What follows is a work of fiction, if I just so happen to take real facts from my life and change every possible detail including my name, their names, dates, places, activities but keep the sex part the same but with more orgasms, it would still be fictional. The characters contained within do not exist, the events as presented in the order presented did not happen to anyone living or dead. No comment on whether or not I stole ideas from the future.
Keep the email to bimartinez@yahoo.com cumming please, it excites me to know I'm giving you an orgasm. Sure you might not be someone I'm attracted to (I don't like muscular guys, for example), but the fact I'm getting you off is sexy to me so let me know what you think of the story and drop your age if you'd like. I'm also curious about your orientation (1 Straight 5 bisexual 10 gay) as I know a lot of people aren't 100% gay and many bi guys don't like guys and girls equally.
This story, while containing sexual acts between fictional characters, is intended for adults. By continuing to read you are 18 years old or the age of viewing pornography in your country, whichever is higher.
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The Sex Life of Brian - Chapter 2: Sophmore Year with Brandon (mm, teen, high school, mutual mast, oral, anal, threesome)
This chapter takes place within an entire year. We had sex at least 4 times every month during the school year, but a lot of that is repetitive. While it feels good to have oral sex the exact same way many times with the same person, it doesn't make for great stories. If you want to know more about our second, third, and every time up until we introduced new activities described in this chapter, just read chapter 2 again but pretend there was no awkwardness and that we both knew what we were doing and the story will read about the same.
You're up to speed with my first time with Brandon. Strictly speaking, we were not each other's first times. He had sex with a girl before me and I had sex with his nephew (who was only 2 years younger and they called each other cousins) Clay before him. I was the first boy he ever has sex with and we were each other's first boyfriends. During our high school years though we were very firmly in the closet. We didn't tell anyone in our families we were gay (I mostly favored guys but had some hetero experiences later on) and bisexual (he ended up mostly favoring women). For now, we had this secret and made each other feel good.
You might be a young person reading this in 2021 or in later years wondering why neither of us were out of the closet (anyone 25 or older in 2021 knows what's up). Because this is written in English and I didn't mention a country, I constantly use inches and Fahrenheit, you probably guessed this took place in an English-speaking country and you would be correct we're both from the United States. But this story doesn't take place in 2021, it took place before 2003, the events of this story were illegal in many states. Had we had sex in Texas, this entire series would basically be a confession to a crime we got away with. While homophobic crime was falling, homophobia was not and it was perfectly acceptable for teachers to tell us they didn't support gay marriage. It was acceptable for students to say, "I strongly support sodomy laws and I think gay people belong in hell" even in the middle of class. Students wouldn't even get so much as a write-up or a talking to. Being anti-gay was an acceptable point-of-view. Same-sex couples were not allowed to attend prom at the couples' rate. My high school actually had a policy that same-sex couples would not qualify for the couples' rate for prom and school dances because too many straight people were going with each other. While not as bad as some of the stories on here that took place in earlier decades, you have to acknowledge we've come a long way in the last 15+ years.
In the last chapter, I said that the first time with Brandon was life-changing. That's because I would be dating him for the next seven years. I even asked him to marry me after we graduated high school (gay marriage was only legal in Canada and Massachusetts when I proposed).
So we never held hands in public, never kissed in public, and didn't call each other boyfriend unless we were alone. In my entire 4 years of high school, I only saw one same-sex kiss in the hallway. Not I didn't know any gay people or didn't see a lot of gay kissing at non-school functions, but nobody felt comfortable except that one brave couple. The fact they were girls helped, I never saw two guys kissing at school.
--Part one: First Intentional Dry Cum during nipple play-- So despite the fact I had a boyfriend, I just assumed this was a phase and eventually I'd be having sex with girls and wouldn't need to have sex with Brandon anymore. During the summer after I had sex with Brandon many times and Clay once I was hanging out with my (straight) cousin Xavier (he didn't care if you called him eks-a-vee-er or ha-vee-air) and he was telling me about his experiences with girls. I found the stories fascinating and he said, "Now you're probably going to need a condom, but I have mastered the ability not to cum during sex" (I later found out one of the girls he slept with had an abortion, so his plan wasn't exactly foolproof). This idea seemed farfetched, how do you stop that from happening, was it even a voluntary thing? I thought cumming was like your heartbeat in that it happens without your mind actually doing it. So I tried myself a few times and it didn't work. I figured I'd need practice for the day I finally have sex with a girl.
However, one day shortly after the school year started I decided instead of taking the bus I biked to school. Brandon said his parents wouldn't be home until 4 pm and we'd have the house to ourselves a few hours. The message was subtle to the others that were with us but loud and clear to me. He wanted to have sex after school. So 6th period ends, we grab our bikes and head to his house which was far closer to the school than mine was so it took only 10 minutes. Both cars were gone and his sister living in her dorm room so we had the house all to ourselves and didn't have to be sneaky about what we were doing or quiet during sex. We took advantage of this by stripping our clothes off immediately upon entering the house. We left our shoes by the back door, took our socks off while walking through the back living room and kitchen. Stripped our pants and underwear off while in the front living room and by the time we reached the top of the stairs we were carrying everything we were wearing except our shoes. He opened the door and put all of them in the dirty clothes hamper while I set mine in the corner.
"If we had our own place, I would not wear clothes unless someone was over," I said, "Jesus when it's over 100° degrees out there (37°C) you want to be wearing as little clothes as possible.
"Unless it was somebody who didn't care", Brandon replied.
"Yeah, like if we invited another guy over", I said
"Oh am I not good enough for you?", he asked with a pretend offense smile I didn't pick up.
"No, it's just that we're both young and still exploring. I don't want either of us to cheat on the other and I figured that could be a way for us to explore without cheating", I said defensively.
He stretched his arms out shocked I didn't pick up on his sarcasm, "No, I'm totally in. I want to find out what I like and don't like."
I was relieved, "All right, would you be open to a girl? I love you, but I'm not sure I'm gay."
He said, "Girls, guys even a foursome would be cool. You already know my first time was with a girl. You never told me about yours."
The time I had sex with Clay flashed through my eyes, then I imagined us kissing, there was no way I was hiding my tension well at all, "Um, yeah well it was with a boy and he goes to a different school." What I said was technically correct, but it wasn't the whole story. I didn't want to say, "Yep, he goes to middle school and it was with Clay you know your nephew you call your cousin" because I felt that would have at best been awkward and at worst could have made him break up with me.
"Well it sounds like I never met him", my heart skipped a beat, "but that's not what I wanted to know." He stepped closer to me and put his arms on top of mine and caressed his fingers from my shoulder to my fingers very seductively. I then remembered we're both naked and we're supposed to be having sex right now so he wanted some sexy talk to get him erect. "Tell me what he looks like." Oh god, no! I'm a terrible liar and if I start describing his cousin he's going to know. He's going to get mad, break up with me without having sex. He'll kick me out without giving me back my clothes and now I'm going to have to ride naked back home, get stopped by the police, go to jail. Get in huge trouble with my mom and when I think it's all over, he's going to tell everyone I'm a cocksucker and I'll be kicked out of my home and be homeless.
If any of that sounded irrational, it was. I told him years later that I had sex with Clay and it didn't bother him at all, but I'd already been his boyfriend for years so maybe it did upset him but he decided not to do anything about it.
I decided to play coy and tell the truth, but not the whole truth. "Well he was skinny like you, younger than us, you know freshman or 8th grade (it was between his 7th and 8th grade), black hair, brown eyes, and like you he was super enthusiastic about sucking me."
He leaned in closer his mouth only inches away, "Did you kiss?"
I replied with a grin, "we did."
He said, "Show me" and I kissed him the same way Clay did me. I even included some of the awkwardness.
"We weren't naked at first, but we started with a kiss. First, we bumped noses because we couldn't figure it out", I bumped his nose with mine, "then we started with a few pecs with our mouths closed." I demonstrated some closed and barely open-mouthed kissing. "Then we had the idea that we should use our tongues too, he knew more than he was letting on and he put his tongue in my mouth first", I then shoved my tongue in his mouth aggressively like Clay did to me. "I took his shirt off and kissed down his chest", I demonstrated this, his nipples were too flat to suck so I just licked them. "He did the same thing to me."
"Well, but I don't want to have milk in my mouth," he said.
"Well somebody didn't pay attention in sex ed, only girls do that, silly, and most of the time only after they've gotten pregnant," I replied almost laughing.
"Oh, well no wonder the first girl I had sex with said she felt deprived. I wasn't her first time and never sucked her nippled for that reason", he said and then he kissed down my chest and started sucking on my nipple. I started moaning as he did that. "So how far did you go?"
"Just Oral", I answered. "He went down on me first and I did him next. We both came in each other's mouths like we do." We were still standing.
"What would happen if you jacked off while I was licking you?" he asked.
"I would cum of course, but I wonder if I would feel any better" I said, he then grabbed my hand and had me lay down on the bed. He walked around to the other side and laid down on my left and leaned over and started sucking my left nipple. I'm right-handed so this worked out perfectly. I started stroking slowly at first but started picking up speed as Brandon did. He bit down, "Oh too hard", he released a little and mostly sucked. I grabbed his head and moved his head over my right nipple and he sucked that too. I moved his hand to my left so he could caress my left nipple. I kept stroking until I came, while I was coming I moaned very loudly since I knew we were alone, through the power of my mind I also braced the pipes in my crotch so I wouldn't fire as I orgasm and it worked. I only needed to know I could do it, it wasn't as good as a wet cum but it still felt great and I recovered a lot quicker.
To this day I have a low bar on sexual satisfaction. I don't need oral or anal to be happy. If all I ever do with a guy is a kiss, hug, dry hump and we lick each other's nipples while the other jacks himself off, I'm fine. I don't know how common this is, but I've been with few guys where this is all we did I was happy to do it. It's way better than jacking off by yourself, plus I like kissing feeling a body, licking nipples, and having mine licked none of which you can do alone.
"You didn't cum", he said.
"I did, it was just dry", I said.
"Did you jack yourself off several times today or what? I've never dry came my first time in a day", he said.
"No, my cousin was talking about controlling yourself so you don't get a woman pregnant. I've been practicing but this is the first time I've been able to do it", I answered.
"Well, you have a front-row seat Brian, so be prepared to get wet", he replied while beginning to stroke himself, I took the hint and started licking his nipples. He moaned quietly and started going faster which led me to go faster, "aaah, this is a little intense", he gently pushed my head away from his chest and continued stroking himself. I stroked whatever body part I could and then I had an idea as he was getting closer, I leaned in and started making out with him. He stroked himself as fast as he could and started moaning in my mouth and through his nose. He came, getting a little bit of cum on my side and back, we continued kissing through his orgasm and didn't stop until about a minute after he did. I laid back down and we held hands. His nearly-concave stomach was just holding his sperm in a pool on top of him. I never had this luxury, even at my skinniest cum would start flowing from the middle of my stomach down one side or the other.
"Wow, as awesome as it is to have you suck me it feels more intimate when we're kissing during the orgasm." He said. I certainly felt more connected to him right now than at any time during our previous oral sessions. He wiped himself with the shirt he put in the hamper and put it back in the hamper.
"Yeah, this was eye-opening. It felt like a new experience", we kissed after I said that. We played video games naked for the next hour. We stayed upstairs so that we'd have advance warning and could put our clothes back on. When we heard his mom come home we kissed and I said, "well time's up", I put my clothes back on while he grabbed new clothes from his closet. When we finished dressing we kissed again and I said, "I had a really good time, I love you" I saw a look of fear in his eyes, "as a friend?"
"I love you too... as a friend" he replied, we kissed for a minute, and we walked down the stairs barefoot. I put my socks on in the kitchen while his mother was getting dinner ready.
"Hello, Mrs. Falls, I was just leaving", I said. "It's okay Brian, you're not doing anything wrong. I figured you kids would do afterschool visits after spending so much time together this summer", she said.
Over our sophomore year, we had many sexual encounters with each other. We became masters of quiet sex because whether at his house or mine, there was usually someone else in the house with us.
--Part Three: Our first anal--
After high school, anal sex was a staple in our relationship and we already mastered our dynamics. I was a bottom (and would continue to be until I was around 25 years old) and he was a top. I was the first to try fucking him and he didn't like it, I could barely even get my pinkie in before he was in immense pain. He then claimed to have bowel issues and said he was, "plugged up." I guess he wanted to avoid telling me he didn't enjoy taking it. Trouble was, at first neither did I. In the entire time we were in high school we had anal sex a total of four times and three of those times were on his birthday. For simplicity, I'll just merge all four instances into one since the first time was a learning process, and each subsequent time after that it was basically like the second.
It one of the chilly months and it was the weekend after Brandon's birthday which was after the first of the calendar year. This was over five years before the song, but Birthday sex was a rule so widely known that even teenagers were aware of it. Birthday sex is, "Obligation-free sex which happens on or around someone's birthday. Usually initiated by the birthday boy/girl's partner, and involving a mix of acts which more favor the birthday boy/girl's preferences.
The usual rules of reciprocation and mutual pleasure are temporarily suspended, and the birthday girl/boy is considered free to cum whenever and wherever the fuck they please."
Basically, during this session, all pleasure was allowed to be his. He was under no obligation to get me off if I happen to cum from mutually pleasurable activity, that was allowed. But today Brandon is the star and gets what he wants. "I want to put my thing in your butt", he said. Saturday morning, he rode up the hill to my apartment. My mom and her husband were out and about so we could hump without worrying about being caught, plus the stairs leading up to the apartment were metal and concrete and were noisy as hell. Even a small child or medium-sized dog would cause banging noises when they went up and down them so we'd have plenty of warning.
The rules of consent still applied. I had the choice and opportunity to back out at any time, but I felt it would have violated the spirit, but not the letter of the birthday sex concept so I agreed to do it. The first time we did it, he went in dry and it was painful for both of us. He came inside my butt but didn't enjoy it very much until after he came. With his jizz acting as a lubricant he kept humping me and he said it felt better after he came. After he pulled out he kissed me, we were hungry so we put our clothes back on and went out to get some pizza.
Towards the end of the year coming up on final exams we were both tense. Our school gave us the Monday before off so I slept over at his house Sunday night. We were on his bed barefoot, his parents were out and about so I had no idea why we weren't naked. I was watching him play a skater video game enjoying seeing him release some steam when I realized we were alone and could have sex. The stress of final exams was a lot for both of us and I realized I didn't give him proper birthday sex. Our first time we didn't know about lube, but since then I researched it on the internet via Usenet groups. These were similar to social media sites like Facebook and Twitter, except people would always go by usernames instead of their real names, and there usually wasn't much sharing of people's personal lives or their pictures, think more like today's Reddit or 4chan. I asked why anal sex was so painful and I got a lot of snarky remarks about how I was too stupid to be allowed to buy lube.
Lucky for me, someone on the forum was actually helpful and said I should use a water-based lube alongside latex condoms which are the most common type of condom. He also said that if I have a steady boyfriend/girlfriend I could use lotion or oil-based lubricants as well. So I got up and found some baby lotion near his bed he sometimes used when his skin was dry (we lived in a dry place). "You know earlier this year I didn't give you a proper present, but with this, I think you'll be able to unwrap it a little easier." He lunged at me with the game still going in the background causing his character to die.
We made out hard, I could see he still had a lot of tension and needed some release immediately. Our mouths were pressed so hard against each other we were basically pinching our skin with our teeth as we kissed. We broke the kiss and started stripping immediately. I got down on all fours and put some lotion on my butt, crack, and used a finger to get a little in the hole. He took the bottle and squirted some on his dick. He entered me, but it was still painful. This was far less than before because I didn't feel any friction of his dick and my butthole, but now he was stretching me which was pretty painful. Wanting to make up for my failure earlier this year I played through the pain, he was moaning without worry since his parents were not home at the time. I was slowly crying, this hurt like a rapid-fire Indian burn, instead of moaning from pleasure like him, I was moaning in pain. A few moments later he came inside me, I moved forward to take him out and it felt very pleasurable to do so. It wasn't just that the pain was over, the head of his dick leaving me and tickling the side of my anus as his dick exited was very pleasurable.
He was out of breath and I recovered quickly since I didn't orgasm. "That was the best thing I ever felt in my life, it was as equally good as that time I fucked a girl in her vagina." I turned around to face him so we could kiss. After about 20 seconds we pulled apart and I looked down at his dick and saw a little poo on it.
"We should probably clean you up", I said. He looked down and saw it too.
"Yes, we should" and he grabbed some fresh clothes and I grabbed mine and we walked through the hallway naked to the bathroom. We set our clothes down and got into the shower. He turned on the shower and hopped in rising his dick off immediately. I hopped in after with him closer to the showerhead and we kissed with a quick peck on the lips. He soaped and washed his body and then we hugged and kissed. During this hug, we rotated so I was closer to the showerhead and then I washed my body even though I was going to bike home and get my clothes soaking wet from sweat, I just wanted the naked intimacy with my boyfriend. I then had an idea, I soaped up my front and his front and we rubbed our bodies together, it felt very pleasurable. "Wow, this feels really good", I moaned, "we should do this again before we cum."
"Yeah, being slippery makes it feel better", he moaned too.
"It's a shame you can't swim, you have a pool in the back. The few times we've been alone we never skinny-dipped", I said looking out the bathroom window at the pool.
"Well that's not the only problem, there are the neighbors so we could only do that at night and we've never been alone here after dark."
"It's always something", we rinsed off and I turned off the faucet. I got out first and opened the bathroom door slowly. "Okay nobody's here still", I toweled off. Brandon got soap in his eyes so he was drying out his eyes with the towel in his hands. While he did that I dried the rest of his body and we finished around the same time. We grabbed our clothes and walked naked back to his room. When his parents arrived, we put our clothes back on and played video games. At around midnight we fell asleep with me on the floor, him on his bed. I wished him luck with his exams and he did the same to me and we kissed, I grabbed my socks and we walked barefoot down the stairs and I put my socks on in the living room as usual.
We both passed our classes and now came the next chapter of our lives: the summer between sophomore and junior year. We had anal sex two more times once on his birthday during Junior year and his birthday during senior year. Our third and fourth times were slightly better than the second time, which again makes for a great orgasm but gets repetitive to read.
--End-- I hate to speculate now, but I imagine the next chapter will be an amalgamation of the rest of our high school years, let's just say it gets a little wilder from here. Not a lot, just a tad. I'm not talking 20-man orgies in the living room, public sex at school or BDSM or anything like that. But we were a little more adventurous from here on out.
Did I get you off? Let me know at bimartinez@yahoo.com and let me know where you are on the gay spectrum. 1-10 to make it simple, the Kinsey scale is not intuitive.
1 Very Straight 2-4 Mostly straight 5 True Bisexual 6-9 Mostly Gay 10 Very Gay