An Adventure with a Third

I woke up that morning more excited than I'd been in a long time. My boyfriend, Evan, and I were at a hotel in NYC. It was no luxury resort, but it was a splurge for our budgets: comfortable mattresses, breakfast that wasn't just stale cereal, and luggage carts. In a few hours, my best friend from high school, Kaitlyn, would be meeting us there for a weekend together. We hadn't seen each other in a couple years thanks to colleges being far apart and life being crazy. Don't worry, I'm not the kind of buzzkill that drags a boyfriend along to a girls' weekend. Evan was here for a very particular reason. For months, we'd been talking about having a threesome. We even had a group chat full of flirty texts and revealing pictures. It would be all of our first times doing something like this, so nerves were high, but it was nothing that dinner and a good amount of drinks couldn't solve.

Evan and I had gotten in the day before, which meant we had the hotel room all to ourselves. We'd made good use of it after we got home from dinner, me a little tipsy and him with his eyes glued to my dress. First we'd fucked on the bed, then he ate me out on the couch, and then we couldn't keep our hands off of each other in the shower. Still, eventually we got to sleep, and I'd spent the night dreaming of the fun we'd have with Kaitlyn.

Kaitlyn was built similarly to me, but our differences were enough to give us different appeals. She was a brunette where I was a blonde, she was toned and athletic while I was more curvy and soft, and she had a few inches on me. We both had medium-sized chests, hers slightly bigger, and our asses were hard to rival - I was very proud of mine, despite the fact that it wasn't earned by any exercise. I'd always found her beautiful, and she had been the reason I realized that I liked girls when we were still in middle school. There had been a tension between us for over a decade now, and we'd finally get to resolve it.

I turned my attention back to Evan, who was brushing his teeth in just his underwear and humming a song softly. In the dim sunlight coming through the curtains, all the contours of his body were highlighted blurrily. He was fit, even more so than Kaitlyn, but still had a relatively small frame. He had thin blonde hair that curled at its ends, only a few inches long. I walked up behind him and put my arms around his waist, laying my head against his upper back. He finished brushing his teeth and turned to me with a sleepy smile. With a kiss on the forehead, he scooped me up and carried me to the bed, tossing me gently onto the mattress. I laughed, but I felt the urge to moan at the mix of tenderness and roughness he always perfectly embodied. Evan crawled on top of me, kissing down my neck as he slid down my PJ shorts, which didn't cover much to begin with.

Now I was really moaning, feeling myself get wet under his touch. Once my shorts were off, he moved his mouth to mine and began to gently grind on me as we kissed passionately. My hands found his back and clawed at him. I wanted him closer - I wanted him inside me. I sat myself up enough to take off my shirt, and Evan was instantly at my bare chest as the top came off, licking one nipple and massaging the other between his fingers. The grinding had stopped, but I didn't mind; this pleasure was its own kind of wonderful.

I let him work on my nipples until the burning in my pussy became too much to handle. At that point, I pulled his face to mine and kissed him hard, pushing him backwards bit by bit until I was no longer beneath him. I stood up from the bed and motioned for Evan to do the same. I threw a pillow on the ground in front of his feet and knelt down. No way was I going to let him cum like this; he was going to finish inside me. But it didn't hurt to warm him up. The more kinds of pleasure I could give him in one session, the more speechless he'd be once it was over.

Evan took a sharp breath as I knelt down, realizing the spotlight of pleasure had moved to him. I pulled his underwear down, revealing his erection. I would normally start by stroking, but I could see he wasn't fully hard, and I wanted to feel him grow the rest of the way in my mouth. So instead, I kissed his thighs a few times and massaged his balls softly, then licked up his length before putting my lips around his tip and working down his cock. Evan grunted and grabbed my hair, leaning with his other hand on the bed for support. I now moved one hand to his cock, stroking quickly over the parts that weren't inside my mouth. I moved my head slowly, never fully releasing him from my mouth but occasionally letting just his tip rest between my lips. His breathing quickened and his hand pulled harder at my hair. I kept up the pace, not wanting to bring him to orgasm before I had my fun. When he began to thrust forward into my mouth, I knew it was time to have him fuck me. I pulled my mouth away from his cock, and his hand fell from my hair.

"Lay down, baby." Evan obeyed, laying calmly on the bed despite the hunger in his eyes. I crawled on the bed and a bit on top of him, reaching over to the other side of the bed where I had put the condoms. As I leaned over, I left my ass and pussy right in front of Evan, and I soon felt his fingers on my clit. Condom in my hand, my elbows gave out a bit under me, and my face was lying on the edge of the bed. Evan and I moaned in sync, and he slipped two fingers inside of me, moving them in and out slowly a few times. It felt amazing, and I laid there in a bit of a trance, forgetting my goal. Soon, he stopped, slapping my ass and pulling on my waist to bring me back over to him. I sat up and got the condom out of the wrapper, placing it on him with both hands. I felt him shudder at this, and I knew he was sensitive and would likely orgasm quickly. That was fine; I'd get action plenty of other times today, I was sure.

I placed my hips over him and grabbed his dick to line it up with my entrance. I was slick from my arousal, so he slipped inside me easily, and I began to ride him with slow, hard strokes. The sound of my ass hitting against his pelvis and thighs turned me on almost as much as feeling him inside me. The pleasure was unbelievable, just as it always was, getting better every time he fucked me. He grabbed my ass and moaned my name, eyes shut and head thrown back in pleasure. He looked so beautiful like that. I sped up a bit and felt him finish inside me, moaning as he did. I settled down on his dick one more time, grinding my clit on his pelvis to please myself and take advantage of his sensitivity. Eyes still closed, but more relaxed, Evan let out a couple more light moans. I pulled myself off of his dick and kissed him softly, causing his eyes to open.

"Clean yourself up for me. When you come back, we'll get even," I said with a smirk.

Evan went to the bathroom to clean up, and I laid myself against the pile of soft pillows, closing my eyes to bask in the way it felt to be with him. He walked back into the room, determination in his eyes, and leaned over me from the side of the bed. He placed his hand on the side of my face and kissed me, growing in intensity until I was moaning again.

"Touch me, please," I asked, pulling my mouth away. Evan smirked. He stepped into his underwear and motioned for me to move over, lying beside me. He turned to me, so I rolled on my side to face him as well. His hand landed on my waist, and he pulled me against his body to kiss me. I rested my hand on his face, leaning into the kiss with desperation, as his hand moved from my waist to the inside of my thigh. I instinctively parted my legs, lifting one up to give him access to my dripping wet pussy. His fingers darted to my clit, circling it slowly and building deep moans in my chest. When I let the first moan escape, he moved his mouth away from mine, kissing lightly down my neck. Everywhere he kissed, I felt a spark and titled my neck back a little more. Still circling my clit with his fingers, he began to circle my nipple with his tongue.

Before I could acclimate to the new source of pleasure, Evan's fingers stopped circling my clit and began moving back and forth in search of my entrance. His tongue still dancing over my nipple, he inserted two fingers inside of me. I squealed out a moan at the penetration. My pussy was still a bit sore from being fucked - not only this morning, but the night before - but I liked the way it served as a reminder of all the pleasure of the past. Evan's mouth became more insistent on my nipple, his fingers still working in and out of me slowly.

"Fuck, Evan, fuck me," I begged.

"You like that?" he asked, moving his face back to mine and pressing our bodies closer together.

"Yes, fuck, you feel so good." It felt even better thanks to how close our bodies were. His chest pressed to mine, his face inches away; the comfort and safety that the position exuded made it easier to let go and just feel. Going even farther, Evan used his semi-free hand to nudge my head into the crook of his neck and kissed the top of my head tenderly. I continued moaning, now muffled by his body. His fingers sped up inside of me, and the pleasure grew more intense, especially when his palm hit my clit while he thrust all the way inside. The pleasure was building, and I felt it about to hit the threshold of orgasm.

"Oh, Evan, I'm gonna cum, oh my God!"

My body tensed and relaxed at the same time in a paradox of pleasure, convulsing and moaning in a way I couldn't control. The pleasure filled every nook and cranny of my brain, and Evan's fingers weren't stopping. Finally, my body settled and I began to pant, catching up on the air that I'd missed. He removed his fingers and pulled his chest back a bit so I could look up at him, kissing me sweetly. We both went to the bathroom to clean off the sweat and other wetness on our bodies, and I stared at him in the mirror as we did, still dazed and a bit weak in the knees. He somehow looked even more beautiful than he had while he was brushing his teeth.

Now cleaned up and satisfied, we got dressed. Evan put on a pair of khakis and a t-shirt, his everyday uniform - he'd have to change into at least a polo for dinner. I threw on a long dress, still casual with a light fabric for the fall weather. It was a pale blue, loose below my waist but tight on my chest. I always felt pretty in it. While I was standing in front of the mirror doing my makeup, Evan walked up behind me and put his hands on my waist.

"You look beautiful," he said into my ear. Tingles went down my back, and I think I shivered a bit under his touch.

"Thank you, sweetheart. So do you," I answered, leaning against him a bit and continuing with my makeup. I loved the warmth of his body against mine, a constant reminder of our connection even as I went about mundane tasks.

"What do you want to do until Kaitlyn gets here?"

I thought for a moment before responding. We could lay in bed and fuck all day, but I wanted to save some energy for Kaitlyn. That also eliminated basically any plan that left us alone in the room for extended periods of time, because I wouldn't be able to keep my hands off of him. Maybe we could stroll around a shopping area, or we could sightsee a bit. With the weather as nice as it was, I wanted to take advantage of the outdoors.

"Let's be basic and go to Central Park! I love it there. If we get bored, we can find some shops to go to."

He kissed my cheek. "Sounds like a plan, my love."

After a decent continental breakfast, we headed to Central Park and walked around until lunch time. It was, as it had been every time we walked together in the past, magical to hold his hand and explore together with no destination. For lunch, we went to a cheap Italian place and laughed over a glass of white wine (I know, lunch is early to start drinking, but it was a vacation) and some sandwiches. The afternoon was spent dragging Evan behind me to a bunch of clothing stores where I talked myself out of all my purchases. Well, all my purchases except one - a black, backless dress. It was flowy and didn't hug my curves, but it was elegant and fun, so I got it anyway. Besides, Evan seemed to like it when I stepped out of the dressing room, judging by the glint in his eyes and lack of verbal response.

Finally, it hit 5:00, so we took a taxi back to our hotel to get ready for Kaitlyn's arrival. I poured myself a glass of wine from the bottle I'd brought with us. I didn't want to be drunk before Kaitlyn got here - that would come afterwards - but I wanted to be a bit open. Evan doesn't drink, but I had a way to calm his nerves too. Sipping on my wine and sitting on the edge of the bed, I watched as he stripped off his shirt, facing away from me and revealing the ripples of his shoulders and back. I felt myself start growing wet, thanks to the alcohol and the beautiful man in front of me. Evan turned his head over his shoulder to look at me.

"What shirt should I wear?" he asked me. "Polo or button-down?"

"Hmm," I responded, seeing an opening. "Bring the button down over here."

Evan looked a bit confused but did as I asked, walking up to me with a black button-down in his hand. I took one more sip of my wine and set the nearly-empty glass down on the bedside table. I took the shirt out of his hand and stood up, barely an inch from his chest. Before he could step back at all, I began to slide one of his sleeves onto his arm delicately, letting my fingers run across his bare skin as I did. Evan tensed under me and I felt his breathing quicken. Driving him crazy with horniness was sure to make the nerves irrelevant and help things run smoothly for him that night. Once that sleeve was pulled on, Evan's eyes were beginning to close from the tenderness with which I was touching him. I barely touched my lips to his neck a couple of times, and he moaned absentmindedly. With very little help from Evan, I pulled on his other sleeve in much the same way. As I buttoned up his shirt slowly, skipping the first few to leave a sneak peek of his body, I kissed down his chest with each button. I was beginning to worry that Evan would fall asleep standing up, judging from the way he was melting under my touch, so I twisted us around and laid him on the bed.

I knelt over him, leaning my face into his until I could feel his irregular breathing on my lips. I kissed him softly and began, much more slowly than was necessary, to tuck his shirt into his pants. Occasionally, I would let the tips of my fingers brush over his dick through his underwear. He twitched underneath me, a kind of lazy hardness pressing on the fabric. Once he was practically liquid under me and his shirt was all tucked in, I kissed him once more on the lips, briefly sliding my tongue into his mouth, before I got up and broke his haze by telling him to keep getting ready.

His eyes fluttered open and he groaned in frustration before pushing himself up and off of the bed. I walked over to the mirror to start changing, and he squeezed my ass desperately as he walked up behind me.

"I want you so badly, I'll bend you over right here and fuck you."

I turned to face him, but his hand didn't leave my ass, and he then used that leverage to press his erection into my pelvis. I was undeniably turned on, but I knew the tension could be put to better use later, so I took a second to collect myself and responded.

"Baby," I said, placing my hand on his chest and pushing to create a bit of space between us. "Save this desperation for Kaitlyn and I tonight. I want your everything. I want her to see your passion."

He moaned and tilted his head back a bit just at the thought, agreeing to wait despite how much he was clearly struggling to restrain himself. I watched his eyes follow me as I stripped and changed into my dress and black tights for dinner. It was the kind of dress that a bra simply wouldn't work with, and I was amazed that Evan kept his hands to himself when I let my bra drop to the floor before pulling the black fabric over my chest. As I did my makeup and he touched up his shaving, the tension became less intense, but it remained - precisely what I wanted.

A few minutes before 6:00, Kaitlyn texted me that she'd be at the restaurant in 30 minutes. I relayed the message to Evan and asked if he was ready to go. After a few light splashes of aftershave, he slipped on his shoes and met me at the door. I'd put on my only fun shoes, some black strappy heels that made me almost as tall as him. Looking at him all dressed up, and smelling the aftershave on him, made me worried that I'd sabotage my own plan by getting on my knees right then. Seeing the look in my eyes, and their laser focus on his crotch, Evan chuckled.

"You can suck my dick later, beautiful. Let's get to dinner for now." He opened the door and gestured for me to walk into the hallway ahead of him. I obliged and we walked to the front of the hotel to catch a taxi to the restaurant, which was admittedly not far, but my legs were tired and heels never quite agreed with me. On the drive over, my leg began to bounce up and down, and I wished I'd had another glass of wine. Evan, noticing my nerves, set his hand firmly on my upper thigh and squeezed to bring me back to the moment. I glanced over and smiled appreciatively.

When we arrived at the restaurant, it was only 6:20. The restaurant was nothing crazy, but slightly fancier than we'd usually go, as was the theme this weekend. It was very popular for its mixed drinks, and we'd made the reservation well in advance to make sure we got a chance to try it out. In the time before Kaitlyn's taxi would arrive, Evan and I got us seated at our table for three. The table was in the back corner, dimly lit and away from the noise of both the kitchen and front door. I sat across from Evan, leaving the seat beside me for Kaitlyn. After a minute or two of idle commentary on the restaurant's decor, and a lot of leg bouncing, I caught sight of Kaitlyn walking in the front door. As her eyes caught mine, I waved her over, attempting to look calm despite the rush of adrenaline surging through me.

Kaitlyn began to walk over to us quickly, and I stood up to hug her as she reached us. Our hug lasted several seconds, her toned arms squeezing my chest tightly. She smelled delicately floral, adding to the elegance conveyed by her knee-length, skin-tight black dress with a high neckline. Her body was on full display through the fabric, and I saw Evan working to hide his stare as much as I was. After Kaitlyn had her fill of hugging me, she walked to Evan to hug him in greeting as well. Evan was clearly a bit startled, standing up hurriedly to meet her. Their hug didn't last nearly as long, but I could tell it added to the desperation I'd been encouraging in him tonight.

Kaitlyn returned to the seat beside me that I'd saved for her. The conversation began with urgent pleasantries, catching up on all the gossip we'd missed. I glanced over at Evan occasionally, worried he'd feel left out, but he seemed quite at ease just listening to our conversation. When the waitress came over, I ordered a specialty drink off the menu at random. I was not very adventurous in my day-to-day, but I was about to have sex with my best friend, so what was a little risk that the alcohol wouldn't be to my taste? Dinner flew by, the time blurred by another few drinks. We ate good food and laughed incessantly. As the night began to dawn, I felt Kaitlyn's hand touching my shoulder more and more often. In one laughing fit, I failed to fight the urge to rest my hand briefly on her upper thigh. I felt her tense under my touch, but in a second my hand was gone and we acted like nothing happened.

Evan bit his lip as he watched that, which I caught sight of out of the corner of my eye. Seeing our boldness and slight drunkenness made him bolder too. He began to make flirtatious comments, first to me, then to Kaitlyn. He reached his hand under the table to run his fingers over my thigh, making my panties wet almost instantly despite the relative chasteness of the touch. I excused myself to the bathroom, keeping my balance with a great deal of effort. Once there, I looked around to ensure I was alone, then continued my adventurous streak by lifting my dress to expose my breasts and panties. I took a picture in the mirror and sent it to Evan, knowing it would break any restraint left in his body.