First Vaginal Orgasm -- Ladies, Listen Up!
So much of my life has been spent trying to lose the baggage that held me back sexually. I was determined from my teen years to find a way to discover the sexual being I was meant to be. This basically meant that I had to assume everything my parents ever told me was a lie. Of course, I read everything I could get my hands on about sex, sexuality, sexual technique, statistics about arousal and orgasm, and volumes of other people's fantasies. Still, I had never been able to cum just from having a cock or a dildo inside me. It frustrated the heck out of me. So many men seemed disgusted with me because I could not manage to do this; they acted as though I had cheated them, even though I had given them all that I to give, and then some. It wasn't enough that I enjoyed what we did, and came when they sucked my clit; they felt I was holding something back if I couldn't cum while fucking. Unfortunately, making me feel inadequate didn't help the situation at all.
I thought that somehow, I would just stumble onto the answer by trial and error, which was one of the chief ways I had learned about sex in the first place. I tried being promiscuous in order to get a lot of experiences, but I still had not found the answer, and I even tried 10 years of celibacy, swearing that I would not have another sexual encounter until I had lost every bit of my emotional baggage and was in a position to truly enjoy it.
After 10 years of no sex at all except what my fingers and my vibrators could provide, I woke up one morning at age 34 and suddenly sex made sense to me. I kid you not. I woke up feeling no guilt, no fear, and very much alive! I probably had some incredibly profound dream that I did not remember, prompting me to finally put the pieces together and wake up sexually sane. I also probably got my hormones on straight for the first time in my life, and emerged as the lusty woman I have always been underneath all the baggage.
I decided I needed a boyfriend in order to test out my feeling of sexual wholeness. I had not come out to myself as a bisexual, so I wasn't inclined to search for a girlfriend just then; that would come a couple of years later. I had been so totally out of the loop for so very long that I didn't have a clue where to begin looking for a man to date.
Fortunately, I had been working on my Bachelors degree (the second attempt), so I was in college and surrounded by men. Unfortunately, I was nearly 35, a BBW, and most of them were slender and 10 or 15 years younger than I was. None of them ever gave me the tiniest hint that he was attracted to me; so my university seemed to be terribly fallow ground.
Except for this one guy... Let's call him Ralph. He was only about 9 years younger than I was. I volunteered as a tutor /helper for disabled students, and he was visually impaired. A Southern gentleman he seemed to me, single, extremely intelligent and with a good sense of humor. He was not the best-looking man in the world, but he had beautiful, unearthly eyes that flashed silvery in certain angles of light and changed color with his emotions; his hair was long, a thick, black, unruly mane coursing down his back. I was hooked.
We chatted as I helped him find his classes; I began to sense that his interest in me might be reciprocated. Eventually, he asked me out on a date, and I glowingly accepted. Of course, I drove! I can't remember where we went or what we did, but I do recall we ended up at my apartment. We talked and talked; he smoked on my patio, and we discussed everything from God to politics and back to God again. Ralph finally leaned over and kissed me; I kissed him back, and he began to unbutton my blouse.
"Wait a second. Aren't we moving kind of fast?" I asked him. He was not very pleased with the question, so we talked a little more about the implications of sex on a first date. What we seemed to conclude is that we were both adults; neither of us was a virgin; and since we both wanted each other, there was no compelling reason to go through the mind games of playing hard to get.
So we stripped, and we screwed, and we got into every position we could think of. At the end of it, he asked me about orgasms, which I had only managed to have when he went down on me. He wanted very much for me to have an orgasm while he was inside of me. I told him that had never happened, and I had come to terms with it by enjoying sex to the fullest, appreciating all the sensations I was having, and if I happened to have an orgasm that way, fine, and if I didn't, I would have a great time anyway. What usually happened to me all of my sexual life was that I would get close to orgasm while fucking, closer and closer and closer, but I never quite found the secret of how to leap over that threshold of pleasure, into my full release. I enjoyed it anyway, and most men were good about going down on me to give me the release I craved. Either that, or there was always my fingers or vibrator after the guy left... so in my mind, I was doing OK.
The real problem was that I believed that the right man, with the right penis, would somehow magically grant me an orgasm. Sort of like the princess waiting alone in the tower for Prince Charming to rescue her. I didn't realize that I had a lot of control over my own cumming... and responsibility for it as well.
He wasn't content with my just "feeling good," and kept reminding me that I really should have a cock-fucking orgasm. I kept letting him know that I was enjoying sex with him, and not to worry about it. But he kept dropping hints that he might soon become disinterested if I didn't cum soon. Knowing what I know now, I would have dropped him like a stone, but I was a little lonely, more than a little desperate, and determined after 10 years that I would have a boyfriend, and I would fill in all the gaps that had existed in my life up to then.