[When I was working on my doctoral disstertation on "Introductions To Sex" I posted a note on the student union bulletin board solicitating "anonymous" stories about first time sexual experiences. I was amazed at the variety of experiences. Here are a couple short stories I received. The names and other identifying things have been changed.]
Nick's First Time -
My "First Time" was with my mother. I'm a nerd and never had a girl friend until college. But even nerds masturbate and let me tell you, I masturbated a lot. That's all I did until I came home from college freshman year for Christmas.
Something changed those first few months away from home. On Christmas Eve I was lying on the couch watching TV when I saw my mother with her vacuum cleaner wearing only panties and a cut-off tee shirt.
I've seen my mother doing the housework in her panties for as long as I could remember and never thought much about it. That morning was different though. When I saw my mother in her panties my dick started reaching for the ceiling.
I don't know what came over me but when my mother vacuumed between the couch and the coffee table I reached up and ran my hand between her legs. She stopped vacuuming and just stood there looking at me while I smiled apologetically, not moving my hand.
She said, "You shouldn't be doing that." She pushed my hand away, pulled her panties up tight and continued vacuuming.
About 15 minutes later I went into the kitchen I saw her leaning up against the handle of the vacuum cleaner almost like she was riding one of those old stick horses.
When she heard me she immediately stepped back from the vacuum handle and said, "You shouldn't have seen that." She looked sad and mournful as she said, "I miss your dad so much."
That night about an hour after I went to bed I felt my mother climb into bed with me and spoon me from the rear. She wrapped her arms around me and whispered in my ear, "I love you." I dozed off.
I woke up on Christmas morning dreaming about cumming. I thought it was just another wet dream until I felt my mother's hand squeezing my cock.
When I stirred she woke up and quickly realized she had cum all over her hand. "Oh, God!" she exclaimed. "I'm sorry, I never meant for that to happen," but she kept her hand wrapped tightly around my cock. And it was getting hard again.
I rolled over facing her and reached down between her legs. This was my first time with a woman but I'd seen enough porn on the internet to know where to find her clit.
I dipped two fingers in her wet pussy then slowly pulled them out finding her clit. She let out a small whimper and rolled on her back spreading her legs. She kept squeezing my cock nearly ripping it off as she climaxed.
"You shouldn't be doing that," she said as she let her body relax. She still had a good grip on my dick. She pushed me on my back and straddled me finally letting go of my cock when it was firmly inserted in her vagina.
The feeling was amazing. I've masturbated thousands of times but that first feeling of a warm wet pussy enveloping my cock is something I will never forget.
After my dick finally shriveled up and popped out of her pussy she put her head on my shoulder and whispered, "I shouldn't be doing that."