Sex on the First Date

I met a woman online a while ago. We've talked a few times on the phone and many times by text. Last night was the first time we'd met in person, and we hit it off right away. The conversation is really good, we have a couple of glasses of wine and a couple of appetizers, then I pull her face gently to mine and make out with her in the restaurant for about a minute. The chemistry is obvious, and we are holding hands and I am stroking her leg and arm as we talk. She has beautiful skin and I tell her just that. She says "What am I going to do with you?" My reply is, "Take me home". She agrees, with a shit-eating grin on her face.

She alludes to some skills she has, but I never give her the chance. We start making out on her bed right away, she pulls off my shirt, a button-down one, over my head in haste. I get all her clothes off and take my time, teasing and kissing and caressing everything, at first missing any of the usual erogenous zones. But only by a tiny bit. She's moaning and writhing around on the bed, a big turn-on for me. She's enjoying the teasing, obviously. I massage her feet, kiss slowly all the way up her body, finally giving her a little extra pleasure by sucking on one of her nipples. Or so I think. She's SUPER sensitive in her nipples, and with just a little tongue and lip pressure and movement, she cums for the first time. I've still got my pants on.

This. Is. Hot.

I haven't even touched her pussy, have only felt the warmth so far, but already she's grinding it into my body and arching her back. I'm in heaven, and I'm pretty sure she is, too. I love it when a woman relaxes with me and just lets go. I then put my fingers on her labia majora, stroking to bring in even more blood to the area to engorge and sensitize it. She's in her late 40s, but lubrication is obviously no problem here. She is dripping wet. I don't even have to reach for the lube.

I work in a couple of fingers to hit one of my favorite areas, and obviously hers, while sucking on one of her nipples. She loses her breath, and though she's trying to say my name, only the first syllable of that and any other word she tries to utter will come out. I've apparently interrupted her wiring in all the right ways. She cums and cums. I still have my pants on, hard-on raging behind the denim. I work my way down and start going down on her, she cums even harder. We go on like this for well over an hour, almost two, and she begs me for a break. Yep, I still had my pants on. I was leading her, starting to learn what she likes, finding her favorite spots. I was 100% present and picking up on her non-verbal communication, very helpful especially at those times when she can't talk. She has all three types of orgasms; positive orgasms: "YES! YES! YES!", negative orgasms: "Oh, no! Oh, No! Oh, No!" and religious orgasms: "OH, MY GOD! OH, MY GOD!".

I finally take my pants off, then tease her more by kissing her, rubbing my cock all over her, and bringing her to a few more orgasms with my cock still just pressing against her. At one point she tries to push my hands and face away from her nipples, so I pin her wrists above her head and keep going at her. This turns her on even more. She's a sweaty, wet mess from head to toe at this point.

I finally tease her pussy a little with my cock, then go in. She cums immediately and again a couple of times. I flip her over and before entering her, I whisper in her ear that she has to have my permission before she can cum again. I enter and she asks right away. I hold her off and she starts begging. I finally let her and she starts screaming. I've used this method before to teach a woman to cum on my command, and this is the start. I'm getting the feeling she won't be too hard to train.

She's open to everything so far, so I rimmed her a little and could feel the shivers that causes. Mix that with some fingers inside her dripping wet pussy and then switching to a finger resting on her anus, which she responds to very well. I lubricate my thumb with her juices and press it in a little bit. She responds by cumming, moaning loudly and pressing her asshole back against my thumb. I slide it in and she goes berserk, cumming harder. Next thing I know, she begs me to stick my cock in her ass. Not bad for a first date, eh?

We ultimately collapsed into a sweaty pile on the bed and fell asleep for two hours. I had to hit the head, so she walked me down the hallway in the dark to turn on the light for me. I grab her, press her against the wall and make her cum again before I go into the bathroom. She breathlessly whispers "You are so bad!"

We get in an hour of sleep before her alarm goes off, at which point I make sure she has an orgasm as she wakes up. As I get dressed to leave, she kisses me and asks when she can see me again.

I think I've created another addict!

Booty Call

Last night I was tired after a long day of work, and I had an injured foot that was mending, but I'd been standing on it all day.

Then came the text from "Marjie" (not her real name). She asked what I was doing and if I'd come see her. We'd had sex before and she had a really good time, and we'd sext back and forth from time to time. She begged me to come see her. I knew what she had in mind. It had been over a week since I've had any, so though I was tired, I didn't resist much. I joined her for a cup of tea at a local coffee shop, we talked for a while and I teased her mercilessly, not making my sexual interest a mystery at all. She did the same back, it was really fun and dirty in the best way. She stroked my cock through my jeans when nobody was looking, we kissed a couple of times and at one point I leaned into her and whispered what I wanted to do to her right there. She blushed and admitted how wet she was.

We were a long way from my place and her place had roommates, so she drove me to the gated parking lot where she worked. I teasingly caressed and stroked her leg while she was driving. We crawled into the back of her SUV and she immediately took off her soaked panties from under her dress. It was hot. We started making out, exploring each other with our lips, and the clothing started coming off. I love to tease, so I kissed all the way around any particularly sensitive and potentially orgasm-producing area, letting her know I was there with my lips and my breath.

She moaned, sometimes almost in complaint to the teasing.

She's quite a bit younger, and I usually like women closer to my own age. They appreciate it more. This girl was young and I could tell it was going to take a lot of work over several sessions to open up a few new neural pathways, the pleasure highway to the brain. It's the kind of work I love, but it isn't easy.

I gave her some good oral and worked simultaneously on her G-spot, also working around to see what other areas she liked. Inexperience and being in a car kept her fairly quiet, not the easiest way to work with someone on learning what they love. She was delicious, and wet like no woman I'd ever experienced. I was loving that, and she was, too.

I kept working her up and stopping short of taking her over the edge, getting her really worked up. I'd kiss back up her body, tease and suck her nipples, kiss her neck and make out while still having my fingers exploring her clit, labia majora, G-spot and other areas. I was hard as a rock, because I love all this. She begged me to enter her. I like it when they beg...

I teased a little more, till she had her legs wrapped around me, heels digging into my ass to pull me in. I finally entered her and we both gasped with pleasure. We went faster and slower, had to duck down when some people walked by, and when the parking lot was empty of people and she said "Harder", I did and she came. Repeatedly. When I finally looked at the clock, we'd been going at it in her car for almost three hours! We made out for a while afterward, got dressed, then shared some passionate kisses as she dropped me back off at my car.

It was great, but I worry sometimes. Great sex gets me booty calls, but if the sex is great and the connection good, sometimes the FWB wants more than I want to give. I've learned over the years to be very good, but there are subtle things like eye contact at certain times, etc. that can complicate that. I have been a serial monogamist in the past, but right now I am not looking for a relationship. Or at least, I don't want to get into a bad one. Last night's seems to have started to cross the line. I'm going to have to have a talk with her that hopefully will keep things good and healthy for us both.

*This is a true story. Trying to learn and teach through my writing, and I'm ALWAYS open to constructive comments.