My First Time Chapter 2 [Real Story]

My First Time Chapter 2.

It was the day before the weekend and luckily my parents were going away for the weekend again, as usual they told me to do my chores and look after the pets before they left, a little bit later my mother texted me saying they forgot to tell me they'd be coming back tuesday morning.
So naturally I was very excited (again) because I got to dress up for 4 days without worry, I went upstairs and spread a couple outfits over my bed in the end I went with the second one, a black top with short sleeves and some japanese kanji on it, a short dark red plaid skirt, a fishnet bodystocking with longer sleeves to go underneath the top and skirt, a pair of black thigh highs, wig with long black hair and for the underwear I went with a pair of laced panties & bra both with red accents.
I got dressed and went on to the bathroom to do my make-up, I went with black eyebrows, fake (thick) eyelashes, very soft dark eyeshadow with hints of red, a little bit of eyeliner, a matte red lipstick to match my skirt and I tried to do a few freckles.

After I was done I went downstairs to get my chores done which took way longer than I had hoped so after that I put on a show on Netflix put my laptop on the table to boot up a game to just lay back and relax a little. Just as I was starting to relax my phone went and I saw it was my neighbour who had left me a text message, it startled me a little because I had forgotten about what he said last time.
In the message he said he knew my parents had left and that he wanted a picture of what I was currently wearing, so I sent him the picture and almost immediatly I got a reply telling me I looked amazing and asking for how long my parents would be gone, "until tuesday" I replied and he replied back "great! come on over there is something I want to try and show you!", "ok but I have to finish a couple chores first so it'll be a bit" I replied quickly trying to think of an excuse to buy a bit of time, "it's ok, take your time but try to get here before dinner at least haha" he replied.
At this point I was getting a little nervous since I had completely forgotten all about it but I was also a little excited...

After a couple more hours of 'chores' (was really just gaming) I decided to head over so I texted him I was coming, he replied "ok the gate in the back is open" once I stood in front of the fence gate I was considering going back in and just say I wasn't feeling well but then I remembered the pictures he took so I went ahead anyway.
Once inside I found him waiting for me in his kitchen "well hello there! I wasn't really expecting you for another couple hours to be honest hahah!" he said as I came in, once I stood in front of him and asked him why I was here he told me to spin around slowly to give him a better view, he lifted up my skirt to get a look at my butt and slapped it "you look stunning!" he said and chuckled at my startled face, "now then, follow me I have something to show you" I obeyed and followed him upstairs to a guest room.
In the room were 3 boxes "go ahead open them" he said, inside the boxes were 3 pair of high heels each the same style/shape each with a tiny strap with a lock at ankle hight and each a different size "I didn't know your size so I just got a couple in different sizes to be safe" "anwyay go on, try them on" he said, I did as I was told.
While I was trying on the heels he asked me if I ever tried walking in heels "yes I've got 1 pair myself but they aren't as high as these" I replied, he chuckled and said "well then we'll just have to train you to walk in these!" meanwhile I was trying the second pair and sure enough they fit perfectly "these seem to fit" I said, he came over to inspect (or so I thought) "hmm yes they seem to fit you well" he said and just as he said that he quickly locked the straps on both my ankles and took a few steps back "good now you'll have no choice but to learn how to walk in them" he said with a grin.

It surprised me a bit at first but I quickly regained my balance "alright try to walk to me and back in a straight line" I did was I was told but ofcourse it didn't go well the first couple times which made him laugh a little, but I quickly got the hang of it "good, good! now try swaying your hips a bit more!" which I did.
On the last one I noticed he had a bulge going on and he obviously looked very pleased with himself "looks like you've got the hang of it!" he said, "great so will you please unlocked them?" I asked, he laughed and said "no no princess you'll have to work a bit harder to earn your freedom" "so with that in mind lets have you seated over there" he says while pointing at a seat in front of a table with a mirror on it, on the table is a small box.
He opens the box and inside are fake nails "now then lets put these on shall we" "don't worry they'll come off in a day or 2" he says with a grin on his face, once the nails were on he told me to go ahead and go downstairs to the livingroom while he prepares a few things in the guest room.

While waiting in the livingroom I tried to get out of the heels but ofcourse that didn't work and with the heels locked I couldn't go home or anything either so I gave up and just stayed put on the couch.
He took a while to get downstairs so I decided to walk around a little bit (to be honest I was secretly enjoying to walk in them) and ofcourse he had to come downstairs just as I was walking around, he grabbed my ass cheek and said "hah! see I knew you were enjoying it!", "maybe I am, maybe I'm not" "going to unlock them yet?" I said, he slapped my ass again and said "don't be so cheeky princess!" I apologized "now that's a good girl" he said.
He put me back on the couch and said "alright listen closely I want you to go back upstairs to the guestroom, on the bed you'll find a dildo and a buttplug I trust you'll know how to use them" "I've ordered food and you will open the door once it gets here oh and one last thing, don't go snooping around the wardrobe, I've locked it just in case but still" "okay now you go on play with yourself upstairs and don't forget to put the plug in once the doorbell rings and you're not to take it out until I say so!" he waved the key to the shoes in front of me, I obeyed and went upstairs

After about 30 or 40 minutes the doorbell rang so I put the plug in and went downstairs to answer the door. I opened the door and behind it was a boy about my age he looked a little surprised and stuttered "h-here is y-your order" he smiled to him and went back inside, once back inside I noticed through the window the boy was blushing a little.
When I entered the livingroom my neighbour was laughing and asked "what'd you do to the k**, his face was bright red when he walked back!", "nothing, I just smiled" I replied, my neighbour bursted out laughing again and said "looks like we'll have to invite him in next time!" "anyway let's eat princess".
Before sitting down he checked my butt to see if I did as I was told he slapped my butt again and said "good girl!", after dinner he told me to wash up and wait in the livingroom once I was done as he went back upstairs, again I did as I was told and cleaned the dishes.
He soon came back downstairs and told me to join him in the guestroom when I was done, shortly after I finished and went upstairs as well "alright bend over on the bed" he said I obeyed and bent over he lifted up my skirt and took out the buttplug, at first I thought "here we go again, he's going to fuck me isn't he" but no he started to finger my butt "hmm nice and tight" he said after a while he told me to turn around and kneel in front of him.

I was know on my knees with the bed behind me so know where to go or pull back he dropped his pants and told me to pull his underwear down, when I pulled it down his cock sprung out and slapped me in my face "alright you know the drill" he said. I grabbed his cock and started licking it along the length of his shaft and took his balls in my mouth, after a short while he placed his hand on my head and said "alright princess that's enough teasing" he grabbed his cock and guided it to my mouth touching my lips, as he kept pushing I kept going back a bit further until I hit the bed with the back of my head "alright open up princess" he said smiling, I opened my mouth and he slid his cock in gentlyand taking a step forward so that I couldn't get it out of my mouth anymore.
So I gave in and started bobbing my head working his member, the only break I could get was when I pulled my head back as far as I could but even then the head would still be in my mouth leaking precum. After a while he said "okay time to try something new, expand you jaw as far as you can while keeping your lips wrapped around my cock, hold your breath and keep swallowing" he then pushed forward pushing my head against the bed and his cock all the way into my mouth, he was forcing me to deepthroat him, at first my gag reflex kicked in but after a couple more times I figured out how to control it and he said "great! looks like you won't need much deepthroat training" he pulled out and stepped back letting me catch my breath "alright go lay down on the bed on your back" he then grabbed some lube and climbed onto the bed as well "don't worry I'll go slow, we're going to try out a few different positions anyway so I don't want to cum to soon" he said while lubing up his cock, he then put my legs over his shoulders and slid his cock in with ease, after a little while he rabbed my legs again put them together and held them in the air "aaah you've tightened up, good to know" he said as I started to moan a little, he then climbed onto me further to kiss me and told me to wrap my legs around his waist he kept fucking me for a like this for a bit then stopped and kept kissing me before getting off.
He got off the bed and grabbed something out of a drawer, a pair of cuffs with soft insides, "alright princess, turn around hands on your back" he said, I obeyed and he cuffed my hand behind my back "okay now face down and ass up" he said as he climbed back on the bed, he held on to the cuffs as I burried my face in the sheets. He then grabbed my ass and pushed back inside me, at this point he stood up towering over me and starting to lean down to push me into the sheets further "aaah this is great, you're so tight" he said as he started thrusting faster and faster, in this position he was deeper inside me than ever before and as a result I started to moan out load which made him laugh. After about what I guessed to be 10 minutes of that I felt a familiar warmth rushing inside me, as I felt the warm rush I heard him growl a little and sure enough he had dumped his load inside me again, after he pulled out he told me to push out as much as I could while he was taking pictures again. He then left me laying there on the bed my hands cuffed behind my back and his cum leaking out my ass "I'll be back in a bit" he said, I whimpered "sure".

After a good 40 to 45 minutes he came back in with a strip of blue pills, he uncuffed me and said "how do you feel about staying here for the night?" I didn't want to but then he said "if you'll stay for the night I'll unlock your heels, buuuut there is one more thing I need you to do though" I reluctantly agreed and asked him what he wanted me to do, "well you see these pills?" "I accidentally mistook them for my medicine" he said, "well I still don't really see the problem here?" I said, he laughed and said "well you see these are called viagra and they make your wel... I'll just show you instead" he then whipped out his cock again and I couldn't believe how much bigger it was and how many veins had popped up. He chuckled at how I was in awe of it "you see my problem now?" he said, "alright alright I get it, I'll help you get rid of this but only if you unlock the heels" I replied he laughed and said we had a deal. We then had sex for what felt like hours he finished squirting his load in my mouth demanding I swallow, by the time it was all said and done it was 11pm he told me where to upstairs bathroom was incase I needed the toilet then thanked me, unlocked the heels and kissed me goodnight.
At this point I was too tired to think straight anyway so I just tucked myself in to the bed and fell asleep to the taste of his cum and the feeling of being fucked several times.


The following morning he woke me up at and told me to take a shower and to thoroughly clean myself, while I went to shower he was busy in the guestroom.
Once in the shower I noticed (well how could you miss it lol) a dildo with a suction cup stuck to the wall and thought to myself "great, looks like he forgot to mention something" as I stepped in I noticed I was getting hard and a little horny and thought "ah what the hell he won't notice anyway" and grabbed to dildo guiding my ass to the tip and slowly pushed back on it, it wasn't long before I came and shot my stuff all over the glass door, I dropped to my knees and thought to myself I had to clean this up or else he would know and be all smug about it, not wanting to take any chances I decided to lick it up..

Once done showering I headed back to the guestroom where he was waiting with a grin from ear to ear "it appears you noticed the dildo, didn't you!" he said laughing, I denied it asking what he was talking about "dont deny it princess I could hear you moan! but since you denied it lets have a look shall we" he said, while walking to the bathroom I thought to myself he wouldn't see any evidence anyway since I had licked it all up but once inside "hah! see! the dildo is still on the wall, it's even lower than it was before and it seems you've missed a spot!" "but I have to say, you're a real good girl trying to clean up after yourself!" my cheeks were bright red and he laughed "I hope you had a good time because it'll be your last wank for the day, tonight you'll only be allowed through your ass-pussy!" we went back to the guestroom where he handed me a chastity cage and demanded I put it on and gave him the key, I obeyed and locked myself. He then told me to go downstairs to prepare breakfast while he stayed in the room a while longer.

After breakfast he said he was going to go out to get some supplies for the match this afternoon and he told me to go upstairs and put on the clothes he had prepared "now I want you to do your best and try to be done by the time I get back and if you're a good girl today I'll let you keep everything", "yes daddy, I'll be a good girl" I said, "now that's what I like to hear princess!" he slapped my butt again and headed out.
I went upstairs and found a maid outfit spread on the bed the "main" dress piece was so short it showed the bottom of my ass cheeks peeking out underneath, there were black thigh highs with a white rim with a black ribbon at the top with a matching garter belt and a pair of matching arm sleeves, he had even ordered silicone breastforms (those you put in a bra) which where about 2 or maybe even 3 sizes bigger than what I was used to, they were so much bigger that they created a mini cleavage which I later contoured a bit with make-up to make it seem a bit more realistic, for the underwear the had chosen a pair of string panties and a black lace bra with white accents and pockets for the breastforms there was a note saying I had to put the panties over the garter belt, there was also a wig with long blonde hair and a black choker with a metal heart in the middle and last but not least ofcourse the high heels which had a note with them telling me to lock them again and leave the key on the livingroom table.
He had also ordered bits of make-up in the form of a soft pink lipstick, soft black eyeshadow and some eyebrow powder, there was a note with the make-up as well asking me to do the freckles again.
Once I was finished putting it all on I couldn't help but notice I looked a bit like a bimbo maid, with the heels on my ass was even more in view as well like halfway pretty much, I turned around walked back to the bed and noticed the buttplug was there as well so I sighed and put it in.
I went downstair turned on the tv to wait for my neighbour to return when suddenly the doorbell rang, my heart started pounding like crazy and I remember thinking "great! another thing he forgot to mention! just great!", I opened the door and sure enough there was that delivery boy again from the other day. It appeared that he had some snacks with him that my neighbour had ordered for tonight but he was also holding an envelope, he told me he had to give this to me, as he gave me the envelope he said he was actually just clocking out but this man had come to his workplace asking to get some food (snacks) delivered to his place and also gave him this envelope.
I opened the envelope and saw it had 2 pieces of paper in them, the first one read "I hope you finished in time hahah" "anyway let the boy in, I felt bad for him yesterday so I'll have you be a proper maid and service him" "incase you didn't get it, I want you to suck him off now then show the boy the second piece" my cheeks lit up red and the boy asked if I was alright and nodded while handing him the second piece, it read "come on in boy, my girlfriend will take care of you, she felt bad for you yesterday and wants to make it up to you" "now I agreed with her but on 1 condition, she is only allowed to use her mouth" "oh and forgive her if she doesn't talk much, she's very shy. now go on have fun!" now the boy his face lit up bright red and he showed me the paper, I just smiled and let him in.

He asked "w-w-well what n-now" he was so shy and flustered that I actually thought he was very cute, I kept smiling and stept closer I wrapped my arms around his neck keeping my hands above his head and locking them and went in to kiss him, it startled him so much he fell down taking me with him, my face fell straight in his lap. I then got up on my hands and knees (my ass being pushed up a bit because of the heels and the way the dress was shaped) and unzipped his pants, his cock was already rock hard and sprung out, I smiled and licked the tip, his face was even more red than before and his eyes were really wide looking at me in awe at what was happening.
I smiled one last time and took his head in my mouth slowly starting to suck on it and play with it with my tongue, all the while slowly going down a bit further to try deepthroat him. As he grabbed my head I looked up at him and maintained eye contact as he started to moan "god I'm so jealous of your boyfriend" after one last (loud) moan he started to twitch and shoot load after load inside my mouth, I was so surprised by the amount that I couldn't keep up swallowing, after he was done and I had swallowed it all I let his cock out with a plop and licked my lips.
I went to the kitchen to get him a glass of water, he thanked me and told me I was very pretty, I kissed him one last time and he left thanking me again.

Once he was gone I sat down on the couch my heart racing and feeling extremely horny and frustrated I couldn't cum because of that cage, my phone rang and sure enough a text from my neighbour "I see you and the boy had a great time! I'm proud of you princess!" it read, I asked how he knew "go back to the hallway and look up on the drawer underneath my coats" he replied, I looked and noticed a laptop standing on the drawer opened, I turned the screen on and saw it had a skype call going on with video feed from the laptop going to my neighbour who was apparently watching on his phone.
I turned the laptop off and texted him "you almost coming back or can I expect more food orders", he replied "hahahaha don't worry princess no more surprises I'll be back in about an hour, in the meantime you can do whatever you want, the dildo is in the drawer next to the bed hahahah", I replied "ok see you in an hour" and turned on the tv thinking about what just happened..

At around 2pm my neighbour came back home ordering me to put the supplies away, while I was putting the supplies away he was telling me about this afternoon "alright guess I'll tell you about my friends" he said, "wait, friends?!" I replied a bit shocked, "oh yeah guess I forgot to tell you, I told them about you and now my other friend also wants to come so you'll be serving 3 people today including myself" he said, "you really don't let me in on much do you?" I replied, he laughed and said "well alright I admit I thought it was fun, especially because I wanted to see what you'd do and you didn't fail me princess!".
"But anyway let me tell you a few things about them" "first off, they don't mind you having a dick as a matter of fact one of them actually really enjoys playing with girls like you" "second, your look today was partially influenced by them, I wanted you to dress as a maid and they wanted you with decent sized boobs and as a blonde so we came up with a bimbo maid idea" "so you have them to thank for the clothes as well so you better serve them like you did with the boy today" I just replied with "yes daddy I'll do my best..", "good princess!" "oh that reminds me, when they get here you will adress us with master and properly introduce yourself" he said, "yes daddy" I replied.
We spent the rest of the day getting ready preparing the food etc until 5pm.

It was 5pm, the doorbell rang "go on greet them, properly like I showed you" he said, "yes master I'll be of service" I replied, "good very good! now go" he said as I went to open the door.
I opened the door to greet his friends "welcome masters I've been waiting for you, please come in" I said as they smiled at me, once inside they looked me over "can I take your coats masters?" I asked and they handed me their coats, as I turned around to hang up the coats I accidentally bend a little making the skirt fly up a little showing my ass which prompted one of them to grab a cheek "I can't wait to have a piece of this later tonight" he said with a grin, "I'd be happy to service you master" I replied, they both said "damn he really trained you as a proper maid didn't he!", "I'm glad you're pleased with me masters" I replied as we went to the livingroom.
My neighbour entered with snack and said "welcome welcome! I see you've met my maid already. come on introduce yourself to these gentlemen!", "yes master" I said as I placed my and over each other in front of my belly and lowered my head a little give a slight bow "hello masters, I am Sylvana but please call me Silvy and I'll be your maid tonight" "please don't hesitate to ask for anything, I'll obey your every order" "I am pleased to meet you" they all smiled and the friends introduced themselves (for the purpose of anonimity I'll be calling them Peter and John in this story).

They all sat down and put on the match, my neighbour told me to stand back a little with my hands placed on my belly like before.
About 10 minutes into the match John said "Silvy could you refill my drink please", "yes master I'd be happy to" I replied, as I finished filling his glass he grabbed my waist and pulled be onto his lap "stay here for a while" he said, "yes master" I replied, I now sat sideways on his lap my legs/feet places close together and my hands on my thighs "damn he really made a proper girl outa ya didn't he" Peter said, "yes my master has put a lot of effort into teaching me" I replied, then John said "lets see if he really teached you everything shall we?" even before he said that I already felt his bulge growing against my butt, "kneel in front of me" he said as he spread his legs and unzipped his pants "yes master, whatever you want master" I replied.
I kneeled down and he whipped out his throbbing cock "go ahead baby girl, do your job but don't swallow until I say so!" he said, "with pleasure, master" I replied as I started to service his cock, while I was servicing Peter I could hear my neighbour and John unzipping their pants as well, "good god your a fine maid, I've never had it feel this good!" he said out loud as he came in my mouth, I did as I was told and kept it in my mouth he had me keep it in there for a good five minutes before letting me swallow.
As I swallowed he asked if it tasted good "yes master, please give me more later tonight" I replied, "don't you worry baby girl you'll have plenty!" he said, "now then Silvy how about you service us too?" my neighbour said, "yes master with pleasure" I replied.
For the rest of the match I was made to suck them off and swallow it everytime and to bring drinks and food around, I was also told to properly bend over showing my ass whenever I placed down a glass or tray of snacks.

After the match was over my neighbour took Peter upstairs saying they had a surprise for me, once they'd left John asked me to sit on his lap again but this time facing him and he started kissing me, his hands slowly going down to my ass taking the buttplug out, I knew where this was going, "don't worry this is all part of it, I'll just ease you in a little" he said "yes master please do as you wish" I replied, he grinned and put me down on his cock telling me to ride it and don't stop kissing, I obeyed.
"Good now turn around, it'll go deeper that way" he said "yes master whatever you wish" I replied, this went on for maybe 2 or 3 minutes as my neighbour and Peter came back down "good you worked her in John?" Peter asked, "yeah sure did, she got a fine ass" John replied, "good lets all head upstairs then" my neighbour said.

Once upstairs in the guestroom I noticed they had transformed it into what you could call a sex dungeon with all kinds of toys and restraits, they'd even put up a frame to the wall which I thought was a bedframe at first.
"now then, take your panties off and lay down on the bed on your stomach" my neighbour said, "yes master" I replied and took my panties off.
As I climbed onto the bed they were undressing and grabbing a few thing from the drawer, once again the blue pills and lube appeared, Peter finished first and climbed on top of me cuffing me hand behind my back and cuffing my feet together "right since you already had some fun John we'll go first" my neighbour said as he got onto the bed in front of me "alright guess that's fair and all" John replied.

As my neighbour was positioning himself in front of me, placing my face right on top of his cock, I could feel Peter's cock resting between my cheeks "right you ready for this" Peter said while lubing his cock, "yes master please use me, please make me cum too" I replied, "alright here goes" Peter said as he thrust his cock inside me, he was bigger than my neighbour and John so I couldn't help but moan a little right away which prompted my neighbour to shove my mouth over his cock "damn she's mighty tight" Peter exclaimed.
After a short while Peter took my neighbour's place and John took Peter's place and I soon figured out why my neighbour wanted me to deepthroat having Peter's cock in my mouth. They kept rotating like this until they had all dumped their loads in my mouth but ofcourse this wasn't the end they each took a blue pill and while waiting for it to take effect they uncuffed me and bend me over the bed, cuffing me hands on the other side and my feet on something that was underneath the bed when they finished I was standing cuffed in an X position bend over the bed easy access to my ass.
They each took turn thoroughly fucking me but wouldn't come, this was my first experience being fucked by multiple men and I enjoyed it thoroughly.

After they were done taking turns they uncuffed me again and told me to stand hands and knees over this metalbar which had 5 collar/cuff looking things attached to it, I soon figured out its use, they cuffed my hands and feet again and they fastened the bigger collar looking thing around my neck, locking me in a doggy position they then resumed to take turns on my ass and mouth, I was being spitroasted, they came in my ass and mouth and uncuffed me after but just as I thought it was over I noticed their cocks were still rock hard and as I looked up I saw them grinning at me "don't worry baby girl, these are a bit stronger so the fun isn't over just yet" John said and they all laughed, "yes master I understand" "please masters use me more, make me cum more" "I'm your maid after all, I'll do anything you say" I said, they all smiled and went on to use me until 1am after which John and Peter left saying we should do this again soon (and soon it was, 2 weeks later my neighbour took me to John's house where he was having a party which would become my first real "big" gangbang experience).

Tired and dripping (and covered) in cum I fell asleep on the bed and went back home the next day while still wearing all the clothes, or well.. what was left on anyway.
When I got back home after having showered I noticed a text from my neighbour saying something about a party he wanted to take me to.

The End...


Chapter 3 will be about the party and my first "big" gangbang experience