Chapter 1. The Decision
I had a relationship for about 3 years with a women that absolutely blew my mind. I was 32 and in pretty good shape, and just getting into my career and starting to make good money. I was going out with friends a lot to bars and clubs, when one night I met a gorgeous 34 year old woman named Rebecca. She was a brunette with a great body and we hit it off from the start - we danced together one night and I left with her number.
I called her and we went on our first date. Dinner in the city, and then a movie. Nothing crazy, just a generic first date, but it ended with a kiss and laughs and she said she'd loved to go out again.
The second date I took her to a MLB game. I had some great seats from a work colleague and she said she loved baseball. It was fun but one sided game and We left after the 5th inning--went back to her place for some drinks. She had told me that she could only have a few glasses of wine and then had to sleep because she had an early work meeting. She was an attorney.
So, we went back to her apartment which was a nice condo in the city, overlooking the ocean. We entered and she poured us wine and put on some jazz music. I already had a nice buzz from game drinking but the wine tasted great. We sat down on her couch and immediately started to makeout. She stopped after a minute and said,
"I really like you. You're funny and sweet." She put her hand on the back of my head and fingers ran through my hair.
"I like you too." And then I kissed her more deeply. I moved my hand around her waist and then slowly toward her nice mid sized breasts. She moaned slightly and then gently pulled away.
"I like you a lot. I'd love to go out again but I do need to sleep now for work tomorrow. Is that ok? I hate asking you to leave but I'm nervous about tomorrow's morning meeting."
"Of course" I said. I told her that I'm a gentleman and I just couldn't wait to see her again. I think she could tell that I was slightly disappointed that we weren't going to "do" more.
"Listen...John. Before you go I just want to tell you something." I could tell she was slightly drunk. "I really like you a lot, but there's one thing that is sometimes hard to explain to guys. You all get so defensive." And she laughed while sipping more wine.
"I promise I won't!" I was so attracted to her that I didn't care what she said in that moment.
"Look. I'm a normal person. You're a normal person. But I have to tell you that I have an insatiable appetite for sex." I literally started to get hard. This was any man's dream scenario.
"The problem, though..." she said, "is that I am only really attracted to two types. Very dominant or very submissive."
I didn't know what to say. I was young and although I knew the terms, especially from porn, I didn't really get the psychological aspects. So I said "sure I get that. I tend to be more dominant."
"Ya," she said. "I can see that...you're very confident and assertive and I like that. But in the bedroom it has to be one or the other. But..."
"Ya??" I asked. Very confident because I had always been dominant with girlfriends in bed.
"Well, I'm a bit of a size queen. Sorry...I'm a little drunk." And she giggled. I had heard that term before but wasn't sure if it was a real thing.
"That's fine! I'm glad you told me," I said.
"I can't have one without the other..". I looked at her confused. "If a man has a big dick then I'm ok with him dominating me. But a dominating man with a small dick just doesn't work for me--in which case I love me a submissive guy! But I'm only talking about the bedroom. I like things to be normal outside of that. If that makes sense."
I had no idea what she meant but I said "ok, well I'm pretty sure I'll be your dominant man in the bedroom!"
"We'll see" she said, and wrapped her arms around me and kissed me on the lips. We said good night and I left for my apartment, but not before agreeing in our third date. This time we agreed that I would cook dinner for her at her place. As I walked out her door I was smiling and didn't stop until I got home. I was excited to show off my cooking skills, and, more than that, I knew that a date at her place for the evening likely meant I'd be sleeping over.
All week I thought about what I'd cook, and decided on a light dish. It's funny to think now that I wasn't nervous at all about her dick size comments. In my youth I was very confident, but also naive. I knew I didn't have a big dick, but I assumed inside had average sized dick because not one girlfriend ever seemed disappointed with sex. I also felt that my attitude and the ways I could be rather dominant in bed must have made up for anything I lacked in size. It wasn't until later that I discovered I was, in fact, slightly below average. My length was ok - about 5.5 fully erect. But I had very little girth. I would discover with Rebecca that I was the classic example of a pencil dick. Some women don't mind at all, and in fact prefer it, but not Rebecca, as I would soon find out.
I showed up around 4pm, as she had requested. When I walked into her condo we kissed and I began to unpack my bag of groceries for dinner.
"Ohhh, I don't know what you're making but I love all these ingredients!" She smiled. "While you prep for dinner I'm going to finish my work out, ok?"
"Not problem at all." As she walked back to her elliptical machine set up in her living room across from the kitchen, I watched her ass. It looked so good in her tight yoga style pants. Her long dark hair was in a ponytail against her white tight shirt. It looked wet with sweat and her breasts looked twice as big as they usually looked. I could feel my dick twitch.
As I began prepping everything and occasionally would look over and smile at me. Her breathing was getting heavier as I could tell and was on her last 5 minutes. "Almost done!" She yelled from the living room. I finished prepping and then set everything aside and opened a bottle of wine. I assumed I wouldn't start actually cooking for a few hours, and I had guessed she'd want a shower.
She walked over and threw a towel around her neck. "Wow that was a tough one!" She gave me a quick peck on the cheek and chugged some water. "I have to shower but first I want a glass of wine. You don't mind if I shower a little later do you?" Not at all I said. We sat on her couch.
She finished her first glass pretty quickly and I grabbed her a second. I couldn't stop looking at her body. Very sweaty and just perfectly in shape. I noticed her thighs were very muscular.
"So, you workout a lot huh?" I asked.
"Every day. I love it. It distresses me, and as a bonus I get to look hot." She grinned. It was the first time she said anything even slightly arrogant.
She put her wine glass down and sat even closer to me, placing her hand over my pants near my crotch. I could feel my dick getting hard. She kissed my neck. "Mmm I missed you today." Then her hand found my dick. She whispered in my ear: "so, what will I find here? Is this the moment of truth?" Her fingers were still outside my pants but started to outline my dick which was fully hard.
"Yes" I said. She suddenly stood up and her tight ass was right in front of my face. She turned and looked down at me. "Well, then come take me." I got up and followed her into her bedroom. I knew what to do. I quickly grabbed her waist and kissed her neck from behind. Her eyes closed and she let out a small moan. Then gently placed my hands inside her workout yoga pants and yanked them down. She was wearing a thong and that came off too. I aggressively pushed her on to the bed so she was leaning on it with two hands, basically presenting her ass to me. I immediately dropped my pants and went right inside of her.
In retrospect, I'm surprised at how quickly my dick entered her. She was definitely wet but there was no resistance. In fact, it had been like that my whole life. I just figured that was normal.
I grabbed her hips and began thrusting into her. I wanted to show her that I could most definitely be dominant. I got about four big thrusts in before and let out a small moan. I'm getting somewhere, I thought. Just don't cum yet. I was about to make my sixth thrust when she said "ok stop, stop please." I pulled out and she turned and sat on the bed. "Come give me a kiss" she said.
I sat next to her and kissed her. I figured maybe she wanted a different position but I also had a feeling something wasn't right. "Well, I think I know now." She pulled her pants and thong back on and sat up by the top of the bed, even with her workout sneakers still on. She patted the pillow next to her. "Come sit next to me. And keep your pants off" she said with a grin.
I sat up next to her. She grabbed my dick and started slowly stroking it. She whispered into my ear. "I like you a lot, John. But this is what I would call a pencil dick. I need to thicker and longer." She still kept slowly stroking me."