House-Sitting with a Homosexual

I am a straight male with some bisexual tendencies. I apologise if this story does a poor job of representing gay people or gay culture. It is a fictional story, though it is sort of based on a true life experience. I had the same opportunity as my character Eric, but never followed through with it. I always wondered and fantasized about what could have happened if I did, and that is the basis for the following story. It starts out slow, but I promise that it gets a lot hotter in the second half and then the second part. Without getting to know the characters before the sex starts I never really get too much into the story. This is my first submission to Literotica and was self-edited, so please be kind and constructive with your criticism.

Prologue: A Winter Encounter

Elena and I rushed in from the cold, holding each other's hands. It was late December and it was practically a blizzard outside. The mall we walked into had decked its halls in Christmas lights, Christmas trees, and paper snowflakes. We were both freshman in college and this was the first week of our holiday break. We were trying to do some last minute shopping for each of our parents. This would be the first Christmas we would spend with each others families and so we wanted to make a good impression.

Elena and I had met the second week of the semester and had been dating for about two months. I slept with a few girls back in high school but never felt for any of them the way I did for Elena. I was her first lover, and she was devoted to me. We had been throwing around the "L" word but wanted to take our time before totally committing ourselves.

She had long, dark hair that ended in natural curls. She had a round, but pretty face with a button nose and sensuous lips. Her eyes were a dark brown, almost black. She wore heavy eye makeup and lipstick that made her look like a glamorous movie star from the 1930s.

I looked a bit more conventional. I had shaggy brown hair and blue eyes and had been told I was handsome by many girls but never really felt that confident in my appearance.

"Oh my god, Daniel!" yelled Elena. I looked up to see her running toward another young man she saw from the other side of the lobby and enveloping him in a big hug. She also allowed him to give her a kiss on the cheek. Even though she was getting very friendly with another man, I wasn't jealous in the slightest.

"When did you get back?" asked Elena.

"Late yesterday, my finals were done last Wednesday but I decided to try looking for a job for the spring while I was still in Illinois", Daniel replied.

Daniel was Elena's best friend. He had left go to to Northwestern in Evanston, Illinois while Elena enrolled in our hometown university like I did. I had heard a lot about him but had not met him yet. He was very skinny and definitely had a "hipster" look going on. He had large glasses and a little bit of stubble on his cheeks and chin. He hair was cropped short and beneath his glasses I could see he had blue eyes like mine. He was wearing a striped scarf, a sweater jacket and tight jeans. Daniel had come out as gay before leaving for college and seemed to be very comfortable with his sexuality.

"So this must be Eric," Daniel said as he turned to face me. "I have heard a lot about you." Daniel reached out his hand to shake mine and I returned it. His grip was quite strong, though I didn't really expect it to be effeminate or anything.

Daniel said to Elena, "Wow, he is really hot. You did a nice job this time, Elena." We all chuckled, but I started turning a bit red when Daniel winked at me.. I had never had my looks complimented on by another guy before. "It sounds like he keeps you well satisfied in bed too."

"Oh, will you stop it," Elena said, hitting Daniel playfully. If you thought my face was red before, now I was crimson.

"Who are you kidding girl, you are such a floozy," Daniel replied. "I have got to run though, I am supposed to be meeting someone. It was great seeing you! Hope we can meet up a few times before break is over" Daniel gave me another handshake and gave Elena another hug before he departed.

"So you talked to him about our sex life?" I asked incredulously after he left.

"Who else was I supposed to talk to? He is my best friend," Elena retorted. It was true, she didn't have very many friends, though the ones she did have were very close. "Why does it bother you so much?" she asked.

I replied, "I don't know. It just feels weird. Him thinking about me having sex in that way."

"You are not going to go all homophobic on me now, are you? I thought you were better than that."

"No, not at all. I love gay people!" I said the last part loud enough that a couple people around us overheard and turned their heads. Elena started to snicker and I said, "Not in that way either. Ha ha."

Elena leaned in close to my ear and whispered, "Well, to make it even I can tell you about his sex life. Two weeks ago when we talked on the phone he told me that he had given a blowjob for the first time in his life. Does that make you feel weird?"

"Of course not", I said.

But what I could not tell her was that it did make me feel weird in a way I had never experienced before. And I would be thinking about Daniel's mouth on my penis for months to come.

Act I: Spring Awakening

Daniel found out a few days later that he had scored a job interview back in Illinois that was scheduled two days after Christmas. With all the busyness of the season and Daniel having to go back early, Elena and him never got to meet up again. Elena and I hit it off very well with each other's families and our relationship got even more serious. Even though we were still so young, we had already begun discussing marriage and having kids after we both graduated from college.

While I was still living in the dorm, Elena had moved in with her sister who was a few years older than her and already graduated. Elena had been living in a sorority, but unsurprisingly she hated it and moved out after only one semester. That made meeting up a little more difficult, but her sister was gone from the house a lot so that gave us lots of chances to sleep together.

I ran on the Cross Country and Track team for the University, but blew my knee out in a freak accident during a race at an Indoor Track Meet. It was going to take a year to fully recover enough so that I could run again, and I decided just to quit racing. I had academic as well as athletic scholarships so I could still afford to go to school. Before my accident I was a complete straight-edge. I never smoked and rarely ever drank. After the injury though, I began to drink and go to parties (wearing crutches of course) and I also became a bit of a stoner. Elena didn't care much for me smoking pot but she knew my injury gave me constant pain so she didn't begrudge it too much.

Towards the end of the semester I finally had surgery done on my knee which put me out completely for a few weeks. After a few weeks of recovery I finally could stop wearing the crutches and boot and start bending my knee. I didn't smoke or drink for a few weeks and couldn't be intimate with Elena either. I was practically dying after just a week without any of those things. It sounded like Elena was planning a bit of a surprise for me though.

It turns out that Daniel was finally going to be back in town but unfortunately it was the same week that Elena's family was going on vacation. She was super pissed about it, but glad that they could at least see each other one day before she left and he went back to Illinois. Apparently I wasn't enough a part of the family yet, so I was not invited to go with them on their vacation to California. Elena and her sister did ask me to house-sit and feed their cat while I was gone though, so I decided to just spend the night at their place for a few days instead of at my parents where I had moved back for the summer.

Elena invited Daniel to come over and have a few drinks and watch something with us. Elena and I started a little bit early and were already two drinks in when we heard a knock at the door. Elena opened it to let Daniel in. He was wearing shorts and a Arcade Fire T-shirt and it looked like he had gotten new glasses since I had seen him last. He was also clean-shaven now instead of having the beginnings of a beard. Elena gave him a long, deep hug and then Daniel surprised me by giving me a hug as well.

We weren't 21 yet but Elena's sister did keep beer and other drinks in the house. I told Daniel, "I am not much of a bartender but I can try and make you something. There is instant Cosmopolitan or Margarita mix or we have beer."

"A Cosmopolitan would be great, Eric," Daniel replied.

I made a Cosmopolitan for Elena and Daniel and grabbed a beer for myself then went downstairs where Elena and Daniel were talking on the couch. We decided to watch some episodes of Arrested Development since Elena and Daniel were both in shock that I had never seen the show before. Before we started Elena nodded to Daniel and he pulled a pouch out of his pocket. In it was a bag of weed and a small pipe.

Elena said, "I know how badly you have wanted to smoke these last few weeks. I asked Daniel to pick up some pot so you could smoke together."

"Wow, thanks El! I didn't know you smoked, Daniel."

"On occasion, particularly when I am in the right mood." He filled up the pipe with some very green looking bud. He had definitely spent some money getting that good of stuff. He gestured for me to start and so I took a lighter from him and lit the green in the bowl.. After taking a puff, I asked if Elena wanted to try it and she shook her head. So I handed the pipe to Daniel instead. We started watching a couple episodes, slowly getting high and imbibing more alcohol all the while..

"Lucille Bluth is like my spirit animal," Daniel said during a particularly funny part.

Elena retorted, "Well that makes sense, since you are such a catty bitch!"

"Ouch" I said. "But you really shouldn't be one to talk, Elena." Elena punched me in my side and Daniel howled with laughter.

"Oh, I like him Elena." Daniel said between laughs. "He is a keeper."

While Daniel was laughing I started looking at his face for what looked like the first real time. I don't know if it was because I was a couple drinks in or was in an altered state of consciousness but I started looking at him differently. With his face shaven and with smaller glasses I could tell that he was really pretty. He actually looked prettier than a lot of girls I knew. I quickly banished such thoughts from my mind and kept paying attention to the show.

We watched a few more episodes and then Daniel declared, "I need a cigarette!"

"Ugh, you two go ahead," said Elena. I shrugged and nodded and went upstairs with Daniel to have a smoke. Elena still came outside with us while we smoked and chatted. After a while she excused herself to go to the bathroom and get a new drink. While she was gone Daniel and I just chatted nonchalantly about school and our hometown. Somehow, we got on the subject of his first boyfriend and how much of an asshole he ended up being. It must have been the alcohol or marijuana affecting my inhibitions but I began to just start asking whatever question came to mind.

"So when did you first know you were gay?"

"I suppose in a way I have always known. I definitely knew I only liked boys by the time I was 6 or 7."

"Who was the first guy you were with?"

"That would be the asshole boyfriend we were just talking about. That was at the beginning of fall semester.

"How did it feel to be with a guy for the first time?"

"Why are you so curious, Eric?"

Elena's return saved me from having to answer that question. I quickly changed the subject and said I wanted to watch the next episode. We went downstairs and had a few more drinks and tokes and watched a couple more episodes. Eric decided he had better leave "to give us some private time" he said with a wink and because he estimated he was about one drink away from being over the limit. We each gave him hugs and he left around midnight.

Later that night, I was lying naked in bed while Elena was straddling me. Her dark hair was curling over her breasts as she guided my cock into her wet opening. She was already wet after I had fingered her on the couch earlier and my cock quickly penetrated deep inside her. I would not consider Elena to be sexually adventurous. We tried a lot of different positions when we first started having sex but we had settled into always doing the four or five she liked best. She had a tiny mouth and so blowjobs were never really that satisfying with her. My cock is about 8 ½ inches long so I could only really fit the head and part of the shaft comfortably into her mouth. So she didn't really like doing that. She rarely let me go down on her. We had tried anal sex once, but it had ended with her crying on the bed and begging me to stop.

Her favorite positions from least favored to most favored are missionary, doggystyle, me lying down while she was on top, and her with her knees on the bed and hands on the headboard while I fucked her from behind. Tonight we were doing her second favorite; we decided it would be easiest with me lying down so I wouldn't hurt my knee again.

She had been riding me for about 10 minutes and neither of us were really close to an orgasm yet. This sounds awesome, but it was actually taking too long and starting to get kind of boring. To try and stimulate the situation Elena asked me questions as she bounced up and down on my cock. "So which of my friends to you fantasize about the most?"

I was shocked at her boldness. "Oh, I don't know El. I've never really thought about it."

"I don't believe you. What about Allie."

"She is way to skinny. I like a girl with curves like you." With that I slapped my hand hard across her ass and she made a cooing noise. I brought my hands up to play with her breasts and nipples. She decided to continue: "How about Amber?"

I decided to play her little game. "Yeah, Amber is pretty hot. If I thought you would be into it I would ask her to be in a threesome with us."

Elena actually looked pissed after I said that and stopped moving on my cock as she yelled, "Hey that is not cool. Amber is one of my closest friends."

Seeing that this situation was about to go nuclear, I said, "Well who do I know that you fantasize about."

Elena actually looked embarrassed and said, "Well I kind of have masturbated thinking about Bryan before..."

"What!" Bryan is my twin brother.

"Well, he looks just like you. That is like the farthest thing away from cheating."

I decided to punish her, so I grasped her breast harder in my hand and squeezed her nipple between my thumb and finger. She must have liked the sensation because she gasped and started to fuck me again.

Then she said, "Have you ever thought about Daniel while you masturbated."

I was shocked at the question, but lied to her face.

"No. Never."

"Good," she said. But she got a strange look on her face for a second like she was almost disappointed that I had never thought about her friend while I masturbated.

She was really going to town and was almost burying my entire dick inside her and pulling out all the way as she moved up and down. I could tell she was close to her orgasm and soon enough she began screaming and buried me deep inside her as she rode her climax. She sat still for a moment and then asked, "Have you finished yet?"

"Not quite," I replied.

"Well hurry up, I am tired and it is going to be a long drive tomorrow."

She started moving up and down on my cock again but I just did not feel into it enough to finish. But then I closed my eyes and starting thinking of Daniel. I began thinking that it was his mouth moving up and down on my cock instead of Elena's pussy. I grabbed Elena's ass and moved her up and down on me faster, while imagining that I was holding the back of Daniel's head and making him blow me good. Then a wicked idea came to mind and began to imagine my cock in Daniel's ass instead and before I knew it I was coming and coming inside of Elena. She rolled over next to me exhausted and we both quickly fell asleep.

Act II: Summer Swelter

I woke up early because I wanted to take a shower before Elena's parents came to pick her up and saw me here clearly unkempt and dressed in my clothes from yesterday. Elena's sister had been out drinking with friends and didn't get back to the house until after we were already asleep. I saw her as I went to the bathroom and she looked in pretty bad shape.

I started the hot water and stripped all of my clothes off. I got in the shower and began washing myself. I was still a bit horny from last night from thinking naughty thoughts about Daniel. I started to get excited and thought "what the hell". My dick was already fully erect and I began to slowly tug on it. After that I grabbed it fully in my hand and began pulling up and down. My curiosity over these new feelings I was experiencing took over and I began to move my hand behind my ass. I stuck out my middle finger and rubbed my anus with it. It was the first time I had ever touched myself in that way. I rubbed my finger around it for a minute while my other hand continued stroking my cock. The hot water running over me while I did this felt amazing. My ass had opened enough that I was able to stick the tip of my finger in. It encountered a bit of resistance and it began to feel a little uncomfortable. I just wiggled the tip of my finger in my ass for another minute and then I was able to put the rest of my finger in. All the while I was imagining that it was Daniel doing these things to me instead of myself. Stroking my cock in his strong grip. Putting his finger inside me.

I began to move my finger in and out of my ass while masturbating at the same time. Finally, I stuck my finger in as far as it would go. I could feel the walls of my rectum and began to play with what must have been my prostate because it felt incredible. It was the most intense feeling I had ever had at this point in my life. I kept pulling my cock harder and harder until I exploded and ejaculate began shooting straight up into the air. I got some on my hands and chest and pulled my finger slowly out of my ass to clean up. When I looked at my finger I could see that was a bit of brown fecal matter on my fingernail. All of a sudden I felt disgusted and ashamed with myself and quickly cleaned the filth off of myself.

As I was getting out of the shower I could see Elena was waiting for me outside the bathroom so she could take her turn.

"Damn, you were in there for over 20 minutes."

"Sorry, guess I just needed to get extra clean."

Elena finished her shower and we both got dressed and helped her pack. Her parents soon arrived and we were saying our goodbyes.

"Well take good care of the place. I don't know what I am going to do without you for a week."

"It's going to be torture. I will be so lonely without you here."

"Hey, how about I give you Daniel's number? It seems like you two are becoming friends and I think it would be cool for you two to hang out without me."

"Sure. Why not?" She gave me his phone number and then it was time for her to leave. She gave me a long kiss before she left (I could tell her parents were staring at us) and then turned to leave. Before she did, she turned back and asked, "Did you start wearing product in your hair?"

I replied, "Um, no. You know me, I never wear that stuff."

"Oh. Well there is like some hair gel in your hair or something."

I knew instantly what it was but didn't want to give it away. I mumbled something like "I will take a look at it" and then waved goodbye as she got in the car and started the long drive to California. I went back into the house and went to the bathroom. I looked in the mirror for a minute and then began washing the dried cum out of my hair.