My Graduate School Romance - Lindsey's Perspective

This is a sidebar to the primary story My Graduate School Romance. You do not need to read that story to enjoy this one. Most of this story is set in the nineties and aughts (2000s). Remember things were slightly different then. Everyone is at least 18.

The characters in this story are flawed, just like you and me. Sometimes they make bad decisions as they struggle to live their lives. Sometimes they make life changing decisions. Again, all characters and situations are complete fiction, a product of my fertile imagination. Any similarity to actual people and situations is purely a coincidence. All constructive criticism is welcome.

*****

I began playing piano at a very young age. My mother has an old video of me plunking away when I was about four. I was pretty good. In first grade I started taking lessons. By the time I was twelve I was being described as a prodigy. During high school, I went away to some summer camps where I got to study with world renowned pianists. Not surprisingly, while a senior in high school I received a full scholarship to Juilliard.

The August after high school graduation, I headed off to New York City. Coming from small town America, I was blown away by the Big Apple. I settled in and I really loved my course of study. It was everything I ever dreamed of.

At the end of the first semester I was talking to one of the graduate assistants. She told me how difficult it had been for her to find a full time position that paid well. That got me thinking and by Spring Break I had decided I needed to pursue a degree that would pay the bills. I applied to and was accepted at State and I started their business program the following fall.

Toward the end of my first semester at State I had my first sexual experience. I can't even remember his name. All I remember is that once I got past the initial pain, it was wonderful. I can picture the guy. He was a jock and he treated me like a princess. Having his cock fill me was amazing and afterward I just wanted to do it again.

The following weekend we had sex again and this time I had my first orgasm. It changed my worldview. The pleasure that flowed from my pussy had my body shaking. The endorphin rush was mind blowing. I wanted to experience that again and I started craving sex, craving an orgasm. Later the following spring one of my sexual partners commented on how easy it was for him to make me cum. Word quickly got around that I had hinges on my heels and I had guys constantly asking me out.

Toward the end of the semester I caught my first STD and the folks at the campus clinic gave me some lessons on how to protect myself. While I became a little more discriminating on who I would fuck, I was craving sex more than ever.

*****

That summer back home, I took my sexual activity to the next level. This was the late Nineties. I bought a small white bikini and started hanging out at the lake when I wasn't working. The lifeguards had a shack and I'd fuck them on their breaks. Most days I'd get fucked at least three times.

In the evening I had a waitressing job at a diner out by the interstate. I didn't pick up any guys. I just did my job and took home shitty pay. Then one evening, an older gent came in. He just drank coffee and read the paper. I'd come over and give him a warm-up and he'd chat me up.

After about an hour he said, "Lindsey, don't you hang out down at the lake?"

I smiled. I didn't know where he was going with this.

He continued, "I love your white bikini. I love watching you come out of the water."

He's hitting on you. I continued smiling. It was nice being admired.

"I see you go into the lifeguard shack. My naughty mind thinks of all sorts of things going on in there. If you were to do some of those things with me, I'd make it worth your while."

What?

"You don't know what I'm talking about do you love?'

"I'm not sure."

"When you get off, we'll go out to my car. We'll have some fun in my back seat. You make me happy. I'll make you happy. Then you'll walk away fifty dollars richer."

Fifty dollars! That more than what I make in an entire shift!

He smiled, "I see that interests you. When do you get off?"

"One a.m."

He looked at his watch, "It's twenty to. I'll leave in about ten minutes. I have a black Jeep Wagoneer. I'll be parked in the back of the lot."

Here was some guy I was going to fuck and I didn't know the first thing about him. I asked, "What's your name?"

"Gary. So will I see you?"

I nodded. What the fuck are you thinking Lindsey? Are you really going to prostitute yourself? You love fucking! Just think of it as getting paid for doing something you love.

I was delayed for five minutes as I was leaving. Gary's Jeep was in a darker spot in the parking lot.

As I approached he said, "I thought maybe you were going to chicken out."

"No. Just had one more chore to do before I left."

He got out and went around to the back door so that we were hidden from prying eyes. "You've never done this before have you?"

"I've had plenty of sex."

"No. I mean get paid for sex."

I shook my head, a little embarrassed.

"It's no big deal really. It's just like doing the lifeguards in the shack."

He was sitting on the back seat with his legs hanging out. He had the interior light off.

I came up to him and he put his hands on my hips, "You are a stunningly beautiful girl, do you know that?"

He had a kind face so I put my arms around his neck and kissed him. Soft lips. So nice.

He spoke into my mouth, "Let's take off your shirt."

I unbuttoned my blouse and unhooked my bra.

Gary immediately latched onto my nipples, groaning with pleasure. "You're amazing."

I was really enjoying the flattery. His sucking was making me wet, sending shivers down my spine. The excitement had me close to an orgasm.

"How about your pants?'

I kicked off my shoes, dropped my pants, and stepped out.

Gary was locked in on my crotch, "I wish there was more light. I bet you have an amazing fire bush."

I hooked my thumbs in my panties and pushed them to the ground. "You can't see them, but you can feel them." The warm summer air flowed over my body bringing my excitement to a fever pitch. I was in heaven.

He ran his finger along my wet cunt, "An amazing pussy."

He stood up and dropped his pants. He sat back down and laid back in the seat. "It is customary for the woman in this situation to ensure the man is as hard as possible. Can you suck me?"

"Gladly."

I loved sucking cock. I climbed in and took his cock in my hand. He was pretty big and rock hard. I took his nob and started sucking and licking. Some bobbing, some stroking. When I thought he was ready I climbed up and straddled him. The seat was wide enough that I had my knees on either side of him. I placed his cock at my opening and pressed him home. God, what a nice stretch. Gary groaned and started playing with my nipples. I was riding him, grinding my hips so that my clit was hitting his pubes. He pinched my nipples and my orgasm came crashing down on me. Pleasure flowing up and down and exploding in the middle.

Gary grabbed my hips, "That's it. I can feel you cumming. Fuck me Lindsey. Your pussy is so tight. Fuck me hard."

I was moving as fast as I could. I threw my head back and it bounced off the top of the car. I could barely breathe, but I kept moving. He thrust up into me and I felt his warm seed deep in my pussy.

I stopped moving, the pleasure still flowing. "That was fun."

"Yes, it was. Maybe we can do this on a regular basis."

"Sure."

I climbed out and found my clothes and got dressed.

Gary handed me some bills, "That was so much better than fifty. I gave you a little extra."

I didn't dare look, so I stuffed the money into my pocket. I kissed him and left. When I got home I found out he gave me seventy. Holy fuck! Seventy bucks to let a guy give me an orgasm!

The next day at work the other waitresses gave me some shit, "Did I see Gary's Jeep rocking away last night?" "Getting a little dick on the side are we?" "Are you doing it for free? He needs to pay for your fine ass."

I mostly ignored the comments or denied them. In fact that summer I became very good at lying. A lie would come out of my mouth and I wouldn't even think twice.

*****

Two nights later, Gary showed up again and I fucked him for $70. I really liked the size of his cock. He'd stretch me nicely and would quickly bring me to an orgasm. In fact he commented on how quickly I would cum.

When we were done, I got dressed and walked over to my car. A cop car pulled up behind it, blocking me in.

Officer McMahon got out, "Hi Lindsey. A little extra-curricular activity?"

What the fuck! I played dumb. "I don't understand."

"You're a smart girl. You just fucked Gary and I'm sure he compensated you nicely for your efforts."

I couldn't run away. I just leaned against my car.

He came over and grabbed my tit, "See, I've been sitting in the diner, drinking coffee and then I saw what I assume is an illegal activity."

Oh shit!

"Let's move over here in the shadows. I wanna see your tits."

Fuck! I unbuttoned my blouse and unhooked my bra.

He stuck his hands under my bra, "See hookers like you usually have a pimp to keep them out of trouble. But you don't have one, do you?'

I shook my head.

He was kneading my tits, "Normally, I would get a cut of what the pimp takes in, but I know you're just a poor college girl. Instead of a cut of the take, I think I want to sample your wares."

He pushed my blouse off my shoulders, then unzipped his fly.

"On your knees girl.'

I knelt in front of him, the grass was damp with dew. He pulled out his cock. He wasn't as big as Gary. Just average.

"Come on Lindsey. You really don't want me to bust you for prostitution do you?"

I took his cock in my hand and began working him. I licked the head.

"You can do better than that. Suck on it bitch."

This guy's mean. I began sucking in earnest. He pushed the back of my head and his shaft went further into my mouth. He stunk like piss. He pushed again and I gagged.

"Oh, you are going to have to get better at sucking dick Lindsey if you want to reach the big time. Let me help you."

McMahon grabbed the sides of my face and began fucking my mouth. I gagged again and pushed him off.

"Jesus! You got to let me breathe!

He cuffed me on the side of my head, "No I don't. Take care of me bitch!"

He actually did lay off me a little, but he was still going pretty hard, pushing my face onto his cock. Soon, he was grunting and I felt him cum in my mouth.

"Swallow it bitch! Swallow all of it."

When we were done, he stepped back and zipped up his fly. "I'll be looking for you when you're turning tricks. When you're done each night, I'm going to want something. Next time I think I'm going to want some of your cunt."

He got in the patrol car and drove off. Fuck! What a creep!

*****

As the summer wore on, I mostly stopped fucking the lifeguards and focused on making money in the diner parking lot. Gary introduced me to another older man. Mister Bradshaw was the father of one of my girlfriends. That felt really weird, but he was very generous. A hundred bucks a pop. Usually I'd have either Gary or Mr. Bradshaw stop by for a fuck.

Of course, Officer McMahon was always there for his piece of the action. Usually he'd bend me over the hood of my car and fuck me from behind, groping my tits. Sometimes I'd see one of the other waitresses leaving to go home and they'd stop and watch me get fucked. Word got out that I was the town slut and I got other customers.

A couple of weeks after all this started, Gary came in and I told him I couldn't go that night. I was on my period.

He smiled, "My sweet innocent girl, you have other holes we can use. I promise to be gentle and I'll show you ways you can make even more money. Double in fact. I'll show you how you can still have a nice orgasm."

Other holes? Shit! He wants to fuck my ass!

Sometime around midnight Officer McMahon came in for his coffee. By now he was asking to be seated at one of my booths. He was very pleasant to me, but he couldn't take his eyes off my tits. When I came to give him a coffee warmup, he'd discretely stroke my thigh. He gave me the creeps.

At the end of my shift, I walked out to Gary's Jeep and he took me around the back of it. "Lindsey, I promise to be very gentle. I have some lube to make this easy." He handed me a wad of money. "That's double what I usually give you. Are you cool with this?"

I wasn't sure, but that was a lot of money. I nodded.

"That's a good girl. Take off your pants and lean on the bumper. I'm going to lube you up."

I dropped my pants and panties and bent over.

He squirted some cool gel on my asshole and began smearing it around, "I'm going to put my finger in you. Tell me if it hurts. Take off your blouse too."

Soon I was naked. I felt his digit probe into my ass. It felt weird, but it gave me shivers. This had possibilities.

Gary smeared some lube on my clit, "Rub yourself so you can cum.'

I rubbed my clit and soon Gary had multiple fingers in my ass. He explained that he was stretching me so I wouldn't tear.

"Okay, Lindsey. You're ready."

He placed his cock at my asshole and slowly started pressing into me. His hands came around and cupped my tits.

I immediately started having doubts, "Oh shit!"

"Be brave young lady. When you get good at anal, you will be able to make a lot of money."

I sucked it up and I felt the head of his cock pop past my sphincter. He slowly fucked me, gradually pressing deeper. The stretch was nice and I could feel him filling my ass.

"Keep playing with yourself."

I had stopped working my clit and I started again. Gary grabbed my hips and started thrusting faster into my ass. I heard myself groaning, partly from pain and partly from pleasure. Soon my orgasm started and pleasure washed over me.

Gary cried out, "Oh fuck Lindsey! Squeeze me!"

When he came I could feel his spunk deep in my ass. "Lindsey, that was fucking great."

"Then I need some too." I nearly jumped out of my skin. It was Officer McMahon.

"Gary, don't drive off just yet. Let her lean on your car. I won't take long. Stay put you bitch.'

I looked back and McMahon had dropped his pants and was jerking himself hard. He got behind me and was soon fucking me as hard as his hips would swing. At least he wasn't as big as Gary, but it was humiliating. The cop treated me like a piece of meat. He was grunting like a pig and I felt him cum inside me.

He pulled out and pulled up his pants. "Much obliged Gary for showing this cunt a new way of fucking."

He strutted off to his cruiser.

Gary looked crushed, "I'm sorry Lindsey."

"It's okay. He's been taking 'his cut' all summer." I used air quotes.

By Labor Day, I had put away over eight thousand dollars. It saved me from taking out a big student loan. I calculated that if I was able to keep this up, I wouldn't have to take out any more loans.

*****

When I got to campus, I saw a problem with that plan - nearly all the guys were as poor as I was. I had to find the rich guys.

School hadn't started yet, so I had some time. I drove around campus and the surrounding environs. On Frat Row I found one house that had some serious cars outside - Beemers, Mercedes, Audis, and a Lexis. I got out and talked to a guy moving in.

"Does your frat throw a lot of parties?"

"Every weekend babe."

"Do you bring in girls?"

"Don't have to bring them in. They just show up. You'd be perfect. You should come over. We're having a pool party on Friday at three."

I looked around for a pool, but I didn't see one."

He laughed, "We just set up a kiddie pool, but it's a great excuse to wear a bathing suit. Bikinis are encouraged. Topless is better."

"Which frat is this?"

"Eta Pi. We joke that it really should be Eta Pussy. Get it? Eat a pussy?"

Guy's a loser. Rich loser. I smiled, "So smart."

When I got back to my dorm, my roommate was moving in. I helped her carry in her stuff. Her father and her big brother couldn't take their eyes off me.

Her name was Jennifer and once her family was gone she opened right up. "Do you have a job?"

"I had one for the summer, but not now."

"Do you like to entertain guys?'

Is she talking sex? "I certainly love being around men."

"Something you might want to think about is our Hostess Program."

"Hostess Program?"

"When the school has visitors or recruits, we 'entertain' them." She used air quotes.

Yup. Sex. "If I'm reading you right, I love entertaining men like that. How are you compensated?"

"Technically you work for Admissions. They call it a work-study, but when I did it last year, they covered my entire tuition, room, and board."

"Okay, now you're talking. So you put out a little, and they take care of everything else?"

"Actually put out a lot. Last year there were twelve of us. We worked every weekend."

"Where do you take the guys?"

"Typically, the school puts them up in a dorm room. You hang out with them from noon on Friday until noon on Sunday. Make them think they're handsome and smart. Show them what a good time a college girl at State can be. Fuck them each night. I would usually sleep in their bed. And that's it."

"That's it?"

"Well, sometimes they ask us to take care of some older guys. Last year I took care of a coach they were trying to recruit. Guy was amazing. I wanted to marry him he was such a good cocksman."

I laughed, "Cocksman? I never heard that term."

"A guy who is good with his cock."

"That's hilarious. So if a girl wanted to pick up some extra money with a cocksman?"

"You do that?"

"Made 8K this past summer."

"No shit? Lindsey, you gotta teach me."

"Well, I'm not that experienced. I did run into some creeps. Had a cop that always wanted his cut, if you know what I mean."

"We just need to be careful. There's the Hilton downtown. Gotta be some rich guys wanting pussy down there."

"Jennifer, you are an absolute gem."

"Call me Jenn. First, I'll take you down to Admissions and sign you up, then we can go downtown and you can show me the ropes."

*****

Marianna was the lady in charge of the Hostess Program. When Jenn said that I would be perfect, she immediately signed me up. Jenn later told me that all the recruiting for the program was through word of mouth. They didn't want it getting out that their hostesses were essentially state employed prostitutes. I didn't care as long as I was getting paid and getting laid. Marianna emphasized that we always had to be very discrete. Someone we were hosting should think we were doing this because we were friendly and liked people.

Afterwards Jenn and I walked into the Hilton like we owned the place. There was a bar. Although we were both twenty, the bartender just smiled at us and never questioned our age. The bartender was a bearded guy named Jake. We introduced ourselves.

I asked, "When does it get busy in here?"

"Usually around eight." He looked at us slyly, "Looking to meet guys?"

I nodded, "Only quality guys."

"We get plenty of quality guys in here. A lot of them are by themselves." He looked at us closely, "If I'm reading this right, you wouldn't mind me steering some in your direction."

"Not at all."

We also found out there was an indoor pool. We thought that might also be a great way to pick up customers, but later Jake said not to bother. Too much hassle.

*****

Over the course of the next two years I earned a ton of money and learned even more about men. First thing, you can't judge a cock by its body. Not all big guys have big dicks. Jenn said the reason some of those big guys have little dicks is from taking steroids all their lives. Not all black guys have big dicks. In fact, they have a distribution in length and girth about the same as other races. Not all little guys have little dicks. In fact one of the biggest cocks I've ever seen was on a little geeky guy.