So first check my post history and check out part 1 of this story. It’ll help everything make sense. As always I’m open to feedback, good or bad. It’s the only thing that’ll make me a better writer. Lastly I’m available for custom stories for free if you want, just PM me and let me know what you want and tell me a bit about you and let’s make it happen. Now – onto the good stuff!!
**Upvote challenge!!**
But first I have an upvote challenge! I’m a new writer, still trying to get my stuff and my name out there. So the more upvotes I get the better the exposure for my stories. So I think it’s a good idea to do this “Kickstarter” style – offering incentives for upvote count.
I wrote this story last week actually and I sent both parts to Stephanie. For two reasons – #1: I wanted to make sure I remembered things correctly and got her side of the story. and #2: I wanted to see if she was interested in getting back into some kind of kink relationship. She was able to help me with #1, correcting some details and reminding me of some things I forgot and she was totally open to #2. In fact we got to talking and she sent me a pair of her used panties! She wore them for four days for me and did a little pee and poo action in them – plus some nice lipstick kisses for me.
So far my best story has **15 upvotes**.
*If this story can match or pass* ***15 upvotes*** *I’ll continue this series with one last true story – it combines both stories. Bill and Stephanie meet and figure out what I’m doing with each of them. It winds up with all three of us meeting for a night!!*
*If this story doubles that and get* ***30 upvotes*** *I’ll share a picture of her panties and of her pussy and asshole, with her permission!! I’ll edit the story and add it once it reaches that point.*
Not sure if this is against the rules or anything but there’s no harm in self promotion as long as everyone involved is good with the outcome right?
**Story**
Steph and I were still on the couch, still soaked and nasty from our little tryst earlier. She was laying on me and I was holding her, smelling her, and looking at her chubby but gorgeous body. I had thought about this moment so many times – every time I masturbated into her panties and so many other times I was jacking off alone. I finally had gotten the chance to see her naked and play with her and I loved it – but I wanted more. All my friends were having sex and I was tired of waiting, I wanted her and I wanted her to take my virginity. It would still be special – she was like my sister and had known her forever and I had a true crush on her for quite a while.
As all that was going through my head I decided to talk with her before we went to the shower. It turned into a rather long conversation, about 30 minutes so I’ll summarize it here rather than type it all out. I asked her why she finally let this happen – we had talked all spring about doing stuff like this but she always said it would never happen. She told me where she had been the past couple days – she was off visiting her boyfriend. She surprised him with a visit only to find another womans clothes there! She questioned him, checked his phone and found out he was cheating. She said she was going there to finally have sex with him so she had been building herself up for a good while and had a huge let down. She broke up with him and came home – only to find me waiting. Someone she had known and trusted for a long time. I asked her if I was a just a rebound from her guy and she told me she could ask me the same. I confessed and told her how long I’d been crushing on her, told her about masturbating into her panties and bras and how much I wanted what we talked about that spring to happen. She confessed that she knew I had been masturbating into her panties and she always left me nice pairs. She also told me she loved to find them after I was done and smell and taste my cum! One time she got to them pretty quickly and she told me she licked up and swallowed all my cum and then rubbed the cum stain deep into her asshole, lubing herself up with my cum. She eventually used a dildo in that hole and came all over the panties, leaving them for me to start the process again. I told her I remember that pair – they were pink lacey boyshorts!
Thinking back to earlier and wanting to finally have sex with her I asked her about all the stuff we talked about that spring – what we just did was pretty raunchy and so was what we talked about. I asked her if she wanted to date or just be FWB and do all that stuff. She turned her whole body to look at me. She reached down and grabbed my soft cock with one hand and grabbed her bush with her other hand. She told me they were meant to be together, ever since we were little kids. She meant everything we talked about and did that spring and she wanted to try all of it, and more. She told me she was always horny and would say yes to anything we want to try.
That was exactly what I wanted to hear. I reached my hand down to hers on her bush and squeezed. She squeezed my cock and it started getting hard. I leaned in for a kiss – she still had a little bit of cum on her chin and I’m sure I still had piss in my beard. But we kissed passionately – tongue, fondling….it was great. When we finished I reminded her we still needed to shower – we were nasty at this point.
She took me by the hand and led me up the stairs towards her parents bedroom. They had build on a huge addition to the house – more than doubling the square footage. Her parents made an awesome master suite, above the new addition. Up the stairs was nothing but their suite – large bedroom with king bed, huge closet and amazing bathroom – complete with double headed shower and jacuzzi tub.
We went up the stairs into the bedroom, she took my shirt off (she was still naked and I had my shorts and underwear off but never had my shirt off) and laid it on the bed. She led me into the bathroom and told me to lie down on the shower floor. I wasn’t sure what she was up to but I wasn’t about to stop her so I did what I was told. I got into the shower and laid down. She quickly came in after me and straddled me – standing up. She had her legs spread and I could see her hairy mound above me. I couldn’t see her face due to her massive tits being in the way.
“Start stroking that pathetic tiny dick slave!” Stephanie boomed, the shower making her voice seem quite loud.
“Yes, my Queen!” I stuttered, grabbing my semi hard cock and stroking as was requested.
“Here’s the only shower you’re going to get!” Steph yelled as she parted her hairy lips and started peeing all over me. A golden shower!! I instantly got hard. Her seeing me get hard made her start fingering herself and flicking her clit – she was still peeing on me but it didn’t take long before she told me she was going to cum and try to squirt!
“May I cum as well my Queen?” I asked, quite close to cumming myself.
“Yes, but only after me – ohhhhhh!!” Stephanie yelled as she stopped peeing and started cumming all over me!! Her spray turned from yellow to clear and and she was buckling at the knees. She didn’t squirt much but I moved forward to catch what I could in my mouth. I continued to stroke and as she was pushing, trying to squirt out more she wound up queefing – quite loudly in the shower – with the walls likely making it seem louder. For some reason that was all it took and I started cumming. It was all over my cock and was still coming out as Steph started to go towards the shower floor by bending her knees.
She continued lowering herself down towards my still hard cock. For a moment I thought she was going to try and put my hard dick inside of her pussy. I was so scared!! I wasn’t ready for my first time to be like this – we didn’t have protection or anything either!! Turns out it was out because I was about half right – she lowered herself down to where her hairy asshole was right on top of my head and with one push and grunt she opened her hole and lowered herself onto my cock! As soon as she was on it she closed up her hole and got back up, turning around and showing me her now quite cummy hairy hole.
“I want you to clean my asshole slave – you made it all dirty!!” Stephanie said as she pushed her huge ass backwards towards my face. Doing as I was told I started licking all of my cum from her ass – eventually moving my tongue to her hole – and with that she started pushing out some of the cum that had made it inside of her. When she was satisfied she turned back around and pulled me up to kiss me – tasting the combo of my cum and her ass. She was kissing so hard and passionately – she couldn’t get enough!
With that she turned back around and turned on the shower. We continued to fondle each other and kiss as we cleaned up. We washed each others bodies, often cleaning with our mouths before using the soap. After about 15 minutes we both decided we were clean and got out of the shower and dried off.
Steph realized we didn’t have any clothes so she offered to run down and grab mine while she got some for her. I continued to dry off and eventually started down the stairs to find her. My clothes weren’t sitting by the couch anymore so I started towards her room. I walked in to see her from behind – she was putting on her bra – a cute little lacey red pair that matched her little g-string that was already on. She turned around and told me my clothes were on the bed – when she turned around it was clear she hadn’t worn that bra and panty set for a while – her huge breasts were spilling out of her bra – so much so that I could nearly see her large dark nipples. And her g-string was pulling hard into her ass from behind and didn’t even cover her bush from the front – it was very tight and pulling into her pussy – separating her mounds a bit. I barely had time to look before she covered it all up with a long t-shirt, that just barely went long enough to cover her panties.
I grabbed my shorts and shirt, which i had brought with me from upstairs. Noticeably my boxers were missing – I didn’t see them by the couch and they weren’t in the shorts like they were when she pulled them off. I didn’t think much of it so I put my shorts and shirt back on.
Stephanie left and brushed past me – saying she was going to run upstairs real quick and then make us some dinner. I told her ok and followed after her, stopping in the living room to sit on the couch and watch some tv. Steph headed up the stairs – my eyes followed her the whole way – finally being able to see under that long shirt, seeing her fat ass eat that g-string and seeing her buns sway back and forth. I was already starting to get hard again!!
I grabbed the remote and turned the tv back on – flipping through the guide to find something I wanted to watch. Steph came down from upstairs and walked past me into the kitchen. I continued to watch TV and was greeted just a few minutes later with Steph walking in with a plate of food – a couple of hot dogs and chips and a soda.
“You did well today slave – you deserve to eat a good meal!” She said while handing me the plate.
I was famished at that point so I thanked her and started wolfing down my food – it tasted great! After we both ate we sat and watched some more TV – interspersed with some heavy petting, fondling and kissing and playing. Even though we had both cum twice that day we were still very frisky and each wanted more.
I asked her if I could stay the night with her – no sense in wasting this time without her parents. She told me I could so I asked what room she wanted me to sleep in. She said we’d both be sleeping in her parents room – in the king bed in the master suite!! I asked her if she was sure and she said she was – she wanted both of us to sleep there together.
“Does that mean we can have sex? I’m ready if you are – I’ve crushed on you basically my whole life and sharing it with you will be special – you’re like my sister. Plus it’s obvious we’re both into the same kinky shit” I asked her, trying my best not to look at her due to my nerves.
“Yes, we can have sex. But it’ll be the way I want and how I want it. You’re my slave and you’ll do as your told. I have ideas for how this will go!” Stephanie said, sitting on the couch with me eating her dinner.
Who was I to argue? I told her it was fine – I was happy to do whatever my Queen wanted.
We sat there and we finished dinner. We started cuddling and I felt my phone vibrate so I reached into my pocket and grabbed it. It was then I realized that something was missing. I was 100% sure that was the pocket I stashed the purple panties in earlier….shit!! Did Steph find them and take them back? What happened to them? I tried to play it cool and pulled out my phone and checked the message and wrote back but Steph knew something was up.
“What’s the matter? Something missing from your pocket?” She said, looking over at me with a shit eating grin on her face.
“I think we both know what was in there and what I was going to use it for – I told you what I do with them, especially yours. But i shouldn’t have taken them without asking you so I’m sorry” I said sheeplishly.
“It’s fine, you’ll get your punishment soon enough!” Steph replied, looking back towards the TV.
The rest of the night went much like that – watching TV with little jabs and statements here and there. Eventually it was close to 11pm and Steph decided it was time to go to bed. I got up to go with her when she pushed me back down into the couch.
“No, you need to give me some time to go up there and prepare!” Steph said, walking away towards her room. “I have to go get a couple things first then I’m headed up stairs. I’ll tell you when I’m ready!” she exclaimed, walking up the other set of stairs towards her room.
I was stunned – prepare? What did she need to prepare for? What was going to happen? All I knew was that I started getting hard almost immediately, I was ready for this.
It only took her about 2 or 3 minutes in her room to get what she needed and she quickly walked by with a bag and walked up the stairs to her parents room. She stopped halfway up and called back to me – “Go ahead and take all your clothes off, you need to be naked when you get up here but don’t you dare come up before I tell you to!” Steph basically shouted at me.
She disappeared further up the stairs and out of sight. I did as I was told and took all my clothes off, sitting naked on the couch, waiting on my Queen to call me.
About 5 minutes later she did just that – “Slave – your Queen and goddess is ready for you!” she said, being heard and not seen.
I got up and started up the stairs. The door to the bedroom was cracked and I could tell it was dark inside.
I opened the door and stepped in. Stephanie was laying on the bed – with a cute baby blue nightgown replacing the long t-shirt from before. I could see she still had the red bra on though, the one that was far too small.
I started to come closer to her, ready to kiss her and get this started when she reminded me that she was in charge and the first thing I needed to do was to get dressed.
“Dressed? You just told me to come up here naked!” I snapped back.
Without saying anything she just pointed to the end of the bed. Sitting there, neatly folded was her purple bra and the purple panties I stole earlier!
“If I remember correctly not only do you like sniffing my panties and cumming in them but you like wearing them too right slave?” she said, still pointing towards the bra and panties she expected me to wear.
I nodded and stepped forward and took the bra in my hands. I slipped them over my arms and onto my shoulders and I turned around to have her help me with the clasp. She clasped them and I was impressed at how well they fit me – sure the cups were too big but the fit elsewhere was ok. Then I grabbed the panties and went to put them on. As I opened them to slide them on my legs I noticed a fresh wet spot in the crotch.
“I thought I’d give you something fresh to smell if you earn it!” she said. I guess she had cum in those panties during the few minutes she was up here! I didn’t date to sniff them now so I quickly pulled them open and slid my legs in, pulling them up. There wasn’t much to the front of them and they barely kept my hard cock inside.
“What a cute little sissy girl you make! Such a perfect little sissy slave aren’t you!” Stephanie laughed. All I could do was nod and blush – partly in shame but partly due to how hot this was making me. I was getting more and more turned on by the second.
Very quickly she said “Time for the first surprise! You’re dressed like a girl so maybe you need to have sex like a girl!” she said as she pulled up her nightgown – revealing a large strapon barely contained by her already too tight panties!
She pulled my head forward – “Better lube up my cock before I stick it in you!” she said, taking her cock out from her panties. She quickly pulled her panties down and laid down on the bed. Being a good slave I did as I was told – taking her cock into my mouth and sucking with all my might. I started letting my other hand play around – first in her extremely wet pussy then I started to go south towards her hirsute butthole but there was something there. I started feeling around and she had a butt plug in!! Where did she even get all this stuff? Was it from her parents? I shuddered at the thought but I started pulling it in and out of her – fucking her asshole with her butt plug.
After a couple of minutes she pulled my mouth off her cock and told me I was ready. She told me to get on my knees, doggy style and I did as I was told. She started by rubbing my asshole through the panties – “Oh what a sweet little pussy you have my slave – I can’t wait to ravish it!! ” She suddenly pulled the panties to the side and started rimming me! Little circles with her tongue, making my hole nice and wet. Finally she stuck her tongue in and out of my hole. “What a tasty little pussy too! I think you’re ready!!” she said as she pulled her face away from my gaping asshole.
She moved forward on her knees – putting the head of her cock right at the entrance to my butthole. Luckily I knew to push out to make it easier to get in and the whole of the cock slid right in me. I yelled in pain and in pleasure. Stephanie reached forward and smacked my head – hard. “You only talk when I say you can talk you slutty slave!!”
She continued to fuck me with her cock, not being gentle at all. My ass was on fire but it felt amazing. She told me her knees hurt and to get on my back – she pulled her cock out and I flipped over on my back. She pulled my panties all the way off and stuffed them into my mouth – “Maybe this’ll make you be quiet!” She then took off her nightgown – revealing her red lacey small bra and her glorious tits and belly. She pulled me to the end of the bed as she stood off the bed – then she quickly put the cock back in my ass.
It was glorious and felt amazing! She was using her hands to pinch her nipples and be rough with her breasts. She also had a hand under her strapon harness – I could hear the wetness of her playing with her clit. Her other hand was busy – smacking and pulling on my balls, hitting my cock, slapping my belly. I was in so much pain but I loved it. It only took a few minutes for the pleasure to be too much and my cock started leaking – I wasn’t cumming but all the pressure on my prostate was forcing out some precum and fluid and it felt amazing.
Stephanie looked and saw what was happening – “Are you such a pathetic slutty slave that you can’t even keep your cum inside when I’m fucking you? You have to save that for later!!” she screamed, forcibly pulling her cock out from inside me and hitting my penis hard with an open hand.
She stood back and slipped off her strapon and harness and reached around and pulled out her plug. “Be a good girl and clean these off for your Queen – use your mouth!” I won’t go into details but they weren’t that clean before I got started. They were sparkling by the time I was done though – at which point she reached down to kiss me – wanting to taste all of that for herself.
“Now pleasure your Queen! If you do well enough I’ll let you cum at the end of the night!” she said as she crawled on the bed and took her panties off. She also unhooked her bra and let her glorious G cup breasts spill out. She laid down and spread her legs, inviting me in.
I moved to her side of the bed, ready with two fingers to give her the shocker. The problem is that the two fingers didn’t do much – she was so wet and her asshole had been stretched by the plug. So I put three fingers in her pussy and one in her ass – she was moaning with each thrust, her pussy and asshole getting wetter and wetter.
“More!” she screamed! So I took the finger from her ass and put it in her pussy – all 4 fingers!
“Fill both of my holes so I can cum for you!” she said. I had to think fast – the plug was decent size but I grabbed the dildo from the strapon and placed the head at her bottom entrance – slowly pushing it deeper and deeper into her until she took the whole of the at least 7″ dildo.
“MORE – Fist me!!” she yelled. I pulled out my 4 fingers and made a fist as she demanded. I had seen some fisting videos but had never tried it – the diameter of my fist was much bigger than just the 4 fingers but I pushed it up against her hairy pussy. I started pushing in – pulling my fist in as small as I could. She was screaming in pain but telling me to keep going so I continued to push. I could feel her strech and rip as my fist made it inside of her. Soon my whole fist and hand was inside of her. I looked down and saw blood and I started to tell her when she yelled at me to fuck her with my fist.
Being a good slave I did as I was told – pushing and pulling my fist in and out of her. It didn’t take long for one of the thrusts to push her over the edge and she yelled “I’m cumming!!” as she started to squirt. I went down with my face to try and drink as much of it as I could. She didn’t squirt nearly as much this time but I got a great taste. I pulled my fist and the dildo out from inside her. Looking at my fist I could clearly see some of her blood – looking down at her gaping pussy I could see we had gotten some blood on the bed. I told her and she didn’t seem to mind – the pain meant nothing to her or she enjoyed it – I’m not sure which.
“Slave, you did a great job – it’s time for your reward. You can fuck me in my pussy but warn me before you cum, I want that somewhere special” she said as she pushed me down onto my back. She crawled up and on top of me, lowering herself onto my hard cock.
She felt amazing!! Yes she was loose but my cock had never felt anything like this. I wish I could say we fucked for 30 minutes before I finally came but let’s be honest – I thrusted and she rode my cock for maybe 3 minutes before I warned her I was about to cum.
She pulled up and pulled my cock from inside her -“Remember what we always wound up talking about this spring? Are you ready?” Before I had a chance to ask which thing she was talking about she lowered her hairy brown hole onto my cock. Her asshole was MUCH tighter than her pussy. I made it maybe 10 thrusts before I exploded in her. I was in ecstasy! I had finally has sex and cum inside a woman! It felt better than any orgasm I had ever had – better than I ever imagined an orgasm could feel. My eyes were rolled back in my head as I was loving it when I came back to reality and realized she was leaning back on her hand – her other hand forward pulling her pussy lips apart and she was peeing on me!! All over my belly and chest!!
I finished cumming inside her ass and she pulled herself off me – she started by sucking on my dick and then started kissing and sucking and drinking her way up the trail of pee she made. She ended by laying on top of me and drawing little circles on my chest with her finger.
“Are you ready to finish this?” she said. I nodded. She kissed me, the smell of pee still on her face and breath. She got on her knees and sort of walked up my body – finishing with her asshole sitting right above my face. She lowered down – her hole right on my lips and her wet pussy sitting on my nose and forehead.
“Eat your own cum you little slut!” She yelled as she started to push with her ass. I opened my mouth as the flow of cum started from her hole and went into my mouth. I was barely able to hold the load when she slid back down my body. She reached her hand down and put my now soft penis inside of her pussy and leaned forward to kiss me.
Gladly I received her kiss, pushing as much cum out of my mouth as I could. She took it into her mouth and swallowed readily. She then slid over, taking my cock out from inside her and laid down next to me.
“I can’t believe we finally did this!” I exclaimed, completely out of breath and energy.
“It was everything I hoped it could be. And we’ve talked about so much more!” She replied, grabbing my hand.
We both laid there for an hour, recovering from the exhaustion of the nights activities. We had given each other our virginity – it was a great night. Who cared about the horribly stained bedsheets now!
The night ended with some wine from her parents liquor cabinet and a long soak for both of us in the jacuzzi – together. Summer was only about halfway over but our relationship and fun was just getting started!!
Source: reddit.com/r/gonewildstories/comments/8vv9y2/mf_first_summer_away_losing_my_hetero_virginity