One last tryst

Things with Larry, the kid, weren't working out at all. Though I had managed to be introduced to his family during the holidays, I knew he wasn't the one.

Girls have that feeling by instinct. To me, if it's not going to happen, I immediately stop trying. However, if I do sense someone could be "the one", I can't get the idea out of my head- which was exactly what the IT Pilot was for me.

I had been texting on a daily basis with my friend out in NYC, telling her of my tryst and feelings about the IT Pilot. "He's not right for you" she'd said. "I know, and it gets on my nerves that he could never figure out what he wanted. I gave him his freedom, let him do what he wanted, but it wasn't enough. Thing is, the IT Pilot was it for me" I told her. "What do you mean?" she asked.

"Well, he's the guy who I saw possibly marrying. He's husband and father material, Larry isn't. We don't get along, and he's too immature for me, it's aggravating" I told her.

"You saw the IT Pilot as husband material?'

"Yes, I do. I know he'd be a great father" I told her.

But the IT Pilot and I never talked about our last encounter; instead, we'd played the quiet game, pretending nothing had happened. A few weeks into the new year, I asked him how things with the new house were going. He had finally moved in and settled, and was very happy. He suggested I come by for a visit sometime to check out the new house.

We began flirting, teasingly jabbing at each other. He asked me if I was still seeing Larry, but I dodged it as best I could to stay away from the subject. I finally got the guts to say what had been on my mind for quite some time. We'd always agreed that sex between us was great, but to me, it had been the greatest I'd ever had.

Ren: I have a question
IT: k?
Ren: Was the sex really that good, or was that my imagination?
IT: The sex was really really good... the best actually.

At least I have some affirmation there.

Ren: Which position did you prefer? You on top or me on top?
IT: Both, but you on top.. I like how you move up and down. I feel more. But I like being on top and making you come. I love to make you scream.
Ren: Both position surprisingly for me.
IT: Really... I thought you liked me on top. I didn't think you liked to be on top.
Ren: I liked making you come when I was on top (but I can't remember if I did)- but I could only orgasm with you pounding.
IT: I think maybe once.... you wanna practice :-p Oh I love it when you come. Wow...

I could feel the hair at the back of my neck standing up.

Just like the month before, we had made plans to meet again, this time for me to visit his new home after we finished playing bingo on Thursday night. I showed up there earlier and we took our seats and made small talk. Soon enough, the beer made its way into our bodies and we started flirting endlessly. I tried my hardest not to make certain advances and didn't touch him inappropriately as I'd done countless times before during bingo. However, at one point during the night, the beer had made me increasingly chipper and I leaned in to kiss him on the cheek. He responded shortly after by putting his arm around me and leaning me into him as he kissed me on my head... to which I heard him breathing in deeply.

By the end of the night, we made our way back to his new home, about 5 blocks away from the bingo hall. He guided me in and gave me the grand tour. It was a beautiful 3 story town-home. The first level had the master bedroom and bath, the second level had the kitchen, living room, and approximately 30 feet ceilings, and the third floor had two extra bedrooms and bathroom. It was eerily quiet and simply organized. The IT Pilot was a minimalist, and didn't have much decor to add to his environment.

We came back downstairs to his bedroom and I gave him his housewarming gift- a bottle of Chilean Cabernet Sauvignon, one of his preferred wines.

"Cabernet? Wow, that's great. Thank you" he said.
"I know, I remembered you liked it" I added.

He pulled me into him and hugged me tightly, to which I became overwhelmed with confusion, urges, and feelings.

"What are you doing? What are WE doing? You need to let me go, let me move on" I told him.
"YOU let me go" he said in a drunken state.
"I did! You gave me my closure last month; You told me it wouldn't happen, and to let you go, so I did! Then you start talking to me again, and here we are" I said to him. "You need to quit me."
"I can't" he said, as he burrowed his head into my chest.
"Quit me" I said once more.
"I can't!" he said again.

We laid back into bed, getting ready to fall asleep when we got on the topic once more of why things had ended. We talked. A lot. It was definitely a lot easier with a lot of beer beforehand. Neither one of us really held back or had a filter. I really had nothing to lose.

I pushed for it telling him to quit me, to let me go, and he kept saying he couldn't- that he ended up missing me and would text me because he cared. Hell, I thought about him too, but I didn't text because I was pretty much convinced that I'd reached my closure. I don't think it's a good idea to date him right now. I mean, yes, I liked him. A LOT. But each time we broke up, a bigger piece of my heart died out.

"I felt like you were hiding something from me. I was walking on eggshells around you" he said.

As soon as I heard him say this, I let out a shocked gasp. Just days before, I had been texting my friend and telling her of my feelings for the IT Pilot.

"I think we didn't last because my guard was completely up. I always went with the reasoning that we were both too proud, both had our walls up, and neither one of us was able to communicate efficiently. That's why we didn't work out. I felt like I was walking on eggshells because I felt he would leave me" I had said to her.

"Eggshells? Really? You know what's funny, is that's exactly what I told Shann on how I felt about you" I told him.

I couldn't believe it. Somewhere in that mind of his, we had shared the same feelings for one another, but never attempted to share it out loud. We were too afraid to come clean, and admit that we cared for the other.

At the end of the night, it wouldn't work. Our time wasn't now, and it wouldn't be any time soon. We laid in bed and held each other. We had one last tryst, and the next morning, he walked me to my car and kissed me goodbye as I left for work.

The next day, I left to NYC to visit my friend Shann for a few days, and the IT Pilot and I managed to get a few texts in here and there, him mainly checking up on me to see that I'd made it there okay.

Even though I cared immensely for him, I had to let him go. Even though things with Larry weren't working to my expectations, I realized the reason being was that I wasn't giving him my full attention, seeing as to how my mind was drifting off to someone else. It was time to move on. Larry had persisted to great lengths to be with me, and I felt I owed him the chance to try to see if something could work between us. So I did.

But it backfired.

I can't feel a thing

As soon as the IT Pilot and I began to have sex, something felt different. I would have thought maybe all the alcohol we'd had earlier in the night played a big factor, but after careful thought, I realized that no, it wasn't that.

I could hardly feel him in me.

F*ckkkk!!!!

Larry who was much larger than the IT Pilot had quite possibly stretched me out, and the feel of the IT Pilot's penis in me was quite different now.

I was pissed.

This is karma, somehow, I thought.

It took a long time for me to reach orgasm with him; Larry had officially ruined sex for me and the IT Pilot. Sex between us had been the best thing I'd ever experienced, and the size had never been a problem (I'd actually enjoyed it because I didn't experience too much pain), but sex was now entirely disappointing.

Wait.... If I can hardly feel him... does that mean that [gasp] I feel looser to him too?

I didn't dare say anything to embarrass him or myself from our sexual tryst, but I was saddened by the situation.

We both came to orgasm together, and soon after fell asleep. The next morning, we laid in bed together, as I stared up at the ceiling rethinking the events of the previous night. The IT Pilot couldn't keep his hands off of me, and it was beginning to smother me. He held me the entire morning, caressing me, running his fingers through my hair and kissing me. A while later, he decided to go with a repeat performance, something that shocked me, considering we'd never had morning sex (it's not my thing) after evening sex.

I was hoping the alcohol had worn off and that things would feel different the second time around- except they didn't. I could hardly feel him in me once again.

I was embarrassed for the both of us.

We went out to Pei Wei soon after for lunch, and had that awkward silence during our meal. Even though we'd had a good sexual chemistry before and got along great, things were very different now that we weren't together. The only thing I really talk about when I'm with friends is guys and work- and with him, I could only discuss one topic.... and that was rather short.

Around 6:00 p.m. I decided it was time for me to retreat on home. Since I didn't have extra clothes with me, and had been wearing a miniskirt and pantyhose from the night before, I had to borrow a pair of sweats and a t-shirt from his closet. This meant I'd have to see him again to return his clothes sometime in the future.

I wonder what's going to happen then.... I thought.

Drinks with the IT Pilot

The IT Pilot and I had been incommunicado ever since our last phone call before Halloween which had resulted in our breakup. Around Thanksgiving, I sent him a friendly text message wishing him a Happy Turkey Day, knowing he'd be couped up with his family in Alabama. He responded, and we exchanged a few friendly words, but nothing more.

The next month, in mid-December, we communicated again and flirted the entire night through texts. It was a side of him I'd never seen, a side which had left my interest piqued. I didn't mention anything about dating Larry, and he told me I was still the last person he'd been with, and hadn't found anyone to date even though he was still on OkCupid. I had expressed confusion about how our relationship had ended, and had asked him to tell me point-blank that it was over so that I could move on. He asked me to tell him why I needed him to say it, and I answered "Because if I don't hear it from you, then I'll never know it's over."

"Yeah, let's move on. I've sort of been stuck in the mud too. It won't work" he replied.

However, we agreed to meet for drinks on Friday night after my department's Holiday Dinner to "talk", something which confused me even more.

I was dressed to the nines from my work dinner, and promptly drove over to his apartment to meet afterward. He drove us out to a bar in the university village area nearby, and for the first time ever, we had drinks and listened to a live band play.

"See, this is fun. Why couldn't we ever do this when we were together?" I asked.
"Yeah, you're right. I don't know" he answered.

We had always been confined to his apartment while we dated, and this was partly the reason why I felt so unhappy. I wanted to go out and experience new things with him, but he was so adamant about leaving the house, that we never went out more than a handful of times for the five months we dated... on and off...

As we drank and listened to the band play, he told me he had finally settled on a house, and it was currently in escrow. If everything went well, he'd be closing in a few days before Christmas and moving in soon after. When he told me where it was located, my heart skipped a beat- "It's really close to your work, you would have a short commute" he said. It was 3 miles down. I almost cried.

He asked me if I was seeing anyone, to which I replied "Sort of, but it's not really working out"

"Why not?" he asked.
"Because he's younger and very immature. He has a son, is a smoker and isn't good in bed. But he's incredibly beautiful. Tall, blond hair, green eyes. " I mentioned.
"What does he do?" he continued.
"He works for National Oilwell Varco and is a commissioner for the oil rigs" I added.
"NOV? They're one of our clients" he added.

As soon as I heard this, I shut up. I didn't want to give more info about Larry in case they did business together; that would have been awkward.

"But I really don't want to talk about him, and I don't want to hear about your girls either" I pressed.
"Why not?" he asked.
"Because I'll be jealous" I said.
"You don't think I'm jealous of this guy?" he asked.
"No" I said.
"Well I am. Why do you think I keep asking about him?" he added.

And with that, we continued drinking our beers, flirting endlessly, until suddenly, he pulled me in and kissed me. His aroma came over me like a wave; I was intoxicated with his scent. I could smell his skin pressed against my face, his tongue in my mouth, as I ran my fingers through his hair. I was completely and immediately absorbed in the moment, locked in a passionate kiss with my ex. I knew I should pull back, but I couldn't bring myself to.

Soon after, we went back to his place and immediately rushed into bed together. I was excited for what was about to come next since the IT Pilot had been the best sex I'd ever had. He could make me orgasm on command.

Except it didn't quite work out that way.....