May Goes Too Far

May Goes Too Far


It was late April and I met a fantastic girl.

The first week I dated May I thought I was the luckiest man in the world. May was the source of the best sex of my life and simultaneously the worst sex event of my life. At five foot two she was one hundred pounds of pure sex appeal. She had long shiny brunette hair that went all the way down to a very curvaceous yet small, muscular, tight, ass. She had a thin waist but could still boast of a full set of 32 B boobs with a nice amount of heft and little sag. Her face was super cute in a girl next door way with freckles except when she wore make-up, then she looked over-the-top elegant.

In short, she was smoking hot - always. She even looked hot when she drank too much and was puking in the toilet. She knew how to pull off any outfit and could make anything she wore look amazing.

Lastly, she loved sex. She loved blowjobs, getting her pussy eaten, as many different positions as the mind could fathom, and she was willing to try anything.

In that first week with her I had more great sex than in the last three months with my previous girlfriend. Not only did she love giving head but she did it with a level of gusto and enthusiasm that rivaled a professional cheerleader's zest for her superbowl team.

We had a blowjob in the car waiting for a movie, a blowjob to say good morning, a blowjob to celebrate that we didn't run out of gas, a blowjob after sex just because, a blowjob with whip cream, a blowjob in public, and a blowjob when she said it had been too long since she had tasted my cum.

On the last day of that first week she taught me that anal sex could be way better than imagined. I fell in love with her larger-than-life personality and was thinking I would marry her. I had no idea how I landed a girl so far out of my league. Nor how she could possibly have been single.

In the second week I saw her kinky side and it was fantastic. I think I became addicted to sex. Also, as we became more relaxed with each other she let her hair down a little and I got a glimpse of her personal demons. She could get a touch neurotic and couldn't let a grudge go. Like with an ex dorm-mate she convinced herself had stolen a boy from her: once a day like clockwork she left a disturbing anonymous voicemail for this unfortunate girl.

In the third week she found a way to make sex touch on my deepest fantasies in ways that reached needs in my soul I didnt know I had. She discovered my fetish for polka dot lingerie I barely knew about and led me to understand that not only did I love her in dotted panties but that I could enjoy wearing them as well.

She also figured out that my unsatisfactory relationship with my father translated into an unfounded fear that my larger than average cock was inadequate. Better than that, she made me feel good about my sexuality and gave me confidence not only in my penis, but also in my performance. She was nothing short of amazing, the good outweighing the bad a hundred fold.

The fourth week sex transcended the physical and became a spiritual thing. The afterglow of sex lasted days, overlapping with the build up to the next sexual event. Though her intensity scared me a little.

Some of her behavior did too. Did you hear the news story about the woman who went into the tiger exhibit at the zoo and was lucky to survive? That was her, and in her mind it wasn't luck but an example of her connection with cats. I was realizing that she was crazy.

Did I let that deter me? As the saying goes "A woman's ass makes a horses ass." I was hooked on her charms and denied the omens.

One night we were just hanging out in my apartment watching a movie. We had had sex over an hour ago but the movie turned out to be bad and she just turned to me and asked me if I could do anything at all to her what would I want to do.

Well, I'm not as creative as she is so all I could come up with was to blindfold and fuck her. In a flash her shirt was off and wrapped around her eyes. She told me to do whatever I wanted to her, adding only that her "safe" word was "Ticonderoga."

I had never heard of a safe word before but she explained it to me. She said a safe word means no but "no" means yes.

I kissed all over her body then touched her in various places with my dick which just may have been the very first thing I introduced to her rather than the other way around. I think it was a new thrill for her.

I wanted to live up to the challenge so after a bit of thinking I tied her up, face down, with the sash from my robe. I tried to think of something that we had never done but it was harder than one might think.

Then I had an idea: I told her I was going to get our next door neighbor to come over to fuck her. She didn't say anything... I got dressed and went next door but had no intention of letting that fat slob have her. Planning quickly I also put headphones on her playing loud.

I knocked on his door and talked to him for a few minutes about nothing to create the illusion. When I returned I did my best to walk around like there was more than one person in the room.

She arched her back presenting her ass and pussy to me. Next I put on a condom (which we never wear) and entered her wet cunt not letting any other part of me touch her. I even tossed a few items to the other side of the room so she might think I was sitting in the chair watching.

I pretended to cum then I "showed the neighbor out." After that I cleaned up her pussy: all part of the show, and fucked her adorable butthole (as if I did not want sloppy seconds). Later she told me she knew it was me all along - but that the game was a lot of fun. What can I say? She's great in the sack!

Unfortunately, this little scenario set the stage for my demise. While I was not willing to have the neighbor fuck my sexpot she did not have the same ability to set restraints on herself or even consider what would be appropriate and what would be out of line. I hadn't fully realized that then.

The following weekend we were just catching our breath after a particularly energetic romp when she asked if she could surprise me. Up to now all her surprises had been incredibly sexy so I agreed.

She jumped on my face, smothering me with her cum-soaked pussy until she had one last orgasm, then jumped off just as quickly getting dressed. I licked the last of my cum off my lips.

She told me that wasn't the surprise. Which I kind of knew because we had done that maneuver many times before. As she left she told me to be ready when she got back. I couldn't wait.

Now we have come to the main part of this story. I guess I needed the catharsis which us why I told you the first part.

There was a knock on the door - she never knocks, choosing instead just to come in. When I answered the door she was standing there in the same clothes she had on before but was holding a brown paper bag full of who knows what. She had a look of anticipation on her face and airily pushed past me with a brief peck on the lips and a smile. As I was closing the door she grabbed me by the hands and dragged me into the bathroom. She closed the apartment door herself instead.

Once there she stripped me down and gave me a quick ball shave and a shower. After I was cleaned up to her satisfaction she blindfolded me and led me through the house, past various obstacles, to the living room, where she had me kneel on the rug. There was something different about the atmosphere in the room. I couldn't place what it was. Was it a candle? Or incense?

I heard her take off her clothes and kneel in front of me. She began fondling my dick and asked me what my safe word was. I don't think I fully comprehended this whole safe word thing or fully understood how important they could be, I told her "Nothing." I don't know if she accepted that I had no safe word or if she thought the word was "nothing". It doesn't really matter for the telling of this story.

She lay down on the rug in front of me then told me that she loved it the other day when "our neighbor" fucked her with only his cock touching her and she wanted my cock all over her body but just my cock. I figured I could move around her touching my cock to various parts of her but would be careful not to let any other part of me come into contact with her. I was hard and ready.

Suddenly, I was grabbed by two strong pairs of hands. They lifted me by my arms and legs and quickly suspended me over her. They moved me up and down her prone body rubbing my cock and just my cock on various parts of her body. I could tell they were men based on how strong they were and initially my cock shriveled with embarrassment but revived when they put me in her mouth.

Under her command they then resumed touching her all over with my cock. Every time it touched a different part of her she gushed at how much she loved the feel of my big cock on her nipples, or lips, or wherever.

She rolled over and had them do the same thing to her backside. She was really getting off on this, cooing and sighing whenever she was stimulated in a way she especially liked.

I got used to the idea that there were two goons in the room. As surprises go, I didn't like it, but I had agreed to be surprised.

When she was ready they put me back where I had started. I felt her ankles next to my knees and felt the heat of her pussy as she backed up to penetrate herself on me doggy style. She couldn't quite hit the target and she asked Jack to put me in.

For the first time in my life another man touched my dick. It made me uncomfortable but I guess it was alright given that my dick was going home. She fucked herself on me for just two or three minutes before growing impatient. Slowly she leaned forward into the prone position and not wanting me to fall out she asked the guys to keep me in.

They put their hands on my shoulders and hips and guided me down. I was laying on her back fucking her with short strokes and had kinda forgot about the guys when she told me she had something planned for me that I was really going to like but she desperately wanted to watch so we needed to get into a sixty-nine.

After our position was switched she was under me. I inhaled deeply and I was really enjoying the musky aroma of her pussy while she played with my balls. Next she spread my buns and told the guys to get the small one out. I was nervous but I still trusted her. I heard the sound of a vibrator being switched on and felt fingers apply cold lube to my ass. I couldn't tell if it was her fingers or one of the guys but I felt better about it being her so I convinced myself that it must be.

With a lot of lube and frayed nerve's the little vibrator entered my ass. Initially the entry was difficult but when I learned to relax it went in ok. It only went in about two inches and was not fat at all. She twisted it around and fucked me back and fourth with it all the while caressing my balls. It was a new and surprisingly pleasant feeling.

By her command, I lowered my head down and layed it on her furry bush so I could just focus in the feelings in my bum.

She told Patty to get the big one. I was a little excited that there was a girl in the room too, but Patty turned out to be the name of the other guy. He lubed it up and proceeded to put the tip at my entrance. It would not go in, but she just told him to keep trying. With some pushing and effort I felt the head pop past my sphincter.

It hurt like a son of a bitch and I yelped. May soothed my wounded ring with calming words, telling me to just relax and that it would only get better from here. I believed her and really did feel reassured.

Patty continued his assault, eventually getting a significant part of the vibrator into me. May took over which did finally turn to pleasure as she had promised.

Maybe ten minute's later she told me that all six inches were in me; It felt more like ten. She continue to move it back and forth and I continued to feel the pleasant manipulations of my balls, gradually realizing that it was the two guys who were playing with them because she had two hands on the vibrator. I accepted this quietly and not without some reservations because it felt dam good.

May set the vibrator aside, instead stroking my back soothingly, telling me that the best was about to begin.

I felt Jack or Patty straddle her head and imagined her view from under him. That view would have grossed me out but I know virtually nothing sexual would have that effect on her.

At his first attempt to penetrated me he missed which gave me the moment I needed to realize what they intended. Why did I not see it coming? May stroked my back some more, Jack, I think, carresed my balls, and Patty lined up with my virgin asshole.

My breathing was erratic and I struggled to get the word's out, but I soon managed to frantically yell out a strained "No."

They didn't stop. instead I felt the head of Patty's penis poised at my entrance. Again I said, "No." I said it again and again but no one was listening. I said that I did not want this. I begged and pleaded and yelled. I told May to tell them to stop but she laughed. I could hardly believe that she had laughed at my plight. She was having a great time licking my balls while Patty inserted himself into me. I could feel him getting deeper and deeper and nothing I said was making any difference. Looking back, I had forgotten that there was a safe-word and apparently May would not have accepted anything else. At no point did I say "nothing."

In theory, I was not opposed to getting fucked by a guy. But this was my first and I was not ready. More importantly, no one had asked me for my permission. Given that I was not ready nor willing this felt like rape.

I felt so helpless and powerless. I had objected and screamed but nothing stopped the invasion. I think I cried a little for the first time in years.

His cock felt much thicker than the large vibrator. My ass was being stretched much more too. It didn't exactly hurt. But it didn't turn me on either.

I tried to inch myself forward to stay the intrusion but found that my movement was limited by her hands on my hips and Jack's grasp of my balls.

I gave one final whimpering objection before abandoning hope of an end to this. Neither Jack nor May gave any indication that they heard nor cared. Patty's excitement I felt intensely in my back door and he certainly cared only about finding release in my ravaged rear.

I laid down on May's soft body resigned to the ordeal, unable to stop it and secretly mad. Mad at May for doing this to me but also mad at myself for getting into this mess.

She took my whole penis into her mouth and despite my unwillingness it grew. My dick wormed it's way into May's throat which she took with great joyful moans. I was excited again. But this was a new kind of sexual excitement for me. This was angry excitement. I pushed into her oral cavity harder than I have before, timing it with the thrusts into my ass so that I would be driven just a tad farther. I hoped, just a little, that it would hurt May like she had hurt my dignity. When I bottomed out I rocked back a little and made an extra attempt to get just one more centimeter into her. I hoped to push so far my balls would fill her mouth as well. A few times I stayed buried deep in her windpipe longer than anyone should, until guilt or fear made me back out. If this was difficult for her she never let on.

My angry-lustful passion took hold of me to the point that other concerns lost meaning. I needed to thrust hard and needed Patty to thrust hard into me as well. My ass accommodated his thick cock now, which was pistoning into my rectum quite rapidly. It burned just a little but the forcefulness of his lust for me inflamed my passions more. My own cock was as hard as it gets. I could no longer fully pull out of May's throat on the backstroke so I satisfied myself with short two inch jabs giving her space to breath only when I absolutely had to.

Jack was now in front of me, poking his cock at my lips insistently. He grabbed my head tightly with an iron grip and continued to aim at my mouth until he managed to get past my lips. My teeth were clenched but he just wormed his way into the cavity of my cheeks. I could taste a copious amount of pre-cum. It didn't feel good to have my cheeks stretched like that so I decided that all the girls who gave blowjobs must think it feels better to actually let a cock in - so I let him in. A cock was now really and truly in my mouth. But I wasn't a cocksucker because I would not suck.

May pushed her throat up onto my dick urging me to fuck it deeply. She took it as hard as I gave it. Patty mistook my throatfucking of May as me willingly fucking back onto his monster cock reaming and stretching my rectum. Jack started to pound into my open mouth right down past my tonsils, yanking my head back and forth to the timing of Patty's yanks on my hips. May dug her hands into her cunt, jerking and writhing as she started on a long series of oxygen deprived multiple orgasms.

All this frenzied action turned up the volume on everybodies level of sexual heat. My throat hurt from the pounding so I gave in and sucked Jack's cock. I sucked with passion and urgency to get him off quick. I bounced back on Patty. And of course, I continued to fuck May's face savagely.

She was trembling and twitching as she came down from her high. Jack and Patty both pulled back on my body simultaneously working against each other. Failing at their attempts to drive me down on their cocks they each leaned forward. My body was crushed between cocks on either end and I just knew they were filling me with their slimy spoo. I felt each cock throb but couldn't feel the cum which pulsed into my slippery anus and deep into my cocksucking mouth. I had forgotten about May whom I had not let breath for at least a minute. Nevertheless, I felt her pulling hard on my balls trying to pull my dick even deeper than I or Patty had driven it yet.

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from the guys, through me, and a gallon would fill her distended stomach. This thought of a gallon of cum, and May's throat spasming on my prick, my stretched ass, and the feeling of strong hands pulling me back on hard cocks sent me over the edge.

My toes curled, my groin tingled, and my urethra felt like a fire hose as I literally shot what must have been the biggest load and longest orgasm if my life.

We all fell into a jumbled mass momentarily, then pulled away from each other, all landing randomly on the carpet.

I was a sticky, sweaty mess with fluids leaking out of me and somehow spread all over my face, back, and balls.

I turned to say something to May (I don't remember what) and was jolted to my knees when I saw her limp unconscious body. Afraid I had choked her I loudly called her name and shook her seemingly dead shoulders.

A smile slowly crept onto her saliva and cum covered face as she weakly croaked "Let's do it again."

The memories of that event haunted everyday, alternately moving me to bouts of unbridled sex with May, a desire to get thoroughly fucked again, and a fear of this crazy unlimited yet amazing woman.

I have gotten fucked again since then. I also broke up with May since I just never could trust her not to go too far in or out of bed. I miss her in my soul but at the same time am relieved for my safety.

Please comment so I can make future stories even better.