that read ‘I <3 Femboys’.
“Yeah, I think that’ll get the message across.” I sarcastically said to myself.
You’re such a dork.
I went to the bathroom and prepared. I had found a cheap, handheld bidet that could be set with more than enough pressure to make sure everything was clean, so I used that before I took a shower. I also took a close guard trimmer and trimmed my body hair, as I found it unsightly. I liked not having much hair, except for on my chest, because it gave me more muscle definition. I took a shower and shaved where I needed to, got out, prepared my hair in the mirror, and went to get dressed.
I put on my ‘going out’ undies, which were tight, black, sheer and slightly see-through boxer briefs that held my ass up. I chose my best pair of jeans, which were denim woven with elastic and contoured my legs well. I put on the shirt and looked in the mirror. I chose well getting an XXL, it made my upper body look huge, and draped over my shoulders nicely. It was tight on my arms, and hid my stomach well enough. I had been bulking this season, and I was up to two hundred twenty pounds. Most of it was muscle, but unlike some guys, I couldn’t be big and absolutely shredded, so I had a small belly to go along with it.
I picked out a brown belt, and brown boots, and headed out the door to the gay club.
The sun was just starting to set as I found parking downtown, and luckily I was able to find a spot for ten dollars nearby the club. When I walked in, I was met with a few stares, and quickly averted my gaze. I was feeling a little overwhelmed, so I kept my eyes to the floor as I walked to the bar. The place was absolutely packed, the music bouncing and thumping, and the atmosphere erotic and exotic. It was amazing, but I was mostly a homebody, so I was very much out of my element. I decided to stand off to the side of the club, within my own space, and just try to absorb and experience everything. I had plenty of time, I didn’t need to rush when I felt uncomfortable.
Several guys came up to me and complimented me on my hair or my shirt, saying it was very bold. I thanked them with a smile. After a while, a man my height, 5’ 10”, approached me.
“Hey.” He said warmly.
He was conventionally very attractive, with longer brown hair and brown eyes, just like myself, except I kept my hair shorter, and I’m sure my eyes didn’t sparkle like his did. I didn’t find him sexually attractive, but he was certainly pleasant to look at.
“Can I buy you a drink?” He asked.
“Please.” I said sheepishly. “It’s so busy, I didn’t even try to get one.”
He smiled with his mouth open. “Oh my god. Big strong man like you and you’re shy?” I heard him as he walked away to the bar. “That is scrumptious.”
He came back a short while later with a fruity drink I had never seen before. He handed it to me and I sipped, it was delicious.
“So, Mr . .” He led on.
“David. Thank you so much, this is really good.” I answered.
“David. I’m Connor.” He took a sip of his own drink, he had got two of the same. “You look completely straight, to be honest.”
I laughed and looked down. “Why’s that?”
He shrugged and sipped. “The jeans.”
“Oh.”
“So are you straight?” He asked.
It was my turn to shrug and sip.
“What does that mean?” He chuckled.
I shuffled my feet. “It’s a long story, and kind of personal . .”
He gestured to our surroundings. “Why else are you here but to get personal? We didn’t come here to judge.” He cocked his head slightly. “Well, some did.” He raised his glass to me. “But I won’t. I may hit on you, but I won’t judge. Promise.”
I smiled, and began. “Well, I’m straight, kind of. When I was in school I assumed I was bisexual, cause of my friend group.”
He looked confused. “Assumed . . You were bisexual?”
I nodded. “My friend group was the gay girls group. They were all anime girls and we hung out all the time.”
“So just you, one guy, and how many girls?”
“Like four core girls, and probably three or four other girls who rotated.”
He nodded. “And you slept with them?”
I shook my head.
“You had a harem and you didn’t sleep with them? Are you sure you’re not gay?”
“Well, I mean, one of them wanted me to teach her how to make out, but we never . . She was catholic. .” I stammered.
He laughed and put his hand on my arm. “Okay, continue.”
“I was friends with all of them, and they were all bi, so I assumed I was bi. I tried to sleep with the hottest gay guy at school, but I guess I came on too strong and never did.”
“Okay . . So, have you slept with a man?”
“I mean, I love women. I mainly hook up with them. But I’ve tried hooking up with guys a few times.”
He nodded, and motioned me to continue.
“The first one was a dud. I feel bad about the second one. I just rode him till I finished and made him leave cause I wasn’t into it anymore.” I said, embarrassed.
He had his hand under his chin, and motioned with his drink. “Okay, so you like butt stuff, at least.”
“Yeah, I always have. It was one of my, y’know, formative . . Masturbatory . . Things.”
You are lethally awkward.
He smiled. “Right. Was there more?”
“There was another guy. He was really nice and cool at first, and we tried to hook up but I wasn’t into it. Afterwards he was kind of obsessed for a bit and I had to go no contact. But that’s been it.”
He nodded acceptingly. “So do you still . . Play? With toys?”
I nodded sheepishly. “Yeah but . . It’s not . . Like-“ I stuttered.
“The real thing.” He finished.
“Yeah.”
“So is the shirt a mating call or a cry for help?” He teased.
“Both.” My face got red.
He smiled. “So you want the femininity, but with the . . Equipment.” He drawled the last word.
I nodded.
“I think my friend would be perfect for you. She’s supposed to be here tonight . .” He looked around. “I’m gonna go give her a call. You hang out here, I’ll be back in a bit!” Connor left, walking towards the door, and said hi to a few people before he went outside.
I stood, silent, and watched all the beautiful men dancing. I saw Connor come back inside rather quickly, much faster than I expected. He was pulling someone behind him, I caught a glimpse of long brown hair. After he navigated through the sea of people, he stood in front of me and presented his friend.
She was shorter than me, probably about 5’ 7”. Her face was exquisite, with sharp feminine features, but a masculine nose and jawline. Her eyes were a catastrophic cacophony of green and brown, perfectly paired into a pleasant hazel. I stared into them, my mouth gaping like an idiot. She was perfect, and I couldn’t breathe.
When she spoke, my knees faltered. “It’s giving younger Fox News dad vibes.”
Her voice was higher pitched than a man’s, but not quite female. I was speechless, and barely registered what she said. She wore a green blouse over budding A-cup breasts, and it complemented her brunette hair. She wore a black pleated skirt with spiderweb stockings that showed off her flawless legs, and I could see an almost imperceptible bulge.
Connor got my attention and motioned to his friend.
I cleared my throat. “Well, I was raised conservative but I’m not, really . . I guess I just have the straight guy style. Sorry, I just . . You’re so . . Wow.” I could barely form a sentence.
She giggled and turned to Connor. “You’re not lying, he is shy. It’s okay, I think it’s cute. Your shirt is a little on-the-nose, but . .” She reached out her hand and dragged her nails down my arm gently, then squeezed. “It makes your arms look really good.” She finished.
Her touch instantly made me erect. I was now regretting wearing jeans. My cock was painfully pressed against the denim, trapped behind the fabric.
“Thanks.” I half said, half whispered.
“David, this is Sierra. Sierra, I think David here has been waiting for you. Right David?” Connor said.
I nodded. “Yes.” I half whispered, half said.
Connor smiled. “This is adorable. Okay, you two hit it off.” He squeezed Sierra’s hand, and left to the dance floor.
Sierra fixed her eyes on me. “So, how old are you?”
“I’m twenty-five. You?”
“Twenty-one. So Connor said you like femboys, but what else are you into?”
I cleared my throat. “Well, I guess you could say I’m a bottom, but, I like being in control.”
“Oh. I haven’t . . Uh . . Done that before.” She stammered.
I stepped towards her, and peered down, inches from her face as she looked up at me. Her eyes flicked from my eyes to my lips as I spoke.
“Learn something new every day, hmm?” I whispered.
“Yeah.” She breathed, her lips parting.
I leaned back, breaking the tension, and saw her bulge had gotten bigger. “Do you want a drink?” I asked.
She nodded, and she closed her mouth as her face flushed with red. “I’ll just, um, I’ll have what you’re having.”
Sierra had sat at a table on the wall while she waited for me. I brought her the drink and sat down next to her, on the same side of the table.
“Here you go.”
“Thank you.” She took a sip. “What do you do for work?”
“Blue-collar labor stuff, basically.”
She swallowed. “So that’s why your forearms are so . .” She dragged her fingers up and down my arm. “Defined.”
I laughed, and dropped the arm she was touching to her thigh. I squeezed it firmly, then moved my hand under her skirt.
“You know I have a-“
I nodded, and slid my hand directly onto her cock. I pinched it gently, feeling it grow in my hand. Her face reddened, and she opened her mouth slightly and I massaged her dick.
“David . . We’re in public . .” She whispered.
I squeezed it gently before slipping my hand back out from her skirt. “What do you do for work?”
She cleared her throat and looked down as she adjusted her skirt so the tent that formed wasn’t as obvious.
“You’re not as shy once you get warmed up, are you?” She accused.
I shook my head. “Is it too much?”
“No, you’re like, heh, exactly my type.” She looked at the ceiling and exhaled loudly. “Oh my goddd.” She snapped her head to me and her hazel eyes pierced my soul. “Are you actually into me, or just trying to fuck cause you don’t pull any girls?”
I met her gaze. “I fuck a few women. They’re not who I want tonight.”
A smile curled on her lips. “Then why don’t you save a girl, and ride a femboy instead?”
“Bet.”
I opened my car door for her and let her get in before shutting it. I got in my side, turned the key, and the engine roared to life. I put it in drive and started heading to my apartment.
“Y’know, driving an automatic sports car is kinda gay.” Sierra teased.
“Is it? Can manual drivers do this?” I replied, then grabbed her thigh, and inched my hand back under her skirt where it belonged.
“David-“ She gasped as my hand felt her hard cock. I slowly began jerking her up and down as I made turn after turn.
After only a few minutes, and more than a few moans, I could feel her precum dripping down my hand. I let go, and raised my hand to my tongue and licked it. Her cum tasted amazing.
Sierra took a deep breath, recovering after I had stopped. She looked at me suddenly.
“Are these windows tinted?” She asked pointedly.
I nodded. “Yeah, why-“
She twisted her knees into the seat, and bent over the center console. Her hands scrambled to undo my belt and pull down my zipper.
Jeans. Bad idea.
After a minute of struggling, she finally freed my cock. I was rock hard, erect at a solid six inches. I was an average length, but I was proud to be nearly two inches thick.
Sierra gasped when she wrapped her hand around me. She could barely touch her middle finger and thumb together. “Oh fuck. We can do what you want, but you have to- you need to fuck my ass with this.” She pleaded.
Before I could reply, she had wet her lips and slid her mouth down over my tip, swirling her tongue and savoring the precum leaking from me.
“Oh fuck.” I moaned, as I used my other hand to recline the seat as far as I could, but still able to see and drive.
Sierra gagged on my cock as she attempted to throat me. She had made it halfway, slobbering sloppily with her saliva dripping down the length of my shaft, though my thighs and down my ass.
She withdrew to take a breath. “I can take this length but . . It’s thick, my mouth is small-“ she wiped her mouth with one hand, then gave me a crazed look. “But Momma ain’t raise no bitch.”
She enveloped my cock once more with renewed vigor, bobbing up and rapidly. Her hand gripped the base of my shaft, and alternated between squeezing tight and soft, while she stroked the several inches she couldn’t take.
“Jesus fuck!” I groaned, her expert head was careening me towards the edge.
I slid my hand down her arched back and lifted her skirt. She was wearing boy shorts underneath. I slid my finger between her ass cheeks and applied gently pressure to her hole. She started moaning on my cock, and I nearly exploded just from that.
“Uuuuughhhhh.” I moaned. I never moaned like this. She was going to make me lose control.
I hooked a finger into the fabric of her underwear, and pulled sharply. I heard and felt it rip under my strength, giving me complete access.
Sierra came up for air, surprised. “Oh fuck.” She whimpered.
I slipped my fingers into my mouth, and put them back where they belonged. I put pressure on her asshole, slowly working it open as she desperately devoured my cock again. She was getting faster and faster, anxious for her reward.
I pressed my finger harder against her hole, and it slipped in to the first knuckle. I moved it, worked it open and loose. She gurgled my cock, clearly enjoying it. I knew I was going to cum soon, so I slowed the car considerably as we approached an intersection. Just as we approached the light, it turned red.
“Relax.” I ordered in a whisper.
I felt her ass loosen, and I plunged my finger deeper, then took my hand from the steering wheel, grabbed her head, and pushed it all the way down.
“Fuuuuuuckkkk I’m cumming. Oh fuck. Holy shit-“ I gasped as I erupted down her throat.
She bobbed up and down, trying to swallow everything of me. I slid my finger out of her, and she lifted her head.
“David!” She yelled.
I looked up and realized the light was green. I kept driving, almost in a daze from ejaculating so hard. Sierra put her head back into my lap and cleaned all the cum she had let spill from her lips. After she was done, she sat back in the seat. She looked very pleased with herself.
After a few moments of heavy breathing, I finally spoke. “I was seriously considering pulling over and fucking you right then.”
“I thought you wanted to bottom?” She asked, puzzled.
“Yeah well, if your mouth is half as good as your ass, I won’t be able to resist fucking you in half.” I growled.
She sat back in the seat and blushed. “We still have all night.” She whispered, then shrugged. “I wouldn’t mind being fucked in half.”
I grinned as we pulled into my complex.
I led her into my apartment, and opened the front door. As we walked inside, I turned to face her.
“Do you wanna take a shower?” I asked.
“Why?” She was puzzled.
I shrugged. “I just wanna try something.”
“Sure.”
We headed to the bathroom and stripped quickly. She followed me into the shower after I had turned it on, and she dragged her nails up and down my shoulders and abs before staring up at me, begging for a kiss. I obliged her, kissing her hard and shoved her against the tile wall, forcing my cock against hers. After a lengthy kiss, I soaped her up and cleaned her well, paying special attention to her ass and cock.
“Are you ready?” I asked after I had rinsed her off.
She nodded eagerly.
I stood her to the side of me, and grabbed a bottle of lube I always kept in the shower. I squirted some on my right hand, and bent down to play with her ass. I played with her cock with my other hand, forcing a moan from her mouth.
“David . . Ugh . . I thought you wanted to fuck?” She asked through gasps.
“We can fuck on the couch. Right now I’m just playing.” I teased.
She leaned her side against the tile and let me continue. After easing two fingers into her ass, I knew she was ready. I pulled out my fingers, then angled my hand downwards, and inserted my thumb inside her. She groaned as I penetrated it fully, then angled it down with force into her prostate.
“Oh fuck. Oh fuck. Wait- oh my gooooood.” She wailed as I stroked her cock at the same time.
Her cock was a little smaller than mine, but I was perfectly happy to stroke her senseless. I kept massaging her ass with my thumb, and soon, I saw precum gushing from her cock.
“Oh fuck- I’m gonna- you’re gonna make me-“
I withdrew my thumb and squeezed the base of her cock, stopping her orgasm in its tracks.
She whimpered as she settled back down.
“Good girl.” I praised.
She flashed her hazel eyes at me. “What are you doing to me?”
I grinned. “Just having my fun.”
After our lovely shower, I left naked, and fetched her a large black hoodie of mine to wear. She snuggled inside of it like it already belonged to her. I sat on the couch and pulled her on top of me. She sat on my lap, straddled my hips, and instantly began grinding into me.
“Is this how you want it, David?” She whispered.
My answer was to reach over to the table at the arm of the couch, and grab a condom and lube. I quickly rolled it into me, and lubed my cock, before lifting her up and aligning at her entrance.
“Be gentle, I’m still really tight.” She pleaded.
I nodded, then inserted myself inside her. She was right, I could barely fit the tip inside her before she stopped.
“Ohhh fuuuucckk.” She moaned.
I reached beneath her and added more lube to my cock and massaged her ring.
“Breathe. Just breath and relax. I know you want all of it.” I cooed.
“Yes Daddy.” She said. She hadn’t realized she had said Daddy instead of David. “Fuck my fucking ass oh my gooood.”
She took a deep breath and sat further down, halfway onto me.
I placed my hands on her hips, applied pressure, and stared into her eyes. “Do you like when Daddy fucks your tight little ass?” I whispered hoarsely.
She glanced at me in panic, realizing what she had said earlier. When her mind caught up to what I had asked, her ass opened and she sat all the way down.
“Daddy yeesssssss.” She groaned to the ceiling.
With my cock fully inside her, I bobbed her up and down my last inch, not wanting her ass empty whatsoever. She moaned incoherently, and her hard cock flopping onto my abs as I fucked her. She seeped precum from her tip onto my stomach, and I knew it would be mere minutes before the dam broke.
Sierras had her hands resting in my shoulders to keep her stable, and she suddenly reached one down to grasp her cock. I grabbed her arms and pinned them to her sides.
“I’m gonna cum. I need to cum!” She begged and whined.
“Not with your hands.” I grunted.
I lifted her up and down using my whole strength, and thrusted using my hips. I fucked her hard and deep, aching for her release and building my own.
“Uuuhh- uhhhhh- uuuhhh- uuuhhhh-“ She belted as her cock began twitching.
“Relax and push.” I ordered.
She breathed deeply out, and as she pushed, her cock poured cum from her prostate orgasm. It sent me over the edge, feeling her warm mess collect on my stomach and spill onto the couch.
I released one of her arms and grabbed her cock, pumping furiously.
“I’m gonna cum. Fuck. I’m gonna cum inside you. I’m gonna cum inside your tiny fucking ass.” I groaned.
“Cum Daddy! Cum in me Daddy! I’m Daddy’s slut! I’m such a good sluuuuuuuuut-“ She squealed.
I erupted inside her, filling the condom to almost bursting, even though I had already cum that night. She could feel it inside her, warm and heavy, and she began shooting rope after rope onto my stomach, my chest, my neck, and I caught a sweet taste in my mouth.
“FUCK!” I slammed her hard onto my lap, and she sat there, quivering and whimpering.
I released her other arm and she fell, her hands catching herself on my chest as she met my lips. Our passionate kiss was fueled by the insatiable lust we had just conquered, yet remained lingering.
She broke the kiss. “That was the hottest fucking thing I’ve ever done.”
“Just wait till I sit on your cock.” I whispered.
We cleaned up our mutual mess and laid on the couch together. We had prepared a few snacks and watched a few show previews, before settling on Bridgerton. After an hour, I realized Sierra had fallen sound asleep, snoring in my lap. I moved all the snacks, turned off the tv, and was easily able to pick her up and carry her to my room. I tucked her in next to me, and when I got naked and crawled into bed, she curled against me.
Not as asleep as I thought.
I fell asleep smiling.
In the morning, I woke up and found that Sierra was still sound sleep. When I pulled back the covers, I saw a big tent formed at the pocket of my oversized black hoodie. I ran to the bathroom, and prepped quickly.
When I came back, I knelt at the side of the bed, lifted the hoodie, and saw a drop of precum formed at the tip. I licked it, tasting her, then slowly enveloped my lips around her. She moaned in her sleep as I went deeper and deeper. I pulled back, spit on it, stroked her a few times, then put all of her in my throat. I swirled my tongue and vacuumed my mouth, and she abruptly woke up and saw what I was doing.
“David- Oh fuck-“ She collapsed back into the bed.
I took her cock from my mouth. “Do you want me to stop?”
“No- please-“ She whimpered. “Keep going.”
I throated her once more, feeling her cock just into my throat. It wasn’t as long as mine, so I didn’t gag. I bobbed up and down, pooling my saliva down into her lap. I undulated my throat right where her tip was and she grabbed my head, and thrusted into my mouth. Quickly, I pulled off her again.
“Not yet” I whispered, knowing she was about to blow.
I grabbed a condom and hurriedly slipped it down over her wet dick, and climbed up onto the bed.
“Oh my gooodd-“ She moaned as she realized what I was about to do. “Am I gonna fuck your ass, Daddy?”
I nodded, then straddled her, my cock rock hard and dripping.
She was about the size of my medium dildo, so as soon as I positioned her at my hole, I slid down completely onto her, and she filled my ass.
“Ohhh fuckkk-“ We both grunted in unison.
Sucking her cock had already got me halfway, and sitting on it almost made me cum. I fucked her hard, my ass slapping onto her thighs, and she grabbed my cock and desperately started stroking. With her other hand she pulled up the hoodie and began tweaking her nipples and playing with her chest.
“Daddy.” She whimpered. “I’m so fucking close. I’m so close oh my god-“
Her whimpering sent me over the edge and my cum shot out of my cock. The first sample hit her neck and chin, and as she felt the warm sensation, she began emptying herself into my ass.
“Uuuuuuunggnggggg” She cried as she came, filling the condom inside me.
She thrusted her hips up, and I slammed hard down, trying to get everything of her. I came and came and came, deluging semen onto her chest and stomach, and she nearly sobbed with joy.
“Oh my fucking god.” I coughed, out of breath after my orgasm.
I crawled off of her, her cock leaving a vacancy in my ass as it slowly closed. I leaned over her, and starting at her abs I slowly licked and sucked all my cum into my mouth.
My tongue on her body made her shiver and spasm as I made my way up her stomach, to her chest, and finally her neck. I collected everything of me that I could without swallowing, then kissed her deeply. She greedily drank my cum from my mouth, swallowed, then sucked my tongue for every last drop. I sat up and straddled her chest and she hungrily cleaned the cum from my dick, milking everything from me.
After she was satisfied, I laid beside her.
“Holy shit.” I gasped, breathing deeply. “Do you have plans for the weekend, Sierra?”
She shook her head, still reeling. “No. I don’t really even have to go home.” She looked over to me. “What are you gonna do this weekend?”
I smiled broadly.
“You.”