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Note: This story is based on earlier story 'Sister-In-Law' (Literotica, June, 2021). That story was true, but this story expands into a fantasy based on one part of that story. Like in the original story, all characters are at least 18 years of age.
It was a warm Friday night in the summer, and Russ and Gary were bored. Like most guys in their early twenties, they wanted to be around other people their own age, and hopefully meet some similar-aged girls. But it was too hot and too muggy to put on dressier clothes needed to get in local clubs. Tonight was a shorts night. And beer night. And car night...
The best place to meet girls without getting dressed up was at one of the local strips frequented by others their age. They loaded into Gary's Mustang, and 15 minutes later they were surrounded by cars popular with young people, and those borrowed from young people's parents. They knew most sporty cars would be piloted by guys, so they timed each trip up and down the two-mile stretch where they would be surrounded by Mom-mobiles.
On their third time up the strip, a blue four-door sedan slowed down next to them. The driver was a cute brunette, and even in the limited light of oncoming cars they could see she had a big smile and vibrant green eyes. Her passenger was an equally-cute blonde who wasn't quite as outgoing as the driver. After quick introductions the sedan followed Gary and Russ to a parking lot where they could get out of their car seats and to get to know everyone better.
When they all exited their cars, the first evaluations took place. Gary was 6' 2" and slender while Russ was 5' 10' and stockier. Lisa was 5' 5" and petite where Tracy was 5' but curvy. There was enough attraction that no one was eager to leave, and by the end of the night, Gary was talking more with Lisa while Russ and Tracy were hanging out. Each new couple set up dates for the following night.
Gary was in college, home for the summer, while Lisa had just moved south from a small town in Michigan. She was a cute brunette with those bright green eyes, but was nothing like other girls he had dated -- she was shorter, and with a more petite figure - than he was used to. But he'd been single for a while, and the way she kissed him after he asked her out - with some heat and a ton of seduction - was definitely intriguing.
'What the heck', he thought as his erection grew in his shorts while her tongue probed his mouth and her body pressed against his, '... it was just cruising and maybe a summer fling'. He'd done the girlfriend thing a couple of times, going out for months before trying anything sexual. Lisa's flirty, outgoing personality had tons of potential and was worth trying a few dates.
On their second date when he kissed her 'good night' at her front door, she ground her hips against his, her forbidden mound of pleasure pressed hard against his dick, which quickly stood at attention. He needed something -- anything -- more than a kiss to get him through the night until he could get home and enjoy the seduction of his right hand.
"You kiss really, really well," he said shyly.
"Really?" she asked.
"Uhhh... YEAH!" he whispered trying not to wake her parents.
He pushed his erection harder against her stomach again for emphasis.
"Better than the girls at college?" she asked teasingly.
"None of those girls ever did this to me with just a kiss..." he said as he again pulled her close and pushed the erection she caused into her stomach.
He kissed her again, and as she ground her body into his, he moaned in pleasure. But there was also desperation in the sounds he made. He was 21 and got hard when the wind blew, but her teasing was much more intense than a blowing wind.
"My first girlfriend would sometimes let me come to her window and watch her change into her pajamas before I went home," he said, trying to not sound like he was begging. "Any chance we could do that? You've gotten me pretty worked up."
Lisa never answered, but again kissed him even more passionately than the first time. She made sure he was even more aroused before whispering, "Good night!".
Gary wasn't sure if that was an invitation or not, but she never said 'no', so he drove around the corner, parked, and snuck back to her window. The light was on and the blinds open, and when he peaked in, Lisa was standing naked waiting on him. It was so much more than he was hoping for, and he quickly took in every part of her body. Her brunette hair was long and fell down her back, and her green eyes seemed to sparkle at the thought of teasing him. She wasn't athletic, but there was not a single ounce of fat on her body. Her boobs were probably 34Bs covered with dark pink nipples that weren't as large as his previous girlfriends but big enough to make his mouth water. Her waist curved sexily into her hips which framed a perfect triangle of dark hair between her legs. After she was sure she had teased him enough, she ran to the window and opened it.
"Wow, this is incredible - you are so sexy!" Gary whispered excitedly as she leaned out and again kissed him. "I was just hoping to see some pajamas, or maybe panties, but this?! SO much better!"
Lisa said nothing, but waved 'good night' as she backed to her bed, giving him a few more seconds of a show. She smiled seductively and she pulled the covers up over her naked body then turned out the light.
If the kiss hadn't been arousing enough, Gary was now about to explode. As he snuck back to his car, he wondered if he could survive the 30-minute drive home before relieving himself. Since his erection was making it difficult to walk, he wasn't sure he could survive the drive. He also didn't want to drive -- he wanted to jack off while the image of his sexy, naked date was still on his mind.
Gary entered his car and looked around. The street he was parked on was a side street with no houses on it. It connected two of the numerous parallel streets of comfortable homes in the comfortable suburban neighborhood. He could see streetlights on the main street ahead and behind him, but neither cast light on the connecting street where he parked. His tinted windows were the final level of security as he decided to undo his shorts and slide them and his underwear down.
'Hello old friend,' he thought as his hand wrapped his erection. 'Something tells be you're going to get to meet Lisa VERY soon...'
He closed his eyes and remembered her naked body. He wanted to fantasize about how she felt to his touch, and how they would get to know each other physically, but after he moved his hand up and down his erection a few times, he knew this would be too fast for much fantasizing. He thought about trying to prolong his orgasm so he could imagine sex with the petite brunette, but that wasn't going to work tonight. He decided his best bet was a quick, rapturous release to enjoy the vision still fresh in his mind.
Gary closed his eyes, and as he remembered her smooth, pale skin, his hand pumped up and down his shaft like so many times before. He remembered her tits, and though they weren't as big as recent girls he'd been with, they were still noticeable for her more-petite body. Then he remembered the hair between his legs and wondered if she would let him taste her womanly essence. Then he remembered that mischievous smile, and the way she kissed him at the window, naked, and oh-so close. Then he felt the familiar pleasure, then tingling he loved so much, and he opened his eyes in time to watch stream after stream of warm, white, sticky fluid shooting out of his purple head. Then the pleasure became too intense, and the streams of ejaculate were mostly done, and he lessened his grip and coaxed the last few drops of cum out. Much of his many streams had landed on his shirt, a few on the car seat, and one even hit the headliner. He took the shirt off, cleaned as best he could, then started the car.
* * * * * * * * * *
On their third date Lisa and Gary got into a hot tub at a friend's apartment complex. It was mostly dark, and they were alone, and when he teasingly tugged at the string holding her bathing suit top in place, she took it and her bottoms off. After watching her at her bedroom window a few nights ago, she was now naked and available for him to touch. She was also very affectionate and never hesitated touching him or asking him to touch her. She sat in his lap facing him, and ground her pussy against his erection, tempting him with the possibility of being inside her. After first seeing her naked a few nights earlier, he could finally touch her body, feel her boobs, put a finger inside her, and have her touch him. There had never been so much promise so soon after meeting someone, but he still believed that women wanted relationships before sex. He didn't realize that she wasn't teasing him - she was offering him everything he wanted. He was aware, though, that for the first time in his life, not everything that happened between he and his sex partner had to be initiated by him.
Gary quickly realized this relationship would be different. There was no trying, then being rejected, then trying again, and maybe getting lucky a few days later. Lisa wanted sex as much as he did and never hesitated to offer herself to him. The next date after the hot tub she got naked in his car and gave him their first blow job, and then asked her if he wanted to fuck her. He desperately wanted to, but the tightness of his back seat stopped them from being together for the first time. This became especially annoying to Gary when he learned she was on the pill.
A few nights later she asked him to again come to her bedroom window. For the second time, she was naked when she greeted him, but this time she opened the window enough for him to crawl in. This time, when she turned her bedcovers back, it was an invitation to him, and he fucked his third girlfriend for the first time. Then, for the first time in his life when he said "I'm about to cum", she said, "you can cum inside me."
* * * * * * * * * *
Russ and Tracy went out a few times, but they soon went their own ways. By July, Gary and Lisa were together most nights, and soon Lisa started inviting her best friend on some outings so they didn't lose touch. Gary didn't mind since their extra partner was very cute, nearly as outgoing as Lisa, very fun to look at. She was exactly 5 feet tall, and even though she was small compared to Gary, she had a very round butt and a chest that seemed large on her tiny frame.
Some nights when they were together, Tracy flirted with Gary nearly as much as Lisa did. He didn't mind, and from the way Lisa acted when they made suggestive comments to each other, she didn't mind, either. Gary enjoyed many naughty thoughts about his girlfriend's best friend and often fantasized about being with her when returning home after being with Lisa. He was very careful, though, to not comment about her friend.
The week before he headed back to school, Lisa was trying to understand how their relationship would work with her home and him away at school. She invited a few friends over to cook out and swim in her parent's pool. Her goal was to have a great time with friends, then have amazing sex with Gary so he would want to come home often for more.
About 11:00, most of the people had left, but Lisa, Tracy, and Gary were still enjoying drinks in the pool. Lisa's mom or dad came out occasionally to make sure no one was getting too friendly, but for the most part they left the young people alone. The three friends laughed and teased each other, then right after Lisa's dad checked on them, Lisa snuck up behind Tracy, quickly untied her bikini top, and swam off with it.
"Gary, you've always wanted to see Tracy's tits -- here they are!"
She giggled as she swam away from her short, topless friend. Tracy knew right away she wouldn't Catch her more athletic friend, and she had enough of a buzz she didn't care who saw what. It was dark, and the cool water and warm night air felt exhilarating on her naked skin. She and Lisa had skinny dipped before, but never with guys in the pool, and this was new and exciting. In the darkness, she could tell Gary was looking in her direction, but she couldn't tell how much he could see, if he was staring at her, or if he was happy with what he saw. She slowly walked to the steps then over to the table where Lisa was waiting.
"I... uhhhh... never said that!" Gary said defensively.
He was 99% sure he'd never said anything about Tracy's boobs, but he knew for sure Lisa had seen him checking her BFF's body more than once. She'd definitely caught him a few times that night when it was hard not to look at her in her tiny bikini. There had been a few other times as well when they were hanging out, especially when Tracy wore very short shorts. Then, there was all the flirting they engaged in. Gary thought he'd been discrete, but maybe he wasn't -- either way, he WAS so happy to finally see them, even if it was in very dim light. But now he also wanted to touch them, hold them, feel their weight in his hand before sucking each of her nipples...
And as his mind quickly rolled through so many possibilities of how he could enjoy Tracy's boobs, he was quickly so erect he couldn't get out of the pool without being obvious. Tracy walked to the patio where Lisa teasingly held her bikini top. She graciously took it with one hand, but with the other, she took Lisa's hand in her own. Lisa was unprepared to resist, and when Tracy pulled it up to her chest, she was mostly helpless. For a second, her hand felt Tracy's boob before she laughed and quickly moved it away.
"Heck YEAH!" Gary yelled out as Lisa's hand briefly touched the boob he wanted to touch so badly.
The girls laughed at Tracy's predicament, then at Lisa's response, and finally at Gary's comment. No feelings were hurt by Lisa's prank. But Tracy wanted the last laugh and turned to directly face Gary as she slowly put her top back on. The two girls were closer to the den window, and in the slightly-better light Gary finally got a better view of her amazing tits. He didn't blink as she purposely put her top back on as slowly as she could. Once she was again dressed, she grabbed her towel and keys.
"It's been fun, guys, but I think I'm going to go meet Antonio," she told them.
"Gary, you probably shouldn't get out of the water -- no need to show us your boner!" she said with a smirk. "You guys have fun, and Lisa can tell me all about it tomorrow."
She gave Lisa a hug then exited the back gate. As they heard her car start, Lisa jumped back into the pool and approached Gary. She snuggled up close to him and felt his erection pushing into her stomach.
"Is Antonio her new boyfriend?" he asked as she continued to tease him.
"No, Antonio's her vibrator. We both bought one as soon as we turned 18."
"You have one, too?" he asked, more than a little intrigued.
"Yeah, I do. Does that bother you?"
"No, not all," he said, excited about more possibilities in their new relationship. "Do you use it?"
"I wouldn't have bought it if I wasn't going to use it. Remember the first night you saw me naked through my bedroom window? And I crawled in bed naked..."
Gary realized his new girlfriend was telling him she'd used the vibrator while he was jacking off in the car a few houses away. He really wanted to talk more about that, but she was rubbing her hip against his erection.
"Oooohhh, someone's horny..." she said as she continued grinding against his hardness.
She kissed him, and as her tongue forced its way into his mouth, she pulled back just enough for her hand to reach between them. She went inside his swim suit, and when she grasped his erection, he moaned.
"Is this because of Tracy's boobs or because I said I have a vibrator?" she asked.
"Oh, fuck that feels good...", he stammered. "It's because you're touching it."
He didn't want to tell her it was also because of seeing Tracy's boobs and learning about her vibrator.
"Better than my mouth?" she asked.
As she waited for his answer, the back patio light came on. Lisa quickly took her hand out of Gary's suit just as her mom stuck her head out the door.
"Leese, we're going to bed. You guys be GOOD!"
She emphasized the 'good' then closed the door and disappeared in the house. She left the patio light on to dampen any extra-curricular possibilities.
Lisa knew her parent's night time drill and knew she would again be teasing her boyfriend in a matter of minutes. She slowly swam around the pool by herself as she watched the window in her parent's bedroom come on. They often did this when she had company so they could keep an eye on her until the last minute. Snuggling up next to Gary too soon would invite them back out. As she swam the light in their bath came on, then a minute later the bedroom light went off.
"Dad's in bed..." she whispered.
She got out of the pool, went to the den door, opened it and turned off the patio light her Mom had just left on. Gary's eyes struggled to readjust to the darkness, and all he could see was the parent's bathroom light and the den door barely illuminated by the distant light from the entryway. It was now mostly dark in the back yard.
Lisa stood at the edge of the pool and looked toward the remaining light. In seconds, it was off leaving the sliver of the moon and a few stars as the last illumination.
"Mom's in bed," she said.
As Gary looked up at her, he could see her taking off her bikini. Once naked, she walked down the stairs and toward her very surprised boyfriend. He'd seen her naked a few times and had committed every bit of her body to memory. But he'd never seen her naked with her parent's home, just one wall separating them.
"Where were we?" she asked as she again slid her hand in his suit.
"Oh yeah, right here," she said with a naughty grin.
She struggled to suppress her naughty giggle as she stroked his dick.
"Does this feel good?" she again asked.
"Oh yeah, it feels really good," he whimpered.
"Better than my lips?" She asked.
She released her grip on his erection, took one step back, undid the snaps on his suit, and pushed it down his legs.
"It feels really good..." he panted, "but your lips feel even better."
He couldn't believe how aroused he was standing in his girlfriend's pool naked - her naked, too -- just a couple of minutes after talking to her parents. He pulled her close so that her body again caressed his erection, and he kissed her mouth, neck, breasts, mouth again. He was in a frenzy, wanting all of her all at once.
"Sit on the side," she whispered when she was finally able to get a word in.
Gary did as she asked, and once on the side she eagerly took him in her warm, wet mouth. She teased him a few times before releasing his cock into the coolness of the night.
"So, you're sure my hot, wet mouth feels better than my hand?" she said seductively while looking through the darkness into his eyes.
"Yeah... a little... but I like both..." he whimpered.
She smiled, stroked his cock a few times, then again took him in her mouth. This time she let her teeth add the smallest amount of pressure as her mouth sucked him. She hadn't tried this on him yet, but it had been well received by other guys she dated.
"Oh fuck, that's amazing!" he moaned.
She again let him fall out of her mouth but quickly stroked him.
"But if you had to choose one way to cum right now -- hand or mouth?"
To emphasize her question, she stroked him a few times then again took him in her mouth. This time her teeth applied a little more pleasure while moving up and down his shaft, and she sucked as hard as she could.
"I want to cum in your pussy!" Gary moaned as she expertly worked his erection, trying to extract its manly fluid.
"That's later," she teased without breaking eye contact. "I want to spend the night with you in the rent house, and make love to you, and feel you cum inside me... more than once. But I know you're a guy and probably can't wait that long. How do you want to cum right now?"
Gary didn't have to think long.
"In your mouth," he almost begged. "Can I cum in your mouth?"
"Good answer," she told him. "I think I give really good blow jobs."
She had given him blow jobs a few times, usually in his car. But she hadn't yet let him finish in her mouth. Tonight was a special night, though, and she had so many plans. She took him in her mouth, this time with a purpose. Tonight, as she tried to convince him she was his girlfriend even when he was away at college, she wanted him to know every treat she had to offer him.
"Are you OK if I swallow your cum?" she again teased.
She wanted him fully aware of what was about to happen, and she wanted him thinking about it while it happened.
"Yeah, I'd love that," he panted. "I've never done that before..."
"And then I'm going to kiss you..." she added.
"OK," he stammered.
He'd definitely never done that before. But as she continued to suck him, he would have agreed to anything she wanted.
"Did you like seeing Tracy's tits?" she asked during a break. "I took her top off because I thought you'd like that."
But before he could answer, she again took him in her mouth. Even though he'd forgotten about his first time seeing her best friend's amazing tits, they were now all he could think about. For a second, he even imagined she was the one between his legs feverishly working for his essence. As he fantasized about the small, busty, blonde sucking his dick, his body began spasming as the first streams of his ejaculate shot into Lisa's mouth. This made her even hornier, and she moaned as she worked for the next spurt, then the one after that. As she felt his body relax, she released him and looked into his eyes, and as she promised, she put her mouth to his. She had swallowed most of his cum, but she shared the last bit with him while again stroking his shaft. Gary was enjoying more firsts -- his first time cumming during a blow job, and the first time tasting himself.
Lisa turned her back to Gary, snuggled in close, and pulled his hands to her tits.
"Did you like that?" she asked seductively.
"Yeah, that was great. I wasn't sure if I'd like the taste of it, but it didn't bother me. It was kind of sexy..."
As they talked, he kissed her neck and enjoyed the feeling of her boobs in his hands. Then he felt down her stomach and finally went between her legs. She whimpered as his finger worked between her legs to her clit.
"Is the rent house still vacant?" she asked as she placed her hand over his, encouraging him to continue touching her.
"Yeah, the new couple doesn't move in for a few weeks."
Gary's parents had a house they were renting that was vacant until the first of the month. They asked him to stop by often, turn on lights, occasionally hang out so it wasn't obvious it was vacant. He had taken Lisa there once when they needed a secluded place for a quick fuck.
"I was thinking maybe we could go there tonight, if that's ok. I want to spend the night with you before you go back to school."
"We can do that," Gary answered.
Most of the sex they'd had that summer had been in his car, or in her bed when he snuck in late at night, or before her parents got home from work. It was better than his car, but there was always the concern that someone could walk in unexpectedly.
"Give me a few minutes..." Lisa said as she got out of the pool.
Gary watched her walk naked across the deck, wrap a towel around her body, and disappear into the house. By the time he retrieved his swimsuit, found the clothes he'd worn to her house that afternoon, cleaned up the beer cans, and straightened up the pool area, Lisa returned in small shorts and a top, carrying a bag and a few blankets.
"I left my parents a note you were dropping me off at Tracy's house," she whispered. "She's going to pick me up there tomorrow and bring me home."
* * * * * * * * * *
Lisa spread out the blankets into a makeshift bed, pulled two pillows out of the bag, and finally lit a candle she'd also pulled out of the bag. Gary was in the bathroom brushing his teeth, and by the time he rejoined her, she was under the covers. He could see her shoulders and head, but the pile of clothes on top of her bag made him believe she was naked.
He stripped off his underwear, and when he sat beside the blankets and flipped them back, he saw Lisa was definitely naked. He stared longingly at her smooth skin illuminated by the flickering candle, but the dark triangle of hair between her legs was more than he could take.
"Gawd, you're sexy!" he growled while crawling in with her.
She loved the excitement that overcame him every time he saw her naked, and giggled with anticipation. She wrapped her arms around his neck and passionately kissed him.
"Tonight, will you make love to me, cum inside me, and then sleep next to me?" she asked softly but seductively.
Lisa was the first girl Gary had been with that liked to talk dirty during sex. She usually asked him to fuck her, to be in her pussy, to make her cum... but this was the second time tonight she had used 'make love' instead.
"I like the sound of that," Gary said as he violently kissed her neck and cheek. "Will you come down one weekend and stay with me at school? I want to introduce my girlfriend to the guys."
That was exactly the response Lisa was waiting for. She never answered verbally, but as she shook her head 'yes', she took Gary's erection and guided it to her pussy. She looked into his eyes with a plea to fill her, and he quickly pushed deep inside her wetness.
"Oh fuck, that feels so fucking good..." she purred as he began thrusting in and out.
Her heals rested in his calves as her legs wrapped around him, and she grabbed his hips to pull each down thrust as far into her as it could go. Gary loved the way she felt, and the way her naked body felt against his. He kissed her again, and as her tongue wrestled with his, exploring his mouth much like his erection filled her body, his thrusts became harder and faster.
"Oh yeah... fuck yeah... fuck me... fuck me... fuck me..." she growled each time he was deep inside her.
Gary was 21, a college junior, had been with two long-term girlfriends. There was a third girl at school he dated long enough they had sex multiple times. There were also a few one-night stands and weekend romps. He always felt he was reasonably experienced in the ways of physical pleasure. Lisa was 18, and they had never talked about her past sexual experiences. But Gary was pretty sure she was more advanced than he was. She let him crawl in her window when her parents were home to have sex, she was on the pill, she let him cum in her mouth, and she owned a vibrator. The previous girls he had been with had shared the learning experience with him, but Lisa was teaching him new things. He didn't mind at all having someone teach him new ways to enjoy sex -- especially someone with such a tight, fit body, and seductive, green eyes.
Lisa wrapped her arms around Gary, and with all her strength, she rolled him over without letting his erection fall out of her. Now on top, she put her hands on his chest to steady herself and began riding him. Once she had her rhythm, she sat straight up and took a boob in each hand. She squeezed, then caressed, then pinched her nipples between her thumb and middle fingers. As each stimulus added to her pleasure, her tempo increased, and the look of desire intensified.
"Is this OK?" she asked as the expression on her face transitioned from sweet to lustful.
"Yeah, I've never done it this way before. I like being able to watch you -- I love your smile and eyes..."
This was the first time Gary had been able to look up at any partner. It was a new experience watching her make most of the effort while he enjoyed the erotic show. As he studied her in the flickering candle light, it looked like the better the sex felt, the less control she had of her body. Her legs lifted her off of Gary's body then slammed hard back on to it, forcing his erection deep inside her. Occasionally she changed motions, sliding her hips forward and back as a different pleasure overcame her, and her hands ran through her hair. Then she would continue up and down as her right hand found its way between her legs and played with her clitoris.
"I'm going to cum!" she screamed as Gary's erection and her hand provided double pleasure. "I'm going to fucking cum!!"
She ferociously rode her boyfriend, her eyes closed, concentrating on making sure every bit of stimulation was guided between her legs.
"I'm cuuuuuuuummmmmmmming!" she screamed as her back arched and waves of pleasure raced through her body.
Gary was ready to join her. Watching his girlfriend cum as she rode his erection, then announcing her orgasm, he felt the familiar tightening between his legs that always preceded his orgasms. He watched her face contort in agony and pleasure as her body convulse as she started to cum, and the first pulse of his ejaculate shot into her pussy. His body became more tense as he released another spurt, then another, inside her.
For Lisa, the pleasure became almost unbearable, and she twitched, then spasmed, as the pleasure reached her extremities then raced back to where it all started. As her first orgasm of the night ebbed from her exhausted body, her eyes opened. As she looked down at her boyfriend, a contented smile spread across her face.
"I've never cum this way before," she said with a girlish giggle. "I like it!"
She collapsed on top of Gary, and even though they'd both just orgasmed, the feel of their naked bodies pressed together was already arousing both of them. He pulled her close and again kissed her.
"Remember earlier tonight in the pool, and everyone was gone, and you'd just seen Tracy's boobs," she teased as she played with his still mostly-hard dick. "... and I was sucking you, and you were really liking it -- you liked it SO much you came in my mouth? And then after you finished cumming, I kissed you?"
Lisa was the queen of the tease.
"Yeah, I remember -- how could I ever forget that?" he said. "Yeah, I remember how sexy you were, and how good it felt, and then the taste... I kind of liked it..."
Lisa's green eyes danced with mischief as she looked at Gary ready to share her next offer.
"Well, if you kind of liked it, and if you're ready to fuck again - If you'll lick the cum out of my pussy, I'll suck your dick until your hard again and we can fuck more if you want to," she purred. "We've got all night, and if you're OK with it, I really want to do it again..."
Gary didn't have to think about her offer at all. Before that night, every sexual experience he had ever enjoyed had been in a car, or in her bed where a parent could walk in any moment, or hook-ups at school that were for quick sexual relief and nothing more. This was the first time he was with a girl he wanted to fuck a second time, and in a place where they could have as much sex as they desired. He rolled her onto her side and crawled between her legs with his barely softening dick available to her mouth.
Gary buried his tongue deep inside her pussy while she took his dick in her mouth. He loved tasting her, and also tasting his ejaculate, while she cleaned their combined taste from his dick. He also loved the feel of giving and receiving pleasure at the same time. He continued licking, and nibbling, and tasting her, and tasting him in her, and enjoying the softness of her lips and mouth on him at the same time.
Soon, Lisa's her hips were in a rhythm, and her moans prevented her from pleasuring him. During their two-plus months together, she'd taught him how she liked to be teased and how she liked to be eaten -- and he knew this was not the time to tease her. He moved his body where he was now going down on her, and listened to her moans, and felt her movements, and reacted to everything that made her feel good. He grabbed her hips, and pulled her pussy hard against his mouth, and In just a few minutes he had given her a second, rapturous orgasm.
When Lisa's spasms subsided, he crawled up her naked body and shared their combined taste with her. She eagerly licked his face until there was no more to be had, then laid her head on his shoulder. For the first time in Gary's life, he wasn't overly aroused and in need of quick release. He'd already cum twice that night, and for the first time he was ready to have sex where the goal was to be with the other person, to feel good, to make them feel good, to talk and learn about each other. He looked in Lisa's eyes, kissed her, then slid his erection inside her. She moaned into his mouth as he filled her, then they slowly fucked -- slowly in, slowly out, slowly in, then an extra push and in a little deeper, a deep moan, and arched back...
"Oh fuck, that feels good..." she purred.
Gary had no idea how long their second sexual encounter of the night lasted. There was no clock in the room, and no risk of getting caught by someone coming home earlier than expected. He had already had all his sexual itches for that day scratched, so there was no need to hurry to orgasm. When he wasn't kissing Lisa, he was listening to the sounds she made, or looking at her expression to see what felt good. It felt like hours that he was inside her, enjoying the pleasure her willing body gave him. There was no dirty talking, no screaming moans -- just the sounds of kissing and the wet sounds of him moving in and out of her. Then, Lisa broke the quietness.
"Gary, I'm going to cum," she whispered before again kissing him.
They kissed softly but passionately as he continued to fill her with his erection again and again. The sounds of her pussy taking him, then releasing him, then taking him again combined with her moans in a powerful, erotic sound track.
"You're going to make me cum..." she followed as her back arched and orgasmic pleasure started where they were joined.
Gary had been trying to hold back, to delay his orgasm as long as possible. But when she told him she was about to cum, he could delay no more. As her back lifted off the floor, he released the first spurt of his third orgasm deep inside her pussy, then pulled out and pushed in again, and again, and again until he had no more to give her. He collapsed on her naked body and felt the final spasms of her own orgasm and listened to the soft, muffled moans of release.
They laid together for a while until Gary was soft and no longer able to stay inside her. He rolled off and laid beside her, trying to catch his breath. They talked for a few minutes, but they were both physically spent. Lisa turned on her side, and Gary conformed his naked body to hers, and for their first time ever, they enjoyed the deep, peaceful sleep of the sexually content.
* * * * * * * * * *
Gary watched Lisa undo Tracy's bikini top, take it off, then throw it to the side of the pool. She then turned her back to her best friend, lifted her hair off her neck, and Tracy took her top off, too. They walked to the side of the pool where he was standing, one on either side, and they both started rubbing his dick through his swimsuit. When he was fully erect and throbbing, Gary woke up from his dream to Lisa's green eyes watching his, her smile again full of mischief as she played with his already very hard dick.
"I never said I wanted to see Tracy's boobs or her naked," Gary said defensively, and the cobwebs of sleep cleared from his brain.
"You didn't?" she asked, appearing to think back on their months together. She continued playing with his hardness.
"Maybe it's all the times I've seen you looking at them," she said with a sly smile.
"I do love boobs," he offered. "I want to see all of them... the girl at the mall, the mom next door, your sisters, your mom. Yes, and Tracy -- she has boobs, and they look huge on her tiny body, so 'yeah', I want to see them..."
Lisa appeared amused at his answer.
"Which sister?" she asked, trying to make him a little uncomfortable.
"BOTH!" he happily replied.
"Were you dreaming of my sisters' boobs when you got this?" she asked, stroking him.
He thought of lying, but he was still too dazed from his deep sleep to pull off a good deception. He decided the truth was safer for the time being.
"Well, I was actually dreaming of yours and Tracy's boob's," he told her. "You were both topless in the pool, playing with my..."
As Gary told her of his dream, a naughty smile spread across Lisa's face. While she played with his erection in anticipation of having sex one more time that night, he decided to embellish a little.
"... then you both made out while playing with each other's boobs. You were so hot for each other you totally forgot about me."
"Ohhhh," she teased, moving her mouth toward his erection. "Typical guy dream -- two girls making out...".
She went down on him, and when he was rock-hard, she laid on her back and spread her legs.
"For now, you'll have to do with just me."
She reached out to him, pulled him on top of her, and guided his erection inside her for the third time that night. He was more than happy to have a willing, insatiable girlfriend that seemed to want sex as much as he did. By the time they both came, there was a purple hue in the sky outside the bedroom windows.
"I need to be ready when Tracy gets here," she told him as she got up from their makeshift bed. "Want to take a shower with me?" she asked.
"Definitely!" he responded. "I love showering with you. But this time we don't have to hurry!"
When she started the water, she turned and kissed him.
"Me too... But this is off limits," she said as she took his hand and placed it between her legs. "I'm going to have a hard time walking for a few days."
* * * * * * * * * *
Lisa called Gary at work. It was back to school for his second junior year Saturday, and he needed to make every dollar he could.
"Tracy and I will do it!" she said with an unusual amount of enthusiasm.
"Do what?" Gary asked, more than a little confused.
"The threesome!!"
"What?!" he asked. "I never said I wanted to have a threesome. I might have fantasized about it once or twice, but I never asked you for that."
"You said you wanted to see both of us together, naked. Isn't that a threesome?"
Gary's overly analytical mind briefly wondered if there were other ways of seeing two women together, naked, without it being a threesome. But he was pretty sure his girlfriend just said they were going to both have sex with him. Did he really think he should argue with her over that?
"Uhhhhh... I think I said I wouldn't mind seeing her naked if you were there, too..."
"That would be together!"
She continued with short, explicit directions.
"Rent house, 9:30" was all she said before hanging up.
That gave him a few hours to pack for school, have dinner, and get a shower.
* * * * * * * * *
It was just after dark when Gary pulled into the rent house driveway, and Lisa's Mom's car was already there. When he opened the front door, he saw a pair of her shorts on the ground just inside. A few steps closer to his old bedroom he saw a second pair of shorts, then two t-shirts, then a couple of bras, and finally two pairs of panties.
'Of fuck, I can't believe this is happening,' he thought as he picked up both pairs of panties and held them to his face. 'Two gorgeous, sexy, naked young ladies... all for me!'
When he got to the door of his old bedroom, he could see a slim band of dim, flickering light shining under the door. When he opened it, Lisa had recreated the pallet they used a few nights ago. She and Tracy were waiting for him, and like that earlier night, he could see from their shoulders up to their naughty, mischievous smiles. Although there was still time for them to prank him, he was fairly sure they were both naked under the top comforter.
"Well, hello ladies," he said with barely controllable excitement. "This is a very nice surprise!"
They smiled as they watched his every move, but there was some nervous excitement as they all faced a very new experience. Gary didn't wait for an invitation, or any instructions -- he ripped off his clothes as quickly as he could. When he pushed his underwear down his legs, he was fully erect, and his hardness bounced as it was freed.
"That's not a surprise!" Lisa said as she looked at his erection. "He's hard all the time!"
Gary lifted the covers, and to his excitement he saw the naked body he'd fucked many times over the summer, and a naked body he'd fantasized about but hadn't seen until this moment -- all five feet, zero inches of hot, compact, sexy curves, luscious boobs, and a triangle of dark blonde hair he planned on exploring in all its glory. He threw the cover away from the group not wanting any of them to be covered and unavailable for study as the night progressed.
Gary kneeled between the two friends, reached out to his girlfriend, and pulled her up to him. He embraced her, feeling her nakedness against his own, and passionately kissed her. He then pulled Tracy up, embraced her, and felt the excitement of new, naked, soon-to-be explored curves against his erection. It throbbed with desire, begging to be put inside her, to feel the warmth and wetness of her womanhood. He kissed her too, but was smart enough to make sure Lisa got more attention.
Now with the two kneeling beside him, Gary turned them facing each other.
"So, ladies -- what's on the agenda for tonight?" he asked.
"It's your 'Going Away' party," Lisa replied. "What do you want to do?"
"I can ask for anything?" he asked.
"Yeah, anything," she said.
"OK, I want to watch you kiss Tracy. Not a peck, but a really good kiss, like when we're having sex."
"Sure, we can do that, can't we Tracy? But I've never kissed a girl before," Lisa said with a shyness that belied her sexual experience.
She looked at Tracy for any signs of hesitance, but Tracy looked ready.
"You mean you two didn't practice any while you waited on me? I bet Tracy won't mind if you two make out for a little while."
Lisa looked at Tracy who looked ready for anything exciting, even kissing her friend for the first time. Gary knew Lisa, who was three years younger than him, was more experienced sexually and hadn't been unwilling to do anything he'd asked for all summer. He wasn't surprised when she leaned in and kissed the short blond.
"Oh yeah, that's so hot..." he told them. "... so fucking hot!"
At first their kiss was timid, even soft, but as they heard his comments, their tongues probed each other's mouths, and their kissing was more intense. Gary let one hand explore Lisa's body, but the other was more animated as it explored Tracy's curves. He pushed the two friends closer together, making sure their naked skin pressed together, then he encouraged their hands to explore each other's back and butts. And when Lisa grabbed Tracy's butt and pulled her body tight against her own, Gary also caressed her rear, and squeezed her cheeks, and ran his fingers between them.
"Wouldn't you be more comfortable lying down?" he asked them.
They paused just long enough to get comfortable on the pile of blankets, then resumed their kissing and caressing. Gary laid behind Lisa, and as he snuggled in close, his erection pressed against her butt. He took his hand and guided one of Lisa's to Tracy's boob where she happily squeezed and massaged it.
"Suck her nipple," he whispered in his girlfriend's ear.
Lisa pushed Tracy to her back, looked quickly at her body, then began sucking the pink nipple closest to her. Gary reached across Lisa and massaged Tracy's other boob while continuing to grind his dick into Lisa.
"Oh yeah, that feels really good..." Tracy softly moaned.
Gary watched his and his girlfriend's hands squeezing and fondling Tracy's boobs, studying, marveling at their size, and lusting at their fullness. As he got more excited, he took Lisa's hand and guided it between Tracy's legs, and she opened them for the couple to explore. Gary's large hand covered Lisa's smaller hand with his fingers between hers. He slid them deeper into Tracy's blonde pubic hair, and when either of them touched her clitoris she would whimper, and her hips would push forward to welcome their touch.
"Wow, this is so fucking hot..." she purred, pushing her pussy even harder into their combined touch. "Two people doing me at the same time - I think I could learn to like this," she added.
Gary then pushed his finger inside Tracy's pussy, while Lisa continued to rub her clit. The combined, intense pleasure caused her to gasp. When he pushed in even deeper, her gasps became moans.
"Unnnnggghhhhh..." she moaned. "You guys feel sooooo good."
He pushed in as far as he could then swirled his finger around putting luscious pressure on all 10,000 nerve endings that provided her sexual pleasure. He couldn't take his eyes off the way her hips moved as he and his girlfriend both explored her body for the first time. When he was covered in Tracy's sexual fluids, he pulled his finger out and rubbed in on Lisa's lips.
"Taste her," he whispered in her ear.
Lisa eagerly sucked on his middle finger while Tracy watched. Then he put his finger in her again and applied it to Tracy's lips.
"Taste yourself," he told her.
She did, sucking every bit of her flavor off of his finger. Not wanting to be left out, Gary fingered her again, this time longer, and deeper, and more intensely. And he watched her hips thrust forward and back, and she even looked into his eyes with a look, that in his mind, told her she needed what he was doing to her, and even more. And then he pulled his finger out and tasted her and craved putting his mouth where his finger had been. But first, his throbbing erection needed some attention.
Gary rolled Lisa on her back, then crawled between her legs. She was wet from making out with her best friend, and when Gary guided his erection between her legs, he was easily inside her. When he pushed in, she moaned and pushed her hips forward to meet him. Gary extended his arms raising him above Lisa.
"Oooohh, I've never watched anyone fuck before. This should be exciting," Tracy said as she rolled in close to Lisa's naked body and spread legs.
Gary watched her watch him and Lisa, and for a few minutes he was happy thrusting in and out of his girlfriend's pussy while looking at Tracy's naked body. Tracy snuggled in close to them, and played with Lisa's boobs while Gary fucked her.
"Is it hot getting fucked while a friend watches?" Tracy asked Lisa.
"Oh, fuck yeah, it feels so fucking good. Do you like watching?"
"Yeah, I do like watching -- it's very sexy..." she answered seductively.
The more Tracy watched, the more excited she got, and as Tracy's gaze went from curiosity to lust, Gary wanted more.
"Suck her tits," he said, looking at Tracy.
Tracy did, and as her best friend sucked one, then the other, nipple, Lisa stroked her hair. She looked at Gary, enjoying his lust, then looked at Tracy's lips and tongue dancing on her nipple. She realized she'd only known her friend for less than six months and no idea what her past sexual experiences were.
"Have you ever done this with a girl before?" she asked Tracy.
"No. you're the first..." she said before reapplying her mouth to the already-wet nipple.
"Never even kissed a girl before?"
"No, you were the first for that, too. I've never been in a threesome before, either. I'm not very experienced..."
Gary wasn't sure which was more exciting -- them touching each other, or them talking about sex. Both were beyond amazing, and he was getting very excited. It felt great fucking Lisa while Tracy watched, but he was ready to get a little more intimate with the new partner. He pulled out of Lisa and laid on his back, his erection glistening in her wetness as it pointed toward the ceiling.
"Tracy, I want you to taste what Lisa's pussy tastes like on my dick."
Tracy looked up from sucking Lisa's boobs and looked quickly at her BFF for guidance. As Lisa smiled excitedly, she took Gary into her mouth and cleaned all of Lisa's taste from his erection.
"How do you like the way she tastes?" he asked her.
She made sure she had cleaned every drop of Lisa's wetness before she answered. She looked at Gary with the sexiest look she could muster.
"I love it -- you both taste like sex..." she purred.
Tracy crawled between Lisa's legs, and Lisa's eyes got bigger and bigger as the tiny blonde got close to her pussy. Tracy looked at Lisa, then at Gary, and then stared at the dark patch of hair between her BFF's legs. When her face was just inches away, she grabbed Lisa's hips and used them to guide the other girl's wetness to her mouth.
"Oh fuck, yeah," Lisa purred. "I really like that..."
She raised her head off the pillow to get a better look and intently watched her best friend licking her pussy.
"Are you sure you've never done this before?" she asked her best friend. "You're better than Gary!"
They all laughed, and Gary considered tagging in to take over for Tracy. But watching her make his girlfriend moan and rock her hips was one of the sexiest things he'd ever seen.
"So now when I call and your mom says your out with Tracy, do I assume she means you are doing each other?"
"Yeah, maybe," Lisa said with a giant smile, knowing Gary loved the possibility of that being true. "You won't mind, will you?"
"No, not at all. I think you two should hook up every weekend I don't come home from school. Someone needs to take care of your appetite, and I'd LOVE knowing it was her if it's not me.
By the time Gary finished his comment, Lisa's expression had changed from someone having fun teasing her boyfriend to someone who was being overcome with pleasure.
"Oh fuck, this is feeling so good..." she purred. "You're going to make me cum."
Tracy was encouraged by her friends comment and knew if she could make her cum, then it should be her turn to be the receiver of pleasure. She'd never eaten pussy before, but she had had hers eaten a few times and knew what felt good. She nibbled on Lisa's clit, then put her tongue deeps inside, then sucked on her clit before doing it all again... and again... and again. Soon Lisa had her head pulled tight between her legs, and was screaming loudly as the pleasure became too intense.
"I'M CUMMING!" Lisa screamed as her orgasm raced through her body causing it to become rigid.
"Oh, fuck -- I'm cumming so HARD!" she screamed again.
The rest of her sounds were loud, random screams that eventually died down as the orgasm her BFF gave her finally subsided. She had cum many times the last few weeks as she and Gary became a couple and explored everything physical each other liked. But this was more intense -- she wasn't sure if it was because Tracy was that good at going down on women, or because of the look of pure lust Gary wore while watching them, or just because it was a little different and kind of naughty. It was amazing, and drained her of any energy for the foreseeable future. She collapsed in exhaustion, and when Tracy laid beside her, Gary pushed her legs open and crawled between them.
"Oooohhhh -- OK, so I guess it's my turn!" she said as he wasted no time tasting her.
As Gary plunged his tongue into her wetness, her legs went into the air, her toes pointed on either side of his head. He had wanted to experience her compact, curvy body pretty much since he got to enjoy Lisa's.
Lisa, still closer to sleep than her own next sexual experience, rolled on to her side so she could watch her friend receive pleasure.
"Does that feel good, Babe," she asked Tracy. "I was just kidding earlier - he really is very good at eating pussy."
"It... feels... great," Tracy panted between breathes. "He... is... good... at... it..."
A smile spread across Lisa's face as she watched her boyfriend go down on her best friend. Gary knew from her smile she was OK with the attention he was lavishing on their third partner. She kissed Tracy, then sucked and caressed her nipples, then rubbed her stomach. Gary was right that she was experienced with guys, but with girls and more than a single partner, everything was new. She realized she was a voyeur, and watching others enjoy pleasure was nearly as enjoyable as getting it herself. She loved watching Tracy's body move with the sexual rhythm she and Gary were developing. She also loved seeing his face covered in Tracy's wetness as he explored the moves that made her moan and writhe.
"Are you about to cum?" she asked as Tracy's moves became more intense.
Tracy was too involved in receiving from Gary to speak, but she was able to shake her head 'yes' as she started to plateau. Lisa took her face and turned it to her own, and as Tracy lost control of her body, Lisa kissed her. Tracy moaned into Lisa's mouth, barely able to return the kiss. But as the orgasm lessened in intensity, she was able to enjoy the feeling of Lisa's tongue in her mouth and Gary's inside her pussy.
As the two girls continued to Kiss, Gary released Tracy's hips and crawled up her body, between her legs. He used his knees to open them, then held the head of his dick to her opening. He looked to Lisa for any signs of regret, but her eyes were open wide, fixed on where he was about to enter her best friend, and her smile showed nothing but desire.
"Are you ready to get fucked" she asked Tracy.
As Tracy excitedly shook her head 'yes', Gary tried to pushed in. He quickly realized her small body housed an equally small pussy, and he barely got the head inside. He pushed again, and her tightness gave way a little more while she lifted her hips off the ground, enticing him to keep trying.
"Oh god, that's feeling good," she almost growled.
She grabbed his hips and pulled hard against them.
"Oh yeah, this is going to be amazing..."
Gary pulled out, and with her help pushed even harder.
"Fuck yeah... keep going... I need you to fuck me..."
Driven as much by her explicit language as her motion, Gary thrusted to a point where he was afraid he would hurt her.
"That's it!" she screamed. "Do that again!"
Gary did, again and again, and then again, and he was finally able to get all the way inside her. She moaned as he stretched and filled her, then she begged him to make her cum.
"Please fuck me hard, Gary. I need to cum when someone's fucking me..."
Gary extended his arms to raise his own body above his tiny blonde partner. He watched her boobs move in rhythm to their movement, then looked at his girlfriend for reassurance, then at his erection as it emerged from her pussy glistening with her wetness. Then he looked at her face as intense pleasure overcame her. It was a different face than he had grown used to that summer - different hair, mouth, and eyes, different sexual looks - that looked back up at him. The familiar eyes eagerly watched them, enjoying the sights and sounds of pleasure instead of enjoying the pleasure itself.
"Oh yeah... fuck me, Gary... fuck me... fuck me... fuck me...".
Gary committed every inch of her body to memory and focused on how amazing her tight pussy felt as it took him in over and over. He would spend many nights alone in his college apartment satisfying his own sexual needs, and he wanted this memory added to the database of sexual experiences he would use during those times.
"Fuck, this feels so good... oh yeah... fuck me... fuck me... oooohhhhh yeahhhhhh..."
Lisa snuggled close to Tracy, and as Gary slowly filled her tightness again and again, she caressed each of their bodies, and occasionally kissed her friend.
"Does that dick feel good?" she asked Tracy.
"It feels so fucking good..." she moaned. "He makes my pussy feel so fucking good..."
"She's really loving this, Babe" Lisa said to Gary. "You better make her cum..."
"Oh yeah, make me cum... please make me cum... please cum in my pussy!"
Gary never had a girl talk dirty to him until he met Lisa. It was an instant turn on and increased the excitement of sex many times. Tonight, it was just as exciting coming from her five-foot-tall friend. He wrapped his arms tightly around her and forced his dick in her with every ounce of his energy.
"Oh fuck yeah..."
Then he pushed in harder.
"God yeah... oh fuck yeah..."
He was fucking her so intensely he was afraid he was hurting her, but her moans suggested otherwise.
"That feels so fucking good... unghhhhh... You're going to make me cum... ooohhhhh... I'm going to cum... I'm going to fucking cum... I'm cumming!"
Tracy's back arched as her orgasm started. Gary pushed in one last time then shot stream after stream of cum into her. It could have been that she was a new partner, or that she was so small, or that there was another naked girl beside them, but the pleasure he was feeling as he filled her with is ejaculate was beyond anything he'd ever felt before. He finally collapsed on top of Tracy's small, voluptuous body and relished in their naked touch as the remnants of his massive orgasm filled her.
Gary laid still. For a short moment he wanted to concentrate on how her naked body felt under him. He glanced at her face to see how she looked after she came, and when he saw her cute, satisfied smile, he kissed her -- more than a peck, but not so long as to anger Lisa. Then like a few minutes earlier, he committed everything about the sex they'd just completed to memory for later masturbatory enjoyment.
Tracy was impressed at how intense her first orgasm of her first threesome was. For the past few months any sexual release was courtesy of her own finger, or sometimes her vibrator, and preceded a night of deep sleep. But even as her body still tingled from that orgasm, she wanted more.
She crawled to where Gary was laying next to Lisa. His dick was still mostly hard and glistened in the wetness of their combined sex. She took him in her mouth, licked him clean, then looked from Gary to Lisa and back again.
"What?" she asked in mock incredulity. "You guys get to have sex all the time, but I may not again for a while. Surely you're ready for a little more..."
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