This is a pure fantasy story of an alternate history of Mina and Jonathan’s sexual past. No, Jonathan would not have liked Mina’s first sexual experience to have been with someone else at the time. Yes, Jonathan was Mina’s first. No, Mina would never have reacted in real life the way she does in the story. However, these kinds of things make for great “old married couple” fantasy fodder, don’t they?
During their early dating years (high school and early college), Mina wanted to save herself for marriage so Jonathan was one frustrated teenage boy, always trying to get her alone and hopeful that if he got her hot enough, she’d just say yes! Alas, all they did was a lot of making out, touching, and getting naked a few times. Sure, they got each other off when they could but getting into her pussy was all that Jonathan could think about. At this time, Mina was 5’3″ at about 110lbs so she had a nice teenage body with small and perky A cups. She had a full bush as she hasn’t discovered shaving yet and while they had seen each other naked at this point, they didn’t get too many chances for that as both lived at home. One thing that Jonathan does remember is that when they used to fool around and he’d reach into her panties to feel her pussy, Mina would get so incredibly wet that her panties would be soaked. He remembers feeling her public hair so matted with her clear juices and how incredible it would feel as he ran his fingers up and down her soaking wet and hairy lips as he teased her opening that he could never get into.
Mina, only Jonathan’s girlfriend at the time, was 18 when she took a job babysitting for a couple in their mid-’30s that had a 3yo child. She typically babysat one or two nights a week so the parents could go out on dates. Mina didn’t have a car so they had to pick her up and drop her off each night she babysat. The first few months went by uneventfully. She would tell Jonathan about the couple and the sweet kid and everything seemed pretty normal. Jonathan did get some pangs of jealousy when she spent the evening babysitting when they could have been hanging out. He also got a little bothered on the nights that she would get dropped off by just the husband as Jonathan knew for dam sure that the husband would do anything to get into his girlfriend’s young and tight pussy.
One evening while babysitting, the couple comes home a little later than usual and the wife looks absolutely smashed. Mina figures she must have drunk too much and smiled at the husband as they pass and he tells her that he’s going to put his wife to bed and will be back down to take Mina home. A few minutes pass and he comes down and they both get into his car. On the 15min ride home, he apologizes for his wife, saying that she had a little too much fun dancing and drank a little too much. The conversation goes back and forth on a variety of things but eventually comes to Mina’s relationship status. She explains that she has a boyfriend and talks a little about how they meet and how often we see each other.
Feeling either emboldened with what he had to drink that night to perhaps noticing Mina’s willingness to open up, he hints at, “extracurricular” activities that she and Jonathan might participate in. Mina, blushing yet feeling comfortable as she has gotten to know the husband for a while now, says that yea, they fool around a bit but that she’s saving herself for marriage. “Ah, interesting,” says the husband. An awkward silence hangs in the car as they pull up to Mina’s house and they part ways.
The next week, Mina sits again and while the wife behaved herself this time, the husband volunteers to drive Mina home. In the car, the conversation of course comes back to sexual things. He inquires as to what kinds of fooling around she and Jonathan do and where do they do it. He talks about how when he was in high school, it was always so hard to find privacy to explore those kinds of things. Mina, smiles and blushes again and says that they usually just make out and touch each other parked in Jonathan’s car near the school. That sometimes they go to Jonathan’s house and nobody will be home and we get naked and explore each other and get each other off.
After describing this, Mina can feel herself getting wet just thinking about it. She glances over to the husband and for the first time, looks at him in a sexual way. She realizes that for someone twice her age, he’s pretty attractive. He’s handsome with short hair and a strong jaw line and from what she can tell, he seems like he’s in shape. He’s good deal taller than she is but he holds himself in a strong yet respectful manner. Thoughts race through her mind about her experiences fooling around with Jonathan. Jonathan’s hand reaching into and rubbing her soaking wet pussy. His fingers pinching her pert nipples and my other fingers gently pressing at her opening in between brushes against her clit and playing with her pussy lips. Only this time, she’s picturing the husband’s face, his body, his hands, that are touching her.
She begins to squirm in her seat. She’s not used to these kinds of feelings away from Jonathan. Every bump in the road and shift in her seat sends pulses of pleasure from her clit. The husband notices that something is up. Even in the dark, he can see that Mina is turning flush and that her breathing is heavier. He asks her if she’s feeling alright and she says yes, that she’s just feeling a little sick. They are driving along some neighborhood roads in a nice part of town before they hit the freeway. It’s quiet out, not many cars driving around and streetlights are sparse.
He pulls the car over and turns it off. He gets out and opens the trunk, then closes it, then walks over to Mina’s door. He opens the car door and crouches down, handing Mina the bottle of water he just grabbed. She grabs it and opens it, taking a swig as she tries to turn her mind to something else, anything else. She glances over at the husband and notices him eyeing her legs. She sees his gaze move from her calves to her thighs that are exposed thanks to the thigh-high skirt she is wearing. She looks away just as she knows he is following her figure up, likely on her small perky breasts and seeing the small valley from her breasts in her v-neck shirt. She’s trying not to look at him but she can feel his eyes on her, trying desperately to see as much of her exposed skin and features as he can in the low light.
He places a hand on her thigh just above her right knee and gives it a small squeeze. He asks her if she’s feeling any better and tells her that maybe she’s a bit car sick. Mina responds that she’s alright, just feeling a bit flushed, as she cracks a smile and glances over at him. She looks down at his hand on her thigh just as he starts to gently rub her thigh back and forth. Her emotions are swirling now as her breathing increases. She knows she shouldn’t be doing this but at this point, she’s so incredibly turned on that she doesn’t know if she can stop herself. Mina rests her spinning head back on the headrest and while lost in her feelings of thinking of Jonathan and how turned on she is, she instinctively relaxes her leg and gently opens her right leg.
The husband sees Mina go into an almost trance-like daze as her knee relaxes and the weight of his hand causes her legs to spread. In the dim light, he can see her white panties. They have a very noticeable wet spot. So wet, in fact, that he could actually make out the matted black public hair and the outlines of her labia clinging to her soaking panties. He wasn’t sure what to do next. Here was this cute and virginal Asian teen soaking wet in his car with his hand rubbing her thigh. He glanced at her face again but her eyes were still closed, mouth slightly agape and her breathing was deep and fast. She was clearly very turned on.
With so much of his attention focused on her, he only now realized how hard he had become. Sure, the babysitter fantasy is something that he thought about, and even jerked off to on occasion, especially after first hiring Mina those few months ago. But he never through he’d actually be in this position. He decided to push his luck and slowly slid the hand on Mina’s thigh higher. Carefully watching her reaction, he saw her body quiver as his hand was only inches away from her panty line. He decided to keep going. When he hit the edge of her underwear, just to the side of her mound, he slowly brushed his fingers over the dark wet patch just above her clit. This sent waves of electricity through Mina’s body as a moan escaped her lips. She again, instinctively, opened her legs wider as she slouched down in the leather seat, giving him greater access and an even greater view.
After the shock wave of his hand touching her underwear, Mina was unbelievably hot. She knew what she was doing but at this point she could not stop herself. She wanted him to touch her. With her eyes closed, she was switching between picturing Jonathan touching her and the husband. The touch was different though. It was bolder, stronger, more focused. “Experienced” is the word that popped into her head. She started to feel guilty about cheating on Jonathan but she had to have this man. She needed to have this man. She wanted to feel his lips on hers, to feel his strong experienced fingers rub her clit and tease her opening, to maybe even touch his cock.
After gently rubbing Mina’s pubic mound, the husband moved his hand down and rubbed over her clit making her jump and moan. Her juices were soaked through her underwear lubricating his fingers as he firmly rubbed over her pussy lips, feeling their outline while gently yet firmly pushing against her sealed opening. He noticed how small and tight her pussy felt against his fingers. How cleanly cut, firm, and young her labia were and, even over her underwear, how tight the entrance to her pussy was.
After rubbing her like that for only a few seconds, he decided to take another chance. He leaned in gently and started kissing and nibbling on her neck. Mina’s head was turned away from him but as soon as she felt his lips and the warmth of his breath on her neck, she let out an audible, “ohhh, yes” as she opened her eyes for the first time. One of her weaknesses is kissing on her neck and at this point, she is in pure lust mode. She turns her head and leans forward and immediately sticks her tongue into his mouth as they start to passionately kiss. Emboldened, the husband returns her kisses with equal passion and intensity.
Desperate to feel her raw pussy, he lifts this hand and works it into the side of her underwear next to Mina’s thigh, slipping it inside and feeling, for the first time, her soaking wet pussy with no barrier. He finds her clit and gently rubs it while exploring her young and perfect labia. Mina is constantly moaning into his mouth as they continue to passionately kiss. She feels her orgasm coming on like a freight train. Sensing this, the husband continues what he is doing, exploring her virgin pussy as he gently starts to press his middle finger on her sealed opening, something that also drives Mina crazy. Between the kissing, rubbing of her clit, and increasing pressure on her vaginal opening, Mina’s orgasm hits as she bucks wildly in her seat on his hand while screaming into his mouth as they continue to kiss.
After what seems like a minutes-long orgasm, they break their kiss and he pulls his now soaking fingers from Mina’s underwear. They look each other in the eyes and he can tell that passion is still filling her body. She looks down at his crotch as he sits on the ledge of the open passenger-side door. She can make out the outline of his cock. Behind his slacks, it looks pretty big, bigger than Jonathan’s, that’s for sure. She reaches down gingerly and for the first time, touches another man’s cock…a much older man’s cock. It feels thick and long and very hard. She starts rubbing it back and forth over his slacks while staring deeply into his eyes. Mina is not terribly experienced at this so she does the best she can.
As Mina is rubbing his cock, the husband is so hot that he knows he’s about to orgasm. He stands up and tells her that he has to open his pants or else his cock is going to explode. Mina blushes as he steps back and starts to unbuckle his pants. This will be only the second cock she has seen in her life and she’s excited and curious. As his pants come undone and he drops his boxers, Mina’s eyes widen as she sees his cock spring to attention, pointing directly at her. It certainly is bigger than Jonathan’s and Mina guess’ it’s about 8″ long and nearly as thick as her tiny wrist. Her jaw drops slightly as she tells him how big it looks. He grabs the base of his cock and starts to stroke it as he’s only about a foot away from Mina’s face.
Mina, still coming down off her incredible orgasm high, leans up and out of the seat, reaching out to better grab his cock. As she grabs it, she realizes that her small hands can hardly wrap all the way around the shaft. She starts stroking it as the husband lets out a moan. He can’t believe that a hot, tight, young Asian teenager is stroking his cock. He closes his eyes and leans his head back to take in the moment. As she continues stroking, she can’t help but wonder if she’s supposed to put it in her mouth. It’s something that she and Jonathan had only done a few times. She was conflicted. She was already cheating on Jonathan but sitting there, stroking an older man’s cock, staring at it, wanting to be seen as a capable and mature woman, she deeply contemplated putting it in her mouth. In a sudden moment of snap judgment, she leaned forward and stuck out her tongue, licking the underside of his cock from the base to the tip then opening her mouth as wide as she could, she closed her mouth over the head of his cock and started to suck.
As soon as the husband felt the warm tongue on the base of his cock, he wanted to explode right there. As Mina enveloped his cock, he could feel her warm and wet mouth beginning to gently suck. It felt amazing. He could tell that Mina was a bit inexperienced. Her movement and confidence was erratic and unsure. He told her to go gently and to use her tongue around the head while sucking and stroking. Mina obeyed and soon she found a rhythm. Her mind flashed back to Jonathan, thinking about how impressed he would be the next time she sucks on his cock. It didn’t take long until the husband was on the brink.
He gently pulled her head off his cock and pulled her up by her hands. Standing together, they deeply kissed as passionately as before. Mina could feel herself dripping wet again as her excitement built about the new and taboo experience she was involved in. The husband broke off the kiss and pulled Mina away from the front door and opened the back door, pulling her towards him he grabbed her shirt and lifted it. Mina raised her arms and just like that, she was standing there in her A-cup bra and short black skirt. He went in again and started kissing her. As she wrapped her arms around his neck to pull him in closer, he reached behind her and masterfully unhooked her bra and pulled it off. There she stood with her perky breasts and hard dark nipples in front of this older man who she only marginally knew.
The husband then gently pushed her back into the backseat. Mina was a little nervous at this point but she trusted him and she was so hot that she just had to see what was going to happen next. As she laid back, he reached for the sides of her panties and slowly pulled them down and off. She scooted in a bit and propped her left foot on the floor and her right foot over the headrest, leaving her perfect pussy wide open for the husband to see. On seeing this, he was amazed. Mina’s young tight teen pussy had perfectly small labia and a cute button clit that was protruding from under its hood. The entire area was glistening with clear slippery fluid and he could see her hymen through her vaginal opening. It was a picture of innocent perfection.
He knelt down as he leaned into the back seat wrapping his arms around Mina’s legs and kissing her inner thighs. He slowly kissed, licked, and sucked her thighs, alternating between both as he slowly made his way down. Mina was almost losing control. She could not believe how turned on she was. She could feel her pussy clenching with each kiss as he made his way closer to her sex. She was in awe at how wet she was. She could feel her own juices leaking from her pussy down to her ass and could feel that she was dripping onto the leather. This only turned her on more.
Soon, the husband reached Mina’s mound and started kissing her public bone and slowly making his way to her clit. He gently blew on it, savoring it’s sweet scent and admiring how perfect it was while in amazement that he was experiencing this. Slowly, he pursed his lips and landed them on Mina’s clit. She came again almost instantly. Her hands grabbed the back of his head and pulled him in deeper as he sucked and gently licked her soaking clit. Her orgasm seemed to last even longer than the first one as it came in wave after wave. She could feel his tongue slowly leave her clit and travel down as it made its way to her opening. Feeling warmth and pressure at her opening, the subsequent waves of orgasmic pleasure hit her hard as he prodded his tongue against her hymen as if trying to work his way inside of her.
As Mina’s orgasm finally came down, she was seeing stars. Never before had she experienced this level of passion and sexual ecstasy. The husband lifted his head and simply gazed at Mina, her young perfect body laying in his backseat. The gentle dome light making Mina’s sweat glisten off her body and the absolute mess of juices that covered her pussy. He waited a minute to let her recover before lifting himself off and slowly crawling in and on top of her. As he made his way up her body, he kissed her stomach and stopped at her perky breasts. He stuck his tongue out and licked them, one at a time. He swirled each of them around his tongue and gently sucked on them as they became harder and harder.
Mina started to moan again as the husband expertly suckled her small breasts. The tingling feeling spreading all throughout her body. She started to breath harder again and could feel herself getting worked up for yet another time tonight. After a few minutes, the husband slowly kissed and licked his way up to Mina’s neck and eventually finding her lips. They kissed again, passionately.
Suddenly, Mina felt something press against her inner thigh, something big. She had gotten so wrapped up in the passion that she forgot that another man, mostly naked, with a rather large and bare erect penis, was now laying on top of her in between her wide open legs. She and Jonathan had done this many times before where he’d rub his erect cock along the folds of her pussy but this was different. Mina was in a state of ultimate relaxation while simultaneously as hot and horny as she had ever been. She felt his cock moving around her pussy. He would press it up against her clit and let it slide the length of the shaft over her clit sending more waves of pleasure over her. This grinding continued for a few minutes until Mina felt like she was building upon yet another orgasm. His cock was fully coated in her ever-flowing juices and the friction of their genitals rubbing together for the past few minutes was driving her wild.
Then, on one of his backstrokes, he went a little further and let his cock drop so that on his forward thrust, it easily slid between the folds of Mina’s pussy lips and pressed against her hymen. Mina jumped a little at the unexpected intrusion and let out a slight yelp. She looked into his eyes and they could both see the absolute passion and lust they had for each other. Her mind went to Jonathan, knowing that he had so badly wanted to pop her cherry and then a feeling of guilt rushed over her body. She started to tense up but never lost eye contact with the husband. She blinked twice then moved forward to deeply kiss him again.
As she did this, she slowly lifted her legs and wrapped them around his thighs, gently pulled him in. She felt a great pressure building at her vaginal opening. He was much bigger than Jonathan was and the feeling of the large head at her opening scared her a bit. She broke the kiss and pulled his head into her neck and whispered, “take me.” The husband knew how lucky he was and didn’t need to be asked twice. He shifted his weight and slowly lowered himself into her. As the pressure grew, Mina closed her eyes and winced at the increasing pain she was feeling. He stopped and backed up slightly, only to lower himself down about an inch or so into her again, this time with more weight. Mina could feel small sharp pains as her virgin pussy started to stretch to accommodate his thick cock. She let out a small yelp of pain and he eased up once more. Taking a deep breath, she steadied herself as he started pushing yet again. Again, she could feel pressure and some pain as she tried to relax but this time she could feel the weight of his body bearing down on her. She instinctively squeezed her legs that were wrapped around his waist, pulling him into her.
The stretching of her pussy was intense until all of a sudden, she thought she heard a pop and a sharp pain in her pussy. She yelped in pain and tried to jump away but he was holding her shoulders tight to his body and she had nowhere to go. Suddenly she was filled with something she had never felt before, stretching her as it continued creeping its way slowly into her. She let out another sharp yelp and a tear started rolling down her eye. She closed her eyes and tried to bear through the pain. He had just popped the head of his bare cock through her hymen and he was slowly inching the rest of his 8″ into her tight virgin pussy, savoring the intensely snug fit as he worked his way deeper. Mina instinctively struggled, trying to move away from the invader but he held her tight yet tenderly and made her slowly feel the full length and girth of his large cock stretch her out for the first time. He didn’t stop after initially penetrating her and over the next few seconds, he slowly fed all 8″ of his cock into her formerly virgin pussy.
There were so many new feelings and emotions going through Mina’s mind that the experience felt like it lasted minutes. before she knew it, she felt his pubic bone resting against hers and she knew that he was fully inside of her. He stayed there for a minute, relishing the feeling. Once he was all the way in, he looked at Mina and asked her if she was alright. She said yes but that it hurt and she needed to get used to it. he started to kiss her softly and she returned his kisses. After a minute or so, their kissing became more passionate and he started to slowly pull back out of her. Again, a new experience for Mina, she gasped with her mouth open and looked down to see his thick cock slowly inching its way out of her pussy. She couldn’t believe that something so big fit inside of her.
Just when she felt an emptiness inside of her as his head was about pop out of her pussy, he slowly thrust forward sinking his cock back into her. Mina’s head rolled back and she moaned out loud in a mix of pain and pleasure this time. The length, the stretch, his heavy body on hers, she was now having sex and it was starting to feel amazing. The husband continued thrusting in and out of Mina for the next few minutes, hardly able to control himself inside of her amazing folds. Sure enough, though, he knew he was about to cum. He looked Mina in the eyes and told her that he was going to cum. She pulled him down onto her and deeply kissed him while wrapping her legs around him tightly, bringing him as deep into her as she could. With that, he made another hard thrust forward pushing all of himself into her, surprising Mina with his forcefulness as he let out a deep moan. Suddenly, she felt a warm gush of fluid deep inside of her pussy. She knew he was cumming in her. It was something she hadn’t experienced but as soon as the second gush hit her cervix, the feeling was too much and she had her final orgasm of the night on his cock. Her already tight pussy started clenching, rhythmically squeezing his thickness as her orgasm hit hard.
After they were done, he climbed off of her and saw the mess that they made. Mina’s copious wetness mixed with the blood from her hymen breaking. He got some napkins and towels from his trunk and they cleaned up as best they could. They didn’t say much the rest of the ride home. Sitting in her room after a shower, Mina felt both an overwhelming feeling of guilt for having cheated on Jonathan…losing her virginity to another, older, man…but also a drug-like high for the amazing experience she just had. She decided that she’d keep her adventure a secret from Jonathan for the time being until she could find a way to break it to him.
When the next week came and the wife rang Mina to see if she could babysit again. Mina was a bit nervous but also excited and said that she would love to babysit. The wife picked Mina up a few days later and as they walked into the house, the wife asked Mina to follow her up to her bedroom as she had something to show her. Mina got instantly nervous as she thought that the wife must have found out about the affair last week. She followed the wife into the room where she saw the husband smiling and sitting in a chair in the corner of the bedroom. The wife turned and closed the door behind her. She took Mina by the hand and sat her down on the bed. She explained that she knew what happened last week and that everything was ok. She explained that she and her husband were swingers and that they had permission to have sex with other people. Mina’s mind was racing as this all new to her. As the wife described their lifestyle and repeatedly expressed how everything was ok, Mina was finally snapped out of her daze when the wife suddenly leaned in and kissed her. She stood up and pulled Mina up with her. She turned Mina around to face the husband as she slowly started to peel off Mina’s clothes. Mina was in for another wild night.