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A Night for Firsts

Category: Group Sex
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“So, come on, tell me!”

Jessica looked up at me, smiling, her head resting on the pillow next to me as we lay in bed, our naked bodies still glistening with sweat. Her left wrist resting on my chest, her thin fingers tracing tiny circles as I breathed heavily, having just had an orgasm a few minutes previously.

“I just want to make sure you’re totally satisfied. I want to be the best you’ve ever had, but I just feel that you’ve had all this experience compared to me,” she said, trying to tease a confession out of me. Jessica was a few years younger than I was, twenty-two years old with long reddish-blond hair and green eyes; soft, pale skin; and lots of freckles. She was alluding to the fact that I had a series of girlfriends before her, some of whom she knew through our mutual friends.

“Are you kidding?” I asked her, as I rolled over onto my left side to face her. I gestured to the little puddles of cum that were still warm on her belly. “I’m obviously very satisfied. You are the best I’ve ever had. Seriously. You’re incredible.” It was true; I had never been with a girl who was so sexually open and enthusiastic, and I told her that.

She grinned, closed her eyes for a moment, and shrugged. “You are pretty incredible yourself, Mister. Seriously, it’s great; I just get the feeling there’s more you want to try.”

I had to admit, she was right. “Well, sure. I haven’t lived out every sexual fantasy. But what about you? There has to be something you want to try.”

“Oh, yeah!” She sat up, her eyes widening. “But I haven’t had the chances you have had.” Before dating me, Jessica had a college boyfriend, but they split up when she joined the army and left him behind. I was four years older and had a string of short-term girlfriends and one-night stands throughout college and all over the world in my four years as an army officer.

“Well,” I said, deciding to turn the tables, “What is your biggest fantasy? What do you want to try?”

She laughed. “Oh no. I asked you first. Plus, I’m way too kinky for you.”

“Try me,” I said, my fingertips trailing the contour of her side, down her thin hips, and along the curve of her ass.

She almost said something right away, but then she bit her lower lip. “I have an idea.” She rolled away and opened the drawer on the nightstand on her side of the bed, pulling out a notepad and pen. “Let’s write down our darkest, kinkiest fantasy.” She tore two pages from the notebook and handed me one. “Then we exchange them and read each other’s. That way, nobody has an advantage.”

“No judgment? This stays between you and me?” I asked, taking a pen.

“Our little secret,” she said, smiling and kissing me. I agreed. She rolled away to write hers down, and I teased her by pretending to peek over her shoulder and read hers. “Hey, no cheating!” she snapped, laughing and hiding her paper with a spare pillow.

I rolled back over and stared at my blank piece of paper. I felt a rush of heat through my body and took a deep breath. I knew what I wanted to write. My most closely guarded secret was that I was sexually attracted to men. I had a secret collection of bisexual and gay porn, although I had never so much as kissed another man. My ultimate fantasy was a bisexual threesome with a gorgeous woman and a muscular stud, but I was afraid to write it down. If I wrote that down, I would be essentially coming out for the first time in my life to another person, and I wasn’t ready for that yet.

“Finished!” She announced, rolling over. “Let’s trade!”

“Hold on; I haven’t finished mine yet. I have so many fantasies, it’s hard to pin down my ultimate fantasy.”

She leaned in close to my ear and whispered. “Just think of your kinkiest … ” I felt the flat palm of her hand slide down my chest to my cock, which had been inside her only a few minutes before.

“Raunchiest … ” She started rubbing my cock playfully, her voice deep and raspy in my ear. I imagined another man behind her, sliding his cock inside her while she began to give me a hand job.

“Hottest … oh, wait … I think we have an idea!” I could hear the pleasure in her voice as she felt my cock growing stiff. I quickly scribbled my answer, a threesome with her and another man, leaving out the bisexuality aspect. If pressed, I decided, I would say I was straight but loved the idea of her being ravished by two men.

We handed each other our little scraps of paper and unfolded them. Hers read: “threesome with two bi guys.” I looked up at her. She had turned my paper around toward me, beaming with a grin. “Oh my God,” she giggled, “that is so fucking hot.” She leaned forward and kissed me passionately, pressing her body against me and tossing the scrap of paper over her shoulder.

I fell back against the pillow, sliding one hand between her legs to the very moist lips of her pussy. She moaned and arched her back as we kissed. I ran my fingers in circles across her clitoris. After a few minutes of fingering her, I lifted her up and rolled her onto her back. She eagerly spread her legs for me, squeezing her left breast with her hand, closing her eyes, and bending her head back. I briefly rubbed the head of my cock down the slick folds of her pussy lips, guiding it with my hand. She pressed hard against me when I slid my hard-on inside her for the second time that night. I rocked back and forth, fucking her face-to-face, and felt her other hand move from my back to my lips.

When I felt her finger on my lips, I opened my mouth to begin to suck it while I pounded her with my cock. “Mmmmhmm,” she gasped. “I want to see you suck a cock … just … like that … while you fuck me.”

I had never been so turned on before. I energetically sucked her finger and could see the lust in her eyes. I was thrusting so hard and so fast that her firm, round breasts were almost vibrating. At that moment, we both came together, something we had never done before.

Jessica strutted confidently around the pool table, lining up her shot. She looked incredible, dressed casually in tight designer jeans and a tight, shiny, short-sleeve, button-up top. She rarely wore heels and was normally a bit of an army girl tomboy, but on this night she was wearing black-and-silver-glitter open-toed pumps. They added two inches to her frame, already a tall girl at five foot nine, and made her almost the same height as the guy leaning against the wall behind her.

She smiled at me from across the table and bent over at the waist, closing one eye and running the pool cue seductively across the top of her hand a few times. This presented Eric, the blond, athletic. and clean-shaven soldier behind her, with a glimpse of the bare small of her back and tight ass. She took her shot, and billiard balls ricocheted around the table. None went in.

“Aw!” She made a teasing, pouty frown toward me. “I missed our shot.” She handed the cue to Eric. “Your turn.” Eric made an attempt to grab the stick from Jessica, but she didn’t let go right away. “Wait. Let me chalk it up a little bit for you.” She took the tiny square of chalk and rubbed the tip slowly at first, then a bit more quickly, running her other hand up and down the shaft, while Eric’s strong hand held it firmly in place. They both laughed. My cock started to get hard in my jeans.

After Eric missed his shot, I pocketed the next few solids and chatted with him while Jessica fetched more beers from the bar. Like us, Eric was in the army, stationed at the nearby base, where he served in a medical unit as an administrator. We talked about our mutual love for the new TV show Arrested Development, the British mockumentary The Office, and the band The Strokes. I did not share his love for soccer, which he played at the college level in California, and I playfully teased him about all games ending in 0-0 ties. He was thin and fit, but with the thick, muscular thighs of a soccer player and the high-and-tight haircut of a professional soldier. I sank the eight ball into the corner pocket to win, and he smiled as he watched Jessica walk back from the bar, carrying three bottles of beer.

“Man, you are such a lucky guy,” he said to me, gazing at Jessica’s long legs and cleavage. “She is so beautiful.”

“Thanks, Eric,” I said, casually taking a bottle from Jessica. “I know how lucky I am.” She winked back at me.

* * * *

“So, what do you think?” I asked Jessica later, the two of us sitting on stools and watching Eric play pool with two of his friends from his unit who had happened to come to the same bar that night.

“I think he’s sexy.” She put her right hand on my thigh and leaned in close to me. “But I want to know what you think.”

I looked back at him, standing with his pool cue and sipping from his bottle. He looked so handsome and confident, but he also seemed very masculine, and I thought he might not be interested in me sexually. I then thought that I was also a relatively rugged, macho military guy and almost no one would imagine my burning desire to suck cock. “I think he’s incredible,” I said finally. “Let’s ask him if we wants to come home with us.”

Jessica clapped her hands together softly and could barely contain her excitement after hearing me say those words. She covered her mouth with one hand conspiratorially and whispered, “Let’s wait until his friends leave first before we ask him. Otherwise that might be a little awkward.”

I laughed. “Yeah, that’s probably a good idea.” It was starting to become real, after months of talking about it together and searching profiles on Internet dating sites, reading personal ads and looking for clues among friends and coworkers, we had finally found Eric. Weeks of the two of us chatting with him on an instant messenger had finally led to this Friday night. But while I was sure that he was into Jessica by the way he looked at her stunning body, I wasn’t yet sure if he was really into me.

“So, we’re really going to try this?” I asked.

“I think we’re really going to try this.”

“My place or yours?”

“My place,” Jessica responded instantly. “My apartment is closer, and I don’t think I can wait the hour drive to your place. I’m so turned on right now, if I have to wait that long, I will get started myself.”

* * * *

“This apartment is really nice,” Eric said, admiring the framed photographs on the wall. “The pictures are really cool.”

“Yeah, I think so too. Jessica actually took all those pictures herself. She’s really good with a camera,” I said, leading him through the hallway and into the kitchen.

“So, do you guys live together?” he asked, as I opened the refrigerator and took two beers from inside, opening them both and handing him one.

“No, actually, we don’t. We’ve only been dating for about six months. We both live on our own but spend almost every night together. We sort-of alternate between apartments. I actually live in Raleigh, about an hour away. She calls it a long-distance relationship.” We both smiled, and I sat on the table in her kitchen, putting more than three feet between myself and Eric. My heart was beating fast, and my palms were even a little sweaty. I was surprised at my own reaction, because I had not expected to be so nervous. My first night with Jessica, a few months previously in the same room, I had been aggressive, making the first move to kiss her while we were washing dishes together after dinner. Now, I was anxious to be so close to another man I was attracted to.

“So,” Eric said after a moment of awkward silence, “I take it you guys have never met anyone like this before?”

“Is it that obvious? No. I mean, we have been interested for a couple months, but it’s just so hard to find the right person. I thought it would be easier, since it turns out we both are into the same kinds of guys.”

“What kinds of guys are those?” Eric asked, taking a swill from his bottle.

“Honestly … a guy like you.” The words that came out of my mouth even surprised me a little. “You know, fit, taller than her, funny, intelligent, straight-acting … being military helps too.”

“Ah, I wish I had known. I would have worn my uniform,” Eric joked. We both laughed.

“Well, yeah, obviously that would have been hot. I bet you look sexy in uniform, but I meant more because we have to be discreet, with don’t ask-don’t tell and everything.”

“I know. I think that’s a big part of why I haven’t done anything with a guy … I mean, physically. I’ve had phone sex with a guy once,” Eric confessed, and I could feel the conversation start to loosen up.

“Really?” I said. “Tell me about that. What was it like?”

Eric started telling his story, but he didn’t get very far before Jessica walked into the kitchen. She was wearing a black lace bra with silver lining; heels from earlier in the evening and stopped and lean against the door of the kitchen, striking a sultry pose like a lingerie model.

“So, what are you boys talking about?” she asked. Eric and I both stared at her, as I slid off the kitchen table.

“Eric was just about to tell me about the time he had phone sex with another guy.”

“Oh really?” Jessica walked over and put her hand on Eric’s abs, staring directly into his eyes. “That sounds so hot. Don’t let me interrupt.”

“You look absolutely fucking amazing,” Eric said breathlessly.

“Thank you.” Jessica looked at me for an instant. “But you boys both have way too many clothes on right now.” With that, she reached down and slipped Eric’s T-shirt over his head and started kissing him before it hit the kitchen floor. I stood a few feet away, holding my beer and gazing at his chest for the first time. His chest was smooth, a runner’s build, with a defined six-pack and a toned, but not bulky, upper body. His hand rested on my girlfriend’s bare hip as they kissed passionately.

I stared at the two of them for a few moments, Eric brought his hand up from her hip to gently squeeze one of her breasts through her black bra. She breathed deeply as they kissed, and suddenly she stretched out her right arm toward me. I extended my arm out to take hers, and she pulled me in with surprising force. She turned away from him to kiss me, and I reached up and grabbed her other breast with my hand. My cock was swollen so hard and pressing up against my jeans that it actually hurt.

I closed my eyes as we kissed, and I heard his belt come unbuckled and the metallic sound of a zipper being undone. As we held hands, I felt her guide my free hand to the waistband of his underwear. She let go of my hand and as I opened my eyes and looked down, she tugged his boxer briefs down, and his cock popped free. He was shaved, and his circumcised cock curved upward sharply.

“Go ahead, baby,” she whispered. “Suck his cock.”

That was all the encouragement I needed. I got down on my knees and wrapped, first, my hand and then my lips around his stiff rod. It felt as if a decade or more of pent-up bisexual tension was released at that one moment, and I ran my mouth up and down his cock vigorously. I had to slow down and then stop as Jessica helped him out of his jeans and underwear, but then returned to gorging myself on his beautiful shaft. Eric soon started moaning and gently thrusting his cock into my mouth, and I felt Jessica’s hands on my back.

“Oh yes … I like that,” she said and resumed kissing him. I pulled away for a moment and his rigid dick jumped right back to the erect position. I ran my tongue from the base to the tip and looked up at the two of them. I was on my knees and, with her in high heels, her pussy was right at my eye level but still wrapped up in her panties. I unfastened her garters from her stockings and then slid her panties down to her ankles. She helpfully stepped up and allowed me to slip them off her high heels one at a time.

However, after a number of beers, standing in high heels on a tile kitchen floor while being fondled by two men, she lost her balance while I was taking her panties off the second heel. She fell into Eric, who fortunately caught her and stumbled a few feet back into the kitchen table.

“This is dangerous!” she said, in Eric’s arms in just her stockings and bra.

“If you think about it, it’s a good thing Eric was here to catch you!” I joked. The three of us laughed. “Still, why don’t we go to the bedroom?”

“Sounds like a great idea,” Jessica said over her shoulder, taking one of each of our hands and leading us to her bedroom. We both walked behind her, staring at her lovely ass, and we turned to each other and smiled.

We hadn’t reached her bed when she abruptly turned around and said, “Jace, why are you still wearing all your clothes?” She pulled off my shirt, as I started undoing my belt and sliding my jeans off. By the time I threw my jeans into the corner, she was already on her knees, sucking Eric’s cock passionately.

Still a little tentative about touching Eric, I stood beside him and started stroking myself while I watched her slide her mouth up and down his rod, which was glistening in the candlelight from both my saliva and hers. She pulled back and smiled up at me.

“Don’t be shy, baby,” she said devilishly. I laughed.

“I’m standing here naked, jerking off while you suck another man’s cock, I’d hardly call that shy, Jess.”

“You know what I mean.” I knew exactly what she meant.

I continued to watch her suck him and jerked off with my left hand while my right hand hesitantly reached over and touched, then squeezed his right ass cheek. He breathed deeply with pleasure, which I interpreted as encouragement. He moaned softly, eyes closed, mouth open slightly, and I moved to kiss him on the lips.

I slipped my tongue into his mouth and it felt electric to kiss another man. He reached his hand to my chest and I pulled his body tighter into mine. Then I felt my cock slip into Jessica’s mouth, and I pulled back and moaned. She went back and forth sucking us both for a while as our tongues explored each other’s mouths, and then I felt his hard shaft rubbing against mine. She was rubbing our engorged cocks together, occasionally licking and running her tongue around in circles around the tips.

“Okay, that’s enough,” she announced after a few minutes. “I can’t take this anymore. This is driving me crazy. II need someone to fuck me right now.” She was no longer on her knees, but sitting on the floor with her legs spread wide, masturbating.

Eric and I stood silent for a few seconds, and for a few seconds, the three of us all just masturbated together.

“Well,” I said finally, “Eric is our guest.”

Jessica stood up, loosely grabbing Eric by the penis, and guided him towards the bed. She crawled onto her back and turned to me. “Condoms!”

It at all happened so suddenly that we hadn’t planned this out. Jessica and I had been monogamous so far, and we were not using condoms because she was on birth control. “Do we have any?” I asked, as Eric stood between her legs, holding his cock a few inches away from her dripping pussy.

“I think here are some in the bathroom cabinet, next to your razors!” she exclaimed.

I left the room, ran into the bathroom, and started looking around. There were no condoms there. I could hear her moaning softly in the other room. My mind race about what they were doing, and I started making a mess, emptying baskets in drawers until I found a single condom. The expiration date on the wrapper was the previous month. Oh well, I thought, this is going to have to work.

When I came back into the room, Eric’s face was buried between her legs, and her bra was gone. The stockings were still on her legs, raised in the air, as he thirstily licked and tongued her pussy. I crawled onto the bed with them, unwrapping the condom and handing it to Eric. She instantly grabbed my bare cock and started sucking while Eric slid his wrapped shaft inside her.

Eric fucked her very differently than I would have. He slipped his feet underneath his ass, almost like a yoga position, and used short, quick, soft thrusts rather than my deep, hard, pounding thrusts. Jessica pulled away from my cock for a moment to scream loudly, and I thought, I am going to need to try that technique sometime.

His shaved pole looked so hot sliding back and forth inside her, her tits bouncing up and down while her head bobbed back and forth on my cock, and I slid my hand down to her pussy. I rubbed his cock between my middle and index finger while I circled her clit with my thumb. I had never felt Jessica so wet before, in fact it was all over Eric’s lower belly, and there was a small puddle underneath her on the bed. Soon, she couldn’t concentrate on sucking me off while he fucked her, and, unable to do both simultaneously, she resigned herself to groaning and squeezing her fist around me tightly.

I knew she was getting close to climax, and from our conversations over previous months, I knew what would instantly put her over the edge. I got down on all fours and kissed her on the mouth. Then I worked my way slowly down her shaking body, kissing, then sucking her nipples. Eventually, I made my way down to her clit and licked her while she was being fucked hard by another man. My tongue traced her clit, but also the latex on the top of his shaft, and I could feel the little tremors that signal the start of her intense orgasm. She pressed my head down with her hands and let out an whimpering cry.

Jessica, as always, immediately pushed us both away forcefully and assumed a fetal position, holding her knees close to her chest and breathing heavily.

“Wow,” Eric said, turning to me. “Does she always cum like that?”

“Sort of,” I said, stroking my dick as Eric did the same. “This time was way more intense. She is super sensitive right now, she’s going to need to take a time out.”

“No problem. I’m good to go. How are you?” he asked me. I just exhaled deeply and smiled, still wanking. “You still need to get yours.”

I took the hint and laid on my back. Eric leaned forward and kissed me, and we rubbed our two shafts together. Then he backed up on the bed to take all of me into his mouth. I ran my hands through his short, prickly, military haircut and relaxed as he fellated me.

After a few minutes of getting head from Eric, I turned over to look at Jessica, and she was looking back at me, grinning, She kissed me deeply and then crawled on her hands and knees down to the foot of the bed and tapped Eric on the shoulder. He stopped and looked at her and they kissed and then started blowing me together. They took turns silkily licking my balls and sucking, until I heard Jessica whisper in my ear. “Does that feel good, baby?” Her hand was still softly rubbing the base of my shaft while Eric sucked the top.

“Yes! Fuck yes!”

“Can I ride you now?” She asked, biting her lower lip. Riding me from on top was normally her favorite, and it was usually the best way to get her to orgasm.

“Oh yeah, baby. Ride my cock.”

Jessica threw one leg around my body and inched her way down toward my cock. Eric stepped back off the bed and just watched her sit on my cock and rock her hips violently back and forth while she grunted with pleasure. I lifted my head up off the pillow, licking and sucking her nipples, when I felt Eric rubbing my balls and her ass, and I spread my legs wider to give him easier access to our pleasure zones. Jessica roared with pleasure and surprised me with the next thing she said. “I want both of you inside me now!”

We had not talked about this, but it sounded hot. I loved the idea of another man’s cock rubbing against mine while inside of her, and I pulled away from her tits for a moment to make eye contact with Eric. “Go ahead, Eric.”

Eric gave it his best effort, sliding his cock up against mine and trying to stuff it into her pussy, but was unsuccessful. Jessica stopped her thrusting to make it easier for him to slip in, but suddenly her hand went back quickly to grab his cock. “Wrong hole!”

“Sorry,” Eric said sheepishly. “Accident.”

“It’s OK,” she replied. “It happens.” She tried to guide his cock inside, rubbing it against mine, sending shock waves of pleasure through me. After some grunting, she slipped off me and announced a new strategy. “Let’s try this.”

I lay on my back, Eric between my legs, our two cocks touching. Jessica started stroking both of them and then pressed them firmly together with one hand. She guided both of them into her soaked pussy that way, and the three of us groaned simultaneously with ecstasy. Jessica started thrusting her hips rapidly and kissed me, her arm reaching behind her to hold Eric close against her neck. I reached around and squeezed Eric’s ass, pressing him into her to counter her thrusts against me.

We got going so hard that Eric slipped out and, instead, walked around to present his cock to me, stripping off the condom. I took it all into my mouth and sucked him intensely while my girlfriend took herself to the brink of another orgasm.

“I’m going to cum again,” she moaned.

I moaned as well. I would have said the same, but my mouth was, at that moment, totally filled with cock. I felt her pussy tighten, her eyes wide with lust, as she watched me suck our friend’s cock, and I was able to shoot my load right before she let out a long, high-pitched squeal. She rolled away instantly, allowing me to devote all my attention to Eric’s cock. I desperately wanted to see him shoot his semen all over me, but it took about ten minutes of feverish jacking before he launched his warm, creamy cum all over my face and chest.

We all collapsed immediately on the bed, panting heavily. “Oh my god, that was incredible,” Jessica said first. “I think I’m done tonight.”

“Me too,” Eric said.

“Ok,” I agreed. I rolled over and hugged my girlfriend. “Did it live up to your fantasy?”

“Are you crazy! That was even better than my hottest fantasy!” I had to agree with her.

“So, Eric,” I rolled over and rested my head in my arm, “what are you doing next weekend?”

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