Her Free PassbyFlynnMichaels©
B was frustrated because I wouldn't play her game. "Come on. Just tell me," she implored. We were in bed and B had asked me who I would choose if I had a "free pass" to have sex with anyone. To me, the question sounded like a trap. In my imagination a number of women jockeyed for position—movie actresses, a few porn stars—but there was no way I was going to tell B.
"I'll tell you mine," she finally said, realizing that I wouldn't be giving up any names. "I'd use my free pass with D." Who? I thought she was asking about our celebrity crushes, but I didn't recognize this name.
B explained that D was a college classmate of hers, a guy she had always lusted after but never dated. Whenever one of them was single, it seemed the other was always in a relationship. B described him as tall, athletic, and an avid cyclist, with dark curly hair. A girl that D dated once had confided to B that he was also very nicely endowed. B said that in her dorm room at night she often fingered herself to climax imagining D's hard cock inside her.
I can't say I was crazy about the idea of B using a "free pass" with a guy she actually knew, as opposed to someone famous and unattainable. I allowed myself to feel the slightest twinge of jealousy.
"It would be great if D were here right now," B sighed into my ear as I felt her take my cock in her hand beneath the covers. However jealous I felt, it was obvious that B had gotten hot thinking of her college crush, and I was always a lucky beneficiary when B was turned on. "I would love to fuck the two of you," she growled, caressing my member.
"What would you do?" I asked, my mouth suddenly dry, as my cock started to grow. We enjoyed describing our fantasies to one another and B's stories frequently involved a threesome, sometimes with a woman, sometimes with a man. An imaginary tryst with another guy didn't bother me—B's stories always succeeded in making me very horny, actually—but this was the first time she talked about us sharing a real person, rather than some fictional hottie.
B described how she would have D and I remove our clothes and masturbate in front of her. She said she would strip off her own clothes and rub her pussy while watching us jerk our cocks. As her fantasy unfolded, I could tell B was stroking herself under the covers while caressing me with her other hand. I pictured myself masturbating with another guy, our hands sliding over our dicks. Jacking off with another man wasn't the kind of thing I would ever consider on my own, but my cock was now solid and throbbing at the idea of doing it while B watched.
"I'd kneel in front of you both so I could see your hot dicks up close. They look so good, I want to suck them. Do you want to see D's cock in my mouth?" I stammered that I did, and B told me how she would lick the length of D's rod before taking as much of it as she could down her throat.
"Mmmm, it tastes so good," B moaned. She had obviously fantasized about giving D a blow job many times before.
"I want to suck him while you fuck me," she said. As B said this, she stopped stroking and mounted me, sliding my rigid member inside of her. "I want you in my pussy while D fucks my mouth." B began riding my pulsing meat, her juices coating my shaft and testicles, and I imagined her college crush thrusting his hard-on between her hungry lips. I felt my climax approaching, B's frothing pussy and wild imagination driving me on.
B was growing more frenzied too, caught up in her tale of taking two cocks at once. "I—I...oh god," she stammered. B descended on my pulsing cock, and pushed her clit hard against my pelvis. "I want you both to come on me!" she whispered. We both imagined D and I erupting in tandem, covering B with thick spurts of cum. B's body tensed, her eyes closed, and her wet pussy pulsated around my shaft as I spurted wave after wave of hot cum inside her.
Needless to say, it was a little awkward a few months later when B told me that D had called out of the blue to ask if he could stay at her place. Apparently, D was driving through town on his way to some bike race and wanted to crash on B's couch. She told him that she would have to check with me first.
"Sure," I said, attempting to sound nonchalant. Notwithstanding B's "free pass" confession, I decided that I would try to be the good boyfriend and tamp down any jealousy. I definitely wasn't going to admit to any insecurity related to B's fantasy threesome.
D showed up a few weeks later, a fancy bike on the roof of his car. He no longer had curly hair—it was cut close—but in all other respects he matched B's description: handsome, with a lean cyclist's physique. Worst of all, he was a really nice guy. Over dinner, D told a number of funny stories and he even did the dishes when we were finished.
Switching from wine to cocktails, we moved into the living room, D and B taking the couch while I sat in the chair nearest B. It was a warm summer evening, the windows were open and we were all clad in t-shirts and shorts. (I had noticed that B happened to be wearing an especially revealing shirt and her shortest pair of cut-offs.) We discussed our long term plans and D and B gossiped about classmates, as we emptied and refilled our glasses a few more times.
"So," D declared, turning to me, "You must be a pretty special guy to keep this girl satisfied."
B responded before I could. "And what do you mean by that?"
"Well, B, you kind of had a reputation as a horny little devil in college." B's jaw dropped and I let out a little chuckle.
"As if you would know!" B said indignantly.
D took another drink. "I probably shouldn't tell you this, but you were pretty notorious as the serial masturbator in our dorm." Hearing this, I could feel a smile spreading across my face as B turned bright, bright red. "Everyone noticed that you were always excusing yourself to go to your room and locking the door behind you. You'd come back ten minutes later completely flushed. Your roommate said sometimes at night you were so loud 'petting your kitty', you'd wake her up."
"Some things never change," I said. This was great. Watching B's embarrassment was very entertaining. And I also felt myself getting a little aroused at the thought of B as a horny coed compulsively pleasuring herself.
"New topic!" B announced after taking a big gulp from her cocktail. She asked D if he was still with his old girlfriend. D said no, that they had broken up over a year ago.
"So, seeing anybody new?" B pressed, obviously curious.
"Not really," D said. He took another long drink before saying, "Well, last summer I had sort of a thing with X..."
B almost spat out her drink with surprise. X was a man's name.
"X was a guy who lived in our dorm!" B informed me before turning back to D. "But he's—but you're not—" B wrestled with this new information for a moment, finally urging D, "Come on! Details, details!"
D looked sheepish as he explained that X was also into cycling and they had stayed in touch after graduation. After D broke up with his girlfriend, he and X had arranged a cycling trip through the Northwest.
"I knew X was gay, but didn't think he was really in to me in that way, and of course I'd never been with a guy before. I just figured two weeks of biking was better than moping around the apartment." D took another long sip off his drink. "I guess it was Day 2, the biking was great, but I started getting a knot in my leg. After we set up camp that night, I told X my hamstring was hurting. He said that he had been taking some massage therapy classes and offered to help me work out the knot. I knew there was a good chance my leg would stiffen up overnight if I didn't do something about it. So we got in the tent, I stripped down to my shorts and X had me lie on my stomach."
B's eyes were huge and she was more than a little flushed. She was hanging on D's every word.
"Anyway, X has great hands. He got the knot out and then started working on my calves and my other thigh. After a long day of riding, it was really relaxing. He was making me feel very good and I think I might have even dozed off a little bit. Then, after a long while, he told me turn over so he could work on the front of my legs and—" D paused for another sip. "—And I realized my cock had gotten really hard. Of course, there was no hiding the boner in my bike shorts. X saw the bulge right away. And he asked if he could take care of it for me."
B's mouth was agape and her freckled cheeks had reddened. She was clearly turned on now, her voice dry as she asked, "Then what happened?"
"You know, I definitely hadn't planned on it. Never been with a guy before. But I figured we were alone in the middle of nowhere, nobody else was around, and I felt like I really needed the release. So I said yes." D got up to retrieve the pitcher and began refilling our glasses. "X pulled down my shorts and gave me an amazing blowjob. Maybe there's something to what they say about a guy knowing what a guy wants. Anyway, I don't think I've ever cum that hard. "
On saying this, I noticed D was making eye contact with me. Now it was my turn to take a large embarrassed drink from my tumbler. If it weren't for the alcohol, D probably would not be giving such an explicit account of his first gay encounter. And I couldn't believe it, but listening to a man describe in detail getting a blow job from another guy—and watching the effect his story was having on my girlfriend—was turning me on as well.
As D was telling his story, I had noticed B shifting in her seat and subtly rubbing her thighs together. She had previously confessed to me that this was her method for gently stimulating her sensitive clit when she was horny in public and unable to touch herself. "So was that it?" B asked.
"Well, at first I thought maybe it would just be a one-off kind of thing, and X didn't say a word about it the next day during our ride. But that evening, as soon as we set up camp, X asked if I needed another massage. I surprised myself with how quickly I said yes. By the time we got back in the tent, my dick was already hard and I could tell X was turned on too. One thing led to another and..." D paused, as if deciding whether to continue with his story. "...and we traded blowjobs."
"Ohmigod!" B gasped, her face a mix of shock and arousal. She was really squirming in her seat now and practically salivating. "You t-traded?!"
"Yeah, I mean after he made me feel so good, it only seemed fair, right?" D smiled. "And I suppose after all the blowjobs I'd gotten over the years, I was curious what it would be like to give one. I gotta say making another guy cum was really hot. So for the rest of the trip after we were finished riding for the day, X and I would get each other off. Don't get me wrong—I still prefer women. But I don't regret my little vacation from being straight at all. And I wouldn't mind doing it again if the opportunity presented itself."
Once again, I noticed D looking at me as he said this. Now I was really self-conscious. The drinks combined with D's hot and detailed story had caused my penis to steadily—if involuntarily—harden. I could feel it straining in my shorts, and I shifted in my seat, hoping no one would notice the unmistakable swelling in my lap.
Too late. "Wow. That story got you excited!" I heard B exclaim. I couldn't believe she was calling attention to my erection.
But when I looked up, she was instead leering at D—an exceptionally large outline was clearly visible pushing against his shorts. Apparently the rumor that B had heard in college was true. B's eyes were practically jumping out of her head, and I could see her erect nipples beneath the fabric of her shirt. I thought she might leap across the couch and start fucking him at any second.
"Hey, I'm not the only one," D smiled, nodding towards me. B turned and gasped at my swollen groin. Looking like she had just won the lottery, B raised her eyes to meet mine, a huge smile on her face. She didn't say anything. She didn't have to.
She was cashing in her "free pass".
"I think it's time for some after-dinner entertainment," B announced. Moving next to D on the couch, B whispered in his ear something I couldn't hear, undoubtedly a confession of her fantasy.
D looked over to me and asked, "You okay with this?" I shrugged my consent—as if my rigid member wasn't agreement enough—and slid over to join them on the couch.
B gave me a long and intense kiss, her hand stroking my cock through my shorts. Then she turned and did the same to D. The realization that I was about to share my girlfriend with another man hit me as I watched her hand move over the generous ridge in D's shorts. Finally breaking off the kiss, B instructed us to remove our clothes. She wanted to "see what we're working with."
"Nice one, bro," D said as I lowered my boxers and my firm cock sprang out. It felt good to free my hardness, and seeing D's impressive rod I'm sure he was more comfortable after shedding his shorts. He was already almost fully erect, long and thick, his athletic frame making his cock appear even larger.
"Did you and X ever jerk off together?" B asked, gazing at D's dick. He confirmed that they had, and B said that she had always wanted to watch two guys masturbating. Taking her cue, D and I began massaging our erections. As I wrapped my hand around my shaft and began caressing up and down, I looked over at D. I had never watched another guy jack off before. His technique involved forming a ring with the thumb and forefinger around his shaft, while using his other hand to massage the underside of his scrotum.
B switched between watching D jerk himself, then me. Gradually her hands made their way down to the front of her shorts. Unbuttoning her fly, B slid her fingers into her sodden panties, using her other hand to caress her pert breasts. The three of us masturbated like that for a while, each of us getting increasingly turned on watching the others pleasure themselves.
I made a point of pacing myself, but as usual B quickly lost control. Breathing heavily, the wet noises of her fingers on her pussy clearly audible, B reached orgasm within a few minutes. She groaned loudly, her body tensing next to me on the couch. Her eyes closed, and she thrust her hips against her slick hands. D and I began jerking ourselves faster, spurred on by the intensity of B's climax.
After taking a moment to recover, B took a penis in each hand and began stroking D and I in tandem. Seeing her masturbate D's massive dick and feeling her sticky palm glide over my rod at the same pace was incredibly intense.
"Oooh!" B exclaimed, noticing a translucent pearl of precum seeping from the tip of my cock. Leaning over, she gently licked off the bead of nectar and swirled her tongue over the crown of my penis, all the while pumping both shafts. D watched intently and shifted even closer on the couch. Reaching over, he began running his fingers through B's short hair and then, after a minute, gently pushing her further down onto my cock. I exhaled heavily, reveling in the sensation of B's eager mouth taking more and more of me.
After what seemed like forever, B came up for air, a long clear strand stretching from the throbbing head of my dick to her smiling lips. Now it was D's turn. B reoriented herself to face D's hard purple column. I pulled her hips up so that she was on her knees with her firm ass towards me, and as I set to work peeling off her tight shorts, B took D's massive dick in her mouth. My view was obscured, but his sigh of pleasure was unmistakable, and he placed his hands on either side of B's head. She bobbed a few times, then turned slightly to look back at me, her freckled cheek distended as she sucked D's engorged rod.
I was frantic to fuck her. Fragrant juices dripped from her as I smoothed the head of my cock over her labia and then not-so-gently thrust inside. I always loved the feeling of taking B doggy-style, surging deep into her soft wetness. But this time I drove into her with a fresh urgency, propelling her forward—further onto D's dick. With each of my thrusts, they both moaned, B's lips easing steadily down D's shaft.
B had been less than enthusiastic about fellatio when we first started dating, but over time had developed a real knack. Now, she was eagerly working her mouth over another man's dick as I filled her from behind. After what seemed like a pleasurable eternity, D looked at me and announced that he was about to cum.
"Mm!" B exclaimed. Sliding her lips off of D's dick for a moment, she insisted, "Come on me—both of you."
B reached up and began to massage the length of D's cock with both hands, and it only took a few strokes before he detonated. As the first wave of D's hot fluid filled her mouth, B let out a muffled but ecstatic sigh, and I felt her pussy contract around me. Her body went taut and she shuddered with a second orgasm, as D threw his head back and released more of his cream. Watching D cum in my girlfriend's mouth, feeling her lose control, it was too much. As B's pussy continued to spasm, I withdrew my throbbing pole, intent on adding my cum to D's sticky load.
B turned to face me just as D released yet another arc of ejaculate, painting a line of semen across her cheek. B looked up at me, smiling in satisfaction, a creamy trail sliding down her chin. God, she looked so hot.
Taking my crown in her already full mouth, B urgently pumped my shaft, providing the last bit of friction needed to send me over the edge. My hips bucked forward and I let out a low grunt of pleasure as I released my pent-up load, feeling it coursing out of me. Looking down, I watched as my cock pulsed between B's lips. Even more frothy white surged from the corners of her mouth. Next to me, D continued to wring spurts of hot fluid from his twitching member on to B's face, neck and breasts. We continued like this until we were all spent, B cooing in satisfaction as she spread the miasma of sweat and semen over her skin.
I collapsed onto the couch, my head reeling, trying to process what had just happened. I heard D mumble his appreciation for our "hospitality," before he stumbled off to the guest room. B leaned over and kissed me hard, the thick saltiness still on her mouth.
After only a moment's consideration, coming up with some candidates for my own "free pass" seemed like a very good idea.