Choosing an Outfit.

(A reluctant crossdresser story.)

After graduating from high school I opted to remain living at my parents house and commuting to the local community college three days a week instead of attending a more traditional university. It gave me a year or two to get my grades up and spend time with my girlfriend Sarah. She was 18, a year younger than me and finishing her senior year at a local all girls catholic school and, yes, before you ask, she wore the uniform and everything. She lived with her mom and stepfather in a neighborhood one over from mine and on the days when I didn’t have classes I’d go over to her house where we’d have hang out, watch TV and if her parents were out, have sex in their backyard hot tub. On that Thursday I’d arrived at her house at two thirty, about an hour before she got home. Sarah’s parents both worked and I knew where the spare key was hidden but to be polite I rang the doorbell first before fishing the key out from under the mat. To my surprise her step father Matt answered the door wearing a tight white tshirt and blue mesh basketball shorts.

“I bet you weren’t expecting me.” He said with a chuckle as I stared at him nervously. Matt was a tall man in his early forties whose short cropped brown hair was flecked with grey. He was a work out guy, who spent evenings on his rowing machine or lifting weights in the basement after dinner. He was surprisingly nice to me ever since Sarah and I had started dating which was more than I could say for the father’s of my previous girlfriends, never giving me a hard time and leaving Sarah and I alone for the most part whenever I visited. “I had the day off, come on in. She’s not home yet but I imagine she will be soon.”

I stepped into the entryway and he shut the door behind me. “Not trying to be rude but I’m watching the last few innings of the Sox game from last night. You’re welcome to join me or you can wait up in her room.” He gestured to the living room where the sounds of a baseball game blared from the sound system.

“Uh, I’ll just wait upstairs…” I said politely and he was already halfway back to the living room before I answered.

“Cool, she’ll be home soon. Sorry, I don’t want to miss the end of the game.” He said before disappearing around the doorway. I hustled upstairs and flopped down on Sarah’s bed, luxuriating in the softness of her fuzzy purple comforter and the lingering scent of her blackberry body spray. ‘Girls have such nice stuff.’ I thought to myself as I looked around her well organized bedroom. Everything was so neat and girly, a stark contrast to my own bedroom with its unmade bed and heaps of dirty laundry festooned throughout. I pulled out my phone and shot her a text.

-IM IN YOUR HOUSE!

A few seconds later her reply came through.

-I’M CALLING THE COPS. Followed by a laughing emoji.

-YOURE STEPDAD IS HOME.

-SHIT. I WAS HOPING WE”D BE ALONE TODAY. I’M SOOO HORNY! HA HA HA Followed by a smiling purple devil emoji.

I laughed and adjusted my hardening cock through my pants. I was horny too and was really looking forward to some quality “alone time” with Sarah. We’d definitely still have sex, I was sure of it but it was always more fun when we had the place to ourselves. My phone buzzed again.

-SEND ME A PIC accompanied by the same purple devil.

I slid my jeans down exposing my tight black bikini style breifs and cupped my thick bulge in my left hand, snapping a photo and sending it off.

-OMG… I WANT IT SOOO BADLY! HA HA HA She replied. I massaged my shaved thickening cock through my underwear and smiled finding myself incredibly turned on to be there in her pastel bedroom, surrounded by all of Sarah’s girly things. I imagined how I was going to slide her pleated skirt up and eat her pussy out the second she walked through the door. I started to type those sentiments when another text came through.

-I HAVE TO FINISH THIS WRITING ASSIGNMENT. CANT REALLY TEXT. WHILE YOU WAIT, GO INTO MY TOP DRESSER DRAWER AND PICK OUT SOMETHING FOR ME TO WEAR WHEN I GET HOME.

My heart fluttered. -YOU MEAN YOUR UNDERWEAR DRAWER?!

-YES! PICK SOMETHING GOOD. I”LL BE THERE IN A BIT!

I jumped up and hurried to her antique oak dresser and slid open the top drawer. Inside was an incredibly expansive collection of bras, stockings, knee socks and panties. I stared almost dumbfounded at the rainbow of silky fabrics. She had so many different styles, string bikinis, boy shorts and my personal favorite, thongs. My hand slid through the drawer, caressing all the soft textures, cotton, silk, lace and lycra picturing each pair hugging the curves of her body and sweet smooth pussy. I knew she’d be home soon and that Matt was deeply immersed in his baseball game so I slid my pants off and closed the door. My erection was at full mast, stretching the microfiber of my tight briefs as I carefully examined the contents of my girlfriend’s panty drawer. I picked up a pink lace thong I’d seen her wear and held it to my face, letting my lips graze the soft fabric as my heart pounded and I excitedly rifled around the drawer. I felt like such a perv going through Sarah’s underwear like this but then again, she did ask me to.

I selected a tiny white gstring with a small pink bow on the thin waistband and laid them out on the bed. Then I picked out a pair of white sheer thigh high stockings with a lace top. Lastly I pulled out a thin white string bikini style bra that was really just two triangles of skimpy fabric connected by a few thin spaghetti straps. My cock throbbed as I stared down at the outfit I’d picked out for Sarah, imagining how sexy she’d look kneeling on the bed wearing only the tiny white lingerie. I could hardly wait for her to get home and checked the clock on my phone and sighed in frustration, 45 minutes felt like an eternity.

I returned to the drawer and continued to peruse the selection. Women’s underwear was so hot! All the thin straps and thin soft fabric, they were so lucky to get to wear all this skimpy sexy stuff everyday. I wondered if it made them feel sexy and turned on knowing that under their clothes they were all wearing beautiful, sexy panties that caressed their curves and soft skin. I picked up a pair of baby blue string bikini panties and held them to my face, rubbing them softly over my cheeks and lips. They were so soft and silky. Suddenly I was overcome with arousal and slid my tight stretchy briefs halfway down my thighs, my hard hairless cock standing straight out, fully engorged. I slipped my tshirt off and wrapped the blue silk panties around my erection, stroking slowly as I shuddered. The silk felt amazing against my smooth shaved cock, slippery and soft. I picked up a tiny black lycra thong and held it to my face, inhaling deeply as I licked at the soft fabric and stroked myself. I felt like such a pervert, such a naughty horny panty loving boy, standing almost completely naked as I played with Sarah’s underwear. I bit my lip to keep from moaning as my hands massaged the baby blue panties up and down my hard cock as I pressed the little thong into my mouth. Then a thought flashed into my mind. I pictured wearing a pair of Sarah’s tight little panties as she humped against my bulge. I imagined her voice, telling me how sexy I looked in her undewear, telling me what a naughty panty boy I was. I sucked at the thong in my mouth and stroked faster, my heart pounding as…

“What are you doing?”

I spun around and froze. Matt was standing in the doorway way with his hands on his hips and an eyebrow cocked. I had been so lost in my fantasy that I hadn’t heard the door open. I blushed and tried to answer.

“Mmmph mmphmr…” the thong in my mouth muffling my words, I yanked it out and hurriedly pulled up my briefs, the blue panties still wrapped around my erection and peeking out over my waistband. “I wasn’t doing anything. I was just… Sarah asked me to…” I scrambled to answer, mortified with embarrassment. There was nothing I could say. Between the white outfit laid out on the bed, the panties wrapped around my cock, my state of undress and the saliva soaked thong in my hand…I was caught.

“Were you perving out over Sarah’s underwear?” He asked as he stepped into the room.

“I…..yes…” I answered bashfully, averting my gaze and staring at the floor. He looked into the open drawer and then down at the bed.

“That’s a lovely ensemble you’ve picked out,” he said gesturing to the stockings and lingerie on the bed. “I bet they’ll look amazing on you.”

“What? Oh… ha ha, no I, I wasn’t… see I was… see…Sarah was…“ My arousal and sheer embarrassment had my words jumbled as I tried to speak as he stepped forward and placed his hand on my smooth chest.

“Shhhhh…. Sarah’s not here.” He whispered with a smile and his hand slid down my stomach and cupped my thick bulge. He gripped the silky blue panties and pulled them out of my underwear before holding them up to my face and feeding them into my mouth with his fingers. I stood frozen, not sure what to do and hornier than I’d ever been in my life. “I think you were looking at Sarah’s sexy panties and wanted to know what they’d feel like to wear. Isn’t that right?”

I nodded as his panty wrapped fingers pumped in and out of my lips, stuffing my mouth with the silky blue underwear.

“Because you’re a naughty panty boy, aren’t you?” He asked and I nodded again. “Mmmm, that’s good… now I want you to get dressed.”

Instinctively I went to reach for my jeans but he stopped me and guided me to the bed. “No… I want you to put on the outfit you picked out.” I stood stone still, unsure of what was happening as his hands caressed the small of my back and he started to slide my tight black briefs down my legs. “Stockings first…” He whispered in my ear. I tried to speak but the silk panties muffled my words so I submitted, sitting down on the edge of the bed and sliding the sheer stockings up over my long smooth legs. He stood watching as I stepped into the little g-string and pulled them up, the tiny pouch stretched tight to accommodate my throbbing erection and I slid the little bra on. He turned me around as I stood and helped me fasten the back before I felt his hands slide down my torso and stomach. “Mmmm, I love how smooth you are… shaved all over just how I like.”

My head was spinning as he pressed his body against mine. I was suddenly aware of the thick bulge in his shorts as he pressed it against my ass and caressed my hard nipples through my bra. His breath was hot on my neck as he turned me to face the floor length mirror. “Doesn’t that feel good?” He whispered. “Doesn’t it feel good to be a sweet panty boy?”

My response was muffled again by my panty stuffed mouth. I stared at my reflection. It did feel good, more than that, it felt incredible. The stockings and bra looked so feminine against my smooth pale skin and felt amazing. My hairless cock strained against the tiny g-string, pulling the straps tight to my body and causing me to shiver with pleasure. He traced his finger around the little pink bow positioned just over my pulsing cock head and I instinctively pushed my body back into his. I felt so sexy, so vulnerable as his hands explored my soft skin and he lightly kissed my neck.

“That’s a good boy…” he whispered as he gripped my hips and nuzzled my neck as I moaned. Matt took my hand and led me out into the hallway and down the stairs. I felt so exposed as I followed him through the house. What if someone saw? What would Sarah say? I was so overcome with arousal that I didn’t really care, I was just eager to see where he was taking me.

He led me into the TV room and slid his tshirt off, exposing his toned muscular chest before sitting on the couch. I stood there feeling dizzy in my sexy white ensemble, bashfully covering my thick panty bulge with my hands as the blue panties hung out of my mouth, soaked with my saliva. Matt patted his lap. “Come sit on Daddy’s lap…” he said with a wry smile and I obeyed. He slid his hand around the small of my back as my long stocking wrapped legs stretched out across the cushions. HIs other hand made its way to my chest and he began caressing my flat boobs and teasing my hard nipples with his fingers through the thin sheer bra causing me to moan. He began kissing my chest, flicking the outline of my hard nipples as his hard cock pressed against my thighs through his blue mesh shorts.

The room was spinning and I felt as though I were drunk. My cock had never been so hard as it strained against the fabric of Sarah’s silky white gstring. It was all so confusing, I knew I was straight and only into women but in that moment, squeezed into the sexy women’s underwear and feeling Matt’s mouth and hands all over my smooth skin I knew I wanted him. I wanted to please him, I wanted him to use my body however he wanted. What was I doing?! This was my girlfriend’s stepfather! And she’d be home soon! What if she caught us? My apprehension began to rise but then Matt pulled the soaked panties from my mouth and turned my face to his before kissing me full on the lips. I melted into him, placing my hands on his chest and sucking his lips and tongue, my hesitation evaporating.

“Mmmm, such a naughty boy…” He said as his hands gripped my hips and he turned me so I was laying across his lap, my hard panty bulges pressed against the thick bulge in his basketball shorts. Matt’s hand caressed my smooth firm ass, kneading it as I whimpered. He stuffed the wet blue panties back into my mouth as he took the thin back strap of my g-string in his hand and pulled it tight causing me to gasp as it pulled tight around my hard cock. His hand came down hard on my cheeks with a slap and I whimpered again. “You’re a naughty panty boy aren’t you?” He asked and I nodded feeling my cheeks flush bright pink as his hand came down again. SLAP. I moaned. SLAP. Whimpering and pressing my bulge against his as he spanked me.

I noticed that I wasn’t resisting him in any way. I was surprised at how quickly I’d given myself over to him, allowing my submissive sissy slide to take control and submit to the sexy older man.

“Can you feel how hard you’ve made me?” He asked and I nodded as another muffled moan escaped my lips. “Get on your knees… it’s time for Daddy to feed his panty boy…”

I knew exactly that he meant and I scrambled to my knees as he slipped his shorts down and off, revealing the biggest cock I’d ever seen. I stared at it stunned. It was so thick and smooth, throbbing just inches from my face. I was shocked at how badly I wanted to taste it, to feel it in my mouth. Not ten minutes ago had someone told me I’d be lusting after a cock before days end I wouldn’t have believed them but now here I was, an insatiable panty boy on his knees, practically drooling as I stared at my girlfriend’s step dad’s erection. He pulled the panties from my mouth and tossed them on the floor before taking my head in his hands and guiding me in. I parted my lips and slid my mouth over his thick pronounced head, moaning as I savored the thickness, massaging it with my tongue as I began to gently suck. It felt so smooth and rigid as It pumped in and out of my wet hungry mouth. It felt incredible, my mouth was so full as I lovingly sucked Matt’s massive erection.

“Ooooh yessss…” he hissed as I bobbed up and down, staring into his brown eyes as he slides his fingers through my hair. “You look so sexy in your slutty bra and panties… do you like sucking Daddy’s big cock?”

I nodded and he said “Say it.”

I gasped as his cock slid from my lips. “I love it Daddy… I love sucking your big cock…”

“Good boy…” he moaned before pushing my head back down and I resumed worshipping his dick with my mouth, taking his enormous erection deep into my throat. Suddenly Matt gripped my hair and pulled my head back, I gasped, my mouth hanging open. He told me to stand and I obeyed, shakily rising to my feet as he placed his hands on my smooth stocking thighs. “Now Daddy wants a taste of this sweet panty cock…”

He leaned in and kissed my throbbing bulge just below the pink ribbon causing me to moan. Matt pulled my little panties to the side and my hard hairless cock sprung out standing at full attention. With zero hesitation he cupped my smooth balls in his hand and sunk his mouth over my dick. I whimpered as he began sucking gently but ferociously, swirling his tongue as his lips slid up and down my smooth rigid shaft.

“Yes Daddy… thank you Daddy…” I moaned as he lovingly devoured my cock. My hands made their way to my chest and I started rubbing my hard nipples through my sheer bra. It was the best blow job I’d ever had, wailing with pleasure as I rolled my hips gently pushing it deeper into his wet hot mouth as he squeezed my ass. Within seconds I could feel my orgasm rising and my thighs began to tremble. He pulled his mouth back and tucked my cock back into my panties. His hand found the back of my neck, pulling me back down to my knees and my mouth back to his hard dick, still glistening with my saliva.

“I don’t want you cumming yet…” he said as I inhaled his cock, sucking with a newfound intensity. “Put your hands behind your back, bad boy…” I did as he commanded, pulling them from his muscular thighs and allowing his hands to guide my mouth up and down, slurping, sucking like a good panty boy.

I was in absolute heaven, completely lost in the moment as I sucked the older man’s massive erection. Savoring every inch as it slid in and out of my wet lips and I drooled down his heavy balls.

“Daddy no!”

Suddenly I heard Sarah’s voice and looked up to see her standing in the doorway. She looked amazing in her white blouse, pleated skirt and navy blue knee socks, her back pack over one shoulder. I felt myself blush again and wanted to explain but Matt’s hands held my head in place, giving me no choice but to keep sucking.

“You promised you wouldn’t turn any more of my boyfriends into cocksuckers! You promised!” She fumed, disappointment all over her face and hands on her curvy hips.

Matt shrugged and laughed, “Oh I’m sorry baby… it just sort of happened.”

I noticed that she didn’t storm out of the room soooo, maybe she wasn’t that mad?

“Oh sure, just like last time with Justin, it just ‘sort of happened?’ Yeah right…” She said setting down her bag.

“What can I say? You and I have similar tastes!” Matt laughed. “And don’t pretend he doesn’t look sooo cute in his little panties and stockings.”

My mouth kept pumping up and down like I was in a sissy trance, unable to stop even if I had wanted to. And I didn’t want to stop. I was confused by the dynamic between Sarah and her stepfather but all I knew was she didn’t really mind and I needed Matt’s big cock in my mouth.

Sarah sighed and slumped down on the plush armchair across from the couch. “I know… he does look cute… but I just wanted to play with him a while longer before you got your hands on him.”

Matt laughed again as he consoled his step daughter. “Oh please don’t be upset baby, just look at it like this, I’m breaking him in for you, plus I know you love watching sexy panty boys suck my cock.”

Then it was Sarah’s turn to laugh. “Ha ha ha, I know… thank you Daddy… you’re so good to me.”

I couldn’t see her but I could tell that her anger had subsided. I raised my ass up in the air so she could see my huge panty bulge. “Oh wow, look how hard he is!” She laughed. What the hell was going on with these two anyway?

“Oh yes…” Matt said, looking down at me. “He’s a naughty panty boy, I caught him going through your underwear drawer.”

“I TOLD him to do that! I asked him to pick out something sexy for ME to wear.” Sarah said.

“Well this is what he picked out!” Matt laughed again. “And I’m not sure but I think it looks much sexier on him.”

Sarah sighed again and responded begrudgingly. “Yeah… it’s a sexy outfit on him…”

“See?” Matt said. “And I’m sure whatever panties you have on will make him more than happy. Isn’t that right, panty boy? You love all of Sarah’s pretty panties don’t you?”

I nodded, my affirmative response muffled by the cock between my lips.

He leaned down and looked me in the eyes. “And now you’re gonna eat Sarah’s pretty pussy while I fuck you, isn’t that right?”

Pure exhilaration pulsed through my body and I nodded again. Matt released my head and I turned to face my girlfriend. She sat in the large chair with one knee over the arm and flipped her skirt up exposing her bright blue silk bikini panties. She looked amazing, her long brown hair up in a ponytail and long bangs framing her face. She flashed me a naughty smile and motioned for me to crawl to her.

“Come here, naughty boy. Daddy’s big cock isn’t the only thing you’re gonna be eating today…” She purred as she slid her panties to the side revealing her smooth glistening slit. I crawled forward and buried my face between her legs, licking hungrily at her soft wet lips as she leaned back and moaned. “Oh yesssss…. I’ve been thinking about this all day.”

I licked slowly, savoring her taste as my tongue parted her lips and dipped inside. My lips closed around her hard little clit and I sucked softly as she ran her fingers through my hair and pushed her pelvis to my face. I felt Matt’s hand slide over my tight smooth ass and dip between my legs, his fingers massaging my trembling hard cock through my little white panties.

“Is that good, baby?” He asked Sarah.

“Oh yesssss… it’s perfect. Thank you for warming him up for me Daddy.” She giggled as he pulled the back strap of my g-string to the side and I whimpered as his tongue slid over my tight pink boipussy. I’d never felt anything like it before, It felt so good, moaning against Sarah’s beautiful pussy as her stepfather ate me out, his wet tongue lubing me up as I gripped the plush carpet. I felt him rise to his knees and press his thick smooth cock head between my cheeks. As my tongue took long languid strokes up and down Sarah’s slit I wondered if he was really going to fuck me but then he pressed in and I felt his glorious cock slide inside of me causing my body to shake. Oh it felt amazing! He began sawing slowly in and out of my tight eager boipussy and I wailed with pleasure, pushing my hips back into his as I sucked Sarah’s swollen clit.

Matt gripped my hips and found his rhythm, pumping in and out slowly, deliberately, sending waves of joy through my whole body. Sarah was moaning as my mouth massaged her smooth wet pussy lips, I didn’t know how long I’d last like this before I came but I didn’t care, I was loving every moment.

“Ooooh, it feels soooo good… you like that don’t you? You love taking my big cock…” He said.

I pulled my head back, gasping and moaned. “Yes! Yes I love it… fuck me Daddy… give me that big cock!”

He pushed my head back down between Sarah’s thighs and I took her clit between my lips and started swirling my tongue in circles. I knew exactly how to make her cum and I set forth to accomplish that before I came from Matt’s powerful fucking.

“That’s it… yes… yes… don’t stop… yes… yes….” She wailed as my tongue became a hurricane of movement, spiraling around her little pink button.

My hips started to shake and my cock throbbed. I was going to cum right there! I sucked down harder on her pussy, my tongue swirling frantically as her thighs started to quiver and she screamed out. “Fuck! Fuck yes! I’m cummmmmMMMMIIIINNNNG!” My face was suddenly drenched with her sweet juice and I tried in vain to lick it all up but then my own orgasm crested. My body bucked and my cock erupted, drenching my tight panties with hot sticky cum as I shuddered and my body went completely limp. I collapsed on the floor, moaning incoherently and drooling as my vision blurred and my powerful orgasm ricocheted through me. Matt pulled out and grunted as I felt my ass and lower back coated in his hot gooey cum.

The three of us stayed just as we were for a few moments, composing ourselves and catching our breath. Sarah slid her panties back into place and smoothed her skirt over her thighs as Matt stood and wiped a paper towel over the mess on my back. He pulled his shorts back on and sat back on the couch as I rose to my knees.

“Well…”Sarah said. “THAT was unexpected… but very nice all the same.”

“It was wasn’t it?” Matt said with a laugh and Sarah stood and took my hand.

“Now if you don’t mind, I’m taking this one upstairs for a stern talking-to.” Sarah said with a grin as I rose and trailed her out of the room.

“Ok, have fun! You too naughty boy!” Matt chuckled as I heard the TV flip back on.

Sarah led me back upstairs and into her room. I sat on the bed, disheveled and dizzy, trying my best to act normal despite what had just happened and what I was wearing. Sarah closed the door and smiled at me. “Was that ok?”

“Oh yes… definitely. But I have to ask, what’s the deal with you and your step dad? Do you two like… you know…like… with each other?”

She scrunched her face up in disgust. “What… with him? EWW, no fucking way… he’s my stepfather, we do’t do that! We just… ha ha ha, he’s just bi… and we have a similar taste in guys.”

I nodded and she leaned down to kiss me. “By the way… you look amazing in that outfit.”

I laughed. “Oh thank god… I didn’t mean to weird you out I just…”

She pressed her finger to my lips. “Shhhhh… it’s ok. I like it.”My heart swelled as she walked to the dresser and slid open the top drawer. “Now come here. I have some other stuff I’d love to see you in.”

THE END.
(copyright 2025 tightpantsxxv.)