My First Time

I began pumping him up and down, awkwardly at first, but soon got into the right motion. He kissed me with mounting passion, and held me tight. In a few seconds, I sensed him tensing his body and thrusting his hips into my pumping hand. I felt a pulsing sensation then heard a kind of groan as he let his breath out. He grasped my hand and held it tight for a long time, relaxing his grip only when I felt his thing begin to shrink. In a minute or two, it was only about half the previous size. The rubber was hanging loosely with a bag of liquid in the end.

Dean pulled it off and handed it to me to look at. I was amazed at the amount of liquid in the rubber! After a while, I handed it back to him, wondering what he would do with it. He casually tossed it out the window, then turned and kissed me again. He was still sitting there with his pants nearly on the floor. I was fascinated at how this formidable thing of a few minutes ago was rather sedate and harmless looking. I couldn’t help but touch it once again, fascinated at how soft and smooth it not felt. Dean made a comment that puzzled me.

It sure is a relief not to hurt all the time we are together.

“What do you mean?” I asked.

“Uh, well, when I am with you and get really hard for a long time, it aches something terrible, but when I come, it relieves the ache.”

Over the next several weeks, Dean would surprise me from time to time by stopping by after work, most often on Friday nights. We kind of fell into a regular pattern, driving to a deserted road close to a country airport. We spent a lot of the time making plans for the wedding about two months hence. Inevitably, we would end up discussing the sex books we were reading, comparing notes, exchanging information, and clarifying questions about each other. We were becoming more at ease with our upcoming marriage and ourselves.

He never did bring another rubber, but one evening he gave me a package from a drug store. His uncle, a doctor, had given him a prescription for birth control cream in a tube, along with an applicator. He had purchased it for me and wanted to look at it together. We opened the package, played with the applicator, and put some of the cream on our fingers and smelled it. It had a pleasant clean fresh smell. I wrapped it up and told him I would take it home and put it in my wedding night bag.

Most evenings, I would help him “not to hurt.” After the first few times, he got so he didn’t come in the first few seconds, so we could play for extended periods of time. He would kiss and caress me, letting his hands roam fairly freely over my upper body. Inevitably, they began to drift downward, until one evening, we crawled into the back seat for more room. Dean had succeeded in removing my blouse and bra, and was played with my bare breasts in earnest. Shortly, he worked his hands under my skirt, and began steadily upward.

I was wearing a long-line girdle, so his progress was seriously impeded. He made some comment about me wearing a suit of armor. I responded that most armor I knew of would come off. Without hesitation, he reached up and pulled it off. I still had my panties on, but their flimsy fabric offered little protection to his probing hands. Moments later, I felt them begin a downward journey as well. I lifted my hips in silent assent to his actions. Moments later, I felt his fingers probing, probing, then find the target. He slipped a finger in and began stroking slowly, up and down, up and down my slit. The feeling was incredible! I could feel my inhibitions melting away, and for a brief moment, I wanted him to jump on top of me and put his penis in me!

I was so startled at my feeling that I kind of jumped.

“Stop, please stop now,” I asked breathlessly.

“Why, don’t you like it?” he asked with a note of hurt in his voice.

“I like it so much I’m afraid I can’t stop, but I just don’t want to go any further right now, please don’t make me,” I pleaded with tears in my eyes.

He complied with my wishes, so I decided to reward him for his actions by helping him not to hurt. After we got dressed again, we talked for a while longer then he took me home. I couldn’t help but think that the wedding better come up fast if I ever hoped to be a virgin on my wedding night!

The next time we had a chance to be together alone, I was wearing slacks. We had been driving and talking about our books, and before long I could see his erection. We headed for our favorite place, and parked. It was a moonless night, so we were doing everything by feel. Since he couldn’t run his hands under my skirt, he simply unfastened my slacks and pulled them off. After some kissing and cuddling, he slid my panties off. By that time, he was naked, and I had only my blouse and bra on. That only lasted for about another ten minutes, until I was completely naked.

I hesitated for a while then pushed him back when he tried to embrace me.

“What’s wrong,” Dean asked.

“We’re not married yet but here we are completely naked!” I replied.

“No we’re not, I still have my socks on!”

We laughed about his comment for several seconds, which broke the tension. I melted into his strong arms, feeling myself kind of soar. We played around for quite a while, feeling each other, exploring our naked bodies, but not able to see much of each other because of the darkness.

After a while, I began stroking his penis, but for some reason, he didn’t come. Finally, he pressed my hand away saying that he was so dry that my hand was starting to irritate the tip.

“We need some hand lotion or something to make it slick,” I commented.

“Hey, I know how to make it slick,” he responded as he rolled on top of me.

“Dean, stop, stop, I don’t want to do it yet, I want to wait until we are married.”

“I’m not going to put it all the way in, I’m just going to slide it in far enough to get it slick.”

“OK, but you got to promise me you will stop when I tell you or I won’t even let you touch me.”

“OK, I promise,” he assured me as he lowered himself into position. I guided his thing toward my opening, tensing up as I felt it touch my hair. He pressed gently forward until I felt the tip engage my swollen lips. I’m not sure just what caused the sudden pain, or if it was my imagination, because he had hardly touched me when the pain caused me to stop him. True to his promise he pulled back, but I could tell how truly reluctant he was. Never the less, it did accomplish getting him slick, and when I again began stroking his penis, he came almost at once. After playing around for another half-hour or so, we reluctantly dressed and drove home.

Over the next couple of weeks, we explored each other in greater and greater detail, but never really saw each other due to the dim light. Dean began probing my virginity, pressing his finger into my vagina, exploring, feeling, and experimenting. Even having a single finger inside me hurt. We began to believe that something was wrong with me such that we could never make love with each other. In retrospect, it escapes me why I didn’t just make an appointment with a doctor to determine what was wrong.

As we talked about it, and read more about what the books said regarding the first time, we began to understand that I probably had an unusually tough hymen. One of the suggestions in the books was that I should stretch it with my fingers over a period of time, which was supposed to gradually enlarge the opening. As I helped Dean not to hurt, he reciprocated by playing with my virginity, gently probing and stretching. It wasn’t altogether unpleasant, but for some reason it didn’t seem as if we were making very good progress.

One Sunday evening as we were driving home, we stopped on a deserted road and began to play around. After about an hour, I was dripping wet, but unsatisfied. I had made Dean come, and his passion had somewhat subdued. I was nearly dressed, and had already put my panties on when Dean began playing with my thighs once again. He slid his fingers under the leg band of my panties and began probing. I felt his finger penetrate and then I felt more pressure than normal. Slowly, slowly he pressed until I felt myself spreading open further and further. When I asked him what he was doing, he told me that he had two fingers inside me.

Oh, maybe we can do it after all, I exclaimed.

Do you want to try it? he asked breathlessly.

Oh yes, let’s see if it will go in, I replied without hesitation, “but be sure you don’t come, I am not very far from my fertile time.”

Dean almost ripped my panties in his haste to get them off me.

“I think I can hold off now that you have made me come,” he replied. “I usually can’t come this soon anyway.”

An instant later he had shed his pants and shorts, and was between my legs. I tried to get ready, but he was almost like a stampede. He settled himself over me and began moving into position. He probed a couple of times, totally missing the target. Finally, I reached down and grasped his throbbing penis and steered it to the right place.

Be careful, and promise you will stop if I say so.

“I will,” he promised sincerely. “Are you ready?”

In response, I tugged his penis until it touched me. I continued to hold the intruder in my hand, and as I felt the invasion begin I began to squeeze it tighter and tighter.

Are you OK? he asked.

Uh, huh, just be careful, I replied with a trembling voice.

He pressed a little harder and I began to feel as if I were being torn apart. I squeezed him as hard as I could and at the same time began pushing back. I didn’t tell him to stop, because I wanted to know if it would go in. Dean didn’t jam it into me; he just held steady pressure, asking every few seconds if I was OK. I didn’t tell him how much it was hurting, I just nodded my head and continued to squeeze him as hard as I could. Suddenly, just when I thought I couldn’t stand another second of the stretching, I felt something give away and he slid in about another inch or two. At the same instant, I felt something warm and wet running down my bottom. My first reaction was that he had come inside me and I might get pregnant. It didn’t dawn on me that if he had come, it wouldn’t be running down the outside. I told him to take it out quick! I could tell that he was most reluctant, but he did pull out.