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What Does Friends With Benefits Mean?

"One friend asks for advice on how to please a woman."

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When we’re very young, boys and girls play together as a matter of course.  Just humans interacting with each other.  It’s only as we age that boy-girl relationships become complicated.  The other sex becomes not friends, but ‘boyfriends’ or ‘girlfriends’ to denote a sexual orientation. 

Which brings us to Billy and Sarah.  They lived on the same block as youngsters, and were fast friends at that innocent age before puberty.  Then Sarah’s parents moved to another part of town.  Naturally, the two kids lost touch with one another.  Years passed, but one day, all-knowing social media offered Sarah to Billy as a ‘friend.’  The childhood friends reconnected via social media.  They renewed their friendship, now through the mature eyes of adulthood.  Each had graduated college and was working in the city.  They’d see each other occasionally after work at a local watering hole, and kept up with the other via on-line posts.  Just the normal stuff friends do.

One night Billy attended a party Sarah threw at her apartment.  Billy was between girlfriends, and hoped to meet someone.  But no luck that night.  He lingered behind after others left to help her clean up. 

When they were finished, Sarah insisted that he stay.  “Let’s catch up in-person.  There is only so much one can say on Facebook.”  They talked until late.  Sarah told him it was silly to drive home after an evening of drinking.  “Spend the night.  I’ll make you breakfast in the morning.”

It was a reasonable suggestion, and Billy went to sleep on the couch.  But the couch was small, such that Billy, at 6' 1”, would have had to sleep with his knees curled.

“That makes no sense.  You’ll sleep with me,” said Sarah.  “We’ll just each stay on our side of the bed.”  And so it was.  Sarah slept in pajamas, Billy just in his briefs.  They each slept soundly without disturbing the other.  Things changed when Billy awoke the next morning with what is euphemistically called ‘morning wood.’  An erection like that happens occasionally to guys, especially if one’s dreams have ventured into the sexual realm.  No big deal.  It’s just a fact of life.  Guys know how to handle it. 

Sarah appeared sound asleep, so Billy quietly began stroking his penis.  He needed to respond to the sexual tension.  He was on his side, stroking himself when Sarah’s voice said, ‘What are you doing?”

Embarrassed, Billy immediately ceased his motions and said, “Nothing, just getting comfortable.”

“You were masturbating, weren’t you?” came the reply.

 “Yes.  I’m very embarrassed,” Billy said.  “It’s been a dry spell since my girlfriend bailed on me.  Couldn’t help myself.  I’ll get going.”

“No, don’t go.  We’ve been friends too long to let a silly thing like that come between us.  Go ahead, finish.”

“No, I couldn’t.  Please, drop it.  I’m fine.”

“No, you’re clearly not fine,” as she looked at the protrusion elevating the covers.  “Do you want me to help?” said Sarah.

“Oh, my God, no.  I’d never ask you to do that,” Billy replied.

“You didn’t ask.  I volunteered.”

Billy didn’t answer.  He just lay there, not sure what to do next.

Sarah pulled the covers off him, exposing his body.  His briefs were tented, with the tip of the erect penis poking out of the top. 

“I’ve never seen a guy masturbate,” Sarah said.  “Actually, I’ve never seen a guy ejaculate – sex is always in the dark, under the covers.  Let me watch.”

“You’re joking.”

“No, I’m serious.  I want to watch.”

Billy cautiously resumed stroking the erect penis through the fabric of the briefs.  The sight of Sarah watching his movements heightened the sexual tension.  He was rapidly reaching a point where there would be no turning back.  He pulled down the briefs, fully exposing himself.  The penis was an impressive, arching shaft straining upward. 

Sarah's eyes were wide, as this voyeuristic view allowed her to fully examine the size and shape of the organ. 

“You’ve grown up nicely,” said Sarah, with a smile.

“Well, you’ve grown up in nice ways, too,” said Billy, as he reached to press against a breast.

“I guess we’re both different now.  For the better, of course.”

Billy continued to rub his exposed flesh, with the expected result.  He groaned as semen began its powerful surge upward.  With a cry, he spurted a stream high onto his abdomen and chest. 

“Wow,” said Sarah.  “That was great.  Amazing thing you’ve got there.”

“Thanks,” Billy said in a quiet voice, as he lay quietly, recovering. 

“Girls don’t have anything like that,” Sarah said.  “Our orgasms are internal.  Maybe we get a little wet, that’s all.”

“Yeah,” said Billy, lying still, coming down from the rush of pleasure.

“Do you want to watch me?” offered Sarah.

“What, watch what?”

“See me masturbate,” said Sarah.

“You would masturbate in front of me?” Billy said in a surprised voice.

“It would be only fair,” Sarah said.  “We used to share everything.  This is just the adult version.”

She had Billy’s full attention now.  “I’ve never seen a woman masturbate,” he said.  “It was years before I even realized they did it.”

“Yes,” Sarah laughed.  “We do it too.  Want to see?”

Billy nodded his head.

Sarah slid the covers off, and began to stroke her groin through the pajama bottom.  Her eyes were locked on Billy, as he stared intently at her.

“Let me see you,” he said.

Sarah slid the pajama bottoms down her legs and pulled the pajama tops above her breasts.  The breasts were beautiful, small but firm and milky white.  Billy stared at the prominent lips of the vagina, crowned with a full mass of unruly pubic hair.  She resumed manipulating her now exposed body, with two fingers sliding into her opening.  Then, with moisture on her fingers, she circled the clitoris.  With the other hand, she squeezed her nipples.  She began breathing heavily and gave off small moans as she worked herself into a state of excitement.  She increased the pace of movement against the clitoris.  But she wasn’t reaching a climax. 

“I need more,” she said.  “Use your tongue.”

Billy eyes widened.  He never in a million years expected to hear her say that.  But a full-blooded guy doesn’t say no to such a request.  He slid down so that his mouth was level with Sarah’s groin.  He slurped at her opening, raking the vulva, then the clitoris, with his tongue.  That quickly gave Sarah the extra stimulation she needed, and she cried out as an orgasm spread through her body. 

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Now it was her turn to lie quietly, seeking recovery from the flood of endorphins. 

“Does this make us lovers?” Billy asked, a little naively. 

Sarah laughed.  “No offense, but you and I are never going to be boyfriend-girlfriend.  We’re just old friends, but we’ll have to expand the definition a little.  Maybe now we’re friends with benefits.” 

That sounded fine to Billy.  Sarah had a great body, but her face was more plain than the women he normally dated.  But beyond that, she was too much a part of his upbringing to be a romantic partner in the Romeo and Juliet model.  They were just friends.

But this ‘with benefits’ concept needed some fleshing out.  What did that mean, anyway? 

“What does it mean to be friends with benefits?” he asked innocently.

Sarah laughed and cupped his testicles with her hand.  “To be determined,” she said.  “I’m sure we’ll encounter sexual issues where one of us could use expert advice from the opposite sex.  Questions we’d normally be too embarrassed to ask because we don’t want to reveal our ignorance.  Stuff like that.”

Simple enough.  So, that’s how it began. 

It wasn’t long before Billy met a new woman.  He liked her, but it seemed she was not committed to pursuing the relationship.  She never said it to Billy, but he heard through a mutual female friend that the woman said that Billy wasn’t satisfying her in bed.  Billy, for his part, didn’t understand.  He thought he was very solicitous, holding off his own pleasure as long as he could before he climaxed.  He needed someone to explain what he was doing wrong. 

“She told her friend I’m a lousy lover,” he confided in Sarah.  “I like her, but that problem can’t continue.  It will break the relationship.”

“Have you talked to her?” Sarah asked.  “Not directly,” Billy replied.  “The friend told me in confidence what she said, so I have to be careful.  But I’m always saying, 'What should I do?'  She says everything is fine – but I know it isn’t.”

“Describe for me your technique in bed,” Sarah asked.

“What technique?  I fuck her brains out.” 

“What kind of foreplay do you engage in?” Sarah asked.

“I guess I touch the breasts.”

“I’m sensing the problem,” Sarah said.  “Women don’t get aroused in a second like men do.  You have to build excitement, let arousal develop slowly.  Come, demonstrate for me what you do.”

“Huh?” said Billy.  “Demonstrate?  What do you mean?”

“I want you to have sex with me the way you’d do it with her.  I’ll tell you what you’re doing right and what you’re doing wrong.”

“You’re joking.  You want me to make love to you?”

“No, we’re not making love.  It’s you demonstrating your technique.”

“Will we be naked?” Billy asked.  (Billy is not the quickest study.)

“Yes, of course, stupid.  But it’s not for titillation – I’ve seen you naked already.  It’s for instructional purposes.  Let me start by asking some questions.”

“Do you have music playing in the background when you’re looking to be romantic?”

“Eh, no.  Why should I put music on?”

“Because you’re building a mood.  Do you dim the lights?”

“Billy’s blank look reflected the depth of his lack of understanding.

“Do you serve alcohol?”

“Yeah, I always have beer, and I drink several.”

“Does your girlfriend like beer?” Sarah asked.

“I guess.  She’s never said, although she never drinks more than half a glass.”

“You’re quite the host,” said Sarah.  “Offer her mixed drinks, like a Cosmopolitan or a Mojito.  Find out what she likes.  You want to get alcohol into her – and by the way, she wants the buzz from alcohol too.  Now show me how you handle foreplay.”

“OK,” said Billy.  “Take off your clothes.”

“My God, were you raised by wolves?  That’s not how it’s done.  We’re not in the college locker room, getting ready for PE.  You should undress a woman, and do it slowly and seductively.  She wants you to be in control, to be the one revealing her womanly features.  Make the removal of clothes a sensuous part of foreplay, a process with kissing and touching.  No wonder you have trouble satisfying women.” 

Billy fumbled his way removing Sarah’s clothes – and she reciprocated by undressing him.  Foreplay works both ways.

When they were naked, Billy squeezed Sarah’s breasts for about 15 seconds, then he positioned himself to enter her.

“No, no, no.  Stop,” said Sarah.  “I’m not even wet yet.  You never checked to find out if I was ready.  Yikes.”

“I guess I’m not a great lover,” Billy said sheepishly.  “What should I do?”

Sarah set about instructing him on the sensuality that gentle stroking of the body can produce.  “Start at the neck, then work your way down the shoulders.  Rub your hand down the center of the chest, avoiding the breasts.  Touch everywhere else.  Save those sensitive parts for last – make me crave that touch, make me hunger for you to touch me there, then circle the nipples.  And don’t rush.”

Together, they used her body as a canvas, a study guide for arousing a woman.  Over the course of a half hour, Billy caressed, massaged, licked, and stroked Sarah’s body.  When she was wild with anticipation, he reached to put on a condom.  “No, wait,” Sarah said.  “Let me do it.”  She slid the condom on his penis, stroking him as she did.  He loved her taking charge.  Then she guided him into her opening.  They rocked together until he exploded inside her.  Sarah felt an orgasm too. 

“Now that’s how to please a woman,” Sarah said.  “Nice job.”

Over the next few weeks, Billy often insisted to Sarah that they practice.  He wanted to hone his technique, he said, now that he understood the power foreplay possessed. This ‘friend with benefits’ thing was turning out to be a fantastic proposition – for both of them.  Their sex life was amazing. 

In bed, Sarah asked questions of Billy.  Do you like girls with pubic hair, or shaven?  What about nipple rings?  Billy asked Sarah how to use a vibrator in sex play and where his tongue felt best.  The more they talked, the more they unraveled each other’s desires and preferences. 

They each dated during this time, but the lure of on-demand ‘benefits’ was complicating their relations with others.  They had become so intimate, so comfortable with each other, that new people seeking to break into their life were almost like intruders.

Billy spent more and more time at Sarah’s apartment.  They stopped dating others.  That no longer mattered as they had so intertwined their inner lives, that there was small room for others anyway.  When she suggested that he move in, it was a foregone conclusion. The ‘friends with benefits’ sex was no longer ‘instructional.’  It was raw and passionate.  Billy didn’t need to practice to satisfy someone.  He was the Romeo he wanted to be, and she was his Juliet.  And they lived happily ever after.

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Written by NotHemingway
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