To paraphrase Bruce Willis in "Pulp Fiction", it was the weirdest fucking day of my life:
I was living with my Rachel as my room mate after she and her ex split. They had been divorced for about a year when she started meeting women and bringing them home. I admit it was a little weird, but listening to Rachel and her girlfriends in her bedroom stoked some of my best ever masturbation sessions.
The sounds seemed to be particularly impassioned when she was with a dark-haired fox, Mon. She was a repeat visitor to Rachel’s room. She was also the only girlfriend that sat down to breakfast with Rachel and me in the mornings.
Ultimately Mon was Rachel’s only girlfriend.
It was a vicarious thrill to sit there with them and some mornings see that one or both of them hadn’t washed her face yet, and was sporting cheeks flaky with dried pussy juice.
I should tell you Rachel is a knock out. About five feet five inches tall, she’s religious about her workouts, she practically lives in her tights, and weighs about one hundred and ten pounds; all finely toned muscle. Her blonde hair? As natural as her 36C breasts.
Mon was Rachel’s antithesis; tall with jet-black hair, loud and tough. I think she could kick the ass of almost any man I know. She was smart as hell and she believed in strict discipline and having everything in it's place..
Almost every night she would tell Rachel, "When are you going to realize the little twerp is going nowhere? He needs to be booted out of here," at least three or four times before they went to Rachel’s room.
Soon after, the cries would echo down the hall, "AHHHHHHH yessss Rachel. That’s my girl! Do me right, you know you like it this way!" and a while later, "Oh yes Mon, yes yes yessssssss!"
Well, a guy just can’t lay there and listen to the things they said, the thumping and crashing and bed squeaks, and not wonder about the things they were doing.
One day I went home from work early. Rachel and Mon were both still at work and I sat down at the PC in the living room. I used a "Hacks & Cracks" floppy I borrowed from Theodore, one of the best geeks at work, to crack Rachel’s password and access her user profile (they don’t call it ‘Windoze’ for nothing!).
Their bookmarks were "interesting" to say the least. Women’s Discussions, online sex toyshops, and Lesbian Erotica web sites seemed to be the top three categories.
I also browsed their private directories, looking at the pictures they had downloaded.
"Cunnilingus and Dildo City," I read out loud. That directory was loaded with pictures of women eating muff and fucking each other’s holes with dildos. My cock was throbbing almost painfully and I opened my pants for the sake of comfort.
Then I accessed a sub-directory called "Special". If the rest of the stuff wasn’t special, this had to be hot stuff!
I gasped. There was Rachel and Mon. Rachel was the centerpiece of this little tableau; tied naked to the bed with a huge dildo wedged in her vagina, and the look on her face was one of either sheer agony, or pleasure. A wire led from the dildo to a little box, some sort of remote control that Mon held. Mon had a shit-eating grin on her face like you wouldn’t believe.
I couldn’t help but stroke my cock as I clicked through the rest of the ‘Special’ directory; Rachel getting things and fingers stuck in her ass and pussy, going down on Mon, even a couple of Mon spanking Rachel, her bare ass glowing red.
Toward the end were some of Mon, no longer the one in charge. Now she was naked and tied on the bed with Rachel sitting on her face and another woman, whose features were blurred out, sticking things in Mon’s pussy.
I looked at the clock. I’d been pretty focused and time had flown, Rachel would be home shortly. I logged out and with my cock pointing the way ran to my room where I finished what I had started.
I was lying on my bed reading, enjoying my post jerk off good feelings when Rachel got home. I heard Mon’s voice too, maybe a little louder than usual. A couple of hours later Rachel poked her head into my room.
"Mon and I are staying home tonight, and she brought dinner, come on out Thomas."
I should have caught the hint. She NEVER calls me Thomas.
"Be right there Rachel," I replied.
I walked into the dinning room, and on the table were the inevitable Chinese food cartons. When Mon bought dinner, it was always Chinese. But the cartons weren’t the only thing, oh no. On the table in front of Mon was a floppy disk.
My eyes went to the disk label; ‘Hacks & Cracks’ in Theo’s flourishing handwriting. I looked up from it and saw Mon’s face. It was red, and she gave me this stare that sent chills down my spin. Rachel walked over and stood behind Mon. I looked at her and she looked away, blushing.
No one spoke for about 100 years. I just stood there. Mon stared, Rachel studied the ceiling, then the floor.
Finally I said, "I’m sorry".
Mon just kept staring. Rachel finally spoke up, "Thomas, how could you? Oh GOD I am so embarrassed!" she cried and covered her face with her hands.
"See what I mean Rachel, he’s a worthless little sneak," Mon finally rumbled without taking her eyes off me.
Rachel just sobbed, but Mon continued, this time talking to me.
"You little brat. Just like her ex. A worthless, sneaky, lazy little fuck. Did you jerk your little pee pee after looking at your roomy and me naked? Huh?"
"N… No!" I replied. But I felt my face burning, betraying me.
"Well let’s just go see shall we?" Mon said very calmly.
She stood up and walked over grabbed me by the back waistband of my jeans, and screamed "March, maggot!" in her best Drill Instructor tone.
My feet barely touched the fool as she shoved and marched me down the hall to my room. She tossed me through the doorway, into the far corner of the room. Rachel had followed us, but she stopped in the doorway, blocking my exit.
Mon went straight to my bed and yanked it away from the wall like it was made of balsa.
Thus was revealed my crop of used tissues.
"Pay dirt!"
I hung my head in shame as Mon shouted.
Rachel let out this terrible moan and sprinted across the room, grabbed my shoulders, and pulled me up so I was on my knees in front of her. She was tiny but strong, and I was weak-kneed in fear and embarrassment.
WHAP! She slapped me across the face.
Mon laughed, not a funny ha-ha laugh either and from across the room said "There’s no porn, the little prick has been listening to us and jerking off, Rach!"
"You little bastard," Rachel yelled, and punctuated it with another slap across my face.
Mon walked over clutching a wad of tissues in both hands. She brandished them at Rachel.
"Look at this," she held up a wad and closed her hand around it, it crunched dryly, "He’s been in jerk off heaven listening to us," she said. This inspired Rachel to slap my face yet again.
"And," Mon continued, "Here’s his dirty work for the day!" She held up a still wet tissue, letting it dangle from her fingertips for Rachel to inspect. I looked up; they were standing on each side of me. There was no running away, and where could I go if I did?
"Let the little fucker eat it," Rachel said.
I was aghast. What did she mean, eat it? I found out real quick as Rachel grabbed me, one hand on each side of my jaw. She dug her thumbs into my cheeks and forced my mouth open, while Mon stuffed the tissue into my mouth.
"Gaaaaaaaaa!"
Mon joined Rachel in helping me to chew the mess, the two of them gripping my head and jaws and forcing me to chew. Finally one of them pinched my nose shut so I had to swallow in order to get a breath.
I gagged and choked as I gulped the soggy sour mess down.
Rachel left to fetch me a glass of water, "To wash down your appetizer," she said.
While she was gone Mon told me, "You are so fucked." I met her stare for a few seconds and her normally brown eyes were dark as the night.
She shifted her grip from my jaws to the back of my neck, she could hold me firmly that way.
Rachel returned and Mon tipped my head back. I opened my mouth and Rachel poured the water into my mouth, I was thankful because I was still choking down pieces of tissue.
"Thomas…. Thomas what am I going to do with you?" she asked as I gulped the water.
"Don’t answer you little jerk off punk," Mon said.
She spoke to Rachel as though I wasn’t there. "This little punk just joined my training program, Rach."
"Training program? What do you mean honey?"
"Since he likes looking at lesbians, he’s going to be one."
I started to protest, but Mon tightened her grip. It felt like she could paralyze me if she wished, so I shut up.
I could see Rachel ‘s face. She wasn’t saying no but I could tell she had more questions for Mon.
"Let’s sit down and talk this over Rach."
Rachel nodded, and headed for the living room. Mon dragged me along and they took seats on the sofa. Mon parked me in front of them, still on my knees.
"Keep your trap SHUT," she said, and I listened as they talked.
"Look Rach, despite all my bitching about him, it’s not really his fault," Mon said. "It’s genetic. He’s a sick little fuck, he's a guy! It’s not your fault either. Without a lot of hard work, it seems like the bad genes always win."
Rachel nodded, she was sniffling as she looked at her lover and listened.
"The only way to erase the bad from Thomas is to turn him into a girl. I trained girls for two years; I was the best in the business, too. I can train him to be a girl. And I know someone who can take care of the surgery."
"Surgery?" both Rachel and I said at the same time.
"You," Mon said, reaching and slapped my face, knocking me over backwards, "Keep your trap SHUT like I said."
"As a matter of fact, I’ll give you something to keep you busy. Strip, horny boy."
No way I was going to strip. I’d be quiet, but not strip naked.
Then Rachel looked at me. With fire in her eyes she said, "Yes why don’t you do that Thomas. Let’s all get on equal terms; you saw us, now we see you."
Mon smiled at me and raised her hand as if to say "or else".
I realized there was no way I could win so I began to undress, very slowly.
"Now, Rachel, as I said it’s genetic. Their testosterone fucks them up. The only way to unfuck him is to eliminate the bad juice, so to speak!"
With that she slid across the sofa and embraced Rachel, giving her a long wet kiss. With one eye on me.
They broke their clench and Rachel looked down at me. "Better get naked faster, Thomas. I want to see that pee pee, while you still have it. After all, you saw my pussy." She had a strange, almost vacant look on her face as she commanded me.
I had my pants off, but all this talk of actually making me a girl was too much and I started to get up, shouting, "No way you are cutting my cock off, crazy bitches!"
Before I was on my feet Mon was up and swinging. Her fist caught me cleanly on the jaw and I went down like the proverbial ton of bricks.
I lay on the floor with a numb jaw, and seeing stars. Rachel sat on the sofa, watching. Mon stood over me, looked down with a very serious expression on her face.
"Call me or Rachel a bitch again, and I’ll do your surgery on the kitchen table with a steak knife. Got that? Just in case you don’t GET IT, your world changed today. Now, get naked like we have both told you to."
My knees were pretty wobbly but I managed to stand up with a hand on the arm of the couch. All resistance was pretty much beaten out of me now. I shucked off my underwear and my shirt, and stood naked in front of my Rachel and her lesbian girlfriend.
"Hmmm not bad," Rachel said mostly to herself as she reached out and grabbed my cock. "You’ve got a nice dick, big and fat. Almost a shame…."
I started to pull away, but Mon literally growled at me and I froze.
"Remember Rach, that’s the thing that causes all of their troubles," Mon growled again.
That didn’t seem to deter Rachel. Her grip and shifted, and she was stroking my cock!
I couldn’t help it, what man could? My cock began to throb. Somewhat half-heartedly perhaps due to the flogging I had given it earlier. Rachel giggled, and began to stroke me in earnest.
"Mon?"
"Yes, Rach?"
"Please darling. Fuck him. Show him what he’ll be in for as a girl."
I was screaming "NO!" to this entire sick tableau, but only in my head. Hormones, and looking back, probably a mild concussion, had robbed me of resistance by now. The loving stroke of my Rachel’s hand on my cock held me in place, almost paralyzing my leg muscles.
Mon got up from the couch. "I’d be happy to, dear. One more cherry notch on my harness!"
I was grunting and trying to minimize the thrust of my hips in response to Rachel’s ministrations, and she was kind of cooing, almost as though she were singing a nursery rhyme under her breath.
My shaky legs were threatening to give way and she noticed, and guided me to the couch.
"Here… No… Don’t sit!" She sat down and then positioned me so I was on my knees, chest resting on the cushion, my ass sticking out into the room. My face was pretty much between her thighs. And I smelled her through her jeans.
I wasn’t a virgin, so I knew that smell. But my two sexual dalliances with Peggy O’Neal had lasted a total of 10 minutes. I really hadn’t done much beyond grope, sniff, lick, and poke in the dark back seat of Peggy’s parents Plymouth Voyager.
"That’s it darling. Nuzzle in there. Um hm. That’s it honey rest easy um hmmmm…" she breathed as she ran her fingers through my hair.
"Hold him tight Rach," Mon’s voice rumbled behind me. As subdued as I was I still tried to turn and look, but Rachel had a good hold on my hair.
"Holy shit Mon! You’re going to make his cherry a memorable experience!" Rachel exclaimed.
I resigned myself and inhaled Rachel's odor. They couldn’t know I wasn’t a virgin and I was relieved I wouldn’t have to fuck Rachel. I was trying to figure out what Mon was doing. In this position all she could do was to slide beneath me and blow me, I thought. But I did wonder what my Rachel was carrying on about.
Then I knew. I felt Mon’s legs brush mine as she knelt behind me. She didn’t waste time, she used one big hand to spread my ass cheeks, holding them open while she lubed my asshole with the other hand, jabbing one, two, and then three of her fingers into my butt hole. She wasn’t particularly gentle as she reamed me out, and I heard her laugh at my failed attempts to escape, which simply forced my face more firmly into my Rachel’s jeans clad crotch!
I screeched and I bucked against her hold on my hair. But I was weak and could get no leverage. Mon’s thrusting fingers were in total control at the other end. I was quite literally, fucked.
I began to cry and ask, then beg, for forgiveness.
"Go on honey, he’s ready now, fuck him," Rachel called over me to Mon.
"Oh yeah Rach, I’m ready too. You’re enjoying this almost as much as I am," Mon replied to her.
Then she spoke to me. "OK boy. I’m going to fuck your butt, and there’s not a damned thing you can do to stop me. You can, ahhh, relax and enjoy it, or resist and I will shred your tight asshole. You are in control!" She laughed at that. No one could be much further out of control than I at that point!
Mon pulled her lube-slicked fingers out of my butt, and wasted no time replacing them with what felt like a log!
"Open wide Thomassssss!" Mon barked and hissed. I felt her lean into me, pushing the log-thing up my ass…. Which opened under the battering assault. It hurt, as my hole was forced open, I had no chance in hell of relaxing and enjoying. My anus was on fire, probably torn.
My screams were now a long keening whine into Rachel’s crotch, who was using my hair as a handle to position my tear stained face as well as keep me firmly under her control.
"Ohhhh yeah Rach, he’s no cherry boy now. I’m past the first sphincter. And I think, despite all his screams he actually enjoys this, don’t you Thomas?" To emphasize her point she gave an extra thrust, drawing another, and higher pitched scream from me.
"Wonderful Mon, wonderful. He’ll make a good lesbian too, I can tell from the way he burrows between my legs. I’ll bet that if I didn’t have my pants on her would have his head up my cunt!"
"Mmmm yeah babeeeee, you know what to say to make me hot!" Mon bantered back. "And the hotter I am the harder I’m fucking nasty boy’s butt!"
She made good on her word by jack hammering her hips against me, driving her thing deep into me, splitting me open. But there was plenty more to come….
"Oh, oh yes. Yes. Half way there, Rach!" Mon crowed. "He’s getting tighter the deeper I go," she said.
I felt Mon’s hands on my hips. They wrapped around me, it felt as though her fingertips were nearly touching beneath my belly, her hands were that large!
Mon began to slowly pull me back, away from Rachel’s comforting crotch where I saw that Rachel and I had combined to thoroughly soak her jeans, and onto her violating thing.
"Come to your new boss, baby. Take my boss cock," Mon shouted. The way I heard her shout when she was sexing Rachel.
Her cock. I knew now this was probably one of the lager dildos she and Rachel had used in their little photo shoot.
Millimeter by millimeter I was stretched and penetrated, Mon’s strong hands exerting the irresistible force of my butt fucking. The giant thing snaked into my guts, I felt my inner passage open inside my abdomen and the second sphincter flower open at the top of my rectum, and allow the intrusion to continue.
I was screaming, crying, and laughing. I had never felt anything like this before. Pain and humiliation that made me want to die, and pleasure that I would pay or do anything for. All wrapped up in one afternoon in my own living room.
"Do him Mon, do him! Do the Titanic thing like you do with me!" Rachel cheered her lover on and scooted forward on the couch in anticipation.
"Sure thing honey, and tonight, it will be your turn."
"But right now it’s Thomas's turn," Mon continued. "Hang on I think you’ll like this butt boy!" she finished.
Next thing I know, Mon shifts her hands a bit further up my body, between my armpits and waist, and stands up! Yes, while impaling me on her cock, handling me like a doll. The woman is that strong.
Rachel reached out and began pumping my cock. It was semi-hard to start, and raged into full blue steel hard on with a couple of strokes.
Semen began to boil up through my urethra. I felt my own drool splash my chest as I went slack-jawed.
Mon leaned back so she held me out in space (think "I’m king of the world" from Titanic) and pumped her hips powerfully. I shrieked as the dildo socketed home in my bowels. I felt lube and stuff squirt around the shaft of the thing as my passage convulsed. At the same time my fantastically rigid cock turned inside out, or felt as though it did… My hot semen jet-squirted onto Rachel….
"Ohhhhhh yeah Mon! It’s like you came on me, through him!" She cried out.
Mon kept fucking me and let out a series of roars, and that’s the only description, she roared! It was really starting to hurt now that I had cum but my protests were rather weak, and I stood no better chance fighting her now than I had earlier, when this entire bizarre thing started!
So she fucked me and I cried, I may have come close to another orgasm a time or two but now Rachel used her touch to pinch the base of my cock and head off the impending pleasure. This was all about me being fucked, pure and simple, no enjoyment promised or implied.
At last Mon tired, I think she had some orgasms herself (and now I know for a fact she did!). She let me down and while I half stood half-laid across the back of the couch she pulled her cock out of me. Things hadn’t changed, she wasn’t very gentle on the withdrawal, either.
While Mon went to clean up, Rachel cleaned my butt and doctored it. "As one would expect, losing your cherry you got torn a little. You’ll be OK though, sweetie."
Mon returned, slapping my ass and then stepping beside me. I turned my head and saw her massive strap on cock for the first time. I swear, it was nearly as big as my forearm.
"Thomas, who’s your boss?"
"You are Mon!"
She grabbed my hair in one hand, and waved the rubber cock at me with the other. "Good answer, now suck, it’s time to do the other end!"
I told you. It was weird.
Kevin G WhackStar Productions © 2002
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