Three-day Marathon

This has basically turned into Joe’s sex journal now.

Christy went to Denver for four nights to visit her aunt, so she said that I could play solo while she’s away. A few weeks ago, I joked that she’s she’d be gone four nights (five days) that I would like to see if she’d permit me having five dates. She agreed, but she probably thought I was joking. I wasn’t. 

As the date for her departure got closer, I was trying to arrange my dating adventures. I told Christy about my plans and she asked that I not have sex with anyone else on the same day that she comes home from her trip so that I’ll be ready to play with her. I of course agreed. So that left me with the option for four dates. I lined up dates with four women.

I’d met Shirley online a couple weeks prior. She started flirting with me and was very direct. She was very nervous about meeting, but loved sending me explicit sexual photos of herself, though she didn’t like showing her face much. (I did confirm that she was the woman in the photos.) She was very worried that I wasn’t going to be attracted to her when I met her. (She was putting a filter on the face photos she sent to make her look a bit prettier. She moved the date from the night that Christy left to the next morning, which would have had me having two dates on the same day. Shirley came to my home. Without a filter, she’s not someone I would normally have been attracted to, but she was enthusiastic and really into me. She basically begged me to fuck her. She was a lot of fun in bed and wanted me to do anything to her. She was the first woman other than Christy with whom I’ve had anal sex. It was a good time. She orgasmed a couple of times and actually I did also twice which really surprised me. Of course there was at least a 30 minute break between those two. It was a pleasant experience, but I don’t have plans to meet her again.

The next woman, Mira, whom I planned on meeting that same night for only a drink, no sex, had to cancel on me due to a last minute family emergency. (She showed me the new story and I saw it on her Facebook profile to know that she was telling the truth. )

Nelly was the next night. (I’d played with her a few months prior.) She came over, we had a little chit-chat and got busy. She’s my age, friendly, Latina, into me, and orgasms easily enough. (She likes being on top and rocking and sliding. Last time we played she almost snapped my penis in half. I actually got damaged that time. So. . .) I was a bit nervous about being hurt again, but it all went well. She got done at least once, and I did too. To prolong the experience, after the woman orgasms once, we take a break, talk and get something to drink (no alcohol), then we go again. I came during the second round. I held off during part one. 

Both women were here for less than two hours each. That’s the standard. Most women don’t want to stay longer than that, and at two hours, I check in via text with my wife. That’s our arrangement. — After Nelly left, I cleaned up: condom wrappers, water bottles, reoriented the tissue box and lube dispenser just as I had after the previous night, but where was that second condom? I know we’d used two. I had two wrappers, so there must be two condoms. I’d flushed the “full” condom, but where was the round-one condom. I was searching everywhere. And I HAD to find it because Melody was coming over the next night. It would be horrible if Melody found a recently used condom in the bedsheets. It look a lot of looking, but I found it plastered under the Kleenex box on the nightstand. Phew! 

The final night was Morry. She’s my new #2* (Christy is of course #1). I’d met Morry on Bumble about a month ago. We’re in the same industry, so she found an excuse to come to my work to meet me in person for about 20 minutes. Our second date was at a swanky bar where we talked for about 3 hours. This night was to be dinner and sex. Morry is high class: well-off, well-dressed, well-educated, fit, intelligent, and a bit intimidating. In may ways, she’s out of my league. I may appear to be “in her league”, but I’m just a man-child trying to fake it and only doing so with women who don’t know any better. Morry has two other girlfriends (one very serious) and another boyfriend. She likes dating a lot of people, and she’s very honest about it. — We met at the restaurant. She’s fancy. She knows wine. I know nothing about wine. We eat and she tells me more of her life story. We then come to my place. I undress her and we hit the bed—the same bed that I’ve had sex in with two other women on the two previous days. (I should say here that their names are not Shirley, Nelly, and Morry, but their names are all two syllables and they all rhyme. So I had to make a very conscience effort each time to be sure to call each by the correct name. They all have very similar hair style, bodies, and physiques. What I was doing was nuts. Seriously nuts.) Morry was the best dressed and most high-end, so I felt like I needed to be careful with her as I undressed her. Her bra and panties were VERY classy. I felt out-classed by her, and that I needed to ask permission with everything—which I do anyway as a matter of getting consent. I ask before going down on her, and I ask her what she wants. With Shirley, we had flirted a lot online prior to meeting, and with Nelly we’d played before, so I knew where to go with those two women. Morry and I hadn’t had much sex-talk prior to this, so this sexual experience was new territory for us. We started playing and about 10 minutes into it, I had a condom on and was on top thrusting. I warned her that if I kept going, I was going to cum. She told me to. — Normally I would have held off until round two, but given that I was tired from the previous two nights and was worried that I wasn’t going to be able to go strong in a round-two and that I really wanted to cum with Morry, I allowed myself to orgasm earlier that I should have. I thought she came also, but she later told me that she didn’t. — I went to the bathroom and cleaned up. We then laid in the bed naked and talked for a while. That’s what I do during the intermission. I then got hard again and we went for round two. Round two consisted of a lot action that went nowhere. I did all the work I could, but she didn’t cum. She actually did seem fine with it. She told me that it’s difficult for her to orgasm. I trusted her. The date was fine. She wrote a note thanking my wife for allowing me to play with her. I do hope to see her again.

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My previous #2 dumped me. There was a nice woman who was into submission. She wanted me to call her “bitch”, “cunt”, “slut” and slap and choke her. We’d played four times. I liked her, but she wasn’t great at communicating. We had plans to meet next week, but she emailed me yesterday to tell me that she’s taking time to work on herself. It was a nice email, and she said that she would like to see me again some in the future, but for now we’re on hiatus.