College Experience: Both Holes of Office Politics (M/F), (M/F/F) | 2016

As chronicled in previous stories, I was dating my wonderful girlfriend Haley for a lot of my college experience (title drop). Haley was tall for a girl, almost 6 foot, had natural honey blond hair, pretty green eyes, gorgeous legs topped topped by a well rounded ass, a nice pair of well rounded C cups, cute dimples, a modest tan, and a truly beautiful smile. We cared about each other a lot and got along splendidly. She was a very "wholesome" girl and had an incredibly sexy "girl next door" thing going on. By this point, we'd been dating for quite a while. Haley was "predominantly homosexual, but more than incidentally heterosexual" (basically gay, but liked certain guys, of which I was very fortunate to be one) and was an insanely good lay. She didn't feel that she could give up on women entirely, so as part of our relationship, she agreed to avoid sleeping with other men and notify me anytime she slept with a woman in exchange for me notifying her if I slept around. It seemed like a fair deal to me.

Haley had really liked fucking other women, and was more or less into what I liked physically in a girl. Previously, the two of us had agreed to make a girl named Cassie our "bitch," essentially we both dated her. Cassie had straight brunette shoulder length hair, hazel green eyes, a flat stomach, a great face, and a killer ass. Best of all though, Cassie had some serious 'tig ol' bitties.... amazingly large 36 Es. She and Haley had gotten "busted" by Haley's folks previously in events detailed here or in my older works:

http://www.reddit.com/r/gonewildstories/comments/22n9bq/college_experience_meet_the_parents_mf_mff/

You can see pictures of both Haley and Cassie here: http://imgur.com/a/w3DXh

When we got back to school, it had been close to two weeks since I'd had sex. And, well I defiantly needed to get laid. Regardless, when the three of us returned to school, we were all interested in taking our relationship to the next level. There was only one obstacle...our workloads. The college we attended can best be described as a "pressure cooker" and Haley and I were both working student jobs (Cassie wasn't, as her family was loaded.)

At the time, both Haley and I were working as paid tutors at the library (we had those jobs before we started dating). I had been there for much longer than she had, was above her in the "chain of screaming." The problem was that we had the boss from hell. The student's name was Isabel; she and I worked together the previous year. Isabel had been bumped up and was effectively in charge of the program. Apparently, Isabel and Haley had previously been involved a few months before Haley and I started going out, and apparently it had ended quite badly. Normally, this wouldn't be a problem...relationships end all the time and people can generally work through the resulting awkwardness, but Isabel was a complete jerk who REALLY abused her power and was kinda a jerk (at one point she tried to force Haley to pay for her coffee from the library's Starbucks equivalent.)

By this point Haley and I were Facebook official (which at the time was THE gold standard for relationships) and our relationship was common knowledge. Isabel seem to believe that it was her life's mission to "bust" the two of us and had repeatedly informed the Dean in charge of the program that the two of us were dating. It was obvious that the Dean really didn't care, I mean interoffice dating happens all the time, and this was college... all that happened was Haley got reassigned to report directly to Isabel (brilliant move there college) and I got a bunch of forms from the college's HR people to fill out. However, after that, the incompetent jerk REALLY had it out for Haley. Haley always seemed to get the worst assignments and her "time-slots" always mysteriously appeared on weekends and Friday nights.

When we returned to school, we knew the "Isabel problem" was only going to get worse and started going out of our way to avoid seeing each other at work so we wouldn't provoke her. In my opinion, the most important part of dating someone is listening to their problems and trying to be somewhat helpful, but to my disappointment, I couldn't think of a solution and the situation just kept getting worse. After only the first week back at school, Isabel managed to so completely desynch our schedules (Ie: I was working early mornings and Haley was working late nights) that we rarely able to spend large amounts of time with one another.

That weekend, Haley, Cassie, and myself met up to discuss what to do about the Isabel problem. Now, I am a relatively patient and calm person....Haley is not and quite frankly...she was pissed. The three of us debated for a long time what to do until Cassie threw her hands up in the air and said "Fuck her...I'm not wasting my Friday on this."

Haley smiled and said "That might work." I argued against it..but from that simple seed a COMPLETELY insane plan was hatched.

Cassie and Haley spent the remainder of the weekend preparing (most of which I wasn't involved with, because I thought the idea was nuts.) That Sunday Haley and I had a meeting with Isabel to sign, yet another, contract stating that I wasn't coercing Haley into sex.

Haley wore a coat to hide her outfit. She had a skirt from yoga pants fabric and was wearing her best push up bra. Her breasts were a good sized C cup, but in that bra she looked like she had DD and was practically popping out of her top as it was. They looked eminently fuckable. Not for the first time, I was simply stunned by what a hot piece of ass my girlfriend was. Honestly, I'm still surprised I managed to make it all the way to the library without throwing her against a wall and taking her right there.

Isabel was at her desk when we arrived. We sat down and talked about how much I wasn't pressuring Haley to date me. Haley began "showing off" almost immediately leaning forward towards the desk, dipping just far enough so Isabel could look directly into her ample cleavage.

Isabel did a good job ignoring this, till we got to the questions about our sexuality (yes, the university had a form for that...told you it was crazy.) I declared myself to be straight (and I was so glad that I was doing so on a legal document to make it official...because that's totally a thing that a college should ask its students on legal documents.) As I passed the document to Haley, Isabel snidely commented "I'd just like to say that, on a personal note, I'm surprised you abandoned your sexuality."

Well, that ticked Haley off. "Who says I abandoned my sexuality?" Haley flushed indigently "I have a girlfriend too." The rest of the interview (it took over an hour) can pretty much be summed up by saying that the two of them sniped at one another in a manner disturbingly reminiscent of my divorced parents.

Needless to say, Haley was furious on the walk back to her dorm. She'd been turned down by an old lover and been in what can only be described as a verbal cat fight. As I entered her room she said "It felt really good having you inside me...I mean there with me."

I laughed as she she scoffed back in sarcasm, "It was a slip. I feel safe when you're with me."

"You mean inside of you" I joked, then winked directly at her and said "Do you want me to test that statement"?.

Haley's cheeks turned red at the joke. Quickly changing the subject I asked "So what happened between the two of you anyway?"

Haley replied "Well, the two of us shared a fantasy...she wanted to do something to me...I thought it was only fair if I got to do it back to her...she refused. We broke up over it."

Well, that merited further investigation...but before I could pry out any of the gory details Haley's phone went off. She glanced at it and said "It's Isabel." She took it. The tone between the two of them was....surprisingly friendly. I only heard half the conversation, but apparently Isabel claimed that she needed Cassie to come in and sign some more papers while the office was still open. I groaned, grabbed my computer, and prepared for a night by myself doing homework. I tried to work for about two hours...but the sight of Haley's outfit earlier had gotten me going and hard as a rock. I really wanted to fuck her.

I groaned and walked back to her room, not bothering to knock. Haley was lying on the bed, sobbing when I entered, still wearing her hyper-hot outfit. I joined her, wrapped my arms around, and asked what was wrong. Apparently, the "Cassie thing" with her parents had gotten them truly furious at her and the Isabel thing had been the metaphorical straw that broke the camel's back. Quite frankly, she was depressed about it. I spent the night with her, not doing anything sexual, just holding her and making sure she knew I cared.

That morning I returned to my place, took a shower, and got ready to go to classes. That evening, my phone let out Haley's special ringtone for a text. I checked the text

Anticipation, for me, has always ranged in degrees. I allow myself to feel a certain level of anticipation for each thing I look forward to. Classes, at the time, rated pretty high, being out with my friends, Haley, or Cassie rated higher. The levels of anticipation I had after reading that text though...those broke the scale.

The text said simply:

"Talked to Cassie. She's down to let both of us do the Isabel thing...need time to prep 4 it...Friday night ok? Her place?"

Rarely had I felt the pulse-pounding, gut-gripping fear and expectation that one single text message could bring her....I wasn't positive what Haley had planned...but it sounded awesome.

I read the text again.

Then once more.

And then a third time.

I grabbed my phone and quickly sent the message "Haley," hoping to force a conversation about what the heck was going on.

A minute later, my phone buzzed.

There was that anticipation again, but I didn't let it drag out and hit the the View button.

It said "CollegeExp"

Dropping to the bed, I sighed heavily. This wasn't going to be easy. She was going to make me ask, and wasn't going to help in the slightest. The beautiful jerk.

While I was contemplating what to follow up with, my phone buzzed again. "Something on your mind?"

Well, two could play at that game. Maybe she felt the same anticipation I did. Maybe the teasing was fun for her...

I wrote back "Maybe."

Seconds later my phone buzzed twice. Obviously, I had her full attention, because the responses were so quick. The texts said "Do tell" and "I'm all ears."

Finally, I wrote back "What's the plan?" to which Haley replied "Its a surprise love...that's all ur getting...."

Well, that made it interesting....especially the inclusion of that L word..which we had been SCRUPULOUS about avoiding to that point, but that's another story.

"Not fair!" I texted back without thinking, and could almost hear her melodious laughter.

About 30 seconds later Haley replied "My friends have been urging me to take all the things I've been denying myself for so long and indulge in them without worrying about the consequences." The a few seconds later "So, I'm taking...even though they were talking about food... I've decided to stop pretending that I don't want it."

I responded "Want what?" to which she responded "Spoilers...no details till Friday."

Over the next week I over-analyzed those texts till I was blue in the face.

The week dragged on until Friday night. I had promised to take the girls out to eat at Subway (I was poor, at the time that was fancy for me.) We had a nice dinner, but I found it impossible to concentrate on the conversation...I was literally so excited that I was shaking.

When we finally went back to Cassie's place I was nearly shaking in anticipation...so I asked "So, what's this surprise?"

Cassie walked over to her dresser, opened it, and pulled out a small, very thin, white dildo. She smiled at me as she dropped her pants and said "Haley's going to fuck my ass with this..."

Well, that was exciting! Cassie laid down on the bed, her rear end propped up on a pillow, wiggling her ass in the air. Haley put a condom on the thin dildo, lubed it up, and EVER so slowly slid the dildo into Cassie's exposed rear. It took Cassie several minutes to take the entire thing inside her ass. When she was finally "full" Cassie let out a deep groan which caused Haley to begin pumping the dildo into her. This continued for several minutes, with Cassie evidently enjoying it (I would later learn that Cassie had a weird submissive anal fetish)...until I got so hard I just couldn't take it any more. I couldn't control what happened next. I grabbed a condom and took Haley's spot perched over Cassie. I pulled the dildo out, then pulled Cassie's arms towards me, lifting her till she was in my lap. Then, I forcefully kissed her. I couldn't get the contact I wanted, so I lifted her out of the chair and took her to the a nearby glass coffee table which was just about the perfect height (and cleared of off, as I didn't want to wreck her desk and computer.)

I laid Cassie' down on top of the cold glass...she let out a moan as I broke away and stood up. I took off my jacket and shirt while Haley in did my belt and pants....my cock springing forth from its cloth prison into her face. She gave it a small lick and watched me shudder.

I looked down at her and simply said, "Haley."

She looked up before taking me into her mouth. She gave him a couple long hard sucks before pulling away and saying "Come on, show her who the boss is."

I bent my head as reverently as a priest in prayer, gently kissing Cassie's magnificent breasts as I situated my body between her legs. The height of the table wasn't quite right, but a pillow solved that problem. I slowly pressed my cock into the soft wetness of her pussy, wanting to get her all warmed up for the main event we all knew was coming. I teased her entrance with my bare cock until she arched her back and let out a deep moan of "Fuck me...." I wrapped my hands around her ample bosom and slid my cock into the warm wetness of her pussy. She was, quite frankly, drenched and perfectly tight. Slowly, I sped up the fucking until we were going at a respectable clip, then turned to Haley and said "Give her a hand will you?"

Haley dropped her hand down to Cassie's clit, massaging it like only another women could. Cassie's moans deepened and got louder as Haley and I worked together to get her hornier and hornier. Not removing her hand, Haley lowered her head around my arms and found Cassie's mouth, planting a deep and passionate kiss on it...then I felt it. Cassie began clenching up and her pussy started doing its distinctive pulsing which always proceeded her orgasm...I felt her come around my cock...and REALLY wanted to join her...but I had other prey in mind.

I pulled out before I could get off, leaving Cassie shuddering as her freshly-fucked pussy met the cool air as she crossed her ankles behind my back, nestling her sex against my,still-erect, manhood.

I looked down at the beautiful, big titted, girl below me and whispered "How would you like to have this thing in your ass?"

Cassie nodded and dragged herself off the table, returning to her bed. Haley helped me put the condom on and put a truly ridiculous amount of lubricant on it. I laid down beside Cassie in the classic "spooning" position around her, my hard cock pressed between her two ass cheeks. As my cock pressed into her ass, I felt a building up of pressure as I tried to push my way into it...and didn't get anywhere.

Honestly, I'm not sure how the whole thing would have happened without Haley...it turns out that getting inside a girl's rear entrance is actually VERY difficult, but my wonderful girlfriend managed to guide my cockhead past the rim so that just the very tip was inside Cassie.

As soon as she felt it, Cassie let out a squeak...but remained still as Haley and I slowly pushed my entire length into her...inch by inch.

It took a long time and immense patience to avoid just shoving it in...but eventually, I managed to slide my entire length into her. After I was buried inside her she clamped her ass down hard on me...I had never felt anything even close to that tight...it was crazy...I could barely move my cock it was so tight.

With me now completely inside Cassie's ass, Haley lay down on the bed facing Cassie and I, lowered her mouth to Cassie's sensitive tits, and both hands to the outside of Cassie's pussy. Cassie moaned loudly, and began to push back against me, deliberately clenching and unclenching her ass rhythmically. Already, after hardly any time inside Cassie's rear, I was close to getting off. The entire situation was just so damn hot.

Knowing that I wanted this to last, I slowed down, only to have Cassie shove her rear end back against me....hard and cry out "No...ugghh...feels pretty good."

""Fuck! I've never felt anything this tight!" I exclaimed...the words more or less just falling out of my mouth. Haley removed her mouth from Cassie's rack, gasped in mock outrage, and gave me a playful slap.

Barely even thinking, I looked at Haley and in an uncharacteristic bit of dirty talk said "Oh, don't worry Haley... I'm going to loosen you up real good. Make sure you're all good and stretched out so I can shove my this thing deep into you next!"

This earned me another playful slap and a peck on the forehead. Then, Cassie began letting out a series of animalistic moans, and began pushing her ass back against my thrusts even harder. It was obvious she was getting off one this.

Seeing that Haley looked at me and simply said "Hold on." She raised her eyes to Cassie and said "Moan for me while he's fucking your ass."

Cassie, unsurprisingly, complied. Haley responded "You're fucking loving this aren't you? First me, then him...right?"

Cassie, let out a yelp of "Yes."

Haley continued "So you like the two of us making you our little bitch? Officially making you our bitch."

Cassie let out another groan and nodded frantically. Haley kept right on going with the dirty talk, saying "It isn't like you weren't before afterall.... you are and always will be, but now I've finally got you completely broken in."

The dirty talk started getting to me...and I felt the distinct swelling in my balls...still, Haley kept going saying "Come on, you know it's true. You can't pretend you're not our bitch...'cause the second we're alone you're on your knees with your pretty face buried in my pussy... you practically shove those tits of yours into my face every time you see me...its your way of spreading those legs of yours and begging to be fucked."

By this point, Cassie was obviously getting into it...yet still Haley continued saying "From now on you're also going to be bending over. You're going to be bend over and give me this tight ass whenever I want it...you're going to beg to get your ass fucked. So why don't you beg for it?"

Right on cue, Cassie let out of cry then of "Please fuck my ass! Fuck it! I'm begging for it" and I began pumping into her even harder and more rhythmically...treating her well lubricated ass in precisely the same way I'd treated her pussy earlier.

Haley grabbed Cassie's head and gave her a passionate kiss the continued "From now on your ass is either going to be stretched around one of our cocks, that gaping asshole is going to make sure you know that you're our bitch."

Gritting her teeth tightly, Cassie was obviously doing her best to keep herself from screaming or trying to keep any moans from escaping her lips again. She failed miserably at both.

Right before I reached the point of no return Cassie cried out "God, please fuck me! Fuck my ass and make me your bitch!" With that, I couldn't stop myself anymore....I went off inside the condom and pretty much filled it completely.

For a few long minutes I simply lay there, still inside Cassie, in a sweaty heap, much to exhausted to stand up. Then, I pulled my entire length out of Cassie' butt with an audible popping sound.

I got up and went to the bathroom. I took me some time to clean myself off, take a short shower, and dispose of the condom properly.

When I returned Cassie's head was buried between Haley's leg, her tongue pressing itself at the very bottom of that little entrance, giving long and slow licks to her pussy.

Already ready to go again, I walked forward, grabbed Haley's head, and kissed her hard on the mouth. Our teethed clack together for a moment before finally finding an angle that’s comfortable, and before I knew it, Haley was pressed back against the headboard, my hand on her lower back (okay, okay, upper ass), with me hovering possessively over her as Cassie went down on her. We parted for a second, and she gave me a you-have-got-to-be-kidding-me look. “A little eager, aren’t you?” she said in a tone which can only be described as "soccermom" and only made me want to fuck her more.

“You just look so…so…” then I shut up and kissed her hard....again. She moaned into my mouth, obviously enjoying the pleasure Cassie was giving her. I knew that there was absolutely 0 chance of getting in her ass that night (Haley had something approaching a complex about her's, believing it wasn't attractive...it was...)

Haley's hands were wrung into the quilt, her chest flushed, as I pull her swollen bottom lip into my mouth. When I sucked on it, she made a low noise in the back of her throat that I suspected she didn't even know she’s making. I’d tease her about it, but then she might stop and I found it impossibly hot.

She was close to coming, I could feel it...could see the rippling tension in her stomach, the inevitable result of Cassie's ministrations. I glanced down at Cassie, still happily lapping away, and said "Let me take over." Cassie stopped, and moved forward to straddle Haley's chest as I dragged her to the edge of the bed.

I spread Haley's thighs open, teasing the edge of her pussy with my cock as her hands unclenched from the bedspread to grab at Cassie, nails digging into the other women's skin. I liked that, grinding my cock right up against her pussy and humming as Cassie's forced Haley's head down in order to sit on her face. Soon, Cassie was facing me, completely nude, straddling Haley's face and evidently enjoying it as I teased Haley's pussy. I saw Cassie's back arch, as Haley's nails dug deeper into her shoulders, leaving little half-moons.

Then, I entered Haley. She was as wet and tight as ever...and her muscles clenched and clenched around me almost immediately, and I knew that it wouldn't be long for her...I could sense how close she was. I distinctly remember thinking "Well, might as well make the most of this" before plunging into her. Her inner muscles clenched tighter and tighter as our rhythm accelerated, until her pussy began pulsing and I felt her get off.

Meanwhile, the view in front of me was...incredible. Cassie was grinding her pussy on Haley's face...which did....fascinating things....to the pair of E cups bouncing less than a foot away from my face. I'm a tall guy, and I just couldn't help staring. Cassie's eyes opened and she caught me of course. She let out what can only be described as a moaning laugh and said "Checking out another women's rack while fucking your girlfriend? Really?"

I smiled at her and replied "Well, your tits are worth that kind of attention..." and bent as far forward as I could to grace those exceptional boobs with a kiss and raising a hand to cup them. (I admit, I have a serious fetish for a nice rack.)

Groping Cassie's rack while fucking Haley really turned me on, and I felt that distinctive tightening in my balls that always proceeded an orgasm. Every time I went deeper into her, they got tighter and I knew I couldn't last much longer.

I looked up at Cassie and said "I'm going to fill your girlfriend's pussy" then exploded inside Haley.

Cassie let out another deep moan, then chuckled, "You two are so lucky I won't tell that human resources bitch you fucked me in the ass."

From beneath Cassie's legs I heard Haley say , "Let them stew... she deserves it after making me get her coffee."

I laughed and replied "I thought you were going to hit her" before pulling out of Haley, then collapsing like I'd just run a marathon.

I woke up to a mouthful of blonde hair. Somehow, in the night Haley and I had become entangled. I was practically on top of her, one arm thrown across her torso, her slender leg pinned between my. I could feel her breath on my shoulder, and felt Cassie move down by the bottom of the bed. I'd never spent the night with both of them before.

I furtively tries to slide away from her so I could go to the bathroom. That was something I'd become quite good at, over the years of extricating myself from the embraces of one-night-stands. But Haley, still asleep, grumbled at the loss and only tucked herself more firmly against me. I laid back and went back to sleep...in bed with my two beautiful women.

Editorial Note:

I'm back...sorry it took so long. Work has been hell blah blah blah. Hope you all enjoyed it! Cassie will be coming through the town I'm based in this weekend. We're supposed to meet up and have dinner. I'll let you guys (and statistically speaking, you're basically all guys) know if it goes anywhere if there's an interest in it. I'm always interested to read your comments. I also respond to PMs.