Heartbroken Hillary - Cover

Heartbroken Hillary

by Tony Tiger

Copyright© 2020 by Tony Tiger

Erotica Sex Story: Rejected girl gets back at her ex by using another guy but that's not all that happens. Life often has surprises.

Caution: This Erotica Sex Story contains strong sexual content, including Romantic   Sharing   Incest   Swinging   First   .

Hillary was in love. Sweet sixteen with a serious crush on a guy who showed a lot of interest in her even though she was ‘pure’. There was plenty of competition for guys who were decent looking and not gay. He was a couple of years older and had a nice car and money to spend on her. Perfect.

As she expected from girl-talk, he wanted in her panties. She wasn’t quite ready even though Mom had gotten her that arm-bump for her birthday. It had to be special that first time, her romantic mind kept insisting, not some bang in a backseat or bouncing on him in a darkened corner.

This BF didn’t catch on to that, getting her top and even her panties off in the above places but hitting a wall when he tried to get more than a blow-job for his pecker. It was a nice one, she thought, but she had little reference other than porn pics to judge by.

He seemed to be catching on when, without warning she saw him at an event with a gal she knew was an easy slut. That hussy was all over him and it was clear he was getting what he wanted from her. No more dates! She cried and cried, so much that her older brother, who she had always called “Bro” checked in on her. She sobbed in his arms as they lay on her bed, pouring out her hurt.

Neither remembered exactly how it happened but they began kissing and holding each other close. It was late and their parents, who slept like logs, were in bed on another floor of the house. The siblings were in robes. Bro’s hand had been stroking her back, trying to sooth her pain when it went lower and followed the curve of her ass. She reached for his butt and pulled him closer which pressed his erection against her belly.

Her latent desire bubbled to the surface as it recognized the kind of scene she’d wanted for her first copulation. There was no stopping, not even to take the robes off. They were opened and it was hot flesh on hot flesh, hands exploring.

He’d done it before so took the lead and gracefully got her wet. He’d eat her another time. She wasn’t letting off the lip-locks right now. Moving on top of her, he entered easily, her hymen long gone from other objects. She moaned into his mouth and pulled on his buns until he was fully buried. Instinctively her hips began undulating and he matched them, not pulling out but just rubbing their pubes together as he stayed deep.

He broke the kiss and she was breathing deeply, making throaty noises as his mouth found her hard nipples and did things to them she definitely liked.

It was impossible for him to hold off. He hadn’t been laid in weeks and this was the finest place his cock could imagine. She began to sob as she felt his strong sports of liquid on the very innermost part of her. He gave her little kisses on her wet cheeks, knowing they weren’t from sadness anymore.

After another and longer connection, he left her to dream in her bed. They had to act the same as usual in the morning, he knew, even though there was no stopping this.

His concerns about her feelings evaporated when they were alone at the breakfast table. She smiled, mouthed “thank you” and blew him a kiss. It was a teacher conference day for her and he called in sick. As soon as their parents left for work they were naked in his room for a change.

Hillary learned a lot about giving and receiving oral sex when their parts weren’t deeply connected. Although it just happened, both would look back at the day as setting personal sex records that may have been tied but never bettered. Lifetime memories for a lifetime connection. Both knew without saying that, no matter what relationships they might get into, this one would never be denied priority. It was a fall-back refuge from the vagaries and disappointments of life.

The first order of business, suggested by Bro, was to make a short and anonymous, but identifiable by her ex, video of her pussy happily accommodating a man. It would be sent with a note that his impatience had cost him this. That done they pursued every opportunity to pleasure each other, even travelling out of town and sharing a hotel room for events. Their parents were so pleased that they got along and he looked after her. He sure did!

Bro offered mature advice, “Hillary, you need to live a normal life too. I expect you to date and I will also. If we don’t, people will get quite suspicious about why we are so close and that could hurt us.” She understood and stopped refusing invitations from guys she thought she might like.

One night she came back from a date and their parents were asleep. She slipped naked into her brother’s bed, awakening him. “I want you right now!” got him inside her quickly. As they lay close together she said, “I really like this guy. We talked about dating but not about sex.” The question was unspoken.

“I thought that was understood,” he replied. “I’m screwing both those gals I’m dating now but didn’t say anything because I didn’t know if you wanted to be aware.”

She shuddered in orgasm. “This cock has been in two other pussies?”

“Yes, and a few before yours too. Doesn’t make me enjoy you any the less nor will anything you do with others. You’ll see.”

She humped him hard and came again as he creamed her. Before they separated she whispered, “I want to know about what you do. It’s hot!”

He kissed her hard and said, “Ditto!”

Two nights later she was late getting home and got in his bed again. When he filled her eager crotch he said, “You’re awfully slippery. Got laid tonight?” He saw her nod and he pounded her so hard she had to bite her hand to keep from screaming with one orgasm after another. “Not ... as ... good ... as ... you ... but ... fun! Glad ... I ... can ... share ... it.” His blast was strong too.

That was a breakthrough, more for her than him. Now a full and independent woman, she blossomed and her brother often sampled her nectar, often enough flavored by visiting bees. She made friends with his women and had things to think about when she was with them that they never suspected. The same for her brother as well with a serious boyfriend of hers.

Then an opportunity came along. They were double dating to an out-of-town concert. “Brother-mine, get a room with two beds.” He raised an eyebrow and she just grinned.

That night, high from the music and alcohol, Hillary was in great spirits, parading nude from the bathroom to the bed where her date, Bill, waited. Pulling the sheet off him she mounted his erection, quite aware of her brother and his date already screwing discreetly under their covers. They stopped and turned to watch. She grinned at them and hopped off to take Bill’s cock in her mouth for a bit then moved up to plant her pussy in his face.

Her brother got in the game, urging his date, Bobbi, to suck on the shaft resting on the stomach in the bed across from them. As she bent over to take Bill in, Bro slid into her from behind and she moaned around the cock in her mouth. Hillary reversed her position so she could see better.

That only lasted a few minutes before Bro went back to their bed and Bobbi mounted his face. The dates gasped when Hillary wrapped her mouth around her brother’s glistening shaft and Bill duplicated the arrangement that had been in the other bed. He couldn’t hold off though after all that stimulation and his grunts were clearly audible. As much as he wanted to bury his bone in his sister’s just-fucked twat, Bro still got gasps as he ate it, licking the oozing cream. He motioned to his date and she cleaned Bill’s drooping dick.

Then he put Bobbi on the bed, deep kissing as he fucked her to an audience. Hillary and her date did cleanup this time and then it was lights out. There was a lot of whispering with curious partners. Nothing would be revealed yet, blaming it on the circumstances. No one slept through the night without getting screwed (in a good way).

Although both dated others, the siblings got steadily closer to the pair that had spent the concert night with them. Another opportunity like before arose and they were in a double room again. Bobbi was pretty perceptive and, after returning to the room, decided under the influence of drink, music, and hornies, to open the issue.

They all got naked for bed, having developed that intimacy before, and were having a nightcap. Bobbi looked at Bro and casually asked, “How long have you been screwing Hillary?” That got her ALL the attention and she noticed how the drink in his hand shook.

Acting blasé, he tried to bluff, “Since I could get a hard on. Why do you ask? Do you want to watch?”

Taking the semi-facetious answer deliberately literally, she was quick to say, “That would be interesting, no doubt, as is most live sex. Bill, what do you think?”

He was stunned at the idea, not having any prior clue, even that his girlfriend was fucking others at all. Hesitatingly, “I don’t know. Isn’t it a sin?”

Bobbi laughed, “Depends on your religion. Egyptians insisted that royalty have babies that way. I’ve bonked both my brothers a few times.”

THAT opened everyone’s eyes! Raised some dicks too. Seeing the reaction she egged them on. “C’mon guys show us!” In encouragement she walked over to the sitting Bill, turned around and sat on his erection, opening her thighs so all could see it penetrating. “Your turn now!” she chortled. Bill did not push her off, it was noted.

Bro muttered, “You asked for it,” and proceeded to vigorously bonk his sister who responded just as strongly with an audience for the first time. Bobbi bounced on Bill and felt him shoot in her even before the performers reached their finale. She was delighted.

The lights went down and the original partners had some serious reconnecting to do with lots of emotional components. More than once before dawn too.

After the room-service breakfast, Bro got a bit more revelation about his girlfriend. He enjoyed her open sexuality as they dated but new layers were being unwrapped. Bobbi said, “I’d like to have a good lay-down fuck with Bill before we check out. You’d be welcome to watch if you don’t have anything else to do. You interested, Bill?” He looked over at Hillary who smiled and nodded.

Bobbi was such a hot piece that he didn’t even notice the audience who were enjoying the remnants of what he had left in Hillary during the night. The siblings had often talked about what they were sharing as they joined after her dates. She asked Bro to not wash his cock until she’d had a chance to taste his lover on it. Not yet mentioned was tasting Bobbi both before and after Bro fucked her. She’d make it happen now that she knew how carnal that woman was. There was barely time to take showers before vacating the room. The ride home was silent and thoughtful.

The uncovering of their long-held secret was a bit liberating and opened the door to some fun group adventures. Bobbi and Bro began talking about their other activities and getting off on each other’s doings but confined swapping to “The Four”, not needing to go out of town since Bobbi had her own apartment with a king-size bed that had quite a few memories. Bill installed a hidden camera and she got vids of them and her other vaginal visitors to share.

 
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