The Ultimate Playboy Pt. 01

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Evie stepped over my body, her beautiful tits hanging wonderfully in my face, still coated with bits of wetness from Daniela's tongue. She took my hand in hers. "I want my first man to be in a proper bed."

I let Evie lead me from the couch and back to her bedroom, simultaneously honored and excited to be her first. We lay onto the bed and kissed tenderly, while Daniela sat down in a comfy chair nearby to the bed. Carmen just climbed into Daniela's lap and began to rub her tits into Daniela's bosom, while lowering her head to nibble at her new lover's neck.

My hands roved over Evie's body, taking care to stay smooth and caressing, I didn't want to frighten her. I positioned my new erection at the third set of wet nether lips I would possess tonight, and gently began to lean in.

Evie went stiff as the head popped through, and I stayed right there to let her get adjusted. Once she relaxed, I let gravity take over as the folds slowly parted and my rod sank more deeply into her.

"Omigod. I'll feel so full," Evie whimpered.

I let my arms sink into the bed underneath her shoulders, kissing her again as I backed myself out before slowly pumping back in again. Evie had a sharp intake of breath as I did this, followed by a light giggle and a happy sigh. "This feels pretty good, actually."

I just smiled and kept on going.

Gradually, we picked up the pace, going faster and harder until Evie was bucking her hips at me to capture more of my meat with every thrust, and I was pistoning in and out of her like a well-oiled machine. She became much more vocal as we kept fucking, my rod carving her out in ways only rubber toys had ever done before, and with a lot more force this time around.

"Oh, fuck me! I'm fucking. I'm being fucked! Fuck me!" Evie was calling out, half in disbelief. I kept pumping until her wails started blending into each other incoherently, and she was just moaning constantly without words. I could hear her speeding up and getting higher and higher in pitch until amidst one of my really fast poundings she suddenly went deathly quiet for five seconds.

And then Evie blew. A shriek, so loud I was sure I'd have hearing problems for hours, detonated in my ear. Her pussy was suddenly juicing out of control and her whole body shaking so the wooden bed started creaking. I was fucking inside of a hurricane and the pressure on my dick was so intense that I knew I was about to lose control.

I pulled out just barely in time and then blew my wad all at once in a single gigantic orgasm that sprayed my cum all over Evie's upper body and face. The milky white jizz was splattered everywhere, coating her entire face, neck, and tits. And she was still trembling uncontrollably in the aftershocks of her climax.

It was one of the most intense orgasms of both our lives.

Carmen and Daniela were just gaping at us. We were both covered in sweat, and Evie leaned up to kiss me with a newfound aggressiveness. "We are soooo doing that again."

***

My trysts with the three babes of Brown 106 continued throughout the year. But that's all they ever were: trysts. No romantic relationships, I was just the guy they kept around for booty calls. Now it's not that I minded, really. Most guys would kill for this kind of no-strings-attached fucking. But I'd gotten used to having an Ashley or a Becky by my side: to have a date on Friday nights, to have someone I could reliably depend on, or even if I wanted to talk to someone. Girls were good for that. My male friends just wanted to video game or play ball.

One night, I found myself plugging away at Daniela doggy-style while she ate out Evie's wet pussy. Carmen was studying in the library, leaving our threesome for a few hours of stress-free playtime. Evie was just crying out her orgasm, and I could feel my balls approaching their climax when a sudden pang of loneliness hit me. It was such a strange sensation, and incredibly, I felt myself starting to soften.

Here I was, screwing one of the most gorgeous women I'd ever met, watching her lesbian munching on another beautiful girl, and I was losing my erection. I found myself mentally checking out, and I stopped thrusting. Daniela misread my intentions and she slipped off of me, turned around and stuck my dick into her mouth. She was still very new to blowjobs, but she was an eager student and was quickly becoming proficient.

When it became clear that I was not as close to shooting off as she'd originally anticipated, she motioned to Evie and soon the both of them were dually licking, sucking, and stroking me, and together they had my rod twitching and swelling of its own accord. No matter what my mental state, the pressure was building and building inside of me until finally, my cannon twitched a final time and then blew, exploding in both of their faces as they took turns milking out each spurt towards their open mouths. I let my head loll back in relief as the pressure in my mind went slack, and I resigned myself to let Evie slurp my other head into her mouth and drink down all my remaining fluids.

Once I was done, I just lay back across the bed and stared at the ceiling while Daniela and Evie kissed each other wetly. Then Evie noticed me first. "What's wrong? Didn't you enjoy that?"

Putting my most reassuring smile on my face, I replied, "Oh, of course. That was fantastic, really, from both of you."

"Then what is it?" Daniela cuddled in behind Evie, their naked bodies pressed against each other while they both looked at me.

"Oddly enough, I think I'm lonely. Don't get me wrong, I enjoy being here. But I realize that you two are a strong couple. I can see the love from here. I guess I wish I had that as well."

They looked at each other for a moment. Then Daniela spoke up. "What about Carmen? She's not seeing anyone."

For a few minutes, Daniela and Evie were all excited about the possible match- making, but when Carmen came home and the question was asked, she said flatly, "No." Nothing personal, I just wasn't her type. Great in the sack, but not the kind of guy to bring home to mom and dad.

For the rest of the year, I played the field. I went to social events, the local college bars that didn't check I.D., even picked up girls at the library. Some of the time, I just wasn't interested. Usually, if I was interested, I got laid. And the frequency with which I was able to meet new women was quickly earning me a reputation at the school.

I was the Ultimate Playboy. I was the quirky freshman who at first glance didn't look like a stud. But women were physically attracted to me for some unknown reason, and I never left a girl sexually unsatisfied. But I never had a long-term relationship. I was the idiot savant, a talented sex machine but incapable of getting a girl to romance.

***

Despite my string of hookups and one-night stands, I always had the girls of Brown 106 to come back to. Many times I passed over a girl throwing herself at me because I just wasn't that into her, and I would rather go back to the dorm and find at least one of my harem waiting for me. But we had a shallow relationship built only on sex, and when the year ended for summer break, so did our arrangement. I was moving on.

I went home for the summer, bringing all my dirty laundry and eager for my mom's cooking. While at home, I seduced a number of hot girls I knew from high school, as well as several townies. All of them were brief summer affairs, none lasting more than a week. I even hooked up with Becky for old time's sake when we met up at a restaurant.

But then it was time to head back to school.

***

CHAPTER 3

Returning to campus and looking around at all the pretty girls, many of them freshman and virginal, I thought about how I could really get used to this playboy lifestyle. I still didn't know what it was about me that attracted these kind of women, but I wasn't about to question my charmed life. I could just kick back, date around, and get laid as often as possible.

That whole attitude got spun on its head when I walked into the Bio building to start my second year. I was one of the first to arrive back on campus for the fall session. There were still a few summer schoolers around, and the new freshman for their Orientation week, but the academic area was fairly deserted. Bored, I decided to go for a walk.

I was cruising by the Biochem lab when a familiar face flashed in the corner of my eye. I stopped dead in my tracks two steps past the door, my jaw on the floor. It couldn't be.

I took two steps backwards, not even bothering to turn around, then peeked through the doorway. "So here's to you, Mrs. Robinson..." I hummed automatically.

My old High School teacher, the woman of my boyhood fantasies, was standing not twenty-feet away from me. Her dark hair was pulled into a neat bun, delicate and impossibly stylish lab glasses perched on her dainty nose, and a short skirt underneath the white lab coat. I was in total shock.

She didn't see me, but instead was concentrating on some complicated experiment that focused on a series of beakers filled with a strange translucent liquid. She would mix up some complicated chemical cocktail, then add a few droplets to the liquid to see if anything would happen.

She had a lab assistant always hovering nearby, a skinny girl with light brown hair in a ponytail who seemed perfectly at home amidst all the lab equipment.

"Gabrielle, would you please set samples 1 through 4 over on the next table?"

"Sure thing Doctor Robinson."

I must have been standing there for five minutes just watching them work, apparently without any positive results. Gabrielle was very efficient, and would glow whenever Mrs. Robinson would praise her. Even I could see the signs of idol worship.

At first I was just very curious, but then as my mind reasserted itself, it fell back on old habits. A few years had gone by, but Mrs. Robinson was still as gorgeous as ever. And she was apparently one of the new teachers at my school.

I was staring at her legs, silky smooth and naked beneath the short skirt. Her lab coat opened up a bit more, and I could definitely see the round curves of her breasts through her blouse. My hormones kicked up again as memories of that illicit kiss in her office came back to me. I remembered her perfect naked tits, the smell of her sweat and arousal, and the taste of her nipples.

I was hard within moments and was staring lasers of heat right at her.

Her head twitched as if she felt my stare, and when she glanced around to look, I automatically ducked myself around the corner of the open door, hiding myself so that I could still see through but she didn't have much of a chance of seeing me. It was strange, a few days ago I was a confident young man hitting on perfect strangers and bedding more than my fair share of them. Now, I was the scared socially-left-behind high school geek once again. So I hid and kept staring at her intently.

Her hands trembling, she put her notes down onto the table, and ran her palms over her body, part drying them and part caressing herself. I felt a surge of hormones kick up in me watching her hands gliding over her breasts, and she gasped at the same time. Maybe I really was having some weird effect on her.

Then something else caught my attention. The liquid in the beakers, ALL of them, were starting to bubble, as if they were boiling over.

Mrs. Robinson and Gabrielle, both, stopped still and were looking at the beakers in shock. Most of them hadn't been touched.

Then I noticed that Gabrielle was sweating, her white skin flushed, a few locks of hair coming loose from her ponytail and falling over her cheeks to frame her face. She was panting, and then her attention moved away from the beakers and over to Mrs. Robinson. I focused in on the assistant, watching her glance at Mrs. Robinson then turn away, clearly waging a war inside of her mind that she seemed to be losing. At last, her eyes sharpened and she started moving with a purpose, right at Mrs. Robinson.

The gorgeous teacher was fighting desperately to keep her composure, oblivious to her lab assistant. But then Gabrielle strode forward, putting her hands on Mrs. Robinson's face, turning her and then planting a fat kiss on her lips.

Whoa, maybe I had idol worship mixed up with an infatuation.

Mrs. Robinson kissed back with full force before backing away, shaking her head. "What's going on? I haven't felt this way since... since that boy in High School."

She grabbed her own head, as if she could mentally squeeze it out of her. "I feel so hot!"

"Me, too," Gabrielle moaned. "I'm so horny..." So when Gabrielle leaned in again and kissed her again, the heat of arousal in both of them took over and then they were Frenching madly.

Mrs. Robinson still had enough sense left in her to realize they were in a very public place. She took Gabrielle by the hand and led her through the lab and into one of the adjoining classrooms. Once they went through I stepped into the lab and followed them to the doorway.

The classroom was in complete darkness, with no windows or light except for the light coming from the lab. I realized that I was silhouetted against the light and it would be impossible for me to escape detection this time, but it turned out that neither of them were even looking in my direction.

Mrs. Robinson was flat on her back across the big island countertop in front of the whiteboards, her head actually falling back into the sink as she stared at the ceiling. Usually there would be some experiment done on the island where anyone in the classroom could see. But now there was just a hot Sapphic encounter there for me to see.

Mrs. Robinson's skirt was hiked up, and her panties were on the floor. Her hands were trying, unsuccessfully, to open her blouse, rubbing at herself in a frenzy. Gabrielle had her face and one hand in Mrs. Robinson's crotch where she was eating her out like there would never be a tomorrow.

"Fuckin' A!" Mrs. Robinson cried out. "I'm not even a lesbian!" Gabrielle didn't bother responding, but just kept licking and sucking until she produced a shrieking, hip-twitching orgasm from the pussy in front of her.

The climax seemed to restore some semblance of sanity to Mrs. Robinson, who blinked her eyes several times as if the reality of what just happened was starting to sink in. Her clothes were scattered. Most of the blouse buttons had been opened and her bra cups shoved to the side. But there was a new alertness to her that worried me.

Gabrielle had just moved around the countertop to where she could get a good handgrip on Mrs. Robinson's perfect tits when they both finally saw me.

Gabrielle gasped and half ducked behind the countertop. But I saw the recognition in Mrs. Robinson's eyes as she looked at me. "Ohmigod, it IS you."

Gabrielle just freaked out, horny or not. Once she realized that Mrs. Robinson wasn't going anywhere, she grabbed her clothes and ran past me, into the lab.

Once Gabrielle was gone, Mrs. Robinson got off the island and walked straight to me. I had to work not to watch her breasts bouncing around. She stopped a foot away from me, her gaze penetrating. I could see her mind whirling behind her eyes as she processed what was going on.

"Mrs. Robinson..." I almost whistled.

"Actually, the 'Mrs.' was just for High School. I'm not married, so it's 'Miss Robinson' or 'Doctor Robinson' around the college. But you..." she stepped forwards, bringing her half naked body right up to me, then put her hands on my chest. "You can call me Fiona."

With that, Fiona leaned forwards and stuck her tongue into the back of my throat. We kissed as if no time had passed since that day in High School. It was wet, it was sloppy... it was the best kiss of my life.

Her hands fumbled at my jeans until my erection sprang up. The hormones inside of me were rapidly rising up again after their brief cooldown, and I could feel the electricity crackling in the air all around us. We finally broke for air after I'd gotten my jeans and shoes off, and then I ripped my shirt over my head.

"I think I like 'Mrs. Robinson' better," I chuckled.

She just smiled at me, then got a firm grip on my shaft. Tugging me by it, she led me to shuffle back towards the island. "I've been dreaming about you for years. And I'm not going to waste anymore time before I get to fuck you."

She turned around, and dropped her lab coat to the floor before starting to finish unbuttoning her blouse. She pulled her hair out the bun, then shook her head to let the dark tresses cascade around her pretty face. She smiled at me, taking her time looking up and down my naked body, then she finally turned around and stuck her ass at me. Mrs. Robinson leaned forwards, bracing her hands against the countertop, then she craned her head to me. "Now get over here and FUCK me."

I stared at the perfect ass and creamy skin, and especially the inviting pink rose between her legs, very wet. "Yes, Ma'am."

I stepped forwards, my hands on her hips. I paused just a moment when my other head nudged between her legs. I wanted to savor this moment. My oldest fantasies were coming true.

Mrs. Robinson moaned as I pushed forwards, my cock slowly parting fold after fold until at last my hips were flush tight with her asscheeks. I leaned my chest down onto her back, wrapping my arms around her in a warm hug. This was really happening.

We both didn't move for a minute, just enjoying the feeling of being coupled together after such a long time. But then her hips twitched, and my rod twitched inside of her. I pulled back slowly, moving my hands to hold those globes of female flesh I had dreamed about so much.

Even after all the pussy I'd had in the last couple of years, Mrs. Robinson was still the goddess of my dreams.

She pushed her hips back at me as I drilled forward into her again, letting out a groan as our hips clashed together. I pulled back, and pushed forward, back and forth, gradually picking up speed.

Mrs. Robinson was moaning in pleasure with every thrust, music to my ears. Her voice was an intoxicating aphrodisiac, getting me more and more aroused until I was blind with lust and a desperate need to fuck her even harder.

I lifted my torso off her back and moved my hands to her hips. We set into a rhythmic slapping noise as I carved her out, faster and harder until we were truly fucking each other.

I could feel the heat boiling inside of me like pressure cooker, the friction on my rod intense. But the friction on Mrs. Robinson's pussy was even more, and after a few minutes her whole body started shaking even as I continued to drive into her, and she screamed out her latest climax.

Her inner muscles were spasming, squeezing my shaft like a hundred hands and I started grunting with exertion. She must have been able to tell that I was nearing my limit from the grunts, because she cried out. "Oh, cum in me! I want to feel it in me!"

Hearing that just about did it for me, I thrust in as hard as I could, burying myself as deep as I could go. I could actually feel the crown of my cock twitch and then split apart, unleashing the torrent of sperm that had been building up inside of me.

She laughed as the warm fluid splashed against her insides, and her hips were sloshing around and around until I felt like I was cumming inside a washing machine. Her inner muscles squeezed and caressed with expert motions, coaxing every last drop out of me.

My eyeballs rolled back in my head as I threatened to collapse, but I could not dream of moving in any way that would pull my cock out of her wondrous pussy.

Finally, she stood up, a satisfied smirk on her face. "Ah, now I've finally been able to do that. I've been dreaming about feeling your spunk in me for years."

She came up right in front of me, looking up into my face with that smirk. She knew exactly how much of an effect she could have on me. And still staring straight into my eyes, she called out. "Gabrielle, come in here."