Life, Love, and Tight Jeans Pt. 01

Deep breath... okay here we go. I stare at the pile of clothing on my bed in front of me, and the makeup, and jewelry,sitting on my dresser. On my bed: a long-sleeve women's plaid western shirt I would tie up above the belly, a pair of pink women's panties, a black studded western women's belt, a very tight pair of blue women's bootcut jeans, and a pair of high-heeled brown cowgirl boots. On my dresser: foundation, lipstick, eyeliner, and a choker necklace. Also, my phone, with several text messages from assraider69, wondering what time I would pick him up.

My name is Alex Silverado. I have a small frame, coupled with an abnormally small penis and naturally plump little "Latina" ass. This was all typically hidden underneath gym shorts and baggy pants, which were all I owned, as a typical 18 year old college student. I stayed away from any men's jeans, as it just didn't feel right.

I didn't go to college far from home, as it was only a two hour drive. This meant that I'd come home most weekends, to see my family that I'd missed. However, this also meant that my parents had found new pastimes with the kids mostly away, and were out around town many weekend nights. As a bored, lonely teenager, I'd found myself with my sister's wardrobe. I decided to indulge my curiosity, and try on my sister's jeans. They felt amazing. My imagination ran wild. I started pretending that I was visting a man's house now, coming in through the front door and taking a seat in the living room. I'd have a pretend conversation, then imagine the man attacking me, knocking me from my seat, and rolling around on the floor, moaning for help. I'd started using an electrical extension cord to swing around and whip my tight jeans-covered ass, and when I'd felt punished enough, I'd mime myself being thrown over an ottoman, jeans ripped down, and act out getting plowed in the ass. I'd moan and scream, and recoil during the man's massive eruption of phantom cum in my ass. I'd imagine the warm feeling of hot semen floating in my guts now, and pretend the man would wrap me gently in his arms while kissing me.

Perhaps this wasn't just an exploratory phase, after all.

Back in college, my roommate Logan's and my schedules lined up so that we very rarely saw each other. His job and girlfriend meant that he was almost never there, leaving me alone most of the time. Since I had some money now too from my part time job working at the school library, I decided to fulfill a lifelong dream of mine: buying my own pair of women's jeans. I found a pair of faded mid-blue bootcut Levi's, a bit tighter and sexier than my sister's old jeans, with various rips and torn knees. The two-day shipping wait was insufferable, and I'd masturbated so much just at the thought of wearing those jeans. Once they came, they were even better than I'd imagined. They fit me perfectly, hugging every curve, and covering almost all of my foot except for the toes. I knew what I needed to do next. I bought the boots next, along with the belt. I scanned Pinterest for ideas for a top, and found a good idea under the category of "cowgirl MILF" for a longsleeve shirt and vest with a fur-lined hood.

I'd dress up in all my clothes and look in the mirror, shocked at how sexy and beautiful I found the person looking back at me. I decided I wanted to just go for it all. I'd been letting my hair grow out, and I used product in it to get it wavy and thick. By now, it was very long and wavy, with blonde streaks. I usually wore it in a man-bun or tied up to hide how feminine it looked, so seeing it free-flowing for once was amazing. I ordered silicone breasts, makeup, and a choker, and watched YouTube tutorials on makeup and voice feminization. After a few weeks of this, I'd gotten to the point where I could dress up completely, look in the mirror, and convince myself that I was an actual, female, slutty girl.

I decided to go another step further.

I decided to post a photo of myself on Reddit under the username "cdcutie18". I used Reddit frequently, and saw the burgeoning trans/crossdresser community on there, and thought it'd be a safe, easy way to see what kind of reaction I would get. My heart was pounding as I threw on my blue bootcut Levi's, black blouse, brown boots, studded black belt, my "Avril Lavigne" wig, and choker. Several photos later, I'd chosen one from my side, with some of my ass visible. My hand was shaky and sweaty as I went to hit the "Post" button on my phone screen. Once I did, I immediately closed the app, masturbated, and went to class.

When I returned to my dorm, I opened my Reddit app. 400 likes. 2 awards. And 55 DMs. I scroll through the list of DMs, seeing many variations of "hey baby", "nice ass", and "sexy jeans". I pick the oldest one, and respond with a smiley face and a hi. Immediately, the guy responds, telling me how hard my photo made his 62 year old cock. My body feels electric, as I realize that my ass in my tight jeans actually made a real, human man sexually aroused. My heart is racing as I continue to respond to DMs, reading those real comments I'd dreamed about for so long. Men telling me how beautiful I am, and the very dirty things they want to do to me. Along with many comments from men who say they'd already jerked off to my photo, I see many, many dick photos. I never thought of myself as gay, but seeing those cocks and knowing that my tight little ass made them stand up the way they are, just sets my insides on fire.

I used my small vibrator on myself at least 10 times that night. I slept with a faded pair of American Eagle bootcut jeans on, blanket heavy in case I was asleep when my roommate returned. I made myself cum by sleeping on my stomach and rubbing the vibrator tip against my tiny penis, soaking my tight jeans. This was it... I'd actually become the tight-jeaned slut I'd always dreamt of being. I sleepily moaned in satisfaction, and dozed off to sleep at around 3AM.

The hot sunlight woke me, around 11AM the next day. Luckily I didn't have class until 4PM, and this was Thursday, the last day of classes of the week for me. My roommate was at his computer, working on schoolwork (or so I thought). I started to climb out of bed, and quickly shot back under the covers, remembering I was wearing a very tight pair of bootcut AE jeans, crotch area now slightly starched with my dried cum. My roommate heard my shuffling and I saw his right hand fly up from his lap and immediately slam shut his laptop.

"Oh hey Alex! You're awake! Cool, cool, just studying."

I looked at him with an unconvinced smile. "Dude, it's cool man, we have our needs, it is what it is."

"Yeah dude, but I don't know, it's kind of weird and awkward."

"No worries man, just let me know when you need to... take care of business... and I can take a walk or something haha. By the way, don't you have a girlfriend who could help you with 'business'?"

His face sunk. "Not anymore. We broke up. I just wasn't feeling it."

"That's cool man, you're a good looking guy, I'm sure you'll find someone soon."

"Heh, you think I'm good looking?"

"Umm... yeah, I mean, as far as a guy goes haha. I'm not into guys or anything, but yeah, you're a good looking dude."

"I'm not sure what I'm into. I hope this doesn't sound weird or anything, but... I think I want to experiment a little, you know? Not with you, of course! Haha no, no worries man, I mean I just... want to explore."

My heart fluttered a little, and my stomach flip-flopped. "That's cool. I... uh... I can relate. I'm not sure about things either. In fact... well since we're being honest and open, I have something to show you." My heart was racing a mile a minute. I was about to show the first actual person who knew me my deepest, darkest secret. "Like a Band-Aid," I thought to myself. I ripped off my bedsheet, revealing my tight white night shirt with short women's sleeves, my black studded belt, and my tight AE jeans. My feet were bare, so I curled my toes inward, feeling like I wanted to hide my parts of myself under the clothes. My roommate stared at me for a second, but it felt like an eternity.

"Are those women's clothes?"

"Yeah... I just... I feel more comfortable in them, I guess."

"Heh, that studded belt and those tight jeans can't be more comfortable than a good pair of sweatpants."

"Haha I guess not, but I feel better in them, I guess."

"They look good on you, Alex."

The compliment sent electricity through my veins. "Really? Thanks Logan, I just haven't been sure about myself or my identity, what I like, stuff like that."

"So... are you into guys?"

"I don't know, I guess so. Whenever I'm wearing women's clothes, I kind of want male attention I guess," I said, as I sat up at the edge of my bed.

"I mean you'd get it, look at you! Stand up, let me see all of you." My stomach fluttered. I stood up and twirled slowly, knowingly slower when my ass was in his direction. "Nice. Very nice," he said strangely slowly and lowly. "Your long hair looks great too, when you're not wearing it up." When I twirled back around to face him, he had a devious smile on his face. "What's going on there?" he asked, pointing at my crotch. "Did you wet the bed?"

"Haha no... honestly, I was really horny last night, and I used a vibrator on myself a lot. I know, gross, but I really needed it."

"Why were you so horny?"

"Umm... no reason, just one of those nights I guess."

"Yeah, but you got cum all over your jeans and the bed. Well the front of your jeans."

"Yeah, I guess I did. I know how to wash it out though, I kind of always have cum in my jeans."

"Have you ever had cum anywhere else on your jeans, like say... your ass?"

"Haha no, I mean it'd be hard for me to cum there, considering.... hahaha." I laughed nervously, wondering if this was leading somewhere.

"Huh. Well let's try an experiment for both of us."

I froze. He stood up, and for some reason, I just noticed how tall he was. He towered nearly a foot taller than me, and he looked like a giant with his broad shoulders. "Uhh... Logan?" He grabbed me by my thin shoulders, picked me up, and threw me on his bed, stomach side down. All I could do was whimper and moan, like a submissive slut. "What the fuck?" I yelped out with a squeaky voice.

"Shut the fuck up, slut" he growled as he pinned me down on his bed. His mattress and bed frame were so squeaky. Suddenly, I felt something hard, warm, and pointy poking my jeans-covered ass.

"Oh fuck" we both let out, him in a gutteral growl, me in a helpless whimper.

"Jinx, you owe me a nut," he said as he let out a devious chuckle.

"What?" I asked incredulously as I craned my head back to see him. He used his strong hand to slam my head back to the mattress, while I suddenly felt him gyrating his hips, grinding his hard cock on my ass.

"Fuck, your tight jeans feel so good on my cock" he breathlessly mumbled. The next two minutes were just alternating visions of daylight and dark mattress, sounds of mattress squeaks and roommate groans, as he dry-humped me into the springs of his mattress. After what felt like simultaneously forever and way too short a time, I felt his whole body tensing up, his groans growing louder and more strained. "Oh fuck!" we both yelled. Suddenly, he froze. Then I felt it. Hot, wet, and thick, exploding all over my ass, soaking through my jeans. Some landed on my lower back too.

"My first lower back tattoo" I thought with a smile. I felt amazing. I felt like a slut, like a true, honest slut. My first sexual encounter, and it was in a pair of tight women's jeans in a hot guy's bed. Yeah okay, it wasn't actual "sex" sex, but it was definitely sex-related. Sex-adjacent. I mean, fuck, a guy just used me as basically his sex toy, grinding away on me until he busted his huge load all over me. The only thing separating this from actual sex was a cum-soaked layer of tight denim. My reverie was quickly interrupted as Logan forcefully rubbed his cock all over my ass, spreading the leftover cum all over my jeans, cleaning himself up. He hopped off me, gave me a hard slap on the ass, and quickly pulled up his shorts.

"Hey look... um... I don't want this to be weird or anything, alright? I was just kind of really horny, and I'm sure you were too, so this doesn't mean that, like, we're... I don't know... together or anything, right?"

I dreamily rolled over to look at this man, and smiled saying "Yeah, yeah, that's cool. We're just roommates, who might help each other out with some 'business' every once in a while, right?"

"Heh, yeah, 'business'. That's cool, I'm really glad you're cool about this, because like I said, I'm not sure where I'm going or what I want. I just kind of... wanted you, in that second, Alex" he said, while giving me another hard slap on the ass.

"Well you definitely got me, sir," I winked. He hesitated, then walked a little closer to me.

"Oh fuck, he's going to kiss me," I thought as my heart began racing again. He leaned in, hesitated again, then planted his soft lips on mine, while caressing my lower back. He bit my lip, let his tongue flit across mine, and devoured my soul with his kiss.

He pulled away and slapped my ass again, saying "Heh, thanks roomie."

As I continued laying in his bed, staring at the ceiling of the now empty dorm room, I felt it hard to shake the thoughts racing through my head. I couldn't be in love with him, no way. He was definitely good-looking and sweet, but this was just some experimentation, that's all. I felt a rush of feelings about him though, and I wanted nothing more than for him to burst back through the door, rip off my tight jeans, and plow me into another century, filling me with his seed. I'd make a good mother, I thought hopefully. What am I thinking? Ugh... I guess this is love... so many weird thoughts and feelings.

Once I'd found the strength to stand, I wobbled over to his desk, and felt warm feelings about him. I missed him in that moment. I grabbed a shirt of his and smelled it, smelling his body spray. It sent sparks of electricity through my body. I knew what to do. We might not be a couple, and maybe that's not exactly what I want, but I know that I want him to use me. I decided to unhide my secret completely (at least to this room), and pulled out my collection of women's clothing I kept stashed in bags under my bed. I replaced the men's shirts, pants, and basketball shorts hanging in my closet with my blouses, jeans, and belts. I placed my boots very conspicuously out in the open, and laid out all my makeup on my dresser. I placed my bodysuits in easy reach in the closet. It looked much more like a college girl's room now, and I'd never felt more authentic and alive.

I looked at the time, 1PM, and decided I should start getting ready for class. I hopped on the class intrasite and checked the discussions. Daydreams of being with Logan kept interrupting my focus. I decided I needed something to distract myself from Logan. I hopped back on reddit, and scrolled through my DMs. I chose one at random to interact with, hoping they were online. Here we go, assraider69.

"Nice ass in jeans, bby" is all he said.

"🥰" I replied, saying "Thank you, so sweet!" I waited a few seconds. Nothing. As I turn my attention back to my laptop screen, I see the chat bubble pop up, indicating he's typing. My stomach flutters.

"Hey bby, wat u up to"

"Hey you! Not much, just bored here studying."

"Lol that sucks, are you in college?"

"Lol ya I'm a freshman. So lame."

"Bet lots of guys give you attention tho, lots of parties."

"Lol no, I'm super shy, and I actually haven't gone out in public dressed up."

"Really? So you've never been with a guy?"

I pause. "Lol umm... well actually my roommate just kind of... dry-humped me, it was the first time I'd ever been dressed up in front of another person."

"No way. That's hot, I bet you'd make a good slut."

"Lol I guess so."

"Did you like it?"

"Umm... ya it was pretty fun, I didn't realize I'd like it so much." I took a breath and had to put the phone down. This was real. I couldn't believe it. I had seriously just shown someone in real life that I, me, like wearing women's clothes, and that person actually pinned me down and dry-fucked me. And now I was telling some horny stranger on the internet about it. Fuck, this is so awesome, but kind of scary. What the fuck do I do? I picked my phone back up. assraider69 had replied.

"So... you've never had actual sex, right? Just the dry humping?"

"Yeah, basically."

A long pause. "Would you want to?"

"Umm... yeah I think I'd at least want to try it."

"Experimentation, right?" The word sent me fluttering. Logan called it "experimentation". Lots of guys seem to want to conduct "experiments" with me. Well let me be their submissive test subject. "Where you at?"

"Umm... California... you?"

"I'm from Riverside."

I ground in my seat with nervousness and excitement. "Lol no way. I'm from Riverside, I go home most weekends from Irvine."

"Yeah? Well... maybe we should hook up."

Oh fuck. This is it.

----

The plan was that once I left class, I would race back to my dorm, get dressed up, then make the drive overnight to Riverside. I could make it in around 2 hours, which means I'd get there around 10-11PM. I'd reserved a room at a cheap motel, because my parents were still in town until Friday afternoon, when they'd be leaving on a trip. They weren't even aware I'd be in town, and I definitely didn't want them knowing. assraider69 sent photos of himself. He was a chubby, hairy, neckbeard type guy, in his early 30s. No car, no college degree, working shifts at the local quick mart. I didn't care that I wasn't super attracted to him, it was the thrill of everything about this trip that got me going. And honestly, the thought of being sexually used by a 30 year old hairy, fat loser made me so aroused for some reason. And maybe I could take some photos to make Logan jealous...

At 7PM, when my class ended, I scrambled back to my dorm, unsure if Logan was there, or planning on stopping by. The sun had set, and the darkness made my pulse race.

---

Deep breath... okay here we go. I stare at the pile of clothing on my bed in front of me, and the makeup, jewelry, and wig sitting on my dresser. On my bed: a long-sleeve women's plaid shirt I would tie up above the belly, a pair of pink women's panties, a black studded western women's belt, a very tight pair of blue women's bootcut jeans, and a pair of high-heeled brown cowgirl boots. On my dresser: foundation, lipstick, eyeliner, and a choker necklace. Also, my phone, with several text messages from assraider69, wondering what time I would pick him up. I got ready, making sure to be careful with the makeup through my shaky hands. I was ready. I stared in the mirror, and a very slutty looking 18 year old girl in tight jeans was staring back at me. I reached around to slap the girl on the ass, realizing it was my own ass I was spanking. I let out a yelp in the mirror, the soft, sexy, distraught face in the mirror. That was my face. Those lips were mine.

I grabbed my suitcase and opened the door slowly. No one in the hall. My cowgirl boots would definitely make noises as I tried to quickly exit the dorm room, but once I made it the elevator, I should be fine. The walk to the elevator felt like an eternity. Once I made it, I waited for the car to come up. I heard talking getting louder down the hallway, so I pulled my hood down. Luckily the door opened before that group rounded the corner, so I snuck in. The elevator opened in the parking garage, and I practically ran to my car, boots clacking all the way. I'm sure someone heard and/or saw me, but no matter, I'm gone.

As I begin the drive and enter the freeway, I take a look down and see my thick thighs covered by very tight, faded jeans. The sight makes me squirm under the halogen streetlights. I remember I have to be careful, I wouldn't want to get into an accident or get pulled over while dressed up. The two hour drive feels like an eternity, but I finally make it to the motel. After parking, I sat in the car for a second, realizing I'd need to go into the lobby in order to check in. The thought makes me terrified. Don't think about it. Confidence is the key. Act like you are who you appear to be. Fuck it. I am a woman tonight. At least if the clerk is a man, if it's a woman, I'm just going to sleep in the car.