Cumming Where No Man Has Cum Before

My stories are in chronological order. I encourage you to follow along and read these stories in this order as a prelude to this one:

I Hire Monica The Maid

Monica's First Day as My Maid

Monica the Maid's Three Hole Day

I Partner with Linda, A Salon Owner

I Massage Monica the Maid

Hot and Sexy Business Opportunities

I Become a Therapeutic Instructor

The Affair Continues in Las Vegas

I Rub an Asian MILF the Right Way

Going Where No Man Has Gone Before

And now, Cumming Where No Man Has Cum Before

For background, let me share the main characters in my stories:

I became a widower unexpectedly in January. I was lonely and in pain; I made an offer my maid Monica could not refuse. She stayed on as my maid and became my part time sexual playmate. (I Hire Monica the Maid; Monica's First Day as My Maid; Monica the Maid's Three Hole Day, I Massage Monica the Maid).

Coming out of my funk, I decided to learn how to give massages and I met Susan, a bathing suit model, who was my massage instructor, and we became friends. Between Susan and Monica I came up with some new business ideas (Hot and Sexy Business Opportunities).

I met Lisa, a divorcee, who was a student of Susan's when I was a substitute instructor. We became lovers. (I Become a Therapeutic Instructor).

Lisa and I went to Las Vegas. (The Affair Continues in Las Vegas and That Was The Weekend That Was). I hired two ladies, Diana and Dana, to be with Lisa at the adult pool. Lisa arranged for my first threesome when we included her friend Michelle. (My Great Night in Vegas -- not written as of this date).

After I met Lisa, and while I was casually dating her, I seduced Akiko, the lady who owned a local dry cleaners. I invited her over for a massage (I Rub an Asian MILF the Right Way). We traveled to Las Vegas (Going Where No Man Has Gone Before) where we met with Susan, Marie and Carmen.

This story takes place the next day in Las Vegas, when I take Susan's virginity and enjoy sex with Dana.

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We were both nude.

We were both consenting adults.

We were staying in a two bedroom suite of a brand new hotel in Las Vegas.

It was Saturday morning.

Susan was sitting between my legs, getting my erection nice and wet and hard before I plowed her tight pussy for the first time.

She had just asked me "How do you want to take me Master?"

I thought about that for a moment as she lowered her beautiful mouth to my cock and French kissed it, causing me to groan loudly in pleasure. My hips left the bed.

I should have known that because she was a good kisser she would be great at kissing cocks, but I hadn't had any coffee yet. My brain was still fuzzy from a short night of fucking Akiko.

She lifted her head up; paused her tongue on the underside of my erection and waited for my answer.

Susan gently moved her tongue back and forth on my corona, her eyes smiling as she watched my face enjoy the pleasure she was giving me.

Her hands were firmly holding the base of my cock and gently cupping my balls, filled with swimmers ready to go where none had ever gone before.

My plan was to introduce them into her virgin pussy.

I looked at her and said to Susan, "Not in this bed and I need some coffee first."

I said to her, "Susan, honey, please call room service and order some coffee and some muffins, bagels, some berries and sliced fruit. Also, call housekeeping and tell them we don't want the room cleaned until 3 o'clock today. Before I forget, get a $100 bill from on top of the dresser and write a note so that the housekeeper will know it's for her. Can you do that for me please?"

She smiled and said, "I sure can Master." We kissed and she had a case of penis breath but it was my penis so I didn't care.

I got off the bed, my hard cock bobbing in front of me and headed for the bathroom.

I heard Susan ordering breakfast and calling housekeeping. I assumed she took care of the note and the tip.

I flushed the toilet, brushed my teeth and used the mouthwash.

I said to Susan "I need a bath. Will you join me?"

She came to me and we kissed; she smiled and said "Yes Master."

I playfully spanked her terrific ass and she jumped and laughed in surprise.

I think she liked that it was just the two of us alone.

She was being amazingly compliant. I wondered if it would last. I hoped so.

I went back into the bedroom looking for my small accessories kit which I take on every trip.

I called out to her, "Susan please take off your all jewelry and put your hair up."

She replied, "Yes Master."

Just then my phone pinged another text message.

It was from Akiko:

'Marie the seamstress is here with my outfits. They fit well and she says I don't need any underwear. She was hoping to speak to you, what do you want me to tell her?'

Holy shit, is it noon already? No, Marie was being her usual super efficient, it was only 11am.

I texted back:

'Have Marie call me in a minute. Please ask Dana if she wants to join us for dinner tonight and if so, maybe Marie has a dress for her to wear off the rack? As for whatever else Dana needs, please call Nancy at the Nordstrom's store and she can come over and do some personal shopping this afternoon. And, if Dana wants her hair done can you call Carmen and see if she can come back to the suite at 6 and quickly do both Dana and Susan's hair and Marie's too if she wants to join us for dinner. Ask Carmen if she wants to go to dinner with us too. But I also need for Marie to come up when she is done measuring Dana so she can measure Susan--hopefully she has something off the rack for Susan to wear tonight. Can you handle this?'

Akiko texted me: 'Consider it done, Master.'

I set my phone down and asked Susan "Please call Morton's and see if we could get a table for six people at 8pm tonight. Give them my American Express Card and pre order three bottles of their most expensive French champagne. Please ask them to put us in their small private room the one with the round table, whatever it costs."

I kissed Susan and said "Thank you, sweetie." I rubbed her ass -- it felt damn fine -- and she turned and said "Thank you, Master."

She looked down at my rapidly deflating cock.

I smiled at her and said "Don't worry, it will grown big again. You always make me big even when you don't think you are."

I laid down on one of the living room sofas and listened as she made the call.

When she finished I said to Susan, "Make me big again, honey."

She smiled and got situated on her knees between my legs and lowered her mouth.

Just then my phone rang and it was Marie.

"Hi Marie, thanks for coming to the pool today to drop off the dresses. Do you want to come up? Okay, we'll be waiting for you. See you in a few."

Susan stopped with her licking and looked at me with a panic stricken face.

"Susan, what are you worried about? Marie's seen you naked before. Keep licking sweetie. You're doing a great job" as my hand moved to the top of her head and held her there as her tongue continued to work its magic.

She played the skin flute very well.

When the knock on the door came, I went and got a robe while Susan answered the door. Susan's faced was flushed and her nipples were evidence she was aroused.

God bless Marie, she wasn't fazed at Susan's nudity or me being in a robe. She knew what was going on.

She quickly measured Susan and said to Susan "I have the perfect dress for you. I can have it delivered by 2 and then you can get shoes and hose from Nordstrom."

I asked Marie, "Will she need underwear?"

Marie shook her head, "No, I don't think so, unless she wants to."

I answered for a Susan and replied "I think commando is the way for her to go tonight."

I thanked Marie; she gave me a little wink and a smile and told her we'd see her later.

Closing the door, I took Susan's hand and we headed back to the bathroom.

I had her turn the water on and I poured in some bath bubbles.

Susan rubbed my ass and smiled at me as we climbed into the tub.

"Susan, let me tell you what we're going to do now. When room service comes, you get the door, nude. You said you would do whatever I asked and well, that is the first thing you're going to do. If anyone else knocks on the door this weekend you will answer it nude. Second, I'm not going to shave your pussy just yet. I will shave it off completely on Monday morning but today and tomorrow I am going to trim it. Third, we are going to wash each other so we're nice and clean and then we're going to adjourn to the bedroom and fool around. Sound okay?"

Susan laughed and smiled, and said "Thank you Master."

I started off washing her back, butt, legs, chest, belly, pussy, legs and feet. Susan was literally purring when as I gently and carefully reached in to every crevice she had.

Then I had her drain the tub and sit with her legs wide apart so I could trim her wet soapy beaver.

As I mentioned, I hadn't seen a red haired beaver in real life and I liked what I saw. It looked quite edible.

I hadn't said anything to anyone about the adult pool going nude at 3pm the next afternoon but I knew Susan was going to be major eye candy when it did.

With her red bush she was going to stand out nicely.

I knew she would be pretty hot being topless with a crowd but being naked with a flaming red bush was going to get her engine going.

I combed out the fine, silky hair using a small moustache brush and then comb, and asked "Susan, why does your pussy hair grow so fast? A couple of weeks ago when you were with Monica you didn't have any hair and now you have this bush. What happened?"

Susan looked at me with a wry smile on her face and replied "Master, swimsuit models have all kinds of tricks to make it look like nothing is there when something is there. Let me keep my professional secrets, please, Master."

I didn't pursue it but I wondered how that would be incorporated into the new swimsuit lines.

I had just finished the trim job and was washing off the loose hair when there was a knock on the front door of the suite.

Without a word, but smiling at me, Susan got up, stepped out of the tub, grabbed a towel and went out to answer the door.

Before I could say anything, she returned to the bathroom and dropped the towel on the floor, looked at me laughing and said "I almost forgot Master, but I didn't."

I heard her answer the door, some conversation and then the front door closed.

Susan came in with a cup of coffee for me, saying "Master, here is your coffee, cream only."

Her face was flushed and her nipples were bigger. Being naked in front of a total stranger does that to you.

I was thinking that Susan enjoyed the experience. Just wait until later today out by the pool. It's one thing to be in a topless photo shoot with no one by the photographer present. It's something very different to be topless and hundreds of men and women ogling you for hours, wishing they were fucking you.

I thanked her and said, "Susan, please go get your coffee and get back into the tub sweetie, we're not done here yet."

She smiled, said "Yes Master" and returned in a minute with her coffee and climbed back into the tub.

We kissed and I said to Susan, "You made me very horny in bed this morning and I want you to relieve me with your mouth now. Do you know about hot coffee blowjobs?"

Susan laughed and said "Monica and Akiko both explained what it was Master and how much you liked them. Should I start now to please you that way Master?"

I nodded and then, before she bent her head to take me into her mouth, Susan said, "Master, my goal is to provide you with the most pleasure possible so please help me by telling me how you want me to please you."

Her tongue worked its magic as the sleeping dragon awoke from its slumber. My balls tingled as her finger nails played with my sack, stimulating them.

As she mouthed me, drank coffee and mouthed me again, and again, I grew rapidly.

I put my hand on her head to guide her efforts.

I told Susan, "You cannot believe how many times I have dreamed of you sucking my cock. Since we had the breakfast together every time Monica sucks me I closed my eyes and dreamed it was you. When I came down her throat I dreamed it was you swallowing my load. When I fucked Monica I closed my eyes and pretended I was making love to you and coming in your pussy. When I came in Monica's ass I was hoping I could do it someday with you. I love you Susan."

I let her lick, kiss and suck for a few more minutes.

She looked up at me and smiled t me with her eyes. Then, taking her mouth off of my cock, said, "Master I knew you always cared for me and now it's my turn to care for you."

I didn't want to cum just yet, so I pulled Susan off of my dick and told her "I want you to lie back in the tub and close your eyes and pretend I am making love to you. I want you to masturbate for me. Play with yourself for me. "

Susan got into it, although once or twice she opened her eyes to see me watching her face as her body revved up.

As she started rubbing her newly trimmed pussy with her right hand, her left hand began rubbing her breasts and pulling on her nipples.

Her fingers began rubbing her clit and her hips began moving and it didn't take too long and she came, and she let me know it.

I asked her "How did the make you feel?" and she said "Master, it felt great to have you fucking me."

By now, between the hot coffee blow job and Susan's performance, I was rock hard and ready to fuck her.

I told Susan, "Come up here and straddle me. You're going to lower yourself on me."

Susan looked and me and complied.

I had her on her knees, squatting over my cock.

I told her "Put your hand on the base and put it in."

She looked a little scared and I gently pulled her face to mine and kissed her.

"In a minute I am going to be in your pussy for the first time of many times. Your fantasies are about to become real. For a little pain now you're going to get years of pleasure."

Susan started rubbing my cock along her slit and then she looked at me, smiling and sat down, taking me all the way in.

The pain showed up on her face, like she had been given a shot with a long needed (no pun intended) but I told her "Just breathe baby, and try to relax."

We kissed and she said "That wasn't so bad. But my God Jack, you have a big cock!"

I laughed and said, "You make it big Susan."

We kissed.

I just went somewhere no man had gone before, Susan's pussy.

Just as she was getting comfortable sitting on me and feeling filled up, I told her to start riding. It took a few seconds for her to get a rhythm going but she started see seesawing on me.

I just wanted her to get used to me being in her so I let her ride. I did start playing with her clit and she liked it.

I asked her to bend forward and I sucked on her nipples.

After a couple of minutes I said "Let's head to the bedroom."

++++

I was hard, large and ready to enter her.

I was kneeling between her spread legs.

She didn't have a stitch of clothing on.

There was nothing between us but a few inches of air.

The aroma of her pussy had reached my nose, and in fact, permeated the room.

Her trimmed strawberry red bush was wet and her lower lips were visible and slightly opened.

She was ready for my cock.

I was in her in the tub, but we didn't fuck but for a few minutes.

I wanted her to get past me being in her for the first time.

After the tub, I got her naked on the bed.

The build-up had been going on for months.

She had come twice already as a result of my tongue and once by me playing with her clit while were making out on the bed.

I made sure that she was enjoying herself and was laughing and smiling as my hands roved her entire body for the first time.

No place was off limits to me and she loved the attention I gave her.

I stoked her hair, her neck, her arms, her breasts, her belly, her back, her legs, her flanks.

Susan looked up at me with half lidded eyes, ready to be taken, fully and finally.

I had been looking forward to this since the moment I met her at the massage school.

I leaned down to kiss her, my cock following my advance.

Susan reached down to guide me in.

My tip reached her open lower lips.

I asked her "Do you want me to fuck you or do you want me to make love to you?

"Master, please fuck me."

I plunged into her near virgin pussy with a vengeance. I went in balls deep with one thrust. She screamed and held on for dear life as I started pumping in and out of the warm, wet and very tight sleeve of her womanhood.

Instinctively her legs moved wider to allow me access and her arms and hands held on tight as I thrust in, over and over, full, long strokes, letting her feel every millimeter of my erect manhood.

After a few minutes in missionary, I pulled out, ordered "Get on your knees, and then took her from behind, entering her in a single stroke balls deep. She groaned in pleasure and at once her fingers found their way to her pussy to play. I took her by the hips and pounded her, fast and deep.

After a few minutes of this I pulled out, and took her by the hand, and went out to the living room. I had her bend over the back of the sofa as she looked out at the city below and I entered her again from behind. Grabbing her by the hips I started pounding and then I stopped.

I pulled her up, my cock still inside of her, and played with her nipples as I kissed her neck. Her hands reached around me to pull my face to hers to kiss.

My right hand snaked its way down her taut belly and found her clit barely hidden by the strawberry hair of her pussy. I started to gently pump while my fingers teased Susan's clit.

"Do you like this sweetie?" I asked as I continued to pay with her body.

"Jack, I love your cock!" Susan replied between small groans.

I pulled out and sat down on the sofa.

"Come over here and ride me Susan, just like in the tub."

With a smile, she complied and this allowed us to kiss and for her to rub her clit on me.

She leaned back and put her hands on my knees, allowing me access to her clit and her succulent nipples.

All the while she is pumping me, as I played with her clit and teased her nipples with my teeth, creating some pain and pleasure.

In no time she was humping me with a quest to cum and she did, with wild abandon. I am sure the maids heard her down the hallway but neither of us cared.

She collapsed into me, her arms around me and her face buried next to mine.

"That was so good Jack, Oh My God; I never knew it would feel so good."

I was still hard inside of her, wedged in that hot cavern.

Susan shyly smiled at me "Jack, I am glad I wanted for you to be my first."

I kissed her and we just held each other.

After a couple of minutes, Susan licked my neck and kissed me like a lover and said, "Master, I need to make you cum now. Will you cum inside me?"

She climbed off of me, shakily, and got down on her knees and looked at my wet, large and angry cock and said, "Please let me clean this for you."

I said, Susan, "Lay down on the sofa."

She climbed up on the sofa and spread her wet thighs, and still hard, I pushed into her, kissing her and reviving her napping vagina. We made love and she came again, holding me tight, and then I literally poured my balls into her pussy with a groan when I came, finally.

We lay on that sofa for a few minutes until I shrank and plopped out of her.

She looked at my deflating cock and said, "Let me clean you Master."

Using her tongue, mouth and lips, Susan did a great job of removing our juices.