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Mistress Lisa - Part Two

"A pegging session turns into a FWB relationship"

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Author's Notes

"Part 2 of 2."

I waited two days before I called Lisa to set up our “date.” Due to her schedule, we agreed on Sunday afternoon at 4:00 pm. That would be four days since we had seen each other.

My manscaping schedule was usually once a week. I had shaved on Wednesday morning before my pegging session. I went the extra mile by shaving again on Friday and Sunday mornings. My pubic area was smooth as a baby’s butt, as the saying goes. Since Lisa had briefly licked and sucked my cock previously, I was hoping she’d orally worship my big nine inches on Sunday.

On my way to Lisa’s, I stopped at a liquor store and picked up a nice bottle of wine for us to enjoy before or after our play date. When I arrived, I wasn’t sure what to do, so I texted her, “I just parked.”

Her reply was priceless, “You and your big cock can come to the door now,” with a laughing emoji followed by the eggplant emoji.

Just like before, Lisa opened the door as I approached. This time I was greeted by a stunning forty-year-old woman in a pink summer halter sundress, with no bra, and casual leather sandals. Her long black hair was pulled back into a loose ponytail. She wore just a tad less makeup and was more appropriate for a Sunday afternoon. No heavy black eyeliner or sultry eyeshadow on this day.

“Wow, Lisa, you look great!” I told her. “I wondered what you’d look like in normal clothes.”

She laughed, “Yeah, I’ve run into a few clients in public. Most didn’t even recognize me. Only two looked me in the eyes to acknowledge me.”

I handed her the wine and she asked if I’d like a glass. “I already started with an Old Fashioned. Would you like something else to drink?”

“Sure, I’ll have a short Old Fashioned,” I told her. “I don’t want to drink too much.”

“Yeah, you better not get whiskey dick on me!” Lisa giggled.

I had wondered how this hookup might go as far as kissing, getting naked, and such. Would we make out on the couch first? Would we just go to her bedroom and get naked? What are the rules? I was naturally hoping that this would be a “Girl Friend Experience,” with everything on the table.

I gently approached the subject, “So, how do you want to do this? Kiss on the couch and go from there? Go to your bedroom and get naked? And what are the rules? To be honest, I’m a bit confused and nervous about doing something wrong,” I honestly told her.

“To be honest, I’ve been thinking of those exact same things. I’ve never done this with a client. I have sex with most clients, but that is always on the clock. Today is for our fun and pleasure,” Lisa said.

“Look, why don’t we just slowly start to kiss and see where we go? I’m guessing you want to end up in your bedroom?” I asked.

“Not necessarily. I’m open to fucking anywhere we feel like it,” she said.

I moved around her kitchen island, and put my arms around her waist, and kissed her cheek. My hands slid down to her fine ass and gently squeezed. My next few kisses were on her lips. She took the initiative and plunged her tongue into my mouth.

Lisa stopped and looked me directly in the eyes. “Like I said, I’ve never done this before with a client. In fact, I haven’t been on a real date in over five years. I get enough cock in this line of work, and I am usually sexually satisfied. But today is different. I want your big cock. I want to lick and suck it. And I want to fuck in several positions,” she told me. “And the biggest difference is that I want you to be the lead today.”

I laughed. “I always lead.”

“I had a feeling. I get guys like you who just want to try pegging. To do something different,” Lisa said. “I could tell the moment I saw you walk up to my door the other day that you’re an alpha dog.”

“Yes, I am. OK, what about rules?” I asked.

She giggled, “None. Well, except no fucking me in the ass. You’re way too big!”

“Yeah, I’ve heard that more than a few times,” I told Lisa.

“Have you ever fucked a woman in the ass?” she asked.

“Just once. Another provider. I told her how big I was when we talked, and she agreed. But she did charge me an extra fifty bucks,” I said. “She told me she prepped by using several butt plugs earlier that day.”

We soon moved to her living room and simply started to kiss on the couch. As things progressed, we were both naked after about ten minutes. Lisa wasted no time in taking my cock into her mouth.

“Look at this delicious cock. Not only are you really big Paul, but you have such a nice fat mushroom head,” she said. As she held my manhood with two hands Lisa licked my head and swirled her tongue around the crown several times before removing one hand and taking half of my shaft into her warm wet mouth. “And feel free to cum in my mouth. I love the salty-sweet taste of cum,” Lisa giggled.

For the next fifteen minutes, she teased my head, shaft, balls, and browneye with her tongue and mouth. I was brought to the edge twice and she instinctively knew when to back off, change techniques, or simply stop, to prevent me from cumming. And she really seemed to enjoy my dirty talking.

I asked if she’d like me to return the favor, but Lisa told me, “I’m so fucking wet already I don’t need to be licked. I’m ready for you to fuck me silly.”

Since she had said she was open to having sex anywhere in the entire house I told her to get on her knees on the couch and lean over the arm roll. I placed my right knee on the couch near the back cushion and stood on my left foot as I slid my crown up and down her soaking wet slit.

“Mmmmm, that feels good,” said Lisa. “Fill me up with that big cock.”

I slowly pushed my meaty mushroom head into her love tunnel. I stopped, just to tease her. I slowly, and I mean s-l-o-w-l-y, pushed my entire nine inches into her wet pleasure palace. When I bottomed out, I stopped.

“You feel so good in me,” she moaned. “Ohhhhh, please, go slow to start.”

So, I did. I slowly pulled back my hips, resulting in my cock retracing its route. As I was admiring Lisa’s glistening juices on my manhood, I left just my head in her box. I then moved forward as I held Lisa by the hips. “Like this, baby?”

“Yes,” she moaned. “Ahhhhhhh, shit. I just know I’m going to cum quickly.”

“Want me to stop?” I asked.

“No. Go a little faster,” Lisa requested.

As I slowly built up the speed of my thrusting, I resumed talking dirty to her. “Oh, does the whore like my big cock. Is the whore enjoying getting fucked?”

“Yes, I love your big cock Paul,” she stammered as I fucked her. “I’m really close. Fuck me hard now.”

“Hard and fast, baby?” I said.

“Yes. Make me cum. I need to cum,” Lisa whimpered.

I took hold of her hips extra tight and started driving my big tool deep into her tight kitty. I’m used to having “experienced” women feel tight due to my girth, and I was quite surprised at how good Lisa felt.

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She was moaning and groaning as I got faster and faster. Thankfully, the way she was leaning over the arm roll of the couch kept Lisa fairly still as I pounded her from behind. I leaned forward and with my left hand found her large boob. As I grabbed a fleshly handful, she released a loud “Ooohhhhh!” My fingers instantly found her rock-hard nipple. I rolled her nipple in my fingers before finally pinching it. “Oh yes! Harder!” Lisa yelled.

By now I was slamming my love snake into her snatch as fast and hard as I could. The sound of my balls slapping against her pussy was loud. I then felt her inner kitty walls start to spasm and tighten. I knew what was coming next, no pun intended.

“Yes! Harder! Faster!” she yelled.

“Tell me how much you love my cock, bitch!” I fired back at her.

“Oh, fuck yes! I love your cock, Paul! Fuck me hard!” she grunted, then started yelling, “I’m cumming! Don’t stop! Fuck me through my orgasm,” she commanded. This woman knew what she liked, and I bet there was a reward if I did as requested.

Her pussy started to clamp down on my penis. She was moaning, groaning, and stammering “Fuck me, Paul. Make me your bitch!”

As she was almost done cumming I knew I was close. “I’m going to cum soon. Where do you want it? Pussy? Face? Tits?” I asked. I reached up and grabbed her ponytail, pulling her head back.

“Pussy. Just keep fucking me. Don’t stop!” she mumbled as her pleasure wave was just about over.

My balls tightened, my legs shook, and I yelled like a caveman, “AGH! UGH!,” as I emptied my balls into her hot wet pussy. I made sure to keep thrusting as she asked.

“Don’t stop. Keep pounding me,” Lisa said.

Thankfully, my cock does not go soft quickly. I kept up the rhythm and I soon knew why she wanted me to keep fucking her, as she had another small orgasm.

“Don’t stop, I’m cumming again!” she panted as she tried to breathe and enjoy her sexual high. And then she began yelling, “Yes! Yes! Yes!” Lisa was now squirting, shooting liquid all over her couch and me. It was then she told me to pull out. When I did it was like a river of water and my milky white cum. As I admired my work Lisa’s legs went limp and she fell onto the couch.

“Oh my god. That was amazing,” I told her. I fell back on my heels. I could see her body shiver as she was still surfing her wave of orgasmic bliss.

Lisa was silent. After about a full minute she slightly turned to look at me, “Best fuck of my life. Thanks Paul. That big cock is fabulous,” she said with a devilish grin.

“Oh, you say that to all the guys,” I teased, laughing.

“I might need to see you once a month for a free session. I will want, and need, to be fucked by you again and again,” Lisa said quietly. We slowly moved into the kitchen where we talked as we sipped on water.

I asked Lisa how she got into the business. “My cousin was living high off the hog and she said she had this great part-time job. I asked her about it three or four times before she finally told me,” Lisa said. “She was seeing up to ten clients a week. She was making over twelve grand a month. About a month later I asked her to teach me the business. The rest is history.”

We finally made it into her master bedroom where she rode me in reverse cowgirl. As she did, she had me finger her ass which she really seemed to enjoy. After several minutes she spun around. Her big tits were now right in my face and I couldn’t resist sucking on her milk melons. She moaned as I lightly bit down on her giant nipple.

“Are your tits sensitive? Want me to suck on them more?” I asked.

“Yes. I love having my boobs sucked,” she lightly moaned.

As I squeezed her tits, I alternated sucking on each boob. Flicking her nipples with my tongue, and simply sucking like a Hoover vacuum. All the while she kept an even rhythm riding my nine inches.

“Oh fuck. I’m going to cum again. Your big dick is magical,” she whispered.

“Good, because I’m real close. I want to cum on your tits,” I told her.

Lisa started rocking faster and harder trying to induce her climax. She was soon breathing heavily, moaning, and had her head looking up towards the ceiling. “Yes! Yes! Keep fucking me,” she stammered.

“Let it go,” I told Lisa. “Cum for me, baby! Ride my big cock!”

Lisa began yelling, “Oh, oh, oh!” She started thrashing a bit too. “YES!” she screamed as she shook and summited the mountain.

As soon as she was finished, I told her, “Get on your knees. I’m going to cover your tits with my big load!”

Lisa quickly moved to her knees on the floor as I stood up. She grabbed my cock and started stroking me. “Shoot that cum on my tits, Paul!”

After about twenty seconds I told Lisa, “Suck my cock for a bit.”

She began bobbing up and down on my big, long shaft. Next, she teased me by licking my upper shaft and mushroom head. “Give me your load, Paul!” she said.

I pulled out as I knew I was about to blow. I started jerking off and Lisa held up both tits giving me a great target. “I’m going to cum!” I yelled as my first big spurt landed on her clavicle and went down toward her nipple, easily five inches in length. The second gusher landed right in her upper cleavage.

“Yeah, Paul, cum on me, baby!” Lisa said.

I shot a few more nice pearl bullets of jizz on her tits. Lisa took control of my dick and milked out several big globs of cum which she licked off my head. As I surveyed my white gold on her tits, I smiled.

I bent over and licked up one of the big pools of cum and moved towards Lisa’s face. “Kiss me.”

After we kissed she said, “Oh, you’re a nasty one. Not many guys would lick up their own cum and snowball me. That’s hot!” Lisa continued with a big smile, “You are a bit of a freak. Pegging, snowballing… what else do you do?”

I laughed, “I’ve had a gal snowball me after I blew my load in her mouth. I checked that off my sexual bucket list, just like pegging. I doubt I’ll do either again.”

“But you just snowballed me,” she said.

“True, but I didn’t swallow a big load. The other time I did,” I confided.

Lisa giggled, “And how did you like the taste?”

“Meh. A tad salty and tart,” I told her.

We moved up onto the bed and spooned. “I have to admit, that big cock of yours is something. I’ll probably want to see you again. If you’d like to hook up with me occasionally?” Lisa said.

“Are you kidding?” I said. “Of course, I’d enjoy hooking up with you. You’re so hot!”

We ended up in the shower and afterward she took me out to dinner at a Chinese restaurant in her neighborhood. We kissed goodbye and Lisa said she’d be in contact with me in a month or so.

Three weeks later I received a text on a Saturday morning. “Sunday 4 pm again?”

I replied, “Yes. But I’m buying dinner this time.”

Not ten seconds later Lisa texted, “Sounds great.”

The End Part Two.

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Written by Taco4x4
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