Ann

This story is true, and as vivid in my memory as if it happened only yesterday.

It was the summer after I'd turned 18, and she was the best friend of a girl in my summer school French class. Her name was Ann and we met one afternoon when she came to pick up her friend, Lynn. That night I called Lynn with a million questions about Ann. She laughed and told me she'd just gotten off the phone with Ann, who had a million questions about me.

The first couple of times we went out were pretty innocent. I was a virgin, but had done about everything but had sex with a couple of former girlfriends. I wasn't sure whether Ann was a virgin or not, and it didn't really matter to me.

On our third date, we went to a drive-in movie. Midway through the movie, the rain began to come down too hard to see the screen. One thing led to another, and soon we were into serious foreplay. Before I knew it, we were both partially undressed and I was fumbling to find the condom I kept hidden in my car, "just in case" this moment came. (No pun intended)

Let's be honest – something which may be rare in discussion of first time experiences – my first time was a disaster. We determined the front seat was too confining, so we moved to the backseat. In the move, I lost my erection. By the time it came to putting on the condom, I was only –semi-hard and all but over the edge. Before I had the head of my cock completely in her, it was over. I learned – in a matter of words – that she was not a virgin, though from my struggle to enter her, and her unexpected vocal response to my efforts, I honestly thought she was. I apologized, thinking I may have taken HER virginity. She said little, and thankfully, forgave my clumsiness and didn't disagree when I promised to make it up to her.

The following weekend, we hooked her best friend up with my best friend, Donnie. We went to a movie and then to a local hangout, which was kind of dead. Knowing that my parents were at our lake house, Donnie suggested we go back to my house and shoot a couple of games of pool on my father's table.

As soon as we pulled into the driveway, Ann told me that she wanted a "tour" of the house before we shot pool. The last room on "tour" was my parent's bedroom. As we started to leave, I turned her around and kissed her. It was our first time alone since my "first time." Alone in the privacy and comfort of my parents house, her reaction to our kiss was even more electric than our first time together. After a few minutes of making out standing up, I suggested we'd be more comfortable on my parent's bed. She told me to lock the door so our friends couldn't surprise us. I turned to lock the door and dim the lights, and when I turned back around she had already climbed on my parent's old antique bed and was reaching out for me to join her. Though we had had sex once, I was taking nothing for granted.

After a LOT of deep, passionate kissing I had her blouse unbuttoned. As I started kissing her breasts, she began unbuttoning my shirt. After more kissing and petting, I let my hand wander down to the bottom of her skirt. When I started moving my hand slowly up the inside of her thighs, she stopped me, but didn't make me move my hand. The longer and more passionately we kissed, the further my hand moved up her thighs, until I could feel the heat coming through her wet panties. When I started to slip my fingers under the legband, she again stopped me, but didn't make me move my hand. I was beginning to wonder if I would get as far with her as our previous weekend.

When I finally got one finger under the legband and slipped it into her, she moaned loudly and gripped my shoulders so hard I wondered if her fingernails were going to rip my shirt. In the excitement at the drive-in, I had thought her "tightness" was because she was also a virgin. Now, with us stretched out on my parent's bed and able to be relaxed, I realized – at least in my own mind – she was "small."

After a long time of kissing and "finger play" I was able to get her skirt and slip off, but not her panties. The longer we kissed and played, the more delirious with passion she became. As we continued kissing, I used my free hand to carefully unbuckle and unzip my pants, and slowly moved around until my pants and boxers were below my hips, releasing my erection. As we continued kissing and petting, I moved over her in the missionary position and we began moving like we were having sex. With her panties between us, she didn't seem to realize how little was keeping me from penetrating her. When my cock finally "found" its way past the legband of her panties, and she felt it against her soft, silky curls and wetness, she quickly reached down and grabbed me with one hand as she pushed me away with the other. "OH GOD, STOP!" she cried. I stopped, but didn't move. I felt like I was going to explode. She moaned loudly as she continued holding my cock in what felt like a death grip.

"Ann, I want you." I whispered. In the dim light she looked at me with tears in her eyes and told me she was scared. She said that while she was not a virgin, the only two other guys she'd been with weren't close to my size and that she was afraid it was going to hurt. My cock went soft as we lay there for what seemed an eternity, talking. She said the first time we were together, she was glad I came before getting into her, because I felt big when only semi-hard. Finally, after a lot of promises that I would never force myself on her, we started making out again. After a lot of passionate kissing, I once again moved over her and started moving like we were having sex. This time when she felt the head of my cock rubbing against her very wet opening, she didn't stop me. When the head found its way between her lips, and tried to slip in, she cried out and gripped my shoulders until I wondered if she was drawing blood.

Her body slowly and begrudgingly opened to my near-virgin cock as we passionately kissed and rocked against each other. Like the first time, I felt my cock erupt before I was really in her; the only difference was that this time I was hard as steel and at least the head of my cock was in her. The feeling was even more overwhelming that the first time, and I kept trying to push deeper, without realizing that she was trying to keep me from going too deep. Though I was lost in the moment, her cries had brought a heavy knock on my parent's bedroom door!

As her friend Lynn kept calling her name and asking if she was okay, Ann held me close; through sobs assured Lynn that she was okay; and whispered for me to "please don't take it out." We lay there with her body gripping my softening cock until her friend was convinced that she was okay and left us alone again. In the dim light, her beautiful blue eyes glistened with tears as she looked up at me and whispered, "Please get it hard again, I've got to have you – and this time I want to feel all of you in me."

We both felt it growing hard inside of her as we looked into each other's eyes and began to move as one. Once again, as our passion grew, her tears began to flow, but this time, thanks to us having overlooked a condom in the heat of passion, her love tunnel was WELL lubricated with my cum, and her tears were of joy. This time I knew to muffle her cries with deep, passionate kisses. When it was over, she giggled and whispered, "I feel like I just lost my virginity, again." Since I hadn't actually penetrated her the "first time" we tried in the backseat of the car, I felt like this was my "real" first time.

When my parents returned home, my mother was more skeptical than appreciative that I had washed all of the linens "just to help her out." Personally, I was just thankful she found no blood stains!

Though my lover and I were only 18; I was a virgin, and she wasn't far from it, my "first times" were without question among the most unforgettable memories of my life. And in my 50-some years, only one other lover has expressed both pain and pleasure as loudly and with tears. I would give anything to know where Ann is today. She will forever hold a special place in my heart and memory.