A Couple of Wishes Pt. 01

Hi! This is the first creative writing that I've done in over twenty years, and the first I've ever written of the erotic variety. I hope you enjoy it at least a little bit. I really enjoyed writing it.

All characters in this story that engage in any kind of sexual activity are consenting and over the age of 18. If you don't enjoy stories where the characters end up with genitalia that belong to the opposite sex and then enjoy using it, this probably isn't for you.

The Wish

Ashley was excited, it was the first night of the two weeks he and Jessica would have without their 'tween kids. The kids had gone to Europe with his in-laws to visit Germany and France and "practice" the languages they had been learning during the school year. Ash had made a nice dinner, and cocktails for both of them, and it was the first dark sky night of the summer. Their town had decided to designate 4 nights each summer as "dark sky" nights. The streetlamps were all turned off until midnight, the shops downtown turned off all their outside lights, and households had to turn off all their outside lights and use a minimum of indoor lights unless they had blackout curtains. Most folks thought it was a great idea and participated. Stars that you usually couldn't see were visible and if you tried, you could just make out the milky way. Jessy was already outside waiting for her third Manhattan.

Ashley, known to most as Ash, was 39 years old, 5'11" and 170 lbs. If he's honest with himself, has a bit of a dad bod. He had always had longer lean legs and his arms have never been bulky, but he had gained some extra weight around his middle that he would love to get rid of but just hasn't spent the time. Jessy at 35 is 5'6" and 140 lbs. with a toned full hour glass figure that has filled in a bit in the middle but she keeps in shape by running and swimming, her breasts are a full C cup with a little sag from breastfeeding their kids, great hips with toned thighs and a nice butt that honestly wasn't as round and lifted as she wanted it to be. She didn't have to time to work out as much as she used to, so it just wasn't as toned and lifted as it was back in college.

Ash was hoping to jumpstart a little intimacy while their kids were out of the house. Things had been stale recently and sex had been sporadic at best the last few years. He felt like he had been praying for just a glimpse of Jessy's breasts as she changed for work or got out of the shower. He had fantasized for the last few weeks about having sex at least every other day while the kids were gone, with a little extra fun. Maybe breaking in all the rooms in the house they hadn't had sex in. Which was all of them except their bedroom and bathroom, the laundry room, and the basement living room. To meet his goals, they had a lot of ground to cover. Ash was usually little submissive in bed and went along with anything Jessy wanted to do. He had discovered anal play in college and owned and used a few anal toys. He had asked years ago if Jessy would try pegging him, but she felt a little weird about it and it never became a normal part of their sex life much to Ash's disappointment. It had been relegated to the occasional birthday when he had begged for it. He not so secretly loved to read erotic stories. He'd confessed his favorite vice to Jessy years ago, she had of course responded with a "Why?". He really enjoyed the kind of story where the guy gets pegged, gender swapped, fucked by a girl with a dick, or all three.

Jessy had thoughts of getting laid over the next two weeks without the kids around, but it was going to be a challenge to get in the mood. Work had been crushing lately and she'd even had to work some weekends. She had been planning to use the kid free time just to decompress when she was home, a nice back massage in the evening after work and a glass of wine in the hot tub, she had planned a visit to the spa next weekend. She was generally the dominant one sexually but hadn't been pushing for sex as much since their second child was born. Her need for sex had dwindled over the last 10 years to occasional moment where she basically jumped Ash. Not so much horny minx she had acted like when they got married. She had always been pretty vanilla with Ash in bed, sure she experimented a little in college but since then, their wildest sex has been limited primarily the female superior position and a little light bondage. She liked being tied up and teased but hadn't done it in more than a few years. The times they had tried it she had gotten off on letting Ash tease her to distraction and then mounted him until he was sore. She had never been into receiving oral and she hadn't enjoyed pegging her husband the few times she tried it; she just didn't feel of using a lifeless dick on his ass.

Ash brought out two cocktails and a bottle of wine and two glasses. He opened the wine to let it breathe and sat down. He reached over to touch the back of Jessy's hand. She pulled away knowing he was looking for sex tonight and she just honestly just wanted to relax for the evening and watch the stars. She looked over at his drink raised an eyebrow which he could barely make out, "What's with you and those girly drinks. If you ordered that at a bar you might have guys hitting on you!" She took a big sip of her Manhattan. Ash gave her a dirty look and responded, "No martini is girly even if it ends up pink." He took a sip holding up his pinky. She could only really see his outline in the dark so she couldn't see his expression or the color of his drink. He looked over and watched her looking up at the sky, enjoying the stars. Ash spoke up "I wasn't sure about this whole dark sky thing when we voted on it last year, but it's really nice to not have the light pollution, I didn't realize how much I missed the stars." Jessy paused before responding and cocked her head listening. She could hear what sounded like someone having sex in their back yard a few doors down. "Ash, do you hear that?" "Yup" he whispered, "sounds like someone is enjoying the dark, probably not the only couple tonight out there getting to fulfill a little backyard fantasy."

Ash chuckled to himself, "You always told me you didn't want to do it in the back yard. Too cold and dirty. I always offered to a blanket."

She smirked at him "Well I don't like a cold butt. I can't afford to freeze any more of it off."

Ash says "Hey I like your butt, just enough for a grab and it's fun to give a little slap. Well, except when the kids see and make gagging noises, that's does ruin the mood."

Jessy thought a little about those slaps as she listened to the neighbors really getting into it.

"Ash do you have any fantasies that you've never told me about?" He took a sip of his martini so he could pull his thoughts away from what sounded like the couple a few doors down reaching their climax, "Well... I think you know them all. Pegging we've tried and you didn't love. We talked about swapping my dick for your pussy or swapping bodies and seeing what that's like. I've always wondered what sex is like for a girl, that's always been a fantasy. Hmm..." he turned a little red, the second martini helping him keep talking, "I've always had a fantasy of getting fucked by a woman with a penis. But you know I've read stories about that," he rushed out. "What about you?"

Jessy paused, some of that he hadn't said anything about in years. "Do you still read those stories?

Ash gulped, "Umm yeah... Is that ok?"

She savored her last sip of her drink, "I guess, I mean it makes sense, I always figured the strap-on would be better for you if it was real. Do you want to be fucked by a real dick?

Ash drained the rest of his drink, he was getting hard, "Umm, kind of, but really only if its attached to you. I mean I've always wondered what it's like from a woman's perspective. I've definitely had dreams I was having sex as woman, no idea if it was a guy or a girl fucking me. 'm not into guys so a strap-on and some dirty stories are as close as I will ever get."

Jessy paused, maybe she should try the strap-on again sometime this week, she could hear him getting turned on just talking about it. They hadn't done that in years. The strap-on was so lifeless though, it would probably be much better for both of them if she had a real dick.

Ash coughed, "Umm what about you?" She laughed, "Well getting a little tied up, sex on the conference room table at the office, and giving you a BJ to wake you up, blindfolding you and riding you till your sore. You know all those, and we've done most of them." She mentally added, "and now I'm gonna add fucking you with my own dick."

They sat there quietly for a moment staring up at the sky. A shooting star steamed by overhead gone in a blink as they watched.

Jessy said, "Do you believe in wishing on shooting stars?" Ash deflected, "Sure, I wish my drink wasn't empty." Jessy reached her foot over and poked him with a toe. "Pour that wine and give me a glass and that wish will come true." Ash stood and poured two glasses until Jessy stopped him with a hand "Look babe! Another shooting star!" This one lasted much longer, starting low in the sky and easily crossing three quarters of the visible sky.

Jessy stared at the streak of light with a look of awe on her face and whispered, "I wish that wishes on a shooting star would come true." They stared at the point the shooting star disappeared for a moment until Jessy paused and said, "Too bad they are just space rocks getting vaporized in the atmosphere..." as Ash sat back down, she added. "Hey, would you toss me that blanket, I'm a bit chilly." Neither of them noticed the bits of star dust drifting down into their wine glasses and the bottle as Ash leaned too far over, almost tipping over his chair in his attempt to grab an almost out of reach the blanket without getting back up. The wine seemed to glow for a moment before becoming a dark red, almost black in the near darkness.

Ash handed Jessy the blanket and snuck his feet under the edge after she settled the blanket over her stomach and legs. He handed her a glass and held it up for a toast.

Jessy sat up and lifted her glass and tapped it against his, "to shooting stars and wishes. May we both get what we wish for." They both took a sip, Jessy thinking to herself, "I wish I could try fucking him with a real dick", while Ash thought "I wish I could find out what sex was like from Jessy's perspective..."

Ash swallowed and paused. Was this the wine he pulled out? It tasted sweet and floral with an almost honey like aftertaste. Jessy spoke up, "What wine did you pull out, it's a lot different than I expected. I thought you were pulling out a Malbec? This is a lot darker in flavor, almost musky."

Ash paused, "Huh that's not what I got at all. I got more floral flavors, maybe it our cocktails changed how we are perceiving it."

Jessy took another swallow swishing it around her mouth for a moment, "Nah it's just a Malbec nothing special. They both had a few sips staring at the stars. Ash spoke up first, "Would you wish for anything if you saw another shooting star? Jessy smiled coyly, "If I did, I couldn't tell you now could I? It wouldn't come true. Did you wish for anything?" Ash turned red, looking up at the stars again

"Well, if I did, I wouldn't want to ruin the surprise, would I? But I didn't wish for a million dollars, and I already have you, so I really have everything I need."

Jessy snarked back, "You are so sappy, you sure I'm everything you need? What about those stories you read? Do you want me to have more?" She raised an eyebrow.

Ash turned even more red and was grateful it was so dark. "Honey, you have everything I need, the stories are just stories. Don't pretend you don't watch a movie with a sex scene and wonder what that would be like? What about your sex on conference table fantasy? I know that came from somewhere..."

Jessy gave him an impish grin he probably couldn't see and finished her wine and pulled the blanket up further exposing his feet. Ash finished his too and stood up, feeling a little tired, he gathered the glasses and bottle and brought them inside, corked the wine and put it in the fridge. When he walked back outside Jessy had fallen asleep. He gently nudged her awake and asked if she was ready for bed. she mumbled yes and sleepy wandered inside the dark house. "There goes my chance for sex tonight," thought Ash. Maybe some morning sex if he played his cards right and followed Jessy to bed.

Ash had strange dreams that night, dreams that he was shifting like sand, pulling him one way then another until he woke up in a sweat. He quietly got up and went to the bathroom in the dark, he felt a little out of it, walking differently, almost stumbling, he chalked it up to too much booze and too little water. Sitting to pee so he didn't turn have to turn on the light, his arms brushed the sides of his chest and he thought to himself that he really should lay off the extra sweets at work, that extra chub around his belly was making its way to his chest. He'd have man boobs soon if he didn't change something. Shaking his dick twice, he pulled up his pajamas washed his hands and went back to bed.

Jessy was having her own strange dreams, she dreamt she was really turned on and her clit was so hard it begged to be touched but she couldn't touch it, it just kept getting harder and her underwear tighter. This morphed into her walking up behind Ash who was bent over picking marbles off the floor, grabbing his nice wide hips and grinding into his ass. She wasn't sure why his hips were so wide, but she wasn't complaining, and it was just a dream right? The dream faded and another started, the memory of the first time they had tried pegging and she had joked that she had a dick. She had tried sword fighting Ash by swatting his dick with the dildo. The difference was this time her dick was real, and she could feel the heat of his stomach on the head of her penis as Ash leaned forward to kiss her.

Ash meanwhile was having another dream where he was getting pegged by Jessy. He was on top, slowly sliding up and down on the dildo. He was really enjoying the dream he could almost feel his dick flopping up and down and the firmness of the dildo inside him. Suddenly dream Jessy thrust up and he felt hot jets of liquid spurt from the dildo deep inside him. He stopped bouncing, pinched her nipple and whined, "Why didn't you tell me you were going to cum! What if I get pregnant?" Jessy reached up, cupping his breasts, and murmured "Don't worry honey, it's only a dildo." and pinched his left nipple. He squealed in pleasure as the sound of his squeal changed to a scream, Jessy's scream.

Ash woke up startled, still half in his dream, as Jessy screamed again, this time a little more quietly. He jumped out of bed and scrambled to the bathroom feeling out of sorts and off balance. "Jessy what's wrong?" he mumbled, she was standing next to the toilet facing away from it, as though she was about to sit down and pee. Her pajama pants and panties pooled at her feet. She was staring down. Ash followed her gaze past her covered breasts and exposed belly, he noticed what she had screamed about. In her one hand she held a dick, in the other she cupped a set of balls. "What is going on?" Jessy squeaked out, panting with anxiety. Ash reached out and removed her hands for her dick. She them fall to her sides, staring down. All she could see was a dick standing out from her body, just like it had been when it bounced out of her PJs as she pulled them down. It was uncut and curved just a little up and to the right. Most of the head was exposed as the foreskin had pulled back about halfway. Her glans were just a bit redder than the shaft and it pulsed gently with her rapidly beating heart.

Ash reached out and gently touched it, holding it from the underside, he knelt down on the tile floor to get a closer look, feeling his chest brushing the inside of his arms. He cupped her testicles with his other hand and gently moved them like he would his own. He changed his grip on her shaft and moved it slowly up and down as he shifted his other hand behind her balls finding the familiar folds of her labia coming to a point where her clit hid.

He looked up and her to see her slack jawed staring at him while he continued to slowly stroke her shaft.

"Ash!! You, you have tits!" "What?!" He mumbled as he pulled his hands from her new package and to down to his chest. Sure enough, his hands found what could only be described as breasts. More than he could cup in each hand soft but still firm he squeezed them, brushing a nipple as he did. He felt a little electric thrill as his nipple hardened, as if his dick was wired to his nipples.

Jessy reached out to his head turning it from side to side. "Your hair is longer too, your face still looks like you, just more... feminine." As she turned his head the tip of her new cock brushed his lips leaving a small trail of precum as it went.

Ash paused and licked his lips. He'd tasted his own precum before, it was similar, a little salty with a texture similar to his own. He'd had dreams about sucking a cock before, mostly his own, and had offered to suck Jessy's if she ever woke up with one so she understand why he enjoyed it so much.

Well, no time like the present he thought, and opened his mouth. The next time she moved his head he pushed forward sucking it in and used one hand to pull her hips forward. Jessy tried to pull back a little bit, he didn't let go. Ash used his other hand to cup her balls and make sure she couldn't pull away. He wasn't quite sure what to do with it now that he had it in his mouth. Sucking on it was fun, it tasted like well, skin mostly, with a little sweat and a hit of musk. Her reaction so far had been good, but he knew that sucking alone wouldn't have gotten him off. So started bobbing his head up and down while pressing his tongue against the bottom of her glans, he hummed occasionally like he had read about in stories, while fondling her balls. She started to move in rhythm with his head while moaning softly. Jessy placed her hands on the back of his head to help her keep up with his rhythm. Ash pulled her almost all the way out and swirled his tongue the head looking up to see if she liked it. Her breasts and shirt were in the way so he couldn't see her expression. He went back to work, thankful her new dick wasn't too big, he could get almost all of it in his mouth. He was starting to get really turned on, he could his arousal building like an itch inside him. He felt like he was sweating right behind his balls, he was so turned on. He was going to have to get off after this. Maybe Jessy would return the favor.

Jessy was stunned, Ash looked like a woman, his hair was down to his shoulders, and he had boobs... boobs at least as big as hers. She moved his head slowly back and forth as she tried to take it all in. Suddenly he pushed his head forward swallowing her new cock. She tried to pull back, but he stopped her. She resisted for a moment but gave in once his tongue started moving around her glans. It felt kind of like when he sucked directly on her clit but more diffuse, and definitely not as intense. He started playing with her balls and bobbing his head back and forth. She moaned a little and threw back her head, she was starting to get wet, this felt really good, different than what she was used to, but really good. Different definitely but really good especially when he hummed. Panting a little, she felt something building and started to thrust, using her hand on his head to get the timing right. He started to pull off and she pushed him back down. "No, don't stop now honey, it feels so good. No wonder you ask me to do this!" He responded by cupping both testicles and pulling her deeper in his mouth and starting to swallow. Her whole dick disappeared in his mouth. The swallowing motion put her over the edge; she pulled his head hard into her and came. It felt like she was shooting hot jets out of her very core, and he just kept trying to swallow making her legs start to tremble and her dick twitch.