[f/M/M] My very first threesome! | 2016

Note: This event was more or less planned out. The guy I'd been fucking at the time asked if I eventually wanted to have a threesome with he and his friend, Dan. I had never been in a threesome, and I was curious so I agreed. But for the longest time, it had only just been talk. What would I be willing to do? What would I be ok with? I asked questions as well. Would he tell his friend what I was comfortable with? Would his friend be ok playing by our rules? Yes, we made rules. Jack would be the only one allowed to physically hurt me. He knew what I could and could not handle. If I asked them to stop, they would stop and leave if I wanted. Or we would stop and take a break. Jack and I wound up talking about this for nearly a year. It got to the point that I didn't think it would actually happen and that it was just a fantasy that he got off to. I'm basically writing this little note to say that this event wasn't some random occurrence. It was kind of planned and talked about for a very long time so that by the time it happened, I had a fair idea of what would happen and that I would be completely safe and comfortable when it did happen. Basically, Jack put a lot of thought and effort into grooming me for this so that I wouldn't be a total akwo taco.

It all started one quiet Friday night when Jack, called and asked if I wanted to fuck him and his friend, Dan. I'd just gotten back from a volleyball game and was planning on spending the night watching movies after a long, hot shower. At first I was hesitant because I was really looking forward to a quiet night in, but that all changed when Jack mentioned that they wouldn't be around until much later. So I agreed. I mean, I'd never been in a threesome before, and Jack and I had talked about it a lot, so it wasn't like this was a total surprise. So why not?

"You sure you'll be ok with the two of us fucking you?" he asked.

"Yes, Jack," I said as I stripped down and wrapped myself in a towel and walked to my bathroom.

"Baby, you don't have to do this just for me. I want you to do this because you want to," he gently explained. My reflection in the mirror got a silly smile on her face when Jack called me "baby". The silly smile stayed as I turned away to start my shower.

"No no, I really want to. You know I want to. I promise I'll be fine." My skin was covered in goose flesh and I could see the steam rising out of the shower as I danced back and forth in my tiny bathroom in an effort to stay warm. "Listen, Jack, I'll be ok. I'm about to hop in the shower so I'm going to let you go, ok?"

"Wait," he called out as I was about to hang up.

"Yesssss?" I hissed back in the phone.

"I care about you. Yeah, doll?"

"Yeah, dude. Right back at ya."

"Ok. I'll text you later when we're on our way," he said and hung up.

Hours later I was curled up in my bed watching a second movie (Sweet Home Alabama, I believe) while I ate leftover stuffing that my roommate had randomly made us for dinner the night before. It was nearing midnight and I hadn't heard anything from Jack. I caught myself nodding off a few times towards the end of the movie, and decided to stop fighting it and go to sleep.

I got up and padded out to my entry way and left my key under a plant for Jack to find, locked the door behind me, and went back to bed. As I was snuggling under my blankets, I shot Jack a text message telling him where the key was and to come in quietly if he and his friend were still coming over.

Then I promptly passed out, hoping that I didn’t drool too much in my sleep.

Hours later Jack gently shook me awake.

"Rasp, it's time to wake up, doll."

I flipped my blankets up over my head and burrowed into the nest that I'd made. "Five more minutes," I demanded.

"Not exactly the willing slut you promised there, Jack-o," a deep voice laughed.

I stuck my hand out from under my blankets and waved, "Hi, I'm Raspberry. You must be Dan."

A calloused hand firmly gripped mine and shook it gently, "Hi Raspberry. Yes, I am Dan."

As I let go of his hand Jack pulled my blankets back until it was just me sitting in the middle of my bed. "You sure you need five more minutes?" he asked.

"Nope," I yawned and stretched.

"Good. Stand up and take those ridiculous pajamas off," he demanded. "You weirdo."

I scrambled out of bed and looked down at my Tickle Me Elmo boxers and sports bra that I'd had custom made with watermelons over the boobs. I stood in front of Jack and quickly pulled my bra over my head and tossed it somewhere in my room. Jack is all of 6 feet tall, with light brown hair, hazel eyes, and all around average build. He's a firefighter so he's well-muscled, but drinks way too much so he has quite the beer gut and is slowly going bald. I really like looking at his biceps.

As I started to slide my boxers off my hips, Dan grabbed me and turned me around. I let my boxers drop to the ground the same time that he leaned down and kissed me. His tongue was instantly in my mouth and it felt like the time that someone had dared me to eat a goldfish and it had flopped all over the place before I'd managed to swallow it.

As he pulled away, I really looked at him for the first time in the dim light of my nightlight. He was easily 6'3" or 6'4", blond haired, blue eyed, with broad shoulders and a very full beard. He reminded me of a Viking. Except he had a little bit of a beer belly and smelled like whiskey. I didn't get to study him for long before he was leaning back down and kissing me. This time I kept my mouth closed so his goldfish tongue couldn't try and choke me again. I moved my hands up to his face and ran my fingers through his beard as I slowly kissed him back. His hands came to rest on my hips and he pulled me closer, dragging my body up against his, and his lips started to follow mine.

I nearly jumped out of my skin when I felt a second set of hands squeeze my ass and lift me up onto my tiptoes. I'd never felt two sets of hands touch me like that before. Then Jack gently bit my shoulder before he slapped my ass.

The slap didn't hurt in the least so I broke away from kissing Dan to turn and face Jack and tell him that he hit like a bitch.

Immediately he reached around and crashed his hand into my ass. My room was filled with the cracking sound that his hand made slamming onto my butt. I gasped and bit my lip to keep from screaming in pain. Jack's hand grabbed where he slapped and he pulled me up against him.

"You sure I hit like a bitch?" he was squeezing tighter and I knew I'd have bruises later.

I nodded, "uh huh."

He laughed and kissed me and I happily kissed him back.

This time I didn't jump as much when I felt Dan's hands slide down my back before he started to kiss and suck my neck. He pressed his hips against mine and I slowly wiggled my butt back and forth against him. One of Jack's hands came up to squeeze one of my tits while one of Dan's hands slid in front of me to slide between my legs. I whimpered as he dipped one of his fingers inside of my pussy and slowly swirled it around. Once his finger was covered in my juices he slid it up to carefully circle my clit. I gasped into Jack's mouth and tangled my tongue with his as Dan started to twirl his finger around my clit. Soon I had my arms wrapped around Jack's shoulders as he kissed me and he was helping to hold me up as Dan teased me to the point that I was shaking and twitching.

I'm not sure when it happened, but Dan had stripped out of all of his clothes. As his finger continued to tease me, I felt his cock rubbing up and down my ass. I was getting close to orgasm and started to grind my ass against him. I could feel myself getting closer and closer to cumming. I couldn't help moaning and gasping against Jack's mouth while he continued to play with my tits.

"You're so wet, honey," Dan whispered against my ear. "I can feel your pussy juices soaking my hand and your legs. Do you like this? Do you like making out with Jack while another man fingers you? You're such a slut. You're going to cum all over my hand. Look at you. All that cunny juice lubing you up so you can get fucked like a bitch in heat."

Then he stopped. I wanted to scream in frustration as his hands gripped my hips and turned me around. As I spun around, Jack's hands forced me down onto my knees in front of Dan. Without a word Dan's cock was rubbing against my lips and I was opening my mouth to suck him deep. Immediately the thick head of his 6 inch cock was pressing the back of my tongue down and I was gagging and pulling away. My tongue swirled around the tip before I pushed him back into my mouth and forced myself to gag on him again. I looked up to meet his eyes as I wrapped my hand around his cock and started to move my mouth and hand up and down his length together.

Out of the corner of my I saw Jack undressing. As soon as he was naked he grabbed my free hand and wrapped it around his cock. He kept his hand over mine and started to move it back and forth over his soft cock, showing me how to jerk him off. I felt him slowly getting harder and harder in my hand as my mouth and other hand continued to work Dan's dick up and down. I stumbled a lot working with the two dicks because it was kind of like patting your head and rubbing your tummy at the same time. You can totally do it, but you have to think about it a bit while you're at it, and it's easy to lose track of what you're doing. More than once I would stop working Jack's cock and just hold it in my hand while I sucked Dan off, or I would stop using my mouth on Dan while I jerked Jack off. A couple times I got confused about which hand was doing which and accidentally hit myself in the face.

After a few fumbling minutes like that, Jack pulled me up off the ground and pushed me into my bed. Dan grabbed me and positioned me on my back while Jack moved to kneel beside my head. Right away I was leaning up on my elbows to wrap my lips around Jack's gorgeous 7 inch dick moments before Dan shoved himself balls deep inside of me. Jack's hands slid into my hair and he held my head in place as he started to pump his cock in and out of my mouth. He wouldn't push himself all of the way in, but would stop every time he felt me gag. I'd puked on him once before so he was always really careful when he used my mouth. With Dan pounding into me from the top and Jack using my mouth as his fuck hole, all I could do was lay there and let them both do what they wanted.

Once again, Dan started to work my clit with one of his fingers. Then he shifted so his thumb was rubbing circles around my sensitive little nub while he fucked me. Jack groaned as I whimpered and moaned around his cock. My tongue and tongue stud dragging back and forth along the underside of his dick as he fucked my mouth. Before I knew it, I was cumming. My entire body spasmed and my pussy shivered all around Dan as he kept pounding himself inside of me. He didn't stop rubbing my clit and soon I was screaming around Jack's cock again as my body convulsed and shook. I felt like the back of my skull had exploded, and pure sunlight and rainbows were shooting out my fingertips. I could feel my pussy juices dripping down my ass and pooling beneath me on my bedsheets.

Before I could recover from my orgasms, Jack and Dan were moving and shifting me into a new position on my hands and knees. Jack moved to kneel behind me and Dan moved to kneel by my head.

Jack's hand crashed down on the same spot he'd slapped earlier and I screamed as he grabbed onto my sore ass and squeezed tightly while he shoved himself inside of me. He was longer and thicker than Dan and I gasped at the small twinge of pain I felt. He'd pushed too deep and it had hurt. I tried to wiggle away, but was stopped when he grabbed both my shoulders in his hands and pulled me back onto his cock again. Another twinge of pain. He was pushing too deep, too fast, but my sopping wet pussy let him easily shove himself inside of me again and again. Each time I felt a small pangs of pain. He didn't stop hammering into me as I whimpered in pain and told me what a good fuck puppet I was.

At that point Dan tilted my head up and slid the head of his cock over my lips. I obediently opened. Every time Jack would slam himself into me, I would bounce forward and my mouth would slide down on Dan's cock. Dan carefully wrapped one of his hands around my throat, not squeezing, just holding, and forced me to look up at him. He didn't move at all. The both of us let Jack's fucking bounce my mouth up and down on his cock.

My eyes started to water from the pain I was feeling every time Jack shoved himself too deep inside of me. I could feel the tears getting ready to leak down my cheeks. Dan never let go of my throat and he made me look up at him as he and his friend fucked me. He watched as I started to cry with my mouth filled with his cock. He watched as I whimpered and screamed around his length. He watched as my third orgasm started to build.

Dan called me a kinky bitch once he saw that I was going to cum. He told me I was a dirty slut that needed to be degraded to get off. His hand tightened around my throat and I couldn't breathe. No air. I was gasping, trying to get air around his dick and Jack was brutally pounding himself into me over and over again. Dan told me I was a dumb whore for being able to get off on being used like I was. I came as he called me a nasty girl for liking pain and slapped my face. All I could do was moan and gasp around his dick as my body tensed up and then convulsed uncontrollably. He never let go of my throat as my body continued to jerk. All of my muscles were spasming and shaking. The last of any air I had in my body got wasted on my screams as I came.

And then I passed out.

I don't know how long I was out, but I woke with Jack leaning over me, asking if I could hear him. I opened my eyes and smiled weakly. I was still having a hard time breathing so I asked for my inhaler and Dan quickly grabbed it off my desk and passed it to me. Jack helped me sit up and take a couple of hits before letting me lean against him while I took slow and deep breaths.

Once I was breathing normally I wiggled my shoulders back against Jack's chest and asked if that was it.

He said no, and tipped my head back so he could kiss me. He reached around to gently toy with my nipples and Dan moved between my legs so he could push himself into me. Slowly he started to fuck me as I made out with Jack. My moans of pleasure were all the encouragement he needed and he carefully picked up his pace until he were both gasping and he was hammering into me. Once again he started to use his thumb to work my clit and before I knew it, I was cumming. Then I was cumming again, and again. Jacks mouth never left mine as I screamed, gasped, and moaned my way through each orgasm.

I was limp from so many orgasms that I didn't have the energy to move when Jack started to chant that he was going to cum. I felt like a used, wet rag as both his hands grabbed my hips and he started to drill into my faster. He was pumping short, quick strokes into me as he repeated that he was going to cum. He asked me where I wanted it, but I couldn't think.

In the end Jack's mouth left mine and he told his friend to pull out.

With a shout, Dan pulled out of my pussy and shot his load up my stomach and chest, and event to my face! Jack joked about how Dan was a squirter. He seemed kind of proud of how far his friend's cum had shot up my body.

As soon as Dan had squeezed the last drops of his cum out on top of my clit, Jack flipped me onto my stomach and pulled my ass up so he could push himself inside of me. Dan got up and disappeared into my kitchen while Jack slowly started to saw himself in and out of me. His pace never changed. Even when I begged him to fuck me harder, he didn't. He kept up the same slow pace. Each stroke was short and slow. When I tried to push back against him to make him go faster, he grabbed my hips and made me hold still. It was agonizing and I called him all kinds of mean names while cursing him to every Hell I knew. I just needed him to fuck me faster because I could feel another orgasm slowly building. The pressure started in my stomach. A tightening of my abdominal muscles and butterflies in my tummy. Then slowly the tension built throughout all of my limbs until my spine was tingling and I felt like there was an unbearable pressure sitting at the base of my skull.

Then there was a new pressure.

Jack's thumb was pushing into my ass.

Up until then I'd refused to have anal sex, but that never stopped him from playing with my ass. He'd never actually pushed a finger inside of me though. Or at least he hadn't until that night.

It hurt, but it hurt in the best of ways. It also hurt in all the wrong ways. Then carefully he matched his thumbs movements with his thrusts. Every time he'd push into me, his thumb would push into my ass. He kept up the same slow pace and my orgasm continued to build. He told me that I was going to cum with his thumb in my ass. He said he was going to fill my cunt up with his sperm while he played with my tight little rosebud. I laughed when he called it a rosebud, but stopped when he pushed his thumb in as deep as it could go.

Jack kept the same pace up and my orgasm kept building. I'd never felt as degraded as I did with his thumb in my ass. He kept telling me about how some day it would be his cock fucking my last virgin hole and how I was going to cum while he did it. I'd never actually felt dirty doing something sexual before, but that time, I definitely felt dirty. Over and over he told me how I was going to be his anal cum slut. The entire time his thick length continued to work itself in and out of my dripping pussy.

He told me to cum for him. I didn't want to. It just felt gross and wrong and…dirty.

I tried to hold on, but then he sunk his thumb deep into my ass and shoved himself balls deep inside of me. I couldn't help it. It hurt. It felt good. I was confused. I was disgusted. I was cumming. This time I came quietly with soft whimpers and gasps as my body crumbled onto my bed because I couldn’t hold myself up anymore. At the same time, I felt Jack's cum shooting deep inside of me. I could actually feel his cock pulsing load after load into me as he collapsed on top of me. We stayed like that for long minutes. I was too exhausted to move and he seemed content to leave his softening cock inside of me.

Eventually Dan came back into my room with sandwiches and a couple bottles of Gatorade that he'd found. He proudly declared he'd only used the stuff on the shelf with my name on it while he rolled Jack off of me and gave me a bottle of Gatorade to sip on. Jack got up and plugged Finding Nemo into my laptop and we all sprawled out on my bed to eat and watch the movie. I'm not sure when they left, but I know they both kissed me good night before leaving me to zonk out under a pile of my blankets and pillows.