Steven knocked three times on his sister’s door. Tricia quickly opened, revealing her messy dorm room behind her. She had been crying.

“I hate him,” said Tricia.

“Well, that’s why I brought this,” said Steven, holding up his book bag. Tricia retreated back into her dorm room and collapsed forward onto her futon.

“I appreciate you coming over, but you’re not going to make me feel any better,” said Tricia, her face smashed into a pillow. Tricia had just been dumped by her boyfriend Kyle.

“I beg to differ, Miss Emo,” said Steven. He opened up his bag and pulled out the contents one at a time. “Two bottles of white wine, a whole bag of mini Milky Ways, your favorite, and… some French movie I found at the rental place.” Steven examined the cover of the movie. He hadn’t had much time to pick one out, and wasn’t really all that sure what it was about. “And, if the movie sucks, we won’t even know because we’ll be too drunk. Drinking in the dorms; naughty us.”

Steven had come over to console his sister as soon as she had called him. Tricia and Steven had always had a close relationship with each other. Tricia was only a year older than Steven and they both went to the same college. It hadn’t been until Tricia was in her final year of high school that their relationship had evolved into what it currently was. That year, Tricia had discovered that Steven was gay.

It came as quite the shock at first. Steven was a pretty popular guy in school. He was a swim team star, all-academic, and he was very handsome; tall, jet-black hair, muscular with piercing eyes. He had been very popular with the girls in his school. It wasn’t until Tricia had found out about him that she realized why he had never actually dated anyone. Steven never came out to his parents, so he had bonded with Tricia over their shared secret. It brought them close together.

Tricia loved having a gay brother. She had always wanted a sister when she was younger, but found having a gay brother to be even better. She naturally felt more comfortable around him than she would have if he was straight. She could talk about anything with him and not put him off or make him uncomfortable. Tricia and Steven loved talking about boys together, and, once Steven started dating in college, they would even talk about their sex lives.

So, naturally, Steven was the first person Tricia called when Kyle dumped her. Steven, committed to cheering up his poor sister, tossed the bag of Milky Ways at the futon. They bounced off of the back and settled on Tricia’s shoulder. Then Steven started opening both of the bottles of wine.

“Come on, tell me what he did,” said Steven. Tricia rolled over and grabbed the bag of candy off of her shoulder. Steven had been right to bring them. Tricia really couldn’t say no to one. She reluctantly opened up the bag and reached in.

“Why are you opening both bottles?” said Tricia. Steven cocked his head to the side and raised his eyebrows.

“What?” he said. “Did you think we were sharing?” Steven popped the cork out of one of the bottles. He brought the bottle up to his lips and took a long drink from it. Steven passed Tricia the other bottle. “Here’s yours,” he said. Tricia smiled. Steven always knew what to say to her. “Ah, there’s that pretty face,” said Steven.

Tricia really did have a pretty face. In fact, she had a pretty head on top of a pretty neck attached to a pretty body. She shared some of the same physical features as her brother – she also had jet-black hair and narrow, piercing eyes. Tricia’s face was more angular than her brother’s though, and, where Steven was muscular, Tricia’s body was sleek. Her skin was incredibly smooth and she always kept it nice and tan. She had a cute, tight butt that stuck out just the right amount to make boys fawn over her, and a pair of perky c-cup tits she used to get free drinks at night clubs.

Tricia and Steven found some plastic cups to pour their wine in and started the slow process of killing both bottles. Steven popped in the movie, but neither one of them was really paying much attention to it. Tricia began telling Steven about what had happened with Kyle. It took quite a while and quite a lot of wine. It was a messy break up and Kyle came out looking like an asshole. Apparently, he had dumped her so that he could start going out with some girl named Trixie.

“Seriously,” said Tricia, “what dumbass names their daughter Trixie? I mean, unless you’re anticipating her going into porn and want to save her the trouble of changing her name.” Tricia was getting drunk very quickly. After an hour or so, Tricia was letting everything come out.

“Did you know he stopped having sex with me?” she said. “Yeah. He always came up with some excuse not to. ‘Oh, I’ve got a big test tomorrow.’ ‘Oh, I’ve got a headache.’ He used the fucking headache line on me.” Tricia laughed a little and so did Steven.

“What a little bitch,” said Steven.

“I know, right?” said Tricia, slurring the occasional word. “I think he felt guilty. I bet he was fucking his little whore on the side the whole time. Well, I’m glad there’s at least someone out there getting laid! I haven’t been fucked in over a month!”

Steven laughed. “Well, if I had known that, I wouldn’t have wasted time buying you Milky Ways. I would have gotten you something very different.” He laughed loudly. Tricia did too.

Between fits of laughter, Tricia managed to say, “Oh no. Believe me. Dr. Carter has put in a lot of overtime this past month.” Steven burst out in uncontrollable laughter.

“Oh my God! Are you serious?! Do you really still name your vibrators after E.R. characters?!”

Tricia snorted into her cup of wine. “I can’t believe I just told you that.”

“I can, you little slut.” Tricia threw a pillow at Steven. “I just hope Mom doesn’t find Dr. Carter like when she found George Clooney when you were sixteen.”

“Oh my God! Do you remember her face? It was just like….” Tricia changed her face into an overly frightened expression. Steven almost fell out of his chair. “Then she fucking threw it away! I paid Sandy Donalds forty bucks to go into that store and buy it for me! Money down the drain.”

“Yeah, but, all things considered, why did you name it George Clooney when it was black?!” Steven almost couldn’t finish his sentence before exploding with more laughter. Tricia and Steven carried on like that, bitching about boys, eating Milky Ways, and drinking.

Soon, they finished all of the wine. Steven wasn’t a big drinker, so Tricia finished her bottle before he did. Being a bit of a light weight, Steven gave the rest of his wine to Tricia, who chugged it down quickly. After they ran out of wine, they both ended up sitting together on the futon trying to catch up with the movie.

“Good God, how long is this thing?” said Steven. “I don’t even know what’s going on, do you?”

“Not a clue,” said Tricia. Both of them were very drunk. Just then, a man and woman on screen began passionately kissing.

“Oh. Ok, here we go,” said Steven. “I’ll give you ten to one odds we’re about to see the gratuitous sex scene.” The man and woman on screen quickly began tearing each other’s clothes off. “You see? There it is. Called it.” The man and woman were both speaking in hushed voices. The subtitles flashed across the bottom of the screen, but Tricia and Steven were both having trouble reading them; only retaining the occasional phrase.

Tricia watched attentively as the lovers on the screen mauled at each other’s bodies with their hands. The woman’s top was stripped off, exposing her smallish tits. Her nipples were hard. It was clear that the man was the dominant one in the relationship as he made the woman shiver in anticipation with his touch. He pulled her face close to his and said something in French.

“Holy shit,” said Tricia as she read the subtitles.

“What?” said Steven. He hadn’t seen the words correctly.

“He just told her he wants to fuck her in the ass!” Tricia’s jaw fell open slightly from the surprise.

“Are you sure?”

“Pretty fucking sure.”

“Damn. French movies are intense.”

On the screen, the man bent the woman over and pulled her pants down. Then he reached into his pants and pulled out his cock. The camera was angled behind the man, so almost everything was hidden.

“Hmmm,” said Steven as he watched. “It looks like you might be right.” Tricia was captivated by the scene. She watched intently as the man thrust into the woman. The woman whimpered as he entered her. Tricia suddenly felt very warm. A combination of the wine and the graphic scene was beginning to make her stir. She had always been turned on by dominant men, and the man in the film was definitely that as he forcefully fucked the woman.

“Holy shit, that’s hot,” said Tricia.

“Oh really? You’re into that?” said Steven. He turned his head to face his sister. “Are you….What the fuck? Tricia, are you touching yourself?!”

Tricia snapped out of the trance she had gone into while watching the scene and looked down. Sure enough, her right hand had found its way to the crotch of her jeans and she was gently rubbing herself through her pants. She quickly moved her hand away.

“Sorry, Steven,” she said. “You know white wine makes me horny.”

“Oh yeah?” said Steven in a teasing tone. “Does sodomy usually get you hot too?” Tricia didn’t answer right away.

“Honestly, I’ve kind of always wanted to get fucked in the ass.”

This sudden change in conversation intrigued Steven’s curiosity. Tricia had often talked about her sex life with Steven, but it usually wasn’t that… graphic. He turned away from the screen and gave his sister his full attention.




“Yes, I really do.”

“You want some guy to stick it in your butt?”

“Oh, come on. You make it sound so dirty.”

“It is dirty. It’s filthy. It’s naughty. Who knew I had such a naughty sister?”

“What? You do it all the time, you fucking gay-bo.”

“Well, most of the men I sleep with don’t have pussies, so I don’t have as many options. Besides, when I do it, it isn’t dirty. It’s beautiful.”

“Oh, now it’s beautiful.”

“There is a certain beauty to anal sex. It makes me feel at one with the world. Some people have tits, some people have dicks. Some people are ugly, some are hot. However, we all have a butthole. It doesn’t matter who you are, we all have at least one thing in common. Anal is the most progressive and accepting form of sex if you think about it.”

Tricia didn’t know exactly what happened to her at that point. A mixture of being extremely drunk and extremely horny must have sent a random neuron firing into the portion of her brain controlling her mouth because suddenly she just blurted out,

“Will you fuck my ass?” Steven took a second to make sure he had heard his sister correctly. He couldn’t believe she had just said that.

“Wha… WHAT?” said Steven. His entire body tensed at the idea of having sex with his sister. “Are you fucking crazy?”

“Is it really that crazy?” said Tricia.

“Yes! Yes it fucking is,” said Steven.

“No, seriously think about it for a second. You were just talking about how everyone has an asshole and how it doesn’t matter who you are and….”

“Not the point!” said Steven. “So not the point. You’re a fucking girl! I’m gay. Not to mention you’re my fucking sister for Christ sake!”

“Well, don’t think of it like that.”

“How am I supposed to think about it?” Steven cut off Tricia.

“It’s not like I’m asking you to have sex with me. I mean… not like the ‘I love you, let’s make love under the fucking stars’ sex. It’s just your dick in my butt. It’s nothing really. I just want to know what it’s like.”

“If you want to know so badly, why don’t you just ask someone else to do it? We could go downtown right now and find a hundred different guys who would fuck you.”

“Yeah, but….”

“But, what?”

Tricia lowered her voice a little. “I’m scared,” she said. “I don’t want to do it with some douchebag I met at a club. I’ve wanted to try it for a long time, but I don’t trust anyone else to do it to me for my first time.” Tricia moved closer to Steven on the futon and placed her hand on his knee. “I trust you more than anyone in the world. Please do this for me?”

Tricia and Steven went back and forth for a long while. Steven was still very resistant to the idea and Tricia did her best to convince him it wasn’t as big of a deal as he was making it out to be. After several minutes, the initial shock of the situation began to wear off for Steven and he gave it some serious consideration.

“Don’t even think about it like sex because it won’t be really,” said Tricia. “It’s just a brother helping out his sister. We don’t have to do anything else. I just don’t want my first time trying anal to be with some jerkoff.”


“I won’t even moan. Pinky swear. You can just stick your dick in me, think about James Franco, and shoot your load into a towel.” Steven was beginning to give ground; a lot of ground.

“Tricia, I want to help you out. I really do. But, I just…. How can you expect me to just… just stop being a gay man for you? Believe me, your ass would be the first ass I’d fuck if I could, Tricia.” Tricia thought about this for a second. Steven seemed to have gotten past the incestuous factor. But, she wasn’t sure how she was going to convince him to fuck a girl. Then she thought about something Kyle had left in her room awhile back.

“I’ve got an idea,” she said. Tricia went to her dresser and started pulling clothes out of drawers. Then she took off her shirt and pants, throwing them in the corner. Underneath, she was wearing a white bra and a black thong. With her back to Steven, he got a full view of her tight ass. He was disturbed to discover that he was not repulsed by the sight.

‘I must be drunker than I thought,’ thought Steven. ‘Obviously, I’m not as drunk as Tricia, but that ass isn’t looking half bad right now.’

Tricia slipped into a long sleeve plaid shirt and a pair of baggy men’s jeans left in her room by Kyle. Then she pulled her hair up and put on a baseball hat. She turned back to Steven, presenting her make-over.

“What do you think?” said Tricia. She had undoubtedly made herself more passable as a boy. No one would ever confuse her for a one if they looked at her face, but the effect had been created.

“I… ummm.” Steven really didn’t know what he thought. He was very confused as he realized that, on some level, he actually found himself wanting to fuck her.

Tricia saw that she was starting to break his will and decided to take a more aggressive approach. Tricia walked back over to Steven, still seated on the futon. She turned around and slowly moved her ass close to his face. Then she hooked her thumbs into the waist of her jeans and panties. Very delicately, she slid both of them over her ass and held them just under her cheeks, using the pants to shape her beautiful ass as well as hide her pussy from him. Steven didn’t say a word, staring straight ahead at his sister’s bare ass in front of him.

“It’s nice and soft,” said Tricia, seductively. “In fact, I bet my ass is softer and tighter than any boy’s you’ve ever fucked.” Those words hit Steven like a fucking baseball bat to the head. The idea definitely appealed to him. Tricia stuck the middle finger of her right hand into her mouth, making sure to get the whole thing wet with saliva. Then she reached behind her and touched her finger to her tight hole. Steven watched wide eyed as Tricia pressed against her asshole. Her finger slowly made its way inside, almost as if her ass were wrapping itself around it.

“Just think about it, said Tricia. “You can have this virgin ass all to yourself. No one will ever find out. It will be our special secret.”

That was the last thing Steven needed to hear. What did he have to lose now? With all of the alcohol floating around in his head, Steven reached down and unbuttoned his pants almost absentmindedly. Tricia smiled wickedly to herself as she heard the sound of his zipper being pulled down. She was finally going to get what she wanted.

“Does that mean you’ll do it?” said Tricia.

Steven had to catch his breath before he answered. “Yeah. I’ll do it. I’ll fuck your ass.” Tricia squealed in delight. “On my terms though,” continued Steven. “You keep the clothes on, we do it doggystyle, and we only do anal; nothing else. And, I can stop if it gets weird.”

“Agreed,” said Tricia. She reached over into a nearby drawer in her desk and pulled out a bottle of KY jelly. Then she got down onto all fours on her floor. “Here,” she said, holding the lube behind her for Steven.

Steven tentatively came down to the floor, kneeling behind Tricia. He grabbed the bottle and squirted some into his hand. Then he reached forward and slowly began spreading it into Tricia’s ass. It took all of his will to actually touch her in that way. Once he got going though, he started to become more comfortable.

‘You can do this Steven. This is no different than having sex with a guy. It’s just an ass…. An incredibly tight ass belonging to your sister.’ Steven shook his head. He had committed to doing this. He wasn’t going to back out now. He worked some of the lube inside Tricia’s ass using his fingers. Her anus involuntarily tightened up.

“Relax yourself,” said Steven. He waited for Tricia to regain control over her asshole and then resumed lubing her up. From behind, with all of the clothing she was wearing, she could have passed for an effeminate boy. Steven took comfort in that and imagined she really was a boy.

Steven pulled his finger out of Tricia and slid off his pants. He had thought that he’d stroke himself to get hard, but was surprised to find that he already had a sizable erection. His seven inch cock was standing at attention when he pulled his pants down. Steven thoroughly coated his dick in lube, and then it was time. Steven moved closer to Tricia. He lay his cock across Tricia’s crack and rubbed it up and down the length of her ass. She hadn’t been kidding about how soft her ass was. Her soft skin felt heavenly on Steven’s cock and he considered not going any further.

“Are you going to fuck my crack all night or are you going to stick it in?” said Tricia. The anticipation was killing her. Steven lined up the head of his penis with Tricia’s puckered asshole.

“Push back against it while it’s going in; like you’re trying to shit it out,” said Steven. Then he started pushing. Tricia did as Steven told her, pressing against his cock. To her surprise, it actually worked. The head of Steven’s cock, along with maybe half an inch of the shaft popped inside.

“Oh my God,” said Tricia in a low voice. She groaned as she experienced a cock in her ass for the first time. Steven paused for a while to allow Tricia’s ass to adjust to the size. Her breathing intensified just from imagining Steven’s cock stretching her hole. After she grew accustomed to the size, Steven began to thrust more of himself inside of her.

Tricia clenched her teeth together as another few inches slid inside. The sensation in her ass was intense. It hurt a little, but it mostly felt good. It was such a foreign feeling to her, but she found herself liking it.

Steven continued sliding in a few inches at a time, allowing Tricia to adjust every now and then. As her ass neared the hilt of his cock, Tricia began to yelp each time Steven pushed deeper. Finally, she felt her ass press up against his hips and Steven could go no deeper.

“Oooooooh,” moaned Tricia.

Steven had to admire how easily Tricia had taken him for this being her first time. He also couldn’t help but admire how nice Tricia’s ass looked with his dick shoved balls deep inside it. As they waited for Tricia to adjust, Steven reached down and grabbed a handful of her soft ass cheek.

July 2018
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