34 comments/ 565176 views/ 248 favorites A Friendly Bet By: damonX BRRRRIIIIIINNNNG! "Shit," I muttered to myself. "It never fails! Every time I get in the shower!" With that, I jumped out of the shower and grabbed a towel, heading for the phone. "Hello," I panted after running half naked through my house, picking up the phone, and dripping water all over the floor in the process. "Hey. What's up?" a feminine voice asked. "Oh, hey Jen. I'm just about to have a shower." "What are you doing tonight?" "Uh, nothing. Why? "I'm bored. You up for some foozeball?" "Sure. If you're up for getting your ass kicked again." "Hey Mr. Cocky! You better watch out. I've been practicing." "Sure, sure. Just remember to bring the case of beer you owe me from last time." "Yah, yah. I'll be there around eight." "Okay. See you then." I hung up the phone and made my way back to the shower. Playing foozeball wasn't my idea of a good way to spend my Saturday night, but I didn't exactly have anything else to do. Besides, Jen and I always have fun. As eight o'clock rolled around, I pulled the foozeball table out, put on some music and began to wait. I had known Jen for a couple years and I didn't remember her ever being on time. True to form, as it neared nine o'clock, the doorbell rang. Before I could answer, the door opened and Jen marched in, pushing a case of beer into my arms. "Here asshole!" she said jokingly. "This will be the last time I'll ever have to give you anything." "Whatever you say princess," I answered sarcastically. I had to admit Jen looked good. She was wearing a pair of low-riding jeans with a studded belt that allowed the crack of her ass to peak out over the top. The little black top she was wearing would have been more suited to a nightclub than a foozeball game but I wasn't complaining. "You'd better put those in the fridge." Jen said with a wave of her hand. "We wouldn't want any warm beer would we?" "We?" I asked. "Who said you're getting any bitch?" Jen opened her mouth in mock surprise. We joked around like that all the time so it wasn't unusual for us to trade insults. "You're the one that will be the bitch tonight," she countered. "My bitch!" "Dream on. Let's play." I took out a couple beer and put the rest in the fridge before making my way over to the table. Jen was waiting, tapping her fingers impatiently and glaring at me with her dark, almond shaped eyes. I tossed her a beer and raised my own. With a final "Good luck" we started to play. Jen and I were starting to make our foozeball games a weekly tradition, with me winning every single time. We would always wager something which is why my fridge is usually well stocked with beer. In all fairness, however, it was my foozeball table. I won the first two games easily and downed two beer in the process. Jen was taking it a little easier on the booze but was still drinking her fair share. "I have to admit," I said after scoring the game winning goal in the second game. "You are getting better." "Gee thanks," she drawled. "Just drop the ball." "Are you sure you want to keep going? I usually get better as I drink more." "Best of seven series bitch! It's not over yet!" "I think so far, you've been MY bitch." My final comment shut Jen up and we began our third game. Ten minutes later I was up 3-0 and Jen was head for the fridge to grab another beer. "So where's Carrie tonight?" Jen asked, speaking in a baby voice as she spoke my girlfriend's name. It was no secret that Jen disliked Carrie, as she always seemed to dislike my girlfriends. "She's out with her friends," I answered. "Uh oh! I bet she's getting fucked right now!" "Settle down," I said dryly. "Why would she go out to get fucked when she has this waiting at home?" Jen let out a laugh. "I'm just kidding," she giggled. "By the way," I began. "Where's Kevin?" referring to her significant other. "Same." I gave her a look of concern in an attempt at teasing her in the way she had teased me. "Don't even say it!" she blurted out. "He's not a cheater." "What ever you say," I said with a smile. "He's not." "Okay." "Fuck you!" Jen said, half laughing and tossing a bottle cap at me. "Let's play. I'm just getting warmed up." I took it easy on her that game and she managed to squeak out a meager victory. "Three to one, bitch!" she howled, dancing with excitement. I could tell she was starting to get buzzed. Surprisingly it was making her play better however and after she grabbed another drink we jumped into our fifth game. "Hey," I said halfway through the game. "How come we never hooked up?" "What?" "Why didn't we ever get together and... you know." "Fucked?" "Yeah." I was always impressed my Jen's bluntness. "Well," she said, cocking her head to the side as if in deep thought. "I guess I don't like ugly guys." "Ouch!" I said cringing. "That hurt." "Just kidding," she returned. "We almost did. Don't you remember?" "You mean...?" "Yeah. Halloween. The night we met. I kind of wanted you." "Really?" I asked as I scored another goal. "Yeah. After we danced you probably could have taken me home." Although I already knew everything she was telling me it was strange hearing her say it. The fact was that I wanted her that night as well. "I guess I missed my chance." I said in a over the top, resigned tone. "You sure did." We had become friend soon after that night and stayed ever since. Except for the occasional flirting nothing had gone on between us. "Oh well," I muttered. "I don't think you're dirty enough for me anyway." "Excuse me?" "You heard me." "I think I could handle anything you could give me." Our conversation was starting to turn me on but I let the subject drop. Jen ended up winning that game which brought our total to 3-2 in favor of me. "So you really think I'm not dirty enough?" It was obvious that Jen wasn't ready to let the subject drop. "I didn't say that. I said you're not dirty enough for me!" "I think you would be surprised." Her response peaked my curiosity and I took the bait. "Okay, what's the dirtiest thing you've done?" "I'm not telling!" "Oh come on! You can't say something like that and then not tell me." I had to admit I was very curious as to what Jen had experienced. Although we joked around about sex all the time, we never really talked about it seriously. "I'll tell you what." she said. "If I win this game I'll tell you." That's not fair! I..." Jen cut me off by raising her hand. "That's the deal. Take it or leave it." Needless to say I took a dive and we were soon tied at three games a piece. "Okay, let's hear it." I said after admitting defeat for the third time that night. "And this better be good." "Okay, okay, Jen said, fidgeting with the handles on the foozeball table. "Remember when I went to Mexico last year?" "Yeah." I leaned in closer, anxious to hear the story. "Well I met a couple Australian guys. We hung out a few times and stuff. "And..." On my last night there I had sex with both of them. "Wow," was all I could say. After a few moments to collect my thoughts I began to drill her for details. "Did they take turns or do you at the same time?" I asked, trying to hide my growing erection. "Same time." "You slut!" I said laughing. "I would never have guessed!" "Hey!" Jen answered, trying to sound hurt. "I was really drunk!" "So they spit roasted you?" "Spit roasted? What the hell do you.... Oh I get it. Yes. They spit roasted me." "Does Kevin know about this?" I asked, continuing my interrogation. "Of course not. How would you feel if Carrie told you she got double teamed?" I was still too shocked to think about anything other that my friend getting fucked like a cheap whore. "Did they DP you as well?" "DP?" "Yeah. Double penetration. In the pussy and ass at the same time." "In my ass!? Yuck. No, I don't do that!" "What? Not at all?" "Nope." "So you'll get spit roasted like a dirty porn star but you won't even try it in the butt?" "It just doesn't appeal to me." "Have you ever tried it?" "No." "Then you never know. You might like it." "I doubt it." "I told you you're not dirty enough for me." "Oh yeah? And how many girls have you fucked in the ass before?" "A few." "Really?" "Yeah. It's the best." "Maybe for you." "Hey, the girls enjoyed it too!" "Yeah, I'm sure they did." I let the subject drop, but unfortunately my dick did not. As we started the next game I found myself staring at Jen, imagining her on her hands and knees sucking some guy's dick while she gets fucked from behind. In fact I was so distracted that she managed to score a few goals before I realized what the score was. "You're looking a little shaky," she said after scoring her fifth goal of the game. "Did you drink a little too much?" "I don't think that's it," I responded. Jen tossed back her lustrous brown hair and flashed me a smile before scoring another goal. I let go of the handles and began to rub my wrist which was starting to get a little sore. "Oh, poor baby," Jen cooed. "It's probably all that jerking off you do." Little did she know that she was going to be the subject of my masturbatory fantasies that night. Although I tried my hardest, Jen scored a few more lucky goals and pretty soon I was down 9-0 and Jen was on the eve of her first victory ever. "So by the way," she said in a overly confident manor. "What are we betting?" "How about...If I win, I get to fuck you in the ass." Jen stared at me with those sexy dark eyes, a crooked little smile forcing it's way on to her face." "Sure." I was taken aback. "Really?" "Yep. If you win you can fuck my ass. But if I win, you have to wear a shirt that says "Jen's bitch" on it for a week." "Are you sure you want to do this?" I asked. "Absolutely. What are the chances you will win? I'm up nine to nothing!" "Okay," I said. "You're on." With that I let the ball drop. Within five seconds I had a goal and Jen was giving me an evil smirk. "Don't worry," I said. "I'll be gentle." I scored three more quick goals and Jen was starting to look nervous. "No backing out now," I warned. "I know, I know." After the next goal, the smile was gone from her face. She anxiously sipped down the remainder of her beer before concentrating back on the game. "That's it," I joked. "The more you drink, the better it will feel." "You still have five more to go asshole," she countered as she dropped the ball. "It's funny that you used the term "asshole."" I stated, blasting in another goal. "Since soon, I'll be in yours!" "Fuck," she cursed. "It's not fair. You keep distracting me." "Don't cry about it," I laughed popping in yet another goal. As much as I didn't want to wear a shirt that labeled me as anyone's bitch, it was the prospect of fucking my good friend in the ass that was driving me on. "Fuck!!!!!!!!!!!" she yelled as I scored my seventh. I just laughed and we continued. After I shot in number eight I expected Jen to continue ranting, but to my surprise she didn't say a word. She calmly retrieved the ball and dropped it back into the table. No sooner had the ball touched the surface then I had fired in the tying goal. Jen dropped her head and banged it lightly on the table. My palms were sweaty with anticipation and I urged her to hurry up and drop the last ball. She looked up at me through her messy, but still sexy, hair and dropped the ball. I fired it right away, but she caught a lucky bounce and saved what would have been the winning goal. She quickly shot it back and almost scored herself. I made the save and then waited, just holding on to possession of the ball as I looked at Jen and smiled. "I bet your ass is so tight!" With that, I fired the ball into the back of her net. Jen stood there dazed for a moment before she spoke. "Rematch?" "I don't think so." "Come on! I can't let you do that. I have a boyfriend!" "You should have thought about that before you made the bet." "But here was no way you could win!" "Apparently," I stated with an air of sarcasm. Jen walked over and slumped down on the couch, dropping her head into her hands. I finished my beer and then joined her. After about a minute of contemplation she looked up at me. "I'll give you a blowjob," she suggested. I just shook my head. As nice as it would be to have Jen suck my dick, I'm sure it would feel much better imprisoned in the confines of her beautiful ass. "Fine." she resigned. "Let's get this over with." "Let's go to the bedroom," I suggested. Jen agreed and we made out way to my room. She looked nervous as she sat down on my bed. "Do we need any lube?" she asked. "Aren't you supposed to use lube?" "Sorry," I said. I don't have any. I guess you'll just have to suck it first." "No way! You're not getting a blowjob too!" "Okay then. What about condoms? Do you want me to wear one?" Jen thought about it for a moment before answering. "Nah. Just do it." Suddenly I felt very uncomfortable. Jen took off her socks, tossing them to the side. As she started to undo her pants she looked up at me. "Aren't you going to undress?" "I thought I'd just watch you first," I answered wryly. "Well, you thought wrong. Get 'em off!" I let out a laugh as I pulled my shirt over my head. I wondered if I looked as nervous as Jen. As I started to undo my pants, my eyes wandered back to my friend, who was sliding hers down her tanned, muscular legs. It wasn't the first time I had snuck a peak at Jen's body. She was the only person I knew who spent more time in the gym than me, and I could see it was paying off as I gawked at her legs and the tiny pair of black underwear adorning the area between them. I slid my pants off and kicked them aside, trying hard to conceal the massive erection that was doing its best to pop out of the hole in the front of my boxer shorts. Jen was sitting on my bed, fidgeting nervously but looking cute in her little black panties. "Aren't you going to take off your shirt?" I asked. "I don't need to take my short off to get my ass fucked do I?" she snapped back. The fact was, was that Jen was more than a little self conscious about her less than average sized breasts. I knew that was the case but didn't press the matter. Besides, it wasn't her tits that I was interested in. We sat there for a moment, each not wanting to be the first to be completely exposed. Finally, without a word, Jen slipped off her panties and pulled her knees up to her chest as she sat there looking up at me. Taking her cue, I pulled down my boxers and stepped out of them to stand before her, completely naked. "Okay, " she said. "How do we do this?" "The easiest way is if you get on your hands and knees." Jen moved to roll over but stopped and looked back at me. "Do you think we could turn the light off?" she asked. I shook my head. "I like to see what I'm doing," I replied. "Fine." I expected her to put up more of a fight, but to my surprise she complied with my wishes and rolled over, propping herself up on her hands and knees. I took a moment to relish the sight of my best friend bent over naked on my bed before climbing down behind her. Gently, I placed my hands on her taut ass cheeks and pried them apart to expose her asshole to my view. "What the fuck are you doing?" Jen scolded, reaching back to swat my hands away. "I'm just looking." "Just do it." "Are you sure you don't want to suck it first?" I asked hopefully. "Just stick it in and get it over with." "Okay, but I don't want to hear you whining that it hurts." With that, I placed the head of my dick at the entrance of her puckered little rosebud and pushed. "Owwwww," Jen yelped as the first couple inches disappeared inside her asshole. "Okay!okay!okay! I'll suck it! Just take it out." I smiled to myself as I withdrew my cock from Jen's ass. With little hesitation and to my surprise she promptly spun around and grabbed my dick in her tiny hand. With a final, resigned look my way, she pushed my cock past her lips into her mouth. I threw my head back and moaned as Jen's head bobbed back and forth on my dick, coating it with saliva. I wanted the blowjob to go on forever, but to my disappointment Jen backed off as soon as my shaft was good and wet, resuming the position on her hands and knees. I spit in my hand for good measure and smeared it along her ass crack, rubbing my thumb into her hole for added lubrication. I then placed my newly glistening cock back at the entrance of her dark inviting hole and pushed. "Relax," I suggested, as the head of my dick slipped inside her. Jen put her head down and exhaled as I felt her asshole's grip on my shaft weaken considerably. "Good girl." My praise apparently went unnoticed as Jen remained silent. I pushed forward a little more, feeding more of my cock into her ass. Jen let out a quiet moan although I couldn't tell if it was from pain or pleasure. I was about halfway in when I reached down and pulled her ass apart, treating myself to exceptional site of my best friend's little pink butt hole hugging my dick. At that moment I only wished I had a camera. "You.. can put it in... farther now," Jen wheezed, through clenched teeth. I complied and thrusted my hips forward a little more, burying another couple inches of meat in her ass. "Play with your clit," I suggested. "It will make it easier." Jen took my advice and reached back between her legs as I bottomed out in her asshole. My balls were pressed against her pussy lips, which I noticed were a bit moist. As I began to gyrate slowly, moving my cock in and out in small increments, I could feel the pace of Jen's fingers increase. "How does it feel?" I asked, picking up the pace. "It's...okay," she stammered, obviously preoccupied with the area between her legs. I was moving in and out with long, slow strokes as Jen became more comfortable. I gazed at her impossibly tight asshole as it repeatedly swallowed my cock. If not for my agonizingly slow pace I definitely would have cum already. "Oh Fuck Jen," I moaned. "Your ass feels so good!" "Your cock in my ass feels so good!" she returned, as her fingers increased to a frantic pace. I was surprised to hear Jen talk like that, but it was definitely a turn on so I encouraged her to continue. "Yeah, you like that?" I asked giving her a light slap on the ass. "You like getting your ass fucked?" "Yes!" she moaned through labored breaths. "Yes! Fuck me! Fuck my tight ass! Oh! Oh my fucking god! I'm gonna cum! I'm gonna... Oh! Fuck! I'm cumming! I'm cumming with your cock in my ass..." Jen's voice trailed off as her orgasm subsided. She raised her head from the bed and swept the hair from her face. "That didn't take long," I commented, continuing to slide my dick in and out of her anus. "Are you almost done?" she asked. "It's starting to hurt again." "Just relax," I said. "I'm almost there." I increased my pace even more as Jen dropped her head down and bit her arm to keep from howling in pain. "Where are you going to cum?" she asked, her voice muffled by her own arm. "In your ass," I replied bluntly. "No, you can't do that!" "Okay then. I'll cum in your face." Jen was silent for a moment before answering back. "Okay," she said quietly. "Do it." "Where?" I goaded. I could feel the beginnings of that unmistakable feeling arise in my balls. "You know where!" she shot back. A Friendly Bet "Tell me." "No." I was getting closer. "Tell me!" "In my ass! Alright?! Cum in my fucking ass!" On cue, I unleashed a torrent of hot cum into Jen's asshole. I continued fucking her as I spurted stream after stream into her body. Jen through her head back and moaned loudly as my balls slapped violently into her pussy lips. After I had shot my last drop I continued sliding my dick in and out of her now slippery ass, causing my cum to ooze out from around my shaft and drip down onto my bed. As my dick became too sensitive I pulled it out of Jen's well-fucked asshole with a lewd slurping sound. Immediately, Jen collapsed to the bad and rolled over on her side, reaching back with a hand to touch her recently abused hole. "Owww! Fuck that hurt!" She exclaimed, softly rubbing herself. "You liked it," I said snidely. "I did not! It was awful!" "Yeah? Is that why you were telling me how good my cock felt in your ass?" "Shut up. That was the heat of the moment." I just laughed. Jen began to shift uncomfortably, pursing her lips up in a makeshift snear. "What's wrong?" I asked. "It feels weird." "What's that?" "The cum in my ass. It feels weird." "Hey! Don't let it drip out all over my bed!" I ordered, half jokingly. "It's your jizz ya know?" she countered before reaching back to stroke her asshole again. "Fuck it hurts." she complained. "Aww, poor baby," I teased. "Do you want me to kiss it better?" "Yes!" she responded, although I could tell she was joking. "Okay," I said. "Bend over." "Uh, that's okay," Jen stated deliberately. "Nope. Bend over. Come on." I said giving her a playful slap on the side of her ass. "Noooo," she whined, reaching for her panties. With a lightning quick movement, I snatched her underwear from her grasp, holding them out of her grasp. "Hey, give those back!" Jen rose up to her knees and reached out, but I dropped the panties behind my head and grabbed her around the waist, pulling her down to the bed. Jen giggled and tried to squirm free, but I was too strong for her. Rolling her over, I pinned her face down on the bed. She was laughing, but her voice was muffled by my cum soaked bed sheets. I grabbed one of her arms and pinned it behind her back, completely immobilizing her prone, tanned body underneath me. I took a moment to gaze at her body before dropping my head to her ass. "Hey! What are you doing?" she asked, half giggling. "I told you." I replied. "I'm going to kiss it better." With my free hand I pulled one of Jen's ass cheeks to the side, exposing to my view, the tiny asshole that I had just violated. It looked a little red and swollen with a tiny rivulet of cum running from it. "No!" she squealed. "You can't do that! You can't...Oh....Mmmm." Jen's voice trailed off as the tip of my tongue flickered across her puckered little pink ring. She stopped resisting but I remained holding on to her arm as I lapped at her asshole. Jen's cries of protest turned to moans of pleasure as I planted a deep kiss on her butthole, surrounding it with my lips. I let her arm go free and she immediately reached back to grab her ass with both hands, spreading her cheeks wide. I smiled to myself as I resumed licking. My best friend was fast becoming my own personal anal plaything! "Oh my god that feels good," she moaned. I moved up, planting soft kisses up to her tailbone as I gently grazed a finger over her wet little hole, which was slippery with two of my bodily fluids. I pushed the tip of my finger inside her ass as she reached under to slide a finger into her pussy. When she didn't protest, I slipped my finger in farther as her slippery little asshole swallowed me up to the knuckle. I could feel Jen's own fingers through the thin wall separating her pussy and ass. "I want it again." she moaned. "I want you to fuck my ass again." "Really," I asked, sliding my finger in and out of her butt on a river of warm cum. "I thought you didn't like it?" "Just do it. Please! "Fuck my ass! Fuck my dirty little cum filled asshole!" How could I resist. Withdrawing my finger, I positioned myself behind Jen once again as she assisted by spreading her ass cheeks wide. I swiped a finger down her crack, collecting as much of my own cum as I could before slathering it all over my cock to use as lubricant. As the tip of my dick touched her sensitive ring, she grabbed me by the shaft and pushed her hips backwards, forcing my dick back inside the tight confines of her delicious asshole. I was surprised, but pleased with Jen's newfound aggression and scolded myself for not trying anything with her before. She wiggled her hips as the remainder of my cock slipped easily into her slick little butt hole. "Mmmm," she moaned. "It feels way better with a little lube." "Good thing I didn't cum on your face then huh?" "Yes. I love the feeling of your cum in my ass. I feel so dirty! I feel like a... Like a whore!" Jen was slowly grinding her ass backwards into me, urging me to fuck her. "Come on! Fuck me. Fuck me hard this time." "Okay," I said. "You asked for it." With that I grabbed Jen's hips and slammed myself into her, driving my cock deep into her tight little cum filled asshole. "Oh fuck!" she squealed. I smiled to myself as I withdrew only to drive back into her. Each thrust emitted a lewd squelching sound due to the liberal amount of jism I had recently injected into Jen's hole. I looked down and marveled at the sight of my glistening cock sliding in and out of my friend's impossibly tight butt hole. The movement of my dick was forcing some of my cum out of her ass, which squeezed out from around my shaft, dribbled down the back of her thighs and dripped down onto my bed sheets. "Fuck. Fuck. Fuck." Jen muttered as each thrust of my hips repeatedly buried the length of my cock into her well-fucked asshole. Driving my hips down hard, I pinned her petite body against the bed, with my cock firmly embedded inside her. Reaching out, I took hold of her arms and held them in place as I slowly gyrated my hips, grinding my dick into her ass. The entire length of my body was pressed against the entire length of her body, the sweat from out skin forming a cohesive seal between us. As I gyrated my hips, I kissed her ear before whispering to her. "Do you like it?" I asked. "Do you like my dick in your tight little asshole?" "Yessss," she gasped. "I love it!" I smiled to myself as I peeled my body off hers and propped myself up with my arms. Then, withdrawing my hips, I pulled my cock free of the confines of Jen's impossibly tight hole. "What are you doing?" Jen asked, looking back over her shoulder with a disappointed but confused look on her face. Without a word I grabbed Jen's petite body and flipped her onto her back. Then, hooking my hands under her legs I pushed her knees up to her head, exposing her ravaged asshole to my view. I smiled as I gazed down at her glistening hole, which was also becoming quite red and swollen. "Quite looking at it and fuck it!" Jen ordered, grabbing her own ankles. I snickered and dropped my head down between her legs. "What the hell are you....ohhhhhhh." Jen's voice trailed off in a low sexy moan as my tongue touched her abused and stretched asshole. I circled her anus, running my tongue around her rim before sliding it inside. "Oh my God!" she exclaimed. "That feels so fucking good!" I pulled my tongue from her ass and quickly replaced it with my dick, which slid easily inside. Jen was holding her own legs by her head, splaying herself wide open for me as I resumed fucking her wonderful little hole. "You know, I've never done it this way before," I stated, sinking my cock up to my balls in her ass. "Well, don't I feel special!" Jen blurted back. I smiled at her sarcasm and started fucking harder than ever before. I soon lost track of time as I concentrated on the feeling of my friend's tight asshole swallowing my cock. Our new position gave Jen the perfect opportunity to play with her clit, and she released her legs to work at a second orgasm. "Oh fuck I'm going to cum!" she gasped. "Oh fuck! Oh fuck! Oh fuck!" I could feel myself getting close as well. "Where do you want me to cum?" I asked, now frantically plowing her poor little asshole. "Fuck, I don't care!" she yelled. "On my face! Cum all over my fucking face! Cover me in cum! Ass fuck me and then cover me in cum! Jen's words must have had the same effect on her as they did on me, because soon she was screaming her way through her second anal induced orgasm of the night, as her asshole clenched around my cock. While she was in the throws of her climax, I yanked my dick from her butt hole and lurched forward in an attempt to get closer to her face. "Yes! Yes! Yes! Yes!" she howled as the hot cum fired from my dick onto her pretty face, splattering her lips and chin, and dripping into her mouth. I collapsed back onto the bed as Jen lay there panting. It took a few moments for both of us to regain our composure, and a few more for either of us to speak. "Well?" she asked. "Was that dirty enough for you?" I laughed. "How about double or nothing?" Jen scoffed and reached down to gently stroke her severely abused asshole. "I think I need a few days to recover," she answered. I just laid back and smiled. I knew that things would never be the same. And I liked it. The End Send comments and suggestions to the address in my profile. A Friendly Breakup Beth sat down opposite me at the table in the secluded part of the coffee shop. She was very beautiful and the way her hair glowed in the noon sun made me feel very small for what I was about to do. I used to have the image in my head that a girl named Beth would have black hair and fairer than average skin, my Beth wasn't like that at all. She was a blond with an athletic build and stunning eyes. She reminded me a lot of comic book character's girlfriend with the way her smile was completely adorable and she could hypnotize you just by biting her bottom lip. "This is a nice place. When did you find it?" she commented. "Um, about a year ago, I guess." "You have to take me here more often." "Anyway, There's something we have to talk about." "Before I forget," she interrupted, "My cousin is getting married next month." "Wait. I need to get this out." She stopped and then put her hands in her lap which gave me the signal to go ahead and that she was listening. "This isn't working for me." I said. She slanted her eyes and tilted her head as if her mind was trying to figure out where I was going to go with this as if it wasn't completely obvious. "Um. You are a really great person. I care about you a lot but I have issues that I have to deal with and I'm not going to be a very good boyfriend for the foreseeable future. You deserve to be with someone who will be totally dedicated to making you happy and I can't do that right now." "You're breaking up with me?" I had planned for her to say this of course. I had thought that I had everything planned out. The truth was, I really did care about her. I really did think she was an amazing person and if it really was my choice I would stay with her. But I'd had enough girls break up with me in high school and college that I knew the signs. Beth was loosing interest in me. She was starting to be less and less impressed with my life and my accomplishments. Our previous date together had been a test. I tried to score for the first time one last time but she said she wasn't in the mood. When a girl says no you have to respect that and stop pressing so I backed off. We'd been dating for three months at that point and I knew that if I wasn't getting her into bed by then that it was only a matter of time before I'd find her in bed with someone else. I had learned the hard way, multiple times, that you just can't leave it to the girl to end things. If you do, then she will go for maximum pain. She will belittle you. She will insult you. She will convince herself that you are the most vile thing on the planet and that you deserve all the hatred and venom she can throw at you. With me in control I can be gentle about it. I don't have to go for the jugular. I didn't want to hurt her. "I don't want to but I have to do this. I can't put it off any longer." "Why?" "You deserve better than me." "That's just an overused, bullshit excuse." she was getting mad. "I have something very serious that I have to deal with. I won't have time to be there for you." "What is it?" "I can't tell you." "You better start making some sense." "This is hard enough for me to do without you yelling at me." "You owe me more than just vague, I have to do this." "You're right, but I can't say any more. It would be wrong. I can't put this on you." "Look, whatever it is, we can deal with it. I'm here for you. I'm ready to support you." "It's too big. It's too hard." She looked at me with concern. "What is it? Let me help." "I'm afraid, it's too late." "Are you going to jail?" "No." "Then what? You got a girl pregnant?" "No." "What is it? You can trust me." "I know I can. And I love you for that but for right now I have to find a way to deal with this myself before I could even ask for help." "You're gay." "No. Just trust me. It's big and it's complicated. You don't need a mess like me in your life. I'd wish anything if we could stay together but I just can't see that happening right now. I'm sorry." That seemed to be the end of it. She sat quietly in acceptance. "Fine. I'll wait for you." "You don't have to do that." I rebutted. "I insist. I'll wait for you. You go conquer your demons and when you're ready, I'll be here for you. I love you." The "I love you" part of that shocked me. She'd never said it before. I wish she had at least just said that on our last date and I might not be doing this but now I was committed. "You don't understand. I may never be able ..." "You're dying." "No. I ..." "You have cancer." "No, just listen. I may never be able to come out of this and even if I do I don't know how long this is going to take or what sort of condition I'll be in when it's all over. I can't ask you to wait that long. It wouldn't be fair." I tried to get up and leave the table but she grabbed my arm. "Wait. I don't want to loose you. Not like this. I'll be a good girlfriend. I want to be with you. Together, we can defeat anything." "Not this." "Now you listen. We can defeat anything. Anything. We can do it together. Just let me in. Don't you trust me." "I do but ..." "Then tell me what's going on. NOW!" This was dragging on too long. I should have been out of there by then. She would feel good about herself and not feel angry towards me but the relationship would be over. But she wasn't going to let that happen. So I had to be the bad guy. Time for plan B. Sure, I thought up plan B on the spot and in retrospect it was a bad plan but I was growing nervous more and more by the second and the other customers were starting to look over at us. "I had sex with my next door neighbor." Her mouth dropped. "You did what?" This was a lie but at the same time it was the truth. I should probably explain that. My next door neighbor was named Liz. We'd met in college but weren't really friends or anything. She was just someone whose name I knew really. After moving to the city I happened to bump into her at a party held by a mutual friend and I mentioned that I was looking for an apartment. She mentioned that the apartment next to her was empty so I applied for it and got it. Once I moved in, we really hit it off. We became really good friends. It seemed like I was always over at her place or she was over at mine. We went to baseball games together. We ran in a marathon together. We could talk about anything and it wasn't weird. She was my best friend. We were joking one night about how people make pacts with each other that if they aren't married or had a family by a certain age then they would hook up. We laughed about it but then decided that we would make a pact. If we were both childless and unmarried by the age of 35 we'd tie the knot and have some kids. Why not? It was never really going to happen. Then came the night that we both came home after really bad dates. We were both feeling pretty low about ourselves but once we were in each other's company, we cheered each other up. Then we made a new pact. We were going to have sex that one time, no strings attached and in the morning we had to go back to being just friends. Our friendship was way more important than anything else we had going on and Liz especially didn't want to jeopardize it with dating drama. Like an idiot I agreed to this. So we slept together that one night. It was amazing and I really started to feel like maybe I was falling in love with her. But she held firm. We could not become a couple because our friendship was too important and might be destroyed if we dated and then broke up. But then we had sex again. And then again. She was my best friend and I was totally comfortable with her. I could marry her. I felt like asking. But she didn't want anything to get weird. I knew I was starting to have much stronger feelings for Liz. If things continued like this I was going to get hurt when she eventually decided to date someone else. As soon as I felt myself becoming possessive of her I knew things had to change. I met Beth at a very opportune time. I took her out and we hit it off. On our second date I brought her back to my place and we got surprised my Liz, who cooked a very big dinner and invited us over. The night was a bust sex wise but the two ladies seemed to be pleasant with each other. After dinner was over, Beth had to go home and then I had to have the talk with Liz. I remember it well. "She seems nice." said Liz. "I like her a lot." "I can see that." "I hope you aren't mad." "Why would I be mad?" "You know." "You were great but one of us had to move on eventually. No tears." "I wanted to tell you ..." "Don't make it complicated." "I wanted to tell you that I would have wanted to date you. I really would have." "I know. But this will be good for you. She's nice and cute." "Yeah. She's really great." "So, I'm here for you, as your friend. That's what we agreed. Now make it work with Beth and I'll be happy for the both of you." But of course it hadn't worked out with Beth. As the weeks dragged on, I still wasn't getting any sex. She just never wanted to and I knew enough not to push a girl for sex after she already said no. Then she started wanting to spend less time with me and more with her friends. Again, that's perfectly ok but it is a clear sign that things are off. Then we were out on a date at an amusement park and I thought things were going well but she wanted to sit and get our portrait done by a painter and the price he asked for the painting was more than I had on me. It was embarrassing and then after Beth paid for it I felt really small. She didn't seem to be happy with me anymore. She smiled and all but there was less energy in it. The break up was coming, she just had to talk herself into it. She didn't' see me as exciting or interesting anymore. She made up excused as to why we couldn't spend time together. She was tired of me. I knew the steps after that. She'd start to resent me and then feel like I was holding her back. She'd start to see me as needy or somehow below her. She'd break up with me in the most hurtful way she could think up and I'd be devastated. She'd leave a black hole of white hot pain in my chest just to make herself feel good. So I decided to be proactive. I was going to break up with her. She might get mad but at least I'd make an effort to not hurt her and since I was the one doing the breaking up my emotions would be safe. Yet, there I was in the coffee house with her looking pissed and not wanting to let my arm go. "You did what?" she accused me. "Ok. Fine. You want it to be like this then that's how it has to be." I was going on the offensive. "I had sex with Liz. I admit it. I'm a bad boyfriend. You're entitled to hate me." She was speechless but she also wasn't letting my arm go so I pressed on. "I'm not the kind of guy who's going to lie to you or keep secrets from you and I don't expect you to forgive me. Don't ask me why I did it. There is no why. I obviously have issues I need to figure out and you can't help me with that and I wouldn't expect you to." I tried to get away. I tried to pull my arm away. But she wouldn't let me go. "We can." she said. I didn't understand what she meant. "We can ..." she continued. "We can work through this." "Um, say again." "You were honest. You cared about my feelings and you didn't want to hurt me. You'd rather break up with me than hurt me. That just tells me that what we have is special. It's worth fighting for." Now it was my turn for my mouth to drop. "W ... wwwwhat?" I sat back down. I had to hear this. "You know. I knew it. When I saw you together with her there was something going off in my head. I knew something was up. I knew you had some kind feelings for her but you both insisted so much that you were just friends." "We are. I'm not leaving you for her. It was just something that happened." "You love her, don't you?" I decided not to lie. "Yeah. I love her. I care about her a lot. But she made it very clear that she wasn't going any further with it." "I'm so sorry." "For what?" "I can only imagine the pain you must feel. You're caught between two women you care so much about." I wouldn't have phrased it like that but ok. This was my opening. I was going to go for the break up again. "That's why I think it might be best if I was just alone for a while. I'm confused. I don't know how I'm supposed to feel and I never wanted to hurt you. So please, just give me some time." "Hey. I'm here for you. Whenever you need me. I don't hate you." "You don't?" "How could I hate you? I love you. We can get through this. I want to be there for you." "You do?" "Of course I do." I looked at her. Was she trying to one up me on the break up thing? She seemed so sincere. "Ok, so then, what do you want to do? You probably can't ever see yourself having sex with me after what I did. Without that, I don't see how a relationship could even work." "Our love is too strong for something like this to bring it down. We'll make it work." "How?" "With love." I returned to work after my extended lunch break and the strangeness of the conclusion was on my mind all day. Beth was still my girlfriend and as seemingly as much into me as she had ever been. My walk home I almost felt like I was going in slow motion as I changed from one form of public transportation to another. I walked up the steps to my apartment building and got past the auto lock. I took the elevator up to the 12th floor where my apartment was. It was like I was on automatic pilot. I put the key in the lock for my door and then someone tapped me on the shoulder. "Guess who." said Beth. "You're here?" "Yeah. I came to talk to Liz." Then I was scared. "Was she home?" "Oh, yeah. And we had a nice long talk." "Oh, really." I got the door open and then retreated into my kitchen. "I asked her about what you said." "Why?" "I'm a woman." "I can't have any violence here. I serious." "It wasn't like that. Calm down." "What did she say?" "It's funny. I asked her what she thought you might be like in bed and you know she said she wouldn't know." I shook my head. "That's the wrong way to go about it. Of course she's not going to fall for that." "You didn't just make all that up, what you told me before?" "No. Why would I make up something like that." "I don't know. Maybe you didn't like me anymore. Maybe you were trying to hurt me." She was starting to sound a little crazy. "Maybe you really are just an asshole." she continued. Now she had come full circle. She had convinced herself to hate me. "Fine. If that's what you want to believe then go. Go think whatever you like about me. Just not here." "Not until I get to the bottom of this." "There is no bottom. You did you investigation." "No. Now you have to ask her." "Why would I ask her? I know very well what happened. I was there." "Keep your phone on and I'll listen from this side." "That's illegal." "Then I'll listen at the door." I shook my head. A plan formed and I executed it. I marched over to Liz's door and knocked hard. Liz answered. "Liz. I'm really sorry to bother you and I apologize for being a kiss and tell but please let my girlfriend know about what we did." "What do you mean?" asked Liz. I gave her my wide eye look so she hopefully would get the hint. "About the times we ... you know." Liz rolled her eyes and then took in a deep breath. She turned to Beth. "Ok, yes. We did. But it was months ago before he even met you." "All you had to say was 'yes'." I was frustrated at this point. "What?" Liz asked in her own defense. "You wanted me to tell her so I'm telling her." "Then, he didn't cheat on me?" asked Beth. "Victor? Cheat? No way." said Liz. I had to take control of the conversation again because who knows what would happen if you just left it to two women to handle. "Beth, the problem is, I have feelings for Liz. I have very strong feelings for Liz. I have to say it Liz. I love you. I'm in love with you. And Beth I care a lot about you but it would be wrong of me to stay with you as long as I feel about Liz the way I do." A tension hung in the air and for a moment no one spoke. Then the silence was broken by Beth. "Liz, I think I'll have one of those cookies now." "I got them right in here." Beth entered Liz's apartment. I tried to follow but Liz stopped me. "Hey, um. I don't know what all this was, but you suck at it." She closed her door on me and I was left in the hallway alone. I was very nervous back in my apartment. I knew I shouldn't have been. If Beth left me then that's what I was aiming for. But the thing I was really worried about was losing my friendship with Liz. I think I might have botched it. She might never forgive me. She might never want to see me again. If that happened, I couldn't stay here. I'd have to move. I couldn't stand living next to her and everyday feel myself pine after her. I'd have to move. I'd have to find new friends. Change could be good. I'd never be able to show my face around here again but change could be good and maybe in the nine years we still had left before the pact came due one of us would get married and even that would go out the window. Anyway, it was dinner time. My frig was empty. I so often went over to Liz's place for dinner or went out with Beth that I just never had anything. I flipped a coin. Heads, order pizza. Tails, buy groceries. Tails. Damn. I meandered through the supermarket for an hour or more and in the end I bought very little. I saw a sign that said "organic coffee" and I started laughing so hard I nearly fell down. Of course coffee is organic. It could never be otherwise. Caffeine is a natural insecticide and coffee blooms all year long so farmers have no incentive to ever use fertilizers or chemicals on the trees. So while technically it was true that the coffee was in fact "organic", why would you pay more for that when literally all the other coffee in the world was also "organic". I had little in my bag but at least I had a smile on my face. I was alone but at least I was happy. I passed Liz's door on my way home and it was open. I was actually going to rush past and save myself any more humiliation for the day but Liz called to me. "Vic, come see." "I have ice cream. I have to get it into the freezer." "Put it in mine." she said and then I got a look at what she was wearing or rather the lack of what she was wearing. She grabbed my tie and pulled me into her living room and shut the door behind me. She took my bag and brought it into my kitchen. "What's going on?" I asked. "What do you think?" "Where's Beth?" "She's gone." "Oh. I guess..." "Don't worry about her. She's not here." "Still, I didn't want ..." "Shhhh. Relax." Liz said and put a finger up to my lips. She then started to unbutton my shirt. I didn't dare protest. "Are you sure?" I asked. "Do I look at all unsure to you?" No she did not. In fact, she was the sexiest thing on the planet as her skimpy lingerie barely covered her and she was very aggressively getting my shirt and tie off. I moved in for a kiss and unlike previous times when we had sex where the kisses seemed functional enough for what we were doing, she kissed me back with great passion. I wrapped my arms around her and I just wanted to hold her forever. The word propose went through my mind. Did I really have to wait until I was 35 to marry this woman? I didn't want to take any chances. Liz began kissing me all over and her kisses moved down to my belt line. She got my pants undone and started pulling them down. She wasted no time and got my cock into her mouth. A Friendly Breakup I already knew that Liz gave great blow jobs but this one was fantastic. She couldn't take all of me into her mouth but I really didn't want her to. She wrapped her hands round my shaft and lubed them up with her spit. Then the head and just a bit more was in her mouth but the entire combination together gave me the sensation of extreme pleasure. I could have cum right there. But I didn't. There were further attractions and I wanted to see them. She led me into the bedroom and I took my time undressing her. I wanted to savor this. I kissed her slowly and made sure every inch of her body got a little attention. Her breasts were the most perfect things on the planet. They were all natural and wonderful and I enjoyed not only sucking the nipples but lightly brushing the sides of her breasts and then moving my lips from there, down the side of her body and then to her panty line. It was finally time to remove her panties. She was so wet that they were almost soaked through. I was going to go down on her but she actually pulled me back up to her. She kissed me fiercely. One hand grabbed some hair on the back of my head and the other hand guided my cock into place. I was again inside her. We fucked slowly and deliberately. Each thrust lasted half a minute or more and we sought to put the maximum effort into each one. My cock did not just go directly in and out. She had her hips at some soft of angle where she was actually able to glide her clit up and down the shaft of my penis before slamming it into my pubic bone and then we would hold it there and press for a moment. It wasn't wild sex. It wasn't kinky sex. It was passionate sex where there was a lot more going on between our bodies than just our movements. We were both sweating. We were both gasping for air and we both climaxed at the same time. She arched her back under me and dug her nails into my shoulders. I ejaculated and filled her pussy with my cum and with each blast I felt my entire body tense up and release. We both needed a rest. Eventually Liz spoke. "I thought we had a rule." "I didn't know if we were going by that any more." "Well we are. So, for the future, please remember." "We have a future?" I asked. "Of course we do. You're the best I've ever had. If I get a boyfriend and he can't live up to you I may just have to go next door and jump your bones behind his back." Then she added, "If you don't mind." "Why would you need to find another boyfriend?" She looked at me. "We'll talk about it later." "But ..." "Right now, you need a shower." She waver her hand in the air. "Smell that? You definitely need a shower." She wouldn't let me protest. She got the water going and then pushed me in. When I was done I just felt like going to bed. I wasn't even hungry anymore. I just wanted to get right back in bed with this woman. But when I got out of the she shower she was waiting for me with my clothes. I was confused. "What did you think?" she asked. "You aren't sleeping here. That's what you have your apartment for." I tried to protest but I was speechless. Did she have a guy coming? Another guy? She got me dressed and the pushed me out of the front door and into the hallway. "Hey, stud. I'll see you tomorrow. Have fun." Then she slammed the door. What was that supposed to mean? I was so confused by everything I even forgot to get my ice cream. I let myself into my place and by this time I was awake enough to realize I had nothing to eat in the frig and the food I had bought was locked away from me. I didn't feel like going out again so I started to order a pizza. "Tell them I want pineapple." said Beth's voice from my bedroom. I hung up the phone to investigate. There on my bed, in my covers was Beth who was clearly in some stage of undress. "What are you doing here?" "You gave me a key. Remember?" That was not the answer to my question and in fact I did not remember giving her a key. "We can't do this." I said. "Why not?" "Because I just ..." She didn't let me finish. "You didn't do anything. Shhhhhhh. I know I've been holding out on you but honestly I just thought you wanted to wait. Most other guys are so pushy about wanting it now, now, now. But you were so sweet the way you listened to me and didn't try to force me. You're the best. You let me wait until I was ready and I'll always love you for that." "I have to tell you ..." "I can't hear you." she said. Then she did that thing where she bit the corner of her bottom lip and smiled and I almost melted. "I want you to feel about me the same way you feel about Liz. So I want you to remember the last time you were with her and then imagine I'm her and all those things you remember doing to her; I want you to do them to me." I hesitated but she wrapped the sheet around herself and came up to me. "I'm your girlfriend. You owe this to me." I couldn't argue with that so I went in. I didn't expect her to give me a blow job so I aimed for her breasts and took my time heating her up. She took a bit longer. Unlike Liz, every part of Beth's body was new, virgin territory for me. I had to learn her sweet spots. I had to see how she reacted. Also, unlike Liz, she was much more willing to explore with her hands as well. She ran her fingers over my chest muscles and down my abs. She grabbed at the muscles on the back of my arms and giggled. When she was finally ready, she grabbed at my butt and seemed to take pleasure in getting a handful. Being inside Beth wasn't the same as Liz. We didn't have the same intense dynamic. There was more thrusting, Beth did a lot more moaning and yelling, and we eventually had to switch positions. Beth got on top of me and lowered herself down onto my cock. Up and down she slammed her hips into mind and finally found the sweet spot where she could press her clit along the shaft of my dick as it went out and the she would tilt her hips so the head of my cock pushed up into her G spot for a brief but wonderful moment before submerging completely into her pussy again. She started to have her orgasm and as it powered through her body I thought perhaps I might not have one but as she was finishing hers and had her eyes shut tight I started to have mine and I tried to tell her to get off of me. That signal snapped her back to life and I tried again to let her know I was going to cum but she resisted me and forced herself down on me even more. I had no choice but to cum inside her. I was spent. I had never in my wildest dreams thought I would be with two different women on the same day. I could go more, mind you but you have to warn a guy so he can get ready. I took a shower, again, and got dressed, again. I was going to order pizza but then there came a knock at my door. "Room service." said Liz when I answered and she carried in a feast she had prepared. She was wearing only a bathrobe as she set the food out on my little used dining table. Beth came and sat down at the table with only my bed sheet around herself. The two women shared a knowing glance between each other. "There you go. Y'all eat up. I'll leave you two love birds alone." Liz said and then headed for the door. On her way out she turned to me. "And Vic, tomorrow, try to remember the rule. She likes that stuff in her, but I don't."