First Threesome (anal sex, bisex, first time)

JK's sex story
It was her first threesome and she was really nervous. Excited as Hell, but nervous nonetheless. Drinks had been flowing for a couple hours and I could see the flush on Jen’s face. I’m sure other parts were flushed too.



We’d been talking about including a plaything in our bedroom for some time. This was the first person we’d met. I’d lost the coin toss fair and square so this time we’d met a guy. Of course technically he was for both of us…

Steve was eyeing Jen like a lion looks at a Gazelle. I knew he wanted her badly. I knew I did too. It was time to take this to a more private location.

“Steve, I’m not sure I can get her upstairs on my own without getting mauled in the elevator. Care to accompany us so we don’t get arrested by the Hotel Security?”

“Sure, I think I can help. You take that hand, I’ll take this one.” We helped Jen to her feet and walked to the elevator. Her thighs swished softly in the black leather skirt. Steve had found out accidentally that she wasn’t wearing any panties early in the evening. He’d been waiting for us outside by the street and the curb was quite high. When we got out of the cab he got quite an eyeful. The amazed look on his face made the whole trip to Santa Fe worthwhile all by itself! After that he couldn’t take his eyes off her, undressing her with his mind. I knew what he was thinking and so did Jen.

I opened the door and we walked in to the Jacuzzi suite. All eyes fell on the tub. “I think I need to relax and unwind. Anyone care to join me,” I asked. The hotel staff had filled the tub and lit the candles for our arrival. It looked like a resort.

“Oh Jeff, this is so nice!” Jen exclaimed.

Steve put his arms around her and slowly undid the line of buttons down the middle of her back. I could see her shudder when he brushed her neck with his lips. She pulled his head up and kissed him slowly, deeply. She looked at me out of one eye to gauge my reaction. When she saw my encouragement she gave into her body and melted against him, clawing at his shirttails and belt buckle.

Steve shrugged off his shirt and Jen ran her fingernails across his muscular chest. He was young, muscular and very cute. She sure knew how to pick them! Now if only he wasn’t a two-pump chump in the sack…

Jen finally got his pants loose and slowly lowered them to the floor, running a trail of kisses down his smooth chest. His hands were in her hair, guiding her lips further and further south. We were both pleasantly surprised to see he was going commando. His huge erection stuck out the top of his pants and Jen ran her tongue along the sensitive underside, making him squirm. He stepped out of his pants and guided himself back into her warm waiting mouth. With time she was able to get almost the whole thing down her throat, letting him fuck her face with more and more force. I knew where this was going to end so I got in the tub and splashed them both hard. They about jumped out of their skin when the water hit them, having completely forgotten that I existed. Jen laughed and got in motioning Steve to sit on the other side of her. In no time she had an erection in each hand and teased us mercilessly. The hot water, bubbles and alcohol made her crazy with desire and she took turns sucking our tongues. Steve ran a hand between her knees and stroked between her thighs, working his way north. She parted her knees and when his hands brushed her freshly shaven lips she couldn’t take any more. Standing up in the tub, she grabbed Steve’s head and thrust her hot, throbbing pussy against his face, grinding his nose against her clit. She shrieked and came right then and there. After winding down a bit and regaining her composure, she got out and dried off, lying face down in the middle of the bed.

“That water sure made me tired. Why don’t we take a bit of a rest and then see what comes up?”

In seconds Steve was lying beside her. She rolled towards him and kissed him deeply again. Their bodies were pressed tightly together and soon he was thrusting his cock between her thighs, rubbing his length across her sopping slit. She ground herself against his shaft, her body begging him to enter her. He finally obliged, tilting his hips and placing his tip right against her opening. She grabbed his ass and pulled herself onto his length, groaning and gasping as he slid home.

I figured it was time to get in the pile so I quietly lay down behind Jen. Taking two fistfuls of hair in my hands, I pulled her head back towards me while inching up against her quivering body. Her slit and ass were soaking from her desire and I easily slid back and forth across her puckered asshole. I could feel my tip against the bottom of Steve’s shaft. Jen could feel cock against her from clit to the top of her ass cheeks. We worked up a rhythm, working over Jen’s body literally from stem to stern. I wrapped my hands around her waist and fondled her luscious breasts while Steve held her head in his hands, making her stare directly into his eyes.

She tilted her head back against my shoulder and whispered “I want you deep in my ass. Will you do that for me? Now?” Of course I would! She thrust her ass back away from Steve, letting me get a clear shot at her puckered hole. I rubbed the tip against her and worked an inch inside. Jen moaned hard on Steve’s tongue, then reached back and pulled more of me into her. Steve hadn’t quit thrusting and now I could feel his cock inside her, with just a few membranes between us. His tip rubbed against the bottom of my cock and the extra stimulation was almost more than I could handle! Within a few strokes I was balls-deep in her lovely ass with Steve pounding her from the front. I thought she was going to die from the pleasure. Her shrieks of pleasure made me certain the cops were going to show up to see who was getting killed in the room.

The pleasure was more than we could sustain for long. Steve quit thrusting. “I’m so close you guys! We have to stop for a minute or I’m going to be in trouble!”

Jen laughed and twisted her hips, sending Steve right to the edge. I was getting pretty close to the edge of the cliff myself. We thrust against her, pinning her between us so she couldn’t move. This also meant she had two huge cocks buried to the hilt in her lithe body. Steve twitched his cock, and I could feel it deep in her ass. I responded with a twitch of my own and the combination made Jen’s eyes roll back in her head. We traded twitches until Jen screamed through another orgasm. Finally it was too much and we started pounding in and out of her, reaching the edge and falling into a massive orgasm. I could feel Steve’s cock spew its load in her cunt and then I came – harder than I’d ever come in my life. My spasms seemed to never quit and I dumped load after load after into her tight ass.

Eventually we all stopped coming and lay there panting like we’d run a marathon, still entwined in one big knot on the bed.

“Ok, if that was foreplay, we’re both dead men,” Steve said, only half joking. With that everyone got in the tub and washed up. Jen soon had us back on the bed.

“So what do you want from us,” Steve asked Jen quietly.

“I have an idea!” And she looked at me with a devilish grin that I knew only too well. Usually when I saw that look there was a new toy involved and I was invariably asked to push my personal boundaries. My heart nearly stopped when I thought of the possibilities available to her tonight. I wasn’t wrong to be worried.

“Climb on board, my dear,” she said to me with a wicked wink. I did as I was told and sank my hardening meat into her wonderful body. I could tell she was motioning for Steve to do something but I wasn’t sure what it was until I felt his huge meat rubbing up and down the crack of my ass.

“Oh Jen, I’m not sure about this at all,” I complained.

She lay perfectly still for a second. “Do you remember all the times you’ve had my ass?”
“Well, yes.”
“And do you remember whose idea that was? And who had to convince who that it would be ok?”

I was seriously screwed. Or more accurately was about to be, literally.

“Um, he’s way bigger than I am. Doesn’t that count for something?”

“Yes, it means that I have instructed him to be very gentle.”

“OK, just please go slowly.”

Steve worked his tool up and down between my cheeks as I lay buried in Jen. I’d involuntarily twitch, which would send shivers through her. Steve was putting more and more pressure on the tip of his cock, slowly opening up my virgin rosebud. Then he lifted his hips off me and got lined up to thrust in earnest. Ever so slowly he applied pressure, allowing me to open up to his probing. Jen was twisting her hips under me and sending these wonderful shivers through my cock. My ass was way more sensitive than I expected and it was shooting sparks directly into my brain. Finally the head of his cock slipped in and I had to stop him for a minute.

“Hang on man, that is all I can take for right now,” I said breathlessly. It didn’t really hurt. Pain wasn’t the right word, but I was definitely feeling my ass resist any further advances.

“Ok, I’ll hold still. Tell me when you’re ok again.”

Jen grabbed my ass and pulled me into her deeply, pulling me off of Steve a bit. Then she pushed my hips up, burying Steve deeper into me. It just felt amazing so I let her do some more with my help. Soon I was banging back and forth between them and before I knew it I was taking almost all of Steve! He started groaning and I knew he was getting close. We all were.
“Go ahead, pound my virgin ass,” I hissed over my shoulder. He responded by thrusting in earnest, forcing me down into Jen as far as I could go. His thrusts were pounding my prostate and I knew I was going to come hard – and really soon. I started yelling that I was coming, Steve bellowed something, Jen was frantically screaming “YES!”.

She was the first to go over the edge and her sopping hole clamped down on my cock and shoved me over the edge. I started coming in waves. Steve thrust one last time and pinned me to Jen, unleashing a torrent of cum deep in my ass. I could feel his cock convulse and spew inside me. It was unlike anything I’d ever felt and was astounded it didn’t hurt.

It took a long time for us all to wind down and untangle. Showers were next on the agenda and we saved water by all getting in together.

Once Jen gets wound up she is simply insatiable and soon had both of us in her hands again, working us hard again. She dropped to her knees in the shower and took turns sucking us deeply. Her smoldering gaze locked onto mine and I was sure I was about to try something new.

“Why don’t you get down here and help me?” she said quietly. It wasn’t like I could say no, so I obliged, kneeling next to her in front of Steve. She slowly inhaled his meat while staring into my eyes, then pulled it out and pointed it towards me. I tentatively leaned over and opened my mouth. Steve grabbed my head and gently pushed his tip between my lips.

Funny, I’d thought about this before, but never had the courage to try it. So here I was, on the floor of a hotel bathroom with my girlfriend beside me, sucking another man’s cock that had just come deep in my girlfriend. And I loved it. It was warm, and alive, and smooth, and silky, and smelled of Jen. I took more in my mouth and ran my tongue under the head of his cock. He moaned and thrust deeper into my mouth. As he reached the back of my throat my eyes got wide and I gagged, pulling off his cock.

“Sorry, that was a bit much for a newbie,” Steve said apologetically “I’ll let you set the pace,” and he held perfectly still. I sucked his tip, teasing him with my tongue and eventually took more and more in my mouth. I wasn’t anywhere near as good as Jen but I did like it. I could feel him tense up when I got it right. His legs would go hard and his breathing would get ragged, just like Jen’s did when I was rolling her clit just right with my tongue.

Steve was getting close again and Jen pulled me off him. She kissed me deeply, her eyes telling me how much she was enjoying the evening. We kissed for a long time, enjoying the intimacy. We’d all but forgotten Steve until he smacked us both with his erection snapping us back to reality. Jen grabbed it and pushed it between our lips. We worked up and down in unison, making Steve crazy with desire. He grabbed the back of our heads and thrust between us, reaching the point of no return and blasting another huge load against the shower door. He sank to the floor, knees too weak to hold him upright.

Finally it was time for Steve to go. We said our goodbyes to Steve and then got back into bed. I kissed her gently and held her in my arms until dawn…
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