The Craziest Sexy Love Story Ever


"Earth to Eric," Karen said, squeezing my hand.

"What? Oh, so sorry, I'm kind of out of it today," I said, which was definitely the truth.

"So it seems," she said. "Are you coming over tonight after parents are gone for the night and I will be home alone."

Karen was sexually insatiable, which is of course any high school boys' dream, but it was hard to do much with her other than sex. She was rather vapid in regards to academics and thus always talked about superficial things like pop music or shoes. During the election last year she asked who that black guy was. My heart sank, but she was so hot, so good in bed, that it was usually easy to ignore. Did I plan to marry her? God, no! But she was a good time throughout high school.

I glimpsed back at Beth sitting with a couple other girls and imagined her on her knees sucking Derrick's black cock. She is so pasty white and Derrick as black as night it would be a crazy contrast.

"Is that a yes?" Karen asked, her tone implying she was annoyed.

"What? Yes, of course," I replied, suddenly turning on the charm. "Tonight you are all mine."

Just as quickly as she was annoyed with me, she was smitten again as she kissed me and slyly squeezed my cock under the table. "I'm going to even wear something special tonight just for you."

"I can't wait," I said, even as I took a sideways glance at Beth.

We finished lunch, and I returned to the monotony that is learning. Usually, I would be counting the seconds until I was on the court, yet today that was not the case. I knew I would eventually have to be face to face with Derrick and I really had no idea what to say.

Thankfully, the practice went like it usually did no hint of anything different. The coach ended the practice with a speech and saying the first cuts will be posted on the wall in fifteen minutes and a reminder of our after school pre-season game tomorrow night. Being a veteran I wasn't worried about being cut, but I was curious which of the young players Coach thought could be key players in our journey to state. We lost in the semis last year and with six seniors this year we figured to be a threat to go all the way, especially with the addition of Derrick.

I went to the locker room and suddenly was paralyzed. I had showered after practice every day since my freshman year, yet now all I saw in my head was coach sucking cock. Yet, I knew I couldn't look like yesterday fazed me to Derrick who implied I may be a cocksucker too. So I got undressed, grabbed my towel and headed to the shower. Of course, nothing happened in the shower and I was just leaving when Derrick walked in.

"How's the water?" He asked me.

"A little cold," I shrugged.

"I may need something to warm me up," he quipped back, the innuendo only obvious to me.

Standing firm on my straightness I countered, "I hope you don't freeze then."

He laughed, as he finished, whispering in my ear, "It's only a matter of time, cocksucker."

Flushed and pissed off, I stormed out of there, got dressed and headed straight to Karen's to prove my straightness to myself.

I texted her I was on my way and she texted back saying to just come in and come straight to her room. Wondering what her surprise was and desperate to get laid, I sped there and quickly made it to her room. She was under the covers.

"Get naked, stud," she said.

I didn't need to be told twice.

"Already rock hard, what have you been thinking about?" she teased.

"You on all fours begging to be fucked," I answered, I loved fucking her from behind.

"I have something a little different planned for you tonight," she smiled playfully.

I began moving towards her but she said, "Stop and Close your eyes," she said.

I did as requested curious as hell.

I heard her move off the bed and walk towards me. "No peeking," she said, grabbing my hand and leading me to the bed.

"Lie on your back, but keep your eyes closed," she ordered.

I again did, dying to know what she had in mind. As I mentioned earlier, she was pretty sexually aggressive. She gave me a hand job in a pretty packed movie theatre on our first date, finishing by sucking my cum off her hand; she rubbed my cock under the table with her foot the first time she met my parents for dinner; she sucked my cock while I drove her home including when we went through a drive through; she made me finger her in the library at school; she fucked me in the boys' washroom after school one day. Anyways, the point is she was always full of surprises.

As I lay on the bed, I felt her join me and a moment later I felt her feet, her nylon covered feet, stroking my cock. I moaned as I opened my eyes to see she was completely naked except for a pair of black thigh highs.

She smiled, "You like?"

"Fuuuuck, yes," I moaned, the stocking sensation feeling so good. I had jerked off with my hand in Mom's stockings before, but this was way a good way.

"I thought you would," she said coyly, as she moved her feet up and down my stiff cock.

I joked after only a minute, "I am not going to last long like this."

"Are you going to come all over my stocking feet?" She asked, continuing her sensual foot job, putting a bit more pressure on my rock hard rock.

I moaned in response.

"Do you want to come on my feet, baby?" She asked.

"God, yes," I moaned, my balls beginning to boil.

"You've already come on my hands, face, tits, belly, pussy and ass I guess my feet seem like a natural next spot," she teased, reminding me of all the different ways she had got me off.

I quipped, "Don't forget down your throat and in that sweet pussy of yours."

"I guess the only place left is in my ass," she smiled, pumping her legs furiously, teasing me about the one thing we had not yet done.

"Shhhhhit," I grunted, the naughty innuendo the final push needed to let my cock erupt as my cum shot in the air and then onto her feet.

"So you want to fuck my ass, do you?" She teased, once I finished coming.

"That is a dangerous question to answer," I said, still out of breath.

She moved her cum covered toe to her mouth and licked my cum off it.

Karen was a cheerleader and a gymnast and ridiculously flexible, but this was a new moment of hotness.

"I love your flexibility," I said.

"Go open my drawer," she said, as she scooped some cum off the sheets.

I quickly did, curious what else she could have in store.

It was a butt plug and lube. I returned to the bed with a questioning look.

"Do you want to fuck my ass?" She asked again.

"Yes," I admitted.

"Right here, right now?" She questioned, her hand moving to her cunt and rubbing her clit.

"Anything you want," I said, my cock never shrinking after my first load.

"I was hoping you would say that," she said, reaching for the butt plug and lube. I watched her lube it up as she explained, "I had this in my ass all day today, preparing myself for your big cock, baby."

"Oh, God," was all I could muster in response, imagining her at lunch sitting beside me or walking down the hallway with this four inch plug in her ass.

"But I want you to do something for me too," she said.

"Anything," I said, willing to do just about anything to get her ass.

"Bend over, baby," she smiled.

"What?" I asked.

"Bend over, you said you would do anything," she said, her hand giving my cock a tug.

"T-t-that's for me?" I stammered, Derrick's promise to Coach suddenly popping into my head.

"It is now," she smiled. "Now bend over."

"I-I-I don't know," I hesitantly said, suddenly worried that it would make me gay.

"Baby, if you want my ass, I want yours," she said, her tone implying that this was the deal, take it or leave it.

I hesitated, but my cock was doing the thinking, and I ended up moving onto my knees. I felt warm liquid between my ass cheeks as she said, "I have been thinking about this all day, baby."

"Plugging my ass?" I asked.

"Both of us taking each other's ass," she said. "I considered buying a strap-on, or borrowing one from one of the girls, but I figured that might freak you out."

"Other girls," I asked, focused more on that then what was about to happen to me.

"Honey, almost all the girls in my gymnastics' club are either full out lesbians or at least bi," she revealed, as I felt the plastic toy pressing between my ass cheeks.

This was news. She had never mentioned any interest in other girls before. I asked, "Have you played with them?"

She pushed the plug and I let out a small yelp as the butt plug slipped into my ass. "That is for me to know and you to find out. How does that feel baby?"

"Strange," I answered, which was true. A slight burn occurred at first, but overall it felt natural.

"Fuck I wish I would have borrowed the strap-on," she said, as she stared at me bent over.

"In not sure I'm ready for you to fuck me," I said.

"Well, I'm ready for you to fuck me," she countered as she stood up, tossed the lube to me, walked over to the wall and bent over. Looking back at me still on my knees, "What are you waiting for?"

I didn't need to be told twice. I stood up, the plug in my ass shifting, but staying in me, I grabbed the lube and went to my bent over girlfriend. Reaching her, she said, "Lube that cock of yours generously and also my ass, baby."

"Sure," I agreed, quickly pouring excess lube on my cock. My hand coated, I moved between her ass cheeks and lubed her pretty butthole well.

"Fuck my ass, baby," she said.

"As you command," I replied, moving behind her.

"You understand I want to fuck your ass too one day soon," she said, as my cock moved between her ass cheeks.

Not really listening, but focusing on the task at hand, I agreed, "Sure thing."

"You will let me fuck your ass?" She repeated, as my cock poked at her rosebud.

Again my brain on auto-pilot, I agreed, "Yes, you can have my ass."

"Goooo slow," she moaned, as my mushroom top squeaked past her tight entrance. "Your cock is a lot longer and wider than that plug I wore all cheerleading practice."

The listing made my cock flinch and she giggled, "You like thinking of me with a plug in my ass don't you?"

"It's fucking hot," I agreed, as I slowly pushed deeper into her ass. It was so tight I wasn't sure I would be able to pull out.

"Does your cock in my ass feel hot?" She asked.

"My cock anywhere in you is hot, but this is so fucking tight," I replied, the plug in my ass poking a bit deeper in me as I pushed forward.

"Fuck, it burns baby, I'm burning for you," she moaned, even as her body trembled.

"Do you want me to go deeper?" I asked. "I'm only half way in."

"Yes, baby, I want all of you in my ass," she replied, sounding as if her teeth were clenched.

I continued the slow push forward, my head suddenly going to imagining Derrick's cock slowly going into coach. "Fuck," I said, annoyed.

"What, baby?" She asked.

"Nothing baby, your ass just feels so fucking good," I said, which was true as I tried to get Derrick and coach out of my head.

Yet, as I pushed further I wondered if the thing about Beth was true, had he fucked her, taken her ass? My mind envisioned Beth dressed in her usual conservative school attire, in the boys' locker room, bent over and getting fucked by Derrick's cock.

Karen moaned. "Slowly fuck me now, baby. I want you to fuck my ass."

Karen's words brought me back to reality and I held onto her hips and began slowly pulling back out. It was so tight my whole cock tingled with pleasure.

"Back in, baby, slam it into me," she begged.

I did, and as my body collided with hers, she screamed, "Fuuuuck, shiiiit."

I grunted too, as the plug in my ass readjusted itself in me, "Ohhhhh God."

"Now pound me, Eric, fuck my ass hard," she demanded.

Imitating Derrick, I asked, completely out of character for myself, "You want all my cock, slut."

As soon as I said it I was mortified, yet her response eased my concern that I had gone too far. "Yes, fuck your slut's ass, fuck it hard and deep."

I obliged as I began fucking her ass. Perspiration dripped off me, as I thrust deep into her again and again. Each hard thrust my body slammed into hers had the plug in my ass poking into me. The double sensation was very stimulating and my head again played tricks on me.

I imagined that instead of a plug, it was Derrick fucking my ass as I fucked Karen's; in essence I was the middle piece of a sex sandwich both giving and getting thick meat. As soon as the thought popped into my head, I shook it out focusing on being a dominant man.

"Beg for my cock, bitch," I demanded, again a derogatory word I would normally use.

"Oh yes, Eric, fuck my slut ass, make me your cum hungry bitch. You have come in my mouth and in my cunt baby; I want this load of yours to explode in my ass."

"I can make that wish a reality, my little ass slut," I grunted, continuing to fuck her ass harder than I ever had before.

"Oh shit, oh yes," she moaned, "it feels so goooooood."

"What does slut?" I questioned, getting turned on in this new dominant persona.

"Your cock in myyyyy ass," she screamed, holding herself up with one hand as she moved her other to frantically rub herself.

"Only dirty ass sluts come from getting ass fucked," I teased, even as I began to feel my balls boil.

"I guess I'm a dirty ass slut theeeeeen," she moaned, before shifting to screaming, "because I'm about to come from getting ass-fuuuuuuucked.

I kept fucking her hard as her orgasm coursed through her.

"Oh yes, keep fucking your slut's ass," she demanded, as she babbled, "so good, best, ev-ev-ever, fuck, god, soooo, shit, can't quiiiit comiiiing."

Suddenly her legs gave out and she fell to the ground.

"Shiiiit," she whimpered, as she fell onto her side.

I pulled her up onto her knees and shoved my cock in her mouth and fucked her face. She slobbered and gagged a couple of times as I roughly fucked her face, my own orgasm near eruption. I asked, pulling my cock out of her mouth, "Mouth or ass, slut."

"Fill my ass," she answered, getting on all fours.

I quickly got behind her and filled her ass with one deep hard forward thrust.

"Mother fucking Chriiiiiist," she screamed, as I learned from this angle I could go even deeper into her ass.

"Beg for my cum, Karen," I ordered, as I continued to drill her ass.

"Oh God, come, come, come, in my, my, my, asssss," she struggled to beg, the mixture of pleasure and pain obvious.

Suddenly Beth bent over taking Derrick's cock popped back into my head and my balls erupted and I shot my second load deep into Karen's ass.

"Yeeeeeees," Karen moaned, "Fill my ass with your cum."

I continued pistoning in and out of her ass until every last drop of my cum was unloaded. Pulling out, I ordered, "Clean me off, slut."

Her orgasm done, I worried she would not be so friendly to name-calling, but she quickly turned around, still on her knees and deep throated my cock.

As she did, she surprised me as she moved her hand and pushed the butt plug deeper into my ass, my whole body moved forward and my cock went so deep down her throat she gagged and fell backwards.

Laughing, she said, "Apparently you have an ass reflex."

Laughing back, I pulled her up, "Looks like you have a gag reflex."

"I never had complaints before," she pouted.

"Nor will you again," I said, kissing her hard.

We kissed for a couple of minutes before she said, "We should probably get dressed. The parents will be home in half an hour."

I reached behind to pull out the plug but Karen said, "Keep it in baby. I want that ass nice and ready for me."

"Are you serious?" I asked, the idea of a butt plug in my ass kind of gay.

"Deadly," she said, spanking my ass. "You did me, I get to do you."

"Is that so?" I asked, her brief submissive behaviour gone.

"Tit for tat or in this case ass for ass," she shrugged.

"But it's kind of gay," I said, Derrick's big cock again popping into my head.

"Only if you think of it that way," she shrugged, keeping the thigh highs on under her sweats.

"How so?" I asked, getting dressed myself, the plug still in me.

"I am a girl and you are a guy, thus it can't be gay," she said, rather matter-of-factly.

Her logic made sense. It can't be gay if I am having sex with a woman. "When you put it that way, I guess it isn't gay."

"Sucking a real cock is gay, sucking my cock will be fucking hot," she said, a twinkle in her eye.

"Why do you want to fuck me?" I asked, the timing so strange after all I saw recently.

"I want to do everything with you," she admitted, kissing me, her hand squeezing my cock.

"Tough to argue that logic," I gave in.

"Good, tomorrow night I plan to take your cherry," she said, talking in a deep voice, trying to act manly.

"Don't you ever use that tone again," I laughed, thinking it was strange to hear her talking of taking my cherry.

"Tomorrow after the game, your ass is mine," she said, slapping my ass directly where the butt plug was.

"Fuuuuck," I yelped, the plug going where it wasn't supposed to go.

"And keep it in until you get ready for the game," she ordered.

"Yes, Mistress," I joked, as I followed her downstairs.

"Mistress, I like that," she said.


I hurt myself twice, forgetting the plug was in my ass when I got in my car and when I fell on my bed to go to sleep. Oddly, as I lay in bed, I wondered what it would be like to have the toy in my ass moving in and out. I moved my hand to my ass and moved the toy in and out of my ass. I can't explain it but the feeling was indescribable. I wanted more. I wished it was longer so it would go deeper. Closing my eyes, I tried to imagine Karen with a strap-on fucking me from behind. I pumped the small plug in and out of my ass while simultaneously stroking my suddenly rock hard cock.

Pumping my cock while I tried to fuck myself, I continued envisioning what Karen had planned for Saturday night for me. I imagined me on my knees, as she again in sexy thigh high stockings slowly fucked my ass. I fantasized her telling me how hot it was to see me with her cock in my ass and how she planned to fuck me all the time. I moaned in response as my own orgasm began to boil. I imagined her moving faster in my eager ass when suddenly there was a deep hard thrust and I screamed and heard Derrick's voice, "That's it my straight faggot. You love big black cock up your man cunt don't you?"

I whimpered, "God yes, I love your cock in my man cunt," just as my cock erupted spewing my cum all over my sheets.

Opening my eyes, I gasped at the words I said out loud; mortified my parents might have heard me. I quickly pulled the plug out of my ass, wiped it off with my socks, and went to my bathroom.

Looking in the mirror I was mortified at how Derrick kept getting pulled into my sex fantasies, even during sex with my girlfriend. I just had the most amazing sex of my life and yet images of Derrick popped into my head while I fucked Karen's ass. I'm not gay, or bi, or curious, I said to myself. I need to focus on basketball and Karen. In the end, I thought even though my mind was playing tricks on me, the key was I stayed a man if these strange situations continued to arise, which they did the next morning.


I had just got out of the shower, my usual early bird self, when I got a text from coach, which wasn't unusual.


Please come over to my office ASAP to discuss the game.

Knock three times.

I often met with coach before the game so this wasn't new, but knocking three times was strange. I hoped it was just game talk, but a feeling in my gut told me Derrick was up to something.

I pondered whether to put the plug in my ass, but decided not to, mostly because I didn't have any lube and well it was really gay.

Report Story

bysilkstockingslover© 25 comments/ 107690 views/ 87 favorites

Share the love

Report a Bug

6 Pages:1234

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: