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My First Three-Way: A Gay Man, a Stranger, and Multiple Orgasms


Most of us have fantasized about having a three-way at some point whether or not we want to admit it. There are all sorts of different gender combinations, but my first three-way was with two males. That’s many a girl’s ultimate fantasy, but mine was a little bit different – one of the men is gay and the other is straight.

I can’t quite remember how the idea surfaced or whose it was, but when I was 19 or 20 my gay friend Brandon and I decided we wanted to experiment with a three-way. None of our friends knew each other, so we had to find someone that only one of us knew. I struggled to think of someone it wouldn’t be awkward with, but he thought of a friend he figured would be interested. I have no idea how he possibly propositioned him, but it worked. I was immediately nervous, and all I was able to picture was 3 meerkats humping – but I was also extremely excited.

meerkats

My friend was house-sitting for his parents in their beautiful alpine cabin one weekend and we decided it was a perfect opportunity. While getting ready for the evening I scrubbed and shaved nearly everything I have; then hid some sexy, yet discrete lingerie under my clothing. I wore a skirt to allow easy access, so naturally I wore nylons and heels to go with it. To the average person I looked dressed for a business meeting, but it’s what I wore underneath that completely changed the tone of the outfit.

My thigh-highs were black and transparent showing my milky, white skin underneath; with a jet black seam all the way up the back of them. My skirt was leather so it was suggestive, but long enough down my thighs that it left something to the imagination. The thigh-highs were attached to a black lace garter belt with a matching lace bra and panties, with a light top that revealed my midriff.

skirt

I arrived a bit early so I could have a couple of drinks with Brandon to relax. I’d never had sex with him before, let alone be in a threesome, so I was pretty anxious. After a few shots in the kitchen, talking, and my friend kissing me, I felt a little more at ease.

When the mystery man showed up, we decided to hug instead of shake hands under the circumstances and all. The three of us enjoyed a couple of drinks together and listened to music until Brandon’s friend leaned over me and began kissing my neck. Signaling that it was time to do what we all came for, Brandon grabbed my hand and led us through the house and into his old bedroom. He dimmed the lights, lit a few candles, turned on some music, and I sat down on his bed.

The two men walked over and sat on either side of me on the king-sized bed. Brandon lightly kissed me while his friend touched my inner thigh and then my breast. They were both gorgeous and I was dying to see them naked; so I took Brandon’s t-shirt off, then his friend’s, and revealed two perfectly groomed and sculpted chests that I immediately wanted to devour.

They were both wearing light blue jeans, and one at a time I unbuttoned and unzipped them while they explored me. I kissed each of them as I released their penises from their zippers, then held one in each hand. I stroked their cocks simultaneously as we sat on the edge of the bed; each of them touching, kissing, or licking some part of me.

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Wanting to give them my body, I removed my top revealing my black, lace bra underneath. Brandon stood up and took his jeans and boxers off, then pushed me flat on my back and climbed up onto the bed. He straddled my chest and put his cock in my mouth while his friend got down on the floor between my legs.

Brandon pumped in and out of my mouth and I loved the feel of his thick cock on my tongue. His friend began kissing my legs making his way up to my inner thighs, and soon he was pushing my skirt up to my hips revealing my thigh highs and garter belt. Moaning his appreciation for my outfit, he caressed my inner thighs, pushed aside my panties, and playfully flicked his tongue at my labia. Intense house music blanketed the room and muffled our cries of pleasure. With Brandon’s cock down my throat and his friend’s face buried in my pussy, we all were in our own happy place.

After a while Brandon jumped off and the friend rose up from the floor, shimmied my skirt and panties off, and took the rest of his clothes off. He flipped me over onto my knees, then knelt on the bed behind me and caressed every curve of my tits, hips, and ass. I heard a condom being ripped open and my nipples hardened because I knew I was about to get fucked by a stranger. Brandon left the bed and walked to the corner of his room where he took a seat in his leather armchair to watch.

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Bent over and ready, I felt his cock nuzzle against my cunt as I squeezed Brandon’s comforter between my fingers in anticipation. I felt his hand move from my ass up my spine to grab a fistful of my long hair, and his engorged head began rubbing my clit rhythmically. Then with a shift of his hips he was inside of me and I gasped as he pushed in deeper.

He fucked me gently from behind; his thick cock spreading me wide open and brushing against my clit. Knowing that Brandon likes to watch, I glanced over at him in the corner and saw him jerking off watching his friend thrust inside of me. After a few minutes of doggy-style, he flipped me onto my side and penetrated me from behind with one arm wrapped around my waist.

I felt his broad chest against my back, and his free hand started exploring my breasts, then grazed down my stomach and rested on my pussy. With him grinding against me and gently fingering me, Brandon came to the edge of the bed and fucked my face.

I turned over and shoved the friend onto his backmmf2 to take control of his chiseled body. I mounted him, kissed his chest, and rode him like a cheap carnival ride. Brandon came up behind me, reached around, and fingered me as I fucked his friend. I was delighted to screw such a hearty cock, and when Brandon started circling my clit with his ring finger I completely lost control. Before I could try to stop it, an explosion erupted inside of me as an orgasm radiated out to my fingertips and toes; followed by my uninhibited screams.

When I had finished coming down, he slid out of me and they both knelt on the bed on either side of me to give my vagina a break. Sitting in between them, I pumped them both with each of my hands and massaged their balls. Then as I jerked one cock off, I’d suck the other; then alternate. No matter what I did I always had hands on me; on my tits, fingering me, on my ass, or running up and down my thigh highs.

To my surprise, Brandon pushed me onto my back on the bed and climbed on top of me. He grabbed a condom from the night stand, put it on, and leaned over to kiss me. His friend knelt beside me and as I began blowing him, Brandon slowly entered my pussy saying he’s “always wanted to try one of these.” He and his friend have similar gear, so I enjoyed being spread open and pumped. I slid my hand between us to finger my clit, and within minutes I was cumming again.

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The friend went over to a leather couch against the wall and sat down on it. We headed his way, then I knelt between his knees to service his cock once more. With my pussy and ass exposed and up in the air, Brandon couldn’t resist and proceeded to fuck me from behind while taking my bra off. After some time teasing and suckling the friend’s glistening, hard cock, he said he was close to cumming. I wanted him to experience the intensity of cumming inside of my tight pussy; so I flitted my tongue around his bulging head a few seconds longer, then slowly unraveled a condom down his shaft with my mouth.

Still leaning back on the couch, I mounted him, put my tits in his face, and he proceeded to suck on my nipples. I reached down and grabbed his cock, then guided it inside of me and lowered myself onto him. Brandon sat down on the couch next to us, so I stroked his cock and thumbed his asshole as I rode his friend.

Soon the friend grabbed my hips and slammed me down onto his thick cock over and over until his face scrunched up in pleasure and he shot his load inside of me. I slowed my hips down and my pussy squeezed every drop out of him; then I dismounted and sat between them for a minute to catch my breath.

Suddenly Brandon said, ” I really want to eat some pussy right now…”, so I mentioned I thought he was gay and he said, “I guess I’m not as gay as I thought!” He dropped to his knees in front of me, spread my legs open, and dove straight into my pussy with his tongue. He enthusiastically buried his face between my legs licking my clit and fingering me with a free hand. I ran my fingers through his golden waves of hair thinking I never would have known he hadn’t touched a pussy before.

Soon he stood up, scooped me up in his arms, then set me back on my knees on the couch facing the wall. He stood behind me, gently tugged on my hair, then slapped my ass. I felt my nipples perk up again as he pulled on my hips slamming my ass against his stiff dick. He fingered me for a minute as he caressed my ass, then pointed his cock inside me and thrust his hips forward.

doggy

As Brandon pounded me from behind, his friend leaned back against the arm of the couch and began stroking himself. He found it incredibly hot to watch us having sex, so I gripped the back of the couch and took the cock that was given to me. He stuffed me hard and deep making my tits bounce in the air for his friend to watch, and quickly I felt a third orgasm building.

Still thrusting himself inside of me, Brandon leaned forward pressing his hard body against mine and started kissing my shoulder blades. Not knowing that it’s my weak spot, he lightly bit my shoulder, licked a spot, then kissed it. My nipples were so hard that they almost hurt, and the waves of pleasure began forming between my legs again.

A cry escaped my lips and they knew I was about to cum. Brandon intensified his drive and forced his cock up against my g-spot sending me spiraling into climax. His friend leaned forward and inched closer to us; his thick phallus gleaming with pre-cum and getting choked by his own right hand. Without the use of any other stimulation, a thunderous orgasm rippled throughout my body; I screamed and moaned as Brandon kept pounding me, intensifying and stretching out my orgasm.

As I came, my vaginal walls contracted around his cock causing him to be thrown into orgasm with me. While we both shouted in ecstasy and he slammed inside of me, his friend pumped his own cock fervently and soon ejaculated his load onto us. His cum splattered across our arms, my tits, and Brandon’s chest simulating paint on canvas like some kind of incredibly hot, erotic, abstract art.

Once we all slowed down and caught our breath, Brandon pulled out, switched to some calmer music, and I sat between them on the couch finally taking my heels off. Brandon put his arm around me like he always did when we hung out and we all discussed our favorite highlights from the evening. After a while it had gotten pretty late, so we decided to part ways and I went home.

As I’ve mentioned before I tend to block out some memories, but this is definitely one I remember. The guys were hot, the sex was amazing, and the orgasms were plentiful. I don’t know about you, but I’m wet just remembering it.

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2 comments on “My First Three-Way: A Gay Man, a Stranger, and Multiple Orgasms

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