Hi it's Carleigh ;)

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[carleighhalla]

This old bull likes your stories but you have not posted anything in quite a while. Are you still active or have you quit Tumblr like so many others are doing?

I haven't quit, I'm just went back to school so I've been pretty busy. Not sure when I'll post again sorry!

[carleighhalla]

Free use slut for friends Dad Part 2

My long term memory is rather impressive and this day is ingrained in there. I have a fairly detailed memory of this day as it was the first time he properly used me and set the context for the rest of this ... life defining experience of mine ... that's not to say everything below is 100% how it happened. Just enjoy the write up. You all clearly enjoyed Part 1. It is LONG.

I moved in on Sunday. My friend helped. It wasn’t much but she insisted. She wanted to see the condo and was glad her dad gave it to me for such a low price. She knew her dad furnished the condos he rented out but she didn't think it was to this extent. She admired the condo and all I could think of was how I had been violated like a little slut by her father the day before.

She was moving out of town for her university so I was rather relived. There was no way this would’ve been kept a secret if she were around.

He sent over the lease papers to sign via email. After I had sent them back he sent a money transfer to buy the suit along with a few suggestions.

I should mention he was well off. He pulled in 500k with his job, investments and properties a year according to my friend. He was paying for her own condo as well near her university. Anyways, I digress.

I picked up something that was in stock from the mall that fit with his suggestions.

The anxiety and confusion of it all was killing me and I just sort of went about my life like a zombie until Tuesday.

Tuesday rolled around and I was freshly bathed and all dolled up in the attire as instructed. A full hour before he said he would come. I kept checking my phone to see when he'd message to pick him up from the lobby. I was startled by the door opening. Silly me, of course he has a key. It's his condo after all. The thought of that made me slightly uncomfortable.

We could've been in matching outfits. He was in an all black suit with a white shirt. After our initial encounter I was starting to take a liking to his looks. I had masturbated to what had happened and imagining to what was going to happen several times in those three days. I greeted him with a smile.

"Hii" I said standing up and adjusting my skirt

He came over and we kissed as he felt up my body. Hands making his way up the slit to my ass and down the shirt to my tits.

"Let me look at you" he said as he twirled me around "Beautiful ... " I lost my balance a little on my heels and he caught me. Clearly I was nervous.

"Thank you" I replied relieved he liked it and then he added "...too beautiful for a worthless whore" ... that cut through my soul a little and I felt small ... I didn't say anything

He put his hand behind my head and pulled my hair back, leaned in and whispered in my ear "You remember your safe word?" I nodded "say it" I said it, again thinking to myself at its ludicrousness. I was half terrified half turned on as to what this man was going to do to me.

Let me just say I had been fucked by dicks of all shapes and sizes by then. But that was it, just fucking. By the end of the evening this dick would have thoroughly used every orifice I had like it had never been used before.

"Don't worry I'll go easy on you today whore" as he examined my body once more still holding my hair.

"Now be a good little whore and bend over" he said letting go of me and pointing to table "hands on table, head down, ass out, legs spread" I did as instructed and got into position removing my jacket in the process. The table was against the floor to ceiling windows. I scanned the view and I couldn't make out anything in the adjacent apartments. I doubt anyone would see me like this.

He walked over and felt up my ass and grabbed my hair again lifting my head up, "I let you off too easy last time whore." he spanked my ass with his other hand as I moaned

"Didn't fuck you." he spanked and I moaned

"Didn't get you naked" spank moan

"We'll have to correct that today" spank moan

"Pussy sure was tight" spank moan I felt his hardness as he rubbed up against me

"Lift up your skirt" he said as he let go of my hair

I managed to lift it up enough to expose my ass and underwear.

He let out a laugh, pulled my hair and leaned in close my face "You wanted me to use you today didn't you? You don't need to answer ... the lingerie is answer enough. Is there a matching bra under that shirt?" I nodded my head "Good"

I felt small again and realized he was right. I could've thrown on any old pair and it wouldn't have mattered. I wanted to turn him on. I wanted to impress him. I was a slut.

He began to rub my pussy through my underwear and I realized he was on his knees when he kissed my ass. I moved my hips and moaned to his touch. I was wet. I could feel it. Really wet. He was good at this. Really good. I suppose experience from all the escorts he had experience with. I'm sure he had fucked them where my face was right now. Some of the odd furniture placement was starting to become more obvious to me now that I was being used within the condo.

He stood up, grabbed me by the neck and lifted me up and started to kiss me. His hand never stopped pleasuring my pussy and I continued moving my hips to his touch. Even as we kissed.

He stopped turned me around and had a lustful desire in his eyes. I grabbed his neck and brought him in for another kiss as my free hand went to rub his dick. He was hard. He was big.

He broke off the kiss and grabbed me by the neck again as both my hands went to his dick.

"Tell me what you want"

"I want you to use me. I want you to use me for your pleasure" I said breathlessly as I continued rubbing him with both hands and he leaned it to kiss me again passionately. He was ... really good at this ... if there is anything I miss. It's the kissing.

He let me go completely and walked away, I started to follow, a little confused "Stay there!" I froze and walked back to where I was. He came back with a pair of cuffs and cuffed my wrists. I let him without any hesitation.

He held me by my ass and walked me towards the window, put my hands up above my head on the window and started to lift my skirt up again. I positioned my self for him, sticking my ass out and spreading my legs.

He began alternating between spanking my ass and rubbing my pussy. My moaning and breathing became louder. He pulled my underwear down, I brought my legs closer so it was easier to remove them. I stepped out of my underwear and spread my legs again. He knelt and began to eat my pussy, face buried in my ass, and spanking my ass sporadically. He moved to fingering me again and began to rim me.

I had an orgasm in what seemed like seconds of him licking my ass and somehow managed to keep my balance in my heels. He continued through my orgasm as I experienced waves of pleasure.

Once I had stopped, he stood up turned me around and started making out with me again. I decided to try and take some level of control from him as I broke the kiss, squatted on my heels, hands still in cuffs and started to rub him through his pants, biting his dick a few times. But he wasn't prepared to give me any control.

He knelt down with me started to finger me, we were facing each other and I leaned to make out with him but he denied me. I knelt there in pain and pleasure and I managed to finally say "I need to take my heels off...it hurts..." ... "good...suffer" he responded and continued fingering me rapidly.

I climaxed again and threw my cuffed hands over his head to balance myself.

He stood up and brought me up along with him. I began rubbing his dick again recovering from my orgasm. He pulled me in towards him and started to unzip my skirt and let it drop to the floor. Finally I thought to myself as I hurriedly stepped out of my skirt and tried to take the heels off

"Leave them on" he said sternly smacking my face

"It's uncomfortable" I protested ...

"Leave them on" he smacked my face again ...

My hands went back to rubbing his dick as he pulled me in to make out with me again. He spanked my ass a few more times during this. Eventually letting me go he started to undress himself. When he took his shirt off it was the first time i had seen his naked upper body. He was built. I wouldn't say jacked but he definitely had muscle definition. My hands involuntarily moved away from his dick to feel his abs and chest and we kissed again. My ass got spanked again. My cheeks were pretty sore by then so each spank stung a little.

His hand moved to my throat and he pushed me away. At this point he could tell I wanted his dick. My mouth. My pussy. My ass. Any hole would do. I just needed it. He held me there as he smiled. He reached into his pocket and pulled out my underwear. I didn't know when he had done that. He bunched them, rubbed them against my wet pussy and shoved them in my mouth.

Blowjob is out of the question now I thought to myself as my juices flowed into my mouth. I was disappointed. Having my underwear, freshly rubbed against my wet pussy, in my mouth was probably the lowest I felt that day. It also turned me on even more.

He walked me back to the desk, bent me over, pushed me down, held me there and spanked my ass again.

I heard him undoing his belt and pants. I parted my legs in anticipation not knowing which hole he was going to use. This was taking longer then I thought so I looked back and saw him putting on a condom and lube in another hand. I was surprised he wasn't going to fuck me raw, but I was relieved with his escorting habit it was good.

"You ever take a dick up the ass whore?" he put the tip against my hole, poured some lube

"Yes" I mumbled through the underwear in my mouth and yelped at the lube

"Figures. Fucking teenage slut. How big?" he leaned in and pulled the underwear out

"Smaller than yours...5 inches maybe...not as thick..."

"Good luck" he began to enter me and shoved the underwear back in

"Slowly please" I mumbled back at him

"Don't worry slut I won't hurt you" he pushed me back down

He stayed true to his word. He gently pushed in stopping each time I winched or moaned a little too loud. He pulled out and pushed in a few times. Each time going in deeper and deeper.

Eventually my ass adjusted to being impaled by his dick and he picked up his pace when I started moving my hips with him. He bunched up my hair, pulled my head up and began pounding me. I was moaning probably screaming loudly at this point at the pleasure but the underwear muffled my noises.

I had never been fucked like this before. Hair being pulled. Dirty underwear in my mouth. Full view of an open window. Thick dick in my ass balls deep. This man knew what he wanted. I don't know how long this lasted but eventually I had another orgasm. The biggest one of the day. He kept pounding me through it as I shook violently in pleasure.

He slowed down and spanked both my ass cheeks again and kissed them as he pulled out of me.

I stayed in position recovering, grateful for the break. He had stamina for someone his age. I wonder how long we had been fucking.

"Kneel..." i heard him say

I slowly got up off the table and started to get down on my knees

"Heels young lady ... kneel on your heels ..." he demanded.

Young lady that was nice for a change I thought to my self as I reluctantly squatted on my heels.

He removed the condom and walked over in front of me, hands still cuffed I began to jerk him off. He removed the underwear from my mouth.

"You know what to do...I'm keeping these by the way" he threw my underwear towards his bag "bra too". My shirt was still on but had my hands not been cuffed I might have taken it off right there and give it to him to add to a collection I assumed he had.

I was exhausted and these heels were killing me but I went in to begin servicing his dick with my mouth. I knew he liked deep throat so I went into that rather quickly. After a few seconds though I couldn't take it anymore. I pulled him out grabbed his hand and stood up.

"I'm sorry I can't with these heels" as I took them off "and you need to sit if you're not going to uncuff me...I need support"

He starred at me. I starred back at him. "Yes ma'am" he responded walking over to the couch. I felt a small wave of power. It was soon to be taken away once I was in kneeling in front of him dick in my mouth.

I took him back in slowly this time. Swirling my tongue around his head, sticking my tongue into the opening, before slowly making my way back down to the base. I held him there. He groaned in pleasure. My eyes watered immediately and water started rolling down my cheeks.

"You slut choke on that" as he put his hands on my head. I tried to come up for air but he pushed me back down. His hands kept my head in place. I gagged a few times. My head buried in his crotch. Hands cuffed on the ground. I couldn't do anything. He bent over and spanked my ass a few times. He let me up after what seemed like an eternity as my lungs started to give out.

I gasped for air and coughed turning away from him. "Don't demand...beg...never demand. Get back down there"

I had just been disciplined. I was wrong. This was the lowest I felt that day. I nodded my head. I took him back in and continued to service him.

I stopped. Jerked him off looked at him and asked him "I want you to fuck my throat...please"

He stood up and took control. He held my hair in one hand and my jaw in the other and throat fucked me until he climaxed. There was a lot of gagging. spitting. choking. droll was every where, even my brand new shirt. I was in slut heaven.

I thought his load was huge last time maybe because it had been a while. No. I would learn this is just how much he cums. A lot. He pulled out of my mouth as he got close and just unloaded something like 10 streams of cum on to my face. I was covered. It was in my hair. It was on my face. Some had dropped on my legs. Some on my shirt. Some on the floor.

He fell down on to the couch and I went back to sucking his dick as he slowly went limp, swallowing up any cum that came up.

I looked up at him and smiled, dick still in mouth and he laughed. I was utterly satisfied. So was he. He undid my cuffs as I sat there at his feet exhausted. Covered in his cum. I eventually got up to go clean my self.

"Where are you going?"

"To the bathroom I need to clean"

"No. You need to swallow..."

"What...how?" I retorted

"You have fingers don't you. Get back down here and clean yourself."

I was wrong. THIS was the lowest. Was this condo worth all of this? I'm sure I could get something before university started. I thought to myself as I stood there starring at him. Should I use the safe word?

I sighed, answering myself, and got back down to my knees and cleaned my face with my fingers. Did I mention it was a lot? It probably took less than a minute but it felt much longer. He watched me with a smirk on his face and kept pointing out areas I had missed. Once I was done with my face, body and legs, I sat there almost defeated. I ran my fingers through my hair to see if anything was there, licked my hands and looked back at him.

He ran his hands through my hair and simply said "Good girl..." I let out a smile. At least I think I did. He eventually let me go clean up. He joined me in the shower. We made out. He got hard again and we fucked in the shower. Raw. "Condoms only for anal" he said as he pushed into me. I had two more orgasms. I got on my knees and swallowed when he told me he was getting close.

We made out some more. Had dinner. We talked about normal stuff. He told me he was surprised I never used the safe word even though it was relatively vanilla. He assumed it was the first time I had been roughed up like that. I told him I came close when he told me to clean my face but I was a big girl. Nothing I couldn't handle. I asked him if he collected lingerie from his escorts. He did. I asked if mine were the youngest. He assumed they were. I smiled. We made out again. I gave him another eye watering blowjob. Swallowed his load. I gave him my bra for his collection. He spanked my ass one more time and went home.

My first night as a free use slut was over. I went to bed with sore ass cheeks, sore ass hole, sore throat and sore pussy. I was satisfied.

He texted me to be ready for Friday at 5 PM with a school girl outfit request. I smiled. I would have to have him review my class schedule so he knew my free times.

I woke up to a money transfer with a message "Your weekly allowance. It only seems fair." It was a lot.

And just like that I was an escort. I think.

I would later find out he was trying to reenact a porno with me. He didn't get every detail right but he was damn close before the anal. I sure felt like I was in porno cleaning my face. I pleasure myself to this porn to this day. No I'm not going to say which.

[carleighhalla]

Some basic housekeeping

1. Some details are left vague of my own choosing or cause I don't remember every word that was said

2. Everything is consensual

3. No I wasn't taken advantage of

4. I did everything of my own volition

5. Currently 20

I had recently turned 18 when this happened about to enter university.

A little while before university started I found myself needing a place to stay for a few months, maybe even first year, due to a mix up at the university dorms.

I was at a friends place and the topic came up. My friends were obviously worried and my financial situation wasn't the best that I would be able to afford a decent place for rent this short notice.

Her dad happened to overhear the conversation. He mentioned he owns a few units up the street and has a place for rent. He offered me his business card to make an appointment to work something out. One of his units was empty for a multitude of reasons and he could afford reduced rent for a while longer. Or so he told us. After he left I asked my friend if she'd be comfortable with the idea and she didn't mind. I suppose everyone thinks their parents are harmless.

Now keep in mind this is a man I've known since I was 14 in a passing capacity. We would exchange pleasantries as he would be coming or going. Always well groomed and usually in a suit and you could tell he took care of himself. I would like to say I had lusted after him ever since I saw him. But no. I can't say that I was attracted to him though I wasn't not attracted to him either. I had never thought of him that way. So I had nothing but harmless thoughts in my head as well.

I texted him later that night and he said he could show me the unit that weekend. We settled on Saturday at noon.

I reached the condo and he was waiting for me in the lobby. We exchanged pleasantries and went into the elevator. Small talk ensued I told him I needed a place in August until the end of 1st semester when I would likely get into housing on campus. I thanked him profusely for his generosity but didn't know how I could ever afford the rent. He simply mentioned to see the place first and we could talk.

Enough back story though. Long story cut short he blatantly propositioned me after we were in the condo. Told me this was a personal unit he used for escorts. I would later come to learn more about the escorting business and it's prevalence in my city. The unit was mine as long as I needed it as long as I was his to use or he got bored of me. But he would promise it to me until the end of first semester.

I was taken aback. In utter shock. My mind in disarray. I told him I needed to think about it. He said I have his number and left me to my thoughts and wandered away to the bedroom.

I decided to leave as he walked away. On my walk home I was still thinking about it. Confused. Shocked. Unsure what was going on. I was a slut at heart. I enjoyed all things sex. I enjoyed being used. I was a conquest for many boys in high school and had given myself to older guys in university. I had never sold myself before though. I wasn't desperate or anything either. I'm sure I would find something soon. This wasn't a good idea. I kept walking. Something snapped in me and I called him back.

(The conversation is paraphrased and not word for word)

Him: "So you're considering it?"

Me: "um ... What would I have to do?"

He chuckled "Anything I want is sort of the deal but I want you to be comfortable with this. We can discuss boundaries"

Me: "How would it work?"

Him: "Well we'll sign a lease contract until the end of first semester so you legally have a place to rent.."

Me cutting him off: "I meant the other thing..." my heart was racing at this point what was I about to get myself into

Him: "Come back and we can talk it out"

I turned around and looked back up at the building. It was still visible. There was a long pause. He didn't say a word. My breathing was getting loud and I could hear myself breathe. Something snapped again.

Me: "I'll meet you in the lobby"

10 minutes later I was back in the lobby. The elevator ride up was silent and awkward for me at least. We went back to the condo and the moment the door was closed he had me against the wall back to him. He pulled my waist towards him to grind up. With his other hand he moved my hair and began kissing my neck. His hands then wandered amply across my body. Ass. Tits. Lips. Pussy. I could feel his hardness against me.

I was super turned on and at the same time super confused. I was about to sell myself for an apartment.

"We really should talk this out" I managed to say as he groped me.

He stopped, turned me around and kissed me. I won't lie he was a really good kisser maybe even the best I had kissed until then. I got lost in the kiss and relaxed entirely. He broke off the kiss after a while but still held me close.

He lifted my dress, put his hand down my underwear and stuck a finger in me. I gasped and held his hand as he worked me. He then casually started to list out his demands. He wanted access to me 4 times a week, lunch, dinner, overnight or even an entire weekend. Sexually he wanted to explore my boundaries as he liked rough play "Don't worry I'm a gentle dom", verbal degradation, anal and he expected that I would swallow him even if he came in a condom. He continued fingering me and I was lost in the pleasure. My eyes were closed and I was just barely registering what he was saying.

"Choose a safe word also"

"A what?" he continued pleasuring me he now had two fingers in there. I still held his hand but was now encouraging him to move faster. I was getting close.

"A safe word ... so i know to stop if you're ever uncomfortable" he dug into me sensing I was getting there.

I muttered a most ridiculous of words but it was uncommon.

"That's my slut" and he kissed just as a wave of orgasm took over me. He continued kissing me through my orgasm, fingers still inside me but i held his hand more firmly to stop him from moving. My knees buckled and he made no effort to hold me up.

I was well and truly his slut after that. I had agreed to free use of my body for this condo. I felt worthless.

As I sat there recovering, he towered over me and began to undo his belt. He stopped and just starred at me with this look in his eyes. Eventually I took his pants and boxers off knowing what he wanted. His cock sprung out it was a decent 7 inches with the right amount of thickness to go with. I would like to say it was the biggest dick I had ever seen but it wasn't. It was the oldest though. It was still glorious.

I positioned myself on to my knees, grabbed the base of his shaft and parted my lips to take him in my mouth. I heard him moan. Now by this time I've had a lot of experience sucking dick and I had received several compliments. I worked my magic on his shaft taking about 4-5 inches of it in with every move. I kept a steady pace going. I maintained eye contact with him the whole time as if seeking his approval on how well I was servicing him. Eventually he removed my hand from his shaft and held them by his hip. "Take it all the way in" he demanded. I pulled out took a few breaths sucked on his balls licked up from the base to the tip and started to taking him all the way. I have no gag reflex and a lot of practice so he went in effortlessly. I held him there for a few seconds as I swallowed. "That's my slut" he moaned again clearly enjoying himself. I repeated again and again. Balls. Base to tip. deep throat. hold. swallow. release. My eyes had watered almost immediately and by the end of it tears were running down.

I lost track of how long this went on but I was his slut now. Well and truly. Droll dripping down my my chin and on to my dress.

He put his hands on the back of my neck eventually, which I took to mean he was getting close. I increased my pace, but focused on his head and without warning he began to cum in my mouth. I slowed down my pace and let him finish. It was a lot. And extremely sweet. I could barely keep it in my mouth though as he pulled out a considerable amount spilled out, i tried to save it but on to my dress it went.

He was standing, with his head tilted back recovering from his orgasm. I kept my mouth open for him to see as I gently stroked him. A small amount came out which I immediately licked in to my mouth. He eventually looked down at me and told me to swallow it.

I closed my my mouth, swallowed, opened to show him it was gone.

"Good slut..." he said as he gently slapped my face. He knelt down, grabbed my hair "...you enjoyed that didn't you? Admit it"

I looked at him for a while and yes I well and truly had enjoyed that. I had had sex with random guys before. I had even had sex with a few older guys but never he could be my dad old. The slut in me was truly satisfied.

He gave me the keys and told me I could move in whenever I wanted. He'd send over the paperwork for the lease with a nominal rent, which I could tell I pay if it ever came up. As he was leaving he told me he'd see me on Tuesday after work. I should be in the condo by 6PM and wearing a black business suit with a white shirt and high heels. If I didn't own one he'd send me the money to go buy it.

I spent an hour in the condo by myself and pleasured myself to the thoughts of what had happened, climaxed and went to pack.

In the elevator I texted him I didn't own a black business suit.

I ended up spending the entire 1st year in the condo as his free use slut. Things got hot and heavy real fast and I opened up sexually even more, especially to kink. I started referring to him as daddy and he never used my name when we were alone. I was his slut to be referred to as such. He was generous with his gifts to me and we wined and dined across the city.

[carleighhalla]

I want to fuck the DoorDash delivery guy

I have gotten free Doordash multiple times recently in exchange for showing off my body to my delivery guy.

I’m a college gal home for the summer (and COVID). Like many others, I’ve been using Doordash a lot both for safety and convenience. And also like most people, DD in my area leaves the food outside your door for contactless delivery. I’ve used it regularly since I’ve been home and it’s always been normal. That changed about a week and a half a go.

Due to the heat of the summer and because I like being comfy at home, I often hang out in large, flowy tshirts. I usually wear short track shorts or no pants at all, and I go barefoot. Last Monday I ordered food. When it was delivered I went out to the porch in this outfit, still barefoot, to get it. I took a quick glance in the bag as I was picking it up, when I heard a shout of “All good?”

I looked up. The yell had come from a Hispanic guy, probably in his mid-30’s, who was sitting in a car by my curb with the window rolled down. I live in a suburban area with a bunch of cars parked in the street so I hadn’t taken notice of one more.

“Are you the driver?” I called back. He nodded, so I made another check of the of food and gave him a thumbs up. He returned the gesture and drove off. It was a quick and innocent encounter and I didn’t think anything of it.

The very next day I ordered food again and one of my moms had asked me to check the mail while I was stepping out to get the food. It turned out to be the same driver, and he again waited to ask if things were good. I said yes, and began heading down my driveway to the mailbox while he got ready to drive off. Our pavement was boiling so I had to sort of skip/tip toe quickly to avoid burning my feet. As I made my way back to the house I heard him laughingly ask from his car, “Why aren’t you wearing shoes?”

“Too lazy!” I called back, laughing along with him, and he just waved and took off. Again, very innocent.

Things took a turn on Thursday. More food ordered, and when I went to get it I saw the same driver’s car parked but his window was up and he didn’t call out as he had before. There was a glare on his window from the sun so I couldn’t totally see if he was looking at me or just checking his phone for the next order. I went back inside and as I was unpacking my food, I found a sticky note with a handwritten note:

“Happy I can keep delivering to you.” And a phone number.

I thought it was a sweet bit of flirting, and though I knew nothing about the guy I didn’t see the harm in texting him to at least thank him for the note in case he was nervously wondering how his move would go. I shot him a text thanking him and also thanking him for always waiting to make sure my order was right. We spent a bit of time doing the usual introductory stuff. I told him my name and that I was in college. His name is Maxiano and he is 33, he’d just started dashing recently to make some extra money but mainly worked as a cook at a local Mexican restaurant. When he found out the age different he apologized and offered to leave me alone, but I told him I didn’t mind just chatting. I asked him why he’d left the note, and he admitted he thought I was very pretty. I was flattered, but I could tell there was more to it. He was the type of guy who, when texting, would say things like “I wanted to say more but I’m not sure” or “Can I ask you something?” ...”Nevermind”. Some guys do it to be coy or mysterious but I could tell Maxiano was just actually nervous and second guessing himself. After some gentle prompting, I finally got him to admit the truth:

“You have very pretty feet, and I have been staying to watch you get your orders to see your feet and legs.”

I know a lot of girls would be creeped out by an older delivery guy saying this to them. And yes, logically I probably should have been too. But I love exhibitionism and I also love feet, so this scenario was a literal fantasy of mine come true! I assured him that I was flattered and not put off by his confession, and told him I’d always be sure to get my orders barefoot whenever he was my dasher. The fact that I was into our little secret arrangement excited Maxiano a lot. He giddily explained how much he admired my feet and how he’d like to rub them and massage them, and I was living for it. We concluded our day of texting with a goodnight, and I was really excited by the new development.

On Saturday, Maxiano texted me in the afternoon to ask if I’d be getting food today since he was out on a shift. I told him I hadn’t planned on it. He offered to pick me something up for free. I did my best to insist against it, telling him I couldn’t accept that and he was out to make money, not spend it on me, but he was extremely stubborn and assured me about a hundred times that he wanted to do it to thank me for not being upset at his confession. The more this went on the better free food sounded, so I finally caved and agreed to let him grab me something cheap from a fast food place. He texted me when he arrived, and I knew I had to repay him somehow for his kindness. When I went out onto the porch this time, I took my time, milling about and lifting my feet to tap my toes on the tile and flash my soles at Maxiano in his car. I even sat on our porch swing, propping one foot up on my knee, and ate a few fries while waving at him. I could see him smiling in his car as he waved back before driving off.

Within minutes, my phone was blowing up with emojis and texts from him thanking me for showing off and complimenting my feet. He told me how sexy I was and that I’d even turned him on.

“Can I say something else?” He asked eventually.

“Sure!” I replied.

“You have a really sexy butt too” he told me.

As my username indicates, I have a nice ass and I’m proud of it, so I was thrilled to hear Maxiano compliment it!

“Thank you! Too bad you delivered on a day when I was wearing shorts. Sometimes I’m not”.

After about five minutes of stop-and-start typing, Maxiano finally said: “Would you ever get food on your porch like that?”

“Only for the right driver!b” I teased back.

“What do I need to do to be the right driver?”

“Keep complimenting me!”

I’d been joking of course, but Maxiano was clearly determined to get the show I’d teased because he lavished me with compliments and practically begged me to accept more food from him the next day so he could watch me again. I was totally down to continue our exhibitionist game, so I didn’t play hard-to-get for too long before agreeing. He had a later shift the next day so he’d bring the food by in the evening.

I had butterflies all day waiting for our little exchange. I had decided what to do to give Maxiano a fun show. When he said he’d dropped the food, I went out in shorts that barely came down to the hem of my long sleep shirt. It was dusk by now and our porch light was on, illuminating me like a spotlight, but I couldn’t see Maxiano through his car window. I knew he was watching though, and I also knew he was probably confused as to why I was wearing shorts after our agreement. I held up a finger to indicate to be patient, and proceeded to turn around and work off my shorts from under my shirt. I let them drop to my ankles, and playfully kicked them away, flaunting my feet as well for Max. I bent down to get the food, knowing that my shirt was pulling up enough to give him a taunting flash of my panty-clad cheeks. I straightened up and checked the food, then reached back and quickly tugged my shirt up to give him a brief, full-on view of my ass in cheeky undies. I then grabbed my shorts and scurried inside, my heart pounding with exhilaration.

Just as before, Maxiano blew up my phone almost instantly. First he just sent about twenty different emojis expressing his elation. Then came a stream of texts: “That was incredible” “So sexy” “I have you stuck in my head” You get the idea. Knowing Max enjoyed it as much as me was honestly a huge turn on. I went to my room and began to play with myself while we continued to text. Max kept thanking me for being a good sport, and said I was the sexiest girl he’d ever seen. As nice as his words were, I wanted to push him further. Though Max was obviously attracted to me, he kept his words very PG-13. He rarely cursed, and most of his texts were about wanting to pamper me and my feet, make me feel good, etc. He didn’t really talk about himself, but I knew he probably had some very dirty thoughts running through his mind. And I wanted to hear them.

“If I ask you something will you be honest with me?” I asked at one point.

“Yes always” he said.

“What did watching me make you want to do? You can tell me, whatever it is. I won’t be upset.”

This time a solid fifteen minutes passed before he answered. I’ll copy/paste his message here:

“To tell you the truth Carleigh you made me so turned on. Whenever I see you I feel so hot for you but tonight when I saw you take off your shorts for me and show me that big, beautiful butt I got so hard. 🙈 You are so perfect and have the sexy body that drives me wild’!! I wanted to see that big butt up close and feel it in my hands, feel how soft it is and make it jiggle right by my face. Does it jiggle Carleigh? I bet you would shake it so nice for me and let me touch it and kiss it. And then I would put your sexy sexy feet in my lap and rub them and feel them against me. I get so hard picturing your toes and feet in my lap. I want them on every part of me, loving them like they need it.”

Hearing Max talk dirty like this was making me super wet. I rubbed my clit feverishly, pausing to reply:

“I loved showing off for you. It made me feel so sexy and naughty to know you were watching. I’m glad I could put on a good show for you!”

We continued this back and forth, with Max saying much of the same type of things, until he sent: “I want to spread that big white ass and lick your ass and wet pussy and make you creamy for me”. Hearing Max use such naughty, vulgar language put me over the edge. I sank two fingers into my pussy and worked myself hard for a second until I came, waves of pleasure rolling through my body and down my limbs while I imagined Max’s eager face buried in my ass.

I responded by asking when we could do another show. Max wouldn’t have a shift until Thursday (yesterday), so we planned to do it again in the evening.

As the week crept by I’d get random texts from Max. They seemed to waver between asking how I was and other sweet things, and super dirty reminders of how he wanted to suck my toes and spread my cheeks to admire my asshole. It was clear that Max definitely had a thing for voyeurism and oral play. Though he was becoming more comfortable saying naughty things he still never mentioned actual fucking or anything like that. It was all about how he wanted to watch me, admire me, and worship me with his mouth. In a way this made our arrangement even hotter. It felt different and more forbidden, and it was driving me mad with delight and desire.

So yesterday finally came and Max delivered the food as normal. This time I exited with only a skimpy thong beneath my t-shirt. I started with the usual, showing off my feet and lifting my shirt so he could see my booty. Then I slipped off my thong as I’d done with my shorts before, leaving me naked under my shirt. I held up the tiny panties for him to see, then teasingly held them in my teeth while slowly pulling my shirt up once more. I gave him several seconds to admire my bare ass, then cupped my cheeks and jiggled them playfully before letting my shirt drop back down. I waved, blew Max a kiss in his car, and turning to the door I gave my ass a quick little slap before going back inside.

Max was overwhelmed with delight. I wanted to make sure he knew how much I liked making his day, so I asked him if he was home. He said he was and that his shift was over.

“Are you going to jerk off now? 😏” I asked.

The typing/stopping started, but I was impatient.

“Don’t be embarrassed. I want you to.”

The typing stopped. I could picture him pulling his cock out, stroking it after it had been aching all day, his eyes glued to my words on his phone screen.

“I want you to jerk off to my jiggly ass that you saw tonight, ok?”

The typing started again. “You have the nicest and fattest ass Carleigh baby. I wanted to touch myself all day thinking of you and then seeing you get naked for me. I’m rubbing it now.”

I kept encouraging him, weaving images of my soft soles working his dick in his lap and my booty bouncing for him, all the things I knew would drive him crazy. Sure enough, after just a few minutes he told me he’d finished, and that it had been of the best ones he could remember. He thanked me and fell asleep not long after.

Which brings us to now! What should I do next to entertain Maxiano?

[carleighhalla]

I wore a butt plug to dinner with my best friend

I hope everyone is enjoying my posts as much as I do! Here is Part 3 (final). 

Some of you might remember Jason from my story I posted about making him cum in his pants and taking his virginity. For those that didn't see it: one summer while home from college I began fucking one of my friends that I've always been a tease towards. This story takes place in August, about a month after the first time he fucked me. 

Jason's parents were rich, and always inviting me out to do things with them. They either thought Jason and I were together or wanted us to be, so I was always his "date" for fancy parties and dinners and stuff like that. This particular time, they were going to a really nice, set-menu French restaurant, the type that costs hundreds a person.

 I got ready for the night, curling my hair, doing my makeup, and picking jewelry. I picked out these matte black three and a half-inch heels, putting me a little taller than Jason with them on. I also found a bright red dress, as short as you can get away with at this kind of restaurant. It was flowy, but you could make out what my body's shaped like without too much imagination.

 As I got ready, I found a cute little Victoria's Secret thong that I hadn't worn for too long. It was pink and meshy, transparent all around, with some lace edges. While I stood at my underwear drawer, something from the back of the drawer caught my eye: a pink jewel buttplug. Without even thinking about it, I made a decision, sucked on it for a second, added enough lube, and stuck it in my tight little asshole. I slipped on the thong over it, snapped a quick pic for later, and got dressed.

 I showed up to Jason's parents' house, looking my best, and said hi to his mom and dad. Jason came down, and I immediately ran up and hugged him, making sure to press my breasts into his chest so he knew I wasn't wearing a bra. I took his hand in mine, and we all headed out to the car. They ordered an Uber Black and I arrived right on time. His parents got in the first row of a fancy SUV and the two of us got in the back row.

 They spent the drive talking to me about how college was going, but they didn't look back much. I told them about my classes and how I liked the area my school was in. Meanwhile, I moved Jason's hand onto my thigh. As I caught up with his parents, I slowly moved his hand up my thigh. "Stop," he whispered under his breath. “Don’t be a baby, Jason,” I whispered back. I let his fingers brush up against my pussy the slightest bit, then let go, giving him his hand back. My panties felt wet from the plug thrusting into me with every little bump on the drive.

 We got to the restaurant, sat down, talked for a while. With the softness of the booth, the plug actually felt comfier than I expected. Finally, they asked us about us. This was the first time they'd seen me act so flirty and touchy around Jason, so they must've figured we were dating. I made eyes at Jason and said, "Go on, tell them, baby." We weren't dating, but putting him on the spot was so fun. "We've started going on a few dates," he said, lying and blushing. All we'd been doing was fucking.

"Looks like you owe me a few dates," I texted him from under the table. "Not in front of my parents, please," he texted back. I replied, "Oh okay. Try your hardest not to picture my lips around the head of your cock." I turned back to his parents and kept chatting as he squirmed.

 After appetizers, I said that I needed to run to the restroom. I got up, setting my hand on his thigh as I did. I let the backs of my fingers graze against his hard cock through his dress pants. "I'll be right back baby," I said. I popped in the restroom and fixed my makeup and hair. I went into a stall and pulled out the plug to reapply some lube from my purse. Once I slipped it back in, I pulled down my dress halfway and licked my fingers and circled my nipples gently, until they both perked up, as hard as I could get them. I immediately headed back out.

 I came back to my seat, a little bit of an extra sway in my step, with my nipples clearly poking through the thin red fabric of my dress. I noticed both Jason and his dad staring at me, his dad stopping mid-sentence for a second before catching himself. I leaned in to Jason and whispered, "Aww, are you gonna cum in your panties again?” and kissed him on the cheek. Pretty soon after I sat, the main course arrived. I had drunk a few glasses of red wine in my already, and torturing Jason like this really turned me on.

 As we ate, we all fell silent, digging into the food. I subtly reached down and slipped off my heels. I ran my big toe all the way from Jason's foot up his calf and the inside of his knee, and then across his thigh as slowly as I could. I reached his cock, still hard, and rested my foot on it, feeling it throbbing. I sat across from him, and the tablecloth gave us plenty of cover, but it still felt like we were going to get caught any second.

 I stroked up and down, gingerly, across the whole length of him, clenching my toes around his shape a little bit. He felt bigger than the seven inches I was used to, and it was easy to feel his heartbeat. "How’s your food, baby?" I asked. He glared at me and squeaked out, "It's good," sounding out of breath. "Oh, are you okay?" I said. "Yeah, something down the wrong pipe a bit," he said, struggling for the words.

 I moved my other foot into his lap, using my toes to hold his cock in place while I stroked harder and faster with the first foot. My nails were painted red from a pedicure a few days ago, which I know drives him crazy. He let out a small moan, and I set my feet back down. He grabbed some water and caught his breath. Seeing him like this, combined with the sensation of the plug inside me, made me soaking wet.

 We finished up the meal and I decided it was time to ramp things up. I sent him the picture I took earlier of the jewel of the buttplug peeking out the side of my thong, along with a text, “Hope you aren’t getting too hard next to your parents.” He peeked at his phone, then his eyes shot up to me. They looked like big puppy-dog eyes, pleading with me to go easy on him. I made a show out of readjusting how I was sitting and bouncing up and down on my seat, staring him dead in the eye the whole time. His breathing got faster as he watched me.

 As his parents made small talk with me, I reached my hand under the table and rubbed my fingers around my pussy. They seemed clueless, as I told them about how my parents were doing and my plans for an apartment for next year, but Jason knew exactly what was happening. I was so horny, and it felt like electricity every time I touched my clit. The waiter walked up with desert, and so while everyone was distracted, I slipped my panties off, down to my feet, the wet seat right up against my toy and my pussy.

 As he took his first bite, I used my toes to drop my panties right in Jason's lap. I did it lightly, making sure not to touch him. I ate my souffle slowly, making sure Jason watched my lips. He reached down into his lap for his napkin and felt my panties. They were soaked all the way through, and his eyes flashed to me briefly. He fiddled around, presumably sticking them in his pocket.

 As everybody kept eating, I licked some chocolate off my finger and moved my hand to my lap. I ran my fingers in circles around my clit, and brushed my lips, growing fuller with each touch. I stuck my middle finger inside myself and eased it in and out, back and forth. I stuck in my pointer finger, rubbing up against the top wall of my pussy. I gently pressed my toy in deeper with my other fingers.

 After Jason took his last bite, I pulled my hand out and said, "Babe, you've got a little something on your upper lip." He wiped, "Did I get it?" "No, here," I said. I took my soaking wet fingers and lightly brushed them over his lip, right underneath his nose, letting him smell me right in front of his parents. "There, got it," I said, as he quickly wiped his mouth again.

 I slipped my shoes back on and we stood up. I made sure to leave my napkin on the seat, covering up the little wet spot I made. I made sure there was a slight sway in my step again. Jason's parents were pretty drunk by this point, and I'm sure they hadn't noticed anything, but Jason was still a nervous wreck. We got another Uber Black and headed back to his parents' house. I moved his hand up my skirt right when we got in, and guided his fingers to graze up against the base of my plug. He pulled his hand away and we sat there quietly, as I felt myself clench with every bump on the road.

 Once we got to his house, Jason had been sitting there stewing in his own horniness for a while. We stepped out of the car and I could see how hard he was through his thin little dress pants. I stepped in front of him, barely brushing my ass against his cock, and headed inside. We said goodnight to his parents and they went off to their bedroom to watch a movie, and we headed to Jason's room. The second the door closed, he turned to me.

 “Why would you do that?” he said. “I’m sorry,” I said softly, smirking a little, walking closer to him and laying my hand on his chest. “You aren’t!” he said. He looked so hot, as if maybe he was on the verge of crying. “It couldn’t have been that bad, Jason,” I said. “What if my parents figured out what you were doing?” he asked. “Umm, I wasn’t the one moaning at the table. Maybe you should learn to control yourself,” I said as I walked up to him and grabbed his cock through his pants.

 Jason stared at me for a while. “Just don’t do that again, okay?” “Fine, I’m sorry,” I said as I slipped my dress’s straps off of my shoulders. It billowed down to my feet, and I stood there naked in front of him. He looked my up and down, looking at my red toes, and the drops of wet dripping down my thick thighs. Looking at my little waist and my perky tits, nipples still hard. He looked me in the eyes, then gazed at my red lips and my brown hair bouncing down around my shoulders. “You forgive me, right?” I said. He nodded. “Good.”

 I walked up to him, grabbed his jaw, and kissed him, shoving my tongue into his mouth from the first kiss. I let my teeth catch on his bottom lip a few times, then moved down to his neck and started biting and sucking, giving him a hickey. I backed him up to the edge of his bed, pushing him down, and crawled on top of him, me completely naked, him fully clothed. I mounted him and bit at his ear before moving back to his mouth. I grinded my pussy up against him, then sat up.

 “You haven’t had a good look at it yet, have you?” I said. I turned around, put a knee on either side of his body, and backed my ass down right into his face. “Oh my god,” he muttered, inches away from the shiny pink jewel on the end of my plug. “I’m such a mess, clean me up,” I said. He started licking at my thighs, working his way to my pussy. Once he got there, I shoved myself down onto his face, riding his lips with my lips, letting his face press into my cheeks. As he thrust his tongue into me, I let my weight down onto his face, sitting on him. He grabbed my thighs and dug his nails in.

 “You like that? I bet so,” I said, “God, you’re just such a stupid little slut for me aren’t you?” I leaned forward, pressing my clit onto his tongue, and started undoing his pants. I licked at the tip of his cock, just teasing, while he ran his tongue in circles around the outside of my clit, swiping across every now and again. I wrapped my lips around the head of his cock, and swirled my tongue around for a second. As I came off for a second, my teeth light grazed him. He moaned, and I could feel the sound vibrating my pussy. “I love it when you moan into me.” I started sucking on him as he lapped at my vagina.

 I rolled over and moved up to kiss him. “How does my cunt taste, princess?” I asked, kissing him before he could answer. I moved a hand to his cock to keep teasing his head while we made out. I sat on him and let his cock press between my folds, not inside me yet, but rubbing up and down his length with the sleek area between my lips. I spun the plug around inside me to make sure the whole area was wet, then pulled it out. It felt so good to finally take it out, and I began to clench over and over, hard.

 I looked Jason in the eyes and brought the toy up to my lips. It was clean, so I gave it a little suck for show. “Do you wanna turn? I know you do. Be a good boy,” I said as I moved in towards him with it. He swallowed, looking hesitant. Right as he opened his mouth, I pulled back and set it on his nightstand, laughing. “Were you really going to suck on my buttplug for me? You’re such a nasty little whore,” I said, still giggling. I rolled back down and cuddled up next to him, “You know what I do want you to do? I want you fuck me in the ass. Do you think you can handle that? Not too scary?”

 My ass was still completely lubed up from last time I adjusted the plug. I laid down, face down ass up. He took off his pants and positioned himself behind me. He slipped inside my ass and thrust in deep. I gasped under my breath. It felt so good, but I grunted out, “Is that all you’ve got? Fuck me like a man.” This did something for Jason, and he dug his fingers into my sides, grabbing me and throwing me onto himself as hard as he could, hitting me in some deep spot that felt amazing.

 I had fucked myself in the ass with toys plenty of times, and always liked getting rimmed, but I had never actually let a guy into my ass. It felt too intimate for the slutty hookups I was used to. Jason didn’t know this, though, and it was fun not letting him know yet. I made sure that every time he got deep, I clenched hard and gently let go as he slid out, so it felt like I was sucking his dick with my ass.

 He pulled out of me and flipped me over. “Oooh look who’s in charge now. What a big boy,” I said. He slipped back inside me, pressing my legs into my body, curling me up into a little ball. It felt incredible, even though there was a little throbbing pain from it. I had never felt something quite like that before. Every time he would thrust in, a little moan would come out, getting louder and louder. “You have to stop, my parents are in the other room,” he said. “Make me,” I growled at him. I took a deep breath and started yelling, but before any sound could come out, he pressed his hand down over my lips and smothered me. “I can’t believe you’re making me do this,” he said. He kept fucking me, then began to move his hand off of my mouth. I got a millisecond into an ecstatic scream before his hand came down on me again.

 “You’re such a bitch,” he said, thrusting into me as hard as could. I moved a hand down to my pussy and fingered myself while he fucked my ass. I could tell he was getting close, so I started trilling my finger on my clit. I came through my whole body, clenching him, my legs shaking. I moaned under his hand, and I squirted all over both of us. I don’t usually squirt, but it happens occasionally, and the anal made me so sensitive. The second my squirt hit him, Jason groaned out, “I’m gonna cum,” letting go of my mouth. “Creampie my ass,” I demanded. He started cumming, with me squeezing down on him. He pulled out, a string of cum hanging off the tip of his cock. I leaned down and gave him one sensual suck of his cock, licking up all the cum on the tip, a little of it dripping down my lip.

 I cleaned up for a second, so did he, and we laid down together. I cuddled up with him. “I hope I didn’t go too hard on you,” I whispered. “I can take it,” he said, smiling. “You know I really like you, right?” I asked. “I like you, too,” he whispered back. “I have a confession,” I said, “This is actually my first time ever doing anal.” “How was it?” he asked. “You were amazing, I said. I gave him a few passionate kisses, then laid with him while we listened to music, running my fingers through his hair, and we fell asleep, still naked, lights on, for the night.

[carleighhalla]

I took my best friends virginity (part 2)

Hey everyone! Here is part 2, hope you enjoy! Take a look on my profile if you missed part 1.

"Because you're hot Jason. And I like watching you get all embarrassed. I like the way you look at me. And I think I wanna fuck you." He seemed dumbfounded. He didn't say anything for a while. "You wanna fuck me, right?" I asked, "'cause I'm saying I wanna fuck you." He just stared at me, as if he wasn't sure if this was real. I loved how confused he looked.

"I've never done that before," he said quietly after a while. I was surprised. I knew he was sort of innocent, but he's good looking and in college. “Wait, are you a virgin?" I asked. "I had never even seen a girl topless until tonight," he confessed, blushing again. I smiled. "Do you wanna kiss me for a bit?" "Okay," he said, "but I don't wanna be a sympathy case." "I promise you, I wouldn't do that,"

I leaned in close to him, closed my eyes, and grabbed his neck just behind his ear. I let him move in most of the way, and I gave him a long, passionate kiss. I kissed him again and again. Soon, I let my tongue lightly brush up against his bottom lip. He got the hint and started making out with me. He was following my lead, but he was a really good kisser. I could tell how passionate he was about me, and I felt my nipples get hard at the thought of how much he wanted me.

I moved his hands to my hips and kept making out. "Oh my god," he sighed. He felt around, working up the courage to move a hand onto my ass. He held my cheeks, but I had to move a hand down there and squeeze his hand to get him to really squeeze my ass. He began feeling me, grabbing a handful of my ass in each hand. "Harder," I whispered between kisses. I threw my head back, and he kissed and licked at my neck. He gave me a hickey, which I loved.

I let myself fall back onto the bed. He crawled over me and kept going at my neck. He worked his way down to my collarbone, so I untied the top string on my bikini. I could tell now that he was starting to get hard again. He kept working his way down my chest into my cleavage, so I pulled my bikini top off completely. "Oh you're so fucking hot, oh my god," he whispered, and sat up, grabbing my tits. They fit so perfectly in his hands as he gently squeezed and bounced them.

"God, use your mouth, Jason," I said, back to the teasing tone I'd been using with him all night. He kissed his way to my nipple and began flicking his tongue on it, sucking, nibbling at it. He kept muttering, "Oh my god," under his breath. He squeezed my other breast with his free hand. He looked up at me and said, "Your tits are so perfect. You’re the sexiest girl I've ever seen." It felt nice being with someone who really meant it when he said things like that.

I wrapped my legs around him and made out with him hard, biting at his lips a little and digging my nails into his back. He began grinding up against me, and I could feel how big his cock was right up against me. "You wanna lick my pussy, Jason?” I whispered in his ear. He barely whimpered out a little, "Yeah," and I spread my legs and looked him dead in the eyes. He crawled back a bit and shoved his face between my thighs. He started kissing around my inner thighs and licking right at the line on my little thong bikini. I could feel myself getting so wet.

"Take it off," I told him, "You think you can do that for me?” He peeled my bikini off of me and stared at my pussy for a little while, completely clean-shaven since I'd been in a bikini a lot lately. He crawled towards it, and I was so wet it looked like I had been oiled up or something. He said, "You smell so good," and made some big, slow licks up my whole pussy. He kept doing this, hands digging into my ass, pulling me into him, letting his tongue slide right between my lips. I was trying not to squirm as he worked his tongue in little circles around my clit.

He got more adventurous; I think he was doing the alphabet trick or something, but it was definitely working. I was really surprised since he said he had no experience, but he was so attentive. He clearly cared about my pleasure a lot. "You're so perfect," he said. I moaned and blurted out, "I want you to lick my asshole." He panted some and dove down, moving his tongue in little circles around my rim.

I moved my hips a little, really riding his tongue. I was getting wetter and wetter, I'm not sure if I had ever been this wet. "Oh my god, you've got me so hard," he said. "Show me," I shot back. He stood up and pulled off his swimsuit. His cock was probably about seven and a half or eight inches, and about average girth for that size. It was sticking up and had a teeny bit of precum dripping out of the tip. My jaw literally dropped. "Oh my god, Jason!" I laughed. He smiled, seeming slightly more confident, finally.

I got off the bed and got down on my knees and spit in my hand. I stroked him, making sure I got everything nice and wet. After a while, I pulled my hair back like I was going to make a ponytail and handed it to him. He grabbed my hair, and I wrapped my lips around his cock. "Oh fuck," he moaned. I made sure to lock eyes with him as I started sucking on him, bobbing my head up and down. Finally, I went all the way down to the base, letting him slide down my throat, and I kept looking him dead in the eyes. "You're so fucking hot," he whispered again. I held it there until my eyes were watering, and then pulled back, letting my spit pour out of my mouth and onto my tits.

I began stroking him with my hand again while I took his balls in my mouth, one at a time. I licked my way back up his shaft and put my lips on his cock again. I sucked on him, running my tongue on the underside of his head for a while, and then pulled back. I stood up, walked right up to him, wrapped my arms around him, and let my still wet pussy brush right up against his cock.

"You never answered me earlier. Do you wanna fuck me, Jason?" I batted my eyelashes at him. He grabbed me and shoved his tongue into my mouth, digging into my sides with his hands, and walking towards the bed. He pushed me down onto the bed and got on top of me. I spread my legs for him, and he grinded his cock on the outside of my pussy, letting the shaft ride between my lips. He panted and grunted, tossing his head back. He leaned down and said, "I don't have a condom." “I don’t care,” I said. I was on the pill and had been tested fairly recently. I knew he was a virgin, so I wasn't worried about him.

He gave me a long, passionate kiss, took the base of his cock in his hand, and moved to go inside me. He didn't have the best aim, but I'm pretty good at shifting around and helping guys get in. He slipped inside me fairly quickly; he felt even bigger than he looked. He closed his eyes and thrust back and forth really slowly, savoring it. "Tell me about it," I giggled, “Tell me how I feel.” "You're so warm. And it's so smooth," he said, "you feel so good." I leaned in for a passionate kiss, but instead bit into his lip, hard. He grabbed my shoulders, pumping into me harder and faster.

"How about you flip me over," I moaned. He pulled out and grabbed my arm, still kind of gently, and I got face down ass up for him. He slid back into me, and I moved too this time, bouncing my ass onto him while I shoved my face into the mattress. I let out a little whimper every time he thrust into me and hit me just right in that spot. "You have the most perfect ass I've ever seen," he said. I loved how much he seemed to worship me. "I know," I responded.

He stopped to catch his breath for a second, so I told him to get on his back. He laid down, and I got up on top of him and started riding him. I moved my hips in little circles while I moved up and down on his cock. He had his eyes closed and grabbed at the sheets. "You're so fucking big," I told him, "I love feeling your cock inside me." He looked like he was getting close, so I got off, leaving him on the edge.

I laid back down on my back, and I told him to fuck me as hard as he could. I held my thighs and put my feet up over his shoulders, letting him bend me in half. "I want you to hit it as deep as you can," I said. He began thrusting in, slamming away at me. I whispered, "How does my cunt feel, baby?"

"I'm about to cum," he groaned. This put me right on the edge too. "Cum inside me," I said, "I want you to fill me up. Do you wanna fill me up, baby? Do you wanna fill my pussy up with your cum?" He started cumming, holding himself deep inside me. I licked my finger and rubbed it back and forth on my clit. "Can you keep going for me?" I said. He did, and soon I felt my leg shaking. "Oh, I'm cumming for you!" I screamed. "Cum on me," he said. I came for probably about a minute while he moved back and forth gently. He pulled out and took a big breath.

"That was so amazing," he said, "oh my god, oh my god." I cuddled up against him for a while, kissed his cheek, and ran to the bathroom to clean up. We talked about how crazy it was we had never done this earlier. We both got dressed and headed back out to everybody. They didn't say anything, but I'm sure towards the end they could hear me moaning and shouting. We all finished the movie they had put on and people fell asleep on the couches and floor. I took Jason back to my bed and we fell asleep.

[carleighhalla]

I made my best friend cum in his pants

This is my first post, but hopefully not the last. Let me know if you like it or wanna hear more! It's a long story, but it has a lot of action, so don't worry.

A tiny bit of backstory, I've had this guy friend ever since middle school: Jason. He’s always been one of my closest friends; he's who I'd go to to complain and cry to a lot of the time. Everybody always said he was completely in love with me, and at first, I thought they just didn't get us. But it became pretty clear they were totally right. He was kind of all over me. And it's not even that I didn't think of him that way; he just never stepped up and made the move.

We went off to separate colleges, as did the rest of our high school friend group, but we'd still hang out all summer every summer. After my sophomore year at college, we were hanging out a lot at my place since my family had gone on a summer vacation, and I was home alone. This all happened when Jason and five other friends of ours (four girls and one guy) were all swimming at my place.

I wore this cute little plain, black thong swimsuit, really slutty. I bought it specifically because I knew my parents wouldn't be around. From the start of us swimming, I kept catching Jason looking at my ass. He didn't notice that I noticed, but he wasn't exactly being subtle.

Quick aside, so you have an idea of how I look: I'm about 5'5", brunette, shoulder-length hair at the time, small waist, a little on the skinny side, C cups, but some hips and a pretty big ass. Jason was kind of skinny, a little baby faced, but still good looking. He just had no confidence.

Anyway, I must have seen Jason staring at my ass at least a dozen times while we were swimming. One of our friends, Casey, suggested, "We should have a chicken fight!" So I, wanting to have some fun, immediately shouted, "I call Jason!" He went underwater and picked me up on his shoulders. I made sure to immediately move forward so he could feel my pussy pressing up against the back of his neck.

We had one round, and Casey beat me pretty easily, so I got back on and said, "Hold me further up on my thighs, it'll be sturdier." It wasn't sturdier at all, which I knew it wouldn't be, but I was having a lot of fun messing with Jason.

We had all been drinking, and as it turned to evening, we started feeling a little drunk. Eventually, we were all out of the pool and drying off. I was rapping along to some song playing on the speaker and jokingly twerked up on Sydney, another girl there. She grabbed my hips and grinded up on me, holding her beer up in the air with her other hand and wooing. So I bent over and tried throwing my ass back as well as I possibly could.

Jason and Danny, the other guy there, were both sitting and staring at me. They had been smoking a little bit of weed, but stopped smoking and were just staring, mouths open. I locked eyes with Jason and kept going for it. After a while, I turned around and danced facing Sydney, shaking my ass a bit more, really putting on a show.

I don't know why I was teasing Jason so much all of a sudden. I've always loved doing things like pulling my shirt down a little bit when he's not looking and calling him out for staring at my cleavage. Other stuff like that, but it’s just been little things. I've never really gone at it like this before. Maybe I had been too slutty at college and it was getting to me. Maybe he was finally starting to look a bit older and sexier. Maybe I was just feeling a little mean.

Anyway, cut to later that night. It was about eleven and we were all hanging out in my living room. We had ordered some pizza, ate, and were still drinking a fair amount. We played some games (we always end up playing games like Truth or Dare, Never Have I Ever, Paranoia, The Yellow Light Game, etc.). After some tamer rounds of things, we broke out a Jenga set I had made freshman year of college. It was a normal set that had either truths, dares, challenges, or requirements to drink written on each piece you pull out.

This was, surprisingly, the first time I had broken this game out with this group. I usually would bring it out with my sluttier, drunker college friends. We were drunk enough that we were all in the mood, though. A couple of fun things happened. Jason had to give Danny a little peck on the lips. I had to kiss Casey, but we let it turn into a full-on makeout for a second there. Kylie, another girl there, had to turn all the lights off, flash us, then turn the lights back on. Danny made out with Alison, the last girl there. Stuff like that. Mixed in with truths about our slutty encounters at college and a fair amount of drinks.

Anyway, things started taking a turn when I got a piece that said to take off an article of clothing. I was just in a bikini, so I asked, "how long does it have to be off for?" We all decided on thirty seconds. So I took my bikini top off, and people looked and giggled and it was actually pretty chill. Except Jason was straight up looking the other direction.

I teased him. "What's wrong Jason?" He said he wasn't sure what to do with his eyes. "Would it make it better if I told you to just stare for a bit, get a really good look?" I asked, giggling. So he turned his head back around and looked, almost locking his eyes on them. He blushed really bad and clearly got flustered. Something about fucking with him was really starting to turn me on. Kylie yelled, "Thirty!" and I put my top back on. We kept playing for a while and things got back to normal pretty quickly, for the most part. I could tell Jason was still a bit shook up. I kept shooting him looks.

I had some truths and drinks and next time I got a dare, it was to give one person playing a lap dance. So I obviously immediately mounted Jason. I turned up the Spotify playlist we had on in the background, and I started really grinding on him. I guess our thirty second rule was still probably in play, but I didn't time anything out; I just kept going for the whole song.

I moved my hips in circles for a while, putting my face up in his, letting my lips get really close to his, flipping my hair, and making eye contact the whole time. I let my tits brush up against his bare chest a little bit. After a while, I turned around and just bounced my ass right up against him, facing away, letting him really stare at it. The other girls were cheering me on; they were super drunk. Definitely more so than me and Jason, who were more like tipsy, really.

I turned back around after another thirty seconds or so and sat on him again. This time he was visibly nervous, and I realized it was because he was rock hard in nothing but a swimsuit. I should have stopped, but I grinded up against his cock. I let myself get carried away and tried to really stroke him with my ass, clenching and trying to squeeze on his cock a little. He breathed heavier, and I moved his hands onto my hips. The song was almost over, and so I leaned up to his ear and whispered, "I didn't know you were so big Jason" and giggled.

He moaned under his breath and suddenly went completely red. He pushed me off, stood up, and walked across the room to grab his clothes and his stuff, clearly really upset. He was still hard and had a big wet spot on his swimsuit now. It became clear that I had made him cum. “Oh my god!” I laughed. I was smiling pretty big but tried to hide it. The other girls stifled some giggles. I tried to say sorry, still smiling a bit, before he interrupted me, almost shouting, "No, you knew what you were doing! You've been fucking with me and laughing at me all night!" He grabbed his stuff and started trying to leave.

I stood up, trying not to smile, and said, "Jason, relax, I'm sorry. Why don't we go back to my room and talk." He agreed, and we left the rest of them out there to watch youtube videos and went to my room and closed the door. Once we closed my door, he sat on the bed. He looked like he was about to cry. "I don't get why you decided to pick on me today," he blurted out. "I wasn't picking on you," I said. "But you know I like you! I know you know I really like you! You're just torturing me and rubbing it in." I didn't know what to say. Finally, he just asked, "Why?"

"Because you're hot Jason. And I like watching you get all embarrassed. I like the way you look at me. And I think I wanna fuck you." He seemed dumbfounded. He didn't say anything for a while. "You wanna fuck me, right?" I asked, "'cause I'm saying I wanna fuck you." He just stared at me, as if he wasn't sure if this was real. I loved how confused he looked.

To be continued...

Let me know what you think so far!