Back in College, My Shy Redhead Friend Became My Sex Slave to Help Me Get Over a Bad Break Up, and Gave Me Her Virginity in All Three Holes

Kelly squirmed as my cock slid into her pussy, the tight fit of her lips gripping and distending around my swollen tool as I slid back out before pitching forward once more. With her on all fours in front of the mirror, I could see her face distort in pain and pleasure as I pulled her hair hard, making her arch her back and thrust her sunburnt tits forward.

“Oh my god!” she wailed, letting out a sob as I kissed her neck.

“Do you like it?” I snarled in her ear.

“Yes,” she gasped before her voice turned into a stutter, like the words themselves were frightening: “B-b-break me…”

Let me back up a bit.

Kelly and I met on a blog platform that will be familiar to Millennials. I had my public facing page, that my friends knew about, like an online diary, but after I turned eighteen, I started a secret blog to post erotic short stories on. Some things never change. Kelly was one of my most loyal readers, and we got to know each other as a result—it seemed too good to be true that she would be a girl my age (actually a few days older than me, both November babies!) would be hanging on my every word, reading my stories and getting soaked from them, but, in fact, that’s what happened. Not everyone on the internet is a creep—just most of us.

Kelly lived in Florida, quite far away from my home in the Midwest, with a pretty chaotic family life. She was a redhead, and both proud of it and resentful of the fact, in the way that people who had their lives defined by one physical characteristic often are. She was more cute than pretty, with a pretty average body, but absolutely gorgeous green-grey eyes, and a sweet little smile.

Now, Kelly was incredibly shy and incredibly inexperienced. At eighteen, not only had she never had a boyfriend, she’d never even masturbated. I guided her through her first time touching herself over the phone, jacking off to her desperate little moans as I told her to play with her clit and lick her juices off her fingers. I got a girlfriend shortly after those first few calls, alas, and so we stopped doing that part, but we stayed friendly and chatted a few times a week into college.

During my junior year of college, my very serious relationship blew up sometime early into spring semester, leaving me depressed. It was my first really bad break up—drink a whole bottle of wine while watching a movie on my laptop bad.

And it would have been a lot worse, had Kelly not been eager to cheer me up.

She’d really had a glow up over the last few years. She’d spent the first year or two of college at a community college to save money, and then transferred to a prestigious state school and joined a sorority. I don’t think she ever quite fit in with the Greek scene—she was from a working class family, and always needed to have a part time job or two to survive in college, whereas her sorority sisters all got big allowances from daddy and drove new SUVs, while Kelly had inherited her step-mom’s station wagon from the late ‘90s. She was still pretty shy, and pretty nerdy—a huge Harry Potter fan at the time—and, crucially, still a virgin. She occasionally went out with friends and made out with guys at bars or frats, but that was the farthest she’d ever gone.

On the other hand, with me, she was open. Very open. We talked about fantasies, sexting daily, and soon, she was sending me nudes, showing me her gorgeous pink little slit. Maybe it’s just nostalgia, but I do seriously believe this girl had the pinkest pussy I have ever seen—when I had her spread herself wide for me, blushing the whole time, she looked practically neon pink inside.

Over the first few weeks after my break up, Kelly did more and more for me. Almost every night, we’d get online and she would strip for me, taking orders—fingering herself, making herself cum, and then sticking pens and markers inside her pussy and ass. Anal scandalized her at first, even though she read plenty of slash fanfiction, but before long, she was volunteering her butt to me, shyly spreading her plump pale ass cheeks to show me how her hole had relaxed from all the fingering I made her do. I joked that I was training her for her future boyfriend, that I would deliver her to him, whenever he materialized, ready to offer herself for pleasure in myriad ways. Almost every evening, she texted me to ask if I wanted to train her—sometimes, I worried that I was exploiting her, that I was making her do things she didn’t want to do—after all, she was so shy, she’d never had a boyfriend—but no, she really was insanely horny and excited to explore. She loved being told what to do, and she loved being praised for being a good girl. She just also happened to be shy and nerdy and lacking in disposable income, all of which kept her from finding a boyfriend the first few years of college.

We often fantasized that I might take her virginity—not only in her pussy, but her mouth and ass as well. I’d keep her on edge, making her touch herself until she was nearly cumming, and then ordering her to stop, all the while making her beg me to fuck her. She took orders well, and she was naturally eager to please. She loved being praised, and loved seeing how much I liked what she did for me.

In other words, we sort of invented for ourselves a dom-sub relationship from first principles, just by doing what felt natural. But of course, it couldn’t progress any further: she was in Florida, and I was in an arctic tundra.

That all changed, though, when spring peeked out of the snow, and my parents surprised me with cash for a spring break trip.

“You’ve just been so down after the breakup,” I remember my mom saying on the phone. Unlike Kelly’s family, mine was and is very well off, and while I made a point to never ask my parents for money beyond the basics, I was grateful for this sudden influx of cash—because I knew this was a chance to spend my spring break with Kelly.

I booked us a room at a budget hotel a few blocks from the beach—I remember everything being way more expensive than I expected, what with it being prime spring break season, but we didn’t near much. Just a private place to have our fun. Part of me was worried that Kelly, being so shy, would flake on me, and I’d end up on a weird solo vacation, but she seemed just as excited as I was.

I still remember getting off the plane shortly after eight-am, and finding Kelly waiting for me near baggage claim. She’d worn exactly what I told her to wear: a crop-top with no bra, and a hilariously short pair of short-shorts, that showed off her shapely ass cheeks. She had her arms crossed until she saw me, and when she raised a hand to wave, I could see that her nipples were clearly visible through the thin fabric of her top. She usually dressed way more modestly, and I knew she’d be burning up with embarrassment, but at the same time, this was Florida during spring break—she didn’t actually stand out. Ever other girl was dressed more or less the same.

“Um, hi,” she said, brushing some of her curls behind her ear when I made my way over to her. I leaned in to kiss her, and she whimpered into the kiss. “I’ve been waiting a long time for you to do that.”

I couldn’t wait to get my hands on her. We made awkward small talk until we got into the elevator to the parking garage, and as it descended, I wrapped her in my arms, kissing her, forcing a hand down the front of her jean shorts.

“Oh my god,” she gasped as my fingers glided over her silky wet lips. She was absolutely drenched and her pussy practically sucked my finger inside.

“You’re so fucking wet,” I whispered.

“Well, of course I am! I’ve been waiting for this for a long time too!”

I stroked her until the elevator was about to ding open, pulling my hand out right before a posse of senior citizens bustled past us into the elevator. My hand was still glistening with her juices, and her face was tomato red as she clung to my arm, panting softly as we stepped out of the elevator.

I’m still amazed we managed to get to her car without fucking right then and there. Once we were in the car, we made out in the backseat, my lips on her neck, leaving marks.

“Everyone’s going to know you’re getting fucked this week,” I said, teasingly, running my fingers over the hickeys I’d left on her neck. “Just from looking at you.”

“I don’t mind people knowing,” she said softly, and seemed to be trying to suppress a little grin as I rolled up her top, revealing her perky breasts, each topped with a hard little nipple, like a ripe berry waiting to be plucked. I pushed her down on the seat, so she wouldn’t be visible from outside the car, and lay myself over her, suckling her nipples as she whimpered and moaned.

Somewhere in the process, I got her shorts and panties down around her ankles, and, pinning her wrists behind her head with one hand, dug the fingers of my other hand into her eager little pussy. Her hole gripped me eagerly, and when I pulled out my fingers, I guided them to her lips and made her suckle them.

Now, before you start wondering—we did have a safe word system set up, and we had already talked through everything we did that weekend. Kelly knew full well that I had no intention of keeping my hands to myself the moment I saw her, though she’d requested that I wait until the hotel to actually take her virginity. She wanted to be on a bed, and to be able to look at me and kiss me while I deflowered her, and I wanted that too—we’d been friends for several years at that point, and the idea of finally taking her virginity, of making it special, really sounded perfect.

But that didn’t stop me from fingering and stroking her till she came. I don’t think I’ve ever met a girl who came as easily as she did—it’s honestly kind of amazing she didn’t become a slut, considering how easily she came from my fingers pistoning in and out of her pink little mound. She dripped all over the back seat and the whole car smelled like her as she writhed beneath me, her insides spasming around my digits as I pressed another kiss to her lips.

At that point, I decided I was going to take her virginity—her oral virginity. I sat back, and took her by the hair—she really had a lot of hair, mounds and mounds of the curly stuff, and I guided her face to the bulge in my pants. She was still panting and giggly from her orgasm but she set to work, undoing my belt buckle and my zipper before sliding down my boxers and pulling out my cock.

She stared at it for a moment, actually entranced. She’d seen my dick over video calls dozens of times, but I knew this was the first time she had actually seen a man’s cock up close, the first time she’d touched one. Her beautiful grey-green eyes seemed to glaze over with lust as she leaned in close, not quite touching my dig with her lips yet.

“It smells… meaty,” she said, finally, after several seconds. “It’s making me hungry.”

She giggled and reached her tongue out to tease the tip. She swirled her tongue around the head of my cock, and flitted her eyes up to watch my reaction.

“It tastes good,” she added, continuing her review. “Not as meaty as I thought. Maybe a little salty.”

She licked down my shaft to my balls, and began suckling them. Over the next few minutes, she absolutely bathed my cock and balls and until they were almost dripping with her spit, as though she were cleaning me like a cat, and only then did she take me into her mouth.

Her training had included a fair amount of oral training. I’d explained to her that most girls simply can’t suck cock worth a damn, and she’d have to practice, and she really took that to heart. She’d gotten several dildos of various sizes and almost every day, she practiced with them, recording herself for me so I could just her progress. At first, she’d barely been able to get through a practice session without gagging, but after a few weeks, she could bob her head on her largest dildo, swallowing it like it was nothing even as her eyes filled with tears.

Now, I was enjoying the rewards of that practice. She slurped happily on my cock, pressing her face into my pubic hair as I felt my dick press against the back of her throat. I felt her shudder on my cock as she pushed down the gag, and then finally slide off my dick, gasping. She looked up at me beaming, tears rolling down her flushed cheeks.

“Am I doing good?”

“You’re doing great,” I whispered and kissed her forehead. That was more than enough encouragement for her. What followed was and still is perhaps the greatest, most enthusiastic blowjob I have ever received. They say one of the secrets to giving a good blowjob is acting like there’s nothing else you’d rather be doing in the world, and for Kelly, I actually believed it, from the way she slurped and sucked and gargled on my cock, sighing with contentment every time she took a break from throating it to grip me with her lips and mouth the sheathe of my cock up and down. Finally, I blew in her mouth and she latched onto me, sucking and swallowing, her throat working overtime, practically nursing at my cock until she had drained every drop.

“I don’t know why girls complain about the taste,” she said, wiping her lips and gargling with a bottle of water once she’d finished. “It doesn’t taste like much of anything. Just kind of salty and sticky. I thought it was gonna’ taste way nastier.”

“Maybe I just have tasty cum.”

She grinned.

“Maybe you do. I’ll have to drink more of it.” She kissed my dick and put it back in my shorts. By this point, we’d been sitting in the station wagon for more than half an hour, and seeing as it was still morning, we were both getting hungry.

We stopped off at a diner for a light breakfast, and, since we couldn’t check into the hotel yet, went straight to the beach. Again, I had picked out beforehand what she would be wearing. Normally, when swimming, Kelly went for a modest one piece, too shy to show off her pierced belly button, but I’d instructed her to wear the bikini that had been hanging in her closet for over a year, unworn. Now, she modeled it for me in person, breaking into giggles now and then.

Running my hands over her as I applied sunscreen to her back and legs, a kind of bliss descended on me that I’ve never really felt since. I had a week of beach and sex stretching out ahead of me, and not a care in the world. I don’t think I’ve ever been so happy since, as though this had been the last gasp of my adolescence.

We did end up getting sunburned after not reapplying in time, so, let this be a lesson to everyone this summer. Finally, in midafternoon, both of us flushed red and positively radiating UV light, we rolled up to the hotel and checked in.

The room that would be our home for the next week had clean sheets, an HD TV, a small table and chairs, a mini-fridge, a microwave, and, much to my surprise, a balcony. The balcony, admittedly, only looked out over the street and not the beach, giving us little more than a view of some trash cans and the side of another, much nicer hotel, but it was a balcony nonetheless, and throwing open the balcony door to allow the sea breeze in suddenly made the room seem far more luxurious than what I had actually paid for.

As did the girl who’d just stripped naked, standing nervously behind me.

Here was another rule I’d given Kelly for our weekend together. Unless I specified otherwise, she was always to be naked when alone with me in our hotel room. I didn’t even need to remind her—she undressed without needing to be told, and stood, awaiting further instruction.

“On the bed,” I told her, and she bit her lip, grinning, and obeyed me, laying back on the bed, gazing up at me. “Spread your legs.”

She did so, revealing her pinkness once more.

“Spread your hole.”

She stifled a little noise of embarrassment but did what I said. She was plenty sticky with arousal, and her pussy lips seemed to want to adhere together as she pulled them apart. I undressed myself and mounted her, holding her face head with one hand while I took one of her breasts in my other. I slid my cock over her, letting it slide along her wetness while she whimpered. I flicked her nipples, twisting them, tugging at them, making her gasp as the underside of my shaft rubbed against her clit.

“Please,” she whimpered finally.

“Please what?”

“Fuck me,” she whispered.

I sank myself into her virgin pussy, her wetness absolutely engulfing me. She let out a soft wail as I took her virginity, as I impaled her with my cock, burying myself inside of her. She wrapped her legs around my waist and I held her there, letting her feel me deep inside of her.

“There you go,” I whispered in her ear. “You’re twenty-one and not a virgin.”

“Finally,” she snorted. “To think you’d be the one to take it.”

“Lucky you.”

“Yeah, lucky me,” she said, and kissed me hard as I began to move inside of her, thrusting into her. Her pussy seemed to suck me inside, just like it had my finger when I first touched her, as though making up for the years she’d gone untouched but stewing in her secret arousal. She yelped softly with each thrust, and angled her hips up, pulling me in deeper and deeper.

Since I’d already cum once, I had a bit more stamina than I might normally have had, and what’s more, I didn’t want her first time to be over too quickly. I slowed my thrusts down, focused on her breasts, sucking and biting her nipples as she whimpered and whined. I dug my teeth into the soft flesh, and she turned to bite the pillow as I bit her, marking her.

“You’re gonna’ devour me,” she whimpered breathlessly.

“You’d like that.”

“Yes,” she gasped. “Do whatever you want to me. You know I’ll let you.”

At that, I put my hand around her throat, applying gentle pressure as I fucked her faster and faster. Her pretty eyes widened and she squealed like a stuck pig. As I applied more and more pressure—never so much that she wouldn’t actually be able to breathe—I felt her body react, and she began, her chamber spasming around my cock as her sweet face shattered into pleasure.

After that, I ordered her onto her hands and knees. I’d noticed the mirror and I made her face it as I mounted her once more, making her watch herself get fucked, watch her own face as I took her harder and faster, pulling her hair hard, slapping her ass. I loved seeing her pink little asshole flex as she took my cock and she all but shrieked when I pressed a finger inside it.

Before long, I’d reached my end, and buried myself inside of her once more, pumping deep and emptying my load into her formerly virgin pussy while she sighed and moaned.

Now, before you worry—I had budgeted for Plan B, so we’d be able to have raw sex. The thrill of knowing that I had just cum into her unprotected pussy was delicious, and one I wouldn’t risk now, but I was young, dumb, and full of you-know-what, so it felt natural to us.

“Suck me,” I ordered, and she didn’t waste a second turning around, on her hands and knees, taking my sloppy cock into her mouth. She looked up at me wide-eyed, her eyes a little teary, as she rolled my soft cock back and forth in her mouth till I began to harden, and before long, she was impaling her throat on my dick.

This time, I had her ride me, and she came twice in quick succession, grinding herself into me as she dug her nails into my chest hair, a huge smile on her face. I gripped her ass and spanked it, even slapped her while she pressed her hips into me, and she threw her red mane back, let out a sob, and I felt her pussy spasm once more as another orgasm descended on her.

Afterwards, we snuggled on the bed, exhausted from the sun and the sand and the sex.

“So,” she said after we’d been quiet for a long time. “That’s sex.”

“That’s sex. Did you like it?”

“Uh-huh,” she said, nodding. “I kind of feel like I was missing out.”

“Selfishly, I’m glad you waited.”

“You would be, perv,” she said, kissing my cheek.

Later, in the shower, I lubed up my fingers and began exploring her ass while she bent over, bracing herself against the shower wall as the water poured down on her. She’d fucked herself in the ass for me on video calls before, but she’d never taken anything quite as big as my cock, and so I wasn’t totally sure she’d be ready. Much to my delight, her ass was relaxed and eager, probably from cumming a few times first, and when I pressed inside of her, she let out a moan and clamped down on me.

“How does that feel?”

“Good, I think…” she said, thoughtfully. “It’s like… If you were stretching me any more, it would hurt, but this is just enough. I think it feels good.” She sighed, grunting as I started to move inside of her. “Yeah. Yeah, I like this.”

She moaned softly as I stroked her back, whispering what a good girl she was in her ear as I fucked her ass. The sex was slow and deep, and looking back, I feel bad for how long we were running the shower, but being so deep inside the guts of a girl I’d been thinking about fucking for years was such a transcendent experience, I couldn’t tear myself away.

Finally, I blew my load inside of her, and slid out of her asshole, which was now quite a bit wider and more swollen than when we began.

“You did it, Kel,” I told her. “You’re no longer a virgin anywhere.” We kissed and then high-fived.

I took her out for pizza after that, and we bought a six pack of beers to split. One of the really fun things about Kelly was that, despite being a liberal, well-educated Millennial, she also strongly identified as a redneck (her words, not mine), and so she was more than happy to knock back beers and watch football. Despite her shyness and nerdiness, she had a tomboy streak that meant she wouldn’t back down from a challenge, whether it was bodysurfing a big wave or taking my dick in her ass.

But when she had her choice, aftercare looked more like a Harry Potter movie marathon, which is what we ended up watching that first night, cuddled up in bed. We were both too exhausted for more, after adding beer and pizza to the heady mix of sex, sand, and sun.

We went to sleep fairly early and I remember waking up with the sunrise and feeling enormously fortunate—I had this beautiful naked girl here in my hotel room bed who would let me do anything to her. She was still sleeping as I slid the covers off her.

One of Kelly’s fantasies was to be fucked while sleeping. Anecdotally, this seems to be a common fantasy—I think every girl I’ve been with since has nurtured some version of this fantasy. That having been said, talk it over before you try it—consent is sexy, and discussing what you both want can be a form of foreplay.

She wasn’t wet, so I needed to spit on her pussy to build up just enough lubrication to force my way inside of her. Her snores turned to moans as she arched her back and her eyes fluttered open. So much for doing it while she slept. I felt her grow wetter as I took her, and she bucked against me, holding onto me and whimpering until I emptied the first load of the day into her.

“I guess in my fantasy, I stay asleep,” Kelly said, craning her neck forward to see the bruises that had blossomed on her breasts and hips overnight, and the cum leaking out of her swollen pussy. “But that was pretty hot too.”

“I think you’d need to be drugged or drunk to stay asleep if I’m trying to force it in dry,” I pointed out.

“Yeah, even that kind of hurt. But… I kind of liked that.” She grinned at me, and I recognized the shy girl I’d first started talking to on the phone when we were both eighteen. “Like you were taking me by force.”

I took her to breakfast after that, both of us having applied a thick layer of high-SPF sunscreen. The week was only just beginning and we had plenty of beach and sex ahead of us. But I’m going to stop here for now—if there’s interest, I’ll continue with more from that week.

And yes, for those of you curious, I am still in touch with Kelly. She’s married now, and she’s a successful pediatrician—I’m very proud of her. Her husband knows about our past relationship, and even though I wasn’t invited to the wedding, they did take me out to dinner the last time I was in their neck of the woods.

“I still can’t believe what a lucky man I am,” her husband said as we both watched Kelly, a form-fitting dress hugging her swaying ass, make her way through the crowded restaurant bar to the bathroom. We were drinking Mint Juleps and waiting for our table when he lowered his voice, grinning conspiratorially. “It’s like you trained her to be the perfect wife for me. I owe you, brother.”

It was exactly what Kelly and I had joked about all those years back on our video calls. I drained my drink, and felt a peculiar sense that I’d let something very valuable slip through my fingers, like dropping a priceless family heirloom into a storm drain.

But that’s all for now. My messages are open if you have praise and compliments for me, but be advised that I’m not going to share pictures of Kelly or do anything to compromise her privacy. It should go without saying, but Kelly is not her real name either.