College Chronicles Ep. 05

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College Freshman Sam spends the day with Cindy.
12.4k words
4.64
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Part 5 of the 22 part series

Updated 09/09/2023
Created 11/15/2020
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When I woke up I was in bliss, surrounded by a warm, tender embrace.

Then I was hit by my ridiculous, dehydrated hangover. That, and my memories of debasement from the previous night. The bar, dancing with Cindy and being so fucked up...the bathroom, eating Cindy's pussy and sucking Jaxx's balls... Both of them getting cum on me... Cindy bringing me home... putting panties on me... making me cum like a girl...

I suddenly became aware of my aching hard cock, still covered by the now soiled baby-blue panties. In panic I glanced at Jaxx's bed. Who would be there to laugh at me? But it was empty; Jaxx had not come home last night. I was relieved, one less thing for him to bully me about. Life would be hard enough having sucked his balls.

Then I turned over slightly to look at Cindy. She lay on her back next to me, a picture of beauty. Her copper hair shone in the morning light and fell in effortless curls, framing her face and slim, long neck. As she breathed in and out lightly, her beautiful breasts rose and fell slightly, aching to be cupped. Her eyelashes fluttered lightly as she slept, and I just stared at her for a bit, captivated. There was no trace of the sex-crazed succubus of the previous night. Now she was a goddess, pure and holy and an incredible blessing, to be in my bed.

I could feel my hard-on, erect and desperate. And suddenly, foolishly, I thought now was my chance to prove I was a man after all. That I wasn't just happy with Cindy fucking me; I would fuck her.

So I slowly and carefully climbed on top of her. I maneuvered myself between her legs—they were so muscled, and it seemed like she resisted me as she slept, making me work hard to pull her legs apart enough to slip my waist in-between. I was face to face with her perfect, medium tits, and lowered my mouth to one, then the other, sucking on her soft little nipples. She was somehow both sweet and musky, still tasting of sweat from the night's adventures.

I had, without intending to, started humping at her, small penis nowhere near her hole but enjoying the friction of her soft skin. So I blushed hot red when I felt her breasts jiggle in my mouth and heard her gleeful giggle above me.

"Oh my GOD Sami! You dumb, horny slut! Are you trying to fuck me??"

I was speechless. What had I been thinking? Of course she would wake up. Was she right? Was I a dumb slut?

"Uhhh... Uhm... I was... Hard..."

Proving her point, I realise in hindsight.

"Well I figured that! Alright, you're lucky I'm still in a good mood from last night." She smiled, viciously. "Pull your panties down." She waited a moment as I scrambled at her instruction, leaning on her and awkwardly pulling the panties down my smooth legs. "Now get the fuck over here."

And in one smooth motion she had yanked me to the side, flipping us over, so I was on the bottom and she on top. She had my legs pressed together between her powerful thighs, and as I felt my tiny penis slide into her already wet, clutching pussy, I was surprised that I could feel her so tight around my little nub. She brought one hand to her pussy, stuffing two fingers inside while rubbing her clit with her palm. She brought her other hand to my face, and caressed my cheek in the soft but powerful way she had, that felt both reassuring and intimidating; threatening and promising. She traced my cheekbone, my jaw, down and across my neck.

"You really are sooo pretty Sami. I'd bet you'd look really good with a little bit of makeup on!"

She smiled down at me as she rode. It was nothing like when she fucked Jaxx, panting and moaning and giggling. She was totally composed, as if she were undergoing some routine business arrangement. I blushed, both at her suggestion and the delusion that I would have been able to fuck her. Then her hand stretched around my neck to grip tightly, and she began to rock forward and back on my penis harder, masturbating herself more fervently. My heart beat faster, and I couldn't help but think back to my first time, when she had taken me against my will. Now I was willing—I had started this after all—but I had bitten off more than I could chew. She was going to fuck me again, raw and hard, and I had no say in it.

Her hand tightened further around my neck, squeezing at the sides and cutting off my blood flow. It shocked me that something so soft and dainty-looking could exhibit such a severe and unrelenting hold. I brought my hands up my neck and pulled at her hand, trying to remove it from my neck as I felt my vision fading slightly. Even together they failed to budge her fingers, and she giggled at my weak protests. My sight was quickly shrinking circle, centered on Cindy's smirking, beautiful face.

Then she released me and I gasped in a deep breath, feeling my penis twitching in her wet, tight pussy. Suddenly her hand was at my face, slapping me repeatedly.

"Fucking!" *slap* "Cum!" *slap* "For!" *slap* "Me!" *slap* "PUSSY!" *slap*

Under her combined physical and verbal assault I had no chance. My face was red hot in pain and shame, and I came, writing and gasping like a fish out of water. She laughed loudly and leaned back, finger and touching herself with both hands now. She was literally getting off on humiliating and dominating me. I wondered how I could have been so stupid to think I could fuck HER. She was a goddess compared to me.

So I worshipped her; gasping, still reeling from my orgasm,

"Cindy... I love... how you fuck me... I only want... To please you... Please keep me as your... boyfriend? I'll... I'll try... Try to do... what you want..."

A strange look had come upon her face, and she leaned forward and kissed me deeply, moaning and cumming on her fingers and my tiny offering.

As we lay in our post sex glow, she again let me cuddle up to her. We even pillow-talked! Just talking about our lives, our studies, our homes. She never mentioned my embarrassing worship of her as we had cum together, and I couldn't detect a shred of bullying, domination, or humiliation, so I quickly grew comfortable. Cindy asked if I wanted to get lunch and run errands; freshman meet week ended that day, and classes would begin the next. It somewhat surprised that she would even want to be seen with me, so I quickly agreed before whatever was happening could end.

I showered and changed, but just as I was ready to go, Cindy tutted,

"Are your dressed to impress, Sami?"

I knew what she was talking about, and blushed. I had hoped we could both just forget about the panties.

"The ones you gave me are... Dirty... And I don't... Have any others..."

I wilted under her unmoving gaze, hoping I hadn't spoiled the day before it began. Then she giggled and shoved me playfully.

"I'm just kidding silly! I've got another pair you can wear for now."

She fished into her purse again, quickly withdrawing another pair of panties. This time they were boy-shorts style, white, with a cute cartoon monkey face on the front and a little monkey tail printed on the back. She handed them to me and I returned to the bathroom to change. As I pulled them up I strangely enjoyed how they hugged my package, and when I turned to look at them in the mirror I noticed they clung to and lifted my fit butt in an appealing way. I didn't think to wonder why Cindy had had two pairs of spare panties on her, or what she meant by "for now."

Then we went to back to Cindy's so she could change as well. It turned out Cindy already lived at a sorority house, despite the fact that she was only a freshman. I was too impressed to ask why, and a bit disappointed when she asked me to wait outside for her,

"Sami, it'll take sooo long if any of the girls see you." She could tell I was let down. "Don't worry, I promise I'll introduce EVERYone." She thought I wanted to meet the others—really I just wanted to see her room. But I smiled through it, and sat on a stoop nearby, watching the gorgeous girls that came and went from the sorority house, and occasionally shifting uncomfortably, trying to relieve the tight pressure that Cindy's panties applied to my penis and testicles.

Finally Cindy re-emerged, a vision in a yellow sundress to match the pleasant weather, with low black heels on her feet and a small leather purse over one arm. Her tawny hair was pulled into a loose ponytail, highlighting her long neck and, as always, contrasting her flashing green eyes.

We got so many looks as we walked around campus, it was like I was with a celebrity. Men's heads turned as we passed, sometimes ogling Cindy, others eyeing me with jealousy or mocking derision—but I didn't care. Like at the bar, *I* was the one with her, not them, so they could think what they wanted. Women also turned as we passed, subtle admiring peeks at Cindy's assets or scornful whispers to their friends. But Cindy wasn't just beautiful, she was also clever. I was impressed by her breadth and depth of knowledge on everything we talked about, and she always had a new piece of witty, flirty banter ready to diffuse my sometimes stumbling, awkward conversation. We rode a bus into the city center and passed the day preparing for classes; buying school supplies and books, as well as simply getting to know each other better, window shopping, getting coffee, and sitting down in a park to eat lunch from a food cart. It was almost enough to distract me from the constant, nagging pull of the women's underwear I wore.

Then there was a...shadow... on the day. As we were walking down one street, Cindy jumped, and grabbed me by the arm, pulling me towards a little shop with mannequins modeling skimpy lingerie in the window. For a second I was gleeful—was she getting underwear for me? Then my heart sunk—no, she was probably getting underwear for Jaxx. I didn't realise that both of my guesses were at least partially true.

She eagerly pulled me in through the door to the cool, sweetly perfumed store's interior. I would have been lost in here by myself, wandering the racks and aisles forever to find anything. But Cindy moved like she was born there, flitting from display to display with girlish, youthful energy. As she went, she was picking up different pairs of panties; bright pink to plain white, boy shorts to skimpy g-strings and much in-between. She spoke as she shopped, talking to herself and thinking out loud as she made decisions.

"Oh that feels nice... this one is so sexy!... And maybe... How about one of these?... Oh I have a pair just like this..."

The first choice she threw playfully at me—before long I had a small pile in my arms. After a bit of this she turned to me.

"So, what do you think?"

"Uhh... I think you'll look really sexy in all of these."

She giggled, bubbly and condescending,

"They're not for me, silly! They're yours! Or will be, once we've tried some on!"

I vividly remember staring at her, my jaw on the floor, totally speechless at her (in hindsight obvious) intentions.

"...Wha... Uhh... I... I... I'm not!—"

I paused, looking around to see if I had caught anyone's attention with my indignant volume, then ran to catch up with Cindy, who had continued moving without me. I whispered this time, quick stepping in Cindy's wake,

"I-I'm not going to wear panties, Cindy!"

I stood behind her as she picked two more panties from a display, then she turned to me briskly. I caught the end of an eye roll, before she flashed her bright smile at me, and deposited a small pile of cloth from her hand into the larger pile in my arms.

"But you already are! Let's just try a few on, huh? For me? Pretty pleaseeee? I'll put some on too, it'll be fun!"

"I... Uh... Wha? T—Try on underwear? I-I don't think... That's allowed..."

She winked roguishly at me and brought a slim finger to her lips. "I won't tell if you don't! Plus I'll just end up getting them anyway, can't have too many cute panties!"

She grabbed my arm and pulled me along after her, almost yanking me into the back of the store, where a few changing stalls stood with floor to ceiling doors. The changing room was simple; a small wooden bench, a hook with a few hangers, and a floor to ceiling mirror covering one side. Once inside, she turned and locked the door with a satisfying clunk. This diminished my anxiety a little—but not entirely, still holding an armful of pretty girls underwear.

I looked down at my arms—into the pile of clothing I carried. The colors were largely neon shades; acid greens, tickle-me-pinks, canary-yellows, deep purples and sky-blues. I realised most of them were thongs, with a few boy-shorts in the mix. I was appalled—did she actually want me to buy these? I had let her put them on me, yesterday and today... but buying more? It was a bridge too far!

I looked up, ready to draw a line, and barely mumbled "Cin..."

Totally unabashed, she had pulled her yellow sundress up over her head, and was in the process of tugging past her breasts, which fell slightly and bobbed perky and tight. She was now totally naked, no panties or bra, just Cindy standing tall in black heels. I was, once again, overwhelmed by her sheer beauty; she was just so fit! Healthy, toned, and muscled, with just a bit of fat in all the right places. Her tan was flawless, and her curves led my eyes naturally down her body to her sex, a perfect mound hiding between her defined legs. Her naked glory made my penis twitch anxiously against me, a reminder of the panties that proved I was hers.

Catching me ogling her, she winked at me while approaching slowly, stalking towards me, hips swaying. I wondered if she practiced her wink on Jaxx while he practiced his smirk, and suddenly she was in my face, grabbing my hair at the back of my head and pushing her tongue into my mouth. I was jealous of her kisses, how confidently she strode up to me and took me in her arms. How assertively her tongue pried my lips open each time to delve my deeps. I was starting to think she had an abnormally long tongue; it so thoroughly dominated mine, pushing it to the floor and holding it down. She took my breath away, and I melted into her chest, one hand massaging a breast, while kissing with my head up to match her height in heels. It felt right.

So when I felt her beginning to slip my shirt up over my head, I complied readily, putting my arms straight up. She threw it in her floor with one hand, the other was already unbuckling my jeans. I realized I was already hard, my little penis making a small bulge in my trousers. Cindy didn't notice, or pretended not to, but when the jeans came down it was obvious. The cute monkey face jutted out on top of my small, rock hard penis, looking up at Cindy and I, and she couldn't help but giggle.

"Oh come on Sami, that's funny! And soo fucking cute! I love your little clit, it gets so hard for everything!"

I looked down at my penis, standing in front of this beautiful girl, and didn't know how to react. It was like Cindy had a super sense for all of my buttons, knew exactly how to press and flick and squeeze to keep me off balance and desperate for approval. Cruel and friendly, kind and degrading.

She sensed my discomfit. "Ohhh, Sami, don't be like that!" her hand was on my chin, lifting my face up to hers again. "Look, do you like me?"

Her earnest look and question shocked me. Shining green eyes that I wanted to live for, pouty lips and angular bone structure that made my knees weak. For once I was shocked into speech;

"W—wuh... What?"

"Do you like me? Do you enjoy hanging out with me, and fucking me?"

In my head I thought 'more like being fucked BY you,' but my mouth wasn't as clever.

"Uhmm... Well... Yeah..."

"Well I like it too! I like YOU! You're different from other guys. Guys like Jaxx." She smiled softly at me, and there was a hint of greater depth in Cindy. "I... Recognise you, Sami. I can't explain any better what I mean. But I want you to do this. I think it's best for you."

Then she was close to me, one arm wrapped around my shoulders, and her mouth in my ear. I don't know what happened, but the panties were around my knees, and she had her hand on my package, four long, delicate, strong fingers underneath, grazing my wrinkled little sack, while her unwavering feminine thumb stroked from the top. My penis was entirely hers, and she wasn't feeling merciful.

"Do you want to come for me Sami? I want you to come. So badly. It's so easy. Beg me to cum."

She yanked my head to be facing her again and stared at me coquettishly, biting her lip, while she palmed my entire package. Squeezing—not enough to hurt, but so that I had nowhere to go, no possible escape. Her grip on my throbbing penis was torture, because I wanted so badly to rub and dry-hump my way to orgasm.

"Oohh cin—unnh—I... Please lemme cumm! Please!" I whined, hating myself for my high pitching near squeal that I choked back to a whisper.

Her mouth was back in my ear, hot and breathy, "I need you to wear panties for me Sami! Will you do that for me? I want you to cum sooo badlyy..." her hand was a vice on my cock, unrelenting, never punishing but never pleasing, simply holding me. I was staggering against her, my head leaned into her chest and shoulders for support. You can probably guess what came next. Can you blame me?

"P—please Cindy... I'll wear... Ugh... I'll do it... I'll do it pleasee... Please let me cum I'll do anything." I couldn't tell if I was whispering or shouting anymore, just that I needed her to release me, to help me give in to the pressure that built deep inside me.

"Sami baby I need you to tell me you'll wear the panties. Not just today, from now on. I promise, I know best. Ugh your clit is so hard you're gonna squirt so much, please just say it!"

"Cindy I'll wear the panties from now oNNNN!"

As I finished the promise her hand relented and stroked me. The relief of her movement now clearly caused me to shout, but Cindy brought her hand from the back of my head around my neck to cover my mouth. It only took one slow, sure, caress from her soft hand to send me over the edge, and I swear my entire body came. I would have fallen to the floor or hit my head against the wall if it weren't for Cindy's calm, firm grip that kept me secure against her. I grunted into her hand the entire time,

"CIINNnnghhh."

My little penis stood as erect as it ever had and shot one spurt of cum, before it dribbled weakly into her still massaging hand. She giggled as my seed seeped between her fingers.

"Awwweee! It's so cute when it jumps like that!" then she half carried me a bit to my side, before releasing me to slump onto the bench. "Good girl. Let's get you cleaned up Sami, so we can try some of these on!"

She had produced some wipes from her purse, and she gave me some to clean myself off with as she did the same for her hand and arm. Then she turned back to me, her eyes green fire. Mentally exhausted by her torture, I had no argument—she had won, I was going to wear panties.

First she gave me the acid green pair, a stretchy, shiny thong that rode up high on my hips and cradled my spent genitals softly and firmly. It was unexpectedly nice. Cindy watched me pull them up, then instructed me to spin around. After a moment's hesitation I slowly yielded, and when I had turned 180 degrees, she gasped.

"Oh. My. God! Sami, you have, like, a perfect little bubble butt! Do you do ass workouts?!"

I was speechless. I had a bubble butt? She couldn't be serious.

"I'm serious! Look, stand like... This." And she stood on her tiptoes, with her back to the mirror, chest slightly pushed out and back arched to present her rear towards its reflection. She had pulled on a small white thong, and it and the position complemented her perfectly round ass, framing her little mound between two tantalising ass cheeks. I turned to stand next to her, imitating her stance, and it hit me like a ton of bricks.