Try as he might Jeff had a tough time getting over how embarrassed he had felt most of the time on his first date with Ashley. He knew Ashley's red dress had been pretty casual in style, but she looked so good and made-over in it that he had felt under-dressed by comparison. He felt like he had just rambled the entire time. He especially felt bad about he had mumbled and rambled around trying to dodge Ashley's question about why he was doing better at sports. He had no idea how to tell her he was simply feeling way more confident because he had a super model's vagina between his legs. Worse than all that, though was feeling awkward in how to end the date he decided to hug her goodbye which was maybe not the best way to end a date. He hadn't realized how much his arousal during the date had caught up with him until that hug and started to worry if she could feel how wet he was, how close he was to humping her hip with his pussy. He broke up the hug earlier than he would have liked to try to keep that secret between his legs.
Despite how embarrassed Jeff felt about the date, Ashley was still talking with him and hanging out with him in school. More than that she was often finding excuses to hang out with him in classes they didn't even have together, and some of her practice cheers while Jeff was playing sports were starting to sound very Jeff-specific. (Ashley probably wished Jeff would see all the subtle things too like the way she was playing with her hair all the time when Jeff was around or the way she was always gently touching him on his arm or his shoulder or his chest.)
What finally helped Jeff's confidence despite the embarrassment he felt was how much the school was abuzz with the chatter about how great Jeff and Ashley were a school power couple. There were even rumors that "Jeffley" might be the ticket to beat for Homecoming King and Queen. Jeff had never thought about being Homecoming King before, but it sounded exciting that everyone was talking about it, even to his face.
Jeff knew that if "Jeffley" was to be a thing he'd really have to make up for his mistakes on their first date. He found a suit he could borrow and set up an RSVP at a fancy restaurant in town, Galileo's. He waited for the quiet bit at the end of their end of day study hall where all the other students were off rushing home or to after school activities like sports and the teacher stepped out into the hall to direct traffic, where Ashley and he had found that if they didn't worry about being a few minutes late for after-school sports/cheer practice they could just chat for a bit in semi-private. "Hey Ashley," Jeff started, "I was thinking about our last date and thinking that I could do better. Would you like to try again Friday night?"
Ashley swept her hands into the air like she was tossing her pom-poms and squealed a little before catching herself from letting the traffic monitoring teacher hear to much and letting her hand back on Jeff's shoulder pulling him close; not quite into a hug but something more of a conspiratorial huddle. "I'd love to!" she shout whispered directly into Jeff's face. "I was worried I did something wrong. I had the best time and then you left without even giving me a kiss goodbye!"
If Jeff weren't in a huddle with the school's prettiest cheerleader he probably would have smacked his own head for not thinking about a asking for kiss on the first date, "Well, we could do that now if yo–" He didn't even have to finish the question as Ashley's head was already close enough to catch him mid-syllable in a kiss. It was breathtaking for Jeff, quite literally, as he had been mid-sentence and thus mid-breath already. It took him a few seconds to remember he could breathe through his nose and really settle into enjoying the kiss.
When they finally broke apart Ashley asked where Jeff was taking her and Jeff named the restaurant he had gotten an RSVP for. Ashley blushed and after a minute or so of moving her mouth she finally admitted to Jeff in a whisper, "Jeffy hun, you really don't have to work so hard to get into my panties. You are the most interesting guy in school. I'd probably have made out with you on the second date even if we just went back to the Turntable Diner again." She glanced around the room to check for prying eyes and then in a surprisingly swift, practiced motion, yanked panties down from under skirt, pulled them off her legs, then stuffed them into Jeff's hands. "Proof." They were very wet in Jeff's hands. They were the black "granny" panties required for her cheer uniform and Jeff couldn't imagine they could get that soaked, they were so thick. She pulled Jeff in for a brutal, quick hug then whispered, "Now I've got to rush or I'm going to be really late for Cheer, because I have to run past my locker again to grab a pair of emergency panties." She kissed Jeff on the cheek and dashed out of the room. Jeff made a mental note that keeping emergency panties in his locker was probably a great idea, realizing how soaked his own panties felt between his legs.
On Friday, in his borrowed suit (and a very lovely and frilly thong beneath his suit pants), Jeff picked up Ashley up with perfect timing to arrive at Galileo's with a table already waiting for them (but not yet in a way that the staff was upset they were late). As they sat down Jeff again admired Ashley's amazing dress. It was red like her dress from the previous date, but this time an off-the-shoulder ball gown that very tightly followed her curves. So tightly that Jeff was starting to speculate if she was wearing a g-string or no panties at all to pull off that lack of a visible panty line. Jeff thought about his own thong and if that had been a consideration in his case as well. Was he wearing the thong to keep no visible panty line in the somewhat tight suit pants or was he wearing it hoping Ashley would see it and want to explore his little secret? Jeff realized he didn't know. To distract himself from his own thoughts there he thought to ask Ashley if red was a favorite color of hers. She smiled and was so glad that Jeff had noticed. Then she admitted that Jeff was getting a sneak peak at her Homecoming Dance dress and she would not have worn it yet for anyone else but Jeff and for any other reason but a fancy dinner at Galileo's. Jeff had no probably admitting that he felt very special to see such a gorgeous sight. (Ashley could not love Jeff more for starting the date by asking about her interests and complimenting her and her dress so well so very early.)
Four courses and then a shared dessert of luscious chocolate espresso cake that the waiter insisted was on the house for such a lovely couple passed seemingly in the blink of an eye as Jeff and Ashley found so many things to chat about or just got lost in each other's eyes. Jeff remembered this time to lead with a kiss, out front of Ashley's while trying to drop her off at home. After the kiss she invited him inside and he agreed. Jeff was surprised at the sight in front of him as they got to Ashley's den. On her coffee table was a bowl of condoms and note that read "Have fun! Stay safe! Back tomorrow! XOXO, Mom and Dad" and Jeff did not expect that, even with Ashley's "proof" earlier in the week what she was planning for their second date.
Ashley caught Jeff's expression like a deer in headlights, "Relax, hun. Don't feel pressured if you don't want to do it just yet. I am happy to take this as slow or as fast as you want, babe."
"I can't," was all Jeff could think to reply. His arousal was off the charts and this was possibly the weirdest sexiest thing he hadn't thought to expect in his girlfriend's house after only their second date. Was she really his girlfriend? He wondered and was starting to think the signs were pretty obvious at this point.
She sighed, "My parents are super progressive and I didn't expect them to be this obvious about it, but I did tell them you were taking me to Galileo's and they did realize I had chosen this fancy Homecoming Dance dress gown so I guess they made assumptions and got a hotel room for the night. I'm sorry they pushed you like this."
"No I mean. I want to. I really want to. I just," Jeff realized that somewhere between the amazing meal together and realizing he had an amazing girlfriend (with apparently amazing and caring parents) he just wanted to tell her everything, no matter how much of a risk it was to let her know his secret, "I can't keep this a secret from my girlfriend. I don't have the equipment for those," he nodded at the condom bowl to distract from unzipping and pulling his pants down a little. Jeff knew it definitely was not as slick a maneuver as Ashley's panty drop at school, but it did the job of revealing how tightly his pussy was snuggled in his frilly lingerie.
Ashley responded after only a couple seconds of shock, "Oh, that's really sexy, babe. Did you wear such pretty lingerie just for my eyes only?"
Jeff nodded and Ashley wolf-whistled and pounced. Her cheerleading skills closed the distance between the two of them very quickly. Her hand gently and lovingly grabbed Jeff's crotch to get a lay of the land, "Wow, I can't believe my boyfriend is just as wet as I am right now," she whispered directly into Jeff's ear, "I can't believe how lucky I am to have the most interesting boyfriend in the whole school." She stepped back to squeal as loudly as she felt like with no teachers or parents to overhear her wild burst of joy. She grabbed a few of the condoms from the bowl, "So my parents don't ask the wrong questions in the morning, now come along to my bedroom," stuffed the condoms into Jeff's suit pockets, and then zipped up Jeff's pants for him and grabbed his hand so he'd have no excuse not to follow.
There was lots for the two of them to do in Ashley's bedroom. Kissing, petting, heavy petting, positions Jeff didn't know names for, but Ashley was happy to help explain. ("You learn some things in cheerleader camps, about what girls like," was the only explanation she was willing to give for why she knew such things, though. Jeff didn't mind because they were busy enough that night to get into such backstory.)
The biggest surprise of the night though was when they were cuddling after all of those fun things they did together that Ashley made a surprise move and pinned Jeff below her on the bed. Jeff was exhausted and as much as he rarely understood where all of Ashley's cheerleading energy came from, he really had no idea how she had so much energy and weight to trap him on the bed all of a sudden. "Now tell me how you did it!" she accused him. "How did you get such a lovely pussy between your legs? And don't tell me you were just born with it. You are still acting like it is new to you and this was all a first experience. I wouldn't believe you if you told me you've even masturbated with a pussy weeks ago."
Jeff's eyes widened. He was too tired to try to escape. He didn't have an excuse ready, and wasn't sure he was capable of lying at all in this post-pleasure state. All he could think to do was ask the easiest dumbest question his tired brain could managed, "Why?"
Ashley leaned down and rubbed Jeff's nipples a bit. "You know that model Alexandra? Super beautiful and does those men's underwear ads sometimes?"
Jeff nearly jumped as that was not at all a question he expected to hear in return. Did she somehow know he had swapped his original penis with her to get the gorgeous pussy between his legs? Did she somehow suspect his pussy's origin story despite how much the timeline seemed to change around that? "Yes?" Jeff hated that it came out as a very weak squeak.
"I've always admired her. Her career. Her beauty," Jeff thought he could see a tear rolling down Ashley's cheek and Ashley leaned down further still until she was basically laying on top of Jeff. Her tone shifted again to a bedroom whisper, "That magnificent bulge. Oh my, that magnificent bulge. Since you shared a deep secret with me already, thank you, I'll share one with you: at first as a little girl jilling myself off to sleep to some of those ads I used to imagine a beautiful woman like that wanting and desiring me. But eventually I had to admit that what I really was excited by was the other promise of that bulge: perhaps I could be that beautiful and perhaps I could be that well equipped, too." Ashley gently stroked Jeff's hair, "I realized that I wanted one."
Jeff stared at her. His girlfriend had just snapped from terrifying to loving and secret sharing in far too short of a time span for Jeff to process in his sleep deprived mind.
Ashley assumed things in Jeff's silence, "I'm sorry, babe. I didn't mean to scare you. I just got caught up in my imagination for a second that magic exists to do things like that somehow. I forgot for a second that a guy keeping such a beautiful pussy a secret all to himself would have a lot fewer reasons to use it, and definitely nothing like a cheerleading camp to explore with like minded girls in a safe space. I'm sorry."
Jeff patted Ashley on the back, "No, it's fine. You are right, I don't have a lot of experience, and…" Jeff can't hold back a deep yawn any longer.