My name is Robert, but I was always “Bobby” growing up. Our dad was “Big Bob” so I suppose it could have been a lot worse; I could have been “Bob junior” or “Little Bob” or something like that. Dad was an offensive lineman in high school and college, so the name fit. I’ve seen pictures of him from back then; he was an imposing figure. He’s still tall and very strong, but he has slimmed down a lot since his playing days. Our mother is more than a foot shorter than me and Dad, but both of them keep in really great shape.

My older sister is named Karen, and we have always been fairly close. She is two years older than me, but she is rather petite like our mother is. I was taller than her once I reached junior high, and I was always protective of her. She never seemed to mind. Despite my taller stature, I have always looked up to my sister. She was always there to offer me advice if I asked, and she occasionally let me know when I was doing something particularly stupid without being mean about it.

It’s not like we were a particularly “touchy-feely” family, but our parents gave us hugs pretty regularly, I was comfortable hugging my sister, and she enjoyed it when we sat on the couch and I reached over to scratch her back for her. I wasn’t as keen to have her scratch my back—I was too ticklish to enjoy it.

We grew up in a fairly small Midwestern town. Both of our parents worked, but they were home almost every evening. Our folks raised us to be respectful members of the community. We went to church every Sunday, I was a Boy Scout, I played football and baseball for our school, and I dated in high school. There was nothing about my life that really stood out—at least to me. I considered my life completely normal…except for one little thing.

I was obsessed with anal sex.

I can trace the origin of my fixation easily enough. My senior year of high school our old computer died and I needed a new one for my school work. Karen was already away at college and both of our parents were busy at the time. During their weekly phone call, they mentioned the computer to my sister and she recommended the laptop she had purchased for her college classes. Karen sent them a link, and my mom made the purchase online. They had me pick up the laptop from the store the following evening.

No big deal, right? Except, for once, I had my computer before my parents could lay hands on it. Our old computer had draconic parental controls installed. They had installed those when I was twelve. There had never been porn in our house, and that had been the case for so long that it completely escaped my parents’ attention that they had not bothered to put those same parental controls into place on my new laptop.

I had porn!!

However, I was so busy with school at the time that I didn’t think about it for two weeks. I was dating a girl named Betty at the time, and we were in the middle of our football season. Betty and I got together and made out a few times, but never had enough time or privacy to actually have sex like we wanted to. She was gorgeous, with curly black hair and an incredibly stacked, petite body. I was lying in my bed late one night, idly stroking my hard dick and thinking about Betty’s fantastic tits, when it suddenly hit me.

I had porn!!

I sat bolt upright in my bed and my body shook with excitement when I stealthily locked my bedroom door and opened my laptop computer on my desk. Sure enough, I had unfettered access to all the porn the internet had to offer. I jacked off seven times that night, watching a smorgasbord of varied sex acts.

That was the first time I saw anal sex. I’d never even thought about it before that night, honestly. After I watched that first clip, I stared at the screen with my mouth hanging open. I don’t know why it turned me on so much, but it made me harder than I had ever been before. Naturally enough, that video had dozens more linked to it that featured sexy women taking hard cocks in their asses.

I watched two straight hours of anal sex clips and jacked off three more times before I realized how long I had been at it. Then I shut down my laptop and retreated back to bed on shaking legs. I lay awake for another hour feeling like my head was spinning as a montage of butt-fucking clips played in my mind.

In the morning, I awoke with my usual morning erection, but I found myself thinking about sticking that hard dick into some woman’s wet, welcoming asshole. At the time, it bothered me. I had enjoyed the pleasure of having sex with girls I dated in high school, and had never once even considered putting my dick in a girl’s ass. The way I had been raised, it felt like there was something wrong about doing something like that; like it was just perverted and dirty.

After that first night, I watched a lot more internet porn. I might go two or three days without looking at anal sex clips, but invariably found myself drawn back to watching more of them. Those always got me harder than anything else I watched, and got me off quicker as well. By the time Betty and I finally got to spend an afternoon together while my parents were still at work, I found myself staring at her sexy ass as she stripped in my bedroom.

The thing was, Betty had really nice, big tits—especially for an 18-year-old high school girl. Up until I started watching all those anal sex clips, I had practically drooled at the thought of seeing, fondling, and sucking Betty’s incredible tits. When I finally got to see them in all their naked glory, I really wanted to flip her back over onto her knees so I could feast my eyes on her asshole while I fucked her.

That didn’t happen, and I really did enjoy sucking her hard nipples and squeezing her breasts while we fucked on my bed. Her wet, tight pussy felt sensational, and I came hard inside her after she told me it was okay. It was incredible, really. But…damn, I wanted to play with her ass.

Betty and I hooked up another four times, and she was really very sexy. The thing was that I really wanted to do something with her sexy backside. Well, not necessarily her sexy backside. At that point I was contemplating the tight teenage butts of many girls in my school. I wanted to try anal sex with any woman who might be interested. That woman wouldn’t be Betty. When I tried to broach the subject of anal sex with her, she looked really angry.

“I don’t know what kind of dirty slut you think I am, Bobby, but there’s no fucking way…” she started.

I held up both hands defensively and did my best to act like I wasn’t actually interested in trying it.

“Whoa!” I said. “I just saw it on the internet for the first time, Betty. It wasn’t something I ever even thought about. Seriously! It was just one of those things, you know? I saw it and it made me curious. Like, I wondered if girls liked that sort of thing.”

She sneered, making it clear what her opinion was of women who “liked that sort of thing.” I was more careful for the remainder of high school and the following summer, but it was obvious to me that I was obsessing over women’s sexy butts. I know I wasn’t as careful as I thought I was. I have to wonder now how often I was caught staring at the sexy asses of every girl in our school, as well as some of the younger teachers, without ever realizing I had been caught.

Once I even caught myself staring at my own mother’s shapely butt! That was when I really became concerned, but it wasn’t like I had anyone I could talk to about my fixation. For three days after that happened, I refused to look at any internet porn. Then I was right back to watching anal sex clips and jacking off like mad. I just hoped I would eventually get over it.

* * *

My sister came home for a month that summer. She had a part-time job near the campus, but the place basically shut down with all the students gone. Karen and I had always gotten along well growing up, but we weren’t so close that I could discuss my sex life with her. I knew that she had dated since she’d started college, but she wasn’t in a serious relationship. Twice, my parents had taken me along when they went up to visit her at school the previous year.

I had applied to go to the same state college, and got my acceptance letter while Karen was home. She looked surprisingly happy about it. I had harbored some concern that she would resent me for following her to the same college, but she was all smiles and looked genuinely excited that I would be going to the same school.

Our baseball season wrapped up the following weekend. We’d had a winning record, but failed to win our district so we did not advance to the state playoffs. In a small town like ours, it wasn’t like athletic scholarship offers were pouring in for anyone. It was my grades that had secured a small scholarship that would pay for my dorm room and books. So, I wasn’t some world-class athlete. What I failed to take into account was that I was in really good shape compared to a lot of the guys my sister and her friends knew.

Hell, that’s not accurate. Next to those guys, I looked like a superhero. It took me a while to figure that out, though.

I was just shy of six-foot-three, and a little over 200 pounds, but I was extremely “ripped” and “buff” following my senior year. It was just that most of my friends were also athletes and I didn’t think I was that extraordinary because I was comparing myself to those guys. For example, there was a black guy named James who had huge tree trunks for legs. My legs were muscular, but not in that league. Likewise, my friends Chuck and Gordon spent hours on end hitting the weights in the gym—far more time than I had, unfortunately. Their arm and chest muscles were absolutely huge and made them look like a wrestling tag-team.

I knew I looked good, but I didn’t think I was amazing. Still, I got my share of female attention and never questioned my good fortune. My sister had a couple of photos of me without a shirt on from our spring break. I didn’t know she had even taken them. Those pictures had circulated among her friends, and those girls were far more impressed than I would have imagined.

Karen was excited because she knew her friends would be.

Now, I knew that my sister had an apartment near the campus and that she had a roommate named Sherry. I’d never met Sherry, but I overheard my sister talking about Sherry’s boyfriend. It was clear that Sherry was in a serious relationship with this guy, and that my sister didn’t like him much. My sister really did like her roommate, though. That was why she didn’t like the guy Sherry was dating.

“She could do so much better,” I heard my sister sigh into her phone. “That guy is such a tool.”

I just shook my head at the time and kept walking past the couch where she was sitting. None of this would have mattered at all, but it became a factor at the end of that month. My sister needed to head back to her apartment because she had to get back to work two weeks before the campus re-opened for the fall, and I would be going with her.

Like most major college campuses around the country, parking was an absolute nightmare. Karen had her own car, but she had brought it home and left it for me to use just three weeks into her freshman year.

“Honestly, Bobby,” she reassured me at the time, “You’ll be doing me a favor. The car nearly got towed twice while I was in class, just because I parked in the wrong spot. Even at our apartment complex, I had trouble finding a parking place after I got off work. Everything is in walking distance anyway. I really don’t need the car.”

The next time we’d visited I had witnessed the parking nightmare firsthand. It was mind-boggling just how bad it was. So, when it was time for her to return to campus, my parents figured they should take both of us up there along with all of our stuff. We wouldn’t want to be burdened with having a car while we were there. I know that sounds crazy, but it was true. Neither of us wanted to have to deal with having a car while we were in college.

The campus was like a ghost town when we arrived, and I would not even be able to move into the dorms until everything opened almost two weeks later. I worried that it would be an imposition, but Karen was happy to let me stay at her apartment until the dorms opened and I could get settled in there. I wound up crashing on her couch, and still did not meet her roommate that first night.

My sister pulled a face when she explained that Sherry had been staying with her boyfriend, Darren. She seemed apologetic that she couldn’t offer to let me stay in Sherry’s room, but I understood that would be an invasion of her roommate’s privacy. I just smiled and rubbed her shoulders reassuringly.

“It’s fine, Karen, really,” I said. “Honestly, I’m just happy to have a place to crash without having to stay in the hotel with Mom and Dad. Staying here with you makes me feel like a real grown-up, if that makes any sense.”

She gave me a dazzling smile in reply. I’ve never lusted after my own sister, but she is one attractive woman. When she turned away I had to suppress a groan. My sister has got a gorgeous, heart-shaped ass, and she was wearing snug shorts…

What the fuck is wrong with me?

* * *

The next evening my sister brought up the costume party that would change my life forever. Sorry, that’s “cosplay party.” My sister and her friends were into dressing up in these costumes. A lot of guys were into it as well, but it wasn’t something I’d ever been interested in. When she asked me if I wanted to dress up in a costume and go to the party with her, I looked at her and shook my head.

“It’s not even Halloween!” I objected. “Why would you have a costume party?”

“That’s just it,” she countered, “Why wait for Halloween and only have one party a year? We have one or two of these every month, and they’re a blast! Seriously, Bobby, you need to go to this party.”

I shook my head again. I really didn’t want to go, but it was obvious my sister really wanted me to.

“Where would I even get a costume?” I asked. “The party is this evening, right?”

“Oh, there’s a costume shop here in town. We can rent you something cool. You’ll love it, Bobby!”

I think I would have objected and tried to talk my way out of going, but Karen showed me some of the costumes she had hanging in her closet. There were a lot of skimpy-looking outfits, with lace panels, plunging necklines, and high-cut bottoms. She had an assortment of stockings and garter belts hanging on the inside of her closet door, and I had to gulp repeatedly as I stared at those costumes and imagined some of her friends wearing them.

I wasn’t imagining my sister dressed like that, of course. No, really! I wasn’t imagining my sister; it was two of her friends I had met on a previous campus visit that I envisioned wearing those lacy stockings.

So I let her talk me into it, and when our folks showed up with the minivan the four of us drove down to the costume shop. Karen was so bubbly and enthusiastic that I didn’t want to dampen her mood, but I was embarrassed to have our parents along.

When I saw the costumes they had for rent, I was even more dubious. There were very few in my size, and I could not have told you who 90% of those characters were supposed to be. I wound up getting a Captain America costume, but not a cool one. It was the dorky one from the movie, where Cap was selling war bonds. You know, the one with the bright blue mask that had white wings on the sides? I thought it looked stupid, but my sister looked me over and clapped.

“Perfect!” she announced.

I rolled my eyes briefly, but then gave her a weak smile. I love my sister and didn’t want to ruin this for her by being a jerk.

My parents also got costumes, and that was when I realized there was no way this was going to be as cool as my sister thought. Dad was in a Zorro costume while my mother was in some medieval gown with a ridiculous amount of cleavage showing. I think she was supposed to be Marie Antoinette, but I’m not sure. What those costumes told me was that my parents would be going to this party with us, and that meant they would make sure I did not have a good time.

It’s not like my parents are bad people, you understand. They have always been caring, loving and supportive. They also seemed to think I was a virgin and needed to stay that way. There was no way I would be able to meet college girls and have any chance with them while my parents were watching me. I tried to give them a smile and tell them they looked great—and to be fair I thought their costumes were cooler than mine was—but inside I was certain this evening would be a disaster for me.

A little over an hour later we were at my sister’s apartment when she got a phone call. It was her job, calling her in at the last minute because someone else had called in sick. I was relieved, thinking this would get us out of attending what I was thinking of as “this dorky party.” I was also relieved because my sister looked far too sexy in the skimpy, mostly transparent fairy princess costume she was wearing.

My sister had other ideas.

“I’ll run you guys over to the party and make sure you get in before I change for work,” she insisted.

* * *

That was how it happened. I was at this party in a big house not far from my sister’s apartment. There were some very attractive women there, and some of them were dressed in very sexy costumes. That just made it more embarrassing to be standing next to my parents and my sister before she left, and of course I felt like a dork in that rental costume. Three different gorgeous college girls came up and talked to me. Well, they tried to, but my Mom or Dad butted in before I could utter a word.

On the bright side, there was beer. My Dad actually joined me in grabbing a big plastic cup of beer there in the kitchen while my mother talked the ear off of some poor girl who had come up to me ten minutes earlier. I shot the girl an apologetic look, but felt like there was nothing I could do without coming off as extremely rude to my mother.

After that, I just sipped beer and talked with my parents for fifteen minutes. It felt like the safe move; it would spare any other girls having to go through what that one…I think she was supposed to be some anime character? Maybe it was from a video game instead. Anyway, she looked relieved to make her escape when I drew my mother into a different conversation.

After fifteen minutes and a second beer, though, I started looking around for a bathroom. I spied a fellow coming out of a room down the hall, and he had a disgusted look on his face. I stifled a chuckle, and was worried what sort of smell I would be walking into. I excused myself and walked over to that door, and took a big breath before opening it. I was still holding that breath when I stepped into the room and pulled the door closed behind me.

Inside, I froze before my hand reached the light switch.