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From Sam to Sarah: A Genre-Bending Story of Sexual and Personal Discovery. Chapter 1

Sam's trajectory takes a turn when Aubrey comes into his life.

It began in the fall of 2004. I was a junior in college. I was slightly chubby, shy, a virgin, and an otherwise completely average boy who listened to pop-punk, got decent grades, and was about to embark on a great and unexpected journey of personal and sexual discovery.

I lived in an off-campus apartment, but my roommate had graduated, so I had a two-bedroom to myself. This suited my shy personality well, but eventually I needed to find a roommate. My parents were not in the picture and I had to support myself. After a while, it became apparent that my mediocre income from tutoring local high school kids wasn’t going to cut it.

I posted ads around campus. A few people showed up, but none stuck. I think I was a little too introverted for them. Then she came. Her name was Aubrey. We spoke on the phone, and I could tell she had a cute voice, but I was completely unprepared for how gorgeous she would be in person.

She came into the apartment and had this confident aura that was instantly attractive. She was tall, about 5’10” with shoulder length, straight dirty-blonde hair. Her hourglass figure, flat stomach, and perfectly shaped C cup breasts had my heart racing before she said hello. In comparing her to a celebrity, the best description would be an early twenty-something Hillary Duff.

Her smoky eyes stared back at me, and when her full, pink lips began moving, she told me that she was a grad student looking for a room because she had just moved out from her current apartment because she could not get along with her roommate. I stammered at first, completely intimidated by her beauty and confidence, but eventually spoke. I asked if it would be weird for her to have a guy roommate.

“Absolutely not,” she replied, “I’m a free and open person and hope that you are too.”

She obviously could not possibly have known that my whole life had been spent trying to fit in, but not being able to, that girls laughed when I tried to approach them, that guys picked on me. Somehow, however, I mustered the confidence in the moment to tell her that I was a free and open person.

“Great!” she said, “then we should get along perfectly. When can I move in?”

We lived together for about three months and became fast friends. She was working on her PhD in bio-chemistry. I was working on my undergrad in history. She was a bit of a partier and ventured out on the weekends. She invited me, but I always found some excuse not to go. I liked the relationship that we had at home and did not want to be embarrassed when she saw how I was in public.

Everything seemed to be going normally, until that fateful day that set the whole course of events of then next three years in motion. We were hanging out at our apartment watching some HBO show that had strong sexual content. We were both drinking while sitting around in our pajamas, and I was feeling particularly good.

On the show, the lead actress was naked and about to climb on top of the male lead for a good old fashioned soft-core fucking. When she did, though, she apparently was straddling the actor too low on his legs to be considered realistic.

“Oh my god, that’s so fucking fake!” Aubrey giggled.

I was confused. Being a virgin, I guess I couldn’t tell.

“What do you mean?” I asked.

“She’s clearly not anywhere near his dick, Sam, has a girl ever ridden you that low?” she asked.

I began to blush and didn’t respond. There was a clear moment of realization in her eyes. She was putting together my introverted personality with my social awkwardness and coming up with the inevitable conclusions.

“Wait. Sam, are you… Are you a virgin?”

By now my face was beat red and my ears were hot. I didn’t know what to say. I could feel the sweat beading up on my forehead.

“It’s totally cool if you are,” she said, “it’s just not something you expect at your age.”

The jig was up, so I confessed. A new look came over her that I had not seen before. She was always confident, but, just then, it grew to a new level. She became slightly aggressive and it felt like she was in complete control of the situation, and me.

“Haven’t you ever wanted to fuck a girl before?”

I laid my whole high school experience out for her – that I had a few crushes in high school that didn’t pan out, that women were just so beautiful and alluring to me that I always felt uncomfortable around them because I held them in such high esteem, that everything about women turned me on, but something always held me back.

She bit her bottom lip and twisted a finger through her hair.

“Well. The first one is always the hardest. After that, it’s easy.”

She paused for a second.

“Why don’t you let me make a man out of you tonight?” she said.

My heart was racing. Did the most beautiful girl I had ever seen just offer to take my virginity? The mere thought of it sent blood rushing into my cock. We were both wearing pajamas, so she noticed this physical change quite easily.

“Looks like your little friend there is answering for you.”

That comment did put a slight damper on the situation for me. I sort of implicitly knew from watching porn that I was smaller than most guys in that department, but this moment seemed to be too good to pass up. Before I could say another word, she leaned over on the coach and stuck her tongue in my mouth.

Everything about her was driving me wild! Her soft lips, the way her tongue danced its way around mine, the feel of her breasts rubbing on my chest, and her coconut scented blonde hair. She straddled me and started grinding her hips into my lap.

Her warm pussy was separated from my cock by a few millimeters of fabric. I could feel the heat radiate off it. I could tell that it was wet. My hands reached up to start to feel her ass, but she pushed them to the side.

“Let me handle this,” she said.

Her hand reached into my pants and started stroking my rock-hard, undersized cock. Precum was oozing out. She pulled her hand out.

“It feels like you’re about to cum already,” she said, “but try and hold off. Think about something else.”

I tried my hardest to think about my upcoming homework and quizzes as her head slowly drifted down. She pulled off my pajama bottoms and, before I knew it, my cock was in her warm, moist mouth. With each bob up and down of her head, my body electrified from within. I finally understood why the end goal of every guy is sex. Nothing I had ever experienced had felt this good.

Her lips gripped my cock and slid up and down the shaft, while her tongue worked circles on the head. My cock was small enough that she easily allowed it to hit the back of her throat. While my now wet cock was gliding back and forth on her juicy tongue, she pulled off blowjob magic and start tongue-flicking my testicles while deep-throating me. I wasn’t sure how much longer I could hold off until exploding.

She took her shirt off. She made her way back up to my mouth letting her nipples drag up my exposed chest. When she kissed me again, I could taste my own salty, musty precum on her lips. She stood up and took off her pajama bottoms, leaving on her lacey white, v-cut panties.

She straddled me again and hovered her sopping pussy over my cock, letting her lips just barely touch it.

“Are you ready, Sam? You’re about to get your cherry popped,” she laughed.

“Oh my God, Aubrey. Yes!” I yelled.

And with that, she lowered herself onto me. Her velvet pussy hugged my cock as she slowly grinded her hips against mine. Her perfect tits rubbed on my face. I licked her nipple and she moaned. I couldn’t bear it any longer. It couldn’t have been thirty seconds since she let me penetrate her before I shot my load into her pussy. She twisted her hips as my cock erupted and stuck her tongue in my mouth one more time. She held herself there for a few seconds and then dismounted.

“How was that? How do you feel? Was I a good first lay?” she asked.

“Holy fuck, Aubrey, you’re incredible!” I panted.

She let out a little giggle and went into the bathroom. When she came back, she put her clothes on, sat next to me and put her head on my shoulder. We fell asleep just like that.

Over the next few weeks, we fucked a few more times. She got more aggressive in her love making each time, but I really liked how she took control. She was clearly wearing the pants, and neither of us seemed to mind. The only problem was that I could never last more than a few minutes.

A couple of times she seemed a little frustrated at this, but ultimately accepted it for what it was. I was in my own little heaven with her and thought nothing could go wrong. That is, until she insisted that I get out of this apartment and go with her to a party.

I told her how I was nervous at those things, and that I would rather not, but she told me that if I didn’t her pussy would be closed for business. She seemed to have no problem delivering that sexual threat. Of course, I didn’t want that to happen. How could I say “no” if that meant not being able to be with the most gorgeous visage of the female form I had every had the pleasure of laying my eyes upon.

The end of the week came, and it was time for the party. She told me it was going to be mostly other grad students and that I probably wouldn’t know anyone, but that she would stick by my side. She bought me a new designer button-down shirt for the occasion so that I would look a little older. When she emerged from the bathroom ready to go, I couldn’t help but take her all in.

She was wearing a green peasant top and a shiny black tulip skirt that came just about 1/3 of the way down her thigh. Her shiny white pumps accentuated her long, luscious legs. She was going to be the center of attention at this party. I was sure of it. Was I going to be up to the challenge of being the guy on her arm?

When we got the party, my suspicions were confirmed. Every guy in the place was ogling her from the get-go. They all looked at me, sizing me up, and I was averting eye contact, completely intimidated by the situation. There were about seventy-five people in this little three-bedroom house, and she seemed to know all of them.

Everyone kept coming up and bringing us drinks. A seasoned partier, Aubrey was knocking them back, while I slowly sipped. The party cruised along as expected, but the more drunk everyone got, the more the other guys kept getting between me and her. They were clearly flirting with her, but she didn’t seem to notice, or so I thought.

A few hours into the party, everyone was fairly trashed, including Aubrey. We were playing beer pong. It was me and her playing against two guys that she knew from classes. Being partners, we were on opposite sides of the table, and I was watching as the guy she was next to, who was a foot taller than her, kept finding ways to look down her shirt.

The guy standing next to me made a shot and they both yelled, “Drink!”

Aubrey, being a good sport, picked up the red solo cup and tilted her head back. In doing so, she lost her balance and stumbled back. The guy on her side caught her, thankfully, but I was certain he got a handful of her ass in doing so. He looked over at me just when he did it, I guess to see how I would react. He seemed like he was twice my size (I was 5’7”, he was 6’4”) and my pudgy exterior seemed no match for his muscular build, so I wasn’t looking for a fight. I let it go.

After the game was finished, Aubrey came over and gave me a big sloppy kiss, which made me feel better about the situation.

“Why don’t we find a room, so you can lick my pussy,” she said a little too loudly in my ear.

People could over hear. I don’t know what happened, but all my insecurities rushed to the surface, and I froze. She backed up and looked into my eyes with disappointment at my inability to take control of the situation.

“Let’s get out of here, babe. Let’s go back home,” I said.

“Well, I’m not ready. I still want to have fun!” she said looking around the room, “who wants to dance?”

It took about one second for the guy that had just had a handful of her soft, supple ass cheek to run over and grab her arm and lead her to the living room, where several couples were dancing to whatever rap/dance music happened to be playing.

I didn’t know what to do. I sat there stewing, watching from afar as Aubrey rubbed her ass into this guys crotch. His hands started on her hips, but were travelling up and down her sides. He put one hand on her stomach and the other on her back. He gave her a little push and she instinctively bent over, putting her hands on the ground and wiggling her ass back and forth in front of him.

Her skirt was short enough that her black, lacey cheeky panties peaked out the bottom. I saw his hand reach down to her knee and glide up her smooth legs, his fingers on the inside of her thigh. He tightened his grip as it got higher and I was sure that I saw him cup her ass with his fingers grazing her panty covered slit, rubbing on her most intimate of areas – the one that I had just been given the pleasure to know so well!

I couldn’t stand it any longer. I started to make my way to break this thing up when two guys got in my way.

“Where do you think you’re going?” one of them said.

“Get out of my way,” I said trying to push by them.

They were just as big as the guy manhandling who I thought was my girlfriend, and I was not the least bit intimidating to them.

“Come on, man. Chill out. Your girl clearly is having a good time. Let her have fun. Let’s get you a drink,” one of them said.

They each grabbed one of my arms and led me back into the kitchen. I was scared that I was going to get my ass kicked if I resisted, so I followed. They poured me a drink and then proceeded to engage in the most boring small talk, making sure to keep commenting on how hot Aubrey was, and that girls like that don’t like to get smothered by needy guys like me, so I should play it cool.

I finished the drink and, thankfully, it appeared as though they had lost interest in me, so I went in search of Aubrey. When I got to the living room, she was nowhere to be found. My heart began racing. I was in a panic. There a bunch of people smoking outside, and I knew her to be one that had an occasional social cigarette, so I check out there.

At this point, there were probably two-hundred people outside and the scene was wild. I looked around and was asking people if they had seen her. No help came. Twenty minutes had gone by and I was starting to get worried. I texted her, but didn’t receive a response. My heart beat at a fever pitch and my mind raced with possibilities. It felt like a panic attack.

I went back inside and sat on a chair in the kitchen, just about ready to give up, when I saw a door further down a hallway open. Aubrey stumbled out. Her hair was messy and her makeup a bit smeared.

“Oh my god, she’s been puking,” I thought.

“Sam!” she yelled as she stumbled her way toward me.

She threw her arms around my neck and planted a kiss on my lips. I expected to taste vomit but, somehow, what I tasted was much worse. It was the same salty-musty taste I had experienced that night when she took my virginity. It was the taste of pre-cum, although this time, I guessed there was nothing “pre” about it.

“Let’s go home,” she said, leaning her full weight against me.

It was then that I noticed her breasts were not pushed up and perky like they had been. She wasn’t wearing a bra. I looked down and saw her bra shoved in her purse. And, worst of all, I suppose, I saw those same black, lacey cheeky panties, that Mr. Beerpong’s fingers had brushed against twenty minutes earlier, balled up in there too.

My heart sank. But the deepest depth hadn’t been reached. That happened when I saw a glistening trickle of liquid dripping down her inner thigh. I realized she had just been fucked by someone else and that she had let him fill her with his cum. She saw that I saw and pulled herself in closer.

“Let’s go home,” she whispered in my ear, “I’ll explain everything on the way.”

I was heartbroken, but I didn’t know what else to do. I let her lead me out of the party. Several of the other party-goers gave me knowing glances. I was ashamed. It was clear that I had let the girl I brought to the party get fucked by someone else while I was searching around for her like a little imp.

The car ride home was silent. When we arrived back and were in the living room of our shared apartment, she could tell I was despondent.

“Look, let me make it up to you,” she said, implicitly acknowledging what had just happened – that her pussy had just been filled by someone else, that her lips had been rapped around the probably much larger cock of another man, that she probably loved the fact that someone was able to stretch her pussy and fuck her for longer than a minute.

“How are you going to do that?” I whined, a tear forming in my eye.

“Oh, don’t cry!” she said, “I’ll make it better.”

She started to kiss me and something I didn’t think possible began to happen. Even though I knew she had just cheated on me, my cock was still growing because of her embrace. Even though I could taste a cock that wasn’t mine on her lips, I was getting aroused, maybe it was arousing me more.

We moved to the bedroom and she stripped my pants off. She didn’t have anything to take off, her panties already wadded up in a ball in her purse. She sat on my 4” flesh rod and it slipped in without resistance. Her pussy had obviously been stretched by a superior cock. But there was also another factor. Some of that superior cock’s cum was still in her, and was now acting as a lubricant.

As she bounced up and down on me, I could feel this foreign seed leaking down on me. As much as I wanted to hate it, I didn’t. I was enjoying whatever this was. Who was I? Three weeks ago, I was a shy, virgin, pop-punk listening, introverted, chubby kid who lived by himself, and now I had what was most likely the most strikingly sexy girl at the university riding my cock with another man’s cum trickling down on me.

I couldn’t contain myself. I burst into her, sending my seed to mix with that of the muscle-bound man that had fucked her less than an hour prior. We didn’t even bother to clean up. We just lay there afterword and passed out.

When we awoke. She made me breakfast. I was still confused by what had happened the previous night. As I sipped on my morning coffee, she laid it out for me.

She said she that she had always been polyamorous, but that she really liked me. She wanted to keep our relationship intact, but that she would always need the occasionally fling with a strong, sexy, alpha male – it was just something that she needed. She said I was great, but that I was submissive, which was great for ‘sometimes,’ but that ‘a girl just needs to get fucked hard by a strong, dominant man from time to time.’ She said there was just something about me that was different than that.

She reminded me about how when we first met I said I was a free and open person and hoped that was still true, that I could live with this new arrangement. My mind raced. If someone had asked me a month prior if I would have ever gone for this, I would have said ‘no way’. But here I was, and I was thinking of accepting.

I thought about it for ten minutes. She kept looking at me and biting her bottom lip waiting for my reply. She was so fucking adorable. All I wanted to do was please her.

“I like you too much to not want to be in a relationship with you, Aubrey,” I said.

“I get it. I’m not the strong ‘alpha’ male you need, but I am something else that you do. I understand. I like it when you take charge and I follow your lead. If this is where you want to lead, then I’ll follow. Just promise me you won’t be sneaking around. I need to know what you’re doing.”

That is how it went for the next few months. We were living together as a couple, but about every other weekend, she would tell me she was going to a party and not to wait up. She would get all dolled up for another guy. She would do her hair, her makeup, and put on sexy panties underneath her jeans or skirts, making sure she was wearing something sexy to please someone else. I would sit and watch with envy.

I would send her off with a kiss, and when she came back she would kiss me again with the smell of a man’s cock on her breath and her pussy filled with cum. She told me who it was. Sometimes it was different guys, but she had been seeing more and more of Mr.Beerpong – whose name I now knew to be Scott.

She took my statement, that I liked to follow where she leads, to heart and started pushing the boundaries of our relationship. After one of her “dates” with Scott, as she took to calling them, she came home, and I was already asleep. She woke me with a whisper in my ear.

“I have a present for you,” she said.

She proceeded to gently straddle my face, telling me make her cum. I licked her swollen, used pussy as her “date’s” cum fell into my mouth and on my chin. She moved her hips back and forth, rubbing her clit on my tongue until she screamed in orgasmic pleasure, and then she curled up in bed, leaving me to jerk off next to her. She was awake, but pretended she wasn’t.

The weeks went by, but I started to miss her more when she would be out. The image of her getting her brains fucked out by a strong, muscular man danced around my mind and drove me crazy. Eventually, I told her about what I had been feeling.

“I just think that I would like to start being in the room with you. I want to be there with you so that I can be a part of your pleasure and make sure you’re okay. Do you think that would be okay with Scott?” I asked.

She sat there thinking. I could almost see the wheels spinning.

“I don’t think he would be okay with you being in the room with us while he fucks me,” she said.

The phrase “while he fucks me” simultaneously filled me with a sense of helplessness and a sense of erotic pleasure. My heart sank, and my crotch bulged.

“But I think I have a plan that could work,” she followed up.

My anticipation built waiting to hear her plan. Where would this journey take me next?

… to be continued …

 

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