True-Life Confessions of a CD

November 3

My hole is sore. But it's a good kind of sore. It feels s-t-r-e-t-c-h-e-d. More on the reason for this in a minute.

Sex-wise I had a good day yesterday—one of the best ever. I invited three guys over to my house and two showed. (The third emailed me later saying he'd fallen asleep. "Are you available tomorrow?" "NO!") For fickle Craigslist, especially all on the same day, that's a pretty good result. I replied to the first guy's ad; the second replied to mine: Crossdressing sub will suck your cock on your way home...Et cetera, et cetera. The usual shit—though I haven't been haunting the hallways of CL for some time now. Sometimes it's good to get away for awhile. Which makes it all the more pleasing, yesterday's results.

For my guests I wore my platinum-blonde wig, green eyeshadow, red lipstick, black bra, matching microfiber panties and my last remaining pair of thigh-highs, which were kind of a tan-charcoal in color. There are two problems with thigh-highs: they're expensive and they're only good for one wear. They develop runs, get holes in the toes...I much prefer pantyhose, which can be machine-washed and usually worn multiple times. The problem is pantyhose can be, shall we say, somewhat problematic if your partner wants quick access to your bottom. I also slid my slender feet into a cute pair of black-strapped, open-heel flats (I'm tall enough as it is without donning heels, which I don't even own). I decided to do the CL thing on short notice, so I didn't have time to apply a fresh coat of red lacquer to my toenails. As a final touch I adorned my left leg with a red-beaded anklet. I was ready—but not perfectly so.

The first guy arrived on time at about five p.m. There were no preliminaries aside from the fact that he asked if he could use the bathroom. I thought about asking if I could hold his cock while he peed but decided against it. I didn't know him and thought the offer might seem weird, or off-putting. He wanted a BJ pure and simple. We went in the livingroom, he remained standing, I dropped to my stockinged knees as he lowered his pants. Despite having blown him only yesterday, I don't have a clear memory of his cock. It wasn't anything special; not overly long or thick. I took him deep without a problem, without gagging. Despite him having just peed his cock tasted fresh and clean.

He came moderately quickly—in my mouth. I swallowed. His cum salty and potent, cutting right through the saliva. I hadn't swallowed cum in months and it tasted delicious. What a treat!

The guy was already pulling his pants up when I got to my feet, pleased with the result and smiling. I asked if he wanted me to clean him up. He said it wasn't necessary. I asked him if he was married. He said yes. Of course he was. They almost always are. As with most guys guilt or self-disgust had just displaced the reservoir of wild, same-sex desire he'd had prior to cumming. He couldn't get out of there and back to the wife fast enough. I followed him to the door as he hurried away. Wham, bam...Typical male.

My second guest arrived, also on time, at about 8:30. The first guy had been a white-bread Caucasian; this guy was, I think, Hispanic. A slight accent. Upon arrival he reached out and gave my pantied balls a quick fondle; a quick hello. This being something I enjoy very much. It sends the signal that he at least finds some aspect of your gender duality sexy. I asked him if he wanted anything to drink. A beer? Water? He said he didn't drink. This being another thing I've noticed about Craigslist sex partners over the years, and I've had dozens and dozens of them. Maybe a hundred altogether. In addition to almost invariably being married, they almost always never drink. I wonder how they do it. I'm way too inhibited to do this kind of thing sober. In fact—although I try to hide it best I can—I'm usually smashed by the time a guest arrives. Strict religious upbringing at work, I guess...

The guy was concerned about people being able to see us. I have a two-story house and the livingroom has an array of six big windows that look out on the backyard. I turned the floods on to prove to him that my backyard is basically a wilderness area. "No one is back there," I explained. I asked if he wanted me to get down on my knees and start sucking him but he surprised me by asking if he could fuck me instead. I said sure. But...I hadn't expected this and so hadn't prepared my ass for that pleasurable eventuality. Meaning I hadn't "douched" myself. (I keep a multi-pack of disposable enema bottles in a cabinet under the bathroom sink.) He said he didn't care and asked if I had condoms.

I ran upstairs and returned with Trojan packets (receptacle-end) and a tube of K-Y. I was thrilled, but wary. This was a totally unexpected turn of events. If only I'd douched myself! I asked him where he wanted to do it—the couch?—but he said first he wanted me to suck him. He removed his pants as I sank to my knees again just outside the kitchen. His cock was enormous. Dark-skinned. Uncircumcised. It was a beauty. A wild animal. Already mostly engorged. I paid my obeisance. I kissed and sucked it. But his mind was entirely on fucking me. I have these several wooden barstools with ribbed backs. He told me to sit on one facing backwards, with my now bare ass hanging over the edge. Condom on, he fucked me standing up, penetrating me in one very thick, very long continuous entry. It hurt. I thought my prostate was going to explode! Normally if I know I'm going to bottom for a guy I not only douche myself, maybe even twice, but then open my hole up in the shower with my dildo. I like to be prepared. I like to offer my partner a completely clean, accessible hole. I like to cover all eventualities.

This was not something I'd prepared for or expected. It hurt. At first. But I had to grin and bear it. I'd had bigger cocks in my mouth and up my ass before, but not by much. After pushing in I think he asked if I was OK. I said yeah. I wasn't, quite. But...

He fucked me on the stool for a few minutes then had a better idea. He wanted me to kneel for him on the carpeted stairs just behind us. He pulled his condomed cock out. It was—predictably—dirty. I was embarrassed. He said don't worry about it. He wiped himself off. I got him more wet paper towels. He thanked me, lubed up. I kept apologizing. He said to kneel on the stairs. Higher. Up one more. Spread your legs. Wider. Wider!

In addition to his cock and his desire to fuck me, I liked him for another reason. He liked to be in charge; play the Dom to some extent. (I used to have a semi-regular Dom until he injured me with a sound. I initially used to get together with him at a condo in a nearby clothing-optional resort. Then we lost contact for a while. Then we reunited. We made all kinds of plans for exotic Dom/sub activities. Then I ended up in the ER...) He enjoyed barking orders and I enjoyed obeying them. Wider! Curve your back! He kept saying that as he, standing, bending over, fucked me on the stairs. A novel position from my point of view. Different! Fun! When he entered me the second time it was not painful. It was fine. He more than filled my rectum but...it was OK now. (My prostate still felt like it was about to explode, though.)

He fucked and fucked me. He slapped the side of my ass occasionally—something I really enjoy. He asked me if I was his slut. I told him I was. He asked when he could come back to fuck me again. I replied... "Tomorrow?" He laughed.

His motion slowed. He pulled out of my ass. I asked him if he'd cum. He said yes. His orgasm had been a completely silent one. He handed me the dirty condom. I apologized again. He said no problem. I asked if he wanted me to get on my knees and suck the (residual) cum off his cock, but he said no. Had to get going. Home to the wife in all probability.

What a great, unexpected, hole-stretching fuck it had been, however. I would like to think the guy was serious when he asked when he could come back, but I have my doubts. I met him on Craigslist, after all.

Coda: Earlier in the evening I'd corresponded with a guy a few miles away who was offering his beautiful young (relatively speaking) ass to any takers. His pic showed him sprawled belly-down on a bed, legs spread. Great ass. Hot! (He was not a crossdresser.) He emailed me late to say he hadn't had any takers and was going to bed. Goodnight.

I emailed him back that I'd just had the most amazing luck. I told him about my second visitor; his unexpected desire to fuck me; and how big his cock was. My new "friend" asked me to send him a pic of it. I did. He replied back: "Holy shit! Latin?"

I felt naïve. The guy sure knew his cocks.

This could be a recurring series of true-life posts, I don't yet know. Depends of mood, compelling experiences, etc. We shall see...