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Double Penetration

This is an adult sex story.

All the characters are of the age of consent or far over it!

Any children named are not involved in anything sexual.

This story follows “I Learn about the Hot To Trot Club!

Enjoy and thanks for the views and votes.



I sleep pretty well for a 35 year old.

You might think with a pregnant wife and two (girlfriends? mistresses?) that were also pregnant thanks to me plus having a growing business empire (LOL) I would toss and turn all night long with worry but I don’t.

If you remember Mad Magazine, you remember Alfred E. Neuman, the cover boy.

His famous line was “What –Me Worry?”

That was me. I didn’t worry about much of anything. Maybe I should have …

I didn’t take a sleeping pill; I just went to bed at the same time each night and woke up at the same time each morning.

My preferred style is to sleep in the nude and I don’t mind saying that I like to snuggle up to my wife in our big bed.

We both like being close to one another as we drift off to sleep and during the night, she sometimes chases me around the bed and sometimes I play the game of pin her to the mattress.

It’s a nightly struggle about control … control of the blankets and the mattress space.

Many times my wife has literally forced me off the bed in her middle of the night quests to get close to me.

She, in turn, has accused me of being insatiable … wanting sex at all hours … in many positions from her. And if not sliding my erection into her pussy then getting a blow job or maybe an ass fucking.

She says this while she is laughing, rubbing her swollen belly and telling me “This is what happens when we have sex! You and that big cock of yours got me into trouble!” and then she laughs louder.

(I do want sex from her at all hours. I’m not going to apologize for it.

If you saw my wife you’d want to have sex with her too.

My wife sleeps in one of my used workout tee shirts.

She said she likes my scent.

Beneath it she is naked, and she loves it when I snuggle behind her in the bed, pull the tee shirt up to her waist and plant my firm cock between her butt cheeks.

My arms surround her, my hands move to cup her big and growing soon to be milk producing breasts and then my right hand wanders down to her massage her swelling belly and then to her shaved pussy where I cup it and then diddle it before going back up again to those orbs.

By now I am hard as Mt. Whitney.

And Catherine can feel me; she can feel my need.

I have to be careful with her tender nipples because sometimes they are overly sensitive.

I bury my nose into her shoulder length natural blonde hair and take in her fragrance.

She smells like she looks, beautiful.

With a hard cock in her crack, I’ve made it pretty clear what I want.

(Yes, I am a horny, selfish man who wants to mate / fuck / make love with his wife. So sue me).

Most nights she’ll gladly suck me off or welcome me into her pussy (and if I want it, her still tight ass) but last night despite my wanting to blow a load she said to me “I’ll take care of you in the morning. Good night. I love you.”

She fell asleep in seconds and I fell asleep too, but it took a bit longer.

So I woke up at my usual time, 5am, and my daily plan was to workout upstairs in a spare bedroom that I had converted to a small gym.

If I exercise first thing in the morning I feel good all day.

If I have sex before work, or the night before, I feel fucking great all day long.

My sleeping wife Catherine, now about four months pregnant, was snoring softly as I quietly slipped out of the master bedroom dressed in only a tee shirt and gym shorts. I carried my workout shoes and a pair of socks with me.

I silently climbed the stairs to the second floor, went down the hall, noticing that the lights were already on by the light emanating from beneath the door.

Which was funny because before I go to bed at night I have a ritual of going to every room in the house, and check to make sure that windows are locked, nonessential electric appliances are unplugged and that all is well.

Cautiously, I opened the door to the room, not sure what I would find.

I was facing a toned, tanned female ass and a great pair of legs.

“What took you so long?” she whispered to me. “Close the door and lock it.”

It was Janet (The MILF), nude, in a downward dog yoga pose on one of the matts; her ass to the door by design.

She was covered in a light sheen of sweat, and I could see that her shaved lower lips were puffy and moist.

Between her thigh gap I could see her large erect clitoris. She was turned on.

Below that I could see her swelling baby bump; she was several months pregnant with our little boy.

Further below were her heavy, heavenly breasts.

She had ambushed me again.

“Like what you see?” she teased me as she wiggled her ass.

At my first glance I had missed the new butt plug Niğde Escort she had in.

The design and colors caught my attention.

At the end of the plug, facing me, was a small, maybe the size of a quarter, red stop sign.

I laughed and smacked her ass.

“What’s this?” I asked, “Are you denying me my favorite hole?”

She knew I was kidding but she also knew how much I liked sticking my hard dick up her ass, even with her discomfort taking it.

Janet replied in a low voice “Catherine helped me put it in last night and I slept with it in me all night. We thought you would like it.”

I pulled it out a maybe an inch and then slid it back in.

“Just so this is a temporary thing. Coming in your ass is one of the best things in my life.”

With that Janet just laughed and shook her ass again at me.

My hands stayed on her bare butt; Janet had a great ass, despite the fact that it was getting a bit bigger.

My morning erection hadn’t really gone away; it had been in hibernation and with the sight of this MILF ready to take me I rose to the occasion quickly.

Janet responded with “You know you can have my ass anytime Jack, but please not with the girls in the house. I scream too loudly. Get those shorts off lover and scratch my itch. I want you in my pussy. Now. Please honey.”


I had gotten in something of a short second workout after bringing Janet to two quick orgasms and then unloading deep into her.

She got what she wanted and so did I.

After coming inside of her, we stood up and I got behind her and held her, my hands rubbing her burgeoning belly and then lifting the heft of her big breasts.

My cock shrank rapidly, post deposit.

Janet gently freed herself of my embrace, turned around and dropped to her knees, taking my deflating wet cock into her mouth for a cleaning.

After a few moments of her sucking and licking I felt that an erection could soon return and so I put my hands on her head, suggesting nonverbally that a blow job would be nice as the second act of the morning.

“That should keep you happy for a few minutes” Janet laughed as she rose to standing, kissed me with a slight penis breath and headed back to her bedroom to shower and dress while I climbed back on the exercise machine for a few more minutes to watch the morning news.

I was tempted to whack off in the shower but I didn’t have to; fortunately, newly pregnant Julie joined me.

She washed my hair, the stuff on my head and the stuff around my cock then soaped up the rest of me, from my head to between my toes.

She worked quickly and happily, and while she was on her knees washing my thighs, she started sucking on my cock.

Which I love; I love getting head.

I came in her pussy from behind as we fucked in the steamy shower.

So, this was the life of a married man with a wife and two … girlfriends?

When you come twice before you leave for work, it’s the best.

After a hectic morning at home trying to have breakfast and get kids off to school and then a busy time at work I was sitting in my office about 11:30 thinking about that morning’s hot and sweaty fuck session with Janet.

There was something magical about her.

Janet was an “It Girl.”

I started to grow a woody under my desk, visualizing Janet in that yoga pose, remembering how she matched me stroke for stroke, our flesh meeting as we moved in sync with each other.

The sound of bare flesh slapping on bare flesh is one I enjoy.

Nut to butt.

Many women enjoy being taken from behind and I like it because I get to go deep in the pussy but also because I can control the pacing.

My lovers find it maddening that I delay their orgasms with my hands on their hips, varying the depth of my penetration and the speed of my stroke.

Some of my lovers have literally been in tears as I drug out the sex until they were begging me to come.

I sometimes have to hold their arms behind their back so they won’t be diddling themselves to climax.

I do it because an orgasm delayed is a better, stronger and more fulfilling climax.

For both parties.

Janet had started doing something that really enhanced our sex; when I was buried into her balls deep, she moved the insides of her pussy and the only way I can describe is was that she was milking my cock from the base to the tip in an effort to maximize my pleasure before, during and after coming.

I have no idea where she learned this technique; as far as I knew I was the only one she had had sex with in months.

This was the same technique Missy had used on me.

Even without this new milking technique, Janet knew she could get to me, meaning, get me to cum quickly in our sexual wrestling matches.

I had to pull out three times to avoid overheating —- to keep from coming too soon.

I’ll give the excuse that I was still worked up from last night but the truth is Janet’s pussy was unbelievably pleasurable.

My lewd thoughts Niğde Escort Bayan were interrupted by a question: how soon could I get to Santa Fe, New Mexico?

The question got me aggravated and pissed off in mere seconds and for only one reason.


Tony was one of the newest consultants.

He had abandoned his wife Janet (The MILF) and kids at Christmas for woman he was working with.

Within hours of finding this out and having Janet file for divorce, I seduced and fucked, actually, I pounded his soon to be ex wife for a full night and all the following day, without protection because I thought she was on the pill.

It was some of the best sex I had ever had and I have been hungering for her pussy ever since; just looking at her got me hard and when she wore sexy clothes are started flirting, I had a redwood in my pants very quickly.

But in the process of having sex with her, I got her pregnant.

I was turning into Clint Eastwood.

Who knew how many kids Clint had, with how many different women?

This is what money allows you to do, spread your seed around.

Clint, my idol.

Back to the present …

Eva, who headed up the business exit consulting practice, had signed on a client late the previous year based in the southern Rocky Mountain city of Santa Fe and she was standing in my office asking me a question about the place.

We had our people working in the client company since the January 2nd.

Eva wanted to know when I could get out to see the client.

The client had something to discuss with me.

He would only discuss whatever it was with me.

And it had to be in person.

Eva would travel with me on the private jet, along with two others but we would need to go and come back to LA the same day.

Catherine, my very pregnant wife, wanted me, well, allowed me, to travel two days a week.

On Tuesdays I focused on Seattle or Las Vegas; if I had to go on a Thursday I would go east (usually Scottsdale) or south (San Diego).

Catherine wanted me traveling with my secretary (actually she was my Personal Assistant) on these trips; she knew that Sabrina would keep me focused on business and would not allow me to think with my little head.

My wife knew that thinking with my little head gets me into trouble.

Catherine was the perfect wife.

Why is that?

Catherine did not mind me having sex with other women; and specifically she did not object me to fucking Janet or Eva.

But when I was fucking Eva, Eva was to be busy eating Catherine’s shaved pussy.

When I was fucking Janet, Janet needed to be satisfying Catherine orally. (Catherine gave Janet a pass on these 5:30am booty calls with me).

When I ran that vision though my mind, taking Eva from behind, pumping either her semi-virgin, still very tight ass or her hot wet pussy as she licked Catherine to orgasm after orgasm, I grew a harder than when I was just thinking about me fucking Janet that morning.

Eva quietly closed my office door giving us total privacy.

I stared at Eva as she walked, paced actually, in front of my desk.

Eva was even hotter, if that was possible, than I had ever seen her.

I stayed seated behind my desk, my erection growing as I watched the entire package: expensive Italian shoes; gorgeous tan legs encased in nylons which were probably thigh highs; a dark blue skirt that started about five inches above her knees; a white silk blouse that did nothing to hide her formidable and firm breasts.

Her arms were fit and tan, a gold bracelet accenting the fashion; small but expensive earrings and no engagement or wedding ring.

Eva had told Catherine that I was the only man she had slept with in years and that she wanted to continue to sleep with me but only with Catherine’s blessing. Catherine agreed on the one condition … Eva would be pleasing Catherine while I was taking Eva.

Eva, still pacing, was talking about something and I could hear her but I wasn’t listening.

I was straining to see large her dark areoles and eraser size nipples through her tight white blouse but I gave up my search only to find her standing still, silent, in front of my desk grinning at me.

I had been caught, like a deer in the headlights, my arousal evident as I tried discretely to shift my cock to a more comfortable position within my slacks under the desk.

I smiled back at her, a beautiful woman with a face that any man would love to go to bed and wake up with, and I heard her ask “Did you hear a single word I said Jack?”

“Not really. I got distracted when you took off your suit coat. I’m sorry.”

Eva laughed, leaned forward, those healthy breasts filling my vision and with her eyes twinkling at me she whispered “Should I put it back on?”

I laughed back, shook my head no, my eyes still straining to see the peaks of her tits and then I said “You now have my undivided attention.”

“Do I Jack? Really?” she laughed as she walked around behind my Escort Niğde desk.

I didn’t dare turn to face her.

My erection was at now full strength and it would be awkward to explain.

It could be considered sexual harassment.

Of course, so could what Eva had on.

Eva came up directly behind my leather chair and put her hands on my shoulders.

I could smell her perfume.

It only served to aggravate the situation under the desk; she knew I liked the fragrance because she had dabbed it in all the right places when we got naked together.

Eva dabbed it around her pussy, behind her ears, near her nipples and even on the top of her feet so I could enjoy it while I sucked on her toes. (Women like to have their toes sucked and their feet massaged).

I grew even harder as my carnal thoughts of taking Eva’s ass for the first, then the second time and finally third time on my birthday in Las Vegas ran through my brain.

Eva’s hands, though small, were strong and felt good on me.

I thought for a second of those small fingers wrapping around me as she stroked me to heaven, catching my explosion in her open mouth.

While I preferred my cock to be in her mouth, pussy or ass, I always enjoyed her hands on me and she loved my hands on her because they brought her pleasure.

I liked her mouth, but preferred her pussy but if you asked her, she’d tell me I loved her ass more.

Even without a drop of alcohol in her system, Eva wouldn’t hesitate to share with anyone that I would fly across the country just to fuck her ass.

It had that kind of attraction for me.

We used to call this an “E Ticket” ride at Disneyland.

But that was a conversation for another day as she started to massage me through my dress shirt, with the goal of removing the tension out of my neck, shoulders, upper back and upper arms.

Eva had strong hands, stronger than I remembered.

She bent down and whispered into my right ear “Relax for a few minutes Jack, close your eyes and just breathe. Slowly, and just take it easy.”

Amazingly, my erection slowly shrank and the tension left my body as her hands did their magic.

I broke the silence with “Did you take a massage class?”

She whispered, in soft and very sexy voice “Yes, but no more talking lover. Hush.”

In a few minutes my blood pressure had returned to normal, and I was relaxed once again.

I thought for a moment that it would be nice to get that kind of stress relief on a daily basis.

Sabrina was already blowing me once a day and that was a great bonus but I could use a massage too.

I’d ask Sabrina about helping me out with that, or finding someone who could.


Catherine, Janet (The MILF), Eva and I had lunch in the employee cafeteria at the dealership.

Julie would have joined us but she was at her doctor.

We found a table in the corner so we wouldn’t be disturbed.

Eva recapped the status of the consulting engagement in Santa Fe, New Mexico.

She spent much more time talking about the after work fun and games than the work time spent with the client.

Catherine and Janet really just wanted the dirt on Tony, and Eva delivered.

Eva had selected Kayla and Tony, who was Janet’s soon to be ex, to work with her on the assignment.

While having Tony and Kayla go through a training program was great in theory we didn’t have a program set up.

So, we just threw the two junior consultants into it, trusting they would learn on the fly, with Eva leading them.

During the day, all went well. The client seemed pleased as the team wasted no time getting into things. Numbers, operations, policies and procedures, cost centers.

After work, things got very interesting.

On her previous trips, Eva had stayed at a few different hotels and then selected one that had a nice two bedroom, two bathroom unit with a kitchen and a living room.

It was kind of an extended stay place.

She also found a local gym that offered yoga classes after work for a nominal fee.

Eva and Kayla arrived in Santa Fe on a Sunday night and then when Tony arrived on Monday at noon they left the client office to pick him up. Why he didn’t fly in the night before I have no idea. That was in my mind the first strike against him.

On that first day, on their way home from the office, Eva and Kayla went to the gym, changed into workout clothes and took a 75 minute yoga class.

Tony, on the other hand, wasn’t used to working out, so he waited in the car (Eva wouldn’t let him drive the car because his name was not on the contract) until the hot and sweaty girls climbed into the car to go to the hotel.

Tony could have shown some initiative so he could join them at the gym. Strike Two.

Once they got to the hotel room, without preamble, Eva had Kayla strip off until she was nude and then Kayla undressed Eva in the living room.

This took place right in front of Tony, who thought for a brief second he was going to get in on the action.

He was sure that this would be his first three way; more pussy than he had ever had in his life.

Remember, Eva and Kayla had been lovers a few times so they knew how to put on a show. They put on a show for me and just thinking about it gave me a woody.

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