I met someone new on Friday. We enjoyed lunch and then went back to my place. He’s someone who doesn’t have time for a relationship, but of course would like some sex and companionship now and then. This is ideal for me as I’m not looking for another serious relationship. Lunch with him was pleasant, and we know a few people in common. He gave me a ride on his scooter back to my place, and it was the first time I ever rode a scooter (haven’t been on a motorcycle yet). In my usual ladylike manner (har) I threw my leg over the back of the scooter despite wearing a dress. Thankfully I had worn a stretchy casual dress.
I clenched my thighs around his hips as we got started. He took things slow since it was my first time. It was fun and yes, I did wear a helmet. At the stop light, he reached down to caress my bare leg. Rowr. Some small part of me was still thinking, “Am I going to fuck him today or just make out or something?” But my subconscious knew I’d go all the way.
This guy is 10 years younger than me, and I’ve been questioning if this makes me a cougar. I think not since he wrote to me and I’m not exactly out trying to find younger men. He seemed to know what he was doing sexually, unlike too many men in their 20s. We got to my apartment, kissed and he suggested we get more comfortable. When I caught a glimpse of him in just his boxers, with a hard-on raging, I was delighted to see it was a substantial size. I don’t consider myself a size queen, but a little larger than average is always a bonus.
Since I didn’t think to put the air conditioning on until part-way through, it was hot, sweaty sex. I usually hate sweating for any reason, but it was sexy how our bodies slipped easily against each other. He had difficulty in that he’s similarly endowed as MasterDoc, and I mainly had the NYC condoms on hand – they run a bit small. (What’s up with that, NYC??) He didn’t try to get out of wearing them, he just pointed out that coming was going to be difficult with the condom so tight. I said that I’m sure we could figure out a way to make him come. I sucked his cock deep which he loved but it didn’t lead to orgasm.
While fucking younger men makes me worry they’ll be clueless sexually, this guy paired youthful energy with some expertise. As he pounded me into the bed he made me come over and over. I had to speak up a few times as my cervix can get cranky being pummeled like that. He could flip me over without ever taking his cock out. I ended up on top where I could control the depth more. I squirted a bit and he loved to hear that I did. It turns him on a great deal. That early on, however, it was difficult to tell the little bit of girl come from the copious amounts of sweat.
We went on playing without much of a break for much longer than most sexual encounters I have. (He accosted me in the kitchen as I tried to get a drink of water. Ha ha.) Again, I said a silent word of thanks to the weight loss and exercise. In the past I would have had to cry uncle. He asked if I like anal, and I said yes. I lubed my ass up and yet again this slut had anal on a first date.
Yeah well, you know my philosophy – if it feels good and I want to do it, why should I not? This is an area in which being an atheist is so liberating. I don’t have some fictional god telling me sex is wrong, or clergymen claiming to know how we should all live our lives. If it’s consensual and both parties want it? I can’t see why not to do it. The fucking went on a long time and I came countless times. I was glad that he knew he could go pussy to ass with the same condom, but needed a new condom to go back to the pussy. Sexual knowledge is sexy.
After much rolling around and rubbing body parts against each other (including more girl come as lubricant), I mentioned that I know how to do prostate massage. He was up for it and I lubed up his ass and slowly worked a finger in. Eventually, I took the time to work a second finger in. He writhed around and said it was too intense at times. He said it was the best prostate massage he’s ever had – the others didn’t know what they were doing. (I told him to thank MasterDoc.)
While the massage felt good, the intensity made him need a break, and he ended up jerking off while hovering over and intently examining my pussy. He complimented me on it, and while the skeptic in me thinks, “He must say that to all the girls!” it was still nice to hear. I didn’t hesitate to compliment his cock that day too. He came on my tummy and I felt glad that both of us had come. We each showered off the sweat and come we were pretty much covered in. He took his time getting dressed and soon after we said goodbye. I then proceeded to work on packing up my apartment for my upcoming move.
I was exhausted that night. I had worked out hard in the morning, and then there was that pleasurable second workout in the afternoon. I tried to cuddle with MasterDoc a bit, as I wanted to reconnect with him after having had recreational sex with someone else. On Saturday night, I hoped that he and I would get it on (we haven’t since Tuesday) but he was feeling like having time alone. I felt emotionally needy and luckily managed to strike a balance between asking for and getting attention, and giving him space to be by himself. We cuddled, and MasterDoc picked up on the fact that a beating would do me good. He whacked away at my ass with various implements. Sometimes I think there’s no way I can handle the pain, but then as soon as the beating stops the pain lowers to a manageable level. He made me come with the Hitachi magic wand and after I felt so much better. I had really needed the beating for the endorphin release, and the orgasm to round out the relaxation. I was able to go amuse myself after that and give MasterDoc more time alone. (My current addiction is figuring out how Sims Medieval is played.)









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