Benefits Of Friends

Do you want to fuck me, Chan?

Chan stared at his phone, contemplating on how to respond to the unexpected and very forward text he had just received from his friend, Cleo. Chan had just returned from a wedding reception where the tequila was flowing, which meant his wife went straight to bed and was fast asleep. Tequila, however, had the opposite effect on Chan, making him horny as fuck and not of completely sound mind.

To date, Chan and Cleo has been purely platonic friends. Cleo had been a widow for a few years and was busy raising her three children. Chan's kids were already out of the house and was in the empty-nester stage of life. Sure, there was the occasional flirting between them, but never anything that indicated it would escalate beyond friendship. Truth be told, Chan had always been very attracted to Cleo, especially since she was now a widow of a few years.

She was a sultry blonde beauty with smooth alabaster skin that liked to flaunt her buxom tits and had a curvaceous ass that most black men would drool over. Further, Cleo had a witty and lewd mind that Chan found to be a very endearing quality. Cleo didn't shy away from exposing her sexuality and is definitely the type of woman that he would pursue if not married.

Chan, however, had a history of misreading women, recently being told from a couple of friends that they wanted to fuck him back in high school, which resulted in a "now you tell me" moment. Suddenly Chan finds himself in a situation where a woman he is very attracted to is blatantly asking him if he wants to fuck her...so he is fairly confident he is not misreading this.

Chan is running every response option through his head. If I say yes, then I get to fuck a woman that I've wanted to for several years. But maybe this is a trap question - though not friends, Cleo and Chan's wife did know each other. If I say no, then I miss out on the opportunity to experience what he knew would be an incredible sexual experience....and declining such a forward question would likely make things awkward in their friendship moving forward. After what seemed like an eternity he was about to text his response when he noticed that Cleo was sending a follow-up text.

Was it just me or was there something different about our chemistry when we met for drinks a few weeks ago?

Cleo texted. She was referring to a meeting over cocktails that they had earlier in the month when Chan was visiting his hometown. While Chan and Cleo were hometown friends he no longer lived in the area, so they would occasionally meet over cocktails to catch-up when he was in town.

Cleo continued,

As I was driving to the pub that night I had the realization that I wanted more from you than just friendship. I started fantasizing that after a few drinks we would go back to my house for a nightcap. But when we entered the front door I would drop to my knees, pull down your pants and start sucking your cock until you were rock-hard

.

Chan's eyes popped out of his head as he couldn't believe what he just read...but Cleo continued typing.

I would then stand up, bend over my couch, yank my pants down, pull my thong to the side and tell you to fuck my wet pussy like an animal. Not ask you to fuck me...TELL you to fuck me. You would plow into me, alternating between a fast and slow rhythm until I moaned uncontrollably. You would pull my hair back, call me a whore and tell me that you owned my pussy. You would randomly smack my ass until it turned red, aggressively grab my hips while thrusting into me, causing a flow of my white cream to cover your cock. I would ask you to tell me when you were about to cum, at which point I would spin around, and you would unload all over my face and tits. Afterwards I would scoop up your cum and lick it off my fingers...and then lick all of my pussy juices off your cock.

Chan was in disbelief at what he was reading, but the hardness of his cock was proof enough that he indeed did want to fuck Cleo. And Cleo was absolutely right - there was a different chemistry between them the last time they met. It was a very intense flirty and touchy-feely meeting, bordering on PDA. Had they been in a quaint hotel lounge bar instead of a local restaurant bar Chan had no doubt they would've ended up together in a hotel room that night.

In a response that would change the course of his life Chan texted,

yes, of course I want to fuck you...I always have.

This set off a chain reaction of primal back-and-forth texts, each revealing sex acts and kinks they wanted to do to each other.

I'm a very independent woman

, typed Cleo

but I love being controlled in bed...I want to be subservient to you...I want you to be rough with me...I want you to tell me what to do and I will do it without question

.

Despite having a couple too many tequila drinks, Chan's cock had never been harder in his life. Though he had a wife lying in a bed no more than 15 feet away that he could arouse from her slumber and fuck senseless, his total focus was playing this fantasy out with Cleo.

Chan texts,

OK, now this is my version of how that night would've played out. After having a late Friday afternoon drink at the pub, we adjourn to your house and have dinner with your kids. The kids bolt for the door to attend high school parties as soon as the last dish fills the sink. You saunter over to the sink to start rinsing off dishes before placing in the dishwasher.

You are wearing your cut-off jean shorts and your tight green button-up short-sleeve shirt that flaunts your tits. As I stare at your body and your flowing blonde hair I catch your beautiful face in the reflection of the window above the sink. All of this imagery makes my cock stiffen quickly. I approach you from behind as you are finishing up the last few dishes. My cock is so hard it hits your ass as I wrap my hands around your sides and massage your tits. You let out a slight moan as I lean in further and whisper 'I have the perfect idea for dessert'.

With that I rip open your shirt, unclasp your bra, and massage your tits even deeper. I turn you around and we lock lips, which quickly turns into our tongues dancing aggressively in each other's mouths. I reach my hands around and grab your ass, lifting you off the ground and onto the nearby island. While we continue to probe each other's mouths, I reach down to unzip your shorts. As I shimmy them off I notice you have no panties on and I say, 'what a good girl'. This comment makes your freshly shaved pussy quickly glisten, but I intend to make it gush. I push your legs apart and slightly up, giving me the perfect angle to feast. I dive in ferociously - kissing, licking, and sucking every inch of your inner legs and pussy

.

Wait, wait, wait,

texts Cleo, adding,

I need to get my dildo out to virtually live this out. I am SO FUCKING WET right now

and adds multiple water droplet emojis to her text.

Chan continues,

I sink my index and middle finger into your pussy while starting to lick and suck on your clit. Your moans get more intense, indicating that my fingers have found the right spot, so I start rubbing inside you more aggressively. As I simultaneously suck on your clit your pussy starts flowing with your sweet juices, which I lap up with abandon. Though I have not satisfied my craving for your pussy I pull my fingers out and put them near your mouth and say, 'have a taste'. You have a ravenous look on your face as you gladly accept my fingers into your mouth and suck all of your pussy juices off

.

Please tell me you're going to fuck me Chan

, interrupts Cleo.

Between your texting and my dildo, I've already cum twice. I NEED YOU TO FUCK ME!

and adds an eggplant emoji.

Impatient, aren't we?

replies Chan with a wink emoji.

As I continue my tongue assault on your pussy I look up and see that you've braced yourself on the island with one hand but are massaging your tits with the other. 'Let me help you with that' and I reach up and start to massage your tits and gently pinch your nipples. I raise my eyes back up and see your mouth agape with a vacant stare into space, as if you are trying to curb your need to orgasm. I replace my tongue with my fingers in your pussy, kiss my way up your torso and stick my tongue in your mouth. You accept it greedily as you love the taste of your pussy.

As we continue to explore each other's mouths I reach down and subtly remove my pants and boxers. I line up my cock with your entrance and slowly push in. You let out a muffled moan as we are still hungrily kissing. Realizing the island is too high off the ground to gain full penetration I ask that you wrap your arms around my neck. I slowly wiggle your ass off the island while holding underneath your knees with my arms and your pussy drops onto my cock to the base.

FINALLY!!!

, interrupts Cleo.

My arm is getting tired from thrashing my pussy with this dildo. I'm getting my vibrator out to take over from here.

Once off the island I look around the kitchen to determine the best place to rest you for full penetration. The kitchen table is the perfect height and made of very sturdy oak. I rest your back on the table, lift your legs akimbo and start rhythmically plunging my cock into your soaking wet pussy. I wet my thumb and reach down to stroke your clit. I pick up my cadence and my balls are smacking your asshole with each thrust.

The vacancy in your eyes returns and I know you are on the verge of cumming, as am I. Ultimately you scream out that you are cuming and that sends me over the edge. After a few more strokes I pull out as ropes of my cum spray all over your tits and stomach. Silence fills the room as we look deep into each other's eyes and lean in for a passionate kiss

. Chan stops texting to wait for her response. A 1/2 minute passes with no response.

Well Cleo?

Oh, my fucking god!!! I'm sorry, that was so intense I nearly passed out...and my bed is an absolute swamp right now. We need to make this happen, Chan...but how do we do that with you in town so infrequently?

Chan quickly surveys his work calendar and realizes there is an industry trade show scheduled in a couple of months within 40 miles of where Cleo lives. The bonus is that he will have his own private room in a nice hotel, making it perfect for a covert rendezvous.

Block off May 14-16 and we will make this work

, texted Chan.

Well, Chan, I still have kids at home and I can't abandon them for days. But they are fairly self-sufficient, so I can definitely figure out how to make it for one of those nights. Does that work?

responded Cleo.

W

ell then, we are going to have to make a VERY memorable night,

Chan texted

. One that is fueled by passion and filled with frequent fucking

, adding several eggplant emojis, peach emojis, lip emojis and water droplets emojis.

OMG, you are making it rain again

, responded Cleo.

Now the hardest part begins...waiting 7 weeks for fulfillment...the 7 longest weeks in the history of time.

Although the rendezvous was 7 weeks away, Chan and Cleo kept in touch frequently. Like every day and multiple times a day, sharing things they have never really discussed before. They still texted about normal every day stuff like politics, family matters and the mundane. One of the many things where they discovered an unknown commonality was their love of Formula 1 Racing. With the Spring schedule being raced on the other side of the world all of the start times were early on Sunday mornings. Chan's wife typically did not roll out of bed until 10am on Sunday so this gave them ample time to privately text about a sport they loved while watching the early morning races.

Of course, both of them frequently had sex on their minds so these text threads were often filled with double entendre such as Chan texting,

the track is getting wet.

And Cleo responding back,

that is not the only thing getting wet...my pussy is aching to feel you inside me

. It is no wonder that when Chan's wife did descend from the upstairs he typically had a raging hard-on.

That initial text thread had opened up a broad new conversation, often focused on sexual preferences and desires. They both knew they had perversions that they hadn't readily shared with each other, but that had changed. This had now become a relationship with much more openness and transparency.

Cleo had been single for a while and was looking for something more concrete for her remaining days. Something that Chan couldn't currently offer her. Maybe had they met at a different time and a different place in their lives, it would've been different. Who knows. Wondering about 'what ifs' is a fruitless endeavor.

Chan was certainly not blind to the fact that Cleo had a life outside of their texting binges, including pursuing a relationship with another man that might become her husband someday. Chan was encouraging with respect to Cleo going out to find Mr. Right - she was a good friend, a better person and all he wanted for her was the happiness she deserved.

She never shared all of the details, but Chan was certainly aware that Cleo loved the company of men and pursued it aggressively. Was there jealousy? Absolutely not. Was there envy? Absolutely...I mean one would have to be a eunuch not to be envious of another man that got to have sex with Cleo. But there was something else that Chan felt...utter and total arousal. When Cleo would mention she had a date, he fantasized about being in a hotel room with them as a voyeur, sitting adjacent to the bed and watching her get railed by some other man or multiple men. If someone viewed Chan's browser history it would show that spent a vast portion of his free time searching Reddit for amateur porn, with a penchant towards voyeurism, multi-partner sex, interracial sex and lesbians. So, it was no surprise that his fantasies about Cleo revolved around these themes.

As the weeks slowly rolled by they continued their text thread, which had escalated to 75+ exchanges a day. These exchanges eventually got flirtier as Cleo would send pics of herself in leggings and sports bras while doing Pilates. Seeing her ass and tits wrapped tightly with slight perspiration on her body was thrilling to Chan. If her intent was to give Chan wood, then mission accomplished. More than that it inspired Chan to up his game at the gym, increasing his weight and core training. She had already admitted to liking it rough in the bedroom and he wanted to be prepared to toss her around like a ragdoll.

The daily exchanges continued to get more and more bold, including Cleo sending pics of her dressed in sexy lingerie or in a halfway unbuttoned shirt exposing her bountiful cleavage. Chan would respond with pics of him lying in bed in just his boxers with a clear bulge protruding to the side, adding comments like

this is what happens when I think of you

.

On one particular night the texting went next level. During their routine exchanges that night Chan mentioned his wife had already gone to bed for the night. Knowing this information Cleo then sent a pic of her favorite vibrator strategically placed between her tits with the comment

this is where I want your cock right now

.

Chan's cock quickly stiffened and responded,

are you going to use that tonight when you think of me?

Chan waited for what seemed an eternity for a response. Finally, his phone buzzed. When he opened the message, it was a pic of Cleo with her vibrator buried inside her wet pussy. It seemed impossible, but Chan's cock got even harder and he felt compelled to show Cleo the impact it had on his shaft. He quickly moved to his downstairs guest bedroom to ensure privacy.

Before he could get in position to take some dick pics his phone buzzed again...upon opening the message he could see it was not a pic from Cleo, but a video clip. The video clip was dark at first, but Chan could definitely hear a humming noise and Cleo moaning. As her camera adjusted to the low light he could see that Cleo had her panties pulled to the side. She had her g-spot vibrator inside of her while rubbing her clit on the outside. Her panties were getting soaked as she continued to maneuver the vibrator in various positions, moaning the entire time.

The skin on Chan's cock could not stretch any further - he hadn't felt such hardness since he was in his teens. He quickly snapped some photos of his cock in various positions and sent to Cleo.

THAT is what I've been wanting to see. Your cock is beautiful. I can't wait to have it inside me. Inside my mouth, inside my pussy, and pulsating deep loads of cum inside of me

, Cleo texted.

I cannot wait for that to happen

, Chan responded. While Chan never had any doubts, this rendezvous was going to happen, this night sealed the deal in his mind.

As the calendar rolled from April to May Chan was starting a new job and had to drive to his new company's headquarters, which was a 6-hour drive. At the same time Cleo was returning from a quick trip to the west coast, where she had visited a friend and attended a retirement event. When she arrived back on the east coast Chan was halfway through his drive to HQ.

Chan loved hearing Cleo's voice, so he called her. They shared a lively conversation filled with laughter. It was a great reminder that they were still very good friends that could have normal conversation. Chan spent a few days onboarding with his new company during the day and continued his text exchanges at night with Cleo. Chan stayed over in his HQ's city over the weekend as he had to attend a company retreat about two hours away in a very rural setting.

During the weekend Cleo sent Chan a text inquiring,

Do you think we need to talk about...um...protection for our get together in a couple of weeks?

Chan hadn't worn a condom in almost 30 years and didn't relish the idea of doing so.

Is there a reason for concern? There certainly isn't on my end

, Chan responded.

Well, you know I don't practice celibacy and I have been on a few dates the past couple of months

, Cleo responded with a wink-wink emoji.

Oh, I know. I've never considered this an exclusivity thing between us and I know your libido is as high as mine. You know I want you to find a guy that will make you happy. I was just questioning if you had sex with someone that you later found out passed something onto you?

questioned Chan. And in this moment, he speculated that Cleo's friend visit on the west coast was more than just platonic. He frankly didn't care if it was or not as he knew Cleo was as sexual as he was.

Well, I don't know at this point as STDs sometimes take time to rear their ugly head. I just don't want to put you at risk for having to explain how you picked up an STD to your wife. Understand?

Cleo asked.

Chan responded

well, if we must, we must,

with a crying emoji added on. Bareback is all Chan had known for 3 decades and the thought of using one now would lessen the spontaneous passion that he had planned for their night together. He could tell that Cleo was a little taken aback at how nonchalant Chan was being about this.

The next day Chan drove to his company retreat and pinged Cleo to see if she could talk to fill the void. She called Chan and the conversation was much different than they had a few days ago. There was no off-the-cuff dialogue, there were many moments of dead silence and it seemed like they had to think hard how to fill the time. It was an awkward conversation. One you might have with someone you barely knew...not someone that had been a long-time friend. Chan went to bed that night with an uneasy feeling, thinking that maybe his questions about condom use had swayed this in a negative direction.