Boys Will Always Be Boys Phase 01

My brother Tommy and I were 18 and 19 at the time of this story. Our parents and their friends were well into their 40's and all events happened many years ago.

The Beatles once wrote, "A bad little kid moved in to the neighborhood,"

They might as well have been describing me or my older brother Tommy.

Our family moved into a nice suburban neighborhood back in the early 70's and my brother Tommy and I quickly gained a reputation for being incredibly successful having sex with a lot of girls our age. 18 year old teenage tits and pussy became our mission in life.

Our ability to bring young 18 year old girls to multiple twitching orgasms became very well known around our high school campus. Not only among the students, but also with their mom's and the female faculty members.

Girls like to talk. Our secret was oral sex. Tommy and I were masters at taking our time with the girls to make sure they had at least 2 orgasms before we started to attack their young pussies with our cocks.

After we had tapped out most of the teen pussy at school, we started to wonder if the saying was true that apples don't fall far from the tree.

Tommy and I were both bad to the bone and had a dark passion and interest in mature women. We not only wanted to fuck the daughters, we also wanted to fuck their moms.

We developed an obsession to peep on mature women in very discrete ways. We both liked to watch. We would later find out our passion for watching might have been hereditary.

We liked to watch mature women at the beach, at the pool, at our sporting events, getting out of their cars looking for a leg spread, stealing looks up our teacher's skirts, and watching mature porn. We had a particular obesssion with stewardesses probably because our mother was also a stewardess.

As a family we took a lot of airline flights on our vacations. Tommy and I were very good at staging and setting up the stewardesses for up skirt shots with their short skirt uniforms.

Another one of our favorite games was to discreetly work up a hard on and then have a mature stewardesses help us with our seatbelts. That required them to get close, bend over and buckle our belt occasionally brushing up against our hard cocks.

Dropping an item on the floor or creating a distraction while a stewardess was bending over helping a passenger across the aisle were two of our favorite tactics. Stealing an up skirt beaver shot of the top of their stewardess nylons, girdles or panties was a major victory for us.

Another favorite trick of ours was to ask the stewardess if she could get our bag out of the overhead luggage compartment for us. That gave us the chance to smell their perfume up close and to accidently brush our cheek against their hanging mature tits or her soft exposed mature stomach. Cheap tricks for sure, but well worth the risk.

We even pulled the same stunts with our own mother if she was working our flight. Our mom stewardess was a kockout. In her early 40's with flaming red hair, large breasts, long legs and a great smile.

It was arousing for us to watch other male passengers manipulate and try to touch our mom. They would try to get our mom to reach up and retreive an item in the overhead bin and have her brush their face with her magnificent tits.

Male passengers would also intentionally drop an item on the floor of the plane and have her bend over to pick it up providng them with a full shot of her thighs and her ass. They were playing the same game with our mom as we were playing with the other stewardesses.

More than once Tommy and I watched men run their hand over our mom's firm ass or run their hand up her skirt, to feel the inside of her soft mature thighs while she was bent over and vulnerable serving passengers.

It was almost as if our stewardess mom Jean was teasing and tempting them to touch her inappropriately. We know our dad also saw it happen and seemed to enjoy watching his wife Jean being discreetly touched and fondled by other strange men. We both found that very interesting about their relationship.

When it came to older women Tommy and I knew who all the good looking mature wives and moms were in the neighborhood. Tommy and I would make it a point to make friends with their sons or daughters so we could be around the lovely mature moms and housewives and see if we could score some mature pussy.

Neighborhood pool parties at our house were our favorites. We would try to get a peek at the mature wives and mothers in one of their vulnerable moments such as rubbing suntan lotion on their bodies, changing into their swimsuits, sunbathing, showering, using the bathroom.

We also became sneaky at spying on them in their homes having sex with their husbands and lovers or masterbating. We caught moms doing all of the above. We were very good at what we did.

I remember when we became old enough for Eagle Scouts our troop had a couple big tit moms in the neighborhood that volunteered as den mothers for our troop. They would let us scouts tie them up at every meeting to perfect our knot tying skills and earn our badges.

We would always have them sit on a kitchen chair, pull their arms back and tie their wrists and elbows behind their backs totally exposing their mature milkers. We always had a small kitchen fan nearby that we would purposely turn on to blow a light breeze across their tits making their nipples stand at attention.

One den mother in particular had very pronounced nipples. I remember at one meeting after tying her up Tommy went to the kitchen drawer and brought back a couple clothespins. We knew what Tommy had in mind, and our helpless, vulnerable den mother also knew what Tommy had in mind.

Her nipples looked like hard pencil erasers straining against her khaki den mother blouse. We were all encouraging Tommy to use the clothes pins as nipple ornaments on our middle-age den mother.

Tommy raised the clothes pins up to her face and pinched them open and shut a couple times to get her reaction. Tommy then started to lower the clothes pins towards her nipples.

All of us scouts were mesmerized with anticipation. Would Tommy really be bold enough to hang clothespins on this woman old enough to be our mother? The den mother then said what we did not want to hear,

"Don't you dare young man or I will tell your parents."

That really pissed off Tommy. He now really wanted to clamp her nipples and humiliate this middle aged big tit bitch and make her squeal in pain.

Tommy pinched open the clothes pins and put them within an inch of her protruding nipples, but then backed down not wanting to deal with the consequences.

We had another den mother, Mrs Vandenberg who was divorced and in her 50's. Mrs V. was like one of those mature school teachers you read about that gets fired and arrested for seducing young students. She would not only allow us to tie her to the chair, but would also let us blindfold and gag her with our troop bandannas.

Once we had Mrs. Vandenberg tied and blindfolded she was helpless and defenseless. The best part was that she could not tell which of us nasty scouts was messing with her body.

We would unbutton her blouse down to her stomach, pull it open and get a good look at her mature tits and erect nipples through her bra. We would then slowly slide the straps of her bra off her shoulders and lift her large tits out of her bra cups for us to admire.

Our favorite thing to do with Mrs. Vandenberg was to rub ice cubes over her mature nipples to get them fully erect. Tommy finally had his chance to use his clothespins on a mature den mother, and he took it.

Her nipples would get so hard and pronounced that it was easy work for Tommy to pinch and clamp her nipples. She would whimper and moan and thrash her head back and forth trying to shake off the blindfold. Looking back we think she climaxed a couple of times. She got off on it.

Some of the scouts just looked, but most of us gave her mature hooters a workout with our hands and our tongues. We would also gently lift up her khaki den mother skirt and get a good look at a her mature thighs and panties.

At one of our meetings a particularly nasty scout grabbed a cucumber from the fridge and slowly dragged all twelve inches of it across Mrs. Vandenberg's cheeks, her gagged mouth, and her lips.

Mrs. Vandenberg immediately knew what is was. Her breathing rapidly increased as her large mature tits heaved up and down decorated with clothespin nipple clamps.

We removed her bandana gag and we each took turns working the cucumber into her mouth with a jerking motion as if we were jerking our own cocks into Mrs. Vandenberg's mouth.

We then rubbed the sliva covered cucumber across her exposed thighs teasing her into thinking we were going to run it up her skirt and bury it in her pussy. It wasn't necessary.

The feel of the stiff hard object laying between her tightly tied thighs was enough to send her into a body shaking, toe curling orgasm.

This was quite a life changing experience for young scouts. We just stood back and watched Mrs. Vandenberg moan and squirm and rock the kitchen chair off the floor as if she was going through an exorcism with the tit ornament clothespins dancing on her chest.

After we untied Mrs. Vandenberg she just sat in the chair for minutes recovering from her massive climax. I removed her blindfold and Tommy removed the clothespins from her nipples. She wanted to keep them.

She dried off her sweat covered tits and tucked them back in her bra. She buttoned up her den mother blouse and then left. We noticed she also took the cucumber home with her.

Stay overs at friends houses were always the best. We always liked to mess around with the mothers. We would distract the mom so we could go through her underwear drawer and check out her bras and panties. We always believed that you can learn a lot about a woman by the type of panties she wears.

Some of the moms were prim and proper women wearing granny panties and traditional bras. Some of the moms were potential sluts who preferred to wear thongs and crotchless lacy panties with see through bras. We figured the moms with the slut underwear were probably getting the most cock action from their husbands and lovers.

We would find out very quickly what type of woman she was by going through her dresser drawers. Tommy and I would focus our seduction and surveillance efforts on the nasty underwear moms. Our system was 100% accurate as a result of their panties.

It wasn't so much about having sex with them, but really more about watching them when they felt comfortable which would make them more vulnerable. They had no idea they were being watched. We were true voyeurs.

Long story short, if we couldn't yet have sex with them ourselves, we wanted to find a way to watch them having sex with their husbands, boyfriends, lovers, neighbors and even relatives.

Our passion for voyeurism started out very innocently enough as it does with a lot of guys that have a high sex drive at a young age. Spying on our mom while she was getting dressed or taking a shower were a couple of our favorite activities. We also enjoyed messing around with her underwear.

Almost on a daily basis, Tommy and I would either pick out a pair of her used panties or a thong from the hamper, or some fresh panties from her dresser drawer. She had a nice variety of thongs and bikini style underwear in all colors and texures. The more texture, the better.

We would spray her panties with her unique perfume before sneaking them off to our rooms. We would wrap her perfume laced thongs or panties around our cocks and unleash a healthy load of teen boy jizz in her panties fantasizing that we were actually fucking her. Tommy and I rarely ever jacked off without a pair of her perfumed textured panties wrapped around our cocks.

She once worked up the guts to confront us about her clean panties being hard and crusty. We acted as if we were totally innocent and turned the tables on her. We put her on the spot.

We asked, "Mom, what are you accusing us of doing? Are you accusing us of messing with your underwear? What could we possibly do to make your underwear hard and crusty?

She just stood there and stared at us speechless. We wanted to hear her say the words, "Boys I think you are jacking off in my expensive underwear." We were intimitating her and repeated,

"Come on mom, what in the fuck are you acussing us of doing with your underwear?"

We all knew damn well why her sexy panties and thongs were hard and crusty. We just wanted to hear our sexy prick teasing mom say it out loud. She backed down.

In essence we had just told our 40 plus year old sexy stewardess mom to mind her own business and to go fuck herself without saying it to her face.

Just to piss her off, and further intimidate her, we doubled up our efforts and jacked off in her panties and thongs twice a day, and starting including her bras. We noticed she started doing laundry more often.

As I mentioned earlier, our mom Jean was a stewardess in her early 40's and was a mature knockout. Flaming red hair, nice tan for a fair skinned redhead, big smile, large freckled breasts, and long legs. The older Tommy and I got, the more aggressive we got with our mother.

For years Tommy and I would check her out in her swimsuits on vacations or at our backyard pool. My brother and I would literally fight for the right to rub her down with suntan lotion.

Unknown to her, we would sneak her suntan lotion into the house or a hotel restroom and fill it with our jizz to rub on her later in the day. It was arousing to see our mom getting a nice tan from our potent, healthy jizz rubbed all over her mature body including her face.

Occasionally when our mom was showering my brother and I would wait and listen for her to turn off the water and then intentionally walk into her bedroom acting as if we needed to talk to her right away.

We caught her many times stepping out of the shower soaking wet with her large tits jiggling and her red full bush on full display. She never acted embarrassed or tried to stop us.

She had large pink nipples and a stunning full bush of nicely trimmed red pussy hair. Getting a good look at her full mature body to jerk off to later in the evening with her underwear was definitely worth the risk.

If we owed our buddies a favor or we wanted something from them, we would pull the same stunt and let them get a peek at our mom. I remember one day we had three of our buddies with us when our mom stepped out of the shower.

Her tan body with bikini lines was glistening with water dripping off her full heavy tits and her red bush as she stretched to reach a towel.

Our friends were mesmerized watching our mature mom's tits hang, sway and smack together as she bent over to dry her legs.

The five of us stood there for minutes and watched our milf mom stewardess dry herself off without her knowing we were there. Two of our buddies noticeably jizzed their pants just watching our mom's swaying tits and full bush beaver.

We had to literally pull them out of the bedroom thinking that they might try to force gang bang our mom. Stewardess Jean never knew that she was seconds away from having our three friends shove their unrelenting teenage cocks up her mature hairy pussy. Our buddies were in debt to us forever.

We always thought she had no idea we were watching. However, we later found out that she knew damn well we were watching.

You see, our mom had been an addicted exhibitionist for years and our dad was fully aware of it. They both also knew that Tommy and I were born voyeurs. Our father was also a dedicated voyeur. That is why Tommy and I thought being a voyeur was hereditary.

We also knew our mom was aware of our stash of porn magazines. One day Tommy and I came home early from our college classes, and found her down in our bedroom. She had no idea we were there.

She had a couple of our nasty bondage magazines open and spread out on our bed. She was stark naked sitting in a chair with her legs spread wide and her ankles resting on the bed. She had fingers up her pussy rubbing her clit while looking at the magazines.

All of a sudden she grunted, threw her head back, and unleashed multiple squirts of pussy juice all over our magazines and our bedspread in a twitching toe curling orgasm.

It almost appeared as if she was pissing on our collection of porn to get revenge for jizzing in her underwear. When she was finished, she got dressed and left the bed covered with magazines and pussy squirt.

We confronted her about it that night, and she acted as if she knew nothing about it. She had turned the tables on, and she had won. We no longer jacked off in her panties.

Our dad was also a voyeur and was a conisour of high quality porn magazines and videos. He was a big fan of True Detective magazines and snuff porn.

He and our mom loved to watch videos of mature women getting abducted, bound and gagged, stripped and fucked and sometimes snuffed out. Tommy and I also loved the bondage videos.

Sometimes Tommy and I could hear the videos playing while dad was fucking our mom Jean. She also enjoyed watching the videos while getting fucked and she did her best to try to control her screaming orgasms but she was not very good at it.

She was a true screamer and Tommy and I jacked off many times outside their bedroom door just listening to our mother scream and moan as our dad relentlessly pounded her to orgasm.

Sometimes our mother would let us stand in the bathroom and talk to her while she was showering. When she was done she would shamelessly let us watch her dry herself off with her big swinging tits and full red haired pussy right in our faces.

Our mother was intentionally taunting and teasing us by letting us watch her shower knowing that her sons would jack off later while thinking about her lovely mature body. She got off on it. She was an exhibitionist and we were voyeurs. A perfect match.

I would be lying if I said we hadn't thought many times about force fucking our mom after one of her showers. It would have been so easy for Tommy and I to grab her and drag her naked mature body into the bedroom, tie her to the bed with her bras and panties, and work her over and enjoy her mature stewardess pussy for hours.

We both dreamed of feeling the tightness of her mature pussy wrapped around our teenage cocks the same way that our dad had experienced her pussy for years. It felt like she was almost begging for us to take her. It was so tempting.

Well, we didn't let our sexual urges get the best of us. We didn't know if she would keep her mouth shut about her adult teen sons using her as a fuck toy or what our dad would do if she told him. We decided to back off, however the thought of violating her mature pussy always lingered in the back of our minds.

Our dad knew very well that Jean had the exhibitionist kink and he took advantage of it by showing her off and having her tease his buddies and even strangers. He would have her wear her stewardess uniform out to dinner even when she wasn't working because let's face it, everybody wants to fuck a stewardess.

We always knew that if they went out and mom was wearing her stewardess outfit, they were going to have nasty sex when they got home that night and Tommy and I were always well positioned to watch or listen.

Dad loved to fuck our mom while she was wearing her stewardess uniform. So did some of their friends including our American Legion baseball coach Mr. Trudell.

We would find our coach dropping by our house unexpectedly many times after practice to just visit with our mom and dad. Our mom always seemed to be wearing her stewardess uniform when coach Trudell stopped by to visit.

Tommy and I suspected there was something going on with our parents and Mr. Trudell. One day when coach Trudell was visiting, Tommy and I acted as if we were leaving but then snuck back into the house through the basement door.