Thank You Sarah

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Memories of My First Time.
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Every writer who has had any degree of success has been asked, "How do you become a writer?"

Every good writer will respond to that question with some variation of "If you want to be a writer, start writing."

I am going to elaborate on my version of that recommendation, start with a journal. A journal gives you a place to begin to explore your own story without the need to be vulnerable to anyone else in the world, and in my own experience, I've had no greater venue in which to practice, build techniques and grow as a writer. If you don't know what to write in your journal, begin with an internet search of the phrase "Journal writing prompts."

I'm looking right now at a shelf in my office on which sit a dozen or so notebooks that I've filled over the last few years largely by answering these sorts of prompts and recording whatever thoughts they brought up. Because sex is such an important part of who I am, (and because it makes me so happy to write or talk about sex) I have searched a lot of phrases like, "Sexual Journal Prompts," and "Sexual Discussion Questions." Several of my journals are filled with nothing but sex: my memories, fantasies, insecurities and successes. Lots of those journal entries have served as the basis for stories on this site. For me, the practice of journaling has been incredibly valuable.

Just about every list of sexual journal prompts or discussion questions that I've come across is going to include (Usually even start with) "Write about your First Sexual Experience," or "Describe your First Time."

So, I'm going to write about Sarah.

I was 18 and she was... she was older than me. Not really feeling like the number is relevant here. We met through a charity organization where we both regularly volunteered. When the days were done, I would walk her to the car and we would end up talking sometimes hours into the night.

I recognized at the time that she was someone who was profoundly lonely. She would light up when I talked to her. I gave her attention and really listened to what she had to say. Seeing the way I made her happy...  it was one of the best feelings I'd ever known at the time.  We got to the point that we were talking almost constantly. She had a long commute to work and we'd spend most of her drive on the phone. Then we'd use messenger throughout the day while she was at her desk.  

I realize, as I'm sitting here smiling, that I haven't thought about those days in a long time.

We agreed to get together one evening and met at Odyssey Park. I haven't been there in years but I bet if I was there tonight, I could find the exact spot where I had my first kiss. She was shorter than me so we were standing on opposite sides of this wooden fence with me on the lower side. It brought her up to my eye level. We were facing one another, talking and gradually our bodies were moving closer, tighter together, our voices lowered in this intimate whisper until I kissed her on the cheek. I could hear her moan, reacting to the way my lips on her skin made her feel... so I kissed her more and I started moving around her neck. Then, she grabbed my face with both hands and kissed me on the lips. It was a pretty spectacular first kiss.

There was something very empowering about kissing her. I was able to bring pleasure to a woman's body. It was something I'd been dreaming about as long as I could remember, but it was finally real. There I was with my lips on a woman; making her moan, squirm and press her body into me. It was validating and invigorating. Intoxicating how confident I felt when I kissed her the first time until she couldn't stand it and kissed me back.

After that, things sorta snowballed. I had several firsts over the next few days, one after another. The day after our first wonderful kiss, I drove her to work in my old green pickup truck. I can still vividly see the dress she wore that day: blue and green pattern with flowers and a black ribbon beneath her chest. And it was short. I mean it wasn't like a mini-skirt or anything, but it revealed a lot of her legs. She was stunning in that dress. I had my hand on her thigh as we drove. I can remember the soft sensation of her skin against my palm. I slid my hand higher and higher throughout the trip. A big part of me was expecting that she would get upset or offended by me. She didn't, and each moment that she didn't react, didn't get insulted or tell me to stop... each minute made me a little bit braver. So, my fingers climbed just a little higher until they were beneath that soft cotton fabric of her dress. It was just as we were turning onto the street where her office was that my fingertips made their way to her panties. I was able to feel that they were wet.

This next part's dumb, but I hadn't kissed anyone before and I had watched A LOT of movies. I took a piece of mint gum and I was chewing it when we kissed good-bye. I used my tongue to pass it to her mouth. I thought this would be the most romantic thing but she just scrunched her face at me and said, "I didn't want that." Still, at the end of the day, as she was walking to the truck, I watched her pop a piece of gum into her mouth, which she then passed to me as we kissed Hello. It amuses me now.

I hung out in a big bookstore while she was at work, using sci-fi comics to keep me distracted from the monumental bridge I'd just crossed, all while I eagerly counted down until I could pick her up at the end of the day. This time, my hand went almost immediately beneath her skirt and back to her underwear. I started exploring, moving my fingertips this way and that, feeling the moist contours of her lips. As I look back on it now, I realize just how fortunate I was that my first lover was so expressive. The things she reacted to were very evident and I paid a lot of attention to her, feeling the spots on her body that she responded to the most. When she moaned, and I could hear that I was pleasuring her, it felt as if the sound was moving through my entire body. After a while, she said my name, slowly, and she asked, "Do you want my first orgasm with you to be in this truck?" I grinned and I felt very sheepish. I knew it would be more romantic if we were in her bed, but I didn't want to wait. I nodded and told her Yes.

She said she was impressed by how safe I'd been driving so far, but suggested a space we could pull over, in a large shaded parking lot that sits high above the freeway at the Mountain View exit. I do occasionally travel that freeway now, though not that often, and each time I pass by that exit, I still smile at the memory. Her panties came off and she laid across my lap so I could lean down to kiss her and watch her face. My fingers were inside of her then. I felt the delicious heat and moisture of her lips swallowing me into her. Her whole body pressed into me tighter. I held her, clung to her tightly. I can't say I had a real clear plan with my fingers. I was just moving them slowly back and forth, feeling her reactions to my touch. I doubt I had any real technique by that point, but I was clearly doing something right. Her orgasm was intense. Her eyes squeezed shut, moaning so loud it was almost a scream and waves of impulse making her body tense. Like I said, quite the confidence boost.

Naturally, I was hard as stone through all of this. My jeans felt so tight and cumbersome. From the way she was laying across my lap, I imagine she could feel my cock pulsing and throbbing against her back. She adjusted so she could grab my erection through my jeans. I gasped aloud and my eyes went wide like I was suffocating for air. It was the first time I was ever touched and it was thoroughly overwhelming for me.

Sarah immediately pulled her hand away and said, "It's been a looong time since I touched a virgin." I would later learn that made her very uncomfortable, but in that moment, there was so much wonder and newness to it all. I drove her home shortly after that. I can only guess that the expression on my face was a bit manic, because I had a lot to process.

So the night we kissed was a Tuesday, which meant that the night in the car was Wednesday. That would mean Thursday was the first night I stayed at her house. I was trying to work my way back just now to reconstruct the timeline. This all was a lot of years ago. Thursday night...

As soon as we got into her bedroom, I had her lay down on the bed. I remember the thrill of pulling her black panties down her sexy legs, looking with awe at her body lying there before me. Then, with her soft thighs draped across my shoulders, I got to taste her for the first time. It was incredible. It was just like using my hands, exploring with my tongue and my lips; watching for her reactions. Oh, that wonderful feeling, that sweet taste, the magnificent sounds she made when she came in my mouth...

She later told me that if that was our only experience together she would not have believed that I was a virgin. "You must have watched porn and REALLY studied." She didn't touch me that night. I wore underwear to sleep. Actually, I remember it being really important to me that I bought a new pair for the first time we were in bed together. I took them off at one point, once she was already asleep. Even then, it was so unbelievably amazing that a woman and I were nude in bed together. She said something the next day to the effect of "I wondered when those came off."

Oh. Here's a detail that was actually funny. Before she went to sleep, after she'd been in my mouth, she told me, "Do not freak out." Then, she got out of bed, lifted up the mattress and pulled out a gun, a pistol in a leather case. She had forgotten it was there, but felt it when I laid her down. I was very very grateful she warned me beforehand.

Now, I know that I stayed with her Friday night, and I know that I made her orgasm more than once and she didn't touch me, but apart from that, I don't recall any details or moments from Friday night. Saturday, she didn't have to work. By that morning, I'd spent two nights naked in bed with a woman beside me. I'd barely been able to sleep. As much as I was exhilarated, I was also exhausted.  

It was the first time I was ever inside of her.  She was on top of me, and almost immediately, she asked if I felt like I lost something. I was so confused, but the feeling was amazing. It was somewhat intuitive from that point, caressing her breasts and kissing her neck as she rode me. She climaxed very quickly. I did not.  

So, she took me in her mouth then. Again, such an amazing sensation, but I couldn't climax. I could see that she was disappointed, and I felt awful about it. That is a feeling I have grown quite accustomed to over the years. Sarah looked at me, after she'd given up... No. She didn't give up. I didn't remember this part at first. I was lying down on the left side of the bed, she was kneeling beside me as she tasted me. She said something about letting me play. I know she said the word play. While she had my cock in her mouth, I had my fingers from my right hand inside of her. I'd had a few days of experience at that point, and I was coming to know her body well.

I had her feeling so much pleasure she couldn't go on with her mouth. She laid down on top of my torso and I held her body with my left hand while my right brought her to orgasm. Wow, I cannot believe I forgot that until just now. That was amazing. Recalling that now, I still feel pretty proud of myself. When she had recovered, she looked at me and she could see how exhausted I was. Her expression was very kind when she put her hand on my chest and physically pushed me back, "Lie down, Babe. Rest." I wasn't awake very long after that, definitely didn't have the energy to protest. I slept for about three hours into the early afternoon. She had some food and watched a movie I think. 

When I woke up, we made love again. This time, I did climax inside her, and so did she. She was grabbing hard onto my shoulders as her body rocked with pleasure. She was gasping for air, but her smile was downright giddy when she said, "We came together."

A few minutes later, I was in her mouth again. I remember telling her that I was going to come, warning her. She surprised me by sucking harder, making me climax into her mouth. She was very proud of herself after that. She told me she'd been disappointed that she hadn't made me orgasm the first time, but she had more than made up for it.

I was not disappointed in the least.

Sarah and I were a couple for maybe six months. I would stay with her most weekends. I learned that she would respond to Chinese Food and white wine just about as if she was having an orgasm. She'd shout "PUPPY," any time she saw a dog anywhere on the street and never passed an opportunity to talk to a dog with endessly loving enthusiasm. She told me that she'd always dreamed of going ice skating, but never had the opportunity where we lived. She was over the moon when I got her tickets to an Ice Dancing Show for her birthday. Being around her, and learning to be a part of a couple now that I was an adult were wonderful experiences. I treasure those days.

Of course, I remember the reasons we broke up, but I don't think they really matter. Most relationships don't last forever. When I think about Sarah, it's all happy memories. I always picture her smiling, the way she would smile just for me.

There's one night with Sarah that I think about more often than any other from that time in my life. She had a friend staying over that night in the room next to the two of us. The walls were thin, so we knew we had to be quiet. I wasn't expecting sex to happen at all that night. We were in bed. She had her back pressed up against me and she surprised me by reaching her hand behind her and taking hold of my cock. She was slowly stroking me and I reached my arm around to slide between the lips of her sex. As my fingers were working her, I heard her moan. So, I reached my other hand up to her face and quietly whispered, "Bite." She bit down onto my hand, the space between my thumb and pointer finger and stroked my cock while I made her climax with my fingers. What I remember about that night was the feeling of urgency she had. She needed to feel my cock and needed to feel me pleasuring her in that very moment regardless of circumstance.

That's something I tried to express to her and I hope that she knows how grateful I am to her for the way she made me feel. Sarah made me feel wanted, desired like no one in my life ever had, and knowing that I was able to bring pleasure to her body and make her happy when I could, that gave me a level of confidence and love of myself I didn't know I could have at the time.

Thank you Sarah.

Thank you.

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AnonymousAnonymousabout 1 year ago

Such a great story with a meaningful message.

I will take some ideas for my first time. :)

AnonymousAnonymousabout 1 year ago

Gratitude is important and I'm so glad you have so much for which to be grateful. Thanks for sharing.

AnonymousAnonymousabout 1 year ago

I liked it!! You stated you were 18, but how old was Sarah? I love it when a young man, as yourself, satisfies an older woman sexually and fills her mature womb with his young seed.

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