“Wonder Woman” Takes it in the Ass

The Usual Disclaimer: This is a work of fantasy. All characters featured in sexual situations are over 18. The characters in these stories are fictional. Any resemblance to actual persons living, dead or undead is purely coincidental. Do not try this at home.

I sat down and jotted the first scene I had in mind for this story, and immediately became concerned. It just felt too much like I was “ripping off” desurtdawg’s marvelous story, My Sister Eva Started it All. I sent him an e-mail voicing my concerns, but did not hear back from him. I let the rest of the story take shape in my mind over the following day, and realized that the story I had in mind didn’t really have anything else in common with his Literotica classic, other than that one scene.

Still, I would be remiss if I did not recognize how his story inspired mine. I hope you are well, sir.

* * * * *

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.

This wasn’t a bathroom. It was a bedroom. And someone was here!

The room was dimly lit by a night light, and I recognized the boots and skirt of the Wonder Woman costume immediately. I thought that I had seen this girl earlier out in the living room but wasn’t sure. None of that mattered at that moment, though. What mattered was that the skirt was pushed up over her back, completely exposing her naked, sexy ass!

She was moaning softly as she reached back and spread her ass cheeks, and my eyes were glued to the slick ring of her asshole as it opened slightly right in front of me. Her pussy was also spread open, but I couldn’t take my eyes off of her asshole. It was obviously lubricated. I felt like I was in a dream or some kind of trance as I stepped forward and pulled my dick out of those costume pants. My body felt like it moved on its own, without any conscious control from me.

I barely dared to breathe as I watched the throbbing head of my dick closing in on her asshole, and then it was pressing its way inside. In that instant, I spied the metallic gleam of a butt plug sitting on the bed to her right. It was coated with lube, and I just knew that this girl wanted to be fucked in the ass. I was impossibly turned on, and could not possibly have stopped myself.

Now, if she had screamed or objected, I think I would have stopped immediately. Instead, though, she just seemed a little surprised.

“What…what are you doing?” she groaned groggily.

I licked my lips and stared as the tight rubbery ring of her asshole spread around the head of my cock. It looked so fucking hot! I still could scarcely believe this was really happening. It felt like this had been my ultimate fantasy for so long. It had cost me, that last semester of high school. At least two gorgeous girlfriends had dumped me when they suspected I wanted to fuck them in the ass.

Now it was finally happening! My dick was sliding into a woman’s sexy, tight asshole, and it felt absolutely incredible!

“Ohhh! Oh God, you’re in my ass!” she groaned.

She didn’t stop me, though. Nor did she protest as I started slowly thrusting in and out. She just grunted with each thrust, and it was music to my ears. Here was a woman who knew how to take a cock in the ass! I knew there had to be such women in the world, of course. It had just been my misfortune to grow up in a small town where none of them lived.

Then it only got better—she moaned and pushed that sexy ass back toward me, forcing me balls-deep inside her. My eyes rolled up in my skull and I had to take a slow, careful breath. This was a woman who actually wanted my cock in her ass! The very idea almost made me come prematurely. I stared down at the tight globes of her perfect, sexy bottom and shook my head as I slowly pulled my slick cock back and prepared to push back in.

“Where have you been all my life?” I murmured as I grabbed her tight cheeks and started to fuck her.

“Oh, yeah,” she panted. “That’s so perfect. It’s just what I needed tonight, baby. Oh! Oh yeah! Fuck, you’re so hard!”

I grinned when I heard that last bit and savored fucking this college chick in her tight ass. She probably had a boyfriend, and thought I was that guy. I shook my head again as I watched my dick piston in and out of her horny asshole.

Whoever that guy is, he is one lucky bastard—getting to enjoy this perfect ass all the time, I thought.

Then I realized her boyfriend was probably the guy I had seen walking out of the room minutes earlier, and that he might come looking for his girlfriend. That could not possibly end well if he found us like this. I picked up the pace and let myself go, pounding her sweet back door fast and deep. In just a couple of minutes I felt my orgasm rapidly approaching, but this dream girl actually beat me to the punch, so to speak.

“Oh God, I’m coming!” she cried out.

Her body shook and looked even sexier, and her asshole squeezed my shaft delightfully. It pushed me right over the edge.

“Me too,” I gasped. I was as turned on as I had ever been when I added, “I’m going to come in your ass!”

We gasped and shook together as I unloaded deep inside her, and I leaned down to kiss her exposed shoulder and reached around to fill my hands with her tits. I got another shock when I did that—her tits were huge! My hands were both completely full as I palmed her thick, hard nipples, and there was far more tit flesh than I could possibly hold overfilling both of my hands.

I love big tits, and feeling hers made my dick lurch inside her. Hell, I was already coming like a fire hose inside her perfect ass but it felt like I got even harder!

Then I felt a pang of regret. This would be a one-time thing. My perfect mystery woman was taken, and I had fucked her in the ass without even asking. I didn’t even dare risk taking a peek at those magnificent breasts of hers for fear of being caught.

With that thought firmly in mind, I pulled my spent cock out of her and tucked it into my underpants before carefully pulling up my costume pants. I quickly checked to make sure I hadn’t left some obvious sign that I had been having sex. I really doubted my sister or my parents would appreciate it any more than the people at the costume rental place would have. “Wonder Woman” slumped forward onto the bed with a happy-sounding moan, and I managed to scurry out of the room before she rolled over and saw me.

I was still terribly paranoid as I made my way out of that bedroom. I eventually located the bathroom, but I had to wait several minutes before I got in and relieved my bladder. After washing my hands and carefully checking my reflection, I made my way out to the kitchen once again. The entire time, I was wondering over and over, Did anyone see me go into that bedroom?

A sudden realization had me in a cold sweat: I was the only one wearing a Captain America costume, and my sister knew I was the guy wearing it. My sense of anonymity had been a complete delusion. If anyone tried to figure out who had taken advantage of the busty Wonder Woman in that darkened bedroom, it wouldn’t take long for them to narrow it down to me. Images of me in that costume, standing in a police line-up immediately flashed through my mind.

Shit! I needed to get out of there!

Once I made that decision, I went looking for my parents. They were still in the living room, but I stopped dead in my tracks when I saw they were talking to Wonder Woman. Now that I could see her clearly in the well-lit room, I realized that the costume was rather conservative. The skirt was longer than I thought, coming down almost to her knees, so there was only a tiny gap of skin before those long boots took over. The top did a masterful job of concealing her massive breasts, now that it was pulled up properly, but it did display a creamy expanse of cleavage. The biggest difference between the costume and the movie version of Wonder Woman was the mask; it was a stylized Greek helmet that completely hid her face and it evidently had a wig built in to it.

I had no idea what her actual hair color was. It was hidden beneath the thick black curls of the wig.

My eyes took all of that detail in an instant, and then I panicked and fled the house entirely. Halfway back to my sister’s apartment, I finally calmed down and figured I needed to let my parents know where I was. After some thought, it seemed like a good, safe idea to send them a text. My phone was still at Karen’s apartment, and I snagged it and texted as soon as I got there.

After I had done that, I quickly stripped out of the costume and checked it carefully. I let out a huge sigh of relief when I saw that I hadn’t gotten any cum stains on it. I hung it back on the hanger and then got dressed in shorts and a t-shirt. When my folks arrived two hours later, I was chilling on my sister’s couch watching television.

* * *

“You could have at least tried to enjoy the party,” my father grumped as soon as he was in the front door.

“Oh, no, Dad, it wasn’t like that at all,” I replied, shaking my head and giving them what I hoped was a rueful smile. “I just…I should have gone to the bathroom before we left. I really had to go, and someone was in the bathroom there. I just couldn’t wait any longer, if you know what I mean.”

I’d had time to come up with that lie while I waited for their return. They chuckled and shook their heads, but they bought my story. They took turns in the bathroom getting changed, and then we watched television together for the next hour or so until my sister returned from work.

My parents had stuck around so that they could hug her and say goodbye before they hit the road. Karen and I stood out front and waved as they drove away, and then headed back inside. As soon as we closed the door behind us, my sister fixed me with a penetrating look.

“So, how was the party, really?” she asked.

“It was fine, really,” I replied. “I would have enjoyed it a lot more if Mom and Dad hadn’t been there, though.”

Karen snickered. Then she pulled out her cell phone and I could see a series of text messages.

“I knew you’d be popular with my friends,” she said with a grin. “By the time I finished my shift and checked my phone, I had eight different girls all begging me to give them your number.”

I cocked my head and looked at her in disbelief. I really thought she was messing with me, and could not figure out why she would do such a thing. Then my eyes drifted down to the phone in her hand and I read, “OMG!! You weren’t kidding! You have to set me up!” After that was an emoji I didn’t recognize. I only got a glimpse, and then the phone rang and she pulled it back around to look at it.

I smiled when I heard the ring tone. It was from the intro to Depeche Mode’s Sea of Sin–one of my favorite songs of all time, and one not too many people were familiar with. It was from the B-side of the extended version of their hit single World in My Eyes, but even that song wasn’t one most Americans would know. At least, nobody our age.

“It’s Sherry,” my sister explained before answering the phone.

My eyebrows rose at that revelation, and Karen grinned and nodded at my reaction. The phone call was brief, and my sister sighed as she hung up.

“Sherry’s coming home tonight,” she said. “It’s such a shame she’s dating Darren. You two would be perfect together.”

I laughed softly and shook my head again.

“I’m not even here a week and you’re already pimping me out to your friends,” I accused playfully.

Not that I would mind, of course. The handful of her friends I had met had been very attractive. She laughed a little harder than I had. For just a moment, she looked like she was going to say something, but then she changed her mind and licked her lips as she gazed thoughtfully at the wall. Before she could figure out what she wanted to say, we heard the key in the front door and we both turned to face the door.

I damned near fell back into the couch when Sherry walked in the front door. She was wearing a long trench coat, but it was open in front and revealed the Wonder Woman costume she had worn to the party. She held the helmet under her left arm, and her smile took my breath away. She was blonde, with slightly lighter hair than my sister’s. My sister bit her lip when she saw my face, and then she shook her head and turned back to her roommate.

“Sherry, this is my brother, Bobby,” she said. “Maybe you two already met at the party this evening?”

Once again, I felt like I was in a trance as I walked up to Sherry and held out my hand. We shook hands slowly as she looked up at me.

“I don’t think we were introduced,” she said.

“I think I saw you talking with our parents as I was leaving,” I managed to say.

My voice sounded far calmer than I felt in that moment. As soon as I said it, though, I realized I had messed up. Admitting I had seen her then meant that I had still been there when she had surrendered her asshole to a guy she had never even met. My parents had been under the impression I had left some time earlier.

Sherry smiled and released my hand. “Sorry, but I need to change out of this costume and shower.”

As soon as her bedroom door closed behind her, my sister looked thoughtful again, but she wasn’t looking at me. She was looking at Sherry’s bedroom door after it closed and she seemed preoccupied. I was just grateful she wasn’t looking at me. I can’t imagine what my expression was in that moment, but I can tell you what I was thinking.

Holy fucking hell! I just met my dream girl and fucked her in the ass—and she’s my sister’s roommate!!

I plopped my butt down on the couch once again, and turned on the television. I have no idea what was on. My eyes were on the television screen, but my focus was on the conversation my sister and her roommate were having behind me. They were keeping their voices down, but I had no problem hearing every word clearly.

Sherry let out a surprised gasp when she went from her bedroom to the bathroom and saw the costumes hanging up in there.

“Oh! Bobby was Captain America?” she blurted.

“Mmm-hmm,” my sister replied.

“Shit! You weren’t kidding,” Sherry said softly.

“If you ever get tired of Darren…” my sister started.

“Not after tonight,” Sherry replied dreamily. “He finally gave me what I wanted, thanks to that Wonder Woman costume.”

“Really?” my sister gasped. “I thought that was never going to happen.”

“I was completely surprised when it happened,” Sherry whispered. “But, oh God, it was absolutely perfect.”

I stared dully at the screen in front of me, stunned. Then I had to wonder if I was mistaken; maybe they were talking about something else? I didn’t dare look in their direction. Once again I was certain my expression would give me away. I damned near jumped up out of my seat when my sister plopped down next to me on the couch.

“Mind if I check the weather?” she asked, reaching for the remote.

“Go right ahead,” I replied automatically.

She looked at me after she had changed the channel, and I hesitated before meeting her gaze.

“Looks like it will be a nice day tomorrow,” I said, echoing the statement of the woman on screen.

Karen nodded, looking from my face to the television and back. She looked like she wanted to ask me something, but thought better of it. After a couple of minutes she changed the channel again. It took me a while to figure out that it was a movie we both liked since I was so preoccupied with my thoughts. I was trying to figure out what Sherry had actually been talking about.

My anal-sex-obsessed mind had automatically wanted to think she was talking about when I had fucked her in the ass in that dark bedroom, but that just seemed too unlikely to be true. The problem was, I couldn’t think of anything else that made sense. I figured it had to be something I just didn’t know about Sherry and Darren’s relationship—something my sister was aware of, from her comments.

Maybe he had proposed, or given her a ring or something? My heart sank when I pictured that scene, knowing how incredible Sherry was. Immediately my mind replayed that unforgettable moment of my cock pressing into her tight little welcoming asshole, and I knew that was never going to happen again. By the time I cleared all those thoughts from my mind, Sherry had finished her shower and gone back into her bedroom.

I blew out a long, slow breath and focused on the movie. Right at that moment one of our favorite scenes played out on the screen, and I joined my sister in a heartfelt laugh. We looked at each other and shared a smile before turning back to the television. In that moment I felt like I was going to be alright, and that my life would be better now that I was here with my sister.

Then Sherry plopped down on the other side of me and I had to struggle not to stare at her. She was wearing a white undershirt without a bra, and her huge tits were impossible to ignore. I glanced at my sister, but she seemed oblivious to the show her roommate was giving me. I realized then that my sister wasn’t wearing a bra either, and her perky nips were just as obvious through her snug red tank top.

I had seen her wearing that tank top before, at home. This was the first time I’d seen her wear it without the obvious bra showing through. It was surprising how large and firm her breasts actually were. I guess I’d always assumed her bras made them look bigger and firmer than they were, but I think the opposite was true. Her bras had squashed her breasts, rather than showing them off. I realized they probably dressed like this all the time when it was warm, and then I felt a pang of guilt for checking out my sister’s tits.

Just a few minutes later, Sherry’s phone rang on the kitchen counter and she gave me one hell of a show as she popped up from the couch and bound over to grab it. Not only were her huge tits bouncing like crazy as she moved, but her shirt rode up and displayed her perfect bottom encased in tight, soft shorts as she leaned over to pick up her phone.

“Hey, Darren,” she gushed. “Thank you so much, baby. That was exactly what I needed tonight.”

I couldn’t help but stare at the way she wiggled her bottom when she talked to him, and then I was surprised that we could hear his voice so clearly when he replied. Darren’s voice immediately set my teeth on edge. A glance to my left showed it wasn’t just me; my sister grimaced when she heard him.

“Well, I’m glad you could hang out with your friends and have a good time after I had to leave,” he replied. His tone made it sound like he wasn’t glad at all. This guy sounded like a condescending prick.

Sherry turned, and I watched the loving, happy smile melt from her face. I felt bad for her.

“That wasn’t what I was talking about…” she started, but Darren cut her off.

“Oh, and you really need to get rid of that tacky costume,” he huffed. “Honestly, it was embarrassing to see you flouncing around like that. I’m just glad my parents didn’t see you dressed like that.”

“But…but you…” Sherry mumbled, clearly hurt and at a loss for words.

“I’m going to sleep now,” Darren continued, and we could hear him stretch and yawn. “I have an important meeting in the morning, and I’ll be driving back to my parents’ house after that. I’ll call you when I get there.”

“O-okay,” Sherry muttered. “Sweet dreams.”

Darren hung up with an audible click. Sherry stared at her phone for a long moment before setting it on the counter and wandering back over to the couch to sit next to me again.

Once again, I could not help myself. I reached over and started rubbing her back and shoulder the way I would have if she was my sister. Sherry looked hurt and I wanted to comfort her. I also wanted to punch her boyfriend in the nose at that moment, but I wouldn’t have actually done it. Probably.

“Are you okay?” I asked softly.

She licked her lips and swallowed before looking up at my face and giving me a weak smile. Even though I was doing my absolute best not to stare, I saw her nipples harden as she looked into my eyes.

“Yeah, I’m fine,” she replied. She didn’t sound fine, though.

Then she glanced down and saw how hard her nipples were. She leaned forward quickly to hide them by pressing her breasts against the tops of her thighs, and she sighed again before turning her head to look at my face. I was still scratching her back lightly, but wasn’t sure I was free to touch her like that until she spoke.

“That feels nice,” she murmured. “Please keep going.”

“Me too!” my sister said with a chuckle, drawing my gaze in her direction.

I smiled at her and reached over with my left hand to rub and lightly scratch her back as I did the same to Sherry on my right. They sighed happily and often as I worked them over and we watched the movie. We laughed together at all the funny scenes, even though we had all seen the movie several times. I probably spent a little over an hour scratching their backs and lightly massaging the muscles around their shoulders and upper backs. The way they were both leaning forward while I did it hid their breasts from my view, but I could tell that they both wore thongs beneath their soft shorts.

It was already pretty late when we started, so I wasn’t surprised that they were both ready for bed after the movie ended. What did surprise me was the way my sister pulled me to my feet and gave me a tight hug, holding my body against hers for a long moment.

Then she shocked me by kissing me softly on the lips—we had never kissed like that before.

“Thanks, Bobby,” she murmured afterward. “That was really nice. Sweet dreams.”

“Sweet dreams, Karen,” I replied. I didn’t know what else to say.

My sister slipped from me and her left hand turned me to face Sherry as she stood up from the couch. Then Sherry was in my arms, looking surprised as we hugged for the first time. I was equally surprised, and I was embarrassed to realize I was hard and she had to be able to feel it. I pulled my hips back self-consciously, but that put my face closer to hers and then we were kissing.

No tongues or anything, but it was nice to feel her soft lips against mine. We both murmured a soft “sorry” after we broke off the kiss, and then we shared a guilty smile. I felt like I needed to say something to her, but I could have chosen my words better.

“I thought you looked amazing in that costume,” I blurted.

As soon as I said it, I felt my face get hot with embarrassment, but she just laughed softly and kissed me again.

“Thanks,” she replied. She chuckled and added, “Maybe I should wear it for you.”

I was too tongue-tied to reply, but my sister stepped in at that point and saved me from embarrassing myself further. She cleared her throat and we both looked over at her.

“Sherry, mind if I talk to you for a minute?” she asked.

“Sure!” Sherry replied with a smile.

They walked around the couch and into my sister’s room, and Karen turned to grace me with another smile.

“Good night, Bobby,” she said.

“Good night,” I replied, but they had already pushed the door closed.

Well, most of the way closed. I sat down and shook my head, and tried to figure out what to do. I was far too keyed up to fall asleep, and a glance down at my lap made me groan. Jesus, I was pitching a tent in those shorts! I wondered how they could have missed it, but what I should have realized was that they hadn’t. It was me who had missed it when they had seen my dick bulging out the front of my shorts obscenely halfway through the movie.

I pushed my dick down the left leg of my shorts and started flipping through channels. I didn’t feel like watching television, really, but I figured I would see what was on. I turned the volume all the way down so I didn’t have to listen to the commercials as I flipped through channel after channel. Then I stopped and turned my head, straining to hear their conversation after I caught one little bit.

“I thought you said he gave you what you wanted?” my sister asked.

“I thought so too!” Sherry replied. “I’m so confused right now.”

“Wait,” my sister said, so softly I could barely hear her, “We are talking about the same thing, right?”

“Yes. I did exactly what you said. I wasn’t wearing panties, and I had lubed up ahead of time. I had that butt plug you gave me…”

My eyes shot open at that revelation, and I swallowed heavily, so I missed the rest of what Sherry said. What had my mind reeling was that my sister even owned a butt plug. For a fleeting moment my mind insisted on going there—picturing my sister with a horny expression as she reached back to insert that slick metal plug into her shapely ass. I shook my head, feeling guilty for even thinking such a thing. It took another minute for me to manage to hear my sister gasp.

“Jesus! You know what? I think it wasn’t Darren! I think someone else came in there, found you like that, and just—”

“Oh God no!” Sherry groaned. I could easily picture her clapping her hands over her mouth in horror. “That’s so fucked up! Don’t even say that, Karen!”

“Well, you’ve got to admit; it makes more sense than Darren leaving and then coming back to take you like that. Jesus, that’s hot. I wonder who it could have been?”

“Oh, dear God, do you think it was Mark?”

“No. He wasn’t there, remember? He and Allison had that thing at her parents’ house.”

I heard Sherry blow out a relieved breath, and then they quietly discussed several other guys they knew. Some of them had been at the party, but they tentatively ruled out most of them over the next fifteen minutes. When I heard my sister suck in a sharp breath, I had a sinking feeling in my stomach. Somehow I just knew she had figured out that it was me.

I know, it’s immature as all hell, but I turned off the television and quickly spread the blanket over my body. I wanted to act like I was asleep in case they came charging out to confront me. I don’t know why, but it felt like I would seem more innocent if I were somehow sleeping when they figured it out. I closed my eyes and tried to breathe slowly and evenly.

After that, I could feel how tight the muscles in my shoulders and neck were and made an effort to relax them. If it looked like I was flexing in my sleep, they weren’t going to buy it. Once I managed to relax my shoulders, several other muscle groups in my neck, back, and legs gradually uncoiled and let me breathe easier. I thought I heard soft footsteps approaching, and hoped they would buy my act.

I managed not to flinch when I felt warm breath on my cheek. My sister gave me a soft peck on the cheek, and whispered, “Sweet dreams, Bobby.” Then she padded away, and I heard her door close. After that, I heard their soft voices continuing their conversation for several more minutes but I could no longer make out their words.

* * *

It shocked me that I had fallen asleep, but I had done such a great job of systematically relaxing all my muscles that I had drifted off. When I woke up in the morning, there was already bright sunshine streaming into the room. After a minute of my eyes fluttering open and taking in my surroundings, I sat bolt upright on the couch and looked around in alarm.

Both bedroom doors were closed. I glanced down at my arms, like I was looking for stab wounds, and I recall thinking, Well, at least they didn’t kill me in my sleep. As I reviewed last night’s events in my mind, I wasn’t entirely sure that was a good thing. Maybe I would have been better off if they’d killed me in my sleep.

I had a horrible sense of foreboding, like I was doomed to pay a heavy price for what I had done.

My sister had figured it out. I was certain of it. What I didn’t know now was whether she had told Sherry or not. I figured she had to be mad at me for taking advantage of her roommate and friend that way. As I worked through it in my mind, though, I realized it could have been a lot worse. If Karen had revealed to Sherry what I had done, and she’d been outraged enough to call the police, I would not have gotten the chance to sleep through the night. I would already be in jail.

I figured I was at least a little ahead in the ballgame, so to speak, as I made my way into the bathroom to start my morning routine. I was still brushing my teeth when Sherry came stumbling in. It was evident she’d sweated slightly in her sleep from the way that white undershirt was plastered to her massive tits. I could see her nipples and areoles clearly, and she immediately noticed me staring.

“Oh!” she breathed, covering her breasts with her left forearm. “I totally forgot you were here. Mind if I use the bathroom real quick?”

I spat out my toothpaste and quickly rinsed out my mouth. “No problem,” I replied.

We both shivered as I tried to sidestep past her. My “morning wood” had brushed right across her pubic mound. I closed the bathroom door as soon as I stepped out, and I retreated to the couch so I could cover my obvious boner with the blanket. After a dozen seconds of slow breathing I knew I wasn’t going soft anytime soon. I just couldn’t stop picturing Sherry’s incredible body.

I figured it would be a smart idea to put on some snug underpants beneath my shorts, and maybe to find some heavier shorts that would do a better job of concealing the blatant erections I kept getting around Sherry—and my sister! I reminded myself. I got up and shook my head as I pulled my overnight bag onto the couch and selected cargo shorts, boxer-briefs and a fresh t-shirt. I had already put on deodorant before I brushed my teeth, so I figured I could go ahead and change my t-shirt.

Naturally, Sherry emerged from the bathroom just after I had whipped off the shirt I had slept in. I heard her gasp, “Oh!” and looked over to see her feasting her eyes on me. All I had on were those thin, gray workout shorts, and they did nothing to hide my completely hard dick. I contained a groan, but realized it wasn’t my crotch that held her attention at that moment; she was looking up and down my chest and abdomen and practically panting. Her eyes widened even further when she finally noticed the tent in the front of my shorts.

I watched her breasts heave with arousal, and that only made me harder. Her nipples were completely hard and pushed out more than half an inch against the tightly-clinging fabric of her white undershirt. I was a little embarrassed to be caught this scantily clad and with such an obvious boner, but I couldn’t take my eyes off of Sherry or think clearly enough to put that shirt on.

We stood and stared at each other for several seconds until our eyes met, and then we both blushed and smiled. I finally managed to pull my t-shirt on over my head, and Sherry turned and let out a soft gasp when she noticed how obvious her nipples were. She covered her chest again and scampered into her bedroom. As soon as I had pushed my head through the neck opening of my shirt, my eyes automatically settled on the tight globes of Sherry’s ass.

They were only partially covered by her undershirt, and she was wearing that tiny pink thong I had caught glimpses of the night before. Only now she was no longer wearing shorts over it. That tiny wisp of cloth disappeared between her shapely cheeks, and it gave me an amazing view.

I was mortified to hear the lusty groan that came out of my throat, but I couldn’t help it. Damn, her ass looked incredible! Sherry turned her head and looked over her shoulder at me, and she saw where I was looking. She also couldn’t miss the way my hard dick lurched up in my shorts. I watched her shiver as she swallowed heavily, and she hesitated a long moment before she reached over and pushed her bedroom door closed behind her.

I was shaking as I made my way back into the bathroom. I pulled that t-shirt off again and washed my face in the sink, splashing cold water over my face three times to try to calm down. After I dried my face and changed into the boxer-briefs, t-shirt and cargo shorts, I was relieved to see that my dick was far less obvious. Just as I prepared to leave, there was a soft tapping at the door.

I opened the door and gave my sister a grin as I slid past her and let her in. I returned to the couch and put away my overnight bag, and then I put the shorts and shirt I had worn to sleep in into a plastic shopping bag along with my other dirty clothes. After clearing that stuff out of the way, I folded up the blanket I had been using and laid it across the back of the couch before sitting down and turning on the television.

The kitchen was just past Sherry’s bedroom door. When I walked out there to look for something to eat, I couldn’t help but stop just outside her door. She was moaning, and that was what initially drew my attention. I swallowed hard when I heard rapid, rhythmic, wet sounds accompanying those moans. I couldn’t help but picture her pushing her fingers in and out of her wet pussy and squeezing her hard nipples. I wanted so badly to push open that bedroom door and walk in there!

Instead, I forced myself to keep walking into the kitchen, and I blew out a big, long breath as I opened the refrigerator. A soft intake of breath behind me drew my attention back toward Sherry’s bedroom door. This time it was my sister who had stopped when she heard the obvious sounds of her roommate masturbating. I grinned at her and she shook her head.

Karen blushed slightly and bit her lip, and I was surprised to see her nipples were hard and protruding noticeably through her tank top. I only glanced there for a second, but I’m pretty sure she noticed. I did my best to play it off by turning back to the fridge and pulling out the milk. When I stood upright and closed the refrigerator door, I was surprised to feel my sister hug me from behind. I could distinctly feel the hard points of her nipples against my back.

“I’m so glad you’re here,” she murmured into my shoulder blade.

I looked over my shoulder at her and grinned. “Thanks for having me,” I replied.

She sighed and released me, and we sat down at the little round dining room table to have breakfast together. Sherry was still flushed when she joined us a few minutes later, but we just smiled and acted like we hadn’t heard her moaning and getting herself off in there. It helped that she had changed into a longer, thicker and darker t-shirt. Well, it helped me anyway. I managed not to stare at her tits while we ate our cereal and then cleaned up afterward.

Of course, what gave me the most relief was the way my sister was smiling happily at me. I was still pretty sure she had figured out what had really happened at the cosplay party, but she wasn’t upset with me. If anything, she seemed happy. That didn’t add up in my mind, but I wasn’t about to question my good fortune. I was just enormously relieved that the two of them hadn’t confronted me angrily about the incident.

* * *

After breakfast, I excused myself to go out for a jog. It was something I was used to doing every day, and I felt like the girls wanted some privacy to talk. I wound up going much further than I had planned. I jogged onto the campus and found my way to one of the tracks around a training field. There were four other students running laps, but we were pretty well spaced out and I really didn’t try to engage any of them. I just ran and thought.

As soon as I had gotten up to speed, about a block from my sister’s apartment, my erection had finally subsided enough for me to think straight again. I managed not to get hard as I thought about that party again. This time, I was focused more on the rest of the people at the party. There had been about thirty women there and seventeen or eighteen guys. It bothered me now that so many of those college girls had been watching me closely, because I was pretty sure at least one of them had to have seen me go into that bedroom where Sherry was waiting for me.

Well, that wasn’t entirely accurate—she hadn’t been waiting for me—but it was how I thought of it.

The more I went over it in my mind, though, the more I was certain nobody was looking in my direction when I came out of that bedroom. I had been so fucking paranoid, looking all around, that I would have noticed anyone looking my way. So, I had probably gotten away with it. Except…

I frowned as I thought about my sister’s words from last night. I was still pretty sure she knew what I had done. The way she had hugged me at breakfast, and smiled at me while we ate, made it pretty clear she wasn’t mad at me. I shook my head as I thought about her happy face at the breakfast table. I really didn’t know what to make of that. Was she happy that I had fucked her friend in the ass? That just seemed too ludicrous for me to believe it.

Then I thought about Sherry’s boyfriend, Darren. I hadn’t met the guy, but thought I had gotten a glimpse of him leaving that bedroom. Just from hearing him talk on the phone I already didn’t like him. Maybe that was just my sister’s opinion influencing my own. I knew she couldn’t stand the guy.

When I tried to picture him from that brief moment at the party, I couldn’t really recall any significant details. If he jogged right up next to me on that track, I wouldn’t have known it was him. He’d been wearing some kind of hat and a loose, flowing costume. It might have been a robe or cloak, or perhaps at that angle it was a cape. All I could recall clearly was that look of disgust on his face. My eyes shot open when I realized what must have happened.

Sherry had presented her boyfriend with her sexy, lubricated asshole, and he had marched right out of the room in disgust. I stumbled a bit and had to take a moment to regain my stride. I looked around but nobody had been watching me. Then I shook my head again as I analyzed that scene again and again. It made perfect sense, but I struggled to accept Darren’s reaction. Mine would have been the exact opposite, of course. If sweet, sexy Sherry had been offering me her ass like that…I had to stifle that thought so I wouldn’t immediately have a full-blown erection.

It’s really difficult to jog like that.

My sister’s words ran through my mind again, and I knew she had said, “You two would be perfect for each other,” or something close to that, several times. Putting aside the undeniable physical attraction I felt for Sherry, I knew that I really liked her already. It had felt like the most natural thing in the world when I had hugged her to me the night before, and she had been the one to kiss me that second time. I reminded myself that was still technically “physical attraction” when I had touched her, when we hugged, and when we kissed.

I smiled then as I recalled laughing along with her and Karen while we watched the movie. Our conversation at breakfast had been just as fun. Sherry seemed like someone I would really enjoy spending time with, even if we weren’t having sex. Then I shivered as I recalled the way she had looked at me. It would be tough to spend time around her and not have sex…

There was a couple who had been jogging around the track a little slower and talking. I had passed them three times, and I noticed that they were leaving. A quick glance around me showed that there was only one other guy still puffing along on the other side of the track, and I looked down at my watch. Wow. I’d been jogging along at a pretty good clip for more than half an hour already. I slowed my pace to an easy, loping jog for my “cool-down lap,” but as soon as I did that I heard the unmistakable sounds of weights being lifted and set onto metal supports.

My ears pricked up at that familiar sound.

I turned and headed in the direction of the sound, and found a small gym that was open just across the street from the practice field. There were only a handful of guys in there working out, and three of them were athletes I recognized. They were in amazing shape, and played for the school’s football team. Those guys were surprisingly nice, and welcomed me to join them. I spent the next hour lifting weights and talking with them. It felt like I was making friends, and I managed to forget my concerns about my sister and her roommate.

* * *

When I returned to the apartment, I was drenched with sweat. I hadn’t tried to push more weight than I could handle—hadn’t tried to show off in front of guys who were in such obvious great shape—but I had gotten a really intense workout. They had pushed me to work a little harder and put in more reps than I would have otherwise. Of course, just having a spotter allowed me to push a lot more weight.

I blew out a big breath when I walked in the door of the apartment, feeling the cool air inside blowing over me. Out of habit, I pulled my sweat-soaked t-shirt over my head and headed toward the bathroom. Out of the corner of my eye I caught the bulging eyes of Karen and Sherry as they stared at me open-mouthed. It was a nice little ego boost, but I had my heart set on a shower.

There’s just something magical about a hot shower after a good workout. It feels like you are being cleansed in spirit as well as body. The hot water felt like it was sinking into my aching muscles, soothing them to the core as I lathered up and scrubbed myself. Of course, I hadn’t bothered to bring clean clothes into the bathroom with me, so I emerged from the bathroom just wrapped in that bath towel.