tagMatureYear of 1966: Late Winter

Year of 1966: Late Winter



This is the on going saga of two ladies training of a young man into the appreciation of bust, mature, oversexed women. PLEASE read Lawn Works Rewards and Winter Weekend (all chapters) too understand the previous training that has accrued.

I had had a long and “fun” filled Christmas break and was now wondering how my parents would take the news of me taking the spring term off from school to assist Jeanne and Bertha with their “cabin” work. I was relieved to hear them tell me that it was OK! to take a term off to make some money for spending and such. (Come to find out Jeanne and Bertha had talked to my parents before hand and used some lame reason they needed me to assist them and were willing to pay me for the help.)

I started working again at my father factory until the weather got nice enough to go up and work on the “cabin.” I would work in the shipping department and help the receiving clerk when the truck arrived.

When I got home from work one evening about three weeks after the start of the New Year I was surprised to find my mother and dad sitting on Berthas porch. (They called to me as I walked to the house from the garage) They asked me to come over, as they needed to talk to me.

Bertha had asked them if I could live in the fixed up basement, as she was afraid to be alone in the house with Lenny gone. Bertha had told my parents, as we had send the going on, that she had had many a “bad” phone calls and people knocking at her door at all hours of the night. (We had seen the police cars some nights and were wondering what was going on. Come to find out later the cop was a friend of hers, and she had set it all up so I could live with her.)

My parents even had agreed to me living at Bertha house, even though it was next door to their house, till Lenny got back from his “trip.” (He never did return as he ran off with this bimbo from his last job that was half his age. He did not know what a “horny” wife he had and though a younger one was better.)

Bertha had cleaned up the basement rooms for me. (There were no windows and you could not hear anything that was going on outside so we could enjoy each other without being disturbed) The next weekend I started to move some of my things into her basement. The first day I started to move my clothes and thing over she was laying on the bed naked when I walked down the steps. She just spread her legs and started fingered her pussy. She licked her lips and patted the bed for me to join her. I hung up the load of clothes I was carrying and sat down next to her. I leaned over and kissed her and fondled her “big” tits. I told her I had better go get another load before my parents wondered where I was at, She agreed and told me to hurry.

When I got back to the house Mon asked if all was OK? I said Yes!, and grabbed another load of stuff. She told me to tell Bertha that she would have supper for all of us in about an hour, so to make sure Bertha was informed, as it was just a spur of the moment thing.

When I told Bertha about supper, all she said was “I was to be your supper.” I told her she could be “desert and midnight snack.” She smiled and got up to get dressed. She walked over to me and rubbed my crotch, which already hard a raging hard on going. She licked her lips and gave me a squeeze and kiss at the same time. She held on to my balls and with the other hand unzipped my fly. My cock sprang out of my pants and bounced against her arm. She let go of my balls and reached for my cock. She started stroking it and with her still naked I pushed my cock into her belly. (She was only 5’ 1” tall and I was 6’ so no way could I make my cock meet her pussy directly) She fell back on to the bed and spread her leg. Her pussy was so wet from her fingering herself, that when I leaned over as I was standing between her leg, my cock slide into her. I started moving my hips back and forth slowly and within a couple to strokes I blew a load into her pussy. She looked up at me and smiled. Just then the phone rang and I jumped. As I did my cock came out of her and the last few spurts flew onto her belly. She reached for the phone and told my mother we would be there in five minute for supper as we were straightening up the room and lost track of the time.

Bertha hurriedly wiped off my cum off her belly and got dressed, but without putting on and under pants. As she walked up the steps my cum ran out of hr pussy and she had to go change pants. (This time she put on underwear and a skirt)

When we got next door for supper we found Jeanne sitting there also. She just smiled and lightly licked her lips so my parents did not see. She said that she had gotten “cut” from the golf match for having to high a score and had come home early.

Mom had fixed goulash and salad for us for supper. Dad came home late as he had had a problem at the factory. When supper was done I got up to help mom with the dishes and stuff. Jeanne and Bertha said they were going to run to the store and get some fresh apple pie and ice cream for desert and to have coffee ready when they returned. I walked them out to the car, as Jeanne had asked me to get her clubs out of the trunk. In the garage they told me that after the ice cream they both wanted some “hot” cream filling. I kissed both of them and patted their butt’s and smiled.

When they got back they told my parent to come over to Jeanne house for the desert. We walked over and upon entering the back door I saw Bertha out of the corner of my eye winking at me and cupping her breasts. It was then that I notice that neither one of them had a bra on.

Mom and dad went home after desert as dad was tired and wanted to retire early.

I told them I was going to stay and look over the plans for the cabin I was drawing for our summer work.

As soon as they left Bertha walked over to me and kissed my cheek. I reached up to feel the breast when Jeanne grabbed my hand and pushed it into her crotch. Bertha just smiled and said, “a little horny their Jeanne?” Jeanne just said ye, and I get firsts today.

Bertha said, “Sorry I already had firsts this afternoon.”

Jeanne then grabbed my arm and led me to the bedroom with a rush of desire. She was taking off her blouse with her other hand as we went down the hall. I assisted her by pulling down her pants and panties. She turned around as we got into the bedroom and grabbed by belt and off came my pants with a yank. She pulled my sweatshirt over my head and we fell onto the bed naked. She rolled me over and sat on top me with her massive tit’s hanging inches from my mouth. I raised my head and licked her left nipple. She leaned forward so I could get at it better and moaned as I lick and sucked. She raised up and moved back a little so my cock was centered on her pussy. She lowered herself down and with one quick push had me into to her up to my balls. She just rode me like a piston moving up and down. It did not take her long before she orgasmed and fell forward onto my chest. I had not cum and she knew that, so she started moving her pussy up and down again. She blew two more loads before I did. All the time we were going at it I had noticed a light in the hallway that seemed brighter then normal. When we got up Bertha just said, “Got it on the movie Jeanne.”

Come to find out Bertha was filming us on a new 16 mm camera she and Jeanne had bought for just for the upcoming “cabin” work.

Jeanne asked if Bertha wanted to get into the show and she said, “Next time it is all mine.”

Bertha then said, “We need to let him rest tonight, as I think both of us have ridden him hard today.” Jeanne agreed with her and went home to sleep.

The next day, Saturday, I finished moving my things into Berthas basement and that evening I went bowling a couple of friends from church. (This was just to make things look ordinary for my parents.)

When I got back too Berthas house she was sitting up watching the news and having a drink. She asked how the bowling went and told me to get a beer or something to drink. (I could never think of drinking at home, so this was one of the other “perks’ of living with Bertha)

She had a loose top on that just came to her waist. Her boobs keep it from hanging down further. I sat down next to her and put my arm around her. She snuggled into my armpit and laid her hand on my leg. I reached down and cupped her left boob. She moaned and turned a little so I could get at it better. I flicked her nipple and slowly rubbed her breast. She moved her hand further up my leg and found a raging hard on growing even larger. She asked if I had had a good night and I told her of all the young, small titted girls at the bowling alley that were ‘eyeing” us guys.

She undid my zipper and reached in and released my cock from it hiding place. She started stroking it and asked if I wanted to screw on of the young girls that I had seen tonight. I said like large breasts better than the small things they have to play with. Bertha looked at me and said, “ I guess Jeanne and myself have trained you well my boy.”

II just told her to come down to the basement and see what I had bought at a store that was not for the average person. (Remember this was 1966 and adult bookstores were not around most cities and I head gotten this copy in

She looked at me and said,”‘ I hope it is 16 mm to work on the new equipment we bought.” I said,” Most certainly and lets go watch it.”

She said OK! “But we had better call Jeanne to come watch it with us.”

I said “NO! This is just for us tonight.”

I want to enjoy you by myself after we get horny watching this movie. Besides I bet Jeanne is already in bed playing with herself and we don’t want to disturb that action.

I put the film into the projector and turned off the lights as Bertha lay on the bed with just her bra and panties on. She had left the rest up stair where I had been playing with her. Her crotch was wet and shiny with pussy juice and as I put my hand between her legs she whispered, “take them off with your teeth.”

I put my face between her legs and bit the crotch and pulled ever so slowly making sure I did not get any hair, she raised her hips and assisted me by sliding her fingers in the tops and pushing down.

I flung the panties on the floor and put my face right back in her pussy and licked. She said, ‘aren’t you going too watch the movie.” I just keep licking and slurping her juices. She started to raise her hips off the bed when I reached up and ran one of my fingers between her bra and boob. She just semi sat up and took her bra off and wrapped it around my head like a “red Barren flying hat”. The cups fit over my ears just right and she just laughed.

I stood put and took off my pants and throw them on the floor along with my shirt. She pulled me down on to the bed and rolled me over so my ridged cock was straight in the air.

My eight inches stood at attention and she mounts my penis and impales herself. She is riding my rod as her tits swayed before me. Her puffy nipples are such and incredible turn on that I just reached up and pinched them lightly and fondled her breasts as she rode me. She would sit all the way down smashing my balls against the bed and then raise up till the head of my cock almost popped out of her slippery cunt. All of a sudden she tighten her cunt muscles around my cock and slid down till I though I was going too have my balls inside her. She exploded with suck an orgasm that the juices squirted out of her pussy and ran down my legs. The time this was going on Ii had her nipples in each hand “tweaking” them ever so lightly.

She rolled off me and instantly put her mouth on my cock and tongued it till I came in her mouth. She swallow as much as she could and let the rest leak out and down onto my balls.

We never watched the movie as it was over way before we were. I fell asleep with my head between her breast and her hand on my sticky cock.

We awoke the same way the next morning, really it we very late morning, as Jeanne came down the basement steps. She took one look at us and smiled / laughed. She saw the movie on the projector and asked what movie was playing. I told her, “It was for us three to watch together later.”

Jeanne smiled and said that “we” were to go to visit some friends of hers today.

Bertha asked who?

Jeanne just smiled and said, “Remember that women you met with me last Halloween at the party?” She called and wants to get together to see if we “mesh.”

Bertha asked if I was to go with and Jeanne said, “ most certainly, as he is why she wants to get together. Come to find out this women works at the dry cleaners Jeanne took over since her husband passed away.

Later in the day I left in my car and they in Jeanne’s as not to arouse to many questions. I parked my car at a local restaurant lot and went the rest of the way with them.

I asked about this lady we were to meet and all I got for and answer was, “ you will truly like her and her daughter?”

I said, “daughter!”

They said she had been in high school with me and wanted too see if things could “click.”

I asked the gals, “ are you OK with me going out with someone when we were so active?”

They smiled back and nodded their heads YES!. They informed me that this would keep peoples eyes and minds off me living with Berthas. They did not want people asking to many questions.

When we got to the woman house I was hoping that they were right in doing this.

We sat around and talked for a while till we heard a car drive in the driveway. It was the daughter coming home from the library. As soon as she walked in I remember her from high school. Her mane was Karen and she was two years younger then me and had just graduated from high school last June. I stood up to let her sit in my chair and she said, “sit down as I always sit on the floor.”

We all sat around talking and after a while the mother suggested that us “kids” go into the kitchen and get all of us something too drink.

I got up and held out my hand to assist Karen off the floor. She smiled and took my hand. I also noticed that she gave my crotch a good looking over. As I was helping her up I could not but notice the view down her top. She had firm and medium sized breasts. (Her mother was built like Bertha and Jeanne, LARGE breasts)

When we were in the kitchen we started talking about what I had been doing and how college was. She hoped to go to the junior college locally this next fall term. I said the school was great BUT you had to study harder then in high school. We went back out to the den with the drinks and continued the talking for a short time more.

About 5:30 Her mother told us that she had too leave and go visit her mother at the nursing home. (Her normal Sunday task)

Bertha and Jeanne said they had to leave also, But If I wanted to stay and talk some more, they wee sure that Karen would take me back to my car.

I suggested that she ride with Bertha, Jeanne and me back to my car and then we would got\ get a pizza or something. She liked that idea and her mother agreed.

This was going to be our first of many dates as it turned out.

I got back to Bertha’s house around 10:00 PM.

I park the car in my parent’s garage and walked the few step to Bertha’s back door. I notice the house was all-dark but the door was unlocked. I went in and turned on the hall light to the basement and heard a whirring sound.

I went down the basement and found Bertha and Jeanne watching the movie that we tried to watch the previous night.

Jeanne stood up and kissed me and asked how things went. I said, “ fine, we had a pizza and talked till she asked me to take her home. Bertha stood up and gave me a peck on the check and said,” I smell perfume on you and it is not one of ours.” I smiled and said that we had sat in a booth at the pizza joint and she had sat real close with head on my shoulder. I told them I had been a perfect gentleman and only kissed her goodnight. I also told them I had a date with her next Friday night to go too a movie.

They both said at the same time, “perfect.” We were hoping things would work out for you two so the neighbor would not talk about me living here.

I put my arm around each of the gal’s waists and pulled them into me with a tight squeeze. Bertha said, “Not tonight, you have to go to work in the morning.”

But I replied, “Being with her made me so horny.”

Jeanne patted my crotch and said to Bertha, “Let me suck him off so he can sleep.” Bertha just smiled and nodded her head OK!

Jeanne led me over to my bed and pushed me backwards onto it. She loosened my belt and pulled off my pants. She kneeled down between my legs and gently cupping my balls mounted my semi hard cock with her mouth. My cock instantly got rock hard and she just slowly moved her head up and down. My cock was going in and out of her mouth like a steam engine piston. Bertha came over to the bed and got on all fours hanging her massive boobs over my face. I reached up and raise her blouse so I could suck on the nipples. She let out a scream and lowered her breasts down onto my face. I had not seen Jeanne reach up and put her fingers into Bertha pussy. Bertha raised back off my face and wiggled her ass in the air while Jeanne was suck me and fingering Bertha. All I could do was explode in Jeanne mouth and suck at the same time. Jeanne straighten up after drinking as much of my cum as she could and gave Bertha a kiss to share the um. With that the two ladies lay down net to me and fingered each other to simultaneous climaxes.

The next morning I got up and left them still on the bed sound asleep in each other arms.

About a month later I was going too go out with Karen on a Saturday evening bowling, and as I left Bertha handed me a couple of “rubbers” (that is what they called them in the 1960’s) and said, “just in case you need them. I said, “I know I have been telling you able how we are progressing and all, but I do not think we are quite that far along yet.” She just answered, “ If not tonight or next week, but I am sure she will come to see what you have and put it to good use.” I looked at her funny and went out the door wondering, “What does she know that I do not.”

I picked up Karen about 6:30 PM and headed to the bowling alley. She sat as close to me as she could with the head resting on my shoulder and my arm around her neck. When we go to the alley I got my stuff out of the locker and got her some shoes. I then helped he pick out a proper weight ball. We bowled three games and decided to go get something too eat. We went to one local drive inn’s and parked in the back row. We ordered burgers and fries all the while holding hands and giving each other “evil looks of desire.” While we were waiting for our food she took the first step and leaned over and kissed me while putting her hand on the very top of my leg. I gave her a deep kiss back and raised my hand too met her hanging breast. I at that time notice she must have taken her bra off when she went too the ladies room at the bowling alley. She kissed me harder as I squeezed her breast. She straighten up just as the food was getting too the car. We eat with smiles on our faces and wild thoughts running through our heads. I do not think I tasted the food at all, but could only think of her thought at that ever moment.

Just as we were about to leave a car pulled in that had some of her friends in it. She waved to them and said she wanted to say a quick hello.

I shut off the engine and waited for her to come back. When she did she was in tears and was all upset. Asked what was wrong?

She said that one of the girls that she was going to go to school with had just found out the her mother was going to leave her father and there would be no money for her to go to school on. That ruined the rest of the night for us.

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