Nervous Nancy

Note: All characters in this story are age 18 or over. This work is based on hearsay that was garnered years ago from a coworker. There can be no confirmation of any of this being true, but it does have a certain plausibility.

Nervous Nancy

This is a story told to me by a friend who we will call Ed. Ed and I were summer employees of the local power company upstate New York and had become good friends. Since we were both away from home there were many nights when we would go to a local bar and tip a few. As we got more friendly we would tell of life experiences and one night it got around to telling about when we first got laid. This is Ed's story:

I was a senior in high school and during those four years hardly ever dated and only had two girlfriends. In February I had started hanging around with Nancy, a petite blond who, like me, it turned out was still a virgin. Having never had sex myself the idea of getting into Nancy's pants became an obsession, but she was pretty determined to keep her cherry intact. That wasn't to say that we wouldn't go parking where we would neck and over time I was able to get my hands on her modest boobs. Still, that was some progress, but things changed as we got to the end of the school year when we were also busy with graduation.

A couple of weeks before graduation Nancy and I had a date to go see a movie and then on the way home I found a back road that seemed like the perfect place to park. At the time I didn't have a car of my own so I would borrow my father's mammoth 1975 Chrysler, which had an immense front seat that would have been perfect for sex if I ever got that far with Nancy.

It wasn't long after a few kisses and my hands up under her bra that I decided to do a little further exploring. After unzipping her shorts, I got as far as Nancy's panties and could feel her pussy just beyond their sheer cotton barrier. As I inched my way to one of the leg openings intent on at least fingering her, I noticed a car pull up behind us and soon came a knock on the window. I looked up and there was a deputy sheriff.

I rolled down the window and said, "Good evening, officer."

"Are you guys alright?" he asked.

"We're fine," I replied.

He shined his flashlight into the car and got a look at our faces. Although Nancy had had time to button her blouse it was evident that he knew what we were up to. "You might want to find a better place to park. It's a little too desolate out here," he said. "Have a good evening." And at that he was gone.

Nancy, the demure virgin, was extremely embarrassed and the mood for the evening was most-assuredly killed. Although the deputy could have been a real pain, he had been very nice and there were no repercussions other than the fact that my exploration had been cut short. We would have to try again on the next date.

The following weekend we did have another date and, hence, my expectations of continuing my sexual adventures were high. Only it was not to be because after considerable kissing and getting my hands on her boobs once more, I had no sooner started to let my hand roam up Nancy's skirt when she announced that that was as far as we were going that night. Yes, of all the rotten luck, Nancy was having her period. So it was more kissing and boob feeling, but that was all. I was so horny that after I dropped her off the only thing that I wanted to do was go home, masturbate and go to bed. So close, but so far. My biggest worry by now was that I was about to graduate from high school and would still be a virgin.

Now we were down to the night before graduation. We had gone to a party at a friend's house but left early. The weather was warm and Nancy suggested that we go back to her parent's house and go for a swim in their pool. It sounded like a great idea, but better still was that her parents were out for the evening. Nancy was able to find one of her brother's swimsuits for me to wear and then she changed into a two-piece suit that surprised me in that it revealed more than I was expecting. . . a lot more. We both dove into the pool and after a lap or two wound up in a corner of the deep end that had her neck deep.

I leaned over to kiss her and soon after that I felt her hand groping for my crotch. "It's a lot easier when we start with fewer clothes," she said completely catching me off guard. I could not have agreed more and soon had removed the bra to her swimsuit. While I had felt her boobs several times before, this was the first that I had ever seen them—not very large, but wonderfully perky with erect nipples, which I was not sure was a result of the cool water or the excitement from my touch. Not happy with just her boobs, I once more attempted to touch her pussy and easily had my hand down the front of her suit. After groping around with her hairy bush, I finally managed to find my prey—her labia. Nancy seemed to love my touch and in all honesty I had no prior experience with a woman's anatomy. I inserted my middle finger up to the second knuckle. Gosh, but she was tight, but nevertheless she seemed to enjoy what I was doing, a fact that I became more aware of when she started French kissing me.

Not being a great conversationalist at times like these all I could muster saying was, "Are you OK with this."

"Oh, am I ever. Don't stop what you are doing."

I wiggled my finger and inserted it to the next knuckle, but in the meantime my member was now incredibly erect. Since Nancy had a firm grip on me, this fact was not lost on her either. "So that's what happens to a guy," she whispered.

"I'm afraid it is."

"I've always been curious. I think what I'd like to do is replace your finger with that."

"What?" I couldn't believe what I was hearing.

"Yes, I want you inside of me. Let's get out of the pool, grab a towel, and go over to that chaise lounge."

"Are you sure?"

"I've never been more sure in my life. Look, we're both graduating tomorrow night and right now we're both virgins. I don't want to graduate from high school still being a virgin. Besides most of my friends have had their cherry popped already," she said boosting herself up onto the edge of the pool.

I was not far behind and in what seemed like no time at all we had made our way over to the lounge where Nancy pulled off the bottoms to her swimsuit. This was another first because I had never seen an actual naked woman before—heck, I had only fingered one for my first time just minutes prior.

I took my swimsuit off and Nancy was as curious of what my male equipment was as I was for hers. As we sat there, I again began fingering her and soon she leaned back and spread her legs wide.

"I think the time has come, she said. "Just put it in slowly, OK? It's probably going to hurt a little and if my friends are right, I might even bleed some when you finally pop my cherry."

I started to introduce my organ into her pussy and she was right, she was unbelievably tight. I went as slow as I could and noticed Nancy would grimace and take a few deep breaths before telling me to continue. A tear formed in each eye.

"Are you sure you're OK with this?" I asked still pushing in further.

"I am, but it does hurt."

"I never knew girls were so tight down there."

"Some of my friends weren't because their moms let them use tampons. My mom insists that I only use sanitary napkins at those times when I'm on my period. Still, keep going. I've just got to do this."

A few more minutes and I was fully inside Nancy's vagina. It squeezed around my penis as I began gentle in and out motion, which she seemed to love. Her eyes teared some more. "I love it. I was worried that my first time was not going to be good, but I was wrong," she wept with joy.

More in and out motion and I could feel that my penis was ready to explode. I couldn't suppress that feeling any further and soon let go with my load. I could feel it, but so could Nancy.

"Oh! That's amazing. You're filling my pussy aren't you?"

"Yes," I grunted with a bit of elation as the last of my spasms ended.

"Are we crazy?" she exclaimed with a complete change of mood. "You could have just knocked me up!" I pulled out of her, put my arms around Nancy's shoulders. She was now crying almost uncontrollably.

"It'll be alright. I know it will."

"How can you know? I'm going to be an absolute nervous wreck until I get my period. Assuming, that is, that I really do get my period," she bawled.

"Don't think that way."

"What am I supposed to think?"

To say that we were both on edge would have been an understatement. When all of our friends were elated about graduation, both Nancy and I were more than a little reserved. Still, counting those days waiting for Nancy's menstrual cycle were some of the most unnerving days of my life. I say this, but Nancy was totally freaked out yet was still able to keep outwardly upbeat that her parents didn't become concerned.

A little over a week later, I was home and the phone rang. "Hello," I said,

"It's me. I've got some great news."

"Oh, wow. I never thought I'd be happy about a day when you got your period. Assuming, that is, that that is what you mean."

"It is. And other than that first time that I got my period, I have never been especially thrilled about getting it, but that is other than today. I'm cramping, but crazy as it seems, what a great feeling."

"So we're still friends? I'd like to still date you if that's OK."

"Oh, yes, we're still friends and I want to have more sex with you, but only if you promise to buy us some rubbers. I'm not going through this nerve-wracking routine ever again. Promise?"

"I promise," I responded.

A few days later after I had made an embarrassing visit to the pharmacy, which is a whole other story, I was back at Nancy's house out on the patio around the pool. The good thing about their pool is that it is shielded from view from the house by a row of high evergreens. As before Nancy and I were on what we now considered the "famous" chaise lounge although just to be safe we didn't take our swimsuits off but still found a way to access her precious pussy. I also have to admit that using a rubber is not only safer, but keeps things much more tidy. . . up to a point.

I don't know how many times Nancy and I got laid that summer out at the pool, but there came a day when Nancy said to me "We need to be a bit more careful."

"But we're very careful. We use a rubber every time we do it."

"I know, but that is not what I mean. Apparently, the last time you were here you left some evidence."

"Evidence?"

"Mmmm. Like the wrapper that the rubber comes in. The good thing is that mom still thinks that I'm a virgin, the bad thing is that she found the wrapper. So far she is only blaming it on my brother," explained Nancy with a smile.

"Ooops. Sorry!"

"It just makes me really nervous that I might get found out. Although not anywhere as nervous as when I had to wait to see if I got my period. Maybe we need to find another place, but most of all now that I have tried sex I'm not about to give it up either so you better continue buying rubbers for us."

"I never thought that she was called 'nervous Nancy' for nothing.