Josh, Greta, Ted and Carla

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My Girlfriend Gets my Little Brother Ready for College.
15.2k words
4.62
37.5k
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Part 1 of the 3 part series

Updated 06/10/2023
Created 12/12/2020
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inafantasy
inafantasy
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A totally fictional story about a brother trying to get his shy little brother ready for college and all the coeds he will encounter there. All fictional characters are over 18. Self edited and proofed with software, so there may be some things I did not catch. Comments on story are always welcome.

It is difficult bonding with a brother almost 10 years younger than you, when you do not have the same interest. I am outgoing, an athlete, and he is not quite a nerd, but he is smart, and introverted, and that will get him labeled as one. He is athletic, it is just not in his interest to be involved in group sports. He likes Sci-Fi, video games, and sport car racing on TV.

I have taken him to some races, at a local road course. I even went once on an open day, and let him take my Porsche around the track, he was timid with it, I am sure I would be too if it was his car. I think it was as close as we got to each other.

Ted, no longer Teddy as he is 18, and is heading off to college this fall, and I worried that he was not very good with the ladies. I knew he liked them, he likes my live-in girlfriend, and lets it show. I wanted to find a way to give him advice about not being so afraid to pursue girls. I told him the pretty ones like Greta, my girl, tend to get ask out less. Guys are intimidated by women that are too beautiful, they just think they are out of their league, and pass them up. I did not get much of a reaction, we were both feeling awkward I think. I remembered how I felt in my teens about that kind of advice, and stopped the conversation.

He had a job for the summer, but it was seasonal work, and he ended up with a few weeks left before he had to start school. I checked with Greta, and she was fine with him spending a week or two with us. I wanted to get him out of the house, away from my parents. We have a pool he can spend some time in, we are both professionals, and live a lot better than our parents. I thought it might give him a reason to set bigger goals for himself, he is smart enough to be a physician if he wanted to. Investment banking is my field, it has been good to me. Greta is a attorney, and specializes in divorce law. I am not sure we will ever tie the knot, she has seen too many ugly splits, mostly from infidelity. This has even caused us to live more like roommates, close ones, with benefits. We still date, mostly just hook-up others, but only on occasion, it's more of a time constraint thing.

Ted came over on a Friday, I thought it would be better to start on a weekend, as Greta and I both try to keep them clear. When you have jobs that are intense, you need your weekends.

I saw his pre-owned Camaro muscle car, in the drive when I got home, and remembered I gave him the codes to the alarms, and locks, I don't want him to think he is being babysat. I also had seen Greta's BMW in behind his, she must have had an early day. I was glad her car was behind his. She has a habit of shedding her clothes as soon as she gets home, sometimes just grabs a beverage, heads to the pool to swim or sunbathe that way. She would just love being caught that way, she is a closet exibitionest, but my little brother would likely freak. We were drinking one night and she talked me into role playing, I had to be the pool boy catching her, and doing some freaky things with her.

My brother and girlfriend are fond of each other, but I think it is more of a brother sister love they have. Although I have caught them both checking each other out.

Greta, my girlfriend/roommate, met our freshman year, but were not a couple, until after graduation, and have been living together for just over 7 years in most states we would be considered married by common law. Despite having an open relationship, we don't exercise that right often. Occasional sex with someone else just seems to add fire to our relationship to keep it fresh. We have no hard rules laid out for our relationship, but found it is better to share our sexual exploits, secrets can cause problems, sharing the details often led to great sex for us.

Greta got her Scandinavian first name from being the first generation of her family line born here. She is a pure Scandi, by that I mean both her mother and father are blond blue-eyed handsome people. They say to look at a woman's mom to see what to expect as they get older. Her mom is still ravishing in her late 40s, she gave me a boner when I had first seen her in her two piece at our pool, she could have pulled off a modest bikini easily.

Greta, is not only beautiful, she has one of the most perfect bodies I had ever encountered. She is 5 ft 4 and very fit, despite her busy life as an attorney, she gets to the gym more than I. I can't tell you what size her breast are, or what cup, I don't buy her bras. I can tell you they are perfect in proportion to her build, she has a tiny waist, I can almost wrap my hands around, and I am not an exceptionally big guy, at 6ft. She is tiny to me, but has a big personality, and takes no shit from anyone. Those blue eyes of hers turn to fire if you piss her off enough. She keeps her blond hair, shoulder-length, and natural of course.

Naked, Greta just melts me, flawless, no tattoos. I am not fond of them on either sex, she does have a couple of piercings that really accentuates her beauty. I can't get enough of her pussy, it is well-defined, and her clit is not hard to find when she is excited, it's my favorite low cal snack! My brother has never spent any time alone with her because of her schedule, and his schooling. I am anxious to see how they get along being in the same house for a week or two. I think she will be kind, and patient with him, teens can be annoying.

I went in the house, it was quiet except for pool noises coming from the back of the house, walked around, and looked out the sliding doors. I backed up, so I could just observe. Greta was laying out with one of her briefest bikinis on. Ted was in the pool, but as I watched I could tell he was taking in the view. He climbed out of the pool, and I watched him check, and then rearrange things in his trunks. Something I had done many times around hot girls at his age, still do on occasion. I got my trunks on, and joined them for a swim. We shot some hoops, he discovered the movement in Greta's breast as she took a shot, and I could see he was now focused on it. He had another bulge to deal with as he left the pool the next time, it looked quite large, but his trunks were kind of tight.

We had a nice evening, and I slept in the next morning. When I awoke, I saw that Greta was already up, she is an early riser. She is used to getting up early for court, Judges like an early start, so they can get a round of golf in later in the day. I headed down to the kitchen to see her and Ted there, I stopped before I entered, stood next to the wall in the hall to observe. I know Greta is an exibitionist, so I expected her to show at least some of herself, she has done it before to some of my friends.

Greta was busy cooking some pancakes, and frying some bacon. She had one of my tee shirts on, and Ted's eyes were focused on her bare butt cheeks when she leaned over. For a minute I thought she was pantie-less, but she is a thong wearer. I don't know how girls can wear those, they look uncomfortable as hell. I wondered if her clothing of choice was deliberate, it was a hot show for both me, and my brother. I have ended up fucking her in the kitchen when she was horny, and wore the same thing without panties.

I joined them, and could tell she was aware of his attention, and playing to it. We finished our breakfast, and Greta was picking up the plates. I was proud of Ted for telling her what a great breakfast it was, we were raised that way, but his shyness often rules. Greta responded with, "your so sweet," and kissed him on his forehead.

Just that peck, turned him red, and he was again adjusting things in his workout shorts as he got up, I just loved the whole scene. I got up after he left the room, and cornered her at the counter, lifted my shirt, that she had on, and gave her a kiss on both nipples. Then I told her how good breakfast was, and how hot the chef that prepared it is, and that it gave both me and Ted hardons, and turned him red.

Greta, chuckled, and said, "yes, I saw that I have that effect on him, I noticed it happened in the pool yesterday, he had to push it between his legs as he got out. I really think that brother of yours is hung, you were left out I guess, the gene pool can be partial some times."

I had an answer for that, "well come with me to the bedroom, and I will give you another look at mine, you must have seen it without your contacts in."

We walked by the guest bedroom as we went to ours, the door was closed, I figured my brother was probably busy with himself.

I could not wait to get busy with Greta, watching all that interaction with my brother, and girlfriend had me hard. I felt a little bad, that I had a real girl, and he was probably jerking off from his memory of Greta's ass, or some porn. We did not have a long session, mostly just fucked, I mean I had to eat her pussy too. I can't look at her naked without wanting my face in it. No need for fluffing, I just went from using my tongue to my cock on her, and finished her off, and came on her belly. I figured we would probably get to have a good session that night but wanted to spend some time with Ted.

We had a nice shower together, and were getting dressed. I ask her if she was aware of what she was doing to him, and if it was deliberate?

"Yes, and kinda, he is a nice, good-looking young man, and has little experience, and is a virgin. I can tell because I seduced his shy brother, and he is reacting the same way to my flirting. I guess the thrill of showing some skin to someone new it hard to resist, and being able to turn on a guy 10 years younger has made it become more deliberate."

I responded, "I would like him to get some confidence with women before he goes off to school. I don't want him to be as shy as I was."

Greta, "well I can turn up the heat, I would love to show him more, but if I am successful, what do you expect from me? I want to at least see it angry, would you be upset if I gave him a pity blow job?"

"I would be thankful to you for taking his blow job virginity, if he is one in that area too, maybe even all of his virginity if you want. He would not be the first younger guy you have flashed, and eventually fucked since we have been together. I think however, if you want to really help him, and not just fuck a young guy you think is hung, try to get him to make the first move. I want him to feel like he seduced you, and you are the one that gave in because of his suave moves. That would give him confidence."

Greta, "Like I did with you, and you almost immediately used that confidence on some of my girlfriends, and ended up fucking them too?"

See that's an example of why we should not get married, the thought of you bringing that up at every possible chance for the next 50 years. I just wanted to make sure I had the best one I keep telling you!

"Well it is not like you got it out of your system, I went away for a legal conference for three days, and you fucked my paralegal, that was hitting close to home."

"Yes, I have had more success than you lately, but it sure made for good phone sex with you that night. It was your idea to send her over here with some papers you probably did not even need, you were out of town. Telling her she could use the pool, if it was OK with me. Of course, it was OK, she is a babe, that likes to drink in the afternoon, and still manage to give a good blow job, and fuck."

"Well, I owe you one, are you prepared to hear about me having sex with your little brother if he gives in?"

"Not sure about being prepared, I was worried you would find him annoying, now you want to fuck him. It is hot to think about though, you dirty little Cougar. Just a thought, you might want to expedite a flash of those wonderful breast of yours, I know you want too, he has seen most of your ass, he needs to know what you are hiding under your tops. If your nipples were hard when you do, that would be even better."

"Tit flash, is pretty easy, but with hard nipples, that's a challenge. I will try to come up with a way to do it while you are around, so he sees you don't have a jealous reaction. Not to mention that you will enjoy seeing what his is."

We had no plans for the day, other than to maybe enjoy the pool, and hot tub. Have a light lunch, and then I was going to take him out to a nice restaurant, somewhere he has never been. We had decided to convene at the pool around 11, and did. I jumped off the side, Greta and Ted, went for the diving board. I knew he liked to swim, took swimming and diving lessons, and is qualified to lifeguard. He never went as far as trying out for the swim team, or try to lifeguard. It would have been better than the summer job he had, his shyness I guess might have been what kept him from group sports.

Ted made just a beautiful dive, and Greta followed him with I just have to say was, a quite pitiful one. She challenged him to a dive off, with me as the judge. I had a feeling she had motives, I thought she might just want him to feel good about what he could do so well. Greta is not a good swimmer or diver, and rarely dives other than when getting into the pool.

They made a couple of dives, and I put my fingers up to give them a number rating, just like they do in competition, and I was honest. The next dive, was beautiful, Ted is quite a diver, he was having fun, more relaxed around Greta in her bikini by then. He made a beautiful dive, for me a layman when it comes to diving, it was perfect, and I gave him a 9. He waited to see Greta's, not for her dive I am sure, but to watch her breast bounce as she did. She stood there, and waited for his attention, and then dove.

I am not sure how she did it, I was not looking that close. But when she came up from her worst dive so far, she was topless, and trying to act like she did not know she was, and was just standing there, tits out. She had to make the view even hotter, so she lifted her arms up, elbows forward, to slowly push back her wet hair, making sure her breast, and not to mention hard nipples from the pool water stood out. Ted did not know what to do, but he did not look away until he checked them out. I paused before I announced her score, then I jumped up, and made a loud whistle, and put up both hands for a perfect 10, and I added, nice tits. Ted did not contest my decision, and just took it all in.

Greta pretended to be surprised hearing the nice tits, and looked down to pretend to check her breast, and unlike what a lot of girls do, she did not try putting an arm up, and hiding them from him. Her top was right there in the water, in front of her within her range of vision, but she pretended to not be able to find it. She claimed she did not have her contacts in. Ted could see it, I could see it, so he went over to her to fish it out of the water as it sank. She did not take it from him as he tried to hand it to her, and just put it on, nor did she ask for his help to tie it. No, not my girl, she just stood there next to Ted, tits out, her nipples hard from the pool water, like I suggested. She pulled him down by one of his arms, to give him another peck on the cheek to thank him for getting it. She managed to rub a nipple against him in the process. Then she stood right in front of him, as he tried to hand it to her again, and ask him to help her with it, then she slowly turned around. He was just standing there with a topless girl expecting him to put her top on. I could tell she was more than happy to show him, more than the flash I suggested.

I hoped he had a clue, surely he had been to first base a few times, but likely he never put a girl's bra back on, I don't remember ever getting that request. Her top was like a bra, only much smaller. I could see him fumble with it, as he put his arms around her trying not to press his body to hers, to help her, she could have helped guide it in place, but did not, he was on his own. I had a front view, he could not help but to feel her up trying to center it before tying the back. She had winked at me as she pushed back her ass to press against his trunks, she later told me she was sure he is hung now. He was embarrassed, clearly hard, but he handled it well.

It was about 1 pm, so we had sandwiches for lunch, Greta brought them out to the pool with some ice tea.

Greta was not done for the day, that accidental titty exposure was not enough for her. It just made her want to go for more, she won't be happy till she is naked for him. She whispered in my ear, "watch this" when we moved from the little table back to our loungers. Greta, took her lounger right between me and Ted, and before she laid back said, "well Ted, since you already got a pretty good look, and feel of my breast, because of my poor tying skills, and bad technique in my diving. I hope you don't mind if I leave my top off a while, and sun them a little in front of you. I noticed my tan lines are coming back when it fell off. She reached around, and undid it, and took it off and said, "well, Josh since you know your way around them so well, how about making sure they are covered with oil. If your busy, your little brother has a softer touch, it turned me on, having such a strong young man helping me put it on.

Now he was red-faced as she joked about his soft touch, and him getting her aroused as he felt up her tits while putting her top on. When I started to oil them up, he was watching. I tried to make it look hot, in fact I gave myself a boner.

We left for the restaurant about dusk, and Greta gave up the passenger seat, we took the Porsche, and there is not a lot of room in the back. It was Greta's idea of course, she was really taking this seduction thing seriously. She had a cute, short, and low cut, black dress on, and sexy pink thong, with flowers on the skimpy cloth part that barely covered her labia. I could see in my rearview mirror that the way she was sitting, with her hemline pushed up, putting all of her beautiful tanned legs, and thong on display. She spotted me looking, and mouthed "watch this", I can read her lips pretty good after 6 years together. I wondered how she was going to give him a look, unless it was later when she asked him to help her out, but he did not have to wait.

She asked him to hand her a Kleenex, so he had to turn around to hand it to her. I watched it all go down in the mirror, she made sure her legs were spread enough to give him a good look. He turned back, and she leaned forward to get it, her top hung down then, exposing both her thong, and her breast, he turned quickly thinking it was accidental.

Sunday morning, was almost a repeat of Saturday, except we both woke up about the same time. I went into the bathroom to pee, and there was Greta, sitting on the toilet, sitting back giving her pussy, a touch up shave. I told her to hurry, or I would go in the sink.

She barked, "and risk nicking myself in such a sensitive place, no, you go to the guest bath, or just go in the shower, it is less gross there, you can just rinse it down with the hand held."

I ask her, "I hope you don't plan on debuting that fine shaved pussy at breakfast it might be too much too soon?"

"Don't worry, I know what I am doing, if it shows it will just be a little flash first."

I went back, and laid down, and she came out naked, and I was treated to her naked ass, and pussy, she is just ravishing. If she ever shows him everything at once, she will likely have him, the animal in him will just have to kick in, and his little brain will take charge. She was rummaging through my tee's, she was comparing them to see how short they were. She would put one on, and turn, then lift her arms, turn around, and say "how's that one?"

inafantasy
inafantasy
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