My First Time

Story Info
His neighbor teaches him.
2.3k words
4.27
158.3k
9
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
gamma33
gamma33
100 Followers

This is the story, actually, the factual relation of my first sexual relations with a woman. I was well past my eighteenth birthday when it happened. We, my mother, father and me, lived on the outskirts of a small Midwestern town, right in the bible belt. I was home schooled by my mother in the hours that she wasn't at church, so that I had no contact with others my age.

Father was not as religious as she, only going to church on Sundays, while I attended Sunday School in the church basement where Mrs. Saxton, the only other woman I'd had contact with, the teacher, would hold forth for about an hour before we were shoo'd upstairs to join our parents. There was another boy in Sunday School, but he was much younger than me, Johnny Desmon, about ten years old..

Never a curse word was heard in our house, fathers strongest word was 'Dang!' and mother would chastise him for using that word. Apparently it was permissible for the preacher, The Reverend Snodgras, to use the words 'hell' and 'damn', but only in his sermons, preaching for two or three hours without letup during services. I know father would often go to sleep during the orations Mother made sure I remained awake.

It had been two years earlier that I suffered my first 'wet dream' and it scared me something awful. Somehow knowing that it was 'wrong', I hid my bedsheet and pajama bottoms from mother until wash day and throwing them into the washing machine as she was loading it. Somehow, I managed to control myself after that, but found that when my penis did grow longer and hard, there was a most pleasurable feeling when, with a little help from my right hand, I could shoot a white paste into the palm of my other hand.

My innocence ended during the summer of 1982. Mrs. Mullens, our next door neighbor died in early spring of the previous year, leaving her husband, Mr. Jonas Mullen alone. Mother took it upon herself to help Mr. Mullen in his housework, even doing his laundry on laundry day. Then, in late spring, early summer, Mr. Mullen's niece, Gertrude, moved into the house. She had lived in Chicago until a divorce from her husband, and having nowhere to go, came to live with her uncle. .

Gertrude was a rather tall, thin woman of about forty, her black hair beginning to streak with white. She had a rather pleasant face, seemingly to always have a smile, full lips, usually bright red with lipstick, something my mother didn't approve of, wide set, nearly oriental almond shaped, deep blue eyes, and a rather thin, somewhat longish, nose.

Of course, she took over all of the household chores my mother had been performing before she came. On occasion I would encounter her on the street when she had gone shopping, but, other than than we had no contact. Like Mr. Mullen, she never attended church, another thing of which mother didn't approve.

In December, just before Christmas, Mr. Mullen became quite ill and right after the first of the new year, passed away. At first we wondered what would happen to Gertrude, but soon learned that Mr. Mullen had signed the house over to her months before and, in addition, had left her, as mother put it, a rather tidy sum of money. He had always been very frugal and we never realized just how much money he had.

While Gertrude had always been very conservative in her dress, you can imagine mother's reaction when, on a rather warm spring day, she left her home to go shopping, dressed in shorts. Not only were they shorts, they were VERY short, displaying from behind, the lower parts of her buttocks. While mothers face became crimson and she turned away, father gave a low whistle and, under his breath, exclaimed, "Look at the legs on her!" Mother exploded. "Franklin Adams, shame on you, and right in front of the boy!" Father chuckled. "Marian, he's got to learn someday. You can't keep him a virgin all his life."

Indeed, she did have very attractive legs, long and shapely and they were accented by the high heeled shoes she wore. I had never seen her wear high heels before, always she had worn flat heeled shoes and, of course, had never seen her legs like this. For some reason, my penis began to grow and get hard. I sneaked away to our bathroom and massaged it till it spurted out that white paste again.

It was a week or so later that it happened. I was in our side yard, cutting the grass, when Gertrude appeared in her yard, again in her short shorts, topped with a white shirt, the material so thin I could see her breasts with their coral tipped nipples. I know I turned red as a beet and became slack jawed and my penis jumped to its full growth, causing a bulge in the denim pants I was wearing.

"Why, Andrew, I believe you like my clothing," she laughed at me. Foolishly, all I could do was to repeat my father's observation. "You've got very nice legs, Miss Gertrude." With her eyes fixed on the bulge in my pants, she replied, "And it looks like you have a very nice third leg, Andy. You'll have to show it to me sometime. And, don't call me 'Miss Gertrude', call me Trudy, please." With that she turned and returned to her house.

I left the mower where it was and dashed into the house, headed for the bathroom, I had to relieve the pressure in my penis. Mother stopped me as I entered the house, asking, "Where are you going in such a hurry, Andrew?"

I...uh...I need to go to the bathroom, mother," leaving her with a perplexed look on her face as I passed her. Once safely in the bathroom, the door locked, I whipped out my turgid penis, and after spitting on my right hand, began to rigorously stroke it. It took several minutes before the feeling of euphoria came over me and the white paste spurted, not once, but, three times. My knees grew weak and I nearly fell, catching myself on the wash stand.

When I had recovered, I flushed the toilet and then washed the paste off my hand, returning thru the kitchen, smiling at mother as I passed, and outside again, to finish mowing.

I was putting the lawn mower away in the shed at the back corner of our yard when Gertrude appeared again. She came up to me and softly said, "Feel better after you jacked off?" I looked at her, I had never heard the term 'jacked off' and she saw the question on my face. "Didn't you pump your cock till you came?" When I still had a quizical look on my face, she asked, "Andy, are you a virgin?" I shrugged. "I guess so, at least that's what father said." It was her turn to look surprised. "Well, we'll have to take care of that, Andy. Don't you go to school?"

I explained to her how I was home schooled except for Sunday School and Mrs. Saxton was my teacher there. "Mother was a school teacher before she married my father. She doesn't like schools, except for church school. She's very friendly with Mrs. Saxton too.." Then I asked her, "What's jacked off?"

She laughed. "What you did with your prick to make you cum, silly. Don't you know anything?" She looked down at my crotch, where my penis was again beginning to grow. "Open your pants, Andy. Show me what you've got hidden in there."

"Oh, I shouldn't. That wouldn't be nice," I answered quickly. But she wouldn't take 'no' for answer and moved to touch my growing penis through the denim material. Of course her touch caused a rapid hardening, making it most uncomfortable. "Come on, Andy, let me see it. I'll show you my cunny if you do." Stupidly I asked, "What's your cunny, Miss Trudy."

"Jeezus, Andy, my cunt, my pussy, my quim. my gash. Don't you know anything at all?"

Now, besides being uncomfortable in my pants, I was becoming completely embarrassed in not knowing what she was talking about. "Come on, into the shed, Andy. We can both take our pants off and look at each other. You've got a lot to learn." Dumbly, I followed her inside the shed and she began to unfasten the waist band of her shorts. "Come on, Andy, get those pants off."

Slowly I began to follow her lead, unbuttoning and pushing the zipper fly down. While I had underpants on, Gertrude wore none and I was suddenly gazing at her hairy crotch. My penis poked its way thru the fly in my underwear, as though to also gaze. Miss Trudy ran her fingers through the hair, moving it so I could see a slit peeking through the hair. "There now, Andy, there's my cunny, my cunt, and it's getting very hungry for your beautiful cock and I think you'd better feed it." "Huh?" was all I could say.

She jumped up onto the work bench my father had built, sitting right on the edge, her legs splayed. "Come here, Andy, feed my cunny, it's awful hungry." With my pants around my ankles, I shuffled towards her and when I was within arms reach, she grabbed my arms and pulled me close to her. Somehow my penis had penetrated her cunny, sliding right inside her. It felt wonderful, much better than when I'd hold it in my hand. "Do it, Andy, fuck me now. Cum in me, feed my cunny."

I tried to pull away but the wonderful feeling on my penis made me push it back inside and I just kept doing it over and over. "That's it, Andy, do it hard, drive that prick in deep. Jeezus! I think you're gonna make me cum. Faster, do it faster." I had my hands on her waist now, holding myself to keep from coming all the way out of her.

Gertrude's head was thrown back and she was breathing heavily through her open mouth. "God, Andy, I'm gonna cum," she sobbed. Her cunny seemed to be gripping my penis as I continued thrusting in and out. Then I felt it. My penis was pumping my white paste into her and, without knowing why, I pushed into her as hard and as deep as I could, holding myself there as more and more flowed from my penis.

"HARLOT! What are you doing to my boy?" Mother was standing in the doorway of the shed, her eyes blazing, drool running from the corner of her mouth. She looked like a crazed woman, and at that moment she was. "GET AWAY FROM HIM," she screamed as she reached out to grab my arm, yanking me away from Gertrude and out through the shed door. With my pants around my ankles, I was not able to walk, let alone, run, I fell to the ground.

Gertrude had began laughing boisterously in the midst of all the commotion, pointing a finger at mother. "Some teacher you are, Andy doesn't even know what a cunt is, doesn't even know about fucking. What? Are you saving him for yourself?" Mother's jaw dropped as she heard those words. "Get away, you...you...Jezebel. I know, the devil himself sent you to corrupt my beautiful child."

By this time, I managed to regain my feet but before I could pull my pants up, mother began pulling me towards our house. I managed to stay on my feet this time, hopping along behind her, my now flaccid penis, bobbing up and down with each hop..

Before we had made it half way to the back door, it suddenly opened and father emerged. "What the Hell?" he exclaimed. He had cursed, and loudly too. "For god's sake, Marian, what are you doing?" She appeared to be speechless hearing her husbands words, stopping her race towards our house. "Andrew, what's going on," father asked.

"Father, Miss Trudy and me, we were just showing each other our,,,uh... privates and mother found us in the shed." At that moment, Gertrude appeared from inside the shed, her shorts back where they should be. She was still laughing loudly. "Frank," she said, this poor boy doesn't know anything. I just took his cherry, he isn't a virgin any more."

Mother found her voice then and screamed at my father, "Franklin, they were fornicating. She's ruined my sweet boy." Tears were streaming down her face. "What am I going to do now?"

To my relief, fathers face broke out in a broad grin. "Good for him," he said softly. "It's high time he learned what that thing is for. Lord knows I haven't been a good teacher; you've always said it wasn't time. You only give me a chance to use mine so seldom for all these years. Now let go of him so he can at least pull his pants up and stop hopping around like a rabbit."

Mother released her grip on my arm and collapsed to the ground, sobbing loudly. "What will people say? How can I tell Reverend Snodgras what a failure I've been. Help me, Franklin."

"Marian, the only way I can help you is to do just what Andrew just did with Gertrude; fuck you good. It's about time I had a good piece of ass. Gertrude, take him back in the shed and do, uh, whatever, while I take Marian in the house and...well...see if I can do...whatever."

And that's how it happened. Gertrude, Trudy, took me back into the shed and proceeded to teach me what my penis...uh...cock...was for. After the second time, she had to suck it in her mouth to get it big and hard for a third... uh, fuck.

Mother stopped spending so much time at church after that and I noticed that she and father seemed to be smiling a lot more. I guess the 'whatever' worked for them.

gamma33
gamma33
100 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
AnonymousAnonymousalmost 10 years ago
what a comedy

what a comedy

AnonymousAnonymousover 16 years ago

WOULD LIKE TO SEE MORE LIKE THIS

don87654don87654over 18 years ago
Hilarious!

My dick got hard and I practically died laughing, because I lost my virginity nearly the same way, 45 years ago alongside a river in central Idaho when in a skinnydipping party at night and drinking lots of beer, away from home and strict parents for the first time.

AnonymousAnonymousover 18 years ago
Nice story

Humorous and sexy with a great ending. Thank You. Ronnie W.

AnonymousAnonymousover 18 years ago
loved it

loved it laughed my ass off

Share this Story

Similar Stories

Milf for Hire! Nick finds out what his friend's mother really does for work.in Mature
Neighborhood Milf Life long dream fulfilled when he has her.in Mature
Mom's Best Friends Ch. 01 An invitation to a good dinner and a fantastic dessert.in Mature
A Summer's Education A college student's first sexual education.in First Time
Seduced by Best Friend's Mom Pt. 01 Best friend's mom is an MILF and she seduced me.in Mature
More Stories