tagFirst TimeThe Male Virgin

The Male Virgin

bytheoutcast©

Now, I didn't normally date men younger than I but when you're a twenty-four years old unwed mother, good dates are scarce. On top of that, I got knocked up so young that I never attended a college prom -- like never - and when twenty-two year old Tom asked me to go to his senior prom, I accepted. Tom was a shy, quiet boy who worked as a bundle boy at my cash register in the supermarket.

My mother was thrilled to learn that I had a date with a college boy and I was thrilled to be attending a college prom. Mom agreed to tend my two-year-old child overnight.

I wore the same light blue strapless gown that I had worn to my high school prom six years earlier. A new petticoat restored its fullness. Tom bought me a beautiful orchid wrist corsage. He was dressed in a white tuxedo with a red cummerbund. We took pictures that I still cherish..

The evening was wonderful. Two bands kept us dancing until midnight. After the prom, six of us - three couples - went to a Chinese restaurant in Central City's Chinatown. It was my first trip to Central City at night and my first time to eat at a Chinese restaurant, ever. Although the youngest member of our party was my twenty-two year old date, none of us had more than one drink. In retrospect, budget constraints.

It was during the after dinner conversation in the ladies room that the other two women, and I learned that all of our three men were virgins. None of us were virgin, but our men were. While there in the ladies room, we pledged to "un-virgin" them..

The other two couples drive home together. I never met any of them again. Tom and I drove home alone.

On a quiet stretch of road I said, "Will you stop the car so I can get out and pee."

The use of the word "pee" startled him such that I had to repeat the request.

He stopped the car. I told him not to peek. I got out of the car, walked behind it, lifted my gown, lowered my panties, and peed in the street. No passing car came by to embarrass me.

When I got back in the car, I asked him if he had peeked. He said, "No." I believe him. He was so shy.

A short distance later he asked, "Can we stop somewhere and talk?"

I knew he wasn't looking for conversation but I wanted his night to be as memorable as mine and I remembered my pledge to the other girls. I had no doubt in my mind that I could change his status as a virgin.

"There is plenty of privacy in the far end of my driveway," I told him. We ultimately parked under a tree in my backyard.

Thinking of my personal comfort while he fucked me, I said, "There's more room to sit and chat in the back seat." Quickly we were in the back seat.

"May I have a kiss," he asked.

I gave him a hug and a kiss. We sat back.

The scarf I had worn to cover my shoulders became tangled in my arms. I draped it over the front seat.

He leaned towards me for another kiss. As he put his arms around me his hand landed "accidently" on my breast. I pretended not to notice.

We kissed a little more heavily. His hand explored my bare chest above my gown. His fingers dawdled at the top of my strapless gown.

"You can pull lit down," I whispered as I took a breath between kisses.

I was bare breasted before we finished the next kiss.

He leaned back and looked at my breasts. "I've never seen a woman's tits before."

"Haven't you ever felt up a girl's tits," I asked.

"The girl I dated last year let me feel her up under her blouse but she never let me see them."

"Did she let you do anything else?"

"She let me feel her stomach and the hair she had in her panties."

"What else did she let you do?"

"She let me put my fingers in the hole between her legs."

"Did you play with her clit?"

"What's a clit?"

"It's a little button in the front part of a girl's pussy that excites her."

I could tell he was shocked by my use of the word "pussy."

Without any further ado, I stripped naked. I was going to give this naïve collegian a lesson in female anatomy.

"It's okay. You can look. You won't be struck blind," I assured him.

"Wow. You're pretty," he said.

I guided his hand to my crotch. "Put two of your finger inside me," I told him.

He did.

"Now feel around with your thumb. Do you feel that bump? That's my clit. Use your thumb to flick it around; to stimulate it."

He kissed me ardently while he played with my clit. I think I was more excited that I taught him something than I was with the way he played with it.

"Go in and out with your fingers while you play with my clit. Let your fingers explore my insides," I whispered in his ear.

I took his hard-on out of his pants while he played in my pussy. He didn't resist. I guided his dick towards my opening. He resisted gently.

His fingers left my vagina and caressed the runway between it and my anus. When he reached my asshole, his moist finger circled it over and over. It was tantalizing. No one had ever played with my asshole, especially like that. I was ready to scream when he finally entered it. Instead, I gave him a hard kiss and hug.

It was then I felt his cum spilling onto my pussy. He came before I could get him into me. I failed in my mission to un-virgin him.

We drifted off to sleep. It was daylight before we awoke. We had slept the night through. When he awoke, he said, "Oh, my mother will kill me. I was supposed to be home by two AM." The fright he felt of his mother had him almost in tears. He left for home. I went into the house.

Monday, at the supermarket, the head cashier introduced me to a new bundle boy. When I asked where Tom was my boss answered, "He quit last Friday. He's going in the army."

I haven't heard from or about Tom in the thirty years since that memorable evening.

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by Anonymous

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by nortythorts05/05/18

Great read, and convincing

Well written, I liked the "dawdled" term for the lad's exploration, and liked the slight failure of the mission - more realistic than the lad becoming an instant stud/expert.

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