Heathers Virgin

"Gerald, I'm going to say goodbye to you here." She put her arms around me and gave me a hug. She whispered softly into my ear, "You'll always hold a special place in my heart." Then she gave me a brief but sensual kiss on the lips. And I watched her walk away.

Gerald

When I moved to Manhattan a couple of years ago, I had hoped I would date more. I was always shy with girls and never dated much in high school or college. At the age of twenty-six, I had never been in a relationship, and I hoped that would change in New York. I did meet a few girls on an online dating service, and had a few dates, but nothing that developed into a relationship. I was a graduate student in English Lit at Columbia University, about to start on my thesis. That part of my life was fine, but not the relationship part. Then, Heather came into my life.

I met her at a symphony concert at Lincoln Center. She happened to sit nearby, I thought she was kind of cute, but I could also see that she was shy. Dirty blonde hair, carrying some extra weight (I didn't mind as I'm kind of heavy myself), and dressed in a loose fitting sweater and skirt, sort of like she was hiding in her clothes. I chatted her up at intermission, and then when the concert was over, i got up the nerve to ask if she wanted to go for coffee. She accepted. I felt very at ease with her. We just sat and talked, it felt like for hours. We talked about Dickens, the Brontes, Beethoven, Phillip Glass, Star Wars... everything.

We started dating in earnest. We were really shy with each other at first. It was our fourth date before we even really kissed. We were sitting right by the fountain at Lincoln Center, the one you've probably seen it in the movies. It was magical. After a few more dates, we had our first intimate conversation about sex. And we admitted to each other that we were both virgins.

Heather

Gerald was just so sweet and shy. Kind of a Teddy bear, and somewhat baby faced...a big kid, really. He knew more about English Lit and classical music than anyone I've ever known. I was an undergrad in library science, so we had a shared interest in books and writers. I thought it was really sweet that he was still a virgin at twenty-six, in fact, I admired him for that. At twenty-one, I was a few years younger, and waiting for someone special before I parted with my virginity. In Gerald, I thought maybe I had found him.

Gerald

As anxious as I was to lose my virginity, I also knew it might be wise to wait awhile. We would spend time together and get to know each other. We actually decided to wait a year... I know that sounds crazy in this day and age, but we felt that if we were still together after a year, then we would share ourselves with each other. It was a mutual decision, and I didn't have any problem with it. Of course we did some things like kissing, holding hands, cuddling, but not much more than that. I loved being with her. I loved her.

Heather's room mate was named Cassandra. You might say Cassandra was Heather's complete and total opposite. She had a slim, sexy build, dark seductive eyes. She was also very sexually active. Sometimes she would bring guys over for one night stands. I also heard she'd had a couple of affairs with married men.

While Cassandra was nice enough to me, I never really felt comfortable around her. I assumed that she knew that Heather and I were waiting to have sex. Sometimes I felt like she was giving me teasing looks behind Heather's back. One night, when Heather and I were alone in the apartment, cuddling, Cassandra came in with a guy, She said hello, and the two of them headed straight to her room. A couple of minutes later, we could hear them. There was no mistake about what they were dong. We were both a little embarrassed, but we managed to laugh a little. We left and went for a walk in the park. But I couldn't help but think that Cassandra had something in mind for me.

Cassandra

Sure, Gerald was a sweet boy, but the operative word here is boy (as in adult boy). I guess the fact that they were both virgins and saving themselves, so when the time came, it would be "special", was kind of sweet. But I adored my shy, innocent room mate, Heather, and I knew what she needed...she needed to get fucked. And if she stayed with this guy, it was going to take forever. And really, what was he going to be able to teach her? Well, it's been said that I have a manipulative personality. Maybe it was time to put it to use.

Gerald

A few months into our relationship, Cassandra started to take Heather under her wing. They started going to the gym together. In what seemed like a very short period of time, a few weeks, really, Heather started to lose weight and began to develop a really nice figure. Her face thinned out too, and her features, which I thought were pretty to begin with, started to become more apparent. Next, Cassandra did a makeover on her hair and clothes. In just a few months, Heather went through a real transformation. It was amazing. She really became a swan.

One thing I noticed was that guys started turning their heads, checking her out. It was something they weren't doing when we first started going together. It didn't worry me, because Heather still seemed into me and was still very affectionate with me. And besides, now i had this great looking girlfriend. And we were getting closer to the end of the year I would fantasize almost every night about how our first time would be.

Heather

We were getting close to our one-year anniversary, Of course, I would imagine what it would be like. I knew sex with Gerald would be warm, tender, sweet. I knew we would both be very nervous, but we would learn from each other. Would I orgasm the first time? I didn't know. Would Gerald orgasm prematurely? Probably. But if he did, and if it embarrassed him, I would hold him and reassure him that he did fine and that everything would be alright. We were about a month away, and I was so looking forward to it. And then... then came the night of party.

Gerald

We had about a month to go, and I was so excited, I was about to bust. One night we went to this party. I'm not even sure why we went, Cassandra brought us along. It was mostly her friends, her crowd. Well, there was a guy at the party who was definitely very interested in Heather... He was dark and had a gym rat type of body, a real six-pack kind of guy. I found out later his name was Dominic. Somehow, he sort of paired off with Heather. It was a crowded party. I would be in one corner of the house, talking to someone and look across the room and see the two of them talking. He seemed to be bringing something out in Heather that I hadn't seen before. She seemed very animated, not shy at all. And I could look at him and tell he really wanted Heather.

Heather and I had never had an argument, and I didn't want to start one then, but I said something about him later on, after the party.

"That guy, Dominic seemed pretty interested in you."

She just sort of blew it off, "Oh, he's just arrogant, really full of himself."

So I didn't worry too much

Heather

Before the party that night, Cassandra had gone on ahead of us. Gerald came and picked me up at the apartment. We had a little time, so we cuddled for a few minutes on the sofa It was sweet, like it always was with Gerald. But when we were in the elevator together, on our way up to the party, something came over me. I couldn't explain it, but I started to get really aroused. I didn't know why at first. Then I started to understand that maybe I was having some kind of premonition. I knew something special was going to happen that night.

Cassandra

I had known Dominic for awhile. I don't quite know how it is that we had never fucked. We ran in the same circles and were certainly attracted to each other. We just never got around to it. But I knew after two tours of duty in Afghanistan, that he was the kind of guy who usually got what he wanted. And I could tell that night he really wanted my beautiful room mate, Heather. After I pulled him aside and told him that Heather was a virgin, I could see that he wanted her even more.

Heather

Despite what I had told Gerald earlier about not being impressed with Dominic, when I got home that night, I couldn't stop thinking about him. But I was committed to Gerald, and I was going to fight it.

Gerald

So, I didn't worry much about the guy from the party, Two weeks later, Heather and Cassandra went down to Florida to stay at a place on the beach for a week. I was really busy with my thesis so I couldn't take any time off. Maybe I should have, but as I think back, it might not have made any difference.

Here is what think happened: Dominic, the guy from the party, and another guy, one of Cassandra's sex buddies went down to Florida at the same time and rendezvoused with Heather and Cassandra. I may be naive, but I honestly don't think Heather knew this guy was going to be there. I'm sure it was all engineered by Cassandra. But, while they were down there together that week...that's when she gave him the gift of her virginity.

Heather

I was so mad at Cassandra, when those guys showed up at the bar on our first night. I knew why he was there, and I knew who was responsible. I owed Cassandra so much for helping me lose weight and feel beautiful, but that night, I just wanted to kill her.

The next day, through no desire of my own, we paired off, Cassandra went off with her sometime boyfriend Matt, and I spent the day with Dominic. We had lunch and went swimming, When I saw him in his swimsuit, I knew there was no use fighting it. I wanted him as badly as he wanted me.

We made out on the beach for awhile, then we went back to our room. I knew Cassandra wouldn't be back for awhile. We made love on top of the bed. He was so gentle and reassuring, and yes, I came the first time... together...with Dominic.

Cassandra

We were on the plane coming home at the end of the week. I knew that Heather would be mad at me for setting her up, but I also knew by the end of the week, she would be grateful.

"I'm so proud of you," I said. "You came down here an innocent little virgin and now you're going home a woman. Did you learn how to fuck?"

"Yes," she said with a slight smile. "I learned how to fuck. But, I'm still mad at you," she said playfully. "Because of you, I've got a big problem to deal with when I get back."

"I wouldn't worry too much about Gerald," I said. "He'll get over you in time. And besides, he's still got his fist."

"Dominic wants me to live with him."

"Are you going to do it?" I asked.

"I don't know yet. I think so. I know I i'm going to want him every night."

"When we get back, I'll help you get set up with some contraception." She laid her head on my shoulder and went to sleep.

I knew Dominic came down to Florida to take Heather's virginity. But something else had also happened. Once he fucked her, I knew he wouldn't just leave. He wanted to train her, to teach her, to turn her into a great lover. And she would be a willing student.

Gerald

When Heather got back, she was honest with me. She told me what happened. She told me who it was. She said she felt like she wanted to be with this guy. I was crushed, She held me while I cried. We had only been one week from the end of the first year.

I pleaded with her. I called her every night for the next two weeks. Finally, one night I said, "If you think you've got him out of your system, you can always come back."

She said, "Gerald, I'm moving in with him." I knew then, I had no chance of getting her back.

That was six months ago. She moved in with Dominic and she's living with him now.

I saw her for the first time since we broke up about a week ago. We had talked on the phone from time to time. I think she was a little worried about me. It was in her nature to be very nurturing and she wanted to know that I was all right. And maybe we could both say some things that needed to be said.

After work, (she was working at a library now, I was working at a small literary journal) we met at a little coffee bar on Columbus Avenue that we used to go to together. She was sitting there waiting for me. Needless to say, I felt a little awkward. I had always felt that the fact that we were both virgins was something that bound us together. And of course, now she wasn't a virgin anymore and I still was. She looked even more fit and trim since the last time I had seen her. She wore a tight fitting white turtleneck sweater and jeans. She was no longer the shy girl hiding in her clothes. She was a woman. I also knew after six months of living with Dominic, that she was now an experienced lover with a skill set that I had yet to acquire.

We sat and talked for awhile, I didn't feel that she owed me any explanation as to why she broke up with me. I was sad, but not bitter. Maybe I was a little bitter toward Cassandra, but not Heather. But anyway, she told me that after she lost weight and went through her transformation, she started noticing the guys that were looking at her. And something happened inside of her. She started thinking about being with a different kind of man. I didn't ask her what she meant by that, but I knew. Someone who could handle her needs and desires. Someone like Dominic.

"I really miss you", I said.

"I know you do, Gerald. But you know things are different now. I'm with someone else."

Then I said something I probably shouldn't have said, but it just came out. "I still fantasize about you."

She paused. Then she said, "Do you mean when you masturbate?" I know I must have turned red as a beet, because I certainly didn't mean for the conversation to go in that direction. I nodded my head.

She took my hand, "That's all right. It's natural, It's a natural thing to do." We sat in silence for a minute as she held my hand. She was so sweet, so nurturing, i loved her so much at that moment.

"Gerald, I want to tell you something. When I first met you, I loved the fact that you were still a virgin. I admired you for waiting for someone special. And maybe you don't want to hear this, but I still think it's a really wonderful thing. Maybe it makes you different from other men your age, but not in a bad way. It's nothing to be ashamed of. I know things didn't work out the way you expected them to between you and me, I went in another direction. But if there is anything you could do for me now, it would be to stop being ashamed and maybe even...embrace it, take a little pride in it. I'd be so proud of you. Can you do that for me?"

"Yes," I said. "I'll try."

We got up and went for a walk. She held my arm and we didn't say anything. We were a few blocks from where she lives now.

"Gerald, I'm going to say goodbye to you here." She put her arms around me and gave me a hug. She whispered softly into my ear, "You'll always hold a special place in my heart." Then she gave me a brief but sensual kiss on the lips. And I watched her walk away.

Heather

As I started to walk away from him, my eyes filled with tears. I felt so bad about what I had done. I don't know if it could have ended any other way. I hoped he would find someone someday, but I knew it would take him awhile to get over me. In the meantime, I really did mean it when I asked him to embrace his virginity. He was twenty-eight years old...a grown up boy...my sweet, innocent boy.

As I got closer to my building, another feeling started to take over. i knew Dominic was home. This was the time of day that he worked out on his machine. I knew the amount of work he put into maintaining such a beautiful body, and it's one of the things that attracted me to him.

As I got to our door, I couldn't get the key in fast enough. It was good timing, as he had just gotten out of the shower. I slipped my sweater off over my head there in the living room. I pulled off my boots, my jeans. He came up behind me and gently removed my bra. He pulled my panties part of the way down. I pulled them the rest of the way off. He wrapped himself around me from behind and buried his face in my neck. He had taken my virginity, taught me how to fuck, and now I was going to reward him by being the skillful lover he had always wanted. I turned around and slipped my tongue into his mouth, slowly massaging his tongue with mine. "You'd better fuck me", I whispered... I was so wet, so aroused, more aroused than I had ever been. As he took my hand and led me to the bedroom, I thought of Gerald. Sweet Gerald, on top of his bed, stroking himself, thinking of me. Someone who wanted me so badly, but couldn't have me. I was still thinking of him when we moved onto the bed. Dominic slowly slid on top of me, inside me. I was still thinking of my sweet boy when I came. Maybe he'd be glad to know his desire for me was a factor in the super intensity of my orgasm. Maybe I'd tell him the next time i saw him, Maybe.

Gerald

When I got home, I could still feel the warmth of her breath in my ear. Her scent, the soft feel of her hair when she held me. I knew she would be making love to Dominic by now. I took off my clothes. I looked at myself in the mirror for a minute. I looked at my smooth chest, my soft tummy. I knew that if we had ever given our virginity to each other, my small penis wouldn't have been a problem for her. I lay down on my bed and began masturbating, thinking of her, just like I told her I did.

I repeated her name, softly. "Heather...Heather...Heather."

I stroked even faster when I remembered the last thing she said to me.

"You'll always hold a special place in my heart...You'll always hold a special place in my heart...You'll always hold a special place in my heart."

I came all over my tummy, my chest, my sheets.

Then I burst into tears.