I Am One Tricky & Lucky Bastard

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Brad develops a plan to have both his sister and girlfriend.
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imhapless
imhapless
3,576 Followers

While primarily a heterosexual story this offering does have some female-on-female sex. If that offends you, don't read on.

__________________

I'm Brad. I live in the "Bible Belt" in the US. Except for the last three paragraphs, the events related in this story took place about eighteen months ago, and the ages indicated are as of that time.

I'm twenty five years old. I have judgmental, surly parents and a twenty year old sister Emily. Neither Emily nor I ever got along with our parents. Emily and I are both tolerant and friendly. I had always hoped that we were adopted, but I'm afraid that we weren't – we just developed better personalities than our parents. We always were straightforward with each other growing up; we were very close because we had a common enemy in our parents.

Emily is a sophomore in the local college, on a partial scholarship; she's real smart. Until recently she had to rely on our parents for whatever financial support the college didn't provide.

Emily is one of the best looking women I have ever seen. She has long auburn hair, an endearing bulb at the end of her nose, perky almost conical average size tits, and a killer ass above long sleek thighs with sexy quads. Especially if she is wearing eye makeup, the gaze from her enormous steel blue eyes can pierce your skull, and turn your brain into mush.

Almost everyone – male or female – tries to hit on Emily, but she may be the most discriminating person I know when deciding who she has a relationship with. She shoots almost everyone down so kindly that they feel like thanking her – but they've crashed and burned nevertheless.

A few months ago Emily came out to our parents as a lesbian. Those assholes kicked her out of the house (it's hard to believe there are still people like that nowadays especially even when our ultra-right wing former Vice President's daughter came out and he publicly embraced her), but that shows you what jerks they are. Fortunately, Big Bro Brad had a great job and a two bedroom apartment, so I welcomed her to live with me so she wouldn't have to quit school, and she readily accepted.

Since I hadn't lived with Emily on a daily basis for several years, I wasn't prepared for the non-brotherly feelings she would stir in me, but I loved her more than anyone else in the world, and was really happy to help her out.

One of the only people that Emily always seemed to have some sort of attraction to is my twenty four year old on-and-off-again girlfriend, Jaime. Jaime is about five feet, seven inches tall, has big beautiful tits (36D, large areola, and exquisite puffy nipples), long light brown hair, hazel eyes, fantastic facial features, a pelvis to die for (slim, flat, waist and 35 inch hips), and a dick devouring cunt. I didn't think about Emily's fondness for her until Emily came out of the closet, but once she did it made sense.

However, Jaime was homophobic and bigoted in general, and her lack of tolerance is the reason why our relationship is on-again, off-again. She seems to really have it bad for me, though, and is a fantastic fuck. Except for her bigotry she otherwise has a truly wonderful personality and is really intelligent, but when she makes comments that remind me of my mother, she turns me off.

I didn't tell Jaime that Emily was a lesbian.

Enough background.

Having Emily live with me was so great in many ways, but as I earlier indicated, I started having non-brotherly thoughts; shit why am I trying to be soft pedal this? I wanted to fuck her brains out! It didn't help that she supposedly did her best studying when naked, and always seemed to have her legs apart exposing a gorgeous prominent-lip shaved pussy that was constantly purring at me! She often asked me about Jaime – including sexual details – and never bothered to try and cover up if she was naked when Jaime came over.

After a few weeks of living with Emily I decided I couldn't continue to live with my attraction for her, Jaime's intolerant comments, and hiding aspects of both of their lives from each other. I decided that I would either ruin my relationships with both of them, or fulfill my fantasies, so I cooked up a plan.

I started by intentionally leaving my door open when I had Jaime over for fuck sessions, and Emily was home. I got Jaime used to me pounding the shit out of her, and then afterward eating her. I had her put a pillow over her face while I ate her, telling her we didn't want Emily to hear her pleasure moans, which I made out to be louder than they really were. I placed her on my bed so that from the door Emily could easily see her cunt – it truly is a beautiful edifice – as I mercilessly tongued and fingered it.

I know for sure Emily had watched us on several occasions when one day I straight out said to her "Well, from the lesbian perspective, what do you think of Jaime's cunt?"

She blushed, but knew better than try to bullshit me, so she shot back. "It's gorgeous. Too bad you don't know how to eat it properly."

I asked if she could do a better job, and she replied "Hell yes," exactly what I was looking for.

I told her that I could arrange for her to eat Jaime's pussy, but she would have to do it, at least initially, without Jaime knowing it. This got her so excited that her nipples got hard and she started rubbing her crotch. "Who do I have to kill to get that chance?" she asked.

I was then straight with her again.

"Your constant prancing around in the nude with your beautiful and over-the-top sexy body is driving me nuts. Although I will always love you as a sister, I can't stand having you around the apartment like that without a 'different' relationship."

As I suspected, she didn't seem surprised and sarcastically said "So that's why you're always tenting your pants. All right, what do you want?"

I quickly replied "Every time you get to eat Jaime, you have to give me a blowjob; and if I talk Jaime into eating you, I get to fuck you."

To my surprise, this didn't seem to faze her one bit. She said she always wanted to eat Jaime, she knew I would treat her with respect, she was very grateful for my financial and emotional support, she was sorry for teasing the shit out of me, and if she'd get what she wanted, why shouldn't I. Then she matter-of-factly asked "How's it going to work?"

The next night I had Jaime over. While she usually doesn't drink much, I was as sweet as I could be to her, and got her tipsy, though not really drunk. Then I did everything in the bedroom that I know that she liked most, including stroking her hair while she laid on the bed, then nuzzling erogenous zones on her neck and hips while gently massaging her spectacular puffy nipples, and occasionally passionately licking or softly biting them. I then bypassed her clit and went straight for her G-spot, with three fingers, and titillated the hell out of it.

After bringing Jamie to two orgasms, I lifted her feet over her head, moved my dick over her slit a dozen or so times, and then completely buried it in her in a single thrust. I pumped her like I was an oil derrick, and blasted one of my better loads in her just as she was climaxing again, within seconds of perfect timing. After we lay there cuddling for a few minutes, I told her to cover her face because I was going to eat her.

[Before I go on, let me tell you as earlier indicated that Jaime has one spectacular cunt. While it is tight, it seems to have a number of cascading interior levels of skin, almost like sets of inner pussy lips. It is a perfect, clean, well defined slit with the outer lips bulging uniformly upwardly, and seems to constantly be moist.]

I turned to Emily, who was at the door on her hands and knees and had obviously relished watching the entire episode, and motioned for her to come forward. She crawled up to the edge of the bed and proceeded, in a frenzy, to lip, tongue, and finger Jaime's pussy. I watched in amazement and appreciation as she drove Jaime stark raving lunatic, and hoped to learn from her techniques. After escalating Jaime to several more orgasms, it was clear that Jaime had bottomed out, and Emily slinked away, licking her lips, while I crawled onto the bed with Jaime and held her in my arms.

Jaime had to be at work early the next day and couldn't stay the night, so I roused her after an hour, helped her dress, and took her home. As I walked her to her door she planted a big sloppy kiss on me and said "Sex with you is always the best I've ever had, but tonight was on a different level. You fingered and fucked me as well as I possibly could be, and your pussy eating was so awesome no words can properly describe it."

I took that opportunity to say, "If we have a couple of repeats of that performance, will you do anything I want?"

She probably thought I meant anal, which she had always resisted, when she answered "Fuck yes, anything."

My plan was working!

The next morning Emily couldn't thank me enough, and said she loved every minute of it. I told her she WAS going to properly thank me that night, so when evening rolled around and Emily was done with her homework she came up to me in her study outfit (naked) and said "I'm ready to pay up; but what do I do with the cum?"

I asked her "Did Jaime taste good?"

Emily replied "No, she tasted great!"

"Well," I said, "some of that was my cum so you apparently have no problem putting it in your mouth or swallowing it."

At first she got this look of like "Oh, gross," but it changed to an "Okay, might be good," look.

I gave her a brotherly kiss and hug, then a short but lascivious kiss and hug. She pulled down my pants, got down on her knees, grabbed my already completely erect cock, and started sucking it like it was the tastiest lollipop in the world. She was actually really good, better than most girls who sucked me off, and her inherent talent combined with my erotic feelings toward her had me ready to explode in no time, especially since I was stroking and lightly pinching her perky tits as she sucked me off. I told her that I was cumming, but again to my amazement she just kept sucking and swallowed a good percentage of my ejaculate before gagging a little and allowing some to leak out.

After I was completely drained she said "You know, it does taste kinda good, though much better in a pussy juice cocktail," and proceeded to lick her face and my dick clean.

We went arm-in-arm to sit on the couch and watched the news together while cuddling. She fell asleep in my arms so I carried her to her bed and tucked her in. Just as I was leaving she opened her eyes and I said "Thanks, Emily. You're fantastic!" She smiled broadly, chuckled, and then closed her eyes.

While I was worried that my wonderful personal relationship with Emily might worsen as a result of the last two nights' activities, actually it got even better. However, she did keep pestering me about when Jaime was coming over again.

Over the next two weeks, on five separate occasions, I serviced Jaime as well as I had the first time that Emily ate her. Each time that I serviced Jamie, Emily may have done an even a better job of eating her, if that is possible, than the first time. Emily continued her blowjobs, and improved to the point that she was as good as anyone who ever sucked me off, and in view of the attraction I had for her actually produced the best blowjobs in my experience. I had a tremendous inner glow after each session.

After each episode I reminded Jaime that I was going to call on her to do something for me and she always smiled and said she definitely would.

On the next occasion – to be seventh time that Emily ate Jaime – I planned to set the stage for the "next level." I told Emily what I was up to – and I would do my best to get her eaten by Jaime.

Since I was setting the stage for fucking Emily, the next night my motivation was so strong that – in all modesty – I have to say that I fingered and fucked Jaime better than I ever had done either before in my life. She was close to comatose by the time that Emily started in on her. After Emily ate Jaime to her first orgasm, and started in again, I crawled on the bed with Jaime and started sucking her astonishing tits. At first she was clearly enjoying this even more than anything else ever; but suddenly a realization apparently dawned on her; "If someone is sucking my tits, who is licking my clit?"

Jaime sat up with a jerk, pulled the pillow from her face, looked at me next to her, and then looked at Emily licking her cunt. She freaked. Emily left the room. I finally calmed Jaime down, and she demanded that I take her home.

As we were riding back I told her that Emily was a lesbian, was attracted to her, was the one who had eaten her the last six times, and reminded her how good it felt to her. Then I also reminded her that she had promised to do anything I wanted as payback for the way I had serviced her, and that I wanted her to eat Emily!

Jamie was very quiet the whole way back. With about a block to go I told her that except for her intolerance, she was the perfect woman for me, and if she got over it we had a long term future together. She still said nothing as she stormed out of the car.

When I got back to my apartment, Emily was distressed, but I consoled her and waxed philosophical when I told her that "what will be, will be."

I waited a few days and then sent two dozen roses to Jaime's workplace with a note that said "Please call me. I want a future with you."

In a time filled with surprises, I got another one. Jaime did call and asked me to come over to her place. When I got there she was crying. She said she hadn't been getting much sleep, but she had started to think back on her life and ideas, and had an epiphany. She was sorry for her intolerant comments in the past, had really enjoyed Emily's attention and knew that Emily was very important to me, and was willing to do anything to further our relationship.

Always one to strike while the iron is hot, I kissed Jamie fervidly, then said "move in with me and Emily". Once her initial shock passed she started crying again and said "I've hoped that you'd ask me to move in with you for a long time! Yes, yes, yes!"

I laid out the ground rules. Once a week Emily would eat her while I fucked Emily. Once a week she would eat Emily while I fucked her. This did not make her a lesbian. She and I would be exclusive at all other times, no exceptions, and if things worked out like I hoped we would end up engaged. She smiled, said she could live with that and may even find it to be a wonderful relationship. She moved in the next weekend.

The first time that I fucked Emily was straight from fantasy land. As she was eating Jaime, Jamie's stupendous massive tits were swinging as she writhed back and forth, providing a spectacular backdrop. Just as spectacular was Emily's consummate ass sticking out into contact with my waist. I grabbed two handfuls of those phenomenal hemispheres as I thumped for all I was worth.

Emily's cunt felt as good as she looked, with just the right tightness, just the right amount of moisture, and just the right length; like it was molded to my cock. Her cunt lips almost reached out and grabbed my cock, and she had great muscle control. Emily groaned as I unloaded copious amounts of ejaculate into her, but she never missed a beat in eating Jaime. After I deposited my load I laid my head gently on her back, wrapped my arms around her, and expressed eternal gratitude and love.

The three of us got to really look forward to our twice a week sessions. While I never let on, although fucking Jaime was great physically and perfect psychologically, I found fucking Emily the epitome of physical satisfaction. However, upon my questioning Emily admitted that fucking a guy was not physically satisfying for her, and she never had anything more than a mild orgasm. However, she loved me unconditionally, and she knew how happy it made me, therefore mentally she really enjoyed doing it.

Emily also made it clear – although she certainly didn't have to since I wanted no part of sharing her with any other guy – that no other guy's dick would ever enter her vagina. She was also really satisfied with Jaime eating her, especially since Jaime improved her skills in that regard with each session.

Fast forward about eighteen months to the present. Jaime and I both got promotions, we bought a house together, and of course Emily lives with us. Emily is slated to graduate college in a few months, and now has a girlfriend almost as cute as she is who stays over two or three nights a week. The girlfriend doesn't know about Emily's relationship with Jamie and me, as we still have our twice weekly fuck sessions.

Jaime and I are now engaged, and true to her word Jaime has seemingly purged herself of bigotry, and now is the perfect mate. I am totally in love with her!

Life is REALLY good

imhapless
imhapless
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  • COMMENTS
10 Comments
Rapier875Rapier8756 months ago

Whole thing was too rushed.

Rancher46Rancher46over 1 year ago

Story was kind of disappointing in the end with Emily still being a Lesbian, was hoping that Brad would convert her back to become the third part of a polygamous family with Brad and Jaime. 3/5

DYNO224DYNO224over 9 years ago
just about me

You do a great job with your stories though I myself am not tolerant I guess it is good that some are.Not thrill with full fledged lesbians just seems to be another group even more prejudiced and inflexible than myself.I try to be kind and not hurt anyone's feelings but just avoid proximity to things that tend to unsettle my somewhat aggressive nature.

Epiphany_JonesEpiphany_Jonesover 9 years ago
To the previous comment, regarding "tolerance":

Take a long, unbiased, look around. There are websites devoted to pix and vids of girls kissing other girls. When a girl (or woman) wants to turn on a guy, or show how daring she is, she might kiss or make out with another woman in front of him. Hell, there are even RELIGIONS and entire CULTURES where men are allowed, and even encouraged to have multiple wives and/or mistresses.

Now, how many websites are devoted to images of guys kissing other guys? Honestly? I'm sure there are some out there, but do they get as many hits as the girl on girl? If a guy wants to turn on a woman, does he do it by making out with another guy? Again, I'm sure it happens on occasion, but those who are involved are a MINORITY, and a SMALL minority at that!

Picture a typical college bar. Picture the reaction to two girls who start making out at the bar. Now picture the reaction to two guys making out at the bar. Which one do YOU think is more likely to get applause, and which one will just get shocked stares?

Our society is changing, and part of that change is a greater acceptance of people's sexuality. But, not speaking about the past or the future, speaking just of the PRESENT, there is a clear trend to be MORE accepting of women who experiment than MEN who experiment. That's not a judgement. That's an acceptance of HOW THINGS ARE.

Speaking JUST for myself, I'm not a homophobe. I'm actually a supporter of GLBT rights. But actually living a gay lifestyle has no appeal for me. There's no attraction or curiosity to experiment with another guy. I don't judge those who do feel that attraction and/or curiosity, and if nobody is getting hurt, I don't see any reason to object or complain. Just as some guys have a desire to be with "Big Beautiful Women", or like some black guys have a desire to be with white women (or vice versa), or if a guy has a particular desire for Asians, or Latinas, or blondes, or red-heads, or petite women, or younger women, or OLDER women... If a guy has no DESIRE to be with another guy, WHY would that make him INTOLERANT?

If anything, your comment suggests you have your own intolerance.

AnonymousAnonymousover 10 years ago
Are YOU more tolerant now?

OK - It's always the babes. Now the girlfriend is 100% 'cause she will do other babes. What about you? Will you do guy action?

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