My father left when I was 12 years old and shortly after that my Godmother Betty began to take a special interest in me. She stopped at our house often, brought meals and took me out to plays and concerts. Betty was about 40 at the time, a large woman with huge voluptuous breasts. She was five years older than my mother and treated her like a little sister.
My general impression was that Betty was a lesbian, since she lived with a woman and my mother always avoided questions about her, including why she never got married. By the time I was 13 I had begun to have fantasies about Betty and would always try to find ways to see her in her underwear or her night clothing. I was always trying to peek down her cleavage and she often caught me doing it, but seemed amused by it.
For my 15th birthday, Betty offered to take me on an overnight trip to Chicago by train. She was going to introduce me to all of the big museums in the city. Betty was a cultured person and worked as a director of the small town philharmonic where we lived.
The train left my town at 6:00 AM and it was to a six-hour ride to Chicago. I was surprised when Betty told me that she had reserved a small sleeping compartment so that we could rest and arrive fresh in the late afternoon. I was even more surprised to see the compartment. It was tiny, being barely larger than a single bed.
Betty made the two seats into one flat surface and then spread a blanket over it. Closing the door she told me that we should get out of some of our clothing so that we could rest. With that she turned and took off her dress. Then she asked me to unsnap her bra after which she twisted it off pulling it up and out of her slip. Her breasts were clearly visible through the loose nylon of her slip and her nipples seemed to poke out and be bigger than I had ever imagined, clearly outlined through the fabric.
She curled into the corner of the berth and told me to take off my pants and shirt. I was so embarrassed, since I knew that I had a massive erection, but she insisted. I turned away to hide it from her and she laughed. 'Have a little tent problem there?' She chuckled.
Then she said, 'Don't worry I've seen them before.'
I got on the bed next to her and she pulled me closer to her even though I was facing away.
'Turn this way.' She said gently, and told me to put my face against her. As I did she suggested, 'Maybe you can get to sleep.'
I was afraid to get close because of my problem, but Betty pulled herself up and pushed my face against her. I was nuzzling against her breasts and she was rubbing the back of my neck and stroking my hair.
'Is that better?' She asked.
As the train rumbled along the tracks my erection grew and slowly I relaxed, letting myself melt into her. Suddenly I realized that Betty had released her breasts from her slip and that my nuzzling had led me almost to a nipple.
Go ahead and nurse she whispered. Pretend you are a baby. I kissed and licked them, sucking her nipple. As I did I began humping against her leg.
'Go ahead!' She moaned, 'Let yourself go.'
Her breathing quickened and I went off, blasting cum through my underpants, all over myself. She said I must have been tense and reached down, taking my still firm penis out of my underpants. She examined it and said 'Its so big for a 15 year old.'
Then she put it back in my pants pushed me onto my back, before crawling on top of me. Balancing herself on her elbows she pressed her vagina against my penis and began rocking back and forth, as she whispered, 'My turn!'
She ground away for several minutes, gasping and moaning as she continued. She got much wetter and I could feel her vagina against my penis, even though we both had out underpants on. Then she raised herself on her fists made a series of quick grinding strokes and collapsed onto me. She had cum and I was hard as a rock again.
'Go ahead. Masturbate yourself.' She whispered, as she rolled away to the side, saying, 'Masturbate yourself, you are hot again and I want to see it.'
I did and as I came close to another orgasm she began playing with herself. We both came a second time and fell asleep holding each other. We had a wonderful time in Chicago.