Bye Bi Viginity

It amazed me what could happen when you didn't expect it. Hell, I didn't even think it was a possibility for it to occur. I have been going out with my girlfriend for over a year now, and we are both very happy with each other, but there are just some things I thought she could never do. After all, she didn't have a cock, and that was what I wanted. I had these thoughts for a long time, but never had acted on them.

I was an avid chatroom watcher, sometimes interjecting a comment here or there when I had an opinion, whether it was asked for or not. It was then that it started with a friendly IM. His screenname was 'GoodTimeCharlie'. He wrote that he liked my profile and I thanked him for the comment. We talked for a little while longer about little stuff before he started asking questions. "How old are you? What do you look like? Where do you live?"

"25; 6'1", 200lbs, blonde hair, blue eyes, clean shaven; where I live is on a need to know basis, when I think you need to know, I'll tell you." were my answers.

That last question kind of threw me a little bit. "What are you into?"

"What am I into? In what way do you mean?" I asked.

"You know, sexually."

"Women." I replied.

"I'm sure you are, most of the good guys I talk to seem to be, but can you honestly tell me that you've never thought about having sex with another guy? I mean, come on. It's just you me and the computer. I won't judge you for what you think about."

"Well, I guess I have had thoughts about being with another guy. I mean, hasn't everybody at one time or another?" I questioned.

"I'm sure they have. Have you ever done anything with another guy before?"


"Not even in school or anything?"

"Nope, not even then."

"Alright, so what is it that you think about doing?" Charlie prompted.

"You know, the usual stuff." I answered, feeling myself start to get hard just discussing it. "I think about going down on another guy's cock, him blowing me, getting fucked, and fucking him."

"At least you're honest with yourself. Which part would you play, the dominent, submissive, or would you prefer to be on equal terms?"

"I guess I would be more submissive. I like being told what to do by my girlfriend, she just doesn't do that often enough for me."

"Ahhh, you like to be controlled." Charlie typed. "Hey that's cool. Myself, I like to be the one in control. I like to make the person do what I want to make me feel good. But don't get me wrong, I like to make them feel good too. I like to be able to tell them to get on their knees and suck me. I like telling them to bend over the table and spread their ass open so I can enter them from behind. I also like it just before I cum to make them kneel in front of me and open their mouths as I cum all over their faces. Sometimes I like to tie them down and do what we both want, for me to be in control, them to be helpless, and us both to enjoy what happens. Sometimes I like to discipline them a little, some light spanking or using a soft whip."

"Wow, I guess you really know what you like." I said.

"Yeah, if you don't then you don't fully enjoy sex." he stated. "So, when would you want to come over here?"

"W-what?!" I was shocked. Talking to me for only fifteen minutes, and this guy thought I would rush right over there to have sex with him!

"That's right, you like to be told. Alright then. You will be over here at 1pm, and not a minute later. If you are late, you will be taught to do what you are told, when you are told." Charlie stated.

He proceeded to give directions to his house, after having me tell him where I was starting from. I couldn't believe this. I actually told him what town I lived in and he told me how to get to his place. It was about half an hour drive, and it was only 11am. After I got offline, I thought about everything that we had discussed. My cock was rock hard and I was absently strocking it, but my mind was replaying our typed conversation. I decided not to go over to his house after all. I was not gay, and I loved my girlfriend.

I got into the shower and let the hot water run over my body. I was not going into that chatroom for awhile anyways. I didn't want to end up with a stalker or anything. At about noon, I was reading my mail, but without actually reading it. All that kept going through my mind was Charlie's orders. I was astounded that he actually expected me to be there in an hour. The nerve of that guy, asking me questions like that and then using my own answers against me. I decided to go for a drive and see the scenery. It was my day off, and I didn't want to spend all of it at home.

After about 15 minutes, I stopped for a drink at a gas station. I reached into my pocket to pay for it, and I pulled out the directions I had written down for Charlie's. I just stared at it for a few seconds, and then paid for my drink and left. I put the piece of paper into the passenger seat and drove onward. After some time, I realized that I was close to where I would have to go to get to Charlie's house. I didn't fully realize where I had been going, but it seems like a part of me knew exactly where I was headed, whether I thought I wanted to or not. It was two minutes before 1pm according to my watch when I rang the doorbell. I figured that I would tell him off and go home, feeling much better. I just needed closure about this, I thought.

"Good, you're right on time. I knew you would be." Charlie said as he stood in the doorway. "Come on in and make yourself at home."

He directed me to the couch and as I sat down I realized what was playing on the television. The sound was lowered, but now that I was really listening, I could hear every moan and grunt from the two studs that were going at it on the screen. It was an XXX-rated gay porno! This guy had some nerve! I just came in to speak my peace, and here I was being subjected to such a movie. I didn't say anything as I watched. I could feel myself getting harder as I watched, and I could sense him watching me. Then he sat down next to me and watched the show with me. One guy was down on his knees in front of another guy, and the guy standing was slowly feeding the other a long thick cock. The guy being sucked had a deathgrip on the back of the other guy's head, and there was no way he was going to get away, not that it looked like he wanted to. As I sat there transfixed by the scene, Charlie unzipped his cut-off shorts and pushed them down enough so he could take out his cock and start rubbing it. After a couple minutes he moved closer to me, even though I really didn't register that fact. I only noticed when he took ahold of my hand and guided it to his hard 7" long shaft.

"Here," he said to me. "You need to feel this." My brain never even thought about jerking my hand away. It stayed around his cock as he guided my hand up and down. Soon he let go of my hand, letting it do what it wanted. The up and down motion didn't stop when he stopped. I was slowly jerking him, listening to his moans. His hand found it's way to my lap, and stared feeling me through my pants. My cock was already hard, and wanting the attention. He reached over with both hands now and undid my pants, indicating that I should push them out of the way. I did as I was directed without my hand removing itself from his hardness. We were slowly rubbing and jerking each other while watching the movie.

"Take off your clothes and get on your knees between my legs." Charlie suddenly said to me. I must have had a blank look on my face when I looked at him, and I hesitated for a moment. His voice never got louder, but it did get a hard edge to it. "Now."

I undressed with Charlie watching me the entire time. I lowered myself off the couch and slowly got into the position he indicated. "Good." he said. "Now I want you to lick my cock and balls, but don't put it in your mouth until I say so."

I took his cock into my hands again, and lowered my mouth to it. My tongue ran over the skin of his hard meat, proceeding south where I licked all over the soft, smooth skin of his balls. He gasped with pleasure at my tongue's first touch, and remained moaning all the time I licked over and under him. He let this activity go on for quite awhile, alternating between watching me and watching the movie.

"Enough. Now open your mouth and stay still until I tell you that you may move." Charlie ordered. Charlie stood up and grabbed his own cock. He put a hand to the back of my head, and began feeding me his tool, slowly but insistantly. My mouth closed down upon it and I sucked him inward, trying to otherwise remain still. "Good," he moaned. "That feels good. I knew you would like this as much as I do. Go ahead, suck me off."

With his permission given, I devoured him like a starving wolf. My hands grabbed his ass and pulled him into me, and I was taking as much as I could into my mouth and down my throat. He tasted wonderful, and I couldn't seem to get enough. He was moaning loudly and gasping as he thrust his cock into my more than willing orifice. His grip tightened on my hair and his breathing increased it's rapidity. His voice was a low pitched growl of pleasure when he next spoke.

"I'm gonna cum, and I want you to swallow it all for me."

I had never done that before, and really wasn't sure I wanted to at all. His grunts increased and I felt his cock inflate even more. I tried to pull back but his grip was too strong. He was forcing his cock in and out of my mouth while holding onto the back of my head. He started to shoot and I had little choice but to swallow him. It was seven or eight spurts before he slowed, just holding me in place as he growled like an a****l. I was looking at his face and saw the raw lust plainly in his eyes.

"Oh god that was good." he said as his breathing slowed. "I felt you try to pull back though. For that, you will have to be punished."

Without another word, he led me out of the living room and into his bedroom. My mind was racing as I thought about what he meant by 'punished'. He led me to the bed and pushed me backward onto it.

"Put your arms over your head." he ordered.

I did as I was told, and he grabbed each one and shackled me to the posts of his headboard. Then he grabbed each of my legs, pushing them up and securing them to the same posts as my arms with longer straps. There I now was all tied up, with my knees on either side of my head, and my ass in full view and exposed for whatever punishment he was thinking. It was kind of dark in the room, but I could make out what he was doing clearly enough. He reached into his dresser drawer and pulled out a long and wicked looking cat-o-nine-tails. My eyes went wide as I saw him approach me holding it easily in his hand, casually swinging it back and forth.

"I told you to swallow my cum. If I hadn't held you there, you would have pulled away, wouldn't you? Well, that is going to cost you." he smiled as he told me.

"P-please, don't hurt me!" my voice was a whisper in the dark as he stepped closer. "Please, I'll do anything you want! I'm sorry I tried to pull away, it will never happen again! Please don't hurt me!"

"Oh don't worry, this won't hurt much."

His hand swung back and forward so fast I didn't have time to yell out before the second swing was under way. The cat snapped my ass five more times before I could catch my breath in order to cry out. The pain wasn't as bad as I thought, but pain is pain, and my ass felt like it was getting a good beating. I tried to move away, but I wasn't going anywhere until he let me. Five more cracks and it stopped as suddenly as it started.

I could hear him as he came closer to the bed, and I tensed myself up for another blow. Instead, my eyes shot open and I moaned loudly as I felt his warm, wet tongue against my virgin hole. He licked and fucked my ass with his tongue as I lay there panting and groaning. Soon his tongue was replaced by a finger, and then by two. He was slowly finger fucking my asshole, and I loved it, but I knew what he was preparing me for, and I wasn't sure I wanted that. He continued to open my asshole as he inserted three fingers into my hot ass. My moaning was drowning out the movie sounds coming from the living room. Every so often, he would run his tongue over my ass again, sending new pleasure though me. His fingers slowed and then stopped and I opened my eyes to see him approach my waiting ass as he watched me. "You know what's coming next. I'm going to fuck you. I'm going to take your ass' virginity, and you are going to make me cum. How long that will take depends on you. But first, I want to hear you beg me to fuck you."

"No please don't!" I pleaded. "You're too big. You're going to kill me if you fuck my ass. I've never done that before! Please don't fuck me yet." My asshole was open and wet from his fingers and tongue having their way with me. He never took his eyes off mine as he leaned against me, placing his hard cock against my virgin hole.

"Like I said, I'm going to fuck you. You're mine until I cum, so just relax and let it happen."

With those words he pushed into me, slowly forcing the thick shaft into my unwilling ass. "AAAAaahhhhh!!" I shouted in pain. "Please stop! Please!!"

He kept pushing until he was all the way inside of me, and then he stayed still as my asshole adjusted to this intrusion. When The pain had subsided, and my pained groans had stopped, he pulled out of my ass, only to slowly drill it into me again. This time he started a long slow fuck. His deep breathing was in time with my own, and soon the fucking I had just begged not to happen was feeling beter and better. He smiled down at me as he fucked my ass, knowing what I was thinking.

"Yeah, I knew you would like this. You do like this, don't you?"

"Oh yes! I love it! Fuck me Charlie, fuck me hard!"

I couldn't believe those words were coming out of my mouth. Only a moment ago I had been begging to be released. I was again begging for release, but it was Charlie's releasing his load of cum that I was after now. Answering my request, he started fucking me harder. He would pull all the way out of my ass, and then drive it all the way back into me in one smooth long hard stroke. I was loving it. My cock was rock hard and I was panting and gasping as much as Charlie was. Too soon for me though, Charlie's strokes were getting faster and shorter. He was really pounding it into me now, and his face told me that it was only a matter of seconds before I would recieved his cum once again. The a****listic growling started as he looked me in the eyes.

"Fuck me Charlie! Fuck me hard and fill my ass with your cum!" I begged him. "Give me your cum! Give it to me! Yes, you feel so good. Shoot your cum inside of me! Come on, give me your cum. Give it to me. Cum in me!"

Charlie grabbed me and pulled himself into my ass as far as he could make himself go. There was a second of pause, and then with a loud growl he started to empty his load of hot, sticky cum deep into my waiting ass. He started fucking me again, making my ass milk his cock until there was nothing left to shoot. Then he collapsed on top of me, his dick sliding out of my hole. His mouth drove straight for my own cock, taking it into his mouth and down his throat. Because I was so excited, it was only a few seconds before his expert mouth coaxed my own cum from my balls and onto his tongue. He conitinued to lick and suck me clean, and then realeased me from the restraints, bringing himself up to give me a long, slow, cum covered kiss. Charlie sent me home with a smile on my face and a sore but eager ass.

My girlfriend got home a couple hours after me. I had taken a long hot bath, letting my muscles relax, and my ass recover. She told me that she had taken the following day off, and wanted to spend it with me doing whatever we wanted. That night, I was out like a light as soon as my head hit the pillow. I was awakened the following morning with a warm wet mouth covering my cock. My girlfriend was waking me up in my favorite way, by sucking me. I was hard in no time, and had my hand in her hair, guiding her up and down my pole.

"I want to try something new today." she whispered to me. "I want to tie you up, and have my way with you."

Images of the previous day ran through my mind, and I became harder than I had been the minute before. Immediately I agreed, and she opened her nightstand drawer to get to toys she wanted. Soon I was tied up on my back, spread-eagled, and my girlfriend Jenn was running her hands as well as her mouth up and down my body. She straddled my head, and lowered her pussy down to my waiting mouth. Her moans started the moment my tongue found her clit. I licked her up and down, quickly bringing her to orgasm. Usually she stops there and goes for my cock. To my surprise, she stayed there, grinding herself onto my mouth.

"I didn't tell you to stop!" she said. "Keep licking me!"

I liked this side of her, even though I rarely saw it. This was how she needed to be more often. While I worked her towards a second orgasm, she reached back and started stroking my hard cock. Then she clicked on the TV and started one of our tapes. We had a small collection of x-rated movies, and she liked to play them during sex. It wasn't the picture she cared about, she liked listening to the sounds. She had told me that it made her feel like someone was watching us fuck. I guess there was a little exhibitionist in her. The groaning from the TV matched our own sexual sounds. While I licked and sucked her cunt, she reached farther down and started massaging my ass. She always liked playing with my ass. She told me so on countless occasions. It never, however, went any further than that. Yesterday with Charlie was the first time my ass had been entered, but not the last I hoped.

Jenn started cumming once again and I kept my lips and tongue working on her sensitive clit as her second orgasm subsided. She moved down the bed and positioned herself between my legs once again, sucking all of my cock into her waiting mouth. It was now that I could see the movie she had chosen to listen to. I didn't recognize it at first, which was odd, since we had seen them all numerous times and listened to them even more. Then I saw a guy on his knees, giving head to another guy. We had a few bisexual movies, mostly because Jenn wanted to see them every once in a while. She seemed genuinely curious about it. A blonde guy was sucking on anther guy's cock. The camera angle wasn't that good and you couldn't see the face of either guy, but you knew what was happening. Both seemed to be enjoying it immensely.

"Which movie is this?" I asked Jenn as she continued to suck on me.

She simply took out a gag and put in into my mouth, effectively cutting off further questions from me. Being tied and gagged always excited me, and she knew it. I was getting close to cumming, and by the way Jenn was deep-throating me, she knew it too. My balls tightened up and I could feel my cum start to race up when I finally saw something in the movie I remembered seeing before. It was Charlie! And the guy going down on him was ME! Oh GOD where did this tape come from?!? Suddenly my cum was shooting into Jenn's waiting mouth. I gasped and groaned through the gag as I shot my load. Jenn climbed back up the bed and removed the gag, but before I could say anything, she kiised me deeply, feeding me the cum that was still in her mouth. Once done with that, she replaced the gag and kneeled over me, looking down at me. I knew my eyes were as wide as they would go, and didn't know what would happen next. I imagined Jenn with my cock in one hand, and a large butcher knife in the other.

"I knew that given the right opportunity, I could get you to have a large cock in your ass." she said as she smiled. "Charlie eagerly volunteered when I told him what I wanted to do to you. He works with me you know, and I knew he would be eager to get his cock into your tight ass if I let him. I've always wanted you this way, but I didn't think you would let me, so I had to kind of arrange it this way. I hope you don't mind."

Still smiling, she left the room. I could hear her make her way through the house and I heard a door open and close. She returned shortly with Charlie following close behind. "You've cum once already today, don't you think it's fair for Charlie to cum also?"

They both lay down on the bed and started touching each other and kissing like they had obviously done before. I wondered how long she had been fucking him, but at that moment, I guess I didn't care. Still tied and gagged, I could do nothing but watch as Charlie took my rightful place between Jenn's legs, sliding his cock into her still wet pussy. Both of them let out a low, mutual groan. they slowly fucked in full view of me, letting me watch as they drew each other closer and closer to orgasm. I heard the now familiar growls of Charlie, who was about ready to cum. Jenn started first though. Her orgasm ripped through her and left her panting and limp. She was still in control though, and made that apparent with her next words.

"Charlie, I want you to cum in his mouth. He already came in mine, and I think it's his turn now."

Charlie removed his shaft from Jenn's cunt and continued to stroke it as he moved above me. He pulled the gag from my mouth and replaced it with his cock. Each was as effective in making sure I could not protest. Jenn lay beside me as the cock was thrust into my mouth.

"That's right Brad, I want you to suck him off and swallow his cum. This isn't over, it's just beginning. Come on, make him cum." Charlie started unloading right in my mouth as Jenn continued to encourage me. "Yeah, you like that, I know you do. Take all his cum. Swallow it all. Good boy, swallow all he has for you."

When Charlie finally withdrew his cock from my lips, Jenn continued to instruct me. "Now you are going to get fucked, and you'll like it as much as you did yesterday, I promise."

I thought that Jenn was going to get Charlie hard again and watch as he fucked me in front of her, but once again, she was full of surprises. She went back to her drawer full of goodies and pulled out something I had never seen in our collection. It was a 10 inch long, thick, black strap-on dildo. The thing was monstrous in my opinion. Jenn put it on, and stood next to the bed letting me admire her and think about what was about to happen. It looked kind of obscene having that long black cock sticking out from where I usually plunged into her cunt. She stroked it as if it were her own and looked at me in pure lust.

"I got this just for you Brad." she said as she climbed onto the bed. "Just for days like this." Charlie unstrapped my legs and got behind me, pulling my legs up and out so Jenn would have unlimited access to my ass. My head was in Charlie's lap next to his rapidly inflating cock. "I've always wanted to do this to you Brad." Jenn told me. "Ever since I let you fuck my ass. It feels so good I knew you had to try it too."

"Oh my god Jenn, please don't do this to me!" I begged.

"That's what you said to Charlie, and see how much you enjoyed him? You'll enjoy this too, just relax. You're getting it whether you think you want it or not."

Charlie held my legs up as Jenn lowered her mouth to my ass. She licked and tongue fucked me just as Charlie had the day before. It was just as intense of a feeling and I immediately began moaning. Even though I didn't want this giant black cock going up my ass, my body started to respond.

"Hold him tight Charlie, I'm ready to fuck him now. Get ready Brad, here it comes."

Jenn gripped the her black strap-on as she ran it up and down my asshole. I was wet with her saliva and the fake cock looked wet as well, possibly from some sort of lube. Jenn pushed into me a little ways, slowly but f***efully. At that moment, Charlie decided to place his cock into my mouth once again. Jenn never let up and never stopped. She just kept sliding the enormous penis into my ass. Charlie released my arms from their prison just long enough to turn me on my stomach. Then I was strapped in place on my hands and knees, with a cock in my mouth and asshole. My grunting was muffled by Charlie's cock filling my mouth. He face fucked me as Jenn ass fucked me, both of them working on me from either end. Jenn grabbed my hips and started pulling me onto her fake cock.

"Charlie, come over here and fuck my ass while I fuck his!" Jenn demanded. Charlie did just that, entering Jenn's ass with more ease than she had entered mine. Every time Charlie pushed into her, she pushed into me. It was like a sexual train, back and forth. My ass was being taken by the woman I loved, and hers was being taken by the guy who had taken my anal virginity.

"You like this don't you Brad?" she asked.

"Yes!" I yelled. "I love it! Fuck my ass Jenn. Fuck me! Fuck me!"

She pounded away at me for a long time. Suddenly she pulled out and had Charlie replace her cock in my ass with his own. She took off the strap-on and lay down so my mouth was at her pussy once again.

"Make me cum you slut!" she demanded. My tongue immediately went to her throbbing clit, and she was thrashing back and forth as she came in record time.

"Shoot your cum into him Charlie. Fill him up!" Jenn ordered.

Charlie was well on his way to that anyhow, and he held me in place as he fucked my ass without mercy, finally spurting deep into my ass. I was then uncuffed, and Jenn positioned Charlie in front of me while she got behind me. "Your turn love."

I rammed my own cock into Charlie's tight ass in one stroke, making him grunt. Jenn lay down on her back behind me and started licking my balls and ass as I fucked Charlie. Her head was between our legs, and she got a good view of me finally getting to fuck the man who had twice now filled my ass with his cum. I fucked him hard and fast, my cum building until I couldn't hold it back anymore. Jenn pushed her tongue up into my ass as I shoved into Charlie hard and held him there as I shot stream after stream of cum into the waiting ass in front of me. All of us collapsed in a heap, none of us really caring where we landed on the bed. Jenn crawled up beside me and kissed me deeply while lightly stroking my sensitive shaft.

"You liked that didn't you?" she accused.

"Mmmmm, you know I did." I replied.

"Good because Charlie is moving in with us, and you're going to get that much more often now. Whenever we want you. You're our little slut, and I know you will do whatever we want."

100% (33/0)
Categories: AnalFirst TimeTaboo
Posted by kinkybipaul
1 year ago    Views: 2,360
Comments (10)
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10 months ago
hot story made me cum
1 year ago
what a great story.i want to live it out for real
1 year ago
Damn.... That was really hot. I'm rock hard and throbbing now. That follows one of my biggest fantasies. Thanks :-)
1 year ago
great story
1 year ago
hard as a rock now! thanks. really liked the idea of Charley moving in>
1 year ago
Great story really turned me on!
1 year ago
Very nice!
1 year ago
great story very hot hope to hear more
1 year ago
hot story!!
1 year ago
very hot..thanks