Ambiguous [First time][Crossdress][Gay]

This is quite long as these are the first few paragraphs of a possible novel, hopefully it is worth the read!

**Paragraph 1:**
The referee blew his whistle to signal that the game was over. Our team gathered in the locker room for a quick evaluation before heading into the showers. As the water hit my sweaty blonde curls I took a look at my teammates. Out of all of them I was definitely the smallest with my 5’6” but that didn’t bother me, at least not within my team because as a midfielder I was the free kick and corner specialist so I didn’t need length. At school however I’d always been the target of bullying because of my appearance, Not only because of my length but also because of my skinny-fat body in which most of my fat accumulated into small man boobs while still being skinny enough to see my ribs. Luckily I had my soccer friends to make my life a bit less miserable. All they did was call me Jackie instead of Jack, but because they did it in jest it was no big deal. The primary reason for all of these friends was Louis.

Louis had been my best friend since before I can remember. We grew up at the same street and were almost inseparable. We always played games together, gossiped about classmates and he comforted me when the bullying at school got to me. Louis is physically speaking quite the opposite of me: with his 6’2” he towered above me and as he used to be chubby we would often be called “Laurel and Hardy”, “Timon and Pumba” or “Baloo and Mowgli” by our classmates. Louis always seemed to shrug the name calling off, which in turn gave me the confidence to do the same. They would also often call us gay because we were so inseparable. Although the gayest thing we did was sleep in the same bed during sleepovers and having his sister dress us up as the Spice Girls for a playback show, we didn’t take offense at it because you aren’t true best friends until someone accuses you of being gay.

Unfortunately Louis’ parents decides to move away when we were 16. Their new house was located about 10 miles from mine. As an effect Louis switched schools which left me alone to deal with all the bullying. He quickly gained some new friends at his new school so our contact became less and less frequent. As a way to stay in touch we decided to join a soccer club which was located at around the halfway point between our houses. We also sometimes had sleepovers at his house because his bedroom was in an outhouse separate from his parents house resulting in being able to play video games, drink and smoke weed all night. Now at 19 years old school was coming to an end and we were both contemplating what to do with our lives.

We were both still single. My small statute combined with the confidence issues that followed wasn’t exactly a recipe for success with the girls. In Louis’ situation it had more to do with his awkwardness and his habit of saying stupid stuff at the wrong moment. This kept biting him in the leg even after he started lifting weight and lost his chubby demeanor. But who needs girls when you’ve got friends like us?

After showering and getting dressed I walked towards my bicycle and looked around searching for Louis. Usually we’d stay talk a bit after training, but this time he was nowhere to be found. I chalked it up to him having some other obligation het forgot me to tell about. It was only until that evening and I received a text from him, that I knew the real reason for his silent exit.

Louis:
*“Hey man, can I ask a weird question?”*

Jack:
“*Probably, why didn’t you ask after training?”*

Louis:
*“Yeah sorry for that, but I was kind of nervous and chickened out.”*

Jack:
*“Well now you’ve got me wondering what your question is.”*

Louis:

*“Do you remember how we used to play dress up as kids and you loved being Baby Spice? Would you like to try that again?”*

Jack:

*“Yeah I remember, but what do you mean?”*

Louis:

*“Well, one of my classmates is giving this big End of School party next thursday and I’m invited but almost all of the guys are bringing their girlfriend or a date and I just feel like such a loser for not having either. So I thought maybe you could revive your Baby Spice imitation for just this one time…”*

Jack:
*“Lol, wtf are you thinking. Everyone will see right through and think I’m a sissy or something.”*

Louis:
*“I’m sorry! But no one knows you there and your imitation was always pretty convincing to me. Please think about it. I will be forever in your debt.”*

Jack:

*“I’ll think about it.”*

I didn’t wait for his reaction before putting away my phone. That night in bed my mind was racing about his proposal. On the one hand if anyone found out about this my reputation in this city would be destroyed. On the other hand I did really like playing dress-up and pretending to be someone else because I felt like I didn’t have to be my timid self. Furthermore Louis had always been a great friend supporting me through good and bad, so I kind of owed him.

The next morning I picked up my phone and texted him back.

Jack:
*“I’ll do it, but on a few conditions. It’s just gonna be this one time, you can’t ever make fun of me for this and if I don’t look convincing after dressing up I’ll immediately seize all of the shenanigans. See you on friday.”*

Louis:
*“Deal! My sister will do your make-up, so no worries. Thank you so much, it’ll be fun, I promise!”*

**Paragraph 2:**

Thursday after school I took a shower at home before going to Louis’ place. Although my legs naturally aren’t very hairy, I still started to shave them. If I was going to do this I was going to do this right. So while I was at it I also shaved my pubes and ass, who knows what kind of clothes Louis is going to try and make me wear. Luckily for me most of my hairs are soft and blonde. Eventually I found the results satisfactory. To be honest my smooth legs actually felt quite nice. After I was done admiring my work I put on some shirt and sweatpants and took off on my bike towards Louis.

He greeted me at his front door by thanking me again and again. When he was done thanking me he led me to his main bathroom where his sister Mary was already waiting for us. I didn’t really like the fact that someone else knew about our weird plan, but her make-up skills were essential for this plan to succeed. She did tell us we were “fucking weird” but luckily Louis told her to shut up because she’d always wanted to do a guys make-up. Mary begrudgingly agreed and told me to take off my shirt and sit down on a stool she’d already put down.

Mary started by straightening my curls. Normally my hair ended at around the bottom of my cheeks, but when Mary was done straightening, my hair was almost twice as long and reached to just over my collarbone. After she was done with my hair she started on my make-up. Using a lot of creams and powders she tried to soften my facial shapes. When she started applying mascara she complimented my long eyelashes and said she was jealous of them. Lastly she applied some bright red lipstick. To create somewhat realistic boobs she taped my chest together and made me wear two push-up bras on top of eachother. To complete my makeover I had to put on one of Mary’s dresses. It was a tight sleeveless black dress. At first she wanted me to wear a panty, but after noticing I’d shaven my legs she decided that bare legs would be better looking. She also found that the edges of my boxer briefs were showing and insisted I’d have to wear one of her “invisible panties”. At first I didn’t like the idea of wearing women’s underwear, but after a quick examination while wearing them I agreed that it looked way better. And to be honest the soft fabric on my smooth skin felt quite nice and their tightness kept my male bits securely tucked between my legs.

I walked over to Mary’s room to examine myself in her big mirror. As I walked past Louis he slapped my ass and told me I looked great. Although we’d slap eachothers asses often during soccer, this slap was different. Was it softer? Did he wait a short while before pulling his hand from my ass? I couldn’t put my finger on it so I chalked it up to the nerves.

When I looked in the mirror for the first time I couldn’t do anything but agree with Louis’ statement: I did look good! The tight dress hugged my skinny upper body while it accentuated my slightly muscular ass and toned legs. Mary’s make-up skills were impeccable and together with my straight hair it made me totally unrecognizable.

Louis threw his arm around me and told Mary to take a picture of us. Before I could protest she’d already taken the picture. She showed it to us while telling us we looked like a cute couple. I didn’t have time to tell her to delete it because Louis told me to hurry up as the party had already started. The party was a 10 minute walk from Louis’ home so we decided to walk. Louis’ mother has the same size shoes as I have so I took a pair of her black leather heels with me. They were actually quite comfortable so I put them on for our walk so I could practise moving in them.

On our way to the party Louis wouldn’t stop alternating between talking about how thankful he was and how great I looked. I wanted to tell him to shut up, but his compliments were actually kind of flattering. All of his compliments actually got me a bit shy and he teasingly put his arm around me while telling me:

“Don’t worry, tonight will be fun. Just try not to worry too much.”

I ducked from underneath his arm. “All I’m worried about at the moment is you forgetting I’m not real girl.”

Louis laughed. “I know you’re a guy. We just have to make sure that no one else gets to know. So for tonight your name is Jennifer.”

I quickly agreed as we walked up to the party house. The door was already open and loud music sounded from inside. Louis told me to grab a drink while he was going to find Katie, the hostess. I tried to protest because I didn’t want to be left alone, but Louis’d already sped off.

**Paragraph 3:**

The party:

I wasn’t feeling in my place at all: The short dress was already riding up my leg, the heels felt wobbly and some guys kept staring at me. Were they onto me? Everyone is going to think I’m a fag. Louis said I looked pretty and I actually believed the jerk, this plan is a disaster. Maybe I’ll have fun if i get wasted. At the very least I won’t remember this humiliating night.
All of a sudden a girl tapped my shoulder. I turned around towards her and noticed it was Katie, the hostess. She already had her hand extended towards me, so I took the invitation to shake her hand.

“I’m Katie” She said with a friendly smile.

“I’m Jaeniffer, Jennifer hehe” My nervous mumbling made her smile transform into a laugh.

“You’re Louis’ girl right? You don’t really seem to enjoy yourself, is anything wrong?” Her question seemed genuine, so I tried to stick as close to the truth as possible.

“I don’t really know anyone at this party and I’m too sober to not care about it.”

“Why don’t you just go and dance with Louis?” She pointed towards the dancefloor where Louis was dancing with a bunch of people.

“I really can’t dance.” This wasn’t even a lie. As a guy my dancing was awkward at best, but as a girl I probably couldn’t dance even if my life depended on it.

“Do you need some help with that? I want everyone to have a good time at my party.” Her friendly smile turned into a suspicious one.

Katie put her hand in her pocket and pulled out a little plastic bag with about 10 tiny yellow pills in it: undoubtedly XTC. Now I do have some experience with XTC and it does indeed make my dancing less awkward. Also, the chance of me doing something to blow my cover would be way smaller if I were rolling on molly than if I were to get shitfaced.

I stuck out my cupped hand towards her. “Fuck it, let’s do this, I might even have fun.”

This was all Katie needed to hear to open the bag and take out one of the pills. She broke it in two uneven halves and put the biggest half in my hand while putting the other half in her mouth, quickly swallowing it with a sip of her drink. As she handed her drink to me I did the same and felt the cold liquid escort the pill down my throat.

Katie put her hand on my bare shoulder and rubbed it. “Relax, try to have some fun, I’ll keep an eye on you.” She winked and walked off towards some other people.

As I waited for the molly to start its effects I realised I had gotten a bit thirsty. So I set way to the kitchen to fetch myself a drink. My choice had fallen on a rum ‘n coke. Not too much rum, but my talk with Katie had given me some new excitement, so a little bit too much rum probably wouldn’t hurt. As I walked back towards the edge of the dancefloor my ears started feeling warm and the music started to sound more intense. All of a sudden one of my favourite songs came on so I couldn’t resist the urge to dance.

I downed my drink and walked up to Louis while my body started to vibrate with the song. My dancing still felt a bit unnatural so I looked around at the other girls for inspiration. They were all rocking their hips and while some threw their hands in the air others rubbed their hands on their bodies or had them around their partners waist. I figured my hands in the air would be the safest bet. While they were in the air I met eyes with Louis for the first time since we arrived at the party. He stepped towards me and lowered his head near my ear.

His soft breath tickled my ear. “What has gotten into you?” He asked with a bit of surprise in his voice.

A pleasant mixture of his cologne and musk filled my nose as I tilted my head towards him. “Katie gave me a bit of party spirit in pill form.”

Louis laughed. “She definitely knows how to host a great party”

He brought his head back up but didn’t step back. Our bodies remained pressed against each other and I felt the heat from his waist radiate into mine. The dance floor started getting more crowded and someone bumped into us, this pushed my cheek against Louis’ chest. The softness of his shirt combined with the heat of his robust pecs felt amazing against my drugged body. I wrapped my arms around his waist in an attempt to catch even more of his soft warmth. His big hands rubbed my exposed shoulders and started to drift down my backside, stopping in the hollow of my lower back. My thoughts started to wander as Louis’ hands pressed me even tighter against his body. The intimacy felt weird, but in a good way and besides we did have to at least make it believable that we’re a couple. Why did this feel so good though? We’d hugged before, what was different about this time? Was it the drugs? Probably. But there was also a little bit of unknown excitement. I couldn’t really put my finger on the feeling, but chalked it up to the anonymity of my costume.

While my body felt like it was dissolving into the music and Louis’ torso, he started grinding his hips to the tune of the music. Without thinking my hips answered his’ by following the grinding. Before I knew it Louis started moving his hands all over my back while sometimes letting them stray over my hips and the top of my butt. The friction from his grinding and rubbing felt too good on my burning skin to care about the implication. All I cared about was how great this moment was. His hands lowered themselves onto my butt and started softly petting my ass. The soft petting slowly turned into a gentle massage as he began to squeeze and pull apart my ass cheeks. This quickly turned into groping and soon his hands found their way underneath my dress. At first the pleasure of his hands against the sensitive skin of my butt caught me off guard. So for a short while I let him have his way underneath my dress. But soon I realised I didn’t want everyone seeing my bare ass and possibly ruining my cover so i pushed his hands away and turned away from him. I don’t know if he got the hint or was just distracted, but he used my sudden movement to turn me around and press his crotch against my ass. This made me miss his glowing chest against my cheek, but at least he kept my dress in place, and his hands pressing my ass into his crotch also felt kind of nice in a weird way.

Our movements synced up again and soon we were almost dancing as one. The back of my head rested on Louis’ shoulder as I put my arms around his neck, his hot breath covering my jaw and neck. His hands moved their way from my hips to my sides and began to run over my stomach and thighs. Louis increased his pressure against my ass and all of a sudden I realized I could feel something hard through his dress pants. Did he have something in his pocket? I tried to feel what it was by pressing my ass into his hips to increase the pressure. All of a sudden I realised it was his dick. He had an erection! Was our dancing getting him horny?

To be honest; our bodies dancing against each other so intimately combined with his firm hands all over my glowing body got me a little bit hot too, but luckily the drugs prevented me from getting hard, thus keeping our secret safely tucked away into my tiny panties. Well safely might be a bit too optimistic because Louis’ hands started wandering underneath my dress again. This time he was more careful and started to softly caress my thigh with his left hand while slowly working his way up. His right hand firmly around my waist gently squeezing my side. His left hand eventually stopped at my loin, where he started to very delicately rub the fringe of my panties. With his tenderness he probably tried to avoid a similar reaction as the first time his hands found their way under my dress. It worked; the pleasure that arose from his gentle tickles drowned out any embarrassment I had left. Even when his fingers began to lift the edge of my panties and started to find its way inside I couldn’t muster up a protest. All I could do was close my eyes and let out a soft moan while his fingers invaded my pubic area. Luckily for my cover Katie did muster the kind of protest neglected to give.

She pressed her body against mine, tightly sandwiching me between her and Louis, pressing his hard cock even more tightly so against me that I could feel it throbbing against my ass. This sudden attention made Louis pull his hand away from my crotch.

“Hey there lovebirds” Kate said it with an almost evil grin. “The party’s almost over and I think you two need to get to somewhere private because I would like to preserve the little bit of civility my party still has left.”

Louis and I laughed awkwardly in agreement while I took a quick look around the dancefloor. Kate was right; most people had left and the people that were still around all giggled our way. Louis quickly took action with Kate’s suggestion and hastily made us two drinks for on the road. Kate waved us goodbye from her door and wished us goodnight.

While standing on Katie’s driveway Louis conjured a joint from his back pocket. He lit it in silence and we smoked and drank while we walked towards his home. Our conversation started with a bit awkward small talk but after a few minutes and and a few puffs from his joint the conversation became quite natural again and our friendship felt like normal again, although for just a few minutes.

**Paragraph 4:**

Coming home and elsewhere

We snuck through the back garden towards Louis’ outhouse. When we finally arrived I realised my “normal” clothes were still in his parents’ house.

“Shit I have to get my clothes from your parents’ bathroom”

“Nah man, you’ll wake them up. You can pick them up in the morning when my parents are at work.”

He was right, I couldn’t wake up the whole house, especially not when I was dressed like this. “But what do I have to wear to bed then?”

Louis shrugged. “You can just wear this, no one is going to see you except for me.”

The idea of staying dressed like a girl for the rest of the night felt a bit strange, but I didn’t have much choice because the alternative would be to wear just these frilly little panties and that would be even stranger.

Louis quickly stripped down to his boxers and jumped into his bed. I turned off the lights in his room and stumbled through the dark to find his bed. Because of the darkness I clumsily lied down with my head on top of his bicep. Louis didn’t seem to mind this and I kinda liked the warmth and firmness of his muscle. The effects of the xtc hadn’t worn off quite yet so I was still a bit chatty. Combined with Louis’ drunkenness this resulted in a late night conversation. We quickly ended up talking about Louis’ fitness transformation.

“Do you have a six pack already?”

I already knew the answer as I’d seen his abs plenty of times during training and showers, but I still jokingly poked his side. This prompted a sudden movement from him which moved my head onto the inside of his shoulder.

“Yes of course I have a six pack, haven’t you been paying attention? Want to feel?” Louis sounded almost insulted as he grabbed my hand and put it at the top of his stomach.

My hand rubbed over his rock hard abs while I started counting the blocks. “One, two, three, fo…”

As my hand moved over his belly button I touched something sticky. My finger stopped in the little puddle and started moving downward. Just below his belly button I touched something. Was that his dick? That’s impossible, it must be huge if it comes all the way up to there! To make sure what I was feeling I slowly ran my finger down over this unknown object until I reached his balls. Jesus, it was really his dick! He must be rock hard! To confirm this I wrapped my hand around his shaft and softly squeezed it. This made a silent moan escape from Louis’ mouth. It was hard as a rock.

I was flabbergasted. “Am I getting you getting aroused?!”

Louis moved his arm pressing my body against his side making me feel the warmth of his torso radiate into me again. His cock pulsated in my hand as he started stammering.

“I.. I’m so sorry! You just look so good in that dress and you were dancing so sexy.”

I had to admit to myself that he was right; I did look good and if a girl like me would dance like that I’d get a bit horny too. I even did! but that was almost half an hour ago at the party. He couldn’t still be this hard.

“You can’t still be that aroused from only that, I mean it feels like a steel pipe and it’s huge.”

Louis’ blushing was almost audible as he stuttered on. “It isn’t that big, is it?”

To prove how big he actually was I ran my hand up and down his shaft, pulling back his foreskin and making him twitch in my hand. The width of my hand fitted almost three times over his length, it must’ve been almost ten inches.

I wanted to tell him how big he actually was while my hand kept moving over his penis, but Louis moaned again, now louder and put his finger on top of my lips to shush me. Slowly he started caressing them at first softly, but after a while my lips parted from his rubbing.

“It’s just… all I can think about is.. Is those sexy red lips wrapped around my hard dick.”

What did he just say? My heart skipped a beat but my lips instinctively closed around his finger as he slid it over my tongue. I wanted to protest but I automatically closed my eyes as I started sucking on his index finger. His cock throbbed in my hand as he slid it further into my mouth, my hand still steadily moving up and down his long shaft.

“I’ve just never been with a girl and have never even gotten attention from a girl as hot and sexy as you. I just can’t help it but you make me really horny, it’s all I can think about.” His tone had shifted from shy to sensual. He started slowly bucking his hips into my hands while he also slid his middle finger further into my mouth. Meanwhile his precum had covered my entire palm.

My mind was racing from all the booze and drugs so I couldn’t think straight. Did Louis’ really want me to suck his dick or was he just drunk mumbling. What am I thinking? Of course he doesn’t want me to suck his dick, he’s straight, just like me right? But getting horny from a hot chick dancing against you and sucking your fingers is pretty straight, right? Everyone probably believed we were a real couple and even I enjoyed the grinding of our bodies. What girl wouldn’t like to grind like that against an attractive guy like Louis?

My body couldn’t handle all of the sensations and I lost control of my thoughts. Louis’ finger slid out of my mouth and started wandering downwards. Without a thought my head followed his finger, barely touching it as it made its way down Louis’ hard stomach, leaving a trail of little kisses and licks from his chest to his stomach.

My head was now resting on his abs with my mouth on top of his bellybutton. I could smell the hypnotic combination of his musk and precum. Was I really going to do this? I’m not gay, right? But at the moment I’m a girl so it wouldn’t be gay? I’d also already just sucked on his finger so what’s the difference between that and sucking on his big, pulsating, juicy cock?

My drugged arousal and excitement took over from my common sense as I slowly moved my head towards the puddle of precum that’d formed beneath his bellybutton. My cheek got coated in his warm fluids while my lips softly touched the tip of his penis, coating my lips in his sticky juices. I licked my lips and my mouth filled with his sweet and salty taste. It felt incredible and tasted like more.

Slowly my lips started sucking on his tip making Louis’ loudly moan as the head of his penis penetrated my mouth. His moaning only got louder when I increased the pressure. His juices filled my mouth when I twirled my tongue around his tip and started moving my hand up and down his shaft. The taste of his precum became even stronger, but i wanted more. So I sucked his hard cock deeper into my mouth. Louis’ didn’t even try to cover up his sounds and moaned loudly into the air. The smooth flesh of his hard dick rubbed over my eager tongue as I started bobbing my head up and down. His member went deeper and deeper into my mouth until it reached the back of my throat.

All of a sudden Louis put on a little bedside lamp which blinded me for a second. This scared me and I recoiled from his dick, lifting myself on my knees.

Louis started apologizing. “Sorry, I didn’t want to scare you. But I just had to get a better look at those slutty red lips greedily sucking me off.”

I was appalled by his words, slutty? He was the only guy I’d do this for! But didn’t get a chance to react because his hand pressed my face into his balls. In an almost instinctual reaction I began sucking them and swishing them into my mouth. His grip on the back of my hand softened a bit and I began to kiss and lick his shaft slowly inching towards his delicious tip. I arrived and started bobbing on his hard member again. Louis started applying more pressure to the back of my head, pressing his tip deeper into my throat. He started bucking his hips, keeping my head in place and fucking my mouth even deeper than before. I tried my best not to gag, but his dick was so big I eventually had to. Louis didn’t care and probably didn’t even hear my gagging through his almost feral moans. I couldn’t think while he began to roughly fuck my mouth and just held my mouth open and tried to suck his taste into my mouth. A mix of saliva and precum coated my hand and his dick.

Louis suddenly removed his hand from my head and I kept on sucking his member deep into my mouth. We both knew how this was going to end when I didn’t stop. His hand went under my skirt and into my panties where it started massaging my ass. Eagerly his massage inched towards the inside where his fingers started massaging my anus. At first gently, but his fingertips quickly found their way inside of me. This felt surprisingly good and I moaned hard and as girly as possible into his crotch.

This apparently was too much for Louis. His grip on my ass tightened and pulled my cheeks apart, pressing his ring- and middle finger further into my tight hole. We both moaned loudly and he pushed his hips deep into my mouth, His pulsating cock started squirting the taste of his cum into my mouth and made me moan again as I started swallowing in a panic. Beam after beam squirted into my mouth and I couldn’t think of anything other to do than to swallow it all down. Louis kept moaning and I kept swallowing. In the moment it all tasted amazing. I lost count of how much I’d swallowed and had to come up to breath. As I removed his tip from my mouth a last few spurts of salty sperm hit me on my lips. The final few drops of his seed oozed down his shaft and blended itself into the mixture of fluids. I couldn’t resist the temptation and licked his delicious milk from his balls and shaft and sucked everything out of him.

With Louis’ cum still on my lips I turned to look at him. He still had his eyes closed and was panting. One hand still on and in my ass and the other on his chest. He removed his fingers from my ass and went to the lightswitch. Right before he could switch off the lights he tilted up his head and looked me in the eye. My lips were still covered in his milk, my tongue licked my lips and my eyes were asking for more. Without a word Louis turned off the light.

“Let’s go to sleep.” he told me as he pulled the blanket over his naked body. I didn’t know what to say. Now I was the only one who had sucked a dick, while Louis just had an orgasm down my throat. It was unfair! My body was still raging from hormones and arousal, but my dick was still soft because of the XTC and booze. I didn’t know how long I sat on my knees in Louis’ bed with his cum on my lips, but when I heard him snore I knew that the evening was over. I laid my head to rest and licked the last bit of his fluids from my lips. With the taste of Louis’ cum still in my mouth I quickly fell asleep.

Source: reddit.com/r/sexystories/comments/ayqrm6/ambiguous_first_timecrossdressgay