I Cheated on My Date

Dear Diaries,

I thought I would share with you one of the most mind-blowing sexual experiences of my life. Granted I am still young at only age 25, but I imagine this will stick with me for a while.

In traditional fashion, this didn't happen today, but a couple of weeks ago during the holiday break. Names have been changed to protect the innocent, or in this case, not so innocent. This story will be a little long, as I think a short back story will help set the mood and scenario up a bit better.

Last year I finished my degree in Electrical Engineering and immediately took a job in Detroit. Because of my busy school schedule and then the load of starting a new high paced career, I haven't had much time to get back home to see my parents. So I decided I would use my saved up vacation time to take a couple of weeks off for the holidays and head home.

At 25, I am the oldest of three, so I am first to graduate, and the first to move away. As you can imagine this has been a bit hard on my mom. Especially since I haven't been back as much as she would like me to be. She has also started to take way too much interest in my "love life". Always asking if I have met any nice girls. Telling me that now that I have a good job, I need to meet a nice girl, and give her some grandchildren, and so on.

I won't lie, part of me thought about not going back home for Christmas just so she wouldn't have as many opportunities to nag at me about being "SOOOOO" far away, and needing a girlfriend. But I wanted to be a good son and hoped that maybe being home for a few days would help ease her mind a bit. Oh, how I should have known better!

I got home late in the evening on Saturday a week before Christmas. A bit too late for dinner, but not so late as to be rude. I did that on purpose as I didn't really want to have to go do some big meal after a long drive. Of course, my mom was having none of that. As soon as I walked in the door, I could smell dinner. The scowls I was getting from my brother and sister made it pretty clear they hadn't been allowed to eat until I got there.

So we got the hugs, kisses, and a good ole fashion arm punch out of the way and hurried up to dinner. Once my siblings got to eat, they were a bit happier, and most of the dinner was spent telling everyone about my job and apartment in Detroit. By the time we started finishing up, it was around 9:30 pm or so. Mom asked if I wanted to hang out and do anything, but I told her that I really just wanted to get some rest after my drive. Not that Chicago is that far of a trip, but still. After a little initial disappointment, she agreed.

Just as I was getting up from the table though, she stopped me and informed me that we "WOULD" be going to church at 7:30 in the morning. I started to protest, but she quickly made it clear it wasn't an option. I grumbled a little bit but didn't figure there was much point being too prickly about it. So I started to head upstairs to my old room. My dad got up and helped with one of my bags. My mom said she would be up in a minute too, as she needed to grab my sheets from the dryer.

Dad and I had a couple of minutes of banter before mom got up there and then he excused himself once she arrived on the premise that I needed my beauty rest. My mom, of course, had other ideas. She wanted to make my bed for me, made sure I had clean clothes for the next day, etc. I tried to politely shoo her away telling her that I could make my own bed, and all my clothes were clean. After some persistence, she conceded and headed for the door. Before she closed it though, she took a moment to remind me that I needed to be ready to leave at 7:30 sharp. I should also dress fancy because she has someone special she wants me to meet.

I think we all know where that was heading. My mom is a great mom, but I honestly have no desire for her to play matchmaker for me. I just sighed and re-assured her that I would be ready. I'm not however sure that anyone can ever really be prepared for their mom to try and introduce them to girls.

Sunday morning came, and we all loaded into the family SUV and headed off to church. The service went as well as can be expected, and surprisingly other than a few "mom gushes" over me being back home, it wasn't a bad time. As we filed out of service though, my mom was quick to start pulling me around to meet different people. Most were just her normal friends, but then we ran into Mrs.Tucker. She was a single mom that I had met a couple of times when she came over to hang out with my mom. At first, they just seemed to be saying hello, but then the bomb dropped. My mom asked her if "they" were still good to meet up for brunch.

Unless things had changed in the last couple of years, Mrs. Tucker was still single. (Rightfully so if you ask me, she's a bit out there.) That meant the "they" would include her daughter. My mind started to race. I had met her daughter a couple of times in passing. We lived several miles apart, so we hadn't attended the same schools. As we milled around and made our way back to the car with the rest of my family, I started to put bits and pieces of old memories back together.

Brunch was only a couple miles from the church, so it didn't take long to get there. Long enough for me to remember that Sarah Tucker wasn't a bad looking girl, but had always seemed a bit too much like her mom for my tastes.

We walked in at nearly the same time as Sarah and her mom. My memory wasn't wrong, she was indeed a looker. Long blond hair, blue eyes, and a pretty decent body. Maybe not all so bad? I gave her a quick smile, and I think I got a bit of a grin back, but it was very fleeting before she returned to her phone and whatever she was doing on there. With church just letting out, and this being a favorite spot for brunch afterward, it took a few minutes to get seated. We didn't really interact during that time. She mostly texted on her phone, and I spent the time catching up with my brother and sister.

They sat us at a set of two tables pulled together. My mom was quick to ensure that the seating arrangements had me sitting on one end, with Sarah sitting at the side next to me. Both our moms quickly pointed out that we should get to know each other a bit better. This was all a bit embarrassing for me, but I figured I wouldn't hear the end of it if I didn't at least try and satisfy my mom.

The first few minutes were filled with awkward silence, and a little too much attention being paid to the menus in front of us. Neither of us really saying anything. I'm generally not all that shy, and I didn't get the feeling that Sarah was either. I think neither of us just really felt all that comfortable with our moms trying to set us up. The waiter finally came around taking orders and breaking the silence. I decided then, I would try and break the ice and at least make some conversation. I mean she was beautiful so it couldn't be that bad, right?

The waiter took my order first, and then hers. After he took her order, she reached over to take a sip of her water, and I used that moment to get things going. "So what are you studying in college?" I asked. I guess she was off in her own thoughts as it took her a moment to realize that I was looking at her, and must have asked her a question. "I'm sorry did you ask me something?" she responded, using her napkin to dab excess water from her lips.

I smiled and repeated my question, this time with her attention turned my way. "Well, I'm not really in college right now. I'm focusing on my career instead," she said with a smile. I could tell she was excited about her career from the inflections in her voice. So I continued the conversation by asking her what she was doing as a career. She proceeded to tell me how she was going to be an actress and was planning to move to Hollywood and star in the movies.

With a considerable amount of prodding to keep the conversation going, I learned that she had starred in a commercial for a car dealership she was working as a receptionist at. This gave her the acting bug, and she had decided to focus all her energy on being the next big star. While she seemed excited about the fact that she was going to be a huge star, it was evident that she was far more interested in whatever was happening on her phone than having a conversation. As the food was delivered, I decided to give up on the conversation and just eat my food.

I could at least tell my mom I tried right? If it was only that easy! As though our moms had some kind of "silence" detection alarm, they both seemed to immediately notice that after we finished eating, we weren't really interacting. Her mom reached across my sister who was sitting between her and Sarah and pushed her daughter's phone screen down. "So are you two getting along well?" Ms. Tucker asked. Sarah glared at her mom but put her phone down on to the table with a bit of a huff. My mom took this as a sign that she also needed to get involved. "Have either of you seen that new movie? A Star Is Born. It's excellent," she asked. Sarah and I both shook our heads no, and Ms. Tucker took that as her queue. "Maybe you guys could go see it together this week?" she said. "Oh that's a great idea." my mom chimed in.

At this point, neither Sarah or I were really involved in the conversation, other than as servants to our mother's will. By the time we all got up from the table, the mothers had decided I would be taking Sarah to see the movie on Tuesday afternoon. The only interjection we got into the mix was that I would be meeting Sarah there, instead of me picking her up to take her.

*****

I spent the rest of the day hanging out with my siblings and avoiding my mom. I knew she would be a little naggy about getting a girlfriend, but this was overstepping as far as I was concerned. Especially since it was clear that Sarah really wasn't interested. I seriously considered just not going. Boy am I glad in hindsight that I went.

Tuesday came around pretty quickly, and I found myself just lounging around waiting for the inevitable. Sarah and I had texted a couple of times to confirm the plans, but nothing really beyond that. I guess honestly, I didn't really try that hard to engage her in conversation, as I didn't get the initial impression she was interested.

The movie was at 5:30 pm, but the afternoon seemed to be dragging on forever. The theater was one of those newer, fancy theaters, with a bar in the lobby, the big comfy recliners, and so forth. So I decided about 4:30 to head on over. It was a bit early, as I was supposed to meet Sarah at 5:15 in the bar area. However, I wanted to grab a long island iced tea beforehand, just to loosen my social anxiety a bit. Who knew, maybe if we each had a couple of drinks, we could break the ice a little better.

Being a Tuesday night, it wasn't super busy. I got parked and headed on in. The place was nice for a theater, and the bar area was bigger than I expected. I had planned to just sit down at the bar and grab a quick drink. As I approached the bar, I noticed it was mostly empty. There was however a group of girls around one of the tables, giggling about something. Their giggles caught my attention, and I noticed Sarah was one of them.

As I walked up, she saw me and waved briefly. She was still conversing with her friends, so I found a table nearby. The waitress came over and took my order for a drink, and about the time it arrived Sarah also came over.

We exchanged a few pleasantries, and I confirmed she had gotten the tickets. Since they sold the tickets online and reserved specific seats, it had been easier just to send her the money for mine and let her get both ours at the same time. She handed me my ticket and then ordered a refill for her drink.

We made some small talk about what we expected from the movie, and if we wanted to get any popcorn or anything. It wasn't long though before Sarah was back on her phone texting away with someone.

It didn't take much time for me to realize that her messages and brief smiles on her face seemed to coordinate with the girls she was initially talking to giggling. I mentally sighed to myself and sipped my long island down a little faster than is probably acceptable. I thought a couple of times about pulling my own phone out but decided I would try and avoid going down that road.

As I sat stirring the last of the ice in my glass around with my straw, I noticed one of the girls at the other table also seemed to be spending a little too much time nursing her drink and not engaged with the other girls. They were all standing around their bar height table, mostly paying attention to their phones, but she seemed to be staring into the abyss of the bottom of her glass.

About that time she looked up and caught me staring at her. As is customary, I quickly glanced away and back to my now empty drink. For some reason though, I found my eyes gravitating back up towards her. Where I promptly found her eyes still fixed on me. I felt my cheeks blushing, and gave a bit of a stupid little grin. I'm not sure why, but at that moment my brain decided to pick up my glass and give a mock toasting gesture.

To my surprise, she smiled back and returned the gesture. Before my brain had more than a few milliseconds to ponder this interaction, it registered that Sarah was no longer looking at her phone but at me. I wasn't really sure what to do here. I mean I had just made toasting gestures with some girl I didn't know at all while sitting at a table with my "date." Probably a total dick move, but what could I say, she had been ignoring me. Still, my brain said I needed to save face, and I quickly asked if she wanted a drink refill.

Sarah looked back to see who I had been looking at, and then with a bit of an eye roll accepted my offer for a drink refill. Not seeing the waitress handy, I decided this was an excellent opportunity to step away from the table for a second. I grabbed both our glasses and headed for the bar.

My brain was starting to feel the first drink, but only a little. Not enough to help me figure out what I was doing here. Then for some reason, as the bartender took my order for refills of our drinks, I also blurted out that I wanted to order a refill for the brunette with shoulder length curly hair at the other table.

He gave me a bit of a questioning look and then just shrugged. "I think she was having a long island iced tea as well," he said. I asked if he could send it over to her, and he agreed. Grabbing my drink and Sarah's cosmo, I headed back to our table. I set the glasses down and tried to pay attention to Sarah again. She took a sip of her drink, but never stopped looking down at her phone.

This was growing a bit old quickly, and I was starting to wonder if I should just leave. Then I saw the waitress heading over to the other table carrying a long island iced tea. She set it in front of the brunette at the other table and then after exchanging a couple of words pointed at me. This promptly resulted in our eyes meeting again, and her raising her glass with a nod in my direction.

I smiled a little and then looked down. Was I really sitting here flirting with another girl while on a "date" with Sarah? What did that say about me? As I sat there for a moment pondering what I was doing, Sarah stood up and asked if I was ready to go get seated. I snapped out of my thoughts and agreed that it was time.

This theater had reserved seating, so we quickly found our exact seats. They were plush leather recliners with little pull out trays for your drinks/food. After we sat down, a waitress came by and offered us some small airline pillows and blankets. She also offered to get us some new drinks and asked if we wanted to see menus. I decided the two drinks I had were enough but accepted a blanket and pillow. Sarah and I were paying for ourselves on this "date," and she ordered some caramel corn and a bottle of water.

A couple of minutes after we sat down, the group of girls that Sarah had initially been with came in. They immediately made their way right to where we were sitting. Three of the girls made their way past us and sat on the other side of Sarah who was on my right. Given that the theater was not expected to be full, I suspected this was on purpose. As I was looking in their direction, I felt someone sit down in the chair on my left. Looking over to see who was sitting there, I quickly froze up. It was the brunette I had been flirting with at the bar.

After a couple of moments of shock, I snapped out of it and sat up a bit straighter in my seat. Nothing was said by Sarah, the brunette, or myself, but I certainly was starting to feel a little uncomfortable. Why had I bought this other girl a drink, why did I keep finding myself staring at her. While I knew that nothing was going to develop between Sarah and me, it just felt wrong to be thinking about this other girl while here with Sarah.

The theater started to darken, and the pre-movie trailers started to play. As the waitress took other people's orders, and eventually brought the items Sarah had ordered, I reclined my seat a bit and covered up with the blanket. I think they intentionally keep it too cold in here just so you will have to cover up.

Sarah offered me some of her caramel corn which I declined, and it was then passed down to her other friends. Finally, the movie started, and for a change, Sarah actually put her phone down.

We were about 20 minutes into the movie when something very unexpected happened. I was sitting there reclined with the little blanket they gave me covering me up. My arms were under it with my hands crossed in my lap. At first, I thought Sarah had just bumped me by accident, but it only took a second for my brain to realize that the fingertips moving down my arm were searching for my hand. I adjusted my arm moving it up onto the armrest between the chairs, but still covered by the blanket. I felt her hand slip into mine. It was so warm, and her skin felt like soft velvet. Our fingers interlaced and I felt a little squeeze.

I absolutely wasn't sure what to make of this, I certainly hadn't expected it. My brain started to race a bit, trying to figure out what Sarah was doing. I started caressing her hand a bit with my thumb, rubbing it gently along the side of her thumb. I think it was mostly nervous energy causing me to do this. Then I suddenly froze my movement. I was moving my left thumb, not my right thumb.

Those long island teas must have been stronger than I realized. My brain was clearly running slow because I should have realized this much sooner. Sure it had only been a few seconds, but when the wrong person is holding your hand, you would generally know it pretty damn quick. I wasn't sure what to make of this at all. There was no one on the other side of this mysterious woman holding my hand. Was she doing this on purpose? Was she holding my hand out of habit from going to the movies with her boyfriend? Did she realize what she was doing?

I started to try and slip my hand free of her gently, but she just squeezed harder. Looking directly at her, I saw she was focused on the screen but had a grin on her face. I stopped trying to free my hand and returned to caressing her thumb with mine. I may not have understood what was going on here, but I certainly wasn't going to pass on an exquisitely beautiful woman holding my hand.

My mind raced down a thousand different possibilities of what was going on here, some of them weird, some of them erotic. None of them reconciling with any basis of reality that I might have. This just seemed to out there in the realm of possibilities for my brain to really put a valid scenario together.

I started to worry about what might happen if Sarah realized what was going on. I glanced over at Sarah, she was focused on the movie, and turned about a quarter turn up onto her side in the chair, showing me a bit of her back. She likely wouldn't see the lump of our arms on the armrest. We were under the blankets, but anyone looking could have seen that our arms were entangled under them. What if she turned or got up?