Date: Sun, 21 Mar 2021 13:56:13 +0000 From: Smut Butt Subject: Trans And Trans (TG/Teen) Hello! Long time reader, first time author. I wanted to write a story of gender discovery/exploration and romance featuring a trans girl, a trans boy and mutual teenage awkwardness. It's the first full-length story I have ever written so I hope it's any good. Be aware the story does contain misgendering and deadnaming as a part of the plot. This story is 100% fiction. It contains underage characters engaging in sexual activities. If this offends you or is illegal for you to read, please close this window. Thank you to Nifty.org. ------------------------ Trans And Trans ------------------------ I met Jay at an anime convention. Well, not quite at the con proper. We happened to have a mutual friend who offered us a place to stay for the duration of the event. My parents were a little hesitant to let me travel to a different city - after all I was only 13 years old - but relented, knowing I would be taken care of by the host family. On the first day there I was introduced to Jay by our mutual friend. We did not get to know each other well during the con as we both had our own friends to hang out with. I did chat a little bit with him some evenings after coming back from the con and he seemed like a fun dude. Sometimes I look back and wonder how our lives would look had we ended up going separate ways. After the last day of the convention, we were back at our friend's house. I was in a t-shirt and a pair of jeans with a towel tossed over my shoulder, about to go for a shower. When I opened the unlocked bathroom door I was met by the sight of Jay's back, his hair tied in his distinctive ponytail. He was changing clothes and had stripped down to a pair of boxers and what I immediately recognized as a binder. I noticed he had heard the door open but before he could react, I blurted out "Sorry, sorry!", closed the door and retreated back to the guest room. I may have panicked a little on the way but managed to make it to my bed. He showed up some minutes later clad in board shorts and a sleeveless shirt, looking frustrated to say the least. I was not sure if he had cried but his eyes did look a little red and puffy. I was not doing much better, having no idea how to handle this situation and therefore just sitting on my bed in silence, nervously scratching the back of my left hand as I tended to do when anxious. He must have noticed how uncomfortable I was because his expression mellowed out a fair bit. "Hey... Sam, right?" he gently began, standing in front of me a few steps away. "Y-yeah", I stammered, my hands now separated and curled up into tight fists on my lap. "Jay, I'm sorry, I didn't realize-" "Nah, it's fine", he said, acting quite nonchalant, though I could tell he was still not happy to be in this situation. "I thought I locked the door but the locks are different than at home." I nodded but wasn't sure what to say so we spent a few seconds in silence. "So, uh..." I eventually managed mumble. Jay must have known what was coming but he was letting me do the honors. Or dig myself into a hole. I couldn't tell how he was going to react but I sighed and took a deep breath to gather my nerves. "I won't tell anyone what I saw", was the wording my brain eventually decided on. Jay's expression slowly turned into a gentle smile and he maneuvered to sit down next to me. "Thanks. I appreciate it." I looked at him and despite the smile he did not look happy. "Sorry, I didn't want to stress you out. Once I'm home it's gonna be back to being a girl for me, so I'm a little... On edge, I guess", he explained, laying back across the bed with his hands under his head, looking up at the ceiling. "I'm sorry", I said, looking at him. "I know how you feel." His gaze immediately met mine and I could feel him wordlessly pleading me to go on. It did not help me with my nervousness. "I mean, I don't know what I am, but, uh... You saw my cosplay, right?" "Oh yeah, Madeline from Celeste!" he replied, letting out a little laugh, clearly cheering up. I couldn't help but giggle with him. "You pulled it off really well, too!" "Thank you." I'm sure I was blushing very noticeably. It felt really nice to hear. "I didn't realize there was any deeper meaning to picking a transfem character. A lot of people like that game for other reasons too", he pointed out and he was right: I had picked a multi-faceted character on purpose. "Well, to be honest, I don't know either what the meaning is. I guess I'm still figuring things out", I explained, facing forward again, finding it a little easier to talk to the otherwise empty guest room. "I'm afraid to try anything out back home... School is hard enough as it is." He sat back up and put a hand on my shoulder. "Yeah. Don't worry, I won't tell anyone either." His words felt warm, compassionate, understanding. I don't know what took over me but without saying a word of warning I hugged him. He was surprised but soon wrapped his arms around me. We stayed in the embrace for ten, maybe fifteen seconds before he gave me a pat on the back as if to signal that was enough for now. I pulled back, embarrassed, but he laughed quite heartily. "I definitely needed that hug too", he said between bits of chuckling, and once again his laughter was contagious. "Hey, I should probably start to get going, but we should keep in touch", he then said, pulling out his phone. We exchanged details and he gave me another hug, though a lot briefer than the first, and then headed out. It was only then I noticed the towel I had left on the floor and remembered it was time for a shower. --- We found ourselves chatting online just about daily for the next week. The subjects were pretty mundane, basically just getting to know each other. He's 14, has a younger brother, a mom and a dad, loves sports and gaming, sometimes gets into trouble in school but never anything serious... This kind of stuff: "got detention today" "Oh what happened?" "pe teacher went somewhere i snuck on the boys team he came back and noticed the girls loved me though :) i was kicking their asses lol" "Wow the boys' asses? The boys here are super good at sports" "nah the girls they were happy i stopped destroying them :D with boys im only like top 5" We didn't talk about gender though. Jay mentioned in the only voice call we managed to have that he was concerned his mom might snoop around, so he did not want anything "too incriminating" in the chatlog. I felt he might have been a little paranoid but it was better to be safe than sorry. I found myself craving more on that subject but did my best to keep it bottled up. We were still able to share some common experiences without looking too suspicious... "Hey, just wanted to know how you feel about going swimming sometime? News says it'll be a hot summer" "i used to love swimming well beaches are still pretty nice sometimes but swimming classes in school..." "Oh yeah. Too many people" "yea need some space :/" It also turned out he lived just one town over, about 15 kilometers away. We decided that the next weekend I would bike over and we could spend some time hanging out outdoors, enjoying a picnic. He did say his mom insisted on meeting me at least briefly before letting him hang out with me so for clothing I picked a generic black t-shirt and a pair of unisex shorts - nothing too controversial. --- Saturday turned out to be a hot day so the bike ride was a bit uncomfortable, though not unbearable. Jay's house was a cute, older two-story wooden building, nothing extraordinarily fancy but likely upper middle class. I pushed the doorbell and was soon greeted by a woman who I could best describe as a 1950s housewife with a modern twist. She couldn't have been older than 40. "Ah, you must be Sam!" she said, all peppy and friendly. "Hey, Cassandra, your friend is here!" she called out. It took me a moment to connect the dots as I had never heard that name before. "Come on in, welcome!" She moved aside to let me into the foyer. "Thank you, Mrs. Young", I replied as I stepped in, having snatched the surname from their mailbox. "Why, you're an observant and polite boy", she said, smiling. "Cass could use more friends like you." I found her tone of voice a little too syrupy, but then again Jay's friends in school were a little on the rebellious side from what he had told me. Jay showed up shortly after, once again wearing a sleeveless shirt though this time with a bra underneath judging by the slight impression it left on the shirt's fabric, along with a pair of loose boys' shorts. His hair was tied back with the same style of ponytail he had worn at the convention. "Hey!" I said, thinking what a great greeting "Hey Jay" would have been - I had to save that for later - and he gave me a similar greeting back. His mom, though, seemed to sour pretty quickly. "Cassandra. What did we discuss yesterday?" She sounded very stern. Jay looked disappointed if not defeated and retreated back without a word. "I apologize, but I want her to look presentable when she's out and about. I'm sure you understand", she explained to me and I nodded along. As if he wasn't presentable like that - he looked like any other boy. But I guess that was the problem... Being a little sweaty I did not dare to come too far in, so aside from a quick trip to the bathroom I stayed on a wooden chair in the foyer, drinking a glass of cold orange juice Jay's mom brought me, having a bit of small talk with her. She also gave me a small cold box with our picnic goods which I stuffed in my backpack. Jay returned after a few minutes. This time he was wearing a gingham dress with a pink and yellow plaid pattern with his long hair loosely falling onto his shoulders. I was fortunate not to have any juice in my mouth to choke on. He looked sullen, maybe even trying to hold back tears but also doing his best to keep his cool. "There we go, was that so difficult?" his mom asked him. She looked satisfied and maybe even a little smug. Some part of me wanted to speak up but I continued to just sit there, glass in hand, watching the scene unfold. "No, mom", Jay muttered, his expression stiff and eyes looking down. He quickly grabbed his large messenger bag, tossed it over his shoulder and gave his mom a hug and a kiss, though it looked to me like he was just going through the motions. They exchanged "love you"s and we were out the door almost immediately. "Let's go." His voice was cold and a little shaky. He jumped straight in the saddle of his bicycle. I got on my bike and let him lead the way without any words. He was pedaling like hell and I had trouble keeping up, but every now and then he peeked back and stopped for a moment to wait for me, though he avoided eye contact. It took us about five minutes to come to a secluded, wooded spot beyond the neighborhood and Jay maneuvered his bike onto a trail that was probably not used as more than a shortcut. "Jay", I started, hoping to cheer him up a little, but he merely grunted in reply before coming to a stop on the path. "Keep watch", he said, letting his bike fall aside as he got off it. It took a moment for me to realize what he meant, but when he pulled the hem of the dress up and over his head I caught on and turned around. Fortunately, it seemed like a rarely used path. My ears were alert but all I heard was him rustling with his clothes, followed by what sounded like him quietly sobbing. I turned around and saw him slumped in a sitting position on the ground, back in his sleeveless shirt and shorts, the dress crumpled up on top of his bag. He had his legs pulled up and his face in his knees, with his hair still loose, draped all around his head. I quickly walked over, let my bike fall by his and kneeled down to wrap my arms around him. His restrained sobs soon turned into open crying as he let his legs fall and buried his face in my shoulder. I just held him tight, feeling some tears in my eyes as well. I wondered if I should say something but in the end I decided to let him get it all out of his system, just telling him to take deep breaths. It took him some minutes to calm down enough to ask for a tissue from the front pocket of his bag, which he then used to dry his eyes and blow his nose as I backed up from the embrace, sitting down on the forest floor in front of him. "Sorry", he eventually muttered between continuing but smaller sobs, "I was hoping I'd get away with it, but mom... I don't know, she thinks I'm just going through a phase", he explained, avoiding harsher words out of love for her, I think. I put a hand on his leg just below the knee, gently rubbing it while he wiped his cheeks and chin with another tissue. "Sorry I didn't say anything", I apologized in return. "Probably best you stayed silent", he said, glancing at me, I think hoping I did not take offense. I nodded, agreeing I most likely would have just made the situation worse. "She thinks she's doing what's best for me, but..." His words trailed off and he sighed. "Ah, let's not talk about it, not now... Not when I get to be me." "You're always Jay to me." I don't know how those words came to my lips but Jay managed to crack a small smile despite still sobbing a bit. "Thanks, Sam", he softly replied, reaching in to give me a quick hug. "I'm gonna sit down for a little bit longer. Gotta catch my breath." He threw his head back and started to work his hair into a ponytail. "Yeah, that's fine, take your time." I looked around to make sure the coast was still clear and then got up to take a few steps toward Jay's bag. "I'll fold this thing", I said as a I picked up the dress, "And stuff it in my backpack so you don't have to look at it." "Sounds like a plan. Maybe I'll forget that I have to wear it again later", Jay said with a small, dark chuckle. Before folding, though, I examined the dress a little more closely. It was a lovely dress for sure and the soft fabric felt wonderful in my hands, but it was definitely not Jay's style. "This would probably suit me better anyway", I said in a half-joking tone, but I noticed from the corner of my eye that Jay perked up immediately. "Do you want to try it on?" he asked. I turned to look at him, and in spite of the clear signs of crying just moments ago he seemed serious and eager. "Of course you don't have to", he quickly added, "But if you want to, you can. I think we're the same size." I looked at the dress again and could feel my breath growing more rapid and tight. Something about it was tempting and alluring, and I knew Jay was going to be supportive no matter how it looked on me. "Your turn to keep watch", I eventually said, my voice squeaking out of nervousness. Jay stood right up with a grin and turned around. My hands were a little shaky, but I managed to lay the dress neatly down on our bags. I pulled my t-shirt up over my head, popped my shorts button open, pushed them down and slipped my flippers off my feet, soon standing in the middle of the woods in just a pair of boyshorts - my treasured girly-but-not-suspiciously-girly underwear. Picking the dress back up, I admired it for a moment more while trying to figure out how to best get it on, and soon realized it could just be slipped on like a shirt. Taking a deep breath, I pulled the hem over my head and dove into the dress. It really wasn't difficult to get it on, though it did take me a few tries to get my arms and head through the right holes purely due to how shaky I was. I exhaled. I was wearing a dress. I looked down and watched the hem sway lightly in the gentle breeze. It was an intoxicating sight. I don't know how long I spent there in my hypnotized state. Eventually I took a few deep breaths to calm down and straightened the dress up, making sure it looked good. "How does it look?" I hoarsely asked, only now realizing how dry my throat was. Jay turned around and took a long, good look at me, even taking a few steps around me to see me from different angles, clearly admiring the sight before him. To this day I don't know how to fully describe the feelings I had in that moment, but I felt vulnerable yet somehow empowered. "It looks amazing", he eventually declared, moving back in front of me with a broad, toothy grin on his still red face. "Daaaamn fine", he added with a laugh, making me giggle as well. "I'd let you keep it if I could." "I know you want to get rid of it pretty bad", I said, though I regretted my words almost immediately, thinking I sounded a little rude. "No, seriously!" he quickly replied, clearly not willing to accept my dismissive comment. He raised his gaze from the dress and we looked each other in the eyes. "You look really good in it." If there was not a blush on my cheeks already there certainly was one now. We both averted our gazes pretty quickly and he coughed. "T-thank you", I managed to stutter after a few seconds. I was not even sure how he meant those words, but in any case they made me feel warm inside, if a little awkward as well. I was a little lightheaded, feeling a little foreign yet oddly at home in my new attire. It was a lot to take in all at once. "So... Do you want to change back or keep it on?" Jay asked. I did not have to think about it for long. "Before we go... Can you take a picture of me? I, uh... I want to see how I look", I replied while grabbing my water bottle for a sip. I did not question Jay's judgement but I did also want to see it for myself. "Sure!" It seemed like Jay was full of energy again, quickly digging his phone out of his pocket and stepping back to get a good photo. "Alright, smile!" he ordered as he brought the phone up, snapping a few photos in quick succession, walking back to me immediately after and standing by my side, showing me the pictures. It was a bizarre sight. I saw myself, I recognized myself, I knew that was just me in a dress. But it also felt like I was looking at a different person. A girl. A beautiful girl, enjoying the summer heat in her pretty dress. Thoughts raced through my head. Was this just a fun little experiment? Was this a side of me? Or was this all of me? "I told you you looked good", Jay eventually commented as if to break me free from the spell before he tucked the phone back in his pocket. "C'mon, let's get going. We got a picnic to enjoy!" he reminded me as he picked his bag and bike back up. I followed suit and soon we were underway again. --- I don't remember much about the next fifteen minutes. We made our way through the forest path, mostly walking our bikes because of the tree roots breaking ground, making the path way too bumpy to ride on. Jay seemed to give me some mental space, if it can be described as such, to get used to... Well, everything. Feeling my legs so exposed underneath the hem, the wind tickling them higher up than ever before. Feeling the seat of the bike directly against my underwear for the brief moments we were able to ride them. Looking down and seeing the slightest appearance of breasts due to the dress leaving just a bit of room for them. The more I grew used to it, the more comfortable it all felt. Jay spent most of the time chatting about how he was able to be a little more boyish in school but how their dress codes were limiting. I just listened, giving him a few words at a time at best. He seemed to be willing to carry the conversation completely on his shoulders - I just made a mental note to participate more later, when I felt capable of doing so. Somehow, I did notice that the forest, so far quite uniform and dense, was about to end judging by the lack of treetops following the next small hill. Jay guided me up the slope which seemed to be just about pristine, very rarely climbed by more than a few people. Once we were at the peak, before us was a large, clear lake with bare bedrock leading down to it after the final line of trees. "Welcome to Spring Lake!" Jay announced triumphantly. "At the other end there's a beach just about everyone goes to, especially when it's hot because the water's always cool", he said as we were making our way down to the lakeside, "But this here is my secret spot. No one ever comes here!" Jay placed his bike on the stone surface and turned to look at me, as if expecting a comment. "We're definitely coming here again", I said, trying my best to sound impressed by the place - which I was, to be fair. "But I didn't bring swimwear." It was definitely a bummer to miss out on swimming, but at the same time I was a little relieved to have an excuse to keep the dress on. "Don't worry, I brought extras!" Jay said, digging into his bag. I let out a soft sigh, both happy and disappointed, and started to unpack as well, placing the cold box in a shady spot. I noticed he had placed a pretty standard pair of boys' black swimming trunks, quite similar to the ones I usually wore back home, on the ground. Maybe it was not going to be too bad after all. I could always get a little more dress time after a refreshing dip in the lake. "So, uh", he continued, seemingly a little hesitant and maybe even a bit fidgety. "Let me know if this is going too far for you, but I also brought... This", he said as he pulled out a black, sporty one-piece swimsuit. I had no idea how to react, but I guess Jay was able to tell I was flabbergasted and kept talking: "My school swimsuit from last year. It might be a little small, but I decided to take it... You know, just in case." "It does look small", I said, trying my best not to sound dismissive. Jay seemed apologetic anyway. "I don't want to make you uncomfortable", he began to explain but I interrupted him. "I want to try it on", I dared to say, gulping audibly. Jay nodded and handed the swimsuit to me, a little nervous himself. "I'll look away while you change", he said, turning around and pulling his shirt over his head, leaving his binder on. I don't know why, but I continued to watch him as he dropped his shorts and kicked them off, followed by his pair of boxers. My eyes were fixed on his bare butt for a few seconds after which I turned away, ashamed to have stared for so long. I took one more good look down at my dress before pulling it over my head, leaving me in just my boyshorts and shoes, the latter of which I kicked off my feet. To my embarrassment my crotch was bulging a little - whether it was due to the swimsuit I was about to put on or the sight of Jay, I could not tell. I slowly slipped my underwear down, revealing a hairless crotch and my small, half-erect, lightly throbbing penis. I was expecting to not like the sight of it while feeling so girly, but now that it was there, I did not mind it nearly as much as I thought I would. Figuring I should get changed before Jay turned around, I slipped my feet through the holes of the swimsuit and pulled it up in one smooth motion, surprising myself with how naturally I managed to get it on. It was definitely a tight fit - the swimsuit was just form-fitting, and the crotch in particular squeezed me firmly, only aggravating my stiffness, stretching the fabric even further. I covered the bulge with my hands. "U-uhh, Jay", I mumbled. He had already set everything up and had slipped on the pair of swimming trunks I had left unused. "Can I look?" he asked, continuing to face the lake. "No, please don't. It's... Tight", I managed to say. I tried to keep my hands still, but some part of me wanted to rub myself through the swimsuit. Jay shrugged. "That's fine. You don't have to wear it if you don't want to", he said in a maybe slightly disappointed tone. "No, I want to, but it's... Really tight", I tried to clarify using the tone of my voice. Jay was silent for a moment. "Oh, you mean..." My reply was some kind of a mutter in the affirmative. There was another brief silence before he started chuckling. "You can slip in the water. I'll follow you", he suggested. "The water should, uh... Calm you down." I let out a little giggle as well, though it probably sounded somewhat forced. Stumbling a little, I managed to make it past Jay, still covering up with my hands. I could hear his footsteps behind me as I reached the waterline. The water was cool so I tried to stop myself, but I slipped down the underwater bedrock, just barely managing to keep myself standing. I think I yelped because of the coldness enveloping my body. After a few meters of sliding, I finally managed to stabilize myself on a flatter portion, already chest deep in the water. I turned to look at Jay and we both cracked into laughter. "Forgot to warn you", Jay said between fits of laughter, sitting down and holding his stomach. The embarrassment that had just moments ago filled my mind was completely wiped out. I don't know how long we spent laughing, but eventually we managed to calm down. The water no longer felt cold, but rather refreshing and invigorating on such a hot day. "Oh, speaking of forgetting", Jay suddenly said, "I meant to ask, do you want me to call you by a different name?" The question came out of the blue and yet almost immediately I knew what to say. "Emily", I answered. His warm smile grew wider. "Emily", he repeated and I could not help but smile with him. The name and his voice rang in my ears. It felt wonderful. He picked up a few steps of speed and jumped into the water right next to me, drenching the rest of my body. --- I don't know how long we ended up spending in the water. We swam, we dived, we played, we did everything kids do in the water. It was just like any other time I swam in a lake with a friend, except I just felt more... Natural. It's hard to describe in words, but I think instead of constantly thinking about my body I could just be in the moment and enjoy it. Instead of having to concern myself with how I was seen, I was able to simply be. Eventually though the coolness of the water started to creep in and we needed a break to rest as well. Jay got out first and I followed suit. We made it to our picnic blanket and grabbed our towels, drying out what we could. I didn't even care how the swimsuit looked on me though I did notice Jay sneaking a few quick glances. Not that I was any better. The binder did its job making him just about flat and the swimming trunks looked great on him, although he did not have the same bump I did down there. Fortunately, the cool water had done its job so I did not look nearly as obscene as earlier. "I need to get out of this binder... It's going to stretch if I wear it when it's wet", he said, sounding a bit dissatisfied. He grabbed his shirt, looked at it for a moment, and then turned to face me. "Mind if I go topless?" he asked, his voice cracking just the slightest bit. I gave him a smile. "Go ahead, you're a guy after all", I said, a little nervous as well. He hesitated for a second, but soon enough pulled the binder up over his head. His breasts were small but clearly budding, with hard pointy nipples due to the cool water. There was a clear tanline left by his binder, but I could tell his chest had still received some sunlight. I thought he looked great but I could understand he was not happy with his chest so I avoided staring too intensely. He seemed a little more timid than usual but nevertheless gave his now-bare upper body a drying with his towel in full view. "That suit's really digging into you", he pointed out, nodding at the shoulder straps. I could feel them along with quite a few other spots. "Yeah, it's getting pretty uncomfortable", I had to admit. I looked at my options - the dress was still there, but I wanted to soak in the sun with Jay. I had my own clothes but they did not feel appealing in the least right now. "I don't have any extra underwear that you'd like, sorry", Jay said, realizing my predicament. "But whatever you're fine with is cool with me, Emily." Mentioning my name felt very pointed but made me feel oddly confident and secure. I flashed a bit of a devious smile at him. "You sure?" I asked. Jay was clearly a little puzzled, but gave a confirming nod. I slipped the shoulder straps aside, revealing the red marks they left behind, and pulled the swimsuit down, showing my flat chest, my small nipples also hard due to the cool water. Jay gulped. I could feel his eyes on me, watching my every move. Inch by inch, the one piece peeled off of me, revealing my smooth, pale belly. I stopped for a moment, taking a quick peek at Jay who averted his gaze. "Not looking", he said, looking to the side, blushing very noticeably. "No, it's okay", I told him, though my hands were a little shaky already. I continued my stripping, easily pulling the swimsuit over my soft penis, revealing it to Jay. He tried to keep his eyes higher up but I did see them wander down for some quick glances. Soon enough I was out of the swimsuit and set it aside to dry in the sun. I sat down onto my towel which I had placed on the blanket. Jay looked down at me and I looked up at him. I could not decipher his expression and in that moment my newly found confidence did crack - I thought I had made a grave error. "Sorry, I-I got carried away, I-", I tried to explain. Jay said nothing, but flashed a nervous smile and interrupted me by grabbing the waistline of his trunks, pushing them down in one smooth motion and kicking them aside. My eyes were mostly looking into his but I did notice his small bush of pubic hair right at my eye level, just enough to hide what was underneath. He sat down next to me, wrapping an arm around my body. I leaned into him, enjoying the innocent way his hand explored my side. My hand was on his lower thigh, gently rubbing him. "I thought I was pushing you to try new things but here you are, pushing me", Jay spoke into my still wet hair, using his nose to play with it. I giggled, very much relieved. "You did push me, but in all the right ways", I replied. Jay pulled me a little closer. We sat there in silence, naked as the day we were born, enjoying each other's presence. I had never felt this close to anyone but in that moment I felt I didn't need to feel this close to anyone else. Jay eventually broke the silence, barely above a whisper, "I think I have a crush on you." I turned my head and we gazed into each other's eyes for a moment. I leaned in a little closer and he met me halfway, pushing his lips against mine. I don't think either of us knew how to kiss, but we just went with it, starting with gentle pecks. I turned my body to face his while he placed his other hand on my cheek, softly rubbing it, while my hand rubbed up and down his leg, not daring to wander too close to his crotch. Soon we were laying down on our sides, cuddled up in an embrace. At first it was somewhat decent, chest to chest but a bit of distance between our lower bodies. Our kisses gradually grew bolder and more passionate. Jay tentatively poked his tongue out and I replied with mine, our tongues softly gliding against one another. He scooted a little closer and I suddenly felt his pubic hair tickling my half-stiff dick. He gasped softly and pulled back from the kiss for a brief moment. "Emily..." he said hoarsely. I could feel his hand making his way from my side to my back and then butt, giving it a quick, gentle squeeze. After that the hand began ever so slowly rounding my hip. I think he was lightly shivering, not from cold but from excitement. "It's okay", I said, my voice shaking, "Y-you can touch it." I then put my hand on the back of his head and gently pulled him back into a kiss. This emboldened him and his hand traveled quickly, finding my penis and gently grabbing onto it, squeezing and rubbing it, clearly with the purpose of exploring and learning. I gasped into his mouth and he took the opportunity to slip his tongue in, poking around in my mouth before meeting my tongue and wrestling with it. My hand was gently rubbing his upper body, tentatively gliding all over his front. I could feel his lovely abs but I maneuvered around his breasts and did not dare to return the favor, trying to be careful not to make him uncomfortable and ruin the moment. His hand kept jerking me slowly, sometimes making me fidget. It felt great and I think he could tell. I could feel him shifting slowly but constantly. It took me a few moments to realize he was trying to rub himself without touching himself. "Jay", I said after pulling back from our smooching. With his attention I moved my hand down until I could feel his pubes, stopping there to wait for his reaction. His hand stopped, merely holding my penis still. I'm sure he could feel it throbbing. He seemed hesitant, nervous, maybe even anxious. "I don't know..." he mumbled. I understood but could tell he was considering it. "You don't have to if you don't want to", I said, softly, poking my nose at his neck, nuzzling him. "I want to, but..." he said, trailing off, gulping and closing his eyes. I felt his free hand on mine, taking a shaky grasp of the back of my hand, slowly guiding me down. His chin was digging into the top of my head. "I've never actually done anything with, uh...", I had to admit, not sure how to refer to his genitalia. He did not say a word, but with his guidance my fingers ran through his pubes before feeling his heat and wetness. He clumsily tried to push my index finger between his lips. Getting the hint, I slipped the finger where I thought he wanted it and with my help he was able to place its tip on a small, stiff button - his clitoris. "Right now you can rub this here... Just be gentle." "Your dick", I blurted. Jay pulled his head back to give me a 'did you just say that' kind of look. I was embarrassed, briefly even convinced I had just ruined it, but he quickly burst into laughter. "Yeah, sure, my dick", he repeated, still chuckling, much more relaxed than mere seconds ago. Resuming jerking me off he said, "It's not as big as your clit though." It was my turn to laugh, though it soon turned into a gasp as he spread my precum all over the head, lubing it up. I started tentatively rubbing him, sending small jolts through his body. It was an awkward position with our arms squished in between us, but we kept at it, both of us occasionally gasping and moaning. Jay closed his eyes and I followed suit, concentrating on the sensations as well as his cute noises. I don't know how long we spent there rubbing each other but it couldn't have been more than a few minutes. "Sorry, hand's starting to cramp", Jay eventually said, a little apologetic, his hand giving me one more squeeze before pulling back. "Really not used to doing that." He gave his wrist a good couple of flicks and stretched his hand, his fingers cracking. "Yeah, this position is not good for me either", I agreed, my finger and hand feeling it as well. He seemed to measure our options for moment before giving my shoulder a gentle push. I rolled onto my back, my cock proudly standing up, precum flowing from the tip. Jay quickly got on top of me, one leg on each side of me, and pressed his crotch against mine. I admired his wonderful body, lit up from behind by the late afternoon sun, for a moment before piping up. "Do you have a condom?" I asked, a little concerned. I don't think a surprise pregnancy was in the plans of either of us. "No, but I won't put it in", he replied, adjusting my dick against my belly and starting to slowly grind his pussy against it, looking down at me with his hands on each side of my head. His motions were measured, with a heavier thrust followed by a slower retreat. Every time he pushed up we gasped in unison. I met his thrusts with small ones of my own but he was definitely doing the bulk of the work, some droplets of sweat dripping down onto me. It felt like he was fucking me, the girl I was, like the guy he was. I loved every moment of it. "I'm kinda close..." Jay suddenly murmured, grabbing my hand and guiding it to his pubic area, sideways so that my thumb could reach down. I got the hint and after a few tries managed to maneuver my thumb to his clitoris while he leaned back to give me a little more room to work, his thrusts slowing down to accommodate me. "M-me too", I managed to say, feeling my climax building up but trying to concentrate on pleasuring him. His motions were growing increasingly spasmodic - as probably were mine - but his louder moans indicated I was doing something right, so I just kept going. I could see the pleasure on his face, and it was incredibly erotic and beautiful. "Oh god", Jay gasped as his body suddenly tensed up. He tried keep grinding but the shakes coursing through his body made him fall on top of me, trapping my arm between us. He embraced me and I wrapped my free arm around him, feeling his spasms, first intense but then gradually subsiding until the only thing moving was his chest, working to catch his breath. He cuddled up to me, basking in after-orgasmic bliss and I was happy to have pleased him. However, it did not take long for him to realize I was still rock hard, poking against him. He looked at me, very satisfied but also a bit apologetic. "Sorry. You know how it is, guys always cum more easily", he joked, getting a laugh out of me as he moved down, grabbing the shaft and bringing his face close to my crotch. "I'll take care of it." With that he took the head in his mouth, letting his tongue run all over it, making me thrust my hips. I think he could tell I was still very close so soon he dove deeper, his mouth enveloping most of my length. It was a little rough and clumsy but he was definitely trying his best and soon enough I was at my limit. "J-Jay, I'm going to-", I managed to warn him. He did not back down, his lips wrapped tight around my shaft and tongue working the underside. I could not help but push myself deeper into his mouth, shooting load after load. He dutifully kept me in his mouth, allowing me to fill him up. It was by far the most intense orgasm I had ever had, leaving me lightheaded, gasping for breath. Once I was just about done Jay let my messy, gradually softening member slip out of his mouth and quickly moved back up, coming straight in for a kiss. His tongue began shamelessly exploring every nook and cranny of my mouth and I could taste my own cum, dripping from his mouth into mine. I was shocked at first, but soon took a deep breath through my nose and eagerly kissed him back, pushing him onto his back and letting the shared cum drip back into his mouth. We rolled over a few times more before finally deciding to swallow what was left. "Still got some there", I said, pointing to the side of my mouth. He licked it off me and swallowed, laughing. "You tasted like my juices so it was only fair to do that", he explained, a wide grin on his face. We were sitting on the blanket, drinking the lukewarm water I had in my backpack. "It was really hot", I admitted, blushing. "You... You made me feel like a girl." Jay looked very satisfied with himself. "And you made me feel like a guy, Emily", he replied. We gave each other one more kiss with his hand running through my hair, ruffling it lightly as he pulled to the side, heading for my ear. "A guy with a big, thick dick", he whispered and we both burst into loud laughter. "Anyway, I'm starving!" he then announced, getting up and digging into the cold box. I had almost forgotten about this being a picnic but could feel my stomach rumbling now that he mentioned it. We still had to wash ourselves but that could wait. --- "hey just wanted to let you know we can't meet next weekend im grounded for getting the dress all sweaty it was pretty stinky lol" "Yeah I noticed it on the way back. I'm sorry" "nah not your fault but we can meet up again in two weeks i can wear it again if you want" "You don't need to do that, it's okay" "ill wear it lol you liked it a lot so i dont mind :)" "Well, alright... Thank you"