My First Prostate Massage
It was a warm summer afternoon and I had just finished an airshift at the Country station where I worked in Texas, when a co-worker came up and asked me to accompany her to a function our station was sponsoring. The event was at a local club where Gary Stewart was appearing and the co-worker was what is known as a BBW and she was married, but her husband was in the Marine Corps and stationed in California. And she had four c***dren at home ranging in age from 7 to 14. Now all the girls I'd gone out with before had been petite (and somewhat passive and empty headed) and I had never been with or gone out with a a 'plus-sized' married woman before...that was taboo in my book! So, I declined her offer.
"Aw, c'mon" she said. "It'll be fun...besides, I need an e****t...I can't go to a club all by myself."
She and I had develped a strong friendship at work so I figured, "What the hell". I mean, she was a friend, right, and I'd just be doing her a favor. What would be the harm. Boy, was I mistaken!
I arrived at her house at the appointed time and, wonder of wonders, she was ready! None of the "Make yourself comfortable...I'll be ready in a few minutes" I was impressed. We got to the club and greeted several other people we knew from the radio station and she ordered us both drinks. Ordinarily, I don't drink, but I accepted the beverage the waitress brought and it was pretty good....delicious in fact.
"What is this?" I inquired.
"It's called a pina colada", she replied.
I sucked it down rather quickly and ordered another, not realizing it had a double shot of rum. Before I knew it, the concert was over and I'd put away four of those pina colada 'things' and wasn't feeling any pain.
"Are you ready to leave" I asked.
"Sure," she said. "Want me to drive?"
"No, that's okay", I said. I wasn't thinking clearly or I would have, should have, handed her the keys.
I made it to her house finally and pulled into the driveway. As I look back I realize it was foolhardy (and dangerous) to drive while I was fucked up on all that alcohol, but I'd gotten us there without incident. As I was preparing to do the gentlemanly thing and walk her to the door she said, "Hey?" As I turned to see what was up, she kissed me.
"What was that for?" I asked.
"Well, you took me out for a good time tonight and I just did what any girl would do when a guy brings her home."
"Oh," I said. "Okay."
Then, in an exaggerated Southern drawl, she said, "Please, suh, can I have more?"
Innocently I said, "Sure." So I kissed her again, only this time she snaked her tongue in my mouth.
"Uh...Hon...I don't think this is a good idea."
"Didn't you like it?" she asked.
"That's just it...I think I liked it a little too much"!
"Well, then, let's do it again!"
She kissed me again, with more tongue, and I felt my dick start to get hard in my jeans. This was absolutely not going the way I'd envisioned it in my mind. It was supposed to just be two friends going to a music venue and then each to our respective homes. "Sweetie"," I said, "We need to stop his."
"Why?" She smiled. "I'm having a good time. This is fun!"
"A little too much fun I think. If we keep going one of us will be in trouble".
"Stuff and nonsense" she said. "All we did was kiss."
"Yeah", I replied, remembering my dick that was growing stiffer by the minute. "But your kisses are affecting me in a way that's not so good."
"Oh, how's that? she queried.
"You don't wanna know", I said.
"Yes I do", she shot back.
"Okay', I said, "But it'd be better if I show you" and I put her hand on my crotch.
"Ooooh", she grinned.
"See what I mean?" I said.
"No, I don't see at all. I thought you said you were gonna show me."
"You're serious, aren't you?" I asked.
"Serious as a heart attack," she said. "So, show it to me."
I reached down and unzipped my pants and took out my stiffening manhood and stroked it a couple of times.
"Mmmm', she cooed, "I've always wanted to see that."
"A man's dick? "Dear Lady, you've got four k**s, for heaven's sake".
"No...I've always wanted to watch a man jack off...I think about it sometimes when I play with myself."
"You do that? I thought women didn't do that...only guys." I was very young and naive.
"Honey", she responded, "you've got a lot to learn. Here let me help you", and with that she took my dick in her hand and leaned over and put it in her mouth. God, it felt so good as her head started bobbing up and down on my dick. She was actually masturbating me with her lips and tongue. Before long, she quit jacking me off with her mouth as I had started to move my cock in and out of her mouth, actually face fucking her with my thrusts.
"Let's get in my back seat", I prompted her.
She needed no further encouragement and crawled from the front seat to the back where I quickly slipped out of my jeans.
"Take your pants off", I said. Off came the pants...and the panties. As she parted her legs I was thrilled to see the 'furry triangle'...a modest covering of light, curly brown hair over two moist, juicy pussy lips. Quick as a wink I dove in, tongue first and began to lick up and down her slit, pausing now and then to suckle her clit which was starting to get erect. "No man has ever done that to me before."
"Do you want me to stop?" I questioned.
"God, no!" she responded. "I've thought about it for years and even fantasized about it while I was fingering myself, but my husband never did it and I never pressed the issue...but I know now what I was missing. I'm gonna cum!"
I continued doing what I love to do and she came while I sucked her off.
"Come here and give me some more of that dick," she pleaded. I crawled up so my cock was positioned above her mouth and, once again, she started to suck my length and buried her face in my pubic hair. Then she did something totally unexpected...she put her fingers in her wet cunt and masturbated in front of me. A real turn on for this guy. Suddenly, she took her fingers out and slipped the slippery middle one up my ass...all the way. I had never had a woman do that before, ever, and my cock actually felt like it got harder.
"What are you doing", I asked in surprise.
"I'm finger fucking your ass....but if you don't want me to...."
"No, no! I want you to...I guess I just wasn't ready for it...but don't stop. It feels really good. I have to warn you, though, if you keep doing it I'm gonna cum in your mouth."
"I hope so," she said.
I asked her, "Do you spit or swallow?"
"A lady never spits", she grinned.
Within a minute or so my dick started spurting thick jets of cum down her throat and she greedily drank it all, not missing a drop. She continued to nurse my softening cock, caressing my balls and rubbing my tight pucker that had been recently penetrated and before long I found myself starting to respond to her ministrations. We had sex for another couple of hours in various positions, but I could never get the thought of her butt fucking me with her finger out of my mind. That planted the seed of my fascination with what has become known as 'prostate massage' and an interest in a man's asshole as well as a woman's. We spent the next twelve years exploring our fantasies and each other's bodies and had a wonderful time doing it. I haven't seen her for several years but she taught me about cornholing a man with her fingers and I taught her how to enjoy a good cornhole with a hard dick. I will always` be grateful for her curiousity and openess regarding the pleasures of sex.