Turning Boys Into Men

When I went off to college, my brother was in middle school and now that I'm 22, he is soon to go off to college himself. I love my brother James with all my heart and he is the sweetest person. He is first to help someone in need and would give the shirt off his back if you were cold. I consider myself a sweet person and I get good grades but that is almost where our similarities end, especially our social habits.

In high school, I was very outgoing, played sports, dated, had boyfriends, went to parties, and thoroughly enjoyed the ride. James has always been introverted and extremely shy. He is into computers which is cool but literally has no social life. He has never had a girlfriend, hated sports, and stays home on the weekends. He has a few friends which just might be more socially inept than James if that were possible. Occasionally, they would hang out in our basement, playing video games and goofing around on their electronics. I consider myself a sheik nerd but my brother James and his friends were nerds by every definition of the word.

This past May, my parents were gone on a weekend trip while James and his friends, once again, occupied the basement. My college had already let out for the summer so I was home for a couple of weeks before I had to return to my condo for summer classes. I walked down the stairs to offer them something to drink and some cookies. They were all appreciative and just a great bunch of teens.

I was also doing laundry in the basement when I eavesdropped on their conversation. They talked about which girl at school was hot and which actress they wanted to marry among other things. I felt sorry for them because none of them, with the exception of James, were cute or probably even a girlfriend before. I felt sad that these guys were 18 years old and would go off to college as virgins, at least, that was my assumption.

Later that evening, I was getting ready for my date with Chad. We hadn't dated long and things were starting to heat up even though we hadn't slept together yet. I, myself, hadn't been laid in a month and I was horny, so I figured that it was the night I would give Chad some sex. Just as I finished getting ready, Chad calls and has to cancel because he had forgotten he promised his uncle to help him load something on his farm.

Needless to say, I was disappointed. Not to brag but I was looking good in my gray skirt, with a matching blouse, black, strappy, open toed, wedge heels and my dirty blond hair curled. I sat there watching television, contemplating if I should change back into some comfortable sweats or call one of my girlfriends. Three texts later, along with three rejections later, my home girls were all on dates or with boyfriends.

Thirty minutes had passed and I was bored stiff. I froze for a second in my own thoughts and gave myself a devilish grin with an idea. I was going to go down stairs and mess with my brother and his friends. I planned on teasing and flirting with them. "Brittni, you are an evil bitchy slut for even thinking of it, but what the heck, let's play," I thought to myself. I came clunking down the wooden steps in my heels and all the boys' heads turned my direction with the exception of James who had seen me dressed up many times.

"Can you believe that? My boyfriend Chad cancels on me and now this, I spill something all over myself. It has been a bad night," I pretended to be talking out loud to myself to get a reaction out of the guys.

I could hear sympathetic comments from them to "console" me. The washer and dryer are visible from the room they were sitting in, playing their games. I unzipped the back of my skirt and pulled it down, exposing my white, ruffled silk thong. I followed that act with lifting my shirt over my head exposing my matching bra. I could hear a big gulp from Trevor and out of the corner of my eye, I could see Justin tap his friend, who I can't remember his name so I will call him Mark, with his elbow. I thought again, "I'm so bad, but this is going to be so much fun."

I turned and stepped out into the room dressed like a Victoria's Secret runway model, wearing only my bra, panties and high heels before I cooed, "Whatcha doin guys? You havin fun? Do you guys think I look fat? I have been working out religiously and just don't know if it is helping."

Everyone's eyes were wide open and all the guys were speechless. James finally looked up from playing his video game and sneered, "What are you doing? Go get dressed. You are embarrassing us."

"Really?" I replied coyly. "Are you sure?" I walked over and sat on the couch between Trevor and Justin where my bare legs were touching theirs. "Boys, am I embarrassing you?" I asked in my phony innocent tone.

"Nah, I'm good," chuckled Mark.

"Not at all. It doesn't bother me," snickered Trevor.

"Uh, I...I...I think it is fine," stuttered Justin.

James gave in, "Fine. Whatever. Do whatever you want," before he went back to playing his video game.

When I looked side to side, both boys were fighting erections in their pants. I leaned forward off the couch to first let them check out the thong string riding up my crack and secondly, I shut off the PlayStation.

"Hey, what the heck Britt? You can see I was playing that," huffed James.

"I think it's time we all play another game. All you guys do is sit down here playing games. I think you guys need a change. We are going to play truth or dare and the rules are absolutely no lying whatsoever and the dares have to be something realistic in this room. It will be all you guys at the same time against me," I suggested.

The guys agreed as this provided a different excitement than they were used to. I went first, asked them which choice was their wish and 3 of the 4 responded with "truth." Since majority rules and adding a little of my own rules, I informed them that my question is a 4 part question.

I began my 4 part interrogation, "Ok boys, and remember you have to tell the truth like you are on the witness stand, how many of you have ever had sex, meaning sexual intercourse?" Zero hands went into the air. "Alright, question two, how many of you have every had any other type of sex like a blowjob, handjob, fingering a girl or even feel a boob?" Once again nobody raised their hand.

My third question was had anyone ever kissed a girl? Two hands went up and those were Mark and Trevor but each had only kissed one girl apiece. My final question was, as I reminded them, "Last question and don't be embarrassed because it's natural for boys your age, well any age for that matter," I chuckled, then asked, "How many of you guys have ever masturbated...you know... jacked yourself off?"

At first I think they were all embarrassed but after they looked around at each other, two hands went up and they were Trevor and Justin. To be honest, I thought all four hands would go up. That certainly explained James's wet dream stained underwear whenever I helped my mother do the laundry on weekends I came home.

When it was the guys' turn, I chose "dare" as my challenge. Mark did the talking when he smirked, expecting me to refuse, "We dare you to take off all your clothes."

I put my hands on the boys' crotches, confirming my suspicion of hard-ons, and used them as arm rests to stand up while I turned to face them, "Ok, let's see if you guys can handle it," I confidently replied as I unhooked my bra and let it fall to the floor. I slid my panties off and tossed them to Mark as if to validate my willingness.

All the boys' eyes were once again wide open, even my brother James. As I stood there wearing nothing except my shoes, I pushed my breast together and asked, "Do you guys like these?" I reached down and spread my pussy lips and asked, "How about this? I just shaved it before I got ready."

"Oh shit, I like it very much," snickered Justin while I all the other boys nodded their head in agreement.

I had a change of plans when I blurted out, "Alright, game over. I think it's time I teach you guys about sex. None of you have been laid and I would just feel horrible if you guys went off to college and had no clue, especially at your age. You guys are all smart guys and had health class which didn't teach you anything but the basics. I have had college level anatomy not to mention my own experiences, so I'm going to give you guys the 'hands on' version."

"Bub (That was James's nickname our family called him), get in the closet and bring out 4 of those folding chairs and sit them right here facing the couch. After that was finished and the chairs were lined up in a semi-circle, I ordered all the boys up and sitting on the chairs, while it was my turn to take a seat on the couch. Using my wedges as traction, I dug both heels into the cushion to spread my legs and prop them up so the guys could get a good view of my vagina. The only things missing were the stirrups and white lab coats as my position had a gynecological feel. Again, all the guys were showing laser focus on what I was showing them.

"Someone use their phone and shine a light right here on my pussy," I instructed. So now I'm pulling on my outer lips, spreading my inner lips, using two fingers to pull back the hood covering my clit, among other things as I'm teaching, "These lips are the labia and as you can see I have one that is slightly puffy and if you are with a girl who has that, we like it softly sucked on. As you can see inside, this is the inner vaginal walls with the G-spot, upward toward the abdomen. If you can massage that, you can give us girls a major orgasm and some girls, like me, can even squirt which is female ejaculation. If you are going to be good in bed, you have to learn this little guy right here. This is the clitoris or clit. It is sensitive and rubbing or vibrating it gives us a lot of pleasure."

Justin interrupted curiously like he was asking a question in class, "Can you have an orgasm with someone playing with it or do you have to have sex?"

I assured him with a smile, "Oh, we definitely can have orgasms by stimulating just the clit. There are basically two different types of orgasms we have and those are clitoral which we do about 80 percent of the time we masturbate or penetration orgasms we have during sex. Occasionally we get frisky and use dildos when we masturbate but mostly we got off with our vibrators or fingers right here on the love button."

"Learn it, love it, know it," I giggled. I added, "When we get really excited or horny, our pussy lips swell up and the clit pops out because of increased blood flow just like your hard-ons. If you make that happen, you have done your job as a lover."

I stuck my finger inside my pussy and I was wet. Just the situation with me being an exhibitionist, naked and spreading my legs for all the boys to see, was erotic. After wiggling it to gather juices, I showed the shiny digit to the guys before instructing the guys, one at a time, "Bub, you're first. Come over here and taste me. First I want you to smell my finger,"

James scrunched his eyes and cheeks indecisively, "I don't know. I feel kinda weird with you being my sister."

I quickly put his mind at ease, "Yes, it might be a little weird in the beginning but you are a teenage boy and I'm a girl, and this is just nature. You have hormones and needs just like us. Tonight, just think of me as a girl teaching you the necessities of sex."

James thought about it while the others waited for his response. He agreed and got on his knees in front of my spread legs. I calmly put my finger under his nose and slowly moved it so that he could successfully take in my pheromone fueled pussy scent.

"Open up," I requested as my brother shifted his eyes in uncertainty but followed my request. I stuck my wet finger in his mouth as he clamped his lips around it. I withdrew and pushed it back in a few times so he could savor my juices before I leaned back for my next request.

"I want you guys to take turns smelling it, then lick it," I directed while looking down at my pussy. "Bub, go first,"

He leaned in and took a short controlled sniff to my correction, "No, take a deep smell. Inhale it. Pretend you're an animal trying to get your mate's scent to prepare yourself to breed."

James did as I asked and not only did he take a huge sniff, he inhaled it several times. I could tell, he was enjoying it when I gently put my hand on the back of his head, and lowered his face to my pussy, "Go ahead and lick it. Taste it. Don't forget what we talked about and use your tongue to find the clit."

James, did as I asked. He was definitely inexperienced as he recklessly licked my lips and inside my hole. His mouth worked its way up to my love button and with my direction, he was starting to get the hang of it. I helped him by mashing his face deeper into my crotch. When I let him up, his face was glistening in my juices like he had just ate a fried chicken dinner.

He wanted assurance that he did it correctly when he asked, "Was that good?"

I affirmed his efforts and periodically did the same to each boy, even though I used a different finger each time, so that they would get their own private scent, I had them smell my finger, suck it, smell my pussy, and then lick it. It seemed as though as Mark spectated, he took mental notes because he was last and the best at eating my box. It was feeling really good and I thought, with my direction, I could squeeze out an orgasm in front of the guys.

I was specifically directing him while the others watched the back of Mark's head between my legs, "Slow down and lick on the outside of the lips...yes like that. Oh! (I cleared my throat), put your tongue in as far as you can...deeper...go in and out really fast...Aw...Aw...now suck the clit...yes...faster...faster...Oh...Oh," when my pussy started twitching in orgasm, I held his head still so that he couldn't stop until I had finished on his face.

It was time to switch gears when I told all the guys to stand up and take off their clothes. They were understandably hesitant and shy. My intentions were completely educational and I had no desire to ridicule or humiliate.

I lightly reassured them, "Guys, if you want to learn and have sex, it can't be done with your pants on."

They all reluctantly started removing their clothes. Shoes, socks, shirts and eventually pants and underwear were hitting the ground off to the side. I wanted all the guys to stand in a line so I could assess the situation. All four of them had hard-ons that could've cut glass. Each dick was sticking up proudly while each head was sparkling under the light with sticky precum.

Let me give a deeper description of each boy and their junk. Justin was about 5'6, chubby with a gap in his teeth. He wore his black hair with bangs. His cock was short as it looked about 5 inches but was the thickest among all the guys. Mark was one of these guys who, even though he was 18, looked like he was about 12 because he hadn't hit puberty yet. He was under-developed, about 5'3, brown hair, wore glasses with a thin 6 inch cock. Trevor was a 6'1, tall goofy looking redhead with freckles and a long neck. He was battling acne on his white, pasty skin. He had the longest cock among the boys at about 7 ½ inches with a slight curve. My brother James is 5'10, with light brown hair, light complected, with a thin 7 inch cock.

Using my middle finger, I rubbed the tip of Trevor's cock, eventually, with the aid of my thumb, pinching a large glob of precum to show the guys, "This is precum. It is a clear and sticky and nature's way of cleaning out the penis to allow a higher percentage of untainted sperm to be ejaculated." I then added as I sucked it off my fingers, "It also tastes good."

While on my knees, I scooted in front of each guy, before grabbing their cock, squeezing hard to milk out their precum and sucking it off the head. Each guy tasted about the same.

"Can you get pregnant from precum?" Trevor asked as I was now slurping the end of his manhood.

My mouth disengaged from his mushroom head with a pop when I responded, "Great question. The answer is no because it doesn't contain sperm but there could be some sperm left over from a previous ejaculation so even though it is highly unlikely, you still want to use precautions."

I knew if I had sex with these guys, they wouldn't last 3 minutes apiece. That is when I decided I was going to suck off each one of them before we had intercourse. At their age, they wouldn't have any problem getting immediately hard again and they would have a little more stamina as I reflected back to my high school boyfriends' abilities as my reference.

"Guys, before we get started, you're gonna need to get your dicks sucked on. We can use this as a learning experience as well, plus you will be able to last longer when we fuck," I, nonchalantly, told them.

Each guy had that surprised, excited look on their face as they glanced at each other. I thought it would be a good idea to start with the two guys who "claimed" they haven't even masturbated before. If that were true, the "pipes had to be way backed up" and needed cleaned out.

"Mark, you are going first. Sit here on the couch. The rest of you pull up a chair so you can watch and learn some things. I'm going to suck it without using my hands," I taught.

Mark spread his legs as he sat. While kneeling between them, I engulfed his leaking cock with my mouth and began to suck it. I bobbed my head up and down with no problem taking every inch. Mark's body began to shift on the couch and his thighs quaked.

"Oh! I can't hold......Ohhhh! Augghhh!" Mark yelled as he started spurting his thick cum into my mouth after only 6 or so bobs.

Even though I knew he would be quick, I had no idea it would be that quick! Catching me unprepared, his warm cum slightly gagged me before I was able to shake it off and allow him to finish without stopping. He finally stopped cumming and began gurgling in pleasure. When I raised my head, I had a mouth full of thick, nasty cum with the consistency of yogurt.

I closed my eyes and swallowed the bitter cum down while Mark kept apologizing for cumming so quickly, "I'm sorry. I couldn't help it. It felt so good. I...I...I am so sorry."

I held up my finger and calmed him down, "First of all, don't ever apologize for cumming quickly during a blowjob. That is great. We love that. As that one girl in Sex in the City said, 'They don't call it a job for nothing.' Now, if you cum too quickly during sex, that is a different story and we will get to that. The second thing I need to tell you, and all you guys listen up, when you're getting a blowjob and you're about to cum, it is common courtesy to let your partner know with some type of signal so not to catch her, or him if that is your preference, off guard and choke them. I can usually tell with non-verbal signals but it is nice to say, 'Hey, I'm about to cum,' or tap us on the head. It is just proper oral sex etiquette."

I continued, "Alright Bub, your turn. Instead of sitting, I want you to lay down flat on your back. Your cock is a little longer so I want everyone to see me deepthroat it."

I had James take his place on the couch lying flat on his back. With me on my knees beside it, I leaned in, turned my head sideways and rested my cheek on his belly. Using my hand, I guided his leaking cock to my lips. I licked around the rim just to give the other guys a visual. I quickly gobbled his prick until my lips were being tickled by his pubic hair. I sucked up and down, prepared for him not to last very long. While I sucked, I reached across his body, took hold of his hand and placed it on top of my head.

As I come up for air and holding his hand to my hair, I educated the boys, "See how I put James's hand on my head. When a girl is blowing you, don't forget you can guide her head, showing her what you like, almost like a gear shift. You can let her know if you want it faster, slower, deeper, or anything. We don't mind the guide and encouragement, just don't force our head down too far. The girl controls the depth." I then looked up to James, "Be sure to use my head and show them how to do it. One last thing, it is cool to be verbal and give your girl some feedback. We get more into it if we know you are enjoying it with a grunt or groan, or moan, or something like that."