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Disclaimer: Everyone involved in this story is over the age of 18. Names have been changed (except mine) for privacy reasons. This is based on a true story, some details have been changed. Sorry if it’s a bit long!
Hi! My name is Madison. I am currently an active hotwife with a colourful past that I like to share online. I have told this story on here in DM’s a few times and people have suggested I post it here, so here goes…
Brandon and I had gone to the same school as each other for our entire lives, but our paths never really crossed because we hung out in different friend circles. Until senior year. We had a few classes together and due to the dwindling cohort, we ended up striking up conversation.
We discovered we both have a lot in common. Brandon was funny, smart, and cute. The whole shebang. He eventually reached out on social media and we went from chatting every other day in class to chatting non-stop. All day, every day.
Before long, he got the courage to ask me out. I said yes. Of course, I would. This will sound cliche but he wasn’t like the guys I usually crushed on. He was sweet and kind. He treated me really well. I would spend every afternoon at his place. We would just hang out. I might watch him play video games or we would watch Netflix and chill. No, not that kind of “Chill” we would only chill.
See, we were both still virgins and we had promised ourselves to each other. While I was SO ready to lose mine. I had even started birth control. Brandon was a bit more hesitant though. I would initiate, and we did come close a few times but he would always talk me out of it and we would end up finishing in other ways.
Well, the end of the year came around and Brandon and his family were going to Queensland to visit other family he had there. For two whole weeks. I was distraught. I didn’t know what I was going to do with myself while he was gone. I was bored, and lonely.
We kept DM’ing each other all day, and every night we would facetime before bed, usually for an hour or so.
A few days after he was gone, I did one of the worst things I have ever done to another human being.
My friend, Taylor, was throwing her birthday party. She was 18 and finally allowed to legally drink, so, in true Aussie fashion she was throwing a “piss-up” in the back yard. It was at her boyfriend’s parents place. There was a detached “granny flat” (A small house, separate to the main house) that her boyfriend stayed in and outside we had a fire pit for a bonfire. There were a few tables and things like that set up for “King of Beers” and other such drinking games.
The party was attended by about 60 other people and one of those people was Josh. My friend’s boyfriend’s friend. I knew Josh. I had met him before numerous times. He was older, and cooler. He was one of the many people in my DM’s but he was one that I actually responded to.
We would chat from time to time online, nothing serious, just chatting. And occasionally we hung out when I was with my friend Taylor and her boyfriend. I suppose you could say I had a small crush on him. He was cute, tall, and had that “bad-boy” vibe. He had a reputation as a fuck boy too, but that didn’t worry me because he was nice to me and I wasn’t interested in pursuing him, I had Brandon.
Well, the party went on and Josh had me enamored. He was getting me drinks, introducing me to people I didn’t know and just making me laugh and have a good time. I was tipsy when I realised “Shit!” I hadn’t texted Brandon. I pulled out my phone out and I remember feeling guilty at seeing my last message – “Leaving for the party now, love you xo” – 2 hours ago and Brandon’s FIVE follow up texts. Now, It’s been a long time but they were something like this;
- Ok, have fun!
- Wish I was there
- Thinking of you
- Quick call before bed?
- Don’t drink too much, you don’t want a hangover
“Sorry babe, I’ve been having lots of fun, Taylor’s 18th is going off! I’ll call before bed if it’s not too late”
Josh made fun of me and I felt a little silly for the way I reacted just because I hadn’t texted Brandon in two hours.
The party raged on and Josh and I were getting closer. We were sitting on an outdoor 3 seater lounge, my legs draped over his as we laughed. The people around us were passing a joint around. I didn’t partake but I was hitting Josh’s nicotine vape a lot. I hadn’t vaped before and I was enjoying the banana taste.
Looking back, Josh almost always made sure I had a drink in my hand. But I can wholeheartedly say that what happened next was not because of the alcohol. Josh made an excuse, I can’t remember what exactly it was but he mentioned needing to get something from Taylor and her boyfriend’s room and asked if I wanted to come along.
I did.
He led me away from the party and into the flat. We walked through the living room that had a few people hanging around and into Taylor’s bedroom. I remember my tummy almost aching in worry and anticipation, “What the fuck am I doing,” I told myself, as I thought of Brandon. “Nothing. Just hanging out with a friend. We haven’t done anything wrong.” I said.
I remember being hyper aware of the silence in the room, away from the music and party goers of the evening. I stood awkwardly by the door while Josh fished around for a vape or something or other. He produced one, took a hit and plopped down on the bed, motioning for me to join.
He offered me the vape, “ahh, It’s quiet in here,” he said.
As I hit the vape, Josh produced two drinks, a Vodka cruiser for me and a beer for him. He opened them and passed me one.
I took a sip, and sat down alongside him on the bed, resting my head on his shoulder. I can’t remember what we talked about anymore, but I remember giggling a lot and Josh had moved to drape his arm over my shoulders to cuddle me as we talked.
His phone was connected to Taylor’s BF’s speaker and he played some music, Quietly, just enough to drown out the noises from the other people in the lounge room of the flat.
He had been complimenting me, saying how pretty and funny I was. I was smiling, when he turned his head and kissed me. I did not resist. I let his tongue fill my mouth and I played with it back, swirling my tongue around his as he explored my mouth.
I can honestly say, at that moment I didn’t think of my boyfriend at all. I was so turned on, I climbed Josh to straddle him and make out more. I was grinding my hips into his lap, and could feel his cock pressing against his pants. I was wearing a skirt, with a cropped top so he easily slid his hands under my skirt to grasp my hips as we made out.
He had such big strong hands that made me feel like I couldn’t go anywhere, even if I wanted to. He slipped his hands under my skirt and started playing with my pussy through my panties. I moaned. The aching desire I felt then is one of the most intense moments of my life. I wanted nothing more than to have him fill me right then.
I slid back, and reached down to free his cock from his pants. It was a decent size, bigger than Brandon but not by a lot. His hands ran under my shirt. I have pretty small boobs so I wasn’t wearing a bra. I moaned again as his fingers found my nipples. He kissed me and I raised my arms up, as he lifted the shirt over my head.
Fuck. What was I doing?
His cock stood straight up, aiming at me and waiting, the head slick with pre-cum. He was clearly super turned on. I pumped his cock a few times in my fist as he squirmed under me.
Then, he rolled me over, flat back on the bed and in a quick motion, before I could say anything he was slipping my panties off, down my legs and off my ankles. If he had of fucked me right then and there, I might have not had the chance to say a word. I was terrified, and excited.
Instead, he moved his mouth to my bare, waiting pussy. My head exploded as his tongue immediately found my clit. I don’t know how long he ate and fingered me, but I came at least three times.
My mind was in bliss when he propped up on his knees, “Don’t worry, I won’t cum in you.” he said. The words snapped me back to reality. I propped up on my elbows, to see his cock, long and thick waiting poised at my pussy ready to enter.
“Wait, wait, wait, no, no, no,” I said, “Stop. I can’t.”
He waited.
“Don’t worry about your boyfriend.” he said, with a smile, “He will never know.”
“It’s not that.” I told him, “I’m… I’ve never…” I was suddenly embarrassed as hell.
I remember my cheeks burning of embarrassment as the realisation struck his face.
“Oh. well, we don’t have too…” he said. He was clearly disappointed and frustrated and I felt terrible for teasing him.
“I’m sorry,” I told him.
He was understanding though, he made it into a joke, about using my ass instead that way I stay a “Virgin”
He laid next to me on the bed and went to put his cock away.
“Don’t” I said, as I hopped up onto my knees.
“The least I could do,”
I took his cock into my mouth. He was thick and hard and warm. His cock tasted of pre-cum. I swirled my tongue around the tip, and along the underside then once, twice, three times I bobbed on it, getting it deeper each time. I built up a steady rhythm and before long his hips were bucking underneath me.
“Stop… I’m gonna…c-c-cum”
I didn’t stop and before long he was filling my throat with his load.
I giggled when he said, “Oh fuck. Did you swallow it?”
We cleaned up, dressed and returned to the party. No one noticed a thing. This is when I had a bit of a meltdown. It was around 11pm. I had been at the party for at least 5 hours and I had not only practically been ignoring my boyfriend, I had gotten eaten out by and sucked off someone who was most definitely not my boyfriend. I had ruined everything.
To keep a long story short Taylor found me crying in her bathroom. I immediately confessed to my best friend and she made me feel better. She assured me no one has to know.
I had been drinking, so I couldn’t drive but it was at this point, I should have went straight to bed before I made any more mistakes. Instead, I rejoined the circle around the fire pit. The party was dwindling now, around a third of the guests still remained. The rest had filtered off to various places.
I calmed down a lot and returned to my jovial self as we talked around the fire. Josh was there, sitting next to me. He was still being his nice self, which made everything feel easier.
I went to get myself another drink and when I returned, my seat had been stolen. It was taken by one of Josh and Taylor’s BF’s friends. Looking around for another seat, Josh spoke up, “you can sit here,” he patted his lap.
Why not? I thought. It’s friendly enough. Just sitting on someone’s knee. It would have meant nothing if his cock hadn’t been in my mouth less than an hour ago.
I sat down and it ended up being no big deal. Until, I received a facetime call. It was Brandon. I opened the chat to a plethora of more texts. Saying he loves me, Asking If I’m ok and can we still call before bed. He said he would wait up. That was almost an hour ago and now he’s calling me.
I had to answer.
Still sitting in Josh’s lap I swiped to answer.
Brandon’s sweet face showed up on my screen and I almost burst into tears. I kept it together though and made sure to keep Josh out of frame.
I said a few courtesies, “Sorry, It’s been loud, I’ve been having fun, I didn’t feel my phone going off. Lost track of the time. Love you, goodnight.” kind of thing. Taylor was sitting next to me and I don’t know if she did it on purpose to save me from squirming or what but she said, “Braaaaandon, Heeeeeey,” and snatched the phone out of my hands.
She drunkenly talked to him, passing him around to her other friends, and keeping me out of the spotlight for the next ten minutes.
“Sorry, the girls are drunk,” I texted him, when they had hung up and gave my phone back, “Talk in the morning, night, love you.”
Before long, the part was really winding down now, It was like 1am. Some people were sleeping in the main house, others were in tents in the yard. Some had caught an uber home. Taylor was practically humping her BF by the fire next to me and Josh as Josh ran his hands idly along my thighs as we talked.
We all agreed to go to bed and Taylor assured me she would clear out the loungeroom of her flat, where she had reserved the fold out lounge for me to sleep.
Josh and I followed her and her BF into the flat, luckily the crowd from before had dispersed and my sleeping spot was free. A small, double sized foldout futon lay there waiting. A 2 seater was nearby, where Josh claimed. On the floor, across the room in dark corners of the place about three or so people had found sleeping spots so we weren’t entirely alone.
Taylor and her BF slunk away to their room as I got comfy in bed. Josh wandered off and I asked where he was going.
“Just a sec,” he had said, and ducked into Taylor and her BF’s room.
He returned a few moments later with a small bag. I expected him to hop into his two seater, but instead, he plopped the bag down alongside my bed and climbed in.
“May I?” he said without even waiting for my answer he wrapped his arms around me.
I know if I objected he would have gotten into his bed instead, but I didn’t object.
He played some music on the tv and we just lay there. Talking and giggling quietly. He was running his fingers over my tummy, my thighs, my back. Anywhere he could get his hands and it was driving me crazy.
The music from Taylors room got louder and mixed with the sounds coming from the TV in our room. And then, the unmistakable sound of Taylor’s moans and then screams drifted to us.
We were laughing at them and making jokes but it was definitely making me horny.
Before long Josh was playing with the waistband of my panties, “Wanna fool around again?”
I nodded, and kissed him.
In the dark of the living area, with such low light, all inhibition was lost and again, I didn’t feel any guilt when I thought of Brandon… and before long we were both butt ass naked.
Josh asked if I wanted to sixty-nine and at first I thought the others in the room would hear us but Josh convinced me they wouldn’t so I agreed, so I hopped up on him and started sucking his cock again. He still tasted lightly of cum but he was as hard as ever. I was trying not to gag on his cock at this angle since it got so deep in my throat when something new happened.
A tongue was pressed against my asshole as Josh was the first person to ever eat my ass. I tensed up and almost pulled away, but his hands roamed my body and reassured me before returning back to my ass to keep it spread while he ate me.
It felt so fucking good.
I ended up coming like that while he ate my ass and ran circles on my clit with his thumb.
Looking back, I should have known that this was the point of no return but I didn’t. I still told myself I was waiting for Brandon.
Josh and I talked, and cuddled, and wrestled and played around. Before long, I was on my back and he was between my legs again, with his cock inches away from my virgin cunt.
I still remember the excitement when he said, “I want to fuck you so bad,” as he looked between my legs. “Can I? Just a little. Just the tip?” he smiled.
The excitement and anticipation in my tummy overwhelmed me and, I bit my lip and thought.
“Okay. Just a little. Just the tip.”
You could have sworn I just told him I’d give him a million bucks.
He reached down to the bag he brought from Taylor’s room and retrieved a small tube of lubricant.
He applied some to his cock, running his hand along the shaft, then applied another dollop directly onto my aching pussy. The stark coolness of it made me jump, but soothed me.
My pussy was on fire as he ran his cock along my slit, sending shocks of electricity along my spine, all the way to my neck and scalp.
Then, there was the pressure as he pressed his cock against my waiting hole. It hurt like a bitch. “Ow, slower,” I asked
The pressure lessened and he ran his cock around my pussy for a little while longer, before placing the head against my vagina and applying another dollop of lube. It was cold and then warm as he pressed forward. The pressure was back now, coming and going, but no pain this time.
“Shit,”
I felt stretched, and full and the pressure was building in my pussy. Electricity ran through my body.
“Is, is that the tip?”
I looked down to see, in the dark and at that angle, It was hard to see. But his huge cock was impaling me and it looked like I might break in half. It was definitely not ‘just the tip’
“Not… Not… the tip.” I said.
“Oops. Sorry. Want me to stop?”
I shook my head, lifted my hips and tried to pull him closer.
There was some slight pain as he filled me more and before long, he was buried into me, to the hilt. It felt exquisite.
“Stay there, just let me… adjust.” I said to him,
And so he did. He laid on top of me, with his hard cock deep inside my once virgin cunt. One that belonged to someone else. Brandon. The thought came out of nowhere, but when Brandon’s face filled my thoughts while another man’s cock filled my pussy. It was supposed to be Brandon. I’m ashamed to say, I didn’t feel guilty at that moment. The thought just brought me close to orgasm.
Josh got the cue and started to withdraw from me, before entering again, slowly, slowly, but deep. So fucking deep.
And that was it. I was being fucked for the first time. My mind exploded with my body, shock after shock ran through me. Before long, Josh was ploughing into me, the wet sounds were filling the room but I didn’t care.
Somewhere, Taylor was still screaming.
Josh’s thrusts became more erratic and I knew what was coming.
“I’m on the pill.” I said
“Ahhh,” it was too late, He pulled out and jerked his cock onto my tummy. He shot rope after rope of his thick load onto my pussy and tummy.
* * * * * * *
We woke up early in the morning and fucked again, this time he filled me with his load and then I must have fucked Josh another dozen times over the next few weeks before Brandon got home. And it didn’t stop when he got home either. For months I was taking Josh’s cock anytime I could get it.
Eventually, Brandon was ready and we had sex. I obviously didn’t have the guts to tell Brandon the truth, so, like a coward, I pretended it was my first time when Brandon fucked me. It was fun, awkward and silly. We had some good sex afterwards and at first I tried to stay faithful to Brandon. But, I found out that I couldn’t. Any chance I got I was fucking Josh behind his back, even a few times when we were all hanging out.
Eventually, Josh got a girlfriend and Brandon and I broke up for different reasons but to this day, he still thinks he’s the man that took my virginity.
And that’s the story of how I cucked my first love.
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