Peyton

Well to start, there’s this small family owned Italian restaurant by my house that’s probably my favorite, especially Friday evenings after work, when I need a drink, and something to eat. The staff there is always very friendly, and being I’ve been going there for a very long time, many know me when I walk in, or at least it feels that way. Anyways, the owner likes to hire high school and college kids, trying to give them their first opportunities to work, which I support.

With that said, this one particular Friday, I immediately noticed there was a new hostess they had hired. She was a very attractive young girl, and her friendly smile and, bubbly demeanor almost immediately had me drawn to her. She really was pretty, had a friendly personality, and a smile that made me stupidly smile too.

She had dark straight, shoulder length hair, and being she was petite, small framed, she didn’t have big boobs, which I liked. It really was hard to not check her out every time I’d follow her to my table, and think about being with her, especially seeing that great looking little butt. Furthermore, seeing that pretty face smiling back at you, it really was hard to not get caught staring at her firm little body and tits, especially whenever she happened to wear one of her tight black top.

Most of the times, when I followed her as she took me to one of the booths, continuing to smile, I couldn’t help but look down at the fancy design on the back pockets of her jeans. “Man,” I thought, “she’s got a great little body,” and seeing her shapely little ass and somewhat long legs in those jeans as she walked away, only accentuated the fact.

Sitting down, I couldn’t help but watch as she walked away, and again think about being with her. However, being I had to be more than twice her age, I knew there was no way, but it was still hard to not fantasize about getting her in bed. Every time now, when I visited this restaurant, which was starting to be more and more often, I always found myself looking for her, always hoping to strike up a conversation, hoping there might be that opening to ask her out.

However, being she was obviously a student, she wasn’t there much during the week and when I realized she was usually there only on weekends I tried to go not only Fridays like usual, but Saturdays too. She really was so attractive, naively friendly and whenever we happened to talk, I always ended up clumsily flirting with her. I wanted it to happen but it was easy to see it made her a little uncomfortable, especially when there were other customers or staff nearby. Yea, I know it was awkward, and I didn’t want her to feel uneasy, but I really liked her and continued to hope maybe there would be a chance.

She was all I could think about and after a couple weeks, I got up the nerve to ask her, “What’s your name?”

I already knew the answer, because I asked my waitress one time, and when she smiled and simply replied, “Peyton,” there was an awkward pause.

Smiling too, I introduced myself, and as we shook hands, I stumbled over my words, trying to hold a conversation. It was a little embarrassing and as she eventually left, I couldn’t believe how tongue tied she had made me, which left me again to think, “There’s no way.”

However, the more time I spent there, the more obsessed I was becoming, and when she happened to wear a pair of these tight yoga pants, that more than accentuated her tight little butt, I thought, “My god, I want to be with her.”

I wanted to see her as much as possible, and it had to be obvious I was looking to make something happen. We were becoming more personable, and the more we saw each other, the more it felt like we were becoming more friendly, leaving me to think, she might be attracted too.

Maybe I was giving her a lot of attention, but it was for good reason and maybe it was just me, but every time after taking me to a table, and saying my waitress would be over soon, she’d always give me a parting smile, always leaving me gawking as she walked away.

She had to know I was interested, at least I hoped she did and whenever she’d happen to casually stop by to check in and talk to me it made me think, “Maybe, just maybe, she is interested too,” but then again, I felt it was just her needing to be a good hostess.

I tried to ignore my feelings for her, being she was so much younger, but it was hard, and when I found out from one of the servers that she was actually in college, I again thought maybe, which again had me searching for a way to graciously ask her out.

Yea, I was fantasizing about being with her, and coming to realize there was no way, I left it alone. However, she was always on my mind, and feeling I needed to push it, I went way out of my comfort zone this one time when she happened to stop by my table to talk, and seeing an opening I bravely asked, “Do you maybe wanta go get a drink when you get off work?”

I knew it surprised her, I’m sure of that and after a long pause I said, “Yea, I’m sorry, you probably have a boyfriend.”

It made her smile and blushing she said, “No, I don’t have a boyfriend,” and looking at each other, I smiled, and as I thought of a way to respond, I shifted in my seat, but before I could say anything she said, “Sure I guess.”

It surprised me and as I searched for where we could possibly meet she said, “I’ll be right back.”

I worried that she was blowing me off but she eventually did come back, and seeing her apprehension I waited for her, hoping she’d indicate that she meant it. Wanting to see if there really was a possibility, I smiled and taking the opportunity, I suggested, “ How about somewhere down in olde town?”

She was hesitant how to answer, and I think she was hoping I really didn’t mean it, but then smiling she said, “Sure.”

I couldn’t believe it, but after talking about when and where, and exchanging phone numbers, she again left, heading back to the hostess station.

From a distance, I could see her looking my way, occasionally smiling, and not wanting to appear overly excited, which I was, I tried to not show it. I was so excited to maybe be alone with her and after finishing my drink and plate of spaghetti, I paid my bill and got up to leave. We ended up smiling at each other as I left and when I casually but nervously said, “See you later,” she smiled.

It was an awkward one, and then after quickly looking around, she again turned and smiled as a couple of the other hostesses said, “Bye.”

Maybe it embarrassed her a little, and I really hoped she meant it, but as I sat at home waiting impatiently, and feeling she was just being polite I thought, “It’s not going to happen.”

I wanted to text her, but I didn’t want to look overly anxious, and knowing when closing time was, I waited, continuing to think about being with her. Hoping she’d contact me, I checked my phone often, but after a while, I again felt, “She’s blowing me off.”

Yea, it was for good reason, being I was so much older. I worried it wasn’t going to happen, but then suddenly there it was, a text message. Quickly grabbing my phone and looking, it was her. It made me smile and as I opened it and I saw her message telling me she was off, I immediately responded, “Great!”

I was excited, but nervous, and as I searched for where we could meet, she texted me, suggesting we meet at a little pub down in olde town. I sensed she was nervous too, and maybe a little anxious about meeting, I know I was, however I wanted the chance to be with her.

I knew where the bar was and after a few messages about timing, I got cleaned up a little. I didn’t want to appear too anxious, so I didn’t change my clothes, but I did spray on some cologne and then thinking, hoping, I decide to grab a condom out of my drawer. Smiling, I tucked it in my pocket, and then decided that I should probably bring a Cialis too, just in case. Yea, I know it’s weird, but I had the pre***********ion for those times when, you know, you didn’t want to fail, and this was just one of those times.

Quickly pushing it into my pocket too, I headed off to meet her. I so wanted this to go well and after parking a little ways away, I made my way up to where we were going to meet. It was already kind of dark and when I saw her waiting out front, I confidently smiled, as I continued to walk toward her.

Eventually, Peyton turned and seeing me coming up the sidewalk, she smiled too. It looked to be an excited one but a little nervous too, and after saying, “Hi,” we shook hands and headed inside.

I couldn’t help but think, “This is so nice to finally be with her,” but in the back of my mind I continually thought, “There’s no way,” but convinced myself, “just enjoy it.”

We ended up talking, having a couple of drinks, and jokingly we got to know each other. In conversation I found out she had graduated from a nearby high school and that she had been a cheerleader there. It wasn’t hard to imagine, being she was so attractive and friendly. We were definitely having a good time, but seeing we might be drinking a little too much, too soon, I suggested we order some appetizers.

It really was a good idea, I so wanted this to go well, I didn’t want either of us getting too drunk, and after awhile, when there happened to be a lull in our conversation I brazenly asked, “Do you wanta come over to my place?”

It obviously surprised her, because she seemed to be leery, questioning it. I definitely didn’t want that, and seeing her reaction, I stupidly tried to take it back by saying, “It’s okay, I understand if you don’t want to.”

I could, however see her thinking about it, trying to determine what my intentions might be, but then she smiled and nervously suggested, “How ‘bout we go to my apartment instead.”

I didn’t know if she really meant it, or if she was really looking for a way to end our, let’s say date and escape. In either case, I said, “Okay,” and trying to not act overly excited to be alone with her, I simply smiled.

She still seemed unsure at first, but smiling she too said, “Okay.”

I think in a way she felt obligated, but it still made me smile to think about being with her. I really was excited to go over to her apartment, and as we finished our drinks and the last of our appetizer, I got our waitress’s attention.

Quickly paying the bill, I looked over at Peyton and when I asked, “Are you ready,” Peyton smiled hesitantly, and nodding, we left the bar. I still had a feeling she was maybe a little apprehensive about being with me, but trying to shrug it off, I asked,” Where do you live?”

Smiling she said, “Why don’t you follow me.”

Smiling too I jokingly replied, “Don’t lose me.”

I’m sure she was thinking about it, but being she lived kind of close, it didn’t take us long before we pulled into her complex.