It happened sooner than I would have hoped, but long enough ago now that I can rehash it without having nightmares and cold-sweats.
I took an extended vacation to Colorado two years ago. I was there for three weeks. Assuming I would find moments of boredom in that clean mountain air, I made a Craigslist ad before I left. "In town for a few weeks. Looking for fun things to do while I'm there." It was simple enough, I know. I included a sexy pic and began checking my email on the hour. It was fruitful. I few guys responded, but if they didn't creep me out, they bored me immensely. Then there was Mr. Apologies.
Mr. Apologies was charming, witty and polite. We exchanged a few emails, then I gave him my number. He texted immediately and over the next few days, the excitement built. I boarded the plane, knowing that not only was there a private mountain home and fresh Fall air waiting, but there was also an exciting short romance.
I got picked up from the airport and taken to the house in which I would be staying. It was pretty, but so secluded. As my driver pulled away, I felt a little overwhelmed. My phone rang. It was him. He had taken the day off of work because he knew I would be getting in and he wanted to "make himself available." Perfect. I hopped in the truck supplied by the owner of the house and made my first ever trek through the mountains to meet a man. We met at a local Italian restaurant. He was cute. Not gorgeous. He was tall and athletic. His face and body bore a few minor imperfections that added to his charm. His smile was slightly crooked, but not in the way a swindler's smile is crooked. He would do just fine for the next few weeks.
We went out a few times and it was great. I didn't bring him back to the house for a while. I didn't want to be the city girl that came up the mountains and delivered herself to the psychopathic serial killer that trolled Craigslist for unsuspecting vacationers. If he was going to kill me, he was gonna have to do it in public. But he wasn't a psychopath. He was utterly vanilla. His jokes were witty, but safe. He was timid when he kissed me and apologetic for being too forward.
The night I did decide to bring him back to the house, we had dinner and watched a movie. He brought a bottle of Jameson (upon request) and I made a homemade pizza. It was lovely. I could only imagine how happy he would make some husband-seeker one day. So, so normal. The night progressed and we decided to take the movie upstairs to the bedroom, because it was "warmer." You know ... heat rises.
Once you lay down with a man you have been hanging with every night, it doesn't take long for the hands to stray places they haven't yet ventured. It was hot on paper. A secluded house in the mountains, two virtual strangers, a hot tub in the room, snow capped mountains right outside the window and a bottle of whiskey. We were there. What could go wrong now?
I eased my hand down his bare stomach and unbuttoned his jeans. His hand grabbed for mine and then he relaxed. This was odd, but kind of hot. I felt like he had a momentary lapse in judgment and by that, I mean I felt like he might have considered exercising some restraint. Nah. We kept going. He seemed a little scared. Was this dude a virgin? I pushed that thought out of my mind and recklessly proceeded. I unzipped his pants and slid my hand down the front.
There it was ... The smallest dick known to womankind. I don't even know what to call it. I was amazed. I felt bad for touching it. It felt so ... so delicate. I didn't even really know what to do with it. It was roughly the length of my pinky, a little thicker. When I put my hand around it, I engulfed it. This was awful, but not as awful as it could get. Just as I was snapping to and getting past the shock of it all, he looks me in the eye ... In that way that says "Hey, look at me," and he said it. The worst two words in the world. He looked me in the eye and said, "I'm sorry." Oh God. Why? Couldn't we just let it be the unspoken thing that we both knew? Did you have to make me acknowledge it aloud? I thought about saying "For What?" and feigning ignorance of his small member, but that would have opened the doors for a "For my small dick." I couldn't risk more conversation so I said, "Make love to me." I couldn't bring myself to give him a Fuck me. He was just too nice.
So, I got on my back and he got on top of me. It was awkward. But, Yes. We had sex. Or some weird variation of it. What was I supposed to do, kick this nice man out into the cold snowy night with only his tiny dick to keep him warm? Grow up, people. Sometimes you have to take one for the good of humanity. So I took one. More like half. Ok. One-quarter.
He could barely get it in. I like doggie style, so I thought we could try, but he wasn't able to do that. Because we had had so much luck with the 'dirty talk' this evening, he decided to let me in on the little secret: He had never been able to accomplish the task of doggie style with any lover in the past.
Hoooo ... Okay, buddy. This is not share time. My vagina has officially crawled up into itself.
I was super embarrassed. This wasn't even like sex. It was so awkward. It wouldn't have been so bad if he hadn't kept saying things about it. He referenced the size of his dick with a disappointment that reminded me of the tone my mom took on when being passive aggressive. After the third comment and lack of any enthusiasm, I was about to throw in the towel. Dude, I'm a good person. If you take the time to lay with me and I take the time to lay down with you, I am gonna give your lil dick the ol' college try, but meet me halfway and leave your defeatist attitude at the door.
I guess I could have lied and told him it wasn't small, but what I couldn't muster in lies, I made up for in heart. I gave all I could, and right at the moment when I thought I couldn't do it anymore; right after his last comment, he slipped out of me, but the condom did not. It was too big for him. I pulled back and he went down on me. Disappointing. I'm not even going to go into it. I am not the type of person that feels she has to have company in her misery. Just know, it wasn't good. It even hurt a little.
After it was all said and done, he got up and drove into the night. I didn't have the heart to stop him or ask him to stay. We were both sad and I think we both just wanted to be alone. He called me a few times after and we talked, but on the last call, he brought up the night and apologized again. I couldn't take it. Bad sex once with someone that you cared about is minor, but this was all we were. He and I were just awful sex and apologies. I never answered his calls again. Think what you want of me. I moved my flight up a week and came back to Texas, where apparently everything is bigger. I think he blocked me on YahooIM. I'm not mad at him. I understand. I deleted him from my phone. I don't think either of us are fully over it.