Encouraging My Girlfriend

This is a true story. And I don't mean one of those times where the author claims it's a true story just because it's a fantasy of theirs. All the events entailed actually happened and it's taken a lot for me to write this, but with much encouragement, I finally have. The names, of course, have been changed to protect identities. Sorry if there's a lot of set up but it's the first of several stories I plan on writing so this can be used as a guideline for them all.

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Jessica and I started dating 2 ½ years ago when I was a sophomore in college. We met through Myspace like so many kids our age and things hit off right away. I was just coming off of a long term relationship that began when I was in middle school and she had recently broken up with a guy she dated for 3 years that was a complete ass to her the whole time. We were both in a bad spot and needed someone to be there for us and it just so happens we found each other and fell in love almost immediately.

I am currently 22 years old, 5'11", 160lbs with dark brown hair and eyes. I am an avid soccer and basketball player and I love to run and work-out. Now I'm not completely ripped like some muscle head but I do have a nice six pack and decent musculature going on with my arms and back. Although I've only had 2 serious girlfriends I've had quite a few girls on the side (in between relationships of course) and most girls seem to find me generally pretty attractive. I've also been told that I'm more than adequate downstairs and all the girls I've slept with have praised my abilities in bed. I'm stating these facts not to toot my own horn, but rather as part of a rationale for events detailed later.

And now to the point I'm sure most of you are far more interested in, Jessica. She's 20 years old now, 5'9", 135lbs with long brown hair with a gently flowing wave and beautiful big green eyes. She has a nice waistline, flat stomach, and simply amazing legs. She ran track and swam a lot so she has a really streamlined body. She has a beautiful smile, gentle hands, and extremely sexy feet. Her ass is amazing and not too big but not too small either and she's rocking a large B/small C breast size...she can wear both sizes. And let's just say she is incredible in bed. She's not like most of my buddy's girlfriends who pretty much are just all about the missionary position and making out and that's it. She loves to give head, loves to be ate out, and she likes to give footjobs, handjobs, and titjobs. She's into anal, role-playing, name-calling, light bdsm, sub/dom. She likes it rough and she likes it gentle. Hair-pulling, ass-slapping, being used, everything. I mean she is the perfect girl. And it's not only stuff she'll let me do to her but she loves to do all kinds of kinky things to me! Like I said she likes to dominate sometimes, she also likes to call me names, smack my balls around a little, make me eat her ass, and she loves trying to make me cum in all kinds of new and interesting ways. Like by just rubbing my bulge inside my pants and everything. I mean if you could picture the perfect sex goddess this would be it! Just one more point, some mornings...when I would wake up with morning wood, I would find her on top of me naked riding my cock for all it was worth, moaning and screaming and all. Total nympho is all I can say, I mean I can last for a really long time; we've had sex for over 3 hours before, and I can even cum multiple times a night unlike some guys. But it is still hard for me to keep up with her; she is completely addicted to sex. Even if I fucked her brains out 9 times a day she would still want more. That coupled with the fact that I was always 2 hours away at school lead up to the following events.

It didn't take us long to fuck for the first time after we met, and shortly after we began dating I started to learn about all her crazy sex traits. One of the first things I figured out about her is that she was bisexual. She loved women's bodies almost more than men's, but still preferred dating guys. Not only was she bisexual but unbelievably, she sort of had a thing for seeing her best friends naked. She would jump on any opportunity and told me constantly about how badly she wanted to fuck her friends and how horny they made her. She had a few sexual experiences with her two best friends that she recounted to me on several occasions. One she used to fuck her ex-bf while she was sleeping in the same bed and another she had gotten drunk with and they fingered each other one night. All our pillow talk about the subject eventually lead to her confessing that she would love to see me fucking one, if not both of her friends. This took me aback for a long time and I surprisingly declined the invitation for a long time out of some misplaced sense of moral aptitude. Eventually, however, it led to me having several incredible threesomes at my apartment with two of her best friends. A story I'd be more than happy to account for later if there's any demand. I mean imagine having sex with your girlfriend and the whole time she's saying stuff like, "Call me Kelly" and "God, Jessica doesn't deserve this amazing dick you have fuck me while that stupid cunt watches." Yeah, needless to say I blew my load instantaneously. Hell I probably came faster hearing her talk about it than I did with her licking my balls as I shoved my prick into her friend's tick ass pussy.

So what are you getting at already!? Okay, all of her crazy sex fetishes, along with my openness and willingness to please, and the threesomes with her friends, eventually led to me starting to suggest having a threesome with another guy. The ol' MMF. At first it started with me just bringing it up during one of our many fuck sessions. I would say something like wouldn't it be hot to have another guy with us? Or God I'd love to see you suck someone else's dick. At first I was just saying that stuff because it was something new and the witness her reaction, which was one of instant orgasm. But over time I found that the thought of it was actually turning me on quite a bit. This was unlike me because I'm a pretty protective guy, but I just couldn't stop thinking about another set of balls slapping against that beautiful ass while I watched jacking off from the corner. It eventually led to more serious conversation.

"So you really wouldn't mind watching me with another guy?"

"No babe, honestly, I mean I love you and trust you, and it's just sex."

"Are you sure you wouldn't be jealous, you know get mad afterwards and want to break up or anything?" She asks and she lovingly curls my chest hair.

Looking into those beautiful eyes all I can see is her mouth stuffed full with some other guy's member and her pussy dripping wet the whole time. "Of course I wouldn't babe, as long as you didn't sneak around with him afterwards I would be fine, you can trust me too you know! So what do you think do you want to try it? Please for me?"

I could see the twinkle in her eye, that undeniable gleam of incredible lust. I already knew the answer; we had talked about it several times in the heat of the moment. She had already confessed that she wanted another dick in her so bad. She had told me that mine just wasn't enough and that she not only wanted but needed another cock, that she wanted to be filled up with dick, have one in her mouth and pussy. She had already confessed to wanting me to be forced to watch, so she could stare deep into my eyes while some guy fucked her silly.

"Well okay, but we have to agree on the guy." She smiled almost ear to ear and started kissing me.

"Fine," I said, "But I have a few conditions."

"What would those be?"

"We'll discuss them in a minute," I winked as I rolled over on top of her and began kissing her deeply.

Just from feeling my breath through my nose and my tongue racing in her mouth, Jessica already began arching her back off the bed and moaning against my lips.

"Fuck I want it baby, give me that fat cock!"

I, of course, complied willingly, and we proceeded to have one of the best fuck fests we'd had in several weeks. About halfway through I decided to list my conditions.

"Okay baby, if we're going to do this we need to get a few things straight. I want to pick the guy, but I want you to okay him. I don't want to get a guy that you aren't really attracted to so he has to be in good shape and hot to you. He has to be willing to have some male contact because I want you to get double penetrated. I don't want him to be a close friend of either one of us to avoid awkwardness. He has to live far enough away that we won't have to worry about him being around all the time. He has to be clean. And the last is the most important."

Her eyes closed as I was still inside her, gently pushing the head of my cock in and out of her swollen pussy. "That's all fine with me, but what's the last thing?"

"I want him to be hung; I mean to have a big dick. Bigger than mine."

When I said this she snapped her eyes open and I could swear that I felt her pussy quiver around my dick. "Really? Why would you want that? I mean your dick is plenty big enough, isn't that asking for a lot?"

"I just want to see you get fucked by someone bigger than me; you know the whole humiliation thing"

We had established over the course of our relationship that I did have one fetish in particular. I liked to be humiliated. Not to the extreme, but just a little, and typically a just between me and her kind of thing. Hence the name-calling, ball busting, she would spit on my face sometimes, call me a bitch, and a slut. She would make me do things to her or for her. She made me dress up in her clothes once and she loved playing with my ass, which I tolerated mildly, and pinching my nipples and such. She would shove her ass or feet in my face and make me lick them clean, she would make me stand naked in the room and she would laugh at me sometimes. She made me take the trash out naked before, and would show me messages random guys sent her on Myspace all the time listing things they wanted to do to her. I don't know what it is but something about the whole humiliation thing really turned me on and she was more than willing to cooperate. I think it was that fact that I generally had everything I wanted and was sort of the alpha male type that all my friends and family looked up to. I could have normal sex with most any girl I wanted, crazy sex even, but this was something I couldn't have, shouldn't have, being who I was, so I wanted it and I wanted it badly. It's what led to the whole MMF idea.

"Well honey if that's what you want believe me that's fine with me! I mean I can handle it as long as you can. But you should know that your dick is all I ever need and believe me it fills me up just fine. I love it so much. And uh I love you too! Haha!"

"Well I love you too babe, and yea I know what you mean, but if we're going to do this I just want to make it as awesome as possible for you. Plus something about seeing you enjoying a cock bigger than mine makes me hard as hell." There that pussy was throbbing again. She moans. "You would like that wouldn't you baby? Having a nice big fat cock fill you up? Fill you up more than I ever could? You've been wanting that haven't you?"

"Mmmm Yeah baby. God I want it so bad, nice fat cock stretching my pussy out."

"Admit it, my cock isn't enough for you. You want more, you want bigger, better cock, that I just can't give you."

"God baby I do, I do so bad. I want a big strong man to come fuck me, stretch my pussy out and make me hurt. I want him to fuck me like a real man while you watch like the little bitch you are."

It was all I could do not to blow my load in that sweet pussy right away. I had dropped the bait and she had caught on right away. We did this often, talking about another guy coming in to fuck her. I decided to switch it up a little this time.

"Tell me what a bitch I am, what a fucking fag for letting another guy fuck my girlfriend."

"Mmm you are baby, you're such a bitch. I can't believe I even date your sorry ass. I'm so ashamed of you. I bet you just want that big dick for yourself! Well that's too bad baby, that fat dick is going to go in my pussy not your faggot ass!"

She was taking the bait and more. She was pushing the envelope too.

"Tell me what a little dick I have baby. I know that's why you want more."

"God it is. It's so fucking tiny. I didn't want to say anything before baby, I didn't want to hurt your feelings. I know I always let you think it was big enough, but it's not. It's so fucking pathetic, just like you. God I can barely even feel it in me. I can't wait until I have a real dick in me and not this little thing. I need a real man to fuck me. I need to fill my pussy up like you never can with that fucking thing you call a dick."

"God baby don't stop."

"Mmm I'm surprised I even let you fuck me with that thing. God I've wanted to tell you for so long that your dick just wasn't big enough; ever since we first fucked I've always been thinking how small it is and how much I wanted a bigger dick. Now I'm going to get one. I be surprised if I ever even want to fuck your little faggot dick again after this."

Needless to say I fucking filled her pussy up with a gallon of cum. We had a few more fuck sessions like this. Our new thing was for her to make fun of my dick and tell me it was tiny. I started looking all over for a guy to meet our credentials. In the meantime we ventured on to other things on topic. She would occasionally refuse to fuck me and make me fuck her with the dildo I had bought her instead as it was lifelike and bigger than me. She even made me suck on it one time while she fingered my ass and jacked me off, telling me what a fag and bitch I was the whole time. She started responding to the guys on Myspace that she had previously ignored, flirting with them, and insinuating that they could possibly hook up with her in the future without me knowing, although that has and will never happen, she just did it to show me. We also started getting on yahoo messenger some nights, and she was show pictures of herself, most of the time nude, to other guys and pretends to be single and then proceed to exchange pictures and cyber with them. Sometimes she would get on and tell guys that I was sitting right there as she traded pictures and encourage them to make fun of me. She even sent them pictures of my dick and remarked on how small it was, although most of the guys were like, umm actually that thing is bigger than your face! It was still a turn on to see her tell other guys that. She even called on guy and they moaned on the phone together as they both masturbated, she made me sit naked on the floor this whole time and suck on her toes and feet. I didn't mind.

Eventually I struck gold and found the perfect guy. He was about the size height and weight as me. He had a few tattoos and a close shaved head, but he seemed like a fairly nice, intelligent, and clean guy. I met him through a networking site for swingers, we chatted some, and eventually I called him, then agreed to meet him at a bar a few towns away. I explained the situation to him and he had already sent me a picture of his dick but when we left to the car he whipped it out so I could verify that he was telling the truth and that it was big and not full of warts or something. Turns out I sort of knew the guy because he played soccer at a school in our conference and we had played against each other several times over the years. I eventually showed him to Jessica and she granted her approval.

"Wow he's actually kind of cute, I like buzz cuts and tattoos so that's a plus. What about his, ya know?"

"I don't know you tell me." I showed her the picture of his dick soft and then hard he had sent me and told her that I saw it and he wasn't lying. I instantly noticed that slight change in her look and feel, it was almost like I was balls deep in her and she was about to orgasm. The mere sight of his dick made her pussy ache and my dick spring to attention.

"That will do." She smiled "But what about...oh my God are you hard?" She walked over to me smiling that smile ear to ear.

"Yeah baby I just can't wait to see that thing in you." The smile quickly faded to a look of deep lust and she proceeded to fuck my brains out good ol' fashioned style.

Before long we had arranged a meeting with the guy, Kevin, a few towns away. We agreed to meet at a bar for drinks, and then head back to a hotel I had booked for the night for the festivities. We were both super hyped and nervous with anticipation. We had agreed to film the whole ordeal so I brought my camera and stand with us.

"Are you sure about this? Last chance to back out." I asked of Jessica on our way over the meet Kevin.

"Yeah babe, I'm fine with it as long as you are. It's not up to me it's up to you; you're the one who's got more at stake here."

I agreed that I was ready and we met Kevin for a few drinks. Upon seeing Jessica his face lit up and I could practically hear him think JACKPOT out loud. They hit it off pretty well, I had to break the ice a lot but after we all got a few drinks in us we all softened up and started talking more. Eventually when the place got a little busier I suggested we all go dance together. For a while the three of us danced with her grinding on me and her arms around him in front of her. Eventually I left to go piss and get another beer and encourage the two of them to dance together. As I came back and looked she was grinding her ass all over his crotch and he had one hand feeling her bare stomach dipping down just below the waistline occasionally while the other traced her side, breasts, and back down to her ass. They seemed to be enjoying themselves so I let it go on till they came over to me. Jessica ran right up to me smiling.

"Oh my God his dick is fucking huge." She whispered through her teeth as she smiled at me. I glanced at Kevin and sure enough she was sporting a huge semi that he had tried to conceal in his pants. This got me ready to go and I could tell just from the look of Jessica that she was ready to fuck his brains out.

We headed back to the car and got to the room. Jessica said she wanted to take a shower first so me and Kevin sat outside and talked. Despite the levity of the situation it actually wasn't awkward; it was just like we were good ol' friends.

"So I know we've talked about this, but you really don't mind me fucking your girlfriend with you right there?"

"No dude, honestly I don't. I mean I know it might sound strange to you but it really does turn me on, I don't know why. I mean I'm not going to freak or anything I swear."

"Yeah I believe you man, I'm just double checking, because believe me I want to and hell it sounds like fun, I'm just trying to be respectful."

"And I appreciate it. Oh and believe me she wants to too, I can tell. And like I said don't be shy or afraid, feel free to do whatever you want to her, as long as she doesn't object. And also you can say anything you want to her or me. I mean any kinky fantasy you have or anything you want to do feel free I promise it's straight. Speaking of so am I, so again, I don't mind a little contact just don't try to slip a finger in my ass or my dick in your mouth or anything."

"Haha, well you don't have to worry about that. And I'll try my best just to get into it and have a good time."

"Also she might want you to say or do some stuff, and if she does don't hesitate, we don't mean half the stuff we say in these situations it's just for fun."

"Okay."

Jessica and I had planned out a few scenarios we wanted to try to get Kevin involved in so I figured I'd go ahead and give him a heads up. So we went back into the room and Jessica had finished, we hung out a little more, drank some and popped in a nice long porno flick. I set some music playing and we adjusted the lighting some to set the mood. Before long things kicked off with me and Jessica making out which led to her grinding on me and things starting to get hot and heavy. Right as she was starting to slide her hands down my pants I motioned Kevin over and looked at Jessica.