Sister-In-Law Lessons
Being a little brother isn’t so bad. Not when your big brother is cool. Mike was cool. He was my hero growing up. He was the prototypical all-American kid. We live in a small Midwestern down where football is king. And the king of our championship football team was Mike. He was the all-state quarterback and free safety of the our state championship fighting bulldogs and the entire town loved him. I mean everybody. He was also a straight ‘A’ student, captain of the baseball and basketball teams, captain of the chess club, and senior class president his last year. He worked closely with teachers and administrators for an "Overall School Success" program and they thought of him as highly as his coaches did. His classmates voted him ‘Most Handsome’ and ‘Most Popular’ and he was also a hit with all the girls in high school. He was 6'4" and weighed about 210 pounds, was good looking and was built like a Greek statue. Growing up I must have seen every girl in school come through our house at one time or another either openly visiting, or being snuck into his bedroom late at night when mom and dad were asleep. Being six years younger than him, I could only marvel at him like all the rest. When he graduated, he took an athletic scholarship to play football for a large state school not far off where he was very successful until he suffered a knee injury his senior year that ended his playing career.
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He never let it get him down, though I was crushed. He counted his blessings and let his academics take him to greater heights as a successful self-make businessman back at his hometown. I loved having him back home and visited every day.
I went to visit Mike, but also to pine over his wife. Darla was a girl he had actually dated in high school. She was the homecoming queen and voted ‘Most Beautiful’ the same year Mike won his award. They had graduated together and decided to attend the same college. I figured the relationship would end sometime during the first year, but Mike committed and they stayed together. They were married their last semester of college and they opened their business together after school. She was gorgeous, too. I though it might not last in college because Mike had dated so many girls in high school that I figured it would continue through college. He was kind of a swinger and liked to play the field. It was never because I thought she was sub-par for him. To the contrary, I thought she was the most beautiful girl I had ever seen and still do. She was tall and dark.
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She must have been close to 6' tall and had long dark hair with naturally dark facial features that didn’t even require make-up. To me, she closely resembled Lori Loughlin from the TV show "Full House. " She was nicely tanned and had a body that anyone would drool over. Her breasts were not huge, but big and firm, perfect matches on size and shape. And her ass was simple the best I’ve ever seen. She was athletically built but her ass was small and shapely with the perfect curves. She could really fill out a pair of jeans!
Now to me and the amazing story. My name is Trent. I unfortunately was not as blessed as my big brother. I played on all the sports teams, but my role on each was very average. I wouldn’t say I was bad at any of them but I was certainly not a team captain or the best player on the team as Mike had been when he played. I also didn’t do as well in school and was not involved with any organizations outside of athletics. I was not nearly as popular either, with classmates or with the girls. I am not a bad looking guy, but I was shy and a little awkward around girls. I am about 5'11" tall and not as muscular as my bother.
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I have a very average body, but I do have some of my brother’s looks so it’s not too bad. My biggest problem was sexually growing up. I loved to jack off and dreamed of my first time with a girl. I would even practice kissing with my hand and goofy shit like that. I must have jacked off at least once every day since I was about 12 years old, and most days a couple of times. But every time I tried to make a date with a girl, I was so nervous that most times I chickened out even before I could talk to them. I told myself there was plenty of time, but before I knew it, it was spring of my senior year and I had done nothing more than kiss a couple of girls.
A few weeks before my eighteenth birthday I went to visit my brother. He was at home alone on this particular night because Darla had to go out of town on business. My brother stayed home to man the office. We were just talking like normal until he started to ask about my year and the future. That is when I opened up about my frustrations. I told him about how I really felt like I was missing out because I was still a virgin.
"You know Mike. It’s kind of embarrassing.
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I am about to graduate and I haven’t had sex with a girl yet or even been to second base you know?"
"Don’t worry Trent, it will come. It’s not as big a deal as you think it is. Before you know it you will be married and have kids and wonder why you even spent as much time as you did worrying about it. " Mike said.
"That’s easy for you to say," I replied, "you had sex all the time in high school. You never had to even think about it. You could just say hello to a girl and her panties would fall off. "
He laughed, "It wasn’t quite that easy, but I guess I see your point. Really though, it’s not a big deal. "
"Whatever man. I think about it all the time, and I’m afraid if I’m too nervous now with the girls I’m around all the time, how can I possibly approach a stranger for a conversation. I just think if I could even have sex one time, it would kind of break the ice. " I said
He kept trying to reassure me that everything was fine and that I was certainly not the only seventeen year old virgin in the world. I still couldn’t see his point though, and I was kept venting as long as he would listen. I could tell he was starting to really become concerned with my preoccupation with all of this and he finally told me not to give it another thought.
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"I predict you will have sex before you graduate. I can almost guarantee it. " He said.
"How can you say that Mike?" I asked, wondering what he meant.
"Just trust me. Don’t give it another thought. Now lets go to the basement, I want to show you a project I have been working on for the business. " He said.
I had already been taking with him about going to work for him after college so my mind quickly found interest in the project and I forgot about girls for a while.
The weeks before my birthday flew by as Christmas holiday approached. I was beginning to feel even more pressure and depression over my problem. Now college was close too and I was nervous about that. Everything seemed to be mounting. Then the Saturday before my birthday, five days away on the next Thursday, we were all having dinner at my parents house. Me, mom, dad, Mike and Darla were sitting around the table after our meal talking and Mike announced that he had a surprise for me.
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Mom and dad already knew it was coming by the smiles on their faces as Mike said he was taking me to his college alma mater’s last football game. They were playing for the conference championship and it was a much anticipated game. I was thrilled and jumped up with happiness. Everyone laughed as I went over and hugged Mike.
"Your welcome little brother, you don’t have to choke me!" He said, smiling.
"This is the best, man! I can’t thank you enough! It’s going to be one hell of a game!" I said.
Mom told me to watch my language and then laughed out loud as did everyone else. They were as happy to see me so happy. I guess I had been pretty gloomy the last few weeks and they could see it.
"You and me at the championship game! It’s going to be great!" I said.
"Yes! Well, you, me and Darla. She wants to go too. I hope you don’t mind. " He replied.
I paused and looked at Darla’s lovely face smiling at me and finally said, "Heck no! Of course not!"
I could hardly contain my excitement that whole next week.
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We were going to leave on Thursday, my birthday, skip school Friday and head out for the three hour drive to the college. We were going to stay the night and then go to the game which was actually being played on Friday night because of the TV schedules. That Thursday afternoon, I had everything packed early and was waiting for them to pick me up. It was my birthday so mom and dad gave me a cake and some nice gifts before Mike and Darla arrived to celebrate it. Then Mike and Darla arrived and I jokingly asked them what they got me for my birthday, knowing the tickets and the trip to the game were the gift. Mike did say however, that he had another gift for me that he would give me that night but I couldn’t ask for it until we got to the hotel. I agreed and we said our goodbye’s to mom and dad and left.
The drive was pleasant and comfortable. We talked about all kinds of things, but mostly about the business and what my role might be after I joined their team. This was exiting for me because I knew it would be a job I would love not only for the work, but because I would get to be around Mike too. He was my brother and my best friend. We arrived at the hotel and dropped off our bags before going to a restaurant for dinner. Mike told me not to order too much because I wouldn’t want to get too full. I asked why but all he would say was, "You’ll see. " I figured it was a cake or something they had pre-ordered for after the meal, but when we went to leave without any surprises or cakes, I was a little stumped, but payed it no mind.
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When we got back to the hotel, things started to happen almost immediately that led to the greatest night of my young life.
We had put our things all in one room, but I figured there was another room down the hall somewhere for me.
"I think I will take my things to my room and freshen up a little bit. Is it down this hall?" I asked.
"Actually it’s this room. We are all in this room. " He said.
I gave him a puzzling look, but he only smiled. The hotel room was a nice room with a bar and living area separate from a bedroom area, but the couch was not a foldout bed type couch. I guessed that he wanted me to sleep on the couch so I played it off.
"Oh, ok. I just figured you two would want more privacy. " [and me too] I thought to myself.
Mike was no problem, but Darla was. She was my sister-in-law and we were friends, but I hadn’t ever seen her in night clothes or anything like that before.
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I was a little uncomfortable about it but decided she would probably be discreet and I would never know the difference. I was settling into the couch when the strangeness began. Mike excused himself to the bathroom and almost immediately, Darla came over very close to me and sat down beside me on the couch. Even though the couch had plenty of room, she sat so close our hips were actually touching. I was a little uncomfortable but didn’t want to make a big deal out of it so I said nothing. She grabbed the remote off the table and hit the menu button.
"Let’s see what they have to rent. " She said. "I hope they have a good selection. "
She then went to the adult movie section and began to scan the selections. I was dumbfounded as I began to think how weird this all was. Then she said, "Ah, there’s a promising one. That might be the perfect one actually. " and hit the enter button to rent it. The title was called "Virgin’s First Time" and the first scene was a shy boy being kissed and seduced by an older woman.
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I couldn’t believe what was happening! Darla was actually watching a porno in front of me and was beginning to run her fingers underneath the top of her sundress across her breasts! She seemed to be getting really turned on! Now the woman on the screen was sucking the boy’s cock and I was about to excuse myself from this embarrassing situation. About that time I heard the toilet flush and froze as Mike came out. I figured he would be as shocked as I was but he only glanced at the TV and then back at us with a smile.
"Starting without me, I see. " He said to Darla. "I guess you are even more willing than you had let on. " I was shocked.
"Well Trent, I guess it’s time for your birthday present. " He said. "What do you think of it?"
"Where is it?" I asked nervously.
"Why it’s right beside you. " He replied.
I actually looked on the table beside me before it dawned on me that he was talking about my other side. The only thing on that side was Darla. And when I looked over at her, she was smiling and removed the straps of her sun dress over she shoulders and lowered it to her waist so that her beautiful breasts were exposed.
Her tits were so firm that I hadn’t even realized she wasn’t wearing a bra. I could then see that they were bigger than I had ever noticed and figured she must have had a boob job sometime recently and that is why they were bigger and so firm. I quickly jumped up and went across the room as Mike sat down next to Darla’s other side.
"What’s going on!?" I asked.
"Well, I hope you won’t mind but your problem we talked about a few weeks ago seemed to be really upsetting to you. I thought about what you said and how desperate you sounded, no offense, and I asked Darla to do you this favor. We are very free and adventurous with sex and she said yes right away. Didn’t you dear?" He said looking at Darla.
"That’s right Trent. To tell you the truth, I’ve wanted to have sex with you for a couple of years now. It would have probably happened eventually anyway, but when Mike told me I was thrilled that it was going to be now. And more thrilled that I would have the privilege to be your first. " Darla said.
"You want to have sex with me? No kidding? Your not just saying that?" I asked Darla.
Instead of answering, she smiled and stood up.
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She then pushed her sun dress all the way down to her ankles and rose revealing her completely naked, amazing body to me. She had a dark runway strip of pubic hair above her clit and had no tan lines on her perfect body. She then stepped out of the dress, still wearing a pair of sexy, red high-heels and began to walk toward me. Her athletic body moved amazingly. He stomach was perfectly flat and firm and her tits were mind-boggling. Her seductive smirk was enough to make my cock hard as she stop in front of me, put her warm hands on the sides of my head and came in for a long, slow, open-mouthed kiss. We rolled our tongues against each others for what seemed like forever, before she broke our kiss, reached for the bottom of my shirt and slowly lifted it off over my head and kissing my chest. She slowly kissed her way to each of my nipples before sucking each a little and dropping to her knees. She then looked up at me before delivering little kissed all over my stomach and unzipping my jeans. With a skillful move, she quickly unbuttoned the jeans and pulled them and my underwear to my knees. My hard cock bounced high, smacking my stomach before aiming awkwardly toward Darla’s full lips. Darla is a sweetheart and knew just what to say to help me in my situation. She knew.
"Trent, I know this is your first time and I know what is probably about to happen so don’t feel embarrassed at all. Mike and any other man was no different their first time.
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Just let it happen and enjoy it. I am going to finally find out if my brother-in-law tastes as good as my husband. "
She then took hold of my cock and moved her lips over it’s head and deep into her mouth. I was in ecstacy. I decided to heed her words and let it go. In only a few seconds and a few strokes of her lips, I was dumping what seemed like a quart of cum into my lovely sister-in-law’s mouth. She never paused as she continued her lustful sucks to the last drop before finally removing her mouth with tight-closed lips and looking up at me as she swallowed. She closed her eyes tightly as I saw her throat swallow it all down and then she opened her mouth to show me it was gone before laughing.
"My God!" She exclaimed laughingly. "That’s more than I’ve ever had at once before! You certainly cum more than Mike ever has!"
"Yeah, yeah," said Mike, "you really know how to hurt a guy you know?" He laughed.
"So how was it?" I asked, still coming down from my orgasm. I was embarrassed by the question as soon as I asked it. I couldn’t believe I said it. But Darla showed no hesitation.
"You know, it’s probably a little better than Mike’s.
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" and then turned to him with a laugh. Mike just nodded with a smile and said, "Oh, that’s just great. "
"I’m sorry honey," she said to Mike and then turned to me. "Trent, do you mind if I give Mike a little attention before we continue. It will give you a chance to recover a little. "
I only nodded with a stupid looking smile I’m sure, and she said "good. "
I stripped the rest of my cloths off as I watched Darla take Mike to the bed and they began to work together to get his clothes off. Afterwards, he laid on the bed and she began to stroke and suck his cock. I couldn’t really see it, but I could tell by her movements that’s what she was doing. I however, had my eyes glued on her beautiful ass and her perfect pussy. I watched as she moved her hips how it opened and closed and how wonderful it looked and I began to stoke my cock a little. That’s when I noticed she had stopped her motion and was looking back at me.
"Why don’t you take a closer look while I suck your brother’s cock? I love to have my pussy eaten if you would like. " She said. Mike gave me a thumb’s up and a smile, unbeknown to her.
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That was all I needed as she went back to work and I walked up and hit my knees behind her. It was the first pussy I had ever seen except in magazines and I felt an instinct to sniff it and to taste it. I wanted to take it in all my senses. First though, I wanted to inspect it and learn a little. I began by running my fingers up and down her already dripping hole and then tasting a little from my fingers. It tasted good to me so I began to finger her hole, first with one finger and then with two. I could hear her begin to moan as I increased my speed. I also was interested in the cute, tight little pucker that was her anus. I stuck my tongue to it and she gave a gasp and withdrew a little. I was nervous a few moments as I froze my movements hoping I hadn’t gone too far. Finally I heard her speak.
"Oh my, I’m sorry Trent. I didn’t mean to flinch. It’s just that no one has ever done that, not even Mike. Go ahead if you want to though, I think I might like it.
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"
So I tried it again and she still gasped a little but didn’t withdraw.
I could tell she liked it. I also liked the idea that this was one place that until now was virgin to sex. Knowing I was her first, at least at this, was quite a turn on for me and I began to hope that maybe mine could be the very first cock to invade her ass. For now though I licked and the faster and harder I did, the more she began to moan. I took turns licking her ass and then her pussy, trying every now and then to push my tongue inside of each. It took some work on her ass to get her to loosen up, but after a while I had my tongue in her ass and was banging her hard with my fingers. Then I would switch. I would dig my tongue into her pussy as far as it would go and I began to finger bang her ass with my middle finger. She began to loosen up even more as her moans were turning into occasional screams. And then into uncontrollable screams as I concentrated on her clit as I fingered her asshole. It was then that she started to scream her loudest and she came. It scared me at first because it was so loud, but mostly because she squirted her cum hard out onto my chin and down my chest. I backed away to see another spirt come out and splatter on the floor. Then she turned to look at me and I could see the intense look of ecstacy and lust on her moaning face, as well as a large load of Mike’s cum as he must have shot his load all over her.
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"Oh God Trent that was so good! Please fuck my pussy with your cock now!" She moaned.
I quickly got up and wiped away some of her cum from my mouth as I pushed my hard cock into her pussy. With all the lubrication, it slid in easily and was warm and velvety soft. I loved it as I began to pump her hard, grabbing her by the hips. I could hear her sucking sloppily at Mike’s cock again getting him hard and ready. I was able to control myself better this time and after a few minutes decided to try my wish. I began to spit on her asshole and spearing it around with my thumb. She never did anything to stop me so I took my cock out of her pussy and pushed it’s head into the pucker of her ass. She responded by pushing back and I knew it was coming true. My head finally popped inside her ass as I pushed harder and got the head all the way in. She gave another gasp but didn’t relent as I continued my thrusts. After a few seconds my cock was about half way inside her and she was still pushing back, only paused briefly a couple of time when it seemed to hurt. She was quick to recover though, and before long I was completely inside her and beginning my gentle thrusts. She was so fucking tight I though she might squeeze my dick in two, especially when she would tighten up, but overall it felt extremely good. It wasn’t too long before I could feel another orgasm coming.
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She could sense it too because of my breathing and moans. Suddenly she stopped and told me to come around the side of the bed to her. Mike quickly got up and replaced me at her ass, sticking his dick in and continuing where I had left off. To my surprise, without even wiping it off, she immediately grabbed my cock and stuffed it into her mouth! I couldn’t believe it, but she began to suck my dick that only seconds before had been up her ass! I have to admit she sucked it even better than before, with much more gusto if you will. And she was teasing me a little too. Every time I would be about to blow, she would take me out of her mouth and squeeze my cock hard to keep me from cumming. "Not yet, baby. " She would say and then continue her moans from Mike fucking her ass while holding her grip on my cock. It was more than I could take so I just started to back away.
It was then that she pulled away from Mike and sat up in the bed. She pointed at me and began giving instructions.
"You two fucking studs are going to fill me up now! Trent, come lay on your back on the bed. " She demanded. I quickly did as told. She then straddled me and sat her pussy onto my cock to the hilt and bent over me as I took one of her tits into my mouth.
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"Now Mike, you stick your cock back into my ass and you two can both fuck me. I want it all. " She stated.
I could feel Mike move onto the bed behind Darla and could tell his cock was fully inside her when I felt his balls hit mine. Darla then began to buck as we found a rhythm. It was amazing. Her me and my brother were both fucking Darla at the same time! It was incredible as she moaned loudly while I took turns sucking each of her tits. Then she pulled my head down onto the bed forcefully and kissed me hard, driving her tongue into my mouth. She was being a total slut and I loved it. She was nothing like the sweet little girl that always came to my parents house to visit or who served me and Mike iced tea when I went to their house. She was like a pornstar in a gangbang and it was hot. After a few minutes, she told us to stop as she rose up, spun around and lowered herself back onto my cock, only this time my cock was in her tight little ass. She laid back onto my chest as I reached around and grabbed her tits in each hand. Mike then plunged his cock into her pussy and I could feel his balls slamming against mine again. We were fucking her even harder now as she sat up a little, placing her hands on either side of me and began to buck at our cocks as hard as she could.
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It was sexy having her long silky hair dancing in my face as she fucked my cock with her ass and Mike’s cock with her pussy. It couldn’t last forever I knew as I could feel my balls tightening for an orgasm once again. Mike was about ready to pop also as he pulled out of her pussy and helped her raise up. Her ass made a loud pop as she pulled off my throbbing cock. She quickly moved to the floor on her knees and gave a finger for us to come join her. Mike and I quickly went and stood on either side of her as she took a cock in each hand and began to jerk and suck each one at a time. Then she concentrated on me. She continued to stoke me with one hand while my cock head was in her mouth as she took her other hand off Mike’s cock and began to message my balls with it. Then just before I came, she took the hand that was massaging my balls and reached underneath to my ass. She pushed hard until her finger was up my ass and this only intensified my orgasm as I came hard into her mouth. She held it as she had before until I was completely dry and then backed away. She opened her lovely mouth to show my load sitting inside while pointing at it and looking at Mike. He knew what she wanted as he jerked his cock and carefully aimed it at her mouth. She still had her finger up my ass when she took her other hand and did the same to Mike. I could tell he was a little shocked as he began to shoot a huge load into her already full mouth.
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He missed only slightly as a little hit her cheek and nose. Her mouth was almost overflowing when Mike finished as she paused a moment to show us and then closed her eyes and mouth at the same time to swallow. A little cum flowed out the corner of her mouth as she close it and it took her three swallows to get it all down! She then opened it and showed us it was empty before putting her hand over her mouth and laughing.
"You two guys got me so hot! What I slut I am tonight!" She said laughing.
"You did great darling. " Mike said smiling. "I just can’t believe you let us fuck you in the ass. You told me that would never happen. And what was with putting your fingers in OUR asses before we came! I have to admit it felt great. "
"Well, blame your little brother. I’m not so sure he was a virgin the way he was working back there. I’ve never cum that hard before in my life! I guess he got me a little ass-happy. " She laughed again. "I hope this isn’t a one time thing. I could get used to fucking the both of you.
"
"Well, that’s up to Trent," Mike said, "if he’s game, you know I am. "
I couldn’t believe it! And my only answer was to put my still hard cock into her mouth and say, "Anytime. "
The game the next night was great and the good guys won, but it was not as great as the endless sex we had in the hotel room until it was time to go home. Mike and I must have cum 18 times each, and Darla drank most of them. When we weren’t cumming all over he tits or face or any other part of her amazing body you could imagine. Her pussy and ass were gaping open by the time we finished our last session of the weekend and her jaw had to be sore. She was like a champion slut or something! She still couldn’t get enough though, and I remember after Mike went to bed that she was still tiredly sucking on my limp and spend cock even as I was falling asleep watching TV. I guess she wanted just one more drink of cum before the night was over. I gave her what I could before completely passing out. It wasn’t more than a small spirt, but she drank it down like it was the last drop on Earth. After that weekend, we got together for a threesome almost every night. And sometimes when Mike was gone, just me and Darla would fuck and it could get freaky. Now I especially can’t wait to go to work for them. I have a feeling there will be some extra duties involved and will definitely be perks of the job. Darla has become a regular cum ogre now and is constantly wanting sex.
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Mike said the other day that mom and dad had been having some problems in the bedroom department lately and that Darla had offered to help them out. But that is another story.
.
