Shared Fantasy: Heather's WishbyJamesSD©
"I want to try anal sex."
The six words were written in careful script on an otherwise empty page. The page was in the hands of Tom, a 22 year old college senior. It had recently been inside a blank envelope which Heather, Tom's girlfriend of eight months, had given to him.
Tom was a bit surprised. Was Heather serious? Could real girls, those outside of porn, actually enjoy "butt-sex"? Tom had assumed that women only consented to it to satisfy their boyfriends' desires, and it was never a particular fantasy of his. Yet here in front of him, in his girlfriend's unmistakable handwriting, was her "Biggest sexual fantasy I could never say out loud."
Tom and Heather had met through mutual friends. He admired her independence and fierce wit, in addition to her compact, athletic body. She had initially been drawn to his boyish good looks and cute butt, but found his personality exceeded his appearance. He was a "nice guy" yet neither a push-over nor too clingy. Still, it was she who discretely invited him to have coffee, and she who suggested watching a movie at her place afterwards. Fortunately he had read her clear signals and he had been the one to initiate their first kiss, and things had progressed from there.
Both had experience in long term sexual relationships and had good ideas of what they preferred in bed. Heather usually liked for things to start slow and gentle followed by a build-up to hard fast thrusting and some gentle hair pulling. She had eagerly learned Tom's blowjob preferences and what he enjoyed hearing her say during lovemaking.
It had been Heather's idea for each of them to write down a sexual fantasy they were shy to discuss or afraid would be seen as too kinky. They would read each other's desire in private. If the other person was not interested they would simply not bring up the issue. However if they were willing they would be free to either surprise their partner or bring up a discussion.
Tom had debated what to put on his sheet of paper. Like many young men he had an active sexual imagination. In the end he had been honest, writing his greatest sexual desire. He felt a little guilty about what he had written, but had chosen to seize the chance to bare his soul to the girl he cared so much about. He fully expected her to hide the note away and never mention it again, and felt ok about that.
Now Tom had some thinking to do about Heather's anal sex fantasy. He was intrigued, but a tad intimidated as well. Still, he wanted to make Heather happy, and was willing to do what it took within reason.
Heather couldn't remember exactly when she had started thinking about anal sex. She recalled that even in her first conversations with girlfriends about sex and boys she had never expressed the repulsion towards the act as her peers. Anal sex did seem a bit odd, and she wasn't quite sure how a penis would fit in there, but the idea certainly didn't repel her.
In college she had become an avid reader of online sex advice columns and erotica. Initially she preferred stories of romance, with plots similar to romantic movies yet filling in the "good parts" where most movies would fade to black. As she read more and became more experienced herself her apatite for novelty slowly grew. She wondered what happened to the happy couples in romance stories months and years down the line? Was it still champagne and rose petals? Or did they experiment with other things?
She discovered an essay praising the virtues of anal sex written by a woman. It was not terribly graphic, but rather told the story of the author's first experiences with anal sex. The author wrote from a feminist perspective, first outlining how she felt the societal taboo against anal sex was likely an expression of homophobia. She also theorized that the feminist movement had a few unfortunate sexual side effects. To be respected as an equal seemed to mean rejecting any sexual act that could be deemed too demeaning or submissive. Oral sex was acceptable as long as it was reciprocated. But anal sex would be far too demeaning for a "good feminist" to engage in.
Yet the author admitted it was both the cultural and feminist taboos against anal sex that made it so sexy for her. It would never be an everyday activity. But, when she did engage in anal sex with her partner, allowing him to penetrate her deeply, she was going against everything she believed in, in short "being bad". Yet, at the same time it was an expression of trust and love to give her partner such access. She concluded by stating "Feminism is about a woman's freedom to choose, and this certainly extends to sexuality. So I argue that a woman should feel free to enjoy whatever turns her crank, and not feel guilty about the roots of her desire."
Heather felt as if a door had been opened within her mind, exposing a thought that had been present for a long time yet never explored. She found the thought of a man's cock in her ass aroused her in ways that few fantasies could. She never confessed her desire to anyone, yet it began to consume her private moments. She frequently masturbated imagining her boyfriend fucking her ass, at first it was Tom's predecessor and then Tom once he entered the picture. She even experimented penetrating her own ass with her finger, but couldn't bring herself to do more than a brief, shallow penetration.
Heather's desire to feel Tom in her ass was the reason she suggested writing the fantasies in the first place. She couldn't bring herself to express her hidden desire out loud, but somehow writing it down had made sharing it with him possible.
She sat on her bed, unfolding the paper Tom had written his fantasy on. She smiled at the carefully printed words. It was a common fantasy, but she was impressed Tom had found the courage to put it on paper. It was something she'd given though to doing for him before and now had the impetus to go for it. She wondered how Tom had felt about her desire. She hoped he'd be willing to indulge her wanton craving.
It would be Tom who brought up Heather's fantasy first. It was only days after receiving the paper when he mentioned it while talking with her on the phone.
"Hey," he said, "remember that fantasy you wrote down?"
"Yes," she spoke softly, her heart suddenly racing.
"Can we talk about it?"
"Um ok," Heather said, "what specifically do you want to talk about?"
"Well, I don't mind the idea, and I want to make you happy," Tom said carefully.
"It sounds like there's a "but" coming."
"Well, I'm just not sure about it," Tom stated.
"Ok," Heather said patiently, "what aren't you sure about?"
"Well I trust that it's something you really want to try."
"Good. I'm glad that you don't think I'm lying," Heather said with a touch of defensiveness in her voice.
"Alright, for starters this isn't something you've done before right?" Tom asked.
"No! Of course not, I'd have told you."
"Sorry." Tom paused. "I just guess I worry about hurting you, and about not doing it right."
"I appreciate your honesty Tom. In fact, it probably will hurt a little. It's sort of the point. That whole pleasure mixed with pain thing."
Tom didn't quite understand how Heather's mind worked, but replied, "Right."
"As for not doing it right... just trust me. We'll do this together, and if it doesn't go perfect I'm not going to flip out. I will appreciate you for trying."
"I feel like such a wuss," Tom said.
"Why?" Heather asked.
"My girlfriend has to convince me to fuck her in the ass!" Tom exclaimed.
After a slight hesitation Heather burst out laughing, which caused Tom to do the same.
"I guess it is pretty funny," she said.
"Ok, you've convinced me," Tom agreed. "Maybe we can try it when we get together this weekend."
"Sure, I'd like that," Heather replied. Her heart soared, though a new sense of panic set in. Sometimes the prospect of actually getting what one wants can be a scary thought.
She was too distracted with thoughts of her man's cock deep inside her ass to concentrate much the next couple of days. She was overjoyed when Friday finally arrived. She was frightened but eager, with a sensation of butterflies in her stomach, which always made her feel wonderfully alive.
They didn't bring up their planned activity at first, simply going about their usual Friday night date routine. He cooked a simple meal for her; they chatted about their weeks, and retired to the sofa to watch TV. Without much delay they were embracing and kissing passionately.
He carried her in his strong arms to his bed and laid her down gently. He undressed her carefully, kissing and caressing her flesh as he exposed it. When she was naked before him he parted her thighs and began licking her pussy. His tongue felt lovely on her clit, and he occasionally looked up into her eyes as he pleasured her.
"You're far too dressed," she said and began tearing off his clothes. He helped her remove his t-shirt as she ran her hands across his firm chest, mostly smooth with just a bit of hair in the middle. Her hand ran down his flat stomach to the waist of his jeans. She unbuttoned them and slid them down. She could see his obviously erect cock within his boxers, but she felt a need to see it fully exposed. Once freed, she quickly took his firm organ into her mouth and began sucking it as he untangled his legs from his clothing.
He moved her onto her back and thrust into her pussy powerfully, yet gently. He made love to her deliberately, thrusting into her slowly and letting her feel every inch of him deep within her. He focused on making her feel good, and was rewarded with her cry of pleasure and the feeling of her body shuddering in a small orgasm.
With his cock still deep within her, Heather opened her eyes and said, "You didn't come."
"No, not yet."
"Do you want to?" she asked quietly.
"I will. Let's move to the bed." Tom slid his slick cock out of her pussy and led her to the bedroom. He had other plans for his erection before his climax.
Once back in each other's arms Tom said, "I think I want to grant your wish. But there's a condition."
"I want you to look me in the eyes and tell me exactly what you want me to do to you."
Heather grinned. "You want me to say it out loud? You're going to make me ask for it?"
"I want you," Heather spoke slowly, "to fuck me in my tight little ass. I want you to stick your nice big cock into my butt and take my anal virginity. I can't think of any man who I would prefer to be the first to have anal sex with me."
Tom's cock throbbed as such dirty language escaped his girlfriend's lips. He didn't reply, and instead opened the drawer Heather kept condoms in before they were tested. Several packages sat undisturbed next to a bottle of lube.
"How do you want me?" he asked.
"I think it would be easier with me on my back," Heather said, "But honestly I'd find it sexier if you fucked my ass from behind."
Tom nodded and decided to trust her judgment. "Well then get on all fours for me, baby."
She eagerly sprung onto her hands and knees and wiggled her firm ass at her boyfriend. Tom reached out and caressed her athletic young backside tenderly. He had groped and grabbed it countless times in the past, but it seemed to have new meaning with what he was about to do.
Tom spread her cheeks slightly and brushed his finger against her opening, eliciting a shudder from Heather. "Is this where you want my dick, baby?" he asked.
"Yes," she replied.
Tom squired some lube onto his finger and pushed the tip into her tight ass. Heather squealed.
"Are you sure something as big as my cock will fit in here? I can barely seem to get my finger inside you," Tom teased.
"God, I guess you'll have to open me up with your fingers then," Heather moaned.
Tom felt a rush of power as he pushed his finger past the second knuckle into her ass. He reached around and rubbed her clit with his other hand as he began sliding his finger in and out of Heather.
"You feel that Heather? That's what my cock is going to feel like inside of you, but bigger. You like how it feels?"
"Yes! It feels lovely. Not quite like my pussy, but still good. It's a very new sensation."
"Are you ready for another finger?"
"Yes, but please go slow, lots of lube. You need to get my ass nice and ready for your cock."
Tom worked a second finger inside of her, and slid his left hand up and down her side before resting it on her buttock. He slid his fingers in and out of her silently, hearing her grunt with each insertion. His cock was hard as a bar of steel.
"You ok baby?" Tom asked.
"Yes, Tom. It's intense though. But don't stop. Please, don't stop."
Tom watched his fingers continue penetrating his girlfriend's ass. He felt her relax a bit, as if she had gotten used to the idea of having something inside of her and was learning to simply accept it rather than resist his invasion.
"Please fuck me," Heather said. "Would you fuck my pussy for a little bit before you put your cock in my ass?"
Tom sprung forward and slid his cock into Heather's pussy. He was shocked how insanely hot and soaked she was inside, realizing how much she must have loved having him finger her bum.
"So you want it then?" Tom asked, thrusting into Heather's snug pussy. "You want me to fuck your ass?"
"Yes Tom. Fuck my ass!"
Tom swiftly rolled a condom onto his dick and squirted a liberal amount of lube onto his shaft. He rubbed it around and aimed the head at her asshole. As he pushed forward his cock missed its intended target and slipped up between her buttocks.
"Whoops, guess that's what happens when you apply so much lube," Tom said.
"It's ok, take your time," Heather exhaled.
Tom gripped Heather's buttocks tightly in his slippery palms and spread them slightly. He placed his cockhead at her opening. He used his right hand to steady his cock and gradually pushed forward. On the second try he felt success as his cock pushed into Heather's ass.
"Oh FUCK!" Heather cried out. Tom stopped instantly.
"DON'T stop. Just hold still," Heather said. Tom acutely noticed the pressure on his cockhead. "It's... It's a lot. Let me get used to it." Tom held still until Heather said "Ok, more."
As gently as he could, Tom pressed forward with his dick. He felt Heather's whole body tense up, and suddenly he felt less resistance as his cockhead popped past her opening.
"Oh WOW!" Heather exclaimed.
"Wow in a good way?" Tom asked. Focusing on not hurting her had distracted him from his own pleasure, but he now noticed how nice the novel sensation of being partway in her ass was.
"Yes. In a very good way."
Tom tested the waters and began slowly rocking back and forth, each time easing a tiny bit more of himself into her. He looked down and marveled at the sight of his own cock, penetrating his girlfriend's ass. It was a little obscene, and very visually appealing.
Heather moaned loudly as her boyfriend worked his cock into her ass, little by little.
"Don't take this the wrong way, but it feels kind of like you're splitting me in two. I know that sounds unpleasant, but trust me, I'm enjoying this," Heather stated.
"God, I just want to thrust my whole cock in you and start fucking you hard."
"We'll be there soon. Just keep it up. I'm getting used to having your dick in me this way."
With patience Tom soon found his entire cock buried in his lovely young girlfriend's ass. He continued his small, patient movements. Heather's ass was noticeably more relaxed; it was still tight but he knew he had loosened her enough to allow a true fuck.
"I'm going to start thrusting in and out of your ass Heather."
"Yes, Tom, fuck my ass!"
Tom slid his length most of the way out of Heather before pushing himself back into her ass. She gasped loudly as he slid back in.
"That was nice," Heather said. "Can you do that again?" Tom didn't answer verbally, instead repeating the motion of smooth, deep penetration.
Tom had expected Heather's ass to feel like a really tight pussy. He was surprised at the distinct difference in fucking her pussy and ass. Where her vagina squeezed his cock along the entire length, with her ass the only real point of tightness was the opening. Once inside, he could certainly feel her, but the majority of the sensation came from the point of entry.
"I can hardly believe we're doing this," Tom said to Heather.
"I know, it's so dirty!" Heather agreed. She slid her hand between her legs and began rubbing her clit as Tom continued sliding in and out of her snug channel. "I want to make myself come with you fucking me this way."
Tom watched in awe as he continued his slow fucking of her tightest of openings. While he didn't have much of a view, he could feel her hand rubbing against her clit rapidly. With surprising quickness she cried out in orgasm, her body shuddering.
"That was quick," he joked a few moments later.
"What can I say, you got me really turned on," Heather said.
Heather's needs satisfied, Tom focused on his own pleasure. He watched his cock penetrate Heather deeply, stretching her out and disappearing completely within her. He gripped her hips and enjoyed the novel sensation surrounding his cock.
"Come for me baby. Come in my tight little ass!" Heather cried out. Her words had the desired effect on Tom, as his cock swelled up almost immediately. Tom groaned gutturally as his cock erupted. He steadied himself against Heather's hips as his cock pulsed repeatedly within her ass. When his climax ended he leaned down and kissed Heather between her shoulder blades.
"Thank you," she whispered.
Tom couldn't help chuckling. "I should be thanking you."
"Ok, we'll call that a team effort. It was wonderful. It feels strange, but it definitely stimulates my brain exactly how I thought it would."
"Good," Tom said, "because I find your brain very sexy."
Eventually Tom removed his cock from Heather's ass slowly. She trembled slightly as he slid from her, and shivered with pleasure as he cuddled up behind her on his side.
"I can't even describe how my body feels," Heather said. "Alive. It felt nice when you fucked me, but the removal gives me this amazing feeling. Total bliss."
Tom hugged her tightly and kissed her neck once more.
"Thank you for fulfilling my fantasy," Heather said.
"You know it was my pleasure," Tom replied.
As Heather drifted off to sleep her thoughts drifted to the words Tom had written on his slip of paper: "I fantasize about having a threesome with you and another woman." She smiled slightly, already plotting how she would surprise him and make his wish come true.
Authors Note: Thanks for reading. You could say this story is inspired by my own first experience with anal, but the characters and setting are quite different. Please take a moment to let me know what you thought, either through a vote or a comment. Thanks!