Kinkiest Great Lakes Date I Ever Had

It was a cold, crisp evening and my thigh high boots clip-clopped along the pavement as I walked. I pulled the thick, long coat tighter around me to try and keep out the worst of the weather. I was on my way to see my Dolly date "boyfriend" at his suburban Minneapolis house.   Downtown was fine in Minneapolis in the chill weather, all the major convention hotels and buildings are connected by walk-way bridges to protect business people (and their mistresses!) from the elements.  But now I was making a house call, (which shows you how many times we'd been together and how deeply our trust had been built, for me to make a house call), and there was a chill breeze.  I had the thought, "this isn't even Minneapolis, this is Mendota.  Mendota Minnesota.  Heck, this is really a suburb of St. Paul, not really Minneapolis".  Then I thought of the warm beach and island trips I've shared with Mark.  That's my guy's name.  Mark.  Minnesota Mark.

His wife was away at her parents in Palm Springs so he had invited me for dinner and a night of domestic bliss.  "Mark, I'm very concerned for your protection and mine, leaving evidence..." I began, but he had answered my concerns on the phone.  "Dolly, you remember that threesome we shared with Alyssa, the escort from here who I was introducing to the scene in Miami?"  Sure I did.  Alyssa was attractive in the "oh she's having an affair?  No surprise, look at her, I'd fuck her, too" sort of a way if you saw her and heard the whispering at the country club or dinner party.  "Yes, I remember her, you damn near fucked her bareback until I grabbed your dick while it was on the way into her and reminded you.  I swear, you've never been that eager with me.  Should I have been jealous?  But what about Alyssa -- wait, you've had a threesome with Alyssa and your wife? Holy shit, Mark!"


Mark started laughing.  "No, Dolly.  Alyssa is my wife!"  He's been holding out on me!  "For real?"  "Yep."  Oh this fine fuck of a lover just got so much hotter.  Can't believe he hadn't shared this info.  I'd even scouted her on-line profiles. She was really nice, too, and Mark is giving me really generous presents in envelopes when he has her for a wife.  I was sooooo, going to fuck the shit out of him!  Dinner and a night alone with Mark at his house suddenly sounded like heaven. I couldn't wait.

As I reached the house I slipped slightly on the icy path and pulled my thigh awkwardly. It hurt a little but I recovered as best I could and rang the doorbell. It was opened by a beautiful girl with long blonde hair and a very low cut dress. Her breasts were nearly spilling out and her blue eyes were full of fun and mischief. This was not Alyssa, even if he'd been fibbing about her being away (yeah, right, at her mother's in Palm Springs....seeing Alyssa dates when her mother thinks she's at the spa I'll bet...and suddenly remembering some of the trysts I've enjoyed while telling my family members a cover story.  MILF's who live in glass houses, I thought.)

But back to young blondie here, maybe, oh, twenty-five.  Had I got the wrong address? Or was my GFE-loving temporary Twin cities boyfriend fucking someone else? And if he was, damn she was cute, would he share?  All sorts of combinations shot through my mind. She just smiled at my confusion and said, "Hi! I'm Dave's girlfriend, Monica."

"Oh, you're his girlfriend?" I mumbled stupidly as I stepped into the hallway.  Wait.  "Um, who's Dave again?  And Mark lives here, right?"  

"Yes, she's my son's girlfriend," said Mark, as he came to towards me and kissed me on the lips, slowly, passionately, but not violently.  I was aware this girl knew I wasn't Mark's wife, and she's watching his tongue go into my mouth and his hands reaching inside my coat to cup my tits.   "Monica and Dave are visiting, but Dave got a last second invitation to the Gophers hockey game, and you can't turn a ticket like that down, can you, Monica?  So she's having dinner with us, I hope that's okay, Dolly."


This wasn't what I was expecting or, in truth, what I really wanted, but I'm in the habit of making dreams cum true for the men in my life, and Mark was certainly one of the men in my life.

"Shall I take your coat?" Monica asked.

"Um," I mumbled again.  Monica and Mark looked at me waiting for an answer.  I'd sort of forgotten the infidelity display Mark had put on for Monica when he greeted me.  

"The thing is," I said, trying to string a coherent sentence together, "Um, could I see you alone for a minute, Mark."

"Sure, come upstairs to my room."

On reaching his room he said, "Dolly, are you okay?"

"Well I just thought it was going to be us, so I could share this with you," I answered.

"Oh my God … oh … wow … but … oh." 

Now it was Mark's turn to lose his power of clear speech. I had undone my coat and dropped it to the floor. I was standing completely naked other than for my thigh high boots. My skin was gleaming with a hint of special oils and flavored glitter I had carefully massaged into myself and my pussy was smooth and hairless as always, and in spite of the confusion, I had the beginnings of moisture there seeing as Monica was as young sweet and fuckable as most of the cast of One Tree Hill (for those who used to use that show for jack material. Hint--its on Netflix; you’re welcome).

"I thought it would be just us two for dinner," I explained.

"Oh wow. You look amazing. I love the boots and your … God, you look hot."

 Mark closed in on me and was soon kissing my neck and shoulder, his hands running over my toned back and firm fit ass. I could feel him getting aroused, his hardness began to press against me. I wanted him to just fuck me, as I had planned, and then do with me whatever he wished. His mouth was now on my nipples, sucking and licking them. Shit he paid better attention to my tits than some guys. I tend to attract so many leg and ass men, that it is so nice when I can balance out my splendid Dolly date experiences with variety, like Mark, the good old fashioned boob man. But before I completely fell through the looking glass into fuck all night and half of tomorrow as well land,  I somehow pulled away and said, "Dinner. Your son's girlfriend."

"Oh yes. Dinner. But you can't go down like that! I know, you'll have to wear one of Alyssa's dresses."

"You've got to be joking!"

"I guess I am. I guess your coat back on?"


"I've got something, here."  I pulled a wrap sheer shawl out of my coat pocket. More of a pool cover up, truth be told, it was mostly a sexy feeling next to my skin that covered my pussy and tits and was fun to peel off when sex was imminent.  And given that Monica seemed to be in on the secret family sexual appetite, the see-through nature of it didn't worry me.  What was the deal with her, anyway?

I did my best to compose myself and we went downstairs to join Monica and to, hopefully, enjoy our meal. 

Dinner went okay. Both Mark and Monica seemed to delight in glancing at my nipples and my unrestrained breasts. This made me feel so sexy. Monica really looked incredible as I knocked back the wine. Her breasts and cleavage kept me entertained. I watched them swell as she breathed in and then deflate slightly as she exhaled. I was hoping she would breath extra deep and her nipples would burst free. What would they be like? While I kept watch we got on just great and chatted away like we had known each other for years.  She was unabashed at telling me that she was working her way to a physical therapy degree and licensed practice as a stripper.  Definitely had the body for it, and good for her, no ink.  Too many sexy bodies end up being used for body graffiti and ....sorry, I'm preaching.  Not my preference, end of that discussion.  So let's talk about my night with Mark again. And Monica, of course.

"I saw you were limping a little when you came into the house," she said.

"I pulled my thigh a bit on the path," I told her.

"I'll have a look at it, if you want, after dinner. I'm a physiotherapist, remember? Or about to be, but don't worry, I've done my clinicals."

"Thanks," I agreed. Well it would have been rude to refuse, wouldn't it?

With the dinner debris cleared away Mark watched with a grin as Monica took me into one of the unused rooms and locked the door behind her.

"Okay Dolly, lets have a look at that leg of yours. Florida girls on the ice, I'm amazed you stayed upright.  So many falls in this town.  Sit in the armchair over there."

I did as instructed and she knelt next to me. I looked down her impressive cleavage as she lifted my leg in her delicate hands. Nice French manicure. Nice touch.  I wondered where the surveillance camera was, as there was no way Mark had set this up for my visit and wasn't going to get to watch.

"This boot will have to come off," she said and she lifted the bottom hem of my wrap upwards which quickly revealed my smooth pussy as well. I saw her lick her lips and smile.  "Mmmm, I wax too.  Yours is so pretty.  I can guess you must be an amazing lover."  And then she continued with my leg!


There was a zip on the inside of the boot, but this was high on my thigh. My wrap was soon completely drooping off me, revealing my tits as well as my pussy. She bit her lip, mouthed, "wow" at my nakedness and blurted out, "Fuck, my boyfriend's dad is some lucky guy."

She tossed my wrap aside, stroked my flat, toned tummy, dragging a lovely manicured nail along my belly button and licked her red, full lips. Her fingers then went back to work and she found the zip and she slowly pulled it downwards so that my boot could be removed. Once this had been done she began to manipulate my leg and bend it in various directions.

I was breathing quite heavily as I looked down at my completely exposed body. I felt sure that Monica was moving my leg more and more to one side so that my pussy would be fully on display.

"I'll massage your thigh."

"Thank you, you've got amazing hands, Monica." I touched her wrist as I thanked her. 

Her hands started at my knee and agonizingly slowly rubbed and pummeled my flesh. Gradually her hands moved higher. I allowed my other leg to 'accidently' drift sideways. I wanted Monica to have an unhindered views of my secret valley. Somebody needed to taste me.

Eventually she reached the very top of my thigh and her fingers began to smooth the outer layers of my pussy. It felt so unbelievably sensual that I couldn't help but spread my legs further apart. Monica saw that I was fully on board with this blatant set-up, took the hint and one of her hands started gently stroking my pussy. I trembled with desire and wanting. One of her fingers easily pushed between my moistened lips. I let out a deep sigh as her digit pushed further inside me. I was breathing heavy, my heart pounding away as another finger joined her first. I wanted more but she withdrew her glistening fingers, her previously classy finger nails now somehow slutty, now that they were covered with my juices.

I was almost pleading for her to continue. She placed one hand each side of my vaginal lips and pulled them wide apart. My pink wetness was now fully opened and on display. I could see a look of lust in her blue eyes as she moved her head forward. Her tongue started to lick deep inside my spread open sex and I could feel my orgasm forming as my internal muscles spasmed slightly. Then there was a knock on the door. "Damn!" I thought. Really?  Now?

"Are you nearly done?" I heard Mark ask.

"Yes, won't be much longer. We are nearly there now." Monica called out.  Good.  I sure couldn't speak.

"Okay, don't be too long."

 Monica's mouth returned to my ridiculously wet vagina and she spread my lips again, this time to open up and expose my hard clit.  My breathing was faster.  Was she really a stripper, or had I missed a new star on the great lakes escort scene.  At that moment, who cared?  Sexy chick was amazing!

She started to slowly suck on my magic bulbous button. I couldn't hold back any longer and cried out as I orgasmed, my body shaking with pleasure, and I squirted. I was grabbing at my tits as I did so, pulling on my nipples completely enthralled in pleasure.

I came back to earth as Monica said, "Let's get back to Mark since he's already asked us not to be much longer."  God, one cool customer, this girl.

I pulled my boot back on, zipped up the side and stood up facing Monica. We kissed gently and I could taste my pungent sexy juices on her lips. My hands reached to feel her delicious looking boobs.

"Can I see them quickly?" I asked. "Only fair, I showed you mine."  

She smiled, undid two buttons at the top of her dress and pulled her bra down so that her tits bounced free. They were like white globes, rounded and soft with magnificent proud pink, puffy nipples. I kissed each one, Monica's trained hands on my head, her nails pressing into my scalp, something slightly kinky, a trace of S&M but no harm, so sexy, before she adjusted her dress.

We went to join Mark. My thigh was still aching but I felt much better!

We all had a fun evening until after midnight laughing and chatting away. Mark was very open about the obvious sexual relationship he and I shared, with me on his lap, in all my nude but thigh high booted glory, his hands and mouth on me, kissing, teasing, playfully, and Monica just enjoying the sights. When he yawned around midnight, I'd had such a kinky evening I didn't even mind that I hadn't been fucked, but I hoped he would be awake enough to properly tuck me in, so to speak.  "Can I take you up to bed, dear?" I asked him.  He kissed my shoulder and said, "oh yeah..." We stood.

 "What about you Monica?" I asked.

"I'm staying here for the night," she smiled. "Dave will probably be back unless they get so drunk after the game that they have to stay elsewhere."

"Oh!" I was back to my monosyllable self.

"C'mon, Dolly, bedtime, you promised," said Mark.  Okay, back on track.

I smiled and kissed Mark, standing next to him and molding my body to his.  I was desperate to be fucked. Then I felt extra hands on my skin. Familiar hands.  Soft, skilled fingers on my flesh. Monica kissed me on the neck, erotically, said goodnight and then whispered in my ear, "Have fun."

 Mark and I went up to his room, "Keep your boots on, please."

I took a minute to spruce things up a tad the way I do in the bathroom, and walked back out, still stripped naked except for my boots.

"Fuck, you look so hot," Mark whispered quietly in my ear pulling me to him. "My cock's been aching to be inside you all night."  (So, why had he waited?  Having a naked woman on his lap who wasn't his wife right in the open with his son's girlfriend, it’s not like we had been hiding our intentions.  But I'd already noticed that the envelope was overstuffed and this was an amazing night already, so no complaints from me, just curiosity really).

He let go of me and I spread myself on the bed while he went to the bathroom. I stroked my smooth pussy while I waited. "I want you to really fuck me good Mark, like you always do, just go for it, I won't break."  Was I going to think of him, or Monica, while I got laid?  And which one would he prefer I visualize, I wondered.

Mark returned to the room his penis hard and upright. It wasn't big, just an average size, but it looked very sexy as it bounced against his tummy as he walked towards me. He lay next to me and reached for a drawer in his bedside cabinet. He took out a condom, and rolled the rubber over his hardness.

There was very little foreplay left to do given that the whole evening was foreplay of sorts, and Mark soon moved on top of me, his condom clad cock nudging at my entrance. He didn't have to knock for long as I lifted my leather booted legs around his waist drawing him inside me. I loved the feeling of having him fill me up and feeling the heat of his sperm through the condom, so close, so close..... 

His cock slipped easily in and out of my very wet love hole as he gave me his full length over and over. I was kicking his bottom now with my boots wanting him deeper and harder. He let out an animalistic grunt and he came. I did my best to orgasm with him but it wasn't as hot of an orgasm as I'd had with Monica earlier, I realized.

"Fucking great," he said.

"Mmmmm," I agreed, hoping he'd be up to second helpings soon.

We cuddled for a while talking about nothing in particular. I encouraged him to suck on my tits hoping that would be the start of something big. This he did and after a few minutes he was getting quite enthusiastic about what he was doing - and so was I. I could feel his cock hardening.

He moved away from me, "I've got to use the bathroom for a minute," and I watched him walk out of the room, his penis slapping playfully against his tummy.  "Yummy," I thought to myself, "I'll enjoy sucking on that."

I lay back on the bed fully, my boots still on, opened my legs wide and tested my temperature and moisture level. Both were very high!

With my eyes closed one of my fingers roamed over my pussy, and then I heard a movement in the room. I presumed it was Mark. But it wasn't.

Standing next to me was Monica, completely naked. I looked up at her rounded, swinging breasts and at the wispy blonde hair covering her pussy. She was holding a lighted candle which she placed on the bedside cabinet. She turned the other lights off.

I was wondering what had happened to Mark but she lay down next to me and caressed my hair gently. Her lips touched my neck and shoulder and shivers of delight shot down my spine. Her hands moved to my tummy, round and round they went, tickling and fondling gently until they contacted my bald pubic mound. She squeezed the flesh in one hand before a finger reached to touch my actual pussy. 

Her touch was like that of an angel and I was ready to fly away with her to heights unknown. I moaned, wordless once again in her presence. Then I returned to earth as I saw that Mark had entered the room. I wondered what he would say to seeing the two of us entwined, but he didn't utter a word as he lay down behind Monica with one arm looped around her waist.


Alarms went off in my head.  Son's girlfriend? Really, or another cover story, like with Alyssa?  I didn't know what to think, but I knew Mark would surprise me but never get us in trouble, and oh God, Monica's hands were taking me back to heaven as her fingers slipped between my swollen nether lips.

Suddenly Monica let out a loud moan, a sexual sound, and her bottom pushed back. Mark lifted her upper leg and I watched in disbelief as his cock, sheathed in a fresh condom, entered her pussy. I could just make out her sexual lips almost sucking him in deeper.

"No", I thought, "This can't be happening, not with his son's girlfriend."

But it was and Monica sighed with pleasure as Mark slowly started to fuck her from behind. I didn't know what to do. Should I leave? No, wait, I was on a well compensated Dolly date, I'm supposed to be here.  But I was so aroused that I watched and decided they'd tell me if they had more planned for me during this amazing night. Mark turned Monica on her back and mounted her in the traditional position. I watched his cock glide in and out of her tight young inviting pussy. They were both moaning gently as they continued their love making. And this was love making.  There was passion, heat, and complete surrender from her. "so good, so good Mark...."

I'm not ashamed to say that my own hand moved down to my pussy and like some excited voyeur I plundered my soaking sex target, finger fucking myself with abandon. I knew they were approaching orgasm and suddenly Mark and Monica both cried out, "I love you," and Monica thrust her tongue into Mark's mouth and he reciprocated as her body convulsed in pleasure and release. I could tell that Mark had cum with her, his seed spilling out into his condom deep inside her velvet walls. 

I groaned myself and orgasmed, lifting my pelvis high as my fingers slurped in and out of my cunt. My juices were spilling onto my hand and I came again calling out to Mark and Monica, "So fucking hot, all of this" followed buy a guttural groan.  I was drained emotionally, physically, sexually.  Though I'd have loved either one of them to do me again right then.  I did my best to gain control of my body and lay still asking myself, "Why did he just fuck his son's girlfriend and say I love you?"

The room was quiet and still. I could hear the clock ticking and my heart thumping.

Monica's hand reached out to touch my breasts. As much as I wanted her, desperately wanted her, I felt the wave of exhaustion that punctuated my orgasm continue to take over and curled up. I awoke about an hour later, took off my boots, and went back to sleep. I was surrounded by one of them on either side of me, both affectionately touching me as they slept.

In the morning I woke up, noticed it was just Mark and me, showered and then dressed in the spare, not-attention grabbing clothes I had in my bag, and packed my boots. I kissed his cock, which was surrounded by the sweet scent of Monica, heard him moan, "God you made that so perfect" and he dozed off again.  I went downstairs. Monica was sitting in the kitchen drinking coffee.

"Hello," she smiled, her face aglow with vigor and health. She looked wonderful, like a woman in love.

"Can you explain, please," I asked.

"About Mark and me? Or Dave and me?"

"Let's start with Dave, if you really are his girlfriend."

Monica's face dropped a little and she brushed her hair away from her face. "I am. Well, Dave and I have been lovers since we were seventeen. I was his first fuck …"

"But you are fucking his father now," I interrupted.

"Yes, but even though you heard us say I love you, that's part of the sex, really,  it's only sex and we've always enjoyed it. We are not hurting anyone …"

Again I interrupted, "Hello?  Dave doesn't get hurt?".  Imagine that, Dolly concerned about a little infidelity, especially such hot infidelity with me as the special guest star.  But I just had to know.

"Oh darling", she said, "I'm sorry, we should maybe have explained before we did that in front of you. I was Dave's first fuck, but Mark was mine.  Dave caught us, and ....."


This was all too much.  "Huh?" 


Mark and Dave's mom were divorced, I'd lied about my age and had started stripping on a fake ID, which by the way I'd never do again and I'm so lucky I didn't get a ton of people in trouble, you betcha (a neat Minnesota-ism, that "you betcha").  Dave came over after Mark had charmed me back here...and all I knew was the next time Mark came to see me dance he told me his son had seen us and thought I was beautiful and wanted to take me out on a date.  A date!  Movie, dinner, making out, and brought me back to my apartment and that was it.  Knowing that I was fucking his dad, he treated me like a lady, like a girlfriend."


Mark arrived in the kitchen, in a terry cloth robe with a Royal Caribbean embroidered insignia on it.  "And I had a heart-to-heart with my son, and he told me that he knew I had an appetite for variety in my sex life. He had found my porn folders on the computer and his mother had been honest with him about the break up, though she apparently hadn't condemned me to him, just told it like it was."


Whoa.  Hey, wait a minute....


"So where does Alyssa figure into all this?  Do you two and Alyssa...." my question trailed off as I saw the nodding heads.


"Alyssa was sort of my mentor at the club. She was ready to get out of the smoke-filled club and make better money and have the fulfillment of the sex, not just be worked up and frustrated at the end of the night the same as the men.  So she took the leap into escorting, became a local star, and Mark was attracted to her and it made it seem easier to be sort of cheating on Mark with Dave if Mark had Alyssa," Monica told me without taking a breath.


My mind was spinning.  And my nipples were hard.  "So, um ...well..." I sure was unintelligible around Monica.


"I'm going to marry Dave.  But Mark is my sport fuck, and I'm his favorite "strange" when Alyssa's away." 


I frowned.  Monica saw me, and quickly stood with her hands out apologetically, "No, no, I mean local.  Christ Dolly, when Mark met you, he couldn't stop raving.  He's so cool to be married to Alyssa, and I get to share some, but when he met you, Alyssa and I practically had to have a blow job contest on Mark to see who was going to get to be with you first.  Alyssa won, obviously.  But I'm so psyched I got to join you two last night."


I smiled, I was flattered.  "Felt more like I was joining you two last night, more like it."


I heard the door.  And in walked Dave, a younger, thinner, curlier haired, less thinning on top version of his father.  Same green eyes.  Maroon hockey jersey with a bright gold "M" on the chest.  Monica ran up to him and they hugged and kissed, his hands on her petite cute munchable ass.  "So how was Dolly?" Dave asked.  I wondered who he was asking.


"She's fucking amazing, Dave, just like dad and Alyssa said."


Yes, I'd noticed she called him dad.  Dave noticed that I noticed.


"We're talking about getting married, Dolly, nice to meet you by the way, that's why Monica called my dad "Dad" just now.  You looked like you thought we'd been tricking you and Monica was my sister or something!"


On that note....

 "I'd better go," and a huge smile broke out all over my face.  "This has been one amazing, surprising, ridiculously sexy night."  I walked up to Mark and embraced and kissed him.  He whispered, "So what do you think of Dave?"  I rolled my eyes.

I got up, collected my big topcoat, wrapped it tightly around me and, slightly limping, made for the door.

Monica walked with me, handing me her card. It was a cell number and an address I didn't recognize.

"Please come and see me next visit. I'll still be dancing at the club through at least next May."

She put her arms around me and pressed her lips to mine. I could feel her breasts squashing against me. I didn't know how to respond but I enjoyed returning her kiss passionately. I came to my senses and pulled away. The cold wind would soon cool my desires. I set off on my walk to my rental car.

As the door closed behind me, I heard Monica whisper, "And Dave loves to fuck girls wearing boots, too!"


I just booked my next trip to the twin cities.  Hope Alyssa's home, too.  I'm going to wear the Golden Gophers bikini panties Mark sent me.  You betcha.



Purely fictional fantasy for your reading pleasure! Enjoy!

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