ass fucking

“Are you really going to let me fuck him?” the man said, shocked.



She gave him a wry smile, “Of course, but be gentle. I can’t have you breaking him.”



“Ca…can I have him inside me after?” the man said, rock hard cock throbbing visibly. “Please, Mistress? You could see if we could make each other cum without jacking off…?” The idea was a good one, she had to admit. But did she really want him fucking another man? Even if she had just seen him suck the man? Her soaking wet pussy said otherwise and she had to admit how much the idea turned her on. Besides, she knew the only circumstances where he’d do this would be when she was there…and he had been such a good slave lately, he deserved a treat.



“Yes…you are really going to fuck him.” The man’s cock throbbed visibly. “And yes…he will fuck you after he takes a break to eat my pussy.”



She smiled to herself…her plan taking shape in her mind.



She went to the drawer and withdrew handcuffs, a bottle of lube and her pink rabbit vibrator. She took her boyfriend and led him naked to the desk chair, she slid his hands through the bar on the top and handcuffed him so he couldn’t move.



“Painful?” she asked. He shook his head, she could see his cock growing harder as he prepared himself. “Put one leg on the chair and stick that sweet ass out for me, pet.” He arranged himself for her and she ran her hand over his ass, making him shudder. She tossed the bottle of lube to the man and tied the key to the handcuffs around her neck. “Lube him up and he’s all yours, but be gentle…you’re bigger than what he’s used to and I won’t have you breaking my toys.”



“Thank you, Mistress.” He and the man moaned simultaneously as the man lubed him up. She went and sat in front of her slaves on her bed, she spread her legs so he had full view of her pussy and could watch her pleasure herself as she watched him getting fucked. Her fingers began to gently play between her lips as the man aligned his rock hard cock with her boyfriend’s sweet ass. Both men were breathing heavily and he groaned loudly as the man began to slide his cock inside.



It was bigger than anything he had felt before and when the man pulled out he whined and thrust his ass out, the emptiness was excruciating. The man complied and thrust back in, pumping harder and harder until he was buried to the hilt. He moaned in pleasure and pushed his ass back in hopes of more. His own cock throbbed wildly beneath him and all he wanted was to grab it and squirt hard. The man paused his thrusting to twine his fingers though his hair and run his nails down his back.



He moaned then looked up to see Mistress with her pink rabbit shoved deep inside, her eyelids fluttered and he could smell her juices…she was so close. Yummy



“How does it look, Mistress?” he asked as the man resumed his thrusting. “How does your slave look being fucked hard by your slave-friend? Can you see my cock throbbing? If he fucks me any harder I might cum? Do I have permission to cum for you, Mistress?” this set her off, she began coming all over her fingers, moaning loudly and he could see her juices running down, soaking her sheets. As she regained composure she stood up.



“How does it feel, pet? To have a real man fucking you?” she ran her hand over his lips, letting him taste her. He moaned and thrust his ass back making the man moan.



“Yes…oh god it feels so good…better than anything I’ve ever felt, I’m gonna cum soon, please may I cum soon?!”



“Not yet, darling.” She walked behind the man and stroked his back. “How is my boyfriends ass?” “So tight, Mistress…I’m gonna cum soon, may I cum? Please? I can’t hold off much longer…I’ve been trying not to cum since I got inside him.” She put on hand on both of their heads and pulled their hair slightly. “How badly do you want to cum? Do you need to cum? Is it getting painful holding back?”



Both men nodded vigorously begging her to let them cum. She released their heads and perched herself on the desk next to them. She strokes his hair gently, “Cum for me, pet. Lets see you squirt for me. You know how hard I cum when I see you squirt your cum everywhere.”



The man began thrusting harder and harder into him, he looked down and could see his cock dripping steadily. He could feel the cum boiling in his balls…he was so ready to cum. The man screamed out behind him and he felt his cock expand and pulse his white hot cum into him. The feeling inside him set him off, “Fuck…Mistress…I’m gonna cum…I’m gonna cum. Watch me cum for you!” his hips thrust forward as his contractions milked the last of the man’s cum from his cock as his own cock erupted and she moaned loudly at the sight of it. Stream after stream poured out all over the towel she had laid on the chair.



The man sighed and let his softening cock fall out then went to sit on the desk as he leaned heavily on the chair, still handcuffed. She sauntered over to him, stroking his back and kissing his neck.



“Baby, I’m so proud of you,” she murmured. “Now I want you to eat my pussy and get hard for me again so you can fuck my friend.” He moaned audibly as she grabbed his ass before using the key around her neck to unlock the handcuffs. He rubbed his wrists and stood up as the man came to stand next to him.



“What would you like me to do, Mistress?” he asked, his cock too was soft but that would be easily remedied with what she had planned. She wanted them both rock hard again and begging for Mistress to let them cum.



“You,” she layed on the bed and spread her legs, “can play with my tits while my lovely slave-boyfriend eats my pussy.”



They both looked at her longingly. “Now.” she said and they dove on her. The man caressing and licking her breasts. She moaned loudly as the man sucked on of her nipples into his mouth. Her boyfriend began by removing her panties that were already soaked in her juices. He inhaled her scent and moaned then dove and shoved his tongue deep inside her.



Within minutes she was cumming hard, soaking his face as the man pinched her nipples. She pushed both men away and stood up, regaining her composure as Mistress.



“Stand up, slaves.” She watched as their cocks grew from hard to iron solid before her eyes. “Are you ready?” she asked.



“Ready for what, Mistress?” he asked her as the man nodded.



“Are you ready to fuck my slave-friend?” he moaned loudly.



“Yes, Mistress…please let me fuck him. I want to make him cum.” She nodded and led the man over the bed, she stacked a few pillow and laid the towel over them. The man laid down and she cuffed his hands over his head.



“Lube him up, my pet.” she handed him the lube and the man breathed heavily in anticipation on the bed.



Once the man was sufficiently lubed, he knelt poised over him. He’d never been anywhere but inside his Mistress and he wasn’t sure how he felt about it. He looked at her and she nodded encouraginly. He aligned himself and began to push into the man’s ass. The man moaned and began to push his ass up to take more of his huge cock. It took a bit of work but soon he was burried to the hilt and it was so good.



“How does it feel, pet? How does his ass feel?” she asked, smiling at him. He could only moan as he thrust in and out as the man moaned and writhed in pleasure beneath him. “That’s it baby, fuck him hard. I want him to cum as hard as you did. I want to see it all over his chest. When your about to cum I want you to pull out and cum all over his dick.” She stood up and began to stroke both men’s hair. “How does that sound?”



“Oh god! Yes, Mistress. Please let him cum on my cock! I’m so close…so so close. Please let me cum, Mistress!” the man thrust his ass up.



“Mistress, please let us both cum. I want to cum on his cock. I want you to watch us cum together!” he began thrusting harder and harder into the man. His ass felt so good around his cock, not nearly as good as his Mistress, but so so good.



“Cum for me,” was all she said as her fingers worked furiously in her pussy. He began to thrust his cock deeper and deeper making the man beg for his cock. Suddenly he felt it.



“I’m gonna cum! I’m gonna cum!” the man nodded and shouted the same. He pulled out and jacked his cock a few times just as the man’s cock exploded all over his chest. He began to cum and spurted stream after stream all over the man’s pulsing cock. “Oh fuck! Of fuck!” he moaned as the pulses subsided. He collapsed back on the bed as the man panted.



They looked at each other and at the same time moaned, “thank you, Mistress.”

He treats me just like the woman he’s made me into, like the second wife I’ve become for him. I do all the dirty things his real wife won’t do. I dress however he likes, wear what ever turns him on, do things she would never do for him. The only time I wear male clothing is at the office and he never talks to me there other than in a business-like manner. Our secret is just that…a dirty little secret.



Right now, I’m doing just that, being his dirty little secret. I’m, as always, dressed completely for him. When he arrived he found me in a tight short red dress, barely covered my rear end. It’s off-the-shoulder and very cute. If I bent over you could see everything. I wore red seamed nylons and a lacey red garter belt. I always wear a locked chastity tube for him with a pink ribbon in a bow tied tight around the back of it, pushes my tiny little thing and my balls up and out. I usually wear no panties when he visits. He wants instant access to me, demands it. But this time I wore the special ones he likes, gift for me a week ago. He had them sent to my house, three pair. Sexy, slutty red panties, the kind his wife won’t wear for him. I wore 3″ spike heel shoes for him too, makes me taller but I’m still not as tall as he is. He loves high heels, has me keep them on during sex, he loves that too.



Have my heels on now, up over my head, and my skirt is up over my rear, pulled up to my waist. His big hands are all over my ass. His full weight on top of me, he holds my rear apart so far it hurts, grips my cheeks with both his hands and holds me apart exposing my tight little slippery hole. I say nothing, just moan softly as he fucks me. He fucks me in one of his favorite positions, the missionary position.



He’s huge and when he’s all the way in me I can barely breathe. And he likes to take his time, uses my rear slow and methodically. He likes to fuck. I can tell he likes my tight little rear end, the way he pumps just the head of his cock in and out the tight rim of my little hole. He uses me for his pleasure, not mine. I squeeze as hard as I can and try to please, keep tight around him as he fucks me. He’s been on top of me for an hour.



“Oh, you little bitch.” I feel him slap my rear and then take my cheek back tightly in his hand and pull me apart again, “Ooooo, you love that, tell me. I’m going to cum in your mouth you little whore…Oh….fuck, so tight…” He slides in and out of me, full length so slow and sexy.



I whisper in his ear as he loses himself to my rear, put my legs up high in the air, one leg around his rear end, stockings unhooked from my garters and a complete mess, one down around my ankle. My smooth shaved leg around his back rubbing his ass, other one up over his leg from behind…only sound in the room is the bed springs and his cock moving in and out of my slippery rear. He pumps me the full length of his huge cock, slowly in and out of my tiny hole over and over.



“Daddy, fuck me. I’m your little girl, love it when you do this to me…fuck me. I want you to put it in my mouth, Daddy, please, please cum in your little bitch’s mouth. Please.”



He loves when I talk like that for him, whisper low and soft into his ear, drives him crazy. I run my hands up and over his back, the cheeks of his tight and muscled rear end, my red lace panties dangle from my right ankle, off of my high heel shoe. He’s all man, feels huge as he’s on top of me.



I can feel him getting close, wrap both of my legs tight up and around his back. I feel him start to fuck me hard like he does when he’s ready to cum. It hurts when he fucks me this hard but I don’t say a word about that, just whisper in his ear, whimper for him. He pounds into me, pushes me into the bed, lost to my rear end.



Then he pulls out like he always does, fast and abrupt. He hurries up across the top of me, his stomach on my chest, see his rock hard cock throb as it moves toward my face. Roughly, I feel his hand go to the back of my head, guides my mouth up to him, guides me firmly onto him, my lips wide open. I take it in my mouth, hurry to do that before he spurts onto my face. As he mounts me I put my mouth around him, hold him in place and let him finish. He cums using my slippery lips. Feel him start to fuck me real slow, hear him cry out and moan as I swallow for him. I feel him pump slowly into my wet mouth. It’s how he always finishes. He uses my mouth.



His wife won’t do that for him. He knows I will. He cums in my mouth and makes me suck him until he’s completely finished. I can taste my rear end on him, got used that a long time ago. It’s what he wants, what he wants to know I’ll do for him. I hate the taste but say nothing. I know he likes that too, likes making me as submissive as he can.



*******************



I remember the first time he took me like this and used me rear end, first time he did something other than use me to suck him. I sucked him almost exclusively twice a week for the longest time, he’d cum after I went down on him and then would just leave. As I walk to my makeup table next to the bed I think back on how he first took me like this. Told me to be in only heels and stockings, nothing else, be ready and lubricated, shaved baby smooth, he told me to be on my knees face down on the bed and waiting when he arrived. He said something I’ll never forget, was crude but I said nothing, ‘Make sure that asshole of yours is slippery enough to get my arm up into’.



I did, used half a tube of K-Y Jelly on myself, stayed on my knees for an hour after he called, waiting for him to walk into my house, remember practicing pushing my rear out and back for him .



My heart raced as I heard him come in the door, he had a key to my house at that point. I was upstairs in the bedroom, very ready for my man. I looked back over my shoulder at him as he walked into my bedroom. When he did he just smiled that dirty smile he has. He sent chills up me when he ran his finger up the crack of my rear and then up my back and then back down. Remember him reaching up between my legs, patting my balls. I had never been used like this before, I knew what he wanted to do, was scared and excited at the same time. I watched him from the side of the bed as he took of his pants. He was hard like he always is when he arrives. I love that about him. Took his underwear off and dropped them to the floor. He told me that I was to stay perfectly still and that if I moved he’d blister my rear, spank me hard. He’d never said or done that before. I said nothing. I reached back and held my cheeks open, turned my face away from him to the side. I could feel him as he moved up behind me. I felt him take me by my hips in his large hands and pull me back toward him, felt his hard on run up between my cheeks, just playing with the slippery crack of my rear. I could see my pretty pink lip gloss and dark mascara eyes, felt sissy like and fem as I watched in the bedroom mirror seeing this real man move up behind me.



And then he did it for the first time, put the head of his erection to my little hole and pushed it in. I whimpered, cried out. It hurt, hurt very much. He took his time, made me squirm. It felt like he was too big to fit into me. I felt him slap my rear and tell me to be still, hit me again so hard I closed my eyes. He took it back out, ran it up between my cheeks again and petted my rear.



“You’ll get through this, it’s what you want. It’s what you are. Fuck, you are so tight, I love it!”



I remember him saying that as he put it to my hole again, then he pushed it in slowly. He pushed it in as far as it would go. I started to cry softly, it hurt, really hurt at first. For the next what seemed like an hour he fucked me slow and deliberately. I clenched the sheets of the bed so tight, never let go of them. He just used my rear for his pleasure, used me like the slut I was for him, training me to take his full length. That was the first time.



When he came in me I had my face buried in the bed, fingers dug into the mattress and sheets, my make up smeared all over the sheet in front of me, tears in my eyes. When he completely finished he pulled out of me and patted my rear. He told me I was a very good little boy. I stayed fixed in place, was afraid to move, felt his warm cum run out of me and down my leg, felt it run across my tiny balls. Felt my rear spread like it had never been before, I felt like I was completely his now. He came to the side of the bed and took my head, made me suck him clean. I hated the taste of him after he fucked me but couldn’t deny him.



When I finished cleaning him he pushed my head away. Saying nothing got dressed and left. He just left, left me on the bed a complete mess. I felt stunned, seemed like time stood still.



The next day at work he ignored me, didn’t even say ‘hello’. That was the first time he fucked me. I remember it all.



*****************



He rolled off of the top of me. “Fuck, that mouth of yours never ceases to amaze me, Princess!” He sat up in the bed.



I got up and moved to my makeup table. I hurried to fix my stockings, fastened them slow and sexy to my lacey garter belt, knowing his eyes were all over me.



I’m standing, bending forward at my makeup table. When he finishes I always hurry to do my make up for him, make myself presentable again.



“I do it all for you, Daddy.” I smiled at him.



As I lean forward and apply fresh lip gloss and lip liner I push my rear back out, I know he finds that sexy. My dress is still up over my butt, panties down on the floor, shaved smooth round little rear end for him to look at. I spread my ankles apart slightly, give him a good look. Skirt up, bare butt, sexy stockings and heels, I know I’m just what he wants. I wink at him, “You like what you see, baby? It’s all yours to what you want with.”



He just stares at me.



He moves to the chair next to my bed, sits, watches me fix my makeup, primp for him. He smiles as I wiggle back into my dress without my panties on, pull it down teasingly over my cock harness. I tuck my little thing back down between my legs and pull my dress down, smooth my skirt as it moves down from my waist, feel it cover my rear tightly. I can feel the k-y all over my rear end, know it’s staining the back of my dress, don’t care. I love him on me. I fix my stocking seams and then check my lipstick again. I look at him in the mirror. I’m wearing a blonde wig, big hair…he loves that. Pink bow in the middle front with sexy bangs, I re-apply lip gloss as he leans forward, runs his hand over my rear, over my silk dress.



“So, you ready for the next step, Princess?”



“Daddy, I’m ready for anything you want me to do. You know that.” I smile at him. He’s naked, even soft his cock is huge. He’s all man. Feel the urge to suck him again, want more of him…but he’s done with me now. “I’ll do any dirty little thing you like.”



“I want to take you out in public.” He looks at me, sees the shock on my face. “Take you to a special club, one that you would fit into, want to show off my little slut. I know about a couple of bars that have girls like you in them. I want to take you to them.”



He runs his hand up between my legs, feels my locked cock harness. Feel his huge muscled arm push up at my tight skirt as he feels me under my dress. Then I feel him take my arm tight, pulls me down on his lap. Sitting on his lap I feel him take the back of my neck in his hand.



“That scares you, doesn’t it.” He holds me in place and runs his other hand over my inner thigh, plays with the lace at the tops of my stockings. “Scares you to think about going out on the street like this.” He laughs, “It should. So far you’re a secret. If I make you a public little sissy bitch you’d just have to do it, wouldn’t you?” I feel his hand hold the back of my neck tightly.



“Yes Daddy.” I feel my face turn red. I feel his hand run across my rear, pulls back and spanks me twice, he feels me jump on his lap. His strong hand holds me in place.



“Aren’t you afraid of being found out, your wife finding out about us?” I feel very afraid, have never considered being ‘out’, being known in public as a sissy gay boy.



I feel him pinch my rear, squeeze my cheek firm. “I love this rear end, love it. Knew you’d be a very willing little sissy for me, I like what we’ve turned you into. You’ve become quite the ‘little woman’. Or should I say little sex slave.”



He took his hand out from under my dress and started to stand, I rose as he stood, almost fell off his lap. “I’m not going to get caught, you just do what you’re told like a good second wife does.” He was through with me for the evening.



“I have to go. Have places to be. I’m going to take you out next weekend. Get mentally prepared for that. And the place I’m taking you, get ready to be a very sexy little sissy super model, make me proud of you. We’re going to show you off for the first time. First impressions are everything, Princess.”



He started to get dressed, to put his underwear and pants back on. I sat stunned in the chair he was just seated in, sat down and looked at myself in my makeup mirror. Felt panic, what if I get caught, what if others I know see me, what about others at the office find out about me. My mind raced. I was terrified.



He smiled. As he went to my bedroom door, “I know you’re afraid. That’s part of it for me, I like that” He laughed loud, “You’ll get used to it, just like you got used to me fucking your ass.” He looked at me sternly. You may even start dressing full time.”



He laughed even louder. “You’re mine now, princess. And don’t think I don’t love that! You be a good girl, do what you’re told to do.”



As he opened the door he looked away from me. “I’ll see you at work.” He turned and left.



I just sat and stared at myself. Felt my soft penis strain at my chastity harness, wanted to masturbate. So bad, wanted to play with myself, did what I can only do now, ran my index finger over the wet end of my harnessed little thing. I rubbed my finger over the hole slowly in little circles. With my other hand I fingered my rear end.



I felt his cum run out of me and all over my hand. Wanted to do whatever my man wanted me to do in that instant, never wanted more to be anything other than his sissy, his bitch. I wanted to please my man!



Fingered myself for almost an hour thinking about him, I came in my cock harness. My dirty little secret that he doesn’t know about, know I can do. I was lost thinking about being his in public, truly being his.

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.

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