Tom was #2. After the debacle of losing my virginity whilst trying to maintain my catfishery (and failing miserably), I put up a new profile with my real photos and was happily surprised at the response. I was even more delighted later when I opened the door to my hotel room to find 6'2” of gorgeous hunk standing in my doorway. I love it when a hookup turns out to be cuter than his pics. It's like a little, unexpected gift. Sometimes I intentionally send unflattering pics of myself to potential hook ups so I can give a little, unexpected gift too.
Tom was an easy going but take-charge kinda guy. Lickety split and I was blowing him like a champ. After all the years fantasizing and speculating about what I'd do with a hard cock in my mouth, I was going to make the most of this opportunity. Apparently, I am a natural. Tom was blown away by my oral skills and never knew that his was only the second penis to visit my mouth. At one point he had me lie on my back on the bed with my head hanging over the edge. He fed me his cock slowly and I found I could take him much deeper this way. I'd stipulated that condoms were a must. He rubbered up, positioned me doggy style at the edge of the bed, and standing behind me, slid his hard cock into me. After a while he pulled out of my cunt, placed his cock at my anus and asked, “can I fuck your ass?” I answered yes. I've had an anal fetish for as long as I can remember. Before I ever tried to penetrate my vagina, I would experimentally slide a finger into my asshole in the bath or shower. I thought that was The Hole. It felt good to me and by the time I figured out that the other hole was the primary one, I'd discovered the joys of the backdoor.
I had played with enough toys to know that the initial entry was going to be the hardest part. I also knew to relax and unclench. Tom gave me a moment to acclimate to the new invasion then gave me the assfucking I'd been waiting for all my life. I'm thankful that my first anal sex experience was a good one because I would learn in future that it doesn't take much of an inept or selfish jerk to make a person reluctant to unclench ever again.
Tom took a shower as I lay on the bed purring like a contended cat. As he got dressed, he waxed poetic about my blow job and asked if he could see me again. I told him I was only going to be in town a few more days but sure, hit me up. I ended up booty-calling him a couple days later and he rushed right over. However, having come straight from work, he had no condom. Nor did I since I hadn't expected to be sexually active. I offered to suck him off (I'd already told him the ass was off the menu as I was still a bit sore). What followed was a scenario that would repeat many, many times with many, many men. He begged, pleaded, and cajoled....and I caved. I did ask him not to cum in me since I wasn't on birth control and he agreed. I gave him a nice long blow job and he fucked me sans condom, pulling out as promised, and cumming on my tits.
I'm grateful for Tom. He was gorgeous, well-mannered (good manners go a long way, boys), and a great fuck. He still remains in my Top 5 Hookups of all time. However, hookup #4 would be even better....