Ch. 01 - Popping the Cherry

Ray spent most of his day off taking care of his lawn. He knew he could afford to let someone else do it, but it was a point of pride that he could do it himself, and he liked being active and getting dirty. He lived in what most people would consider to be an exclusive neighborhood. Ray didn't really think of it this way. He wasn't inclined to think of people in terms of their status, but he was aware of his privileges. Mostly what he enjoyed is spending time with people who stimulated his brain and showed signs of emotional intelligence and a modicum of empathy for someone else's perspective. In his line of work, that was a rare combination of qualities, but he appreciated them, nonetheless. His home was close to family and that was important.

In the afternoon, Ray noticed his neighbor, Candy was outside flitting about. Candy was quite attractive. Her hair was perpetually in a mess of curls, she was petite, with an ample and remarkably natural bustline, somewhat talkative, and always seemed like she was late for something. Candy was tending to her rose garden and occasionally they'd chat over the hedge. Ray was usually clothed but today was so darn hot, he had taken off his shirt and he could tell Candy was more observant than usual. She kept stealing glances when he was on his deck. Ray didn't mind this. He had a nice chest and several women commented on how much they enjoyed snuggling up to it. They seemed to love the way he smelled and commented on it regularly. Ray hadn't changed his grooming habits much but chalked it up to the natural soap he used and a healthy diet. Regardless, he was enjoying the attention from his neighbor and started to think of what she looked like underneath that tight white tank top.

Just as he started to feel his cock fill with blood, Candy's husband Corey stepped out with a beer in his hand and a bottle of water for Candy. Occasionally, Corey would come outside when Candy would be sunning herself by the pool and put lotion on her back. He liked to reach around and tweak her tits and Candy would giggle then slap them away only to turn around and kiss him oftentimes taking off her top so he could fondle them freely. Many times, they'd end up making out on the deck chair with Corey pulling off Candy's panties and going down on her on the pool deck. She'd try to keep her moans quiet but eventually she'd cry out as she climaxed. It was quite arousing for Ray. Most of the time, they were blissfully unaware of Ray's presence. He knew it was impolite to stare over the hedge from his deck but occasionally when they made out by the pool, Ray felt his cock get hard and when Candy moaned, he'd stroke his cock while laying on his deck thinking of his face between her legs and Corey's dick in his ass. Ray hadn't explored this side of his desires yet, but they had been with him a while.

Just as he started to feel his dick get full, he heard Candy yell his name. "Ray! Hi Ray!" Candy waved over to him. "It's so gorgeous out, isn't it? My god this heat though? I literally feel like I could be naked and would still feel like I am wearing too much!" Then she kind of giggled. She knew Ray would immediately start thinking of what she looked like without clothes on but couldn't help flirting with him just the tiniest bit. He had such a beautiful chest, and it was a shame women unlike men, had to keep their breasts covered. It was hot and she wanted to be out of every stitch of clothing she had on. Ray waved and replied, "I know! I was dying mowing my lawn. I decided it was time for a break. Just having a beer. I see your flowers are looking great this year! You should come take a break too. Get out of this heat!" Then he remembered that Corey had gotten her some water. "If you want, both you and Corey should come over. We can all chill in the shade for a bit."

"That sounds wonderful, honestly. Corey, you want to go hang out at Ray's for a bit? His deck is in the shade! Bring over a few beers, will ya?" Candy called to Corey as he waved to Ray. "Sure... Be right there!" Corey went to grab some more beer from the outdoor fridge. They always kept some on hand for guests. Then they walked over to the back gate that separated both yards. Several years ago, they had decided to put in the gate when a tree that spanned both yards was being trimmed. It usually stayed unlocked. There was really no reason to lock it. Both households had lived in the neighborhood for years. Occasionally, Ray had girlfriends that would stay for a while but because he traveled so much for work, eventually, they would tire of being home in the house alone and move out. So, the gate became the point at which they would chat occasionally or if necessary, deliver mail that was dropped at the wrong house. Corey and Candy walked through with beers in hand and one for Ray, making their way to his back deck overlooking the luscious and green back yard. Ray sat there relaxing, shirt off, legs outstretched, and his arm draped over the lounge chair like a lazy cat. "Hey folks, I see you two were too weak for the heat. Pull up a chair. Put your feet up." Corey and Candy pulled up their chairs alongside Ray. Candy was in the middle.

They talked a bit about the neighborhood. Ray was privy to some good gossip because as a single man, he was accustomed to the women of the neighborhood trying to find out his story. They'd often find reasons to chat him up, sometimes flirting to see if he would take the bait. Occasionally, he did. Ray had an ongoing liaison with a woman, Peg, who lived two doors down who flirted so awkwardly with him, he found it endearing. Her husband was a real piece of work. He had a need for superiority and made a point to show off his latest toys to every guy in the neighborhood. Peg enjoyed finer things but wasn't nearly as extroverted or conceited. She often placated her husband and acted as a buffer for the rest of the neighborhood. Ray knew they had met in high school and that Peg was quite the beauty. He imagined that she stuck with him out of inertia and fear. Peg wasn't stupid but she hadn't worked much after her kids were born. Divorcing would mean losing everything. Peg had grown up without much. That simply wasn't an option. So, she occupied herself entertaining Ray when her husband was gone on work trips and Ray wasn't traveling. They kept it light, but the sex was amazing. It was the first woman that squirted when Ray made her orgasm, and he loved it. He'd fantasize about being between her legs eating her out and listening to her moan. She tasted so earthy and sweet. She wore this oil that she had gotten at the place where she got waxed and the mixture of her juices and oil were so intoxicating that some days Ray would bury his face in the shirt he wore when he was pleasuring her just to smell her. He thought about that now as he was relaying some gossip he recently heard about Peg's husband. Apparently, he was under indictment for embezzling funds from his law firm. The word on the street was that he was paying for an apartment near his firm in the city out of the corporate accounts. Nobody had talked to Peg for a while, but they all felt empathy for her. Secretly everyone wished she'd leave him.

Corey in a moment of boldness, probably induced by a few drinks said, "Ray, I think Peg had a real thing for you." Ray was shocked to hear someone say that out loud. He thought they were being discreet, but it was hard to not notice the way Peg would stay close to Ray at neighborhood parties or laugh at his jokes. The only one who didn't notice was Peg's husband and it was because he was too busy bloviating about some new thing he had purchased. Ray tried to respond nonchalantly, but he knew he probably didn't sound too convincing. "Oh, I don't know about that. Peg has always been the friendlier one of that pair."

"Oh, come on now, Ray. You're among friends here. Nobody here is going to judge you. She's a beautiful woman and you, in this house by yourself. Don't tell me you weren't tempted!" Corey continued. Ray looked at Corey and then at Candy to try to gauge a reaction and both were sitting there smiling like they knew an inside joke.

"Well, ok so maybe she was hard to resist," Ray said begrudgingly. "Her husband is a creep. She deserves better."

"I knew it!!!" Shouted Candy and told Corey to pony up! Both giggled and told Ray not to worry. Their secret was safe. Peg once alluded to how much she enjoyed having Ray around once during a conversation with Candy. Candy picked up on a vibe but didn't push Peg. She knew better than to pry and was the rare woman who felt it was important to respect someone's privacy. She liked Peg even though her husband was a complete chode.

Ray laughed, "You two had a bet?"

"Oh, we thought maybe you two tore up the sheets occasionally. At least that's what we fantasized about," Candy said with a salacious grin.

"What? You fantasized about me and another woman? Umm...well, I think that's flattering but also, when did you two get so kinky?" Ray asked with a laugh. They had been friends and neighbors for a long time, so it wasn't unusual for them to joke with Ray about his exploits or theirs, but it was the first time that either one had raised the subject of him being part of their fantasy life. "And why, pray tell, was I part of this fantasy?" Candy and Corey weren't exactly shrinking violets. They didn't check to see if Ray was around when they made out by the pool. They assumed he was gone most of the time but once or twice Corey did catch Ray watching and noticed his pants had a bulge. Corey didn't mind it. In fact, thinking about it made Corey hard sometimes. Candy was aware of Corey's bisexuality. They had many liaisons with other men. That they kept discreet, not because they were ashamed but because they felt it wasn't necessarily the neighborhood's business who they slept with. Though, Ray was their friend. He had known them a long time and as people go, Ray was the type to be warm and welcoming to just about anyone.

"Well," said Candy, "We thought wouldn't it be funny to happen upon you two having a fling and then, to break the tension, have you both come over and hang out by the pool. We both like Peg a lot. We know she's not going to leave her jerk husband, but we thought perhaps the four of us would have some drinks and some laughs. Who knows what could happen?" Candy winked at Ray naughtily.

"Oh, my you saucy minx, Candy!" Ray exclaimed. He knew Candy was the more gregarious of the two of them but had no idea she was that adventurous. Then he looked at Corey, "You lucky man! So, you thought Peg was hot too and this doesn't bug Candy? And I think your wife just made a pass at me!"

"Oh, she's just playing, Ray. And besides, Candy can hold her own. I just do what she tells me. Right baby?"

"Ha! Well, if you call, saying 'Yes, dear.' And doing whatever you want means you listen to me, sure! But baby you know, you're my sweet guy. I don't make you do anything you don't want to do," she said in her playful overly sweet voice that she uses when she's buttering up Corey.

"Ray, there you have it. You know who's calling the shots over there. And yes, Peg is HOT." He gave Candy a wink. "My baby is hot too. It's a good thing there's so much beauty amongst all the wildlife in our suburban haven. Speaking of wildlife, I'm sure you've experienced a few things with the women or others...." his voice trailed off slightly "you've been with, no?"

"Well, I'm not exactly the lothario everyone imagines I am, but yea, I've had a few wild nights here and there," said Ray. Ray wasn't one to shy away from awkward topics and he sure wasn't uncomfortable admitting he'd been sexual with other men in the room but to date, he'd never actually voiced any fantasies he'd had about men. Ray suspected Corey had been with men, and it was always something he wanted to ask him about but could never find the right opportunity to raise it. He knew Candy and Corey were discreet but one night, very late, he was up with a migraine and had noticed the two of them saying goodnight to quite a good-looking younger man, when he peered out his front window. He wasn't exactly eavesdropping. He had been up for hours and was bored then heard a car door slam shut. He thought it came from his driveway but looked over and saw it was in Corey and Candy's driveway. He saw Candy kiss the young man on the lips as Corey was standing next to her but then the man did the same thing with Corey. It wasn't the type of kiss you see men giving one another in European countries either. It was a full-on mouth kiss. Ray didn't think much of it. He knew what they did in the privacy of their home was none of his business, but he did feel relief to know someone else that had sexual feelings for men. Most of the men he knew that had sex with other men were gay. And while he wasn't opposed to experimenting with a gay man, he shied away because he didn't have bi-romantic feelings, just sexual feelings. He imagined feeling full or sucking a cock often as he masturbated. He had a larger dildo he'd use occasionally and put in some good MMF porn and jerk off at home. One time he had a wet dream in his early 20's while he dreamt about eating out a woman while a man was cuming inside her. He had heard about "creampie clean-up" as they called it, from a dorm mate who watched a fuck-ton of porn. It sounded gross yet strangely arousing. He once tasted his own cum and it tasted kind of pastey but it wasn't gross. "The craziest night was this night I was out with a friend at a bar in New York. We met two women and then went back to our hotel and both of us fucked in the same room then the gals switched, and we fucked the other one. It was back in my wilder days. I mean we weren't stupid. We used protection but still, it was sort of random. I suppose though if the four of us had hung out together, it would be somewhat like that, no?" as he looked at Candy and Corey.

Corey said, "Yes, probably. Of course, if you wanted to pleasure my wife in front of me, I would find that a huge turn on." Ray looked hesitantly at Candy for a moment then looked at Corey again. "Really? How would you feel about me giving both of you pleasure?"

"We'd love it!" Candy exclaimed! "One of my favorite things is to get railed hard by someone while Corey watches and then have him suck my husband's cock while I watch." Ray could hardly believe what he was hearing. "If you want, Corey will let you finish in his mouth, and I'll take care of Corey's boy pussy." He always cums hard when I pound his ass. Right honey?" Corey nodded, then she said, "Corey just likes to get fluffed up a little but the main event is him sucking a dick and getting rammed at the same time. He especially loves sucking my juices off another man's cock."

Ray's mind was racing and as Candy was talking, had leaned in. Just as she finished saying "...sucking my juices off another man's cock." Ray leaned in to kiss Candy. He had thought about what she tasted like before but always for the sake of their friendship, put it out of his mind. Now that he was hearing what they said, he felt like he was being pushed through a door with a gust of wind. He wanted this chance to feel what he had been fantasizing about for so long! Candy looked at him after what felt like a minute long kiss and said, "Well Ray, it sounds like you are in. Should we head back over to our place?" She offered Ray her hand and then grabbed Corey's too. She led them both through the back gate up to their patio door. They walked silently together but now both men's cocks started to get full.

Candy let go when they got to the door and said to them both, "Give me a few minutes while I get the room ready, then come up. I'll be waiting." Ray and Corey sat in the living room making small talk for what seemed like an eternity. Finally, Corey looked at his watch. Only 10mn had passed but he knew it was enough time for Candy to get the room ready. "Well Ray, I think it's 'go' time." Corey smiled and gestured for Ray to follow him.

Once at the top of the stair, Ray could see a door open to a large master suite. Candy stood in the doorway with a black lacy bodysuit. He could see her gorgeous full breasts. Her nipples were erect and he could see she had a bare pussy with the exception of a small landing strip right above her clit hood. Her legs were muscled but shapely. Corey waved Ray over to her and Ray took a few strides before he stood in front of Candy. She seemed a lot smaller than he imagined but then again, he had never really been this close to her without most of her clothes off. He leaned down and kissed her mouth again but this time he put his arm around her and pulled her in close. She leaned in without any resistance and then he picked up her and she wrapped her legs around his waist, while he walked her over to the bed as they continued to make out. His tongue exploring her mouth and her hips grinding against his now very hard cock. He laid her down on the bed and could see her pussy exposed and she spread her legs. She was wet and her pussy was plump like a ripe peach.

Ray worked his way down Candy's body, and he could feel her shudder as he nibbled on her breasts and stroked her clit ever so slightly. Ray almost forgot Corey was there except he looked up and noticed Corey standing on the other side of the bed. He was fully naked, and his cock was rock hard. Ray self-consciously realized he was still clothed so he stopped to take off his shorts. His shirt had been off all afternoon, and it was way too hot for underwear so once he had his shorts off, he too was naked, and his cock was thick and pulsating. Ray was a well-endowed man. He didn't really think much of it, but he had a few girlfriends remark that his cock was larger than average. Certainly, it wasn't porn star big, but he felt confident that it did the job.

Candy by this time had sat up to take in Ray's body. She thought he looked amazing. Candy always loved Corey's body. He was built like a swimmer. He had a thick broad torso and lean long legs. She always loved that he was so lithe. It made sex fun because he was so flexible. Ray was more of a football player. He had a good 50lbs and 3 inches on Corey. He was hairier too. Corey always had little body hair and he shaved what little he did have. It was a bit of a habit since high school. It made him uncomfortable. Corey's cock always satisfied Candy too. It was smaller but thicker. She called it "cute." Sometimes that made Corey cringe a bit, but he knew she loved every inch of him. He liked being manly but had decided ages ago that comparing his body to every other man was going to make him toxic. He embraced what he had and kept himself fit. He was a confident and skilled lover and if his partners were happy, so was he.

Ray's muscles bulged as his body tensed up. He was fit for the most part, but his six-pack abs had slightly more padding than he was comfortable with, but he wasn't racing to have the body of a 20-year-old anymore either. He noticed how much larger he was than Corey in stature but also how much leaner Corey was. "My god, how does that fucker stay so fit?" he thought, but then quickly put that out of his mind. He wasn't there to concentrate on his body, he wanted all his focus to be on pleasuring someone else. Ray looked down and noticed that Candy had put her hands around to his backside and was nuzzling her face into his groin and working her way down to his hard cock. She was absolutely wild about his treasure trail. She noticed that today when they were sunning on the deck and thought about how much she'd enjoy following it to the prize he kept in his pants.

Ray stopped to enjoy Candy's affection but then gently pulled her away and told her to lean back. He wanted to make her feel good. Candy looked up and smiled and said, "Yes, sir." Oh Ray enjoyed that! He liked being powerful and in control. Ray went back to kissing Candy's neck then breasts while he resumed stroking her clit with his hands. He used his thumb on her clit like a joystick and slipped two fingers inside her to find her g-spot. Every time he hit the spot he could feel Candy tense up. She'd moan a little and say, "oh god, yes." He loved getting that kind of feedback. It made things easier. Every woman was a little different. So, it took time to get to know their body. After getting her worked up with his hands he moved down to her pussy with his mouth and gently started kissing her labia and licking her clit. Sometimes he'd probe her pussy with his tongue slightly but then kept working her clit with his finger to keep the pressure up. He would always get so excited whenever he'd be eating a woman he'd murmur slightly. He had a thing for smells and a woman's wet pussy was about the most delicious thing he could think of to eat. The smell was intoxicating, and the taste was always warm and earthy. In this moment he felt like he was her fuck toy. It felt liberating because he knew this was pure pleasure. That's it. He didn't have to worry about what happened next. He could just remain in the moment.