It was late morning, Jon was struggling to decide on what to wear. He wanted to look nice since it was a date… he was also hesitant to wear a lot of his usual nice clothing, since it no longer fit the same way with his bust. Many of his nice button-up shirts were just too tight: the buttons across his boobs would be struggling to stay closed, and the gaps pulled open between the buttons were too wide for him to consider them anything close to acceptable to wear outside his bedroom, let alone his house. He was pretty sure Karyn would like that look on him… but it wasn’t really something he could wear on a date.
He eventually found one that had been a bit oversized on him but now was still slightly tight on his bust, though it was still a little big down the rest of his body; tucked in, it was not a bad look. The shoulders were just a little loose; the buttons didn’t look like they were barely holding on; the areas between the buttons still had overlap between the two sides of the shirt, though there was a bit of pulling to the sides on the one over the fullest part of his bust. Below his bust the shirt went in a straight line to the waist of his pants, if it loosened it would hang off his boobs a bit, but it looked OK.
He didn’t want to overdress: it was just a movie and dinner, and he didn’t want to make it obvious to his family that it was a date, so he went with jeans and his normal shoes.
Jon arrived at the movie theatre, looking around to see if Karyn had arrived first. He saw her playing a game in the small lobby arcade that the theatre had, and he headed over to her. She was playing some rails-shooter light gun game; it wasn’t one tied to any franchise he recognized, it seemed to be about police officers shooting terrorists or something. The plot of arcade games wasn’t exactly important to playing them. He’d played on the cabinet before, but there seemed to be a set of obscure games that the theatre rotated through, frequently without setting up the marquee and other markings on the cabinet to match the game it was running.
He found himself admiring Karyn as he approached, again realising he hadn’t felt the need to stop himself. She was wearing a checkered flannel shirt and jeans: the jeans were more fitted than the pants he was used to seeing on her and overall the outfit did a good job of showing her figure, he found himself admiring her ass in particular.
Once he got fairly close, he stopped and watched her play for a minute or two. He noticed she was low on health and out of lives.
Karyn jumped, startled by Jon speaking so close to her, and she missed all the current on-screen targets, resulting in her losing her last life in the game.
“Arrrgh!” She turned and saw Jon. “Don’t sneak up, Jon-boyfriend!”
“Er… Sorry, didn’t intend to.”
She grabbed him and pulled him into a quick kiss.
“Eh, no biggie, I was only playing while I was waiting for you. I got our tickets already. Let’s head for the theatre and get seats, or… should we get some popcorn?”
“James Bond is a popcorn movie.”
“You sure we’ll be actually watching it? We are on a date, after all. We could sit at the back and feel each other up,” Karyn said, her tone saying she was joking… part of her expression saying she wasn’t entirely joking.
“I… You’ll get plenty of time to play with these after we eat,” he said while gesturing to his chest, “I do actually want to watch this one.”
“This is why we should have gone to a movie we don’t want to see!” This time she was entirely joking.
Jon smiled, “If you just wanted to get your hands under my shirt we could have just met at your house… You have movies we don’t like there too.”
“Aww, don’t be so boring Jon-boyfriend.”
They went to the concessions stand; Jon bought popcorn and drinks for them to share. They entered the theatre it was still quite a while before the movie would start, so it was empty and they had their pick of seats. They sat in the middle of the room, where looking at the screen would be comfortable, but the screen would still mostly fill their vision. They chatted for a while: Jon mentioned his physics lab partner and how he wasn’t sure how to answer his questions, especially since the wish would end soon so it didn’t really matter. This led off into a weird conversation about if this version of reality continued to exist with alternate versions of them when the wish ended. Eventually, someone else arrived, and they shifted topics without reaching a conclusion on what they believed.
They emerged from the cinema into the bright late afternoon sun.
“I don’t think I’ll ever get used to that. It always feels weird walking out of a theatre into daylight… It feels like it should be later.” Karyn blinked as her eyes were still adjusting to the brightness.. They were walking to the restaurant where they planned to have an early dinner.
“Yeah… did you still like the movie, despite the boobless Bond?”
“I… You’ve been holding on to that one since we decided to watch this movie, haven’t you?”
“Well, later in the evening… but yeah.”
“Obviously, the movie would be vastly improved by Bond having boobs bigger than any Bond girl ever, but it was still fun. Hmmm.”
“I was just wondering which Bond would have the biggest boobs. What would Sean Connery look like? Would he have big ones… Which would carry a busty look best?”
The debate continued, each pushing a ranking for each Bond, who would be able to pull off boobs best, which one would have the biggest—or best—bust, all the way to the restaurant.
They were seated at an out-of-the-way booth in the restaurant, chatting over shared appetizers. Jon leaned forward to get a piece of one off a plate closer to Karyn; in the process he ended up resting his bust on the plate closest to him, tilting it towards him. Fortunately it was empty at the time and only resulted in a loud noise as the plate dropped back to being flat when he settled back. However it did trigger a lot of laughter from Karyn.
“Forgot you take up a bit more space than usual, eh Jon-boyfriend!” She giggled at him as she spoke.
“It’s not that funny.”
“Oh but it is! Better watch out next time you use a computer, Jon-boyfriend, or you’ll be boob-typing!”
Jon felt a bit strange about the fact that he was apparently sufficiently used to his breasts that, at least if he was having an engaging enough conversation, he could, for a moment, lose track of what they were doing. He wasn’t sure if he was glad to be getting more used to them and not being hyper-aware of them at all times or if he was weirded out by not noticing them, even for a moment. He was still decidedly aware of them most of the time… but it was also lessening in intensity and feeling less and less weird every day.
Karyn’s light teasing continued through the rest of the meal, Jon eventually firing jokes back after the main courses arrived. He relaxed again, teasing her back about looking at his bust, which she was doing, frequently.
Even as they ate, Jon was marveling at how lucky he’d gotten, dating Karyn. He was looking at her, the new wish-induced blonde streak in her bangs running down the side of her face, mixing with the waves of red—her original hair, now in a long cut that had never existed prior to her wish that restored her hair. It was beautiful. He too was stealing glances at boobs. Hers were a little less obvious in her flannel button-up: it was just a little tight across the fullest part of her bust and loose everywhere else, but it still showed enough hints at her figure underneath to be flattering.
Karyn had noticed the tightness of Jon’s shirt across his bust when she first saw him in the theatre, but now, sitting across from him, she had had trouble not spending the meal talking to his chest. She found the way a few of the buttons noticeably strained to hold the shirt closed immensely distracting, but she was also enjoying it just as immensely. Jon’s occasional remarks kept her from looking for too long, several times when she hadn’t even realised she was looking.
Eventually the time came to pay the bill and move on.
They arrived at Karyn’s house, it was as the expected empty. Karyn unlocked and opened the door, and as soon as they were both inside and Jon had pulled the door closed behind him, she pulled him into a tight embrace and kissed him.
“So… What now, Jon-boyfriend?”
He kissed her again. “How about we just…”
“Go to my bedroom and see what happens next?” She could tell he was nervous and could feel the tension in his body. She was nervous too, just as unsure, but… she also wanted to get a chance to at the very least make out again before the wish making her like boobs and the one giving Jon his amazing set of them ran out.
“I… I was going to say living room…”
Karyn released him and stepped back, undoing the top few buttons on her shirt as she stepped, just enough to show a decent amount of cleavage. She leaned forward slightly. “C’mon, what would we do in the living room that we couldn’t do in the bedroom? We’ve got lots of time alone for the first time since…”
“I… I wasn’t objecting…”
“Not… sure how… far I want…”
“We’ll go slow… I’m not sure either… C’mon… let’s go.”
She moved back toward him and grabbed his hand, and pulled him along behind her all the way to her bedroom.
“So… where were we…” Karyn turned and went back to slowly undoing her top. She felt silly doing this, but at the same time she was aware that if Jon were doing the same she’d be enjoying it.
Jon for his part enjoyed the show she was putting on. It was having the intended effect on him.
As she ran out of buttons, she let the shirt slide down her arms, exposing her chest and bra.
“Your turn, Jon-boyfriend.”
She pushed him gently and he let himself fall backwards onto the bed. She crawled up the bed and straddled him. She started slowly undoing his shirt buttons; she could feel Jon’s body responding, poking her backside, she felt her own body respond. She smiled down at Jon and continued to unfasten his top: she was reaching the buttons that were tight and had to squish his breasts to give herself enough slack to get the button to come out. She did not consider that to be a bad thing. She was again marveling at how good Jon looked with boobs. She found herself undoing the buttons faster, quickly getting the shirt all the way undone. She pulled it open.
“Wow… you really do have very nice boobs… I… just want to…”
“Your’s aren’t exactly anything to sneeze at. Ahh!” Jon cried in surprise, raising his arms slightly, as Karyn stuck her face into his bust, with his bra still on. He looked down at her, she was looking up at him with a slightly embarrassed, but happy face. “I… was not expecting that… wouldn’t it… have been more fun if I weren’t wearing a bra?”
“Uh… probably…” came her slightly muffled reply.
Jon let his arms close, and ran his hands down Karyn’s back. He lifted the bottom of her shirt and drew it up until it uncovered her bra’s band. With what was now a practiced motion from undoing his own bra, he released the clasp. He felt her bust shift against his tummy as the support from her bra disappeared.
“OK mister, mine are free. It’s your turn.” Karyn pushed herself back up out of Jon’s chest and back into a kneeling position; she pulled her shirt and bra shoulder straps all the way off. “C’mon, lift yourself up a bit so I can undo yours.”
Jon grinned at her, though his eyes were actually on her chest, as he pushed himself up onto his elbows, giving clearance so she would be able to reach underneath him.
She leaned forward again, her bust swinging and dangling as she did so, her hands reaching Jon’s chest; following along the band of his bra under his open shirt, she found the clasp and released it. The tension in the band relaxed, the bra cups lifted up, and his breasts puddled and settled slightly lower on his chest as the pressure holding the bra cups against him went away and, with it, the cups' ability to shape his boobs.
Jon pulled his arms in, through his shirt sleeves and bra shoulder straps, and tossed his bra away, giving Karyn a full view of his bare bust. She brought her hands in and started gently playing with his boobs, cupping them, gently massaging.
For Jon Karyn’s ministrations felt amazing, he found himself groaning from the pleasure of the feeling. “Mmmm, God Karyn, are you ever good at that.”
“Well I’ve had some practice on myself.” She could still feel Jon’s erection against her butt, which was adding to her own arousal as much as playing with Jon’s boobs. She was also mindful of what happened last time they made out, she didn’t want Jon going off too soon. Not much danger of that from just his boobs, it took most of the hour… but caution.
Jon reached up and started feeling her up in return. She felt herself start to moan softly back at Jon; felt what she had thought was his full erection harden more at the sound.
Jon could feel her butt against him, and they were each moving enough that even through his underwear and jeans there was some sensation of movement transmitted. As his arousal grew and even that small amount of stimulation happened, his reservations about not going all the way weakened. He let one hand run down along Karyn’s body, following the curves, feeling the soft skin, down to the waistband of her jeans, then along it, across to the front, to the button.
He paused, even if he did this next part they could still stop. He undid the button, paused and looked up at Karyn for confirmation that she was still comfortable with this. She was smiling and gave him a little nod of encouragement. He felt himself moan again as she combined this with a slightly more aggressive stimulation of one of his nipples. The nod was all he needed, he pulled the zipper closing the fly down, slowly and gently.
He started slipping his hand behind the waistband of her panties, and hesitated.
Karyn sensed that Jon was unsure, “Go ahead Jon-boyfriend, as far as you want. I want you.”
Jon took the invitation, his hand slid down inside the front of her panties, to her vagina, slipping his middle pair of fingers inside her. As they entered Karyn let out a soft gasp. Jon let his palm press against her hoping it would stimulate her clit with pressure. He let the tips of his fingers explore together, rubbing at parts of her insides, pulling towards his palm.
“Mmm… that’s nice Jon-boyfrie….eeeeeee… Don’t stop that, that’s the spooooot!” Karyn spoke in halting breaths. Jon had found her g-spot.
He did as she said, continuing the motion he had been using. Her moans grew in volume and her breathing quickened. Her massaging of his breasts stopped, she was now gently squeezing and releasing them, her palms pressed over his nipples. It didn’t feel bad… but compared to the intentional massaging she had been doing it wasn’t doing much.
Karyn felt herself building, pleasure and warmth spreading from her vagina, the entire meal sitting across from Jon, being distracted by his boobs, the anticipation from the day before. All had left her very keyed up. It didn’t take long before she was getting very close to coming.
“Mmmuh Jon… I gonna… muuaaaaa” She came, and in the process accidentally squeezed Jon’s boobs a bit hard. Waves of pleasure radiated out. She felt herself clamp down on his fingers, rhythmically gripping. As she came down and started to relax she let her weight rest on Jon, she was panting slightly from the exertion.
“Ow Karyn, be careful what you’re holding on to when you get close.”
She looked down at her hands on Jon’s boobs, “OH! I’m sorry, I…”
“Don’t worry about it. It doesn’t hurt anymore.”
“I… I’m still sorry… You were doing such a goOOOOd” Jon wiggled his fingers as she got to the word ‘good’, “job.” She glared at him, playfully.
“OK, mister, what next?” She was feeling more aroused now than she had ever before, Jon’s fingers inside her weren’t enough to help with the feeling of emptiness she felt, she wanted something more substantial, something that was poking her in the butt.
Jon pulled his hand out of her, and her panties. “I… Well we could finish getting undressed. I… want to… um… go all the way.” He had thoroughly enjoyed making her cum, giving such obvious pleasure to his closest friend, turned girlfriend, was one of the best things he’d yet experienced.
Karyn found herself feeling a surge of even more arousal, and joy, she was elated, even more than she thought she would be. All her own doubts had been washed away by the fingering Jon had just given her. Though now without even his fingers inside her the feeling of emptiness was stronger, she felt more need to be filled. She lifted herself back up and shuffled down a bit and started undoing Jon’s jeans, quickly.
“Lift your butt Jon-boyfriend. I want to see…” Having undone his button and fly she now could see what was making the tent in Jon’s pants. She was surprised, it looked bigger than she was expecting, she stopped to just look until Jon did as she asked and lifted his hips off the bed, she excitedly pulled down both his jeans and underwear. Jon’s penis sprung free, standing proud, a slight upwards curve. It was bigger than she expected, it was also nearly as much fun to look at as his boobs.
Jon let his hips drop back down to the bed, triggering a wobbling motion in his penis, which also fascinated Karyn. For a moment she was lost just looking at it, feeling the warm rush between her own legs as her body further ramped up it’s lubrication. Then she snapped out of it, and pulled his pants and underwear below his knees where he kicked it the rest of the way off.
For her part she swung one leg back over him so that they were both on the same side of his body, preparing to discard her own bottom clothing. She quickly pulled them down to her knees and shuffled forward to get them the rest of the way off, with some help from her hands. She crawled back over to Jon and straddled him again, then lowered herself down so that his penis was just in front of her, part of it touching her.
Jon while watching her do this, enjoying the little show, watching Karyn’s boobs move, the reveal of her vagina, and her legs, found himself idling playing with his own boobs. It felt so nice, gently and without much intensity. As she was now in position on him though all of his attention was now on her, and how close her parts were to his.
“OK Jon-boyfriend… are you ready… I… need you.”
“Am I ever!”
Karyn drew a short breath and let it out forcefully, psyching herself up, “OK, I’ll… guide you in.” She lifted herself up and took Jon’s penis in her hand, shuffled forward just slightly. It felt big in her hand, the texture, the soft skin layer over a very solid feeling core. She felt something like how she felt about touching Jon’s breasts, obviously the thing itself was very different, but it brought her a similar enjoyment. It felt weird that she was relating this to liking boobs, she had always been into this, boobs were new, but she had touched boobs before now, she had never held a penis before. She had raised herself up just enough that once she moved forward the tip of Jon’s penis was just touching her, spreading her labia just a little, she lined the tip up and started to lower herself down onto it, slowly. As it started pushing against her, spreading her labia more, then pushing against her vaginal opening, then entering, stretching her a little at first, then more. As the entire head pushed in and she felt the ridge around it she let out a deep moan of pleasure. It felt much bigger inside her than it looked. She continued to slowly lower herself, feeling it push further and further into her, the thickness at her entrance slowly increasing, making her feel fuller and fuller. This was what she needed, by the time she had it all in the sensation of emptiness was gone, replaced with a very satisfying fullness. She squeezed and got a groan of pleasure from Jon in response.
Jon felt the warmth, the wetness, the pleasure as his penis was slowly engulfed. It felt wonderful, he was watching Karyn’s face, enjoying the look on it the entire time. She had her arms up in the air giving him a good view of her entire body, her breasts, the slight tummy she had the curves of her figure, but the look on her face took the cake.
“Oh wow Jon-boyfriend,” She twisted her hips a little, getting a little gasp out of Jon, “mmmm this feels incredible. I just want to… stay like this for a bit… but…” She brought her arms down and her hands came to rest on Jon’s chest, feeling his nipples poking into her palms, she went back to gently playing with his boobs, rubbing around his nipple with a thumb on one side, gently squeezing on the other. She felt him start to squirm under her, his hips moving slightly, moving his penis in and out, just a little, but it was enough to feel nice to her. Looking at him he was obviously too involved in what she was doing to him to return the favour and play with her chest. She kept this up for a little while, enjoying watching him squirm in pleasure while feeling him filling her up.
“Huurg, stop for a bit Kare”
She took her hands off him and was about to lift herself off when he continued.
“Thanks, I… was getting close… I… want to hold on for a bit, just let me uhm… calm down a bit.” He close his eyes
She was still enjoying the full sensation, while also doing her best not to move and stimulate him. She was also enjoying just looking at him, his arms and shoulders, a little tense as he was gripping the mattress, giving his arms a little extra definition, but mostly she was watching his boobs, rising and falling as he breathed, quickly from his arousal. After a minute or two she said “Whatcha thinkin’ ‘bout”
“Oooh, the sexiest school subject!”
Jon giggled slightly. “Aww dangit now all I can think about is curves”
“They’d better be my curves. Jon-boyfriend.”
He opened his eyes, “Those are the best curves, can’t deny that.”
She blushed a bit at the compliment. Then felt silly, blushing at a compliment from a guy while he was balls deep inside her.
Jon felt like he had things under control again; he reached down and put his thumb against her body where his penis disappeared into it, sliding it up against her, looking for the right part.
“What are yoooooooooOOOU”
Karyn’s voice went up in pitch and turned into a surprised moan as Jon found what he was looking for. He felt her clamp down on him as he gently rubbed her clit, she continued to moan.
“I think I’m ready for more fun now,” he said.
“Huuh, I… I… should hooope soOOoo, doooOOooing thaaaAAat toooOoo meeEeEe.”
She started slowly riding him as he continued to rub, He felt her going up and down, his penis going in and out. Heard her moaning as he gently rubbed. Saw her boobs bouncing as her body bounced. She started playing with her own boobs as she rode. He felt a familiar pressure building, a need, it grew, he felt himself moan softly as he got closer and closer. Still he managed to keep rubbing her clit. Then he felt her rhythm speed up, and she spoke.
“I geEeting clooOoose. Doon’t StoooOOop”
He redoubled his effort to focus on what he was doing to her, to maintain his pace. To hold himself back, just a little longer.
“mmmmM, I’m gonnaaaaAA”
He felt her body drop onto him, her vagina clamp down and begin pulsing rhythmically, and her arms came down and she caught herself on them, now leaning forward supported by them, panting as she came.
“Oh wow, Jon-boyfriend, that was.. Incredible. Are you sure you’ve never done this before.” She said with halting breaths.
“Mmmm, very sure.” Jon was close himself, he found himself squirming under her again, desperate to get closer, he needed it, to get more stimulation to cum.
“Now it’s your turn.” She started riding him again, but this time she also started playing with his boobs again. He felt himself start to groan with pleasure, rapidly rebuilding the momentum lost when she stopped for her second orgasm. Building, building, pleasure spreading from his chest, little sparks of it running down his body into his groin, his penis down there in the warmth and wetness, being squeezed as hard as Karyn could manage, after all that she had already done. Closer and closer, until…
“I’m gonna cuuum.” He groaned, and grunted, he felt the push, the burst of pressure move up from inside him and along his penis, and out. Four times he pulsed and pumped, and then he felt his body relax.
Karyn relaxed too, just letting her weight settle onto him. She continued to gently play with his boobs. He was somewhat surprised to find that unlike his penis they didn’t get overly sensitive after he came, it still felt nice to have her touch and squeeze.
“Well Jon-boyfriend, did you have fun?”
“Oh, a little, that was just one of the best things to ever happen to me. Did you enjoy yourself?”
“I…” She was feeling his erection softening and shrinking inside her. “I… I’m pretty sure I made enough noise to make it clear how much I was enjoying myself. I don’t really want it to stop… God I love the way you feel inside me… and I love you…” The words had just come out of her before she really knew what she was saying, but as she said them she was sure she meant them, from the bottom of her heart.
“I… wait what was that last part?”
She stopped playing with his boobs and looked him directly in the eye, “I love you”
A whole cascade of feelings hit Jon, a warm mushy one, a lot of little complicated ones, and one between his legs, he felt his penis stiffen right back up. Before he could get a word out Karyn spoke again.
“Oh! Well, it seems like that made you happy!” She grinned at him.
“Err… Yeah… I love you too…”
“Say it again”
“I love you Karyn.” It wasn’t something he had ever expected to say a week ago, but saying it, he knew it had been true for a long time.
She leaned forward and supported herself on her elbows so she could kiss him. She felt a little bit of his penis slide out as she had to move up to get close enough. The kiss lasted for several minutes. After they broke the kiss she pulled back, to get the full length of Jon’s dick back into her.
“Want to go again Jon-boyfriend? Sure feels like you’re ready for it.”
“I… Karyn if I could I wouldn’t stop for as long as you still want to keep going.”
“Well if all I need to say to get you going is ‘I love you’...”
He felt another thrill of arousal, “As nice as that is to hear, I don’t think it’ll work forever.”
“Oh I don’t think I can keep going for more than one more, I’m pooped. Which is why we’re rolling over.” She leaned back down against his body, feeling their breasts press against each other again. “OK Jon-boyfriend, ready?”
They rolled together, so now Jon was supporting himself on his elbows and she was underneath him. She grinned up at him.
“God Jon-boyfriend, I’ve been thinking about seeing that view… a few times over the last week.”
“Wha? What view?”
She brought a hand up and pointed down at Jon’s chest, his boobs dangling from him. “That one, I… um… yeah… I’ve been thinking about you a lot.” She turned bright red. It felt silly to be this embarrassed to admit to masturbating to someone she had just had sex with and was in fact continuing to have sex with, but she couldn’t help it.
Jon also blushed. “I… is the reality living up?”
“OH! Is it ever! Just one thing… you’re not… um… making them… um… swing…” She felt sillier still having trouble talking about this.
“Hmm? Oh! I see.”
He started thrusting, slowly at first, building up speed. Karyn moaned softly in time with each thrust, watching his breasts swing, and her own jiggle.
Eventually Jon felt himself getting close again and he let her know… then grunted as he came.
“Whew.” Jon rolled off her, and just relaxed for a moment.
“Yeah… That… was quite something…”
“Mmm yeah,” she glanced down at his rapidly deflating erection and said “I love you, Jon, really do.”
“I love you too.”
She glanced down again, “Aww, didn’t work.”
They both started laughing.