Milestone – by iamscrwd

True story: Milestone. Author: iamscrwd. Unintended consequences of events. The story is including of True Story, Blowjob, Cheating, Cum Swallowing, Incest, Teen Male / Female, Voyeurism, Written by women genres.

True story: Milestone – part 1

Author: iamscrwd

That is what it is, a milestone of life that requires something put into the bucket list. My fortieth birthday, the entrenching realization of middle age setting in with a building sense of urgency to experience something or anything that can check mark a life with enough excitement to carry oneself for that long steep decline of age.

Maybe a long ways to go, but I was bound and determined not to go gently into that good night. So I forced the issue, demanded to my family I needed to do something…anything. Thought about a cruise…everything was booked on the major lines for a year or so. Looked into an all-inclusive…the choices were slim, none for the bigger names, but found an opening in one obscure resort that actually got my blood moving.

My husband said that I should do my research and then book it if I wanted, just make sure it would fit within our schedules. I booked it. Only problem was it would be tight for my husband. He was scheduled for a business trip that at the earliest would put him there late on the first day of the ten day reservation. And unfortunately, he would have to leave before the ten days were up. He told me, just in case, to book both of us on the flights as if we both could make it and if not, he would take alternative transportation and we would just eat the added cost.

The resort sounded idyllic…nestled on a secluded area of a small pristine island in the Caribbean. Even though it seemed to be small there was the option of using an adjoining resorts facilities and entertainment events. The one caveat, the other resort was described as pretty risque…promoted their beach as a “clothing optional” area and called their events as “excitement for swingers at heart”. This raised the hair on the back of my neck…in a good way. Thought that this just might be the thing to spice up our lackluster sex life.

My memory raced back ten years and pulled out a chapter in my life I never really shared, to my knowledge, with my husband. I had a three-month affair with a co-worker, he was fresh out of college and the company had me as his mentor before shipping him off to a territory. In reality, he mentored me. He might have been eight years my junior, but his eight inches had decades more experience than me. Never fails, even after ten years, the thought still excites me. Still, there is always the lingering guilt. Not necessarily the infidelity part, but the fact a month after he left, I had an abortion.

Did not take much of a jump to know it was his, my husband had a vasectomy when I was pregnant with our second child. So it was obvious that the fetus was not his.

So the thought of a hedonist resort next door got my juices going. Maybe my husband could be persuaded into a little extracurricular activity…and I could use it as an excuse to pursue my own illicit desires.

I visualized myself with all kinds of different guys, in quite a few different scenarios. The weeks leading up to our trip pretty much wore out my vibrator.

Then the planning of the trip started to hit speed bumps. My sister was going to “baby sit” my son and daughter, but then her mother in law had an accident.

Thankfully, after a week of stress, Megan found refuge with one of her friends. But Mark was without a place, or should I say, someone to watch over him. Granted, Mark was just about to turn eighteen, just so happens two days after my own birthday. When I would be on the island. Still, there was no way I would leave my man-child alone in my house.

Already knew he was not a virgin, and without a doubt he had a lot of girls to choose from. I did not want him knocking up some girl and suffering the rest of his life.

Five days before I was to leave, a friend from work offered to take him in. I was kind of skeptical, because at times Julie seemed to be just a little bit oversexed. Even though she was married, I had caught her looking at Mark as if she was a wolf salivating over a large steak. Or as she kept telling me, she was a Cougar on prowl for the next cub.

The next day, my husband called…he would not be able to make it to the island until the middle of next week at the earliest. At best he would have maybe two full days.

Great…maybe I should cancel too, ran through my mind, the disappointment must have resonated thru the phone.

My husband caught it, and then he hesitantly suggested that I go on the trip.

The rebuttal never made it past my larynx…my mind already envisioned myself as a wild animal feasting on tender flesh. All that escaped my mouth was a sharp grunt.

It was not a grunt of objection. Still, he sounded conciliatory and then asked if Mark was taken care of because maybe he could go with.

I quickly tried to think of an excuse, since I did not tell my husband about my fantasies or the neighboring resorts enticing assets. Shit…hell…I really wanted to go. Told him that I would ask Mark, but he probably would not want to go with his Mom.

I was wrong. That evening Mark gave an exuberant, resounding yes to going. He read the brochures…and Mark being Mark, could not wait to check out the place next door. Even though that was my same intention…I shook at the thought of my son chasing naked women in my presence.

But…if I wanted to go, guess Mark would have to tag along.

Started to repack my stuff, did not think that I would need to bring some of my more intimate items, but then pulled out the string bikini I had bought for just this occasion.

I thought about how I looked when I had tried it on…this might be the last time I could get away wearing something like this…hell, I flat out looked dynamite in it. To heck with it, son or no son, I was not going to let him stop me.

It was just a little amusing when we checked in at the airport, the travel itinerary said Mr. and Mrs. We both laughed, but then again he is a Mr. and I am a Mrs. Joked about it during our travels too.

Kind of played it up also, when they called us to the flight desk by Mr. & Mrs., we walked up with our arms around each other just to get a response.

I got a positive wink and nod from the attendant behind the counter…then she leaned over and whispered in my ear. “I’m jealous…have fun with your cub”.

Don’t know why, my vanity or whatever, but as we turned I grabbed Mark’s ass and gave it a squeeze knowing full well the attendant was watching.

Mark jerked from surprise and then mouthed “what the hell, Mom”. I just playfully smiled back.

When we got to the resort and checked in, we were still listed as Mr. & Mrs. But when the gal asked for our room preference, I said two beds. She looked quizzically at me and then mentioned that the only room left with two beds is the special needs one.

Great…put a cripple out or share a bed with my son. I asked, “King size?”

Glad I did it, our room was awesome, the double doors opened up to the beach. The other resort fence was not more than a few feet from our porch. The iron gate that separated the properties was only twenty feet away, the open bars offered a tantalizing peek into the hedonic environment.

Just on the other side of the gate, a muscular man standing totally unembarrassed…completely nude, his gorgeous penis swinging in front of him as he talked with buxom naked woman.

I could not take my eyes off of them, I was mesmerized…so was my son.

Then he talked, “Wow…nice tits…this room is fantastic”.

I hit him in the arm and feigned anger, “Mark…that is not something you say in front of your Mother!”

“Oh, I am sorry, “ he faked having any remorse; “you have nice ones too”.

“Nice what?” I had thought for a second I might have heard him wrong.

“Tits…you have nice tits too, Mom”.
“Mark…I am your Mom…stop it. Anyway, how would you know?” I quickly scanned my memory banks just in case.

“Just guessing”…then slipped in, “but I am sure I’ll find out”, as he tilted his head towards our neighbors.

I was just a little flabbergasted, but to be honest, a little proud that my just about eighteen-year-old son thought of his mother being able to hold her own.

I quickly took stock of the room. It was not laid out for those with even a smitten of humility. There was a large tub, big enough for multiple people, totally exposed in the corner of the room, right along side a glassed in shower stall.

Thought that there had to be a bathroom somewhere.

Sure enough there was one, but behind the door was just a toilet and sink. Suppose that I would be using the fresh water shower down at the beach…no way I would use these in front of my son.

Mark must have correctly read my consternation, a goofy smile stretched across his face as he looked at the tub and then at me.

“Not in a million years, bucko”, I intentionally spit out to make sure he did not get the wrong idea.

His face contorted into a pout.

“Jeez Mark…I am your Mother for Christ’s sake” but I was actually amused at his reaction.

At this point of time, there was not a deviant consideration in any way or form regarding the possibility of even remotely contemplating something physical happening between my son and I. But…this short back and forth, his expressions and my verbal responses were in a playful mode. So my antenna never went up in defense so to speak.

Ok…we were settled in and I wanted to go to the beach, have a cocktail, unwind a bit from ten hours of total travel time.

“I do not know what you want to do, but I am going to relax on the beach” I said more to myself than Mark.

I grabbed my suit, hesitated when the skimpiness of it hit me, then told myself what the hell and went into the bathroom to change.

Putting on my, err…my suit if you can call it that, as was obvious in my reflection of the mirror that this attire would not be socially acceptable around children back home. Especially considering one of them could possibly be my almost adult son.

Heck, the small triangles covering, barely covering enough of my breasts to hide most of my areola’s, did nothing to leave the size of each of tits to the imagination. My full “C” cup mounds were pretty much out there for display. I wondered for a second if the small strings had enough tensile strength to hold them up.

Scanning down and making a slight twist…the string running between my legs and up my ass crack was nowhere in sight. Fortunately, for my age, my exposed ass cheeks still had enough firmness, so as not to look as though I had saddlebags dragging behind me.

As I turned back… even though I had thought I had trimmed and shaved my lower part back home, the small tuft of hair on my pubic mound could be seen just above the couple square inch patch of cloth covering me down there.

Shit…too late now. I pulled the bottoms off, lathered up a little and with only three of four passes with my razor…my vaginal area reverted back to pre puberty.

Gathered myself up and opened the door.

I do not know who was more surprised.

Mark apparently had decided late that he could quickly change into his swimsuit and figured by standing in front of the bathroom door, he could block it just in case.

That did not happen, I swung the door harder than anticipated, it hit him in the head just as he was bending over to pull up his swimsuit. He went down on his back…his swimsuit around his ankles.

My son’s penis flopped in an arch to his belly; I could not stop my eyes from focusing on it.

My God, my son’s dick is bigger than his father’s is all that came to mind.

Then it started to grow. Mark’s mouth was gapping open…he…he was staring almost in a mesmerizing way. Yet his eyes coursed over my torso…then I realized my jaw was slack too…Holy Shit…my son’s cock was now rigid…it had to be close to my ex lover’s…I shook my head coming to my senses. This all happened in less than a minute.

I gurgled out, “Ah…sorry, should not have opened the door so fast. Uhmm…let me get out of your way” as I stepped over him. In and effort to not step on him…had to look, my eyes automatically went back to his cock.

My psyche tried in vain to supplant morality for the lustful vision of my own son’s penis floating in my brain. Damn…I needed a drink.

Made it down to the beach, spread a towel on a beach chaise, adjusted my sunglasses, and got comfortable. The first daiquiri soothed the quandary of my conflicting thoughts and started me on the path to ignoring some of my inhabitations. I rationalized that maybe my multiple week build up of expectations might have triggered some psychosis, so to get my mind off of “that” penis started to recon my surroundings.

From my vantage point, not fifty feet from the wall separating the two resorts, I had an almost unrestricted view away from the neighbors, but towards the neighbors the wall blocked the angle to seeing more than a few feet of their beach.

I actually thought about moving the chaise closer to the shore in hopes of visually intruding on their privacy. With a warm humor coursing through at the deviant thought, could not help but smile. But, better check out the locals first.

Most of the patrons, from my resort, seemed to be a hundred or so yards away, accept two couples that were maybe twenty yards away.

Noticed the two guys as I was originally walking onto the beach when one of them elbowed the other and nodded in my direction. It fed my ego immensely and it was all I could do so as to not let on. Thankfully my large, dark sunglasses allowed me to check them out without them knowing.

As I settled in with my second daiquiri I had assessed the couple to be beyond the honeymoon stage and before the children raising stage at most in their late twenty’s.

The two women were so engrossed in their own conversation; they completely ignored their two male partners standing with drinks their hands a couple of feet into the turf.

Did not take much of a leap of logic to know that from the two guys vantage point, they had a direct line of sight to the “clothing optional” beach next door.

From my standpoint, they appeared to swivel their heads in my direction more often than down the beach.

Could not help but to check them out, mid to late twenties and physically fit, there was much to see. Let my mind wander as to what they might look like without their hip hanging swimsuits…where they hung? You think they would be interested in a “older” woman? Wonder if they would be interested in a threesome?

That thought came out of nowhere…had never contemplated having two guys at once. The thought tickled my senses right down my spine. My nipples tightened at the thought.

A quick glance at the women, they were completely in oblivion, and with the help of liquid encouragement I stood up and walked towards the water. Could have just gone right in front of me as I could feel their eyes capturing my every move. But…what the hell, let’s see just how interested they really are up close. So I altered my path to within feet of them, making sure that my movements yielded more sway than necessary and not in anyway disguising my sexual intent.

My nipples were in full erection and had their full attention as I approached. While walking by, in a very planned move, I turned my head towards them lifted my sunglasses and checked out the front of their swimsuits. Raising my head I gave each a smile and wink then broke into the surf.

The water was extremely warm, but felt good and still cooled down my libido a tad. Could not help feel a little of accomplishment at seeing the tents rise in those complete strangers.

Movement to my left caught my attention, it was a couple over at the other resort, and even though they were quite a distance away…there was no question as to what they were doing. His back was slightly turned towards me but I could see her, and one copious tit bouncing unencumbered to each thrust he made into her.

My audience was distracted…do not know what made me think they were “my” audience or why I should even care, but like a little kid throwing a tantrum for attention, I had to do something.

I pulled off my skimpy top, stood up, and rubbed my tits as if they were covered in sand and I was cleaning them.

It got their attention; I slowed the rubbing, their eyes glued to my chest. Brought a devious smile to my face…then to theirs.

Did not last long, one of their women saw what was going on. She barked in a not so pleasant manner…like puppy dogs both the guys turned and shuffled back towards them, their heads down as if in guilt. Even from this distance, I could feel the daggers of anger coming from the eyes of the women.

Oh well…so much for that. Returned my attention to the couple obviously fucking in the surf. Like a bug to a light, my feet moved me closer to them, my curiosity greater than my caution.

As their details came into focus, my feet froze.

The female was the one that Mark and I saw by the gate, she had to be at least my age or greater…the guy…it was Mark!

I did not know how to handle this…was I jealous? Not because of my son necessarily, but more from me being extremely horny from teasing a couple of guys. All of which I knew deep down, due to the condition of having their female partners right there, nothing would have come from it.

And here my son was, getting what in my mind was the real reason I wanted this trip.

God damn, this woman…she was living my fantasy, not of my son but a young cock plying its hard youthful strength deep into her vagina…and not mine!

Like stuck in a state of suspended animation, I just watched.

She was driving down more and more violently as my son reciprocated, her head thrown back to the sky. Mark was peppering her neck, upper chest, with nibbling pecks. Then he closed around her nipple…pulling it between his teeth.

I shivered at the thought of someone doing the same to me…

Her breathing, even noticeable from my distance, had changed to gulping…then she arched hard against my son. My God…she just climaxed.

Mark just froze and held her…did he cum too?

A few minutes passed, they were still enjoined, her head now resting on his shoulder catching her breath.

I could see Mark’s lower torso start almost imperceptibly to oscillate.

The woman made a small whimpering sound.

His oscillating movement was now interjected with an occasional thrust.
—————-

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