Failure to Fuck

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About halfway on my journey into anal play, I started fantasizing about getting a live cock in my ass. I embarked on a quest to stretch myself to accommodate the size and girth of the cocks in my daydreams. Anal masturbation is pleasurable, but it’s a solitary pursuit. Sex is always better with a partner. So when I was able to take a large dildo easily, I began my quest to find a man who would help me make my fantasy a reality. The other day I happened to drive past the motel where I had my first chance.

Because I love women, my preferred identity is bisexual. Believe it or not, if you’re not living the gay lifestyle, it’s not easy to get fucked. With high hopes, I signed on to a couple of dating sites, posted a profile and photos, and waited. Responses were few and far between. Most men who responded wanted a hookup. They sent cock pictures in their emails. When I invited a couple of them to meet first, they quickly backed off. As much as I was willing to open my ass to a sizable cock, I wasn’t desperate. I’ve never had an STD and didn’t want any. And the major risk facing the receiver in anal intercourse is HIV. I specified safe only in all my postings. I figured if I met a certified disease-free partner we could always begin barebacking. Eventually I gave up on the dating-site route. I decided to see what CraigsList had to offer. After all, it’s free.

I posted on the “Men Seeking Men” araban escort page on Philadelphia CraigsList. No pics, just a description of what I was looking for and my stats. I offered to trade photos if necessary. I immediately got the cock pictures and offers from the mutts who promised to “fuck me silly” if I could host. Right, moron, I’m going to have a stranger come to my home to have his way with me. I might be a pervert, but I ain’t stupid. And I got plenty of invitations from web whores to visit a page on some sleazy pay site. I was about to give up on CraigsList when I received what appeared to be a real response from a serious guy. He was willing to meet and we scheduled to meet for coffee at a Starbucks about half way between our locations.

I was a bit disappointed when I met Tom R. He was my age, average in all respects, certainly not the handsome stud I saw banging my ass in my fantasies. He assured me that he had poked several guys and had the experience to guide me through the first time. I figured after months of searching for an ideal partner, I couldn’t be choosy if I wanted to get it done. Tom seemed like a decent guy, so I thought, what the hell, let’s do it. I still wasn’t ready to invite a man to my place, so we arranged to meet the next Saturday afternoon at a cheap motel.

Tom showed up in the motel parking lot on time. The room cost $50. I gave him half. The plan was, he would check in and call my cell with the room number and I would join him. Ten minutes later he called and I went to the room. I was wearing sandals, shorts, and a polo shirt, no underwear, and I was naked first. Tom brought a gym bag with a couple of dildos, condoms, and lube. As soon as he got his clothes off, he began lubing a dong, saying, “This will loosen you up.”

I wasn’t letting anything in my ass without a condom. “You have to put a rubber on that.” Tom look disappointed. “Why? It’s clean. I put it through the dishwasher.”

“Sorry,” I said. “Got to have a condom.” He agreed. He wiped the lubricant off the dildo with a motel towel and slipped a condom on it. I climbed on the bed and waited on hands and knees. I spied his erection and thought it was big enough to do the job. He told me to lie on my stomach. He straddled me and began massaging my back, neck, and shoulders. “This will help you relax,” he said, moving his hands down my back. I didn’t think I needed to relax but I humored him. I felt his condom clad cock rubbing against my ass and began to get turned on. Next he began to poke my asshole with the dildo. It was hard and cold, but it increased my excitement and anticipation.

“Tom, I’m ready,” I said. I felt his cock poking between my cheeks, and followed by a comforting thrill when he pushed it against my anxious asshole. That’s as far as we got. Next thing I knew he was off the bed, sitting on a chair between the twin beds, pulling on his cock. He had lost his erection. “Give me a minute,” he said. I sat on the edge of the bed watching him stroking his half hard on. “Can I help?” I asked.

“I don’t understand,” he said, “This never happened before.” At that point in time, I had never sucked a dick, but I offered to blow him with a condom. “That wouldn’t work,” he said. After five minutes frantically manipulating his cock, it was flaccid. It looked like a tiny animal trapped in the sagging folds of the deflated condom. He apologized. “I’m sorry,” he told me, “This never happened before.” I believed he was sincere and felt sorry for him. “Don’t worry about it, Tom. Shit happens. You don’t need to apologize.”

I felt so bad for him I hardly felt my own disappointment. He was obviously embarrassed and couldn’t wait to get out of there. We dressed in silence and walked together to our cars. He apologized again at his car. “Please, don’t worry about it,” I said.

I thought about it for several days afterward. I wondered what had happened. Had Tom exaggerated his experience with men? Maybe he had never fucked a man. I didn’t consider it was my fault. I’m only average on looks, but I’m clean and have a good body and smooth clear skin. I couldn’t believe anything about me had turned him off.

I sent Tom an email a week later, asking if he wanted to try again. He didn’t respond. I had to resume my search.

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