Pt. 05 - Taking it to a New Level

Part 5 - Going to a whole new level

This is my fifth "adults only" fiction sex story.

I strongly recommend you read Parts One through four, in order before reading this story.

This is a work of fiction; all of my stories are.

The characters are all adults over (well over) the age of 21.



As I drove home from the wedding, I counted my blessings.

First there was Natalie, who I had sex with in all three of her holes, including my first anal sex experience.

Actually, I fucked her ass four times over the course of the weekend.

She loved it and I got into it too, especially when she started having orgasms as I slid in and out of her tight ass.

Natalie also wanted me to cum in her ass and who was I to argue?

I started laughing when I remembered us slow dancing at the wedding reception and she teased me with "Once you have a woman's ass, you can never go back to just blowjobs and pussy." Then she slowly looked around and whispered to me "See any asses you'd like to fuck?"

That was an "ah hah" moment for me. Being around someone like Natalie who could open the door to more sexual partners was very appealing.

Imagine, sex by referral only.

No more dating, sending flowers, waiting until the time was right; hoping to get her bra off. No more waiting for ladies like Caroline, my massage schoolteacher, to get beyond comfortable fucking me, and using "it isn't safe" as a BS excuse.

Natalie also paid me for the massages I gave her, legitimate income that, while cash, still had to reported to the taxing authorities. I also got paid by the bride to take candid shots at the Rehearsal Dinner, before and after the wedding when guests were waiting for the newlyweds to start the wedding reception, and then, that morning, I took shots at the brunch before the newlyweds headed off to their honeymoon. That payment, also a substantial amount, was in the form of a PayPal money transfer by the bride done the morning of the wedding once she saw the pictures taken at the Rehearsal Dinner.

Natalie also brought the cousin of the bride from Chicago back into her / our hotel room, where I enjoyed (really enjoyed!) my first threesome. Natalie really got off on watching me grow a redwood tree while she was satisfied by the young blond hottie.

The two ladies got busy on the bed while I took a quick shower.

I came out of the bathroom naked, with a semi.

Natalie caught me a stroking myself as I watched the young Midwestern city girl working her magical tongue on Natalie's hairless pussy.

Miss Chicago had a great taut ass and a pretty shaved kitty.

Natalie startled me by saying very authoritatively in a louder than normal voice: "Stop jacking off Rick and put that cock someplace warm, wet and tight."

With a smile and a hard on I got up on the bed behind the carpet cleaner, pushed Miss Chicago's legs further apart and placed my hard cock right between her cheeks.

That got a nice wiggle in reply and following that I felt her hand reach under to me and she pulled my cock down so I could take her from behind.

I could tell she was horny because she was sopping wet and while she was very tight, I slipped right into her, earning first a groan in a combination of pain and pleasure followed by "Holy Fuck You're Big."

For a second or two she stopped servicing Natalie as her pussy accommodated my girth and length and then, with Natalie's hand on the back of her head, she returned to her first priority, satisfying Natalie, while I started to slowly slide in and out of her snatch.

I was slow and steady in my thrusting, going shallow and then deep, moving my body around a bit to gain purchase and to give her variety. She was not just responsive, matching every thrust with a bump of her own, but she climaxed twice before we both came at the same time, with me unloading a heavy load deep into her welcoming pussy.

I drained my balls into her as she continued to spasm her lower lips around my softening cock.

Natalie pushed Miss Chicago's head away from her well licked pussy, muttering in Hungarian "Nem tobb ...nem tobb" which was "no more, no more."

The Midwestern blonde quickly turned around to find the source of her strong orgasms and found herself face to face with my still large but my now softening cock.

With a look of lust, she got up on her knees and lowered her mouth to clean me of her juices and my baby batter and to suck me back to hardness.

Being young has its advantages. Including a rapid recovery time.

I didn't sleep much that night, with two women to satisfy, but it was a night to remember.


The next morning as I was taking pictures of everyone at the brunch, lots of smiles all around, the bride pulled me aside and said to me "When I get back from my honeymoon, I want to have you take some very special shots of me."

I handed her my card, and she kissed my cheek, thanking me for doing such a great job that weekend on such short notice.

I thought about all this on the drive home, and when I stopped for gas, I checked my phone for messages.

There was a text from the 312-area code: "Hey Rick, thank you for a wonderful time last night. I can't believe how many times you made me cum! You are the best lover! You are still dripping out of me! Let's keep this between us as I am married, but not particularly happy about it. I get out your way about once a month on business and would like to see you when I am in the area. You can text me at this number, it's personal and private. Stay hard! Kisses, Charlene."

I never knew her name until now!

I had no idea she was married!

I texted her back "I'd love to see you anytime, just give me a few days' notice."

And how the hell did she get my cell phone number?


She was a Connector.



At our table at the wedding reception were two women, friends of the bride's mother. Both were married but had left their husbands at home.

Of the two, the prettier was Leeann, a lovely looking woman in her 40's with a slender figure and a nice large rack. Her smile was a friendly one and we flirted a bit.

I noticed immediately the large diamond on her wedding ring, but she wanted to dance with me anyway.

She asked me!

It turned out that she only knew two people at the wedding: the bride's mother and her friend.

She soon became a friend to both Natalie and I, and since I was the only single guy at a table of pretty women, I did a lot of dancing.

Some of the ladies took turns with my camera and took pictures of everyone having a great time.

But Leeann got my attention and at one point she gave me her business card and asked me to reach out to her because she wanted to learn more about me and what I did for a living, besides taking photos at weddings.

I called Leeann just two days later (Monday afternoon) during a break from my day job (working at my home office) at Caltrans and I shared with her all that I had going on.

CPA, attorney, certified (not licensed) massage therapist. Single, looking to meet ladies. Oh, and a part-time photographer too.

When I mentioned massage, she took it upon herself to tell me that she had been looking for a new place to get her weekly massages and was I interested?

Of course, I was interested, and she agreed to meet me after work that afternoon at my place.

I was waiting for my prospective client when she arrived and after giving her a brief tour of the facility had her take a quick shower and then got her under the sheet on my downstairs massage table.

This was truly a gift from heaven, but I want you to know that I was more than professional in my body work.

I kept her very well draped and didn't grope, as much as I wanted to.

Leeann, after being silent during the first part of the appointment except for her groans of pain as I hit some tight muscles, started asking me questions about business income statements, cash flow and balance sheets.

She also asked me about business incorporation, shareholders and all that (boring) stuff.

I wondered why she was asking me all this, but she asked away and I answered as best I could, knowing little about her specific issues.

After the flip, with Leeann on her back and fully covered, her large breasts moving slightly under the sheet as she got comfortable, and me massaging her neck, she spilled the beans: she thought her husband was stealing from the business. That he was having an affair. And she did not know the true condition of the financial status of the business.

She asked me if I would look at the records and see if there was anything amiss.

I agreed to do so, and before she left for home, she wrote my CPA firm a retainer check.

Then we walked out to her car and I carried in a file box filled with paperwork.

Kissing me on the cheek and leaving me two $100 bills for the massage, we scheduled a return visit in a week when she expected to hear from me about the finances.

Leeann also wanted a second look at my studio and said, "I'm going to refer someone who needs some pictures taken."


The very next day I had a call from what sounded like a very young and unsure lady named Melissa.

She told me that Leeann had referred her to me, and she asked if she could meet me at my studio after work, just to do some test shots.

I could tell it was hard for her to make the call and I did my best to put her at ease.

Melissa was someone shy, maybe hesitant is a better word, but once she arrived and took her coat off, she relaxed a bit and when I offered her a glass of cold wine she turned me down but exclaimed "I would love to but I 'm pregnant!"

This got us talking about all kinds of things. And she really opened up. There were some tears, some laughs and I came to see and get to know, a special and beautiful young lady.

It turns out that she worked at Leeann's family business in the accounting department, and had connected or hooked up with Leeann's son, who took a fancy to her at the company Christmas party, dated her, impregnated her but had yet to ask Melissa to marry him.

Like all ladies who get pregnant out of wedlock, Melissa had a decision to make and Leeann, knowing that her son was young and immature, would grow up eventually, and marry her.

So, Leeann persuaded Melissa to keep the baby and took her under her wing.

Leeann's son was a long-distance truck driver for the company and was gone all but a couple of days each month and this was done by design, the kid wasn't an office or management kind of guy. He liked the freedom from responsibility and the open road. When I heard this, I wondered how many other girls he'd gotten pregnant.

In the meantime, Leeann was acting like Melissa's mother and sent her to me for photos. Not just one set, but Leeann wanted a new set each week!

I'd never shot photos of a pregnant woman before, but I was willing to try.

Melissa liked the photos I had up on the walls, and she had checked out my website too, so she was good to go.


Melissa and I sort of fell into fucking.

After the first session in the studio, where she was comfortably dressed, I convinced her to go out to my place in the mountains for some outdoor photos.

We got up there a bit later in the day then I had wanted, and I noticed clouds moving in, but we went out to the creek about a mile from my mobile home to take pictures.

We got in about an hour's worth and then all hell broke loose.

All of the sudden the wind came up, the temperature dropped so we could noticeably feel it, and it started to rain.

These were not just big drops, but cold ones.

Neither one of us was dressed for this; we'd both assumed it would be a nice Spring day.

By the time we got back to my place, not only was it almost dark, but we were also both drenched, head to toe, and the temperature had dropped even further.

The rain had turned to icy drops of sleet.

Melissa started to shiver, and I started up the shower in the back, got out some big fluffy towels for her to dry herself off, and left her to get warmed up.

I turned up the heat, started a pot of coffee and put some logs in my small fireplace in the living room.

The place was pretty well insulated, but I plugged in a couple of space heaters in the living room just in case.

The pounding of the rain on the roof slowed, then stopped.

I walked to the window and looked out to see that snow was staring to fall.

I'd never driven in snow before and wasn't about to try it with a pregnant woman in the car with me.

We were just going to have to wait it out.

I felt pretty good about the electricity because I had a backup generator in case the line went down.

I used propane for the water heater and the stove and that was good.

I checked the freezer and the refrigerator and thanked God that I had my caretakers stock it just the day before.

A couple of minutes after the shower stopped, I heard her call out "Jack, all my clothes are sopping wet what am I going to put on?"

"Just a minute" I replied and then I hunted around in my closet looking for a shirt or something that would fit her.

I found one of those blue button-down denim shirts that I thought would fit her okay, and I handed it to her through the door, not even trying to take a peek at her.

It never occurred to me that while the shirt might fit her okay around her chest and growing belly that the shirt tails might not be very long.

Meaning, leaving her pussy and ass bare.


I thought all was well until she called out again: "I need something to cover my ass, Rick. And socks for my feet."

All I had that was clean in the dresser was some clean underwear of mine, and as I handed a pair to her, I said "These are probably going to be too big so let me see if there are some safety pins you can use."

I found some of those in a drawer in the kitchen and then got her a pair of mid-calf athletic socks to keep her feet warm.


We watched it snow as we sat by the small burning fire and sipped hot coffee.

Melissa was covered in a warm blanket and she assured me that she was okay.

"How long are we going to be stuck here?" she asked.

"I can't say for sure, but if I were to guess I would say we could go home tomorrow afternoon."

She smiled and said, "I've never been able to watch it snow before."


The snow piled up a bit, maybe a couple of inches and the thermometer held steady at 28 degrees.

I cooked a nice dinner and I turned on the television and we watched a movie side by side and then it was time for bed.

I'd already decided I'd sleep on the couch and give Melissa the bed.


When I proposed the sleeping arrangement, she wouldn't hear of it.

Melissa stated, rather emphatically, that she and I were going to share the bed together, just as friends.

"I know you will be a gentleman, Rick."


There was a Fleetwood Mac song that had lyrics that went like this: ..."'Cause when the lights go down and the loving starts ..."

Which is exactly what happened.

When it was time for bed, I moved the space heaters into the bedroom and turned on the electric blanket and left Melissa to get out of the denim shirt, brush her teeth and use the restroom, and put on one of my extra-large tee shirts to sleep in.

I made sure the fireplace was stocked up, locked the doors and turned out the lights, used the restroom and found Melissa already in bed.

I didn't bother to set the alarm clock because I naturally wake up early and so what if I slept in? I wasn't going to be able to go anywhere until the snow melted.

I undressed, quietly, turned out the light and slipped into bed.


It turns out we were both naked and both of had the same idea: to get our rocks off.

As soon as I got into bed, Melissa had her head on my shoulder and her hand began gently rubbing my chest, and her leg swung over into mine, and then her growing breast found its way to my side.

"Want to fool around?" was all she had to say, and we were soon kissing, fondling each other and she was getting my big one right where she wanted it.

Melissa got it pretty much all night long from me, however she wanted it and she continued to get it most of the next day too.

She wasn't too experienced and so I introduced her to some positions I knew she would like, and I have to admit she was a very responsive and vocal lover.

I taught her a few things too, about blowjobs and deepthroating; playing with a prostate and a guy's balls.

She wanted her boyfriend to know she'd been with another guy and she asked me to shave her bush off, which I did with a smile.

I came into her pussy at least six times during our stay at my mountain place, and she told me she was sore when I dropped her off at her place late Sunday evening. "But a good sore" she assured me.

We kissed goodbye and she said to me with a tear in her eye "I wish I had met you sooner" and I replied back "me too."


Look for another chapter soon.


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