My New Girlfriend's Mistress

I had been dating Lisa for three weeks. We had fucked twice, both times at my apartment, both times pretty sedate. In fact, I was starting to think that she was a little too tame for me, and that maybe it was time to move on.
That Friday, we were going to meet at her apartment, have a drink, and go out. I hadn’t been to her place before, and I wasn’t surprised to find a spacious condo with an expansive view of the city. On her lawyer’s salary, she could afford it.
We sat on the sofa in the living room, and she opened a bottle of wine. After a couple drinks, we were having a great time, so we opened another bottle. By the time we’d finished the second one, we were both a little drunk, and were listening to music and dancing. We were talking about our college days, and I told her about the weekly poker game that I used to have, and how much I missed it.
“You play poker?” she asked.
“Sure. It’s hard to find people to play, though.”
“Wait here.”
She walked into her bedroom, and came back a minute later with a deck of cards. “Let’s play,” she said.
We sat down on the floor and she shuffled the cards. She handled them like an expert, and had quickly dealt out a hand of five card draw. I had a nice hand, a pair of kings and an ace kicker. I threw the two junk cards and picked up a second ace. We showed our hands, and my two pair beat her pair of threes easily.
“You win,” she said, and looking at me with a mischievous grin, she peeled off her top. “I guess I have to take this off,” she said.
And with that, we were playing a game of strip poker. My earlier qualms about her raciness started to melt away.
The game went quickly. My straight beat her three of a kind. Her two pair beat my ace high. Soon, we were down to almost nothing—me in my blue boxers, and her in a skimpy pair of black panties. Her long brown hair hung over her beautiful round tits. At 32, she was still in fantastic shape, and her curvy hips flowed into long, taut legs.
As she shuffled the deck to deal the final hand, she asked, “So what does the winner get?”
“I don’t know. What do you want?” I said.
“Hmmm,” she said seductively. “What are you willing to part with?”
I leaned forward. “How about if you win, I eat out your pussy?” I wouldn’t normally have said something this forward, but the wine had emboldened me.
“Oh that’s a given,” she replied. “I was thinking of something a little more . . . involved.”
“Like?”
Now she leaned in. “The loser has to be the winner’s sex slave.”
Now she was talking. Not that this was entirely new to me—at age 30, I’ve had a little S&M from time to time—usually a little spanking, maybe some foot worship, and occasionally fucking a girl in the ass.
“And anything goes?” I asked.
“Anything goes.”
“You’re on.”
With a smile, she dealt the cards. I had three clubs, and also a pair of fours. I could play conservative, keep the fours, and hope to pair up the draw or pull a third four. But on a hand with this much at stake, it didn’t seem right to hold back. I three the fours and hoped to draw two more clubs for a flush.
I got them. With a queen high flush, I was confident. She only took one card. I dropped my flush on the rug in front of her.
“Queen flush.”
“Hmm,” she said, looking at my five cards. “That doesn’t beat a full house, does it?” And she put three jacks and a pair of eights on the floor. My jaw dropped.
“I guess I win,” she said.
“I guess you do.” I was still surprised at the two great hands.
She stood up in front of me. “So?” she said.
“Huh?”
“Your boxers.”
“Oh, right,” I said. I stood up and stripped them off. My cock was hard as steel.
“Mmmm, nice,” she said, running her warm hands over my chest, and reaching down to grab my dick. “So . . .”
“So,” I said.
“Well now, slave. You just wait here a minute.”
She stepped out of the living room into her bedroom. I stood, naked, in front of the large windows.
As Lisa came back into the room, she carried something that made a metallic jangling sound. I turned around to see that she was carrying a pair of black handcuffs. “Okay, slave,” she commanded. “Up against the window.”
I leaned forward against the cold glass. A small spot of precum smudged the window in front of my prick.
“Hands behind your back.” I obeyed. She strapped on the cold steel, and my hands were bound. Reaching around from behind, she grasped my hard cock. She looked down at it, and saw the smudge on the window.
“Look at that. You’re making a mess,” she said. “Clean it up.”
“Clean it up?”
“You heard me. Get down on your knees and lick it off.”
Not quite sure I was hearing this right from my heretofore staid girlfriend, I dropped to my knees and tongued my thick cum off the window. Behind me, I heard her walk to the kitchen. She came back a moment later.
“Turn around,” she said. She had the cordless phone in her hand. I turned around and kneeled in front of her. “Lick my pussy.” I leaned into her crotch and started to lick her through her panties. After a minute, the combination of my spit and her cunt juice had soaked her undies through.
Holding my head against her twat, she punched a button to turn on the phone. She started dialing a number. I had no idea who she was calling, but between the wine and the excitement of being Lisa’s sex slave, I didn’t much care.
“Hi,” she said into the phone. “It’s me.” She paused, listening to the person on the other end. “Yes, he’s here. Yes. Yes. Okay.” She hung up the phone. I kept working on her pussy, trying to slide my tongue under her panties to get at her swollen clit. With my hands cuffed securely behind my back, it was no easy task.
A couple minutes later, there was a knock at the door. I hardly even noticed it until Lisa turned away and started towards it. That had a slight sobering effect on me. I was kneeling in plain sight on the rug, my rock hard cock standing at attention and my hands useless in the cuffs.
Lisa opened the door to reveal a woman in her late thirties, wearing a very short black leather miniskirt, a sheer black blouse, and knee-high black boots. She had straight blonde hair and was carrying a small duffel bag. Without a word and without looking at Lisa, the woman entered the apartment and approached me. Lisa closed the door behind her and stood there in silence.
The blonde woman reached down and took my chin in her hand, turning my head to the left, then the right. She set down her bag, unzipped it, and pulled out a black riding crop. She tapped the end lightly against her hand, testing it. After a moment, she snapped one finger. At that cue, Lisa approached us and kneeled down on the rug, facing the woman.
“Is he drunk?” the woman asked.
“Yes, Master,” Lisa said.
“Good,” the woman said. “That will make him compliant.” She took a step towards me and slid the leather end of the riding crop down my front to my balls, which hung tightly against my cock. She slid the crop up the shaft of my dick. “He’s a little small, but he’ll do. You’ve done well, Delia.”
Finally I summoned the wits to speak. “Delia? Lisa, who is this?”
The woman turned on my with fierce eyes. She reached down and slapped me across the face. “You do not address Delia. You speak only to me, and only when you have permission. I am Master. Nothing else is relevant. Do you understand?”
“Yes,” I eked out.
She slapped me across the face again.
“Yes what?” she said.
“Yes, Master.”
“Better.” She turned to Lisa. “For your good work, Delia, you may service my boot.”
“Thank you, Master,” Lisa said. She got down and all fours in front of Master, who had stuck her right boot forward. Lisa put her face right down to it and began to lick it. She licked all over the leather surface, working her way from the toe to the ankle and then up Master’s leg. After she had finished licking
the entire surface, she sat back up on her knees.
“Oh Delia, you disappoint me,” Master said. “You know there’s more to
do.” Master turned around and bent her right leg, hold up the bottom of her boot to Lisa. Hesitating only slightly, Lisa again bent down, and this time began licking the bottom of Master’s boot. I could hardly believe what I was seeing—this successful, beautiful young lawyer, who probably ordered around the staff in her office, was calling this strange woman Master and licking the bottom of her boot. Once she had finished running her tongue over the entirety of the boot bottom, Master lowered her foot and turned back to me. “Now for you.” She stepped towards me.
“Yes?” I asked, shivering slightly.
She breathed out a heavy sigh, as if I had disappointed her.
“Yes, Master,” I corrected myself.
“I learned long ago,” she said, “that discipline is the only way to teach anything. Stand up.” I did, and she led me over to the sofa. “Back on your knees, slave.” I dropped back down on my knees, facing the sofa. She grabbed the back of my neck and pushed me forward roughly. My face was buried in the sofa cushion. I felt her running her riding crop down my back until it rested on my ass. She drew her arm back and brought the crop down sharply on my ass. And again. And again. She must have whipped me at least a dozen times, and my rear began to sting. Grabbing my hair, she yanked me back up onto my knees. “Yes what, slave?”
“Yes Master!” I cried out.
“Now you’re learning. Now you may service me.”
I turned around. Thinking that I was going to have to clean her other boot, I put my face down to the floor.
“Oh, no, slave, I’m afraid my boot care is reserved for obedient slaves.” She pulled me back up onto my knees. “You’re going to start here.” She turned around and put her ass right up against my face. She pulled up the back of her skirt to reveal a panty-less rear. “Kiss my ass, you little slut,” she said. I put my lips up against her round ass and began to plant kisses all over it. Master turned to Lisa, who continued to kneel nearby. “Do you like that, Delia? Do you like to watch your little pansy of a boyfriend kiss my ass?”
“Yes, Master,” Lisa said.
“Do you want to watch him lick my ass?”
“Yes, Master. Please.” There was a note of real desire in Lisa’s voice.
Master looked down at me. “You heard her, slave. Lick.”
Now I’ve got nothing against women’s asses. In fact, I love looking at them, groping them, and fucking them. I’ve even occasionally stuck a finger into one. But I’ve never had the nerve—or really even the desire—to lick one. I hesitated.
“Did you hear me, slave? Lick!”
I leaned back in and began to run my tongue over Master’s smooth ass cheeks. Master again sighed. “No, slave.” She reached around and took her ass cheeks in her hands. She spread them apart, revealing her tight little cornhole, just inches from my face. “Lick my asshole.”
I swallowed hard, but obeyed. Her shithole was tightly cinched closed, and I ran my tongue around it. Nearby, Lisa moaned with pleasure. Master turned and looked at her. “Did I tell you you could finger yourself?” Master demanded of her.
“No, Master.”
“Get over here and lick my twat.”
Lisa stepped over and kneeled down in front of Master, where she began licking her pussy. Master now had me working on her backside and my girlfriend eating out her cunt. She groaned slightly, holding each of our heads with a hand. “You two know how to service your master, don’t you?” Without replying, we both keep working on Master’s hot spots.
After a few minutes of getting her twat and asshole licked, she stopped us. “You ready?” she said to Lisa.
“Yes, Master,” Lisa replied.
Master looked down at me. “We should make sure he doesn’t go anywhere.” She pulled a rope from her bag. “Lie down!” she commanded. I lay down on my stomach. She tied my ankles together, then tied that line to my handcuffs, hogtying me in place. “On your side, slut,” she commanded. I rolled over on my side, my feet bent up to my shackled wrists.
Master picked up her bag and led Lisa to the bedroom as I lay on the living room rug. From the bedroom, I heard Master pulled something from her bag. A moment later, I heard Lisa start to moan.
“You like that, bitch?” Master said.
“Ooooh, yes, give me more,” Lisa said.
“You’ll take it like the slut you are,” Master said.
From the bedroom, there was a slapping, wet sound. Lisa continued to groan as Master did something to her.
After a solid five minutes of listening to my girlfriend moan to another woman’s touch, the two of them stopped, and Master came back into the living room. Lying on my side, I saw that she was wearing an eight-inch strap-on dildo, which she must have been fucking Lisa with. It was wet with the juice from Lisa’s cunt. “On your knees, slave,” she said. I struggled to climb to my knees, with my feet still tied to my cuffed hands. I knelt in front of her, with her long strap-on sticking in my face.
“Do you like making girls suck your dick, bitch?” Master asked me.
“Yes, Master,” I said.
“Well, now you’re going to suck dick,” she told me. “Suck my cock!”
I leaned forward and took her strap-on into my mouth, sucking Lisa’s twat juice off of it.. Master’s latex dick was hard and smooth. She thrust her hips against me, shoving her cock deep into my mouth, brushing the back of my throat. “Suck it, bitch,” she told me, continuing to pump her strap-on into my mouth. “Suck my cock.”
After a few minutes of deep-throating Master, she called out to Lisa in the bedroom. “Slave girl! This whore out here needs a little more discipline!”
Lisa came out from the bedroom with Master’s bag. “You know what he needs,” Master said.
As I kept sucking Master’s cock, Lisa reached into the bag and pulled out another strap-on. She stepped into the hardness and tightened it around her waist. Now both of them were wearing cocks. Lisa kneeled down behind me and started to finger my asshole. It was a strange sensation. I’ve fucked a few girls in their assholes, but I’ve never had one lick or finger mine. Lisa reached into the bag again and pulled out a tube of lubricant. She squirted a generous portion onto my asshole, then started to rub the head of her strap-on against it. After a minute of working the lube into me, she leaned in with her strap-on and stuck the tip into my asshole. At first I felt too tight, as if she was ripping me open. After she rubbed it back and forth a few times, though, my asshole relaxed, and she started to plunge it in deeper. Now I had two cocks penetrating me—one in my mouth and one in my ass.
“Fuck him,” Master said. “Fuck his little faggot ass.”
Lisa plunged in deeper, reaching way up inside me with her strap-on dildo.
“Do you like that, slave?” Master asked.
“Yes, Master,” I said. “Please make her fuck me harder.”
Lisa continued to pump my ass full of dildo, and Master fucked the same into my mouth. After getting this double-reeming for what seemed liked an eternity, Master spoke again.
“It’s time to give him his final lesson in discipline,” she said. “Lie down.”
Lisa slowly removed her strap-on from my asshole, making me feel momentarily empty. Master likewise pulled her cock from my mouth. “On the floor,” Master said.
I lay down on my back, with my hands still awkwardly cuffed behind my back.
“Do you like making girls eat your cum?” Master said.
“Yes, Master,” I said.
“Of course you do,” she said. “But you’re going to learn what it’s like to eat cum.”
She grabbed my ankles and pulled them up over my head. My cock was now directly over my face. “Are you ready to cum, you faggoty slut?” she asked me.
“Yes, Master,” I said. I had never eaten my own cum, but between the wine and her mastery of me, I was ready for it. “Then eat it, bitch,” she said. She started to jack off my cock, and in my horniness, it was only a few second before I started to spurt my jizz.
“Eat it!” Master commanded. I opened my mouth, and my cock continue
d to spurt my cum into my mouth. “That’s a good little faggot boy,” Master said. “Eat your cum.”

When I was done squirting my jizz, Master dropped my legs back down to the floor. She walked over to Lisa and gave her a peck on the cheek. “Thanks, Lis,” she said. “Call me when you ready to do it again.” With that, she walked out the door.
Lisa leaned over to me and helped wiped the cum off my face. “I hoped you liked my neighbor,” she said. “I think we’re going to be seeing a lot of her.”