my first time

by Sophie

I originally emailed this piece to Jamie months ago. I wrote it early in our interaction, when we were still getting to know each other by sharing stories about sex and numerous other mutual interests.  At the beginning of this one I wrote: “I have never, ever told anyone this story. This one is just for you.”

Oh how things change.

Jamie and I discussed the implications of posting this before we decided to go ahead with it. I know that this story could be construed as some sort of intense age-play fantasy. As the person who lived the experience, I reject that interpretation.  I know that some people will read this and decide that I am so fucked in the head that I am romanticizing a potentially inappropriate encounter with someone who was taking advantage of my youth and inexperience. And maybe I am, and maybe he was, but I don’t think so. I just think that I have always known what I have wanted, and what I wanted was this, and for me it was perfect — and perhaps set off a fascination with older guys that persists to this day.  Jamie and I have spent a little time exploring my love of mature men and we decided to kick off that exploration by posting this story, with more to follow.

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When I was a teenager I spent a lot of time on the Internet. America Online was all the rage and I spent countless hours on it, much to my mother’s extreme displeasure. I still remember that my hometown had to adjust the long distance calling rates because to dial AOL you had to call the closest large metro area, which was a long distance call from my home. (Ah, the economic wonders of the internet.)

I played a lot of online text-based roleplaying games at the time, using chat rooms to become different people in places that weren’t small redneck suburbs. I had several good friends that were scattered across the country. One of them was a guy I will call James. We corresponded feverishly for months, I knew he was in his mid-thirties and he knew I was in my “late teens” — I think to convince himself that what we were doing was okay. We talked about all kinds of things, especially music — he introduced me to a lot of stuff that shaped my basic music taste — and books. He was also an aspiring writer and we would use the message boards dedicated to the game we played together to write these intricate fantasies that were read and enjoyed (at least according to their comments) by hundreds.

I’ll admit it — I had fantasies about flirting with this man. I wanted him to tell me he imagined me as a beautiful woman, or that he thought about me late at night when he was alone, but our interactions were always relatively innocent.

After six or eight months of this intimate-but-not-inappropriate connection, he finally took it there. It was a late spring night, a school night for me, and he sent me a private message at about midnight declaring that he was drunk and that he needed to tell me something. He then proceeded to tell me that he had no idea what I looked like — this was way before “selfies” and cameras on phones — but that he desperately wanted me. That he felt it was wrong because of the age difference and he knew if my father found out about it he might be in potential danger.

“But I don’t care,” the words burned on the screen, “I just have to know what it’s like to be inside of you.”

I remember everything. I remember looking at the screen in my darkened dining room, shocked. In my slowest, most private moments I had imagined us together, but I knew it wouldn’t happen. I never expected him to say out loud what I had been thinking. I wasn’t as good a flirt as I would later become, I didn’t know what to say back. I took so long to reply that he finally prompted me: “Soph? Did I scare you?”

My response was the equivalent of a digital stammer, clumsy.

“I haven’t been with anyone before.” As I wrote the words I felt that familiar ache, the one that coiled in my stomach and spread, hot to the core of me. The itch I had always scratched on my own, middle finger on my clit, eyes shut tight and breath catching in the darkness and privacy of my childhood bedroom. I bit my fingernails as I waited for his response. It came about four minutes later.

“Would you let me be your first?”

That question began a series of events that lead to him flying to my area a month later. He got a hotel room, and I skipped school. I remember frantically searching through my closet, looking for the most provocative clothing a teenager would own, choosing my black underwear and bra because I didn’t own anything lacy or sheer at that age. I remember the knots in my stomach at the thought of meeting him, my hands shaking as I started my car. The forty-five minute drive to the city was brutal. I was wet five minutes into the drive.

He worked in telecommunication in some way and obviously had a good job, for his hotel room was in one of the nicest hotels in the city, true luxury accommodations (circa 1998). The lobby at the time was lots of dark wood and gaudy 90’s chandeliers and ornate carpeting. I had never done something like this before. I pulled the piece of paper with his room number on it out of my purse with still-shaky hands and headed toward the elevator. I remember my skirt brushing the tops of my knees as I entered, goosebumps erupting, swallowing hard.

Oh god, I am just now remembering I still had braces.

When he came to the door, I was surprised by how tall he was. He looked at me for a long minute without an expression on his face. I worried immediately that I didn’t please him, that he had wasted his money on a plane ticket and a hotel room. He finally smiled and sighed a little — he had also been holding his breath.

“You’re gorgeous. You’re so young. Come in.”

I walked in, smiled, dropped my bag. I remember all the chairs in the room were too plush and I sank into the one I chose. He had already been drinking at two in the afternoon and offered me one — bourbon, the first drink I ever had. I told him so. He then nervously told me I didn’t have to take it, but I told him I wanted to. I remember the weird sweetness, the burn. I will always connect bourbon with sexual tension and pleasure.

We made small talk for a while. He was clean cut, professional. Wearing a button down, slacks, nice shoes. Brown hair, brown eyes, cute. I looked down at my beaten up Doc Martens with a bit of shame. He seemed very reticent to make a move, like he knew he was doomed if he did. Finally I stood and moved to the overdressed bed, sat again.

“I want you to touch me,” I said, imagining myself as some sort of wanton goddess with the nerve to see this through. He looked at me with surprise in his eyes.

“Are you sure?” I nodded. He stood up — so tall! — and said, “okay, I am going to touch you, please don’t let me do anything you don’t want. I don’t want to hurt you.”

He came to me and bent down to kiss me. It wasn’t my first kiss, but it was my first real kiss that was going to lead to something. His hands were on my shoulders, his lips firm and insistent. I was shy with my tongue, not sure how to do this. He seemed charmed by my inexperience, and slipped his hand under the neckline of the dress I had chosen for this occasion.

Clothes began to come off, at first slowly and then with urgency. Our breath became ragged and impatient. He expertly removed my bra one handed and said, “turn around.”

He pushed me onto my stomach while I wore only my panties. I could see he was still in his slacks when I turned my head to look at him. I could see the outline of his cock behind the fabric.

“I want to give you a back rub. I know it sounds weird, but that’s what I want to do.”

I tried to shrug nonchalantly. “Sure,” I smiled, and turned to look at the headboard.

At first he was on his knees between my legs, rubbing my back with his warm hands. They were focused on my shoulders at first, then moved slowly down to the small of my back. At some point when I wasn’t paying attention he had gotten close so his heat and stiffness was pressing against my soaked panties. I think he felt it then, because he hooked one finger into my underwear and started to pull them down, past my ass, onto my thighs.

I felt unfamiliar flesh begin to press against my pussy, I could feel my wetness clinging to the hair there. I heard him groan and he finally said, “okay, I am going to fuck you now. I can’t not. If you don’t want this, tell me now.”

I turned my head and looked back at him. It was the first time I ever saw the look I would see later on countless men, a mixture of wonder and lust. “I want you to.”

It took almost nothing for him to slide his cock — which I remember a lot like Jamie’s, though I may be projecting — into me for the first time, the first time anyone had ever been inside of me. It didn’t hurt at all. I didn’t bleed. I did cry out in surprise, which caused his cock to stiffen even further. I arched my back, naturally presenting myself to him.

He then grasped my hips and drove fully into me, sighing, “oh my God, you are so beautiful, I knew this would be special.” He only lasted about twenty minutes, but I only lasted about ten. His fucking was rapid and urgent and intense. The sheets were rolling away from the corners of the bed. We were sweaty and animal. When I came, I could feel my muscles roll over his cock. I almost passed out from the feeling. When he came, he warned me it was going to happen, and then drove into me one last time and cried out.

There’s more to this story, but that’s, technically, how I lost my virginity — to a guy in his mid-thirties who treated me as well as, even better than, a fumbling teenage boy more interested in his own pleasure than mine.

Maybe I do have a type.