My Masturbation Journey

I didn't have a serious girlfriend until my senior year of high school.  We were very much in love, but it took several months of painstaking exploration and persuasion on my part before we reached the point of satisfying each other sexually. This was the late 1950s, before the pill, so intercourse was out of the question. But step by step, we discovered the joys of touching each other’s bodies.  The process was enhanced by the bench seats in 1950’s sedans, which allowed a great deal of contact in the front seat.  My left hand on her shoulder as we kissed put my forearm on her breast, and my hand slowly found its way to her erect nipples, first through her clothes, then inside the bra.  Once we both acknowledged what was going on, I explained how stressful it was for me to get so worked up and explained how I needed to “relieve myself” when I got home.  I then “adjusted” my boner in my pants and asked her to feel it.  Of course, I didn’t stop her in time and came in my pants.  After that, we quickly progressed to fingering and hand jobs, and I brought her to her first orgasm. When I went away to college the next year, she learned to satisfy herself. Her Southern Baptist upbringing prohibited "touching herself down there," but there weren't any rules against humping her pillow or rubbing with the washcloth in the bathtub!  Once I worked up the nerve to buy condoms, we liked to lie on the front seat and put my penis between her thighs, which gave both of us enough stimulation to get off.  The bench seat went back far enough that I could kneel on the floor and give her cunnilingus.

A later girlfriend was an eager student of the art of masturbation and became a passionate and multi-orgasmic partner. As we began dating and making out during summer vacation, she stopped my first attempt to caress her breast with an enticing, “Not yet.”  Of course, that kept me coming back.  In fairly short order, we were masturbating each other on every date.  Once again, I was the agent of her first orgasm.  I particularly remember one night when we had gotten each other off in the car.  As I kissed her goodnight on the front porch of her house, I could tell she was not finished and asked her if she wanted to go again.  As discreetly as possible, I slipped my hand under her skirt and through the leg of her panties and rubbed her to another climax.  I had to jack off again when I got home!  When the time came for us to go back to our separate colleges, we exchanged passionate (and rather explicit) letters about what we wished we could do with each other.  I urged her to masturbate to relieve the tension, something she had not done before.  I recommended several methods:  rubbing her pussy on the mattress, humping her pillow, using her hand.  She wrote back that she tried them all and came three times!  We began to exchange letters describing our masturbatory activities, eventually agreeing to try to do it every night at the same time.  The first week, she wrote that my letter got her so excited that she did it in the afternoon.  When I asked her how she did it, she wrote back, “I just sat on the bed, lifted up my skirt, put my hand in my panties, and rubbed until I reached a climax.”  If her roommate was around, she took a shower: “I just let the water fall on my breasts until I climaxed.”  One night, she wrote, she came 12 times, once from nipple stimulation alone. She came to my school during a vacation, and my roommate gave us privacy.  Naked in my bed, I brought her off with my tongue.  We tried phone sex a couple of times, but the cost of long distance was prohibitive.  Eventually, the distance between our schools was too great to overcome, and we could not sustain the relationship.  Of course, I still jack off to the memories.