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.
