My first time jacking with Jill
(Actually this is about 'Jill' (Ramona) jacking me and showing me how to pleasure her. This took place in about 1947 when I was 14 years old.)
I didn't notice Ramona until my second year in Junior High School when her locker in the hallway was just a few feet from mine.
Several times I saw her watching me and smiling. Then she began to walk by me and smile more and sometimes say, 'Hi'. 'Just a classmate being friendly' I thought to myself as I said, 'Hi' to her.
Near the end of our school day every Friday the entire student body would assemble in the auditorium. Sometimes it was to be addressed by some of the faculty, sometimes we had entertainers such as magicians, but frequently we watched a movie. Somehow Ramona always found me and sat next to me. She would rub shoulders with me and smile, and if the lights were dimmed for a movie she would reach over and hold my hand, or place her hand on my thigh and gently massage it. She never groped my crotch. She just tenderly stroked my inner thigh. When the lights came back on and we were dismissed she would smile at me and say, 'That was fun!'........and then leave.
The last week, or weeks, of school before summer vacation each class would hold a class dance. When the date of our class dance was announced that year Ramona came over to my locker and asked me if I was going to attend the dance. When I told her I wouldn't because I didn't know how to dance she frowned, and then her face brightened and she said she would teach me how to dance so I could go with her as my date. I asked her when she would TRY to teach me, and she wrote her phone number on a slip of paper, gave it to me, and told me to call her Saturday.
Mid-morning on Saturday I decided to call her and ask her when and where she wanted to give me my dance lesson. She said that she would catch the bus near her home and come to mine, but that the weather was so warm that it might be best if she waited until after the sun went down. Then she asked if I had a record player and some records with slow-dance music. I told her I had neither one, to which she replied that she had a portable record player and some good records that she would bring with her. We then set a time for her to arrive at my home.
When she arrived I met her at the door, invited her in, and asked if she would like something cool to drink before we plugged in the record play and got started. She asked what I had, and I told her I had some lemonade, milk from our cow, and water in the refrigerator. She asked for a glass of milk which I brought to her along with a glass of lemonade for myself. We chatted a bit about school and one thing or another as we enjoyed about half of our drinks and then she asked if perhaps we should start some music playing and 'get in a dancing mood'. I said that was OK with me, so she selected several records and stacked them on the spindle and turned the record player on.
Then she beckoned for me to stand up and come to her. When I did she tried to explain, with demonstrations, a few simple dance steps suitable for slow dancing. She showed me how to hold her and then we began to move to the music.....I should say I TRIED to move to the music but wasn't doing very well with my feet. When I apologized she told me to hold her closer and then I could feel her body move and I could just follow her body with mine.
After a few minutes of that, she exclaimed, 'I'm HOT!'. Well, it was a hot day, we had no air conditioning, and I was naive. I had no idea she meant anything other than that the temperature was hot. I told her I would open all the windows in our living room, and I did. Then we went back to my dancing lesson.
After several more minutes she seemed to sag against my body and said that she was hotter now than she was before. I was just joking and embarrassed a bit when I responded that she might be cooler if she took some of her clothing off. Without hesitation she removed her blouse and skirt and stood before me in just her white cotton bra and panties with a grin on her face. Then she said that I wasn't being fair by still being fully clothed and that I would feel better if I took some of my clothing off also.
This situation was becoming more interesting to me.
I had never seen a girl in just her underwear, and I had never had a girl see me in mine, but I removed my shirt and trousers just to be fair to her. We both then kicked our shoes off and resumed our dancing positions.
Soon, she had one leg between mine and was using her upper thigh to apply pressure to my crotch while her crotch was pressing against my thigh and moving in rhythm to the beat of the music. I was a virgin, but I had a good idea where this was going and my cock got hard.
She sensed my cock pressing into her belly, stopped moving momentarily, looked at me, smiled, kissed me on my lips and said, 'That feels good to me, how about you?'
I told her that as long as it was good for her it was good for me too.
After only a few more steps she said she thought we should take a break and lie down to rest a while if I would. I said, 'Sure', and she asked which way we should go to find a bedroom.
The best bed in our house was in my parents' bedroom, so I led her there and told her it was their bedroom. She asked where my parents were, and I told her they were out of town for a few days. Then I happened to think of her parents and what time she might have to get back home. When I asked about her parents she said they had taken a flight to Cuba to visit with relatives there so she could spend the night if I would like her to. I smiled, and kissed her to give her my answer.
I opened the windows in the bedroom which had better ventilation because it was a corner room. Then we lay down on the bed and smiled at one another as we began to chat. She commented that the milk I gave her tasted better than the milk her parents bought at the grocery. Then she asked if I milk our cow. I said that sometimes I do. Then she wanted to know how I get milk out of our cow. I explained how you have to hold the cow's teats and sort of squeeze the milk out of her bag by stroking down on her teats. She said that sounded like it would be a fun thing to do. Then she reached over and pulled my cock out of my boxer shorts and began to squeeze and stroke it as she asked if that was how to milk, and did it feel good to me? About all I could mutter at that time was a low moaning, 'YESSSSSSSSSSssssssssssssss'.
She asked if I had ever sucked on the cow's teats, and I said I hadn't. Then she reached behind her back, unsnapped her bra, and wriggled it off her shoulders after which she asked if I would like to suck on her nipples. Rather than replying I pulled her close to me and began sucking gently on one nipple and then the other while massaging them with my tongue. She began writhing around pressing her lower body against mine and moaning with delight. At the same time she kept her hand on my now quivering cock, massaging its engorged head and stroking up and down its shaft.
Ramona must have sensed I was near to having an orgasm because she released my cock and rolled away from my lips on her small but delicious breasts. We just lay there breathing heavily for a few minutes.
Then she removed her panties and my shorts and rolled back to press her hot body against mine.
She took one of my hands and stuck my middle finger between her lips and sucked on it for a few seconds. Her other hand explored my cock and balls, as she licked and sucked on my nipples in between deep throat kisses with me. Then she said she wanted to milk my cock, asked me it that was OK with me. Of course I said it was OK. Then she took one of my hands and placed it on her fuzzy mound and pressed it against the lips of her warm, moist, pussy and asked me to rub it, so I did. Then she guided my fingers to her very prominent hot, throbbing, erect clit and asked me to massage it gently as she stroked my cock and massaged my balls while we enjoyed deep throat kisses with one another allowing us to not only smell the lustful desire in the other's breath, but to taste it as well.
This was an entirely new exotic and erotic experience for me.....a very blissful one, as Ramona later told me that it was for her also.
We pleasured one another time and time again that night. Our spunk covered one another and the sheet under us until it was slippery just to lie on.
The next morning Ramona helped me wash and dry the sheet and re-make the bed before she had a bite to eat and then went home.