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Deepthroating for the first time [M20s/F20s/NB20s] [First time] [Deepthroat] [Masturbation] [Threesome] [Cum] [Messy] [Uncut]
Author Summary
Decent_Interest5543 is in uncut
Post Body

Elle and I met at a mutual friend’s party a few years ago. We immediately hit it off and ended up talking for hours. Talking to her felt like talking to an old friend. Our conversation eventually led to us sharing some past sexual experiences, both good and bad. It turned out we had some shared sexual proclivities and we ultimately parted warmly, sharing a hug and each other’s phone numbers.

We started texting regularly and developed a really great friendship. Neither of us were ever really looking for a relationship, but we had an on-and-off friends with benefits arrangement and we stayed good friends otherwise.

I always shared as much as I felt comfortable with Elle about my other sexual experiences, and she did the same with me. Elle was pansexual and knew that I had always flirted with guys (particularly more femme ones), but she never really pushed me on why I hadn’t explored that inclination more.

She seemed like the perfect person to tell about something I had been obsessing over for weeks. It was a fantasy she couldn’t quite fulfill herself, since she was cis.

“I haven’t been able to stop thinking about deepthroating. I want a pretty femboy or a trans girl to shoot a load down my throat 😶.” I finally texted Elle one day.

“Um that sounds hot. Hang on.” Elle replied.

I had no idea what I was hanging on for, but I couldn’t stop staring at my phone for the next few minutes.

“What do you think?” Elle replied.

She had included an Instagram link. I opened it and it brought up the profile of someone named Max. I noticed that Elle followed them and that their profile mentioned they were non-binary. Max only had a few photos of themself from over the years, but they were really cute.

“They seem cool. And I guess they’re cute too…” I replied to Elle.

“Lol I know Max is cute. I think they might be into your idea. OK if I text them about it?”

I couldn’t believe how quickly this had happened. I could feel some precum soaking through boxer briefs already.

“Yeah!” I replied.

“If Max is cool with it, do you think I could watch?”

“Sure, maybe you can give me some pointers 😉”

“Lol I bet you’ve been practicing. You’ll do great.”

Elle was right. I had a small dildo I’d been testing my throat with every day for about a week. I couldn’t get the whole thing down my throat yet, but I’d pounded my throat with it while masturbating a few times already. Gagging on that dildo while I came gave me some of the strongest orgasms I’d ever had before. I couldn’t wait to hear what Max thought from Elle.

The next morning, Elle texted me.

“Max is into it”

“omg”

“Dinner at my place on Friday?”

“Yes”

I was in bed on Thursday when Elle texted me again.

“Max said they haven’t been able to stop thinking about fucking your virgin throat. And that you’re cute too.”

“🥺🥹”

I could barely type the last text to Elle before I pulled up Max’s Instagram and took out my dildo. I threw off my sheet, frantically pulled my boxer briefs off over my ankles, and started touching myself. I slid the dildo into my mouth while I looked at Max’s most recent photos, imagining it was them. After a few minutes of this my cock was rock hard and too sensitive to even touch, so I just lied there massaging my balls, not wanting to cum quite yet. I pushed the dildo deeper and met the resistance at the back of my throat. My cock was harder than it had ever been before, and drops of precum were leaking out and running down the head. I kept pushing the dildo, keeping firm and consistent pressure on it. Finally I felt it slide down my throat deeper than it ever had before, and I gagged.

I coughed and spit up all over myself, and immediately felt an orgasm coming.

“Fuuuuuuck!”

My cock was twitching in the air while I kept a tight grip on my balls with one hand and shoved the dildo back down my throat with the other. The first stream of cum hit the side of my face. I felt the hot liquid roll down my cheek, over my jaw, and onto the pillow. The second spurt was even stronger. It hit me under my eye and splattered. Some of it dripped down my face, over my upper lip, and into the corner of my mouth between my lips and the dildo. I could taste the saltiness as it coated the side of my tongue and dripped into my throat.

My body tightened with each shot of cum, and my chest and stomach were absolutely drenched. I finally caught my breath and pulled the dildo out of my mouth.

“Oh my God,” I barely whispered between breaths.

My body finally relaxed. I squeezed the last few drops of cum out onto my stomach. I lied there helpless for a few minutes, catching my breath. Eventually I cleaned myself up and texted Elle back.

“I haven’t been able to stop thinking about it either.”

“🍆🍆 me either! lol,” Elle replied.

“See you tomorrow ☺️. I can’t wait to meet Max!”

I fell asleep thinking about the next day, a little nervous but mostly excited.

Our dinner flew by. Elle cooked a delicious main course, and Max and I brought sides. We all split a bottle of wine, and we didn’t stop talking for the entire meal. Max was outgoing, confident, and just fun to talk to. After we finished eating, we did some light cleaning up, mostly in silence. All of us were probably thinking about what was going to happen next.

Elle opened another bottle of wine.

“Should we have a glass in the living room?”

“Sure,” I agreed.

Max just nodded quickly as if to say, “Of course.”

Elle filled our glasses and we walked slowly to the living room.

“That dinner was so good,” Max said on the way.

“I’m still a little hungry,” I said, smirking to myself.

After a second, Max and Elle giggled.

When we got to the living room, we all put our glasses down on the coffee table. We stood awkwardly, no one sure if they should sit down or if now was the time.

“So we should probably talk about it first, right?” Elle asked.

I chuckled a little.

“Deepthroat is no joke! I want to make sure you’re safe,” Max reassured me.

“I appreciate it.”

“So I’m not going to do anything or go any farther than you want me to. And if it’s ever too much, just tap the back of my thigh with your hand. I’ll never do anything or restrain you in a way that would keep you from tapping to tell me you need to stop. OK?”

“OK!” My voice cracked a little.

Now I just felt eager to get started.

Elle plopped down on the couch and started biting her lip and rubbing her thighs up and down with both hands. She was wearing a short, navy blue dress that rode up a little higher each time she bumped it with her hands.

“I’ll just be here!”

She seemed eager too.

My eyes darted to Max and we made eye contact. I quickly looked away.

They took a slow step toward me and gently took my hand in theirs, caressing my forearm with the other. We were about the same height, and I could feel their long hair brushing against my cheek and neck. They got closer and whispered to me.

“Is this what you want?”

Max placed my palm softly against the fabric of their pants.

I could feel their warmth through the fabric, and I could tell they were already getting hard. I nodded silently.

“Then why don’t you take it?” Max teased, and kissed me.

I kissed them back, pressing my lips hard into theirs. Our tongues found each other, and we took turns taking the lead, testing each other’s mouths. I bit Max’s lower lip, and they bit mine back. I smiled, and so did they, and our teeth clicked lightly together. We both pulled back, laughing softly.

I kissed their neck and eagerly unbuckled their belt with both hands. I squatted down, grabbed their waistband with both hands, and peeled down their tight jeans. They were wearing a cute pair of floral boxer briefs, and I could see a wet spot where some precum had soaked through. Their cock was harder than I had realized, and the head was straining against the stretchy fabric.

Max stepped their feet out of the jeans and kicked them to the side. I was frozen in my squatted position, staring at their cock straining to get out. They reached down with both hands and pulled down their boxer briefs. The elastic waistband slid slowly across the length of their cock. When it reached the head and slipped off, their cock sprang free. It bounced up and down a few times and settled pointing straight out from their body. I was in awe.

Max’s cock was definitely larger than the dildo I had been practicing with. It looked almost seven inches long to me. They were uncut, and I could see their foreskin sliding farther back and forth over their head as their cock grew. They were fully shaven too, which I loved. I couldn’t wait to feel how smooth and soft their sack was. I felt a tingle in my own balls while I was taking it all in. Out of the corner of my eye, I noticed Elle had her mouth slightly open, watching us intently and taking slow, deep breaths.

I fell to my knees from the crouched position I was already in and saw a drop of precum leaking out of Max’s cock. It looked even bigger now that it was right in front of my face. I took a deep breath. This was what I had been fantasizing about for weeks. I reached out with my tongue and tentatively tasted the drop of precum. It was a little salty and it made me hungry for more. I licked my lips, parted them, and slowly slid them around the head of Max’s cock and over their foreskin. I felt their cock twitch as it entered my mouth, and I tried to work up as much saliva as I could for lubrication.

I started moving my lips back and forth over the head and massaging their frenulum with my tongue. I felt their cock grow even bigger in my mouth and they started to rock their hips in sync with my movements.

“Mmmmmm,” Max groaned.

I giggled with their cock still in my mouth. I was glad they were enjoying what I was doing.

After a minute or two of this, Max was fully hard and the head of their cock was soaked in a mix of precum and my saliva. I let it pop out of my mouth and started to catch my breath. It was pointing up at almost a forty-five degree angle now, and I could tell they had wanted to push it farther into my mouth than I had taken it yet. It looked huge.

Elle slid off the couch and squatted beside me.

“Want some help?” she asked.

I just looked at her with wide eyes and nodded.

She put a hand on the back of my head and started massaging it.

“Mmm,” I moaned.

I liked having my head rubbed.

Elle tightened her hand around the back of my head and guided me back toward Max’s cock.

“Yes,” Max whispered.

“Make me take it,” I told Elle.

I could feel Elle smile as she pushed the back of my head. Max’s cock slid quickly through my mouth and met the resistance of my throat. Elle let me pull back a bit and then pushed me down again. She started to bob my head up and down on Max’s cock, slamming it over and over against the back of my throat. I could feel the saliva building up in my mouth and I was gagging a little with every push. Spit started leaking out of the corners of my mouth and I felt it running down my face and dripping into my lap.

Elle caught some with her free hand and reached under her dress to rub it over her bare lips and into her hole. I had been so focused on Max that I hadn’t noticed Elle had taken her panties off and hiked her dress up above her hips. I could hear how wet she was when she touched herself, and thinking about my spit mixing with her juices drove me crazy.

The harder Elle pushed me, the more my own cock grew. Max’s cock pushing into my throat was turning me on so much, and I was rock hard in no time. I knew they weren’t fully down my throat yet, but the anticipation and the feeling of their cock testing my limits was irresistible.

“Unnngghhh,” I groaned as I fumbled to unbuckle my belt and unzip my pants.

Elle reached down and helped me slide my pants and boxer briefs down to my knees, and my aching cock bounced free. I immediately got a hand around it and let out another deep, satisfied moan.

“Mmmnnnggg.”

“Ahhhhhh,” Max whimpered.

They must have felt the vibrations in my mouth because they pushed their hips into me and I could feel their cock pushing to go deeper.

I started stroking myself and massaging my aching balls. I was losing myself more and more in what was happening.

Elle took her hand off of my head but I kept on bobbing up and down on Max’s cock, slamming it into my throat. It felt so good.

Elle let out a breathy little sigh and slid back up onto the couch with a drunk, lustful look in her eyes. She slid her middle finger into her hole, and I could hear how wet she was as she started to fuck herself with it rhythmically, breathing in sync with each thrust.

I finally took a break and slid my mouth off of Max’s cock, slurping up as much spit as I could as pulled my head back. I spit it back onto Max and worked it up and down their shaft and over their balls with my hands.

I was absolutely overcome with lust.

“Put it all the way down. I wanna choke on it.”

Max smiled and slid both their hands over the top of my head. They guided my mouth back to their cock. I swallowed and parted my lips.

“Here you go,” Max offered.

They gripped the back of my head and pushed past my lips, over my tongue, and into my waiting throat. I could feel their head meet the resistance of my throat again, but this time they didn’t stop pushing. After a few seconds of firm pressure, my throat gave way and suddenly my face was pressed into the smooth skin above Max’s cock.

I could feel tears welling up in my eyes and my abdominal muscles tensing, trying to keep myself from gagging. I kept a hand on Max’s thigh, knowing I could tap out at any time.

My body tensed again and I gagged. I felt spit welling up in the back of my mouth. Max held me down firmly and I started stroking my cock furiously with my free hand. I gagged again and coughed up the spit that had been collecting in my mouth. It covered the base of Max’s cock and dripped down their tight sack, some of it landing in my lap and lubricating me. I was in heaven.

Max abruptly pushed my head back but stopped before their cock left my mouth. I gasped for air around their shaft.

“Is that what you wanted?” Max asked.

“Mmhmm,” I murmured and nodded with my mouth full.

“Oh-wee-it. Ewer-eh-ee-roat,” I tried to speak.

Max laughed and pushed my head back, letting their cock out of my mouth.

“Holy shit, you were in my throat!” I exclaimed. “Look what you did to me!” I gestured to my cock that was now standing straight at attention, dripping with precum and covered in the spit that I’d coughed up.

Max laughed again.

“Good boy. Now I’m gonna fuck your throat until I cum.”

I smiled with wide, begging eyes and nodded enthusiastically.

I glanced over at Elle. She had unzipped her dress and pulled the top down around her waist. Both of her feet were up on the couch with her legs spread, and she had two fingers inside of herself. Her other hand was massaging her bare chest and had stopped to play with one of her nipples. She stopped fucking herself for a moment when we made eye contact. She smiled and looked so proud of me. She started moving her hand in a circular motion with her fingers still deep inside of her. Her eyes closed and her head fell back.

“Mmmmmm, just don’t swallow Max’s load, OK? I’m gonna tell you what to do with it.”

Her head snapped back up and she looked at me for confirmation.

“Yes, ma’am,” I obeyed.

Elle smiled.

“And you,” she said to Max, “don’t force it all down his throat, OK?”

Max thought about it for a second and smiled.

“If you insist.”

“And don’t make yourself cum yet either. I want that,” Elle directed at me. She snuck a quick glance at my cock as she said it.

I nodded, excited to do whatever she told me.

I looked back at Max and we locked eyes. I smiled. Max licked their lips. They had a look on their face that told me they were singly focused now on one thing: using my throat to bring themself to orgasm. I couldn’t wait.

Max gently took my head in both of their hands again, and slid their glistening cock between my lips. They fucked my mouth slowly at first, sliding as much as they could in and out without entering my throat. Then they started testing my throat. With a few deeper strokes they pushed hard against me. I knew it was coming. On the next push they held me down, their cock pressing firmly into my throat. This time it slid in more easily, and again I had my face squished into Max’s body with a throatful of their glorious cock.

Max held me there, and I suppressed a couple of gags this time. I could feel the spit running from the back of my mouth down the length of their shaft and out of the corners of my mouth. It was soaking Max’s balls and dripping onto my legs.

I took my hand from Max’s thigh and cupped their balls with it. The skin was so tight; I could tell they were ready to explode. I started to massage them between my fingers.

“Uhhhhhhmmm,” Max moaned.

I started to massage my own balls with my other hand but I had to stop abruptly. I could barely touch myself at this point without feeling like I was going to cum.

Max finally released the pressure on my head and let their cock slide out of my throat. They kept the head in my mouth as I gasped for breath around it. A moment later, they slammed their entire length down my throat again and held me there. They repeated this over and over, holding me down for longer each time. I was suppressing gags and leaking drool all over both of us.

Max pushed me down so deep that my nose was flattened against them. It felt like they held me there for an eternity before I heard them groan.

“I’m gonna cum!”

They started fucking my throat with quick thrusts. Each time they entered my throat I could feel them growing. They pulled back so the head of their cock was just inside of my lips, and I felt the first spurt hit the back of my throat.

I suppressed a gag and was immediately intoxicated by the taste.

Spurt after spurt of hot cum hit the back of my mouth with unbelievable force. I couldn’t believe how much Max was cumming.

I moaned and squirmed, struggling to keep it all in and not swallow. They tensed up and let out a little high-pitched moan with each shot, until finally the deluge subsided. I felt their cock soften slightly and they slowly let it slip out of my lips.

I could feel the weight of Max’s load in my mouth, and I just stared at them with wide eyes.

“Oh my gosh, that was so good,” they said excitedly. “Good boy.”

“Oh my God,” Elle added, looking back and forth between my messy, twitching erection and the white liquid sloshing around my slightly open mouth. “Look at you.”

I tried to smile but stopped myself before anything could spill out of my mouth.

“I’m gonna make myself cum now. I want you to cover me when I say so, OK?” Elle asked, or more accurately commanded.

I nodded and tried to enunciate, “Yes, ma’am,” but I couldn’t get it out with my mouth full.

“And keep that load in your mouth,” she reminded me.

I nodded again as I stood up, my legs a little shaky. Elle slid off of the couch and onto the floor. She spread her feet wide with her knees bent and started rubbing her pussy lips with one hand while the other pinched one of her nipples, hard. I could finally get a good look at her in this position. She was soaking wet between her legs, and the one tuft of untrimmed hair he kept on her mound was matted down with a mix of my spit and Max’s precum.

My cock twitched as I took in the view. I felt controlled but so cared for by both of them.

Max put a hand on the small of my back and gently guided me so that I was standing right in front of Elle. They lightly wrapped their other hand around my shaft and slowly stroked up and down.

I whimpered in pleasure, but it was muffled by the mouthful of cum again.

“Fuck, you two are so hot. I knew this was a good idea,” Elle barely managed to get out between her quickened breaths. Her chest was flushed pink and it was rising and falling deeply now with each thrust of her fingers. Every time her palm slapped against her wet skin she exhaled quickly.

“Ahhhh,” Elle sighed and slapped the hand that was on her chest down on the blanket that was bunched up beside her, squeezing it hard.

She was close.

“Get ready……You’re gonna cum……and swallow……when I say so……OK?” she whispered between breaths.

I nodded.

I reached down quickly and grabbed Max’s wrist to stop them from stroking me too fast. I quickly shook my head. I didn’t want to cum before Elle was ready.

Max giggled, understanding, and started massaging my balls instead. They looked down at my erection and then back up to my face.

“Your cock is so fucking hard.”

Elle had three fingers curled inside of herself now, massaging her G-spot.

I was starting to struggle not to climax, even with nothing touching me except for Max’s fingers lightly circling my balls. I could feel an orgasm building and nothing was going to stop it.

“Swallow! Now!” Elle barely got out between her short breaths.

Max reached for my cock and started jerking me off again, lubricated by my precum and spit.

I closed my eyes and swallowed, and immediately climaxed.

“Fuuuuuuck!” I moaned, finally able to speak.

“Cum for us,” Max whispered in my ear as they pointed my cock directly at Elle and started making quick, short movements over the head.

The first rope of cum hit Elle in the face as she started quivering.

“I’m cumminnngggggg!” she screamed.

I couldn’t believe how intense my orgasm was. The second shot of cum splashed against Elle’s flushed chest, dripping down the curve of her small breast.

Her body convulsed in waves of pleasure as rope after rope of my hot cum splattered onto her. I was covering her face and chest with more semen than I’d ever produced before.

“Fuck yes,” Max whispered.

Elle pulled her knees close her chest and held them tightly together, shaking a little bit less now, but still experiencing diminishing climaxes as my hot cum rolled down her body and collected in the fabric of her bunched up dress.

My knees started to buckle. I thought about the aftertaste of Max’s cum and I dribbled a few more shots onto the floor before my orgasm was finally over.

“Thank you,” I said breathily to no one in particular, and fell into the crook of Max’s shoulder. They held me up.

Elle was curled up and lying on her side now, with her fingers still inside of herself. She whimpered as each smaller and smaller orgasm reverberated through her body.

Max giggled and Elle started to laugh too.

I could still barely stand up so Max helped me sit down next to Elle with my back against the couch.

Max offered me their hand that had been jerking me off. It had a few drops of cum on it that I happily licked up and swallowed.

“What about me?” Elle asked as she sat back up.

Max and I knelt on either side of her and carefully licked each bit of my cum from her face, neck, chest, and the folds of her dress over her stomach.

“Mmmmmm,” Elle sighed in satisfaction as we cleaned her with our tongues.

When we were done, Elle offered us the hand that had been inside of her and we took turns sucking as much of her cum from her fingers as we could. The slight musk of her fluids tasted divine.

“OK, I’m done,” said Elle.

I chuckled.

Max and I sat back on either side of Elle and rested our heads on her shoulders.

I reached an arm across both of them and squeezed us all together.

“Let’s do this again,” I said.

I felt them both quickly nod and murmur tiredly in agreement.

We all closed our eyes and enjoyed the warmth of each other’s bodies for a while.

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