Graduation was fast approaching, and I had finally locked down my first real job. I had been playing golf on a full-ride scholarship at Michigan State with hopes of making the pro tour someday. I had already played some small tour tournaments and done pretty well, but I didn’t think I would be able to make a living as a full-time touring folk pro without another steady source of income.

I took a job as a golf instructor at a nice country club in Cincinnati. I like “Cincy” a lot. It was my first choice of cities to work in, so I was excited to land this job at one of the upscale country clubs in Ohio.

Most of the country doesn’t realize that Cincy is an awesome place, full of attractive young professionals, including tons of hot chicks compared to many other cities. Teaching golf at a high-end club with hopes of going pro, I thought, would also set me up well for a good chance of meeting some hot daughters of wealthy families. Not that being wealthy was what I was looking for in a girlfriend. But, if it happened to work out, I wouldn’t complain!

Another advantage to working up north in the golf industry is a lot of time off. I could travel to other countries during the winter and play tournaments when the frigid temperatures of Ohio made golf impossible to play.

The issue was paying rent. I had no idea how much money I would make in the off-season, so I needed a roommate to share an apartment with. Luckily, one of my golf team buddies had a frat brother who was also graduating and moving to Cincy and wanted a roommate. He set up a meeting, and we got along well. We decided to find a two-bedroom apartment close to downtown, where he would be working, and also not too far away from the country club.

My name is Ryan, and I am now 24 years old. This story happened when I was 22 and just out of college. I am 5’10" tall and weigh about 175 pounds. When I went to college, I was skinny and didn’t have much of a body to look at, but I was able to add a lot of muscle to my thin frame, which has helped a lot with my golf game and gets me a lot of looks from girls. Now I also don’t mind taking off my shirt and showing off my abs and lean, muscular frame.

My new roommate is Alex. He’s a good dude. I would describe him as a typical frat boy. He didn’t play college sports, but he did play lacrosse in high school and played on the lacrosse club team all four years at Michigan St. I am told he was kind of the stud on the team.

Alex is about 6’1" and probably 190-200 pounds, I would guess. He’s a little taller, a little more muscular, and a little better-looking than me. I am a pretty good-looking guy, but he turns heads of super hot girls. I eventually found out that my cock is larger, though, so I will always have that over him.

To be clear, I am not jealous of Alex. I spent a good amount of time in the gym, and trained in a boxing gym through high school and college. I would say I am a funny, well-spoken, good-looking guy. I am confident in myself and hold my own rather well. Up until this all happened, anyway.

I figured Alex and I would crush it with girls if we hung out together and became good friends. He would attract the crazy hot chicks, and I would end up having a shot at her friends. Hot chicks like to hang out with hot chicks, right?

Since it was my senior year in college and I would be leaving soon, I didn’t want to get into a serious relationship. So for the past year, I had only been seeing a few girls casually here and there. Which means I wasn’t having nearly as much sex as compared to most of my time in college.

When it comes to sex, I wonder if I am more kinky and open-minded than the average guy. When my girlfriends have asked me what I am into, I usually answer, ‘What am I not into?’

I had one very active sexual relationship before college and another absolutely amazing sexual relationship in college.

My college girlfriend was Samantha. We had the kind of relationship where we both fell totally in love, and were totally trusting and comfortable opening up to each other about anything. Especially sex. If she wanted me to suck her toes or I wanted to lick her asshole, we could just say what we wanted, and we knew that the other person would be open to it and not judge. Sex with Sam was out of this world!

Sam was a 5’3", 110-pound sex kitten who never said no to anything in the bedroom. I could pull out of her pussy and cum all over her face anytime I wanted, and she would open her mouth and lick every drop, knowing exactly what I wanted her to do.

She would surprise me by kissing me with cum still in her mouth sometimes. We played with each other’s asses a lot. I could fuck her ass anytime I wanted, and she loved to use her toys and fingers and tongue in my ass. We took turns playing dominant and submissive roles, forcing each other to our limits.

Sam also loved to talk dirty. “Does that feel good in your ass, baby? Tell me. Tell me you love my fingers fucking your ass!” she would whisper in my ear.

I complied, of course, telling her how it felt good and begging her not to stop. She would usually be sucking me or jacking me off with lube when she played with my ass, always taking one step further if she could.

“I bet you wish this was a real cock in you, don’t you? Tell me. Tell me you want this to be a real cock!” she demanded. I again complied and told her whatever she wanted to hear.

“Yes… yes, I want a real cock to fuck my ass!” I said in the heat of passion. I really never wanted a guy to fuck my ass, but I knew what she wanted to hear. I mean, it was her turn to be dominant; I might as well do whatever she asked. She wanted to buy a strap-on to fuck me with, but we never got around to that one.

Sam and I also had several threesomes. She loved to pick up other girls when we went out. Sometimes I just watched as she and another girl had sex, and sometimes I fucked both of them. My favorite was to fuck Sam while the other girl licked her pussy and made her cum.

When I asked her if she ever wanted to try a threesome with another guy, she replied, “Of course! I thought you’d never ask. Who wouldn’t want two guys and two hard cocks pleasing them!”

As I said, I am seven inches and rather thick. I know I have a nice cock, especially for my size. All my girlfriends have raved about my member, many of them to their friends.

When Sam told me that I was as big of a dick as she had been with, I asked if she ever wanted to try a really big cock. She said she had fantasized about it, but was worried it would make her pussy loose and not feel as good for me or another normal-sized guy to fuck afterward. I reassured her that would not happen from one escapade.

We eventually found a guy with a big cock and had a threesome with him. He was probably ten inches long and super thick! She loved playing with and sucking his long, thick shaft. Her tiny hands didn’t even wrap around his girth, making him look even bigger.

“Oh my gosh, babe! Look how long and how thick it is?” she purred as she tried wrapping her fingers around it and held it up against her tiny face. His cock dwarfed her little head and hands.

“Come down here and watch me suck him. Move in close and watch me lick his big cock. Take some videos that we can watch later too.” She begged while she licked and kissed one side of his enormous shaft.

I was only a few inches away, in awe, watching her tongue trace up and down his rod when she grabbed my shirt and pulled my face down toward her face… and his cock.

“This is too big for just me. I need some help. You lick one side, and I’ll lick the other,” she insisted.

I had fantasized about playing with a guy's cock before (like most guys have), but I didn’t think I would ever actually do it. In the heat of the moment though, I didn’t even question it. I just started licking up and down the other half of his cock.

“Isn’t pleasing a cock so fun, baby? I knew you’d like it,” she purred. She was right. Licking his cock was fun. I like pleasing when it comes to sex, and I knew that having two tongues licking his cock had to feel good!

We both licked up and down his length for a while, kissing when our mouths met at his head and sharing the pre-cum that we made together. We also each sucked him, taking turns seeing who could get more of his cock in our mouth. I won that contest because Sam was such a tiny little thing and her mouth couldn’t fit much of his fat cock.

She finally climbed on top of him and worked his giant cock into her tiny pussy. What an amazing sight and amazing night that was!

Playing with a guy’s cock wasn’t as big of a deal as I had thought it would be. Which is one reason I say that maybe I am kinkier, or dirtier sexually than most guys. Or, maybe a lot of guys enjoy playing with another cock once they try it. I’m not sure.

Sam eventually transferred to a different school, and we didn’t stay together. I wonder if I’ll ever find another girl that fun in bed.

Ok, back to current times.

Alex and I were getting settled into the new apartment, and I hadn’t had sex in a few months now. The longer I go without sex, the more debacherous and depraved my thoughts become. The porn I watch or read becomes more filthy too.

During this time of unwelcome abstinence, I watched a lot of threesome and foursome porn videos. I like MMF threesomes because they reminded me of Sam from college. That led me into cuckold porn. The thought of watching your woman being fucked was pretty hot. Of course, in my head I imagined it was a girlfriend or future wife, where the man (me in this case) was totally secure in the relationship and could watch his woman being fucked by other guys and it not bother him.

Threesome porn led me into gangbang videos, which really caught my attention as well. It was the evolution of a threesome. In my fantasy mind, I imagined allowing several guys to take turns fucking my woman's pussy and mouth and ass. One thing that always made me cum was seeing or visualizing the man (husband or boyfriend, etc) having to suck the cocks of the guys in the room while his woman was being fucked.

I read one story of a wife being gang-banged, and each time one of the guys shot his load, it was either in the husband's or wife's mouth. That was quite a turn on too, because I've never swallowed or even tasted cum.

I ended up jerking off every day, of course, sometimes two to three times per day.

At my new job as a golf instructor, I was also surrounded by beautiful women, which didn’t help how horny I was. Most of the women there were all older than me, being wives and moms, but many were still smoking hot. There are tons of cougars at a country club!

Most of them showed off their bodies in short tennis skirts and skimpy workout clothes. There were tons of perfect bodies with great boob jobs to match.

They would flirt with me all the time, and some of them acted like they would fuck me if I tried. But I knew they were all off limits, being club members’ wives. That’s one way to lose a job quickly in my business!

Then I met Bailey and everything in my world changed. Bailey is a female tennis instructor at the club. We were introduced at the club cafe one afternoon. I will never forget that moment. I think I completely froze in my tracks! If there is love at first sight, this must have been it.

Bailey is perfection. She is both stunningly beautiful and girl-next-door all at the same time. I was fully taken by her from the very first second I laid eyes on her. I knew this was the girl I wanted to be my next girlfriend!

Let me describe Bailey. She is 5’8” tall and around 120 pounds, and she has the most perfect body you’ve ever seen. Her face glows with the brightest, freshest smile you can imagine. She has blond hair that she keeps pulled back in a ponytail at work. Of course, tennis skirts and tank tops look amazing on her. She looks to have small C or maybe large B cup boobs. I hoped to find out someday!

Once I came to my senses at our first meeting, I knew I had to play it cool to give her a sense that I wasn’t that interested right away. I bet she had guys drooling over her all the time. Plus, girls want what they can’t have.

During the first few weeks after we met, I found reasons to walk by the tennis shop and tried to eat lunch at the same time as her. After about two weeks, we were chatting regularly. Then, I would make sure to ignore her for a day, so I wasn’t obvious.

I was playing games, I know, but she was too hot and had too many guys pursue her through the years. I had to make her curious about me and not be just another guy trying to fuck her.

We were chatting one day when I mustered up the courage and asked if she wanted to grab a drink after work sometime. She said yes and told me a spot she likes to hang out after work. She said yes!!!

Wanting to play it cool, I told her I was busy that day, but the next day should work. She agreed, and I tried to walk away, hiding my smile and not doing cartwheels!

The next day I was pretty nervous awaiting the “date” with Bailey. But right as I was about to leave work and race home to shower, my boss told me he needed me to do him a big favor and take over his golf lesson with one of the most influential wives at the club. Her husband was on the board of directors, and they were considered very important people around here. I really wanted to tell him no, but I was the new guy and didn’t have much choice.

When he tried to cancel the lesson with her, she asked for me specifically to take his place.

I texted Bailey and said I could still meet her, but about an hour and a half after we planned. She said it was no big deal and she would see me then.

After the lesson, I ran home, took a quick shower, and headed to the restaurant. I saw a text from Bailey while I was driving there.

“Hey… I ran into some friends here. We were gonna head downtown to another spot. Do you want to join? Are you close?”

“Shit!” I thought. This wasn’t good. And it didn’t sound like it was going to be very ‘date’ like if I was tagging along with her and these friends, so I declined but told her I’d love a raincheck.

I was mad… I really wanted a one-on-one date with her! I had been thinking about her every day. I turned around and drove home very disappointed.

That night I surfed for videos with anyone that looked even remotely like Bailey. When I found a video with a girl that looked even similar to Bailey, I would cum almost immediately. I liked her too much.

Some odd noises woke me up around midnight. It was coming from Alex’s room. It sounded like he was having sex with someone.

Man, this night was getting worse. I listened to them and pictured what might be happening while I stroked my cock for the second time that night. I pictured Bailey as I got closer to cumming. I couldn’t help it.

I got up and went to work early. As I walked out, I saw women’s shoes on the floor in the living room. Hey, at least someone was getting laid around here.

At work, I texted Bailey to ask if she had fun last night and if she wanted to grab lunch together. She said that last night was fun, but she was going to eat in her office, and then try to catch a nap in the back room between lessons. She must have stayed up late with her friends, which sucks because I could have been there and I decided not to go.

When I came home after work and asked Alex about his night and the noises I heard. He just smiled.

“Yeah, it was a fun night. Sorry if we kept you up,” he snarked back.

“It’s fine… at least someone is getting laid!” I laughed.

“It was the first time for me in a while. Hopefully won’t be the last, because she is a hottie. And she’s either a sexual dynamo, or hadn’t been laid in a while either,” he offered.

I was glad we were starting to talk more and become friends.

I decided not to contact Bailey the next day, wanting to see if she would reach out to me on her own. It was SO hard not seeing her or at least texting her. I didn’t hear from her all day. Kinda heartbreaking.

I usually leave work around four or five, but I decided to stay and work on my game. I needed a distraction from wanting to see Bailey.

When I went home and opened our apartment door, there were women’s shoes on the living room floor again, and this time a bra as well! Good for Alex!

I could hear noises from toward his bedroom. I snuck down the hall and saw that Alex’s door was not closed all the way.

I carefully and quietly crept toward the opening of the door. Moans of sex were getting louder as I approached. I peered in and could see Alex on top of some chick, and he was fucking her good and hard. Her legs were almost wrapped around him as she moaned with each thrust.

“Oh… yeah, yeah!” I heard her moans from underneath him. Alex was vocal as well.

“Ah, fuck you feel so good. I’m gonna fuck you all fucking night!” he exclaimed.

“Yes, yes… fuck me, fuck me so good! I need it so bad,” she screamed.

My cock was pressing against my pants, and I was over the edge horny. I didn’t want to interrupt them, so I snuck out of the apartment. I went to grab a taco and a beer at a local spot and started talking to some girls there. I’m not much on one-night stands, but I needed to get laid!

One of the girls was flirting with me pretty hard. She was below my league, but I had a few drinks in and was horny as hell. I said fuck it and flirted back with her. After about 30 minutes, I made my move.

“You wanna get out of here? We can have another drink on our own… somewhere else.” I asked.

“Like where? Are you inviting me to your place? I just met you,” she replied with a big grin.

“Actually, my roommate is there and has company. Wanna go to your place? I can stop and pick up some drinks on the way.” I offered.

“I don’t know. Are you a good guy?” she played.

“I’m better than good.” I shot back. I decided I was just gonna go for it and let her know what I wanted. “We need to go somewhere besides here… I don’t think you’ll let me see you naked in here,” I whispered to her.

“Well, I don’t know about that, but we can at least have a drink,” she said. I knew she was down.

We went to her place, and I fucked her like my life depended on it! I came three times that night. She couldn’t believe I kept starting up again. My dick and pelvis bone were actually a little sore the next day. Guessing she was too!

When I saw Bailey at work the next day, she skipped over to me and said hi. She was in quite a good mood!

“What’s that smile all about?” I asked, hoping it had something to do with me.

“Me? Oh, nothing, I guess…” she said. But I could tell it was something.

“Okay, raincheck on that drink then?” I asked.

“Umm, sure.” She hesitated. “There’s a group of us meeting at the same place as before around 6. If you want to join?” she offered.

She wasn’t saying yes to a drink with ME; she was only inviting me to hang with a group. And she even seemed unsure about that. This was not a good sign, but it was all I had.

“Sure, that sounds fun. But I don’t want to intrude on your friend group.” I offered her an easy out. She hesitated again.

“Umm… It depends. Are you… asking me out?” she trailed off. “Because… Well… there’s a guy who’s gonna be there. We’ve been talking. Or dating. Sort of, I guess? I’m not sure.”

Now she was clearly frazzled trying to explain. “So, if you’re asking me out, which is fine, then maybe you don’t wanna come there?”

My heart beat started increasing. This was not good at all. I tried to think of a way to play it cool.

I wanted to say, “Fuck no, blow that guy off! WE are supposed to be dating!” But that would sound whiny and miserable.

“Hey, if you’re into someone right now…” I had to be careful how to finish this. I wanted to date her so much and thought about her constantly. “Then, I guess I will wait and see what happens with that.” I kept hesitating, measuring my words. “And, when you’re… umm, more available… or he’s not around… or, ya know, whatever… then we’ll see.”

Every word out of my mouth was more awkward and hesitant.

“Okay,” she replied. “This just got awkward, didn’t it? You seemed bummed.”

“I mean, yeah, a little,” which was a total lie. I felt like jumping off a cliff. “But let’s not make it that way. And I wouldn’t take forever figuring it out. I might not be on the market that long.” I smiled at her.

“I KNOW!” she frustratingly replied. “You’re really awesome. And I’m not in a relationship. We can totally go out. I just didn’t want you to come tonight, and it be weird." She was shaking her head left and right, like she was confused.

I could tell she actually liked me, and this was frustrating for her, which made me feel so good! But I didn’t want to date her if she was seeing someone else, and that was awful.

“So, what about tonight?” she asked.

“I’ll drop by and have a drink. I should check out my competition, right?” I laughed. Her eyes rolled back.

“Sure, if you want to and it wouldn’t be weird,” she replied. “And he’s not my boyfriend; he’s just… a guy,” she finished, still frazzled and not sure what to say.

“Okay, see ya tonight,” I said, walking away, but giving her a wink first, which made her smile.

That night, I ran home, showered, and got dressed in my favorite clothes. I planned to waltz in, barely pay attention to her, probably flirt with any other girl at the table, and waltz out. I would be on her mind the whole night long. Hopefully.

When I got to the place, I went in slowly so I could get the lay of the land and determine where I would sit and such. I saw her at a table with 4-5 other people. The guy next to her must have been the one she was starting to date, or whatever she called it.

He turned halfway around, and I saw his face. My heart almost stopped! It was Alex, my roommate. My heart was almost pounding out of my chest. I was in full freak-out mode, like a panic attack.

Holy shit, this means Bailey is who he had been fucking in our apartment, twice this week!! I had even seen him on top of her once. I jerked off listening to her get fucked!!

I slowly backed out and went back to my car.